WO2002005768A1 - Agents de pretraitement pour colorants capillaires acides - Google Patents
Agents de pretraitement pour colorants capillaires acides Download PDFInfo
- Publication number
- WO2002005768A1 WO2002005768A1 PCT/JP2001/006033 JP0106033W WO0205768A1 WO 2002005768 A1 WO2002005768 A1 WO 2002005768A1 JP 0106033 W JP0106033 W JP 0106033W WO 0205768 A1 WO0205768 A1 WO 0205768A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hair
- pretreatment agent
- acidic
- dye
- hair dye
- Prior art date
Links
- 239000000118 hair dye Substances 0.000 title claims abstract description 99
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 91
- 230000002378 acidificating effect Effects 0.000 title claims abstract description 82
- 229920000642 polymer Polymers 0.000 claims abstract description 25
- 229920006317 cationic polymer Polymers 0.000 claims abstract description 14
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 6
- 229920002873 Polyethylenimine Polymers 0.000 claims description 40
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 25
- 239000004202 carbamide Substances 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 abstract description 36
- 210000004209 hair Anatomy 0.000 description 117
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- WVOXLKUUVCCCSU-ZPFDUUQYSA-N Pro-Glu-Ile Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(O)=O WVOXLKUUVCCCSU-ZPFDUUQYSA-N 0.000 description 32
- 229920001601 polyetherimide Polymers 0.000 description 31
- 230000000052 comparative effect Effects 0.000 description 27
- 238000000034 method Methods 0.000 description 18
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- -1 polyvinylamine Polymers 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000980 acid dye Substances 0.000 description 7
- 238000001000 micrograph Methods 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CUZKCNWZBXLAJX-UHFFFAOYSA-N 2-phenylmethoxyethanol Chemical compound OCCOCC1=CC=CC=C1 CUZKCNWZBXLAJX-UHFFFAOYSA-N 0.000 description 2
- VFKZECOCJCGZQK-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCO VFKZECOCJCGZQK-UHFFFAOYSA-M 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- 102000011782 Keratins Human genes 0.000 description 2
- 108010076876 Keratins Proteins 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229920006322 acrylamide copolymer Polymers 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 230000003766 combability Effects 0.000 description 2
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 210000004517 glycocalyx Anatomy 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- AKQXQLUNFKDZBN-UHFFFAOYSA-N tavapadon Chemical compound C=1C=C(C=2N(C(=O)NC(=O)C=2C)C)C(C)=CC=1OC1=NC=CC=C1C(F)(F)F AKQXQLUNFKDZBN-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- ZYOAELHCOVZCRQ-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.C=CN1CCCC1=O ZYOAELHCOVZCRQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- AACHVWXCVWWMSI-UHFFFAOYSA-N 3-hydroxypropyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCCO AACHVWXCVWWMSI-UHFFFAOYSA-N 0.000 description 1
- BQBYBPAPSIWHCE-UHFFFAOYSA-N 5-(dimethylamino)-2-methylpent-2-enoic acid Chemical compound CN(C)CCC=C(C)C(O)=O BQBYBPAPSIWHCE-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 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
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- 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
-
- 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
-
- 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
- A61K8/88—Polyamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
Definitions
- the present invention relates to a pretreatment agent for an acidic hair dye. More specifically, the present invention relates to a pretreatment agent for an acidic hair dye which improves the colorability and fastness of the acid hair dye.
- Acid hair dyes generally have a weaker dyeing property than oxidative hair dyes. Therefore, various studies have been made in the past to solve such disadvantages.
- a method for improving the dyeing property for example, benzyl alcohol, an acidic water bath containing an acid dye, which is used in a solvent-added dyeing method or a low-temperature dyeing method for wool, is used.
- polyethyleneimine is alkaline, so it can be used for hair dyes using oxidation dyes instead of alkaline agents such as ammonia and monoethanolamine.
- oxidation dyes instead of alkaline agents such as ammonia and monoethanolamine.
- No. 1 bulletin a hair dye that uses polyethyleneimine as the first agent and a second agent containing a melanin precursor such as tyrosine and DL- ⁇ -alanine and a metal salt (Japanese Patent Publication No. Sho 61-205) No. 23) has been proposed.
- the cationic polymer is used not only as an agent for improving gloss, combability and texture, but also as a dyeing aid for improving dyeability.
- no examples have been reported in which cationic polymers were applied to acid dyes.
- the acid dye has a sulfone group in the molecule, and when a cationic polymer is present, an ionic complex is formed between the sulfone group and the cationic group of the dye, and the acid dye is efficiently placed inside the hair.
- a cationic polymer such as polyethyleneimine and an acid dye in combination.
- An object of the present invention has been made in view of the above prior art, and has as its object to provide a means for further improving the dyeability and fastness with an acidic hair dye.
- Another object of the present invention is to provide not only mere destaining properties, but also excellent dyeing properties and fastness when dyeing with an acidic hair dye after destaining, without squeaky feeling during rinsing, and hair It is an object of the present invention to provide a hair dye pretreatment agent which keeps the texture of the hair in a moderate level.
- a pretreatment agent for an acidic hair dye comprising at least one cationic polymer selected from the group consisting of an amine polymer and a quaternary ammonium group-containing polymer.
- FIG. 1 is a photomicrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 21 of the present invention.
- FIG. 2 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 22 of the present invention.
- FIG. 3 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 23 of the present invention.
- FIG. 4 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 24 of the present invention.
- Fig. 5 is a micrograph (magnification: 400x) of the cross section of the dyed hair obtained in Comparative Example 5.
- FIG. 6 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Comparative Example 6.
- FIG. 7 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 25 of the present invention.
- FIG. 8 is a micrograph (magnification: 400 times) of a cross section of the dyed hair obtained in Example 26 of the present invention.
- the pretreatment agent for an acidic hair dye of the present invention comprises: an amine-based polymer; It contains at least one type of thiothion polymer selected from the group consisting of quaternary ammonium group-containing polymers.
- the pretreatment agent for an acidic hair dye of the present invention contains a specific cationic polymer as described above, when the hair is treated by using this before dyeing with an acid hair dye, Since the cations are introduced into the hair, not only the dyeability and the fastness with the acidic hair dye are improved, but also an excellent effect of reducing the squeaky feeling when rinsing the hair is exhibited. The same excellent effects as described above are exerted not only on healthy hair but also on damaged hair.
- amine-based polymer examples include primary amine polymers such as polyacrylamide, polyvinylamine, polyethyleneimine (hereinafter, referred to as PEI) and derivatives thereof; and secondary amine polymers such as polyamine, PEI and derivatives thereof.
- Primary amine polymers such as polyacrylamide, polyvinylamine, polyethyleneimine (hereinafter, referred to as PEI) and derivatives thereof; and secondary amine polymers such as polyamine, PEI and derivatives thereof.
- Amine polymers; tertiary amine polymers such as PEI or derivatives thereof; and the like, and these cationic polymers can be used alone or in combination of two or more. Since PEI or a derivative thereof has a primary amino group, a secondary amino group and a tertiary amino group, any of a primary amine polymer, a secondary amine polymer and a tertiary amine polymer is used. It is a good thing.
- PEI or a derivative thereof is preferably used because of its high charge density and many cation charges in the molecule.
- PEI derivatives include, for example, a secondary amino group or a tertiary ethyleneimino group of PEI, polyoxydiethylene, polyoxydipropylene, polyoxybutylene, and an alkyl group having a molecular chain having 4 to 22 carbon atoms. PEI derivatives added in equimolar or more.
- the number average molecular weight of PEI or a derivative thereof is from 300 to 500, preferably from 300 to 300, more preferably from 500 to 100,000. Is desirable.
- Commercially available products of PE I include, for example, Epomin SP-003, Epomin SP-006, Epomin SP-200, Epomin P-100000 [all, Nippon Shokubai Co., Ltd., trade name], Lup as 01 [BASF, trade name].
- Examples of the quaternary ammonium group-containing polymer include, for example, hydroxyethylcellulose 'hydroxypropyltrimethylammonium chloride ether, hydroxyethylcellulose' dimethyldiarylammonium chloride copolymer, guar gum'chloride Hydroxypropyltrimethylammonium ether, cationized pullulan, dimethyldiarylammonium acrylamide copolymer, vinylpyrrolidone dimethyl sulfate ⁇ , ⁇ -dimethylaminoethyl methacrylic acid copolymer, dimethyldichloride Acrylammonium homopolymer, dimethyldiarylammonium chloride-acrylic acid copolymer, acrylamide 'acrylic acid-dimethyldiarylammonium chloride copolymer, cationized silicone copolymer, etc. These cations polymers one can that you use alone or in combination.
- hydroxyethyl cellulose / hydroxypropyltrimethylammonium chloride ester Commercial products of hydroxyethyl cellulose / hydroxypropyltrimethylammonium chloride ester include, for example, Leogard G, Leogard NGP, and Leogard KGP [all, manufactured by Lion Corporation, trade name], Kachinar HC-100 And LC_100 [above, manufactured by Toho Chemical Industry Co., Ltd., trade name]].
- Examples of commercially available hydroxyethylcellulose / dimethyldiarylammonium chloride copolymers include Cellcoat L-200 and Cellcoat H-60 [all, manufactured by National Starch, trade name].
- Guar gum ⁇ Commercial products of hydroxypropyltrimethylammonium chloride include, for example, Jaguar C-13-S and Jaguar C-15-S (these are products of Celanese Ciutane Hall, trade name) Is mentioned.
- Commercially available dimethyldiallylammonium chloride / acrylamide copolymers include, for example, Markco 550 (trade name, manufactured by Calgon).
- N, N-dimethylaminoethyl methacrylic acid copolymers include, for example, H. Polymer 5 (trade name, manufactured by Osaka Organic Chemical Industry Co., Ltd.), Guff Coat 755 N
- dimethyldiarylammonium chloride homopolymer Commercial products of dimethyldiarylammonium chloride homopolymer include, for example, Macocoat 100 (trade name, manufactured by Calgon). Commercially available dimethyldiarylammonium chloride / acrylic copolymers include, for example, Macocoat 280 and Marcote 295 [these products are manufactured by Tiragon Co., Ltd., trade names]. Commercial products of acrylamide, acrylic acid, and dimethyldiacrylammonium chloride copolymer include Marcote Plus 330 (trade name, manufactured by Calgon). Commercial products of the cationized silicone polymer include SM8704C (trade name, manufactured by Dow Corning Toray Silicone Co., Ltd.).
- the content of the cationic polymer in the pretreatment agent for an acidic hair dye of the present invention is determined by the effects of dyeing performance and fastness, reduced squeaky feeling during rinsing, and economical efficiency (even if the amount exceeds 30% by weight). However, from the viewpoint that the excess amount is washed out by rinsing as a surplus amount), it is desirably 0.01 to 30% by weight, preferably 0.05 to 20% by weight.
- the pretreatment agent for an acidic hair dye of the present invention contains urea as a component other than the cationic polymer in order to further improve the dyeing performance and fastness and reduce the squeaky feeling upon rinsing. be able to.
- the urea content in the pretreatment agent for acidic hair dyes of the present invention is determined by the effects of dyeing performance and fastness, reduced squeaky feeling during rinsing, and economical efficiency (even if more than 60% by weight). From 0.1 to 60% by weight, preferably from 0.5 to 40% by weight, from the viewpoint of rinsing as a surplus part. It is preferable to use an organic solvent in order to promote the penetration into the hair.
- the organic solvent include N-alkylpyrrolidone such as 1-methyl-2-pyrrolidone and 1-ethyl-2-pyrrolidone; lower alkylene carbonate such as ethylene carbonate and propylene carbonate; benzyl alcohol and 2-benzyloxy And aromatic alcohols such as ethanol. Furthermore, it is more preferable to use the aromatic alcohol in combination with a lower alcohol.
- the content of the organic solvent in the pretreatment agent for an acidic hair dye of the present invention is from 1 to 40% by weight, preferably from 5 to 20% by weight from the viewpoint of a sufficient effect of promoting the penetration of the active ingredient into hair. % Is desirable. If the amount is less than 1% by weight, the effect of promoting the penetration of the active ingredient into the hair is not sufficient, and if it exceeds 40% by weight, no further effect can be expected.
- the balance of the above components in the pretreatment agent for an acidic hair dye of the present invention is water.
- water distilled water, city water, purified water and the like can be used.
- the pH of the pretreatment agent for an acidic hair dye of the present invention is desirably 2 to 11, preferably 7 to 11.
- the pH can be easily adjusted using, for example, an organic acid such as citric acid, acetic acid, glycolic acid, levulinic acid, tartaric acid, or a pH adjusting agent such as a phosphate buffer, ammonia, or monoethanolamine. .
- the dosage form of the pretreatment agent for an acidic hair dye of the present invention is not particularly limited, and examples thereof include an aqueous solution, a cream, a gel, a dispersion, an emulsion, and an azole.
- the pretreatment agent for an acidic hair dye of the present invention can be used, for example, as follows. First, hair is immersed in the pretreatment agent for an acidic hair dye of the present invention at a temperature of room temperature to 60 ° C. for about 1 minute to 1 hour, washed with water, and dyed with an acid hair dye.
- acidic hair dye there is no particular limitation on the acidic hair dye, and those that have been used in the past can be used.
- the pretreatment agent of the present invention when the color of the hair dyed with the acid hair dye is changed or when the hair is dyed with the acid hair dye, if the hair is destained with the pretreatment agent of the present invention in advance, the pretreatment is performed.
- the cation is introduced into the hair by the agent, which not only improves the dyeability and fastness of the acid hair dye, but also reduces the squeaky feeling when shampooing the hair. Is expressed. Such excellent effects are also exerted on damaged hair.
- the dyed hair when the dyed hair is destained with the pretreatment agent of the present invention, the dyed hair can be destained effectively. Furthermore, even if the hair is dyed again with an acidic hair dye after destaining, the hair dye is excellent in dyeability and fastness, and has no squeaky feeling during rinsing, thereby improving the texture of the hair. An excellent effect of keeping it moderately is exhibited. Such an effect is hardly reduced even when re-dyeing with a pre-treatment agent and hair dyeing with an acidic hair dye are repeatedly performed. Therefore, hair dyeing with an acid dye and destaining with a pretreatment agent can be repeatedly performed.
- Example 1 Example 1
- the components shown in Table 1 were diluted with distilled water to have the concentrations shown in Table 1 to obtain a pretreatment agent for an acidic hair dye.
- 1 g of the dried hair bundles are immersed in a pretreatment agent for acidic hair dye at room temperature for 15 minutes (bath ratio 15 times), washed with water for 1 minute, and then wiped off the moisture in the hair bundles with a Kim towel.
- a pretreatment agent for acidic hair dye at room temperature for 15 minutes (bath ratio 15 times)
- washed with water for 1 minute and then wiped off the moisture in the hair bundles with a Kim towel.
- the hair bundles of the treated yak were immersed in a 0.1% by weight aqueous solution of orange No. 205 at room temperature for 20 minutes (bath ratio: 15 times), washed with water for 1 minute, and dried sufficiently. By doing so, a dyed hair bundle was obtained.
- the dyed hair bundle thus obtained is directly measured using a spectrophotometer [Nippon Denshoku Industries Co., Ltd., trade name: SII- ⁇ 80, the same applies hereinafter], and the dyed hair bundle and undyed hair are measured.
- the color difference ( ⁇ ) from the bundle was calculated, and the dyeability was evaluated.
- the decrease in squeaky feeling when the hair tresses were washed with water was sensory evaluated by five expert panelists based on the following evaluation criteria.
- PEIs having different molecular weights as shown in Table 2 were dissolved in distilled water so as to have the concentrations shown in Table 2, to prepare a pretreatment agent for an acidic hair dye.
- 1 g of the dried hair bundle was immersed in a pretreatment agent for acidic hair dye at room temperature for 20 minutes (bath ratio: 15 times), washed with water for 1 minute, and the hair in the hair bundle was wiped off with a Kim towel. .
- the hair bundle of the treated yak was immersed in a 0.1% by weight aqueous solution of orange No. 205 (containing 4% by weight of citric acid) at room temperature for 20 minutes (bath ratio: 15 ), Washed with water for 1 minute, and dried sufficiently to obtain a dyed hair bundle.
- the dyed hair bundle thus obtained was directly measured using a spectrophotometer, the color difference ( ⁇ ) between the dyed hair bundle and the unstained hair bundle was calculated, and the dyeability was evaluated.
- PEI urea and 1-methyl-2-pyrrolidone were dissolved in distilled water so as to have the contents shown in Table 3, to obtain a pretreatment agent for an acidic hair dye.
- the dyeability was examined according to the following method, and the fastness and squeakiness were examined in the same manner as in Examples 1 to 5.
- 1 g of the dried hair bundle of hair is immersed in a pretreatment agent for acidic hair dye at 50 ° C. for 15 minutes (bath ratio 15 times), washed with water for 1 minute, and then washed with a Kim towel. The water was wiped off. Next, after being immersed in a 0.1% by weight aqueous solution of orange color No. 205 (containing 4% by weight of citric acid) at room temperature for 20 minutes (bath ratio: 15 times), washed with water for 1 minute and dried sufficiently Thus, a dyed hair bundle was obtained.
- the dyed hair bundle thus obtained was measured using a spectrophotometer, and the color difference ( ⁇ ) between the dyed hair bundle and the undyed hair bundle was calculated to evaluate the dyeability.
- Example 16 to 20 When urea is contained in the pretreatment agent for acidic hair dye (Examples 16 to 20), when the pretreatment agent for acid hair dye not containing PEI is used (see Compared to Example 14), it is clear that the solidity is excellent and there is no squeaky feeling during rinsing. In addition, comparing Example 19 with Examples 14 and Comparative Example 4, the combined use of PEI and urea as a synergistic effect of the combined use of both PEI and urea compared to the use of PEI alone or urea alone was It can be seen that the dyeability and the fastness are improved. Examples 21 to 24 and Comparative Examples 5 to 6
- PEI urea and 1-methyl-2-pyrrolidone were dissolved in distilled water so as to have the contents shown in Table 4, to obtain a pretreatment agent for an acidic hair dye.
- the dyeability was examined according to the following method, and the fastness and squeakiness were examined in the same manner as in Examples 1 to 5.
- 1 g of the dried human hair gray hair bundle is immersed in a pretreatment agent for acidic hair dye at 50 ° C. for 15 minutes (bath ratio 15 times), washed with water for 1 minute, and then washed with a Kim towel. After wiping off the water, it was immersed in a 0.1% by weight aqueous solution of No. 205 (containing 4% by weight citric acid) at 50 ° C for 20 minutes (bath ratio: 15 times). After washing with water for a minute and drying sufficiently, a dyed hair bundle was obtained.
- the obtained dyed hair bundle was measured using a spectrophotometer, the color difference ( ⁇ ) between the dyed hair bundle and the undyed hair bundle was calculated, and the dyeability was evaluated.
- Table 4 The obtained dyed hair bundle was measured using a spectrophotometer, the color difference ( ⁇ ) between the dyed hair bundle and the undyed hair bundle was calculated, and the dyeability was evaluated.
- the pretreatment agent for acidic hair dyes using both PE I and urea is the pretreatment agent for acid hair dyes using PE I alone (Examples). 21-22, in comparison with Figures 1-2), it can be seen that dye penetration and fastness are excellent and that there is no feeling of creaking during rinsing due to the enhanced penetration of the dye.
- the dyeability was examined according to the following method, and the fastness and squeakiness were examined in the same manner as in Examples 1 to 5.
- 1 g of the dried human hair gray hair bundle is immersed in a pretreatment agent for acidic hair dye at 50 ° C for 15 minutes (bath ratio: 15 times), washed with water for 1 minute, and wiped off the moisture in the hair bundle with Kim towel Next, a 0.1% by weight aqueous solution of orange No. 205 (containing 4% by weight citrate) After immersion at 50 ° C for 20 minutes (bath ratio 15 times), it was washed with water for 1 minute and dried sufficiently to obtain a dyed hair bundle.
- the obtained dyed hair bundle was measured using a spectrophotometer, the color difference ( ⁇ ) between the dyed hair bundle and the unstained hair bundle was calculated, and the dyeability was evaluated.
- PEI, Cotamine 86W, urea, and 1-methyl-2-pyrrolidone were dissolved in distilled water so as to have the contents shown in Table 6, to obtain a pretreatment agent for an acidic hair dye.
- a pretreatment agent for an acidic hair dye was obtained by distilled water so as to have the contents shown in Table 6, to obtain a pretreatment agent for an acidic hair dye.
- the dyeing property, the fastness and the squeakiness were evaluated. Table 6 shows the results.
- the dyeability was examined according to the following method, and the fastness and squeakiness were examined in the same manner as in Examples 1 to 5.
- Damaged hair was prepared in advance by bleaching 1 g of the dried gray hair tress (6% hydrogen peroxide solution (pH 0.2), 7.t., 1 hr (bath ratio 1:50)). 1 g of these gray hair tresses were immersed in a pretreatment agent for acidic hair dyes for 5 minutes (TC for 15 minutes (bath ratio 15 times)), washed with water for 1 minute, and then the water in the hair tresses was wiped off with a Kim towel. .
- the obtained dyed hair bundle was measured using a spectrophotometer, the color difference ( ⁇ ) between the dyed hair bundle and the undyed hair bundle was calculated, and the dyeability was evaluated.
- PE I SP-003
- urea urea
- MP urea
- the dyed hair bundle is immersed in the pretreatment agent shown in Table 1 at 50 for 20 minutes (bath ratio: 15 times), washed with water for 1 minute, dried sufficiently, and specialized based on the following evaluation criteria. Sensory evaluation was conducted by five panelists.
- the dyed hair bundle was immersed in a pretreatment agent shown in Table 7 at 50 ° C for 20 minutes (bath ratio: 15 times), washed with water for 1 minute, and dried sufficiently to obtain a destained hair bundle. Obtained.
- the obtained color difference ( ⁇ !) Of the hair bundle after destaining and the color difference ( ⁇ 2 ) of the dyed hair bundle before destaining were measured with a spectrophotometer [SZ- ⁇ , manufactured by Nippon Denshoku Industries Co., Ltd.] 80, the same applies hereafter).
- the destaining property was evaluated according to the following. In addition, the larger the value of the destaining property, the better the destaining property.
- Table 7 also shows the color difference ( ⁇ :) of the hair bundle when 1 g of the dried gray human hair before dyeing was not subjected to the destaining treatment (Reference Example 1).
- Example 31 and Reference Example 1 the dyed hair bundle obtained in the above [Dyeability] was treated with a treating solution [Polyoxyethylene (additional mole number of oxyethylene: 3) sodium lauryl monosulfate (Kao Corporation) (Product name: EMAL 20C) in a 10% by weight aqueous solution] at 40 ° C for 3 hours (15 times the post-bath ratio).
- a treating solution Polyoxyethylene (additional mole number of oxyethylene: 3) sodium lauryl monosulfate (Kao Corporation) (Product name: EMAL 20C) in a 10% by weight aqueous solution] at 40 ° C for 3 hours (15 times the post-bath ratio).
- the dyed tresses were washed with water for 1 minute, dried at room temperature, was determined color difference tuft after performing the processing ( ⁇ ⁇ 4).
- the color difference Senshokuke bundle and (delta E 3), as the difference between the color difference (delta E 4) of the hair bundle after performing the process is small, is excellent in fastness.
- the degree of dye elution (the concentration of the eluted dye in the solution and the absorbance at a wavelength of 487 nm) of a solution obtained by diluting the treated solution 30-fold was measured.
- the dyed hair bundles have the same dyeing performance, the smaller the dye elution degree, the better the fastness.
- Example 31 and Reference Example 1 the dyed hair bundle obtained in [Dyeability] was treated with a treating solution [polyoxyethylene (additional mole number of oxyethylene: 3) lauryl ether sodium sulfate (manufactured by Kao Corporation). And a trade name: 10% by weight of an aqueous solution of Emar 20 C)), and five specialized panelists examined the squeaky feeling when washed with water, and evaluated based on the following evaluation criteria. T / JP01 / 06033
- the following components were mixed to prepare a pretreatment agent for a gel type acidic hair dye.
- Purified water Formulation example 3 Preparation of hair cream type pretreatment agent for acidic hair dye
- the following components are mixed to prepare a hair cream type pretreatment agent for acidic hair dye.
- the pretreatment agent for an acidic hair dye of the present invention has an effect of further improving the dyeability and fastness by the acid hair dye.
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Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001269509A AU2001269509A1 (en) | 2000-07-17 | 2001-07-12 | Pretreatment agents for acidic hair dyes |
US10/333,054 US7037347B2 (en) | 2000-07-17 | 2001-07-12 | Pretreatment agents for acidic hair dyes |
EP01947981A EP1302195A4 (en) | 2000-07-17 | 2001-07-12 | PRE-TREATMENT AGENTS FOR ACID HAIR COLORING AGENTS |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP2000216550A JP3762967B2 (ja) | 2000-07-17 | 2000-07-17 | 酸性染毛剤用前処理剤 |
JP2000-216550 | 2000-07-17 | ||
JP2000-374945 | 2000-12-08 | ||
JP2000374945A JP3647744B2 (ja) | 2000-12-08 | 2000-12-08 | 染料除去剤 |
Publications (1)
Publication Number | Publication Date |
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WO2002005768A1 true WO2002005768A1 (fr) | 2002-01-24 |
Family
ID=26596186
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PCT/JP2001/006033 WO2002005768A1 (fr) | 2000-07-17 | 2001-07-12 | Agents de pretraitement pour colorants capillaires acides |
Country Status (4)
Country | Link |
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US (1) | US7037347B2 (ja) |
EP (1) | EP1302195A4 (ja) |
AU (1) | AU2001269509A1 (ja) |
WO (1) | WO2002005768A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1428497A1 (en) * | 2002-12-12 | 2004-06-16 | KPSS-Kao Professional Salon Services GmbH | Pre-treatment composition applied before colouring hair with acidic direct dyes |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2887147B1 (fr) * | 2005-06-15 | 2009-10-30 | Lcw Les Colorants Wackherr Sa | Compositions de pre-traitement pour colorations et procede de coloration |
US20060292100A1 (en) * | 2005-06-16 | 2006-12-28 | L'oreal | Aqueous phospholipid-containing carrier systems for water-insoluble materials |
US8128917B2 (en) * | 2005-06-16 | 2012-03-06 | L'oréal | Aqueous polyamine-containing carrier systems for water-insoluble materials |
US8128916B2 (en) * | 2005-06-16 | 2012-03-06 | L'oréal | Aqueous fatty quaternary amine-containing carrier systems for water-insoluble materials |
US8128915B2 (en) * | 2005-06-16 | 2012-03-06 | L'oréal | Aqueous fatty monoamine-containing carrier systems for water -insoluble materials |
JP4919961B2 (ja) * | 2005-09-02 | 2012-04-18 | 荏原ユージライト株式会社 | 触媒付与増強剤 |
US7727288B2 (en) | 2005-11-16 | 2010-06-01 | L'oreal | Process for styling dyed hair and inhibiting its color loss during shampooing |
US7449029B2 (en) | 2005-11-16 | 2008-11-11 | L'oreal | Composition and process for color hair |
US20070110691A1 (en) | 2005-11-16 | 2007-05-17 | L'oreal | Process for inhibiting dyed hair fibers from losing their color during shampooing |
US20070169285A1 (en) * | 2006-01-25 | 2007-07-26 | Saroja Narasimhan | Method and kit for coloring hair |
EP2092932A3 (en) * | 2006-09-13 | 2013-05-15 | The Procter and Gamble Company | Processes to pre-treat hair with organic solvents |
CN101516322A (zh) | 2006-09-13 | 2009-08-26 | 宝洁公司 | 用有机溶剂预处理毛发的方法 |
US20080085258A1 (en) * | 2006-10-06 | 2008-04-10 | L'oreal | Aqueous polymaine-containing anti-frizz composition for hair |
US7955606B2 (en) * | 2006-10-19 | 2011-06-07 | L'oreal | Aqueous systems containing polyamine, surfactant and phosphate ester for water-insoluble materials |
JP4628486B2 (ja) * | 2009-04-17 | 2011-02-09 | 花王株式会社 | 液体洗浄剤組成物 |
US8343238B1 (en) | 2011-12-30 | 2013-01-01 | L'oreal Sa. | Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases |
US8506651B2 (en) | 2011-12-30 | 2013-08-13 | L'oreal S.A. | Process for altering the appearance of hair using a composition containing dyes and non-hydroxide bases |
US8556994B2 (en) | 2011-12-30 | 2013-10-15 | L'oreal | Process for altering the appearance of hair using a composition containing direct dyes and non-hydroxide bases |
US8591872B2 (en) | 2011-12-30 | 2013-11-26 | L'oreal | Composition and process for reducing the curl and frizziness of hair |
US10596100B2 (en) | 2012-12-19 | 2020-03-24 | L'oreal | Cosmetic compositions containing an alkoxysilane and a silsesquioxane resin |
FR3061005B1 (fr) * | 2016-12-22 | 2020-10-16 | Oreal | Procede de coloration capillaire a partir de colorants acides comprenant un pretraitement mettant en œuvre un polymere cationique |
EP3342464A1 (en) | 2016-12-27 | 2018-07-04 | Kao Germany GmbH | Method for colouring keratin fibers |
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FR2470596A1 (fr) | 1979-11-28 | 1981-06-12 | Oreal | Composition destinee au traitement des fibres keratiniques a base de polymeres amphoteres et de polymeres cationiques |
JPS5695994A (en) * | 1979-12-28 | 1981-08-03 | Kao Corp | Shampoo composition |
JPS57144213A (en) * | 1981-03-03 | 1982-09-06 | Kao Corp | Hair treatment |
JPH0613451B2 (ja) | 1983-11-29 | 1994-02-23 | サンスター株式会社 | 毛髪染色剤 |
US5338540A (en) * | 1985-02-04 | 1994-08-16 | Conopco, Inc. | Hair waving and straightening composition |
JPH01275519A (ja) | 1988-04-26 | 1989-11-06 | Hoyu Co Ltd | 染毛剤組成物 |
JPH06316512A (ja) | 1993-05-06 | 1994-11-15 | Nikko Kemikaruzu Kk | シャンプー組成物 |
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JP3784536B2 (ja) | 1998-05-26 | 2006-06-14 | ホーユー株式会社 | 半永久染毛料用脱染剤 |
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GB9917453D0 (en) | 1999-07-23 | 1999-09-29 | Unilever Plc | Method of hair treatment using organic amino compounds |
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2001
- 2001-07-12 US US10/333,054 patent/US7037347B2/en not_active Expired - Fee Related
- 2001-07-12 AU AU2001269509A patent/AU2001269509A1/en not_active Abandoned
- 2001-07-12 EP EP01947981A patent/EP1302195A4/en not_active Withdrawn
- 2001-07-12 WO PCT/JP2001/006033 patent/WO2002005768A1/ja not_active Application Discontinuation
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GB2057261A (en) * | 1979-07-02 | 1981-04-01 | Bristol Myers Co | Hair conditioning composition and method |
JP2000169343A (ja) * | 1998-12-04 | 2000-06-20 | Hoyu Co Ltd | 毛髪処理剤組成物 |
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EP1428497A1 (en) * | 2002-12-12 | 2004-06-16 | KPSS-Kao Professional Salon Services GmbH | Pre-treatment composition applied before colouring hair with acidic direct dyes |
Also Published As
Publication number | Publication date |
---|---|
EP1302195A4 (en) | 2004-12-15 |
US20040045099A1 (en) | 2004-03-11 |
EP1302195A1 (en) | 2003-04-16 |
US7037347B2 (en) | 2006-05-02 |
AU2001269509A1 (en) | 2002-01-30 |
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