ALKOXYLATED AMIDES, ESTERS, AND ANTI-WEAR AGENTS IN LUBRICANT COMPOSITIONS AND RACING OIL COMPOSITIONS

Abstract

A lubricant composition includes a base oil, an alkoxylated amide, an ester, and an anti-wear agent including phosphorus. The alkoxylated amide and ester have general formulas (I) and (II), respectively. The lubricant composition may be further defined as a racing oil composition.

Description

FIELD OF THE DISCLOSURE

The present disclosure generally relates to an additive package, a lubricant composition, and a racing oil composition.

BACKGROUND

Performance of lubricant compositions can be improved through the use of additives. For example, certain anti-wear agents have been added to lubricant compositions in order to reduce wear and increase fuel economy. However, further improvements in fuel economy are desired.

It is an object of the present disclosure to provide a combination of additives that improves the wear properties and the fuel economy of an internal combustion engine lubricated with the lubricant composition.

SUMMARY OF THE DISCLOSURE

The present disclosure provides a lubricant composition including a base oil, an alkoxylated amide, an ester, and an anti-wear agent including phosphorus. The alkoxylated amide has general formula (I):

The ester has general formula (II):

In general formulas (I) and (II), each R¹, R², R³, and R⁴ is, independently, a linear or branched, saturated or unsaturated, hydrocarbyl group, at least one of R² and R³ includes an alkoxy group, and R⁴ includes an amine group.

The present disclosure also provides a racing oil composition. The racing oil composition includes a base oil, an alkoxylated amide, an ester, and an anti-wear agent including phosphorus.

The present disclosure further provides a method of maximizing the effectiveness of a friction modifier in a racing oil composition thus increasing the fuel economy of a racing vehicle. The method includes providing the racing oil composition and lubricating an internal combustion engine of a racing vehicle to increase the fuel efficiency of the racing vehicle.

BRIEF DESCRIPTION OF THE DRAWINGS

Advantages of the present invention will be readily appreciated as the same becomes better understood by reference to the following detailed description when considered in connection with the accompanying drawings wherein:

FIG. 1 is a graphical representation of a traction coefficient evaluation of one embodiment of a lubricant composition; and

FIG. 2 is a graphical representation of a fuel consumption evaluation of another embodiment of the lubricant composition.

DETAILED DESCRIPTION OF THE DISCLOSURE

The present disclosure provides an additive package for a lubricant composition. The additive package or the lubricant composition includes an alkoxylated amide, an ester, and an anti-wear agent including phosphorus, molybdenum, or a combination thereof. The lubricant composition also includes a base oil. The additive package may be added to lubricant compositions. Both the additive package and the resultant lubricant composition (upon addition of the additive package) are contemplated and described collectively in this disclosure. It is to be appreciated that most references to the additive package throughout this disclosure also apply to the description of the lubricant composition. For example, it is to be appreciated that the lubricant composition may include, or exclude, the same components as the additive package, albeit in different amounts.

The alkoxylated amide has the following general formula (I):

In general formula (I), each R¹, R², and R³, is, independently, a linear or branched, saturated or unsaturated, hydrocarbyl group.

The ester has the following general formula (II):

In general formula (II), each R¹ and R⁴, is, independently, a linear or branched, saturated or unsaturated, hydrocarbyl group. It is to be appreciated that the hydrocarbyl group R¹ of the alkoxylated amide may be the same or different than the hydrocarbyl group R¹ of the ester.

As referred to herein, the hydrocarbyl groups of R¹, R², R³, and R⁴ are each, independently, a monovalent organic radical which includes, but is not limited to, hydrogen and carbon atoms. Each hydrocarbyl group designated by R¹, R², R³, and R⁴ may be, independently, linear or branched. Each hydrocarbyl group may be, independently, aromatic, aliphatic, or alicyclic. Each hydrocarbyl group may be, independently, saturated or ethylenically unsaturated. Each hydrocarbyl group may, independently, include an alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, alkylaryl, arylalkyl group, or combinations thereof. Each hydrocarbyl group designated by R¹, R², R³, and R⁴ may, independently, include from 1 to 100, 1 to 50, 1 to 40, 1 to 30, 1 to 20, 1 to 17, 1 to 15, 1 to 10, 1 to 6, or 1 to 4, carbon atoms. Alternatively, each hydrocarbyl groups designated by R¹, R², R³, and R⁴ may, independently, include less than 20, less than 15, less than 12, or less than 10, carbon atoms.

Exemplary alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, 2-ethylhexyl, octyl, cetyl, 3,5,5-trimethylhexyl, 2,5,9-trimethyldecyl, hexyl, and dodecyl groups. Exemplary cycloalkyl groups cyclopropyl, cyclopentyl and cyclohexyl groups. Exemplary aryl groups include phenyl and naphthalenyl groups. Exemplary arylalkyl groups include benzyl, phenylethyl, and (2-naphthyl)-methyl.

The hydrocarbyl groups designated by R¹, R², R³, and R⁴ may be, independently, unsubstituted or substituted. By “unsubstituted,” it is intended that the designated hydrocarbyl group, R¹ for example, is free from substituent functional groups, such as alkoxy, amide, amine, keto, hydroxyl, carboxyl, oxide, thio, and/or thiol groups, and that the designated hydrocarbyl group or hydrocarbon group is free from heteroatoms and/or heterogroups.

In some embodiments, the hydrocarbyl groups of R¹, R², R³, and R⁴ are, independently, free from, or includes a limited number of certain substituent groups. For example, R¹, R², R³, and R⁴ may, independently, include fewer than three, fewer than two, one, or be completely free from, carbonyl groups. In other aspects, the hydrocarbyl groups of R¹, R², R³, and R⁴ are, independently, free from an estolide groups (and is not an estolide). In still other aspects, the hydrocarbyl groups of R¹, R², R³, and R⁴ may be, independently, free from metal ions and/or other ions.

In certain aspects, each hydrocarbyl group designated by R¹, R², R³, and R⁴ may be, independently, substituted, and include at least one heteroatom, such as oxygen, nitrogen, sulfur, chlorine, fluorine, bromine, or iodine, and/or at least one heterogroup, such as pyridyl, furyl, thienyl, and imidazolyl. Alternatively, or in addition to including heteroatoms and heterogroups, each hydrocarbyl group designated by R¹, R², R³, and R⁴ may, independently, include at least one substituent group selected from alkoxy, amide, amine, carboxyl, cyano, epoxy, ester, ether, hydroxyl, keto, sulfonate, sulfuryl, and thiol groups.

In certain embodiments, the alkoxylated amide having general formula (I), R¹ may include from 1 to 40, 3 to 35, 5 to 30, 6 to 25, 6 to 23, 7 to 23, 8 to 16, or 9 to 13, carbon atom(s). In some embodiments, R¹ is a linear or branched, saturated or unsaturated, C₇-C₂₃ aliphatic hydrocarbyl group which optionally includes a hydroxyl group. In certain embodiments, R¹ of general formula (I) is derived from coconut oil.

In general formula (I), at least one of R² and R³ includes an alkoxy group. As referred to herein, an alkoxy group is defined as an alkyl group singularly bonded to an oxygen atom. The alkoxy group may be linear or branched. Non-limiting examples of suitable alkoxy groups include ethoxy, propoxy, and butoxy groups. At least one of R² and R³ may include, independently, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more alkoxy group(s). As one example, R² may include 2 alkoxy groups and R³ may include 3 alkoxy groups. As another example, R² may be free from alkoxy groups and R³ may include 3 alkoxy groups. As a further example, R² may include 2 alkoxy groups and R³ may include 2 alkoxy groups.

In certain embodiments, R² includes an ethoxy, a propoxy group, a butoxy group, or a combination thereof. In other embodiments, R³ includes a propoxy group, a butoxy group, or a combination thereof In some embodiments, both R² and R³ include a propoxy group, a butoxy group, or a combination thereof.

R² of the alkoxylated amide may have a general formula (III):

In general formula (III), R⁵ is an alkyl group, each R⁶ is an alkoxy group, and n is an integer from 0 to 5.

In general formula (III), the alkyl group of R⁵ may include from 1 to 25, 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, or 2 to 3, carbon atom(s). The alkyl group may be linear or branched. In certain embodiments, the alkyl group of R⁵ is an ethyl group or a propyl group.

In general formula (III), each alkoxy group of R⁶_n may independently be an ethoxy group, a propoxy group, or a butoxy group such that R² of the alkoxylated amide may include an ethoxy group, propoxy group, butoxy group, or combinations thereof. In certain embodiments, each alkoxy group of R⁶_n is, independently, a propoxy group or a butoxy group. For example, in embodiments wherein n of R⁶_n is R⁶_n may include two propoxy groups, two butoxy groups, or one propoxy group and one butoxy group.

In various embodiments, R³ of the alkoxylated amide is a hydrocarbyl group having a general formula (IV):

In general formula (IV), R⁵ is an alkyl group, each R⁶ is an alkoxy group, and m is an integer from 0 to 5.

In general formula (IV), the alkyl group of R⁵ may include from 1 to 25, 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, or 2 to 3, carbon atom(s). The alkyl group may be linear or branched. In certain embodiments, the alkyl group of R⁵ is an ethyl group or a propyl group.

In general formula (IV), each alkoxy group of R⁶_m may independently be an ethoxy group, a propoxy group, or a butoxy groups such that R³ of the alkoxylated amide may include one or more ethoxy groups, propoxy groups, butoxy groups, or combinations thereof. In certain embodiments, each alkoxy group of R⁶_m is, independently, a propoxy group or a butoxy group. For example, in these certain embodiments wherein m of R⁶_m is 2, R⁶_m may include two propoxy groups, two butoxy groups, or one propoxy group and one butoxy group.

With regard to general formulas (III) and (IV), in some embodiments, 1≤(n+m)≤5. In other words, n+m has a sum of from 1 to 5. Alternatively, 1≤(n+m)≤3, 1≤(n+m)≤2, or n+m=1.

In certain embodiments, the alkoxylated amide having general formula (I) is further defined as having a general formula (VIII):

R¹—C(═O)—N[R⁵—O—R⁶_n—H][R⁵—O—R⁶_m—H]  (VIII)

In general formula (VIII), in certain embodiments, R¹ is a linear or branched, saturated or unsaturated, C₇-C₂₃ aliphatic hydrocarbyl group, R⁵ is an alkyl group, R⁶ is an alkoxy group, n is an integer from 0 to 5, and m is an integer from 0 to 5. In general formula (VIII), in certain embodiments, 1≤(n+m)≤5. In one embodiment, each alkyl group of R⁵ is, independently, an ethyl group or a propyl group, and each alkoxy group of R⁶_n and R⁶_m is, independently, a propoxy group or a butoxy group. Non-limiting examples of suitable alkoxy groups designated by R⁶ include:

The alkoxylated amide, such as the alkoxylated amide of general formula (I), may be present in the additive package in an amount of from 0.01 to 75, 0.01 to 50, 0.01 to 25, 0.1 to 15, 0.5 to 10, or 1 to 5, wt. %, based on the total weight of the additive package. Alternatively, the alkoxylated amide may be present in amounts of less than 75, less than 50, less than 25, less than 15, less than 10, or less than 5, wt. %, based on the total weight of the additive package.

The alkoxylated amide may be present in the lubricant composition in an amount of from 0.01 to 20, 0.05 to 15, 0.1 to 10, 0.1 to 5, 0.1 to 2, 0.1 to 1, or 0.1 to 0.5, wt. %, based on the total weight of the lubricant composition. Alternatively, the alkoxylated amide may be present in the lubricant composition in an amount of from 0.01 to 20, 0.01 to 15, 0.01 to 10, 0.01 to 5, 0.01 to 2, 0.01 to 1, or 0.01 to 0.5, wt. %, based on the total weight of the lubricant composition. Alternatively, the alkoxylated amide may be present in amounts of less than 20, less than 15, less than 10, less than 5, less than 2, less than 1, or less than 0.5, wt. %, based on the total weight of the lubricant composition.

Referring specifically to the ester having general formula (II), R¹, of general formula (II), may include from 1 to 40, 3 to 35, 5 to 30, 6 to 25, 7 to 23, 8 to 16, or 9 to 13, carbon atoms. In some embodiments, R¹ is a linear or branched, saturated or unsaturated, C₇-C₂₃ aliphatic hydrocarbyl group. R¹ may include a hydroxyl group. In certain embodiments, R¹, of general formula (II) is derived from coconut oil.

R⁴, of general formula (II), includes an amine group. The amine group may be a primary, secondary, or tertiary amine. In some embodiments, the amine group is alkoxylated.

In certain embodiments, R⁴ of the ester of general formula (II) has a general formula (V):

In general formula (V), R⁵ is an alkyl group, and each IC and R⁸ is, independently, a linear or branched, saturated or unsaturated, hydrocarbyl group. In general formula (V), the alkyl group of R⁵ may include from 1 to 25, 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, or 2 to 3, carbon atom(s). The alkyl group may be linear or branched. In certain embodiments, the alkyl group of R⁵ is an ethyl group or a propyl group.

In general formula (V), at least one of R⁷ and R⁸ includes an alkoxy group. In certain embodiments, R⁷ includes an ethoxy, a propoxy group, a butoxy group, or a combination thereof. In other embodiments, R⁸ includes an ethoxy, a propoxy group, a butoxy group, or a combination thereof. In some embodiments, both R⁷ and R⁸ include a propoxy group, a butoxy group, or a combination thereof.

In various embodiments, R⁷ is a hydrocarbyl group having a general formula (VI):

In general formula (VI), R⁶ is an alkoxy group, and p is an integer from 0 to 5. In general formula (VI), each alkoxy group of R⁶_p may independently be an ethoxy group, a propoxy group, or a butoxy group. In certain embodiments, the alkoxy group of R⁶_p is, independently, a propoxy group or a butoxy group. For example, in embodiments wherein p of R⁶_p is 2, R⁶_p may include two propoxy groups, two butoxy groups, or one propoxy group and one butoxy group.

In various embodiments, R⁸ is a hydrocarbyl group having a general formula (VII):

In general formula (VII), R⁵ is an alkyl group, R⁶ is an alkoxy group, and q is an integer from 0 to 5.

In general formula (VII), the alkyl group of R⁵ may include from 1 to 25, 1 to 15, 1 to 10, 1 to 8, 1 to 6, 1 to 4, or 2 to 3, carbon atom(s). The alkyl group may be linear or branched. In certain embodiments, the alkyl group of R⁵ is an ethyl group or a propyl group.

In general formula (VII), each alkoxy group of R⁶_q may independently be an ethoxy group, a propoxy group, or a butoxy group. In certain embodiments, each alkoxy group of R⁶_q is, independently, a propoxy group or a butoxy group. For example, in embodiments wherein q of R⁶_q is 2, R⁶_q may include two propoxy groups, two butoxy groups, or one propoxy group and one butoxy group.

With regard to general formulas (VI) and (VII), in certain embodiments, if q is 0, p is an integer from 0 to 5. If q is >0, p is an integer from 1 to 5. In some embodiments, 0≤(p+q)≤5. In other words, p+q has a sum of from 0 to 5. Alternatively, 0≤(p+q)≤3, 1≤(p+q)≤2, or p+q=1. In some embodiments, p is 0 to 3 and q is 0, or p is 1 to 3 and q is 0. For example, in one exemplary embodiment, q is 0 and p is 3 and in another exemplary embodiment, q=0 and p=0.

In certain embodiments, the ester having general formula (II) is further defined as having a general formula (IX):

R¹—C(═O)—O—R⁵—N[R⁵—O—R⁶_q—H][R⁶_p—H]  (IX)

In general formula (IX), in certain embodiments, R¹ is a linear or branched, saturated or unsaturated, C₇-C₂₃ aliphatic hydrocarbyl group, R⁵ is an alkyl group, R⁶ is an alkoxy group, q is an integer from 0 to 5, and p is an integer from 0 to 5. In general formula (IX), in certain embodiments, if q is 0, p is an integer from 0 to 5, if q is >0, p is an integer from 1 to 5, and 0≤(p+q)≤5. In one embodiment, each alkyl group of R⁵ is, independently, an ethyl group or a propyl group, and each alkoxy group of R⁶_q and R⁶_p is, independently, a propoxy group or a butoxy group. Non-limiting examples of suitable alkoxy groups designated by R⁶ include:

The ester, such as the ester of general formula (II), may be present in the additive package in an amount of from 0.01 to 75, 0.01 to 50, 0.01 to 25, 0.1 to 15, 0.5 to 10, or 1 to 5, wt. %, each based on the total weight of the additive package. Alternatively, the ester may be present in amounts of less than 75, less than 50, less than 25, less than 15, less than 10, or less than 5, wt. %, each based on the total weight of the additive package.

The ester may be present in the lubricant composition in an amount of from 0.01 to 20, 0.05 to 15, 0.05 to 10, 0.05 to 5, 0.05 to 2, 0.05 to 1, or 0.05 to 0.5, wt. %, based on the total weight of the lubricant composition. Alternatively, the ester may be present in the lubricant composition in an amount of from 0.01 to 20, 0.01 to 15, 0.01 to 10, 0.01 to 5, 0.01 to 2, 0.01 to 1, or 0.01 to 0.5, wt. %, based on the total weight of the lubricant composition. Alternatively, the ester may be present in amounts of less than 20, less than 15, less than 10, less than 5, less than 2, less than 1, or less than 0.5, wt. %, based on the total weight of the lubricant composition.

The additive package or the lubricant composition may include the alkoxylated amide and the ester in a weight ratio of less than 50:50, 40:60, 30:70, 25:75, 20:80, 15:85, 10:90, 5:95, 3:97, 2:98, 1:99, or 0.1:99.9, of the ester to the alkoxylated amide.

With regard to general formula (VIII) for the alkoxylated amide and general formula (IX) the ester, in certain embodiments, each R¹ is, independently, a linear or branched, saturated or unsaturated, C₇-C₂₃ aliphatic hydrocarbyl group. Further, in these embodiments, each R⁵ is, independently, an ethyl group or a propyl group, and each R⁶ is, independently, a propoxy group. Also, in these embodiments, n is an integer from 0 to 5, m is an integer from 0 to 5, and 1≤(n+m)≤5. Moreover, in these embodiments, q is an integer from 0 to 5, if q is 0, p is an integer from 1 to 5, if q is >0, and p is an integer from 1 to 5, 1≤(p+q)≤5. In these embodiments, the lubricant composition includes the alkoxylated amide and the ester in a weight ratio of less than 70:30 of the ester to the alkoxylated amide.

Exemplary alkoxylated amides include, but are not limited to:

In these exemplary alkoxylated amides, R¹ is a linear or branched, saturated or unsaturated, hydrocarbyl group, n is an integer from 0 to 5, m is an integer from 0 to 5, and 1≤(n+m)≤5.

Exemplary esters include, but are not limited to:

In these exemplary esters, R¹ is a linear or branched, saturated or unsaturated, hydrocarbyl group, q is an integer from 0 to 5, if q is 0, p is an integer from 0 to 5; if q is >0, p is an integer from 1 to 5, and 0≤(p+q)≤5.

It should be appreciated that various mechanisms may be used to prepare the alkoxylated amide and the ester of the additive package or the lubricant composition. For example, in one embodiment, the alkoxylated amide and the ester may be prepared by reacting (a) at least one fatty acid, at least one fatty acid ester, or a mixture thereof, with (b) a dialkanolamide. In this embodiment, 1 mole of the amide and the ester resulting from steps (a) and (b) may then be reacted with from 1 to 5 moles of propylene oxide and/or butylene oxide to form the alkoxylated amide having general formula (I) and ester having general formula (II). In certain embodiments, the alkoxylated amide having general formula (I) and ester having general formula (II) are free of ethoxy groups which can result from alkoxylation with ethylene oxide.

Particularly, the alkoxylated amide having general formula (VIII) which further defines the alkoxylated amide having general formula (I) and the ester having general formula (IX) which further defines the ester having general formula (II) may be prepared by first reacting at least one fatty acid and/or at least one fatty acid ester with a dialkanolamine to form a dialkanolamide having general formula (X) and ester having general formula (XI), as shown below. Next, 1 mole of the dialkanolamide having general formula (X) and ester having general formula (XI) may be reacted with 1 to 5 moles of propylene oxide and/or butylene oxide to form the alkoxylated amide having general formula (VIII) and ester having general formula (IX). In certain embodiments, the alkoxylated amide having general formula (VIII) and ester having general formula (IX) are free of ethoxy groups which can result from alkoxylation with ethylene oxide. The major product is the alkoxylated amide having general formula (VIII), with the ester of general formula (IX) being present in an amount of up to 50, 40, 30, 20, 15, 10, 5, 3, 2, 1, or 0.1, wt. %, by total weight of the alkoxylated amide having general formula (VIII) and ester having general formula (IX).

The alkoxylated amide having general formula II) and ester having general formula (IX) may be formed as follows:

R¹ is a linear or branched, saturated or unsaturated, hydrocarbyl group. R^c is hydrogen or C_1-3 alkyl, and R^d is an alkylene group containing 2 or 3 carbon atoms. If R^c is C_1-3 alkyl, the R^cOH by-product can remain in the reaction mixture (not shown). Optionally, the R^cOH by-product can be removed from the reaction mixture. The amide having general formula (X) and ester having general formula (XI) may then be reacted with propylene oxide and/or butylene oxide to provide the alkoxylated amide having general formula (VIII) and ester having general formula (IX).

Alternatively, the alkoxylated amide having general formula (VIII) can be prepared from a vegetable oil, animal oil, or triglyceride as follows:

R¹ is a linear or branched, saturated or unsaturated, hydrocarbyl group. R^d is an alkylene group containing 2 or 3 carbon atoms. The amide having general formula (X) may be reacted with propylene oxide and/or butylene oxide. In certain embodiments, the propoxylation/butoxylation is the presence of the glycerin by-product. In other embodiments, the propoxylation/butoxylation is after separation of the amide having general formula (X) from the glycerin by-product. It is to be appreciated that the ester having general formula (XI) is formed and, after propoxylation/butoxylation, the ester having general formula (IX) is also formed.

The fatty acid and/or fatty acid ester used in the reaction to form the amide contains from 2 to 24 carbon atoms, from 2 to 20 carbon atoms, or from 8 to 18 carbon atoms. The fatty acid and/or fatty acid ester therefore can be, but not limited to, lauric acid, myristic acid, palmitic acid, stearin; acid, octanoic acid, pelargonic acid, behenic acid, cerotic acid, monotanic acid, lignoceric acid, doeglic acid, erucic acid, linoleic acid, isanic acid, stearodonic acid, arachidonic acid, chypa.nodoic acid, ricinoleic acid, capric acid, decanoic acid, isostearic acid, gadoleic acid, myristoleic acid, palmitoleic acid, linderic acid, oleic acid, petroselenic acid, esters thereof, or combinations thereof. In certain embodiments, the fatty acid/fatty acid ester includes lauric acid, or a compound having a lauric acid residue, e.g., coconut oil.

The fatty acid/fatty acid ester also can be derived from a vegetable oil or an animal oil, for example, but not limited to, coconut oil, babassu oil, palm kernel oil, palm oil, olive oil, castor oil, peanut oil, jojoba oil, soy oil, sunflower seed oil, walnut oil, sesame seed oil, rapeseed oil, rape oil, beef tallow, lard, whale blubber, seal oil, dolphin oil, cod liver oil, corn oil, tall oil, cottonseed oil, or combinations thereof. The vegetable oils contain a mixture of fatty acids. For example, coconut oil may contain the following fatty acids: caprylic (8%), capric (7%), lauric (48%), myristic (17.5%), palmitic (8.2%), stearic (2%), oleic (6%), and linoleic (2.5%).

The fatty acid/fatty acid ester can also be derived from fatty acid esters, such as, for example, glyceryl trilaurate, glyceryl tristearate, glyceryl tripalmitate, glyceryl dilaurate, glyceryl monostearate, ethylene glycol dilaurate, pentaerythritol tetrastearate, pentaerythritol trilaurate, sorbitol monopalmitate, sorbitol pentastearate, propylene glycol monostearate, or combinations thereof.

The fatty acid/fatty acid ester may include one or more fatty acids, one or more fatty acid methyl ester, one or more fatty acid ethyl ester, one or more vegetable oil, one or more animal oil, or combinations thereof. The amide resulting from the reaction can contain by-products, such as glycerin, ethylene glycol, sorbitol, and other polyhydroxy compounds. In certain embodiments, the water, methanol, and/or ethanol by-products may be removed from the reaction to substantially reduce the amount of unwanted by-products. In some embodiments, the by-product polyhydroxy compounds are allowed to remain in the reaction mixture because these compounds may not adversely affect the alkoxylated amide having general formula (VIII). In certain embodiments, the by-products resulting from the reaction which remain in the reaction mixture may be included in the additive package or the lubricant composition.

The fatty acid/fatty acid ester is reacted with a dialkanolamine to provide an amide having general formula (X), such as dialkanolamide. Dialkanolamines contain a hydrogen atom for reaction with the carboxyl or ester group of the fatty acid/fatty acid ester. Dialkanolamines also contain two hydroxy groups for subsequent reaction with alkylene oxides, such as propylene oxide and/or butylene oxide. A portion of the dialkanolamine reacts with the fatty acid/fatty acid ester to provide the ester having general formula (XI) by reaction of a hydroxy group of the dialkanolamine with the fatty acid/fatty acid ester. The amino group of the dialkanolatnine is available for a subsequent reaction with alkylene oxides, such as propylene oxide and/or butylene oxide to form the ester having general formula (XI). In some embodiments, dialkanolamines contain two or three carbons in each of the two alkanol groups, such as diethanolamine, di-isopropylamine, and di-n-propylamine. In one embodiment, the dialkanolamine is diethanolamine.

In a preparation of the alkoxylated amide having general formula (X) and ester having general formula (XI), the dialkanolamine can be present in an equivalent molar amount to the fatty acid residues in the fatty acid/fatty acid ester. In another embodiment, the dialkanolamine is present in a molar amount different from the moles of fatty acid residues, i.e., a molar excess or deficiency. In one embodiment, the number of moles of dialkanolamine is substantially equivalent to the number of moles of fatty acid residue. As used herein, the term “fatty acid residue” is defined as R¹—C(═O). Therefore, a methyl ester of a fatty acid, i.e., R¹—C(═O)OCH₃, contains one fatty acid residue, and the method may utilize a substantially equivalent number of moles of dialkanolamine to methyl ester. A triglyceride contains three fatty acid residues, and the method may utilize about three moles of dialkanolamine per mole of triglyceride. The mole ratio of dialkanolamine to fatty acid residue may be from 0.3 to 1.5, from 0.6 to 1.3, from 0.8 to 1.2, or from 0.9 to 1.1 moles per mole of fatty acid residue.

The reaction to prepare the amide having formula general (X) and the ester having general formula (XI) can be performed in the presence or absence of a catalyst. In certain embodiments, a basic catalyst is employed. In one embodiment, a catalyst can be an alkali metal alcoholate, such as sodium methylate, sodium ethylate, potassium methylate, or potassium ethylate. Alkali metal hydroxides, such as sodium or potassium hydroxide acid, and alkali metal carbonates, such as sodium carbonate or potassium carbonate, also can be used as the catalyst.

If employed, the catalyst may be present in an amount of from 0.01 to 5, 0.05 to 4, 0.1 to 3, or 0.5 to 2, wt. %, based on the total weight of the amide having formula (X) and the ester having formula (XI) to be produced. The reaction temperature to form the amide having formula (X) and the ester having formula (XI) may be from 50° C. to about 200° C. The reaction temperature may be higher than the boiling point of an alcohol, e.g., methanol, and/or water produced during the reaction to eliminate water and/or the alcohol as it is generated in the reaction. The reaction may be performed for from 2 to 24 hours.

Depending on the starting materials, the final reaction mixture in the preparation of the amide having general formula (X) and the ester having general formula (XI) may contain by-product compounds. These compounds can include, for example: (i) a by-product hydroxy compound, e.g., glycerin or other alcohol; (ii) a by-product mono-ester of a triglyceride, e.g., glyceryl mono-cocoate; (iii) a by-product di-ester of a triglyceride, e.g., glyceryl di-cocoate; and (iv) a dialkanolamine, if an excess molar amount of dialkanolamine is employed. The reaction mixture contains the ester having general formula (XI) wherein one or more of the hydroxy groups of the dialkanolamine reacts with the acid, and also can contain ester-amides wherein both ester and amide groups are formed. in certain embodiments, such by-product compounds are allowed to remain in the final reaction mixture containing the alkoxylated amide having general formula (VIII) and the ester having general formula (IX). As a result, in certain embodiments, the by-product compounds that remain in the final reaction mixture may be included in the additive package or the lubricant composition. In other embodiments, the by-product compounds that remain in the final reaction mixture may be excluded from the additive package or the lubricant composition.

After the amide having general formula (X) and the ester having general formula (XI) are formed, by-products optionally can be separated therefrom. For example, if a vegetable oil is used as the starting material for the fatty acid residues, the glycerin by-product can be removed from the reaction mixture. In certain embodiments, the reaction mixture including the amide having general formula (X) and the ester having general formula (XI) is used without further purification, except for the removal of solvents, water, and/or low molecular weight alcohols, e.g., methanol and ethanol. To avoid the generation of a glycerin by-product, a fatty acid or a fatty acid methyl ester can be used as the fatty acid residue source.

After formation of the amide having general formula (X) and the ester having general formula (XI), 1 mole of the amide and ester (in total) is reacted with from 1 to 5 or from 1 to 3, total moles of alkylene oxide, such as propylene oxide and/or butylene oxide. In this step, the amide and ester can be reacted with propylene oxide first, then with butylenes oxide; or with butylenes oxide first, then with propylene oxide; or with propylene oxide and butylene oxide simultaneously. The amide having general formula (X) and the ester having general formula (XI) also can be solely reacted with propylene oxide or solely be reacted with butylene oxide. In certain embodiments, 1 mole of the amide having general formula (X) and the ester having general formula (XI), in total, is solely reacted with about 1 to about 3 moles of propylene oxide.

The propoxylation/butoxylation reaction often is performed under basic conditions, for example by employing a basic catalyst of the type used in the preparation of the amide having general formula (X) and the ester having general formula (XI). Additional basic catalysts are nitrogen-containing catalysts, for example, an imidazole, N—N-dimethylethanolamine, and N,N-dimethylbenzylamine. It also is possible to perform the alkoxylation reaction in the presence of a Lewis acid, such as titanium trichloride or boron trifluoride. If employed, the amount of catalyst utilized is from 0.5% to 0.7%, by weight, based on the amount of the amide having general formula (X) and the ester having general formula (XI), in total, used in the alkoxylation reaction. In some embodiments, a catalyst is omitted from the reaction.

The temperature of the alkoxylation reaction may be from 80° C. to 180° C. The alkoxylation reaction may be performed in an atmosphere that is inert under the reaction conditions, e.g., nitrogen.

The alkoxylation reaction also can be performed in the presence of a solvent. The solvent may be inert under the reaction conditions. Suitable solvents are aromatic or aliphatic hydrocarbon solvents, such as hexane, toluene, and xylene. Halogenated solvents, such as chloroform, or ether solvents, such as dibutyl ether and tetrahydrofuran, also can be used.

In various embodiments, the reaction mixture that yields the amide having general formula (X) and the ester having general formula (XI) is used without purification in the alkoxylation reaction to provide the alkoxylated amide having general formula (VIII) and the ester having general formula (IX). In other embodiments, the reaction mixture that provides the alkoxylated amide having general formula (VIII) and the ester having general formula (IX) also is used without purification. As a result, the reaction product may include a variety of products and by-product compounds including, for example, alkoxylated amide having general formula (VIII), the ester having general formula (IX), the amide having general formula (X), the ester having general formula (XI), unreacted dialkanolamine, by-product hydroxy compounds (e.g., glycerin or other alcohol), mono- and/or di-esters of a starting triglyceride, polyalkylene oxide oligomers, aminoesters, and ester-amides. As a result, in certain embodiments, the by-product compounds that remain in the reaction mixture with the products may be included in the additive package or the lubricant composition. In other embodiments, the by-product compounds that remain in the reaction mixture may be excluded from the additive package or the lubricant composition.

It also should be understood that the propoxylation/butoxylation reaction may yield a mixture of the alkoxylated amide having general formula (VIII) and the ester having general formula (IX). In particular, both CH₂CH₂OH groups of the amide having general formula (X) can be alkoxylated, either to a different degree (i.e., n>0, m>0, and n≠m) or to the same degree (i.e.,n>0, m>0, and n=m). In certain embodiments, only one CH₂CH₂OH of the amide having general formula (X) is alkoxylated (i.e., one of n or m is 0). In other embodiments, the amide having general formula (X), such as dialkanola.mide, is alkoxylated with one mole of alkylene oxide and one mole of propylene oxide. It is to be appreciated that a portion of the amide having general formula (X) will not be alkoxylated, thus n+m can be less than 1, i.e., a lower limit of

In certain embodiments, the alkoxylated amide and the ester are utilized as a fuel economy agent in the lubricant composition. Fuel economy agents may be utilized in mixed and boundary lubricant applications to reduce the friction coefficient of the lubricant composition. Specifically, without intending to be bound by theory, in an engine, it is contemplated that the fuel economy agent may absorb onto metal surfaces of the engine to form a monolayer. It is believed that this monolayer may decrease direct metal-to-metal contacts in the engine when utilized in mixed and boundary lubricant applications. This decrease of metal-to-metal contacts may reduce wear of the engine. In lubricant compositions including the anti-wear agent, it is also believed that the fuel economy agent absorbs onto a layer of the anti-wear agent that is present on metal surfaces of the engine, such as a tribofilm, to reduce the friction coefficient of the layer of the anti-wear agent present on the surface of the engine.

With regard to the anti-wear agent of the additive package or the lubricant composition introduced above, the anti-wear agent includes phosphorus, molybdenum, or a combination thereof. In certain embodiments, the additive package or the lubricant composition may include an anti-wear agent including phosphorus. The anti-wear agent including phosphorus may be exemplified by a dihydrocarbyl dithiophosphate salt. The dihydrocarbyl dithiophosphate salt may be represented by the following general formula (XII):

[R⁹O(R¹⁰O)PS(S)]₂M   (XII)

In general formula (XII), R⁹ and R¹⁰ are each hydrocarbyl groups, independently, having from 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5, carbon atoms. Furthermore, in general formula (XII), M is a metal atom or an ammonium group. For example, R⁹ and R¹⁰ may each independently be C_1-20 alkyl groups, C_2-20 alkenyl groups, C_3-20 cycloalkyl groups, C_1-20 aralkyl groups or C_3-20 aryl groups. The groups designated by R⁹ and R¹⁰ may be substituted or unsubstituted. The metal atom may be selected from the group including aluminum, lead, tin, manganese, cobalt, nickel, or zinc. The ammonium group may be derived from ammonia or a primary, secondary, or tertiary amine. The ammonium group may be of the formula R¹¹R¹²R¹³R¹⁴N⁺, wherein R¹¹, R¹², R¹³, and R¹⁴ each independently represents a hydrogen atom or a hydrocarbyl group having from 1 to 150 carbon atoms. In certain embodiments, R¹¹, R¹², R¹³, and R¹⁴ may each independently be hydrocarbyl groups having from 4 to 30 carbon atoms. In one embodiment, the dihydrocarbyl dithiophosphate salt is zinc dialkyl dithiophosphate (ZDDP). The lubricant composition may include mixtures of different dihydrocarbyl dithiophosphate salts. In some embodiments, the anti-wear agent may be ashless.

In certain embodiments, the dihydrocarbyl dithiophosphate salt includes a mixture of primary and secondary alkyl groups for, R⁹ and R¹⁰, wherein the secondary alkyl groups are in a major molar proportion, such as at least 60, at least 75, or at least 85, mole %, based on the number of moles of alkyl groups in the dihydrocarbyl dithiophosphate salt. In these embodiments, the dihydrocarbyl dithiophosphate salt may include primary alkyl groups and secondary alkyl groups. In general, ZDDP may be formed by reacting alcohols with thiophosphates. ZDDP is generally described by the alcohol that is used in the synthesis process to donate the alkyl groups to the ZDDP molecule. So for instance, a “primary” ZDDP is formed from primary alcohols including, but not limited to, n-decanol, n-octanol, 2-ethyl-1-hexanol, 1-hexanol, 4-methyl-1-pentanol, 2-methyl-1-propanol, 1-pentanol, 1-butanol, 1-propanol and mixtures thereof. Similarly, a “secondary” ZDDP is formed from secondary alcohols including, but not limited to, 2-propanol, 2-butanol, 2-pentanol, 4-methyl-2-pentanol, 2-hexanol, 2-octanol and 2-decanol and mixtures thereof. An “aryl” ZDDP may include those formed from phenol, butylated phenol, 4-dodecyl phenol and 4-nonyl phenol, and combinations thereof.

The anti-wear agent may be further defined as a phosphate. In another embodiment, the anti-wear agent is further defined as a phosphite. In still another embodiment, the anti-wear agent is further defined as a phosphorothionate. The anti-wear agent may alternatively be further defined as a phosphorodithioate. In one embodiment, the anti-wear agent is further defined as a dithiophosphate. The anti-wear agent may also include an amine such as a secondary or tertiary amine. In one embodiment, the anti-wear agent includes an alkyl and/or dialkyl amine. The anti-wear agent may be acidic, basic, or neutral. Structures of suitable non-limiting examples of anti-wear agents are set forth immediately below:

In other embodiments, the anti-wear agent may include molybdenum. For example, the anti-wear agent including molybdenum may be exemplified by any suitable oil-soluble organo-molybdenum compound. Typically, the anti-wear agent including molybdenum includes a molybdenum-sulfur core formed from one or more molybdenum atoms and one or more sulfur atoms. Non-limiting examples of suitable anti-wear agents including molybdenum include molybdenum dithiocarbamates, molybdenum dithiophosphates, molybdenum dialkyldithiophosphates, molybdenum dithiophosphinates, molybdenum xanthates, molybdenum alkyl xanthates, molybdenum alkylthioxanthates, molybdenum thioxanthates, molybdenum sulfides, and combinations thereof.

In certain embodiments, the anti-wear agent including molybdenum is dinuclear or trinuclear. In one embodiment, the anti-wear agent including molybdenum is a tri-nuclear molybdenum compound that may be represented by the following general formula (XIII):

Mo₃S_kL_nQ_z   (XIII)

In general formula (XIII), L is an independently selected ligand having organo groups with a sufficient number of carbon atoms to render the compounds soluble or dispersible in the oil. In general formula (XIII), n is a number from 1 to 4. Also in general formula (XIII), k is a number from 4 to 7. Further in general formula (XIII), Q is selected from the group of neutral electron donating compounds such as water, amines, alcohols, phosphines, and ethers. Also in general formula (XIII), z is a number from 0 to 5. In certain embodiments, at least 21, at least 25, at least 30, or at least 35, total carbon atoms should be present among all the ligands' organo groups of the anti-wear agent including molybdenum.

In various embodiments, the anti-wear agent of the additive package or the lubricant composition may include phosphorus and molybdenum in a single compound. It is to be appreciated that one or more of the anti-wear agents including phosphorus described above may include phosphorus and molybdenum in a single compound. It is also to be appreciated that one or more of the anti-wear agents including molybdenum described above may include phosphorus and molybdenum in a single compound.

In other embodiments, the additive package or the lubricant composition may include the anti-wear agent including phosphorus, such as any of the anti-wear agents including phosphorus described above, and the anti-wear agent including molybdenum, such as any of the anti-wear agents including molybdenum described above. For example, the additive package or the lubricant composition may include ZDDP and molybdenum dithiocarbamate. The additive package or the lubricant composition may also include any other type of anti-wear agent understood in the art.

The anti-wear agent may be present in the additive package in an amount of from 0.01 to 80, 0.05 to 50, 0.1 to 25, 0.1 to 15, 0.1 to 10, 0.1 to 5, 0.1 to 2, or 0.1 to 1, wt. %, each based on the total weight of the additive package. Alternatively, the anti-wear agent may be present in amounts of less than 80, less than 50, less than 25, less than 15, less than 10, less than 5, less than 2, or less than 1, wt. %, each based on the total weight of the additive package.

The anti-wear agent may be present in the lubricant composition in an amount of from 0.001 to 30, 0.005 to 20, 0.005 to 10, 0.01 to 5, 0.01 to 2, 0.01 to 1, 0.01 to 0.5, or 0.01 to 0.2, wt. %, based on the total weight of the lubricant composition. Alternatively, the anti-wear agent may be present in amounts of less than 30, less than 20, less than 10, less than 5, less than 2, less than 1, less than 0.5, or less than 0.2, wt. %, based on the total weight of the lubricant composition.

The additive package or the lubricant composition may include the anti-wear agent including phosphorus and the anti-wear agent including molybdenum in a weight ratio of from 99:1 to 1:99, 90:10 to 10:90, 80:20 to 20:80, 70:30 to 30:70, 60:40 to 40:60, or 55:45 to 45:55, of the anti-wear agent including phosphorus to the anti-wear agent including molybdenum.

In other embodiments, the additive package may consist, or consist essentially of the alkoxylated amide, the ester, and the anti-wear agent. It is also contemplated that the additive package may consist of, or consist essentially of, the alkoxylated amide, the ester, and the anti-wear agent in addition to at least one of the additives that do not materially affect the functionality or performance of the alkoxylated amide, the ester, or the anti-wear agent. When used in reference to the additive package, the term “consisting essentially of” refers to the additive package being free of compounds that materially affect the overall performance of the additive package. For example, compounds that materially affect the overall performance of the additive package may include compounds which impact the TBN boost, the lubricity, the corrosion inhibition, the acidity, the detergency, or the metal surface cleanliness of the additive package.

In various embodiments, the additive package is substantially free of water, e.g., the additive package includes less than 5, 4, 3, 2, 1, 0.5, or 0.1, wt. %, of water based on the total weight of the additive package. Alternatively, the additive package may be completely free of water.

As introduced above, the additive package may be formulated to provide the desired concentration in the lubricant composition. In these embodiments, the lubricant composition includes the alkoxylated amide, the ester, the anti-wear agent, and a base oil. It is to be appreciated that most references to the lubricant composition throughout this disclosure also apply to the description of the additive package. For example, it is to be appreciated that the additive package may include, or exclude, the same components as the lubricant composition, albeit in different amounts.

In certain embodiments, the lubricant composition is further defined as a racing oil composition. Like the lubricant composition, the racing oil composition includes the alkoxylated amide and the ester. The racing oil also includes the anti-wear agent including phosphorus. It is to be appreciated that the racing oil composition may include any of the alkoxylated amides, esters, and anti-wear agents comprising phosphorus disclosed herein. Of course, the racing oil composition may also include any of the other components (such as the base oils and additives) disclosed herein.

Racing oil compositions are lubricant compositions specifically intended to lubricate racing vehicles. Racing vehicles are vehicles intended for use in a racing event and are generally capable of achieving speeds that are greater than conventional vehicles (i.e., non-racing vehicles) used for transportation. Racing oil compositions differ from lubricant compositions intended to lubricant non-racing vehicles in that racing oil compositions generally include a comparatively greater amount of additives. Accordingly, the racing oil composition generally includes a greater amount of the alkoxylated amide, the ester, and the anti-wear agent including phosphorus. In other words, the racing oil composition generally includes the additive package disclosed herein in a greater amount than the lubricant composition. It is generally believed that the increased amount of the alkylated amide, the ester, the anti-wear agent including phosphorus, and the other additives (if included) increases the performance (e.g. fuel economy, lubricity, horsepower, wear protection, etc.) of the racing oil composition in comparison to lubricant compositions containing a lesser amount of these components.

In certain embodiments, the racing oil composition includes the base oil, the anti-wear agent including phosphorus, and a mixture of the alkoxylated amide and the ester, with the mixture of the alkoxylated amide and ester being present in a combined total amount of from 0.01 to 3.0 wt. % based on the total weight of the racing oil composition. Alternatively, the racing oil composition includes the mixture of the alkoxylated amide and the ester in a combined total amount of from 0.1 to 3.0, from 0.2 to 2.5, from 0.3 to 2.0, from 0.3 to 1.5, from 0.3 to 1.0, from 0.4 to 0.8, from 0.4 to 0.6, or 0.5, wt. % based on the total weight of the racing oil composition. The ratio of the amount of the alkoxylated amide relative to the ester is described above.

In certain embodiments, the racing oil composition includes the anti-wear agent including phosphorus in an amount of from 0.01 to 3.0 wt. % based on the total weight of the racing oil composition. Alternatively, the racing oil composition includes the mixture of the alkoxylated amide and the ester in an amount of from 0.01 to 2.5, from 0.02 to 2.0, from 0.03 to 1.5, from 0.03 to 1.0, from 0.03 to 0.5, from 0.03 to 0.4, from 0.06 to 0.40, from 0.08 to 0.40, from 0.1 to 0.40, from 0.2 to .03, or 0.2, wt. % based on the total weight of the racing oil composition. Although not required, the anti-wear agent in the racing oil composition is typically ZDDP. In other embodiments, the anti-wear agent is zinc phosphate.

Alternatively, the anti-wear agent may be included in the racing oil composition in an amount sufficient to include phosphorus in the racing oil composition in an amount of from 10 to 25,000 ppm of phosphorus. Alternatively, the anti-wear agent may be included in the racing oil composition in an amount sufficient to include phosphorus in the racing oil composition in an amount of from 100 to 20,000, from 200 to 15,000, from 500 to 10,000, from 800 to 8,000, from 900 to 7,000, from 1,000 to 6,000, from 1,100 to 5,000, or from 1,100 to 4,000, ppm phosphorus. For example, the racing oil composition may include ZDDP in an amount such that the racing oil composition includes phosphorus in an amount of from 10 to 25,000 ppm of phosphorus or from 1,100 to 4,000 ppm of phosphorus. The racing oil composition may have a sulfur content of less than 6000, less than 4500, less than 3000, less than 1500, less than 1200, less than 1000, less than 700, less than 500, less than 300, or less than 100, ppm, as measured according to the ASTM D5185 standard, or as measured according to the ASTM D4951 standard. Without being held to any particular theory, it is believed that as the amount of phosphorus in the racing oil composition is increased, the effectiveness of the mixture of the alkoxylated amide and the ester as a friction modifier is increased and thus the fuel economy and horsepower of the racing oil is also increased.

In one embodiment, the racing oil composition includes the base oil, the anti-wear agent including phosphorus, the alkoxylated amide having the following formula:

and the ester having the following formula:

with each R¹ being, independently, a linear or branched, saturated or unsaturated, C₆-C₂₃ aliphatic hydrocarbyl group. Although not required, the alkoxylated amide and ester may be present in amount of 0.01 to 3.0 wt. % based on the total weight of the racing oil composition. Moreover, in this embodiment, the anti-wear agent including phosphorus is typically present in an amount of from 0.01 to 5 wt. % based on the total weight of the racing oil composition. Although also not required, the anti-wear agent is generally ZDDP.

The base oil is classified in accordance with the American Petroleum Institute (API) Base Oil Interchangeability Guidelines. In other words, the base oil may be further described as at least one of five types of base oils: Group I (sulphur content >0.03 wt. %, and/or <90 wt. % saturates, viscosity index 80-119); Group II (sulphur content less than or equal to 0.03 wt. %, and greater than or equal to 90 wt. % saturates, viscosity index 80-119); Group III (sulphur content less than or equal to 0.03 wt. %, and greater than or equal to 90 wt. % saturates, viscosity index greater than or equal to 119); Group IV (all polyalphaolefins (PAO's)); and Group V (all others not included in Groups I, II, III, or IV).

In some embodiments, the base oil is selected from the group of API Group I base oils; API Group II base oils; API Group III base oils; API Group IV base oils; API Group V base oils; and combinations thereof. In other embodiments, the lubricant composition is free from Group I,

Group II, Group III, Group IV, or Group V, base oils, and combinations thereof. In one embodiment, the base oil includes API Group II base oils.

The base oil may have a viscosity of from 1 to 50, 1 to 40, 1 to 30, 1 to 25, or 1 to 22, cSt, when tested according to ASTM D445 at 100° C. Alternatively, the viscosity of the base oil may range from 3 to 22, 3 to 17, or 5 to 14, cSt, when tested according to ASTM D445 at 100° C.

The base oil may be further defined as a crankcase lubricant composition for spark-ignited and compression-ignited internal combustion engines, including automobile and truck engines, two-cycle engines, aviation piston engines, marine engines, and railroad diesel engines. Alternatively, the base oil can be further defined as an oil to be used in gas engines, diesel engines, stationary power engines, and turbines. The base oil may be further defined as heavy or light duty engine oil.

In still other embodiments, the base oil may be further defined as synthetic oil that includes at least one alkylene oxide polymers and interpolymers, and derivatives thereof. The terminal hydroxyl groups of the alkylene oxide polymers may be modified by esterification, etherification, or similar reactions. These synthetic oils may be prepared through polymerization of ethylene oxide or propylene oxide to form polyoxyalkylene polymers which can be further reacted to form the synthetic oil. For example, alkyl and aryl ethers of these polyoxyalkylene polymers may be used. For example, methylpolyisopropylene glycol ether having a weight average molecular weight of 1000; diphenyl ether of polyethylene glycol having a molecular weight of 500-1000; or diethyl ether of polypropylene glycol having a weight average molecular weight of 1000-1500 and/or mono- and polycarboxylic esters thereof, such as acetic acid esters, mixed C₃-C₈ fatty acid esters, and the C₁₃ oxo acid diester of tetraethylene glycol may also be utilized as the base oil. Alternatively, the base oil may include a substantially inert, normally liquid, organic diluent, such as mineral oil, naptha, benzene, toluene, or xylene.

The base oil may include less than 90, less than 80, less than 70, less than 60, less than 50, less than 40, less than 30, less than 20, less than 10, less than 5, less than 3, less than 1, wt. %, or be free from, an estolide compound (i.e., a compound including at least one estolide group), based on the total weight of the lubricant composition.

The base oil may be present in the lubricant composition in an amount of from 1 to 99.9, 50 to 99.9, 60 to 99.9, 70 to 99.9, 80 to 99.9, 90 to 99.9, 75 to 95, 80 to 90, or 85 to 95, wt. %, based on the total weight of the lubricant composition. Alternatively, the base oil may be present in the lubricant composition in amounts of greater than 1, 10, 20, 30, 40, 50, 60, 70, 75, 80, 85, 90, 95, 98, or 99, wt. %, based on the total weight of the lubricant composition. In various embodiments, the amount of base oil in a fully formulated lubricant composition (including diluents or carrier oils present) ranges from 50 to 99, 60 to 90, 80 to 99.5, 85 to 96, or 90 to 95, wt. %, based on the total weight of the lubricant composition. Alternatively, the base oil may be present in the lubricant composition in an amount of from 0.1 to 50, 1 to 25, or 1 to 15, wt. %, based on the total weight of the lubricant composition. In various embodiments, the amount of base oil in an additive package, if included, (including diluents or carrier oils present) ranges from 0.1 to 50, 1 to 25, or 1 to 15, wt. %, based on the total weight of the additive package.

The lubricant composition can be employed in a variety of lubricants based on diverse oils of lubricating viscosity, including natural and synthetic lubricating oils and mixtures thereof. These lubricants include crankcase lubricating oil for spark-ignited and compression-ignited internal combustion engines, including automobile and truck engines; two cylinder engines; aviation piston engines; marine and railroad diesel engines, and the like.

The lubricant composition may include less than 50, less than 25, less than 10, less than 5, less than 1, less than 0.1, or less than 0.01, wt. %, of a fluorinated base oil, or the lubricant composition may be free from a fluorinated base oil. The phrase “fluorinated base oil” may be understood to include any fluorinated oil components, such as perfluoropolyethers or fluorocarbons.

In some aspects, the fluorinated base oil may also be generally defined as any component that includes more than 1, 5, 10, 15, or 20 fluorine atoms per molecule.

In some embodiments, the lubricant composition is a ‘wet’ lubricant composition that includes at least one liquid component. The lubricant composition is not a dry lubricant as it requires at least one liquid component to properly lubricate.

In one or more embodiments, the lubricant composition may be classified as a low SAPS lubricant having a sulfated ash content of no more than 3, 2, 1, or 0.5, wt. %, based on the total weight of the lubricant composition. “SAPS” refers to sulfated ash, phosphorous and sulfur.

One method of evaluating the anti-wear properties of a lubricant composition is to determine the friction coefficient of the lubricant composition. In certain embodiments, the friction coefficient of the lubricant composition is determined according to a modified ASTM D 6079 method. The modified ASTM D 6079 method utilizes a High Frequency Reciprocating Rig (HFRR) for determining the friction coefficient. During the determination, the HFRR reciprocates at 10 Hz and has a 1 mm stroke. The determination is conducted at a temperature of 100° C. for duration of 120 minutes with a 400 gram load. The lubricant composition may have a friction coefficient of less than or equal to 0.19, less than or equal to 0.18, less than or equal to 0.17, less than or equal to 0.16, less than or equal to 0.15, according to the modified ASTM D 6079 method.

Another method of evaluating the anti-wear properties of a lubricant composition is to determine the ball scar diameter of the lubricant composition. In certain embodiments, the ball scar diameter of the lubricant composition is determined by a laser profilometer. During the determination, standard HFRSSP steel balls are utilized with the laser profilometer. The lubricant composition may have a ball scar diameter of less than or equal to 260, less than or equal to 250, less than or equal to 240, less than or equal to 230, less than or equal to 220 μm.

The fuel economy increase for vehicles utilizing a lubricant composition may be determined according to the EPA Highway Fuel Economy Driving Schedule (HWFET). HWFET is a chassis dynamometer driving schedule developed by the U.S. EPA for the determination of fuel economy of light duty vehicles. In accordance with HWFET, each vehicle utilizing the lubricant composition is tested for 765 seconds to a distance of 10.26 miles at an average speed of 48.3 miles per hour. The lubricant composition including the alkoxylated amide, the ester, and the anti-wear agent may improve fuel economy by at least 0.75, at least 1, at least 1.25, at least 1.3, or at least 1.35, %, according to HWFET.

The fuel consumption of an engine may be determined by operating the engine at controlled steady state conditions simulating highway temperatures, speed, and load over a designated time period, such as a 70 hour period. During the designated time period, the fuel consumption may be measured with a Coriolis-type fuel flow meter. The engine utilized for the fuel consumption determination may be a 5.7 liter GM crate engine. The fuel consumption of an engine utilizing the lubricant composition including the alkoxylated amide, the ester, and the anti-wear agent may reduce fuel consumption by at least 1, at least 2, at least 3, at least 4, at least 5, or at least 6, %.

The lubricant composition may have a TBN value of at least 1, at least 3, at least 5, at least 7, at least 9, mg KOH/g of lubricant composition, when tested according to ASTM D2896. Alternatively, the lubricant composition has a TBN value of from 3 to 100, 3 to 75, 50 to 90, 3 to 45, 3 to 35, 3 to 25, 3 to 15, or 9 to 12, mg KOH/g of lubricant composition, when tested according to ASTM D2896.

In certain embodiments, the lubricant composition is a multigrade lubricant composition identified by the viscometric descriptor SAE15WX, SAE 10WX, SAE 5WX or SAE OWX,

where X is 8, 12, 16, 20, 30, 40, or 50. The characteristics of at least one of the different viscometric grades can be found in the SAE J300 classification.

In other embodiments, the lubricant composition has a lower viscosity grade than SAE 30, such as SAE 20, SAE 16, SAE 15 SAE 12, SAE 10, SAE 10W, SAE 8, SAE 5, SAE 5W, SAE 4, SAE OW, and combinations thereof, as defined by the Society of Automotive Engineers (SAE) J300.

The lubricant composition may have a phosphorus content of less than 1500, less than 1200, less than 1000, less than 800, less than 600, less than 400, less than 300, less than 200, or less than 100, or 0, ppm, as measured according to the ASTM D5185 standard, or as measured according to the ASTM D4951 standard. The lubricant composition may have a sulfur content of less than 3000, less than 2500, less than 2000, less than 1500, less than 1200, less than 1000, less than 700, less than 500, less than 300, or less than 100, ppm, as measured according to the ASTM D5185 standard, or as measured according to the ASTM D4951 standard.

Alternatively, the lubricant composition may have a phosphorous content of from 1 to 1000, 1 to 800, 100 to 700, or 100 to 600, ppm, as measured according to the ASTM D5185 standard.

The lubricant composition may be unreactive with water. By unreactive with water, it is meant that less than 5, 4, 3, 2, 1, 0.5, or 0.1, wt.,%, of the lubricant composition reacts with water at 1 atmosphere of pressure and 25 ° C.

The lubricant composition may include less than 50, less than 25, less than 10, less than 5, less than 1, less than 0.1, or less than 0.01, wt. %, of a halogen-containing compound, such as a compound that includes fluorine, chlorine, iodine, or bromine, such as alkyl halides or halogen ether compounds, based on the total weight of the lubricant composition.

In one embodiment, the lubricant composition passes ASTM D5185, API GF-5, and/or API CJ-4 for phosphorus content. ASTM D5185 is a standard test method for determination of additive elements in lubricant compositions by inductively coupled plasma atomic emission spectrometry (ICP-AES).

In another embodiment, the lubricant composition passes ACEA 2012 for engine oils. ACEA 2012 is a certification for sequences that define the minimum quality level of a engine oil.

In another embodiment, the lubricant composition passes ASTM D6795, which is a standard test method for measuring the effect on filterability of lubricant compositions after treatment with water and dry ice and a short (30 min) heating time. ASTM D6795 simulates a problem that may be encountered in a new engine run for a short period of time, followed by a long period of storage with some water in the oil. ASTM D6795 is designed to determine the tendency of a lubricant composition to form a precipitate that can plug an oil filter.

In another embodiment, the lubricant composition passes ASTM D6794, which is a standard test method for measuring the effect on filterability of lubricant composition after treatment with various amounts of water and a long (6 h) heating time. ASTM D6794 simulates a problem that may be encountered in a new engine run for a short period of time, followed by a long period of storage with some water in the oil. ASTM D6794 is also designed to determine the tendency of the lubricant composition to form a precipitate that can plug an oil filter.

In another embodiment, the lubricant composition passes ASTM D6922, which is a standard test method for determining homogeneity and miscibility in lubricant compositions. ASTM D6922 is designed to determine if a lubricant composition is homogeneous and will remain so, and if the lubricant composition is miscible with certain standard reference oils after being submitted to a prescribed cycle of temperature changes.

In another embodiment, the lubricant composition passes ASTM D5133, which is a standard test method for low temperature, low shear rate, viscosity/temperature dependence of lubricating oils using a temperature-scanning technique. The low-temperature, low-shear viscometric behavior of a lubricant composition determines whether the lubricant composition will flow to a sump inlet screen, then to an oil pump, then to sites in an engine requiring lubrication in sufficient quantity to prevent engine damage immediately or ultimately after cold temperature starting.

In another embodiment, the lubricant composition passes ASTM D5800 and/or ASTM D6417, both of which are test methods for determining an evaporation loss of a lubricant composition. The evaporation loss is of particular importance in engine lubrication, because where high temperatures occur, portions of a lubricant composition can evaporate and thus alter the properties of the lubricant composition.

In another embodiment, the lubricant composition passes ASTM D6557, which is a standard test method for evaluation of rust preventive characteristics of lubricant compositions. ASTM D6577 includes a Ball Rust Test (BRT) procedure for evaluating the anti-rust ability of lubricant compositions. This BRT procedure is particularly suitable for the evaluation of lubricant compositions under low-temperature and acidic service conditions.

In another embodiment, the lubricant composition passes ASTM D4951 for sulfur content. ASTM D4951 is a standard test method for determination of additive elements in lubricant compositions by ICP-OES. In addition, the lubricant composition also passes ASTM D2622, which is a standard test method for sulfur in petroleum products by wavelength dispersive x-ray fluorescence spectrometry.

In another embodiment, the lubricant composition passes ASTM D6891, which is a standard test method for evaluating a lubricant composition in a sequence IVA spark-ignition engine. ASTM D6891 is designed to simulate extended engine idling vehicle operation. Specifically, ASTM D6891 measures the ability of a lubricant composition to control camshaft lobe wear for spark-ignition engines equipped with an overhead valve-train and sliding cam followers.

In another embodiment, the lubricant composition passes ASTM D6593, which is a standard test method for evaluating lubricant compositions for inhibition of deposit formation in a spark-ignition internal combustion engine fueled with gasoline and operated under low-temperature, light-duty conditions. ASTM D6593 is designed to evaluate a lubricant composition's control of engine deposits under operating conditions deliberately selected to accelerate deposit formation.

In another embodiment, the lubricant composition passes ASTM D6709, which is a standard test method for evaluating lubricant compositions in a sequence VIII spark-ignition engine. ASTM D6709 is designed to evaluate lubricant compositions for protection of engines against bearing weight loss.

In yet another embodiment, the lubricant composition passes ASTM D6984, which is a standard test method for evaluation of automotive engine oils in the Sequence IIIF, Spark-Ignition. In other words, the viscosity increase of the lubricant composition at the end of the test is less than 275% relative to the viscosity of the lubricant composition at the beginning of the test.

In another embodiment, the lubricant composition passes two, three, four, or more of the following standard test methods: ASTM D4951, ASTM D6795, ASTM D6794, ASTM D6922, ASTM D5133, ASTM D6557, ASTM D6891, ASTM D2622, ASTM D6593, and ASTM D6709.

The lubricant composition, such as a crankcase lubricant composition, may include the additive package in amount of (or have a total additive treat rate of) at least 0.1, at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, or at least 8, wt. %, based on a total weight of the lubricant composition. Alternatively, the lubricant composition may include the additive package in amount of (or have a total additive treat rate of) from 3 to 20, 4 to 18, 5 to 16, or 6 to 14, wt. %, based on a total weight of the lubricant composition. Alternatively, the lubricant composition may include the additive package in amount of (or have a total additive treat rate of) from 0.1 to 10, 0.1 to 5, 0.1 to 1, wt. %, based on a total weight of the lubricant composition. The additive package may be blended into the base oil to make the lubricant composition. The term “total additive treat rate” refers to the total weight percentage of additives included in the lubricant composition.

In certain embodiments, an additive is any compound in the lubricant composition other than the base oil. In other words, the total additive treat rate calculation does not account for the base oil as an additive. However, it is to be appreciated that certain individual components can be independently and individually added to the lubricant composition separate from the addition of the additive package to the lubricant composition, yet still be considered part of the additive package once the additive which was individually added into the lubricant composition is present in the lubricant composition along with the other additives. As just one example, a base oil which includes the alkoxylated amide, the ester, the anti-wear agent, and the dispersant, each added to the base oil separately, could be interpreted to be a lubricant composition that includes an additive package including the alkoxylated amide, the ester, the anti-wear agent, and the dispersant.

In certain embodiments, the lubricant composition may consist, or consist essentially of, the alkoxylated amide, the ester, the anti-wear agent, and the base oil. It is also contemplated that the lubricant composition may consist of, or consist essentially of, the alkoxylated amide, the ester, the anti-wear agent, and the base oil, in addition to at least one of the additives that do not materially affect the functionality or performance of the alkoxylated amide, the ester, the anti-wear agent, or the base oil. When used in reference to the lubricant composition, the term “consisting essentially of” refers to the lubricant composition being free of compounds that materially affect the overall performance of the lubricant composition. For example, compounds that materially affect the overall performance of the lubricant composition may include compounds which impact the TBN boost, the lubricity, the corrosion inhibition, the acidity, the detergency, or the metal surface cleanliness of the lubricant composition.

In various embodiments, the lubricant composition is substantially free of water, e.g., the lubricant composition includes less than 5, less than 4, less than 3, less than 2, less than 1, less than 0.5, or less than 0.1, wt. %, of water, based on the total weight of the lubricant composition. Alternatively, the lubricant composition may be completely free of water.

The additive package or lubricant composition may additionally include at least one additive to improve various chemical and/or physical properties of the resultant lubricant composition. Specific examples of the additives include, but are not limited to, anti-wear additives in addition to the anti-wear agent, antioxidants, metal deactivators (or passivators), rust inhibitors, friction modifiers (or antifriction additives), viscosity index improvers (or viscosity modifiers), pour point depressants (or pour point depressors), dispersants, detergents, anti-foam additives, amine compounds, and combinations thereof. Each of the additives may be used alone or in combination. The additive(s) can be used in various amounts, if employed.

If employed, the anti-wear additive can be of various types. Suitable examples of anti-wear agents include, but are not limited to, sulfur- and/or phosphorus- and/or halogen-containing compounds, e.g., sulfurised olefins and vegetable oils, alkylated triphenyl phosphates, tritolyl phosphate, tricresyl phosphate, chlorinated paraffins, alkyl and aryl di- and trisulfides, amine salts of mono- and dialkyl phosphates, amine salts of methylphosphonic acid, diethanolaminomethyltolyltriazole, bis(2-ethylhexyl)aminomethyltolyltriazole, derivatives of 2,5-dimercapto-1,3,4-thiadiazole, ethyl 3-[(diisopropoxyphosphinothioyl)thio]propionate, triphenyl thiophosphate (triphenylphosphorothioate), tris(alkylphenyl) phosphorothioate and mixtures thereof, diphenyl monononylphenyl phosphorothioate, isobutylphenyl diphenyl phosphorothioate, the dodecylamine salt of 3-hydroxy-1,3-thiaphosphetane 3-oxide, trithiophosphoric acid 5,5,5-tris[isooctyl 2-acetate], derivatives of 2-mercaptobenzothiazole such as 1-[N,N-bis (2-ethylhexyl)aminomethyl]-2-mercapto-1H-1,3 -benzothiazole, ethoxycarbonyl-5-octyldithio carbamate, antimony dithiocarbamate, titanium dithiocarbamate, and/or combinations thereof

If employed, the antioxidant can be of various types which include, but are not limited to, aminic antioxidants and phenolic antioxidants. Suitable examples of antioxidants include, but are not limited to, alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2, 6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2, 6-di-tert-butyl-4-methoxymethylphenol, 2, 6-di-nonyl-4-methylphenol, 2,4-dimethyl-6(1′-methylundec-1′-yl)phenol, 2,4-dimethyl-6-(1′-methylheptadec-1′-yl)phenol, 2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol, and combinations thereof.

Further examples of suitable antioxidants includes alkylthiomethylphenols, for example, 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2, 6-didodecylthiomethyl-4-nonylphenol, and combinations thereof. Hydroquinones and alkylated hydroquinones, for example, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5 -di-tert-butyl-4-hydroxyani sole, 3,5 -di-tert-butyl-4-hydroxyani sole, 3,5 -di-tert-butyl-4-hydroxyphenyl stearate, bis-(3 ,5 -di-tert-butyl-4-hydroxyphenyl) adipate, and combinations thereof, may also be utilized.

Furthermore, hydroxylated thiodiphenyl ethers, for example 2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3 -methylphenol), 4,4′-thiobis(6-tert-butyl-2-methylphenol), 4,4′-thiobis-(3 ,6-di-sec-amylphenol), 4,4′-bis-(2,6-dimethyl-4-hydroxyphenyl) disulfide, and combinations thereof, may also be used.

It is also contemplated that alkylidenebisphenols, for example 2,2′-methylenebis(6-tert-butyl -4-methylphenol), 2,2′-methylenebis(6-tert-butyl-4-ethylphenol), 2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4, 6-di-tert-butylphenol), 2,2′-ethylidenebis (4, 6-di-tert-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis [6-(α-methylbenzyl)-4-nonylphenol], 2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4′-methylenebis(2, 6-di-tert-butylphenol), 4,4′-methylenebis(6-tert-butyl -2-methylphenol), 1,1-bis(5 -tert-butyl-4-hydroxy-2-methylphenyl)butane, 2, 6-bis(3 -tert-butyl-5 -methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3 -tris(5 -tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis(5 -tert-butyl-4-hydroxy-2-methyl-phenyl)-3-n-dodecylmercapto butane, ethylene glycol bis[3 ,3 -bis(3′-tert-butyl-4′-hydroxyphenyl)butyrate], bis(3 -tert-butyl-4-hydroxy-5 -methyl-phenyl)dicyclopentadiene, bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-m ethylphenyl]terephthalate, 1,1-bis-(3,5 -dimethyl-2-hydroxyphenyl)butane, 2,2-bis-(3 ,5 -di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis-(5 -tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5 -tetra-(5 -tert-butyl-4-hydroxy-2-methyl phenyl)pentane, and combinations thereof may be utilized as antioxidants in the lubricant composition.

O—, N— and S-benzyl compounds, for example 3,5,3′, 5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3 ,5 -dimethylbenzylmercaptoacetate, tris-(3 ,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl -3 -hydroxy-2, 6-dimethylbenzyl)dithiol terephthalate, bis(3 ,5 -di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5di-tert-butyl-4-hydroxy benzylmercaptoacetate, and combinations thereof, may also be utilized.

Hydroxybenzyl ated malonates, for example dioctadecyl-2,2-bis-(3 ,5 -di-tert-butyl-2-hydroxybenzyl)-malonate, di-octadecyl-2-(3 -tert-butyl-4-hydroxy-5 -methylbenzyl)-malonate, di-dodecylmercaptoethyl-2,2-bis-(3,5-di-tert-butyl -4-hydroxybenzyl)malonate, bis [4-(1,1,3,3 -tetramethylbutyl)phenyl]-2,2-bis(3 ,5 -di-tert-butyl-4-hydroxybenzyl)malonate, and combinations thereof are also suitable for use as antioxidants.

Triazine compounds, for example, 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3 ,5 -di-tert-butyl-4-hydroxyanilino)-1,3 ,5-triazine, 2-octylmercapto-4,6-bis(3 , 5-di-tert-butyl-4-hydroxyphenoxy)-1,3 ,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5 -tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5 -tris(4-tert-butyl-3 -hydroxy-2, 6-dimethylbenzyl 2,4,6-tris(3 , 5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5 -triazine, 1,3,5 -tris(3,5-di-tert-butyl-4-hydroxyphenyl propionyl)-hexahydro-1,3,5-triazine, 1,3,5 -tris-(3 ,5 -dicyclohexyl-4-hydroxybenzyl)-isocyanurate, and combinations thereof, may also be used.

Additional examples of antioxidants include aromatic hydroxybenzyl compounds, for example 1,3,5 -tris-(3 ,5 -di-tert-butyl-4-hydroxybenzyl)-2,4, 6-trimethylbenzene, 1,4-bis(3 , 5-di-tert-butyl-4-hydroxybenzyl)-2,3,5, 6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol, and combinations thereof. Benzylphosphonates, for example dimethyl-2,5 -di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3 ,5 -di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl3,5 -di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid, and combinations thereof, may also be utilized. In addition, acylaminophenols, for example 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3 ,5 -di-tert-butyl-4-hydroxyphenyl)carbamate.

Esters of [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) i socyanurate, N,N′-bis(hydroxyethyl)oxamide, 3 -thiaundecanol, 3 -thiapentadecanol, trim ethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1 -phospha-2, 6,7-trioxabicyclo[2 .2.2] octane, and combinations thereof, may also be used. It is further contemplated that esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl) i socyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thi apentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo octane, and combinations thereof, may be used.

Additional examples of suitable antioxidants include those that include nitrogen, such as amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, e.g., N,N′-bis(3 ,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexam ethylenediamine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyphydrazine. Other suitable examples of antioxidants include aminic antioxidants such as N,N′-diisopropyl-p-phenylenediamine, N,N′-di -sec-butyl-p-phenylenediamine, N,N′-bis (1,4-dimethylpentyl)-p-phenylenedi amine, N,N′-bis(1-ethyl-3 -methylpentyl)-p-phenylenediamine, N,N′-bis(1-methylheptyl)-p-phenylenediamine, N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine, N,N′-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3 -dimethyl-butyl)-N′-phenyl-p-phenylenediamine, N-(1 -methylheptyl)-N′-phenyl-p-phenylenediamine, N-cyclohexyl-N′-phenyl-p-phenylenediamine, 4-(p-toluenesulfamoyl)diphenylamine, N,N′-dimethyl -N,N′-di-sec-butyl-p-phenylenediamine, diphenyl amine, N-allyldiphenyl amine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p,p′-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis(4-methoxyphenyl)amine, 2, 6-di-tert-butyl-4-dimethylamino methylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane, 1,2-bis[(2-methyl-phenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1′,3-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines, mixtures of mono- and dialkylated tert-butyl diphenylamines, 2,3 -dihydro-3 ,3 -dimethyl-4H-1,4-benzothiazine, phenothiazine, N-allylphenothiazine, N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis(2,2,6, 6-tetramethylpiperid-4-yl-hexamethylenediamine, bis(2,2, 6,6-tetramethyl piperid-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one and 2,2,6,6-tetramethyl piperidin-4-ol, and combinations thereof.

Even further examples of suitable antioxidants include aliphatic or aromatic phosphites, esters of thiodipropionic acid or of thiodiacetic acid, or salts of dithiocarbamic or dithiophosphoric acid, 2,2,12,12-tetramethyl-5,9-dihydroxy-3,7,1trithiatridecane and 2,2,15,15-tetramethyl-5,12-dihydroxy-3 ,7, 10,14-tetrathiahexadecane, and combinations thereof. Furthermore, sulfurized fatty esters, sulfurized fats and sulfurized olefins, and combinations thereof, may be used.

If employed, the antioxidant can be used in various amounts. The antioxidant may be present in the additive package in an amount ranging from 0.1 to 99, from 1 to 70, from 5 to 50, or from 25 to 50, wt. %, based on the total weight of the additive package. The antioxidant may be present in the lubricant composition in an amount ranging from 0.01 to 5, from 0.1 to 3, or from 0.5 to 2, wt. %, based on the total weight of the lubricant composition.

If employed, the metal deactivator can be of various types. Suitable examples of metal deactivators include, but are not limited to, benzotriazoles and derivatives thereof, for example 4-or 5 alkylbenzotriazoles (e.g. tolutriazole) and derivatives thereof, 4,5,6,7-tetrahydrobenzotriazole and 5,5′-methylenebisb enzotriazole; Mannich bases of benzotriazole or tolutriazole, e.g. 1-[bis(2-ethylhexyl)aminomethyl)tolutriazole and 1-[bis(2-ethylhexyl)aminomethyl)benzotriazole; and alkoxyalkylbenzotriazoles such as 1-(nonyloxymethyl)benzotriazole, 1-(1-butoxyethyl)benzotriazole and 1-(1-cyclohexyloxybutyl) tolutriazole, and combinations thereof.

Additional examples of suitable metal deactivators include 1,2,4-triazoles and derivatives thereof, for example 3 alkyl(or aryl)-1,2,4-triazoles, and Mannich bases of 1,2,4-triazoles, such as 1-[bis(2-ethylhexyl)aminomethyl-1,2,4-triazole; alkoxyalkyl-1,2,4-triazoles such as 1-(1-butoxyethyl)-1,2,4-triazole; and acylated 3-amino-1,2,4-triazoles, imidazole derivatives, for example 4,4′-methylenebis(2-undecyl-5-methylimidazole) and bis[(N-methyl)imidazol-2-yl]carbinol octyl ether, and combinations thereof. Further examples of suitable metal deactivators include sulfur-containing heterocyclic compounds, for example 2-mercaptobenzothiazole, 2,5-dimercapto-1,3,4-thiadiazole and derivatives thereof; and 3,5-bis[di(2-ethylhexyl)aminomethyl]-1,3,4-thiadiazolin-2-one, and combinations thereof. Even further examples of metal deactivators include amino compounds, for example salicylidenepropylenediamine, salicylaminoguanidine and salts thereof, and combinations thereof.

If employed, the metal deactivator can be used in various amounts. The metal deactivator may be present in the additive package in an amount ranging from 0.1 to 99, from 1 to 70, from 5 to 50, or from 25 to 50, wt. %, based on the total weight of the additive package. The metal deactivator may be present in the lubricant composition in an amount ranging from 0.01 to 0.1, from 0.05 to 0.01, or from 0.07 to 0.1, wt. %, based on the total weight of the lubricant composition.

If employed, the rust inhibitor and/or friction modifier can be of various types. Suitable examples of rust inhibitors and/or friction modifiers include, but are not limited to, organic acids, their esters, metal salts, amine salts and anhydrides, for example alkyl- and alkenylsuccinic acids and their partial esters with alcohols, diols or hydroxycarboxylic acids, partial amides of alkyl- and alkenylsuccinic acids, 4-nonylphenoxyacetic acid, alkoxy- and alkoxyethoxycarboxylic acids such as dodecyloxyacetic acid, dodecyloxy(ethoxy)acetic acid and the amine salts thereof, and also N-oleoylsarcosine, sorbitan monooleate, lead naphthenate, alkenylsuccinic anhydrides, for example, dodecenylsuccinic anhydride, 2-carboxymethyl-1-dodecyl-3-methylglycerol and the amine salts thereof, and combinations thereof. Additional examples include nitrogen-containing compounds, for example, primary, secondary or tertiary aliphatic or cycloaliphatic amines and amine salts of organic and inorganic acids, for example oil-soluble alkylammonium carboxylates, and also 1-[N,N-bis(2-hydroxyethyl)amino] -3 -(4-nonylphenoxy)propan-2-ol, and combinations thereof. Further examples include heterocyclic compounds, such as substituted imidazolines and oxazolines, and 2-heptadecenyl-1-(2-hydroxyethyl)imidazoline, phosphorus-containing compounds, for example: amine salts of phosphoric acid partial esters or phosphonic acid partial esters, molybdenum containing compounds, such as molydbenum dithiocarbamate and other sulphur and phosphorus containing derivatives, sulfur-containing compounds, for example: barium dinonylnaphthalenesulfonates, calcium petroleum sulfonates, alkylthio-substituted aliphatic carboxylic acids, esters of aliphatic 2-sulfocarboxylic acids and salts thereof, glycerol derivatives, for example: glycerol monooleate, 1-(alkylphenoxy)-3 -(2-hydroxyethyl)glycerol s, 1-(alkylphenoxy)-3 -(2,3 -dihydroxypropyl) glycerols and 2-carboxyalkyl-1,3-dialkylglycerols, and combinations thereof.

If employed, the rust inhibitor and/or friction modifier can be used in various amounts. The rust inhibitor and/or friction modifier may be present in the additive package in an amount ranging from 0.01 to 0.1, from 0.05 to 0.01, or from 0.07 to 0.1, wt. %, based on the total weight of the additive package. The rust inhibitor and/or friction modifier may be present in the lubricant composition in an amount ranging from 0.01 to 5, from 0.1 to 3, from 0.1 to 1, from 0.05 to 0.01, or from 0.07 to 0.1, wt. %, based on the total weight of the lubricant composition.

If employed, the viscosity index improver (VII) can be of various types. Suitable examples of VIIs include, but are not limited to, polyacrylates, polymethacrylates, vinylpyrrolidone/methacrylate copolymers, polyvinylpyrrolidones, polybutenes, olefin copolymers, styrene/acrylate copolymers and polyethers, and combinations thereof

If employed, the VII can be used in various amounts. The VII may be present in the additive package in an amount ranging from 0.01 to 20, from 1 to 15, or from 1 to 10, wt. %, based on the total weight of the additive package. The VII may be present in the lubricant composition in an amount ranging from 0.01 to 20, from 1 to 15, or from 1 to 10, wt. %, based on the total weight of the lubricant composition.

If employed, the pour point depressant can be of various types. Suitable examples of pour point depressants include, but are not limited to, polymethacrylate and alkylated naphthalene derivatives, and combinations thereof.

If employed, the pour point depressant can be used in various amounts. The pour point depressant may be present in the additive package in an amount ranging from 0.1 to 99, from 1 to 70, from 5 to 50, or from 25 to 50, wt. %, based on the total weight of the additive package. The pour point depressant may be present in the lubricant composition in an amount ranging from 0.01 to 0.1, from 0.05 to 0.01, or from 0.07 to 0.1, wt. %, based on the total weight of the lubricant composition.

If employed, dispersant can be of various types. Suitable examples of dispersants include, but are not limited to, amine dispersants, alkenyl radicals, polybutenylsuccinic amides or -imides, polybutenylphosphonic acid derivatives and basic magnesium, calcium and barium sulfonates and phenolates, succinate esters and alkylphenol amines (Mannich bases), and combinations thereof.

If employed, the amine dispersant may have a total base number of at least 15, at least 25, or at least 30, mg KOH/g of the amine dispersant when measured according to ASTM D4739. Alternatively, the TBN value of the amine dispersant may range from 15 to 100, from 15 to 80, or from 15 to 75, mg KOH/g of the amine dispersant, when measured according to ASTM D 4739.

In some embodiments, the amine dispersant includes a polyalkene amine including a polyalkene moiety. The polyalkene moiety is the polymerization product of identical or different, straight-chain or branched C_2-6 olefin monomers. Examples of suitable olefin monomers are ethylene, propylene, 1-butene, isobutene, 1-pentene, 2-methyl butene, 1-hexene, 2-methylpentene, 3-methylpentene, and 4-methylpentene. The polyalkene moiety has a weight average molecular weight of from 200 to 10000, from 500 to 10000, or from 800 to 5000.

The amine dispersant may include moieties derived from succinic anhydride and having hydroxyl and/or amino and/or amido and/or imido groups. For example, the amine dispersant may be derived from polyisobutenylsuccinic anhydride which is obtainable by reacting conventional or highly reactive polyisobutene having a weight average molecular weight of from 500 to 5000 with maleic anhydride by a thermal route or via the chlorinated polyisobutene. For examples, derivatives with aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentamine may be used.

To prepare the polyalkene amine, the polyalkene component may be aminated in a known manner. An exemplary process proceeds via the preparation of an oxo intermediate by hydroformylation and subsequent reductive amination in the presence of a suitable nitrogen compound.

If employed, suitable examples of alkenyl radicals include mono- or polyunsaturated, such as mono- or diunsaturated analogs of alkyl radicals has from 2 to 18 carbon atoms, in which the double bonds may be in any position in the hydrocarbon chain. Examples of C₄-C₁₈ cycloalkyl radical include cyclobutyl, cyclopentyl and cyclohexyl, and also the analogs thereof substituted by 1 to 3 C₁-C₄ alkyl radicals. The C₁-C₄ alkyl radicals are, for example, selected from methyl, ethyl, iso- or n-propyl, n-, iso-, sec- or tert-butyl. Examples of the arylalkyl radical include a C₁-C₁₈ alkyl group and an aryl group which are derived from a monocyclic or bicyclic fused or nonfused 4- to 7-membered, in particular 6 membered, aromatic or heteroaromatic group, such as phenyl, pyridyl, naphthyl and biphenyl. Other examples of the alkenyl radicals include poly(oxyalkyl) radicals and a polyalkylene polyamine radicals.

If employed, the dispersant can be used in various amounts. The dispersant may be present in the additive package in an amount ranging from 0.1 to 99.9, from 0.1 to 50, from 5 to 25, or from 5 to 20, wt. %, based on the total weight of the additive package. The dispersant may be present in the lubricant composition in an amount of from 0.01 to 15, 0.1 to 12, 0.5 to 10, or 1 to 8, wt. %, based on the total weight of the lubricant composition. Alternatively, the dispersant may be present in amounts of less than 15, less than 12, less than 10, less than 5, or less than 1, wt. %, each based on the total weight of the lubricant composition.

If employed, the detergent can be of various types. Suitable examples of detergents include, but are not limited to, overbased or neutral metal sulphonates, phenates and salicylates, and combinations thereof.

If employed, the detergent can be used in various amounts. The detergent may be present in the additive package in an amount ranging from 0.1 to 99, from 1 to 70, from 5 to 50, or from 25 to 50, wt. %, based on the total weight of the additive package. The detergent may be present in the lubricant composition in an amount ranging from 0.01 to 5, from 0.1 to 4, from 0.5 to 3, or from 1 to 3, wt. %, based on the total weight of the lubricant composition. Alternatively, the detergent may be present in amounts of less than 5, less than 4, less than 3, less than 2, or less than 1, wt. %, based on the total weight of the lubricant composition.

If employed, anti-foam additive can be of various types and used in various amounts. The anti-foam additive may be present in the additive package in an amount ranging from 0.01 to 1, from 0.01 to 0.5, from 0.01 to 0.1, or from 0.02 to 0.08, wt. %, based on the total weight of the additive package. The anti-foam additive may be present in the lubricant composition in an amount ranging from 0.001 to 1, 0.001 to 0.05, 0.001 to 0.01, or 0.002 to 0.008, wt. %, based on the total weight of the lubricant composition.

If employed, amine compound can be of various types. The amine compound includes at least one nitrogen atom. Furthermore, in some configurations, the amine compound does not include triazoles, triazines, or similar compounds where there are three or more nitrogen atoms in the body of a cyclic ring. The amine compound may be aliphatic.

In certain embodiments, the amine compound has a total base number (TBN) value of at least 10 mg KOH/g when tested according to ASTM D4739. Alternatively, the amine compound has a TBN value of at least 15, at least 20, at least 25, at least 80, at least 90, at least 100, at least 110, at least 120, at least 130, at least 140, at least 150, or at least 160, mg KOH/g, when tested according to ASTM D4739. Alternatively still, the amine compound may have a TBN value of from 80 to 600, from 90 to 500, from 100 to 300, or from 100 to 200, mg KOH/g, when tested according to ASTM D4739.

In some embodiments, the amine compound does not negatively affect the TBN of the lubricant compositions. Alternatively, the amine compound may improve the TBN of the lubricant composition by, at least 0.5, at least 1, at least 1.5, at least 2, at least 2.5, at least 3, at least 3.5, at least 4, at least 4.5, at least 5, at least 10, or at least 15, mg KOH/g of the amine compound. The TBN value of the lubricant composition can be determined according to ASTM D2896.

In some embodiments, the amine compound consists of, or consists essentially of, hydrogen, carbon, nitrogen, and oxygen. Alternatively, the amine compound may consist of, or consist essentially of, hydrogen, carbon, and nitrogen. In the context of the amine compound, the phrase “consist essentially of” refers to compounds where at least 95 mole % of the amine compound are the recited atoms (i.e., hydrogen, carbon, nitrogen, and oxygen; or hydrogen, carbon, and nitrogen). For example, if the amine compound consists essentially of hydrogen, carbon, nitrogen, and oxygen, at least 95 mole % of the amine compound is hydrogen, carbon, nitrogen, and oxygen. In certain configurations, at least 96, at least 97, at least 98, at least 99, or at least 99.9, mole %, of the amine compound are hydrogen, carbon, nitrogen and oxygen, or, in other embodiments, are carbon, nitrogen, and hydrogen.

The amine compound may consist of covalent bonds. The phrase “consist of covalent bonds” is intended to exclude those compounds which bond to the amine compound through an ionic association with at least one ionic atom or compound. That is, in configurations where the amine compound consists of covalent bonds, the amine compound excludes salts of amine compounds, for example, phosphate amine salts and ammonium salts. As such, in certain embodiments, the lubricant composition is free of a salt of the amine compound. For example, the lubricant compositions may be free of a phosphate amine salt, ammonium salt, and/or amine sulfate salt.

The amine compound may be a monomeric acyclic amine compound having a weight average molecular weight of less than 500. Alternatively, the monomeric acyclic amine compound may have a weight average molecular weight of less than 450, less than 400, less than 350, less than 300, less than 250, less than 200, or less than 150. Alternatively still, the amine compound may have a weight average molecular weight of at least 30, at least 50, at least 75, at least 100, at least 150, at least 200, or at least 250.

The term “acyclic” is intended to refer to amine compounds which are free from any cyclic structures and to exclude aromatic structures. For example, the monomeric acyclic amine compound does not include compounds having a ring having at least three atoms bonded together in a cyclic structure and those compounds including benzyl, phenyl, or triazole groups.

The monomeric acyclic amine includes monoamines and polyamines (including two or more amine groups). Exemplary monomeric acyclic amine compounds include, but are not limited to, primary, secondary, and tertiary amines.

The monomeric acyclic amine compound may alternatively include at least one other primary amines such as ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, tert-butylamine, pentylamine, and hexylamine; primary amines of the formulas: CH₃—O—C₂H₄—NH₂, C₂H₅—O—C₂H₄—NH₂, CH₃—O—C₃H₆—NH₂, C₂H₅—O—C₃H₆—NH₂, C₄H₉—O—C₄H₈—NH₂, HO—C₂H₄—NH₂, HO—C₃H₆—NH₂ and HO—C₄H₈—NH₂; secondary amines, for example diethylamine, methylethylamine, di-n-propylamine, diisopropylamine, diisobutylamine, di-sec-butylamine, di-tert-butylamine, dipentylamine, dihexylamine; and also secondary amines of the formulas: (CH₃—O—C₂H₄)₂NH, (C₂H₅—O—C₂H₄)₂NH, (CH₃—O—C₃H₆)₂NH, (C₂H₅—O—C₃H₆)₂NH, (n-C₄H₉—O—C₄H₈)₂NH, (HO—C₂H₄)₂NH, (HO—C₃H₆)₂NH and (HO—C₄H₈)₂NH; and polyamines, such as n-propyl enediamine, 1,4-butanediamine, 1,6-hexanediamine, diethylenetriamine, triethylenetetramine and tetraethylenepentamines, and also their alkylation products, for example 3 -(dimethylamino)-n-propylamine, N,N-dimethylethylenediamine, N,N-diethylethylenediamine, and N,N,N′,N′-tetramethyldiethylenetriamine.

Alternatively, the amine compound may be a monomeric cyclic amine compound. The monomeric cyclic amine compound may have a weight average molecular weight of from 100 to 1200, from 200 to 800, or from 200 to 600. Alternatively, the monomeric cyclic amine compound may have a weight average molecular weight of less than 500, or at least 50. In some embodiments, the monomeric cyclic amine compound is free from aromatic groups, such as phenyl and benzyl rings. In other embodiments, the monomeric cyclic amine compound is aliphatic.

The monomeric cyclic amine compound may include two or fewer nitrogen atoms per molecule. Alternatively, the monomeric cyclic amine compound may include only one nitrogen per molecule. The phrase “nitrogen per molecule” refers to the total number of nitrogen atoms in the entire molecule, including the body of the molecule and any substituent groups. In certain embodiments, the monomeric cyclic amine compound includes one or two nitrogen atoms in the cyclic ring of the monomeric cyclic amine compound.

In some embodiments, the amine compound, such as the monomeric acyclic amine compound or the monomeric cyclic amine compound, may be a sterically hindered amine compound. The sterically hindered amine compound may have a weight average molecular weight of from 100 to 1200. Alternatively, the sterically hindered amine compound may have a weight average molecular weight of from 200 to 800, or from 200 to 600. Alternatively still, the sterically hindered amine compound may have a weight average molecular weight of less than 500.

The sterically hindered amine compound may include a single ester group. However, the sterically hindered amine compound may alternatively be free from ester groups. In certain embodiments, the sterically hindered amine compound may include at least one, or only one, piperidine ring.

If employed, the amine compound can be used in various amounts. The amine compound may be present in the additive package in an amount ranging from 0.1 to 50, from 0.1 to 25, from 0.1 to 15, from 0.1 to 10, from 0.1 to 8, or from 1 to 5, wt. %, based on the total weight of the additive package. The dispersant may be present in the lubricant composition in an amount ranging from 0.1 to 25, from 0.1 to 20, from 0.1 to 15, from 0.1 to 10, from 0.5 to 5, from 1 to 3, or from 1 to 2, wt. %, based on the total weight of the lubricant composition.

The present disclosure also provides a method of lubricating an internal combustion engine for improving fuel economy of the internal combustion engine. The method includes providing the lubricant composition. The lubricant composition, as described above, includes the base oil, the alkoxylated amine, the ester, and the anti-wear agent. The method further includes lubricating the internal combustion engine with the lubricant composition.

The present disclosure further provides a method of maximizing the effectiveness of a friction modifier in a racing oil composition thus increasing the fuel economy of a racing vehicle. As described above, the friction modifier is typically a mixture of the alkyoxylated amide and the the ester. The method includes providing the racing oil composition comprising the base oil, the friction modifier, and the anti-wear agent including phosphorus. The friction modifier includes the alkoxylated amide having the following formula:

and the ester having the following formula:

with each R¹ being, independently, a linear or branched, saturated or unsaturated, C₆-C₂₃ aliphatic hydrocarbyl group. The method also includes lubricating an internal combustion engine of the racing vehicle to increase the fuel economy of the racing vehicle.

It is to be appreciated that many changes may be made to the following examples, while still obtaining like or similar results. Accordingly, the following examples, illustrating embodiments of the additive package and resultant lubricant composition of the present disclosure, are intended to illustrate and not to limit the disclosure.

EXAMPLES

Exemplary Method 1 for Formation of the Alkoxylated Amide and Ester

A. Condensation Reaction to Form a Coconut Oil Diethanolamide Mixture

Coconut oil (3.80 kg, 5.78 mol) was added to a reactor and heated to about 130° C. Diethanolamine (DEA) (1.22 kg, 11.6 mol, 2 eq.) was added, and the resulting mixture was maintained at a reaction temperature of about 130° C., with stirring, for an additional 6 hours. The product was a viscous yellow to brown oil (5.01 kg), which was used in the alkoxylation reaction without purification.

The condensation reaction was performed using the following starting materials.

Common Name    Spec.
Coconut oil    40-50% C12
               15-20% C14
               7-12% C16
Diethanolamine >99% purity

The molecular weight of the coconut oil was calculated from the saponification value.

B. Amine Catalyzed Alkoxylation

The diethanolamide reaction product of step A (869 g, 2.02 mol) was admixed with an amine catalyst (4.9 g N,N-dimethylethanolamine, 0.06 mol, 0.5 w/w %). The resulting mixture was heated to about 110° C. Propylene oxide (117 g, 2.02 mol, 1.0 eq) was added, and the mixture was stirred for additional 12 hours at the reaction temperature. Unreacted propylene oxide was removed under reduced pressure and/or by flushing with nitrogen gas to yield the reaction product.

The following Scheme illustrates the reactions of steps A and B, and the reaction products present after step B.

It is noted that an ester also forms in step A, together with the diethanolamide. This ester and unreacted diethanolamine are present during the alkoxylation step B, and may be allowed to remain in the final product. As noted in the above reaction scheme, the ester of step A also was propoxylated. It is further noted that the above Scheme only depicts the main reaction products. The degree of propoxylation is subject to statistic distribution, and further reaction products in minor amounts such as various ethers and heterocycles, e.g., bishydroxyethylpiperazine, as well as residual unreacted compounds, can be found.

Exemplary Method 2 for Formation of the Alkoxylated Amide and Ester

A. Condensation Reaction to Form a Coconut Fatty Acid Diethanolamide Mixture

Coconut fatty acid (3.05 kg, 14.4 mol) was placed in a reactor and heated to about 80° C. Diethanolamine (1.52 kg, 14.4 mol, 1.0 eq.) was added, and the resulting mixture was heated to reaction temperature of about 150° C., then stirred for additional 8 hours. The product was a viscous yellow to brown oil (3.95 kg), which was used in the alkoxylation reaction without further purification.

The condensation reaction was performed using the following starting materials.

	Common Name	Trade Name	Spec.
	Coconut fatty acid	EDENOR K8-18	45-53% C12
			17-21% C14
			7-13% C16
	Diethanolamine		>99% purity

The molecular weight of the coconut fatty acid was calculated from the acid number.

B. Amine Catalyzed Alkoxylation Reaction

The diethanolamide reaction product of step A (495 g, 1.72 mol) was admixed with an amine catalyst (3.0 g N,N-dimethylethanolamine, 0.03 mol, 0.5 w/w %). The resulting mixture was heated to about 115° C. propylene oxide (100 g, 1.72 mol, 1.0 eq) was added and the mixture was stirred for additional 12 hours at about 115° C. Unreacted propylene oxide was removed under reduced pressure and/or by flushing with nitrogen to yield the reaction product.

The following scheme illustrates the reactions of steps A and B, and the reaction products present after step B.

An ester also is formed in step A, together with the diethanolamide. This ester and any unreacted diethanolamine are present during the alkoxylation step B, and may be allowed to remain in the final product. As noted in the above reaction scheme, the ester of step A also was propoxylated. It is further noted that the above Scheme only depicts the main reaction products.

The degree of propoxylation is subject to statistic distribution, and further reaction products in minor amounts such as various ethers and heterocycles, e.g., bishydroxyethylpiperazine, as well as residual unreacted compounds, can be found.

Evaluation of Lubricant Compositions Including the Base Oil, the Alkoxylated Amide, the Ester, and the Anti-Wear Agent

A. Friction Coefficient and Ball Scar Diameter Evaluation I

The friction coefficient and the ball scar diameter for lubricant compositions including a base oil, the alkoxylated amide, the ester, and an anti-wear agent were evaluated. The friction coefficient of the lubricant composition was determined according to a modified ASTM D 6079 method. The modified ASTM D 6079 method utilized a High Frequency Reciprocating Rig (HFRR) for determining the friction coefficient. During the determination, the HFRR reciprocated at 10 Hz with a 1 mm stroke. The determination was conducted at a temperature of 100° C. for duration of 120 minutes with a 400 gram load using standard HFRSSP steel balls. The ball scar diameter of the lubricant composition was determined by a laser profilometer.

Example 1 includes 100 wt. % of a Group II base oil. Examples 2-7 include a mixture of Group II base oil and an anti-wear agent containing phosphorous. Examples 8-13 a mixture of the alkoxylated amide and ester in an amount as shown in Table 1, and a Group II base oil. Examples 14-19 include an anti-wear agent including phosphorous, a mixture of the alkoxylated amide and ester, and a Group II base oil. Examples 8-19 each also include a minor amount of by-products resulting and reactants remaining from the preparation of the alkoxylated amide of general formula (I) and the ester of general formula (II).

The mixture of alkoxylated amide and ester in Examples 8-19 include the alkoxylated amide and the ester in a weight ratio of 75:25 of the ester to the alkoxylated amide. The anti-wear agent including phosphorous included in Examples 2-7 and 14-19 is zinc dialkyldithiophosphate.

Results of the evaluation are provided in Table 1 below.

	TABLE 1
		Anti-wear	Mixture of	Friction	Ball
		agent	the alkoxyl-	coefficient	scar
	Base	including	ated amide	of lubricant	diam-
	oil	phosphorous	and ester	composition	eter
	(wt. %)	(wt. %)	(wt. %)	(μ)	(μm)
Example 1	100	—	—	0.41	440
Example 2	99.985	0.015	—	0.22	303.5
Example 3	99.97	0.03	—	0.19	294
Example 4	99.94	0.06	—	0.22	301
Example 5	99.92	0.08	—	0.19	300
Example 6	99.88	0.12	—	0.21	296
Example 7	99.8	0.2	—	0.23	264.5
Example 8	99.97	—	0.03	0.33	302.5
Example 9	99.9	—	0.1	0.16	284.5
Example 10	99.7	—	0.3	0.18	274.5
Example 11	99.4	—	0.6	0.18	285
Example 12	99	—	1	0.18	288.5
Example 13	98	—	2	0.17	266
Example 14	99.92	0.08	0.03	0.22	198
Example 15	99.92	0.08	0.1	0.15	190
Example 16	99.92	0.08	0.3	0.17	186.5
Example 17	99.92	0.08	0.6	0.18	186
Example 18	99.92	0.08	1	0.18	208
Example 19	99.92	0.08	2	0.17	206.5

B. Friction Coefficient and Ball Scar Diameter Evaluation II

The friction coefficient and the ball scar diameter for lubricant compositions including the base oil, the alkoxylated amide, the ester, and the anti-wear agent were further evaluated against lubricant compositions including comparative friction modifiers. The friction coefficient of each of the lubricant compositions was determined according to a modified ASTM D 6079 method. The modified ASTM D 6079 method utilized a High Frequency Reciprocating Rig (HFRR) for determining the friction coefficients. During the determination, the HFRR reciprocated at 10 Hz with a 1 mm stroke. The determination was conducted at a temperature of 100° C. for duration of 120 minutes with a 400 gram load using standard HFRSSP steel balls. The ball scar diameter of each of the lubricant compositions was determined by a laser profilometer.

Examples 20-86 include a Group II base oil (Base oil).

Examples 21-32, 39-44, 51-56, 63-68, and 75-80 further include zinc dialkyldithiophosphate as the anti-wear agent including phosphorous (Anti-wear agent).

Examples 27-38 further include glycerol mono oleate as the ester free of nitrogen (Friction modifier I).

Examples 39-50 further include lauryl amide as the amide free of alkoxylation (Friction modifier II).

Examples 51-62 further include lauryl amide and glycerol mono oleate.

Examples 63-74 further include a mixture of the alkoxylated amide and the ester in a weight ratio of 75:25 of the ester to the alkoxylated amide (Fuel economy agent).

Examples 75-86 further include the mixture of the alkoxylated amide and the ester, and glycerol mono oleate.

Examples 63-86 also include a minor amount of by-products resulting and reactants remaining from the preparation of the alkoxylated amide of general formula (I) and the ester of general formula (II).

Results of the evaluation are provided in Table 2 below.

	TABLE 2
		Anti-			Fuel
		wear	Friction	Friction	economy	Friction	Ball scar
	Base oil	agent	modifier	modifier	agent	coefficient	diameter
	(wt. %)	(wt. %)	I (wt. %)	II (wt. %)	(wt. %)	(μ)	(μm)
Ex. 20	100	—	—	—	—	0.411	440
Ex. 21	99.985	0.015	—	—	—	0.22	303.5
Ex. 22	99.97	0.03	—	—	—	0.19	294
Ex. 23	99.94	0.06	—	—	—	0.22	301
Ex. 24	99.92	0.08	—	—	—	0.221	303
Ex. 25	99.88	0.12	—	—	—	0.21	296
Ex. 26	99.8	0.2	—	—	—	0.23	264.5
Ex. 27	99.89	0.08	0.03	—	—	0.154	236
Ex. 28	99.82	0.08	0.1	—	—	0.161	259
Ex. 29	99.62	0.08	0.3	—	—	0.134	168
Ex. 30	99.32	0.08	0.6	—	—	0.12	155
Ex. 31	98.92	0.08	1	—	—	0.118	157
Ex. 32	97.92	0.08	2	—	—	0.135	168
Ex. 33	99.97	—	0.03	—	—	0.168	229
Ex. 34	99.9	—	0.1	—	—	0.13	206
Ex. 35	99.7	—	0.3	—	—	0.106	209
Ex. 36	99.4	—	0.6	—	—	0.112	203
Ex. 37	99	—	1	—	—	0.115	199
Ex. 38	98	—	2	—	—	0.119	185
Ex. 39	99.89	0.08	—	0.03	—	0.15	135
Ex. 40	99.82	0.08	—	0.1	—	0.15	165
Ex. 41	99.62	0.08	—	0.3	—	0.15	184
Ex. 42	99.32	0.08	—	0.6	—	0.16	194
Ex. 43	98.92	0.08	—	1	—	0.16	169
Ex. 44	97.92	0.08	—	2	—	0.17	172
Ex. 45	99.97	—	—	0.03	—	0.16	237
Ex. 46	99.9	—	—	0.1	—	0.17	256
Ex. 47	99.7	—	—	0.3	—	0.16	257
Ex. 48	99.4	—	—	0.6	—	0.16	271
Ex. 49	99	—	—	1	—	0.17	258
Ex. 50	98	—	—	2	—	0.16	252
Ex. 51	99.89	0.08	0.015	0.015	—	0.154	212
Ex. 52	99.82	0.08	0.05	0.05	—	0.157	168
Ex. 53	99.62	0.08	0.15	0.15	—	0.145	189
Ex. 54	99.32	0.08	0.3	0.3	—	0.147	181
Ex. 55	98.92	0.08	0.5	0.5	—	0.142	176
Ex. 56	97.92	0.08	1	1	—	0.141	172
Ex. 57	99.97	—	0.015	0.015	—	0.188	238
Ex. 58	99.9	—	0.05	0.05	—	0.160	231
Ex. 59	99.7	—	0.15	0.15	—	0.169	243
Ex. 60	99.4	—	0.3	0.3	—	0.148	218
Ex. 61	99	—	0.5	0.5	—	0.148	206
Ex. 62	98	—	1	1	—	0.140	200
Ex. 63	99.89	0.08	—	—	0.03	0.22	198
Ex. 64	99.82	0.08	—	—	0.1	0.15	190
Ex. 65	99.62	0.08	—	—	0.3	0.17	186.5
Ex. 66	99.32	0.08	—	—	0.6	0.18	186
Ex. 67	98.92	0.08	—	—	1	0.18	208
Ex. 68	97.92	0.08	—	—	2	0.17	206.5
Ex. 69	99.97	—	—	—	0.03	0.33	302.5
Ex. 70	99.9	—	—	—	0.1	0.16	284.5
Ex. 71	99.7	—	—	—	0.3	0.18	274.5
Ex. 72	99.4	—	—	—	0.6	0.18	285
Ex. 73	99	—	—	—	1	0.18	288.5
Ex. 74	98	—	—	—	2	0.17	266
Ex. 75	99.89	0.08	0.015	—	0.015	0.151	193
Ex. 76	99.82	0.08	0.05	—	0.05	0.154	171
Ex. 77	99.62	0.08	0.15	—	0.15	0.158	186
Ex. 78	99.32	0.08	0.3	—	0.3	0.161	182
Ex. 79	98.92	0.08	0.5	—	0.5	0.165	180
Ex. 80	97.92	0.08	1	—	1	0.158	192
Ex. 81	99.97	—	0.015	—	0.015	0.155	225
Ex. 82	99.9	—	0.05	—	0.05	0.158	258
Ex. 83	99.7	—	0.15	—	0.15	0.158	233
Ex. 84	99.4	—	0.3	—	0.3	0.160	228
Ex. 85	99	—	0.5	—	0.5	0.149	212
Ex. 86	98	—	1	—	1	0.146	184

C. Traction Coefficient Evaluation

The traction coefficients for lubricant compositions including the base oil, the alkoxylated amide, the ester, and the anti-wear agent were evaluated against lubricant compositions including a comparative friction modifier. The traction coefficient of each of the lubricant compositions was determined by utilizing a Mini-Traction Machine (MTM), specifically MTM 2 from PCS Instruments. During the determination, standard steel ball (19.05mm) and discs (46mm) were utilized in the MTM, the load of the MTM was set to 1GPa, and the lubricant compositions were pre-heated to 125° C. The traction coefficient of each of the lubricant compositions was measured from speeds between 0 and 2000 mm/s utilizing a 25% slide/roll ratio.

Examples 87-314 include a Group II base oil (Base oil).

Examples 315-428 include a Group II base oil with an additive package including a dispersant, an antioxidant, a detergent, a pour point depressant, and a viscosity modifier (Base oil with additive package).

Examples 201-428 further include zinc dialkyldithiophosphate as the anti-wear agent including phosphorous (Anti-wear agent).

Examples 125-162, 239-276, and 353-390 further include glycerol mono oleate as the ester free of nitrogen (Friction modifier I).

Examples 163-200, 277-314, and 391-428 further include a mixture of the alkoxylated amide and the ester in a weight ratio of 75:25 of the ester to the alkoxylated amide (Fuel economy agent).

Examples 163-200, 277-314, and 391-428 also include a minor amount of by-products resulting and reactants remaining from the preparation of the alkoxylated amide of general formula (I) and the ester of general formula (II).

Results of the evaluation are provided in Table 3 below and graphically in FIG. 1.

	TABLE 3
		Base oil
		with			Fuel
		additive	Anti-wear	Friction	economy	Rolling
	Base oil	package	agent	modifier I	agent	Speed	Traction
	(wt. %)	(wt. %)	(wt. %)	(wt. %)	(wt. %)	(mm/s)	Coeff.
Ex. 87	100	—	—	—	—	0.962	0.0158
Ex. 88	100	—	—	—	—	1.677	0.1029
Ex. 89	100	—	—	—	—	3.013	0.1033
Ex. 90	100	—	—	—	—	3.8	0.10433
Ex. 91	100	—	—	—	—	5.115	0.1078
Ex. 92	100	—	—	—	—	5.405	0.1162
Ex. 93	100	—	—	—	—	7.042	0.1104
Ex. 94	100	—	—	—	—	7.929	0.1184
Ex. 95	100	—	—	—	—	9.056	0.1102
Ex. 96	100	—	—	—	—	9.667	0.1166
Ex. 97	100	—	—	—	—	19.897	0.0847
Ex. 98	100	—	—	—	—	30.435	0.0811
Ex. 99	100	—	—	—	—	39.999	0.074
Ex. 100	100	—	—	—	—	50.195	0.0601
Ex. 101	100	—	—	—	—	59.658	0.0625
Ex. 102	100	—	—	—	—	70.085	0.0622
Ex. 103	100	—	—	—	—	80.296	0.0582
Ex. 104	100	—	—	—	—	89.799	0.0568
Ex. 105	100	—	—	—	—	100.296	0.0586
Ex. 106	100	—	—	—	—	200.254	0.0457
Ex. 107	100	—	—	—	—	299.662	0.0391
Ex. 108	100	—	—	—	—	400.033	0.0346
Ex. 109	100	—	—	—	—	500.059	0.0309
Ex. 110	100	—	—	—	—	600.25	0.0276
Ex. 111	100	—	—	—	—	699.664	0.0257
Ex. 112	100	—	—	—	—	799.768	0.0245
Ex. 113	100	—	—	—	—	900.358	0.0234
Ex. 114	100	—	—	—	—	1000.968	0.0223
Ex. 115	100	—	—	—	—	1100.521	0.0214
Ex. 116	100	—	—	—	—	1200.297	0.0206
Ex. 117	100	—	—	—	—	1299.564	0.0198
Ex. 118	100	—	—	—	—	1400.009	0.0191
Ex. 119	100	—	—	—	—	1500.357	0.0187
Ex. 120	100	—	—	—	—	1600.239	0.0182
Ex. 121	100	—	—	—	—	1700.373	0.0178
Ex. 122	100	—	—	—	—	1799.935	0.0174
Ex. 123	100	—	—	—	—	1900.163	0.0171
Ex. 124	100	—	—	—	—	1999.889	0.0168
Ex. 125	99.5	—	—	0.5	—	0.949	−0.0016
Ex. 126	99.5	—	—	0.5	—	1.989	0.05
Ex. 127	99.5	—	—	0.5	—	2.882	0.0998
Ex. 128	99.5	—	—	0.5	—	3.891	0.088
Ex. 129	99.5	—	—	0.5	—	5.193	0.0951
Ex. 130	99.5	—	—	0.5	—	6.147	0.0929
Ex. 131	99.5	—	—	0.5	—	7.01	0.0872
Ex. 132	99.5	—	—	0.5	—	8.011	0.0849
Ex. 133	99.5	—	—	0.5	—	9.461	0.0823
Ex. 134	99.5	—	—	0.5	—	9.984	0.0785
Ex. 135	99.5	—	—	0.5	—	19.664	0.0778
Ex. 136	99.5	—	—	0.5	—	29.561	0.0659
Ex. 137	99.5	—	—	0.5	—	39.263	0.064
Ex. 138	99.5	—	—	0.5	—	49.865	0.0628
Ex. 139	99.5	—	—	0.5	—	59.777	0.0591
Ex. 140	99.5	—	—	0.5	—	69.944	0.055
Ex. 141	99.5	—	—	0.5	—	81.048	0.0552
Ex. 142	99.5	—	—	0.5	—	90.596	0.0541
Ex. 143	99.5	—	—	0.5	—	99.734	0.0537
Ex. 144	99.5	—	—	0.5	—	200.362	0.0505
Ex. 145	99.5	—	—	0.5	—	300.581	0.0459
Ex. 146	99.5	—	—	0.5	—	399.704	0.0405
Ex. 147	99.5	—	—	0.5	—	500.203	0.0297
Ex. 148	99.5	—	—	0.5	—	600.131	0.026
Ex. 149	99.5	—	—	0.5	—	700.143	0.023
Ex. 150	99.5	—	—	0.5	—	800.486	0.0211
Ex. 151	99.5	—	—	0.5	—	899.639	0.0197
Ex. 152	99.5	—	—	0.5	—	1000.152	0.0186
Ex. 153	99.5	—	—	0.5	—	1099.66	0.0182
Ex. 154	99.5	—	—	0.5	—	1199.611	0.0177
Ex. 155	99.5	—	—	0.5	—	1300.467	0.0172
Ex. 156	99.5	—	—	0.5	—	1400.157	0.0167
Ex. 157	99.5	—	—	0.5	—	1500.177	0.0163
Ex. 158	99.5	—	—	0.5	—	1600.206	0.016
Ex. 159	99.5	—	—	0.5	—	1699.844	0.0158
Ex. 160	99.5	—	—	0.5	—	1799.844	0.0156
Ex. 161	99.5	—	—	0.5	—	1899.764	0.0153
Ex. 162	99.5	—	—	0.5	—	2000.249	0.0151
Ex. 163	99.5	—	—	—	0.5	1.092	0.011
Ex. 164	99.5	—	—	—	0.5	1.934	0.03
Ex. 165	99.5	—	—	—	0.5	2.961	0.0595
Ex. 166	99.5	—	—	—	0.5	4.092	0.0552
Ex. 167	99.5	—	—	—	0.5	4.815	0.0757
Ex. 168	99.5	—	—	—	0.5	6.335	0.0746
Ex. 169	99.5	—	—	—	0.5	7.213	0.0734
Ex. 170	99.5	—	—	—	0.5	8.136	0.0702
Ex. 171	99.5	—	—	—	0.5	9.169	0.0708
Ex. 172	99.5	—	—	—	0.5	10.071	0.0729
Ex. 173	99.5	—	—	—	0.5	20.335	0.068
Ex. 174	99.5	—	—	—	0.5	30.159	0.0648
Ex. 175	99.5	—	—	—	0.5	40.4	0.062
Ex. 176	99.5	—	—	—	0.5	49.618	0.0557
Ex. 177	99.5	—	—	—	0.5	60.643	0.0523
Ex. 178	99.5	—	—	—	0.5	70.061	0.0516
Ex. 179	99.5	—	—	—	0.5	78.409	0.0473
Ex. 180	99.5	—	—	—	0.5	89.589	0.0446
Ex. 181	99.5	—	—	—	0.5	100.523	0.042
Ex. 182	99.5	—	—	—	0.5	200.258	0.0272
Ex. 183	99.5	—	—	—	0.5	300.799	0.0222
Ex. 184	99.5	—	—	—	0.5	399.724	0.0204
Ex. 185	99.5	—	—	—	0.5	500.002	0.0193
Ex. 186	99.5	—	—	—	0.5	600.839	0.0187
Ex. 187	99.5	—	—	—	0.5	700.435	0.0182
Ex. 188	99.5	—	—	—	0.5	799.378	0.0176
Ex. 189	99.5	—	—	—	0.5	899.755	0.0173
Ex. 190	99.5	—	—	—	0.5	1000.626	0.0168
Ex. 191	99.5	—	—	—	0.5	1100.092	0.0165
Ex. 192	99.5	—	—	—	0.5	1200.543	0.0162
Ex. 193	99.5	—	—	—	0.5	1299.109	0.0159
Ex. 194	99.5	—	—	—	0.5	1400.676	0.0156
Ex. 195	99.5	—	—	—	0.5	1499.969	0.0154
Ex. 196	99.5	—	—	—	0.5	1600.312	0.0152
Ex. 197	99.5	—	—	—	0.5	1699.875	0.0151
Ex. 198	99.5	—	—	—	0.5	1799.9	0.0149
Ex. 199	99.5	—	—	—	0.5	1899.832	0.0148
Ex. 200	99.5	—	—	—	0.5	1999.948	0.0147
Ex. 201	99.92	—	0.08	—	—	0.998	−0.0382
Ex. 202	99.92	—	0.08	—	—	1.981	0.0433
Ex. 203	99.92	—	0.08	—	—	3.09	0.0114
Ex. 204	99.92	—	0.08	—	—	4.067	0.0745
Ex. 205	99.92	—	0.08	—	—	5.155	0.1139
Ex. 206	99.92	—	0.08	—	—	5.823	0.1137
Ex. 207	99.92	—	0.08	—	—	6.766	0.115
Ex. 208	99.92	—	0.08	—	—	8.003	0.1113
Ex. 209	99.92	—	0.08	—	—	8.949	0.1191
Ex. 210	99.92	—	0.08	—	—	9.94	0.1195
Ex. 211	99.92	—	0.08	—	—	19.993	0.1121
Ex. 212	99.92	—	0.08	—	—	29.823	0.1099
Ex. 213	99.92	—	0.08	—	—	39.196	0.1104
Ex. 214	99.92	—	0.08	—	—	49.696	0.107
Ex. 215	99.92	—	0.08	—	—	60.12	0.1057
Ex. 216	99.92	—	0.08	—	—	69.925	0.1022
Ex. 217	99.92	—	0.08	—	—	79.972	0.1022
Ex. 218	99.92	—	0.08	—	—	89.122	0.0992
Ex. 219	99.92	—	0.08	—	—	99.381	0.0999
Ex. 220	99.92	—	0.08	—	—	199.857	0.0866
Ex. 221	99.92	—	0.08	—	—	300.272	0.0801
Ex. 222	99.92	—	0.08	—	—	400.761	0.0709
Ex. 223	99.92	—	0.08	—	—	500.016	0.0625
Ex. 224	99.92	—	0.08	—	—	600.159	0.0582
Ex. 225	99.92	—	0.08	—	—	700.005	0.0561
Ex. 226	99.92	—	0.08	—	—	799.183	0.055
Ex. 227	99.92	—	0.08	—	—	900.07	0.0541
Ex. 228	99.92	—	0.08	—	—	1000.144	0.0534
Ex. 229	99.92	—	0.08	—	—	1100.143	0.0529
Ex. 230	99.92	—	0.08	—	—	1199.947	0.0525
Ex. 231	99.92	—	0.08	—	—	1299.983	0.0521
Ex. 232	99.92	—	0.08	—	—	1400.134	0.0516
Ex. 233	99.92	—	0.08	—	—	1499.927	0.0514
Ex. 234	99.92	—	0.08	—	—	1599.967	0.0509
Ex. 235	99.92	—	0.08	—	—	1699.728	0.0506
Ex. 236	99.92	—	0.08	—	—	1799.952	0.0506
Ex. 237	99.92	—	0.08	—	—	1899.795	0.0501
Ex. 238	99.92	—	0.08	—	—	2000.191	0.0493
Ex. 239	99.42	—	0.08	0.5	—	0.968	0.0128
Ex. 240	99.42	—	0.08	0.5	—	2.082	0.06
Ex. 241	99.42	—	0.08	0.5	—	2.951	0.06
Ex. 242	99.42	—	0.08	0.5	—	3.543	0.0613
Ex. 243	99.42	—	0.08	0.5	—	4.822	0.072
Ex. 244	99.42	—	0.08	0.5	—	5.747	0.0631
Ex. 245	99.42	—	0.08	0.5	—	7.162	0.0596
Ex. 246	99.42	—	0.08	0.5	—	7.964	0.0726
Ex. 247	99.42	—	0.08	0.5	—	9.393	0.0653
Ex. 248	99.42	—	0.08	0.5	—	10.077	0.0623
Ex. 249	99.42	—	0.08	0.5	—	19.795	0.0514
Ex. 250	99.42	—	0.08	0.5	—	30.625	0.0474
Ex. 251	99.42	—	0.08	0.5	—	39.887	0.0462
Ex. 252	99.42	—	0.08	0.5	—	49.646	0.046
Ex. 253	99.42	—	0.08	0.5	—	59.844	0.0436
Ex. 254	99.42	—	0.08	0.5	—	69.66	0.0416
Ex. 255	99.42	—	0.08	0.5	—	79.606	0.0403
Ex. 256	99.42	—	0.08	0.5	—	89.916	0.0414
Ex. 257	99.42	—	0.08	0.5	—	101.33	0.042
Ex. 258	99.42	—	0.08	0.5	—	199.705	0.0451
Ex. 259	99.42	—	0.08	0.5	—	300.217	0.0447
Ex. 260	99.42	—	0.08	0.5	—	400.016	0.0431
Ex. 261	99.42	—	0.08	0.5	—	499.984	0.04
Ex. 262	99.42	—	0.08	0.5	—	600.592	0.0372
Ex. 263	99.42	—	0.08	0.5	—	700.426	0.0344
Ex. 264	99.42	—	0.08	0.5	—	799.998	0.0319
Ex. 265	99.42	—	0.08	0.5	—	899.399	0.0294
Ex. 266	99.42	—	0.08	0.5	—	999.906	0.0272
Ex. 267	99.42	—	0.08	0.5	—	1100.165	0.0246
Ex. 268	99.42	—	0.08	0.5	—	1199.845	0.0221
Ex. 269	99.42	—	0.08	0.5	—	1299.45	0.0208
Ex. 270	99.42	—	0.08	0.5	—	1399.648	0.0198
Ex. 271	99.42	—	0.08	0.5	—	1500.139	0.019
Ex. 272	99.42	—	0.08	0.5	—	1599.762	0.0183
Ex. 273	99.42	—	0.08	0.5	—	1699.628	0.0178
Ex. 274	99.42	—	0.08	0.5	—	1800.018	0.0172
Ex. 275	99.42	—	0.08	0.5	—	1900.062	0.017
Ex. 276	99.42	—	0.08	0.5	—	1999.752	0.0166
Ex. 277	99.42	—	0.08	—	0.5	1.01	−0.0295
Ex. 278	99.42	—	0.08	—	0.5	2.139	0.0503
Ex. 279	99.42	—	0.08	—	0.5	3.01	0.06
Ex. 280	99.42	—	0.08	—	0.5	3.517	0.1155
Ex. 281	99.42	—	0.08	—	0.5	5.01	0.1313
Ex. 282	99.42	—	0.08	—	0.5	6.098	0.1264
Ex. 283	99.42	—	0.08	—	0.5	7.166	0.1084
Ex. 284	99.42	—	0.08	—	0.5	8.218	0.1347
Ex. 285	99.42	—	0.08	—	0.5	8.971	0.1227
Ex. 286	99.42	—	0.08	—	0.5	9.661	0.126
Ex. 287	99.42	—	0.08	—	0.5	19.994	0.1077
Ex. 288	99.42	—	0.08	—	0.5	30.248	0.0892
Ex. 289	99.42	—	0.08	—	0.5	39.726	0.0851
Ex. 290	99.42	—	0.08	—	0.5	50.022	0.0769
Ex. 291	99.42	—	0.08	—	0.5	60.777	0.07
Ex. 292	99.42	—	0.08	—	0.5	70.601	0.0691
Ex. 293	99.42	—	0.08	—	0.5	80.435	0.0632
Ex. 294	99.42	—	0.08	—	0.5	90.376	0.0573
Ex. 295	99.42	—	0.08	—	0.5	98.829	0.0578
Ex. 296	99.42	—	0.08	—	0.5	200.266	0.0384
Ex. 297	99.42	—	0.08	—	0.5	299.232	0.0294
Ex. 298	99.42	—	0.08	—	0.5	400.699	0.0244
Ex. 299	99.42	—	0.08	—	0.5	499.802	0.0213
Ex. 300	99.42	—	0.08	—	0.5	599.696	0.0195
Ex. 301	99.42	—	0.08	—	0.5	700.453	0.0182
Ex. 302	99.42	—	0.08	—	0.5	799.721	0.0172
Ex. 303	99.42	—	0.08	—	0.5	900.499	0.0166
Ex. 304	99.42	—	0.08	—	0.5	999.852	0.0161
Ex. 305	99.42	—	0.08	—	0.5	1099.712	0.0156
Ex. 306	99.42	—	0.08	—	0.5	1199.554	0.0153
Ex. 307	99.42	—	0.08	—	0.5	1299.555	0.0151
Ex. 308	99.42	—	0.08	—	0.5	1400.34	0.0148
Ex. 309	99.42	—	0.08	—	0.5	1500.271	0.0146
Ex. 310	99.42	—	0.08	—	0.5	1599.869	0.0144
Ex. 311	99.42	—	0.08	—	0.5	1699.814	0.0142
Ex. 312	99.42	—	0.08	—	0.5	1800.113	0.014
Ex. 313	99.42	—	0.08	—	0.5	1899.877	0.014
Ex. 314	99.42	—	0.08	—	0.5	2000.132	0.014
Ex. 315	—	99.92	0.08	—	—	0.995	−0.0266
Ex. 316	—	99.92	0.08	—	—	2.126	0.0419
Ex. 317	—	99.92	0.08	—	—	3.029	−0.0178
Ex. 318	—	99.92	0.08	—	—	4.486	0.0436
Ex. 319	—	99.92	0.08	—	—	4.549	0.072
Ex. 320	—	99.92	0.08	—	—	5.818	0.1085
Ex. 321	—	99.92	0.08	—	—	6.79	0.115
Ex. 322	—	99.92	0.08	—	—	8.098	0.1076
Ex. 323	—	99.92	0.08	—	—	8.928	0.105
Ex. 324	—	99.92	0.08	—	—	10.136	0.1055
Ex. 325	—	99.92	0.08	—	—	19.869	0.0984
Ex. 326	—	99.92	0.08	—	—	29.702	0.078
Ex. 327	—	99.92	0.08	—	—	39.919	0.0766
Ex. 328	—	99.92	0.08	—	—	50.076	0.0752
Ex. 329	—	99.92	0.08	—	—	60.442	0.072
Ex. 330	—	99.92	0.08	—	—	69.47	0.0697
Ex. 331	—	99.92	0.08	—	—	79.842	0.0697
Ex. 332	—	99.92	0.08	—	—	90.06	0.0673
Ex. 333	—	99.92	0.08	—	—	99.358	0.0665
Ex. 334	—	99.92	0.08	—	—	201.009	0.0543
Ex. 335	—	99.92	0.08	—	—	300.042	0.0476
Ex. 336	—	99.92	0.08	—	—	401.2	0.0434
Ex. 337	—	99.92	0.08	—	—	499.924	0.0404
Ex. 338	—	99.92	0.08	—	—	599.516	0.038
Ex. 339	—	99.92	0.08	—	—	699.622	0.0358
Ex. 340	—	99.92	0.08	—	—	800.535	0.0339
Ex. 341	—	99.92	0.08	—	—	900.402	0.0323
Ex. 342	—	99.92	0.08	—	—	999.932	0.0308
Ex. 343	—	99.92	0.08	—	—	1100.061	0.0294
Ex. 344	—	99.92	0.08	—	—	1200.049	0.0281
Ex. 345	—	99.92	0.08	—	—	1300.53	0.027
Ex. 346	—	99.92	0.08	—	—	1399.517	0.026
Ex. 347	—	99.92	0.08	—	—	1499.903	0.025
Ex. 348	—	99.92	0.08	—	—	1600.511	0.0242
Ex. 349	—	99.92	0.08	—	—	1699.766	0.0234
Ex. 350	—	99.92	0.08	—	—	1799.715	0.0226
Ex. 351	—	99.92	0.08	—	—	1900.233	0.022
Ex. 352	—	99.92	0.08	—	—	1999.653	0.0215
Ex. 353	—	99.42	0.08	0.5	—	0.981	0.0139
Ex. 354	—	99.42	0.08	0.5	—	2.11	0.0084
Ex. 355	—	99.42	0.08	0.5	—	3.164	0.0659
Ex. 356	—	99.42	0.08	0.5	—	4.289	0.1201
Ex. 357	—	99.42	0.08	0.5	—	5.329	0.0989
Ex. 358	—	99.42	0.08	0.5	—	5.88	0.1219
Ex. 359	—	99.42	0.08	0.5	—	7.336	0.115
Ex. 360	—	99.42	0.08	0.5	—	8.356	0.1177
Ex. 361	—	99.42	0.08	0.5	—	8.958	0.1071
Ex. 362	—	99.42	0.08	0.5	—	10.261	0.105
Ex. 363	—	99.42	0.08	0.5	—	20.472	0.0916
Ex. 364	—	99.42	0.08	0.5	—	29.983	0.0915
Ex. 365	—	99.42	0.08	0.5	—	39.756	0.0897
Ex. 366	—	99.42	0.08	0.5	—	49.896	0.0829
Ex. 367	—	99.42	0.08	0.5	—	60.301	0.0799
Ex. 368	—	99.42	0.08	0.5	—	69.536	0.0812
Ex. 369	—	99.42	0.08	0.5	—	79.903	0.0783
Ex. 370	—	99.42	0.08	0.5	—	90.371	0.0764
Ex. 371	—	99.42	0.08	0.5	—	99.592	0.0743
Ex. 372	—	99.42	0.08	0.5	—	200.567	0.0602
Ex. 373	—	99.42	0.08	0.5	—	299.461	0.0545
Ex. 374	—	99.42	0.08	0.5	—	400.511	0.0489
Ex. 375	—	99.42	0.08	0.5	—	500.106	0.0446
Ex. 376	—	99.42	0.08	0.5	—	600.226	0.0413
Ex. 377	—	99.42	0.08	0.5	—	700.554	0.0385
Ex. 378	—	99.42	0.08	0.5	—	800.185	0.0362
Ex. 379	—	99.42	0.08	0.5	—	899.774	0.0341
Ex. 380	—	99.42	0.08	0.5	—	999.701	0.0324
Ex. 381	—	99.42	0.08	0.5	—	1100.55	0.0309
Ex. 382	—	99.42	0.08	0.5	—	1199.651	0.0294
Ex. 383	—	99.42	0.08	0.5	—	1299.973	0.0282
Ex. 384	—	99.42	0.08	0.5	—	1399.995	0.027
Ex. 385	—	99.42	0.08	0.5	—	1499.916	0.026
Ex. 386	—	99.42	0.08	0.5	—	1599.649	0.0251
Ex. 387	—	99.42	0.08	0.5	—	1699.539	0.0243
Ex. 388	—	99.42	0.08	0.5	—	1800.048	0.0237
Ex. 389	—	99.42	0.08	0.5	—	1899.699	0.0229
Ex. 390	—	99.42	0.08	0.5	—	1999.722	0.0223
Ex. 391	—	99.42	0.08	—	0.5	0.972	0.016
Ex. 392	—	99.42	0.08	—	0.5	1.989	−0.0398
Ex. 393	—	99.42	0.08	—	0.5	3.093	0.0272
Ex. 394	—	99.42	0.08	—	0.5	3.81	0.0674
Ex. 395	—	99.42	0.08	—	0.5	5.287	0.0479
Ex. 396	—	99.42	0.08	—	0.5	5.994	0.1307
Ex. 397	—	99.42	0.08	—	0.5	6.401	0.1235
Ex. 398	—	99.42	0.08	—	0.5	8.28	0.1223
Ex. 399	—	99.42	0.08	—	0.5	8.803	0.125
Ex. 400	—	99.42	0.08	—	0.5	9.711	0.1189
Ex. 401	—	99.42	0.08	—	0.5	20.279	0.1092
Ex. 402	—	99.42	0.08	—	0.5	30.583	0.1117
Ex. 403	—	99.42	0.08	—	0.5	39.219	0.1038
Ex. 404	—	99.42	0.08	—	0.5	49.983	0.0937
Ex. 405	—	99.42	0.08	—	0.5	59.881	0.094
Ex. 406	—	99.42	0.08	—	0.5	69.946	0.0925
Ex. 407	—	99.42	0.08	—	0.5	78.827	0.0886
Ex. 408	—	99.42	0.08	—	0.5	90.666	0.0879
Ex. 409	—	99.42	0.08	—	0.5	99.16	0.0856
Ex. 410	—	99.42	0.08	—	0.5	200.997	0.0692
Ex. 411	—	99.42	0.08	—	0.5	299.773	0.0605
Ex. 412	—	99.42	0.08	—	0.5	399.718	0.0545
Ex. 413	—	99.42	0.08	—	0.5	499.974	0.0502
Ex. 414	—	99.42	0.08	—	0.5	599.895	0.0463
Ex. 415	—	99.42	0.08	—	0.5	700.405	0.0432
Ex. 416	—	99.42	0.08	—	0.5	800.176	0.0405
Ex. 417	—	99.42	0.08	—	0.5	899.676	0.0382
Ex. 418	—	99.42	0.08	—	0.5	1000.108	0.036
Ex. 419	—	99.42	0.08	—	0.5	1099.482	0.0342
Ex. 420	—	99.42	0.08	—	0.5	1200.132	0.0326
Ex. 421	—	99.42	0.08	—	0.5	1299.578	0.0311
Ex. 422	—	99.42	0.08	—	0.5	1399.476	0.0298
Ex. 423	—	99.42	0.08	—	0.5	1499.769	0.0285
Ex. 424	—	99.42	0.08	—	0.5	1600.026	0.0274
Ex. 425	—	99.42	0.08	—	0.5	1700.468	0.0265
Ex. 426	—	99.42	0.08	—	0.5	1799.821	0.0256
Ex. 427	—	99.42	0.08	—	0.5	1899.981	0.0248
Ex. 428	—	99.42	0.08	—	0.5	2000.19	0.024

In FIG. 1, the traction coefficients for each of the lubricant compositions are plotted against the corresponding rolling speeds from 200 mm/s to 2000 mm/s as provided in Table 3 above. Lubricant compositions including the mixture of the alkoxylated amide and the ester (fuel economy agent) and the anti-wear agent including phosphorous exhibit lower traction coefficients at rolling speeds of at least 200 mm/s as compared to lubricant compositions including glycerol mono oleate (friction modifier I) and the anti-wear agent including phosphorous. At rolling speeds of less than 200 mm/s, the traction coefficients for the lubricant compositions including glycerol mono oleate (friction modifier I) and the anti-wear agent including phosphorous exhibit lower traction coefficients as compared to lubricant compositions including the mixture of the alkoxylated amide and the ester (fuel economy agent), and the anti-wear agent including phosphorous..

D. Fuel Economy Evaluation According to EPA Highway Fuel Economy Driving Schedule (HwFET)

The fuel economy improvement for vehicles utilizing lubricant composition was determined according to HwFET which is a chassis dynamometer driving schedule developed by the U.S. EPA for the determination of fuel economy of light duty vehicles. A 2012 Honda Civic (1.8L PFI), a 2004 Mazda 3 (2.0L PFI), a 2012 Buick Regal (2.0L GDI), and a 2012 Ford Explorer (2.0L TGDI) were utilized for the determination.

A total of four cycles were averaged to calculate the baseline fuel economy for each vehicle with each cycle including two HwFETs for a total of eight measurements. A mixture of the alkoxylated amide and ester, or an ester free of nitrogen was then introduced into the lubricant composition at the specified treat rate and four additional cycles were measured to calculate the impact of the mixture of the alkoxylated amide and ester, or the ester that is free of nitrogen on fuel economy. In accordance with HwFET, each vehicle was tested for 765 seconds to a distance of 10.26 miles at an average speed of 48.3 miles per hour. The results in Table 3 for each vehicle utilizing each lubricant composition are based on an average of 6 tests.

Examples 429-436 include the anti-wear agent including phosphorous, the ester free of nitrogen, and a Group II base oil. Examples 437-444 include an anti-wear agent including phosphorous, a mixture of the alkoxylated amide and ester, and a Group II base oil. Examples 437-444 also include a minor amount of by-products resulting and reactants remaining from the preparation of the alkoxylated amide of general formula (I) and the ester of general formula (II).

The Group II base oil of Examples 429-444 also includes an additive package including each of the following additives in an amount based on a total weight percent of the Group II base oil: a dispersant at 3.4 wt. %, a phenolic antioxidant at 0.85 wt. %, an aminic antioxidant at 1.4 wt. %, a detergent at 1.8 wt. %, a diluent at 1 wt. %, a viscosity index improver at 3.2 wt. %, a pour point depressant, and antifoam agent.

The anti-wear agent including phosphorous is zinc dialkyldithiophosphate. The ester free of nitrogen is glycerol mono oleate. The mixture of alkoxylated amide and ester includes the alkoxylated amide and the ester in a weight ratio of 75:25 of the ester to the alkoxylated amide. Descriptions of the formulations of Examples of 87-102 are provided in Table 4 below. Results of the testing of Examples of 87-102 are provided in Table 5 below.

	TABLE 4
		Anti-wear		Mixture of
		agent	Ester	the alkoxyl-
	Base	including	free of	ated amide	Additive
	oil	phosphorous	nitrogen	and ester	package
	(wt. %)	(wt. %)	(wt. %)	(wt. %)	(wt. %)
Example 429	88.734	0.075	0.3	—	10.891
Example 430	88.734	0.075	0.3	—	10.891
Example 431	88.734	0.075	0.3	—	10.891
Example 432	88.734	0.075	0.3	—	10.891
Example 433	88.434	0.075	0.6	—	10.891
Example 434	88.434	0.075	0.6	—	10.891
Example 435	88.434	0.075	0.6	—	10.891
Example 436	88.434	0.075	0.6	—	10.891
Example 437	88.734	0.075	—	0.3	10.891
Example 438	88.734	0.075	—	0.3	10.891
Example 439	88.734	0.075	—	0.3	10.891
Example 440	88.734	0.075	—	0.3	10.891
Example 441	88.434	0.075	—	0.6	10.891
Example 442	88.434	0.075	—	0.6	10.891
Example 443	88.434	0.075	—	0.6	10.891
Example 444	88.434	0.075	—	0.6	10.891

	TABLE 5
		Fuel Economy	Average Fuel
		Increase	Economy Increase
	Vehicle	(%)	(%)
Example 429	Mazda	1.53	0.50
Example 430	Regal	0.11
Example 431	Civic	0.07
Example 432	Explorer	0.30
Example 433	Mazda	1.19	0.73
Example 434	Regal	0.66
Example 435	Civic	0.07
Example 436	Explorer	0.98
Example 437	Mazda	1.30	1.36
Example 438	Regal	1.17
Example 439	Civic	1.68
Example 440	Explorer	1.27
Example 441	Mazda	1.96	1.45
Example 442	Regal	1.00
Example 443	Civic	1.62
Example 444	Explorer	1.23

Lubricant compositions including the ester free of nitrogen at 0.30 wt. % based on total weight of the lubricant composition exhibited increased fuel economy by an average of 0.50% as compared to the lubricant compositions free of the ester free of nitrogen as measured by the HwFET. Lubricant compositions including the mixture of the alkoxylated amide and ester at 0.30 wt. % based on total weight of the lubricant composition exhibited increased fuel economy by an average of 1.36% as compared to the lubricant compositions free of the mixture of the alkoxylated amide and ester as measured by the HwFET.

Lubricant compositions including the ester free of nitrogen at 0.60 wt. % based on total weight of the lubricant composition exhibited increased fuel economy by an average of 0.73% as compared to the lubricant compositions free of the ester free of nitrogen as measured by the HwFET. Lubricant compositions including the mixture of the alkoxylated amide and ester at 0.60 wt. % based on total weight of the lubricant composition exhibited increased fuel economy by an average of 1.45% as compared to the lubricant compositions free of the mixture of the alkoxylated amide and ester as measured by the HwFET.

E. Fuel Consumption Evaluation by Engine Dynamometer

The fuel consumption evaluation by engine dynamometer was conducted on an engine utilizing a lubricant composition.

The fuel consumption evaluation provides fuel consumption results at several time points over a 67.81 hour period. The engine utilized for the evaluation was a 5.7 liter GM crate engine. The engine was operated at controlled steady state conditions simulating highway temperatures, speed, and load. Fuel consumption was measured constantly with a Coriolis-type fuel flow meter.

At 0 hours, the lubricant composition included only Group II base oil. The engine was operated until the fuel consumption stabilized at 14.41 hours. This period from 0 hours to 14.41 hours is described as the “aging period.” At 14.41 hours, an anti-wear agent including phosphorous in an amount of 0.03 wt. % was added to the lubricant composition such that the lubricant composition included the Group II base oil in combination with the anti-wear agent including phosphorous. At 17.08 hours, a mixture of the alkoxylated amide and ester in an amount of 0.3 wt. % was added to the lubricant composition such that the lubricant composition included the Group II base oil, the anti-wear agent including phosphorous and the mixture of the alkoxylated amide and ester.

The anti-wear agent including phosphorous was zinc dialkyldithiophosphate. The mixture of the alkoxylated amide and ester is a mixture of the alkoxylated amide of general formula (I) and the ester of general formula (II) along with a minor amount of by-products resulting and reactants remaining from the preparation of the alkoxylated amide of general formula (I) and the ester of general formula (II). The mixture of alkoxylated amide and ester includes the alkoxylated amide and the ester in a weight ratio of 75:25 of the ester to the alkoxylated amide. Results of the evaluation are provided in Table 6 below and graphically in FIG. 2.

	TABLE 6
	Lubricant Composition
Time		Anti-wear agent	Mixture of the	Fuel
point/Time	Base	including	alkoxylated	Consumption
period	oil	phosphorous	amide and ester	(g/sec)
A/0 to	Yes	No	No	2.388
14.41 hours
B/14.41 to	Yes	Yes	No	2.458
17.08 hours
C/17.08 to	Yes	Yes	Yes	2.392
19.58 hours
D/19.58 to	Yes	Yes	Yes	2.307
67.81 hours

As shown in Table 6 and FIG. 2, during the aging period from 0 hours to 14.41 hours (time point A at 14.41 hours), fuel consumption of the engine stabilized at 2.388 g/sec. After addition of the anti-wear agent including phosphorous to the lubricant composition, fuel consumption of the engine was 2.458 g/sec at 17.08 hours (time point B at 17.08 hours). This addition of the anti-wear agent including phosphorous resulted in an increase of fuel consumption of 2.85% relative to the lubricant composition of the aging period. After addition of the mixture of the alkoxylated amide and ester to the lubricant composition, fuel consumption of the engine was 2.392 g/sec at 19.58 hours (time point C at 19.58 hours). Thus, the addition of the mixture of the alkoxylated amide and ester resulted in a decrease of fuel consumption of 2.76% compared to the lubricant composition without the mixture of the alkoxylated amide and ester. After 67.81 hours (time point D at 67.81 hours), fuel consumption of the engine was 2.307 g/sec.

The fuel consumption of the engine at 67.81 hours utilizing the lubricant composition that included the anti-wear agent including phosphorous, and the mixture of the alkoxylated amide and the ester, decreased 3.51% compared to the fuel consumption of the engine at 14.41 hours utilizing the lubricant composition that included only the anti-wear agent including phosphorous. The fuel consumption of the engine at 67.81 hours utilizing the lubricant composition decreased 6.55% compared to the fuel consumption of the engine at 17.08 hours. It is believed that the mixture of the alkoxylated amide and ester in the lubricant composition including the anti-wear agent including phosphorous mitigates the increased fuel consumption of the engine utilizing a lubricant composition including the anti-wear agent including phosphorous.

In addition to the Fuel Consumption Evaluation by Engine Dynamometer described above, a further Fuel Consumption Evaluation by Engine Dynamometer was conducted. During this evaluation, the mixture of the alkoxylated amide and the ester was added to the lubricant composition after the aging period. After 3 hours, the anti-wear agent including phosphorus was added to the lubricant composition. The results of this evaluation provided that the fuel consumption of the engine only increased after addition of the anti-wear agent including phosphorus. Without intending to be bound by theory, it is believed that the performance of the alkoxylated amide and the ester may be dependent upon the presence of a tribofilm formed from the anti-wear agent including phosphorus.

F. Effectiveness of Bench Tests in Determining Fuel Economy

The evaluations described above utilizing HFRR and MTM for determining concepts related to friction are commonly considered to be bench tests. These tests may be utilized to quickly and cost-effectively screen a large number of lubricant compositions for concepts related to friction. However, looking at the evaluations described above as a whole, concepts related to friction may not necessarily correlate to fuel economy. For example, if one were to only evaluate a lubricant composition including glycerol mono oleate against a lubricant composition including the mixture of the alkoxylated amide and ester utilizing bench tests, one may incorrectly determine that lubricant compositions including glycerol mono oleate exhibit increased fuel economy based on concepts related to friction as compared to lubricant compositions including the mixture of the alkoxylated amide and ester. In view of the HwFET evaluation describe above, which is commonly utilized by OEMs to determine the fuel economy of vehicles, the lubricant composition including the mixture of the alkoxylated amide and ester exhibits increased fuel economy in engines as compared to the lubricant composition including glycerol mono oleate in engines.

It is believed that bench tests which screen lubricant compositions for concepts related to friction may be unable to simulate the complex environment of an operating engine due to bench tests only simulating one set of conditions. The complex environment of an engine includes many moving parts all moving at different speeds, each of the parts with different metallurgy, hardness, stiffness, and geometry with these parts contacting with varying loads and temperatures and with different degrees of boundary lubrication and transient conditions. Further, the lubricant composition is continuously changing as it ages due to heat, the accumulation of combustion products, and changes in chemistry as additives activate, react, and decompose. For example, an engine operating for a longer duration and at a higher temperature may be more likely to exhibit tribofilm formed from the anti-wear additive on surfaces of metal parts of the engine. As described above, it is believed that the mixture of the alkoxylated amide and ester may absorbs onto the tribofilm to reduce the friction coefficient of the layer of the anti-wear agent present on the surface of the engine. Without the formation of the tribofilm during bench tests, the alkoxylated amide and ester may not reduce the friction coefficient of the layer of the anti-wear agent present on the surface of the engine. Accordingly, it is believed that bench tests which screen lubricant compositions for concepts related to friction may not be an effective method of determining the fuel economy of a lubricant composition in an engine.

Evaluation of Racing Oil Compositions Including the Base Oil, the Alkoxylated Amide, the Ester, and the Anti-Wear Agent

Five racing oil compositions were prepared as shown below as Examples A-E in Table 7. Additionally, four comparative racing oil compositions were prepared as shown below as Comparative Examples F-J in Table 7. The value for each individual component is the wt. % of the component based on the total weight of the respective composition.

	TABLE 7
	Friction Modifier
		Mixture of the		Anti-wear
		alkoxylated	Glycerol	agent including
	Base oil	amide and ester	monooleate	phosphorus
	(wt. %)	(wt. %)	(wt. %)	(wt. %)
Example A	99.3835	0.5	—	0.1165
Example B	99.2811	0.5	—	0.2189
Example C	99.1126	0.5	—	0.3874
Example D	99.2076	0.5	—	0.2924
Example E	99.3835	0.5	—	0.1165
Comparative	99.3735	—	0.5	0.1265
Example F
Comparative	99.2811	—	0.5	0.2189
Example G
Comparative	99.1126	—	0.5	0.3874
Example H
Comparative	99.3835	—	0.5	0.1165
Example I
Comparative	99.2076	—	0.5	0.2924
Example J

Example A and Comparative Example F utilized Valvoline Racing VR1 20W-50 as the base oil. Example B and Comparative Example G utilized Champion Racing Oil 15W-50 as the base oil. Example C and Comparative Example H utilized Lucas Racing Oil OW-20 as the base oil. Example D and Comparative Example J utilized Joe Gibbs Driven Racing Oil X1³1 5W-20 as the base oil. Example E and Comparative Example I utilized Royal Purple Racing Oil

XPR 5W-20 as the base oil. The alkoxylated amide in Examples A through E had the following formula:

and the ester included in Examples A through E had the following formula:

with each R¹ being, independently, a linear or branched, saturated or unsaturated, C₆-C₂₃ aliphatic hydrocarbyl group. Examples A through E included ZDDP as the anti-wear agent, and

Comparative Examples F through I included ZDDP as the Anti-Wear Agent

The impact of the pairing of the anti-wear agent and the particular friction modifier was examined by first measuring the traction coefficient of the base oil without the anti-wear agent and without the particular friction modifier (i.e., the traction coefficient of just the base oil was measured). The traction coefficient was determined by utilizing a Mini-Traction Machine (MTM), specifically MTM 2 from PCS Instruments. During the determination, standard steel ball (19.05mm) and discs (46mm) were utilized in the MTM, the load of the MTM was set to 50N, and the lubricant compositions were pre-heated to 125° C. The traction coefficient of each of the lubricant compositions was measured from speeds between 0 and 2000 mm/s utilizing a 50% slide/roll ratio. The traction coefficient pertaining to a speed of 500 mm/s was recorded to obtain the traction coefficient of the base oil. After obtaining the traction coefficient of the base oil, Examples A through E and Comparative Examples F through H were prepared as shown above in Table 7. After the examples were prepared, the traction coefficients of Examples A through E and Comparative Examples I through J were measured with the same procedure used to measure the traction coefficients of the base oil. The difference in traction coefficient for each example relative to the traction coefficient of the base oil for each example is provided below in Table 8.

	TABLE 8
		Anti-wear
		agent including	Delta in
	Racing Oil	phosphorus	Traction
	Composition	(wt. %)	Coefficient
	Example E	0.1165	0.0071
	Example A	0.1265	0.0062
	Example B	0.2189	0.0116
	Example D	0.2924	0.0204
	Example C	0.3874	0.0209
	Comparative	0.1165	0.0009
	Example I
	Comparative	0.1265	0.0107
	Example F
	Comparative	0.2189	0.0062
	Example G
	Comparative	0.3874	0.0044
	Example H
	Comparative	0.2924	−0.0062
	Example H

The difference (i.e., delta) in traction coefficient directly correlates to the effectiveness of the friction modifier. Notably, as shown in Table 8, the effectiveness of the friction modifier for Examples A through E increased as the amount of phosphorus increased. In other words, despite the fact that Examples A through E contained an identical amount of the mixture of the alkoxylated amide and ester (i.e., the friction modifier), as the amount of phosphorus was increased from the inclusion of the anti-wear agent, the effectiveness of the friction modifier increased as evidenced by the larger values representing the difference in traction coefficients. In fact, a near linear relationship is observed when the friction modifier in the mixture of the alkoxylated amide and ester. As such, Examples A through E clearly demonstrate that the effectiveness of the mixture of the alkoxylated amide and ester is increased as the amount of phosphors in the racing oil is increased (i.e., as the amount of the anti-wear agent including phosphorus is increased). The increase in effectiveness of the mixture of the alkoxylated amide and ester improves the fuel economy and horsepower of the racing vehicle lubricated with the racing oil composition. Notably, as demonstrated by Comparative Examples I through J, the increase in effectiveness of the friction modifier is not observed when the friction modifier is glycerol mono oleate. For example, despite the fact that Comparative Example H includes the largest amount of phosphorus (0.3874 wt. % of the anti-wear agent) of all the Comparative Examples, the difference in traction coefficient for Comparative Example H is smaller than the difference in traction coefficient for Comparative Examples F and G, which merely contain 0.1265 and 0.2189 wt. % of the anti-wear agent, respectively. In addition, the effectiveness of the friction modifier was negatively impacted in Comparative Example J.

It is to be understood that the appended claims are not limited to express and particular compounds, compositions, or methods described in the detailed description, which may vary between particular embodiments which fall within the scope of the appended claims. With respect to any Markush groups relied upon herein for describing particular features or aspects of various embodiments, it is to be appreciated that different, special, and/or unexpected results may be obtained from each member of the respective Markush group independent from all other Markush members. Each member of a Markush group may be relied upon individually and or in combination and provides adequate support for specific embodiments within the scope of the appended claims.

It is also to be understood that any ranges and subranges relied upon in describing various embodiments of the present disclosure independently and collectively fall within the scope of the appended claims, and are understood to describe and contemplate all ranges including whole and/or fractional values therein, even if such values are not expressly written herein. One of skill in the art readily recognizes that the enumerated ranges and subranges sufficiently describe and enable various embodiments of the present disclosure, and such ranges and subranges may be further delineated into relevant halves, thirds, quarters, fifths, and so on. As just one example, a range “of from 0.1 to 0.9” may be further delineated into a lower third, i.e., from 0.1 to 0.3, a middle third, i.e., from 0.4 to 0.6, and an upper third, i.e., from 0.7 to 0.9, which individually and collectively are within the scope of the appended claims, and may be relied upon individually and/or collectively and provide adequate support for specific embodiments within the scope of the appended claims.

In addition, with respect to the language which defines or modifies a range, such as “at least,” “greater than,” “less than,” “no more than,” and the like, it is to be understood that such language includes subranges and/or an upper or lower limit. As another example, a range of “at least 10” inherently includes a subrange of from at least 10 to 35, a subrange of from at least 10 to 25, a subrange of from 25 to 35, and so on, and each subrange may be relied upon individually and/or collectively and provides adequate support for specific embodiments within the scope of the appended claims. Finally, an individual number within a disclosed range may be relied upon and provides adequate support for specific embodiments within the scope of the appended claims. For example, a range “of from 1 to 9” includes various individual integers, such as 3, as well as individual numbers including a decimal point (or fraction), such as 4.1, which may be relied upon and provide adequate support for specific embodiments within the scope of the appended claims.

The present disclosure has been described herein in an illustrative manner, and it is to be understood that the terminology which has been used is intended to be in the nature of words of description rather than of limitation. Many modifications and variations of the present disclosure are possible in light of the above teachings. The present disclosure may be practiced otherwise than as specifically described within the scope of the appended claims. The subject matter of all combinations of independent and dependent claims, both single and multiple dependent, is herein expressly contemplated.

Claims

1-20. (canceled)

21. An additive package for a lubricant composition, said additive package comprising: an alkoxylated amide having a general formula (I):

22. The additive package of claim 21, wherein said lubricant composition is a racing oil composition.

23. The additive package of claim 21, further comprising an anti-wear agent comprising phosphorus.

24. The additive package of claim 23, wherein the anti-wear agent comprises zinc dialkyl dithiophosphate.

25. The additive package of claim 21, wherein at least one of R2 and R3of said alkoxylated amide comprises a propoxy group.

26. The additive package of claim 21, wherein R2 of said alkoxylated amide has a general formula (III):

27. The additive package of claim 21, wherein R4 has a general formula (V):

28. The additive package of claim 27, wherein R7 is a hydrocarbyl group having a general formula (VI):

29. The additive package of claim 21, wherein R1 of said alkoxylated amide and said ester are each, independently, linear or branched, saturated or unsaturated, C7-C23 aliphatic hydrocarbyl group.

30. The additive package of claim 29, wherein R1 of said alkoxylated amide or said ester comprises a hydroxyl group.

31. The additive package of claim 21, wherein said alkoxylated amide has a general formula (VIII): R1—C(═O)—N[R5—O—R6n—H][R5—O—R6m—H]  VII;andsaid ester has a general formula (IX): R1—C(═O)—O—R5—N[R5—O—R6q—H][R6p—]  (IX);

32. The additive package of claim 31, wherein each R5 is, independently, an ethyl group or a propyl group,each R6 is, independently, a propoxy group;if q is 0, p is an integer from 1 to 5, andsaid additive package comprises said alkoxylated amide and said ester in a weight ratio ofless than 70:30 of said ester to said alkoxylated amide.

33. The additive package of claim 21 comprising said alkoxylated amide and said ester in a weight ratio of less than 50:50 of said ester to said alkoxylated amide.

34. The additive package of claim 21, wherein the alkoxylated amide has the following formula:

35. The additive package of claim 21, wherein the ester has the following formula:

36. An additive package for a racing oil composition, comprising: an alkoxylated amide having the following formula:

37. The additive package of claim 36, further comprising an anti-wear agent comprising phosphorus.

38. The additive package of claim 37, wherein said anti-wear agent comprises zinc dialkyl dithiophosphate.

39. The additive package of claim 36, wherein each Rlis, independently, a linear or branched, saturated or unsaturated C6-C23 aliphatic hydrocarbyl group.

40. The additive package of claim 36 comprising said alkoxylated amide and said ester in a weight ratio of less than 50:50 of said ester to said alkoxylated amide.