Neutralised cationic polymer, composition containing said polymer and a cosmetic treatment method

Abstract

The invention relates to an ethylene cationic polymer comprising at least one primary, secondary or tertiary protonable amine function which is at least partially neutralized by a polymer organic acid neutralizing agent which contains at least one carboxylic, sulphonic and/or phosphonic acid function. Said invention also relates to a cosmetic or pharmaceutical composition comprising said neutralized polymer in a physiologically acceptable medium, in particular, cosmetically or pharmaceutically acceptable medium. A method for cosmetically treating keratinic materials, such as a body of face skin, nails, hairs, eyebrows and/or eyelashes, consisting in applying the inventive cosmetic composition to said keratinic materials is also disclosed.

Claims

1. A cosmetic composition comprising, in a cosmetically acceptable medium: at least one cationic ethylenic polymer comprising at least one amine functional group chosen from primary amine functional groups that can be protonated, secondary amine functional groups that can be protonated and tertiary amine functional groups that can be protonated and comprising at least one neutralizing agent, wherein said at least one amine functional group being at least partially neutralized by the at least one neutralizing agent, wherein the at least one neutralizing agent is chosen from polymers having the following structures: CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2 R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2 R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2CH.sub.2 R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2CH.sub.2 R.sub.10 CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2OCOCH.sub.2CH.sub.2COOH CH.sub.3O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2OCOCH.sub.2CH.sub.2COOH R.sub.10(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2 R.sub.10 R.sub.10(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2 R.sub.10 R.sub.10CH.sub.2O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2R.sub.10 R.sub.10CH.sub.2O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2CH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2CH.sub.2O(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2CH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2COO(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2OCOCH.sub.2CH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2COO(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2OCOCH.sub.2CH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2CONH(CH.sub.2CH.sub.2O).sub.n-co-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2NHCOCH.sub.2CH.sub.2R.sub.10 R.sub.10CH.sub.2CH.sub.2CONH(CH.sub.2CH.sub.2O).sub.n-b-(CH.sub.2CHRO).sub.mCH.sub.2CH.sub.2NHCOCH.sub.2CH.sub.2R.sub.10 wherein: R is chosen from CH.sub.3, (CH.sub.2).sub.xCOOH; (CH.sub.2).sub.xSO.sub.3H; and (CH.sub.2).sub.xPO.sub.3H.sub.2; wherein x is chosen from an integer ranging from 1 to 8; R.sub.10 is chosen from COOH, SO.sub.3H and PO.sub.3H.sub.2; n is chosen from an integer ranging from 3 to 1000; m is chosen from an integer ranging from 0 to 200, with the proviso that when m is not 0, the n/m ratio is greater than 5 and at least one cosmetic additive selected from the group consisting of water or a mixture of water and hydrophilic organic solvent, waxes, pasty fatty substances, gums, pigments, nacres, fillers, water-soluble dyes, liposoluble dyes, a film-forming polymer other than said at least one cationic ethylenic polymer, surfactant, vitamins, pearlescent agents, thickeners, gelling agents, sequestering agents, fragrances, basifying or acidifying agents, preservatives, sunscreens, antioxidants, agents for combating hair loss, antidandruff agents, propellants and ceramides.

2. The composition according to claim 1, wherein the at least one neutralizing agent is chosen from: CH.sub.3O(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2 R.sub.10; CH.sub.3O(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2CH.sub.2 R.sub.10; R.sub.10(CH.sub.2CH.sub.2O).sub.nCH.sub.2CH.sub.2 R.sub.10; and R.sub.10CH.sub.2O(CH.sub.2CH.sub.2O).sub.nCH.sub.2R.sub.10, wherein R.sub.10 is chosen from COOH, SO.sub.3H and PO.sub.3H.sub.2; and n is an integer chosen from 3 to 1000.

3. The composition according to claim 1, wherein the at least one cationic ethylenic polymer is present in an amount ranging from 0.01 to 50% by weight of dry matter relative to the total weight of the cosmetic composition.

4. The composition according to claim 1, further comprises at least one constituent chosen from: water, hydrophilic organic solvents chosen from linear or branched C.sub.1-C.sub.6 monoalcohols, polyols and hydrophilic C.sub.2-C.sub.4 aldehydes; waxes, pasty fatty substances, and gums; lipophilic organic solvents; hydrocarbon-based oils of animal origin; hydrocarbon-based vegetable oils chosen from liquid triglycerides of fatty acids having 4 to 10 carbon atoms sunflower oils, maize oils, soya bean oils, grape seed oils, sesame oils, apricot oils, macadamia oils, castor oils, avocado oils, caprylic/capric acid triglycerides, jojoba oil and shea butter oil; linear or branched hydrocarbons of mineral or synthetic origin chosen from paraffin oils, vaseline, polydecenes, and hydrogenated polyisobutene; synthetic esters and ethers chosen from Purcellin oil, isopropyl myristate, 2-ethylhexyl palmitate, 2-octyldodecyl stearate, 2-octyldodecyl erucate, and isostearyl isostearate; hydroxylated esters chosen from isostearyl lactate, octyl hydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate, triisocetyl citrate, and heptanoates of fatty alcohols, octanoates of fatty alcohols and decanoates of fatty alcohols; polyol esters chosen from propylene glycol dioctanoate, neopentyl glycol diheptanoate, diethylene glycol diisononanoate; and pentaerythritol esters; fatty alcohols having 12 to 26 carbon atoms; partially hydrocarbon-based or silicone-based fluoro oils; silicone oils chosen from volatile or non-volatile, linear or cyclic polymethylsiloxanes (PDMS) that are liquid or pasty at ambient temperature optionally comprising a phenyl group; ketones that are liquid at ambient temperature; polypropylene glycol ethers that are liquid at ambient temperature; short-chain esters (having from 3 to 8 carbon atoms in total); ethers that are liquid at 25 C.; alkanes that are liquid at 25 C.; cyclic aromatic compounds that are liquid at 25 C.; aldehydes that are liquid at 25 C.; and pigments, nacres, fillers; water-soluble dyes; liposoluble dyes; polymers; anionic surfactants, amphoteric surfactants, non-ionic surfactants, cationic surfactants; vitamins, fragrances, thickeners, gelling agents, trace elements, demulcent agents, sequestering agents, fragrances, basifying agents, acidifying agents, preservatives, sunscreens, antioxidants, agents for combating hair loss, antidandruff agents, propellants and ceramides.

5. The composition according to claim 1, wherein the neutralizing agent is poly(ethylene glycol) bis(carboxymethyl) ether.

6. The composition according to claim 5, wherein the at least one cationic ethylenic polymer is poly(vinylamine-vinylformamide).

7. The composition according to claim 1, wherein the at least one cationic ethylenic polymer comprises at least one residue of monomers of formula (I): ##STR00028## wherein: R.sub.1 is chosen from hydrogen and linear or branched, hydrocarbon-based radicals of C.sub.pH.sub.2p+1 type, wherein p is chosen from an integer between 1 and 12; Z is a divalent group chosen from COO, CONH, CONCH.sub.3, OCO or O, SO.sub.2, COOCO and COCH.sub.2CO; x is 0 or 1, preferably 1; R.sub.2 is chosen from saturated or unsaturated, optionally aromatic, linear, branched or cyclic, carbon-based divalent radical having 1 to 30 carbon atoms, which may comprise 1 to 18 heteroatoms chosen from O, N, S, F, Cl, Br, Si and P; m is 0 or 1; X is chosen from: (a) guanidino groups; (b) amidino groups; (c) groups of formula N(R.sub.6)(R.sub.7), wherein R.sub.6 and R.sub.7 are independently chosen from: (i) a hydrogen atom; (ii) a linear, branched or cyclic, saturated or unsaturated, optionally aromatic alkyl group comprising from 1 to 18 carbon atoms, optionally comprising 1 to 10 heteroatoms chosen from O, N, S, F, Si and P; and (iii) R.sub.6 and R.sub.7 form, together with the nitrogen atom they are attached to, a ring of formula: ##STR00029## wherein the ring is saturated or unsaturated, optionally aromatic, and comprises from 5 to 8 atoms chosen from carbon, O, S and N; said first ring optionally being fused with at least one other ring chosen from, saturated or unsaturated, optionally aromatic rings comprising 5 to 7 atoms chosen from carbon, O, S and N; (c) rings chosen from: ##STR00030## wherein R.sub.4 and R.sub.5 form, together with the nitrogen atom they are attached to, a saturated or unsaturated, optionally aromatic, ring comprising 5 to 8 atoms chosen from, carbon, O, S and N; said ring optionally being fused with at least one other ring chosen from, saturated or unsaturated, optionally aromatic, rings comprising 5 to 7 atoms chosen from carbon, O, S and N; and R.sub.6 is chosen from H, CH.sub.3 and C.sub.2H.sub.5; wherein said at least one residue of monomers of formula (I) comprises at least one at least one amine functional group chosen from primary amine functional groups, secondary amine functional groups and tertiary amine functional groups, wherein said at least one amine functional group can be protonated at a pH ranging from 1 to 12.

8. The composition according to claim 7, wherein the monomers of formula (I) are chosen from dimethylaminopropyl (meth)acrylamide, dimethylaminoethyl (meth)acrylamide, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, tert-butylaminoethyl (meth)acrylate, morpholinoethyl (meth)acrylate, vinylimidazole, vinylpyridine, vinylamine, allylamine, and the monomers below: ##STR00031## wherein R is chosen from hydrogen and methyl.

9. The composition according to claim 1, wherein the at least one cationic ethylenic polymer comprises at least one residue of monomers of formula (II): ##STR00032## wherein R.sub.3 is chosen from hydrogen and linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based radicas1 having 1 to 30 carbon atoms, optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Cl, Br, Si and P, wherein the at least one monomer of formula (II) comprises at least one amine functional group chosen from primary, secondary and tertiary amine functional groups, wherein the at least one amine functional group can be protonated at a pH ranging from 1 to 12.

10. The composition according to claim 9, wherein the monomers of formula (II) are chosen from N-methyldiallylamine and diallylamine.

11. The composition according to claim 1, wherein the polymer comprises at least one residue of monomers of formula (III): ##STR00033## wherein R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, and R.sub.12, independently of one another, are chosen from: a hydrogen atom; an NR.sub.13R.sub.13 groups, wherein R.sub.13 and R.sub.13, independently of one another, are chosen from hydrogen and linear, branched or cyclic, saturated or unsaturated, optionally aromatic alkyls comprising from 1 to 18 carbon atoms, optionally comprising 1 to 10 heteroatoms chosen from O, N, S, F, Si and P; and a linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based radicals having 1 to 30 carbon atoms, optionally comprising 1 to 18 heteroatoms chosen from O, N, S, F, Si and P, wherein monomers of formula (III) comprise at least one amine functional group chosen from primary amine functional group, secondary amine functional group and tertiary amine functional groups, wherein the amine functional group can be protonated at a pH ranging from 1 to 12.

12. The composition according to claim 11, wherein the monomers of formula (III) are chosen from: ##STR00034##

13. The composition according to claim 1, wherein the at least one cationic ethylenic polymer further comprises at least one residue of at least one additional monomer in an amount ranging from 0.01 to 99% by weight relative to the weight of the at least one cationic ethylenic polymer.

14. The composition according to claim 13, wherein the at least additional monomer is chosen from: (i) (meth)acrylic acid esters of formula CH.sub.2CHCOOR1 or CH.sub.2C(CH.sub.3)COOR1 wherein R.sub.1 is chosen from linear, branched or cyclic, saturated or unsaturated, optionally aromatic carbon-based radicals having 1 to 30 carbon atoms, optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12 functional groups chosen from OH (hydroxyl), OR with R being chosen from C.sub.1-C.sub.6 alkyl (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONR, OCONH, NHCONH, NRCONR, CF.sub.3, CN, epoxy, NHCO, N(R)CO wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyls optionally comprising 1-12 heteroatoms; (ii) (meth)acrylic acid amides of formula CH.sub.2CHCONR.sub.2R.sub.2 or CH.sub.2C(CH.sub.3)CONR.sub.2R.sub.2, wherein R.sub.2, R.sub.2, are independently chosen from hydrogen and linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based radicals having 1 to 30 carbon atoms, optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12 functional groups chosen from OH (hydroxyl), OR with R being chosen from C.sub.1-C.sub.6 alkyls (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONR, OCONH, NHCONH, NRCONR, CF.sub.3, CN, epoxy, NHCO, N(R)CO, wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyls optionally comprising 1-12 heteroatoms; (iii) vinyl esters of formula CH.sub.2CHOCOR.sub.3 or CH.sub.2C(CH.sub.3)OCOR.sub.3, wherein R.sub.3 is chosen from linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based radicals having 1 to 30 carbon atoms, optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12 functional groups chosen from OH (hydroxyl), OR, wherein R being chosen from C.sub.1-C.sub.6 alkyls (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONR, OCONH, NHCONH, NRCONR, CF.sub.3, CN, epoxy, NHCO, N(R)CO, wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyls optionally comprising 1-12 heteroatoms; (iv) vinyl ethers of formula CH.sub.2CHOR.sub.4 or CH.sub.2C(CH.sub.3)OR.sub.4, wherein R.sub.4 is chosen from linear, branched or cyclic, saturated or unsaturated, optionally aromatic, carbon-based radicals having 1 to 30 carbon atoms, optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12 functional groups chosen from OH (hydroxyl), OR, with R being chosen from C.sub.1-C.sub.6 alkyls (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONR, OCONH, NHCONH, NRCONR, CF.sub.3, CN, epoxy, NHCO, N(R)CO, wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyls optionally comprising 1-12 heteroatoms; (v) vinyl compounds of formula CHR.sub.5CR.sub.5R.sub.5 wherein: R.sub.5 is chosen from H and COOH, and R.sub.5 is chosen from H, CN and COOH, and R.sub.5 is chosen from: hydrogen, OH, CHO, halogens, COOH, CH.sub.2COOH, NHC(O)H, N(CH.sub.3)C(O)H, NHC(O)CH.sub.3, N(CH.sub.3)C(O)CH.sub.3; rings chosen from: ##STR00035## wherein R.sub.15 and R.sub.15 are independently chosen from hydrogen, linear or branched, saturated or unsaturated, optionally aromatic, cyclic or non-cyclic alkyl groups, comprising 1 to 25 carbon atoms, optionally comprising heteroatoms chosen from O, N, S and P; said alkyl groups may optionally substituted by at least one substituent chosen from OH and halogen atoms; linear or branched alkyl groups comprising 1 to 25 carbon atoms; C.sub.3 to C.sub.8 cycloalkyl groups; C.sub.6 to C.sub.20 aryl groups; C.sub.7 to C.sub.30 aralkyl groups, wherein alkyl having 1 to 4 carbons; heterocyclic groups having 4 to 12 chain members containing at least one heteroatom chosen from O, N and S; and heterocycloalkyl groups, wherein alkyl having 1 to 4 carbons, wherein said alkyl, cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12 functional groups chosen from OH (hydroxyl), OR with R being chosen from C.sub.1-C.sub.6 alkyls (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONR, OCONH, NHCONH, NRCONR, CF.sub.3, CN, epoxy, NHCO, N(R)CO, wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyl optionally comprising 1-12 heteroatoms; and optionally substituted by at least one linear or branched, C.sub.1-C.sub.4 alkyl groups, optionally comprising 0 to 2 ether functional groups (O) and optionally 0 to 12, functional groups chosen from OH (hydroxyl), OR with R a C.sub.1-C.sub.6 alkyl (alkoxy), CN, X (halogen), CO, SO.sub.3H, COOH, OCOO, COO, OCONH, NHCONH, CF.sub.3, CN, epoxy, NHCO, N(R)CO, wherein R is chosen from linear or branched C.sub.1-C.sub.22 alkyl optionally comprising 1-12 heteroatoms, (vii) the following anionic monomers, and salts thereof: maleic anhydride, acrylic acid, methacrylic acid, crotonic acid, itaconic acid, fumaric acid, maleic acid, 2-carboxyethyl acrylate (CH.sub.2CHC(O)O(CH.sub.2).sub.2COOH), styrenesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, vinylbenzoic acid, vinylphosphonic acid, sulfopropyl (meth)acrylate; (viii) the following amphoteric monomers: N,N-dimethyl-N-(2-methacryloyloxyethyl)-N-(3-sulfopropyl)ammonium betaine; N,N-dimethyl-N-(3-methacrylamidopropyl)-N-(3-sulfopropyl)ammonium betaine, and 1-(3-sulfopropyl)-2-vinylpyridinium betaine; and 2-(methacryloyloxy)ethyl phosphorylcholine; (ix) monomers of formula: ##STR00036## wherein R.sub.8 is chosen from H and linear or branched, saturated or unsaturated, optionally aromatic, cyclic or non-cyclic alkyl group comprising 1 to 25 carbon atoms, optionally comprising at least one heteroatoms chosen from O, N, S and P; said alkyl groups optionally by at least one chosen from OH and halogen atoms; (x) quaternized monomers of formula (I), quaternized monomers of formula (II) and quaternized monomers of formula (III; (xi) multivalent compounds comprising at least two polymerizable functional groups chosen from vinyl, (meth)acrylic, allyl and (meth)acrylamide type.

15. The composition according to claim 14, wherein the at least one additional monomer is chosen from vinyl neodecanoate, vinyl tert-butylbenzoate; vinylpyrrolidone; vinylcaprolactam; N-vinylformamide; N,N-dimethyldiallylammonium chloride; triethylammonium ethylmethacrylate chloride; ethyl, methyl, tert-butyl or isobornyl (meth)acrylate; vinyl acetate, crotonic acid; (meth)acrylic acid, methacryloyl ethyl betaine, octylacrylamide; N-methyl-N-vinylimidazolinium chloride, 1-eicosene, tert-butylacrylamide, acrylamide, and hexadecene.

16. The composition according to claim 1, wherein the at least one cationic ethylenic polymer is chosen from: poly(vinylpyrrolidone-co-dimethylaminoethyl methacrylate) copolymers; poly(vinylcaprolactam-co-vinylpyrrolidone-co-dimethylaminoethyl methacrylate) copolymers; poly(vinylpyrrolidone-co-dimethylaminopropyl methacrylamide) copolymers; poly(vinylpyrrolidone-co-polyvinylcaprolactam-co-dimethylaminopropyl methacrylamide) copolymers; poly(vinylamine), poly(allylamine), poly(diallylamine); and poly(N-vinylformamide-co-vinylamine) copolymers.

17. The composition according to claim 1, wherein the at least one cationic ethylenic polymer comprises at least 3 repeating units chosen from: ##STR00037##

18. The composition according to claim 1, wherein the at least one neutralizing agent is present in an amount ranging from 0.01 to 3 molar equivalents relative to the total amine functional groups of the at least one cationic ethylenic polymer.

19. A method for treating keratinous substances chosen from the skin of the body or face, nails, hairs, eyelashes and eyebrows, comprising applying to said keratinous substances the cosmetic composition according to claim 1.

Description

EXAMPLE 1

(1) Introduced into a 500 ml beaker equipped with a magnetic bar were 10 g of poly(4-vinylpyridine) with MW=160,000 g/mol (Aldrich) and the indicated amount of neutralizing agent was added. This mixture, in the form of a white paste, was heated at 60 C. for 30 minutes, then 90 ml of water were added. The mixture was kept at 60 C. for 1 hour. A partially or completely neutralized polymer solution was obtained.

(2) In an identical manner, various homopolymers and copolymers were prepared that were neutralized with the same neutralizing agent.

(3) The results are given in the table below.

(4) TABLE-US-00002 Neutralizing Polymer MW agent* Solution** Poly(4-vinylpyridine) 60,000 0.5 pH = 3.72 22.9% DM Polyvinylpyridine 60,000 0.25 pH = 5.11 18.5% DM Poly(4-vinylpyridine) 160,000 0.125 pH = 4.69 15.01% DM Poly(4-vinylpyridine) 160,000 0.5 pH = 3.53 23.4% DM Poly(vinylpyridine) 5000 0.5 pH = 3.42 8.42% DM Poly(styrene-co-vinyl 130,000 0.5 pH = 3.72 pyridine) 30/70 8.45% DM Poly(styrene-co-vinyl 130,000 0.25 pH = 3.80 pyridine) 30/70 9.02% DM Poly(styrene-co-vinyl 220,000 0.25 pH = 3.08 pyridine) 30/70 9.09% DM Poly(styrene-co-vinyl 220,000 0.5 pH = 3.42 pyridine) 30/70 8.45% DM DM: dry matter *neutralizing agent: amount, in molar equivalent, of neutralizing agent added **pH and amount of dry matter in the solution obtained

(5) For comparison, the following were prepared:

(6) TABLE-US-00003 Neutralizing Polymer MW agent* Solution** Polyvinylpyridine 160,000 Neutralized pH = 1.1 with 1 eq. 10.9% DM HCl Polyvinylpyridine 60,000 Neutralized pH = 1 with 1 eq. 9.75% DM HCl Polyvinylpyridine 5000 Neutralized pH = 1 with 1 eq. 8.68% DM HCl Poly(styrene-co- 220,000 Neutralized pH = 1 vinylpyridine) with 1 eq. 7.5% DM 30/70 HCl

EXAMPLE 2

(7) In an identical manner to Example 1, the following were neutralized with a CO.sub.2H-PEG-CO.sub.2H neutralizing agent: copolymers based on dimethylaminopropyl methacrylamide (DMAPMA) and on vinylpyrrolidone (VP): commercial product Styleze CC10 from ISP; a DMAPMA homopolymer; poly(vinylamine/vinylformamide) copolymers VA/VF: commercial products from BASF: Lupamin 1595 (degree of hydrolysis of VA90%); Lupamin 9095 (degree of hydrolysis of VA90%), Lupamin 4595 (degree of hydrolysis of VA90%); Lupamin 9030 (degree of hydrolysis of VA30%); and poly(allylamine) homopolymers.

(8) TABLE-US-00004 Neutralizing Polymer MW agent* Solution** Poly(DMAPMA/VP) 0.5 pH = 2.78 6.85% DM Poly(DMAPMA/VP) 3 pH = 11.38 24.9% DM Poly(DMAPMA) 0.5 pH = 5.79 29.9% DM Poly(VA/VF), <10,000 0.25 pH = 3.22 Lupamin 1595 55.20% DM Poly(VA/VF), 340,000 0.25 pH = 3.20 Lupamin 9095 25.97% DM Poly(VA/VF), 45,000 0.5 pH =3.05 Lupamin 4595 53.6% DM Poly(VA/VF), 340,000 1 pH = 2.85 Lupamin 3095 36.60% DM Poly(VA/VF), 340,000 0.5 pH = 2.99 Lupamin 3095 30.2% DM Poly(VA/VF), 340,000 0.125 pH = 3.64 Lupamin 3095 16.8% DM Poly(VA/VF), 340,000 0.5 pH = 4.36 Lupamin 3095 19.6% DM Poly(allylamine) 17,000 0.06 pH = 10.06 20.5% DM Poly(allylamine) 17,000 0.2 pH = 8.75 30.9% DM Poly(allylamine) 17,000 1 pH = 3.16 34.1% DM Poly(allylamine) 65,000 0.06 pH = 10.29 17.7% DM Poly(allylamine) 65,000 0.2 pH = 8.70 18.9% DM Poly(allylamine) 65,000 1 pH = 3.45 30.2% DM Poly(allylamine) 3000 0.2 pH = 9.84 44.1% DM Poly(allylamine) 3000 1 pH = 3.43 13.6% DM

(9) For comparison, the following were prepared:

(10) TABLE-US-00005 Neutralizing Polymer MW agent* Solution** Polyallylamine 17,000 Neutralized 7.09% DM with 1 eq. HCl Polyallyamine 65,000 Neutralized 6.8% DM with 1 eq. HCl Polyallyamine 3000 Neutralized 40.0% DM with 1 eq. HCl

EXAMPLE 3

(11) In an identical manner to Example 1, poly(diallylamine) homopolymers were neutralized with the same neutralizing agent.

(12) Poly(diallylamine) were synthesized as follows: diallylamine (5.0 g, 0.0515 mol) was dissolved in 6.18 g (10% excess) of concentrated hydrochloric acid (36% solution). The temperature was kept at 0 C., and the solution was then purged with argon.

(13) The initiator (V50: 2,2-azo-bis(2-amidinopropane) dihydrochloride) (0.14 g, 1 mol %) was added and the mixture was again purged with argon then placed in an oil bath at 60 C. for 24 hours. The viscose yellow solution obtained was diluted (1 volume) with water of HPLC quality. The solution was then cooled by a bath of ice and ethanol. 2 eq. of sodium hydroxide were added very slowly, then the precipitated polymer was filtered, washed with HPLC quality water and freeze dried. This polymer could then be neutralized.

(14) By way of comparison, a neutralization was carried out with 1N HCl (10% aqueous solution) in a stoichiometric amount.

(15) TABLE-US-00006 Neutralizing agent Form Example A 1 eq. of 26% DM aqueous neutralizing solution agent according to the invention Example B 0.75 eq. of 19% DM aqueous neutralizing solution agent according to the invention Example C 0.5 eq. of 19% DM aqueous neutralizing solution agent according to the invention Example D 0.25 eq. of 14% DM aqueous neutralizing solution agent according to the invention Counterexample E 1 eq. HCl *DM: dry matter

(16) 1% of active material (AM) of the above A and E neutralized polymers was introduced into a surfactant base comprising 12.5% AM of lauryl ether sulfate and 2.5% AM of cocoyl betaine, in water.

(17) With the composition according to the invention, a good disentangling in a wet medium and a good cosmetic quality (feel, softness) in a dry medium were observed. Much better disentangling and smoothing were observed with the composition according to the invention relative to the composition comprising the counterexample E.

EXAMPLE 4: STYLING LOTION

(18) Introduced into a pump dispenser were: 6% AM of an aqueous solution of polymer A from Example 3; qs preservative; and qs for 100% water.

(19) The polymer solution was sprayed on to a 1.5 g lock of hair for 5 seconds. The lock was then wound around a 1 cm diameter curler, then dried at 70 C. for 30 minutes. Next, the lock was unwound.

(20) The same thing was carried out replacing the polymer A with the polymer E (counterexample).

(21) The following were noted for the hairstyle treated with the composition according to the invention in comparison with the hairstyle treated with the counterexample: a better hold on the locks of the hair style and the curls when they are present, an improved feel, especially in terms of softness, and also better disentangling.