# US 7,740,873 B2 · Composition comprising a quaternary silicone and a liquid fatty alcohol and method of treatment

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- Number: US 7,740,873 B2
- Document ID: US7740873B2
- Status: Granted
- Kind: B2
- Application number: 10/606,786
- Filed: 2003-06-27
- Published: 2004-07-08
- Granted: 2010-06-22
- Earliest claimed: 2002-06-28
- Assignees: L'oreal
- Inventors: Sandrine Decoster; Benedicte Cazin
- Web page: https://patentgrep.com/patent/US7740873B2

## CPC

- A61K 8/898: containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
- A61K 8/342: {Alcohols having more than seven atoms in an unbroken chain}
- A61K 8/39: Derivatives containing from 2 to 10 oxyalkylene groups
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 19/10: Washing or bathing preparations
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

Composition containing at least one silicone with quaternary ammonium groups and at least one liquid fatty alcohol. Method for the cosmetic treatment of keratinous materials, in particular hair. The compositions preferably are transparent and have a melting texture. Hair treated with these compositions is shiny, feels soft and is free of residues.

## Claims

### Claim 1

A transparent composition having a turbidity of between 10 and 300 NTU comprising, in a cosmetically acceptable medium, at least one silicone with quaternary ammonium groups represented by formula (III):
in which:
R1, which is identical or different, represents a linear or branched C1-C30 alkyl group or phenyl group;
R2, which is identical or different, represents —CcH2c—O—(C2H4O)a—(C3H6O)b—R5 or —CcH2c—O—(C4H8O)a—R5;
R5, which is identical or different, is selected from the group consisting of the groups of the following formula:
the radicals R8 independently represent a linear or branched C1-22 alkyl or C2-22 alkenyl radical, and optionally carrying one or more OH groups or represent a group ChH2hZCOR9;
R6, R7 and R9, which are identical or different, represent linear or branched C1-22 alkyl or C2-22 alkenyl radicals optionally carrying one or more OH groups, or R7 may form with part of R8 a heterocycle,
n varies from 0 to 500;
q varies from 0 to 20;
a varies from 0 to 50;
b varies from 0 to 50;
c varies from 0 to 4;
f varies from 0 to 4,
g varies from 0 to 2,
h varies from 1 to 4,
Z represents an oxygen atom or NH, and
A− represents a monovalent inorganic or organic anion, wherein the silicone with quaternary ammonium groups is present in an amount of 0.01 to 10% by weight relative to the total weight of the composition, and at least one fatty alcohol which is liquid at 25° C. and at 1 atm selected from the group consisting of saturated or unsaturated, linear or branched C8-C30 fatty alcohols optionally oxyalkylenated with 1 to 15 mol of alkylene oxide or polyglycerolated with 1 to 6 mol of glycerol, wherein the liquid fatty alcohol is present in an amount ranging from 0.01% to 15% by weight relative to the total weight of the composition.

### Claim 2 (depends on 1)

The composition as claimed in claim 1, wherein at least one of the following conditions is satisfied:
c is equal to 2 or 3;
R1 denotes the methyl group;
a and b are equal to zero;
n varies from 0 to 100;
q is equal to 0;
f=3;
g=1;
R6 and R7 denote a methyl group;
R8 denotes the radical —(CH2)—NHCOR9.

### Claim 3 (depends on 1)

The composition as claimed in claim 1, wherein said silicone is Quaternium-80.

### Claim 4 (depends on 1)

The composition as claimed in claim 1, wherein the silicone with quaternary ammonium groups is provided in the form of a solution, suspension or dispersion in water.

### Claim 5 (depends on 1)

The composition as claimed in claim 1, wherein the liquid fatty alcohol is selected from the group consisting of lauryl, isostearyl, isocetyl and oleyl alcohols, lauryl alcohols oxyethylenated with 2 to 6 mol of ethylene oxide and mixtures thereof.

### Claim 6 (depends on 1)

The composition as claimed in claim 1, wherein the liquid fatty alcohol is present in an amount ranging from 0.1% to 5% by weight relative to the total weight of the composition.

### Claim 7 (depends on 1)

The composition as claimed in claim 1, further comprising at least one cationic surfactant.

### Claim 8 (depends on 7)

The composition as claimed in claim 7, wherein the cationic surfactant is selected from the group consisting of the salts of optionally polyoxyalkylenated primary, secondary or tertiary fatty amines, quaternary ammonium salts and mixtures thereof.

### Claim 9 (depends on 8)

The composition as claimed in claim 8, comprising a quaternary ammonium salt selected from the group consisting of:
those which have the following general formula (V):
in which the symbols R1 to R4, which may be identical or different, represent a linear or branched aliphatic radical containing from 1 to 30 carbon atoms, or an aromatic radical such as aryl or alkylaryl; X− is an anion selected from the group consisting of halides, phosphates, acetates, lactates, (C2-C6)alkyl sulfates, and alkyl or alkylaryl sulfonates;
the quaternary ammonium salts of imidazoline;
the diquaternary ammonium salts of formula (VII):
in which R9 denotes an aliphatic radical comprising about from 16 to 30 carbon atoms, R10, R11, R12, R13 and R14, which are identical or different, are selected from the group consisting of hydrogen or an alkyl radical comprising from 1 to 4 carbon atoms, and X− is an anion selected from the group consisting of halides, acetates, phosphates, nitrates and methyl sulfates; and
the quaternary ammonium salts containing at least one ester functional group.

### Claim 10 (depends on 8)

The composition as claimed in claim 8, comprising a quaternary ammonium salt of imidazoline selected from the group consisting of those of the following formula (VI):
in which R5 represents an alkenyl or alkyl radical comprising from 8 to 30 carbon atoms, R6 represents a hydrogen atom, a C1-C4 alkyl radical or an alkenyl or alkyl radical comprising from 8 to 30 carbon atoms, R7 represents a C1-C4 alkyl radical, R8 represents a hydrogen atom, a C1-C4 alkyl radical, X is an anion selected from the group consisting of the group comprising halides, phosphates, acetates, lactates, alkyl sulfates, and alkyl or alkylaryl sulfonates.

### Claim 11 (depends on 7)

The composition as claimed claim 7, wherein the cationic surfactant is selected from the group consisting of behenyltrimethylammonium chloride, cetyltrimethylammonium chloride, Quaternium-83, behenylamidopropyl-2,3-dihydroxypropyldimethylammonium chloride and palmitylamidopropyltrimethylammonium chloride.

### Claim 12 (depends on 7)

The composition as claimed claim 7, wherein the cationic surfactant is present in an amount of 0.05 to 10% by weight relative to the total weight of the composition.

### Claim 13 (depends on 1)

The composition as claimed in claim 1, further comprising at least one cationic polymer.

### Claim 14 (depends on 13)

The composition as claimed in claim 13, which comprises at least two different cationic polymers.

### Claim 15 (depends on 13)

The composition as claimed in claim 13, wherein the cationic polymer is selected from the group consisting of those cationic polymers which contain units containing primary, secondary, tertiary and/or quaternary amine groups which may either form part of the main polymer chain, or may be carried by a side substituent which is directly attached to it.

### Claim 16 (depends on 13)

The composition as claimed in claim 13, wherein said cationic polymer is selected from the group consisting of:
(1) the homopolymers or copolymers derived from acrylic or methacrylic esters or amides and comprising at least one of the units of the following formulae:
in which:
R3, which are identical or different, denote a hydrogen atom or a CH3 radical;
A, which are identical or different, represent a linear or branched alkyl group of 1 to 6 carbon atoms or a hydroxyalkyl group of 1 to 4 carbon atoms;
R4, R5, R6, which are identical or different, represent an alkyl group having from 1 to 18 carbon atoms or a benzyl radical;
R1 and R2, which are identical or different, represent hydrogen or an alkyl group having from 1 to 6 carbon atoms;
X denotes an anion derived from an inorganic or organic acid,
(2) cationic polysaccharides,
(3) polymers consisting of piperazinyl units and of alkylene or hydroxyalkylene divalent radicals with straight or branched chains, optionally interrupted by oxygen, sulfur or nitrogen atoms or by aromatic or heterocyclic rings, as well as the oxidation and/or quaternization products of these polymers,
(4) water-soluble polyaminoamides prepared by polycondensation of an acid compound with a polyamine; these polyaminoamides may be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a diunsaturated derivative, a bishalohydrin, a bisazetidinium, a bishaloacyldiamine, an alkyl bishalide or else with an oligomer resulting from the reaction of a difunctional compound which is reactive toward a bishalohydrin, a bisazetidinium, a bishaloacyldiamine, an alkyl bishalide, an epihalohydrin, a diepoxide or a diunsaturated derivative; the crosslinking agent being employed in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamides may be alkylated or, if they include one or more tertiary amine functional groups, quaternized,
(5) polyaminoamides resulting from the condensation of polyalkylenepolyamines with polycarboxylic acids, followed by an alkylation with bifunctional agents,
(6) polymers obtained by reaction of a polyalkylenepolyamine containing two primary amine groups and at least one secondary amine group with a dicarboxylic acid selected from the group consisting of diglycolic acid and saturated aliphatic dicarboxylic acids containing from 3 to 8 carbon atoms,
(7) cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium,
(8) quaternary diammonium polymers containing repeat units corresponding to the formula:
formula (XIV) in which:
R13, R14, R15 and R16, which are identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing from 1 to 20 carbon atoms or lower hydroxyalkylaliphatic radicals, or else R13, R14, R15 and R16, together or separately, form, with the nitrogen atoms to which they are attached, heterocycles optionally containing a second heteroatom other than nitrogen, or else R13, R14, R15 and R16 represent a linear or branched C1-C6 alkyl radical substituted by a nitrile, ester, acyl, amide or —CO—O—R17-D or —CO—NH—R17-D group where R17 is an alkylene and D a quaternary ammonium group;
A1 and B1 represent polymethylene groups containing from 2 to 20 carbon atoms which may be linear or branched, saturated or unsaturated and which may contain, bonded to or inserted into the main chain, one or more aromatic rings, or one or more oxygen or sulfur atoms or sulfoxide, sulfone, disulfide, amino, alkylamino, hydroxyl, quaternary ammonium, ureido, amide or ester groups, and
X− denotes an anion derived from an inorganic or organic acid;
A1, R13 and R15, with the two nitrogen atoms to which they are attached, may form a piperazine ring; in addition if A1 denotes a saturated or unsaturated, linear or branched alkylene or hydroxyalkylene radical, B1 may also denote a group (CH2)n—CO-D-OC—(CH2)n-in which D denotes:
a) a glycol residue of formula: —O—Z—O—, where Z denotes a linear or branched hydrocarbon radical or a group corresponding to one of the following formulae:
—(CH2—CH2—O)x—CH2—CH2—
—[CH2—CH(CH3)—O]y—CH2—CH(CH3)—
where x and y denote an integer from 1 to 4, representing a defined and unique degree of polymerization or any number from 1 to 4 representing a mean degree of polymerization;
b) a disecondary diamine residue such as a piperazine derivative;
c) a diprimary diamine residue of formula: —NH—Y—NH—, where Y denotes a linear or branched hydrocarbon radical or else the divalent radical
—CH2—CH2—S—S—CH2—CH2—;
d) a ureylene group of formula: —NH—CO—NH—;
(9) polyquaternary ammonium polymers consisting of units of formula (XVI):
in which formula:
R18, R19, R20 and R21, which are identical or different, represent a hydrogen atom or a methyl, ethyl, propyl,β-hydroxyethyl, β-hydroxypropyl or —CH2CH2(OCH2CH2)p OH radical,
where p is equal to 0 or to an integer between 1 and 6, provided that R18, R19, R20 and R21 do not simultaneously denote a hydrogen atom,
r and s, which are identical or different, are integers between 1 and 6,
q is equal to 0 or to an integer between 1 and 34,
X denotes a halogen atom,
A denotes a radical of a dihalide or preferably represents —CH2—CH2—O—CH2—CH2—,
(10) quaternary vinylpyrrolidone and vinylimidazole polymers,
(11) polyamines,
(12) the crosslinked polymers of methacryloyloxy(C1-C4 alkyl)tri(C1-C4 alkyl)ammonium salts, and
(13) polyalkyleneimines, polymers containing vinylpyridine or vinylpyridinium units, condensates of polyamines and epichiorohydrin, polyquaternary ureylenes and chitin derivatives.

### Claim 17 (depends on 16)

The composition as claimed in claim 16, wherein said cationic polymer is selected from the group consisting of cationic cyclopolymers, cationic polysaccharides, quaternary polymers of vinylpyrrolidone and of vinylimidazole, and mixtures thereof.

### Claim 18 (depends on 17)

The composition as claimed in claim 17, wherein said cationic polymer is a cyclopolymer selected from the group consisting of homopolymers of diallyldimethylammonium chloride and copolymers of acrylamide and diallyldimethylammonium chloride.

### Claim 19 (depends on 17)

The composition as claimed in claim 17, wherein said cationic polymer is a polysaccharide selected from the group consisting of starches modified with a 2,3-epoxypropyltrimethylammonium salt, guar gums modified with a 2,3-epoxypropyl-trimethylammonium salt and hydroxyethylcelluloses which have reacted with an epoxide substituted with a trimethylammonium group.

### Claim 20 (depends on 17)

The composition as claimed in claim 17 wherein said cationic polymer is a quaternary polymer of vinylpyrrolidone and of vinylimidazole selected from the group consisting of copolymers of vinylpyrrolidone and of salts of methylvinylimidazolium.

### Claim 21 (depends on 14)

The composition as claimed in claim 14 which comprises at least one cationic polysaccharide and at least one quaternary polymer of vinylpyrrolidone and of vinylimidazole.

### Claim 22 (depends on 14)

The composition as claimed in claim 14 which comprises at least one homopolymer of diallyldimethylammonium chloride and at least one quaternary polymer of vinylpyrrolidone and of vinylimidazole.

### Claim 23 (depends on 13)

The composition as claimed in claim 13 wherein the cationic polymer is present in an amount ranging from 0.001% to 20% by weight relative to the total weight of the composition.

### Claim 24 (depends on 1)

The composition as claimed in claim 1, further comprising at least one thickening agent.

### Claim 25 (depends on 24)

The composition as claimed in claim 24 , wherein said thickening agent is nonionic.

### Claim 26 (depends on 25)

The composition as claimed in claim 25, wherein said nonionic thickening agent is selected from the group consisting of:
nonionic homopolymers and copolymers containing ethylenically unsaturated monomers of the ester and/or amide type;
homo- and copolymers of vinylpyrrolidone, and
polysaccharides.

### Claim 27 (depends on 24)

The composition as claimed in claim 24, wherein said thickening agent is selected from the group consisting of polyacrylamides, methyl methacrylate/ethylene glycol dimethacrylate copolymers, butyl methacrylate/methyl methacrylate copolymers, and polymethyl methacrylates.

### Claim 28 (depends on 24)

The composition as claimed in claim 24, wherein said thickening agent is a crosslinked homopolymer of vinylpyrrolidone.

### Claim 29 (depends on 24)

The composition as claimed in claim 24, wherein said thickening agent is selected from the group consisting of glucans, modified or unmodified starches, amylose, amylopectin, glycogen, dextrans, celluloses and derivatives thereof (methylcelluloses, hydroxyalkylcelluloses, ethylhydroxyethylcelluloses), mannans, xylans, lignins, arabans, galactans, galacturonans, chitin, chitosans, glucoronoxylans, arabinoxylans, xyloglucans, glucomannans, pectic acids and pectins, arabinogalactans, carrageenans, agars, gums arabic, gums Tragacanth, Ghatti gums, Karaya gums, carob gums, galactomannans and mixtures thereof.

### Claim 30 (depends on 24)

The composition as claimed in claim 24, wherein the thickening agent is present in an amount of between 0.001% and 20% by weight relative to the total weight of the composition.

### Claim 31 (depends on 1)

The composition as claimed in claim 1, further comprising at least one surfactant selected from the group consisting of anionic, nonionic and amphoteric surfactants.

### Claim 32 (depends on 1)

The composition as claimed claim 1, further comprising at least one additional conditioner.

### Claim 33 (depends on 32)

The composition as claimed in claim 32, wherein the additional conditioner is selected from the group consisting of silicones, carboxylic esters comprising at least 12 carbon atoms, vegetable oils, mineral oils, synthetic oils and mixtures thereof.

### Claim 34 (depends on 1)

The composition as claimed in claim 1, wherein the cosmetically acceptable medium comprises water and, optionally, a cosmetically acceptable solvent.

### Claim 35 (depends on 34)

The composition as claimed in claim 34, wherein the medium comprises a cosmetically acceptable solvent selected from the group consisting of C1-C4 lower alcohols, alkylene glycols, polyol ethers, C5-C10 alkanes, acetone, methyl ethyl ketone, C1-C4 alkyl acetates, dimethoxyethane, diethoxyethane, and mixtures thereof.

### Claim 36 (depends on 1)

The composition as claimed in claim 1 further comprising at least one of the following:
a anionic, nonionic or amphoteric polymer, a nonpolymeric thickener, an opacifier, a pearlescent agent, a vitamin, a provitamin, a wax, a natural or synthetic ceramide, a perfume, a colorant, organic or inorganic particles, a preservative, or a pH stabilizing agent.

### Claim 37 (depends on 1)

The composition as claimed in claim 1, provided in the form of a shampoo, an after-shampoo, a composition for permanent waving, straightening, dyeing or bleaching the hair, a rinse-out composition to be applied between the two stages of a permanent waving or a hair straightening, or a washing composition for the body.

### Claim 38 (depends on 1)

The composition as claimed in claim 1, provided in the form of a rinse-out after-shampoo.

### Claim 39 (depends on 1)

A method for washing or for treating keratinous materials, comprising applying the composition of claim 1 thereto.

### Claim 40 (depends on 1)

A method for making hair shiny, comprising applying the composition of claim 1 to hair in need thereof.

### Claim 41 (depends on 1)

A method for making hair supple, comprising applying the composition of claim 1 to hair in need thereof.

### Claim 42 (depends on 1)

The composition as claimed in claim 1, wherein the liquid fatty alcohol is selected from the group consisting of: linear and saturated C8-C14 fatty alcohols; saturated or unsaturated, branched C12-C30 fatty alcohols; linear and unsaturated C14-C30 fatty alcohols; and mixtures thereof, wherein the liquid fatty alcohol is optionally oxyalkylenated with 1 to 15 mol of C2-C4 alkylene oxide.

### Claim 43 (depends on 1)

The composition as claimed in claim 1, wherein the liquid fatty alcohol is selected from the group consisting of: linear and saturated C8-C14 fatty alcohols; saturated or unsaturated, branched C12-C30 fatty alcohols; linear and unsaturated C14-C30 fatty alcohols; and mixtures thereof, wherein the liquid fatty alcohol is optionally oxyalkylenated with 1 to 5 mol of C2-C4 alkylene oxide.