WO2020002434A1 - Composition comprenant un polyuréthane, un polymère cationique, un organosilane et un polysaccharide - Google Patents

Composition comprenant un polyuréthane, un polymère cationique, un organosilane et un polysaccharide Download PDF

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WO2020002434A1
WO2020002434A1 PCT/EP2019/067014 EP2019067014W WO2020002434A1 WO 2020002434 A1 WO2020002434 A1 WO 2020002434A1 EP 2019067014 W EP2019067014 W EP 2019067014W WO 2020002434 A1 WO2020002434 A1 WO 2020002434A1
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chosen
polymers
mixtures
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Ségolène DE MENTHIERE
Valérie Vieira
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LOreal SA
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LOreal SA
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6651—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D139/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
    • C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C09D139/06—Homopolymers or copolymers of N-vinyl-pyrrolidones

Definitions

  • the present invention relates to a composition, notably a cosmetic composition, notably a hair composition, comprising one or more polyurethanes, one or more cationic polymers, one or more organosilanes and one or more polysaccharides.
  • the invention also relates to a process for shaping and/or conditioning keratin fibres, in particular human keratin fibres such as the hair, comprising at least one step of applying to said fibres the composition according to the invention.
  • the invention lastly relates to the use of the composition according to the invention for shaping and/or conditioning keratin fibres, in particular human keratin fibres such as the hair, and notably for defining the hair curls.
  • the conventional processes for modifying curly hair comprise straightening or relaxing the hair.
  • the processes for straightening or relaxing the hair generally involve reducing agents based on thiol or strong alkaline agents.
  • the first technique consists, in a first stage, in opening the disulfide bonds using a composition comprising a reducing agent, and then, in a second stage, after having generally rinsed the hair, in reconstituting said disulfide bonds by applying to the hair, which has been placed beforehand under tension, for example by means of rollers, an oxidizing composition also known as a "fixer” (fixing step), so as to give the head of hair the desired shape.
  • the second technique consists in performing a lanthionization operation, using a composition containing a base belonging to the hydroxide family. Contrary to the first one, this second technique does not require a fixing step, since the formation of the lanthionine bonds is irreversible. Thus, this technique makes it possible, without preference, to perform waving, relaxing, uncurling or straightening of the hair. In particular, it is mainly used for relaxing naturally curly hair.
  • Formaldehyde subjected to a temperature that may be up to 200°C or more, for example by means of an iron, crosslinks the proteins of the keratin fibres by reaction on their nucleophilic sites.
  • compositions which can maintain hair curls while at the same time giving them good definition and regularity, and which make it possible to obtain good control of the frizziness and volume of the hair, while at the same time providing haircare, which may be persistent on shampooing several times.
  • composition comprising a combination of one or more polyurethanes with one or more cationic polymers, one or more organosilanes and one or more polysaccharides makes it possible to solve the abovementioned problems.
  • composition comprising:
  • organosilane(s) being chosen from the compounds of formula (X), oligomers thereof, hydrolysis products thereof and/or mixtures thereof:
  • R1 is a cyclic or acyclic, linear or branched, saturated or unsaturated C1 to C22, notably C2 to C20, hydrocarbon-based chain, which may be substituted with one or more groups chosen from amine groups NH2 or NHR (R being a linear or branched C1 to C20, notably C1 to C6, alkyl, or a C3 to C40 cycloalkyl or a C6 to C30 aromatic radical); a hydroxyl group (OH); a thiol group; an aryl group (more particularly benzyl) which is unsubstituted or substituted with an NH2 or NHR group; it being possible for R1 to be interrupted with one or more oxygen, sulfur and/or nitrogen heteroatoms and/or with one or more carbonyl groups (CO);
  • amine groups NH2 or NHR R being a linear or branched C1 to C20, notably C1 to C6, alkyl, or a C3 to C40 cyclo
  • R2 and R3 which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms,
  • - y denotes an integer ranging from 0 to 3
  • - z denotes an integer ranging from 0 to 3
  • - x denotes an integer ranging from 0 to 2
  • composition according to the invention makes it possible to obtain well-defined curls, good control of the frizziness and volume of the hair, and to give the hair good manageability, these effects also persisting throughout the day, or even for several days.
  • composition according to the invention affords a hair conditioning effect and makes it possible in particular to give a pleasant cosmetic feel, notably a smooth feel, to facilitate the disentangling of the hair and to provide sheen.
  • composition according to the invention makes it possible to improve the persistence of the shaping of keratin fibres and of the conditioning properties; the shaping, manageability, frizz-control and conditioning properties can in particular be persistent with respect to at least one shampoo wash, in particular to at least two shampoo washes, better still to at least three shampoo washes, or even to at least four shampoo washes.
  • composition according to the invention is easy to use, notably being applied to wet hair after shampooing, to obtain a styling effect.
  • a subject of the invention is also a process for shaping and/or conditioning keratin fibres, in particular human keratin fibres such as the hair, comprising at least one step of applying to said fibres the composition according to the invention.
  • the expression “at least one” is equivalent to the expression “one or more” and can be substituted for said expression; the expression “between” is equivalent to the expression “ranging from” and can be substituted for said expression, and implies that the limits are included.
  • composition according to the invention comprises a polyurethane.
  • the polyurethane may be associative or non-associative.
  • non-associative polyurethanes refers to polycondensates comprising at least one polyurethane block and not comprising in their structure a terminal or pendent alkyl or alkenyl chain, including more than 10 carbon atoms. They are described in particular in the patents EP 0 751 162, EP 0 637 600, EP 0 648 485 and FR 2 743 297, of which the applicant is the proprietor, and also in the patents EP 0 656 021 and WO 94/03510 from the company BASF and EP 0 619 1 1 1 from the company National Starch.
  • the non-associative polyurethanes used in accordance with the invention may be soluble in the cosmetically acceptable aqueous medium, notably after neutralization with an organic or mineral base, or else may form a dispersion in this medium.
  • the dispersion may then comprise at least 0.05% of surfactant allowing the setting in dispersion and the maintenance in dispersion of the non-associative polyurethane.
  • any type of surfactant may be used in said dispersion, but preferably a nonionic surfactant.
  • the mean size of the non-associative polyurethane particles in the dispersion is preferably between 0.1 and 1 micrometre.
  • the non-associative polyurethane may be formed by an arrangement of blocks, this arrangement being obtained notably from:
  • the compounds (1 ) are chosen from the group comprising diols, diamines, polyesterols and polyetherols, or mixtures thereof.
  • the compounds (1 ) that are preferred are linear polyethylene glycols and polypropylene glycols, in particular those that are obtained by reaction of ethylene oxide or propylene oxide with water or diethylene or dipropylene glycol in the presence of sodium hydroxide as catalyst.
  • These polyalkylene glycols generally have a molecular mass of between about 600 and 20 000.
  • polyhydroxylated compounds such as polyether-diols, polyester-diols, polyacetal-diols, polyamide-diols, polyester-polyamide-diols, poly(alkylene ether)-diols, polythioether- diols and polycarbonate-diols.
  • the preferred polyether-diols are, for example, the products of condensation of ethylene oxide, of propylene oxide or of tetrahydrofuran, the grafted or block copolymerization or condensation products thereof, such as mixtures of condensates of ethylene oxide and of propylene oxide, and products of polymerization of olefins, under high pressure, with alkylene oxide condensates.
  • Suitable polyether-diols are prepared, for example, by condensation of alkylene oxides and of polyhydric alcohols, such as ethylene glycol, 1 ,2-propylene glycol and 1 ,4-butanediol.
  • polyester-diols, polyester-amides and polyamide-diols are preferably saturated and are obtained, for example, from the reaction of saturated or unsaturated polycarboxylic acids with polyhydric alcohols, diamines or polyamines.
  • polyhydric alcohols for example, of adipic acid, succinic acid, phthalic acid, terephthalic acid and maleic acid.
  • Suitable polyhydric alcohols for preparing the polyesters include, for example, ethylene glycol, 1 ,2-propylene glycol, 1 ,4-butanediol, neopentyl glycol and hexanediol.
  • Use may also be made of amino alcohols, for instance ethanolamine.
  • Suitable diamines for preparing the amide-polyesters are ethylenediamine and hexamethylenediamine.
  • Suitable polyacetals may be prepared, for example, from 1 ,4-butanediol or hexanediol and from formaldehyde.
  • Suitable polythioethers may be prepared, for example, by condensation reaction between thioglycols alone or in combination with other glycols such as ethylene glycol, 1 ,2-propylene glycol or with other polyhydroxylated compounds.
  • Polyhydroxylated compounds already containing urethane groups, natural polyols, which may be further modified, for example castor oil and carbohydrates, may also be used.
  • the compound of group (1 ) is a polyesterol, notably a polyester- diol formed by reaction of at least one (di)-polyol (1 a ) and of at least one acid (1 b ).
  • the (di)-polyol (1 a ) is chosen in particular from the group comprising neopentyl glycol, 1 ,4- butanediol, hexanediol, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, neopentyl glycol and (di)-polyethylene glycol.
  • the acid (1 b ) is chosen in particular from the group comprising phthalic acid, isophthalic acid, adipic acid and (poly)lactic acid.
  • compound (2) use may be made notably of a hydroxycarboxylic acid such as dimethylolpropanoic acid (DMPA) or a 2,2-hydroxymethylcarboxylic acid.
  • DMPA dimethylolpropanoic acid
  • compound (2) is useful as a coupling block.
  • the compounds that are preferred as compounds (2) are those comprising at least one poly(a,a-dihydroxylated carboxylic acid).
  • the compounds (2) that are particularly preferred in accordance with the invention are those chosen from the group comprising 2,2-bis(hydroxymethyl)acetic acid, 2,2- dihydroxymethylpropionic acid, 2,2-dihydroxymethylbutyric acid and 2,2- dihydroxymethylpentanoic acid.
  • the diisocyanate or polyisocyanate (3) may be chosen in particular from the group comprising hexamethylene diisocyanate, isophorone diisocyanate (IPDI), tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate (DPMD) and 4,4'-dicyclohexylmethane diisocyanate (DCMD), methylenedi-p-phenyl diisocyanate, methylenebis(4-cyclohexyl isocyanate), toluene diisocyanates, 1 ,5-naphthalene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2'-dimethyl-4,4'-diphenylmethane diisocyanate, 1 ,3-phenylene diisocyanate, 1 ,4-phenylene diisocyanate, mixtures of 2,4- and 2,6-toluene diisocyanates, 2,
  • the non-associative polyurethane may be formed using an additional compound (4) generally serving to extend its chain.
  • These compounds (4) may be chosen from the group notably comprising saturated or unsaturated glycols such as ethylene glycol, diethylene glycol, neopentyl glycol, triethylene glycol; amino alcohols such as ethanolamine, propanolamine, butanolamine; heterocyclic, aromatic, cycloaliphatic and aliphatic primary amines; diamines; carboxylic acids such as aliphatic, aromatic and heterocyclic carboxylic acids, for instance oxalic acid, succinic acid, glutaric acid, adipic acid, sebacic acid and terephthalic acid; and aminocarboxylic acids.
  • the preferred compounds (4) are aliphatic diols.
  • the non-associative polyurethanes used according to the invention may also be formed from additional compounds (5) bearing a silicone backbone, such as polysiloxanes, polyalkylsiloxanes or polyarylsiloxanes, notably polyethylsiloxanes, polymethylsiloxanes and polyphenylsiloxanes, optionally including hydrocarbon-based chains grafted onto the silicon atoms.
  • additional compounds (5) bearing a silicone backbone such as polysiloxanes, polyalkylsiloxanes or polyarylsiloxanes, notably polyethylsiloxanes, polymethylsiloxanes and polyphenylsiloxanes, optionally including hydrocarbon-based chains grafted onto the silicon atoms.
  • the non-associative polyurethanes advantageously used comprise a base repeating unit corresponding to the general formula (G):
  • - B is a Ci to C30 divalent hydrocarbon-based group, this group being optionally substituted with a group including one or more carboxylic acid functions and/or one or more sulfonic acid functions, said carboxylic acid and/or sulfonic acid functions being in free form or else partially or totally neutralized with a mineral or organic base, and
  • R is a divalent group chosen from C1 to C20 aliphatic, C3 to C20 cycloaliphatic and C6 to C20 aromatic hydrocarbon-based groups, for instance C1 to C20 alkylene, Ce to C20 arylene, C3 to C20 cycloalkylene groups, or combinations thereof, these groups being optionally substituted.
  • the group R is chosen from hexamethylene, 4,4’- biphenylenemethane, 2,4- and/or 2,6-tolylene, 1 ,5-naphthylene, p-phenylene and methylene-4, 4-bis(cyclohexyl) groups and the divalent group derived from isophorone.
  • the non-associative polyurethane used in the present invention may also advantageously comprise at least one polysiloxane block, the base repeating unit of which corresponds, for example, to the general formula (IG):
  • - P is a polysiloxane segment
  • R is a divalent group chosen from C1 to C20 aliphatic, C3 to C20 cycloaliphatic and C 6 to C20 aromatic hydrocarbon-based groups, for instance C1 to C20 alkylene, Ce to C20 arylene, C 3 to C 20 cycloalkylene groups, or combinations thereof, these groups being optionally substituted.
  • polysiloxane segment P corresponds to the general formula (III’) below:
  • the groups A which may be identical or different, are chosen firstly from C1-C20 monovalent hydrocarbon-based groups that are free or substantially free of ethylenic unsaturation and, secondly, from aromatic groups,
  • - Y represents a divalent hydrocarbon-based group
  • - z represents an integer chosen such that the weight-average molecular mass of the polysiloxane segment is between 300 and 10 000.
  • the divalent group Y is chosen from the alkylene groups of formula - (CH2) a -, in which a represents an integer that may be between 1 and 10.
  • the groups A may be chosen from C1-8 alkyl groups, in particular methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl and octyl groups; C3-8 cycloalkyl groups, in particular the cyclohexyl group; C6-10 aryl groups, notably phenyl; C7-10 arylalkyl groups, notably benzyl and phenylethyl, and also tolyl and xylyl groups.
  • non-associative polyurethanes examples include the dimethylolpropionic acid/isophorone diisocyanate/neopentyl glycol/polyesterdiols copolymer (also known under the name polyurethane-1 , INCI name) sold under the brand name Luviset ® PUR by the company BASF, and the dimethylolpropionic acid/isophorone diisocyanate/neopentyl glycol/polyesterdiols/silicone diamine copolymer (also known under the name polyurethane-6, INCI name) sold under the brand name Luviset ® Si PUR A by the company BASF.
  • dimethylolpropionic acid/isophorone diisocyanate/neopentyl glycol/polyesterdiols copolymer also known under the name polyurethane-1 , INCI name
  • sociative polyurethane refers to a polyurethane bearing at least one terminal or pendent alkyl chain including at least 10 carbon atoms. This type of polymer is capable of interacting with itself or with particular compounds such as surfactants to lead to thickening of the medium.
  • the associative polyurethanes used in the invention may be cationic, anionic or nonionic. They are preferably anionic or nonionic.
  • An example of an anionic associative polyurethane that may notably be mentioned is an alkali-soluble or alkali-swellable acrylic terpolymer. It is characterized in that it comprises:
  • a nonionic urethane monomer which is the reaction product of a monohydric nonionic surfactant with a monoethylenically unsaturated monoisocyanate.
  • the a,b-monoethylenically unsaturated carboxylic acid a) may be chosen from numerous acids and in particular acrylic acid, methacrylic acid, itaconic acid and maleic acid. Methacrylic acid is preferred. A large proportion of acid is essential to give a polymer structure which dissolves and gives thickening by reaction with an alkaline compound such as sodium hydroxide, alkanolamines, aminomethylpropanol or aminomethylpropanediol.
  • an alkaline compound such as sodium hydroxide, alkanolamines, aminomethylpropanol or aminomethylpropanediol.
  • the terpolymer must also contain a large proportion indicated above of a monoethylenically unsaturated monomer b) which has no surfactant properties.
  • the preferred monomers are those which give water-insoluble polymers when they are homopolymerized and are illustrated by C1-C4 alkyl acrylates and methacrylates such as methyl acrylate, ethyl acrylate, butyl acrylate, or the corresponding methacrylates.
  • the monomers that are more particularly preferred are methyl and ethyl (meth)acrylates.
  • Other monomers that may be used are styrene, vinyltoluene, vinyl acetate, acrylonitrile and vinylidene chloride.
  • Unreactive monomers are preferred, these monomers being those in which the single ethylenic group is the only group that is reactive under the polymerization conditions. However, monomers which contain groups that are reactive under the action of heat may be used in certain situations, such as hydroxyethyl acrylate.
  • the monohydric nonionic surfactants used to obtain the nonionic urethane monomer c) are well known and are generally alkoxylated hydrophobic compounds containing an alkylene oxide forming the hydrophilic part of the molecule.
  • the hydrophobic compounds generally consist of an aliphatic alcohol or an alkylphenol in which a carbon-based chain containing at least six carbon atoms constitutes the hydrophobic part of the surfactant.
  • the preferred monohydric nonionic surfactants have the formula:
  • R 1 is a C6-C30 alkyl or C8-C30 aralkyl group
  • R 2 is a C1-C4 alkyl group
  • n is an average number ranging from about 5 to 150
  • preferred C6-C30 alkyl groups mention may be made of dodecyl and C18-C26 alkyl radicals.
  • aralkyl groups mention may be made more particularly of (Cs- Ci3)alkylphenyl groups.
  • the preferred group R 2 is the methyl group.
  • the monoethylenically unsaturated monoisocyanate used to form the nonionic urethane monomer c) may be chosen from very varied compounds. Use may be made of a compound containing any copolymerizable unsaturation such as acrylic or methacrylic unsaturation. Use may also be made of allylic unsaturation imparted by allyl alcohol.
  • the preferred monoethylenic monoisocyanates are a,a-dimethyl-m- isopropenylbenzyl isocyanate and methylstyreneisopropyl isocyanate.
  • the acrylic terpolymer defined above is obtained by aqueous emulsion copolymerization of the components a), b) and c) which is common and described in patent application EP-A-0 173 109.
  • anionic associative polyurethanes that may be used according to the present invention, mention may be made notably of methacrylic or acrylic acid copolymers comprising at least one C1-30 alkyl (meth)acrylate unit and a urethane unit substituted with a fatty chain. Mention may be made in particular of the methacrylic acid/methyl methacrylate/methylstyreneisopropyl isocyanate/polyethoxylated behenyl alcohol (including 40 ethoxy units) copolymer sold under the brand name Viscophobe ® DB 1000 sold by the company Union Carbide.
  • the nonionic associative polyurethanes may notably be polyurethane polyethers including in their chain both hydrophilic blocks most usually of polyoxyethylenated nature and hydrophobic blocks which may be aliphatic sequences alone and/or cycloaliphatic and/or aromatic sequences.
  • the polyurethane polyethers include at least two hydrocarbon-based lipophilic chains containing from 6 to 30 carbon atoms, separated by a hydrophilic block, the hydrocarbon-based chains possibly being pendent chains or chains at the end of the hydrophilic block.
  • the polymer may include a hydrocarbon-based chain at one end or at both ends of a hydrophilic block.
  • the polyurethane polyethers may be multiblock, in particular in triblock form.
  • the hydrophobic blocks may be at each end of the chain (for example: triblock copolymer bearing a hydrophilic central block) or distributed both at the ends and in the chain (for example, multiblock copolymer).
  • These same polymers may also be graft polymers or starburst polymers.
  • the nonionic fatty-chain polyurethane polyethers may be triblock copolymers, the hydrophilic block of which is a polyoxyethylene chain including from 50 to 1000 ethoxyl groups.
  • the nonionic polyurethane polyethers include a urethane bond between the hydrophilic blocks, whence arises the name.
  • nonionic fatty-chain polyurethane polyethers include those in which the hydrophilic blocks are linked to the lipophilic blocks via other chemical bonds.
  • nonionic fatty-chain polyurethane polyethers that may be used in the invention, mention may also be made of Rheolate 205 bearing a urea function, sold by the company Rheox, or Rheolate 208, 204 or 212, and also Acrysol ® RM 184.
  • the product DW 1206B from Rohm & Haas bearing a C20 alkyl chain and a urethane bond, sold at a solids content of 20% in water, may also be used.
  • Use may also be made of solutions or dispersions of these polymers, notably in water or in aqueous-alcoholic medium.
  • examples of such polymers that may be mentioned include Rheolate ® 255, Rheolate ® 278 and Rheolate ® 244 sold by the company Rheox.
  • Use may also be made of the products DW 1206F and DW 1206J sold by the company Rohm & Haas.
  • polyurethane polyethers that may be used according to the invention are in particular those described in the article by G. Fonnum, J. Bakke and Fk. Hansen - Colloid Polym. Sc , 271 , 380-389 (1993).
  • nonionic associative polyurethanes mention may be made of polyurethane polyethers that may be obtained by polycondensation of at least three compounds comprising (i) at least one polyethylene glycol comprising from 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate.
  • Aculyn 46 ® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of stearyl alcohol and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 15% by weight in a matrix of maltodextrin (4%) and water (81 %);
  • Aculyn 44 ® is a polycondensate of polyethylene glycol containing 150 or 180 mol of ethylene oxide, of decyl alcohol and of methylenebis(4-cyclohexyl isocyanate) (SMDI), at 35% by weight in a mixture of propylene glycol (39%) and water (26%).
  • the polyurethane is non-associative.
  • the polyurethane is in the form of an aqueous dispersion of polyurethane particles.
  • the dispersion(s) may be simple dispersions in the aqueous medium of the composition.
  • dispersions mention may be made of latexes.
  • polyurethane(s) present in the aqueous dispersions used in the present invention result from the reaction of:
  • - Ri represents a divalent radical of a dihydroxylated compound
  • R 2 represents a radical of an aliphatic or cycloaliphatic polyisocyanate
  • R 3 represents a radical of a low molecular weight diol, optionally substituted with one or more ionic groups,
  • n an integer ranging from 1 to 5
  • R 4 represents an alkylene or alkylene oxide radical which is not substituted with one or more ionic or potentially ionic groups
  • At least one chain extender according to the formula H2N-R5-NH2 (C), in which R 5 represents an alkylene radical substituted with one or more ionic or potentially ionic groups.
  • dihydroxylated compounds having a high molecular weight mention may be made of polyol polyesters, polyol polyethers, polyhydroxylated polycarbonates, polyhydroxylated polyacetates, polyhydroxylated polyacrylates, polyhydroxylated amide polyesters, polyhydroxylated polyalkadienes, polyhydroxylated polythioethers, and mixtures thereof.
  • the hydroxylated compounds are chosen from polyol polyesters, polyol polyethers, polyhydroxylated polycarbonates, and mixtures thereof.
  • the polyisocyanates that may be used according to the present invention are notably chosen from organic diisocyanates with a molecular weight of about 1 12 to 1000, and preferably about 140 to 400.
  • the polyisocyanates are chosen from diisocyanates and more particularly from those represented by the general formula R 2 (NCO) 2 , in which R 2 represents a divalent aliphatic hydrocarbon-based group containing from 4 to 18 carbon atoms, a divalent cycloaliphatic hydrocarbon-based group containing from 5 to 15 carbon atoms, a divalent araliphatic hydrocarbon-based group containing from 7 to 15 carbon atoms or a divalent aromatic hydrocarbon-based group containing from 6 to 15 carbon atoms.
  • R 2 represents an organic diisocyanate.
  • organic diisocyanates the following may notably be chosen: tetramethylene diisocyanate, 1 ,6- hexamethylene diisocyanate, dodecamethylene diisocyanate, 1 ,3- diisocyanatocyclohexane, 1 ,4-diisocyanatocyclohexane, 3-isocyanatomethyl-3,5,5- trimethylcyclohexane isocyanate (isophorone diisocyanate or IPDI), bis(4- isocyanatocyclohexyl)methane, 1 ,3-bis(isocyanatomethyl)cyclohexane, 1 ,4- bis(isocyanatomethyl)cyclohexane, bis(4-isocyanato-3-methyl-cyclohexyl)methane, isomers of toluene diisocyanate (TDI) such as
  • the diisocyanates are aliphatic and cycloaliphatic diisocyanates, and are more preferentially chosen from 1 ,6-hexamethylene diisocyanate, 3- isocyanatomethyl-3,5,5-trimethylcyclohexane isocyanate, and mixtures thereof.
  • low molecular weight diol refers to a diol with a molecular weight from about 62 to 700, and preferably from 62 to 200.
  • These diols may comprise aliphatic, alicyclic or aromatic groups. Preferably, they comprise only aliphatic groups.
  • R 3 represents a low molecular weight diol containing more than 20 carbon atoms, more preferentially chosen from ethylene glycol, diethylene glycol, 1 ,2- propanediol, 1 ,3-propanediol, 1 ,4-butanediol, 1 ,3-butylene glycol, neopentyl glycol, butylethylpropanediol, cyclohexanediol, 1 ,4-cyclohexanedimethanol, 1 ,6-hexanediol, bisphenol A (2,2-bis(4-hydroxyphenyl)propane), hydrogenated bisphenol A (2,2-bis(4- hydroxycyclohexyl)propane), and mixtures thereof.
  • the low molecular weight diols may optionally comprise ionic or potentially ionic groups.
  • Examples of low molecular weight diols containing ionic or potentially ionic groups are notably described in patent US 3 412 054. Such compounds are preferably chosen from dimethylolbutanoic acid, dimethylolpropionic acid, polycaprolactone diols containing a carboxyl group, and mixtures thereof. If low molecular weight diols containing ionic or potentially ionic groups are used, they are preferably used in an amount such that less than 0.30 meq of COOH per gram of polyurethane is present in the polyurethane dispersion.
  • the prepolymer is extended by means of two chain extender families.
  • the first chain extenderfamily corresponds to the compounds of general formula H2N-R4-NH2 (B), in which R 4 represents an alkylene or alkylene oxide radical which is not substituted with one or more ionic or potentially ionic groups.
  • the chain extenders of formula (B) are preferably chosen from alkylenediamines, such as hydrazine, ethylenediamine, propylenediamine, 1 ,4-butylenediamine, piperazine; alkylene oxide diamines, such as 3- ⁇ 2-[2-(3- aminopropoxy)ethoxy]ethoxy ⁇ propylamine (also known as dipropylamine diethylene glycol or DPA-DEG available from Tomah Products, Milton, Wis.), 2-methyl-1 ,5- pentanediamine (Dytec A from DuPont), hexanediamine, isophorone diamine, 4,4- methylenedi(cyclohexylamine), ether-amines of the DPA series, available from Tomah Products, Milton, Wis., such as dipropylamine propylene glycol, dipropylamine dipropylene glycol, dipropylamine tripropylene glycol, dipropylamine polypropylene glycol), dipropyl
  • the second chain extender family corresponds to the compounds of general formula H2N-R 5 -NH2 (C), in which R 5 represents an alkylene radical substituted with one or more ionic or potentially ionic groups.
  • R 5 represents an alkylene radical substituted with one or more ionic or potentially ionic groups.
  • Such compounds preferably have an ionic or potentially ionic group and two groups that can react with isocyanate groups.
  • Such compounds can optionally comprise two groups that react with isocyanate groups and one group which is ionic or capable of forming an ionic group.
  • the ionic or potentially ionic group may preferably be chosen from ternary or quaternary ammonium groups or groups that can be converted into such groups, a carboxyl group, a carboxylate group, a sulfonic acid group and a sulfonate group.
  • the at least partial conversion of groups that can be converted into a ternary or quaternary ammonium group salt may be performed before or during the mixing with water.
  • the chain extenders of formula (C) are preferably chosen from diaminosulfonates, for instance the sodium salt of N-(2-aminoethyl)-2-aminoethanesulfonic acid (ASA), the sodium salt of N-(2-aminoethyl)-2-aminopropionic acid, and mixtures thereof.
  • ASA N-(2-aminoethyl)-2-aminoethanesulfonic acid
  • ASA sodium salt of N-(2-aminoethyl)-2-aminopropionic acid
  • the polyurethane that may be used according to the present invention may optionally also comprise compounds which are located, respectively, at the chain ends and terminate said chains (chain terminators). Such compounds are notably described in patents US 7 445 7 452 770 and/or US 7 452 770.
  • the aqueous dispersion of polyurethane particles has a viscosity of less than 2000 mPa.s at 23°C, more preferentially less than 1500, and even better still less than 1000. Even more preferably, the aqueous polyurethane dispersion has a glass transition temperature of less than 0°C.
  • the aqueous polyurethane dispersion has a solids (or active material, or dry matter) content, on the basis of the weight of the dispersion, of from 20% to 60% by weight, more preferentially from 25% to 55% by weight and even better still from 30% to 50% by weight.
  • a solids (or active material, or dry matter) content on the basis of the weight of the dispersion, of from 20% to 60% by weight, more preferentially from 25% to 55% by weight and even better still from 30% to 50% by weight.
  • the polyurethane content (dry matter) of the aqueous dispersion is preferably from 20% to 60% by weight, more preferentially from 25% to 55% by weight and even better still from 30% to 50% by weight, relative to the total weight of the dispersion.
  • the aqueous dispersion of polyurethane particles has a glass transition temperature (Tg) of less than or equal to -25°C, preferably less than -35°C and more preferentially less than -40°C.
  • Tg glass transition temperature
  • the polyurethane particles may have an average diameter ranging up to about 1000 nm, for example from about 50 nm to about 800 nm, better still from about 100 nm to about 500 nm. These particle sizes may be measured with a laser particle sizer (for example Brookhaven BI90).
  • a laser particle sizer for example Brookhaven BI90.
  • Baycusan ® As non-limiting examples of aqueous polyurethane dispersions, mention may be made of those sold under the name Baycusan ® by Bayer, for instance Baycusan ® C1000 (INCI name: polyurethane-34), Baycusan ® C1001 (INCI name: polyurethane-34), Baycusan ® C1003 (INCI name: polyurethane-32), Baycusan ® C1004 (INCI name: polyurethane-35) and Baycusan ® C1008 (INCI name: polyurethane-48).
  • aqueous polyurethane dispersions of isophthalic acid/adipic acid copolymer/hexylene glycol/neopentyl glycol/dimethylol acid/isophorone diisocyanate (INCI name: polyurethane-1 , such as Luviset ® Pur, BASF), the polyurethane of polycarbonate, polyurethane and aliphatic polyurethane of aliphatic polyester (such as the Neorez ® series, DSM, such as Neorez ® R989, Neorez ® and R- 2202).
  • the aqueous dispersion of polyurethane particles may be chosen from aqueous dispersions of adipic acid copolymer/hexylene glycol/neopentyl glycol/hexamethylene diisocyanate/sodium N-(2-aminoethyl)-2- aminoethanesulfonate/ethylenediamine.
  • the polyurethane is the compound having the INCI name polyurethane-34, preferably in the form of an aqueous particle dispersion.
  • composition according to the invention may comprise a total amount of one or more polyurethanes ranging from 0.01 % to 20% by weight, preferably from 0.1 % to 10% by weight, more preferentially from 0.2% to 5% by weight and better still from 0.3% to 2% by weight, relative to the total weight of the composition.
  • composition according to the present invention also comprises one or more cationic polymers other than polyurethanes, preferably having a cationic charge density greater than or equal to 4 milliequivalents/gram (meq/g), better still greater than or equal to 5 meq/g, or even ranging from 5 to 20 meq/g.
  • cationic polymers other than polyurethanes preferably having a cationic charge density greater than or equal to 4 milliequivalents/gram (meq/g), better still greater than or equal to 5 meq/g, or even ranging from 5 to 20 meq/g.
  • the cationic charge density of a polymer corresponds to the number of moles of cationic charges per unit mass of polymer under conditions in which it is totally ionized. It may be determined by calculation if the structure of the polymer is known, i.e. the structure of the monomers constituting the polymer and their molar proportion or weight proportion. It may also be determined experimentally by the Kjeldahl method.
  • cationic polymer denotes any non-silicone (not comprising any silicon atoms) polymer containing cationic groups and/or groups that can be ionized into cationic groups and not containing any anionic groups and/or groups that can be ionized into anionic groups.
  • the cationic polymers preferably have a weight-average molar mass (Mw) of between 500 and 5x10 6 approximately and preferably between 10 3 and 3x10 6 approximately.
  • cationic polymers mention may be made more particularly of:
  • R3 which may be identical or different, denote a hydrogen atom or a CH3 radical
  • - A which may be identical or different, represent a linear or branched divalent alkyl group of 1 to 6 carbon atoms, preferably 2 or 3 carbon atoms, or a hydroxyalkyl group of 1 to 4 carbon atoms;
  • R4, R5 and R6, which may be identical or different, represent an alkyl group containing from 1 to 18 carbon atoms or a benzyl radical, preferably an alkyl group containing from 1 to 6 carbon atoms;
  • R1 and R2 which may be identical or different, represent a hydrogen atom or an alkyl group containing from 1 to 6 carbon atoms, preferably methyl or ethyl;
  • X- denotes an anion derived from a mineral or organic acid, such as a methosulfate anion or a halide such as chloride or bromide.
  • the copolymers of family (1 ) may also contain one or more units derived from comonomers that may be chosen from the family of acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides substituted on the nitrogen with lower (C1-C4) alkyls, acrylic or methacrylic acid esters, vinyllactams such as vinylpyrrolidone or vinylcaprolactam, and vinyl esters.
  • crosslinked polymers of methacryloyloxy(C1-C4)alkyltri(C1- C4)alkylammonium salts such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homopolymerization or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide.
  • Use may be made more particularly of a crosslinked acrylamide/methacryloyloxyethyltrimethylammonium chloride copolymer (20/80 by weight) in the form of a dispersion comprising 50% by weight of said copolymer in mineral oil.
  • This dispersion is sold under the name Salcare® SC 92 by the company Ciba.
  • Use may also be made of a crosslinked methacryloyloxyethyltrimethylammonium chloride homopolymer comprising approximately 50% by weight of the homopolymer in mineral oil or in a liquid ester. These dispersions are sold under the names Salcare® SC 95 and Salcare® SC 96 by the company Ciba.
  • the cationic polymers of family (1 ) are chosen from quaternized or non-quaternized vinylpyrrolidone/dialkylaminoalkyl (meth)acrylate copolymers; crosslinked polymers of methacryloyloxy(C1 -C4)alkyl tri(C1 -C4)alkylammonium salts, such as the polymers obtained by homopolymerization of dimethylaminoethyl methacrylate quaternized with methyl chloride, or by copolymerization of acrylamide with dimethylaminoethyl methacrylate quaternized with methyl chloride, the homo- or copolymerization being followed by crosslinking with an olefinically unsaturated compound, in particular methylenebisacrylamide; and mixtures thereof.
  • an olefinically unsaturated compound in particular methylenebisacrylamide
  • cationic polysaccharides in particular cationic galactomannan gums and celluloses.
  • cationic polysaccharides mention may be made more particularly of cellulose ether derivatives including quaternary ammonium groups, cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer and cationic galactomannan gums.
  • the cellulose ether derivatives including quaternary ammonium groups are notably described in FR 1 492 597, and mention may be made of the polymers sold under the name Ucare Polymer JR (JR 400 LT, JR 125 and JR 30M) or LR (LR 400 and LR 30M) by the company Amerchol. These polymers are also defined in the CTFA dictionary as quaternary ammoniums of hydroxyethylcellulose that have reacted with an epoxide substituted with a trimethylammonium group.
  • Cationic cellulose copolymers or cellulose derivatives grafted with a water-soluble quaternary ammonium monomer are described notably in patent US 4 131 576, and mention may be made of hydroxyalkyl celluloses, for instance hydroxymethyl, hydroxyethyl or hydroxypropyl celluloses notably grafted with a methacryloylethyltrimethylammonium, methacrylamidopropyltrimethylammonium or dimethyldiallylammonium salt.
  • the commercial products corresponding to this definition are more particularly the products sold under the names Celquat L 200 and Celquat H 100 by the company National Starch.
  • guar gums comprising cationic trialkylammonium groups.
  • Use is made, for example, of guar gums modified with a 2,3-epoxypropyltrimethylammonium salt (for example, a chloride).
  • a 2,3-epoxypropyltrimethylammonium salt for example, a chloride.
  • Such products are in particular sold under the names Jaguar C13 S, Jaguar C 15, Jaguar C 17 and Jaguar C162 by the company Rhodia.
  • polymers constituted of piperazinyl units and of divalent alkylene or hydroxyalkylene radicals bearing linear or branched chains, optionally interrupted with oxygen, sulfur or nitrogen atoms or with aromatic or heterocyclic rings, and also the oxidation and/or quaternization products of these polymers.
  • water-soluble polyaminoamides prepared in particular by polycondensation of an acidic compound with a polyamine; these polyaminoamides can be crosslinked with an epihalohydrin, a diepoxide, a dianhydride, an unsaturated dianhydride, a bis- unsaturated derivative, a bis-halohydrin, a bis-azetidinium, a bis-haloacyldiamine, a bis- alkyl halide or alternatively with an oligomer resulting from the reaction of a difunctional compound which is reactive with a bis-halohydrin, a bis-azetidinium, a bis- haloacyldiamine, a bis-alkyl halide, an epihalohydrin, a diepoxide or a bis-unsaturated derivative; the crosslinking agent being used in proportions ranging from 0.025 to 0.35 mol per amine group of the polyaminoamide; these polyaminoamide
  • polyaminoamide derivatives resulting from the condensation of polyalkylene polyamines with polycarboxylic acids followed by alkylation with difunctional agents Mention may be made, for example, of adipic acid/dialkylaminohydroxyalkyldialkylenetriamine polymers in which the alkyl radical includes from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • alkyl radical includes from 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl.
  • these derivatives mention may be made more particularly of the adipic acid/dimethylaminohydroxypropyl/diethylenetriamine polymers sold under the name Cartaretine F, F4 or F8 by the company Sandoz.
  • Polymers of this type are sold in particular under the name Hercosett 57 by the company Hercules Inc. or else under the name PD 170 or Delsette 101 by the company Hercules in the case of the adipic acid/epoxypropyl/diethylenetriamine copolymer.
  • cyclopolymers of alkyldiallylamine or of dialkyldiallylammonium such as the homopolymers or copolymers including, as main constituent of the chain, unite corresponding to formula (V) or (VI):
  • R12 denotes a hydrogen atom or a methyl radical
  • R10 and R1 1 independently of each other, denote a C1-C6 alkyl group, a C1-C5 hydroxyalkyl group, a C1-C4 amidoalkyl group; or alternatively R10 and R1 1 may denote, together with the nitrogen atom to which they are attached, a heterocyclic group such as piperidyl or morpholinyl; R10 and R1 1 , independently of each other, preferably denote a C1 -C4 alkyl group;
  • Y- is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulfate, bisulfite, sulfate or phosphate.
  • dimethyldiallylammonium salts for example chloride
  • Merquat 100 by the company Nalco
  • the copolymers of diallyldimethylammonium salts for example chloride
  • acrylamide sold in particular under the name Merquat 550 or Merquat 7SPR.
  • R13, R14, R15 and R16 which may be identical or different, represent aliphatic, alicyclic or arylaliphatic radicals comprising from 1 to 20 carbon atoms or C1 -C12 hydroxyalkyl aliphatic radicals;
  • R13, R14, R15 and R16 together or separately, form, with the nitrogen atoms to which they are attached, heterocycles optionally comprising a second non- nitrogen heteroatom;
  • R13, R14, R15 and R16 represent a linear or branched C1 -C6 alkyl radical substituted with a nitrile, ester, acyl, amide or -CO-0-R17-D or -CO-NH-R17-D group, where R17 is an alkylene and D is a quaternary ammonium group;
  • A1 and B1 represent linear or branched, saturated or unsaturated, divalent polymethylene groups comprising from 2 to 20 carbon atoms, which may contain, linked to or intercalated in 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 a mineral or organic acid
  • A1 , R13 and R15 can form, with the two nitrogen atoms to which they are attached, a piperazine ring;
  • A1 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical
  • B1 may also denote a group (CH2)n-CO-D-OC-(CH2)p- with n and p, which may be identical or different, being integers ranging from 2 to 20, and D denoting:
  • a glycol residue of formula -0-Z-0- in which Z denotes a linear or branched hydrocarbon-based radical or a group corresponding to one of the following formulae: - (CH2CH20)x-CH2CH2- and -[CH2CH(CH3)0]y-CH2CH(CH3)-, in which 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 an average degree of polymerization;
  • a bis-secondary diamine residue such as a piperazine derivative
  • X- is an anion such as chloride or bromide.
  • Mn number-average molar mass
  • R1 , R2, R3 and R4 which may be identical or different, denote an alkyl or hydroxyalkyl radical containing from 1 to 4 carbon atoms, n and p are integers ranging from 2 to 20, and X- is an anion derived from a mineral or organic acid.
  • R18, R19, R20 and R21 which may be identical or different, represent a hydrogen atom or a methyl, ethyl, propyl, b-hydroxyethyl, b-hydroxypropyl or - CH2CH2(OCH2CH2)pOH radical, in which p is equal to 0 or to an integer between 1 and 6, with the proviso that R18, R19, R20 and R21 do not simultaneously represent a hydrogen atom,
  • - r and s which may be identical or different, are integers between 1 and 6,
  • X- denotes an anion such as a halide
  • - A denotes a divalent dihalide radical or preferably represents -
  • cationic polymers that may be used in the context of the invention are cationic proteins or cationic protein hydrolysates, polyalkyleneimines, in particular polyethyleneimines, polymers comprising vinylpyridine or vinylpyridinium units, condensates of polyamines and of epichlorohydrin, quaternary polyureylenes and chitin derivatives.
  • the cationic polymers are chosen from those of families (1 ), (7) and (8) mentioned above, and mixtures thereof.
  • cationic polymers use may preferably be made of cationic cyclopolymers, in particular homopolymers or copolymers of dimethyldiallylammonium salts (for example chloride), sold under the names Merquat 100, Merquat 550 and Merquat S by the company Nalco, optionally crosslinked homopolymers or copolymers of methacryloyloxy(C1 -C4)alkyltri(C1 -C4)alkylammonium salts, and mixtures thereof.
  • dimethyldiallylammonium salts for example chloride
  • the cationic polymer(s) are chosen from:
  • alkyldiallylamine or dialkyldiallylammonium cyclopolymers alkyldiallylamine or dialkyldiallylammonium cyclopolymers
  • the cationic polymer(s) are chosen from 2-methacryloyloxyethyltrimethylammonium chloride homopolymers or copolymers, dimethyldiallylammonium chloride homopolymers, and mixtures thereof.
  • the composition comprises at least two cationic polymers other than polyurethanes.
  • the total content of the cationic polymer(s) other than polyurethanes present in the composition is preferably between 0.01 % and 15% by weight, preferably between 0.05% and 10% by weight, even more preferentially between 0.1 % and 5% by weight and better still between 1 % and 3% by weight, relative to the total weight of the composition.
  • composition according to the present invention comprises one or more organosilanes.
  • organosilane(s) that may be used according to the invention are preferably chosen from the compounds of formula (X), oligomers thereof, hydrolysis products thereof and/or mixtures thereof:
  • R1 is a cyclic or acyclic, linear or branched, saturated or unsaturated C1 to C22, notably C2 to C20, hydrocarbon-based chain, which may be substituted with one or more groups chosen from amine groups NH2 or NHR (R being a linear or branched C1 to C20, notably C1 to C6, alkyl, or a C3 to C40 cycloalkyl or a C6 to C30 aromatic radical); a hydroxyl group (OH); a thiol group; an aryl group (more particularly benzyl) which is unsubstituted or substituted with one or more NH2 or NHR groups; it being possible for R1 to be interrupted with one or more oxygen, sulfur and/or nitrogen heteroatoms and/or with one or more carbonyl groups (CO);
  • amine groups NH2 or NHR R being a linear or branched C1 to C20, notably C1 to C6, alkyl, or a C3 to C40
  • R2 and R3 which may be identical or different, represent a linear or branched alkyl group comprising from 1 to 6 carbon atoms,
  • - y denotes an integer ranging from 0 to 3
  • - z denotes an integer ranging from 0 to 3
  • - x denotes an integer ranging from 0 to 2
  • oligomer refers to the polymerization products of the compounds of formula (X) including from 2 to 10 silicon atoms.
  • R1 is a linear or branched, more preferentially linear, saturated C1 to C22 and notably C2 to C12 hydrocarbon-based chain, which may be substituted with an amine group NH2 or NHR, R being a C1 to C20, and notably C1 to C6, alkyl.
  • R2 represents an alkyl group comprising from 1 to 4 carbon atoms, more preferentially a linear alkyl group comprising from 1 to 4 carbon atoms, and in particular the ethyl group.
  • z ranges from 1 to 3.
  • y is equal to 0.
  • z is equal to 3.
  • x and y are equal to 0 and z is equal to 3.
  • the organosilane(s) are chosen from the compounds of formula (X) in which R1 represents a linear alkyl group including from 1 to 18 carbon atoms and more particularly from 1 to 12 carbon atoms, or a C1 to C6 and preferably C2 to C4 aminoalkyl group. Particularly preferably, in this embodiment, R1 represents a methyl or octyl group.
  • the organosilane(s) are chosen from the compounds of formula (X) in which R1 is a linear or branched, saturated or unsaturated C1 to C22 hydrocarbon-based chain, substituted with one or more amine groups NH2 or NHR, R being a linear or branched C1 to C20, preferably C1 to C6, alkyl, or a C3 to C40 cycloalkyl or a C6 to C30 aromatic.
  • the organosilane(s) are chosen from the compounds of formula (XI), oligomers thereof, hydrolysis products thereof and/or mixtures thereof:
  • radicals R which may be identical or different, are chosen from linear or branched C1 to C6, more preferentially C2 to C4, alkyl radicals;
  • n is an integer ranging from 1 to 6, more preferentially from 2 to 4.
  • the organosilane(s) that may be used according to the invention are chosen from methyltriethoxysilane, octyltriethoxysilane (OTES), dodecyltriethoxysilane, octadecyltriethoxysilane, hexadecyltriethoxysilane, 3-aminopropyltriethoxysilane (APTES), 2-aminoethyltriethoxysilane (AETES), 3-aminopropylmethyldiethoxysilane, N- (2-aminoethyl)-3-aminopropyltriethoxysilane, 3-(m- aminophenoxy)propyltrimethoxysilane, p-aminophenyltrimethoxysilane, N-(2- aminoethylaminomethyl)phenethyltrimethoxysilane, oligomers thereof, hydrolysis products thereof, and mixtures thereof;
  • the organosilanes used in the composition of the invention may be partially or totally neutralized in order to improve the water solubility thereof.
  • the neutralizer may be chosen from organic or mineral acids, such as citric acid, tartaric acid, lactic acid and hydrochloric acid.
  • the optionally neutralized organosilane(s) that may be used according to the invention are water-soluble and notably soluble at a concentration of 2% by weight, better still at a concentration of 5% by weight and even better still at a concentration of 10% by weight in water at a temperature of 25°C and at atmospheric pressure (1 atm).
  • the term“soluble” implies the formation of a single macroscopic phase.
  • the total content of the organosilane(s) present in the composition is between 0.1 % and 15% by weight, preferably between 1 % and 10% by weight, and more preferentially between 2% and 8% by weight, relative to the total weight of the composition.
  • composition according to the invention comprises one or more polysaccharides other than the cationic polymers described previously.
  • the polysaccharide(s) according to the invention are chosen from nonionic, anionic and amphoteric polysaccharides.
  • polysaccharides refers to a polymer constituted of sugar units.
  • sucrose unit refers to an oxygen- bearing hydrocarbon-based compound containing several alcohol functions, with or without aldehyde or ketone functions, and which includes at least 4 carbon atoms.
  • the sugar units may be optionally modified by substitution, and/or by oxidation and/or by dehydration.
  • sugar units that may be included in the composition of the polysaccharides of the invention are preferably derived from the following sugars: glucose, galactose, arabinose, rhamnose, mannose, xylose, fucose, anhydrogalactose, galacturonic acid, glucuronic acid, mannuronic acid, galactose sulfate, anhydrogalactose sulfate and fructose.
  • Polysaccharides that may notably be mentioned include native gums such as: a) tree or shrub exudates, including:
  • gum arabic branched polymer of galactose, arabinose, rhamnose and glucuronic acid
  • - ghatti gum polymer derived from arabinose, galactose, mannose, xylose and glucuronic acid
  • karaya gum polymer derived from galacturonic acid, galactose, rhamnose and glucuronic acid
  • gums derived from algae including:
  • - alginates polymers of mannuronic acid and of glucuronic acid
  • - carrageenans and furcellerans polymers of galactose sulfate and of anhydrogalactose sulfate
  • gums derived from seeds or tubers including:
  • locust bean gum polymer of mannose and galactose
  • microbial gums including:
  • - xanthan gum polymer of glucose, mannose acetate, mannose/pyruvic acid and glucuronic acid
  • - gellan gum polymer of partially acylated glucose, rhamnose and glucuronic acid
  • the polysaccharide(s) of the composition according to the invention may also be chosen from mixtures of the polysaccharides above.
  • These polymers may be physically or chemically modified.
  • physical treatment mention may notably be made of a heat treatment.
  • Chemical treatments that may be mentioned include esterification, etherification, amidation and oxidation reactions. These treatments make it possible to produce polymers that may notably be nonionic, anionic or amphoteric.
  • these chemical or physical treatments are applied to guar gums, locust bean gums, starches and celluloses.
  • nonionic guar gums that may be used according to the invention may be modified with C1-C6 (poly)hydroxyalkyl groups.
  • C1-C6 (poly)hydroxyalkyl groups examples that may be mentioned include hydroxymethyl, hydroxyethyl, hydroxypropyl and hydroxybutyl groups.
  • guar gums are well known from the prior art and may be prepared, for example, by reacting corresponding alkene oxides, for instance propylene oxides, with the guar gum so as to obtain a guar gum modified with hydroxypropyl groups.
  • the degree of hydroxyalkylation preferably ranges from 0.4 to 1.2 and corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functions present on the guar gum.
  • Such nonionic guar gums optionally modified with hydroxyalkyl groups are sold, for example, under the trade names Jaguar HP8, Jaguar HP60 and Jaguar HP120, Jaguar DC 293 and Jaguar HP 105 by the company Rhodia Chimie or under the name Galactasol 4H4FD2 by the company Aqualon.
  • the botanical origin of the starches that may be used in the present invention may be cereals or tubers.
  • the starches are chosen, for example, from corn starch, rice starch, cassava starch, barley starch, potato starch, wheat starch, sorghum starch and pea starch.
  • Distarch phosphates or compounds rich in distarch phosphate will preferentially be used, for instance the product sold under the references Prejel VA-70-T AGGL (gelatinized hydroxypropyl cassava distarch phosphate), Prejel TK1 (gelatinized cassava distarch phosphate) or Prejel 200 (gelatinized acetyl cassava distarch phosphate) by the company Avebe, or Structure Zea from National Starch (gelatinized corn distarch phosphate).
  • amphoteric starches may also be used, these amphoteric starches comprising one or more anionic groups and one or more cationic groups.
  • the anionic and cationic groups may be bonded to the same reactive site of the starch molecule or to different reactive sites; they are preferably bonded to the same reactive site.
  • the anionic groups may be of carboxylic, phosphate or sulfate type, preferably carboxylic.
  • the cationic groups may be of primary, secondary, tertiary or quaternary amine type.
  • the starch molecules may be derived from any plant source of starch, notably such as corn, potato, oat, rice, tapioca, sorghum, barley or wheat. It is also possible to use the hydrolysates of the starches mentioned above.
  • the starch is preferably derived from potato.
  • the polysaccharides that may be used according to the invention may be cellulose- based polymers.
  • cellulose-based polymer refers to any polysaccharide compound bearing in its structure sequences of glucose residues linked together via b-1 ,4 bonds; in addition to unsubstituted celluloses, the cellulose derivatives may be anionic, cationic, amphoteric or nonionic.
  • the cellulose-based polymers that may be used according to the invention may be chosen from unsubstituted celluloses, including those in a microcrystalline form, and cellulose ethers.
  • cellulose ethers cellulose esters
  • cellulose ester ethers are distinguished.
  • the cellulose esters are mineral esters of cellulose (cellulose nitrates, sulfates, phosphates, etc.), organic esters of cellulose (cellulose monoacetates, triacetates, amidopropionates, acetatebutyrates, acetatepropionates and acetatetrimellitates, etc.), and mixed organic/mineral esters of cellulose, such as cellulose acetatebutyrate sulfates and cellulose acetatepropionate sulfates.
  • the cellulose ester ethers mention may be made of hydroxypropylmethylcellulose phthalates and ethylcellulose sulfates.
  • nonionic cellulose ethers mention may be made of (C1 - C4)alkylcelluloses such as methylcelluloses and ethylcelluloses (for example Ethocel Standard 100 Premium from Dow Chemical); (poly)hydroxy(C1 -C4)alkylcelluloses such as hydroxymethylcelluloses, hydroxyethylcelluloses (for example Natrosol 250 HHR sold by Ashland) and hydroxypropylcelluloses (for example Klucel EF, Klucel H, Klucel LHF, Klucel MF and Klucel G from Aqualon and Cellosize Polymer PCG-10 from the company Amerchol); (poly)hydroxy(C1 -C4)alkyl-(C1 -C4)alkylcellulose mixed celluloses such as hydroxypropyl-methylcelluloses (for example Methocel E4M from Dow Chemical), hydroxyethyl-methylcelluloses, hydroxyethyl-ethylcelluloses (for example Bermocoll E 481 FQ from Akz
  • anionic cellulose ethers mention may be made of (poly)carboxy(CI - C4)alkylcelluloses and salts thereof.
  • examples that may be mentioned include carboxymethylcelluloses, carboxymethylmethylcelluloses (for example Blanose 7M from the company Aqualon) and carboxymethylhydroxyethylcelluloses, and the sodium salts thereof.
  • composition according to the invention comprises one or more nonionic polysaccharides.
  • Nonionic polysaccharides that may notably be mentioned include those chosen from glucans, modified or unmodified starches (such as those resulting, for example, from cereals, such as wheat, corn or rice, from legumes, such as yellow pea, or from tubers, such as potato or cassava), amylose, amylopectin, glycogen, dextrans, celluloses and derivatives thereof (methylcelluloses, hydroxyalkylcelluloses, ethylhydroxyethylcelluloses), mannans, xylans, lignins, arabans, galactans, galacturonans, chitin, chitosans, glucuronoxylans, arabinoxylans, xyloglucans, glucomannans, pectic acids and pectins, arabinogalactans, carrageenans, agars, gums arabic, gums tragacanth, ghatti gums, karaya gums, locust bean
  • the polysaccharide(s) according to the invention are chosen from guar gums and/or derivatives thereof which are nonionic, and/or mixtures thereof; more preferentially from nonionic guar gums modified with hydroxyalkyl groups.
  • the total content of the polysaccharide(s) other than cationic polymers is between 0.01 % and 20% by weight, preferentially between 0.1 % and 10% by weight, even better still between 0.2% and 5% by weight, and better still between 0.5% and 3% by weight relative to the total weight of the composition.
  • composition according to the present invention may also comprise one or more fixing polymers other than the polyurethanes and other than the cationic polymers described previously.
  • fixing polymer refers to any polymer that is capable of giving a shape to a head of hair or of maintaining a head of hair in a given shape.
  • the fixing polymer(s) used may be chosen from anionic, cationic, amphoteric and nonionic fixing polymers, and mixtures thereof.
  • Anionic fixing polymers that may be mentioned include polymers including groups derived from carboxylic, sulfonic or phosphoric acids, and having a number-average molecular mass of between 500 and 5 000 000.
  • the carboxylic groups are provided by unsaturated monocarboxylic or dicarboxylic acid monomers, such as those corresponding to formula (XII):
  • n is an integer from 0 to 10
  • A denotes a methylene group, optionally connected to the carbon atom of the unsaturated group or to the adjacent methylene group, when n is greater than 1 , via a heteroatom, such as oxygen or sulfur,
  • R1 denotes a hydrogen atom or a phenyl or benzyl group
  • R2 denotes a hydrogen atom, an alkyl group including from 1 to 4 carbon atoms or a carboxyl group
  • R3 denotes a hydrogen atom, an alkyl group including from 1 to 4 carbon atoms, a -CH2-COOH group, a phenyl group or a benzyl group.
  • alkyl group including from 1 to 4 carbon atoms may in particular denote methyl and ethyl groups.
  • the anionic fixing polymers bearing carboxylic or sulfonic groups that are preferred are:
  • A) copolymers of acrylic or methacrylic acid or salts thereof including copolymers of acrylic acid and acrylamide, and methacrylic acid/acrylic acid/ethyl acrylate/methyl methacrylate copolymers, particularly Amerhold DR 25 sold by the company Amerchol, and sodium salts of polyhydroxycarboxylic acids. Mention may also be made of methacrylic acid/ethyl acrylate copolymers, in particular in aqueous dispersion, such as Luviflex Soft and Luvimer MAE, which are sold by the company BASF.
  • a monoethylenic monomer such as ethylene, styrene, vinyl esters and acrylic or methacrylic acid esters
  • a polyalkylene glycol such as polyethylene glycol and optionally crosslinked.
  • Such polymers are described in particular in French patent 1 222 944 and German application No. 2 330 956, the copolymers of this type including an optionally N-alkylated and/or hydroxyalkylated acrylamide unit in their chain as described notably in Luxembourg patent applications 75370 and 75371 . Mention may also be made of copolymers of acrylic acid and C1 -C4 alkyl methacrylate.
  • anionic fixing polymer from this class, mention may also be made of the butyl acrylate/acrylic acid/methacrylic acid branched block anionic polymer sold under the name Fixate G-100 L by the company Lubrizol (INCI name AMP-Acrylates/Allyl Methacrylate Copolymer).
  • C) copolymers derived from crotonic acid such as those of which the chain includes vinyl acetate or propionate units and optionally other monomers such as allyl or methallyl esters, vinyl ether or vinyl ester of a saturated, linear or branched carboxylic acid bearing a long hydrocarbon-based chain such as those including at least 5 carbon atoms, it being possible for these polymers to be optionally grafted and crosslinked, or alternatively a vinyl, allyl or methallyl ester of an a- or b-cyclic carboxylic acid.
  • Such polymers are described, inter alia, in French patents Nos.
  • Such polymers are described in particular in US patents 2 047 398, 2 723 248 and 2 102 1 13 and GB patent 839 805, and notably those sold under the names Gantrez® AN or ES by the company ISP.
  • Polymers also falling within this category are the copolymers of maleic, citraconic or itaconic anhydrides and of an allylic or methallylic ester optionally including an acrylamide or methacrylamide group, an oolefin, acrylic or methacrylic esters, acrylic or methacrylic acids or vinylpyrrolidone in their chain, the anhydride functions being monoesterified or monoamidated.
  • these polymers are described, for example, in French patents 2 350 384 and 2 357 241 by the Applicant.
  • polymers comprising sulfonic groups.
  • These polymers may be polymers including vinylsulfonic, styrenesulfonic, naphthalenesulfonic, acrylamidoalkylsulfonic or sulfoisophthalate units.
  • These polymers may be notably chosen from:
  • polyvinylsulfonic acid salts with a molecular mass of between 1000 and 100 000 approximately, and also the copolymers with an unsaturated comonomer such as acrylic or methacrylic acids and esters thereof, and also acrylamide or derivatives thereof, vinyl ethers and vinylpyrrolidone;
  • the grafted silicone polymers used are preferentially chosen from polymers bearing a non-silicone organic backbone grafted with monomers containing a polysiloxane, polymers bearing a polysiloxane backbone grafted with non-silicone organic monomers, and mixtures thereof.
  • Polymers containing sulfoisophthalate groups such as the polymers AQ55 and AQ48 sold by the company Eastman, may also be used.
  • the anionic fixing polymers are preferably chosen from acrylic acid copolymers, such as the acrylic acid/ethyl acrylate/N-tert-butylacrylamide terpolymer sold under the name Ultrahold Strong® by the company BASF, methacrylic acid/ethyl acrylate copolymers, notably in aqueous dispersion, such as Luviflex Soft and Luvimer MAE sold by the company BASF, crotonic acid-based copolymers, such as the vinyl acetate/vinyl tert-butylbenzoate/crotonic acid terpolymers and the crotonic acid/vinyl acetate/vinyl neododecanoate terpolymers sold under the name Resin 28-29- 30 by the company National Starch, polymers derived from maleic, fumaric or itaconic acids or anhydrides with vinyl esters, vinyl ethers, vinyl halides, phenylvinyl derivatives, acrylic
  • amphoteric fixing polymers that may be used in accordance with the invention may be chosen from polymers including units B and C distributed randomly in the polymer chain, in which B denotes a unit derived from a monomer including at least one basic nitrogen atom and C denotes a unit derived from an acid monomer including one or more carboxylic or sulfonic groups, or alternatively B and C may denote groups derived from carboxybetaine or sulfobetaine zwitterionic monomers; B and C may also denote a cationic polymer chain including primary, secondary, tertiary or quaternary amine groups, in which at least one of the amine groups bears a carboxylic or sulfonic group connected via a hydrocarbon-based group, or alternatively B and C form part of a chain of a polymer bearing an ethylenedicarboxylic unit in which one of the carboxylic groups has been made to react with a polyamine including one or more primary or secondary amine groups.
  • amphoteric fixing polymers corresponding to the definition given above that are more particularly preferred are chosen from the following polymers:
  • the vinyl compound may also be a dialkyldiallylammonium salt such as diethyldiallylammonium chloride.
  • At least one basic comonomer such as acrylic and methacrylic acid esters containing primary, secondary, tertiary and quaternary amine substituents, and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
  • N-substituted acrylamides or methacrylamides that are more particularly preferred according to the invention are groups in which the alkyl groups contain from 2 to 12 carbon atoms and more particularly N-ethylacrylamide, N-tert-butylacrylamide, N- tert-octylacrylamide, N-octylacrylamide, N-decylacrylamide and N-dodecylacrylamide, and the corresponding methacrylamides.
  • the acidic comonomers are more particularly chosen from acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid and alkyl monoesters, containing 1 to 4 carbon atoms, of maleic or fumaric acids or anhydrides.
  • the preferred basic comonomers are aminoethyl, butylaminoethyl, N,N’-dimethylaminoethyl and N- tert-butylaminoethyl methacrylates.
  • R4 represents a divalent group derived from a saturated dicarboxylic acid, from a mono- or dicarboxylic aliphatic acid with an ethylenic double bond, from an ester of an alcohol containing 1 to 6 carbon atoms with these acids, or from a group derived from the addition of any one of said acids with a bis-primary amine or bis-secondary- derived amine
  • Z denotes a group of a bis-primary or mono- or bis-secondary polyalkylene-polyamine, and preferably represents:
  • this group being derived from diethylenetriamine, from triethylenetetramine or from dipropylenetriamine;
  • the saturated carboxylic acids are preferably chosen from acids containing 6 to 10 carbon atoms, such as adipic acid, 2,2,4-trimethyladipic acid, 2,4,4-trimethyladipic acid and terephthalic acid, and acids bearing an ethylenic double bond, for instance acrylic, methacrylic and itaconic acids.
  • the alkane sultones used in the alkylation are preferably propane sultone or butane sultone, the salts of the alkylating agents are preferably the sodium or potassium salts.
  • R5 denotes a polymerizable unsaturated group such as an acrylate, methacrylate, acrylamide or methacrylamide group,
  • y and z each represent an integer from 1 to 3
  • R6 and R7 represent a hydrogen atom or a methyl, ethyl or propyl group
  • R8 and R9 represent a hydrogen atom or an alkyl group such that the sum of the carbon atoms in R10 and R1 1 does not exceed 10.
  • the polymers comprising such units may also include units derived from non- zwitterionic monomers such as dimethyl- or diethylaminoethyl acrylate or methacrylate or alkyl acrylates or methacrylates, acrylamides or methacrylamides or vinyl acetate.
  • R10 represents a group of formula (XX):
  • R1 1 , R12 and R13 which may be identical or different, each represent a hydrogen atom, a methyl, hydroxyl, acetoxy or amino residue, a monoalkylamine residue or a dialkylamine residue that are optionally interrupted with one or more nitrogen atoms and/or optionally substituted with one or more amine, hydroxyl, carboxyl, alkylthio or sulfonic groups, an alkylthio residue in which the alkyl group bears an amino residue, at least one of the groups R1 1 , R12 and R13 being, in this case, a hydrogen atom;
  • R1 1 , R12 and R13 each represent a hydrogen atom, and also the salts formed by these compounds with bases or acids.
  • R14 represents a hydrogen atom, a CH30, CH3CH20 or phenyl group
  • R15 denotes hydrogen or a C1 -C4 alkyl group such as methyl or ethyl
  • R16 denotes hydrogen or a C1 -C4 alkyl group such as methyl or ethyl
  • R17 denotes a C1 -C4 alkyl group such as methyl or ethyl or a group corresponding to the formula: -R18-N(R16)2, R18 representing a -CH2-CH2-, -CH2-CH2-CH2- or -CH2-CH(CH3)- group, R16 having the meanings mentioned above,
  • E and E’ denote a divalent group that is an alkylene group with a straight or branched chain including up to seven carbon atoms in the main chain, which is unsubstituted or substituted with hydroxyl groups and which may include, in addition to oxygen, nitrogen and sulfur atoms, one to three aromatic and/or heterocyclic rings; the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxide, sulfone, sulfonium, alkylamine or alkenylamine groups, hydroxyl, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and/or urethane groups;
  • E denotes the symbol E or E’ and at least once E’;
  • E having the meaning given above and E’ is a divalent group that is an alkylene group with a straight or branched chain containing up to six carbon atoms in the main chain, which is unsubstituted or substituted with one or more hydroxyl groups and which includes one or more nitrogen atoms, the nitrogen atom being substituted with an alkyl chain that is optionally interrupted with an oxygen atom and necessarily includes one or more carboxyl functions or one or more hydroxyl functions, betainized by reaction with chloroacetic acid or sodium chloroacetate.
  • amphoteric fixing polymers that may be used in the invention may be chosen from branched block copolymers comprising:
  • the amphoteric polymers have at least two glass transition temperatures (Tg), at least one of which is greater than 20°C and the other of which is less than 20°C.
  • amphoteric polymers are polymers including units derived:
  • basic comonomer such as acrylic and methacrylic acid esters bearing primary, secondary, tertiary and quaternary amine substituents, and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
  • the nonionic fixing polymers that may be used according to the present invention are chosen, for example, from:
  • vinyl acetate copolymers for instance copolymers of vinyl acetate and of acrylic ester, copolymers of vinyl acetate and of ethylene, or copolymers of vinyl acetate and of maleic ester, for example of dibutyl maleate,
  • styrene copolymers for instance copolymers of styrene and of alkyl (meth)acrylate, such as the products Mowilith® LDM 691 1 , Mowilith® DM 61 1 and Mowilith® LDM 6070 sold by the company Hoechst, and the products Rhodopas® SD 215 and Rhodopas® DS 910 sold by the company Rhone-Poulenc; copolymers of styrene, of alkyl methacrylate and of alkyl acrylate; copolymers of styrene and of butadiene; or copolymers of styrene, of butadiene and of vinylpyridine,
  • vinyllactam homopolymers such as vinylpyrrolidone homopolymers and the polyvinylcaprolactam sold under the name Luviskol® Plus by the company BASF,
  • vinyllactam copolymers such as a poly(vinylpyrrolidone/vinyllactam) copolymer sold under the trade name Luvitec® VPC 55K65W by the company BASF, poly(vinylpyrrolidone/vinyl acetate) copolymers, such as those sold under the name PVPVA® S630L by the company ISP, Luviskol® VA 73, VA 64, VA 55, VA 37 and VA 28 by the company BASF; and poly(vinylpyrrolidone/vinyl acetate/vinyl propionate) terpolymers, for instance the product sold under the name Luviskol® VAP 343 by the company BASF, and
  • the alkyl groups of the nonionic polymers mentioned above preferably contain from one to six carbon atoms.
  • the fixing polymer(s) are chosen from nonionic fixing polymers and anionic fixing polymers, and mixtures thereof. More preferentially, the fixing polymer(s) are chosen from nonionic fixing polymers such as those described above, and even more preferentially from vinyllactam homopolymers and/or copolymers, such as vinylpyrrolidone homopolymers, poly(vinylpyrrolidone/vinyllactam) copolymers, poly(vinylpyrrolidone/vinyl acetate) copolymers, poly(vinylpyrrolidone/vinyl acetate/vinyl propionate) terpolymers and mixtures thereof.
  • vinyllactam homopolymers such as those described above, and even more preferentially from vinyllactam homopolymers and/or copolymers, such as vinylpyrrolidone homopolymers, poly(vinylpyrrolidone/vinyllactam) copolymers, poly(vinylpyrrolidon
  • the total content of the fixing polymer(s) other than the polyurethanes and the cationic polymers, preferably nonionic polymers, present in the composition is preferably between 0.01 % and 10% by weight, preferably between 0.1 % and 5% by weight, and more preferentially between 0.2% and 2% by weight, relative to the total weight of the composition.
  • the composition according to the invention comprises one or more fixing polymers other than the polyurethanes and other than the cationic polymers and other than the polysaccharides, more preferentially chosen from anionic fixing polymers, nonionic fixing polymers, amphoteric fixing polymers, and mixtures thereof; even more preferentially from anionic fixing polymers, nonionic fixing polymers, and mixtures thereof; more better still nonionic fixing polymers and even better still from vinyllactam homopolymers and/or copolymers, such as vinylpyrrolidone homopolymers, poly(vinylpyrrolidone/vinyllactam) copolymers, poly(vinylpyrrolidone/vinyl acetate) copolymers, poly(vinylpyrrolidone/vinyl acetate/vinyl propionate) terpolymers, and mixtures thereof.
  • fixing polymers other than the polyurethanes and other than the cationic polymers and other than the polysaccharides more preferential
  • the total content of the fixing polymer(s) is between 0.01 % and 10% by weight, preferably between 0.1 % and 5% by weight, and more preferentially between 0.2% and 3% by weight, relative to the total weight of the composition.
  • composition according to the invention may also comprise one or more additional compounds chosen from surfactants, preferably chosen from nonionic, anionic, cationic and amphoteric surfactants, silicones other than organosilanes, natural or synthetic thickeners or viscosity regulators other than the compounds described above; UV filters, fillers such as nacres, titanium dioxide, resins and clays, fragrances, peptizers, vitamins, preserving agents, acidic agents, alkaline agents.
  • surfactants preferably chosen from nonionic, anionic, cationic and amphoteric surfactants, silicones other than organosilanes, natural or synthetic thickeners or viscosity regulators other than the compounds described above
  • UV filters fillers such as nacres, titanium dioxide, resins and clays, fragrances, peptizers, vitamins, preserving agents, acidic agents, alkaline agents.
  • additives may be present in the composition according to the invention in an amount ranging from 0% to 20% by weight relative to the total weight of the composition.
  • the pH of the composition according to the invention generally ranges from 2 to 12, preferably from 2.5 to 7, preferentially from 3 to 6 and better still from 3.5 to 5.5.
  • the pH of the composition may be adjusted to the desired value by means of basifying agents or acidifying agents that are customarily used.
  • basifying agents examples that may be mentioned include aqueous ammonia, alkanolamines, and mineral or organic hydroxides.
  • acidifying agents examples that may be mentioned include mineral or organic acids, for instance hydrochloric acid, orthophosphoric acid or sulfuric acid, carboxylic acids, for instance acetic acid, tartaric acid, citric acid and lactic acid, and sulfonic acids.
  • a subject of the present invention is also a process for shaping and/or conditioning keratin fibres, in particular human keratin fibres such as the hair, comprising at least one step of applying to said fibres a composition as described previously.
  • composition according to the invention may optionally be preceded by at least one step of washing said fibres using a shampoo.
  • this or these steps of applying the composition according to the invention may optionally be followed by a step of leaving the composition on, for example a leave-on time of 1 to 15 minutes, in particular 2 to 5 minutes; then followed by an optional rinsing step, for example with water; and/or a drying step.
  • the keratin fibres are not rinsed after the step(s) of applying the composition according to the invention.
  • the expression“are not rinsed” means that no step of rinsing the keratin fibres is performed for at least 30 minutes, preferentially 1 hour, after the step of applying the composition according to the invention.
  • a subject of the present invention is also a use of the composition as described previously for shaping and/or conditioning keratin fibres, in particular human keratin fibres such as the hair and notably for defining the hair curls.
  • composition as described previously is used on curly hair, to define the curls.
  • the examples that follow serve to illustrate the invention without, however, being limiting in nature.
  • composition 1 according to the invention and a comparative composition 2 were prepared using the following ingredients, the contents of which are indicated in the tables below (as g of starting material in unmodified form).
  • the control of the volume and frizziness was evaluated on locks of natural Caucasian hair of frizziness type IV, each weighing 2.7 g and measuring 26 cm.
  • Protocol 1 the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water. They were then disentangled and left to dry naturally.
  • Protocol 2 the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water. They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.4 g per gram of hair. The locks were then disentangled and left to dry naturally.
  • Protocol 3 the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water. They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.4 g per gram of hair. The locks were then disentangled and left to dry naturally. The locks were then washed using a standard shampoo, rinsed with water and left to dry naturally.
  • Protocol 4 the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water. They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.4 g per gram of hair. The locks were then disentangled and left to dry naturally. The locks were then washed with four successive standard shampoos, each shampoo washing step being followed by rinsing and drying naturally.
  • Protocol 1 b the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water (35°C, flow rate 300 l/h). They were then disentangled.
  • Protocol 2b the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water (35°C, flow rate 300 l/h). They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.45 g per gram of hair. The locks were then disentangled.
  • Protocol 3b the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water (35°C, flow rate 300 l/h). They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.45 g per gram of hair. The locks were then disentangled. The locks were then washed using a standard shampoo and rinsed with water (35°C, flow rate 300 l/h).
  • Protocol 4b the locks were washed using a standard shampoo at a rate of 0.4 g per gram of hair and then rinsed with water (35°C, flow rate 300 l/h). They were then disentangled. Composition 1 according to the invention was then applied to the wet hair, at a rate of 0.45 g per gram of hair. The locks were then disentangled. Next, the locks were washed with four successive standard shampoos, rinsing with water (35°C, flow rate 300 l/h) and drying with a hairdryer (50-55°C) between each shampoo wash.
  • the surface state of the hair thus treated was evaluated by means of a sliding test.
  • the sliding test measures the force required to move a lock sandwiched between two other locks placed in the opposite direction. This test, performed on wet hair, reveals the surface quality of the fibre. Specifically, the ease of sliding of the hair depends on its surface quality.
  • Locks of hair are superimposed head-to-tail and kept in perfect contact.
  • a device drives the central lock in a rectilinear movement.
  • a dynamometer measures the force developed to effect this movement. The smoother and more homogeneous the surface of the hair, the weaker the sliding force.
  • the average force obtained with protocols 2b, 3b and 4b is markedly lower than that obtained with protocol 1 b: the surface state of the locks treated with the composition of the invention according to protocols 2b, 3b and 4b is smoother and more homogeneous than that of the locks treated according to protocol 1 b, even after shampoo washing several times.
  • lock A After rinsing, lock A is disentangled with a comb and then left to dry naturally. The lock was then subjected to a standard shampoo wash, and was then rinsed and left to dry naturally. (Control lock) After rinsing, locks B and C are treated, respectively, with compositions 1 and 2 described above, at a rate of 0.4 g of composition per gram of hair, and are then disentangled with a comb and then left to dry naturally. The locks were then subjected to a standard shampoo wash, and were then rinsed and left to dry naturally.
  • lock B has a more beautiful visual effect, in terms of sheen, than lock C.
  • composition A according to the invention and a comparative composition B were prepared using the following ingredients, the contents of which are indicated in the tables below
  • compositions (in grams of active material per 100 g of composition)
  • compositions A and B were applied comparatively on a malleable head with curly hair, which had been washed and wrung dry beforehand, at a rate of 2 g per half-head. The hair was then dried with a diffuser. “curl definition and regularity” and“frizziness control” evaluation
  • The“curl definition and regularity” and“frizziness control” were evaluated in a blind test by five experts: each of the five experts gave his opinion regarding which side of the head had the better curl definition and the better frizziness control.
  • the evaluation of the curl definition and regularity is visual: the expert states whether the curl is well shaped, geometrical, with a regular pitch. A well-defined curl is formed by hair strands that are grouped together.
  • the expert observes whether the hair strands are grouped together well, or if there are isolated strands which give the hairstyle a“vague” and poorly shaped look.

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Abstract

La présente invention concerne une composition, notamment une composition cosmétique capillaire, comprenant un ou plusieurs polyuréthanes, un ou plusieurs polymères cationiques autres que les polyuréthanes, un ou plusieurs organosilanes et un ou plusieurs polysaccharides. L'invention concerne également l'utilisation de la composition selon l'invention pour mettre en forme et/ou conditionner des fibres de kératine, en particulier des fibres de kératine humaines telles que les cheveux, et notamment pour définir les boucles de cheveux.
PCT/EP2019/067014 2018-06-29 2019-06-26 Composition comprenant un polyuréthane, un polymère cationique, un organosilane et un polysaccharide Ceased WO2020002434A1 (fr)

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FR1855923A FR3083115B1 (fr) 2018-06-29 2018-06-29 Composition comprenant un polyurethane, un polymere cationique, un organosilane et un polysaccharide

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US11357714B2 (en) 2020-07-21 2022-06-14 Chembeau LLC Diester cosmetic formulations and uses thereof
CN117524347A (zh) * 2023-11-20 2024-02-06 中南大学 机器学习加速的酸根阴离子水化结构第一性原理预测方法

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11357714B2 (en) 2020-07-21 2022-06-14 Chembeau LLC Diester cosmetic formulations and uses thereof
US11491092B2 (en) 2020-07-21 2022-11-08 Chembeau LLC Hair treatment formulations and uses thereof
US11801211B2 (en) 2020-07-21 2023-10-31 Chembeau LLC Hair treatment formulations and uses thereof
US12214065B2 (en) 2020-07-21 2025-02-04 Chembeau LLC Diester cosmetic formulations and uses thereof
US12285508B2 (en) 2020-07-21 2025-04-29 Chembeau LLC Hair treatment formulations and uses thereof
CN117524347A (zh) * 2023-11-20 2024-02-06 中南大学 机器学习加速的酸根阴离子水化结构第一性原理预测方法
CN117524347B (zh) * 2023-11-20 2024-04-16 中南大学 机器学习加速的酸根阴离子水化结构第一性原理预测方法

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