EP2793830A2 - Shaping agent for keratinous fibres and hair shaping method - Google Patents
Shaping agent for keratinous fibres and hair shaping methodInfo
- Publication number
- EP2793830A2 EP2793830A2 EP12790878.8A EP12790878A EP2793830A2 EP 2793830 A2 EP2793830 A2 EP 2793830A2 EP 12790878 A EP12790878 A EP 12790878A EP 2793830 A2 EP2793830 A2 EP 2793830A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- acid
- shaping
- pas
- keratin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 238000000034 method Methods 0.000 title claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 88
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- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 16
- 239000000835 fiber Substances 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 17
- 102000011782 Keratins Human genes 0.000 claims description 13
- 108010076876 Keratins Proteins 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 9
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- 230000009471 action Effects 0.000 claims description 4
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- 125000002091 cationic group Chemical group 0.000 description 7
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- 238000010348 incorporation Methods 0.000 description 6
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 6
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- 229910052742 iron Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 239000008107 starch Substances 0.000 description 4
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- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000021239 milk protein Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 229940078812 myristyl myristate Drugs 0.000 description 1
- 229940049292 n-(3-(dimethylamino)propyl)octadecanamide Drugs 0.000 description 1
- WWVIUVHFPSALDO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCN(C)C WWVIUVHFPSALDO-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 229940120511 oleyl erucate Drugs 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- JYTMDBGMUIAIQH-ZPHPHTNESA-N palmityl oleate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC JYTMDBGMUIAIQH-ZPHPHTNESA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 230000016446 peptide cross-linking Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920002553 poly(2-methacrylolyloxyethyltrimethylammonium chloride) polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- FJWSMXKFXFFEPV-UHFFFAOYSA-N prop-2-enamide;hydrochloride Chemical compound Cl.NC(=O)C=C FJWSMXKFXFFEPV-UHFFFAOYSA-N 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229940079053 quaternium-27 Drugs 0.000 description 1
- 239000010667 rosehip oil Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 239000010496 thistle oil Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- FAGMGMRSURYROS-UHFFFAOYSA-M trihexadecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC FAGMGMRSURYROS-UHFFFAOYSA-M 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229940119423 ultracare Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8105—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- A61K8/8111—Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; 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
-
- A—HUMAN NECESSITIES
- A45—HAND OR TRAVELLING ARTICLES
- A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
- A45D7/00—Processes of waving, straightening or curling hair
- A45D7/06—Processes of waving, straightening or curling hair combined chemical and thermal
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8194—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
Definitions
- the present application relates to a method for the permanent deformation of keratinous fibers, in particular for smoothing keratinic fibers, as well as deformation means for carrying out this method.
- the cosmetic, permanent deformation of keratinous fibers is based essentially on the mechanical deformation of the chemically pretreated fibers.
- the fibers formed in this way are finally finally fixed by means of a suitable fixing agent.
- the keratinic fibers are treated with an aqueous keratin-reducing substance.
- the keratin-reducing substance cleaves some of the disulfide bonds of the keratin to -SH groups, resulting in a loosening of the peptide crosslinking and, due to the tension of the fiber due to the mechanical deformation, to a reorientation of the keratin layer.
- the aqueous preparation of the keratin-reducing substance is usually adjusted to be alkaline in order to allow deep penetration of the keratin-reducing substance into the fiber by swelling of the fiber and to ensure adequate deprotonation of the thiol functions of the hair.
- the fiber may be treated with the aqueous preparation of an oxidizing agent. Under the influence of the oxidizing agent again disulfide bonds are knotted, and in this way the Keratinge circage is re-fixed in the predetermined deformation.
- the method described above can be used both for the production of curls and waves in straight hair and for the smoothing of curled hair.
- the results obtained in the hair straightening with this method are in need of improvement.
- a first object of the present invention is a process for the permanent transformation of keratin-containing fibers, in particular human hair, in which
- the deformation agent acts for a contact time Z1
- the fibers are deformed under heat.
- the methods according to the invention are particularly suitable for hair straightening. Preference is therefore given to processes for the permanent transformation keratin restroomr fibers, especially human hair, in which
- the deformation agent acts for a contact time Z1
- the fibers are smoothed under the action of heat.
- a second subject of the present application is a shaping agent, in particular a smoothing agent for keratin fibers containing
- a third object of the present application is the use of polyisoprene-containing deforming agents, preferably deforming agents containing keratin-reducing Substance (s) and at least one polyisoprene, for permanent deformation, preferably for permanent smoothing, keratinic fibers.
- the agents used in the method according to the invention preferably contain the active ingredients in a cosmetic carrier.
- this cosmetic carrier is aqueous, alcoholic or aqueous-alcoholic.
- aqueous-alcoholic carriers are water-containing compositions which, based on their total weight, contain 0.5 to 30% by weight, preferably 2.5 to 25% by weight and in particular 5 to 20% by weight. % of a Ci-C4 alcohol, preferably ethanol and / or 2-propanol and / or 1, 2-propylene glycol.
- an aqueous carrier contains at least 30% by weight, in particular at least 50% by weight, of water, based on the total weight of the application mixture.
- Preferred agents contain, based on its total weight, 40 to 99 wt .-%, preferably 50 to 98 wt .-%, particularly preferably 60 to 95 wt .-% and in particular 70 to 90 wt .-% water.
- the pH (10% solution, 20 ° C.) of preferred agents is from 2 to 12, preferably from 7 to 11 and in particular from 8 to 10.
- Preferred processes according to the invention are characterized in that the shaping agent has a pH (10 % solution in water, 20 ° C) of 2 to 12, preferably from 7 to 1 1 and in particular from 8 to 10.
- the deformation agent under normal conditions (20 ° C, 1013.25 mbar) has a viscosity (Brookfield RTV, spindle 4, 20 U / min) of from 7.5 to 500 Pas, preferably from 10 to 400 Pas, more preferably from 12.5 to 300 Pas, more preferably from 15 to 200 Pas, even more preferably from 17.5 to 100 Pas, most preferably from 20 to 100 Pas, more preferably from 21 to 75 Pas and in particular from 22.5 to 50 Pas.
- the agents according to the invention and the agents used in the methods according to the invention contain as a first constituent keratin-reducing substance (s).
- keratin-reducing substance (s) sulfites, preferably alkali metal, ammonium and / or alkanolammonium salts of sulfurous acid and the desulfurous acid, in particular sodium sulfite (Na 2 S0 3 ) and / or sodium disulfite (Na 2 S 2 0 5 ), Mercaptans, preferably Bunte salts, thioglycolic acid, thiolactic acid, thiomalic acid, mercaptoethanesulfonic acid and their salts and esters, cysteamine, cysteine, preferably the alkali metal or ammonium salts of thioglycolic acid and / or thiolactic acid used.
- Preferred shaping agents contain the keratin-reducing substance (s) in amounts of from 1 to 30% by weight, preferably 2.5 to 25% by weight, particularly preferably 3 to 20% by weight and in particular 5 to 15% by weight, each based on their total weight.
- the agents according to the invention and the agents used in the method according to the invention obtain polyisoprene.
- the use of the polyisoprene improves the results achieved in hair shaping, in particular hair straightening, both in terms of the degree of deformation and in terms of the holding time of the deformation.
- the proportion by weight of the polyisoprene in the total weight of the shaping agent is preferably from 0.01 to 10% by weight, preferably from 0.1 to 8.0% by weight .-% and in particular 0.5 to 6.0 wt .-%.
- reaction time Z1 is 1 to 60 minutes, preferably 2 to 50 minutes, more preferably 5 to 40 minutes and in particular 10 to 30 minutes.
- the keratin-containing fibers are deformed during or after the end of the reaction time under the influence of heat.
- the keratinic fibers in step iii. a heat treatment using a heat source, wherein the heat source has a temperature of 50 to 200 ° C, preferably from 90 to 180 ° C and in particular from 120 to 160 ° C.
- the heat source has a temperature of 50 to 200 ° C, preferably from 90 to 180 ° C and in particular from 120 to 160 ° C.
- a strand of hair is wound around a suitably tempered, rounded body, for example a rod-shaped or tubular body, and unwound again after a residence time of 10 to 30 seconds.
- Particularly preferred uses or methods are characterized in that the shaping of the hair is in a smoothing, preferably using a flat iron.
- a mechanical smoothing is understood according to the invention to mean stretching of the curly hair along the longest spatial extent of the hair fiber.
- the hair shaping agent may contain other ingredients. These will be below described.
- polymers which can be used with particular preference in the processes and compositions of the invention are described below.
- R is a Cp to C 30 alkyl group, a Cp to C 4 aralkyl group, a C 2 to C 6 alkenyl group or a C 2 to C 6 hydroxyalkyl group and
- n 1, 2 or 3 as the number of methylene units.
- Film-forming and / or consolidating copolymers B are known. These copolymers have at least one structural unit of the formula (B-1) and at least one structural unit of the formula (B-II) and may moreover comprise further structural units which are copolymerized by the addition of corresponding monomers during the polymerization.
- R represents a Cp to C 30 alkyl group, a Cp to C 4 aralkyl group, a C 2 - to C 6 alkenyl group or a C 2 to C 6 hydroxyalkyl group.
- Preferred groups R are, for example, -CH 3 ; -CH 2 CH 3 , -CH 2 CH 2 CH 3 , CH (CH 3 ) 2 , - (CH 2 ) 3 CH 3 , -CH 2 -CH (CH 3 ) 2 , CH (CH 3 ) CH 2 CH 3 , -C (CH 3 ) 3,
- X " represents a physiologically acceptable anion
- preferred anions are chloride, bromide, iodide, sulfate, methosulfate, ethyl sulfate, tosylate and tetrafluoroborate.
- Particularly preferred hair shaping compositions according to the invention are characterized in that they contain, as copolymer B, a copolymer B1 which
- Very particularly preferred copolymers B1 contain 10 to 30 mol%, preferably 15 to 25 mol% and in particular 20 mol% of structural units of the formula (B1) and 70 to 90 mol%, preferably 75 to 85 mol. % and in particular 80 mol .-% of structural units of the formula (B-II).
- the copolymers B1 in addition to polymer units resulting from the incorporation of said structural units of the formula (Bl) and (B-II) in the copolymer, a maximum of 5 wt .-%, preferably at most 1 wt .-%, Contain polymer units, which are due to the incorporation of other monomers.
- the copolymers B1 are composed exclusively of structural units of the formula (B-1) and (B-II) and can be represented by the general formula
- Such N-methylvinylimidazole / vinylpyrrolidone copolymers are, according to INCI nomenclature as Polyquaternium-44 and are for example available under the trade names Luviquat ® Ultra Care from BASF.
- Particularly preferred hair shaping compositions according to the invention comprise a copolymer B1 which has molecular weights within a certain range.
- hair shaping agents are preferred in which the copolymer B1 has a molecular weight of 50 to 400 kDa, preferably 100 to 300 kDa, more preferably 150 to 250 kDa and in particular 190 to 210 kDa.
- the hair shaping compositions according to the invention may also contain copolymers B2 which have as additional structural units of the formula (B-II) in which n represents the number 3.
- hair shaping agents are characterized in that they contain, as copolymer B, a copolymer B2 which
- - contains at least one further structural unit according to formula (B-II), wherein n represents 3 methylene units.
- the copolymers B2 in addition to polymer units resulting from the incorporation of said structural units of the formula (B1) and (B-II) into the copolymer, a maximum of 5 wt .-%, preferably at most 1 wt .-% , Contain polymer units due to the incorporation of other monomers.
- the copolymers B2 are composed exclusively of structural units of the formula (B-1) and (B-II) and can be represented by the general formula
- N-methylvinylimidazole / vinylpyrrolidone / vinyl caprolactam copolymers are referred to as Polyquaternium-46, according to INCI nomenclature and are obtainable for example under the trade name Luviquat Hold ® from BASF.
- Particularly preferred hair styling agents contain a copolymer B2 having molecular weights within a certain range.
- hair shaping agents are preferred in which the copolymer B2 has a molecular weight of 100 to 1000 kDa, preferably from 250 to 900 kDa, more preferably from 500 to 850 kDa and in particular from 650 to 710 kDa.
- the hair shaping compositions may also contain copolymers B3, which have as additional structural units structural units of the formula (B-II) in which n is the number 3 and further structural units from the group of vinylimidazole units and further structural units from the group of acrylamide and / or methacrylamide units.
- compositions are characterized in that they contain, as copolymer B, a copolymer B3 which
- the copolymers B3 in addition to polymer units resulting from the incorporation of said structural units of the formula (B1), (B-II), (B-III) and (B-IV) in the copolymer, a maximum of 5 Wt .-%, preferably at most 1 wt .-%, polymer units, which go back to the incorporation of other monomers.
- the copolymers B3 are composed exclusively of structural units of the formula (B-1), (B-II), (B-III) and (B-IV) and can be represented by the general formula
- N-methylvinylimidazole / vinylpyrrolidone / vinylimidazole / methacrylamide copolymers as Polyquaternium-68, according to INCI nomenclature and are obtainable for example under the trade name Luviquat ® Supreme by BASF.
- Particularly preferred hair styling agents contain a copolymer B3 having molecular weights within a certain range.
- hair shaping agents are preferred in which the copolymer B3 has a molecular weight of 100 to 500 kDa, preferably from 150 to 400 kDa, more preferably from 250 to 350 kDa and in particular from 290 to 310 kDa.
- the total amount of copolymers B based on the weight of the ready-to-use hair styling agent, 0.05 to 5 wt. -%, preferably 0, 1 to 4 wt .-% and in particular 0.25 to 3 wt .-%, is.
- preferred hair styling agents contain at least one copolymer F selected from
- MTAC Methacrylamidopropyltrimethylammonium chloride
- hair styling agents containing polymer F as copolymers of vinylpyrrolidone with methacrylamidopropyltrimethylammonium chloride are preferred (b1).
- indices m and n vary depending on the molecular weight of the polymer and should not mean that they are block copolymers. Rather, structural units can be present in the molecule in a statistically distributed manner.
- Particularly preferred hair shaping agents are characterized in that they contain, as cationic polymer f1, copolymers of methacrylamidopropyltrimethylammonium chloride (MAPTAC) with vinylpyrrolidone, which contain 40 to 95 mol%, preferably 42.5 to 90 mol%, more preferably 45 to 85 mol. % and in particular 50 to 80 mol .-% vinylpyrrolidone.
- Particularly preferred hair shaping compositions are further characterized in that the copolymers f1 have molecular weights of from 10 to 1000 kDa, preferably from 25 to 900 kDa, more preferably from 50 to 800 kDa and in particular from 100 to 750 kDa.
- copolymers f1 are preferably used within certain quantitative ranges.
- Preferred herein are hair styling compositions which, based on the weight of the ready-to-use hair styling agent, contain from 0.05 to 5% by weight, preferably from 0.1 to 4% by weight and in particular from 0.25 to 3% by weight of copolymer (s) f1 included.
- a very particularly preferred copolymer f1 is designated as Polyquaternium-28 according to the INCI nomenclature. Such a polymer is available, for example under the trade name Gafquat ® HS-100 (ISP).
- the hair styling agent may also contain polymers f2 from the group of copolymers of vinylpyrrolidone with dimethylaminoethyl methacrylate.
- indices m and n vary depending on the molecular weight of the polymer and should not mean that they are block copolymers. Rather, structural units can be present in the molecule in a statistically distributed manner.
- Particularly preferred hair shaping agents are characterized in that they contain, as cationic polymer f2, copolymers of vinylpyrrolidone with dimethylaminoethyl methacrylate containing 40 to 95 mol%, preferably 42.5 to 90 mol%, more preferably 45 to 85 mol% and in particular 50 to 80 mol .-% vinylpyrrolidone.
- Particularly preferred hair shaping agents are further characterized in that the copolymers f2 have molecular weights of from 100 to 2500 kDa, preferably from 250 to 2000 kDa, more preferably from 500 to 1750 kDa and in particular from 800 to 1500 kDa.
- the copolymers f2 be used within certain ranges.
- Preferred herein are hair styling compositions which, based on the weight of the ready-to-use hair styling agent, contain from 0.05 to 5% by weight, preferably from 0.1 to 4% by weight and in particular from 0.25 to 3% by weight of copolymer (s) f2 included.
- a most preferred copolymer f2 is referred to according to the INCI nomenclature as Polyquaternium-1 1.
- Such a polymer is available for example under the trade name Gafquat ® 755 N (ISP).
- the hair styling agents according to the invention may also contain polymers f3 from the group of copolymers of vinylpyrrolidone with dimethylaminopropylmethacrylamide and alkyldimethylpropylmethacrylamidoammonium salts.
- indices m, n and o vary depending on the molecular weight of the polymer and should not mean that they are block copolymers. Rather, structural units can be present in the molecule in a statistically distributed manner.
- Particularly preferred hair shaping agents are characterized in that they contain as cationic polymer f3 copolymers of vinylpyrrolidone with dimethylaminopropylmethacrylamide and lauryldimethylpropylmethacrylamidoammonium salts.
- Particularly preferred hair shaping agents are further characterized in that they contain as the cationic polymer f3 copolymers of vinylpyrrolidone with dimethylaminopropylmethacrylamide and Alkyldimethylpropylmethacrylamidoammoniumsalzen which 40 to 95 mol .-%, preferably 42.5 to 90 mol .-%, more preferably 45 to 85 mol. % and in particular 50 to 80 mol .-% vinylpyrrolidone.
- Very particularly preferred hair shaping compositions are furthermore characterized in that the copolymers have f3 molar masses of from 10 to 1000 kDa, preferably from 25 to 900 kDa, more preferably from 50 to 800 kDa and in particular from 100 to 750 kDa
- copolymers f3 are preferably used within certain quantitative ranges.
- Preferred herein are hair styling compositions which, based on the weight of the ready-to-use hair styling agent, contain from 0.05 to 5% by weight, preferably from 0.1 to 4% by weight and in particular from 0.25 to 3% by weight of copolymer (s) f3 included.
- a very particularly preferred copolymer f3 is designated as Polyquaternium-55 according to the INCI nomenclature. Such a polymer is available, for example under the trade name Styleze® ® W20 (ISP).
- the agents used in the process according to the invention and the agents according to the invention may contain further substances, in particular care substances.
- Preferred hair styling agents additionally comprise cationic surfactant (s), preferably in amounts of from 0.5 to 15% by weight, more preferably from 1 to 10% by weight and in particular from 1.5 to 7.5% by weight. %, in each case based on the total mean.
- Cationic surfactants of the quaternary ammonium compound type, the esterquats and the amidoamines can be used 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.
- the long alkyl chains of the above-mentioned surfactants preferably have 10 to 18 carbon atoms.
- QAV QAV with behenyl radicals, in particular those which have the name: behentrimonium chloride or bromide (docosanyltrimethylammonium chloride or Bromide) known substances.
- Other preferred QAV's have at least two behenyl residues, with QAV being particularly preferred, which are two behenyl residues on an imidazolinium backbone.
- these substances for example, under the names Genamin ® KDMP (Clariant) and Crodazosoft ® DBQ (Crodauza) are.
- Esterquats are known substances which contain both at least one ester function and at least one quaternary ammonium group as a structural element.
- Preferred esterquats 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® ®.
- 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.
- fatty substances or cosmetic oil body are fatty substances or cosmetic oil body.
- the amount used of the natural and synthetic cosmetic oil body in the hair treatment compositions is usually 0.1 to 20 wt.%, Preferably 0.2 to 10 wt .-%, and in particular 0.25 to 7.5 wt .-% based on the total Medium.
- the preferred oil bodies include in particular:
- oils examples include amaranth seed oil, apricot kernel oil, argan oil, avocado oil, babassu oil, cottonseed oil, borage seed oil, camelina oil, thistle oil, peanut oil, pomegranate seed oil, grapefruit seed oil, hemp oil, hazelnut oil, elderflower seed oil, currant seed oil, jojoba oil, cocoa butter, linseed oil, macadamia nut oil, corn oil, almond oil, marula oil , Evening primrose oil, olive oil, orange oil, palm oil, peach kernel oil, rapeseed oil, rice oil, sea buckthorn pulp oil, sea buckthorn seed oil, sesame oil, shea butter, soybean oil, sunflower oil, grape seed oil, walnut oil, wheat germ oil, rosehip oil and the liquid components of coconut oil.
- triglyceride oils such as the liquid portions of beef tallow as well as synthetic triglyceride oils.
- Preferred cosmetic agents according to the invention are characterized in that the oil body b) is a natural oil.
- the proportion by weight of the natural oil in the total weight of preferred cosmetic compositions is 0, 1 to 10 wt .-%, preferably 0.2 to 8.0 wt.% And in particular 0.4 to 5.0 wt .-%.
- liquid paraffin oils and synthetic hydrocarbons and di-n-alkyl ethers having a total of from 12 to 36 carbon atoms, in particular 12 to 24 carbon atoms, such as di-n-octyl ether, di-n-decyl ether, di-n-nonyl ether, di n-undecyl ether, di-n-dodecyl ether, n-hexyl n-octyl ether, n-octyl n-decyl ether, n-decyl n-undecyl ether, n-undecyl n-dodecyl ether and n-hexyl n-undecyl ether and di-tert-butyl ether, di-iso-pentyl ether, di-3-ethyldecyl ether, tert-butyl-n-octyl ether, iso
- the compounds are available as commercial products 1, 3-di- (2-ethyl-hexyl) -cyclohexane (Cetiol ® S), and di-n-octyl ether (Cetiol ® OE) may be preferred.
- Ester oils are to be understood as meaning the esters of C 6 - C 30 fatty acids with C 2 - C 30 fatty alcohols.
- the monoesters of the fatty acids with alcohols having 2 to 24 carbon atoms are preferred.
- isopropyl myristate IPM Rilanit ®
- isononanoic acid C16-18 alkyl ester Cetiol ® SN
- 2-ethylhexyl palmitate Cegesoft ® 24
- stearic acid-2-ethylhexyl ester (Cetiol ® 868)
- cetyl oleate glycerol tricaprylate, Kokosfettalkohol- caprinatV caprylate (Cetiol ® LC), n-butyl stearate, oleyl erucate (Cetiol ® J 600), isopropyl palmitate (Rilanit ® IPP
- Preferred cosmetic agents according to the invention are characterized in that the oil body b) is an ester oil, preferably isopropyl myristate.
- the proportion by weight of the ester oil in the total weight of preferred cosmetic agents is from 0.1 to 30% by weight, preferably from 0.2 to 27% by weight and in particular from 0.4 to 24% by weight.
- 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,
- the group of the preferred fatty alcohols includes the C 8 to C 2 2 fatty alcohols, preferably the C 10 to C 2 o fatty alcohols and in particular the C 12 to C 18 fatty alcohols.
- Preferred cosmetic agents according to the invention are characterized in that the oil body b) is a fatty alcohol.
- the proportion by weight of the fatty alcohol in the total weight of preferred cosmetic agents is 0, 1 to 10 wt .-%, preferably 0.2 to 8.0 wt.% And in particular 0.4 to 5.0 wt .-%.
- Fatty acid partial glycerides which are understood to mean monoglycerides, diglycerides and their technical mixtures. When using technical products, manufactur- due to the fact that even small amounts of triglycerides are contained.
- the partial glycerides preferably follow the formula (D4-I),
- R 3 in the R, R 2 and R 3 are 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 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 acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, Elaeostearic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
- oleic acid monoglycerides are used.
- Preferred hair shaping agents are characterized in that they additionally comprise polymer (s), preferably nonionic and / or cationic polymer (s), preferably amounts of from 0.1 to 20% by weight, more preferably of 0.2 to 15 wt .-% and in particular from 0.3 to 10 wt .-%, each based on the total agent included.
- Preferred cationic polymers are, for example
- Celquat ® quaternized cellulose derivatives, such as are available under the names of Celquat ® and Polymer JR ® commercially.
- JR® 400 are preferred quaternized cellulose derivatives
- honey for example the commercial product Honeyquat ® 50,
- cationic guar derivatives in particular those sold under the tradename Cosmedia Guar ® and Jaguar ® products,
- Such compounds are sold under the names Gafquat ® 734 and Gafquat ® 755 commercially,
- Vinylpyrrolidone vinylimidazoliummethochloride copolymers such as those offered under the names Luviquat.RTM ® FC 370, FC 550, FC 905 and HM 552,
- Polyquaternium 2 Polyquaternium 17, Polyquaternium 18, Polyquaternium 24 and Polyquaternium 27 with quaternary nitrogen atoms in the polymer main chain.
- particularly preferred 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 commercial product Honeyquat ® 50, cationic Alkylpolyglycodside according to DE-PS 44 13 686 and polymers of the type Polyquaternium-37.
- protein hydrolysates of plant, animal, marine or synthetic origin can be used as polymeric cationic care substances.
- Animal protein hydrolysates are, for example, elastin, collagen, keratin, silk and milk 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) and kerasol tm ® (Croda) sold.
- protein hydrolysates according to the invention are of maritime origin. These include, for example, collagen hydrolyzates of fish or algae as well as protein hydrolysates of mussels or pearl hydrolyzates.
- pearl extracts according to the invention are the commercial products Pearl Protein Extract BG ® or Crodarom ® Pearl.
- Cationized protein hydrolysates are also to be counted among the protein hydrolysates and their derivatives, wherein the underlying protein hydrolyzate from the animal, for example from collagen, milk or keratin, from the plant, for example from wheat, maize, rice, potatoes, soy or almonds, from marine life forms , for example from fish collagen or algae, or biotechnologically derived protein hydrolysates, may originate.
- the protein hydrolysates (P) are present in the compositions in concentrations of 0.001% by weight up to 20% by weight, preferably from 0.05% by weight up to 15% by weight and very particularly preferably in amounts of from 0.05% by weight up to 5% by weight.
- Suitable nonionic polymers are, for example:
- Vinylpyrrolidone / vinyl ester copolymers as sold, for example, under the trademark Luviskol ® (BASF).
- Luviskol ® VA 64 and Luviskol ® VA 73, each vinylpyrrolidone / vinyl acetate copolymers, are also preferred nonionic polymers.
- Cellulose ethers such as hydroxypropyl cellulose, hydroxyethyl cellulose and hydroxypropylcellulose Methylhy-, as sold for example under the trademark Culminal® ® and Benecel ® (AQUALON) and Natrosol ® grades (Hercules).
- Starch and its derivatives in particular starch, such as Structure XL ® (National Starch), a multifunctional, salt-tolerant starch;
- Siloxanes These siloxanes can be both water-soluble and water-insoluble. Both volatile and nonvolatile siloxanes are suitable, nonvolatile siloxanes being understood as meaning those compounds whose boiling point is above 200 ° C. under normal pressure.
- Preferred siloxanes are polydialkylsiloxanes, such as, for example, polydimethylsiloxane, polyalkylarylsiloxanes, such as, for example, polyphenylmethylsiloxane, ethoxylated polydialkylsiloxanes and polydialkylsiloxanes which contain amine and / or hydroxyl groups.
- the preparations used contain a plurality, in particular two, different polymers of the same charge and / or in each case an ionic and an amphoteric and / or nonionic polymer.
- these may contain further ingredients. These are described below.
- the agents according to the invention and the agents used in the methods according to the invention therefore contain surfactants.
- Suitable anionic surfactants are, in particular, alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, sulfosuccinic acid mono- and dialkyl esters having 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkylpolyoxyethyl ester with 8 to 18 C atoms in the alkyl group and 1 to 6 oxyethyl groups, Monoglycerdisulfate, alkyl and Alkenyletherphosphate and protein fatty acid condensates.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as N-alkyl-N, N-dimethylammonium glycinates, for example cocoalkyl dimethylammonium glycinate, N-acylaminopropyl N, N-dimethylammonium glycinates, for example cocoacylaminopropyl dimethylammonium glycinate, and 2-alkyl 3-carboxymethyl-3-hydroxyethyl-imidazolines having in each case 8 to 18 C atoms in the alkyl or acyl group, and also the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
- a preferred zwitterionic surfactant is the fatty acid amide derivative known by the INCI name Cocamidopropyl Betaine.
- ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids each having about 8 to 24 C Atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethylaminopropionate and the d 2 -C 8 -acylsarcosine.
- the preferred nonionic surfactants are the alkylene oxide addition products of saturated linear fatty alcohols and fatty acids having in each case 2 to 30 moles of ethylene oxide per mole of fatty alcohol or fatty acid. Preparations having excellent properties are also obtained if they contain fatty acid esters of ethoxylated glycerol as nonionic surfactants.
- the alkyl radical R contains 6 to 22 carbon atoms and may be both linear and branched. Preference is given to primary linear and methyl-branched in the 2-position aliphatic radicals.
- Such alkyl radicals are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl. Particularly preferred are 1-octyl, 1-decyl, 1-lauryl, 1-myristyl.
- oxo-alcohols compounds with an odd number of carbon atoms in the alkyl chain predominate.
- nonionic surfactants are the sugar surfactants. These may preferably be contained in the agents used according to the invention in amounts of 0.1 to 20% by weight, based on the total agent. Amounts of 0.5-15% by weight are preferred, and most preferred are amounts of 0.5-7.5% by weight.
- the agents used in the process according to the invention may contain emulsifiers.
- the agents used in the process according to the invention preferably contain the emulsifiers in amounts of 0.1-25% by weight, in particular 0.5-15% by weight, based on the total agent.
- the compositions used in the process according to the invention may preferably contain at least one nonionic emulsifier having an HLB value of 8 to 18. Nonionic emulsifiers having an HLB value of 10 to 15 may be particularly preferred according to the invention.
- the agents used in the process according to the invention may also contain plant extracts.
- plant extracts are particularly preferred.
- penetration aids and / or swelling agents are contained in the agents used in the method according to the invention.
- agents used in the method according to the invention include, for example, urea and urea derivatives, guanidine and its derivatives, arginine and its derivatives, water glass, imidazole and its derivatives, histidine and its derivatives, benzyl alcohol, glycerol, glycol and glycol ethers, propylene glycol and propylene glycol ethers, for example propylene glycol monoethyl ether, carbonates, bicarbonates, Diols and triols, and in particular 1, 2-diols and 1, 3-diols such as 1, 2-propanediol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-dodecanediol, 1, 3-propanediol, 1 , 6-hexanediol, 1, 5-pentanediol, 1, 4-
- oxidizing agents eg. For example, sodium bromate, potassium bromate, hydrogen peroxide, and the usual stabilizers for stabilizing aqueous hydrogen peroxide stabilizers.
- the pH of such aqueous ⁇ O 2 preparations which usually contain about 0.5 to 15% by weight, usually about 0.5 to 3% by weight, of H 2 O 2, is preferably from 2 to 6, in particular 2 to 4; it is adjusted by inorganic acids, preferably phosphoric acid.
- Bromate-based fixatives are usually used in concentrations of from 1 to 10% by weight and the pH of the solutions is adjusted to 4 to 7.
- enzymatic-based fixatives for example peroxidases
- the fixing agents preferably contain at least 50% by weight of water.
- Another object of the present invention is a hair styling kit containing
- a preferred subject of the present invention is a process for the permanent transformation of keratin-containing fibers, in particular human hair, in which
- the deformation agent acts for a contact time Z1
- a fixing agent containing at least one oxidizing agent applied to the fibers and rinsed again after a contact Z2.
- the fixing agent contains at least one of the abovementioned polymers, preferably in amounts such that the total polymer content of the fixing agent is 1 to 15% by weight, preferably 2.5 to 12.5% by weight. , more preferably 4 to 10 wt .-% and in particular 5 to 8 wt .-% is.
- the exposure time of the fixing agent is preferably within narrower ranges.
- preferred processes according to the invention are characterized in that the exposure time Z2 is 1 to 60 minutes, preferably 2 to 50 minutes, more preferably 5 to 40 minutes and in particular 10 to 30 minutes.
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE201110089573 DE102011089573A1 (en) | 2011-12-22 | 2011-12-22 | Deformation agent for keratinic fibers and hair shaping procedures |
PCT/EP2012/073168 WO2013092077A2 (en) | 2011-12-22 | 2012-11-21 | Shaping agent for keratinous fibres and hair shaping method |
Publications (1)
Publication Number | Publication Date |
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EP2793830A2 true EP2793830A2 (en) | 2014-10-29 |
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EP12790878.8A Withdrawn EP2793830A2 (en) | 2011-12-22 | 2012-11-21 | Shaping agent for keratinous fibres and hair shaping method |
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US (1) | US20150114424A1 (en) |
EP (1) | EP2793830A2 (en) |
DE (1) | DE102011089573A1 (en) |
WO (1) | WO2013092077A2 (en) |
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DE102013225916A1 (en) | 2013-12-13 | 2015-06-18 | Henkel Ag & Co. Kgaa | Hair straightening with carbocysteine |
Family Cites Families (12)
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GB654077A (en) * | 1946-10-31 | 1951-06-06 | Monsanto Chemicals | Improvements in or relating to processes of finishing textile fabrics |
GB1067903A (en) * | 1966-04-26 | 1967-05-03 | Internat Synthetic Rubber Comp | Improvements relating to the treatment of wool |
US4387090A (en) * | 1980-12-22 | 1983-06-07 | The Procter & Gamble Company | Hair conditioning compositions |
EP0196896A3 (en) * | 1985-03-27 | 1987-02-04 | Nitto Denko Corporation | Method and composition for removal of hair from skin |
DE3631991A1 (en) * | 1986-09-20 | 1988-03-31 | Wella Ag | MEANS AND METHOD FOR PERMANENT HAIR DEFORMING |
DE4413686C2 (en) | 1994-04-20 | 1996-10-24 | Henkel Kgaa | Cationic sugar surfactants, process for their preparation and their use |
DE19756454C1 (en) | 1997-12-18 | 1999-06-17 | Henkel Kgaa | Surface-active compositions, especially cosmetics, containing glycerol carbonate as emulsifier |
JP2001139438A (en) * | 1999-11-12 | 2001-05-22 | Kao Corp | Premix composition |
ITMI20030385A1 (en) * | 2003-03-04 | 2004-09-05 | Intercos Italia S P A Ora Intercos S P A | COSMETIC COMPOSITION INCLUDING POLYISOPRENE. |
DE102005061021A1 (en) * | 2005-12-19 | 2007-06-21 | Henkel Kgaa | Permanent shaping of keratin fibers, useful especially for human hair, by treatment with an emulsion containing a keratin-reducing agent, shaping, then treatment with oxidizing agent |
FR2939670B1 (en) * | 2008-12-16 | 2013-07-05 | Oreal | PERMANENT DEFORMATION METHOD USING A HEATING MECHANICAL POWER-ON DEVICE |
DE102009047528A1 (en) * | 2009-12-04 | 2011-06-09 | Henkel Ag & Co. Kgaa | Use of ester oil in permanent hair shaping processes |
-
2011
- 2011-12-22 DE DE201110089573 patent/DE102011089573A1/en not_active Withdrawn
-
2012
- 2012-11-21 WO PCT/EP2012/073168 patent/WO2013092077A2/en active Application Filing
- 2012-11-21 EP EP12790878.8A patent/EP2793830A2/en not_active Withdrawn
- 2012-11-21 US US14/367,808 patent/US20150114424A1/en not_active Abandoned
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US20150114424A1 (en) | 2015-04-30 |
WO2013092077A2 (en) | 2013-06-27 |
WO2013092077A3 (en) | 2014-06-05 |
DE102011089573A1 (en) | 2013-06-27 |
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