EP2323620A2 - Agents destinés à des fibres kératiniques, contenant au moins un polymère cationique amphiphile particulier et au moins un polymère qui présente des chaînes latérales, contenant des silicones, et des groupes anioniques - Google Patents

Agents destinés à des fibres kératiniques, contenant au moins un polymère cationique amphiphile particulier et au moins un polymère qui présente des chaînes latérales, contenant des silicones, et des groupes anioniques

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Publication number
EP2323620A2
EP2323620A2 EP09780876A EP09780876A EP2323620A2 EP 2323620 A2 EP2323620 A2 EP 2323620A2 EP 09780876 A EP09780876 A EP 09780876A EP 09780876 A EP09780876 A EP 09780876A EP 2323620 A2 EP2323620 A2 EP 2323620A2
Authority
EP
European Patent Office
Prior art keywords
group
polymer
monomer
monomers
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP09780876A
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German (de)
English (en)
Inventor
Dirk Hentrich
Sabine Albrechtsen
Esma Alanya
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP2323620A2 publication Critical patent/EP2323620A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/18—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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
    • 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

Definitions

  • the present invention relates to hair treatment compositions containing a combination of at least one particular amphiphilic cationic polymer with at least one polymer having silicone-containing side chains and anionic groups, the use of these agents for temporary shaping and / or care of keratin-containing fibers and hair gels based on these agents ,
  • all animal hair e.g. Wool, horsehair, angora hair, furs, feathers and products or textiles made from them.
  • the keratinic fibers are human hairs.
  • Corresponding temporary shaping agents usually contain synthetic polymers as the shaping component.
  • Preparations containing a dissolved or dispersed polymer can be applied to the hair by means of propellant gases or by a pumping mechanism.
  • hair gels and hair waxes are generally not applied directly to the hair, but distributed by means of a comb or hands in the hair.
  • the most important property of a composition for the temporary deformation of keratinic fibers is to give the treated fibers in the produced form the strongest possible hold. If the keratin fibers are human hair, it is also referred to as a strong hairstyle or the high degree of retention of the styling agent.
  • the hairstyle hold is essentially determined by the type and amount of the synthetic polymer used, but also an influence of the other constituents of the styling agent may be given. In addition to a high degree of hold, styling agents must meet a whole range of other requirements.
  • properties on the hair may be broadly subdivided into properties on the hair, properties of the particular formulation, eg properties of the foam, of the gel or of the sprayed aerosol, and of properties which affect the handling of the styling agent, whereby the properties on the hair are of particular importance. Particularly noteworthy are moisture resistance, low tackiness and a balanced conditioning effect. Furthermore, a styling agent should be universally applicable as possible for all hair types.
  • the polymers can be subdivided into cationic, anionic, nonionic and amphoteric film-forming and / or setting polymers.
  • the polymers when applied to hair, the polymers give a polymer film which, on the one hand, gives the hairstyle strong hold but, on the other hand, is sufficiently flexible not to break under stress. If the polymer film is too brittle, it results in the formation of so-called Filmpiaken, that is residues that detach during the movement of the hair and give the impression that the user of the corresponding styling agent would dandruff.
  • the object of the present invention was therefore to provide a means for temporary deformation of keratinous fibers, which is characterized by a high degree of retention and in particular has excellent handleability during application to the keratin-containing fibers, is not sticky and the keratin-containing fiber while a gives a good grip but no sticky film.
  • the polymer combination according to the invention causes, in addition to a strong hold, especially in its application form as a gel, a convenient handling, since the gel has a doughy consistency, yet can be easily distributed and feels barely tacky.
  • a first subject of the present invention are therefore agents for treating keratin-containing fibers, in particular human hair, contained in a cosmetically acceptable carrier (a) at least one amphiphilic, cationic polymer comprising at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III) and at least one structural unit of the formula (IV)
  • R 1 and R 4 independently of one another represent a hydrogen atom or a methyl group
  • X 1 and X 2 independently of one another represent an oxygen atom or a group NH
  • a 1 and A 2 independently of one another represent a group of ethane-1,2-diyl, Propane-1, 3-diyl or butane-1, 4-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent a (C 1 to C 4 ) -alkyl group, R 7 represents a (C 8 to C 30 ) -alkyl group and
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • Examples of (C 1 to C 4 ) -alkyl groups according to the invention are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl.
  • Examples of (C 8 to C 30 ) -alkyl groups according to the invention are octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl), docosyl ( behenyl).
  • amphiphilic cationic polymers are preferably used in the agents according to the invention if the amphiphilic cationic polymers fulfill one or more of the following characteristics:
  • R 1 and R 4 each represent a methyl group
  • X 1 stands for a group NH
  • X 2 stands for a group NH
  • a 1 and A 2 are each independently ethane-1, 2-diyl or propane-1, 3-diyl,
  • R 2 , R 3 , R 5 and R 6 independently of one another represent methyl or ethyl, (particularly preferably methyl),
  • R 7 is a (Ci 0 to C 24 ) alkyl group, in particular decyl (caprinyl), undecyl,
  • Dodecyl (lauryl), tridecyl, tetradecyl (myristyl), pentadecyl, hexadecyl (cetyl),
  • Octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).
  • the structural unit of the formula (IV) is selected, to consist of at least one structural unit of the formulas (IV-1) to (IV-8)
  • each R 7 is a (C 8 to C 30 ) alkyl group.
  • particularly preferred structural unit of the formula (IV) are the structural units of the formula (IV-7) and / or the formula (IV-8), wherein in each case R 7 is octyl (capryl), decyl (caprinyl), dodecyl (lauryl ), Tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl (arachyl) or docosyl (behenyl).
  • the structural unit of the formula (IV-8) represents according to the invention a very particularly preferred structural unit of the formula (IV).
  • a very particularly preferred amphiphilic, cationic polymer comprises at least one structural unit of the formula (I), at least one structural unit of the formula (II), at least one structural unit of the formula (III-8) and at least one structural unit of the formula (IV-8),
  • R 7 is a (C 8 to C 30 ) alkyl group (especially octyl (capryl), decyl (caprinyl), dodecyl (lauryl), tetradecyl (myristyl), hexadecyl (cetyl), octadecyl (stearyl), eicosyl ( Arachyl) or docosyl (behenyl)).
  • amphiphilic, cationic polymers according to the invention preferably have a molecular weight of from 10,000 g / mol to 50,000,000 g / mol, in particular from 50,000 g / mol to 5,000,000 g / mol, more preferably from 75,000 g / mol to 1,000,000 g / mol.
  • a very particularly preferred amphiphilic, cationic polymer according to the invention is the copolymer of N-vinylpyrrolidone, N-vinylcaprolactam, N- (3-dimethylaminopropyl) methacrylamide and 3- (methacryloylamino) propyl-lauryl-dimethylammonium chloride (INCI name:
  • Polyquaternium-69 containing 300 (for example, under the trade name Aqua Style ® marketed 28-32 wt .-% of active substance in ethanol-water mixture) by the company ISP.
  • Preferred agents according to the invention comprise the above-described amphiphilic cationic polymers in an amount of from 0.05% by weight to 10.0% by weight, particularly preferably from 0.05% by weight to 5.0% by weight. %, very particularly preferably from 0.1 to 4.0% by weight, in each case based on the weight of the composition.
  • the agent according to the invention contains, in addition to the previously defined amphiphilic, cationic polymers, at least one anionic polymer with silicone-containing side chains.
  • Preferred agents according to the invention comprise the above-described silicone-containing side chains and polymers comprising anionic groups in an amount of from 0.05% by weight to 10% by weight, particularly preferably from 0.05% by weight to 5.0 Wt .-%, most preferably from 0.1 to 2.0 wt.%, In each case based on the weight of the composition.
  • the polymers (a) and (b) are used according to the invention preferably in a weight ratio of 5: 1 to 1: 5, in particular 4: 1 to 1: 4.
  • silicone-containing side chains of the anionic polymer are selected from representatives of the group of silicone copolyols.
  • Silicone copolyols are silicones which contain in their structure at least one unit of one or more alkylene glycols, in particular ethylene glycol and / or propylene glycol.
  • the polymer having at least one silicone-containing side chain and at least one anionic group (hereinafter also referred to as polymer (b)) is preferably selected from at least one polymer obtained by (co) polymerization of the monomers (i) and optionally (ii) ( i) at least one monomer which is an olefinically unsaturated group, a silicone radical and, if no further anionic monomer (ii) is used, at least one anionic
  • Monomers, associative monomers or crosslinking monomers are particularly preferred for use in the composition according to the invention.
  • at least one polymer (b) which is obtained by copolymerization of at least the monomers (i) to (v) (i) at least one monomer which carries an olefinically unsaturated group and a silicone radical and (ii) at least one additional monomer selected from (preferably olefinically unsaturated), anionic monomers, (iii) at least one additional nonionic monomer, (iv) optionally at least one additional associative monomer, (v) optionally at least one additional crosslinking monomer.
  • a preferred variant of the polymer (b) is obtained by copolymerization of at least the
  • At least one monomer bearing an olefinically unsaturated group and a silicone radical at least one additional monomer selected from (preferably olefinically unsaturated), anionic monomers, (iii) at least one additional nonionic monomer, (iv) at least one additional associative monomer, (v) at least one additional crosslinking monomer.
  • the monomer (i) at least one monomer selected from the group consisting of compounds of the formulas (A1) and (A2) is preferably used
  • R 1 and R 2 independently of one another represent a (C 1 to C 30 ) -alkyl group, a (C 1 to C 2 o) -alkyl group substituted by at least one halogen atom (for example -CCl 3 , -CBr 3 , -CF 3 ) , a (C 3 to C 8 ) -cycloalkyl group, a (C 6 to C 14 ) -aryl group or (C 2 to C 2 o) -alkenyl group, R 3 is a (C 1 to C 30 ) -alkyl group, a (C 1 to C 20 ) -alkyl group substituted by at least one halogen atom (eg -CCl 3 , -CBr 3 , -CF 3 ), a (C 3 to C 8 ) - cycloalkyl group, a (C 6 to C 14 ) -aryl group or (C 2 to C 2 o) -alkeny
  • R 4 independently of one another represents a (C 1 to C 30 ) -alkyl group, a (C 6 to C 14 ) -
  • Aryl group a (C 2 to C 20 ) alkenyl group
  • R and R ' at least one of the two radicals R or R' is an ester group of an olefinically unsaturated carboxylic acid according to one of the formulas (Est1) to (Est7), the other also also one of these ester groups of the formulas (Est1) to (Est7) means or represents a hydrogen atom,
  • E is an ethane-1,2-diyl group
  • P represents a propane-1,2-diyl group or a propane-1,3-diyl group
  • a, b and c independently of one another represent a number from 0 to 100
  • n represents a number from 0 to 1000
  • x represents one Number 2 or 3
  • v represents a number from 0 to 200
  • y represents a number from 1 to 200
  • z is less than or equal to y.
  • the EO or PO or OE or OP fragments can be present in the block or randomly distributed in the monomer.
  • the agent according to the invention contains as polymer (b) at least one polymer having silicone side chains and at least one anionic group which is formed by copolymerization of at least the monomers (i) to (iii)
  • R 1 and R 2 independently of one another represent a (C 1 to C 30 ) -alkyl group, a (C 1 to C 2 o) -alkyl group substituted by at least one halogen atom (for example -CCl 3 , -CBr 3 , -CF 3 ), a (C 3 to C 8 ) -cycloalkyl group, a (C 6 to C 14 ) -aryl group or (C 2 to C 2 o) -alkenyl group,
  • R 3 is a (C 1 to C 30 ) -alkyl group, a (C 1 to C 20 ) -alkyl group substituted by at least one halogen atom (eg -CCl 3 , -CBr 3 , -CF 3 ), a (C 3 to C 8 ) - cycloalkyl group, a (C 6 to C 14 ) -aryl group or (C 2 to C 20 ) -alkenyl group,
  • R 4 independently of one another represents a (C 1 to C 30 ) -alkyl group, a (C 6 to C 14 ) -
  • Aryl group a (C 2 to C 20 ) alkenyl group
  • R and R ' at least one of the two radicals R or R' is an ester group of an olefinically unsaturated carboxylic acid according to one of the formulas (Est1) to (Est7), the other also also one of these ester groups of the formulas (Est1) to (Est7) means or represents a hydrogen atom,
  • E is an ethane-1,2-diyl group
  • P represents a propane-1,2-diyl group or a propane-1,3-diyl group
  • a, b and c independently of one another represent a number from 0 to 100
  • n represents a number from 0 to 1000
  • x represents one Number 2 or 3
  • v stands for a number from 0 to 200
  • y stands for a number from 1 to 200 and z is less than or equal to y
  • x represents the number 3 according to formulas (A1) or (A2).
  • the monomer (i) is selected from at least one monomer selected from the group consisting of the formulas (A1-1), (A1-2), (A2-1 ) and (A2-2)
  • R 1 , R 2 , R 3 , R 4 , E, P, a, b, c, x, n, v, y and z are defined according to formulas (A1) and (A2), R 7 is a hydrogen atom or a methyl group in which one of R 5 or R 6 is a methyl group and the other is a hydrogen atom and R is a hydrogen atom or a radical of the formulas (Est8) or (Est 9),
  • R 5 , R 6 and R 7 are as defined above.
  • suitable monomers are those in which x is the number 3 stands.
  • the nonionic additional monomers according to all the aforementioned embodiments are preferably selected from the group formed, (C 1 to C 30 ) -alkyl (meth) acrylates, cyclohexyl (meth) acrylates, 3,3,5-trimethylcyclohexyl (meth) acrylate, (C 1 to C 30 ) -alkyl (meth) acrylamides, styrene, substituted styrenes (such as vinyltoluene derivatives, eg 2-methylstyrene, butylstyrene, isopropylstyrene, p-chlorostyrene), vinyl esters (such as vinyl acetate, vinyl butyrate, vinyl caprolate, vinyl pivalate, vinyl neodecanoate) , unsaturated nitriles (such as methacrylonitrile, acrylonitrile), unsaturated silanes (such as trimethylvinylsilane, dimethyle
  • Dihydroxypropyl) acrylamide, t-butyl (meth) acrylamide, N-vinylcaprolactam, N-vinylpyrrolidone, methacrylamidoethyl-N-ethyleneurea (eg CH 2 C (CH 3 ) C (O) NHCH 2 CH 2 -N-ethyleneurea), C 1 to C 6 ) -alkoxy-substituted (meth) acrylates, (C 1 to C 6 ) -alkoxy-substituted (meth) acrylamides (such as, for example, methoxyethyl (meth) acrylate, 2- (2-ethoxyethyloxy) ethyl (meth) acrylate, Allyl alcohol, glycerol monoallyl ether, 3-methyl-3-buten-1-ol.
  • the additional nonionic monomers may be water soluble. Furthermore, the nonionic monomers can be used as a lipophilic monomer
  • the additional anionic monomers according to all the aforementioned embodiments are preferably selected from the group which is formed from acidic, polymerizable, ethylenically unsaturated monomers which preferably contain at least one carboxyl group and / or sulfonic acid group and / or phosphoric acid group which form an acidic and acidic group.
  • Base dissociation also provides an anionic group.
  • acid groups are derived, for example, from mono- or diacids, anhydrides of dicarboxylic acids, monoesters of dicarboxylic acids or the salts of the abovementioned compounds.
  • Preferred additional anionic monomers are selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, (C 1 to C 18 ) monoalkyl esters of maleic, fumaric, itaconic acid (such as methyl maleate, monoisopropyl maleate , Butyl fumarate), maleic acid anhydride, itaconic anhydride,
  • Suitable salts of the aforementioned additional anionic monomers include, for example, alkali metal salts (such as sodium, potassium and lithium salts), alkaline earth metal salts (such as calcium and magnesium salts), ammonium salts (NH 4 + ) and salts by reaction with alkanolamines (such as 2-amino). 2-methyl-1-propanol, 2-aminoethanol, diethanolamine, triethanolamine, triethylamine).
  • Suitable additional cationic monomers are basic, polymerizable, ethylenically unsaturated monomers which preferably have at least one amino group. These basic amino groups are derived, for example, from mono-, di- or polyaminoalkyl groups or nitrogen-containing heteroaromatic groups.
  • suitable additional cationic monomers are selected from the group consisting of mono- (C 1 -C 4 ) -alkylamino (C 1 -C 6 ) -alkyl (meth) acrylate, di- (C 1 -C 4 ) - alkylamino (C 1 to C 8 ) alkyl (meth) acrylate, mono (C 1 to C 4 ) alkylamino (C 1 to C 8 ) -alkyl (meth) acrylamides, di (C 1 to C 4 ) -alkylamino (C 1 to C 8 ) alkyl (meth) acrylamide, nitrogen heterocycle-containing (meth) acrylamide, nitrogen heterocycle-containing (meth) acrylates, in particular from 2- (N, N-dimethylamino) ethyl (meth) acrylate (DMAEMA), 3- (N, N) Dimethylamino) propyl (meth)
  • DMAEMA 2- (N, N-di
  • R is a hydrogen atom or a methyl group
  • R ', R "and R” independently of one another represent a (Ci to C 2 o) -alkyl group, X stands for an oxygen atom or a group NH,
  • A is an ethane-1,2-diyl group or a propane-1,3-diyl group, as well as salts of all the abovementioned compounds.
  • cationic monomers (ii) are all possible physiologically acceptable anions, such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • Suitable salts of the additional cationic monomers thus include salts of mineral acid (such as hydrochloric acid or sulfuric acid), (C 1 to C 7 ) alkyl sulfates, phosphates, salts of organic acids (such as acetates, citrates, maleates, tartrates).
  • such additional associative monomers are suitable for the synthesis of polymers (b) according to the invention which contain an ethylenically unsaturated end group (1) for addition polymerization with other monomers of the monomer mixture, a polyoxyalkylene-containing Middle group (2) for a contribution to the hydrophilicity of the polymeric end product and a hydrophobic end group (3) for a hydrophobic contribution of the polymeric end product.
  • the end group (1) is preferably derived from ethylenically unsaturated monocarboxylic or dicarboxylic acids or their anhydrides, more preferably from mono- or di-carboxylic acids having 3 or 4 carbon atoms or their anhydrides. Further, the end group (1) of the additional associative monomers can be derived from allyl ethers or vinyl ethers; nonionic vinyl-substituted urethane monomers or vinyl-substituted urea derivatives.
  • the middle group (2) preferably consists of a polyoxyalkylene segment of from 5 to 250, more preferably from 10 to 120, and most preferably from 15 to 60 repeating (C 2 to C 6 ) alkylene oxide units.
  • Very particularly preferred middle groups (2) include polyoxyethylene segments and / or polyoxypropylene segments and / or polyoxybutylene segments, containing a total of 5 to 150, preferably 10 to 100, particularly preferably 15 to 60, of said alkylene oxide units.
  • the hydrophobic end group (3) of the additional associative monomer preferably represents a hydrocarbon radical selected from one of the following classes: linear (C 8 to C 40 ) alkyl group, aryl substituted (C 2 to C 40 ) alkyl group, (C 2 to C 40 ) -alkyl-substituted phenyl group, branched (C 8 to C 40 ) -alkyl group, carbocyclic (C 8 to C 40 ) -alkyl group, esters having 8 to 80 carbon atoms as a complex ester.
  • Said complex esters according to the invention in an esterification of a polyol with a saturated or unsaturated, long-chain fatty acid with hydroxy group (s) understood. By long-chain, the skilled person understands a number of 10 to 30 carbon atoms.
  • suitable polyols are glycerol, sorbitol, pentaerythritol, trimethylolpropane.
  • Suitable hydrophobic end groups (3) of the additional associative monomer are linear or branched, saturated or unsaturated hydrocarbon radicals of 8 to 40
  • Carbon atoms such as capryl, isooctyl, decyl, lauryl, myristyl, cetyl, stearyl,
  • Isostearyl arachidyl, behenyl, cerotyl, montanyl, melissyl, lacceryl, hydrogenated peanut oil, hydrogenated soybean oil, hydrogenated canola oil, hydrogenated tallow oil, hydrogenated (Ci 0 to C 30 ) terpenes (such as hydrogenated geraniol, hydrogenated farnesol, hydrogenated phytol
  • Examples of suitable (C 2 to C 40 ) alkyl-substituted phenyl groups are octylphenyl,
  • carbocyclic (C 8 to C 40 ) alkyl groups examples include sterol derivatives (such as cholesterol, lanosterol, 7-dehydrocholesterol, phytosterol, stigmasterol,
  • Pinene hydrogenated retinol, camphor, isobornyl alcohol.
  • aryl-substituted (C 2 to C 40 ) alkyl groups are styryl (eg, 2-phenylethyl), distyryl
  • esters having 8 to 80 carbon atoms as the complex ester are hydrogenated castor oil, 1,2-diacylglycerides (such as glycerol 1,2-distearate, glycerin).
  • R 2 is a hydrogen atom or a methyl group
  • R 3 is a linear (C 8 to C 40 ) alkyl group, an aryl-substituted (C 2 to C 40 ) -
  • Alkyl group (C 2 to C 40 ) -alkyl-substituted phenyl group, branched (C 8 to C 40 ) -
  • Alkyl group C 8 -C 40 -alkyl carbocyclic group, esters with 8 to 80 carbon atoms as complex ester, X independently represents a C 2 H 4 group, a C 3 H 6 group or a C 4 H 8 -
  • n represents a number from 5 to 250, preferably from 5 to 100, particularly preferably from 10 to
  • Very particularly preferred additional associative monomers of the formula (Assi) are selected from the group formed from cetyl polyethoxylated methacrylate (CEM), stearyl polyethoxylated (meth) acrylate, arachidyl polyethoxylated (meth) acrylate, behenyl polyethoxylated methacrylate (BEM), lauryl polyethoxylated methacrylate (LEM ), Cerotyl polyethoxylated (meth) acrylate, montanyl polyethoxylated (meth) acrylate,
  • CEM cetyl polyethoxylated methacrylate
  • BEM behenyl polyethoxylated methacrylate
  • LOM lauryl polyethoxylated methacrylate
  • Cerotyl polyethoxylated (meth) acrylate montanyl polyethoxylated (meth) acrylate
  • Tristyrylphenol polyethoxylated methacrylate (TEM), hydrogenated castor oil polyethoxylated (meth) acrylate, canolapolyethoxylated (meth) acrylate and cholesteryl polyethoxylated (meth) acrylate, wherein the number of polyethoxy units in the monomer (ii) is 5 to 100, preferably 10 to 80, particularly preferred 15 to 60 is Ethyleneoxidiseren.
  • the anionic polymer according to the invention having at least one silicone-containing side chain is preferably crosslinked according to the invention.
  • At least one additional crosslinking monomer is preferably selected from the group consisting of polyunsaturated aromatic monomers (such as divinylbenzene, divinylnaphthalene, trivinylbenzene), polyunsaturated alicyclic monomers (such as 1,2,4-trivinylcyclohexane), di-functional esters of the present invention Phthalic acid (such as diallyl phthalate), polyunsaturated aliphatic monomers (such as dienes, trienes, tetraenes such as isoprene, 1, 3-butadiene, 1, 5-hexadiene, 1, 5,9-decatriene, 1, 9-decadiene, 1, 5 Heptadiene), polyalkenyl ethers (such as triallylpentaerythritol, diallylpentaerythritol, diallylsucrose, octaallylsucrose, trimethylolpropane diallyl ether), poly
  • Particularly suitable polyunsaturated additional crosslinking monomers are derived from ethoxylated polyols such as diols, triols and diphenols, each ethoxylated with from 2 to 100 moles of ethylene oxide per mole of hydroxyl groups and terminated with a polymerizable unsaturated group such as vinyl ethers, allyl ethers, acrylate esters, methacrylate esters.
  • additional crosslinking monomers include bisphenol A ethoxylated di (meth) acrylate, bisphenol F ethoxylated di (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylates, acrylate and methacrylate esters of polyols having at least two acrylate ester or methacrylate ester functionalities (such as Trimethylolpropane triacrylate (TMPTA), trimethylolpropane ethoxylated (15) triacrylate (TMPEO15TA), trimethylolpropane dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), bisphenol A dimethacrylate ethoxylated with 30 moles of ethylene oxide (EOBDMA).
  • TMPTA Trimethylolpropane triacrylate
  • TMPEO15TA trimethylolpropane ethoxylated (15) triacrylate
  • TEGDMA triethylene glycol dimethacrylate
  • compositions according to the invention preference is given to adding at least one anionic polymer having silicone side chains which is obtained by copolymerization of at least the monomers (i) to (v) (i) at least one monomer which carries an olefinically unsaturated group and a silicone radical and
  • Methacrylic acid optionally at least one additional associative monomer, (v) optionally, at least one additional crosslinking monomer.
  • a preferred variant of the polymer (b) is obtained by copolymerization of at least the
  • a particularly preferred anionic polymer having silicon-containing side chains is under the tradename Fixate ® Super Hold (30 wt .-% polymer active substance, INCI name: Polyacrylate-2 Crosspolymer) from Noveon expelled.
  • composition according to the invention additionally contains at least one film-forming and / or setting polymer in a preferred embodiment.
  • Film-forming polymers are polymers which leave a continuous film on the skin, the hair or the nails when drying.
  • Such film formers can be used in a wide variety of cosmetic products, such as for example face masks, make-up, hair fixatives, hair sprays, hair gels, hair waxes, hair treatments, shampoos or nail varnishes.
  • Particular preference is given to polymers which have a sufficient solubility in water or water / alcohol mixtures in order to be present in completely completely dissolved form in the agent according to the invention.
  • the film-forming polymers may be of synthetic or natural origin.
  • film-forming polymers are understood as meaning polymers which, when used in 0.01 to 20% strength by weight aqueous, alcoholic or aqueous-alcoholic solution, are capable of depositing a transparent polymer film on the hair.
  • Firming polymers contribute to the maintenance and / or build-up of the hair volume and hair fullness of the overall hairstyle. These polymers are also film-forming polymers and therefore generally typical substances for shaping hair treatment agents such as hair fixatives, hair foams, hair waxes, hair sprays.
  • the film formation can be quite selective and connect only a few fibers.
  • composition of the invention preferably comprises at least one film-forming and / or setting polymer selected from at least one polymer of the group formed from non-ionic polymers, cationic polymers, amphoteric polymers, zwitterionic polymers and anionic polymers.
  • the additional film-forming and / or setting polymers are in the agent according to the invention preferably in an amount of 0.01 wt .-% to 20 wt .-%, in particular from 0.5 wt .-% to 15 wt .-%, very particularly preferably from 2.0 wt .-% to 10.0 wt .-%, each based on the weight of the composition.
  • These quantities also apply to all subsequent preferred types of film-forming and / or setting polymers which can be used in the compositions according to the invention. If differing preferred quantities have been specified below, the latter are considered to be even more preferred amounts.
  • agents which, in addition to the previously defined amphiphilic cationic polymers, contain at least one film-forming and / or setting polymer which is selected from at least one polymer of the group formed from nonionic polymers based on ethylenically unsaturated monomers, in particular out
  • Nonionic polymers based on ethylenically unsaturated monomers which are suitable as film-forming and / or setting polymers are those nonionic polymers which comprise at least one of the following structural units
  • R is a hydrogen atom or a methyl group
  • R ' represents a hydrogen atom or a (C 1 to C 4 ) acyl group
  • R "and R” independently represent a (C 1 to C 7 ) alkyl group or a
  • R '" represents a linear or branched (C 1 to C 4 ) -alkyl group or a (C 2 to C 4 ) -
  • Preferred nonionic film-forming and / or nonionic hair-fixing polymers are homopolymers or copolymers composed of at least one of the following monomers: vinylpyrrolidone, vinylcaprolactam, vinyl esters such as vinyl acetate, vinyl alcohol, acrylamide, methacrylamide, alkyl and dialkylacrylamide, alkyl and dialkylmethacrylamide , Alkyl acrylate, alkyl methacrylate, wherein in each case the alkyl groups of these monomers are selected from (C 1 to C 3 ) alkyl groups.
  • Nonionic polymers based on ethylenically unsaturated monomers which are particularly suitable for the compositions according to the invention comprise at least one of the following structural units
  • R ' represents a hydrogen atom or a (C 1 to C 30 ) acyl group, in particular a
  • nonionic cellulose derivatives are also suitable for use as film-forming and / or setting polymers which are preferably selected from methylcellulose and in particular from cellulose ethers such as hydroxypropylcellulose (eg hydroxypropylcellulose with a molecular weight of 30,000 to 50,000 g / mol, which is marketed for example under the trade name Nisso Sl ® from Lehmann & Voss, Hamburg), hydroxyethyl cellulose, such as (e.g., under the trademark Culminal® ® and Benecel ® AQUALON) and Natrosol ® - Types (Hercules) are distributed.
  • cellulose ethers such as hydroxypropylcellulose (eg hydroxypropylcellulose with a molecular weight of 30,000 to 50,000 g / mol, which is marketed for example under the trade name Nisso Sl ® from Lehmann & Voss, Hamburg), hydroxyethyl cellulose, such as (e.
  • Cationic polymers are to be understood as meaning polymers which have a group in the main and / or side chain which may be “temporary” or “permanent” cationic.
  • "permanently cationic” refers to those polymers which have a cationic group, irrespective of the pH of the agent. These are usually polymers containing a quaternary nitrogen atom, for example in the form of an ammonium group.
  • Preferred cationic groups are quaternary ammonium groups.
  • those polymers in which the quaternary ammonium group is bonded via a C 1-4 hydrocarbon group to a polymer main chain constructed from acrylic acid, methacrylic acid or derivatives thereof have proven to be particularly suitable.
  • a cationic film-forming and / or cationic setting polymer which is preferably suitable according to the invention is at least one cationic film-forming and / or cationic setting polymer which contains at least one structural element of the formula (M9) and additionally at least one structural element of the formula (M 10)
  • R is a hydrogen atom or a methyl group
  • R ', R "and R” independently of one another represent a (C 1 to C 6 ) -alkyl group, X represents an oxygen atom or a group of NH,
  • A is an ethane-1,2-diyl group or a propane-1,3-diyl group, n is 1 or 3.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • the cationic film-forming and / or cationic fixing polymers are particularly preferably selected from cationic, quaternized cellulose derivatives.
  • Suitable cationic and / or setting polymers are preferably cationic, quaternized cellulose derivatives.
  • Such cationic, quaternized celluloses prove to be particularly advantageous for the purposes of the invention, which carry more than one permanent cationic charge in a side chain.
  • cationic celluloses such cationic celluloses with the INCI name Polyquaternium-4 in turn, are particularly suitable, which are sold for example under the names of Celquat ® H 100, Celquat L 200 ® by the company National Starch.
  • Cationic polymers which are particularly preferably used in the context of the invention furthermore include those cationic film-forming and / or cationic consolidating copolymers which contain at least one structural element of the formula (M11)
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group, and additionally has at least one further cationic and / or nonionic structural element.
  • physiologically acceptable anions such as chloride, bromide, hydrogen sulfate, methyl sulfate, ethyl sulfate, tetrafluoroborate, phosphate, hydrogen phosphate, dihydrogen phosphate or p-toluenesulfonate, triflate.
  • Including vinylpyrrolidone / i-vinyl-S-methyl-I H-imidazolium chloride copolymers are (for example that with the INCI name Polyquaternium-16 under the trade names Luviquat ® Style, Luviquat ® FC 370, Luviquat ® FC 550, Luviquat ® FC 905 and Luviquat ® HM 552 (BASF SE)), vinyl pyrrolidone i-vinyl-3-methyl-I H-imidazolium copolymers (such as for example that with the INCI name Polyquaternium-44 under the trade names Luviquat ® Care (BASF SE) / ), vinylpyrrolidone / vinylcaprolactam / i-vinyl-3-methyl-I H-imidazolium terpolymer (such as that with the INCI name Polyquaternium-46 under the trade names Luviquat ® Care or Luviquat ® Hold (BASF SE)), vinyl
  • cationic polymers which can preferably be used in the agents according to the invention are the so-called "temporary cationic" polymers. These polymers usually contain an amino group which, at certain pH values, is present as quaternary ammonium group and thus cationic.
  • Chitosans include, for example, chitosans.
  • Chitosan and / or chitosan derivatives are very particularly preferably suitable film-forming and / or setting polymers in the context of the present invention.
  • Chitosans are biopolymers and are counted among the group of hydrocolloids. Chemically, these are partially deacetylated chitins of different molecular weight. For the production of chitosans is based on chitin, preferably the shell remains of crustaceans, which are available as cheap raw materials in large quantities.
  • the chitin is usually first deproteinized by the addition of bases, demineralized by the addition of mineral acids and finally deacetylated by the addition of strong bases, wherein the molecular weights can be distributed over a broad spectrum.
  • Preferably used are those having an average molecular weight of 800,000 to 1,200,000 daltons, a Brookfield viscosity (1% by weight in glycolic acid) below 5000 mPas, a degree of deacetylation in the range of 80 to 88%, and a Have ash content of less than 0.3 wt .-%.
  • chitosans as typical cationic biopolymers
  • cationically derivatized chitosans such as, for example, quaternization products
  • alkoxylated chitosans are also suitable for the purposes of the invention.
  • Agents preferred according to the invention are characterized in that they comprise as chitosan derivative (s) neutralization products of chitosan with at least one acid selected from lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid, hydroxyisovaleric acid or mixtures of these neutralization products.
  • chitosan derivative (s) neutralization products of chitosan with at least one acid selected from lactic acid, pyrrolidonecarboxylic acid, nicotinic acid, hydroxyisobutyric acid, hydroxyisovaleric acid or mixtures of these neutralization products.
  • Suitable chitosan are, for example, under the trade names Hydagen ® CMF (1 wt .-% active ingredient in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g / mol Cognis), Hydagen ® HCMF (chitosan (80%) deacetylated), molecular weight 50,000 to 1,000,000 g / mol, Cognis), Kytamer ® PC (80 wt .-% of active substance of chitosan pyrolidoncarboxylat (INCI name: chitosan PCA), Amerchol) and Chitolam ® NB / commercially 101 freely available.
  • Hydagen ® CMF (1 wt .-% active ingredient in aqueous solution with 0.4 wt .-% glycolic acid, molecular weight 500000 to 5000000 g / mol Cognis)
  • the chitosan or its derivatives are preferred in the inventive compositions in an amount of 0.01 wt .-% to 20 wt .-%, particularly preferably from 0.01 wt .-% to 10.0 wt .-%, completely particularly preferably from 0.1% by weight to 1% by weight, based in each case on the weight of the composition according to the invention.
  • suitable temporary cationic polymers are also those which have at least one structural unit of the formulas (M 1-1) to (M 1-8)
  • those copolymers are preferred which contain at least one structural unit of the formulas (M 1-1) to (M 1-8) and additionally at least one structural unit of the formula (M 10),
  • n 1 or 3.
  • Vinylcaprolactam / vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer (for example as a 35-39% solids in ethanol in the form of the commercial product Advantage LC E with the INCI name: vinyl caprolactam / VP / dimethylaminoethyl methacrylate copolymer, alcohol, lauryl pyrrolidone (ISP)),
  • Vinylpyrrolidone / dimethylaminopropylmethacrylamide copolymer for example INCI name: VP / DMAPA Acrylates Copolymer under the trade name Styleze CC-10 (ISP)
  • ISP Styleze CC-10
  • compositions of the invention may also contain at least one amphoteric polymer as a film-forming and / or setting polymer.
  • amphoteric polymers includes both those polymers which contain in the molecule both free amino groups and free -COOH or SO 3 H groups and are capable of forming internal salts, as well as zwitterionic polymers which in the molecule have quaternary ammonium groups and -COO ' or -SO 3 ' groups and those polymers comprising -COOH or SO 3 H groups and quaternary ammonium groups.
  • an inventively amphopolymer suitable is the acrylic resin commercially available as Amphomer ®, which is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and their simple alkyl esters.
  • Amphomer ® is a copolymer of tert-butylaminoethyl methacrylate, N- (1, 1, 3,3-tetramethylbutyl) -acrylamide and two or more monomers from the group of acrylic acid, Methacrylic acid and their simple alkyl esters.
  • the latter have in addition to the cationogenic group or positively charged group at least one negatively charged group in the molecule and are also referred to as zwitterionic polymers.
  • the amphoteric polymers are preferably present in the compositions according to the invention in amounts of from 0.01% by weight to 20% by weight, particularly preferably from 0.05 to 10% by weight, based on the total composition. Quantities of 0.1 to 5 wt .-% are very particularly preferred.
  • At least one anionic film-forming and / or anionic setting polymer can be used as the film-forming and / or setting polymers.
  • the anionic polymers are anionic polymers which have carboxylate and / or sulfonate groups.
  • anionic monomers from which such polymers may consist are acrylic acid, methacrylic acid, crotonic acid, maleic anhydride and 2-acrylamido-2-methylpropanesulfonic acid.
  • the acidic groups may be wholly or partly present as sodium, potassium, ammonium, mono- or triethanolammonium salt.
  • copolymers of at least one anionic monomer and at least one nonionic monomer are preferable to use copolymers of at least one anionic monomer and at least one nonionic monomer.
  • anionic monomers reference is made to the substances listed above.
  • Preferred nonionic monomers are acrylamide, methacrylamide, acrylic esters, methacrylic esters, vinylpyrrolidone, vinyl ethers and vinyl esters.
  • Preferred anionic copolymers are acrylic acid-acrylamide copolymers and in particular polyacrylamide copolymers with sulfonic acid-containing monomers.
  • a particularly preferred anionic copolymer consists of 70 to 55 mol% of acrylamide and 30 to 45 mol% of 2-acrylamido-2-methylpropanesulfonic acid, wherein the sulfonic acid group is wholly or partly in the form of sodium, potassium, ammonium, mono- or triethanolammonium Salt is present.
  • This copolymer may also be crosslinked, with crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylenebisacrylamide are used.
  • crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylenebisacrylamide are used.
  • crosslinking agents preferably polyolefinically unsaturated compounds such as tetraallyloxyethane, allylsucrose, allylpentaerythritol and methylenebisacrylamide are used.
  • Such a polymer is contained in the commercial product Sepigel ® 305 from SEPPIC.
  • This compound which in addition to the polymer component contains a hydrocarbon mixture (Ci 3 -Ci 4 -lsoparaffin) and
  • anionic homopolymers are uncrosslinked and crosslinked polyacrylic acids. Allyl ethers of pentaerythritol, sucrose and propylene may be preferred crosslinking agents. Such compounds are for example available under the trademark Carbopol ® commercially.
  • Copolymers of vinyl acetate and crotonic acid such as, for example, as a commercial product Aristoflex ® A 60 with the INCI name VA / Crotonates Copolymer by CIBA in a 60 wt .-% - marketed dispersion in isopropanol-water
  • copolymers of ethyl acrylate and methacrylic acid as sold for example under the trade name Luviflex ® soft having an acid number from 84 to 105 under the INCI name of Acrylates copolymer in an about 20 to 30 wt .-% dispersion in water by BASF SE
  • Luviflex ® soft having an acid number from 84 to 105 under the INCI name of Acrylates copolymer in an about 20 to 30 wt .-% dispersion in water by BASF SE
  • Polyurethanes having at least one carboxyl group such as a copolymer of isophthalic acid, adipic acid, 1, 6-hexanediol, neopentyl glycol and isophorone diisocyanate as sold under the trade name Luviset PUR with the INCI name Polyurethane-1 from BASF SE).
  • Copolymers of maleic anhydride and methyl vinyl ether, especially those with crosslinks, are also color-retaining polymers.
  • a 1, 9-decadiene crosslinked maleic acid-methyl vinyl ether copolymer is available under the name ® Stabileze QM.
  • the agents according to the invention preferably additionally contain at least one surfactant, nonionic, anionic, cationic, ampholytic surfactants being suitable in principle.
  • the group of ampholytic or amphoteric surfactants includes zwitterionic surfactants and ampholytes.
  • the surfactants according to the invention may already have emulsifying activity.
  • the additional surfactants are in the inventive composition preferably in an amount of 0.01 wt .-% to 5 wt .-%, particularly preferably from 0.05 wt .-% to 0.5 wt .-%, each based on the Weight of the agent, included. It has proved to be particularly preferred if the agents according to the invention additionally comprise at least one nonionic surfactant.
  • Nonionic surfactants contain as hydrophilic group e.g. a polyol group, one
  • Such compounds are, for example
  • alkylphenols having 8 to 15 carbon atoms in the alkyl group, such as those available under the trade names Dehydol ® LS, Dehydol ® LT types (Cognis), C 2 -C 3 o-fatty acid mono- and diesters of addition products of 1 up to 30 moles of ethylene oxide with glycerol,
  • Hydroxy mixed ethers as described, for example, in DE-OS 19738866, sorbitan fatty acid esters and addition products of ethylene oxide onto sorbitan fatty acid esters, for example the polysorbates,
  • alkylene oxide addition products of saturated linear fatty alcohols and fatty acids with in each case 2 to 100 mol of ethylene oxide per mole of fatty alcohol or fatty acid have proven to be very particularly preferred nonionic surfactants.
  • Preparations with excellent Properties are also obtained when they contain as nonionic surfactants C 2 -C 30 fatty acid mono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol and / or addition products of 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil.
  • Suitable anionic surfactants are in principle all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. As a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule.
  • anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 to 4 C atoms in the alkanol group, linear and branched fatty acids having 8 to 30 C atoms (Soap),
  • Ethercarbon Acid the formula RO- (CH2-CH2 ⁇ ) ⁇ -CH2-COOH, in which R is a linear
  • Alkyl group having 8 to 30 C atoms and x 0 or 1 to 16,
  • Sulfosuccinic acid mono-alkyl polyoxyethyl esters having 8 to 24 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates having 8 to 24 carbon atoms, linear alpha-olefin sulfonates having 8 to 24 carbon atoms,
  • Alpha sulfo fatty acid methyl esters of fatty acids having 8 to 30 carbon atoms, - alkyl sulfates and alkyl polyglycol ether sulfates of the formula RO (CH 2 -CH 2 O) x -OSO 3 H, in which R is a preferably linear alkyl group having 8 to 30 carbon atoms and x 0 or 1 to 12,
  • Amino acids and their derivatives which are known to the skilled person as protein fatty acid condensates, such as Lamepon ® - types Gluadin ® - types Hostapon ® KCG or Amisoft ® - types.
  • Preferred anionic surfactants are alkyl sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic mono- and dialkyl esters having 8 to 18 carbon atoms in the alkyl group and sulfosuccinic monoalkylpolyoxyethylester with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, monoglyceride disulfates, alkyl and alkenyl ether phosphates and protein fatty acid condensates.
  • Zwitterionic surfactants are those surface-active compounds which carry in the molecule at least one quaternary ammonium group and at least one -COO () or -SO 3 () group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyldimethylammoniumglycinate, N-acylaminopropyl-N, N-dimethylammoniumglycinates, for example cocoacylaminopropyldimethylammoniumglycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamid
  • Ampholytes are understood as meaning those surface-active compounds which, apart from a C 8 -C 24 -alkyl or -acyl group in the molecule, contain at least one free amino group and at least one -COOH or -SO 3 H group and are capable of forming internal salts.
  • ampholytes are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 24 C atoms in the alkyl group.
  • Particularly preferred ampholytes are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and C 12 -C 18 acylsarcosine.
  • compositions according to the invention contain the ingredients or active substances in a cosmetically acceptable carrier.
  • Preferred cosmetically acceptable carriers are aqueous, alcoholic or aqueous-alcoholic media with preferably at least 10% by weight of water, based on the total agent.
  • alcohols it is possible in particular to include the lower alcohols having 1 to 4 carbon atoms usually used for cosmetic purposes, such as, for example, ethanol and isopropanol.
  • co-solvents are unbranched or branched hydrocarbons such as pentane, hexane, isopentane and cyclic hydrocarbons such as cyclopentane and cyclohexane.
  • particularly preferred water-soluble solvents are glycerol, ethylene glycol and propylene glycol in an amount of up to 30% by weight, based on the total agent.
  • compositions according to the invention preferably contain from 0.01 to 30% by weight of glycerol and / or propylene glycol and / or polyethylene glycol and / or polypropylene glycol, based on the total agent.
  • the agents preferably have a pH of 2 to 11.
  • the pH range between 2 and 8 is particularly preferred.
  • the pH value in the context of this document refers to the pH at 25 ° C., unless stated otherwise.
  • compositions of the invention may further contain the auxiliaries and additives which are usually added to conventional styling agents.
  • auxiliaries and additives in particular additional care substances are mentioned.
  • a care substance according to the invention preferably at least one silicone oil and / or at least one silicone gum is used.
  • Silicone oils or silicone gums which are suitable according to the invention are in particular dialkyl and alkylaryl siloxanes, for example dimethylpolysiloxane and methylphenylpolysiloxane, and also their alkoxylated, quaternized or else anionic derivatives. Preference is given to cyclic and linear polydialkylsiloxanes, their alkoxylated and / or aminated derivatives, dihydroxypoly-dimethylsiloxanes and polyphenylalkylsiloxanes.
  • Silicone oils cause a wide variety of effects. For example, at the same time they influence the dry and wet combability, the grip of dry and wet hair and the shine.
  • silicone oils is understood by the person skilled in the art as meaning several structures of silicon-organic compounds. Initially, this is understood to mean the dimethiconols.
  • Examples of such products include the following commercial products: Botanisil NU-150M (Botanigenics), Dow Coming 1-1254 Fluid, Dow Corning 2-9023 Fluid, Dow Corning 2-9026 Fluid, Ultrapure Dimethiconol (Ultra Chemical), Unisil SF- R (Universal Preserve), X-21-5619 (Shin-Etsu Chemical Co.), Abil OSW 5 (Degussa Care Specialties), ACC DL-9430 Emulsion (Taylor Chemical Company), AEC Dimethiconol & Sodium Dodecylbenzenesulfonate (A & E Connock (Perfumery & Cosmetics) Ltd.), BC Dimethiconol Emulsion 95 (Basildon Chemical Company, Ltd.), Cosmetic Fluid 1401, Cosmetic Fluid 1403, Cosmetic Fluid 1501, Cosmetic Fluid Dow Corning 1401 Fluid, Dow Corning 1403 Fluid, Dow Corning 1501 Fluid, Dow Corning 1784 HVF Emulsion, Dow Corning 9546 Silicone Elastomer Blend (all
  • Dimethicones form the second group of silicones which may be present according to the invention. These may be both linear and branched as well as cyclic or cyclic and branched. Dimethicone copolyols form another group of silicones that are suitable. Corresponding dimethicone copolyols are commercially available and are sold, for example, by Dow Corning under the name Dow Corning® 5330 Fluid.
  • the teaching according to the invention also encompasses the fact that the dimethiconols, dimethicones and / or dimethicone copolymers can already be present as an emulsion.
  • the droplet size of the emulsified particles is according to the invention 0.01 to 10000 microns, preferably 0.01 to 100 .mu.m, more preferably 0.01 to 20 microns and most preferably 0 , 01 to 10 ⁇ m.
  • the particle size is determined by the method of light scattering.
  • Particularly suitable silicones are amino-functional silicones, in particular the silicones, which are summarized under the INCI name Amodimethicone. It is therefore preferred according to the invention if the agents according to the invention additionally contain at least one amino-functional silicone. These are silicones which have at least one, optionally substituted, amino group. These silicones are referred to as amodimethicone according to the INCI nomenclature and are available for example in the form of an emulsion as a commercial product Dow Corning ® 939 or as a commercial product Dow Corning ® 949 in a mixture with a cationic and a nonionic surfactant.
  • those amino-functional silicones are used which have an amine number above 0.25 meq / g, preferably above 0.3 meq / g and especially preferably above 0.4 meq / g.
  • the amine number stands for the milliequivalents of amine per gram of the amino-functional silicone. It can be determined by titration and also expressed in mg KOH / g.
  • the agents contain the silicones or silicone gums preferably in amounts of from 0.01% by weight to 15% by weight, particularly preferably from 0.05 to 2% by weight, based on the total agent.
  • the agent may optionally contain at least one protein hydrolyzate and / or one of its derivatives.
  • the protein hydrolysates are present in the agents according to the invention, for example, in concentrations of from 0.01% by weight to 20% by weight, preferably from 0.05% by weight to 15% by weight, and very particularly preferably in amounts of 0 , 05 wt .-% up to 5 wt .-%, each based on the total application preparation included.
  • the agent according to the invention may further comprise at least one vitamin, a provitamin, a vitamin precursor and / or one of their derivatives.
  • vitamins, provitamins and vitamin precursors are preferred, which are usually assigned to groups A, B, C, E, F and H.
  • the group of substances called vitamin A includes retinol (vitamin A 1 ) and 3,4-didehydroretinol (vitamin A 2 ).
  • Vitamin B 1 thiamin
  • vitamin B 2 riboflavin
  • vitamin B 3 nicotinic acid and / or nicotinamide (niacinamide)
  • vitamin B 5 pantothenic acid, panthenol and Pantolactone
  • vitamin B 6 pyridoxine and pyridoxamine and pyridoxal
  • vitamin C ascorbic acid
  • vitamin E tocopherols, in particular ⁇ -tocopherol
  • vitamin F lactioleic acid and / or linolenic acid
  • the agents according to the invention preferably contain vitamins, provitamins and vitamin precursors from groups A, B, C, E and H. Panthenol, pantolactone, pyridoxine and its derivatives as well as nicotinamide and biotin are particularly preferred. Very particular preference is given to using D-panthenol as care substance, if appropriate in combination with at least one of the abovementioned silicone derivatives.
  • compositions according to the invention may contain panthenol instead of or in addition to glycerol and / or propylene glycol.
  • the agents according to the invention contain panthenol, preferably in an amount of 0.05 to 10% by weight, particularly preferably 0.1 to 5% by weight, in each case based on the total agent.
  • the compositions according to the invention may further contain at least one plant extract.
  • these extracts are produced by extraction of the whole plant. However, in individual cases it may also be preferred to prepare the extracts exclusively from flowers and / or leaves of the plant.
  • the agent may further contain at least one lipid as a care substance.
  • Lipids suitable according to the invention are phospholipids, for example soya lecithin, egg lecithin and cephalins, and also the substances known under the INCI names linoleic amidopropyl PG-dimonium chlorides phosphates, cocamidopropyl PG-dimonium chlorides phosphates and stearamidopropyl PG-dimonium chlorides phosphates. These are sold, for example, by the company Mona under the trade names Phospholipid EFA® , Phospholipid PTC® and Phospholipid SV® .
  • the agents according to the invention preferably contain the lipids in amounts of from 0.01 to 10% by weight, in particular from 0.1 to 5% by weight, based on the total application preparation.
  • oil bodies are suitable as a care substance.
  • the natural and synthetic cosmetic oil bodies include, for example: vegetable oils.
  • vegetable oils examples include sunflower oil, olive oil, soybean oil, rapeseed oil, almond oil, jojoba oil, orange oil, wheat germ oil, peach kernel oil and the liquid portions of coconut oil.
  • triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
  • Ester oils are to be understood as meaning the esters of C 6 - C 30 fatty acids with C 2 - C 30 fatty alcohols. The monoesters of the fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
  • isopropyl myristate IPM Rilanit ®
  • isononanoic acid C16-18 alkyl ester Cetiol ® SN
  • 2-ethylhexyl palmitate Cegesoft ® 24
  • stearic acid-2-ethylhexyl ester Cetiol ® 868
  • cetyl oleate glycerol tricaprylate, Kokosfettalkohol- caprate / caprylate (Cetiol ® LC)
  • n-butyl stearate oleyl erucate
  • isopropyl palmitate IPP Rilanit ®
  • oleyl Oleate Cetiol ®
  • hexyl laurate Cetiol ® A
  • di-n-butyl adipate Cetiol ® B
  • myrist IPM Rilanit ®
  • Dicarboxylic acid esters such as di-n-butyl adipate, di- (2-ethylhexyl) adipate, di- (2-ethylhexyl) succinate and di-isotridecyl acelate
  • diol esters such as ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di (2- ethylhexanoate), propylene glycol diisostearate, propylene glycol di-pelargonate, butanediol diisostearate, neopentyl glycol dicaprylate, symmetrical, asymmetrical or cyclic esters of carbonic acid with fatty alcohols, for example described in DE-OS 197 56 454, glycerol carbonate or dicaprylyl carbonate (Cetiol ® CC),
  • Fatty acid partial glycerides which are understood to mean monoglycerides, diglycerides and their technical mixtures. With the use of technical products production reasons may still contain small amounts of triglycerides.
  • the partial glycerides preferably follow the formula (D4-I), CH 2 O (CH 2 CH 2 O) m R 1
  • R 3 in the R 1 , R 2 and R 3 is independently of one another hydrogen or a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18, Carbon atoms are provided with the proviso that at least one of these groups is an acyl radical and at least one of these groups is hydrogen.
  • the sum (m + n + q) is 0 or numbers from 1 to 100, preferably 0 or 5 to 25.
  • R 1 is an acyl radical and R 2 and R 3 are hydrogen and the sum (m + n + q) is 0.
  • Typical examples are mono- and / or diglycerides based on caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic , Elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
  • oleic acid monoglycerides are used.
  • the amount used of the natural and synthetic cosmetic oil bodies in the compositions according to the invention is usually from 0.1 to 30% by weight, based on the total application preparation, preferably from 0.1 to 20% by weight, and in particular from 0.1 to 15% by weight. %.
  • UV filters are not subject to any general restrictions with regard to their structure and their physical properties. On the contrary, all UV filters which can be used in the cosmetics sector and whose absorption maximum lies in the UVA (315-400 nm), in the UVB (280-315 nm) or in the UVC ( ⁇ 280 nm) range are suitable. UV filters with an absorption maximum in the UVB range, in particular in the range from about 280 to about 300 nm, are particularly preferred.
  • the inventively preferred UV filters can be selected, for example, from substituted benzophenones, p- Aminobenzoic acid esters, diphenylacrylic acid esters, cinnamic acid esters, salicylic acid esters, benzimidazoles and o-aminobenzoic acid esters.
  • the UV filters are usually contained in amounts of 0.01-5 wt .-%, based on the total application preparation. Amounts of 0.1-2.5 wt .-% are preferred.
  • the composition according to the invention also contains one or more substantive dyes.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones, indophenols or cationic substantive dyes used.
  • Particularly preferred cationic dyes include cationic triphenylmethane dyes (such as Basic Blue 7, Basic Blue 26, Basic Violet 2 and Basic Violet 14), aromatic systems substituted with a quaternary nitrogen group (such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17) as well as direct dyes containing a heterocycle having at least one quaternary nitrogen atom.
  • the dyes which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are here very particularly preferred cationic substantive dyes.
  • the cationic direct dyes which are sold under the trademark Arianor ®, according to the invention are also very particularly preferred cationic direct dyes.
  • the agents of the invention may also contain naturally occurring dyes, such as those in henna red, henna neutral, henna black, chamomile flower, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
  • the agents according to the invention according to this embodiment preferably contain the substantive dyes in an amount of 0.001 to 20 wt .-%, based on the total agent.
  • the agents according to the invention are free of oxidation dye precursors.
  • Oxidation dye precursors are classified into so-called developer components and coupler components.
  • the developer components form the actual dyes under the influence of oxidizing agents or of atmospheric oxygen with one another or with coupling with one or more coupler components.
  • compositions according to the invention can be carried out in all forms customary for styling agents, for example in the form of solutions which can be applied to the hair as hair lotions or pump or aerosol spray, in the form of creams, emulsions, waxes, gels or surfactant-containing foaming solutions or other preparations suitable for use on the hair.
  • the agents according to the invention are preferably made up as hair cream or hair gel, in particular as hair gel.
  • Hair creams and hair gels preferably contain, in addition to the polymer combination of the invention, at least one thickening polymer. This addition is optionally preferred and rounds off the desired consistency in the compositions according to the invention.
  • Structurants and / or thickening polymers are typically used in an amount of from 0.1 to 10% by weight, based on the total product. Amounts of 0.5 to 5 wt .-%, in particular 0.5 to 3 wt .-% are preferred.
  • Polymers can increase the viscosity of aqueous and non-aqueous phases in cosmetic preparations.
  • aqueous phases their viscosity-increasing function is based on their solubility in water or their hydrophilic nature. They can be used in both surfactant and emulsion systems of the invention.
  • As structurant preferably at least one polyethylene glycol having a melting point of 2O 0 C.
  • Such polyethylene glycols preferably have a Molegularthe of greater than 550 g / mol, in particular greater than 1000 g / mol containing compositions of the invention.
  • the inventive compositions contain said polyethylene glycols in an amount of 0.1 wt .-% to 10 wt .-%, in particular from 0.2 wt .-% to 5 wt .-%, each based on the weight of the composition.
  • a second object of the invention is the use of the compositions according to the invention for the temporary deformation of hair and / or hair care.
  • compositions of the invention and products containing these agents are characterized in particular by the fact that they give the treated hair a very strong, lasting hairstyle hold and the hair remains flexible. If the product is formulated as a hair gel, the result is a gel with a doughy consistency, which nevertheless can be distributed evenly and without dripping on the hair.
  • agent of the first subject of the invention as a leave-on hair treatment agent.
  • a third aspect of the invention is a method for treating keratin-containing fibers, in particular human hair, wherein the agent according to the invention of the first subject of the invention is applied to the keratin-containing fibers.
  • the keratin-containing fibers are brought into shape before, during or after the application of the agent according to the invention.
  • the styling gels A to C according to the invention were prepared according to the following table.
  • Silicone glycol copolymer (INCI name: PEG-12 dimethicone) (Dow Corning) copolymer of N-vinylpyrrolidone / N-vinylcaprolactam / N- (3
  • Gels A to C were all non-sticky and had a doughy rheology as a plastic fluid. Despite the doughy rheology, the gels were excellent on the hair as described below.
  • Each of the formulations A to C was tested on a test person on the hair. For this purpose, a sufficient amount of gel was placed on the palm and distributed in the hair. The hair was then styled and shaped. The resulting hairstyle had a perfect fit without leaving a sticky feeling and the hair was cared for.

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Abstract

La présente invention concerne des agents destinés au traitement de fibres kératiniques, en particulier de cheveux humains, et contenant dans un support (a) cosmétiquement acceptable, au moins un polymère cationique amphiphile qui comprend au moins une unité structurale de formule (I), au moins une unité structurale de formule (II), au moins une unité structurale de formule (III) et au moins une unité structurale de formule (IV), où R1 et R4 représentent indépendamment un atome d'hydrogène ou un groupe méthyle, X1 et X2 représentent indépendamment un atome d'oxygène ou un groupe NH, A1 et A2 représentent indépendamment un groupe éthane-1,2-diyle, propane-1,3-diyle ou butane-1,4-diyle, R2, R3, R5 et R6 représentent indépendamment un groupe alkyle en C1 à C4, R7 représente un groupe alkyle en C8 à C30; et (b) au moins un polymère qui présente une ou plusieurs chaînes latérales, contenant des silicones, et un ou plusieurs groupes anioniques. L'invention concerne également l'utilisation de ces agents pour la mise en forme temporaire des cheveux et pour les soins capillaires, en particulier sous la forme d'une crème pour les cheveux ou d'un gel pour les cheveux.
EP09780876A 2008-08-18 2009-07-21 Agents destinés à des fibres kératiniques, contenant au moins un polymère cationique amphiphile particulier et au moins un polymère qui présente des chaînes latérales, contenant des silicones, et des groupes anioniques Withdrawn EP2323620A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008038104A DE102008038104A1 (de) 2008-08-18 2008-08-18 Mittel für keratinhaltige Fasern, enthaltend mindestens ein spezielles amphiphiles kationisches Polymer und mindestens ein Polymer mit silikonhaltigen Seitenketten und anionischen Gruppen
PCT/EP2009/059356 WO2010020504A2 (fr) 2008-08-18 2009-07-21 Agents destinés à des fibres kératiniques, contenant au moins un polymère cationique amphiphile particulier et au moins un polymère qui présente des chaînes latérales, contenant des silicones, et des groupes anioniques

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US9884004B2 (en) * 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US9801804B2 (en) * 2013-06-28 2017-10-31 L'oreal Compositions and methods for treating hair
US9795555B2 (en) 2013-06-28 2017-10-24 L'oreal Compositions and methods for treating hair
US9788627B2 (en) * 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US20150004120A1 (en) * 2013-06-28 2015-01-01 L'oreal Compositions and methods for treating hair
US9884003B2 (en) * 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US9789051B2 (en) * 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US9789050B2 (en) * 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US9795556B2 (en) * 2013-06-28 2017-10-24 L'oreal Compositions and methods for treating hair
US9839600B2 (en) * 2013-06-28 2017-12-12 L'oreal Compositions and methods for treating hair
US9884002B2 (en) * 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US10709657B2 (en) * 2017-06-29 2020-07-14 L'oreal Hair-styling compositions comprising a combination of latex film-forming polymers

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US20110142780A1 (en) 2011-06-16
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WO2010020504A2 (fr) 2010-02-25

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