WO1999037278A1 - Composition pour la coloration de fibres keratiniques depourvue d'ammoniaque - Google Patents
Composition pour la coloration de fibres keratiniques depourvue d'ammoniaque Download PDFInfo
- Publication number
- WO1999037278A1 WO1999037278A1 PCT/FR1999/000114 FR9900114W WO9937278A1 WO 1999037278 A1 WO1999037278 A1 WO 1999037278A1 FR 9900114 W FR9900114 W FR 9900114W WO 9937278 A1 WO9937278 A1 WO 9937278A1
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- WIPO (PCT)
- Prior art keywords
- composition according
- quaternized
- copolymer
- acrylic
- weight
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000004043 dyeing Methods 0.000 title claims abstract description 9
- 238000004040 coloring Methods 0.000 claims abstract description 32
- 229920001577 copolymer Polymers 0.000 claims abstract description 30
- 230000001590 oxidative effect Effects 0.000 claims abstract description 15
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 13
- 239000002243 precursor Substances 0.000 claims abstract description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000003113 alkalizing effect Effects 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 6
- 210000004209 hair Anatomy 0.000 claims description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
- 239000000835 fiber Substances 0.000 claims description 22
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- -1 polyoxyethylenes Polymers 0.000 claims description 11
- 102000011782 Keratins Human genes 0.000 claims description 9
- 108010076876 Keratins Proteins 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 239000002610 basifying agent Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical group CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940100459 steareth-20 Drugs 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 230000009965 odorless effect Effects 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- 239000000975 dye Substances 0.000 description 20
- 239000002453 shampoo Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 241001070941 Castanea Species 0.000 description 3
- 235000014036 Castanea Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 230000037308 hair color Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Natural products CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 210000004761 scalp Anatomy 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical class NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 1
- NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ICIDSZQHPUZUHC-UHFFFAOYSA-N 2-octadecoxyethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCO ICIDSZQHPUZUHC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920000289 Polyquaternium Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 229940056318 ceteth-20 Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N propylene glycol methyl ether Substances COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229940079864 sodium stannate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- A61Q5/10—Preparations for permanently dyeing the hair
-
- 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
- A61K8/22—Peroxides; Oxygen; Ozone
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
Definitions
- composition for dyeing keratin fibers without ammonia
- the present invention relates to a composition devoid of ammonia for the coloring of keratin fibers.
- the only hair dyeing processes capable of covering the hair perfectly and durably are the dyeing processes by oxidation which result in dyes called permanent dyes.
- the dye precursors which are aromatic compounds belonging to the families of diamines, aminophenols (or aminonaphthols) and phenols (or naphthols) are oxidized in the presence of hydrogen peroxide and an alkaline base, preferably ammonia.
- these precursors are transformed into very reactive intermediate radicals which couple together to form, during the second step of oxidative condensation, colored polymers which can be fixed firmly in the keratin fiber.
- hydrogen peroxide has two functions: to discolor the pigments in place in order to avoid variations in dyeing resulting from the initial color of the hair, and to trigger the oxidative process of the dyes.
- the ammonia facilitates the dissolution of the dyes, and by alkalizing the medium, promotes the bleaching action of the peroxide by participating in the release of active oxygen.
- ammonia also acts on the swelling of the fiber, causing the scales to open. It thus facilitates the penetration of dye precursors and ensures a homogeneous distribution of pigments up to the heart of the fiber.
- This permanent coloring technique has always given excellent results, both with regard to the coverage of white hair (close to 100%), the range of shades offered, and the resistance to washing of the coloring obtained. Indeed, this type of coloring which irreversibly modifies the pigmentation of the hair, resists very well to successive shampoos.
- Ammonia is a strong, highly volatile base which gives off an unpleasant and suffocating odor during the preparation of the product and during application.
- the evaporation of ammonia poses problems for maintaining a constant alkalinity during the manufacture of the product. This is why, in recent years, new compositions of so-called “tone-on-tone” or almost permanent, non-lightening oxidation dyes have appeared on the market. These new types of coloring involve the same dye precursors as traditional oxidation coloring, but very often ammonia is replaced by monoethanolamine or amino methylpropanol, and the peroxide content of the oxidant is reduced approximately by half,
- Acrylic-itaconic copolymers are used, at high concentrations, as thickeners in coloring compositions.
- the acrylic-dimethyl diallyl ammonium chloride copolymer is used in formulations of shampoo. However, no compositions containing these two compounds are known.
- the Applicant has shown that it is possible to obtain such a coloration thanks to the use in the coloration compositions of a ternary complex.
- the present invention therefore relates to a composition for dyeing keratin fibers, and in particular hair, devoid of ammonia, comprising an oxidizing compound, dye precursors and a non-volatile and odorless alkalizing agent, characterized in that it also includes:
- quaternized polymer a quaternized copolymer of dimethyldiallyl ammonium and of acrylic acid, hereinafter called quaternized polymer
- the quaternized copolymer, the quaternized silicone and the acrylic-itaconic copolymer form a complex within the composition.
- This ternary complex in itself constitutes an object of the present invention.
- the quaternized copolymer of dimethyldiallylammonium and of acrylic acid can correspond to formula I in appendix, in which x can be included between 1 and 1000, preferably between 1 and
- y and z can be independently between 0 and 1000, preferably between 0 and 100.
- the quaternized polymer is preferably a polyquaternium, such as a polyquaternium-22 or a polyquatemium-39. These compounds can be present at concentrations of between 0.1 and 1.5% by weight of the composition.
- a composition according to the present invention will comprise from 0.5 to 1% by weight of polyquaternium-22.
- the quaternized silicone can be a polyquaternized polydimethylsiloxane corresponding to formula II in the appendix, in which Ri represents a C 6 to C 2 alkyl group and n is between 1 and 1000, preferably between 1 and 100, such as a diquaternized polydimethylsiloxane.
- the group Ri represents one or more alkyl groups derived from coconut oil.
- the acrylic-itaconic copolymer is substituted by one or more C 6 to C 2 o alkyl groups, at least one of which is polyoxyethylenated, and corresponds to the general formula III, in the appendix, in which R 2 and R ' 2 represent alkyl groups, x ', y' and z 'are whole numbers between 1 and 1000 and preferably between 1 and 100, and n' is between 1 and 100, preferably between 10 and 30, and again more preferably is 20.
- R 2 represents an ester of acrylic and / or methacrylic acid, in particular an ethyl, butyl or methyl ester and R ′ 2 a stearyl or cetyl radical.
- Such copolymers advantageously have a molecular weight of between 10 5 and 10 7 , and preferably close to 10 6 .
- the concentration of acrylic-itaconic copolymer can be between approximately 0.1 and 10% by weight of the composition.
- a copolymer consists of a mixture of acrylate-steareth-20 or ceteth-20-itaconates copolymers, included in amounts of 0.3 to 4% by weight of the composition.
- the composition according to the present invention can contain from 0.2 to 12% by weight, and preferably from 0.8 to 5% by weight of the ternary complex formed by the three compounds identified above.
- the three components of the complex are included in amounts making it possible to obtain a synergistic effect. These quantities correspond to the preferential ranges indicated above.
- the composition according to the present invention comprises at least: - between approximately 0.1 and 1.5% by weight of a quaternized copolymer,
- composition according to the invention may also comprise between 2 and 30%, and advantageously between 10 and 25% by weight of an alcohol. or of a mixture of preferably C 2 to C 8 alcohols, such as ethanol, propanol or isopropanol.
- Dye precursors include bases and couplers.
- the primary bases or intermediates can be aromatic amines, diaminophenols and aminophenols in which the NH 2 and OH groups are in the ortho or para position with respect to each other. They are responsible for the deep nuance and can couple on themselves to form very colored pigments. They can be in particular para-phenylenediamine (pPD), ortho-aminophenol (oAP), para-methylaminophenol (pMAP), para-aminophenol (pAP), para-toluylenediamine (pTD) and / or N- phenyl-para-phenylenediamine (NpPD).
- the couplers or modifiers can be metadiamines, metaaminophenols, polyphenols or naphthols. Taken individually or in combination with one another, they give only a very weak coloration; when coupled with a base, they modify the shade.
- mAP meta-aminophenol
- R resorcinol
- 1-naphthol (1-N) meta-phenylenediamine
- mPD meta-phenylenediamine
- pAOC para-aminoorthocresol
- Hq hydroquinone
- the overall formulation must be adapted to the desired coloristic result. Most often, a plurality of base-coupler associations is used.
- the composition contains from 1 to 30% by weight of an basifying agent which can be in particular, amino methylpropanol, monoethanolamine, diethanolamine, triethanolamine, or mixtures thereof, and preferably, from 5 to 20% monoethanolamine.
- an basifying agent which can be in particular, amino methylpropanol, monoethanolamine, diethanolamine, triethanolamine, or mixtures thereof, and preferably, from 5 to 20% monoethanolamine.
- composition may also contain various usual adjuvants for oxidation colorations.
- adjuvants can be natural or synthetic fatty amines, oxyethylene or polyglycerolated; oxyethylenated natural or synthetic fatty alcohols or polyglycerolated; anionic, nonionic, cationic or amphoteric surfactants; solvents, sequestering agents and perfumes.
- the oxyethylenated fatty amines used can be tertiary amines consisting of an alkyl group derived from fatty acids having 12 to 18 carbon atoms, and two polyoxyethylenated groups linked to the nitrogen atom. These fatty amines can be used at concentrations of 5 to 20% and preferably from 10 to 20%.
- the natural or synthetic, oxyethylenated or polyglycerolated fatty alcohols used can be oleic, lauric, myristic, cetyl or stearyl alcohol. These fatty alcohols can be used at concentrations of 1 to 25%, and preferably from 3 to 15%.
- the surfactants used can be anionic, cationic, nonionic or amphoteric surfactants. They can be used at concentrations of 2 to 20%, and preferably 5 to 15%.
- the solvents which can be used alone or as a mixture can be ethyl alcohol, propyl or isopropyl alcohol and glycols such as propylene glycol, diethylene glycol, butyl glycol, hexylene glycol and diethylene glycol monoethylether. They can be used at concentrations of 5 to 30%, and preferably from 10 to 20%.
- the pH of the composition can be between 7 and 11 and preferably between 8.5 and 10.5.
- the composition for coloring according to the invention is conventionally obtained by adding an oxidant to the rest of the components in a weight ratio of 1: 1.
- the oxidant may in particular be a solution of hydrogen peroxide with a concentration of between 1.5 and 12%, preferably between 6 and 9%, in which case the final concentration in the composition is between 0.75 and 6%, and preferably between 3 and 4.5%.
- This composition makes it possible, despite the absence of ammonia, to color the hair with a covering and a strength greater than that of the compositions already known. It allows to combine the softness and the comfort of a coloring without ammonia and to obtain coloristic results comparable to those of a permanent coloring with ammonia.
- this composition avoids the drawbacks linked to the presence of ammonia and makes it possible to cover gray hair perfectly and durably.
- the colors cover white hair at a rate close to 100%, without overloading on the sensitized areas and show very good washing stability.
- the composition according to the invention makes it possible to obtain natural shades. The reflections are more intense on the day of coloring and do not lose their radiance as the shampoos.
- One hypothesis that can be formulated, without the depositor being bound to it, is that the complex formed improves the solid fixation of the dyes in the fiber.
- the cationic compounds included in this composition would have a protective role during the oxidative reaction and a conditioner of the surface of the fibers.
- the hair keeps after coloring a soft and silky touch. They retain the suppleness, firmness, elasticity and shine of healthy hair.
- the composition further facilitates the disentangling and styling of the hair after treatment. It is also devoid of aggressiveness vis-à-vis the scalp of the majority of individuals treated.
- composition according to the present invention may be in the form of a liquid, a gel, a gelling liquid or a cream.
- gelling compositions are preferred for their ease of application and the brightness of the shades obtained.
- the gelling liquids can be prepared either from polyoxyethylene or polyglycerolated nonionic compounds and from solvents, or from soaps of liquid fatty acids and solvents.
- composition according to the present invention lies in the possibility of avoiding the use of polyoxyethylenated alkylphenols in the support to form a gel by dilution.
- These gelling compounds formerly widely used in this type of composition, are today considered to be very little biodegradable and toxic to aquatic life. They are said to have a hormone-like activity that can disrupt the development of river fauna and they are today threatened with prohibition.
- composition which is the subject of the present invention can be produced by mixing, in a manner known to those skilled in the art, the various constituents which it comprises.
- composition according to the present invention can be used in a process for coloring keratin fibers, and in particular hair, comprising the following steps:
- compositions A and B are mixed, in equal parts, in a non-metallic bowl or an applicator bottle.
- suppliers of the products, as well as possibly the names under which they are marketed are indicated in brackets.
- composition A gelable support of formula (% by weight): - acrylic copolymer-dimethyl diallyl ammonium chloride (MERQUAT 280 - Calgon- Chemviron) 0.8%
- Composition B oxidizing solution 20 volumes, of formula (% er weight):
- the gel obtained is applied to the hair with a brush and left on the hair for approximately 30 minutes. We rinse.
- composition A gelable support of formula (% by weight):
- Composition B identical to Example 1
- the coverage of white hair by the brown shade composition containing the acrylo-cationic complex according to Example 1 is compared to the coverage by a similar composition but not containing said complex. It is quantified by image analysis on cross sections of locks containing 80% white hair, having undergone coloring and then six successive shampoos (sh). Cross sections of a few tens of ⁇ m 15
- the coloring composition containing the complex covers 96% of white hair before shampooing against 78% for the composition without complex, an efficiency gain of 18%. After six shampoos (sh) the composition with complex still covers 88% of white hair against 71% for the composition without complex. These results demonstrate a lasting efficiency gain for white hair coverage of 17% thanks to the acrylo-cationic complex.
- EXAMPLE 4 Resistance to shampooing of the coloring according to the invention.
- the resistance of the coloration to successive shampoos is quantified by measuring the% of reflected light (luminance) on woolen fabrics which have undergone a coloration of chestnut shade using a composition containing or not containing the acrylic cation complex. in alcoholic solution.
- the measurements are carried out using a MINOLTA CR 210 colorimeter (coordinates x, y, Y) on woolen fabrics after coloring followed by four successive shampoos with a specific shampoo for colored hair in 10% aqueous solution.
- the protective effect of the acrylo-cationic complex is quantified by measuring the mechanical properties (elasticity modulus) of the hair after dyeing using a composition containing or not containing the acrylo-cationic complex in alcoholic solution.
- the elasticity module of a wick is obtained by measuring the slope of the force / elongation curve (in N /% elongation).
- the ratio of the two modules measured in the presence and absence of the complex makes it possible to evaluate its effect on the mechanical properties of the hair. The results are shown in Table 3.
- composition according to the invention makes it possible to color the hair with very satisfactory results despite the absence of ammonia. It offers the color performance of a true oxidation dye while providing the comfort and softness of an ammonia-free coloring.
- the presence of the acrylo-cationic complex promotes the setting of dyes, which results in an improvement in the coverage of gray hair and a better solidity of the dye on successive washings.
- the cationic nature of the complex gives it good substantivity with respect to keratin, which allows it to protect the hair during treatment and to preserve its mechanical properties. After coloring, the hair is flexible, easily detangled and has a very soft feel. The shades are bright and retain their shine for a long time as you shampoo.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/600,834 US6423101B1 (en) | 1998-01-23 | 1999-01-20 | Ammonia-free composition for dyeing keratinous fibres |
AU20610/99A AU754260B2 (en) | 1998-01-23 | 1999-01-20 | Ammonia-free composition for dyeing keratinous fibres |
EP99900972A EP1047385A1 (fr) | 1998-01-23 | 1999-01-20 | Composition pour la coloration de fibres keratiniques depourvue d'ammoniaque |
CA002319266A CA2319266A1 (fr) | 1998-01-23 | 1999-01-20 | Composition pour la coloration de fibres keratiniques depourvue d'ammoniaque |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR98/00738 | 1998-01-23 | ||
FR9800738A FR2773992B1 (fr) | 1998-01-23 | 1998-01-23 | Composition pour la coloration de fibres keratiniques, depourvue d'ammoniaque |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999037278A1 true WO1999037278A1 (fr) | 1999-07-29 |
Family
ID=9522107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1999/000114 WO1999037278A1 (fr) | 1998-01-23 | 1999-01-20 | Composition pour la coloration de fibres keratiniques depourvue d'ammoniaque |
Country Status (6)
Country | Link |
---|---|
US (1) | US6423101B1 (fr) |
EP (1) | EP1047385A1 (fr) |
AU (1) | AU754260B2 (fr) |
CA (1) | CA2319266A1 (fr) |
FR (1) | FR2773992B1 (fr) |
WO (1) | WO1999037278A1 (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1048290A3 (fr) * | 1999-04-30 | 2001-05-02 | Bristol-Myers Squibb Company | Teinture d'oxydation pour les cheveux avec des propriétés conditionnantes et une déposition améliorée de la couleur |
WO2002000177A3 (fr) * | 2000-06-26 | 2002-05-10 | Henkel Kgaa | Systeme epaississant |
FR2817467A1 (fr) * | 2000-12-04 | 2002-06-07 | Oreal | Composition de teinture pour fibres keratiniques comprenant un polymere associatif et un polymere a motifs acrylamide, halogenure de dialkyldiallylammonium et acide carboxylique vinylique |
AU2002302544B9 (en) * | 2001-04-27 | 2002-11-11 | Henkel Kommanditgesellschaft Auf Aktien | Active ingredient combinations for hair-dyeing agents |
EP1287810A1 (fr) * | 2001-08-31 | 2003-03-05 | Wella Aktiengesellschaft | Gel pour traitement des cheveux comprenant copolymère acide itaconique monoester/acrylat |
DE19921962C2 (de) * | 1999-05-12 | 2003-10-23 | Wella Ag | Mittel und Verfahren zum oxidativen Färben von Haaren |
WO2009024362A1 (fr) * | 2007-08-20 | 2009-02-26 | Henkel Ag & Co. Kgaa | Agents de traitement capillaires contenant un dérivé d'acide acylaminé, une hydroxyalkylamine et une 2-(2-hydroxyéthyle)-p-phénylènediamine |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2803195B1 (fr) * | 1999-12-30 | 2002-03-15 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant un polymere epaississant comportant au moins une chaine grasse et un alcool gras mono-ou poly-glycerole |
FR2803198B1 (fr) * | 1999-12-30 | 2003-09-26 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant deux polyammonium quaternaires particuliers |
US6558654B2 (en) | 2000-04-11 | 2003-05-06 | Mclaughlin Gerald | Composition and method for whitening teeth |
DE102004018723A1 (de) * | 2004-04-17 | 2005-11-03 | Wella Ag | Itaconsäuremonoester/Acrylat Copolymer und Polystyrolsulfonat enthaltende Haarbehandlungsmittel |
DE102004052480A1 (de) * | 2004-10-28 | 2006-05-04 | Henkel Kgaa | Reduktionsmittel-haltiges Mittel zum Färben von keratinhaltigen Fasern |
CA2557429A1 (fr) * | 2005-08-26 | 2007-02-26 | Farouk Systems Inc. | Composition et methode d'application capillaire de rayonnement infrarouge et de particules a charge ionique |
JP2007302736A (ja) * | 2006-05-09 | 2007-11-22 | Kawaken Fine Chem Co Ltd | 塩素捕捉剤およびそれを含有する化学剤 |
EP2018842A1 (fr) * | 2007-07-26 | 2009-01-28 | KPSS-Kao Professional Salon Services GmbH | Composition de conditionnement et de coloration pour les cheveux |
DE102007046628A1 (de) * | 2007-09-27 | 2009-04-02 | Henkel Ag & Co. Kgaa | Haarfärbeverfahren mit oxidativer Vorbehandlung |
DE102009029548A1 (de) * | 2009-09-17 | 2011-03-24 | Henkel Ag & Co. Kgaa | Schonende Färbe- und Aufhellmittel mit verbesserter Aufhellleistung |
FR2966725B1 (fr) * | 2010-11-02 | 2013-02-22 | Oreal | Composition de coloration a faible teneur en ammoniaque |
EP2476407A1 (fr) | 2011-01-18 | 2012-07-18 | The Procter & Gamble Company | Procédés pour préparer des colorations des cheveux |
EP2476405A1 (fr) * | 2011-01-18 | 2012-07-18 | The Procter & Gamble Company | Compositions de coloration capillaire avec un agent alcalisant sans ammoniac |
EP2898874A1 (fr) * | 2011-09-12 | 2015-07-29 | The Procter and Gamble Company | Procédé de coloration capillaire |
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EP0593038A1 (fr) * | 1992-10-13 | 1994-04-20 | Combe Incorporated | Composition colorante pour la coloration graduelle des cheveux par oxydation à l'air, et procédé utilisant cette composition |
DE19527121A1 (de) * | 1995-07-25 | 1997-01-30 | Henkel Kgaa | Oxidationsfärbemittel |
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FR2769217B1 (fr) * | 1997-10-03 | 2000-03-17 | Oreal | Composition oxydante et utilisations pour la teinture, pour la deformation permanente ou pour la decoloration des fibres keratiniques |
US5849042A (en) * | 1997-11-19 | 1998-12-15 | Bristol-Myers Squibb | Hair dye compositions containing 2,3 dialkyl-4-aminophenol and a 2-alkyl-1-naphthol |
-
1998
- 1998-01-23 FR FR9800738A patent/FR2773992B1/fr not_active Expired - Fee Related
-
1999
- 1999-01-20 EP EP99900972A patent/EP1047385A1/fr not_active Withdrawn
- 1999-01-20 US US09/600,834 patent/US6423101B1/en not_active Expired - Fee Related
- 1999-01-20 CA CA002319266A patent/CA2319266A1/fr not_active Abandoned
- 1999-01-20 WO PCT/FR1999/000114 patent/WO1999037278A1/fr not_active Application Discontinuation
- 1999-01-20 AU AU20610/99A patent/AU754260B2/en not_active Ceased
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GB2188948A (en) * | 1986-04-10 | 1987-10-14 | Oreal | Cosmetic compositions for dyeing or for bleaching hair |
EP0593038A1 (fr) * | 1992-10-13 | 1994-04-20 | Combe Incorporated | Composition colorante pour la coloration graduelle des cheveux par oxydation à l'air, et procédé utilisant cette composition |
DE19527121A1 (de) * | 1995-07-25 | 1997-01-30 | Henkel Kgaa | Oxidationsfärbemittel |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1048290A3 (fr) * | 1999-04-30 | 2001-05-02 | Bristol-Myers Squibb Company | Teinture d'oxydation pour les cheveux avec des propriétés conditionnantes et une déposition améliorée de la couleur |
DE19921962C2 (de) * | 1999-05-12 | 2003-10-23 | Wella Ag | Mittel und Verfahren zum oxidativen Färben von Haaren |
WO2002000177A3 (fr) * | 2000-06-26 | 2002-05-10 | Henkel Kgaa | Systeme epaississant |
WO2002045674A1 (fr) * | 2000-12-04 | 2002-06-13 | L'oreal | Composition de teinture pour fibres keratiniques comprenant un polymere associatif et un polymere a motifs acrylamide, halogenure de dialkyldiallylammonium, et acide carboxylique vinylique |
FR2817467A1 (fr) * | 2000-12-04 | 2002-06-07 | Oreal | Composition de teinture pour fibres keratiniques comprenant un polymere associatif et un polymere a motifs acrylamide, halogenure de dialkyldiallylammonium et acide carboxylique vinylique |
US7364594B2 (en) | 2000-12-04 | 2008-04-29 | L'oreal S.A. | Dyeing composition for keratinous fibres comprising an associative polymer and a polymer with acrylamide units, dialkyldiallylammonium halide, and vinylic carboxylic acid |
AU2002302544B9 (en) * | 2001-04-27 | 2002-11-11 | Henkel Kommanditgesellschaft Auf Aktien | Active ingredient combinations for hair-dyeing agents |
WO2002087515A3 (fr) * | 2001-04-27 | 2003-10-30 | Hans Schwarzkopf & Henkel Gmbh | Combinaison de principes actifs a effet traitant pour colorants capillaires |
JP2004529933A (ja) * | 2001-04-27 | 2004-09-30 | ハンス・シュヴァルツコプフ・ウント・ヘンケル・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンディットゲゼルシャフト | 毛髪染色剤用の活性成分混合物 |
AU2002302544B2 (en) * | 2001-04-27 | 2007-02-01 | Henkel Kommanditgesellschaft Auf Aktien | Active ingredient combinations for hair-dyeing agents |
US7179303B2 (en) | 2001-04-27 | 2007-02-20 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Active ingredient combinations for hair-dyeing agents |
JP2009051857A (ja) * | 2001-04-27 | 2009-03-12 | Henkel Ag & Co Kgaa | 毛髪染色剤用の活性成分混合物 |
EP1287810A1 (fr) * | 2001-08-31 | 2003-03-05 | Wella Aktiengesellschaft | Gel pour traitement des cheveux comprenant copolymère acide itaconique monoester/acrylat |
US6716455B2 (en) | 2001-08-31 | 2004-04-06 | Wella Aktiengesellschaft | Hair treatment gels containing itaconic acid monoester/acrylate copolymer |
WO2009024362A1 (fr) * | 2007-08-20 | 2009-02-26 | Henkel Ag & Co. Kgaa | Agents de traitement capillaires contenant un dérivé d'acide acylaminé, une hydroxyalkylamine et une 2-(2-hydroxyéthyle)-p-phénylènediamine |
Also Published As
Publication number | Publication date |
---|---|
AU754260B2 (en) | 2002-11-07 |
EP1047385A1 (fr) | 2000-11-02 |
CA2319266A1 (fr) | 1999-07-29 |
US6423101B1 (en) | 2002-07-23 |
FR2773992A1 (fr) | 1999-07-30 |
AU2061099A (en) | 1999-08-09 |
FR2773992B1 (fr) | 2000-06-16 |
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