DE19834651C1 - Hair color based on an oxidation dye precursor reacting with peroxide contains 1-hydroxyethoxy-2,4-diaminobenzene and aminobenzene, aminophenol and 4-aminopiperidinoaniline compound(s) - Google Patents
Hair color based on an oxidation dye precursor reacting with peroxide contains 1-hydroxyethoxy-2,4-diaminobenzene and aminobenzene, aminophenol and 4-aminopiperidinoaniline compound(s)Info
- Publication number
- DE19834651C1 DE19834651C1 DE1998134651 DE19834651A DE19834651C1 DE 19834651 C1 DE19834651 C1 DE 19834651C1 DE 1998134651 DE1998134651 DE 1998134651 DE 19834651 A DE19834651 A DE 19834651A DE 19834651 C1 DE19834651 C1 DE 19834651C1
- Authority
- DE
- Germany
- Prior art keywords
- diaminobenzene
- aminophenol
- amino
- aminopiperidinoaniline
- hydroxyethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000002978 peroxides Chemical class 0.000 title claims abstract description 8
- 239000002243 precursor Substances 0.000 title claims abstract description 5
- 230000003647 oxidation Effects 0.000 title abstract description 7
- 238000007254 oxidation reaction Methods 0.000 title abstract description 7
- 230000037308 hair color Effects 0.000 title abstract 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title description 3
- -1 4-aminopiperidinoaniline compound Chemical class 0.000 title description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title 2
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 title 1
- 239000000126 substance Substances 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- WCPGNFONICRLCL-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C(N)=C1 WCPGNFONICRLCL-UHFFFAOYSA-N 0.000 claims abstract description 6
- QIELWBSPBOKMMP-UHFFFAOYSA-N 1-N-phenylpiperidine-1,4-diamine Chemical compound NC1CCN(CC1)NC1=CC=CC=C1 QIELWBSPBOKMMP-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims abstract description 5
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 claims abstract description 4
- HFYPXERYZGFDBD-UHFFFAOYSA-N 4-amino-2,6-dibromophenol Chemical compound NC1=CC(Br)=C(O)C(Br)=C1 HFYPXERYZGFDBD-UHFFFAOYSA-N 0.000 claims abstract description 4
- CBQJZWGBFZAUEV-UHFFFAOYSA-N 4-amino-2-bromophenol Chemical compound NC1=CC=C(O)C(Br)=C1 CBQJZWGBFZAUEV-UHFFFAOYSA-N 0.000 claims abstract description 4
- WACZDUCWYAIUCI-UHFFFAOYSA-N 2-(4-amino-2-methylphenyl)ethanol Chemical compound CC1=CC(N)=CC=C1CCO WACZDUCWYAIUCI-UHFFFAOYSA-N 0.000 claims abstract description 3
- ISCYHXYLVTWDJT-UHFFFAOYSA-N 2-[4-amino-n-(2-hydroxyethyl)anilino]ethanol Chemical compound NC1=CC=C(N(CCO)CCO)C=C1 ISCYHXYLVTWDJT-UHFFFAOYSA-N 0.000 claims abstract description 3
- KRQUHMFZMVSALZ-UHFFFAOYSA-N 4-amino-2-(diethylaminomethyl)phenol Chemical compound CCN(CC)CC1=CC(N)=CC=C1O KRQUHMFZMVSALZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims abstract description 3
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000118 hair dye Substances 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 7
- KWSVXCAQFTWTEF-UHFFFAOYSA-N 2-(2,5-diaminophenyl)ethanol Chemical compound NC1=CC=C(N)C(CCO)=C1 KWSVXCAQFTWTEF-UHFFFAOYSA-N 0.000 claims description 3
- KGEXISHTCZHGFT-UHFFFAOYSA-N 4-azaniumyl-2,6-dichlorophenolate Chemical compound NC1=CC(Cl)=C(O)C(Cl)=C1 KGEXISHTCZHGFT-UHFFFAOYSA-N 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 2
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 abstract 1
- 238000004040 coloring Methods 0.000 description 10
- 210000004209 hair Anatomy 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- SYEYEGBZVSWYPK-UHFFFAOYSA-N 2,5,6-triamino-4-hydroxypyrimidine Chemical compound NC1=NC(N)=C(N)C(O)=N1 SYEYEGBZVSWYPK-UHFFFAOYSA-N 0.000 description 2
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 2
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JSYBAZQQYCNZJE-UHFFFAOYSA-N benzene-1,2,4-triamine Chemical compound NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 229940075142 2,5-diaminotoluene Drugs 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- BMTSZVZQNMNPCT-UHFFFAOYSA-N 2-aminopyridin-3-ol Chemical compound NC1=NC=CC=C1O BMTSZVZQNMNPCT-UHFFFAOYSA-N 0.000 description 1
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- WTLVAFTZNBFKTI-UHFFFAOYSA-N 2-methylbenzene-1,4-diamine;4-methylcyclohexa-1,5-diene-1,4-diamine Chemical compound CC1=CC(N)=CC=C1N.CC1(N)CC=C(N)C=C1 WTLVAFTZNBFKTI-UHFFFAOYSA-N 0.000 description 1
- OBOSXEWFRARQPU-UHFFFAOYSA-N 2-n,2-n-dimethylpyridine-2,5-diamine Chemical compound CN(C)C1=CC=C(N)C=N1 OBOSXEWFRARQPU-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- ZQBHGSSAKLGUBH-UHFFFAOYSA-N 4,5,6-triamino-1h-pyrimidin-2-one Chemical compound NC1=NC(=O)NC(N)=C1N ZQBHGSSAKLGUBH-UHFFFAOYSA-N 0.000 description 1
- PLISWDVQSUTGTR-UHFFFAOYSA-N 4-amino-2-(diethylaminomethyl)phenol;dihydrochloride Chemical compound Cl.Cl.CCN(CC)CC1=CC(N)=CC=C1O PLISWDVQSUTGTR-UHFFFAOYSA-N 0.000 description 1
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 description 1
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 description 1
- ATCBPVDYYNJHSG-UHFFFAOYSA-N 6-methoxy-2-n-methylpyridine-2,3-diamine Chemical compound CNC1=NC(OC)=CC=C1N ATCBPVDYYNJHSG-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- WRPSKOREVDHZHP-UHFFFAOYSA-N benzene-1,4-diamine Chemical compound NC1=CC=C(N)C=C1.NC1=CC=C(N)C=C1 WRPSKOREVDHZHP-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- KDNFLUWYIMPBSA-UHFFFAOYSA-N hydrogen peroxide;1,3,5-triazine-2,4,6-triamine Chemical compound OO.NC1=NC(N)=NC(N)=N1 KDNFLUWYIMPBSA-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 1
- 229960004963 mesalazine Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940101267 panthenol Drugs 0.000 description 1
- 235000020957 pantothenol Nutrition 0.000 description 1
- 239000011619 pantothenol Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- A61K8/30—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
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- 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
- A61K8/415—Aminophenols
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft ein Haarfärbemittel auf Basis eines mit Peroxid reagieren den Oxidationsfarbstoff-Systems, das dauerhafte intensive Farbtöne liefert, die entweder als solche angewandt werden, oder, in Kombination mit weiteren Entwickler- und/oder Kuppler substanzen, zur Erzielung weiterer Farbnuancen benutzt werden können und das Haar selbst bei kurzfristiger wiederholter Anwendung nicht schädigt.The present invention relates to a hair dye based on reacting with peroxide the oxidation dye system, which provides permanent intense hues, either as such are used, or, in combination with other developer and / or coupler substances can be used to achieve further color shades and the hair itself does not damage with short-term repeated use.
Die nach wie vor in Haarfärbemitteln meist eingesetzten Entwicklersubstanzen sind 1,4-Di aminobenzol (p-Phenylendiamin) und 1-Methyl-2,5-diaminobenzol (p-Toluylendiamin). Die Verwendung dieser Substanzen wird den farbtechnischen Wünschen der Anwender zwar weitgehend gerecht, es gibt jedoch immer noch Farbnuancen, die dadurch nicht voll erreicht werden können. Darüberhinaus können diese Zusammensetzungen bei sehr empfindlichen Personen, sogenannten "Para-Allergikern", auch zu Hautreizungen führen.The developer substances that are still mostly used in hair dyes are 1,4-di aminobenzene (p-phenylenediamine) and 1-methyl-2,5-diaminobenzene (p-toluenediamine). The The use of these substances does indeed meet the color requirements of the users largely fair, but there are still color shades that are not fully achieved can be. In addition, these compositions can be very sensitive People, so-called "para-allergy sufferers", also cause skin irritation.
Es wurde auch bereits vorgeschlagen, diese Nachteile durch Verwendung alternativer Ent wicklersubstanzen zu beheben. Dies ist in beschränktem Umfang möglich durch den Einsatz von Tetraaminopyrimidin oder 2-(2,5-Diaminophenyl)ethanol (vgl. EP-A 7537 und EP-B 400 330); jedoch müssen dann Abstriche in der Farbintensität mancher Nuancen hingenommen werden.It has also been suggested to overcome these drawbacks by using alternative Ent to fix winder substances. This is possible to a limited extent through use of tetraaminopyrimidine or 2- (2,5-diaminophenyl) ethanol (cf. EP-A 7537 and EP-B 400 330); however, the color intensity of some shades has to be accepted will.
Eine weitgehend optimale Lösung dieses Problems wird durch den in der EP-A 615 743 be schriebenen Einsatz von 2-(2'-Hydroxyethylamino)-5-aminotoluol bzw. dessen wasserlösli chen Salzen und die aus der EP-B 467 026 bekannten Triaminohydroxypyrimidine, insbeson dere 2,5,6-Triamino-4-hydroxypyrimidin, 2,4,5-Triamino-6-hydroxypyrimidin, 4,5,6- Triamino-2-hydroxypyrimidin bzw. deren Salze, insbesondere die Sulfate, als Entwicklersub stanzen in Haarfärbemitteln erreicht.A largely optimal solution to this problem is described in EP-A 615 743 Written use of 2- (2'-hydroxyethylamino) -5-aminotoluene or its water-soluble Chen salts and the triaminohydroxypyrimidines known from EP-B 467 026, in particular 2,5,6-triamino-4-hydroxypyrimidine, 2,4,5-triamino-6-hydroxypyrimidine, 4,5,6- Triamino-2-hydroxypyrimidine or its salts, especially the sulfates, as developer sub punching achieved in hair dye.
Selbst dadurch bleiben jedoch noch farbtechnische Wünsche offen.Even so, color-technical wishes still remain open.
Die Erfindung geht daher von der Aufgabenstellung aus, ein Haarfärbemittel zu schaffen, das zur Herstellung einer großen Anzahl von Farbtönen geeignet ist, keinerlei hautsensibilisieren de Reaktion hervorruft und das Haar selbst bei kurzzeitiger wiederholter Anwendung nicht schädigt. The invention is therefore based on the task of creating a hair dye that suitable for the production of a large number of shades, do not sensitize the skin at all de causes reaction and the hair does not, even with short repeated use harms.
Diese Aufgabe wird dadurch gelöst, daß ein solches Haarfärbemittel ein mit Peroxid reagierendes Oxidationsfarbstoff-System enthält, das aus einem Gemisch aus 1-β- Hydroxy-ethyloxy-2,4-diaminobenzol bzw. dessen wasserlöslichen Salzen und mindestens einer weiteren Substanz, ausgewählt aus 1-(β-Hydroxyethyl)-2,5- diaminobenzol, 2-(2'-Hydroxyethyl)-5-aminotoluol, N,N-Bis-(hydroxyethyl)-1,4- diaminobenzol, 4-Amino-3-methylphenol, 2-Amino-5-diethylaminotoluol, 3-(Di ethylaminomethyl)-4-hydroxyanilin, 2-Chlor-4-aminophenol, 2-Brom-4-aminophenol, 2,6-Dichlor-4-aminophenol, 2,6-Dibrom-4-aminophenol, 2-Amino-4-chlorphenol, 2- Amino-4-methylphenol und/oder 4-Aminopiperidinoanilin bzw. deren wasserlöslichen Salzen, besteht.This object is achieved in that such a hair dye with a peroxide reactive oxidizing dye system, which consists of a mixture of 1-β- Hydroxy-ethyloxy-2,4-diaminobenzene or its water-soluble salts and at least one further substance selected from 1- (β-hydroxyethyl) -2,5- diaminobenzene, 2- (2'-hydroxyethyl) -5-aminotoluene, N, N-bis (hydroxyethyl) -1,4- diaminobenzene, 4-amino-3-methylphenol, 2-amino-5-diethylaminotoluene, 3- (Di ethylaminomethyl) -4-hydroxyaniline, 2-chloro-4-aminophenol, 2-bromo-4-aminophenol, 2,6-dichloro-4-aminophenol, 2,6-dibromo-4-aminophenol, 2-amino-4-chlorophenol, 2- Amino-4-methylphenol and / or 4-aminopiperidinoaniline or their water-soluble Salting.
1-β-Hydroxyethyloxy-2,4-diaminobenzol ist bereits als Kupplersubstanz in Kombination mit 1,4-Diaminobenzol bzw. 2,5-Diaminotoluol vorgeschlagen worden und aus der DE 27 37 138 C2 bekannt.1-β-hydroxyethyloxy-2,4-diaminobenzene is already in as a coupler substance Combination with 1,4-diaminobenzene or 2,5-diaminotoluene have been proposed and known from DE 27 37 138 C2.
Weitere in Kombination mit dem erfindungsgemäßen Gemisch einsetzbare Kupplersubstanzen sind vorzugsweise ausgewählt aus der Gruppe 1-Methoxy-2- amino-4-(β-hydroxy-ethylamino)benzol, 2-Amino-3-hydroxypyridin, 2,5- Diaminopyridin, 2,6-Diaminopyridin, 3-Amino-2-methylamino-6-methoxy-pyridin, 2- (Dimethylamino)-5-aminopyridin, 1,3-Diaminobenzol, Resorcin, 2-Methylresorcin, 4- Chlorresorcin, 1-Naphthol, 2-Chlor-4-amino-phenol, 2-Aminophenol, 3-Aminophenol, 1-Methyl-2-hydroxy-4-aminobenzol, 5-Amino-2-methoxyphenol, 5-Amino-2- methylphenol, 2-Amino-4-β-hydroxyethylaminoanisol, bzw. deren wasserlöslichen Salzen.Further usable in combination with the mixture according to the invention Coupler substances are preferably selected from the group 1-methoxy-2- amino-4- (β-hydroxy-ethylamino) benzene, 2-amino-3-hydroxypyridine, 2,5- Diaminopyridine, 2,6-diaminopyridine, 3-amino-2-methylamino-6-methoxy-pyridine, 2- (Dimethylamino) -5-aminopyridine, 1,3-diaminobenzene, resorcinol, 2-methylresorcinol, 4- Chlororesorcinol, 1-naphthol, 2-chloro-4-aminophenol, 2-aminophenol, 3-aminophenol, 1-methyl-2-hydroxy-4-aminobenzene, 5-amino-2-methoxyphenol, 5-amino-2- methylphenol, 2-amino-4-β-hydroxyethylaminoanisole, or their water-soluble Salt.
Damit soll jedoch der Zusatz weiterer Entwickler- und Kupplersubstanzen keineswegs ausgeschlossen sein.However, this is intended to add further developer and coupler substances by no means be excluded.
Bei Anwendung dieser Zusammensetzungen auf Basis einer üblichen Grundlage werden nach der Oxidation mit Peroxid sehr ausdrucksvolle, intensive, dauerhafte Haarfärbungen erhalten, die durch Zusatz entsprechender weiterer Entwickler- und Kupplersubstanzen noch zu anderen Farbnuancen variiert werden können.Using these compositions on a common basis become very expressive, intense, lasting after oxidation with peroxide Obtain hair colorations by adding appropriate further developer and Coupler substances can be varied to other color shades.
Auch die zusätzliche Mitverwendung weiterer, an sich bekannter Entwicklersubstanzen ist möglich. Hierbei sind insbesondere noch 5- Aminosalicylsäure und/oder 1,2,4-Triaminobenzol zu erwähnen. Also the additional use of other, known per se Developer substances are possible. There are still 5- Aminosalicylic acid and / or 1,2,4-triaminobenzene to mention.
Die Gesamtkonzentration der Entwicklersubstanzen liegt üblicherweise zwischen etwa 0,05 und 5%, vorzugsweise 0,1 und 4%, insbesondere 0,25 bis 0,5% und 2,5 bis 3% Gew.-% der Gesamtzusammensetzung des Haarfärbemittels (ohne Oxidationsmittel), wobei sich die An gaben jeweils auf den Anteil an freier Base beziehen.The total concentration of the developer substances is usually between about 0.05 and 5%, preferably 0.1 and 4%, in particular 0.25 to 0.5% and 2.5 to 3% by weight of the Overall composition of the hair dye (without oxidizing agent), the An each related to the proportion of free base.
Das bevorzugte Gewichtsverhältnis von 1-β-Hydroxyethyloxy-2,4-diaminobenzol zu den weiteren genannten Substanzen liegt dabei zwischen etwa 1 : 8 bis 8 : 1, vorzugsweise etwa 1 : 5 bis 5 : 1, insbesondere 1 : 2 bis 2 : 1:The preferred weight ratio of 1-β-hydroxyethyloxy-2,4-diaminobenzene to further substances mentioned are between about 1: 8 to 8: 1, preferably about 1: 5 up to 5: 1, in particular 1: 2 to 2: 1:
Die Kupplersubstanz(en) als Reaktionspartner der Entwicklersubstanz(en) liegen in den erfin dungsgemäßen Haarfärbemitteln grundsätzlich etwa im gleichen molaren Anteil wie die Ent wicklersubstanzen vor, d. h., also in Mengen von 0,05 bis 5,0%, vorzugsweise 0,1 bis 4%, insbesondere 0,5 bis 3 Gew.-% der Gesamtzusammensetzung (ohne Oxidationsmittel), wobei sich die Angaben jeweils auf den Anteil an freier Base beziehen.The coupler substance (s) as reaction partner of the developer substance (s) are in the inventions hair dyes according to the invention basically in about the same molar proportion as the Ent developer substances, d. that is, in amounts of 0.05 to 5.0%, preferably 0.1 to 4%, in particular 0.5 to 3 wt .-% of the total composition (without oxidizing agent), wherein the information relates in each case to the proportion of free base.
Die erfindungsgemäßen Zusammensetzungen können erwünschtenfalls auch sogenannte Nu anceure zur Feineinstellung des gewünschten Farbtones, insbesondere auch direktziehende Farbstoffe, enthalten.If desired, the compositions according to the invention can also contain so-called nu anceure for fine adjustment of the desired color, especially direct ones Dyes.
Solche Nuanceure sind beispielsweise Nitrofarbstoffe wie 2-Amino-4,6-dinitrophenol, 2- Amino-4-nitrophenol, 2-Amino-6-chlor-4-nitrophenol, etc., vorzugsweise in Mengen von et wa 0,05 bis 2,5%, insbesondere 0,1 bis 1% Gew.-% der Farbzusammensetzung (ohne Oxi dationsmittel).Such nuances are, for example, nitro dyes such as 2-amino-4,6-dinitrophenol, 2- Amino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, etc., preferably in amounts of et wa 0.05 to 2.5%, in particular 0.1 to 1% by weight of the color composition (without oxi dation means).
Die erfindungsgemäßen Haarfärbemittel können die in solchen Mitteln üblichen Grund- und Zusatzstoffe, Konditioniermittel, etc. enthalten, die dem Fachmann aus dem Stand der Tech nik bekannt und beispielsweise in der Monografie von K. Schrader, "Grundlagen und Rezep turen der Kosmetika", 2. Aufl. (Hüthig Buch Verlag, Heidelberg, 1989), S. 782 bis 815, be schrieben sind. Sie können als Lösungen, Cremes, Gele oder auch in Form von Aerosol- Präparaten vorliegen; geeignete Trägermaterial-Zusammensetzungen sind aus dem Stand der Technik hinreichend bekannt.The hair colorants according to the invention can be the basic and Contain additives, conditioning agents, etc., which the expert from the prior art nik known and for example in the monograph by K. Schrader, "Fundamentals and Recipe turen der Kosmetika ", 2nd edition (Hüthig Buch Verlag, Heidelberg, 1989), pp. 782 to 815, be are written. They can be used as solutions, creams, gels or in the form of aerosol Preparations are available; suitable carrier material compositions are known from the prior art Technology well known.
Zur Applikation wird das erfindungsgemäße Oxidationsfarbstoff-Vorprodukt mit einem Oxi dationsmittel vermischt. Bevorzugtes Oxidationsmittel ist Wasserstoffperoxid, beispielsweise in 2- bis 6-prozentiger Konzentration.The oxidation dye precursor with an oxi is used for application dation agent mixed. The preferred oxidizing agent is hydrogen peroxide, for example in 2- to 6-percent concentration.
Es können jedoch auch andere Peroxide wie Harnstoffperoxid und Melaminperoxid eingesetzt werden. However, other peroxides such as urea and melamine peroxide can also be used will.
Der pH-Wert des applikationsfertigen Haarfärbemittels, d. h. nach Vermischung mit Peroxid, kann sowohl im schwach sauren, d. h. einem Bereich von 5,5 bis 6,9, im neutralen als auch im alkalischen Bereich, d. h. zwischen pH 7,1 und 10 liegen.The pH of the ready-to-use hair dye, d. H. after mixing with peroxide, can both in weakly acidic, d. H. a range from 5.5 to 6.9, in neutral as well as in alkaline range, d. H. are between pH 7.1 and 10.
Im folgenden werden verschiedene Ausführungsbeispiele zur Erläuterung der Erfindung gege ben.Various exemplary embodiments are explained below to explain the invention ben.
Die erfindungsgemäßen Oxidationsfarbstoff-Kombinationen wurden, unter entsprechender Verringerung des Wassergehalts, in diese Grundlage eingearbeitet. The oxidation dye combinations according to the invention were, with corresponding Reduction in water content, incorporated into this basis.
Die Ausfärbungen erfolgten jeweils an Woll-Läppchen und Strähnen aus gebleichtem Men schenhaar, durch Aufbringen einer 1 : 1-Mischung aus Farbstoff-Vorprodukt und 6%iger Was serstoffperoxid-Lösung (pH-Wert der Mischung: 9,8) und zwanzigminütiger Einwirkung bei Zimmertemperatur, folgendem Auswaschen und Trocknen.The dyeing was done on wool patches and strands of bleached men human hair, by applying a 1: 1 mixture of dye precursor and 6% water Hydrogen peroxide solution (pH value of the mixture: 9.8) and exposure for 20 minutes Room temperature, subsequent washing and drying.
Es wurden die folgenden Färbungen erzielt:The following colorations were achieved:
0,40 Gew.-% 4-Aminopiperidinoanilin
0,54 Gew.-% 1-β-Hydroxyethyloxy-2,4-diaminobenzol
(A 42)0.40% by weight 4-aminopiperidinoaniline
0.54% by weight of 1-β-hydroxyethyloxy-2,4-diaminobenzene (A 42)
Glänzendes Graublau.Shiny gray-blue.
0,54 Gew.-% A 42
0,56 Gew.-% 1-(β-Hydroxyethyl)-2,5-diaminobenzolsulfat0.54% by weight of A 42
0.56% by weight of 1- (β-hydroxyethyl) -2,5-diaminobenzenesulfate
Glänzendes Tiefblau.Shiny deep blue.
0,54 Gew.-% A 42
0,71 Gew.-% 2-(2'-Hydroxyethylamino)-5-
aminotoluolsulfat . 3H2 0.54% by weight of A 42
0.71% by weight of 2- (2'-hydroxyethylamino) -5- aminotoluenesulfate. 3H 2
OO
Glänzendes Tiefblau. Shiny deep blue.
0,54 Gew.-% A 42
0,48 Gew.-% 2-Amino-5-diethylamino
toluolhydrochlorid0.54% by weight of A 42
0.48% by weight of 2-amino-5-diethylamino toluene hydrochloride
Glänzendes Grüntürkis.Shiny green turquoise.
0,54 Gew.-% A 42
0,60 Gew.-% 3-(Diethylaminomethyl)-4-hydroxy
anilindihydrochlorid0.54% by weight of A 42
0.60% by weight of 3- (diethylaminomethyl) -4-hydroxy aniline dihydrochloride
Glänzendes Mittelbraun.Glossy medium brown.
0,54 Gew.-% A 42
0,32 Gew.-% 2-Chlor-4-aminophenol0.54% by weight of A 42
0.32 wt% 2-chloro-4-aminophenol
Glänzendes Pupurbraun.Shiny copper brown.
0,54 Gew.-% A 42
0,40 Gew.-% 2,6-Dichlor-4-aminophenol0.54% by weight of A 42
0.40% by weight 2,6-dichloro-4-aminophenol
Glänzendes Tiefblau. Shiny deep blue.
0,54 Gew.-% A 42
0,60 Gew.-% 2,6-Dibrom-4-aminophenol0.54% by weight of A 42
0.60% by weight 2,6-dibromo-4-aminophenol
Glänzendes Tiefblau.Shiny deep blue.
0,54 Gew.-% A 42
0,32 Gew.-% 2-Amino-4-chlor-phenol0.54% by weight of A 42
0.32 wt% 2-amino-4-chlorophenol
Glänzendes Gelbbraun.Shiny tan.
0,54 Gew.-% A 42
0,28 Gew.-% 2-Amino-4-methylphenol0.54% by weight of A 42
0.28 wt% 2-amino-4-methylphenol
Glänzendes Gelbbeige.Shiny yellow beige.
Claims (1)
- a) 1-β-Hydroxyethyloxy-2,4-diaminobenzol bzw. dessen wasserlöslichen Salzen, und
- b) mindestens einer Substanz, ausgewählt aus 1-(β-Hydroxyethyl)-2,5- diaminobenzol, 2-(2'-Hydroxyethyl)-5-aminotoluol, N,N-Bis-(hydroxyethyl)-1,4- diaminobenzol, 4-Amino-3-methylphenol, 2-Amino-5-diethylaminotoluol, 3- (Diethylaminomethyl)-4-hydroxyanilin, 2-Chlor-4-aminophenol, 2-Brom-4- aminophenol, 2,6-Dichlor-4-aminophenol, 2,6-Dibrom-4-aminophenol, 2-Amino-4- chlorphenol, 2-Amino-4-methylphenol und/oder 4-Aminopiperidinoanilin bzw. deren wasserlöslichen Salzen.
- a) 1-β-hydroxyethyloxy-2,4-diaminobenzene or its water-soluble salts, and
- b) at least one substance selected from 1- (β-hydroxyethyl) -2,5-diaminobenzene, 2- (2'-hydroxyethyl) -5-aminotoluene, N, N-bis (hydroxyethyl) -1,4-diaminobenzene , 4-amino-3-methylphenol, 2-amino-5-diethylaminotoluene, 3- (diethylaminomethyl) -4-hydroxyaniline, 2-chloro-4-aminophenol, 2-bromo-4-aminophenol, 2,6-dichloro-4 -aminophenol, 2,6-dibromo-4-aminophenol, 2-amino-4-chlorophenol, 2-amino-4-methylphenol and / or 4-aminopiperidinoaniline or their water-soluble salts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998134651 DE19834651C1 (en) | 1998-07-31 | 1998-07-31 | Hair color based on an oxidation dye precursor reacting with peroxide contains 1-hydroxyethoxy-2,4-diaminobenzene and aminobenzene, aminophenol and 4-aminopiperidinoaniline compound(s) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1998134651 DE19834651C1 (en) | 1998-07-31 | 1998-07-31 | Hair color based on an oxidation dye precursor reacting with peroxide contains 1-hydroxyethoxy-2,4-diaminobenzene and aminobenzene, aminophenol and 4-aminopiperidinoaniline compound(s) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19834651C1 true DE19834651C1 (en) | 2000-03-02 |
Family
ID=7876046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1998134651 Expired - Lifetime DE19834651C1 (en) | 1998-07-31 | 1998-07-31 | Hair color based on an oxidation dye precursor reacting with peroxide contains 1-hydroxyethoxy-2,4-diaminobenzene and aminobenzene, aminophenol and 4-aminopiperidinoaniline compound(s) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19834651C1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1197202A1 (en) * | 2000-10-14 | 2002-04-17 | GOLDWELL GmbH | Hair dye composition comprising 2,6-diaminopurine |
| WO2002032379A3 (en) * | 2000-10-14 | 2003-01-23 | Henkel Kgaa | Oxidation colorants containing 2-chloro-4-aminophenol |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2737138C2 (en) * | 1976-08-20 | 1985-01-10 | L'Oreal S.A., 75008 Paris | Colorants for keratin fibers |
-
1998
- 1998-07-31 DE DE1998134651 patent/DE19834651C1/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2737138C2 (en) * | 1976-08-20 | 1985-01-10 | L'Oreal S.A., 75008 Paris | Colorants for keratin fibers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1197202A1 (en) * | 2000-10-14 | 2002-04-17 | GOLDWELL GmbH | Hair dye composition comprising 2,6-diaminopurine |
| WO2002032379A3 (en) * | 2000-10-14 | 2003-01-23 | Henkel Kgaa | Oxidation colorants containing 2-chloro-4-aminophenol |
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