WO2009103735A1 - Composition contenant un copolymère ampholytique à base de monomères contenant de l’azote quaternisé et d'au moins un polymère différent de ceux-ci, et son utilisation - Google Patents

Composition contenant un copolymère ampholytique à base de monomères contenant de l’azote quaternisé et d'au moins un polymère différent de ceux-ci, et son utilisation Download PDF

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Publication number
WO2009103735A1
WO2009103735A1 PCT/EP2009/051920 EP2009051920W WO2009103735A1 WO 2009103735 A1 WO2009103735 A1 WO 2009103735A1 EP 2009051920 W EP2009051920 W EP 2009051920W WO 2009103735 A1 WO2009103735 A1 WO 2009103735A1
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weight
copolymer
composition according
alkyl
ethylenically unsaturated
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PCT/EP2009/051920
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German (de)
English (en)
Inventor
Simon Champ
Marc Vesper
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Basf Se
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Publication of WO2009103735A1 publication Critical patent/WO2009103735A1/fr

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    • 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)
    • 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
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/732—Starch; Amylose; Amylopectin; 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
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; 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
    • A61K8/73—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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; 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
    • A61K8/8141—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
    • A61K8/8141—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
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; 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
    • 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)
    • A61K8/8176—Homopolymers of N-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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5428—Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • a composition comprising an ampholytic copolymer based on quaternized nitrogen-containing monomers and at least one different polymer, and their use
  • the present invention relates to a novel composition
  • a novel composition comprising at least one ampholytic copolymer A) based on quaternized nitrogen-containing monomers which has a molar excess of cationogenic / cationic groups over anionogenic / anionic groups, and at least one different polymer B) selected from the group consisting of polymers containing at least one ionogenic and / or ionic group in the molecule, ampholytic polymers and nonionic polymers.
  • the present invention relates to a novel process for the preparation of a composition
  • a composition comprising at least one ampholytic copolymer A) based on quaternized nitrogen-containing monomers, which has a molar excess of cationogenic / cationic groups towards anionogenic / anionic groups, and at least one different polymer B) selected from the group consisting of polymers containing at least one ionogenic and / or ionic group in the molecule, ampholytic polymers and nonionic polymers.
  • the present invention relates to the use of the novel composition
  • the novel composition comprising at least one ampholytic copolymer A) based on quaternized nitrogen-containing monomers which has a molar excess of cationogenic / cationic groups with respect to anionogenic / anionic groups, and at least one different polymer B), selected from the group consisting of polymers containing at least one ionogenic and / or ionic group in the molecule, ampholytic polymers and nonionic polymers, as well as the composition prepared by the new process as a hair treatment agent or for their preparation.
  • Polymers having a larger number of ionically dissociable groups in the main chain and / or a side chain are referred to as polyelectrolytes. Do these polyhedra Both anionogenic / anionic and cationogenic / cationic groups are amphoteric polyelectrolytes or ampholytic polymers. Ampholytic polymers with a sufficient number of dissociable groups are water-soluble or water-dispersible and have found various uses in the field of paints, paper auxiliaries, hygiene agents, in textile production and especially in the pharmaceutical and cosmetics industries.
  • Cosmetically and pharmaceutically acceptable water-soluble polymers are used, for example, in soaps, creams and lotions as formulating agents, eg. As a thickener, foam stabilizer or water absorbent or even to alleviate the irritant effect of other ingredients or to improve the dermal application of drugs.
  • Their job in hair cosmetics is to influence the properties of the hair. In pharmacy, for example, they serve as coating agents or binders for solid dosage forms.
  • film-forming polymers containing ionic groups for example, as conditioners, are used to improve the dry and wet combability, the feeling of touch, the shine and the appearance of the hair and to give the hair antistatic properties.
  • water-soluble polymers with cationic or anionic functionalities are used.
  • polymers with cationic functional groups structurally have a high affinity to the negatively charged surface of the hair.
  • Polymers with anionic functionalities such as. B. optionally crosslinked polyacrylic acid, for example, serve as a thickener, also carboxylate-containing polymers are used for example for the consolidation of hairstyles.
  • film-forming polymers continue to be used as setting resins to give the hairstyle a foothold.
  • Requirements for setting resins are, for example, a strong consolidation in high humidity, elasticity, leachability of the hair, compatibility in the formulation and a pleasant handle of the treated hair.
  • For the consolidation of hairstyles for example, vinyllactam homo- and copolymers and polymers containing carboxylate groups are used.
  • the desired property profile can only be achieved by using a plurality of cosmetically active components, for example a plurality of polymers having ionic groups.
  • a plurality of cosmetically active components for example a plurality of polymers having ionic groups.
  • this often shows an incompatibility of the various components with each other, which, for example, can lead to the fact that no clear formulations can be produced.
  • the use of several polyelectrolytes which are not sufficiently compatible with one another can lead to undesirable precipitation.
  • EP-A-0 330 174 describes a hair fixative gel composition
  • a hair fixative gel composition comprising a partially or completely neutralized salt of a crosslinked carboxyl group-containing polymer, an amphoteric resin and a solvent.
  • the amphoteric resin may be copolymers having betaine moieties or copolymers obtainable by copolymerizing at least one monomer having acidic groups and at least one monomer having basic groups.
  • GB-A 2,088,209 describes a hair treatment composition based on amphoteric polymers and anionic polymers.
  • the amphoteric polymer may contain monomer units which are derived from dimethylsulfate or diethylsulfalt quaternized dimethylaminoethyl methacrylate.
  • WO 01/62809 describes a cosmetic agent containing at least one water-soluble or water-dispersible polymer which
  • ⁇ , ⁇ -ethylenically unsaturated compound which may be compounds having at least one anionogenic and / or anionic group per molecule
  • US 3,927,199 describes a hair setting composition containing a film-forming binder resin based on a copolymer containing 1) N-alkylacrylamides or methacrylamides, 2) acid group-containing monomers and 3) at least one further comonomer in copolymerized form.
  • No. 4,237,253 describes copolymers for hair treatment compositions which copolymerize 22 to 64 mol% of N, N-dimethylamino-2-ethylmethacrylate, 13 to 71 mol% of methyl methacrylate, 6 to 23 mol% of methacrylic acid and up to 22 mol% of further monomers contain.
  • WO 95/35087 describes an amphoteric hair fixative polymer for use in hairsprays and gels comprising 40 to 90% by weight of a hydroxyl-containing monomer, 1 to 20% by weight of an acid group-containing monomer and 1 to 20% by weight of an amine-containing monomer contains polymerized.
  • WO 2004/058837 describes an ampholytic copolymer obtained by free-radical copolymerization of
  • polyelectrolyte complexes which contain such an ampholytic copolymer and cosmetic or pharmaceutical compositions based on these ampholytic copolymers and polyelectrolyte complexes.
  • WO 2004/022616 describes the use of polymers obtainable by
  • WO 2005/005497 describes an aqueous polymer dispersion Pd) which is obtainable by free-radical polymerization of a monomer mixture M) containing
  • R 1 and R 3 together with the amide group to which they are attached, represent a lactam having 5 to 8 ring atoms, b) at least one free-radically polymerizable crosslinking compound having at least two ⁇ , ⁇ -ethylenically unsaturated double bonds per molecule,
  • compositions in an aqueous medium in the presence of at least one polymeric anionic dispersant D). They are suitable as conditioners for cosmetic preparations, in particular shampoos.
  • WO 2005/058988 describes ampholytic copolymers which contain a molar excess of anionogenic and / or anionic groups and which are prepared by free-radical polymerization of
  • European Patent Application EP 1 712 255 discloses cosmetic preparations which comprise a copolymer formed from the monomers N-vinylpyrrolidone (VP), N-vinylimidazole (VI), methacrylamide (MAM) and quaternized N-vinylimidazole (QVI), and at least one nonionic polymer.
  • European Patent Application EP 1 712 256 discloses cosmetic preparations which comprise a copolymer formed from the monomers N-vinylpyrrolidone (VP), N-vinylimidazole (VI), methacrylamide (MAM) and quaternized N-vinylimidazole (QVI), and at least an anionic and / or amphoteric polymer.
  • the international patent application WO 2007/010035 discloses the use of an ampholytic copolymer which has a molar excess of anionogenic and / or anionic groups towards cationogenic and / or cationic groups or which has a molar excess of cationogenic and / or cationic groups towards anionogens and / or having anionic groups and which is obtainable by radical copolymerization
  • ampholytic copolymers which have a molar excess of cationogenic / cationic groups to anionogenic / anionic groups and by radical polymerization of
  • R 1 is hydrogen or C 1 -C 8 -alkyl
  • X 1 is O or NR 3
  • R 3 is hydrogen, alkyl, cycloalkyl, aryl or hetaryl
  • R 2 is branched C 3 -C 8 -alkyl
  • amide group-containing monomer which is selected from ⁇ , ⁇ -ethylenically unsaturated amide-containing compounds of the general formula II
  • R 4 and R 5 together with the amide group to which they are attached may also stand for a lactam having 5 to 8 ring atoms
  • R 5 and R 6 together with the nitrogen atom to which they are attached may also stand for a five- to seven-membered heterocycle
  • compositions may contain as active ingredient at least one polymer which is different from the ampholytic copolymer.
  • These polymers may be nonionic, anionic, cationic, amphoteric and neutral polymers act. However, a quantity range is not specified.
  • compositions can be used in hair cosmetics.
  • examples 21 to 40 of the European patent application describe aerosol hairsprays which
  • Luviskol® VA 64 powder (copolymer of BASF SE, which contains 60 parts by weight of N-vinylpyrrolidone and 40 parts by weight of vinyl acetate copolymerized),
  • Luviskol® Plus polyvinylcaprolactam from BASF SE
  • aerosol hairsprays of Examples 21 to 80 of the European patent application contain a polymer other than the ampholytic copolymer in an amount of ⁇ 1% by weight.
  • At least one ampholytic copolymer having a molar excess of cationogenic / cationic groups to anionogenic / anionic groups and by radical polymerization of
  • R 1 is hydrogen or C 1 -C 8 -alkyl
  • X 1 is O or NR 3 , where R 3 is hydrogen, alkyl, cycloalkyl, aryl or hetaryl, and
  • R 2 is branched C 3 -C 8 -alkyl
  • amide group-containing monomer which is selected from ⁇ , ⁇ -ethylenically unsaturated amide-containing compounds of the general formula II
  • R 4 and R 5 together with the amide group to which they are attached may also stand for a lactam having 5 to 8 ring atoms, where R 5 and R 6 together with the nitrogen atom to which they are attached may also stand for a five- to seven-membered heterocycle,
  • composition according to the invention composition according to the invention.
  • At least one ampholytic copolymer having a molar excess of cationogenic / cationic groups to anionogenic / anionic groups and by radical polymerization of
  • R 1 is hydrogen or C 1 -C 8 -alkyl
  • X 1 is O or NR 3 , where R 3 is hydrogen, alkyl, cycloalkyl, aryl or hetaryl, and
  • R 2 is branched C 3 -C 8 -alkyl, b) at least one compound having a free-radically polymerizable, ⁇ , ⁇ -ethylenically unsaturated double bond and at least one cationogenic and / or cationic groups per molecule, with the proviso that at least some of the compounds b) have at least one quaternary nitrogen atom,
  • amide group-containing monomer which is selected from ⁇ , ⁇ -ethylenically unsaturated amide-containing compounds of the general formula II
  • R 4 and R 5 together with the amide group to which they are attached may also stand for a lactam having 5 to 8 ring atoms
  • R 5 and R 6 together with the nitrogen atom to which they are attached may also stand for a five- to seven-membered heterocycle
  • process according to the invention the new process for producing a composition is referred to as "process according to the invention”.
  • composition according to the invention and of the composition produced by the process according to the invention was found as a hair treatment agent or for its preparation.
  • alkyl includes straight-chain and branched alkyl groups. Suitable short-chain alkyl groups are, for. B. straight-chain or branched Ci-Cz-alkyl, preferably d-C ⁇ -alkyl and particularly preferably Ci-C4-alkyl groups.
  • Branched C 3 -C 5 -alkyl is preferably isopropyl, isobutyl, sec-butyl, tert-butyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 2-dimethylpropyl, 1, 1-dimethylpropyl, 2,2- Dimethylpropyl, 1-ethylpropyl. Preference is given to tert-butyl.
  • Suitable longer-chain Cs-Cso-alkyl groups are straight-chain and branched alkyl groups. These are preferably predominantly linear alkyl radicals, as they also occur in natural or synthetic fatty acids and fatty alcohols and oxo alcohols. These include z.
  • Suitable longer-chain Cs-Cso-alkenyl groups are straight-chain and branched alkenyl groups which may be mono-, di- or polyunsaturated. Preference is given to predominantly linear alkenyl radicals, as they also occur in natural or synthetic fatty acids and fatty alcohols and oxo alcohols.
  • octenyl nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, n-eicosenyl, n-docosenyl, n-tetracosenyl, hexacosenyl, triacontenyl, etc.
  • Cycloalkyl is preferably Cs-Cs-cycloalkyl, such as cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • Aryl includes unsubstituted and substituted aryl groups and is preferably phenyl, ToIyI, XyIyI, mesityl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, naphthacenyl and in particular phenyl, ToIyI, XyIyI or mesityl.
  • N, N-dialkylamides also includes compounds in which the amide nitrogen is part of a five- to seven-membered heterocycle which additionally has a heteroatom selected from oxygen, sulfur and NR a , where R a is hydrogen, alkyl or Cycloalkyl is, may contain.
  • water-soluble monomers and polymers are understood as meaning monomers and polymers which dissolve to at least 1 g / l at 20 ° C. in water.
  • Water-dispersible monomers and polymers are understood as meaning monomers and polymers which decompose into dispersible particles with the aid of shearing forces, for example by stirring.
  • Hydrophilic monomers are preferably water-soluble or at least water-dispersible.
  • the copolymers A) according to the invention are generally water-soluble.
  • the first essential constituent of the composition according to the invention is at least one copolymer A).
  • the copolymers A) to be used according to the invention comprise, in copolymerized form, at least one monomer of component d).
  • the copolymers A) to be used according to the invention have no silicon atom-containing groups in a specific embodiment.
  • the monomer mixture used for the preparation of the copolymers A) to be used according to the invention comprises monomers having cationogenic and / or cationic groups and monomers having anionogenic and / or anionic groups.
  • the amount of monomers used for the polymerization with ionogenic and / or ionic groups is dimensioned such that, based on the total monomers used for the polymerization, the molar fraction of cationogenic and cationic groups is greater than the molar fraction of anionogenic and anionic groups.
  • the copolymers A) to be used according to the invention therefore have on average a molar excess of cationogenic / cationic groups with respect to anionogenic / anionic groups.
  • the molar ratio of cationogenic / cationic groups to anionogenic / anionic groups is preferably at least 1:01, more preferably at least 1.2: 1, in particular at least 1.4: 1, especially at least 1.5: 1, more particularly at least 2 : 1.
  • copolymers A) to be used according to the invention are obtained with particularly advantageous properties when monomers with cationic groups which have at least one quarternary nitrogen atom are used for the polymerization.
  • the cationogenic and / or cationic groups of component b) are preferably nitrogen-containing groups, such as primary, secondary and tertiary amino groups, and quaternary ammonium groups. At least part of the monomers b) has quaternary ammonium groups. Quaternary ammonium groups, d. H. charged cationic groups can be generated from the amine nitrogens by quaternization with alkylating agents.
  • C 1 -C 4 alkyl halides or sulfates such as ethyl chloride, ethyl bromide, methyl chloride, methyl bromide, dimethyl sulfate and diethyl sulfate.
  • a preferred quaternizing agent is diethyl sulfate.
  • Charged cationic groups can also be generated from the amine nitrogens by protonation with acids. Suitable acids are, for. For example, carboxylic acids such as lactic acid, or mineral acids such as phosphoric acid, sulfuric acid and hydrochloric acid.
  • copolymers A) to be used according to the invention comprise, in copolymerized form, at least one compound which is preferably selected from isopropyl acrylate, isopropyl methacrylate, isopropyl acrylamide, isopropyl methacrylamide, isobutyl acrylate, isobutyl methacrylate, isobutyl acrylamide, isobutyl methacrylamide, sec-butyl acrylate, sec.
  • the copolymers A) to be used according to the invention preferably comprise from 15 to 90% by weight, particularly preferably from 20 to 85% by weight, in particular from 25 to 75% by weight, based on the total weight of the monomers used for the polymerization, of at least one monomer a ) polymerized.
  • copolymers A) to be used according to the invention comprise as compound b) at least one compound polymerized with a free-radically polymerizable, ⁇ , ß-ethylenically unsaturated double bond and at least its cationogenic and / or cationic group per molecule. At least part of the compounds b) according to the invention have a quaternary nitrogen atom.
  • the copolymers A) to be used according to the invention preferably contain from 3 to 98% by weight, more preferably from 5 to 90% by weight, in particular from 7 to 80% by weight, based on the total weight of the monomers used for the polymerization, of at least one monomer b ) polymerized.
  • component b) is selected from esters of ⁇ , ⁇ -ethylenically unsaturated mono- and dicarboxylic acids with aminoalcohols which may be mono- or dialkylated on the amine nitrogen, amides of ⁇ , ⁇ -ethylenically unsaturated mono- and dicarboxylic acids with diamines which contain at least one primary or secondary amino group, N, N-diallylamine, N, N-diallyl-N-alkylamines and derivatives thereof, vinyl and allyl-substituted nitrogen heterocycles, vinyl- and allyl-substituted heteroaromatic compounds, the quaternization products of these monomers, and mixtures thereof.
  • component b) comprises at least one N-vinylimidazole compound as the vinyl-substituted heteroaromatic compound.
  • component b) is selected from N-vinylimidazole compounds and mixtures containing at least one N-vinylimidazole compound.
  • Suitable N-vinylimidazole compounds are compounds of the formula
  • R 8 to R 10 are independently hydrogen, Ci-C 4 -AlkVl or phenyl.
  • R 8 to R 10 are hydrogen.
  • the copolymer contains as monomer b) at least one N-vinylimidazole compound of the general formula
  • R 8 to R 10 independently of one another represent hydrogen, C 1 -C 4 -alkyl or phenyl.
  • Preferred monomer b) is 1-vinylimidazole (N-vinylimidazole) and are mixtures containing N-vinylimidazole.
  • Suitable monomers b) are also the compounds obtainable by protonation or quaternization of the abovementioned N-vinylimidazole compounds.
  • Examples of such charged monomers b) are quaternized vinylimidazoles, in particular 3-methyl-1-vinylimidazolium chloride, methosulfate and ethosulfate.
  • Suitable acids and alkylating agents are those listed above.
  • Suitable compounds b) are also the esters of ⁇ , ß-ethylenically unsaturated mono- and dicarboxylic acids with amino alcohols.
  • Preferred amino alcohols are C 2 -C 12 -amino alcohols which are mono- or dialkylated on the amine nitrogen by C 1 -C 8.
  • the acid component of these esters are z.
  • the acid component used is preferably acrylic acid, methacrylic acid and mixtures thereof.
  • Preferred monomers b) are N-tert-butylaminoethyl (meth) acrylate, N, N-dimethylaminomethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N- Dimethylaminopropyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate and N, N-dimethylaminocyclohexyl (meth) acrylate.
  • N-tert-butylaminoethyl (meth) acrylate and N, N-dimethylaminoethyl (meth) acrylate are particularly preferred.
  • Preferred monomers b) are, in particular, also the quaternization products of the abovementioned compounds.
  • Suitable monomers b) are furthermore the amides of the abovementioned ⁇ , ⁇ -ethylenically unsaturated mono- and dicarboxylic acids with diamines which have at least one primary or secondary amino group.
  • diamines having a tertiary and a primary or secondary amino group.
  • Preferred as monomers b) are z.
  • B N- [tert -butylaminoethyl] (meth) acrylamide, N- [2-dimethylamino) ethyl] acrylamide, N- [2- (dimethylamino) ethyl] methacrylamide, N- [3- (dimethylamino) propyl] acrylamide, N- [3- (dimethylamino) propyl] methacrylamide, N- [4- (dimethylamino) butyl] acrylamide, N- [4- (dimethylamino) butyl] methacrylamide, N- [2- (diethylamino) ethyl] acrylamide, N- [4- (dimethylamino) cyclohexyl] acrylamide and N- [4- (dimethylamino) cyclohexyl] methacrylamide.
  • N- [3- (dimethylamino) propyl] acrylamide and N- [3- (dimethylamino) propyl] methacrylamide DMAPMAM.
  • a specific embodiment relates to copolymers A) which contain copolymerized N- [3- (dimethylamino) propyl] acrylamide and N- [3- (dimethylamino) propyl] methacrylamide.
  • component b) consists only of N- [3- (dimethylamino) propyl] acrylamide and / or N- [3- (dimethylamino) propyl] methacrylamide.
  • Suitable monomers b) are furthermore N, N-diallylamines and N, N-diallyl-N-alkylamines and their acid addition salts and quaternization products.
  • Alkyl is preferably Ci-C24-alkyl. Preference is given to N, N-diallyl-N-methylamine and N, N-diallyl-N, N-dimethylammonium compounds, such as. As the chlorides and bromides. Particularly preferred is N, N-diallyl-N-methylamine.
  • Suitable monomers b) are furthermore vinyl- and allyl-substituted nitrogen heterocycles, other than vinylimidazoles, such as 2- and 4-vinylpyridine, 2- and 4-allylpyridine, and the salts thereof.
  • component b) comprises at least one monomer selected from N, N-dimethylaminoethyl (meth) acrylate, N- [3- (dimethylamino) propyl] (meth) acrylamide, quaternized N, N-dimethylaminoethyl (meth) acrylate, quaternized N- [3- (dimethylamino) propyl] (meth) acrylamide and mixtures thereof.
  • component b) preferably comprises N, N-dimethylaminoethyl (meth) acrylate quaternized with methyl chloride, dimethyl sulfate or diethyl sulfate.
  • the terms “quat DMAEMA” and “Quat 31 1” are used synonymously with respect to the term “diethyl sulfate quaternized dimethylaminoethyl methacrylate”.
  • component b) comprises diethyl sulfate quaternized N, N-dimethylaminoethyl (meth) acrylate.
  • the copolymers of the invention contain preferably 2 to 97 wt .-%, more preferably 3 to 96 wt .-%, in particular 4 to 60 wt .-%, based on the total weight of the monomers used for the polymerization, at least one monomer b) in copolymerized form ,
  • the copolymers A) to be used according to the invention comprise as compound c) at least one compound having a free-radically polymerizable, ⁇ , ⁇ -ethylenically unsaturated double bond and at least one anionogenic and / or anionic group per molecule.
  • the component c) is preferably used in an amount of 0.1 to 30 wt .-%, particularly preferably 1 to 25 wt .-%, in particular 1, 5 to 20 wt .-%, used.
  • component c) comprises at least one compound selected from monoethylenically unsaturated carboxylic acids, sulfonic acids, phosphonic acids and mixtures thereof.
  • the monomers c) include monoethylenically unsaturated mono- and dicarboxylic acids having 3 to 25, preferably 3 to 6, carbon atoms, which can also be used in the form of their salts or anhydrides. Examples thereof are acrylic acid, methacrylic acid, ethacrylic acid, ⁇ -chloroacrylic acid, crotonic acid, maleic acid, maleic anhydride, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid and fumaric acid.
  • the monomers c) further include the half esters of monoethylenically unsaturated dicarboxylic acids having 4 to 10, preferably 4 to 6 carbon atoms, for. B.
  • the monomers c) also include monoethylenically unsaturated sulfonic acids and phosphonic acids, for example, vinylsulfonic acid, allylsulfonic acid, sulfoethyl acrylate, sulfoethyl methacrylate, sulfopropyl acrylate, sulfopropyl methacrylate, 2-hydroxy-3-acryloxypropylsulfonic acid, 2-hydroxy-3-methacryloxypropylsulfonic acid, styrenesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, vinylphosphonic acid and allylphosphonic acid.
  • monoethylenically unsaturated sulfonic acids and phosphonic acids for example, vinylsulfonic acid, allylsulfonic acid, sulfoethyl acrylate, sulfoethyl methacrylate, sulfopropyl acrylate,
  • the monomers c) also include the salts of the abovementioned acids, in particular the sodium, potassium and ammonium salts and the salts with amines.
  • the monomers c) can be used as such or as mixtures with one another. The stated proportions by weight are all based on the acid form.
  • Component c) preferably comprises at least one compound selected from acrylic acid, methacrylic acid, ethacrylic acid, ⁇ -chloroacrylic acid, crotonic acid, maleic acid, maleic anhydride, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, glutaconic acid, aconitic acid, 2-acrylamido-2-one methylpropanesulfonic acid, vinylphosphonic acid and mixtures thereof.
  • component c) comprises at least one compound c) which is selected from acrylic acid, methacrylic acid and mixtures thereof.
  • component c) comprises methacrylic acid or consists of methacrylic acid.
  • copolymers A) to be used according to the invention preferably comprise from 5 to 95% by weight, more preferably from 10 to 90% by weight, based on the total weight of the compounds used for the polymerization, of at least one monomer d).
  • component d) selected from primary amides of ⁇ , ⁇ -ethylenically unsaturated monocarboxylic acids, N-vinylamides of saturated monocarboxylic acids, N-vinyllactams, N-alkyl and N, N-dialkylamides ⁇ , ⁇ -ethylenically unsaturated Monocarboxylic acids and mixtures thereof.
  • Preferred monomers d) are N-vinyl lactams and their derivatives, the z.
  • one or more alkyl substituents such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, etc. may have. These include z.
  • N-vinylpyrrolidone N-vinylpiperidone, N-vinylcaprolactam
  • N-vinyl-5-methyl-2-pyrrolidone N-vinyl-5-ethyl-2-pyrrolidone
  • N-vinyl-6-methyl-2-piperidone N-vinyl-6-ethyl-2-piperidone
  • N-vinyl-7-methyl-2-caprolactam N-vinyl-7-ethyl-2-caprolactam, etc.
  • Particular preference is given to using N-vinylpyrrolidone and / or N-vinylcaprolactam.
  • Suitable monomers d) are also acrylamide and methacrylamide.
  • N-alkyl and N, N-dialkylamides of .alpha.,. Beta.-ethylenically unsaturated monocarboxylic acids which have at most 7 further carbon atoms in addition to the carbonyl carbon atom of the amide group are, for example, N-methyl (meth) acrylamide, N-ethyl ( meth) acrylamide, N-propyl (meth) acrylamide, N- (n-butyl) (meth) acrylamide, N-tert-butyl (meth) acrylamide, n-pentyl (meth) acrylamide, n-hexyl (meth) acrylamide, n-heptyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, piperidinyl (meth) acrylamide, morpholinyl (meth) acrylamide and mixtures thereof.
  • NC 8 -C 3 o-alkyl and N- (Ci-C 3 o) alkyl-N- (C8-C 3 o) alkylamides c) are z.
  • Suitable open-chain N-vinylamide compounds as monomers d) are, for example, N-vinylformamide, N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinylpropionamide, N-vinyl N-methylpropionamide, N-vinyl-butyramide and mixtures thereof. Preference is given to using N-vinylformamide.
  • Suitable monomers d) are also compounds of the formula
  • copolymers A) to be used according to the invention may additionally comprise, in copolymerized form, at least one monomer e) other than components a) to d) copolymerizable therewith.
  • the component e) is preferably selected from esters of ⁇ , ⁇ -ethylenically unsaturated mono- and dicarboxylic acids which differ from component a) with C 1 -C 30 -alkanols, unsaturated C 8 -C 50 -fatty alcohols and C 2 -C 30 -alkanediols, and amides ⁇ , ⁇ -ethylenic unsaturated mono- and dicarboxylic acids with C2-C3o amino alcohols having a primary or secondary amino group, esters of vinyl alcohol and allyl alcohol with d-Cso monocarboxylic acids, vinyl ethers, vinyl aromatics, vinyl halides, vinylidene halides, C2-C8 monoolefins, non-aromatic Hydrocarbons having at least two conjugated double bonds and mixtures thereof.
  • Suitable additional monomers e) are furthermore 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate,
  • Suitable additional monomers e) are also 2-hydroxyethylacrylamide, 2-hydroxyethylmethacrylamide, 2-hydroxyethylethacrylamide, 2-hydroxypropylacrylamide, 2-hydroxypropylmethacrylamide, 3-hydroxypropylacrylamide, 3-hydroxypropylmethacrylamide, 3-hydroxybutylacrylamide, 3-hydroxybutylmethacrylamide, 4-hydroxybutylacrylamide, 4-hydroxybutylmethacrylamide , 6-hydroxyhexylacrylamide, 6-hydroxyhexylmethacrylamide, 3-hydroxy-2-ethylhexylacrylamide and 3-hydroxy-2-ethylhexylmethacrylamide.
  • Suitable monomers e) are also polyether acrylates, which in the context of this invention are generally understood to mean esters of ⁇ , ⁇ -ethylenically unsaturated mono- and dicarboxylic acids with polyetherols.
  • Suitable polyetherols are linear or branched, terminal hydroxyl-containing substances containing ether bonds. In general, they have a molecular weight in the range of about 150 to 20000 on.
  • Suitable polyetherols are polyalkylene glycols, such as polyethylene glycols, polypropylene glycols, polytetrahydrofurans and alkylene oxide copolymers.
  • Suitable alkylene oxides for the preparation of alkylene oxide copolymers are, for.
  • alkylene oxide copolymers may contain randomly distributed alkylene oxide units or in copolymerized form in the form of blocks. Preferred are ethylene oxide / propylene oxide copolymers.
  • component e are polyether acrylates of the general formula IV
  • H 2 C CC Y 2 (CH 2 CH 2 O) k (CH 2 CH (CH 3 ) O), Ri 1
  • k and I independently of one another represent an integer from 0 to 1000, the sum of k and I being at least 5,
  • R 11 is hydrogen, C 1 -C 30 -alkyl or C 5 -C 8 -cycloalkyl
  • R 12 is hydrogen or C 1 -C 6 -alkyl
  • Y 2 is O or NR 13 , where R 13 is hydrogen, C 1 -C 30 -alkyl or C 5 -C 8 -cycloalkyl.
  • k is an integer from 1 to 500, in particular from 3 to 250.
  • I is an integer from 0 to 100.
  • R 12 is preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl or n-hexyl, in particular hydrogen, methyl or ethyl.
  • R 11 is preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-pentyl, n-hexyl, octyl, 2-ethylhexyl, decyl, lauryl, p-mityl or stearyl.
  • Y 2 in formula IV is O or NH.
  • Suitable polyether acrylates e) are, for.
  • Suitable polyetherols can easily be prepared by reacting ethylene oxide, 1,2-propylene oxide and / or epichlorohydrin with a starter molecule, such as water or a short-chain alcohol R 11 -OH.
  • the alkylene oxides can be used individually, alternately in succession or as a mixture.
  • the polyether acrylates e) can be used alone or in mixtures for the preparation of the polymers used according to the invention.
  • Suitable additional monomers e) are methyl (meth) acrylate, methyl methacrylate, ethyl (meth) acrylate, ethyl methacrylate, n-butyl (meth) acrylate, tert-butyl methacrylate, tert-butyl methacrylate, n-octyl (meth) acrylate, 1, 1, 3,3-tetramethylbutyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, n-undecyl (meth) acrylate, tridecyl (meth) acrylate, Myristyl (meth) acrylate, pentadecyl (meth) acrylate, palmityl (meth) acrylate, heptadecyl (meth) acrylate,
  • Suitable additional monomers e) are also vinyl acetate, vinyl propionate, vinyl butyrate and mixtures thereof.
  • Suitable additional monomers e) are furthermore ethylene, propylene, isobutylene, butadiene, styrene, ⁇ -methylstyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, vinyl fluoride, vinylidene fluoride and mixtures thereof.
  • the copolymers A) to be used according to the invention preferably comprise in copolymerized form at least one compound e) which is selected from C 1 -C 3 -alkyl methacrylates, hydroxy-C 1 -C -alkyl methacrylates and mixtures thereof.
  • special Preferred are ethyl methacrylate, hydroxyethyl methacrylate and mixtures thereof.
  • ethyl methacrylate is used.
  • the copolymers according to the invention contain these monomers preferably in an amount of from 0 to 50% by weight, more preferably 0 to 45% by weight, based on the total weight of the compounds used for the polymerization, in copolymerized form.
  • the copolymers A) to be used according to the invention preferably contain 0 to 25% by weight, more preferably 0 to 20% by weight, in particular 0 to 15% by weight, based on the total weight of the monomers used for the polymerization, at least one Monomers e) copolymerized. If a monomer e) is used, then preferably in an amount of at least 0.1 wt .-%, particularly preferably at least 1 wt .-% and in particular at least 5 wt .-%.
  • the copolymers A) to be used according to the invention may contain at least one crosslinking agent, ie. H. in copolymerized form contain a compound having two or more than two ethylenically unsaturated, non-conjugated double bonds.
  • Crosslinkers are preferably used in an amount of from 0.01 to 3% by weight, more preferably from 0.01 to 2% by weight, in particular from 0.1 to 2% by weight and especially from 0.1 to 1% by weight. , based on the total weight of the monomers used for the polymerization.
  • Suitable crosslinkers f) are, for example, acrylic esters, methacrylic esters, allyl ethers or vinyl ethers of at least dihydric alcohols.
  • the OH groups of the underlying alcohols may be completely or partially etherified or esterified; however, the crosslinkers contain at least two ethylenically unsaturated groups.
  • Examples of the underlying alcohols are dihydric alcohols such as 1, 2-ethanediol, 1, 2-propanediol, 1, 3-propanediol, 1, 2-butanediol, 1, 3-butanediol, 2,3-butanediol, 1, 4- Butanediol, but-2-en-1, 4-diol, 1, 2-pentanediol, 1, 5-pentanediol, 1, 2-hexanediol, 1, 6-hexanediol, 1, 10-decanediol, 1, 2-dodecanediol, 1, 12-dodecanediol, neopentyl glycol, 3-methylpentane-1, 5-diol, 2,5-dimethyl-1,3-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,2-cyclohexanediol, 1, 4-cycl
  • block copolymers of ethylene oxide or propylene oxide or copolymers which contain incorporated ethylene oxide and propylene oxide groups are examples of block copolymers of ethylene oxide or propylene oxide or copolymers which contain incorporated ethylene oxide and propylene oxide groups.
  • Examples of underlying alcohols having more than two OH groups are trimethylolpropane, glycerol, pentaerythritol, 1, 2,5-pentanetriol, 1, 2,6-hexanetriol, triethoxycyanuric acid, sorbitan, sugars such as sucrose, glucose, mannose.
  • the polyhydric alcohols can also be used after reaction with ethylene oxide or propylene oxide as the corresponding ethoxylates or propoxylates.
  • the polyhydric alcohols can also be first converted by reaction with epichlorohydrin in the corresponding glycidyl ether.
  • crosslinkers f) are the vinyl esters or the esters of monohydric, unsaturated alcohols with ethylenically unsaturated Cs-C ⁇ -carboxylic acids, for example acrylic acid, methacrylic acid, itaconic acid, maleic acid or fumaric acid.
  • examples of such alcohols are allyl alcohol, 1-buten-3-ol, 5-hexen-1-ol, 1-octen-3-ol, 9-decen-1-ol, dicyclopentenyl alcohol, 10-undecen-1-ol, cinnamyl alcohol , Citronellol, crotyl alcohol or cis-9-octadecen-1-ol.
  • esterify the monohydric, unsaturated alcohols with polybasic carboxylic acids for example malonic acid, tartaric acid, trimellitic acid, phthalic acid, terephthalic acid, citric acid or succinic acid.
  • crosslinkers f) are esters of unsaturated carboxylic acids with the polyhydric alcohols described above, for example oleic acid, crotonic acid, cinnamic acid or 10-undecenoic acid.
  • crosslinkers f) are urethane diacrylates and urethane polyacrylates, as described, for. B. under the name Laromer® are commercially available.
  • Suitable crosslinkers f) are also straight-chain or branched, linear or cyclic, aliphatic or aromatic hydrocarbons which have at least two double bonds which must not be conjugated in aliphatic hydrocarbons, eg. As divinylbenzene, divinyltoluene, 1, 7-octadiene, 1, 9-decadiene, 4-vinyl-1-cyclohexene, trivinylcyclohexane or polybutadienes having molecular weights of 200 to 20,000.
  • crosslinkers f) are the acrylamides, methacrylamides and N-allylamines of at least divalent amines.
  • amines are, for example, 1,2-diaminomethane, 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1, 6-diaminohexane, 1, 12-dodecanediamine, piperazine, diethylenetriamine or isophorone diamine.
  • amides of allylamine and unsaturated carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, or at least dibasic carboxylic acids, as described above.
  • triallylmethylammonium chloride or methyl sulfate, as crosslinker f) suitable.
  • N-vinyl compounds of urea derivatives at least difunctional amides, cyanurates or urethanes, for example of urea, ethyleneurea, propyleneurea or tartaramide, eg. N, N'-divinylethyleneurea or N, N'-divinylpropyleneurea.
  • crosslinkers f) are divinyldioxane, tetraallylsilane or tetravinylsilane.
  • mixtures of the abovementioned compounds f) can also be used.
  • water-soluble crosslinkers f) are used.
  • Crosslinkers f) which are particularly preferably used are, for example, methylenebisacrylamide, triallylamine and triallylalkylammonium salts, divinylimidazole, pentaerythritol triallyl ether, N, N'-divinylethyleneurea, reaction products of polyhydric alcohols with acrylic acid or methacrylic acid, methacrylic acid esters and acrylic esters of polyalkylene oxides or polyhydric alcohols which have Ethylene oxide and / or propylene oxide and / or epichlorohydrin have been implemented.
  • Very particularly preferred crosslinkers f) are pentaerythritol triallyl ether, methylenebisacrylamide, N, N'-divinylethyleneurea, triallylamine and triallylmonoalkylammonium salts and acrylic esters of glycol, butanediol, trimethylolpropane or glycerol or acrylic esters of glycol reacted with ethylene oxide and / or epichlorohydrin, butanediol, Trimethylolpropane or glycerin.
  • Preferred copolymers A) to be used according to the invention are those which are
  • copolymers A) to be used according to the invention consist of repeating units of
  • tert-butyl (meth) acrylate at least one compound b) selected from N, N-dimethylaminoethyl (meth) acrylate,
  • copolymers A) to be used according to the invention consist of repeating units of
  • partially or completely quaternized monomers b) are used to prepare the abovementioned copolymers A) to be used according to the invention, dimethyl sulfate or diethyl sulfate, in particular diethyl sulfate, being used as the quaternizing agent.
  • copolymers A) to be used according to the invention is carried out by customary methods known to the person skilled in the art, eg. B. by solution, precipitation, suspension or emulsion. Also suitable is the VWW
  • Preferred solvents for solution polymerization are aqueous solvents, such as water and mixtures of water with water-miscible solvents, for example alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-hexanol and Cyclohexanol and glycols, such as ethylene glycol, propylene glycol and butylene glycol, and the methyl or ethyl ethers of dihydric alcohols, diethylene glycol, triethylene glycol, polyethylene glycols with number average molecular weights up to about 3000, glycerol and dioxane.
  • alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-hexanol and Cyclohex
  • the polymerization temperatures in the solution polymerization are preferably in a range from about 30 to 120 ° C., particularly preferably 40 to 100 ° C.
  • the precipitation polymerization is preferably carried out in a substantially anhydrous, aprotic solvent or solvent mixture, preferably in ethyl acetate and / or n-butyl acetate.
  • a substantially anhydrous, aprotic solvent or solvent mixture is understood as meaning a solvent or solvent mixture having a water content of at most 5% by weight.
  • the precipitation is preferably carried out at a temperature in the range from 70 to 140 0 C, preferably 75 to 100 0 C, in particular from 80 to 95 0 C.
  • the resulting polymer particles precipitate out of the reaction solution and can ren by conventional procedural, such as filtration using Negative pressure, to be isolated.
  • Negative pressure for precipitation polymerization, it is possible to use surface-active, polymeric compounds, preferably based on polysiloxanes.
  • polymers are generally obtained with higher molecular weights than in the solution.
  • the polymerization is usually carried out under atmospheric pressure, but it can also proceed under reduced or elevated pressure. A suitable pressure range is between 1 and 5 bar.
  • the monomers can be polymerized with the aid of free-radical initiators.
  • the peroxo and / or azo compounds customary for this purpose can be used, for example alkali metal or ammonium peroxydisulfates, diacetyl peroxide, dibenzoyl peroxide, succinyl peroxide, di-tert-butyl peroxide, tert-butyl perbenzoate, tert.
  • initiator mixtures or redox initiator systems such as.
  • all inorganic or organic bases are suitable, in particular those which undergo no reaction with the monomers apart from any salt formation. Suitable bases are, for.
  • tertiary amines such as triethylamine, and amino alcohols such as triethanolamine, methyldiethanolamine or dimethylethanolamine.
  • the polymerization can be carried out in the presence of at least one regulator.
  • a regulator the usual compounds known in the art, such.
  • B. sulfur compounds for. As mercaptoethanol, 2-ethylhexyl thioglycolate, thioglycolic acid or dodecyl mercaptan and Tribromchlor- methane or other compounds which act in a regulating manner on the molecular weight of the polymers obtained.
  • a preferred regulator is cysteine.
  • the K value of the copolymers according to the invention is 18 or higher, preferably 25 or higher, more preferably 42 or higher.
  • the K value of the copolymers A) to be used according to the invention is 120 or lower, preferably 80 or lower, particularly preferably 70 or lower. Most preferred are K values in the range of 42 to 70 (Fikentscher, Cellulose Chemistry, Vol. 13, pp. 58 to 64 (1932)).
  • the K value determination is carried out as a 1% solution of the copolymer in N-methylpyrrolidone.
  • K values in the range from 28 to 42 are also preferred.
  • a postpolymerization step can follow the polymerization (main polymerization).
  • the post-polymerization can be carried out in the presence of the same or a different initiator system as the main polymerization.
  • the postpolymerization is preferably carried out at least at the same, preferably at a higher temperature than the main polymerization.
  • the reaction mixture may be subjected to steam stripping or steam distillation following the polymerization or between the first and second polymerization steps.
  • the resulting solutions or dispersions of the copolymers A) to be used according to the invention can be prepared by various drying methods, such as. As spray drying, fluidized spray drying, drum drying or freeze drying can be converted into powder form. Preferably, the spray drying is used.
  • the dry powders thus obtained can be advantageously converted by dissolving or redispersing in water again in a solution or dispersion.
  • Powdery copolymers A) to be used according to the invention have the advantage of better storage stability, easier transportation and generally show a lower tendency for microbial attack.
  • the content of the composition according to the invention on the copolymers A) to be used according to the invention can vary very widely and can therefore be perfectly adapted to the requirements of the individual case.
  • the content is preferably from 0.01 to 60% by weight, preferably from 0.05 to 55% by weight and in particular from 0.1 to 50% by weight, based in each case on the composition according to the invention.
  • the second essential constituent of the composition according to the invention is at least one, in particular a polymer B) other than the copolymer A) to be used according to the invention, selected from the group consisting of polymers which contain at least one ionogenic and / or ionic group in the molecule , and non-ionic polymers.
  • the polymers B) which contain at least one ionogenic and / or ionic group in the molecule are selected from the group consisting of anionic polymers which contain at least one anionogenic and / or anionic group in the molecule; cationic polymers containing at least one cationogenic and / or cationic group in the molecule; and amphoteric and neutral polymers containing at least one anionogenic and / or anionic group and at least one cationogenic and / or cationic group in the molecule.
  • anionic polymers B) are homo- and copolymers of acrylic acid and methacrylic acid or salts thereof, copolymers of acrylic acid and acrylamide and their salts; Sodium salts of polyhydroxycarboxylic acids, water-soluble or water-dispersible polyesters, polyurethanes, eg. B. Luviset PUR® Fa. BASF, and polyureas.
  • Particularly suitable anionic polymers B) are copolymers of t-butyl acrylate, ethyl acrylate, methacrylic acid (for example Luvimer® 100P), copolymers of ethyl acrylate and methacrylic acid (for example Luvimer® MAE), copolymers of N-tert-butylacrylamide , Ethyl acrylate, acrylic acid (Ultrahold® 8, strong), copolymers of vinyl acetate, crotonic acid and optionally other vinyl esters (eg Luviset® brands), maleic anhydride copolymers, if appropriate reacted with alcohol, anionic polysiloxanes, eg.
  • carboxy-functional carboxypolysiloxanes for example, carboxy-functional carboxypolysiloxanes, copolymers of vinylpyrrolidone, t-butyl acrylate, methacrylic acid (eg Luviskol® VBM), copolymers of acrylic acid and methacrylic acid with hydrophobic monomers, such.
  • B. C4-C3o-alkyl esters of (meth) acrylic acid, C4-C3o-alkyl vinyl esters, C4-C3o-alkyl vinyl ethers and hyaluronic acid.
  • anionic polymers are furthermore vinyl acetate / crotonic acid copolymers, as are commercially available, for example, under the names Resyn® (National Starch) and Gafset® (GAF) and vinylpyrrolidone / vinyl acrylate copolymers, obtainable, for example, under the trademark Luviflex® (US Pat. BASF).
  • Further suitable polymers are the vinylpyrrolines available under the name Luviflex® VBM-35 (BASF). don / acrylate terpolymer and sodium sulfonate-containing polyamides or sodium sulfonate-containing polyesters.
  • vinylpyrrolidone / ethyl methacrylate / methacrylic acid copolymers such as those sold by Stepan under the names Stepanhold-Extra and -R1 and the Carboset® grades from BF Goodrich.
  • suitable anionic polymers B) are known from European Patent Application EP 1 712 256, page 3, paragraphs [0022] and [0023].
  • Suitable cationic polymers B) are z.
  • Vinyl imidazolium salts (Luviquat® FC, Luviquat® HM, Luviquat® MS, Luviset Clear®, Luviquat Supreme®, Luviquat® Care), copolymers
  • Suitable cationic (quaternized) polymers are also Merquat® (polymer based on dimethyldiallyl ammonium chloride), Gafquat® (quaternary polymers which are formed by reaction of polyvinylpyrrolidone with quaternary ammonium compounds), polymer JR (hydroxyethylcellulose with cationic groups) and cationic polymers based on plants, eg. As guar polymers, such as the Jaguar® brands of Fa. Rhodia. Also suitable are cationic polyurethanes B), such as those described in WO 2006/069742.
  • cationic copolymers preparable from N-vinylpyrrolidone (VP), N-vinylimidazole (VI), methacrylamide (MAM) and quaternized N-vinylimidazole (QVI), as described in European patent applications EP 1 712 255 and EP 1 712 256 will be described.
  • VP N-vinylpyrrolidone
  • VI N-vinylimidazole
  • MAM methacrylamide
  • QVI quaternized N-vinylimidazole
  • Very particularly suitable polymers B) are neutral polymers, such as polyvinylpyrrolidone, copolymers of N-vinylpyrrolidone and vinyl acetate and / or vinyl propionate, polysiloxanes, polyvinylcaprolactam and other copolymers with N-vinylpyrrolidone, polyethyleneimines and their salts, polyvinylamines and their derivatives Salts, cellulose derivatives, polyaspartic acid salts and derivatives.
  • neutral polymers such as polyvinylpyrrolidone, copolymers of N-vinylpyrrolidone and vinyl acetate and / or vinyl propionate, polysiloxanes, polyvinylcaprolactam and other copolymers with N-vinylpyrrolidone, polyethyleneimines and their salts, polyvinylamines and their derivatives Salts, cellulose derivatives, polyaspartic acid salts and derivatives.
  • Luviflex® Swing partially sapon
  • Suitable polymers B) are also nonionic, water-soluble or water-dispersible polymers or oligomers, such as polyvinyl caprolactam, z. B. Luviskol® Plus (BASF), or polyvinylpyrrolidone and their copolymers, in particular with vinyl esters, such as vinyl acetate, z. Luviskol® VA 37 or VA 64 (BASF); Polyamides, z. B. based of itaconic acid and aliphatic diamines, as described, for. B. in DE-A-43 33 238 are described.
  • nonionic, water-soluble or water-dispersible polymers or oligomers such as polyvinyl caprolactam, z. B. Luviskol® Plus (BASF), or polyvinylpyrrolidone and their copolymers, in particular with vinyl esters, such as vinyl acetate, z. Luviskol® VA 37 or VA 64 (BASF); Polyamides, z. B. based of ita
  • Suitable polymers B) are also ampholytic, i. amphoteric or zwitterionic polymers, such as those available under the names Amphomer® (National Starch) octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers and zwitterionic polymers, as described for example in German patent applications DE 39 29 973, DE 21 50 557, DE 28 17 369 and DE 37 08 451 are disclosed.
  • Acrylamidopropyltrimethylammonium chloride / acrylic acid or methacrylic acid copolymers and their alkali metal and ammonium salts are preferred zwitterionic polymers.
  • zwitterionic polymers B) are methacroylethylbetaine / methacrylate copolymers, which are commercially available under the name Amersette® (AMERCHOL), and copolymers of hydroxyethyl methacrylate, methyl methacrylate, N, N-dimethylaminoethyl methacrylate and acrylic acid (Jordapon®). Also suitable are the ampholytic copolymers, as described in the international patent application WO 2007/010035 A1, page 7, line 14, to page 66, line 27, and page 78, line 36, to page 93, line 12, and BASF SE under the brand name Luvigel® Advanved.
  • Suitable polymers B) are also nonionic, siloxane-containing, water-soluble or -dispersible polymers, for.
  • polyether siloxanes such as Tegopren® (Goldschmidt) or Belsil® (Wacker).
  • the content of the composition of the invention on the polymer B) is from 1 to 60 wt .-%, preferably 1 to 55 wt .-% and in particular 1 to 50 wt .-%, each based on the composition of the invention.
  • composition of the invention contains at least one additive C).
  • the composition according to the invention preferably contains at least two, preferably at least three, more preferably at least four and in particular at least five additives C).
  • All additives C) which are customarily used in the field of cosmetics and pharmacy, preferably in hair-treatment compositions, in particular in foam-like dressings, hair sprays, hair gels and mousses, are suitable.
  • the additive C) or the additives C) from the group consisting of water, alcohols, blowing agents or propellants, defoamers, anionic, cationic, amphoteric and neutral surface-active compounds, ie surfactants, emulsifiers, foaming agents, solubilizers, preservatives, perfume oils, opacifiers, active ingredients, UV filters, care ingredients such as panthenol, collagen, vitamins, protein hydrolysates, alpha- and beta-hydroxycarboxylic acids, stabilizers, pH regulators, dyes, viscosity regulators, Gelling agents, dyes, salts, humectants, rehydrates Dr., thickeners, styling and conditioner polymers, conditioning substances based on silicone compounds and complexing agents, preferably alcohols, blowing agents and emulsifiers.
  • defoamers anionic, cationic, amphoteric and neutral surface-active compounds, ie surfactants, emulsifiers, foaming agents, so
  • alcohols C) are mono-, di- or polyhydric alcohols having preferably 1 to 8 carbon atoms, such as ethanol, n-propanol, isopropanol, propylene glycol, glycerol and sorbitol.
  • Propellants or propellants C are the propellants commonly used for hair sprays or aerosol foams. Preference is given to mixtures of propane / butane, pentane, dimethyl ether, 1,1-difluoroethane (HFC-152a), carbon dioxide, nitrogen or compressed air, in particular propane / butane.
  • HFC-152a 1,1-difluoroethane
  • Suitable anionic surfactants C) are, for example, alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkoyl sarcosinates, acyl taurates, acyl isothionates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha-olefin sulfonates, in particular the alkali metal and alkaline earth metal salts, eg. As sodium, potassium, magnesium, calcium, and ammonium and triethanolamine salts.
  • the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 to 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units in the molecule.
  • Suitable amphoteric surfactants are, for. Alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines, alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates or -propionates, alkylamphodiacetates or -dipropionates.
  • cocodimethylsulfopropyl betaine, lauryl betaine, cocamidopropyl betaine or sodium cocamphopropionate can be used.
  • Suitable nonionic surfactants C) are, for example, the reaction products of aliphatic alcohols or alkylphenols having 6 to 20 C atoms in the alkyl chain, which may be linear or branched, with ethylene oxide and / or propylene oxide. The amount of alkylene oxide is about 6 to 60 moles per mole of alcohol.
  • alkylamine oxides are also suitable.
  • mono- or dialkylalkanolamides are also suitable.
  • fatty acid esters of polyethylene glycols are also suitable.
  • ethoxylated fatty acid amides are also suitable.
  • alkylpolyglycosides are also suitable.
  • emulsifiers C all emulsifiers commonly used in hair foams can be used. Suitable emulsifiers may be nonionic, cationic or anionic or amphoteric.
  • nonionic emulsifiers C) are Laurethe, z. Laureth-4; Cetethe, z. Cetheth-1, polyethylene glycol cetyl ether; Cetearethe, z. Cetheareth-25, polyglycol fatty acid glycerides, hydroxylated lecithin, lactyl esters of fatty acids, alkylpolyglycosides.
  • cationic emulsifiers C) are cetyldimethyl-2-hydroxyethylammonium dihydrogenphosphate, cetyltrimonium chloride, cetyltrimmonium bromide, cocotrimonium methylsulfate, quaternium-1 to x (INCI).
  • Anionic emulsifiers C) can, for example, be selected from the group of alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl succinates, alkyl sulfosuccinates, N-alkyl sarcosinates, acyl taurates, acyl isethionates, alkyl phosphates, alkyl ether phosphates, alkyl ether carboxylates, alpha-olefin sulfonates, especially the alkali and alkaline earth metal salts, e.g. , As sodium, potassium, magnesium, calcium, and
  • alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 to 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units in the molecule.
  • Suitable silicone compounds C) are, for example, polyalkylsiloxanes, polyarylsiloxanes, polyarylalkylsiloxanes, polyethersiloxanes, silicone resins or dimethicone copolymers (CTFA) and amino-functional silicone compounds such as amodimethicones (CTFA).
  • the choice of the additive C) or of the additives C) depends on whether the composition according to the invention is to have a solid or a liquid consistency. In addition, the choice depends on whether the composition according to the invention is to be used in the context of the inventive use as a hair treatment agent as a mousse, hair gel, hair spray with and without propellant gas or as a mousse.
  • the selection can be made by the person skilled in the art on the basis of his general Expertise on the specific effects of additives C), where appropriate, with the aid of a few preliminary preliminary experiments. As for general knowledge, reference is made to HP Fiedler, Encyclopedia of Pharmaceuticals, Cosmetics and Related Areas, Fourth Edition, Aulendorf: ECV Editio Kantor-Verlag, 1996.
  • the content of additives C) of the composition according to the invention can vary widely and depends on the requirements of the individual case within the context of the use according to the invention. Again, the skilled person can determine the proportions based on his general expertise on the effective amounts of the additives C), where appropriate, with the help of a few orienting experiments.
  • the content is from 1 to 98.99 wt .-%, preferably 10 to 98 wt .-% and in particular 20 to 97 wt .-%, each based on the composition of the invention.
  • compositions according to the invention are used in the context of the use according to the invention as hair treatment agents, in particular in the form of mousses, hair gels, hair sprays, mousses, shampoos, conditioners or shower gels.
  • the hair sprays according to the invention may contain or be free of propellants C).
  • the mousses, hair gels, hair sprays, mousses, shampoos, conditioners and shower gels according to the invention preferably comprise predominantly or exclusively water-soluble or water-dispersible components.
  • the compounds used in the mousses, hair gels, hair sprays, mousses, shampoos, conditioners or shower gels according to the invention are water-dispersible, they can be used in the form of aqueous microdispersions having particle diameters of usually 1 to 350 nm, preferably 1 to 250 nm ,
  • the solids contents of these hair treatment compositions according to the invention are usually in a range from about 0.5 to 20% by weight.
  • these microdispersions do not require any emulsifiers C) or surfactants C) for their stabilization.
  • compositions according to the invention in particular the hair treatment compositions according to the invention, in each case based on the composition according to the invention
  • composition according to the invention for use as aerosol and pump hairsprays, in each case based on the composition of the invention, from
  • composition according to the invention for use as a mousse, in each case based on the composition of the invention, from
  • composition according to the invention is preferably carried out by means of the process according to the invention by
  • R 1 is hydrogen or C 1 -C 8 -alkyl
  • X 1 is O or NR 3 , where R 3 is hydrogen, alkyl, cycloalkyl, aryl or hetaryl, and
  • R 2 is branched C 3 -C 8 -alkyl
  • amide group-containing monomer which is selected from ⁇ , ⁇ -ethylenically unsaturated amide-containing compounds of the general formula II
  • R 5 and R 6 together with the nitrogen atom to which they are attached may also stand for a five- to seven-membered heterocycle
  • the protic polar organic solvent is one of the above-described alcohols C), in particular ethanol or isopropanol.
  • the process according to the invention offers no special features, but can be carried out with the aid of customary and known mixing units, such as stirred tanks, Ultraturrax, inline dissolvers, microfluidizers, extruders or kneaders.
  • customary and known mixing units such as stirred tanks, Ultraturrax, inline dissolvers, microfluidizers, extruders or kneaders.
  • the resulting composition according to the invention which contains water and / or alcohol C), can already be supplied as such to the use according to the invention or it can serve for the production of hair treatment compositions according to the invention.
  • compositions according to the invention can, however, also be dried, resulting in compositions according to the invention which preferably have a solid consistency and, in particular, are pulverulent.
  • drying the drying methods described above can be used.
  • the dried compositions according to the invention can be stored without problems, transported and for purposes of the inventive use in water and / or alcohol C) redispersed and / or dissolved again.
  • DMAEMA dimethylaminoethyl methacrylate quat DMAEMA dimethylaminoethyl methacrylate quaternized with diethyl sulfate
  • DMAPMAM dimethylaminopropylmethacrylamide quat.
  • DMAEMA dimethylaminoethyl methacrylate quaternized with diethyl sulfate
  • EGDMA ethylene glycol dimethacrylate
  • PETAE Petaerythritol triallyl ether
  • the mousses of Examples 25 to 64 were prepared by combining the ingredients listed in Tables 3 to 7 in the indicated amounts and homogenizing the resulting mixtures.
  • Copolymer 2 1 3 - - - - - - - - -
  • the hair gels of Examples 65-118 were prepared by combining the ingredients listed in Tables 7-12 and in the indicated amounts and homogenizing the resulting mixtures.
  • Polymer B Polyquaternium 46 1 1
  • Copolymer A ⁇ 3 3 5 2 5 1 1 1 1 2 2
  • the aerosol hair sprays with propellant gases of Examples 119 to 133 were prepared by combining the ingredients listed in Tables 13 and 14 and in the indicated amounts and homogenizing the resulting mixtures.
  • Copolymer A6) 33 3 2 3 3 3 3 3 2 3
  • the pumped hairsprays without propellant gases of Examples 134 to 143 were prepared by combining the ingredients listed in Table 15 in the indicated amounts and homogenizing the resulting mixtures.
  • Vinyl acetate-crotonate-vinyl neodecanoate copolymer , , , , , 3
  • PEG 12 Dimethicone 0,1 - - 1 - - 0,5 - Aminomethylpropanol _ 2 - - - 2 - - - -
  • the hair treatment compositions of Examples 25 to 143 had excellent performance properties. They caused a high elasticity in treated hair with strong consolidation (even at high humidity), especially in the sense of curl retention and the prevention of curling when spraying with hydrous hair fixatives ("initial curl droop prevention "). The treated hair had a very good grip and a very good handling.
  • Examples 25, 35, 45, 64, 68, 77, 85, 99, 105, 11 1, 122, 129 and 140 were repeated except that instead of the copolymer A6) the copolymers A1) to A5) and A7) to A24) of Examples 1 to 5 and 7 to 24 were used.
  • the resulting hair treatment agents 144 to 442 had advantageous properties that were completely comparable to those of the hair treatment compositions of Examples 25 to 143.
  • Examples 65 to 104 of Tables 7 to 10 were repeated, with the difference that in addition to the polymers B) used in the respective formulations, in each case 1 wt .-%, based on the respective formulation, of the ampholytic copolymer of Example 23, Page 78, line 38, to page 79, line 27, Table I, page 81, the international patent application WO 2007/010035 A1 as a further polymer B) was used.
  • the resulting hair gels 443 to 482 had the same advantageous properties as the hair gels 65 to 104.
  • Examples 95 and 100 of Table 10 were repeated, with the difference that the acrylate copolymer B) used in the formulations in question by 1 wt .-%, based on the particular formulation, of the ampholytic copolymer of Example 23, page 78, line 38 until page 79, line 27, Table I, page 81, of international patent application WO 2007/010035 A1 has been replaced.
  • the resulting hair gels 483 and 484 had excellent performance properties.
  • Example 98 of Table 10 was repeated, with the difference that the acrylate-allyl-methacrylate copolymer B) used in the relevant formulation represented 1% by weight, based on the formulation, of the ampholytic copolymer of Example 23, page 78 , Line 38, to page 79, line 27, Table I, page 81, the international patent application WO 2007/010035 A1 has been replaced.
  • the resulting Haargel 485 also had excellent performance properties.
  • Examples 96, 97.99 and 101 to 103 of Table 10 were repeated, with the difference that in addition to the polymers B used in the respective formulations, in each case 1 wt .-%, based on the particular formulation, of the ampholytic copolymer of Example 23, page 78, line 38, to page 79, line 27, Table I, page 81, of international patent application WO 2007/010035 A1 was used as further polymer B).
  • the resulting hair gels 487 to 492 had the same advantageous properties as the hair gels 96, 97, 99 and 101 to 103.
  • Examples 105 to 108 of Table 11 were repeated, with the difference that the carbomer used for the formulations in question polyacrylic acid B) by 1 wt .-%, based on the particular formulation of the ampholytic copolymer of Example 23, page 78, line 38 until page 79, line 27, Table I, page 81, of international patent application WO 2007/010035 A1 has been replaced.
  • the resulting hair gels 493 to 496 had the same advantageous properties as the hair gels 105 to 108.
  • Examples 109 to 118 of Table 12 were repeated, with the difference that in addition to the polymers used in the formulations in question B) in each case 1% by weight, based on the respective formulation, of the ampholytic copolymer of Example 23, page 78, line 38, to page 79, line 27, table I, page 81, of international patent application WO 2007 / 010035 A1 was used as further polymer B).
  • the resulting hair gels 497 to 506 had the same advantageous properties as hair gels 109 to 118.
  • Examples 507 and 520 were prepared by combining the ingredients listed in Table 16 in the indicated amounts and homogenizing the resulting mixtures.
  • Examples 507 to 520 were outstandingly suitable as easily washable shampoos, conditioners and shower gels.

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Abstract

Composition contenant : A) un copolymère ampholytique présentant un excédent de groupes cationogènes/cationiques par rapport aux groupes anionogènes/anioniques, pouvant être préparé par polymérisation radicalaire a) d’un monomère éthylèniquement insaturé en α,ß de formule générale (I) où R1 = hydrogène ou C1-C8-alkyle, X1 = O ou NR3, sachant que R3 = hydrogène, alkyle, cycloalkyle, aryle ou hétaryle et R2 = C3-C5-alkyle ramifié, b) d’un composé présentant une liaison double éthylèniquement insaturée en α,ß, polymérisable par voie radicalaire, et un groupe cationogène et/ou cationique par molécule, sachant qu’au moins une partie des composés b) présentent un atome d’azote quaternaire, et c) d’un composé présentant une liaison double éthylèniquement insaturée en α,ß, polymérisable par voie radicalaire, et un groupe anionogène et/ou anionique par molécule, et d) éventuellement d’un monomère contenant des groupes amide ; B) 1 à 60 % (en poids), relativement à la composition, d’un polymère non ionique différent de A) et/ou d’un polymère contenant des groupes ionogènes et/ou ioniques; et C) au moins un additif. L’invention concerne également un procédé pour préparer cette composition, et son utilisation comme produit de traitement capillaire ou pour préparer ce produit.
PCT/EP2009/051920 2008-02-21 2009-02-18 Composition contenant un copolymère ampholytique à base de monomères contenant de l’azote quaternisé et d'au moins un polymère différent de ceux-ci, et son utilisation WO2009103735A1 (fr)

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* Cited by examiner, † Cited by third party
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EP2098217A3 (fr) * 2008-03-07 2015-06-17 Basf Se Fixateur de cheveux donnant du volume doté d'un copolymère ampholytique
FR3045360A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant un copolymere vinylformamide/vinylamine, un polymere fixant, un agent tensioactif cationique et une silicone aminee
WO2017108565A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition comprenant un copolymère vinylformamide/vinylamine, un polymère de fixation et une combinaison particulière de tensioactifs
WO2017108564A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition pulvérisable sous forme de mousse comprenant un copolymère vinylformamide/vinylamine, un tensioactif particulier et un propulseur d'aérosol
WO2020053108A1 (fr) * 2018-09-14 2020-03-19 Unilever Plc Composition de mousse
EP3275425B1 (fr) * 2016-07-26 2021-03-03 Kao Germany GmbH Composition de coiffure
WO2022048856A1 (fr) * 2020-09-07 2022-03-10 Henkel Ag & Co. Kgaa Masque de soin capillaire liquide clair à changement d'aspect sans effet alourdissant
WO2023247793A1 (fr) * 2022-06-24 2023-12-28 Nouryon Chemicals International B.V. Polymères filmogènes d'alcool polyvinylique pour formulations de fixation des cheveux à base d'alcool et leurs procédés d'utilisation
CN117701065A (zh) * 2023-11-24 2024-03-15 广东新辉化学有限公司 一种水性聚氨酯油墨连接料及其制备方法和应用
US12031128B2 (en) 2022-04-07 2024-07-09 Battelle Memorial Institute Rapid design, build, test, and learn technologies for identifying and using non-viral carriers

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WO2004058837A2 (fr) * 2002-12-30 2004-07-15 Basf Aktiengesellschaft Copolymere ampholytique et son utilisation
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WO2004058837A2 (fr) * 2002-12-30 2004-07-15 Basf Aktiengesellschaft Copolymere ampholytique et son utilisation
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2098217A3 (fr) * 2008-03-07 2015-06-17 Basf Se Fixateur de cheveux donnant du volume doté d'un copolymère ampholytique
FR3045360A1 (fr) * 2015-12-21 2017-06-23 Oreal Composition comprenant un copolymere vinylformamide/vinylamine, un polymere fixant, un agent tensioactif cationique et une silicone aminee
WO2017108565A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition comprenant un copolymère vinylformamide/vinylamine, un polymère de fixation et une combinaison particulière de tensioactifs
WO2017108564A1 (fr) * 2015-12-21 2017-06-29 L'oreal Composition pulvérisable sous forme de mousse comprenant un copolymère vinylformamide/vinylamine, un tensioactif particulier et un propulseur d'aérosol
EP3275425B1 (fr) * 2016-07-26 2021-03-03 Kao Germany GmbH Composition de coiffure
CN112689497A (zh) * 2018-09-14 2021-04-20 联合利华知识产权控股有限公司 摩丝组合物
WO2020053108A1 (fr) * 2018-09-14 2020-03-19 Unilever Plc Composition de mousse
CN112689497B (zh) * 2018-09-14 2023-08-15 联合利华知识产权控股有限公司 摩丝组合物
US11884901B2 (en) 2018-09-14 2024-01-30 Conopco, Inc. Mousse composition
WO2022048856A1 (fr) * 2020-09-07 2022-03-10 Henkel Ag & Co. Kgaa Masque de soin capillaire liquide clair à changement d'aspect sans effet alourdissant
US12031128B2 (en) 2022-04-07 2024-07-09 Battelle Memorial Institute Rapid design, build, test, and learn technologies for identifying and using non-viral carriers
WO2023247793A1 (fr) * 2022-06-24 2023-12-28 Nouryon Chemicals International B.V. Polymères filmogènes d'alcool polyvinylique pour formulations de fixation des cheveux à base d'alcool et leurs procédés d'utilisation
CN117701065A (zh) * 2023-11-24 2024-03-15 广东新辉化学有限公司 一种水性聚氨酯油墨连接料及其制备方法和应用
CN117701065B (zh) * 2023-11-24 2024-05-28 广东新辉化学有限公司 一种水性聚氨酯油墨连接料及其制备方法和应用

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