# US 7,612,160 B2 · Polyether urethane containing allyl groups > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,612,160 B2 - Document ID: US7612160B2 - Status: Granted - Kind: B2 - Application number: 10/538,760 - Filed: 2003-12-16 - Published: 2006-11-02 - Granted: 2009-11-03 - Earliest claimed: 2002-12-17 - Assignees: BASF SE - Inventors: Son Nguyen-Kim; Klemens Mathauer; Claudia Wood - Web page: https://patentgrep.com/patent/US7612160B2 ## CPC - A61K 8/046: {Aerosols; Foams} - A61K 8/87: Polyurethanes - A61Q 5/02: Preparations for cleaning the hair - A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring - A61Q 5/12: Preparations containing hair conditioners - A61Q 19/00: Preparations for care of the skin - C08G 18/61: Polysiloxanes - C08G 18/6795: {Unsaturated polyethers} - 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 - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract The present invention relates to a mono- and/or polyallyl-polyether-urethane, to water-soluble or water-dispersible polymers which comprise such a polyether-urethane in copolymerized form, and to cosmetic or pharmaceutical compositions which comprise a water-soluble or water-dispersible polymer based on a mono- and/or polyallyl-polyether-urethane. ## Claims ### Claim 1 A hair treatment composition comprising water-soluble or water-dispersible polymer which comprises at least one free-radically polymerizable compound which has at least one α,β-ethylenically unsaturated double bond and at least a polyether-urethane in copolymerized form, where the polyether-urethane comprises at least one allyl group, and, in incorporated form, a) at least one polyalkylene glycol monoallyl ether having a number-average molecular weight in the range from 300 to 5000, b) optionally at least one compound which comprises at least two groups reactive toward isocyanate groups, and c) at least one polyisocyanate, as setting agent and/or as conditioner. ### Claim 2 (depends on 1) The hair treatment composition as claimed in claim 1, where the composition is in the form of a hair gel, hair mousse, shampoo, setting foam, hair tonic, hair spray or hair foam. ### Claim 3 A polyether-urethane comprising at least one allyl group, which comprises, in incorporated form, a) at least one polyalkylene glycol monoallyl ether having a number-average molecular weight in the range from 300 to 5000, b) at least one compound chosen from compounds b3) wherein b3) is at least one compound chosen from: polysiloxanes of the formula I.1 in which a and b, independently of one another, are 1 to 8, c is 2 to 100, R1 and R2, independently of one another, are C1-C8-alkyl, benzyl or phenyl, Z1 and R2, independently of one another, are OH, NHR3 or a radical of the formula II —(CH2CH2O)v(CH2CH(CH3)O)w—H (II), where in the formula II the alkylene oxide units can be in any order, and v and w, independently of one another, are an integer from 0 to 200, where the sum of v and w is >0, R3 is hydrogen, C1-C8-alkyl or C5-C8-cycloalkyl; polysiloxanes of the formula I.2 in which the siloxane units can be in any order, the radicals R4 are each, independently of one another, C1-C8-alkyl, d is an integer from 5 to 1000, e is an integer from 2 to 100, f is an integer from 2 to 8, Z3 is OH, NHR3, where R3 is as defined above, or a radical of the formula III —(OCH2CH2)x(OCH(CH3)CH2)y—OH (III), where in the formula III the alkylene oxide units can be in any order, x and v independently of one another, are an integer from 0 to 200, where the sum of x and v is >0, and mixtures thereof, c) at least one polyisocyanate. ### Claim 4 (depends on 3) A water-soluble or water-dispersible polymer which comprises, in copolymerized form, at least one polyether-urethane as defined in claim 3, and at least one free-radically polymerizable compound which has at least one α,β-ethylenically unsaturated double bond. ### Claim 5 (depends on 4) A polymer as claimed in claim 4, which comprises, in copolymerized form, at least one free-radically polymerizable hydrophilic nonionic compound M1). ### Claim 6 (depends on 5) A polymer as claimed in claim 5, where the compound M1) is chosen from primary amides of α,β-ethylenically unsaturated monocarboxylic acids, N-vinyllactams, N-vinylamides of saturated monocarboxylic acids, esters of α,β-ethylenically unsaturated mono- and dicarboxylic acids with C2-C4-alkanediols, amides of α,β-ethylenically unsaturated mono- and dicarboxylic acids with C2-C4-aminoalcohols which have a primary or secondary amino group, vinyl ethers, nonionic, hydrophilic vinyl- and allyl-substituted heterocyclic compounds and mixtures thereof. ### Claim 7 (depends on 6) A polymer as claimed in claim 6, which comprises, in copolymerized form, a compound M1) chosen from acrylamide, methacrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylformamide, N-vinylacetamide and mixtures thereof. ### Claim 8 (depends on 5) A polymer as claimed in claim 5, which additionally comprises, in copolymerized form, at least one free-radically polymerizable compound M2) with an α,β-ethylenically unsaturated double bond and at least one ionogenic and/or ionic group per molecule. ### Claim 9 (depends on 5) A polymer as claimed in claim 5, which additionally comprises, in copolymerized form, at least one free-radically polymerizable crosslinking compound with at least two α,β-ethylenically unsaturated double bonds per molecule. ### Claim 10 (depends on 5) A polymer as claimed in claim 5, which is obtained by free-radical copolymerization in the presence of a component d) chosen from d1) polyether-containing compounds, d2) polymers which have at least 50% by weight of repeat units derived from vinyl alcohol, d3) starch and starch derivatives, and mixtures thereof. ### Claim 11 (depends on 5, 10) A polymer as claimed in claim 5, obtained by free-radical polymerization of 1 to 25% weight, based on the total weight of the components used for the polymerization, of at least one polyallyl-polyether-urethane, 50 to 99% by weight of at least one free-radically polymerizable nonionic compound M1), 0 to 25% by weight of at least one monomer M2) with at least one ionogenic and/or ionic group per molecule, 0 to 10% by weight of at least one crosslinker, optionally in the presence of up to 25% by weight of at least one component d), as defined in claim 10. ### Claim 12 (depends on 5) A process for the preparation of a polymer as defined in claim 5 by free-radical polymerization in an aqueous solvent at a pH of from 5.5 to 8.0. ### Claim 13 (depends on 12) A process as claimed in claim 12, comprising a first polymerization step and a subsequent second polymerization step, where the reaction mixture between the first and second polymerization step is subjected to stripping with steam or to a steam distillation. ### Claim 14 (depends on 4) A cosmetic or pharmaceutical composition comprising A) at least one water-soluble or water-dispersible polymer as defined in claim 4, and B) at least one cosmetically or pharmaceutically acceptable carrier. ### Claim 15 (depends on 14) A composition as claimed in claim 14, where the component B) is chosen from i) water, ii) water-miscible organic solvents, i) oils, fats, waxes, ii) esters of C6-C30-monocarboxylic acids with mono-, di- or trihydric alcohols which are different from iii), iii) saturated acyclic and cyclic hydrocarbons, iv) fatty acids, v) fatty alcohols and mixtures thereof. ### Claim 16 (depends on 14) A composition as claimed in claim 14, further comprising at least on constituent different from copolymer A which is chosen form cosmetically active ingredients, emulsifiers, surfactants, preservatives, perfume oils, thickeners, hair polymers, hair and skin conditioners, graft polymers, water-soluble or dispersible silicone-containing polymers, light protection agents, bleaches, gel formers, care agents, colorants, tints, tanning agents, dyes, pigments, bodying agents, humectants, refatting agents, collagen, protein hydrolysates, lipids, antioxidants, antifoams, antistats, emollients, and softeners. ### Claim 17 (depends on 14) A composition as claimed in claim 14 in the form of a solution, a gel, wax, foam, spray, an ointment, cream, emulsion, suspension, lotion, milk or paste. ### Claim 18 (depends on 4) A cosmetic or pharmaceutical composition comprising a polymer as defined in claim 4 in skin cleansing compositions, compositions for the care and protection of the skin, nail care compositions, preparations for decorative cosmetics and hair treatment compositions. ### Claim 19 (depends on 18) The cosmetic or pharmaceutical composition as claimed in claim 18 in hair treatment compositions as thickener, setting agent and/or as conditioner. ### Claim 20 (depends on 19) The cosmetic or pharmaceutical composition as claimed in claim 19, where the composition is in the form of a hair gel, hair mousse, shampoo, setting foam, hair tonic, hair spray or hair foam. ### Claim 21 (depends on 4) A composition comprising a polymer as defined in claim 4 as auxiliary in pharmacy, or as auxiliary in (a) coating composition(s) for solid medicament forms, or as auxiliary in (a) coating composition(s) for the textile, paper, printing or leather industry, or for agrochemistry.