WO2008068067A2 - Agent fixatif pour fibres de kératine - Google Patents

Agent fixatif pour fibres de kératine Download PDF

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Publication number
WO2008068067A2
WO2008068067A2 PCT/EP2007/059206 EP2007059206W WO2008068067A2 WO 2008068067 A2 WO2008068067 A2 WO 2008068067A2 EP 2007059206 W EP2007059206 W EP 2007059206W WO 2008068067 A2 WO2008068067 A2 WO 2008068067A2
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WO
WIPO (PCT)
Prior art keywords
acid
copolymer
ester
esters
copolymers
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PCT/EP2007/059206
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German (de)
English (en)
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WO2008068067A3 (fr
Inventor
Thorsten Knappe
Ina KRÜGERMANN
Johann Klein
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Henkel Ag & Co. Kgaa
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Priority to EP07803186A priority Critical patent/EP2056786A2/fr
Publication of WO2008068067A2 publication Critical patent/WO2008068067A2/fr
Publication of WO2008068067A3 publication Critical patent/WO2008068067A3/fr

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    • 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
    • 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
    • A61K8/8135—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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid; Compositions of derivatives of such polymers, e.g. vinyl esters (polyvinylacetate)
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • the present invention relates to means for deforming keratinous fibers, containing in a cosmetically acceptable carrier at least one special pressure-sensitive adhesive, and the use of appropriate pressure-sensitive adhesives in styling agents for inducing or improving the remodeling ability of a hairstyle produced or fixed with the styling agent.
  • keratinic fibers in principle, all animal hair, e.g. Wool, horsehair, angora hair, furs, feathers and products or textiles made from them.
  • animal hair e.g. Wool, horsehair, angora hair, furs, feathers and products or textiles made from them.
  • the keratinic fibers are human hairs.
  • a gentle method for the deformation of keratin-containing fibers are the temporary shapes, as obtained for example by conventional hair sprays, hair waxes, hair gels, hair drier, etc.
  • 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.
  • a means for shaping keratinous fibers also referred to below as a styling agent
  • a styling agent An essential property of a means for shaping keratinous fibers, also referred to below as a styling agent, is to give the treated fiber in the produced form the strongest possible hold. If the keratin fibers are human hair, it is also known as a strong hairstyle.
  • the user increasingly expects from a styling agent that the created hairstyle remains deformable without loss of support due to the deformation.
  • Moisture resistance also often plays a role.
  • the created hairstyle should also be resistant to high humidity and sweat.
  • Available styling agents that give the hairstyle good hold are usually based on film-forming and / or setting polymers.
  • the strength of the hold can be adjusted by appropriate choice of the type and / or concentration of the film-forming and / or setting polymer.
  • the polymers form a film on the treated fiber and crosslink individual fibers with each other so that the fibers are fixed in a predetermined position. If a once fixed hairstyle subjected to mechanical stress, so it is easy to break the polymer films, crosslinks are irreversibly solved and the hold of the fibers is lost. Since a reshaping of the hairstyle is inevitably accompanied by a mechanical stress, such styling agents do not allow remodeling of the hairstyle.
  • the object of the present invention was therefore to provide a means for the deformation of keratinous fibers, which on the one hand is characterized by a good setting performance, i. gives the treated fibers strong hold, and on the other hand allows the remodeling of the fibers without the loss of support is lost.
  • a first subject of the present invention is therefore a means for deforming keratinous fibers, comprising in a cosmetically acceptable carrier at least one pressure-sensitive adhesive selected from vinyl ester-ethylene copolymers, modified polyacrylic acid esters and modified polymethacrylic acid esters.
  • pressure-sensitive adhesives are adhesives that are solvent-free form at 2O 0 C and remain permanently tacky tacky and adhere at a low substrate specificity in light contact pressure immediately on the substrates.
  • a variety of such pressure-sensitive adhesives are known and commercially available in the adhesives industry, where they are commonly used to make adhesive tapes, adhesive sheets, self-adhesive labels, self-sticking notes (Post- it® ), and similar products.
  • pressure-sensitive adhesives are suitable which form adhesive bonds which can be achieved without destroying the bonded substrates.
  • modified polyacrylic esters used according to the invention and modified polymethacrylic esters are preferably the esters of the respective acids with non-tertiary alkyl alcohols having alkyl radicals of 1 to 12 carbon atoms, in particular 2 to 4 carbon atoms.
  • Suitable monomers are ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, Isobutyl acrylate, 2-methylbutyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, isooctyl acrylate, isooctyl methacrylate, isononyl acrylate and isodecyl acrylate.
  • the agents according to the invention preferably contain a pressure-sensitive adhesive selected from vinyl ester-ethylene copolymers and modified polyacrylic acid esters.
  • Vinylester-ethylene copolymer the copolymer of ethylene and vinyl acetate and vinyl versatate Vinylestern is preferably used, which is sold by Wacker Vinnapas under the designation ® LL 6050th This is an about 52% by weight plasticizer-free polymer dispersion in water which contains polyvinyl alcohol as a protective colloid.
  • the total amount of pressure-sensitive adhesives in the compositions according to the invention is preferably from 0.1 to 10% by weight, more preferably from 0.5 to 8% by weight. The percentages are based on the total average minus any propellants present in the composition.
  • the pressure-sensitive adhesives are preferably introduced in the form of a solution or a dispersion into the compositions according to the invention, wherein the solvent or dispersion medium used is preferably water, alcohol, in particular ethanol and isopropanol, and mixtures thereof.
  • the agents according to the invention may of course also contain a mixture of several of the pressure-sensitive adhesives mentioned, the total amount preferably not exceeding 10% by weight.
  • compositions according to the invention contain no further pressure-sensitive adhesives in addition to the pressure-sensitive adhesives selected from vinyl ester-ethylene copolymers, modified polyacrylic acid esters and modified polymethacrylic acid esters.
  • pressure-sensitive adhesives are characterized in particular by the fact that they are removed from the treated keratinic fibers almost or completely free of residue in a single treatment with a commercially available shampoo. Under a virtually or completely residue-free removal of the pressure-sensitive adhesives is understood that the washed and dried fibers feel either sticky, or one compared to a Reference fiber which has not been treated with the agent according to the invention has improved durability of a mechanical deformation.
  • the agents In contrast to conventionally available styling agents based on film-forming and / or setting polymers, the agents impart excellent support to the treated fibers, but at the same time allow reshaping of the fibers, such as remodeling a once-formed hairstyle, without loss of support.
  • the agents according to the invention can furthermore contain at least one film-forming and / or setting polymer different from the pressure-sensitive adhesive.
  • the total amount of film-forming and / or setting polymers is preferably 0.1 to 20 wt .-%, more preferably 0.5 to 15 wt .-%, most preferably from 1, 0 to 10 wt .-%.
  • film-forming and / or setting polymers may be both permanent and temporary cationic, anionic, nonionic or amphoteric.
  • they may have different charges.
  • an ionic film-forming and / or setting polymer may be used together with an amphoteric and / or nonionic film-forming and / or setting polymer.
  • the use of at least two oppositely charged film-forming and / or setting polymers is also preferred. In the latter case, a particular embodiment may in turn additionally contain at least one further amphoteric and / or nonionic film-forming and / or setting polymer.
  • 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 setting agents, hair sprays, hair gels, hair waxes, hair treatments, shampoos or hair formulas Nail polishes are used.
  • Particular preference is given to those polymers which have sufficient solubility in alcohol 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.
  • the film-forming polymers may be anionic, amphoteric, nonionic, permanent cationic or temporarily cationically charged.
  • Suitable synthetic, film-forming, hair-fixing polymers are homopolymers or copolymers which are 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, propylene glycol or ethylene glycol, wherein the alkyl groups of these monomers are preferably C 1 - to C 7 alkyl groups, particularly preferably C 1 to C 3 alkyl groups.
  • Examples include homopolymers of vinylcaprolactam, vinylpyrrolidone or N-vinylformamide.
  • Further suitable synthetic film-forming, hair-fixing polymers are copolymers of vinyl pyrrolidone and vinyl acetate, terpolymers of vinylpyrrolidone, vinyl acetate and vinyl propionate, polyacrylamides, for example, under the trade designations Akypomine ® P 191 by the company CHEM-Y, Emmerich or Sepigel ® 305 by the company Seppic be distributed; Polyvinyl alcohols, which are marketed under the trade names Elvanol.RTM ® from DuPont or Vinol ® 523/540 by Air Products as well as polyethylene glycol / polypropylene glycol copolymers, for example, Ucon ® Union Carbide sold under the trade names.
  • Suitable natural film-forming polymers include cellulose derivatives, eg. B. hydroxypropyl cellulose having a molecular weight of 30,000 to 50,000 g / mol, which is sold for example under the trade name Nisso Sl ® from Lehmann & Voss, Hamburg.
  • Firming polymers contribute to the maintenance and / or build-up of the hair volume and hair fullness of the overall hairstyle.
  • These so-called setting polymers are at the same time film-forming polymers and therefore generally typical substances for shaping hair treatment compositions such as hair fixatives, hair foams, hair waxes, hair sprays.
  • the film formation can be quite selective and connect only a few fibers.
  • Substances which further impart hydrophobic properties to the hair are preferred because they reduce the tendency of the hair to absorb moisture, that is, water. As a result, the limp drooping of the strands of hair is reduced, thus ensuring a long-lasting hairstyle structure and preservation.
  • the test method for this is often the so-called curl retention test applied.
  • These polymeric substances can also be successfully incorporated into leave-on and rinse-off hair treatments or shampoos. Since polymers are often multifunctional, that is, show several applications-wise desirable effects, numerous polymers can be found in several groups on the mode of action, as well as in the CTFA Handbook. Because of the importance of polymers in particular, they should therefore be listed explicitly in the form of their INCI names. In this list of polymers preferably to be used according to the invention, it will be obvious, of course, that the above-mentioned film-forming polymers are again used.
  • Examples of common film-forming, setting polymers are Acrylamide / Ammonium Acrylate Copolymer, Acrylamide / DMAPA Acrylates / Methoxy PEG Methacrylate Copolymer, Acrylamidopropyltrimonium Chloride / Acrylamide Copolymer, Acrylamidopropyltrimonium Chloride / Acrylates Copolymer, Acrylates / Acetoacetoxyethyl Methacrylate Copolymer, Acrylates / Acrylamide Copolymer, Acrylates / Ammonium Methacrylate Copolymer, Acrylates / t-Butyl Acrylamide Copolymer, Acrylates Copolymer, Acrylates / CI-2 Succinates / Hydroxy Acrylates Copolymer, Acrylates / Lauryl Acrylates / Stearyl Acrylates / Ethylamine Oxide Methacrylate Copolymer, Acrylates / Octylacrylamide Copo
  • the agent according to the invention preferably contains at least one film-forming and / or setting polymer selected from
  • Vinylpyrrolidone-vinyl acetate copolymers vinylpyrrolidone-vinylcaprolactam-dimethylaminopropylacrylamide copolymers, Copolymers of octylacrylamide with t-butylaminoethyl methacrylate and two or more monomers selected from acrylic acid, methacrylic acid, acrylic acid ester and methacrylic acid ester, and
  • Ci-Ci 2 -alkyl and Ci-Ci 2 alkyl methacrylates more preferably methyl acrylate, ethyl acrylate, propyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate and mixtures thereof.
  • the copolymer with the INCI name AMP acrylate is / AI IyI Methacrylate copolymer used by the company Noveon under the name Fixate TM G-100.
  • the agent of the invention contains this copolymer very particularly preferred.
  • a preferred vinylpyrrolidone-vinyl acetate copolymer is the PVP / VA copolymer 60-40 W (INCI name: VP / VA copolymer, Aqua, Laurtrimonium Chloride).
  • the vinylpyrrolidone-vinylcaprolactam / dimethylaminopropylacrylamide copolymer used is preferably the copolymer obtainable from ISP under the name Aquaflex SF 40 and having the INCI name VP / vinyl caprolactam / DMAPA acrylates copolymer.
  • a preferred copolymer of the Octylacrylamids with t-butylaminoethyl methacrylate and two or more monomers selected from acrylic acid, methacrylic acid, acrylate and methacrylate esters, is that available from National Starch under the name Amphomer ® copolymer with the INCI name octylacrylamide / acrylates butylaminoethyl methacrylate copolymer.
  • compositions according to the invention may furthermore contain care substances.
  • protein hydrolysates and / or their derivatives are suitable.
  • Protein hydrolysates are product mixtures obtained by acid, alkaline or enzymatically catalyzed degradation of proteins (proteins).
  • the term protein hydrolyzates also means total hydrolyzates as well as individual amino acids and their derivatives as well as mixtures of different amino acids.
  • polymers made up of amino acids and amino acid derivatives are understood by the term protein hydrolyzates. The latter include, for example, polyalanine, polyasparagine, polyserine, etc.
  • Further examples of compounds which can be used according to the invention are L-alanyl-L-proline, polyglycine, glycyl-L-glutamine or D / L-methionine-S-methylsulfonium chloride.
  • ⁇ -amino acids and their derivatives such as ⁇ -alanine, anthranilic acid or hippuric acid can also be used.
  • the molecular weight of the protein hydrolysates which can be used according to the invention is between 75, the molecular weight for glycine, and 200,000, preferably the molecular weight is 75 to 50,000 and very particularly preferably 75 to 20,000 daltons.
  • protein hydrolysates of both vegetable and animal or marine or synthetic origin can be used.
  • Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk protein protein hydrolysates, which may also be present in the form of salts.
  • Such products are, for example, under the trademarks Dehylan ® (Cognis), Promois® ® (Interorgana) Collapuron ® (Cognis), Nutrilan® ® (Cognis), Gelita-Sol ® (German Gelatinefabriken Stoess & Co), Lexein ® (Inolex) sericin (Pentapharm) and kerasol tm ® (Croda) sold.
  • silk protein hydrolysates By silk one understands the fibers of the cocoon of the mulberry silkworm (Bombyx mori L.).
  • the raw silk fiber consists of a double thread fibroin.
  • sericin holds this double thread together.
  • Silk consists of 70-80% by weight of fibroin, 19-28% by weight of sericin, 0.5-1% by weight of fat and 0.5-1% by weight of dyes and mineral constituents.
  • the essential components of sericin are with about 46 wt .-% Hydroxyamino acids.
  • the sericin consists of a group of 5 to 6 proteins.
  • the essential amino acids of sericin are serine (Ser, 37% by weight), aspartate (Asp, 26% by weight), glycine (Gly, 17% by weight), alanine (Ala), leucine (Leu) and tyrosine (Tyr) ,
  • the water-insoluble fibroin belongs to the skieroproteins with a long-chain molecular structure.
  • the main constituents of fibroin are glycine (44% by weight), alanine (26% by weight), and Tyrosine (13% by weight).
  • Another essential structural feature of the fibroin is the hexapeptide sequence Ser-G Iy-Ala-G Iy-Ala-G Iy.
  • an active substance complex consisting of the active ingredient (A1) selected from sericin, sericin hydrolysates and / or derivatives thereof, and mixtures thereof, and an active ingredient (A2) selected from fibroin, and / or Fibroinhydrolysaten and / or derivatives thereof and / or mixtures thereof.
  • the active ingredient complex (A) used according to the invention significantly synergistically improves the above-described essential internal and external structural features and the strength and elasticity of human hair.
  • active ingredients (A1) it is possible to use in the active ingredient complex (A): native sericin, hydrolyzed and / or further derivatized sericin, such as commercial products with the INCI names Sericin, Hydrolyzed Sericin, or Hydrolyzed SiIk, a mixture of the amino acids serine, aspartate and glycine and / or their methyl, propyl, iso-propyl, butyl, iso-butyl esters, their salts such as hydrochlorides, sulfates, acetates, citrates, tartrates, being in this mixture the serine and / or its derivatives to 20 to 60 wt.%, The aspartate and / or its derivatives to 10 to 40 wt.% And the glycine and / or its derivatives to 5 to 30 wt.% Are included, with the proviso in that the amounts of these amino acids and / or derivatives thereof preferably add up to 100% by weight, and mixtures thereof.
  • active ingredients (A2) can be used in the active ingredient complex (A): native, converted into a soluble form fibroin, hydrolyzed and / or further derivatized fibroin, especially partially hydrolyzed fibroin, which contains as its main component the amino acid sequence Ser-Gly-Ala-Gly-Ala Gly, the amino acid sequence Ser-Gly-Ala-Gly-Ala-Gly, a mixture of the amino acids glycine, alanine and tyrosine and / or their methyl, propyl, iso-propyl, butyl, iso-butyl esters, their salts such as hydrochlorides, sulfates, acetates, citrates, tartrates, wherein in this mixture, the glycine and / or its derivatives in amounts of 20- 60 wt.%, The alanine and its derivatives in amounts of 10 - 40 wt%, and the tyrosine and its derivatives are contained in amounts of
  • Particularly good nourishing properties can be achieved if one of the two active ingredient components of the active ingredient complex (A) is used in the native or at most solubilized form. It is also possible to use a mixture of several active substances (A1) and / or (A2).
  • the two active compounds (A1) and (A2) in the ratio of 10:90 to 70:30, in particular 15:85 to 50:50 and very particularly 20:80 to 40:60, based on their respective Contents of active substance in the products of the invention can be used.
  • the derivatives of sericin and fibroin hydrolysates include both anionic and cationized protein hydrolysates.
  • the protein hydrolyzates of sericin and fibroin and the derivatives prepared therefrom can be obtained from the corresponding proteins by chemical, in particular alkaline or acid hydrolysis, by enzymatic hydrolysis and / or a combination of both types of hydrolysis.
  • the hydrolysis of proteins usually results in a protein hydrolyzate having a molecular weight distribution of about 100 daltons up to several thousand daltons.
  • cationic protein hydrolysates of sericin and fibroin also mean quaternized amino acids and mixtures thereof.
  • the quaternization of the protein hydrolyzates or amino acids is often carried out using quaternary ammonium salts such as N, N-dimethyl-N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides.
  • the cationic protein hydrolysates may also be further derivatized.
  • the cationic protein hydrolysates and derivatives which can be used according to the invention, those mentioned under the INCI names in the "International Cosmetic Ingredient Dictionary and Handbook", (seventh edition 1997, The Cosmetic, Toiletry, and Fragrance Association 1101 17 th Street, NW, Suite 300, Washington, DC 20036-4702) and commercially available products: Cocodimonium Hydroxypropyl Hydrolyzed Silica, Cocodimonium Hydroxypropyl Silica, Amino Acids, Hydroxyproypltrimonium Hydrolyzed Silica, Lauryldimonium Hydroxypropyl Hydrolyzed Silica, Steardimonium Hydroxypropyl Hydrolyzed Silica, Quaternium 79 Hydrolyzed Silica.
  • anionic protein hydrolysates and derivatives according to the invention those mentioned under the INCI names in the "International Cosmetic Ingredient Dictionary and Handbook", (seventh edition 1997, The Cosmetic, Toiletry, and Fragrance Association 1101 17 th Street, NW, Suite 300 Potassium cocoyl hydrolyzed silica, sodium lauroyl hydrolyzed silica or sodium stearoyl hydrolyzed silica.
  • the derivatives of sericin and fibroin which can be used according to the invention, mention may be made of the products commercially available under the INCI names: Ethyl Ester of Hydrolyzed SiIk and Hydrolyzed SiIk PG-Propyl Methylsilanediol.
  • Palmitoyl Oligopeptide Palmitoyl Pentapeptide-3, Palmitoyl Pentapeptide-2, Acetyl Hexapeptide-1, Acetyl Hexapeptide-3, Copper Tripeptide-1, Hexapeptide-1 , Hexapeptide-2, MEA-Hydrolyzed SiIk.
  • the effect of the active ingredient complex (A) can be further increased by the addition of fatty substances.
  • Fatty substances are to be understood as meaning fatty acids, fatty alcohols, natural and synthetic waxes, which may be in solid form as well as liquid in aqueous dispersion, and natural and synthetic cosmetic oil components.
  • Protein hydrolysates of vegetable origin eg. As soybean, almond, pea, potato and wheat protein hydrolysates are, for example, under the trademarks Gluadin ® (Cognis), DiaMin ® (Diamalt), Lexein ® (Inolex), Hydrosoy ® (Croda), Hydrolupin ® (Croda) , hydro Sesame ® (Croda), Hydro tritium ® (Croda) and Crotein ® (Croda) available.
  • protein hydrolysates are preferred as such, amino acid mixtures otherwise obtained may be used in their place, if appropriate. Also possible is the use of derivatives of protein hydrolysates, for example in the form of their
  • Fatty acid condensation products are for example among the
  • Lamepon® ® (Cognis), Lexein ® (Inolex), Crolastin ® (Croda), Crosilk ® (Croda) or crotein ® (Croda) sold.
  • 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 may contain, for example, at least one cationic surfactant.
  • Cationic surfactants of the quaternary ammonium compounds, esterquats and amidoamines type are preferred according to the invention.
  • Preferred quaternary ammonium compounds are ammonium halides, in particular chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, eg.
  • cetyltrimethylammonium chloride stearyltrimethylammonium chloride, distearyldimethyl ammonium chloride, lauryldimethylammonium chloride, lauryldimethylbenzylammonium chloride and tricetylmethylammonium chloride, as well as the imidazolium compounds known under the INCI names Quaternium-27 and Quaternium-83.
  • the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
  • Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
  • Preferred ester quats are quaternized ester salts of fatty acids with triethanolamine, quaternized ester salts of fatty acids with diethanolalkylamines and quaternized ester salts of fatty acids with 1,2-dihydroxypropyldialkylamines.
  • Such products are marketed under the trade names Stepantex® ®, ® and Dehyquart® Armocare® ®.
  • alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An invention Particularly suitable compound from this group of substances is the commercially available under the name Tegoamid ® S 18 stearamidopropyl-dimethylamine.
  • the cationic surfactants are contained in the compositions according to the invention preferably in amounts of from 0.05 to 10% by weight, based on the total application preparation. Amounts of 0.1 to 5 wt .-% are particularly preferred.
  • Nurturing polymers are also suitable as a care substance. It should be noted at this point that some of the care polymers mentioned below also have film-forming and / or setting properties and can therefore also be found in the description of suitable film-forming and / or setting polymers.
  • a first group of caring polymers are the cationic polymers.
  • 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 4 -hydrocarbon group to a polymer main chain composed of acrylic acid, methacrylic acid or derivatives thereof have proven to be particularly suitable.
  • R 1 -H or -CH 3
  • R 2, R 3 and R 4 are independently selected from C- ⁇ _ 4 - alkyl, -alkenyl or -hydroxyalkyl groups
  • m 1, 2, 3 or 4
  • n is a natural number
  • R 1 is a methyl group
  • R 2 , R 3 and R 4 are methyl groups
  • m has the value 2.
  • Suitable physiologically acceptable counterions X ' are, for example, halide ions, sulfate ions, phosphate ions, methosulfate ions and organic ions such as lactate, citrate, tartrate and acetate ions. Preference is given to halide ions, in particular chloride.
  • a particularly suitable homopolymer is, if desired, crosslinked, poly (meth acryloyloxyethyltrimethylammonium chloride) with the INCI name Polyquaternium-37.
  • the crosslinking can be carried out with the aid of poly olefinically unsaturated compounds, for example divinylbenzene, tetraallyloxyethane, methylenebisacrylamide, diallyl ether, polyallylpolyglyceryl ethers, or allyl ethers of sugars or sugar derivatives such as erythritol, pentaerythritol, arabitol, mannitol, sorbitol, sucrose or glucose.
  • Methylenebisacrylamide is a preferred crosslinking agent.
  • the homopolymer is preferably used in the form of a non-aqueous polymer dispersion which should not have a polymer content of less than 30% by weight.
  • Such polymer dispersions are (under the names Salcare ® SC 95 about 50% polymer content, additional components: mineral oil (INCI name: Mineral Oil) and tridecyl-polyoxypropylene-polyoxyethylene-ether (INCI name: PPG-1 trideceth-6) ) and Salcare ® SC 96 (about 50% polymer content, additional components: mixture of diesters of propylene glycol with a mixture of caprylic and capric acid (INCI name: propylene glycol Dicaprylate / Dicaprate) and tridecyl polyoxypropylene-polyoxyethylene-ether (INCI Designation: PPG-1-trideceth-6)) are commercially available.
  • Copolymers with monomer units of the formula (G1-I) as the non-ionic monomer preferably acrylamide, methacrylamide, acrylic acid and methacrylic acid alkyl esters CI_ 4-C- ⁇ _ 4 -alkyl.
  • the acrylamide is particularly preferred.
  • These copolymers can also be crosslinked, as described above in the case of the homopolymers.
  • a copolymer preferred according to the invention is the crosslinked acrylamide-methacryloyloxyethyltrimethylammonium chloride copolymer.
  • Such copolymers in which the monomers are present in a weight ratio of about 20:80, are commercially available as approximately 50% non-aqueous polymer dispersion 92 under the name Salcare ® SC.
  • cationic polymers are for example quaternised CeIIu lose-derivatives, such as are available under the names of Celquat ® and Polymer JR ® commercially.
  • the compounds Celquat ® H 100, Celquat ® L 200 and Polymer JR ® 400 are preferred quaternized cellulose derivatives, cationic alkyl polyglycosides according to DE-PS 44 13 686, cationized honey, for example the commercial product Honeyquat ® 50, cationic guar derivatives, such as in particular the products sold under the trade names Cosmedia® ® guar and Jaguar ® products, Quaternary group polysiloxanes such as the commercially available products Q2-7224 (manufactured by Dow Corning, a stabilized trimethylsilylamodimethicone), Dow Corning® 929 emulsion (containing a hydroxylamino-modified silicone, also referred to as amodimethicones), SM -2059 (manufactur
  • Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially,
  • Vinylpyrrolidone-vinyl imidazolium copolymers such as those offered under the names Luviquat ® FC 370, FC 550, FC 905 and HM 552, quaternized polyvinyl alcohol, as well as by the names of Polyquaternium 2, Polyquaternium 17, Polyquaternium 18 and Polyquaternium 27, having quaternary Nitrogen atoms in the polymer backbone.
  • Can be used as cationic polymers are sold under the names Polyquaternium-24 (commercial product z. B. Quatrisoft ® LM 200), known polymers.
  • Gaffix ® VC 713 manufactured by ISP:
  • the copolymers of vinylpyrrolidone such as the commercial products Copolymer 845 (ISP manufacturer) are Gafquat ® ASCP 1011, Gafquat ® HS 110, Luviquat ® 8155 and Luviquat ® MS 370 available are.
  • cationic polymers which can be used 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.
  • temporary cationic polymers usually contain an amino group which, at certain pH values, is present as quaternary ammonium group and thus cationic.
  • chitosan and its derivatives are preferred as Hydagen CMF ®, Hydagen HCMF ®, Kytamer ® PC and Chitolam ® NB / 101 are freely available commercially, for example under the trade names.
  • cationic polymers are cationic cellulose derivatives and chitosan and its derivatives, in particular the commercial products Polymer ® JR 400, Hydagen HCMF ® and Kytamer ® PC, cationic guar derivatives, cationic honey derivatives, in particular the commercially available product ® Honeyquat 50, cationic Alkylpolyglycodside according to DE-PS 44 13 686, and polymers of the type Polyquaternium-37.
  • cationized protein hydrolyzates are to be counted among the cationic polymers, wherein the underlying protein hydrolyzate from the animal, for example from collagen, milk or keratin, from the plant, for example from wheat, corn, rice, potatoes, soy or almonds, marine life forms, for example from fish collagen or algae, or biotechnologically derived protein hydrolysates.
  • the protein hydrolyzates on which the cationic derivatives according to the invention are based can be obtained from the corresponding proteins by chemical, in particular alkaline or acid hydrolysis, by enzymatic hydrolysis and / or a combination of both types of hydrolysis.
  • cationic protein hydrolyzates are understood to mean quaternized amino acids and mixtures thereof.
  • the quaternization of the protein hydrolyzates or amino acids is often carried out using quaternary ammonium salts such as N, N-dimethyl-N- (n-alkyl) -N- (2-hydroxy-3-chloro-n-propyl) ammonium halides.
  • the cationic protein hydrolysates may also be further derivatized.
  • the cationic protein hydrolysates and derivatives according to the invention those mentioned under the INCI names in the "International Cosmetic Ingredient Dictionary and Handbook", (seventh edition 1997, The Cosmetic, Toiletry and Fragrance Association 1 101 17 th Street, NW, Suite 300, Washington, DC 20036-4702) and commercially available products called: Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimonium Hydroxypropyl Hydrolyzed Casein, Cocodimonium Hydroxypropyl Hydrolyzed Collagen, Cocodimonium Hydroxypropyl Hydrolyzed Hair Keratin, Cocodimonium Hydroxypropyl Hydrolyzed Keratin, Cocodimonium Hydroxypropyl Hydrolyzed Rice Protein, Cocodimonium Hydroxypropyl Hydrolyzed Soy Protein, Cocodimonium Hydroxypropyl Hydrolyzed Wheat Protein, Hydroxypropyl Arginine Lauryl / My
  • amphoteric polymers are those polymers which are composed essentially
  • R 1 -CH CR 2 -CO-Z- (C n H 2n ) -N (+)
  • R 3 R 4 R 5 A H (II) in the R 1 and R 2 independently of one another represent hydrogen or a methyl group and R 3 , R 4 and R 5 each independently represent an alkyl group having 1 to 4 carbon atoms, Z an NH group or an oxygen atom, n an integer from 2 to 5 and A is the anion of an organic or inorganic acid, and
  • These compounds can be used both directly and in salt form, which is obtained by neutralization of the polymers, for example with an alkali metal hydroxide, according to the invention.
  • Very particular preference is given to those polymers in which monomers of the type (a) are used in which R 3 , R 4 and R 5 are methyl groups, Z is an NH group and A () is a halide, methoxysulfate or ethoxysulfate ion is; Acrylamidopropyltrimethylammonium chloride is a particularly preferred monomer (a).
  • Acrylic acid is preferably used as monomer (b) for the stated polymers.
  • compositions according to the invention preferably comprise the caring, cationic or amphoteric polymers in an amount of 0.01 to 5% by weight, in particular in an amount of 0.1 to 2% by weight, in each case based on the total application preparation.
  • 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, pro-vitamins 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 ).
  • the ß-carotene is the provitamin of retinol.
  • vitamin A component for example, vitamin A acid and its esters, vitamin A aldehyde and vitamin A alcohol and its esters such as the palmitate and the acetate into consideration.
  • the agents contain the vitamin A component preferably in amounts of 0.05-1% by weight, based on the total application preparation.
  • the vitamin B group or the vitamin B complex include vitamin B 1 (thiamine) vitamin B 2 (riboflavin)
  • Vitamin B 3 Under this name, the compounds nicotinic acid and nicotinamide (niacinamide) are often performed. Preferred according to the invention is the nicotinic acid amide, which is preferably contained in the agents according to the invention in amounts of from 0.05 to 1% by weight, based on the total application preparation. Vitamin B 5 (pantothenic acid, panthenol and pantolactone). Panthenol and / or pantolactone are preferably used in the context of this group. Derivatives of panthenol which can be used according to the invention are, in particular, the esters and ethers of panthenol and also cationically derivatized panthenols.
  • panthenol triacetate the panthenol monoethyl ether and its monoacetate and also the cationic panthenol derivatives disclosed in WO 92/13829.
  • the said compounds of the vitamin B 5 type are preferably present in the agents according to the invention in amounts of 0.05-10% by weight, based on the total application preparation. Amounts of 0.1-5 wt .-% are particularly preferred.
  • Vitamin B 6 (pyridoxine and pyridoxamine and pyridoxal).
  • the compounds of the vitamin B 6 type mentioned are preferably contained in the agents according to the invention in amounts of 0.01-5% by weight, based on the total application preparation. Levels of 0.05-1 wt% are particularly preferred.
  • Vitamin C (ascorbic acid). Vitamin C is used in the compositions according to the invention preferably in amounts of 0.1 to 3 wt .-%, based on the total application preparation. Use in the form of palmitic acid ester, glucosides or phosphates may be preferred. The use in combination with tocopherols may also be preferred.
  • Vitamin E tocopherols, especially ⁇ -tocopherol.
  • Tocopherol and its derivatives which include in particular the esters such as acetate, nicotinate, phosphate and succinate, are preferably present in the compositions according to the invention in amounts of 0.05-1% by weight, based on the total application preparation.
  • Vitamin F is usually understood as meaning essential fatty acids, in particular linoleic acid, linolenic acid and arachidonic acid.
  • Vitamin H is the compound (3aS, 4S, 6aR) -2-oxohexahydrothienol [3,4-c /] -imidazole-4-valeric acid, for which, however, the trivial name biotin has meanwhile prevailed.
  • Biotin is contained in the agents according to the invention preferably in amounts of 0.0001 to 1, 0 wt .-%, in particular in amounts of 0.001 to 0.01 wt .-%, each based on the total application preparation.
  • 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 nicotinic acid amide and biotin are particularly preferred.
  • compositions according to the invention may further contain at least one plant extract.
  • 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.
  • extracts of green tea, almond, aloe vera, coconut, mango, apricot, lime, wheat, kiwi and melon are especially suitable.
  • alcohols and mixtures thereof can be used as extraction agent for the preparation of said plant extracts water.
  • the alcohols are lower alcohols such as ethanol and isopropanol, but especially polyhydric alcohols such as ethylene glycol and propylene glycol, both as sole extractant and in admixture with water, are preferred.
  • Plant extracts based on water / propylene glycol in a ratio of 1:10 to 10: 1 have proven to be particularly suitable.
  • the plant extracts can be used according to the invention both in pure and in diluted form. If they are used in diluted form, they usually contain about 2 to 80 wt .-% of active substance and as a solvent used in their extraction agent or extractant mixture.
  • compositions according to the invention mixtures of several, especially two, different plant extracts.
  • short-chain carboxylic acids may in particular be advantageous.
  • Short-chain carboxylic acids and their derivatives in the context of the invention are understood to mean carboxylic acids which may be saturated or unsaturated and / or straight-chain or branched or cyclic and / or aromatic and / or heterocyclic and have a molecular weight of less than 750.
  • preference may be given to saturated or unsaturated straight-chain or branched carboxylic acids having a chain length of from 1 to 16 C atoms in the chain, very particular preference being given to those having a chain length of from 1 to 12 C atoms in the chain.
  • the short-chain carboxylic acids according to the invention may have one, two, three or more carboxy groups.
  • carboxylic acids having a plurality of carboxy groups in particular di- and tricarboxylic acids.
  • the carboxy groups may be wholly or partly present as esters, acid anhydride, lactone, amide, imidic acid, lactam, lactim, dicarboximide, carbohydrazide, hydrazone, hydroxam, hydroxime, amidine, amidoxime, nitrile, phosphonic or phosphate ester.
  • the carboxylic acids which can be used according to the invention may of course be substituted along the carbon chain or the ring skeleton.
  • the substituents of the carboxylic acids which can be used according to the invention include, for example, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, aryl, aralkyl and aralkenyl, hydroxymethyl, C 2 -C 8 -hydroxyalkyl, C 2 -C 8 -hydroxyalkenyl, aminomethyl, C 2 -C 8 -aminoalkyl, cyano, formyl, oxo, thioxo, Hydroxy, mercapto, amino, carboxy or imino groups.
  • Preferred substituents are C 1 -C 8 -alkyl, hydroxymethyl, hydroxy, amino and carboxy groups.
  • substituents in the ⁇ position are hydroxy, alkoxy and amino groups, where the amino function may optionally be further substituted by alkyl, aryl, aralkyl and / or alkenyl radicals.
  • preferred carboxylic acid derivatives are the phosphonic and phosphate esters.
  • carboxylic acids which can be used according to the invention include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, pivalic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, glyceric acid, glyoxylic acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, propiolic acid, crotonic acid, isocrotonic acid, elaidic acid, maleic acid, fumaric acid, muconic acid, citraconic acid, mesaconic acid, camphoric acid, benzoic acid, o, m, p-phthalic acid, naphthoic acid, Toluoylklare, hydratropic acid, atropic acid, cinnamic acid, isonicotinic acid, nicotinic acid, Bicarbaminklare, 4,4
  • dicarboxylic acids of the general formula (NI) which additionally carry 1 to 3 methyl or ethyl substituents on the cyclohexene ring and dicarboxylic acids formed from the dicarboxylic acids according to formula (NI) formally by addition of a molecule of water to the double bond in the cyclohexene ring.
  • Dicarboxylic acids of the formula (NI) are known in the literature. For example, US-A 3,753,968 discloses a manufacturing process.
  • the dicarboxylic acids of the formula (N-I) can be prepared, for example, by reacting polyunsaturated dicarboxylic acids with unsaturated monocarboxylic acids in the form of a Diels-Alder cyclization.
  • a polyunsaturated fatty acid as the dicarboxylic acid component.
  • Preferred is the linoleic acid obtainable from natural fats and oils.
  • the monocarboxylic acid component in particular, acrylic acid, but also e.g. Methacrylic acid and crotonic acid are preferred.
  • isomer mixtures in which one component is present in excess are formed. These isomer mixtures can be used according to the invention as well as the pure compounds.
  • those dicarboxylic acids which differ from the compounds according to formula (NI) by 1 to 3 methyl or ethyl substituents on the cyclohexyl ring or formally from these compounds by addition of one molecule of water are also usable according to the invention be formed on the double bond of the cyclohexene ring.
  • the dicarboxylic acid (mixture), which is obtained by reacting linoleic acid with acrylic acid, has proved to be particularly effective according to the invention. It is a mixture of 5- and 6-carboxy-4-hexyl-2-cyclohexene-1-octanoic acid.
  • Such compounds are commercially available under the designations Westvaco Diacid 1550 Westvaco Diacid ® ® 1595 (manufacturer: Westvaco).
  • salts are the alkali metal salts, alkaline earth metal salts, zinc salts and ammonium salts, which in the context of the present application also includes the mono-, di- and trimethyl-, -ethyl- and -hydroxyethyl ammonium salts.
  • neutralized acids can very particularly preferably be used with alkaline-reacting amino acids, such as, for example, arginine, lysine, ornithine and histidine.
  • 2-pyrrolidinone-5-carboxylic acid and derivatives thereof are inventively preferred as the carboxylic acid.
  • Particularly preferred are the sodium, potassium, calcium, magnesium or ammonium salts in which the ammonium ion in addition to hydrogen carries one to three C 1 - to C 4 -Alkylgmppen.
  • the sodium salt is most preferred.
  • the amounts used in the products according to the invention are preferably from 0.05 to 10% by weight, based on the total application preparation, particularly preferably 0.1 to 5 wt.%, and particularly preferably 0.1 to 3 wt.%.
  • hydroxycarboxylic acids and here again in particular the dihydroxy, trihydroxy and polyhydroxycarboxylic acids as well as the dihydroxy, trihydroxy and polyhydroxy di-, tri- and polycarboxylic acids. It has been found that, in addition to the hydroxycarboxylic acids, the hydroxycarboxylic acid esters and the mixtures of hydroxycarboxylic acids and their esters as well as polymeric hydroxycarboxylic acids and their esters can be very particularly preferred.
  • Preferred hydroxycarboxylic acid esters are, for example, full esters of glycolic acid, lactic acid, malic acid, tartaric acid or citric acid.
  • hydroxycarboxylic esters are esters of .beta.-hydroxypropionic acid, tartronic acid, D-gluconic acid, sugar acid, mucic acid or glucuronic acid.
  • Suitable alcohol components of these esters are primary, linear or branched aliphatic alcohols having 8-22 C atoms, ie, for example, fatty alcohols or synthetic fatty alcohols.
  • the esters of C 12 -C 5 fatty alcohols are particularly preferred.
  • Esters of this type are commercially available, eg under the trademark Cosmacol® ® EniChem, Augusta Industriale.
  • Particularly preferred polyhydroxypolycarboxylic acids are polylactic acid and polyuric acid and their esters.
  • Ectoin or ectoine derivatives, allantoin, taurine and / or bisabolol are also suitable as care substances.
  • ectoine and ectoine derivatives means compounds of the formula (IV)
  • R 10 is a hydrogen atom, a branched or unbranched C 1 -C 4 -alkyl radical or a C 2 -C 4 -hydroxyalkyl radical,
  • R 11 represents a hydrogen atom, a grouping -COOR 14 or a grouping -
  • R 14 may be a hydrogen atom, a C 1 -C 4 -alkyl radical, an amino acid radical, a dipeptide or a tripeptide radical
  • R 12 and R 13 are each, independently of one another, a hydrogen atom, a C 1 -C 4 -alkyl radical or a hydroxy group, with the proviso that both radicals may not simultaneously be a hydroxy group
  • n is an integer from 1 to 3.
  • Suitable physiologically tolerated salts of the general compounds of the formula (IVa) or (IVb) are, for example, the alkali metal, alkaline earth metal, ammonium, triethylamine or tris (2-hydroxyethyl) amine salts and those which result from the reaction of compounds according to the formula (IVa) or (IVb) with inorganic and organic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, branched or unbranched, substituted or unsubstituted (for example by one or more hydroxy groups) C 1 -C 4 -mono- or dicarboxylic acids, aromatic carboxylic acids and Sulfonic acids such as acetic acid, citric acid, benzoic acid, maleic acid, fumaric acid, tartaric acid and p-toluenesulfonic acid.
  • inorganic and organic acids such as hydrochloric acid, phosphoric acid, sulfuric acid, branched or unbranched, substituted or unsubstit
  • physiologically acceptable salts are the Na, K, Mg and Ca and ammonium salts of the compounds of the formula (IVa) or (IVb), and the salts which are obtained by reacting compounds of the formula (IVa ) or (IVb) with hydrochloric acid, acetic acid, citric acid and benzoic acid.
  • Isomeric or stereoisomeric forms of the compounds of the formula (IVa) or (IVb) are understood according to the invention to mean all occurring optical isomers, diastereomers, racemates, zwitterions, cations or mixtures thereof.
  • amino acid the stereoisomeric forms, e.g. D and L forms, the following compounds understood:
  • arginine aspartic acid, glutamine, glutamic acid, ⁇ -alanine, ⁇ -aminobutyrate, N ⁇ -acetyllysine, N ⁇ -acetylornitine, N ⁇ -acetyldiaminobutyrate, N ⁇ -acetyldiaminobutyrate, histidine, isoleucine, leucine, methionine, phenylalanine, serine, Threonine and tyrosine.
  • L-amino acids are preferred.
  • Amino acid residues are derived from the corresponding amino acids. The following amino acid residues are preferred:
  • the short notation of the amino acids was carried out according to the usual notation.
  • the di- or tripeptide radicals are acid amides in their chemical nature and decompose on hydrolysis in 2 or 3 amino acids.
  • the amino acids in the di- or tripeptide moiety are linked together by amide bonds.
  • Examples of di- and tripeptide radicals can also be found in the disclosure of EP 0 671 161 A1.
  • Examples of C 1 -C 4 -alkyl groups in the compounds of the formula (IV) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.
  • Preferred alkyl groups are methyl and ethyl, methyl is a particularly preferred alkyl group.
  • Preferred C 2 -C 4 -hydroxyalkyl groups are the groups 2-hydroxyethyl, 3-hydroxypropyl or 4-hydroxybutyl; 2-hydroxyethyl is a particularly preferred hydroxyalkyl group.
  • compositions according to the invention preferably contain these care substances in amounts of from 0.001 to 2, in particular from 0.01 to 0.5,% by weight, based in each case on the total application time.
  • Mono- or oligosaccharides can also be used as a care substance in the compositions according to the invention.
  • monosaccharides and oligosaccharides such as, for example, cane sugar, lactose and raffinose
  • monosaccharides such as, for example, cane sugar, lactose and raffinose
  • monosaccharides are preferred according to the invention.
  • monosaccharides those compounds which contain 5 or 6 carbon atoms are preferred.
  • Suitable pentoses and hexoses are, for example, ribose, arabinose, xylose, lyxose, allose, altrose, glucose, mannose, gulose, idose, galactose, talose, fucose and fructose.
  • Arabinose, glucose, galactose and fructose are preferably used carbohydrates; Very particular preference is given to using glucose which is suitable both in the D - (+) or L - (-) configuration or as a racemate.
  • sugars are gluconic acid, glucuronic acid, sugar acid, mannose and mucic acid.
  • Preferred sugar alcohols are sorbitol, mannitol and dulcitol.
  • Preferred glycosides are the methylglucosides.
  • the monosaccharides or oligosaccharides used are usually obtained from natural raw materials such as starch, they usually have the configurations corresponding to these raw materials (for example D-glucose, D-fructose and D-galactose).
  • the mono- or oligosaccharides are contained in the hair treatment compositions according to the invention preferably in an amount of 0.1 to 8 wt .-%, particularly preferably 1 to 5 wt .-%, based on the total application preparation.
  • 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.
  • fatty acid components used in the esters are caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitoleic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic Behenic acid and erucic acid and their technical mixtures which are obtained, for example, in the pressure splitting of natural fats and oils, in the oxidation of aldehydes from Roelen's oxo synthesis or the dimerization of unsaturated fatty acids.
  • fatty alcohol components in the ester oils are isopropyl alcohol, caproic alcohol, capryl alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, elaeostearyl alcohol, arachyl alcohol, Gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol as well their technical mixtures, which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
  • 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,
  • 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),
  • 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 inventive compositions is usually 0.1 to 30 wt.%, Based on the total application preparation, preferably 0.1 to 20 wt .-%, and in particular 0.1 to 15 wt .-%.
  • the agent may further contain an enzyme as a conditioner.
  • enzymes according to the invention are selected from a group which is formed from proteases, lipases, transglutaminase, oxidases and peroxidases.
  • Pearl extracts are also suitable as a conditioner.
  • Pearls of mussels consist essentially of inorganic and organic calcium salts, trace elements and proteins. Pearls can be easily obtained from cultivated mussels. The cultivation of the mussels can be done in fresh water as well as in sea water. This can affect the ingredients of the beads. According to the invention, preference is given to a pearl extract which originates from shells cultivated in marine or salt water. The pearls consist to a large extent of aragonite (calcium carbonate), conchiolin and an albuminoid. The latter components are proteins. Also included in beads are magnesium and sodium salts, inorganic silicon compounds, and phosphates.
  • the beads are pulverized. Thereafter, the pulverized beads are extracted by the usual methods.
  • extraction agent for the preparation of the pearl extracts water, alcohols and mixtures thereof can be used. Underwater are understood to mean both demineralized water and seawater.
  • the alcohols are lower alcohols such as ethanol and isopropanol, but especially polyhydric alcohols such as glycerol, diglycerol, triglycerol, polyglycerol, ethylene glycol, propylene glycol and butylene glycol, both as sole extractant and in admixture with demineralized water or sea water, are preferred.
  • Pearl extracts based on water / glycerine mixtures have proven to be particularly suitable.
  • the pearl proteins can be largely in the native state or already partially or largely present as protein hydrolysates. Preference is given to a pearl extract in which conchiolin and albuminoid are already partially hydrolyzed.
  • the essential amino acids of these proteins are glutamic acid, serine, alanine, glycine, aspartic acid and phenylalanine.
  • the pearl extract is additionally enriched with at least one or more of these amino acids.
  • the pearl extract is enriched with glutamic acid, serine and leucine.
  • a preferred extract contains organic and / or inorganic calcium salts and magnesium and Sodium salts, inorganic silicon compounds and / or phosphates.
  • a most preferred pearl extract contains at least 75%, preferably 85%, more preferably 90% and most preferably 95% of all ingredients of the naturally occurring pearls. Examples of pearl extracts usable according to the invention are the commercial products Pearl Protein Extract BG ® or Crodarom ® Pearl.
  • the above-described pearl extracts are preferably contained in an amount of at least 0.01 to 20% by weight.
  • amounts of the extract of 0.01 to 10% by weight, most preferably amounts of 0.01 to 5 wt.% Based on the total agent used.
  • Some of the aforementioned care substances can reduce the bond strength, ie in particular surface tack and adhesion, of the pressure-sensitive adhesives used.
  • the care substances as well as the other ingredients of the cosmetic product must therefore be carefully matched to the pressure-sensitive adhesives used. Type or concentration of these ingredients are chosen so that the bond strength of the pressure-sensitive adhesives also has the desired strength in the finished agent. Suitable combinations can be easily determined by simple preliminary tests.
  • the agent according to the invention is present in a cosmetically acceptable carrier. It is preferably an aqueous, an alcoholic or an aqueous-alcoholic medium with preferably at least 10 percent by weight of water, based on the total preparation.
  • a cosmetically acceptable carrier 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.
  • organic solvents or a mixture of solvents with a boiling point below 400 0 C in an amount of 0.1 to 15 weight percent may be included purchased from 1 to 10 wt percent on the total preparation is preferred.
  • Particularly suitable as additional 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, diethylene glycol and propylene glycol in an amount of up to 30 percent by weight based on the total preparation.
  • the preparation can be carried out, for example, in the form of creams, emulsions, gels or surfactant-containing foaming solutions or other preparations which are suitable for the Application on the hair are suitable.
  • the preparations preferably have a pH of from 2 to 11.
  • the pH range between 2 and 8 is particularly preferred.
  • the information on the pH value in the context of this document refers to the pH at 25 ° C., unless otherwise stated.
  • the agent according to the invention can be present in the known application forms.
  • the agent can be prepared in the usual way as aerosol hair spray, pump spray, hair gel, hair wax or mousse.
  • the agent according to the invention is to be applied in the form of an aerosol spray or aerosol foam consolidator, the agent is filled in a customary manner into a pressure-resistant container and mixed with a propellant. The container is finally closed and provided with a suitable spray device.
  • Suitable blowing agents are the compounds customarily used for this purpose, such as dialkyl ethers, alkanes, N 2 O, CO 2 or air. Preference is given to dimethyl ethers and alkanes having 3 to 5 carbon atoms, such as propane, n-butane, isobutane, n-pentane and iso-pentane; n-butane, propane and mixtures thereof are particularly preferred.
  • 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 UV filters preferred according to the invention can be selected, for example, from substituted benzophenones, p-aminobenzoic acid esters, diphenylacrylic esters, cinnamic acid esters, salicylic acid esters, benzimidazoles and o-aminobenzoic acid esters.
  • UV filters which can be used according to the invention are 4-aminobenzoic acid, N, N, N-trimethyl-4- (2-oxoborn-3-ylidenemethyl) aniline methylsulfate, 3,3,5-trimethylcyclohexyl salicylate (homosalates), 2-hydroxy-4-methoxy-benzophenone (benzophenone-3; Uvinul ® M 40, Uvasorb MET ®, ® Neo Heliopan BB, Eusolex ® 4360), 2-phenylbenzimidazole-5-sulfonic acid and potassium, sodium and triethanolamine salts ( Phenylbenzimidazole Sulfonic Acid; Parsol ® HS; Neo Heliopan Hydro ®), 3,3 '- (1, 4-phenylenedimethylene) bis (7,7-dimethyl-2-oxo-bicyclo [2.2.1] hept-1- yl-methane sulfonic acid) and salts thereof, 1- (4-tert-butyl
  • water-insoluble UV filters In structurally similar UV filters, in many cases the water-insoluble compound has the higher effect over those water-soluble compounds which differ from it by one or more additional ionic groups.
  • water-insoluble UV filters are to be understood which at 20 ° C. do not exceed 1 % By weight, in particular not more than 0.1% by weight, in water.
  • these compounds should be soluble in common cosmetic oil components at room temperature to at least 0.1, in particular at least 1 wt .-%. The use of water-insoluble UV filters may therefore be preferred according to the invention.
  • UV filters which have a cationic group, in particular a quaternary ammonium group.
  • UV filters have the general structure U - Q.
  • the structural part U stands for a UV-absorbing group.
  • This group can in principle be derived from the known UV filters which can be used in the cosmetics sector, in which a group, generally a hydrogen atom, of the UV filter is replaced by a cationic group Q, in particular having a quaternary amino function ,
  • Compounds from which the structural part U can be derived are, for example, substituted benzophenones, p-aminobenzoic acid esters, diphenylacrylic acid esters, cinnamic acid esters, salicylic acid esters, benzimidazoles and o-aminobenzoic acid esters.
  • Structural parts U which are derived from cinnamic acid amide or from N, N-dimethylaminobenzoic acid amide are preferred according to the invention.
  • the structural parts U can in principle be chosen such that the absorption maximum of the UV filters can be in both the UVA (315-400 nm) and in the UVB (280-315 nm) or in the UVC ( ⁇ 280 nm) range. 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 structural part U also as a function of structural part Q, is preferably selected so that the molar extinction coefficient of the UV filter at the absorption maximum is above 15,000, in particular above 20,000.
  • the structural part Q preferably contains, as a cationic group, a quaternary ammonium group.
  • This quaternary ammonium group can in principle be connected directly to the structural part U, so that the structural part U represents one of the four substituents of the positively charged nitrogen atom.
  • one of the four substituents on the positively charged nitrogen atom is preferred a group, especially an alkylene group having 2 to 6 carbon atoms, which functions as a compound between the structural part U and the positively charged nitrogen atom.
  • the group Q has the general structure - (CH 2 ) X -N + R 1 R 2 R 3 X ' , where x is an integer from 1 to 4, R 1 and R 2 independently of one another are Ci_ 4 alkyl groups, R 3 is 22 alkyl group or a benzyl group and x "is a physiologically acceptable anion for a CI_.
  • x is preferably the number 3
  • R 1 and R 2 each represent a methyl group and R 3 is either for a methyl group or a saturated or unsaturated, linear or branched hydrocarbon chain having 8 to 22, in particular 10 to 18, carbon atoms.
  • Physiologically acceptable anions are, for example, inorganic anions such as halides, in particular chloride, bromide and fluoride, sulfate ions and phosphate ions and organic anions such as lactate, citrate, acetate, tartrate, methosulfate and tosylate.
  • inorganic anions such as halides, in particular chloride, bromide and fluoride, sulfate ions and phosphate ions and organic anions such as lactate, citrate, acetate, tartrate, methosulfate and tosylate.
  • UV filters with cationic groups are the commercially available compounds cinnamic acid-trimethylammonium chloride (lncroquat ® UV-283) and dodecyl tosylate (Escalol ® HP 610).
  • the teaching of the invention also includes the use of a combination of several UV filters.
  • the combination of at least one water-insoluble UV filter with at least one UV filter with a cationic group is preferred.
  • 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 or indophenols.
  • Preferred substantive dyes are those having the international designations or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, HC Yellow 12, Acid Yellow 1, Acid Yellow 10, Acid Yellow 23, Acid Yellow 36, HC Orange Disperse Orange 3, Acid Orange 7, HC Red 1, HC Red 3, HC Red 10, HC Red 11, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 11, HC Blue 12, Disperse Blue 3, Acid Blue 7, Acid Green 50, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Acid Violet 43, Disperse Black 9, Acid Black 1, and Acid Black 52 known compounds as well as 1 , 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1,4-bis- ( ⁇ -hydroxyethyl) -amino-2-nitrobenzene, 3-
  • 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
  • Preferred cationic substantive dyes of group (c) are in particular the following compounds:
  • the compounds of the formulas (DZ1), (DZ3) and (DZ5) which are also known by the names Basic Yellow 87, Basic Orange 31 and Basic Red 51, are very particularly preferred cationic substantive dyes of group (c).
  • 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 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 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.
  • 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 substantive dyes each represent uniform compounds. Rather, in the inventive compositions, due to the production process for the individual dyes, in minor amounts, other components may be included, as far as they do not adversely affect the styling result or for other reasons, e.g. toxicological, must be excluded.
  • the agents may furthermore contain all active ingredients, additives and auxiliaries known for such preparations.
  • the agents contain at least one surfactant, wherein in principle both anionic and zwitterionic, ampholytic, nonionic and cationic surfactants are suitable. In many cases, however, it has proved to be advantageous to select the surfactants from anionic, zwitterionic or nonionic surfactants.
  • Other active ingredients, auxiliaries and additives are, for example
  • Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, e.g. For example, methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such. Bentonite or fully synthetic hydrocolloids such as e.g.
  • Antidandruff active ingredients such as Piroctone Olamine, zinc Omadine and Climbazol, substances for adjusting the pH, such as conventional acids, in particular edible acids and bases, cholesterol,
  • Bodying agents such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as spermaceti, beeswax, montan wax and paraffins, fatty acid alkanolamides,
  • Complexing agents such as EDTA, NTA, ⁇ -alaninediacetic acid and phosphonic acids, swelling and penetrating agents such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex, styrene / PVP and styrene / acrylamide copolymers Pearlescing agents such as ethylene glycol mono- and distearate and PEG-3-distearate, preservatives, antioxidants.
  • swelling and penetrating agents such as glycerol, propylene glycol monoethyl ether, carbonates, bicarbonates, guanidines, ureas and primary, secondary and tertiary phosphates, opacifiers such as latex, styrene / PVP and styrene / acrylamide cop
  • a second object of the invention is the use of a pressure-sensitive adhesive selected from vinyl ester-ethylene copolymers, modified polyacrylic acid esters and modified polymethacrylic acid esters in a keratinous fiber-shaping agent for inducing or improving the remodeling ability of the deformation achieved or fixed using the agent.
  • the pressure-sensitive adhesive is added to the keratinous fiber-forming agent in an amount such that the total amount of pressure-sensitive adhesives is 0.1 to 10% by weight, preferably 0.5 to 8% by weight.
  • the percentages are based on the total average minus any propellants present in the composition. Further particular and preferred embodiments of the use according to the invention correspond to those already described in the description of the agent according to the invention.
  • compositions E1 to E6 can be prepared in a known manner by mixing the raw materials according to the following table.
  • Vinylpyrrolidone vinyl acetate copolymer (30:70) (about 48-52% solids in i-propanol, INCI name: VP / VA copolymer, isopropyl alcohol) (BASF)

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Abstract

La présente invention concerne un agent destiné à modeler des fibres de kératine, contenant, dans un support cosmétiquement acceptable, au moins une substance collante choisie entre des copolymères d'éthylène d'ester de vinyle, des esters d'acide polyacrylique modifiés et des esters d'acide polyméthacrylique modifiés. L'invention concerne également l'utilisation de substances collantes correspondantes dans des agents fixatifs pour induire ou améliorer la capacité à être remodelée d'une coiffure produite ou fixée au moyen de l'agent fixatif.
PCT/EP2007/059206 2006-12-08 2007-09-04 Agent fixatif pour fibres de kératine WO2008068067A2 (fr)

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EP07803186A EP2056786A2 (fr) 2006-12-08 2007-09-04 Agent fixatif pour fibres de kératine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610058389 DE102006058389A1 (de) 2006-12-08 2006-12-08 Stylingmittel für keratinische Fasern
DE102006058389.2 2006-12-08

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WO2008068067A2 true WO2008068067A2 (fr) 2008-06-12
WO2008068067A3 WO2008068067A3 (fr) 2008-11-20

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190209445A1 (en) * 2016-04-15 2019-07-11 Manel Torres Sprayable compositions for styling hair

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999061496A1 (fr) * 1998-05-22 1999-12-02 Union Carbide Chemicals & Plastics Technology Corporation Compositions copolymeres de latex d'ethylene
FR2786392A1 (fr) * 1998-11-26 2000-06-02 Oreal Composition de coiffage comprenant un polymere aux caracteristiques particulieres et un polymere non ionique
EP1321130A2 (fr) * 2001-12-20 2003-06-25 L'oreal Composition de coiffage repositionnable comprenant des copolymères (méth)acryliques

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999061496A1 (fr) * 1998-05-22 1999-12-02 Union Carbide Chemicals & Plastics Technology Corporation Compositions copolymeres de latex d'ethylene
FR2786392A1 (fr) * 1998-11-26 2000-06-02 Oreal Composition de coiffage comprenant un polymere aux caracteristiques particulieres et un polymere non ionique
EP1321130A2 (fr) * 2001-12-20 2003-06-25 L'oreal Composition de coiffage repositionnable comprenant des copolymères (méth)acryliques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190209445A1 (en) * 2016-04-15 2019-07-11 Manel Torres Sprayable compositions for styling hair
US10765608B2 (en) * 2016-04-15 2020-09-08 Manel Torres Sprayable compositions for styling hair

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