WO2012084532A2 - Procédé de mise en forme de fibres kératiniques - Google Patents

Procédé de mise en forme de fibres kératiniques Download PDF

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Publication number
WO2012084532A2
WO2012084532A2 PCT/EP2011/072206 EP2011072206W WO2012084532A2 WO 2012084532 A2 WO2012084532 A2 WO 2012084532A2 EP 2011072206 W EP2011072206 W EP 2011072206W WO 2012084532 A2 WO2012084532 A2 WO 2012084532A2
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WO
WIPO (PCT)
Prior art keywords
acid
fibers
hair
keratin
carboxylic acid
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PCT/EP2011/072206
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German (de)
English (en)
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WO2012084532A3 (fr
Inventor
Thorsten Knappe
Helga Flodrop Van
Anna Henschel
Rolf Bayersdörfer
Original Assignee
Henkel Ag & Co. Kgaa
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Application filed by Henkel Ag & Co. Kgaa filed Critical Henkel Ag & Co. Kgaa
Priority to EP11808840.0A priority Critical patent/EP2694161A2/fr
Publication of WO2012084532A2 publication Critical patent/WO2012084532A2/fr
Publication of WO2012084532A3 publication Critical patent/WO2012084532A3/fr

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic acids
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

  • the invention relates to the technical field of reshaping keratin-containing fibers, in particular human hair.
  • the invention relates to the use of at least one specific carboxylic acid having two or more carboxyl groups for the heat-assisted forming keratin inconveniencer fibers, in particular human hair, and a corresponding forming process and usable therein means for forming.
  • keratin-containing fibers in principle all animal hair, e.g. Wool, horsehair, angora hair, furs, feathers and products made therefrom or textiles.
  • the invention is preferably used in the context of a hair shaping, in particular the smoothing of curly human hair and wigs made therefrom.
  • a permanent deformation keratin inconveniencer fibers is usually carried out so as to mechanically deform the fiber and determines the deformation by suitable means.
  • the fiber Before and / or after this deformation, the fiber is treated with a keratin-reducing preparation. After a rinsing operation, the fiber is then treated with an oxidizing agent preparation in the so-called fixing step, rinsed and freed from the forming aids (e.g., winders, papillots) after or during the fusing step.
  • a mercaptan e.g.
  • Ammonium thioglycolate is used, this part of the disulfide bridges of the keratin molecule cleaves to -SH groups, so that there is a softening of keratin fibers.
  • disulfide bridges are knotted in the hair keratin, so that the Keratinge Shege is fixed in the predetermined deformation.
  • sulfite instead of the mercaptans for hair styling.
  • the permanent smoothing of keratin-containing fibers is achieved analogously by the use of keratin-reducing and -oxidierenden compositions.
  • the frizzy hair is wound either on curlers with a large diameter of usually more than 15 mm or the hair under the action of keratin reducing Smooth combed composition.
  • Smoothing boards are usually rectangular boards, for example made of plastic.
  • the fiber is wetted with the keratin-reducing preparation.
  • the known forming methods especially in the case of smoothing, have the disadvantage that the keratin-containing fiber is charged electrostatically.
  • the deformation result of the known methods in terms of the degree of deformation and the uniformity of the deformation is in need of improvement. When an improvement in the degree of deformation is achieved, this is usually accompanied by an increased damage to the keratin-containing fiber.
  • the object of the invention is therefore to provide a shaping method for keratin-containing fibers, in particular for human hair, which provides a very good and lasting deformation result, which cares for the fiber and protects the structure of the fiber.
  • a first subject of the invention is therefore the use of at least one (C 2 to C 0 ) -carboxylic acid, comprising at least two carboxyl groups, for the heat-assisted transformation of keratin-containing fibers, in particular human hair.
  • the carboxylic acid used in the invention may be linear or branched or cyclic.
  • the carboxylic acid used in the invention is preferably aliphatic.
  • the carboxylic acid used according to the invention may carry, in addition to the carboxyl groups, further substituents. It is preferable in the invention, the carboxylic acid used in the invention in the case of a substitution of its hydrocarbon backbone with at least one other group selected from hydroxy, oxo, (C ⁇ to C 4) alkoxy, (C ⁇ to C 4) -alkoxycarbonyl, (C 2 to C 4 ) -acyloxy, (C 1 to C 4 ) -hydroxyalkyloxy.
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent, physiologically compatible cation
  • n is an integer greater than or equal to 2
  • p 0, 1 or 2
  • n 0, 1, 2 or 3
  • R is independently a hydroxy group, a (C 1 -C 4 ) -alkoxy group, (C 1 -C 4 ) -alkoxycarbonyl group, (C 2 -C 4 ) -acyloxy group, a (C 1 -C 4 ) Hydroxyalkyloxy group,
  • n + m + 2p is not greater than 2x + 2.
  • carboxylic acids used according to the invention additionally have a molecular weight of less than 400 g / mol, particularly preferably less than 200 g / mol, very particularly preferably less than 150 g / mol.
  • the carboxylic acids used in the invention has a pK s value at 25 ° C in water of less than 4, in particular of less than 3.
  • the pK s value is the pKa value of the first dissociation stage of polybasic acids.
  • the (C 2 to C 0 ) - carboxylic acid comprising at least two carboxyl groups is selected from at least one aliphatic (C 2 to C 0 ) carboxylic acid having a pK s value at 25 ° C. in water of less than 4 (in particular less than 3), a molecular weight of less than 400 g / mol (particularly preferably of less than 200 g / mol, most preferably less than 150 g / mol), and at least two carboxyl groups,
  • the carboxylic acid used in the invention is particularly preferably selected from at least one compound selected from oxalic, tartaric, 2-hydroxymalonic, malonic, oxomalonic, maleic, malic, 2-oxosuccinic, 2,3-dioxosuccinic, citric acid.
  • At least one (C 2 to C 0 ) -carboxylic acid comprising at least two carboxyl groups for the heat-assisted transformation of keratin-containing fibers, in particular human hair, at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C).
  • a heat source is preferably a hot air blower (for example, in the embodiment as a hair dryer, hood or curling iron), a flat iron or a corrugated iron.
  • At least one (C 2 to C 0 ) -carboxylic acid comprising at least two carboxyl groups (in particular at least one of the abovementioned preferred carboxylic acids) as part of a heat-assisted smoothing of keratin-containing fibers, in particular human hair, at a temperature of 50 ° C. to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C) is used.
  • the cosmetic agent based on the total weight of the composition, at least 2.0 wt .-%, again preferably at least 5.0 wt .-%, more preferably at least 10.0 wt .-% , at least one said carboxylic acid (in particular the preferred carboxylic acids (vide supra)).
  • a second aspect of the invention is a cosmetic composition
  • a cosmetic composition comprising, in a cosmetically acceptable carrier, based on the total weight of the composition, at least 2.0% by weight of a (C 2 to C 0 ) carboxylic acid comprising at least two carboxyl groups.
  • the agent according to the invention comprises the said carboxylic acids (in particular the preferred carboxylic acids of the first subject of the invention (vide supra)) in an amount of at least 5.0% by weight, more preferably of at least 10.0% by weight, each based on the total weight of the composition contains.
  • the composition according to the invention contains the said carboxylic acids (in particular the preferred carboxylic acids of the first subject of the invention (vide supra)) in an amount of from 2 to 60% by weight, in particular from 5 to 30% by weight, based in each case on the total weight of agent.
  • the agents according to the invention contain the ingredients or active ingredients in a cosmetically acceptable carrier.
  • Preferred cosmetically acceptable carriers are aqueous, alcoholic or aqueous-alcoholic media.
  • the agents according to the invention preferably comprise an aqueous or aqueous-alcoholic medium as a cosmetically acceptable carrier. Agents according to the invention therefore preferably contain at least 10% by weight of water, in particular at least 30% by weight of water, in each case based on the total agent.
  • alcohols it is possible in particular to include the lower alcohols having 1 to 4 carbon atoms (in particular (C 1 to C 4 ) monohydroxyalkanes) customarily used for cosmetic purposes, such as, for example, ethanol and isopropanol. It is preferred according to the invention to use at least one (C 1 -C 4 ) -monohydroxyalkane in the agents according to the invention, in particular in an amount of from 1 to 50% by weight, in particular from 5 to 30% by weight.
  • C 1 -C 4 monohydroxyalkanes
  • the cosmetically acceptable carrier of the agent according to the invention very particularly preferably contains at least 10% by weight of water and 0 to 50% by weight of at least one (C 1 to C 4 ) monohydroxyalkane (in particular at least 30% by weight of water and optionally 5 to 30 wt .-% of at least one (C ⁇ to C 4 ) monohydroxyalkane), each based on the total weight of the composition according to the invention.
  • organic solvents or a mixture of solvents having a boiling point below 400 ° C. may be present in an amount of from 0.1 to 15% by weight, preferably from 1 to 10% by weight, based on the total agent according to the invention.
  • 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 and 1, 2-propylene glycol in an amount of up to 30 wt .-% based on the total agent.
  • the agent based on the total weight of the composition, contains less than 0.5% by weight (in particular less than 0.1% by weight) of sulfur-containing keratin-reducing compounds.
  • the agents according to the invention are particularly preferably free from sulfur-containing, keratin-reducing compounds. Keratin reducing compounds are capable of reductively cleaving keratin fiber disulfide groups to form thiol groups.
  • the following embodiments (A) to (H) of the agent according to the invention are preferably suitable according to the invention:
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the composition, at least 5.0 wt .-% of a (C 2 to C 0 ) carboxylic acid having a molecular weight of less than 400 g / mol, more preferably of less than 200 g / mol, very particularly preferably of less than 1 50 g / mol, comprising at least two carboxyl groups.
  • composition comprising, in a cosmetically acceptable carrier, based on the total weight of the composition, at least 5.0% by weight of a carboxylic acid of at least one compound of the formula (I),
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent, physiologically compatible cation
  • n is an integer greater than or equal to 2
  • p 0, 1 or 2
  • n 0, 1, 2 or 3
  • R is independently a hydroxy group, a (C 1 to C 4 ) alkoxy group, (C 1 to C 4 ) alkoxycarbonyl group, (C 2 to C 4 ) acyloxy group, a (C 1 to C 4 ) hydroxyalkyloxy group,
  • n + m + 2p is not greater than 2x + 2.
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the agent, at least 5.0 wt .-% of an aliphatic (C 2 to C 0 ) carboxylic acid having a molecular weight of less than 400 g / mol, more preferably of less than 200 g / mol, very particularly preferably less than 150 g / mol, comprising at least two carboxyl groups.
  • a cosmetically acceptable carrier based on the total weight of the agent, at least 5.0 wt .-% of an aliphatic (C 2 to C 0 ) carboxylic acid having a molecular weight of less than 400 g / mol, more preferably of less than 200 g / mol, very particularly preferably less than 150 g / mol, comprising at least two carboxyl groups.
  • Composition comprising, in a cosmetically acceptable carrier, based on the total weight of the composition, at least 5.0% by weight of one or more carboxylic acids selected from at least one compound of the group formed from oxalic acid, tartaric acid, 2-hydroxymalonic acid, Malonic acid, oxomalonic acid, maleic acid, malic acid, 2-oxosuccinic acid, 2,3-dioxosuccinic acid, citric acid.
  • carboxylic acids selected from at least one compound of the group formed from oxalic acid, tartaric acid, 2-hydroxymalonic acid, Malonic acid, oxomalonic acid, maleic acid, malic acid, 2-oxosuccinic acid, 2,3-dioxosuccinic acid, citric acid.
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the agent,
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the agent,
  • M is a hydrogen atom or one equivalent of a mono- or polyvalent, physiologically compatible cation
  • n is an integer greater than or equal to 2
  • p 0, 1 or 2
  • n 0, 1, 2 or 3
  • R independently represents hydroxy, (C ⁇ to C 4) alkoxy, (CT-C 4) alkoxycarbonyl, (C 2 -C 4) acyloxy group, a (C ⁇ to C 4) - hydroxyalkyloxy,
  • n + m + 2p is not greater than 2x + 2
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the agent, - At least 5.0 wt .-% of an aliphatic (C 2 to C 0 ) carboxylic acid having a molecular weight of less than 400 g / mol, more preferably of less than 200 g / mol, most preferably of less than 150 g / mol comprising at least two carboxyl groups, and
  • Agent comprising, in a cosmetically acceptable carrier, based on the total weight of the agent,
  • carboxylic acids selected from at least one compound of the group formed from oxalic acid, tartaric acid, 2-hydroxymalonic acid, malonic acid, oxomalonic acid, maleic acid, malic acid, 2-oxosuccinic acid, 2,3 - dioxosuccinic acid, citric acid, and
  • the agent according to the invention additionally contains at least one setting polymer selected from at least one compound from the group consisting of strengthening nonionic polymers, setting anionic polymers, setting amphoteric polymers and setting cationic polymers.
  • the agent according to the invention preferably contains at least one consolidating cationic polymer.
  • the additional strengthening cationic polymers have at least one structural unit containing at least one permanently cationized nitrogen atom. Permanently cationized nitrogen atoms are to be understood as meaning those nitrogen atoms which carry a positive charge and thereby form a quaternary ammonium compound. Quaternary ammonium compounds are most commonly prepared by reacting tertiary amines with alkylating agents, e.g. Methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also produced ethylene oxide. Depending on the tertiary amine used, the following groups are known in particular: alkylammonium compounds, alkenylammonium compounds, imidazolinium compounds and pyridinium compounds.
  • Preferred agents in the context of this embodiment comprise the setting cationic polymers in an amount of from 0.1% by weight to 20.0% by weight, particularly preferably from 0.2% by weight to 10.0% by weight, most preferably from 0.5 wt .-% to 5.0 wt .-%, each based on the weight of the composition.
  • the cationic fixing polymers can be selected according to the invention from cationic, quaternized cellulose derivatives.
  • such cationic, quaternized celluloses prove to be advantageous in the sense of the embodiment which carries more than one permanent cationic charge in a side chain.
  • the cationic cellulose derivatives are those which are prepared from the reaction of hydroxyethylcellulose with a dimethyldiallylammonium reactant (in particular dimethyldiallylammonium chloride), if appropriate in the presence of further reactants.
  • a dimethyldiallylammonium reactant in particular dimethyldiallylammonium chloride
  • such cationic celluloses with the INCI name Polyquaternium-4 are particularly suitable.
  • cationic fixing polymers which comprise at least one structural unit of the formula (N1) and at least one structural unit of the formula (N2) and optionally at least one structural unit of the formula (K1)
  • R and R 4 independently of one another represent a hydrogen atom or a methyl group
  • a and A 2 are each independently a group of ethane-1, 2-diyl, propane-1, 3-diyl or
  • RR 22 , RR 33 , RR 55 and IR 6 independently of one another represent a (C 1 to C 4 ) -alkyl group
  • R 7 is a (C 8 to C 30 ) alkyl group.
  • Suitable compounds are, for example, as
  • Copolymers of methacryloylaminopropyllauryldimethylammonium chloride with N-vinylpyrrolidone, N-vinylcaprolactam and dimethylaminopropylmethacrylamide with the INCI name Polyquaternium-69 are particularly preferably usable solidifying cationic polymers continue to serve such festierend cationic copolymers containing a copolymer (c1) which in addition to at least one structural element of the formula (K2) additionally comprises a structural element of the formula (N1)
  • R is a (C 1 to C 4 ) -alkyl group, in particular a methyl group.
  • N-methylvinylimidazole / vinylpyrrolidone copolymers are referred to as Polyquaternium-16 according to INCI nomenclature.
  • the preferred N-methylvinylimidazole / vinylpyrrolidone copolymers are referred to as Polyquaternium-44 according to INCI nomenclature.
  • N-methylvinylimidazole / vinylpyrrolidone / vinylcaprolactam copolymers which according to INCI nomenclature are referred to as Polyquarternium-46.
  • N-methylvinylimidazole / vinylpyrrolidone / vinylimidazole / methacrylamide copolymers which according to INCI nomenclature are referred to as Polyquaternium-68.
  • Very particularly preferred copolymers (c3) contain 1 to 12 mol%, preferably 3 to 9 mol% and in particular 6 mol% of structural units of the formula (K2-a) and 45 to 65 mol%, preferably 50 to 60 mol .-% and in particular 55 mol .-% of structural units of the formula (N1) and 1 to 20 mol .-%, preferably 5 to 15 mol .-% and in particular 10 mol .-% of structural units of the formula (N3) and 20 to 40 mol .-%, preferably 25 to 35 mol .-% and in particular 29 mol .-% of structural units of the formula (N4).
  • the composition according to the invention preferably contains at least one strengthening nonionic polymer as additional strengthening polymer.
  • a nonionic polymer is understood which carries in a protic solvent under standard conditions substantially no structural units with permanently cationic or anionic groups which have to be compensated by counterions while maintaining the electroneutrality.
  • the reinforcing nonionic polymers are preferably contained in the agent of this embodiment in an amount of from 0.1% to 20.0% by weight, more preferably from 0.2% to 15.0% by weight. , very particularly preferably from 0.5 wt .-% to 10.0 wt .-%, each based on the weight of the inventive composition.
  • compositions according to the invention particularly preferably contain at least one chitosan as nonionic setting polymer.
  • chitosans as typical biopolymers come within the meaning of the invention as derivatives alkoxylated chitosans in question.
  • Preferred agents according to the invention are characterized in that they contain as chitosan at least one neutralization product of chitosan with at least one organic carboxylic acid.
  • the chitosans or their derivatives are preferred in the inventive compositions in an amount of 0.01 wt .-% to 5 wt .-%, particularly preferably from 0.05 wt .-% to 2.0 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.
  • the strengthening nonionic polymers are preferably selected from at least one
  • An agent which comprises, as a consolidating nonionic polymer, at least one polymer selected from the group formed
  • Copolymers of N-vinylpyrrolidone with N, N-di alkylamino (C 2 to C 4) -alkylacrylamid, copolymers of N-vinylpyrrolidone with N, N-di (C to C 4!) (C 4 to C!) - Alkylamino (C 2 to C 4 ) alkylacrylamide are very particularly preferred according to the invention. Also preferred are polymers of the INCI name VP / methacrylamide / vinyl imidazole copolymer.
  • compositions according to the invention may also contain as consolidating polymer at least one consolidating amphoteric polymer.
  • An example of a usable according to the invention setting amphoteric polymer 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 Acrylic acid, methacrylic acid and their simple alkyl esters.
  • the strengthening amphoteric polymers are preferably present in the water-based compositions which can be used 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 solidifying anionic polymer can be used as setting polymers.
  • the composition of the invention contains a solidifying anionic polymer, it is preferably in the form of a spray, in particular an aerosol spray.
  • the setting anionic polymers are preferred in the composition according to the invention in an amount of 0.1 wt .-% to 20.0 wt .-%, particularly preferably from 0.2 wt .-% to 15.0 wt .-%, completely particularly preferably from 0.5 wt .-% to 10.0 wt .-%, each based on the total composition.
  • Particularly preferred polymers of this type are selected from at least one polymer of the group formed
  • Particularly preferred polymers are selected from at least one polymer of the group formed from copolymers of acrylic acid and ethyl acrylate and N-tert-butylacrylamide.
  • the water-based composition which can be used according to the invention as an anionic setting polymer may comprise at least one polyurethane having at least one carboxyl group (for example a copolymer of isophthalic acid, adipic acid, 1,6-hexanediol, neopentyl glycol and).
  • the setting anionic polymers are preferably contained in an amount of 0.1 wt .-% to 15 wt .-%, in particular from 0.5 wt .-% to 10 wt .-%, each based on the weight of the water-based composition ,
  • the agents according to the invention additionally contain at least one cationic surfactant.
  • cationic surfactants are selected from quaternary ammonium compounds, esterquats and amidoamines or Mixtures thereof are preferred.
  • Preferred quaternary ammonium compounds are ammonium halides, especially chlorides and bromides, such as alkyltrimethylammonium chlorides, dialkyldimethylammonium chlorides and trialkylmethylammonium chlorides, e.g.
  • 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.
  • the alkylamidoamines are usually prepared by amidation of natural or synthetic fatty acids and fatty acid cuts with dialkylaminoamines.
  • An inventively particularly suitable compound from this group of substances under the name Tegoamid ® S 18 commercial stearamidopropyl dimethylamine is.
  • the cationic surfactants are contained in the agents according to the invention preferably in amounts of 0.05 to 10 wt .-%, based on the total agent. Amounts of 0.1 to 5 wt .-% are particularly preferred.
  • agents according to the invention additionally comprise at least one nonionic surfactant.
  • Nonionic surfactants contain as hydrophilic group e.g. a polyol group, a polyalkylene glycol ether group, or a combination of polyol and polyglycol ether groups.
  • hydrophilic group e.g. a polyol group, a polyalkylene glycol ether group, or a combination of polyol and polyglycol ether groups.
  • Such compounds are, for example
  • R is CO for a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms
  • R 2 is hydrogen or methyl
  • R 3 is linear or branched alkyl radicals having 1 to 4 carbon atoms
  • w is a number from 1 to 20 .
  • Adducts of ethylene oxide with fatty acid alkanolamides and fatty amines Adducts of ethylene oxide with fatty acid alkanolamides and fatty amines
  • R 4 is an alkyl or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10. They can be obtained by the relevant methods of preparative organic chemistry.
  • 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 ,
  • the agents according to the invention as surfactant very particularly preferably contain at least one addition product of from 15 to 100 mol of ethylene oxide, in particular from 15 to 50 mol of ethylene oxide, to a linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ethylene oxide in particular from 15 to 50 mol of ethylene oxide
  • linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ceteareth-15, ceteareth-25 or ceteareth-50 which are marketed as Eumulgin® CS 15 (COGNIS), Cremophor A25 (BASF SE) or Eumulgin® CS 50 (COGNIS).
  • compositions of the invention may further contain the auxiliaries and additives which are usually added to conventional styling agents.
  • a silicone oil and / or a silicone gum can be used as a care material.
  • 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, dihydroxypolydimethylsiloxanes and polyphenylalkylsiloxanes.
  • 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. Particularly suitable silicones are amino-functional silicones, in particular the silicones, which are summarized under the INCI name Amodimethicone.
  • the agents contain the silicones 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 contain, for example, 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.
  • the agent according to the invention may further comprise at least one vitamin, a provitamin, a vitamin precursor and / or one of their derivatives.
  • 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 further contain at least one plant extract
  • Mono- or oligosaccharides can also be used as a care substance in the compositions according to the invention.
  • the mono- or oligosaccharides are preferably present in the compositions according to the invention in an amount of from 0.1 to 8% by weight, particularly preferably from 1 to 5% by weight, based on the total application preparation.
  • the agent may further contain at least one lipid as a care substance.
  • 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:
  • Ester oils are to be understood as meaning the esters of C 6 - C 30 fatty acids with C 2 - C 30 fatty alcohols.
  • 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,
  • the partial glycerides preferably follow the formula (D4-I),
  • R, R 2 and R 3 independently of one another represent hydrogen or a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18, carbon atoms, with the proviso that at least one of these groups represents 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 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 By adding a UV filter, both the agents themselves and the treated fibers can be protected from the harmful effects of UV radiation.
  • the UV filters are usually in Men a gene of 0.01 -5 wt .-%, based on the entire application preparation. Amounts of 0.1-2.5 wt .-% are preferred.
  • the composition according to the invention also contains one or more substantive dyes. This allows the treated keratin fiber not only to be temporarily patterned when the agent is applied, but also dyed at the same time. This may be particularly desirable if only a temporary dyeing is desired, for example, with eye-catching fashion colors, which can be removed again by simple washing from the keratinic fiber.
  • 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 1, HC Red 1, HC Red 1, HC Red 13, Acid Red 33, Acid Red 52, HC Red BN, Pigment Red 57: 1, HC Blue 2, HC Blue 1, 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 and 1, 4-diamino-2-nitrobenzene, 2-amino-4-nitrophenol, 1, 4-bis (ß-hydroxyethyl) amino-2-nitrobenzene, 3-nitro-4- (ß- hydroxyethyl) aminophenol, 2- (2'-hydroxyethyl
  • the dyes 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 substantive dyes sold under the trademark Arianor® are also very particularly preferred cationic substantive dyes according to the invention.
  • 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.
  • a third object of the invention is a method for reshaping, in particular for smoothing, keratin-containing fibers, in particular human hair, in which
  • a cosmetic composition comprising in a cosmetically acceptable carrier at least one (C 2 to C 0 ) carboxylic acid comprising at least two carboxyl groups (in particular the preferred carboxylic acids of the first subject of the invention (vide supra)), preferably a cosmetic agent of the second subject of the invention on which fibers are applied,
  • the fibers are formed with the aid of deformation aids
  • step (i) - deformed after, before or during step (i), and / or
  • auxiliary for a mechanical smoothing such as a comb or a brush, a smoothing board or a heated flat iron in case of hair straightening.
  • Mechanical smoothing is understood according to the invention to mean stretching of the curly fiber along its longest spatial extent.
  • step (ii) it is preferred, in the context of a hair straightening, to smooth the fibers mechanically during the contact time from step (ii), in particular by combing or with the aid of a smoothing board.
  • shaping aids for example winder
  • the fiber by means of a corrugated process for a longer period of time, it is expedient to remove these deformation aids after step (iv).
  • the keratin-containing fibers are moistened prior to step (i). This can be done by spraying the fibers with a liquid, preferably water.
  • a liquid preferably water.
  • the fibers are shampooed with a conventional shampoo, rinsed and then toweled with a towel. After completion of the terry step remains a noticeable residual moisture in the hair back.
  • reaction time of step (ii) is preferably 5-150 minutes, more preferably 10-60 minutes.
  • step (ii) it is preferred according to the invention to dry the fibers in step (ii) before the heat treatment of step (iii).
  • a dry keratin-containing fiber according to step (ii) of the method according to the invention is present when the water residues adhering to the hair have evaporated to such an extent that the hairs fall individually.
  • dry keratin fiber either the moisture content of the fiber is substantially in equilibrium with the humidity of the air, or the fiber absorbs moisture from the ambient air.
  • Such a dry fiber is preferably obtained by drying the wet fiber with hot air using a hair dryer.
  • step (ii) is preferably carried out if after step (ii) a heat treatment takes place in the context of a forming process in which the surface of the keratin-containing fibers is directly treated with a tempered surface of a forming aid (eg flat iron or corrugated iron) during a forming step ,
  • a heat treatment takes place in the context of a forming process in which the surface of the keratin-containing fibers is directly treated with a tempered surface of a forming aid (eg flat iron or corrugated iron) during a forming step
  • the fibers are subjected to a heat treatment with simultaneous deformation of the fiber at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, more preferably 100 ° C to 250 ° C). more preferably 140 ° C to 220 ° C).
  • Simultaneous deformation means that the fiber is brought or held during the heat treatment in a mold, for example by mechanical smoothing or determination
  • a heat treatment with mechanical smoothing of the fiber at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C, particularly preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C).
  • the heat treatment can be done with hot air. In this case, the fiber is heated during the combing exactly at the point where the mechanical smoothing takes place.
  • the heat treatment in the manner of smoothing with the aid of a so-called smoothing iron with appropriately tempered plates, in particular metal or ceramic plates takes place in which the plate is pressed onto the fiber to be smoothed and pressed onto the fiber plate is moved along the fiber.
  • the plates may optionally be coated with heat resistant materials.
  • the keratin-containing fiber to be smoothed is pressed between two appropriately tempered plates and both plates are simultaneously moved along the longest spatial extent of the fiber. It is again preferred that both plates are connected to each other, so that both plates can be moved uniformly along the fiber.
  • the fiber is attached to one end (hair root).
  • the plates in this case are preferably moved evenly away from the hair root along the entire fiber. This movement causes a mechanical smoothing of the fiber.
  • a suitable device for heat treatment for example, the device "Ceramic Fiat-Master” (sold by: Efalock, Germany) or Schwarzkopf Professional: Model No: IP30A.
  • the fibers are heat-treated under mechanical curling of the fiber in a step (iii) following step (ii) at a temperature of 50 ° C to 350 ° C (preferably 80 ° C to 280 ° C , more preferably 100 ° C to 250 ° C, more preferably 140 ° C to 220 ° C).
  • the heat treatment can be done with a hot air blower.
  • the fiber is wound around a corresponding hot air curling iron and heated precisely at the point where the Krausung occurs.
  • the fibers are wound on curlers as a deformation aid and heated with a hair dryer.
  • the fibers can be treated as part of a post-treatment at the end of the process according to the invention with a commercial conditioner.
  • the following cosmetic agent according to the invention was prepared by mixing the components.
  • compositions marked E are according to the invention, the compositions marked V are not according to the invention.
  • composition marked S is the comparison standard.
  • the hair strand became 1 gram for about 1 minute shampooed the said shampoo and then rinsed under clean water (about 1 minute).
  • the strand of hair was as smooth as possible and placed straight on a watch glass and drizzled with the composition of the invention.
  • the product was lightly rubbed in with a finger (wear gloves!).
  • the strand of hair was well moistened.
  • the hair strand was hung for 2 days and allowed to rest.
  • the tress was dipped in a beaker with water until completely wetted. The water was easily expressed between the fingertips. Then the tress was hung on a leash again and allowed to air dry.
  • the hair strand became 1 gram for about 1 minute shampooed the said shampoo and then rinsed under clean water (about 1 minute).
  • the strand of hair was wound with the help of lace paper around a plastic winder, fixed with a hair clip, placed on a watch glass and with the agent according to the invention drizzled. The strand of hair was well moistened.
  • the hair strand was placed on a clean watch glass for 2 days and allowed to rest.
  • the winder and hair strand was again dried at 45 ° C in a warming cabinet, then removed from the oven and allowed to cool.
  • the strands formed with E1 to E7 were compared with the standard S.
  • the standard of evaluation was:

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Abstract

L'invention concerne des acides carboxyliques (C2 à C10) comportant au moins deux groupes carboxyle, qui se prêtent à la mise en forme de fibres kératiniques, sous apport de chaleur, en particulier les cheveux naturels auxquels ils confèrent une bonne tenue durable.
PCT/EP2011/072206 2010-12-23 2011-12-08 Procédé de mise en forme de fibres kératiniques WO2012084532A2 (fr)

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DE201010064052 DE102010064052A1 (de) 2010-12-23 2010-12-23 Verfahren zur Umformung keratinhaltiger Fasern
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WO2014095210A1 (fr) * 2012-12-19 2014-06-26 Henkel Ag & Co. Kgaa Procédé de mise en forme thermique non agressive de fibres kératiniques
WO2015075063A1 (fr) * 2013-11-21 2015-05-28 Unilever Plc Composition
WO2015074970A1 (fr) * 2013-11-21 2015-05-28 Unilever Plc Procédé de mise en forme des cheveux
US9326926B2 (en) 2014-05-16 2016-05-03 Liqwd, Inc. Keratin treatment formulations and methods
US9414999B2 (en) 2012-05-21 2016-08-16 Conopco, Inc. Method of treating hair
US9572761B2 (en) 2012-05-21 2017-02-21 Conopco, Inc. Method of treating hair
US9597273B2 (en) 2015-04-24 2017-03-21 Liqwd, Inc. Methods for treating relaxed hair
US9713583B1 (en) 2016-07-12 2017-07-25 Liqwd, Inc. Methods and formulations for curling hair
US9855447B2 (en) 2013-08-01 2018-01-02 Liqwd, Inc. Methods for fixing hair and skin
US9872821B1 (en) 2016-07-12 2018-01-23 Liqwd, Inc. Methods and formulations for curling hair
US9974725B1 (en) 2017-05-24 2018-05-22 L'oreal Methods for treating chemically relaxed hair
US10058494B2 (en) 2015-11-24 2018-08-28 L'oreal Compositions for altering the color of hair
US10231915B2 (en) 2015-05-01 2019-03-19 L'oreal Compositions for altering the color of hair
US10441518B2 (en) 2015-11-24 2019-10-15 L'oreal Compositions for treating the hair
US10588839B2 (en) 2013-11-21 2020-03-17 Conopco, Inc. Method of shaping hair
US10617615B2 (en) 2013-11-21 2020-04-14 Conopco, Inc. Method of treating hair
US11090249B2 (en) 2018-10-31 2021-08-17 L'oreal Hair treatment compositions, methods, and kits for treating hair
US11135150B2 (en) 2016-11-21 2021-10-05 L'oreal Compositions and methods for improving the quality of chemically treated hair
US11213470B2 (en) 2015-11-24 2022-01-04 L'oreal Compositions for treating the hair
US11419809B2 (en) 2019-06-27 2022-08-23 L'oreal Hair treatment compositions and methods for treating hair
US11596588B2 (en) 2017-12-29 2023-03-07 L'oreal Compositions for altering the color of hair

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EA026458B1 (ru) * 2012-05-21 2017-04-28 Юнилевер Н.В. Способ обработки волос
WO2013174575A1 (fr) * 2012-05-21 2013-11-28 Unilever Plc Procédé de traitement des cheveux
EP2852375B1 (fr) 2012-05-21 2018-04-04 Unilever PLC Procédé de traitement des cheveux
US9414999B2 (en) 2012-05-21 2016-08-16 Conopco, Inc. Method of treating hair
US9572761B2 (en) 2012-05-21 2017-02-21 Conopco, Inc. Method of treating hair
WO2014095210A1 (fr) * 2012-12-19 2014-06-26 Henkel Ag & Co. Kgaa Procédé de mise en forme thermique non agressive de fibres kératiniques
US10639505B2 (en) 2013-08-01 2020-05-05 Olaplex, Inc. Methods for fixing hair and skin
US9855447B2 (en) 2013-08-01 2018-01-02 Liqwd, Inc. Methods for fixing hair and skin
US11446525B2 (en) 2013-08-01 2022-09-20 Olaplex, Inc. Methods for fixing hair and skin
CN105764480A (zh) * 2013-11-21 2016-07-13 荷兰联合利华有限公司 组合物
US10588839B2 (en) 2013-11-21 2020-03-17 Conopco, Inc. Method of shaping hair
WO2015074970A1 (fr) * 2013-11-21 2015-05-28 Unilever Plc Procédé de mise en forme des cheveux
WO2015075063A1 (fr) * 2013-11-21 2015-05-28 Unilever Plc Composition
US10617615B2 (en) 2013-11-21 2020-04-14 Conopco, Inc. Method of treating hair
US9668954B2 (en) 2014-05-16 2017-06-06 Liqwd, Inc. Keratin treatment formulations and methods
US9498419B2 (en) 2014-05-16 2016-11-22 Liqwd, Inc. Keratin treatment formulations and methods
US9326926B2 (en) 2014-05-16 2016-05-03 Liqwd, Inc. Keratin treatment formulations and methods
US10076478B2 (en) 2014-05-16 2018-09-18 Liqwd, Inc. Keratin treatment formulations and methods
US9597273B2 (en) 2015-04-24 2017-03-21 Liqwd, Inc. Methods for treating relaxed hair
US9717668B2 (en) 2015-04-24 2017-08-01 Liqwd, Inc. Methods for treating relaxed hair
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