Arginine derivatives and cosmetic compositions containing the same

Abstract

Emulsifier compositions capable of forming an emulsion which is stable over a wide range of temperatures and contains at least one of a N.sup..alpha. -long-chain acyl arginine higher alkyl ester of the general formula (I) or an acid-addition salt thereof: ##STR1## wherein R.sup.1 CO is a straight-chain C.sub.8-22 acyl group; and R.sup.2 is a straight-chain or branched C.sub.12-22 alkyl group, are disclosed.

Description

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to cosmetics for the skin such as milky lotions and creams, medicines for external use such as ointments, cosmetics for the hair such as shampoos, rinses, hair treatment solutions and hair conditioners, softeners, etc.

2. Discussion of the Background

Emulsifier compositions which are obtained by the emulsification of oily and aqueous components (such as a milky lotion, cream, ointment, or hair treatment solutions) are prepared by employing an appropriate mixture of a hydrophilic emulsifier and a lipophilic emulsifier, which mixture depends on the hydrophiliclipophilic balance of the oily component. More particularly, a composition containing an anionic surface active agent and a nonionic surface active agent of the ether, ester or amide type is usually employed as an emulsifier for preparing an emulsion.

It has however been very difficult to maintain the emulsifying property of such emulsifier composition at a constant level at high and low temperatures and for long periods of time. A greater deal of effort has heretofore been required for selecting appropriate component from the wide variety of emulsifiers available and employing this component in an appropriate ratio when it is mixed with the other components.

There is therfore a need for an emulsifier having improved emulsifiability.

SUMMARY OF THE INVENTION

Accordingly, it is an object of this invention to provide novel arginine derivatives which can be used to provide emulsifier compositions which can form emulsions which are stable over a wide range of temperatures.

The present invention provides arginine derivatives of the formula (I): ##STR2## wherein R.sup.1 CO is a straight-chain C.sub.8-22 acyl group; and

R.sup.2 is a straight-chain or branched C.sub.12-22 alkyl group; and salts obtained by adding an acid to the compounds of formula (I).

The arginine derivatives of formula (I) can emulsify oily and aqueous components uniformly to form a stable emulsion. They can form an O/W (oil/water) or a W/O (water/oil) emulsion as desired if the proportions of the oily and aqueous components are appropriately varied or if another appropriate emulsifier is added.

The emulsifier compositions containing the arginine derivative of this invention can be used to provide, for example, cosmetics for the skin such as milky lotions and creams, medicines for external use such as ointments, cosmetics for the hair such as shampoos, rinses, hair treatment solutions and hair conditioners, and softeners.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present arginine derivatives are particularly useful when employed in cosmetics for hair or softeners, because the arginine derivatives are adsorbed by the hair, or by fibers such as wool or cotton fibers. In these uses, the present arginine derivatives have been found to exhibit, among others, the following advantages:

(1) they remove the roughness of the hair or fibers rendering them soft to the touch;

(2) they smoothen the hair or fibers rendering them easy to comb;

(3) they prevent the generation of static electricity in the hair or fabric;

(4) they give a pleasant and oily feel, such as a smooth or moist feel; and

(5) they have a very low degree of irritability towards the skin of the head or to the eyes.

The inventors have found that an emulsifier composition can form an emulsion which is stable over a wide range of temperatures if it contains at least one of a N.sup..alpha. -long-chain acyl arginine higher alkyl ester of the general formula (I) or an acid-addition salt thereof (hereinafter referred to as the arginine derivative): ##STR3## wherein

R.sup.1 CO is a straight-chain C.sub.8-22 acyl group; and

R.sup.2 is a straight-chain or branched C.sub.12-22 alkyl group.

The arginine derivatives according to this invention are novel compounds which can be manufactured easily and at a low cost using generally known methods. For example, these compounds can be obtained if (1) a halogenated C.sub.8-22 acyl compound and arginine are condensed in the presence of a base and (2) the resulting N.sup..alpha. -long-chain acyl arginine and a primary, secondary or tertiary C.sub.12-22 alcohol are esterified in the presence of an acid catalyst. Examples of acid catalysts which can be employed include hydrogen halides such as hydrogen chloride or bromide, and Broensted acid such as sulfuric, nitric, phosphoric, trifluoroacetic or p-toluenesulfonic acid, a cation exchange resin and Lewis acids such as aluminum chloride

The arginine derivative may be either an optically active substance or a racemic mixture. The salts of the arginine derivative which can be employed include inorganic acid salt such as hydrochloride, sulfate, hydrobromide, hydroiodide or phosphate, or organic acid salts such as acetate, citrate, p-toluenesulfonate, a fatty acid salt, succinate, maleate, lactate, tartrate, glutamate, aspartate or pyrrolidonecarboxylate.

Specific examples of the arginine derivative according to this invention include N.sup..alpha. -cocoyl-L-arginine stearyl ester hydrochloride, N.sup..alpha. -lauroyl-L-arginine stearyl ester lactate, N.sup..alpha. -lauroyl-L-arginine palmityl ester succinate, N.sup..alpha. -lauroyl-L-arginine stearyl ester citrate, N.sup..alpha. -myristoyl-DL-arginine stearyl ester sulfate, N.sup..alpha. -palmitoyl-L-arginine lauryl ester hydrochloride, N.sup..alpha. -palmitoyl-DL-arginine palmityl ester malate, N.sup..alpha. -stearoyl-L-arginine stearyl ester phosphate, N.sup..alpha. -stearoyl-L-arginine stearyl ester DL-pyrrolidonecarboxylate, hardened beef tallow fatty acid acyl-L-arginine lauryl ester hydrochloride, N.sup..alpha. -cocoyl-L-arginine palmityl ester glutamate, N.sup..alpha. -L-arginine laurylester aspartate, N.sup..alpha. -octanoyl-L-arginine-myristyl ester hydrochloride, N.sup..alpha. -cocoyl-L-arginine isostearyl ester hydrochloride, and N.sup..alpha. -myristoyl-L-arginine octyldodecyl ester hydrochloride.

The emulsifier composition of this invention can emulsify oily and aqueous components uniformly to form a stable emulsion over a wide range of temperatures.

Examples of the oily components which can be employed to form an emulsion include hydrocarbons such as liquid paraffin, squalane, vaseline and microcrystalline wax; oils and fats such as olive oil, coconut oil, tsubaki oil, Japan wax and castor oil; waxes such as beeswax, spermaceti, jojoba oil, lanolin and carnauba wax; higher fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid and lanolin fatty acid; higher alcohols such as lauryl alcohol, myristyl alcohol, cetanol, stearyl alcohol, cetostearyl alcohol, oleyl alcohol, cholesterol, lanolin alcohol and octyl dodecanol; and esters such as cetyl lactate, tri(capryl caprylic acid) glyceryl ester, hexyl laurate, glycerol trilaurate, isopropyl myristate, octyldodecyl myristate, cetyl myristate, myristyl myristate, glycerol trimyristate, isopropyl palmitate, butyl stearate, octyldodecyl oleate, decyl oleate, N-acyl glutamic acid higher alcohol diester, N-acyl glutamic acid polyoxyethylene octyldodecyl ether diester and hardened oil.

Examples of the aqueous components which can be employed include purified water, glycerol, propylene glycol, 1,3-butylene glycol, sorbitol, polyethylene glycol, hexylene glycol, hydrolytic protein, amino acid, sodium pyrrolidonecarboxylate and sodium lactate; humidifying agents such as sodium hyaluronate, water-soluble chitin, chitosan and derivatives thereof; alcohols such as ethyl alcohol and isopropanol; and salts.

Salts have hitherto been difficult to employ because they have an adverse effect on the nonionic surface active agent which have heretofore usually been employed as emulsifiers. It is however possible to use salts with the arginine derivative of this invention, as the emulsifying properties of the present arginine derivatives are hardly influenced by any such salt.

A thickener can also be added to the emulsifier composition of this invention to control its viscosity. Examples of thickeners which can be employed include high molecular thickeners such as carboxyvinyl polymer, sodium polyacrylate, sodium alginate, propylene glycol alginate, sodium carboxymethyl cellulose, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyethylene glycol distearate and polyoxyethylene (120)-methyl glucose dioleate; and colloidal hydrated silicates such as colloidal hydrated aluminum silicate (bentonite) and colloidal hydrated aluminum magnesium silicate.

Although the emulsifier composition consisting solely of the arginine derivative according to formula (I) can form a stable emulsion, it can also contain an emulsifier which is conventionally employed, depending on the purpose for which composition is used.

Examples of the conventional emulsifier which can be employed include anionic surface active agents such as polyoxyethylene alkyl ether, polyoxyethylene cholesteryl ether, polyoxyethylene sorbitan fatty acid partial ester, polyoxyethylene sorbitol fatty acid partial ester, polyoxyethylene glycerol fatty acid partial ester, polyoxyethylene phosphoric acid ester, polyoxyethylene fatty acid monoester, polyoxyethylene hardened castor oil, polyoxyethylene hardened castor oil fatty acid ester, polyglycerol fatty acid ester, cane sugar fatty acid ester, N-acyl glutamic acid polyoxyethylene alkyl ether diester, monopyroglutamic acid monofatty acid polyoxyethylene hardened castor oil, monopyroglutamic acid monofatty acid polyoxyethylene glycerol, monopyroglutamic acid monofatty acid glycerol, monofatty acid ethylene glycol, monofatty acid propylene glycol, sorbitan fatty acid partial ester, glycerol fatty acid partial ester, fatty acid alkanol amide, alkylamine oxide, N-acyl glutamic acid, N-acyl aspartic acid, and other N-acyl acidic amino acids, or salts thereof; and cationic surface active agents such as lower alkyl esters of N-long-chain acyl basic amino acids. Each of the alkyl group, acyl group (residual group of fatty acid), etc. noted above may have 8 to 22 carbon atoms.

The emulsifier composition of this invention can form an O/W or W/O emulsion if the proportions of its oily and aqueous components are appropriately varied, or if another appropriate emulsifier is added thereto.

Although the amount of the arginine derivative which the emulsifier composition of this invention can contain may depend on the purpose for which it is used, this amount usually ranges from 0.1 to 10% by weight.

The emulsifier composition of this invention may further contain a preservative, an ultraviolet absorbing agent, a pigment, a perfume, an extract of a crude drug, or other additives, if such additives are required for attaining the purpose for which the composition is used.

The composition can be used for making, for example, cosmetics for the skin such as milky lotions and creams, medicines for external use such as ointments, cosmetics for the hair such as shampoos, rinses, hair treatment solutions and hair conditioners, and softeners. It is particularly useful when used for making a cosmetic for the hair and a softener, as the arginine derivative is adsorbed by the hair and fibers, such as of wool or cotton, and renders them very soft, antistatic and smooth.

Quaternary ammonium sals have usually been employed for imparting softness, antistatic property and smoothness to the hair, or fibers such as of wool and cotton, but there is concern about the safety of their use. On the other hand, the present arginine derivatives are very safe and are, therefore, suitable for any cosmetic for the hair, or softener.

When the composition of this invention is employed for making a cosmetic for the hair or a softener, it may contain other components in addition to the arginine derivative of formula (I), the oily and aqueous components and the thickener if it does not depart from the spirit of this invention. More specifically, it may contain an anionic surface active agent.

Examples of anionic surface active agents which can be employed include N-acyl acidic amino acids or salts thereof, such as long-chain fatty acid salt, alkyl sulfate, polyoxyethylene alkyl ether sulfate, alkyl sulfonate (SAS), .alpha.-olefin sulfonate (AOS), monoalkyl sulfosuccinate, dialkyl sulfosuccinate, polyoxyethylene alkyl sulfosuccinate, acyl monoethanolamide polyoxyethylene sulfosuccinic acid monoester, monoalkyl phosphate, polyoxyethylene alkyl ether phosphate, acyl methyl taurine salt, acyl isethionate, N-acyl glutamic acid and N-acyl aspartic acid; and N-acyl neutral amino acids or salts thereof, such as N-acyl proline, N-acyl serine, Nacyl sarcosine and N-acyl methyl .beta.-alanine. The anionic surface active agent which can be employed is one in which the alkyl and acyl groups have 8 to 22 carbon atoms.

If any salt is employed, it is preferable to use a lithium, potassium, sodium or triethanolamine salt, or a basic amino acid salt, such as of lysine or arginine.

Examples of the cationic surface active agent which can also be used with arginine derivative of this invention include alkyltrimethyl ammonium salts, dialkyldimethyl ammonium salts, alkyldimethylbenzyl ammonium salts, alkyl pyridinium salts, dipolyoxyethylene alkylmethyl ammonium salts, tri(polyoxyethylene)alkyl ammonium salts, and 2-alkyl-1-alkyl-1-hydroxyethyl imidazolinium salts. The cationic surface active agent which can be employed is one in which the alkyl group has 8 to 22, preferably 16 to 22, carbon atoms. Alkyl groups having 16 to 22 carbon atoms are preferred from the standpoint of safety.

The type of salts which can be employed are salts in which the counter ions are a halogen atom, such as chlorine or bromine. Other examples of cationic surface active agent which can be employed include lower alkyl esters of N-long-chain acyl basic amino acids, such as N-cocoyl-L-arginine ethyl ester . DL-pyrrolidone carboxylate.

Examples of the amphoteric surface active agent which can be employed include alkyldimethyl aminoacetic acid betaine, 2-alkyl-N-carboxymethyl-Nhydroxyethyl imidazolinium betaine, higher fatty acid amide propyldimethyl aminoacetic acid betaine, N-alkyl-N,Ndimethyl-N-sulfoalkylene ammonium betaine, and N-mono long-chain acyl-N,N-dimethyl lysine. The alkyl group and the acyl group (residual group of fatty acid) of these materials are each required to have 8 to 22 carbon atoms.

The composition may further contain polyvinyl alcohol, polyvinyl acetate, tragacanth gum, shellac, a methoxyethylene-maleic anhydride copolymer, polyvinyl pyrrolidone, a polyvinyl pyrrolidone-vinyl acetate copolymer, a polyvinyl pyrrolidone-dimethylaminoethyl methacrylic acid copolymer, polypeptide, cationized cellulose, lecithin, methyl polysiloxane, methylphenyl polysiloxane, cyclic and other silicones, polyoxypropylene butyl ether, or any other film-forming agent; and N-lauroyl-L-lysine, zinc pyrithione, 1-hydroxy-2-pyridone salt, or any other agent for removing and/or controlling dandruff.

The emulsifier composition of this invention can be manufactured as easily as any conventional cleansing agent. It can, for example, be manufactured if the oily and aqueous components are mixed separately with heating, then mixed together, and the mixture subsequently cooled to room temperature. It can be manufactured easily by employing any conventional apparatus.

Having generally described this invention, a further understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise specified.

EXAMPLE 1

Synthesis of N.sup..alpha. -lauroyl-L-argininestearyl ester hydrochloric salt (A):

Twenty grams of N.sup..alpha. -lauroyl-L-arginine, 16.7 g of stearyl alcohol and 20.0 g of 3A molecular sieves were added to 400 ml of toluene. The mixture was stirred in an ice bath, and then hydrochloride gas was bubbled into the mixture, which was then allowed to stand overnight at room temperature. The 3A molecular sieves were separated by filtration and then the concentrated filtrate was redissolved with 800 ml of acetone, and then cooled and filtered. The residue was washed with acetone and dried under reduced pressure to obtain 30.5 g of white crystals (A) (84.2%). The physical data of m.p. MS, IR of compound (A) are shown in table 1.

EXAMPLE 2

N.sup..alpha. -Lauroyl-L-argininepalmityl ester hydrochloric acid salt (B) was obtained by following the procedure outlined in example 1 using palmityl alcohol (14.9 g) instead of stearylalcohol. The yield was 27.0 g (78.0%). The physical data of compound (B) are shown in table 1.

EXAMPLE 3

N.sup..alpha. -Lauroyl-L-argininelauroyl ester hydrochloric acid salt (C) was synthesized by following the procedure outlined in example 1 using lauroyl alcohol (11.5 g) instead of stearyl alcohol. The yield was 21.3 g (67.6%). The physical data of compound (C) are shown in table 1.

EXAMPLE 4

N.sup..alpha. -palmitoyl-L-argininelauryl ester hydrochloric acid salt (D) was obtained by following the procedure outlined in example 1 using N.sup..alpha. -palmitoyl-L-arginine (20.0 g) and laurylalcohol (9.9 g) instead of N.sup..alpha. -lauroyl-L-arginine and stearylalcohol. The yield was 23.1 g (77.3%) The physical data of compound (D) are shown in table 1.

EXAMPLE 5

N.sup..alpha. -palmitoyl-L-argininepalmityl ester hydrochloric acid salt (E) was synthesized by following the procedure outlined in example 1 using N.sup..alpha. -palmitoyl-L-arginine (20.0 g) and palmityl alcohol (12.9 g) instead of N.sup..alpha. -lauroyl-L-arginine and stearylalcohol. The yield was 26.5 g (81.3%). The physical data of compound (E) are shown in table 1.

EXAMPLE 6

N.sup..alpha. -palmitoyl-L-argininestearyl ester hydrochloric acid salt (F) was obtained by following the procedure outlined in example 1 using N.sup..alpha. -palmitoyl-L-arginine (20.0 g) and stearyl alcohol (14.4 g) instead of N.sup..alpha. -lauroyl-L-arginine. The yield was 29.0 g (85.3%).

The physical data of compound (F) are shown in table 1.

EXAMPLE 7

N.sup..alpha. -stearoyl-L-argininelauryl ester hydrochloric acid salt (G) was synthesized by following the procedure outlined in example 1 using N.sup..alpha. -stearoyl-L-arginine (20.0 g) and laurylalcohol (8.6 g) instead of N.sup..alpha. -lauroyl-L-arginine and stearylalcohol. The yield was 24.3 g (83.2%). The physical data of compound (G) are shown in table 1.

EXAMPLE 8

N.sup..alpha. -stearoyl-L-argininepalmityl ester hydrochloric acid salt (H) was obtained by following the procedure outlined in example 1 using N.sup..alpha. -stearoyl-L-arginine (20.0 g) and palmitylalcohol (11.1 g) instead by N.sup..alpha. -lauroyl-L-arginine and stearyl alcohol. The yield was 25.5 g (80.2%). The physical data of compound (H) are shown in table 1.

EXAMPLE 9

N.sup..alpha. -stearoyl-L-argininestearyl ester hydrochloric acid salt (I) was obtained by following the procedure outlined in example 1 using N.sup..alpha. -stearoyl-L-arginine (20.0 g) and stearyl alcohol (12.3 g) instead of N.sup..alpha. -lauroyl-L-arginine. The yield was 28.2 g (85.2%). The physical data of compound [I] are shown in table 1.

EXAMPLE 10

N.sup..alpha. -cocoyl-L-arginine stearyl ester hydrochloric acid salt (J) was obtained by following the procedure outlined in example 1 using N.sup..alpha. -cocoyl-L-arginine (70.2 g) and stearyl alcohol (52.1 g) instead of N.sup..alpha. -lauroyl-L-arginine. The yield was 104.5 g (83.0%). The physical data of compound (J) are shown in table 1.

TABLE 1______________________________________Physical data of thenovel arginine derivativesEx- m.p. MS IRample Compound (.degree.C.) (m/e) (cm.sup.-1)______________________________________1 N.sup..alpha. -Lauroyl-L-arginine- 93.3 609 1740 stearyl ester hydrochloric acid salt2 N.sup..alpha. -Lauroyl-L-arginine- 88.6 581 1740 palmityl ester hydrochloric acid salt3 N.sup..alpha. -Lauroyl-L-arginine- 94.5 525 1740 lauryl ester hydrochloric acid salt4 N.sup..alpha. -Palmitoyl-L-arginine- 93.0 581 1730 lauryl ester hydrochloric acid salt5 N.sup..alpha. -Palmitoyl-L-arginine 84.2 637 1730 palmityl ester hydrochloric acid salt6 N.sup..alpha. -Palmitoyl-L-arginine- 80.9 665 1730 stearyl ester hydrochloric acid salt7 N.sup..alpha. -Stearoyl-L-arginine- 89.4 609 1740 lauryl ester hydrochloric acid salt8 N.sup..alpha. -Stearoyl-L-arginine- 76.8 665 1740 palmitoyl ester hydro- chloric acid salt9 N.sup..alpha. -Stearoyl-L-arginine- 76.5 693 1740 stearyl ester hydrochloric acid salt10 N.sup..alpha. -Cocoyl-L-arginine- 114.2 581 609 1740 stearyl ester hydrochloric 637 665 acid salt______________________________________

EXAMPLES 11-15 AND COMPARATIVE EXAMPLE 1

The emulsifier compositions shown in table 2 were prepared and allowed to stand for a month at 45.degree. C. and -5.degree. C. and a microscopic observation (.times.400) of the stability of emulsion was made. The results shown in the table 2 showed that the emulsified compositions of this invention were more stable than the comparative composition (comparative example 1) which used a conventional emulsifier, at both 45.degree. C. and -5.degree. C.

In table 2, 0=uniform emulsion, .DELTA.=partial aggregation, and x=aggregation.

TABLE 2______________________________________ wt. % Com- Example parative 11 12 13 14 15 Example 1______________________________________N.sup..alpha. -Cocoylarginine- 3.0 2.5 2.0stearyl esterhydrochloric acidsaltN.sup..alpha. -Stearoylargi- 3.0nine palmityl esterhydrochloric acidsaltN.sup..alpha. -Lauroylarginine- 3.0palmityl ester aceticacid saltP.O.E. (20) sorbi- 0.5 2.0tane monostearateSorbitane mono- 1.0 1.0stearateLiquid paraffin 27.0 27.0 27.0 27.0 27.0 27.0Cetanol 3.0 3.0 3.0 3.0 3.0 3.0Stearyl aclohol 3.0 3.0 3.0 3.0 3.0 3.0Propylene glycol 5.0 5.0 5.0 5.0 5.0 5.0Water bal. bal. bal. bal. bal. bal.Stability of emulsion:45.degree. C. 0 0 0 0 0 .DELTA.room temperature 0 0 0 0 0 0-5.degree. C. 0 0 0 0 0 X______________________________________

EXAMPLES 16-18 AND COMPARATIVE EXAMPLES 2-4

Hair washed with an emulsifier (Emarl 20C made by Kao Chemicals) was preserved in 0.1% arginine derivatives aqueous solution for one minute, to observe the antistatic effect of the arginine derivatives of this invention obtained by example 1-3.

The treated hair was washed with water and dried. The antistatic value was measured and are reported in table 3. The results showed the antistatic value of the hair treated with the arginine derivatives is smaller than that treated with the conventional emulsifier (comparative example 2: trimethylstearylammonium chloride, and comparative example 3: N.sup..alpha. -cocoyl-L-arginineethyl ester.DL-pyrrolidone carboxylic acid salt), and with a nontreated hair (comparative example 4). These results show that the arginine derivatives of this invention have a good antistatic effect.

The coefficient friction of the hair treated with an arginine derivatives aqueous solution were measured and are reported in table 3. The results show that the coefficient of friction of hair treated in accordance with this invention was smaller than that of hair treated with conventional cation surfactants (comparative example 2: trimethylstearylammonium chloride, and comparative example 3: N.sup..alpha. -cocoyl-L-arginineethyl ester.DL-pyrrolidone carboxylic acid salt), and with the nontreated hair. These results show that the arginine derivatives of this invention have good smoothness. The hair treated with the arginine derivatives was hair free of oil and which could easily be combed.

TABLE 3______________________________________ Antistatic value .times. Coefficient Compound 10.sup.-8 Q friction______________________________________Example16 N.sup..alpha. -Lauroyl-L- 0.13 0.14 argininestearyl ester hydrochloric acid salt17 N.sup..alpha. -Lauroyl-L- 0.14 0.15 argininepalmityl ester hydrochloric acid salt18 N.sup..alpha. -Lauroyl-L- 0.14 0.16 argininelauryl ester hydrochloric acid saltComparativeexample 2 Trimethylstearyl- 0.16 0.17 ammonium chloride 3 N.sup..alpha. -cocoyl-L- 0.16 0.17 arginineethyl ester hydrochloric acid salt 4 untreated 0.67 0.28______________________________________ (cf 1) The antistatic value was measured by UniversalElectrometer (MMAI17 (made by KAWAGUCHI INDUSTRY Co. Ltd.) (cf 2) A Coefficient friction was measured by the Friction Tester (KESSE) (made by KATOHTECH Co. Ltd.)

EXAMPLE 19

Milky Lotion

A lotion of the composition shown in table 4 was prepared to obtain a stable emulsion.

TABLE 4______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-argininestearyl ester 3.0hydrochloric acid saltStearic acid 0.2Cetanol 1.5Vaseline oil 3.0Lanolin alcohol 2.0Liquid paraffin 10.0Glycerine 3.0Propylene glycol 5.0Triethanol amine 1.0Perfume 0.5Antiseptic 0.3Water balance______________________________________

EXAMPLE 20

Emollient Cream

The following components were compounded to prepare an emollient cream. The stability of the emulsion was good.

TABLE 5______________________________________Composition wt. %______________________________________N.sup..alpha. -Lauroyl-L-arginineisostearyl ester 3.0lactic acid saltBees was 6.0Cetanol 5.0Reduced Lanolin 8.0Squalene 37.0Monoglyceride 4.0Sorbitan monostearate 1.0Chitin (partially deactificated 40-60%) 0.4Propylene glycol 5.0Perfume 0.2Water balance______________________________________

EXAMPLE 21

Cold Cream

The materials shown in table 6 were compounded in the amounts shown to prepare a cold cream.

TABLE 6______________________________________Composition wt. %______________________________________N.sup..alpha. -Lauroyl-DL-arginine myristyl ester 2.0sulfuric acid saltLiquid paraffin 20.0Solid paraffin (m.p. 42-44.degree. C.) 9.0Isopropyl palmitate 3.0Cetanol 1.0Lanolin 2.0Nikkol WCB 10.0Sorbitan monostearate 1.5Polyoxyethylene sorbitan monooleate (20) 1.5Sodium pyroglutamate (50%) 3.0Antiseptic 0.2Perfume 0.2Water balance______________________________________

EXAMPLE 22

Hair Rinse Treatment Composition

The composition shown in table 7 was prepared to obtain a hair rinse treatment composition.

TABLE 7______________________________________Composition wt. %______________________________________N.sup..alpha. -Stearoyl-DL-arginine lauryl ester 2.0DL-pyrrolidone carboxylic acidDiglyceride 2.0Liquid paraffin 3.0Stearic acid 1.5Polyoxyethylene (5) stearyl ether 1.0Propylene glycol 10.0Perfume 0.5Water balance______________________________________

EXAMPLE 23

Ointment (O/W Type)

The following components were compounded to prepare a O/W type ointment.

TABLE 8______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-argininestearyl ester 2.0hydrochloric acid saltWhite vaseline 25.0Stearyl alcohol 22.0Propylene glycol 12.0Sodium laurylsulfurate 15.0Ethyl paraoxybenzoate 0.3Propyl paraoxybenzoate 0.1Perfume 0.2Water balance______________________________________

EXAMPLE 24

Hair Rinse Composition

The materials shown in table 9 were compounded in the amounts shown to prepare a hair rinse composition.

TABLE 9______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-argininestearyl ester 1.0hydrochloric acid saltSodium N.sup..alpha. -lauroylsalcosine 0.3Polymer JR-400 (Union Carbide) 0.3Cetyl alcohol 1.0Stearyl alcohol 1.0Propylene glycol 1.0Amiter LGOD-2.5 0.5Glycerine 1.0Perfume proper amountWater balance______________________________________

EXAMPLE 25

Hair Treatment Composition

A hair treatment composition was prepared according to the following formulation.

TABLE 10______________________________________Composition wt %______________________________________N.sup..alpha. -Lauroyl-L-argininestearyl ester 1.0hydrochloric acid salt1-Hydroxy-2-pyrydon salt.sup.1) 0.5Liquid paraffin 15.0Silicone.sup.2) 0.5Trimethyl stearyl ammonium chloride 1.0Cetyl alcohol 1.0Stearyl alcohol 2.0Stearic acid 0.5Glycerine monostearate 1.0P.O.E. stearyl ether 1.0Propylene glycol 5.0Water balance______________________________________ ##STR4## ##STR5##

EXAMPLE 26

Hair Condition

The following components were compounded to prepare a hair conditioner.

TABLE 11______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester DL- 1.5pyrrolidone carboxylic acid saltCocamide DEA (KAWAKEN Chemicals) 1.5Liquid paraffine 10.0Cetanol 2.0Stearyl alcohol 2.0Propylene glycol 10.0Sorbitane monopalmitate 1.0Tetraglycerin monostearate 1.0Pyroter CPI-40 (AJINOMOTO CO., INC.) 0.5Methyl parahydroxybenzoate 0.1Collagen 0.5Zinc pyrithion 0.5Water balance______________________________________

Hair treated with the hair conditioner had the characteristics of softness, smooth and good combability.

EXAMPLE 27 Hair Lotion

The following components were compounded to prepare a hair lotion.

TABLE 12______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine palmityl ester sulfuric 1.0acid saltN-Stearoyl-L-Lysine propyl ester hydrochloric 1.0acid saltSodium hyaluronate 0.5Cetanol 1.0P.O.E. (5) sodium laurylethoxy sulfate 1.0Propylene glycol 4.0Ethanol 2.0Squalan 1.0Water balance______________________________________

The hair treated with the hair lotion had the characteristics of smoothness, good combability and good arrangement.

EXAMPLE 28 Hair Rinse

TABLE 13______________________________________Composition wt %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester 1.0hydrochloric acid saltAlkyl phosphate *1 4.0Chitin (partialy deacetificated 40-60%) 0.1Cetanol 5.0Liquid paraffine 1.0P.O.E. stearyl ether 1.5Propylene glycol 5.0Isopropyl vinyl polymer 0.5N-Lauroyl-L-Lysine 0.5Water balance______________________________________ *1 the mixture A and B, A/B = 1/9-9/1, n = 10-30 ##STR6## ##STR7##

Hair treated with the hair rinse had the characteristics of softness, smoothness and good combability.

EXAMPLE 29

Hair Brushing

The materials shown below were compounded in the amounts shown to prepare a hair brushing composition.

TABLE 14______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester hydrochloric 0.5acid saltN-Lauroyl glutamic acid 0.2Dimethyl silicone 0.3Squalane 0.2Propylene glycol 0.2Perfume 0.2Water balance______________________________________

Hair treated with the hair brushing composition exhibited was softness, good combability and good arrangement.

EXAMPLE 30 Hair Rinse Composition

The following components were compounded to prepare a hair rinse composition.

TABLE 15______________________________________Composition wt. %______________________________________N.sup..alpha. -Palumitoyl-L-arginine lauryl ester 1.5hydrochloric acid saltStearyl alcohol 2.0Propylene glycol 6.0Perfume 0.2Water balance______________________________________

Hair treated with the hair rinse had the characteristics of smoothness, softness, good combability and good arrangement.

EXAMPLE 31

Hair Shampoo

TABLE 16______________________________________Composition wt. %______________________________________N.sup..alpha. -Lauroyl-L-arginine stearyl ester 0.5hydrochloric acid saltAmisoft CS-11 (AJINOMOTO CO., INC.) 5.0Amisoft CT-12 (30%) (AJINOMOTO CO., INC.) 20.0Sodium lauryl ether sulfate (25%) 20.0Cocamide CDE (KAWAKEN Chemicals) 3.0Chitin (partially deacetificated) 0.1Sodium chloride 3.0P.O.E. (10) stearate 1.0Cetanol 1.0Glycerin monostearate 2.0Perfume 0.2Water balance______________________________________

Hair treated with the hair shampoo was soft, had good combability and was smooth.

EXAMPLE 32

Hair Shampoo

The materials shown below were compounded in the shown amounts to prepare a hair shampoo.

TABLE 17______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester sulfuric 0.5acid saltAmisoft CT-12 (30%) (AJINOMOTO CO., INC.) 45.0Cocamide CDE (KAWAKEN Chemicals) 5.0Sodium DL-pyrrolydone carboxylate (50%) 6.0P.O.E. (50%) Distearate 3.0Ethylene glycol distearate 1.5Behenyl alcohol 1.0Perfume 0.2Water balance______________________________________

Hair treated with the hair shampoo has the characteristics of good cleaning, softness and smooth.

EXAMPLE 33

Softening Agent Composition

The following components were compounded to prepare a softening agent composition.

TABLE 18______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester hydrochloric 3.0acid saltLiquid paraffine 2.0Cetyl alcohol 1.0Propylene glycol 2.0DL-pyrrolidone carboxylate 0.5Perfume 0.2Water balance______________________________________

A cotton towel treated with the softening agent was soft and antistatic.

EXAMPLE 34

Softening Agent Composition

The following components were compounded in the shown amounts to prepare a softening composition.

TABLE 19______________________________________Composition wt %______________________________________N.sup..alpha. -Lauroyl-L-arginine 2.0isostearyl ester lactic acid saltSqualane 2.0P.O.E. stearyl ether 1.0Silicone *1 0.3Cetanol 1.0Stearyl alcohol 1.0Stearic acid 0.5Glyceline monostearate 1.0Propylene glycol 1.0Water balance______________________________________ ##STR8##

A cotton towel treated with the softening agent was soft and antistatic.

EXAMPLE 35

Softening Agent Composition

The following components were compounded to prepare a softening agent composition.

TABLE 20______________________________________Composition wt. %______________________________________N.sup..alpha. -Stearoyl-D-arginine lauryl ester DL- 2.5pyrrolydone carboxylic acid saltCocamide propyl betaine CL (KAWAKEN Chemicals) 1.5Liquid paraffine 2.0Cetanol 2.0Stearyl alcohol 2.0Stearic acid 1.0Plopylene glycol 2.0Sorbitane monopalumitate 0.5Tetraglycerine monostearate 0.5Pyroter CPI-40 (AJINOMOTO CO., INC.) 0.5Methyl parahydroxybenzoate 0.1Water balance______________________________________

A cotton towel treated with the softening agent was soft and antistatic.

EXAMPLE 36 Softening Agent Composition

A softening agent composition was prepared by using the compound outlined in table 21 in the amounts shown.

TABLE 21______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-arginine stearyl ester hydrochloric 2.5acid saltN-Lauroyl glutamic acid 0.5Squalane 1.0Propylene glycol 2.0Perfume 0.2Water balance______________________________________

A test piece made of wool was treated with the softening agent composition, and then evaluated. It was soft and antistatic.

EXAMPLE 37

The following components were compounded in the amounts shown to prepare a softening agent composition.

TABLE 22______________________________________Composition wt. %______________________________________N.sup..alpha. -palmitoyl-L-arginine palmityl ester 4.0acetic acid saltTrimethylstearyl ammonium chloride 0.5Cetanol 1.0P.E.O. (5) sodium lauroyl ethoxy sulfate 1.0Carboxy vinyl chloride resin 0.5Propylene glycol 4.0Ethanol 2.0Squalene 1.0Water balance______________________________________

A test piece of wool treated with the softening agent composition was soft, smooth, antistatic and emollient.

EXAMPLE 38 Emollient Lotion

The materials shown in table 23 were compounded in the amounts shown to prepare an emollient lotion.

TABLE 23______________________________________Composition wt. %______________________________________N.sup..alpha. -Lauroyl-L-argininestearyl ester 8.0acetic acid saltLiquid paraffin 22.0Octyl dodecyl mylistate 1.5Amiter LGOD-2 (AJINOMOTO CO., INC.) 0.5Pyroter GPI-25 (AJINOMOTO CO., INC.) 0.5Cetanol 1.1Polyethylene glycol 1000 0.2Amisoft LS-11 (AJINOMOTO CO., INC.) 0.1Propylene glycol 5.0Glycerine 3.0Methyl parahydroxybenzoate 0.1Perfume 0.3Water balance______________________________________

The emulsion of the emollient lotion was stable for at least six months.

EXAMPLE 39 Vanishing Cream

The composition shown in table 24 was prepared to obtain a vanishing cream.

TABLE 24______________________________________Composition wt. %______________________________________N.sup..alpha. -Cocoyl-L-argininestearyl ester 0.5hydrochloric acid saltStearic acid 17.0Stearyl alcohol 4.0Butyl stearate 8.0Glycerine monostearyl ester 1.5Propylene glycol 10.0Glycerin 4.0Perfume 0.2Water balance______________________________________

The emulsion of the vanishing cream was very stable for at least six months.

Claims

1. An emulsifier composition, containing, as an emulsifier, 0.1 to 10% by weight of at least one N.sup..alpha. -acylarginine alkyl ester of the formula (I): ##STR9## wherein: R.sup.1 CO is a mixture of straight-chain C.sub.8-22 acyl groups;

R.sup.2 is a straight-chain or branched C.sub.22 alkyl group;

or an acid-addition salt thereof.

2. The emulsifier composition of claim 1, wherein said salt is a hydrochloride salt, sulfate salt, hydrobromide salt, hydroiodide salt, phosphate salt, acetate salt, citrate salt, p-toluenesulfonate salt, fatty acid salt, succinate salt, maleate salt, lactate salt, tartrate salt, glutamate salt, aspartate salt, or pyrrolidonecarboxylate salt.

3. The emulsifier composition of claim 1, comprising at least one of said N.sup..alpha. -acylarginine alkyl ester of formula (I), an oily component and an aqueous component:

(i) said oily component is at least one member selected from the group consisting of liquid paraffin, squalane, vaseline, microcrystalline wax, olive oil, coconut oil, tsubaki oil, Japan wax, castor oil, beeswax, spermaceti, jojoba oil, lanolin, carnauba wax, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, lanolin fatty acid, lauryl alcohol, myristyl alcohol, cetanol, stearyl alcohol, cetostearyl alcohol, oleyl alcohol, cholesterol, lanolin alcohol, octyl dodecanol, cetyl lactate, tri(capryl caprylic acid) glyceryl ester, hexyl laurate, glycerol trilaurate, isopropyl myristate, octyldodecyl myristate, cetyl myristate, myristyl myristate, glycerol trimyristate, isopropyl palmitate, butyl stearate, octyldodecyl oleate, decyl oleate, N-acyl glutamic acid higher alcohol diester, N-acyl glutamic acid polyoxyethylene octyldodecyl ether diester, and hardened oil; and

(ii) wherein said aqueous component is at least one member selected from the group consisting of water, glycerol, propylene glycol, 1,3-butylene glycol, sorbitol, polyethylene glycol, hexylene glycol, hydrolytic protein, amino acid, sodium pyrrolidonecarboxylate, sodium lactate, sodium hyaluronate, water-soluble chitin, chitosan and derivatives thereof, ethyl alcohol, isopropanol, and salts.

4. The emulsifier composition of claim 1, comprising a thickener which is at least one member selected from the group consisting of carboxyvinyl polymer, sodium polyacrylate, sodium alginate, propylene glycol alginate, sodium carboxymethyl cellulose, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, polyethylene glycol distearate, polyoxyethylene (120)methyl glucose dioleate, colloidal hydrated aluminum silicate (bentonite), and colloidal hydrated aluminum magnesium silicate.

5. The emulsifier composition of claim 1, further comprising polyoxyethylene alkyl ether, polyoxyethylene cholesteryl ether, polyoxyethylene sorbitan fatty acid partial ester, polyoxyethylene sorbitol fatty acid partial ester, polyoxyethylene glycerol fatty acid partial ester, polyoxyethylene phosphoric acid ester, polyoxyethylene fatty acid monoester, polyoxyethylene hardened castor oil, polyoxyethylene hardened castor oil fatty acid ester, polyglycerol fatty acid ester, cane sugar fatty acid ester, N-acyl glutamic acid polyoxyethylene alkyl ether diester, monopyroglutamic acid monofatty acid polyoxyethylene hardened castor oil, monopyroglutamic acid monofatty acid polyoxyethylene glycerol, monopyroglutamic acid monofatty acid glycerol, monofatty acid ethylene glycol, monofatty acid propylene glycol, sorbitan fatty acid partial ester, glycerol fatty acid partial ester, fatty acid alkanol amide, alkylamine oxide, N-acyl glutamic acid, N-acyl aspartic acid, and lower alkyl esters of N-long-chain acyl basic amino acids.

6. The emulsifier composition of claim 1, comprising a preservative, an ultraviolet absorbing agent, a pigment, a perfume, or an extract of a crude drug.

7. The emulsifier composition of claim 1, wherein said composition is a milky solution, a cream, ointment, a shampoo, a rinse, a hair treatment solution, a hair conditioner, or a softener.

8. The emulsifier composition of claim 1, said composition being a hair cosmetic composition or a softener composition, and comprising:

a surface active agent which is at least one member selected from the group consisting of acidic amino acids, long-chain fatty acid salts, alkyl sulfates, polyoxyethylene alkyl ether sulfates, alkyl sulfonates, .alpha.-olefin sulfonates, monoalkyl sulfosuccinates, dialkyl sulfosuccinates, polyoxyethylene alkyl sulfosuccinates, acyl monoethanolamide polyoxyethylene sulfosuccinic acid monoesters, monoalkyl phosphates, polyoxyethylene alkyl ether phosphates, acyl methyl taurine salts, acyl isethionates, N-acyl glutamic acids, N-acyl aspartic acids, N-acyl prolines, N-acyl serines, N-acyl sarcosines, N-acyl methyl .beta.-alanines, alkyltrimethyl ammonium salts, dialkyldimethyl ammonium salts, alkyldimethylbenzyl ammonium salts, alkyl pyridinium salts, dipolyoxyethylene alkylmethyl ammonium salts, tri(polyoxyethylene)alkyl ammonium salts, 2-alkyl-1-alkyl-1-hydroxyethyl imidazolinium salts, N-cocoyl-L-arginine ethyl ester;

or an amphoteric surface active agent which is at least one member selected from the group consisting of alkyldimethyl aminoacetic acid betaine, 2-alkyl-N-carboxymethyl-Nhydroxyethyl imidazolinium betaine, higher fatty acid amide propyldimethyl aminoacetic acid betaine, N-alkyl-N,Ndimethyl-N-sulfoalkylene ammonium betaine, and N-mono long-chain acyl-N,N-dimethyl lysines.

9. The emulsifier composition of claim 1, further comprising polyvinyl alcohol, polyvinyl acetate, tragacanth gum, shellac, a methoxyethylenemaleic anhydride copolymer, polyvinyl pyrrolidone, a polyvinyl pyrrolidone-vinyl acetate copolymer, a polyvinyl pyrrolidone-dimethylaminoethyl methacrylic acid copolymer, polypeptide, cationized cellulose, lecithin, methyl polysiloxane, methylphenyl polysiloxane, a cyclic or non-cyclic silicone, polyoxypropylene butyl ether, N-lauroyl-L-lysine, zinc pyrithione, or 1-hydroxy-2-pyridone salt.

10. A N.sup..alpha. -acylarginine alkyl ester of the formula (I): ##STR10## wherein: R.sup.1 CO is a mixture of straight-chain C.sub.8-22 acyl groups;

R.sup.2 is a straight-chain or branched C.sub.22 alkyl group;

or an acid-addition salt thereof.

11. The free form of the N.sup..alpha. -acylarginine alkyl ester of claim 10.

12. The N.sup..alpha. -acylarginine alkyl ester of claim 10, wherein said salt is a hydrochloride salt, a sulfate salt, a hydrobromide salt, a hydroiodide salt, a phosphate salt, an acetate salt, a citrate salt, a p-toluenesulfonate salt, a fatty acid salt, a succinate salt, a maleate salt, a lactate salt, a tartrate salt, a glutamate salt, an aspartate salt, or a pyrrolidonecarboxylate salt.