WO1982000092A1 - Hair coloration method and composition therefor - Google Patents
Hair coloration method and composition therefor Download PDFInfo
- Publication number
- WO1982000092A1 WO1982000092A1 PCT/EP1981/000057 EP8100057W WO8200092A1 WO 1982000092 A1 WO1982000092 A1 WO 1982000092A1 EP 8100057 W EP8100057 W EP 8100057W WO 8200092 A1 WO8200092 A1 WO 8200092A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hair
- phenol
- composition according
- methyl
- amino
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 9
- 150000002989 phenols Chemical class 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- ROTDRFLEBIUGFT-UHFFFAOYSA-N 2-(hydroxymethyl)-5-methylphenol Chemical compound CC1=CC=C(CO)C(O)=C1 ROTDRFLEBIUGFT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 28
- 239000000118 hair dye Substances 0.000 claims description 25
- -1 hydroxyalkyl radical Chemical class 0.000 claims description 14
- 238000004043 dyeing Methods 0.000 claims description 12
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims description 4
- 229940018563 3-aminophenol Drugs 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- 239000000080 wetting agent Substances 0.000 claims description 4
- NKNCGBHPGCHYCQ-UHFFFAOYSA-N (2,5-diaminophenyl)methanol Chemical compound NC1=CC=C(N)C(CO)=C1 NKNCGBHPGCHYCQ-UHFFFAOYSA-N 0.000 claims description 3
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 claims description 3
- JQVAPEJNIZULEK-UHFFFAOYSA-N 4-chlorobenzene-1,3-diol Chemical compound OC1=CC=C(Cl)C(O)=C1 JQVAPEJNIZULEK-UHFFFAOYSA-N 0.000 claims description 3
- QGNGOGOOPUYKMC-UHFFFAOYSA-N 4-hydroxy-6-methylaniline Chemical compound CC1=CC(O)=CC=C1N QGNGOGOOPUYKMC-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940031826 phenolate Drugs 0.000 claims description 3
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 claims description 2
- 229940075142 2,5-diaminotoluene Drugs 0.000 claims description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 claims description 2
- KJTXCKZBFHBRQT-UHFFFAOYSA-N 2-amino-5-ethoxyphenol Chemical compound CCOC1=CC=C(N)C(O)=C1 KJTXCKZBFHBRQT-UHFFFAOYSA-N 0.000 claims description 2
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 claims description 2
- ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 claims description 2
- HGUYBLVGLMAUFF-UHFFFAOYSA-N 2-methoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=CC=C1N HGUYBLVGLMAUFF-UHFFFAOYSA-N 0.000 claims description 2
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 claims description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 claims description 2
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 239000000982 direct dye Substances 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- BQMNYXSBLZROPA-UHFFFAOYSA-N 2-(2-hydroxyethyl)-5-methylphenol Chemical compound CC1=CC=C(CCO)C(O)=C1 BQMNYXSBLZROPA-UHFFFAOYSA-N 0.000 claims 1
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical compound NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 claims 1
- TVQDIGAZKJXXLX-UHFFFAOYSA-N 3-(3-hydroxypropyl)phenol Chemical compound OCCCC1=CC=CC(O)=C1 TVQDIGAZKJXXLX-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000002110 toxicologic effect Effects 0.000 abstract description 3
- 231100000027 toxicology Toxicity 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract description 2
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000005923 long-lasting effect Effects 0.000 abstract 1
- 230000000149 penetrating effect Effects 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000037308 hair color Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- KZTWOUOZKZQDMN-UHFFFAOYSA-N 2,5-diaminotoluene sulfate Chemical compound OS(O)(=O)=O.CC1=CC(N)=CC=C1N KZTWOUOZKZQDMN-UHFFFAOYSA-N 0.000 description 2
- 229940075147 2,5-diaminotoluene sulfate Drugs 0.000 description 2
- VOQAOTALYZIMDB-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl hydrogen sulfate Chemical compound OCCOCCOCCOCCOS(O)(=O)=O VOQAOTALYZIMDB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion 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
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- 229940113489 2,4-diaminophenoxyethanol Drugs 0.000 description 1
- RUXVXMGMLQZXOL-UHFFFAOYSA-N 2-(4-methyl-3-nitrophenyl)ethanol Chemical compound CC1=CC=C(CCO)C=C1[N+]([O-])=O RUXVXMGMLQZXOL-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- YRUSZWMOVICUOY-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-methylphenol Chemical compound CC1=CC=C(CCO)C=C1O YRUSZWMOVICUOY-UHFFFAOYSA-N 0.000 description 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 1
- WZNKBDUWSKJHEG-UHFFFAOYSA-N 54941-44-5 Chemical compound CC1=CC=C(CC(O)=O)C=C1[N+]([O-])=O WZNKBDUWSKJHEG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 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
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Chemical class 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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/19—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms
Definitions
- the invention relates to an agent and a method for the oxidative dyeing of hair based on a substituted phenol of the general formula
- R 1 represents a hydroxyalkyl radical with 1 to 4 carbon atoms and R 2 represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, as a coupler substance.
- Oxidation dyes have become very important for hair coloring.
- the coloration arises from the reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
- Mainly 1,4-diaminobenzene, 2,5-diaminotoluene, 3-methyl-4-aminophenol and p-aminophenol are used as developer substances.
- the preferred coupler substances are ⁇ -naphthol, resorcinol, 4-chlororesorcinol, 2-methylresorcinol, m-aminophenol, 5-amino-o-k ⁇ esol and derivatives of m-phenylenediamine such as m-toluenediamine and 2,4-diaminoanisole.
- Oxidation dyes which are used to dye human hair, are subject to numerous special requirements. So they have to be safe from a toxicological and dermatological point of view and to achieve the desired coloration
- Allow intensity Furthermore, it is necessary that a wide range of different color shades can be produced by combining suitable developers and coupler components. In addition, good light, permanent wave, acid and rub fastness are required for the achievable hair coloring. In any case, such hair coloring must remain stable over a period of at least 4 to 6 weeks without exposure to light, chemical agents and rubbing.
- agents for the oxidative dyeing of hair which are a combination of developer substances known in hair dyeing with at least one substituted phenol of the general formula
- R 1 is a hydroxyalkyl radical with 1 to 4 carbon atoms and R 2 represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, also in the form of the phenolate with organic or inorganic bases, as a coupler substance, to an outstanding extent meet the task.
- the substituted phenols of the formula given as coupler substances in the hair colorants according to the invention are readily soluble in water with the addition of alkalis such as sodium hydroxide and, moreover, have an unexpectedly good shelf life, in particular as a constituent of the hair colorants according to the invention.
- alkalis such as sodium hydroxide
- suitable coupler substances of the formula given which are contained in the hair colorants according to the invention are in particular
- the coupler substances mentioned of which 2-hydroxymethyl-5-methylphenol and 3- ( ⁇ -hydroxyethyl) -6-methylphenol are preferred, in a concentration of about 0.01 to 3.0 percent by weight, in particular 0.1 to 2.0 percent by weight.
- the hair colorants can additionally contain known coupler substances, in particular ⁇ -naphthol, 3,4-diaminobenzoic acid, resorcinol, 4-chlororesorcinol, 2-methylresorein, m-aminophenol and 3-amino-6-methylphenol.
- coupler substances in particular ⁇ -naphthol, 3,4-diaminobenzoic acid, resorcinol, 4-chlororesorcinol, 2-methylresorein, m-aminophenol and 3-amino-6-methylphenol.
- 4-oxy-l, 2-methylenedioxy-benzene and 4-amino-1,2-methylenedioxybenzene can also be used advantageously as a coupler substance.
- 1,4-diaminobenzene, 2,5-diarainctoluene, 2,5-diaminoanisole, p-aminophenol and also come as a component of the hair colorants according to the invention 3-methyl-4-aminophenol into consideration.
- 2,5-Diaminobenzyl alcohol and 2- ⁇ ß-hydroxyethyl) -1,4-diaminobenzene can also be used advantageously as a developer substance.
- Both the substituted phenols of the formula given and the known couplers and developer substances used according to the invention can each be present in the hair dye alone or as a mixture with one another.
- the total amount of the developer substance-coupler substance combination contained in the hair colorants described here should be about 0.1 to 5.0 percent by weight, in particular 0.5 to 3.0 percent by weight.
- the developer components are generally used in approximately equimolar amounts, based on the coupler components. However, it is not disadvantageous if the developer component is present in a certain excess or deficit in this regard.
- the hair colorants of this application can additionally use other color components, for example 6-amino-3-methylphenol, 6-amino-2-methylphenol and 6-amino-3-ethoxyphenol, and also conventional direct dyes, for example triphenylmethane dyes such as Diamond Fuchsin (CI 42 510) and Leather Ruby HF (CI 42 520), aromatic nitro dyes such as 2-nitro-l, 4-diaminobenzene and 2-amino-4-nitrophenol, azo dyes such as Acid Brown 4 (CI 14 805) and Acid Blue 135 CC.I.
- anthraquinone dyes such as Disperse Red 15 (CI 60 710) and Disperse Violet 1 (CI 61 100), also contain 1,4,5,8-tetraamino-anthraquinone and 1,4-diamino anthraquinone.
- antioxidants such as ascorbic acid or sodium sulfite, perfume oils, complexing agents, wetting agents, emulsifiers, thickeners, care substances and others, can also be present in the hair colorants.
- the preparation form can be that of a solution, preferably a cream, a gel or an emulsion.
- Their composition is a mixture of the dye components with the constituents customary for such preparations.
- the usual constituents of creams, emulsions or gels are, for example, wetting agents or emulsifiers from the classes of anionic, cationic or nonionic surface-active substances such as fatty alcohol sulfates, alkyl sulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides, further thickeners such as higher fatty alcohols, starch, cellulose derivatives, paraffin oil and fatty acids as well as care agents such as lanolin derivatives, cholesterol and pantothenic acid.
- ingredients mentioned are ver in the usual amounts for such purposes uses, for example, the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, while the thickeners can be contained in the preparations in an amount of about 0.1 to 25 percent by weight.
- the hair colorants according to the invention can react weakly acidic, neutral or alkaline.
- they have a pH in the alkaline range between 8.0 and 11.5, the setting preferably being made with ammonia.
- organic amines for example monoethanolamine or triethanolamine, can also be used.
- the hair colorants which contain a combination of developer substances known in hair dyeing with at least one substituted phenol of the stated formula as coupler substance and, if appropriate, additionally known coupler substances, are mixed with an oxidizing agent shortly before use and are worn Mix on hair.
- the main oxidizing agents used to develop hair color are hydrogen peroxide, for example as a 6% aqueous solution or its addition compounds with urea, melamine or sodium borate.
- the preparation of the 2-hydroxymethyl-5-methylphenol is based on the m-cresotinic acid available in industrial quantities, and this is esterified 1) into the corresponding m-cresotinic acid ester and reduced 2) with lithium aluminum hydride.
- 2-hydroxymethyl- ⁇ -methylphenol can be prepared from o-cresotinic acid.
- the hair colorants according to the invention offer a wide range of different color shades, which range from blonde to brown, ashy, purple, violet, golden to blue and matt colors.
- the colors are characterized by their special durability and fastness to wear.
- the observed coloring result is independent of the structure of the hair being dyed. This means that the shades achieved with the hair colorants according to the invention are easily reproducible.
- 50 g of the above hair dye are mixed shortly before use with 50 ml of hydrogen peroxide solution (6%) and the mixture is then applied to blonde human hair. After an exposure time of 30 minutes at about 40 ° C, rinsed with water and dried. The hair is colored with an intense shade of blue.
- this hair dye Shortly before use, 50 g of this hair dye is mixed with 50 ml of hydrogen peroxide solution (6%) and the mixture is left for 30 minutes Apply 40 ° C to blonde human hair. Then it is rinsed with water and dried. The hair has a gray-violet-bluish color.
- this hair dye 50 g of this hair dye are mixed with 50 ml of hydrogen peroxide solution (6%) shortly before use and the mixture is then applied to blonde human hair. After an exposure time of 30 minutes at 40 ° C rinsed with water and dried. The hair is colored light ash brown.
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR8108676A BR8108676A (pt) | 1980-07-07 | 1981-05-27 | Composicao e processo para otingimento de cabelos |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3025715800707 | 1980-07-07 | ||
| DE19803025715 DE3025715A1 (de) | 1980-07-07 | 1980-07-07 | Mittel und verfahren zum faerben von haaren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1982000092A1 true WO1982000092A1 (en) | 1982-01-21 |
Family
ID=6106598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1981/000057 WO1982000092A1 (en) | 1980-07-07 | 1981-05-27 | Hair coloration method and composition therefor |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4755188A (en, 2012) |
| EP (1) | EP0043436B1 (en, 2012) |
| JP (1) | JPS57501126A (en, 2012) |
| BR (1) | BR8108676A (en, 2012) |
| DE (2) | DE3025715A1 (en, 2012) |
| MX (1) | MX152694A (en, 2012) |
| WO (1) | WO1982000092A1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5910304A (en) * | 1982-12-13 | 1999-06-08 | Texas A&M University System | Low-dose oral administration of interferons |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3239295A1 (de) * | 1982-10-23 | 1984-04-26 | Henkel KGaA, 4000 Düsseldorf | Haarfaerbemittel |
| DE3441148A1 (de) * | 1984-11-10 | 1986-05-15 | Wella Ag, 6100 Darmstadt | Oxidationshaarfaerbemittel auf der basis von 4-amino-2-hydroxyalkylphenolen |
| DE3610396A1 (de) * | 1986-03-27 | 1987-10-01 | Wella Ag | Mittel und verfahren zur oxidativen faerbung von haaren |
| US8047024B2 (en) * | 2007-05-07 | 2011-11-01 | Whirlpool Corporation | Control and wash cycle for activation and deactivation of chemistry in the wash bath of an automatic washer |
| FR2974509B1 (fr) | 2011-04-29 | 2013-10-11 | Oreal | Composition de coloration mettant en oeuvre un coupleur phenolique particulier en milieu riche en corps gras, procedes et dispositif |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE660519A (en, 2012) * | 1964-03-02 | 1965-09-02 | ||
| FR2132214A1 (en) * | 1971-03-30 | 1972-11-17 | Procter & Gamble | Hair dye compsn - contg guanidine or arginine oxidation dye precursor and peroxide |
| DE2840830A1 (de) * | 1978-09-20 | 1980-04-03 | Wella Ag | Mittel und verfahren zum faerben von haaren |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU54273A1 (en, 2012) * | 1967-08-08 | 1969-03-24 | ||
| US3861868A (en) * | 1971-03-30 | 1975-01-21 | Procter & Gamble | Dyeing human hair with oxidation dyes and arginine or a protamine protein |
| GB1489344A (en) * | 1974-01-18 | 1977-10-19 | Unilever Ltd | Hair dyeing composition |
-
1980
- 1980-07-07 DE DE19803025715 patent/DE3025715A1/de not_active Withdrawn
-
1981
- 1981-05-27 JP JP56501829A patent/JPS57501126A/ja active Pending
- 1981-05-27 DE DE8181104079T patent/DE3160813D1/de not_active Expired
- 1981-05-27 WO PCT/EP1981/000057 patent/WO1982000092A1/en unknown
- 1981-05-27 BR BR8108676A patent/BR8108676A/pt unknown
- 1981-05-27 EP EP81104079A patent/EP0043436B1/de not_active Expired
- 1981-07-02 MX MX188136A patent/MX152694A/es unknown
-
1987
- 1987-01-20 US US07/005,256 patent/US4755188A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE660519A (en, 2012) * | 1964-03-02 | 1965-09-02 | ||
| FR2132214A1 (en) * | 1971-03-30 | 1972-11-17 | Procter & Gamble | Hair dye compsn - contg guanidine or arginine oxidation dye precursor and peroxide |
| DE2840830A1 (de) * | 1978-09-20 | 1980-04-03 | Wella Ag | Mittel und verfahren zum faerben von haaren |
Non-Patent Citations (3)
| Title |
|---|
| Beilsteins Handbuch der Organischen Chemie, 4. Auflage 4. Erg{nzungswerk, Band 6, 1980 (Springer Verlag, Berlin, DE) Seite 5964, oben, Formel XI, Seite 5970, unten, Formel II * |
| Beilsteins Handbuch der Organischen Chemie, 4. Auflage, 1. Erg{nzungswerk, Band 6, 1931 (Springer Verlag, Berlin, DE) Seite 448,6 * |
| Beilsteins Handbuch der Organischen Chemie, 4. Auflage, Hauptwerk, Band 6, 1923 (Springer Verlag, Berlin, DE) Seite 903,6 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5910304A (en) * | 1982-12-13 | 1999-06-08 | Texas A&M University System | Low-dose oral administration of interferons |
Also Published As
| Publication number | Publication date |
|---|---|
| US4755188A (en) | 1988-07-05 |
| MX152694A (es) | 1985-10-11 |
| DE3025715A1 (de) | 1982-01-28 |
| JPS57501126A (en, 2012) | 1982-07-01 |
| BR8108676A (pt) | 1982-05-25 |
| DE3160813D1 (en) | 1983-10-06 |
| EP0043436A1 (de) | 1982-01-13 |
| EP0043436B1 (de) | 1983-08-31 |
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