Patent Application
20110098363
The present invention is directed to chemical compounds of formula (I)
wherein A1 to A5 together comprise at least one hydrophilic group and at least one hydrophobic group.
Amphiphilic molecules with linear or branched alkyl chains are well known. Whilst some of them are performing well as emulsifiers, dispersing agents and solubilizers most of them do not perform well when used for aromatic hydrophobic actives and performance chemicals. For these purposes—there exists a need for amphiphilic molecules with new structures. These amphiphilic molecules should have an enhanced interaction between each other thus leading to an increase in micellar stability and by that to more stable emulsions, dispersions and interfacial layers.
This need has surprisingly been met by the compound according to claims 1 to 5, the processes according to claims 6 and 7, the compositions according to claims 8 to 11 and the use according to claim 12.
The present invention is directed to a chemical compound according to formula (I)
wherein
also A6 and A7 comprise a polymer selected from the group consisting of
the sum of all k is 6 or >6,
12< sum of all k<120,
With EO having the meaning of ethylene oxide, PO having the meaning of propylene oxide and BuO having the meaning of butylene oxide.
A “block-copolymer” is a polymer in which the different monomer units such as [EO] and [PO] are assembled in a way that they form self-contained units as opposed to being assembled randomly. To achieve this, the reaction with one group of monomers, e.g. [PO], is only started after the reaction with the other monomer, e.g. [EO], has been completed. The length of a block therefore is at least 1, preferably 2 units, even more preferred at least 4 units of one kind of monomer.
In one preferred embodiment of the invention A1 is an alkyl having 1 to 50 C-atoms. A1 being an alkyl having ≦20, preferably ≦18, even more preferred ≦15 and most preferred ≦12 C-atoms, such as 12, 9, 6 or 3 C-atoms is even more preferred. The alkyl can be linear or branched, with linear being preferred.
In another preferred embodiment A1 is an aryl or alkylaryl having 6 to 50 C-atoms. A1 preferably is an alkyl or alkylaryl having ≦20, preferably ≦18, even more preferred ≦15 and most preferred ≦12 C-atoms, such as 12 or 6 C-atoms. A1 being benzyl is particularly preferred.
There exist further preferred embodiments, e.g. a chemical compound as described above, wherein
A1 is alkyl, aryl or alkylaryl and
6<sum of all k<100.
A chemical compound as described above, wherein
A1 is alkyl, aryl or alkylaryl and
8<sum of all k<80 is even more preferred.
Also for chemical compounds as described above, wherein A1 is
there exist embodiments, which are preferred. Chemical compounds are preferred, wherein A1 is
and 6<sum of all k<300 or 6< sum of all p<300. They are even more preferred, in case 8<sum of all k<250 or 8< sum of all p<250.
Depending on the intended use of the chemical compound there exists a variety of particularly preferred embodiments of the present inventions. Such are:
A)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m with [XO] being [PO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6 <sum of all m<300.
They are even more preferred, in case 8<sum of all k<250 or 8 <sum of all m<250.
B)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m with [XO] being [BuO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6 <sum of all m<300.
They are even more preferred, in case 8<sum of all k<250 or 8 <sum of all m<250.
C)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m with m=0 k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30.
They are particularly preferred when 6<sum of all k<300. They are even more preferred, in case 8<sum of all k<250.
D)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q with
p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and
q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30.
They are particularly preferred when 6<sum of all p<300 or 6<sum of all q<300.
They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250.
E)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m[EO]n with [XO] being [PO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30 and
n=1 to 50, preferably n=2 to 40, more preferably n=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
F)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m[EO]n with [XO] being [BuO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30 and
n=1 to 50, preferably n=2 to 40, more preferably n=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
G)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q[XO]m with [XO] being [PO] and
p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and
q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
H)
Chemical compounds, wherein A1 is
and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q[XO]m with [XO] being [BuO] and
p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and
q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
I)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4 and A5 comprise as polymer [EO]k[XO]m with [XO] being [PO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300.
They are even more preferred, in case 8<sum of all k<250 or 8<sum of all m<250.
J)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m with [XO] being [BuO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300.
They are even more preferred, in case 8<sum of all k<250 or 8<sum of all m<250.
K)
Chemical compounds, wherein A1 is selected from the group consisting of aryl and alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m with m=0 k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30.
They are particularly preferred when 6<sum of all k<300. They are even more preferred, in case 8<sum of all k<250.
L)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q with p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30.
They are particularly preferred when 6<sum of all p<300 or 6<sum of all q<300.
They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250.
M)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m[EO]n with [XO] being [PO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30 and
n=1 to 50, preferably n=2 to 40, more preferably n=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
N)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [EO]k[XO]m[EO]n with [XO] being [BuO] and
k=1 to 50, preferably k=2 to 40, more preferably k=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30 and
n=1 to 50, preferably n=2 to 40, more preferably n=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
O)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q[XO]m with [XO] being [PO] and
p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and
q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
P)
Chemical compounds, wherein A1 is selected from the group consisting of alkyl, aryl, alkylaryl and A2, A3, A4, A5, A6 and A7 comprise as polymer [PO]p[EO]q[XO]m with [XO] being [BuO] and
p=1 to 50, preferably p=2 to 40, more preferably p=3 to 30 and
q=1 to 50, preferably q=2 to 40, more preferably q=3 to 30 and
m=1 to 50, preferably m=2 to 40, more preferably m=3 to 30.
They are particularly preferred when 6<sum of all k<300 or 6<sum of all m<300 or 6<sum of all n<300. They are even more preferred, in case 8<sum of all p<250 or 8<sum of all q<250 or 8<sum of all n<250.
Depending on the substitution pattern of the triazine core there exist different processes for producing them, which form further aspects of the present invention.
The process for the production of a compound according to formula (I)
wherein
[EO]k[XO]m[EO]m with [XO] being [PO] or [BuO] and k, m and n independently from each other being
The process for the production of a compound according to formula (I)
wherein
with X being alkyl, aryl or alkylaryl
Step a) is performed using ethylene carbonate or propylene carbonate. One advantage of this is that the reaction can be performed without using a solvent. This would be needed in case the melamine would be reacted with ethylene oxide or propylene oxide directly. A description of the latter process can be found e.g. in DE 2 188 868.
The reaction of step a) according to the invention can be performed batch wise, semibatch wise or continuously. It can be performed at temperatures from 0° C. to 300° C., preferably from 50° C. to 200° C. and particularly preferred from 100° C. to 250° C. It can be performed under vacuum, at atmospheric pressure and under pressure. Also it can be performed using a protection gas.
The reaction of step b), c) and d) can be performed in the same way as step a) in case ethylene carbonate or propylene carbonate is used in the very step.
In case ethylene oxide, propylene oxide or butylene oxide are used, the reaction in step b), c) and d) can also be performed batch wise, semi-batch wise or continuously. It can be performed at temperatures from 0° C. to 300° C., preferably from 50° C. to 200° C. and particularly preferred from 100° C. to 250° C. It can be performed under vacuum, at atmospheric pressure and under pressure, whereby it is preferred that the reaction is performed under pressure. The pressure preferably ranges from 1 to 1000 atm, preferably from 5 to 500 atm and particularly from 10 to 100 atm. The reaction can also be performed using a protection gas. The catalysts used are basic catalysts, such as KOH, NaOH, K2CO3 and DABCO.
The steps a), b), c) and d) can be performed in one vessel or in more than one vessel. It is one embodiment of the invention that the step or steps comprising carbonate compounds, i.e. ethylene carbonate or propylene carbonate, are performed in one vessel and the step or steps comprising oxide compounds, i.e. ethylene oxide, propylene oxide or butylene oxide, are performed in another vessel.
A chemical composition comprising at least one inventive chemical compound is another object of the present invention.
There exist preferred amounts in which the inventive compound is present in the inventive chemical composition. Therefore a chemical composition, wherein the at least one inventive chemical compound is present in an amount of 0.001 to 99.9 mass %, preferably in an amount of 0.01 to 99.5 mass %, more preferred in an amount of 0.1 to 99 mass %, even more preferred in an amount of 1 to 95 mass % and most preferred in an amount of 5 to 50 mass % forms a preferred object of the present invention.
Such chemical composition preferably contains at least one compound selected from the group consisting of surfactant, disinfectant, dye, acid, base, complexing agent, biocide, hydrotope, thickener, builder, cobuilder, enzyme, bleaching agent, bleach activator, bleaching catalyst, corrosion inhibitor, dye protection additive, dye transfer inhibitor, anti-greying agent, soil-release-polymer, fiber protection agent, silicon, bactericide, preserving agent, organic solvent, solubility adjustor, solubility enhancer and perfume.
Surfactants normally consist of a hydrophobic and a hydrophilic part. Thereby the hydrophobic part normally has a chain length of 4 to 20 C-atoms, preferably 6 to 19 C-atoms and particularly preferred 8 to 18 C-atoms. The functional unit of the hydrophobic group is generally an OH-group, whereby the alcohol can be linear or branched. The hydrophilic part generally consists substantially of alkoxylated units (e.g. ethylene oxide (EO), propylene oxide (PO) and/or butylene oxide (BO), whereby generally 2 to 30, preferably 5 to 20 of these alkoxylated units are annealed, and/or charged units such as sulfate, sulfonate, phosphate, carbonic acids, ammonium and ammonium oxide.
Examples of anionic surfactants are: carboxylates, sulfonates, sulfo fatty acid methyl-esters, sulfates, phosphates. Examples for cationic surfactants are: quartery ammonium compounds. Examples for betaine-surfactants are: alkyl betaines. Examples for non-ionic compounds are: alcohol alkoxylates.
A “carboxylate” is a compound, which comprises at least one carboxylate-group in the molecule. Examples of carboxylates, which can be used according to the present invention, are
A “sulfonate” is a compound, which comprises at least one sulfonate-group in the molecule. Examples of sulfonates, which can be used according to the invention, are
A “sulfo fatty acid methylester” is a compound, having the following general formula (III):
wherein R has 10 to 20 C-atoms; preferably 12 to 18 and particularly preferred 14 to 16 C-atoms.
A “sulfate” is a compound, which comprises at least one SO4-group in the molecule.
Examples of sulfates, which can be used according to the present invention, are
A “phosphate” is a compound, which comprises at least one PO4-group. Examples of phosphates, which can be used according to the present invention, are
When producing the chemical composition of the present invention the anionic surfactants are preferably added as salts. Acceptable salts are e.g. alkali metal salts, such as sodium-, potassium- and lithium salts, and ammonium salts, such as hydroxyl ethyl-ammonium-, di(hydroxy-ethyl)ammonium- and tri(hydroxyethyl)ammonium salts.
One group of the cationic surfactants are the quartery ammonium compounds.
A “quartery ammonium compound” is a compound, which comprises at least one R4N+-group per molecule. Examples of counter ions, which are useful in the quartery ammonium compounds, are
Particularly suitable cationic surfactants are:
A “betain-surfactant” is a compound, which comprises under conditions of use—i.e. in the case of textile washing under normal pressure and at temperatures of from room temperature to 95° C.—at least one positive charge and at least one negative charge.
An “alkylbetain” is a betain-surfactant, which comprises at least one alkyl-unit per molecule. Examples of betain-surfactants, which can be used according to the invention, are
Cocamidopropylbetain—e.g. MAFO® CAB, Amonyl® 380 BA, AMPHOSOL® CA, AMPHOSOL® CG, AMPHOSOL® CR, AMPHOSOL® HCG; AMPHOSOL® HCG-50, Chembetaine® C, Chembetaine® CGF, Chembetaine® CL, Dehyton® PK, Dehyton® PK 45, Emery® 6744, Empigen® BS/F, Empigen® BS/FA, Empigen® BS/P, Genagen® CAB, Lonzaine® C, Lonzaine® CO, Mirataine® BET-C-30, Mirataine® CB, Monateric® CAB, Naxaine® C, Naxaine® CO, Norfox® CAPB, Norfox® Coco Betaine, Ralufon® 414, TEGO®-Betain CKD, TEGO® Betain E KE 1, TEGO®-Betain F, TEGO®-Betain F 50 and aminoxides such as alkyl dimethyl amineoxide, i.e. compounds of general formula (VI)
whereby R1, R2 and R3 are chosen independently from each other of an aliphatic, cyclic or tertiary alkyl- or amido alkyl-moiety, e.g. Mazox® LDA, Genaminox®, Aromox® 14 DW 970.
Non-ionic surfactants are interfacially active substances having a head group, which is an uncharged, polar, hydrophilic group, not carrying a ionic charge at neutral pH, and which head group makes the non-ionic surfactant water soluble. Such a surfactant adsorbs at interfaces and aggregates to micelles above the critical micelle concentration (cmc). According to the type of the hydrophilic head group it can be distinguished between (oligo)oxyalkylene-groups, especially (oligo)oxyethylene-groups, (polyethyleneglycol-groups), including fatty alcohol polyglycole ether (fatty alcohol alkoxylates), alkylphenol polyglycolether and fatty acid ethoxylates, alkoxylated triglycerides and mixed ethers (polyethylene glycolether alcoxylated on both sides); and carbohydrate-groups, including e.g. alkyl polyglucosides and fatty acid-N-methylglucamides.
Alcohol alkoxylates, are based on a hydrophobic part having a chain length of 4 to 20 C-atoms, preferably 6 to 19 C-atoms and particularly preferred 8 to 18 C-atoms, whereby the alcohol can be linear or branched, and a hydrophilic part, which can be alkoxylated units, e.g. ethylene oxide (EO), propylene oxide (PO) and/or butylene oxide (BuO), having 2 to 30 repeating units. Examples are besides others Lutensol® XP, Lutensol® XL, Lutensol® ON, Lutensol® AT, Lutensol® A, Lutensol® AO, Lutensol® TO.
Alcoholphenolalkoxylates are compounds according to general formula (VII),
which can be produced by addition of alkylene oxide, preferably ethylene oxide onto alkyle phenoles. Preferably R4=H. It is also preferred, if R5=H,—since than it is EO; in the same way it is preferred if R5=CH3, since than it is PO, or, if R5=CH2CH3 since than it is BuO. A compound is especially preferred, in which octyl—[(R1=R3=H, R2=1,1,3,3-tetramethylbutyl (diisobutylene)], nonyl—[(R1=R3=H, R2=1,3,5-trimethylhexyl (tripropylene)], dodecyl-, dinonyl- or tributylphenolpolyglycolether (e.g. EO, PO, BuO), R—C6H4—O-(EO/PO/BuO)n with R═C8 to C12 and n=5 to 10, are present. Non-limiting examples of such compounds are: Norfox® OP-102, Surfonic® OP-120, T-Det® 0-12.
Fatty acid ethoxilates are fatty acid esters, which have been treated with different amounts of ethylene oxide (EO).
Triglycerides are esters of the glycerols (glycerides), in which all three hydroxy-groups have been esterified using fatty acids. These can be modified by alkylene oxides.
Fatty acid alkanol amides are compounds of general formula (VIII)
which comprise at least one amide-group having one alkyle moiety R and one or two alkoxyl-moiety(ies), whereby R comprises 11 to 17 C-atoms and 1≦m+n≦5.
Alkylpolyglycosides are mixtures of alkylmonoglucosides (alkyl-α-D- and -β-D-gluco-pyranoside plus small amounts of -glucofuranoside), alkyldiglucosides (-isomaltosides, -maltosides and others) and alkyloligoglucosides (-maltotriosides, -tetraosides and others). Alkylpolyglycosides are among other routes accessible by acid catalysed reaction (Fischer-reaction) from glucose (or starch) or from n-butylglucosides with fatty alcohols. Alkylpolyglycosides fit general formula (IXI)
with
m=0 to 3 and
n=4 to 20.
One example is Lutensol® GD70.
In the group of non-ionic N-alkylated, preferably N-methylated, fatty acid amides of general formula (X)
R1 is a n-C12-alkyl-moiety, R2 an alkyl-moiety having 1 to 8 C-atoms. R2 preferably is methyl.
A composition as described, which additionally comprises a disinfectant is preferred. The at least one disinfectant preferably is present in an (overall) amount of 0.1 to 20 mass %, preferably 1 to 10 mass % of the composition.
Disinfectants can be: oxidation agents, halogens such as chlorine and iodine and substances, which release the same, alcohols such as ethanol, 1-propanol and 2-propanol, aldehydes, phenoles, ethylene oxide, chlorohexidine and mecetroniummetilsulfate.
The advantage of using disinfectants is that pathogenic germs can hardly grow. Pathogenic germs can be: bacteria, spores, fungi and viruses.
Dyes can be besides others: Acid Blue 9, Acid Yellow 3, Acid Yellow 23, Acid Yellow 73, Pigment Yellow 101, Acid Green 1, Acid Green 25.
A composition is preferred, in which the at least one dye is present in an (overall) amount of 0.1 to 20 mass %, preferably 1 to 10 mass %, of the composition.
Acids are compounds that can advantageously be used to solve or to avoid scaling. Non-limiting examples of acids are formic acid, acetic acid, citric acid, hydrochloric acid, sulfuric acid and sulfonic acid.
Bases are compounds, which are useful for adjusting a preferable pH-range for complexing agents. Examples of bases, which can be used according to the present invention, are: NaOH, KOH and amine ethanol.
As inorganic builder the following are especially useful:
Useful as oligomeric and polymeric cobuilders are: Oligomeric and polymeric carbonic acids, such as homopolymers of acrylic acid and aspartic acid, oligomaleic acid, copolymers of maleic acid and acrylic acid, methacrylic acid or C2-C22-olefines, e.g. isobutene or long chain α-olefines, vinyl-C1-C8-alkylether, vinylacetate, vinylpropionate, (meth)acryl acid ester of C1-C8-alcohols and styrene. Preferred are the homopolymers of acrylic acid and the copolymers of acrylic acid with maleic acid. The oligomeric and polymeric carbonic acids preferably are used as acids or as sodium salts.
Chelating agents are compounds, which can bind cat ions. They can be used to reduce water hardness and to precipitate heavy metals. Examples of complexing agents are: NTA, EDTA, MGDA, DTPA, DTPMP, IDS, HEDP, β-ADA, GLDA, citric acid, oxodisuccinic acid and butanetetracarbonic acid. The advantage of the use of these compounds lies in the fact that many compounds, which serve as cleaning agents, are more active in soft water. In addition to that scaling can be reduced or even be avoided. By using such compounds there is no need to dry a cleaned surface. This is an advantage in the work flow.
Useful anti greying agents are e.g. carboxymethylcellulose and graft polymers of vinyl acetate on polyethylene glycol.
Useful bleaching agents are e.g. adducts of hydrogenperoxide at inorganic salts, such as sodium perborate-monohydrate, sodium perborate-tetrahydrate and sodium carbonate-perhydrate, and percarbonic acids, such as phthalimidopercapronic acid.
As bleach activators compounds such as N,N,N′,N′-tetraacetylethylendiamine (TAED), sodium-p-nonanoyloxybenzenesulfonate and N-methylmorpholiniumacetonitrilemethylsulfate are useful.
Useful enzymes are e.g. proteases, lipases, amylases, cellulases, mannanases, oxidases and peroxidases.
Useful as dye transfer inhibitors are e.g. homo-, co- and graft-polymers of 1-vinylpyrrolidone, 1-vinylimidazol or 4-vinylpyridine-N-oxide. Also homo- and copolymers of 4-vinylpyridin, which have been treated with chloro acetic acid are useful dye transfer inhibitors.
Biozides are compounds, which kill bacteria. An example of a biozide is glutaric aldehyde. The advantage of the use of biozides is that the spreading of pathogenic germs is counteracted.
Hydrotropes are compounds which enhance the solubility of the surfactant/the surfactants in the chemical composition. An example is: Cumolsulfonate.
Thickeners are compounds, which enhance the viscosity of the chemical composition. Non-limiting examples of thickeners are: polyacrylates and hydrophobically modified polyacrylates. The advantage of the use of thickeners is, that liquids having a higher viscosity have a longer residence time on the surface to be treated in the cases this surface is inclined or even vertical. This leads to an enhanced time of interaction.
The use of a chemical compound according to formula (I)
wherein
also A6 and A7 comprise a polymer selected from the group consisting of
The use of the chemical compound as described above, of the inventive chemical compound or of the inventive chemical composition as washing and cleaning agent, surfactant, detergent, demulsifier, antifoaming agent, rheology modifier, melt-viscosity-reducer for polymers, fluidifier for glues and resins, fluidifier for dispersions, solubilizing agent or carrier or encapsulation agent for aromatic and/or hydrophobic substances, melamine and melamine derivatives, dyes and biologically active substances, crop protection adjuvant in aqueous media and formulations forms as well as the use as demulsifier especially in oilfield applications a preferred object of the present invention.
The use of the chemical compound as described above, of the inventive chemical compound or of the inventive chemical composition as washing and cleaning agent and as surfactant as well as the use as demulsifyier especially in oilfield applications, forms a particularly preferred object of the present invention.
The invention will be described in more detail by the following non-limiting examples:
In the following examples the OH number was determined according to DIN 53240-2. The viscosities given are dynamic viscosities, which were measured according to ISO 3219 using a cone plate viscosimeter. NMR was measured on an apparatus Bruker Avance 300 (300 MHz).
with x+y+w+z=12=sum of all k
93.6 g (0.5 mol) of benzoguanamine and 528.4 g (6.0 mol) of ethylene carbonate were put into a 1000 ml flask. The solid mixture was slowly heated to 170° C. within 2 h under stirring. The reaction start was indicated by the formation of CO2. After the start of the reaction the mixture was further stirred at 170° C. until no gas formation was observed. Finally the product was cooled to room temperature. 360 g of product were obtained, as an orange, homogeneous and viscous liquid. The product was water-soluble.
50 (0.21 mol) of caprinoguanamine (from Degussa) and 223 g (2.53 mol) of ethylene carbonate were put into a 1000 ml flask. The solid mixture was slowly heated to 170° C. within 2 h under stirring. The reaction start was indicated by the formation of CO2. After the start of the reaction the mixture was further stirred at 170° C. until no gas formation was observed. Finally the product was cooled to room temperature.
154 g of product were obtained, as an orange, homogeneous and viscous liquid. The product was water-soluble. OH number: 376 mg KOH/g. 1H-NMR (DMSO): δ 4.7 ppm (singulet, 4H), 3-3.5 ppm (multiplet, 48H), 1.3 ppm (singulet, 16H), 0.8 ppm (singulet, 3H).
The aqueous solution of the amphiphile (1 g/l) had a surface tension of 29 mN/m at 25° C. It exhibited low interfacial tension to polar oils due to its short aliphatic nonyl chain. The interfacial tension between olive oil and a 1 g/l surfactant solution was only 0.45 mN/m at 25° C.
21.2 g (0.247 mol) of dicyandiamide (98%), 51.1 g (0.279 mol) of undecylcyanide (98%) and 3.9 g sodium hydroxide were solved in 150 ml ethanol in a conventional four neck round bottom flask equipped with a stirrer, a distillation column connected to water cooled condenser. The mixture was heated to 78° C. After 10 hours under stirring at 78° C., the reaction mixture was slowly brought to room temperature and filtered. After filtration, 52.0 g of a C11-guanamine is obtained as a white powder after evaporation of the solvent. In a second step, the same procedure as in Example 1 was followed, with 36.05 g (0.136 mol) of the C11-guanamine synthesized above instead of benzoguanamine and 143.7 g (1.63 mol) ethylene carbonate. 109.0 g of product were obtained, as an orange, homogeneous and viscous liquid. The product was water-soluble. 1H-NMR (DMSO): δ 4.7 ppm (singulet, 4H), 3-3.5 ppm (multiplet, 48H), 1.2 ppm (singulet, 20H), 0.9 ppm (singulet, 3H).
The aqueous solution of the amphiphile (1 g/l) had a surface tension of 29 mN/m at 25° C. In addition the molecule exhibited a low interfacial tension both to polar and unpolar oils. Hexadecane: 1.6 mN/m; olive oil: 0.50 mN/m.
The same procedure as in Example 3 was followed, with 14.2 g (0.165 mol) of dicyandiamide (98%), 32.0 g (0.15 mol) of tetradecanoic acid nitrile (98%) and 21.2 g sodium hydroxide in 200 ml ethanol. In a second step, the same procedure as in Example 1 was followed, with 21.9 g (0.075 mol) of the C13-guanamine synthesized above instead of benzoguanamine and 79.0 g (0.837 mol) ethylene carbonate. 56.6 g of product were obtained, as an orange, homogeneous and viscous liquid. The product was water-soluble. 1H-NMR (DMSO): δ 4.7 ppm (singulet, 4H), 3-3.5 ppm (multiplet, 48H), 1.2 ppm (singulet, 24H), 0.9 ppm (singulet, 3H).
The aqueous solution of the amphiphile (1 g/l) had a surface tension of 29 mN/m at 25° C. In addition the molecule exhibited a low interfacial tension both to polar and unpolar oils. Hexadecane: 0.45 mN/m; olive oil: 0.32 mN/m.
The properties of the reaction product from Example 2 were measured:
The result is displayed graphically as quadrats in
The properties of the reaction product from Example 3 were measured:
The result is displayed graphically as triangles in
The properties of the reaction product from Example 4 were measured:
The result is displayed graphically as circles in
As can be seen from the above examples the compounds according to the present invention have both, a small surface tension with regard to non-polar substances such as olive oil, which is typical dirt for textiles, and a small surface tension with regard to water, which is the typical solvent for cleaning textiles.
Reaction step a) to give (i):
50.4 g (0.4 mol) of melamine and 440 g (5 mol) of ethylene carbonate were put into a 1000 ml flask. The solid mixture was slowly heated to 170° C. within 2 h under stirring. The reaction start was indicated by the formation of CO2. After the start of the reaction the mixture was further stirred at 170° C. until no gas formation was observed. Finally the product was cooled to room temperature. 272.8 g of product (i) were obtained as an orange, homogeneous and viscous liquid. (i) was water-soluble. OH number: 470 mg KOH/g. Viscosity: 3740 mPa·s at 25° C. 1H NMR (DMSO): δ 4.6 ppm (singulet, 6H), 3-3.5 ppm (multiplet, 48H).
Reaction step b) to give (ii) from (i):
150 g of (i) as obtained from Example 1 and 1.1 g tertBuOK were introduced into an autoclave and reacted with 69.6 g (1.2 mol) propylene oxide, which was added in portions at 130° C. To complete the reaction, the mixture was allowed to post-react for 8 hours under pressure. The reaction mixture was stripped with nitrogen and volatile compounds were removed under vacuum at 80° C. 69.6 g of (ii) were obtained as brown oil (OH number: 367 mg KOH/g).
Reaction step c) to give (iii) from (ii):
135 g (0.1472 mol) of (ii) resulting from Example 2 and 1.4 g tertBuOK were dissolved in 100 ml toluene and introduced into an autoclave and reacted with 116.6 g (2.65 mol) ethylene oxide, which was added in portions at 120° C. To complete the reaction, the mixture was allowed to post-react for 8 hours under pressure. The reaction mixture was stripped with nitrogen and volatile compounds were removed under vacuum at 80° C. 236 g of brown oil (iii) was obtained (Viscosity: 647.1 mPa·s at 25° C., OH number: 200 mg KOH/g).
Reaction steps b) and c) to give (iii) from (i):
215 g (0.2863 mol) of (i) and 3.7g tertBuOK were introduced into an autoclave and reacted with 516.5 g (11.74 mol) ethylene oxide, which was added in portions at 122° C. To complete the reaction, the mixture was allowed to post-react for 4 hours under pressure. The reaction was stirred overnight at 80° C. After 15 h the reaction mixture was stripped with nitrogen and volatile compounds were removed under vacuum at 80° C. To the product were added 4 g tertBuOK and reacted with 133 g (2.29 mol) propylene oxide, which was added in portions at 130° C. To complete the reaction, the mixture was allowed to post-react for 5 hours under pressure. The reaction was stirred overnight at 80° C. The reaction mixture was stripped with nitrogen and volatile compounds were removed under vacuum at 80° C. 823 g of brown oil (iii) were obtained (Viscosity: 833.6 mPa·s at 25° C., OH number: 118 mg KOH/g).
Reaction step b) to give (ii) from (i):
150 g (0.1997 mol) of (i) as obtained from Example 1, 1.1 g KOH and 205.7 g (1.9971 mol) of propylene carbonate are put into a 500 ml flask. The solid mixture is slowly heated to 180° C. within 2 h under stirring. The reaction start is indicated by the formation of CO2. After the start of the reaction the mixture is further stirred at 170° C. until no gas formation is observed. Finally the product is cooled to room temperature. Approximately 275 g of product (ii) is obtained as a brown, homogeneous and viscous liquid.
Reaction step c) to give (iii) from (ii):
150 g (0.1114 mol) of (ii) as obtained from Example 6, 1.4 g KOH and 97.8 g (1.1114 mol) of ethylene carbonate are put into a 500 ml flask. The solid mixture is slowly heated to 170° C. within 2 h under stirring. The reaction start is indicated by the formation of CO2. After the start of the reaction the mixture is further stirred at 170° C. until no gas formation is observed. Finally the product is cooled to room temperature. Approximately 210 g of product (ii) is obtained as a brown, homogeneous and viscous liquid.
It is clear that in the above examples not all “x” and “y” in one molecule are the same, i.e. that e.g. x in A2 can be different from x in A3. In a single molecule there is always some deviation around an average value. This means that in case x or y is 1 it can also happen, that at one or more ligands A2 to A7 the respective block is missing completely in single molecules. However these structures are still within the scope of the present invention, since the average of x or y is 1.
It can be seen that the compounds according to the present invention exhibit a higher affinity to aromatic substances than linear non-aromatic surfactants such as e.g. Pluronics®.
| Number | Date | Country | Kind |
|---|---|---|---|
| 08157285.1 | May 2008 | EP | regional |
| 08157287.7 | May 2008 | EP | regional |
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/EP2009/056537 | 5/28/2009 | WO | 00 | 11/16/2010 |
