GB2078747A - Meta-phenylenediamine dye couplers - Google Patents
Meta-phenylenediamine dye couplers Download PDFInfo
- Publication number
- GB2078747A GB2078747A GB8120127A GB8120127A GB2078747A GB 2078747 A GB2078747 A GB 2078747A GB 8120127 A GB8120127 A GB 8120127A GB 8120127 A GB8120127 A GB 8120127A GB 2078747 A GB2078747 A GB 2078747A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition according
- composition
- acid
- hair
- compound
- 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.)
- Granted
Links
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 121
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000000975 dye Substances 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
- 238000004043 dyeing Methods 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 40
- -1 alkyl radical Chemical class 0.000 claims description 32
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 22
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 16
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 11
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 102000011782 Keratins Human genes 0.000 claims description 9
- 108010076876 Keratins Proteins 0.000 claims description 9
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 235000006708 antioxidants Nutrition 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- GFHYFPARONGSCD-UHFFFAOYSA-N n-(2-hydroxy-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1O GFHYFPARONGSCD-UHFFFAOYSA-N 0.000 claims description 6
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 6
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 239000002243 precursor 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
- 230000008719 thickening Effects 0.000 claims description 4
- HWWIVWKTKZAORO-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-ol Chemical compound O1CCNC2=CC(O)=CC=C21 HWWIVWKTKZAORO-UHFFFAOYSA-N 0.000 claims description 3
- KZQYIMCESJLPQH-UHFFFAOYSA-N Demethylated antipyrine Chemical compound N1C(C)=CC(=O)N1C1=CC=CC=C1 KZQYIMCESJLPQH-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 3
- ANLILZBBUVRVRP-UHFFFAOYSA-N (3-hydroxy-4-methylphenyl)urea Chemical compound CC1=CC=C(NC(N)=O)C=C1O ANLILZBBUVRVRP-UHFFFAOYSA-N 0.000 claims description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 2
- 229940122930 Alkalising agent Drugs 0.000 claims description 2
- 229920000084 Gum arabic Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 235000010323 ascorbic acid Nutrition 0.000 claims description 2
- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 229960005070 ascorbic acid Drugs 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- QFCGWLMVBQWKLP-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methoxyphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(OC)C(O)=C1 QFCGWLMVBQWKLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 235000010413 sodium alginate Nutrition 0.000 claims description 2
- 239000000661 sodium alginate Substances 0.000 claims description 2
- 229940005550 sodium alginate Drugs 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 claims 1
- KQCPMLJLAVCUOF-UHFFFAOYSA-N 3-methyl-3,4-dihydro-2h-1,4-benzoxazin-7-amine Chemical compound NC1=CC=C2NC(C)COC2=C1 KQCPMLJLAVCUOF-UHFFFAOYSA-N 0.000 claims 1
- QZHXKQKKEBXYRG-UHFFFAOYSA-N 4-n-(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1 QZHXKQKKEBXYRG-UHFFFAOYSA-N 0.000 claims 1
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims 1
- 241000978776 Senegalia senegal Species 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000000850 deacetylating effect Effects 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000118 hair dye Substances 0.000 abstract description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 30
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 14
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
- 235000011114 ammonium hydroxide Nutrition 0.000 description 14
- 229940055577 oleyl alcohol Drugs 0.000 description 14
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 14
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 12
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 10
- 229960003330 pentetic acid Drugs 0.000 description 10
- 238000003756 stirring Methods 0.000 description 8
- 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 7
- 241001024304 Mino Species 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241001070941 Castanea Species 0.000 description 4
- 235000014036 Castanea Nutrition 0.000 description 4
- 241000640882 Condea Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 3
- IALKJCXEPFRYML-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CC1=CC(N)=CC(C)=C1N IALKJCXEPFRYML-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 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 3
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000010902 straw Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- PXRLAWPHECEIOA-UHFFFAOYSA-N 1-[3-(methylamino)-4-nitrophenoxy]ethanol Chemical compound CNC1=CC(OC(C)O)=CC=C1[N+]([O-])=O PXRLAWPHECEIOA-UHFFFAOYSA-N 0.000 description 2
- VXYWXJXCQSDNHX-UHFFFAOYSA-N 2-(2,4-diaminophenoxy)ethanol;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(OCCO)C(N)=C1 VXYWXJXCQSDNHX-UHFFFAOYSA-N 0.000 description 2
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 238000010953 Ames test Methods 0.000 description 2
- 231100000039 Ames test Toxicity 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- QMJDEXCUIQJLGO-UHFFFAOYSA-N [4-(methylamino)phenyl] hydrogen sulfate Chemical compound CNC1=CC=C(OS(O)(=O)=O)C=C1 QMJDEXCUIQJLGO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 description 2
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000002352 nonmutagenic effect Effects 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 229960002969 oleic acid Drugs 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AVTBZCRMQZAKDR-UHFFFAOYSA-N 1-[4-(methylamino)-3-nitrophenoxy]ethanol Chemical compound CNC1=CC=C(OC(C)O)C=C1[N+]([O-])=O AVTBZCRMQZAKDR-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- GIGNQZIJYUEWTI-UHFFFAOYSA-N 2,3,5-trihydroxytoluene Chemical compound CC1=CC(O)=CC(O)=C1O GIGNQZIJYUEWTI-UHFFFAOYSA-N 0.000 description 1
- VKTCQRMXVKTIQJ-UHFFFAOYSA-N 2,6-diaminobenzene-1,4-diol;dihydrochloride Chemical compound Cl.Cl.NC1=CC(O)=CC(N)=C1O VKTCQRMXVKTIQJ-UHFFFAOYSA-N 0.000 description 1
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 1
- UTHUZYBSSBFPES-UHFFFAOYSA-N 2-(4-amino-3-nitrophenoxy)ethanol Chemical compound NC1=CC=C(OCCO)C=C1[N+]([O-])=O UTHUZYBSSBFPES-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- ANHZPHIPRWOGCD-UHFFFAOYSA-N 4-amino-2-methyl-5-nitrophenol Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1O ANHZPHIPRWOGCD-UHFFFAOYSA-N 0.000 description 1
- IQXUIDYRTHQTET-UHFFFAOYSA-N 4-amino-3-nitrophenol Chemical compound NC1=CC=C(O)C=C1[N+]([O-])=O IQXUIDYRTHQTET-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 241000557626 Corvus corax Species 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 240000007582 Corylus avellana Species 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000083869 Polyommatus dorylas Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UMVWJRMJMOPKKM-UHFFFAOYSA-N ethyl n-(3-hydroxy-4-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(C)C(O)=C1 UMVWJRMJMOPKKM-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ODVQLBCSJIDHJL-UHFFFAOYSA-N n-(3-hydroxy-2,4-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(O)=C1C ODVQLBCSJIDHJL-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Coloring (AREA)
Abstract
New dye couplers are disclosed, which are particularly suitable for use in hair dye compositions. These couplers have the general formula: <IMAGE> in which Z represents either a polyhydroxyalkyl radical in which the alkyl group contains from 3 to 6 carbon atoms, the said radical containing 2 or 3 hydroxyl groups, or an alkyl radical containing at least one chain heteroatom and at least one hydroxyl group, the said alkyl radical containing from 4 to 8 carbon atoms, and include their acid salts.
Description
SPECIFICATION
Meta-phenylenediamines and the process for their manufacture, dyeing compositions in which they are present and corresponding dyeing process
The present invention relates to new metaphenylenediamines, a process for their preparation, dyeing compositions, for keratin fibres, in which they are present, and a hair-dyeing process using the said dyeing compositions.
In the field of dyeing keratin fibres such as hair or fur, meta-phenylenediamines have an important function which has been known for a long time; they form part of the class of compounds commonly referred to as "couplers". In association with paraphenylenediamines or para-aminophenols, which are compounds referred to as "oxidation bases", couplers give rise, in an oxidising alkaline medium, to coloured indamines, indoanilines or indophenols.
The association of meta-phenylenediamines with para-phenylenediamines, in an oxidising alkaline medium and more particularly in the presence of hydrogen peroxide, gives rise to indamines capable of imparting very strong blue colorations to keratin fibres. Furthermore, when associated with para-aminophenols, metaphenylenediamines give, in an oxidising alkaline medium, indoanilines which impart, to keratin fibres, red colorations containing a greater or lesser degree of purple. Thus, as couplers, meta-phenylenediamines have a dual function in hair dyeing, namely the provision of blue and the provision of red, that is to say the provision of two fundamental colours which are essential forobtaining not only blacks and greys, but also ashen or coppery chestnuts.
.Despite this important function, such couplers have hitherto been limited in practice to a very restricted number of compounds. This very limited number is explained by the fact that only compounds which can be selected for the dyeing of keratin fibres are those which make it possible to obtain dyes of
good quality, that is to say dyes which do not change with time, and, in particular, do not change when subjected either to light or to adverse weather conditions. Moreover, in the cse of hair dyes, the couplers used must be very harmless ard, in particular, must be virtually non-mutagenic in the Ames test on
Salmonella thyphimurium (TA 1538, TA 98, TA 100, TA 1537 and TA 1 535, in the absence or presence of "S9 MIX" activated by "Arochlor 1254").
The object of the present invention is to provide new chemical compounds serving as meta
phenylenediamine couplers which can be used in dyeing compositions for keratin fibres. The
compounds according to the invention can be used particularly in hair dyeing because they not only
possess the dyeing properties of a good coupler, but they also have the advantage of being very
harmless and are non-mutagenic in the Ames tests as defined above. French Patent Application 2,362,116 discloses meta-phenylenediamines which give satisfactory results in hair dyeing, this
invention provides other meta-phenylenediamines of the same type.
The present invention provides a chemical compound of the general formula
in which formula Z represents either a polyhydroxyalkyl radical in which the alkyl group contains from 3 to 6 carbon atoms, the said radical containing 2 or 3 hydroxyl groups, or an alkyl radical interrupted by at least one hetero-atom and containing at least one hydroxyl group, the said alkyl chain containing from 4 to 8 carbon atoms, and the corresponding acid salts such as the hydrochloride, sulphate, tartrate, phosphate, lactate, hydrobromide and citrate.
Preferably, if Z represents an alkyl radical interrupted by at least one hetero-atom, the hetero-atom (or hetero-atoms) is (or are) an oxygen atom (or oxygen atoms); the hydroxyl group (or groups) of the alkyl radical (chain) may or may not be at the end of the chain.
The present invention also provides a process for the preparation of the compounds of the formula (I) defined above. In this process, a halogen derivative of the formula X-Z, X being a halogen and Z being as defined for formula (I), is reacted with an alkali metal salt of 2-acetylamino-4-nitrophenol so as to condense the radical Z onto the nucleus, an alkali metal halide being eliminated, the nitro group of the product obtained is then reduced and, finally, the product is deacylated to obtain the compound of the formula (I).
In a preferred embodiment, the halogen X which is used is chlorine and the alkali metal is potassium; the reduction of the nitro group is suitably carried out in alcoholic solution, under reflux, using zinc powder in the presence of ammonium chloride.
The present invention also provides a dyeing composition for keratin fibres, and in particular for hair, the said composition containing at least one oxidation base, in a cosmetically acceptable carrier, and being characterised in that it contains, as the coupier, at least one compound of the formula (I) or a corresponding acid salt.
In general, the meta-phenylenediamines of the formula (I) are present in the dyeing composition according to the invention in an amount of 0.001 to 2.5% by weight, relative to the total weight of the composition.
The meta-phenylenediamines according to the invention can be incorporated into dyeing compositions together withs oxidation bases such as:
A. The para-phenylenediamines of the general formula (ill):
or the corresponding acid salts, in which formula Rr, R2and R3are identical or different and represent a hydrogen atom, an alkyl radical having from 1 to 4 carbon atoms or an alkoxy radical having 1 or 2 carbon atoms, and R4 and P5 are identical or different and represent a hydrogen atom, an alkyl or hydroxyalkyl radical, an alkoxyalkyl radical in which the alkoxy group contains 1 or 2 carbon atoms, or a carbamylalkyl, mesylaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbethoxyaminoalkyl, aminoalkyl, monoalkylaminoalkyl, diaikylaminoalkyl, piperidinoalkyl or morpholinoalkyl radical, the alkyl groups in R4 and R5 having from 1 to 4 carbon atoms, or alternatively R4 and P5 form a piperidino or morpholino group together with the nitrogen atom to which they are attached, with the provisos that R, and R3 represent a hydrogen atom if R4 and R5 do not represent a hydrogen atom.
B. The para-aminophenols of the general formula (III):
or the corresponding acid salts, in which formula R6 represents a hydrogen atom, an alky radical containing from 1 to 4 carbon atoms or a halogen atom such as chlorine or bromine.
C. Heterocyclic bases such as 2,5-diaminopyridine, 3-methyi-7-aminobenzomorpholine and 5 aminoindoie.
It has been found that the use of the meta-phenylenediamines according to the invention, with at least one oxidation bass mentioned under A, B or C above, makes it possible to obtain dyeing compositions which give the hair shades of good quality, which are very resistant especially to washing.
In general, the couplers according to the invention make it possible to obtain, with the paraphenylenediamines, blue colorations which are more or less rich in green or purple, and, with the paraaminophenols, red colorations. The dyeing compositionss according to the invention can thus advantageously contain both para-phenylenediamines and para-aminophenols.
It has been found that particularly valuable results can be obtained by using, as the compounds of the formula (I) or their corresponding salts with acids, 2,4-diaminophenyl P-(P'-hydroxyethoxy)-ethyl ether, especially in the form of the dihydrochloride, and/or 2,4-diaminophenyl ,y-dihydrnxyprnpyl ether, especially in the form of the dihydrochloride.
Apart from the coupler (or couplers) of the formula (I) and the associated oxidation base (or bases), the dyeing compositions of the present invention can contain one or more of the following products: 1) either known couplers, for example resorcinol, 2-methylresorcinol, meta-aminophenol, 2-methyl-5a minophenol, 2-methyl-5-[N-(-hydrnxyethyl)-amino]-phenol, 6-hydroxybenzomorpholine, 2,6dimethyl-3-acetylaminophenol, 2-methyl--5-carbethoxyaminophenol, 2-methoxy-5 carbethoxyaminophenol, 2-methyl-5-ureidophenol and 1 -phenyl-3-methylpyrazol-5-one;; 2) ortho-phenylenediamines and ortho-aminophenols optionally containing substituents on the nucleus or on the amine groups, or also ortho-diphenol, it being possible, by means of complex oxidation mechanisms, for these products to lead to new coloured compounds, either by cyclisation with themselves or by reaction with the para-phenylenediamines; 3) dyestuff precursors of the benzene series, containing on the nucleus, at least three substituents selected from hydroxyl, methoxy and amino groups, such as 2,6-diaminohydroquinone dihydrochloride, 2,6-dia mino-4-[N,N-bis-(ethyl)-a mino]-phenol trihydrochloride, 2,4-diaminophenyl dihydrochloride, 1 ,2,4-trihydroxybenzene, 2,3,5-trihydroxytoluene or 4-methoxy-2-am ino-N-(-hydrnxyethyl)-aniline; 4) dyestuff precursors of the naphthalene series, such as 2-hydroxy-1 ,4-naphthoquinone and 5 hydroxy-1 ,4-naphthoquinone;; 5) leuco-derivatives of indoanilines or of indophenols, such as 4,4'-dihydroxy-2-amino-5methyldiphenylamine, 4,4'-dihydrnxy-2-[N-(hydrnxyethyl)-aminoJ-5-methyl-2'-chIorndiphenylamine, 2,4'-diamino-4-hydroxy-5-methyl-diphenylamine, 2,4-dihydrnxy-41-[N-(methoxyethyl)-aminoj- diphenylamine or 2,4-dihydroxy-5-methyi-4'-[N-(/3-methoxyethyl)-amino]-diphenylamine;; and (6 direct dyestuffs, for example nitro benzene dyestuffs, such as 1 -[N,N-bis-(ss-hydroxyethyl)-amino]-3- nitro-4-(N'-methyla mino)-benzene, 1 -[N-methyl-N-(p-hydroxyethyl)-amino]-3-nitro-4-[N'-(X3- hydroxyethyl)-a mino]-benzene, 1 -[N-methyl-N-(/3-hydroxyethyl)-am ino]-3-nitro-4-( N'-methylamino)- benzene, 3-nitro-4-[N-(P-hydroxyethyl)-a mino]-anisole, 3-nitro-4-[N-(p-hydroxyethyl)-a mino]-phenol, 3-nitro-4-aminophenoxy-ethanol, 3-nitro-4-(N-methylamino)-phenoxy-ethanol or 2-ZN-(P-hydroxy- ethyl)-amino]-5-nitroanisole.
The pH of the dyeing compositions according to the invention is basic, for example, from 8 to 1 1.5. Amongst the alkalising agents which can be used to adjust the pHs there may be mentioned ammonia, alkylamines such as ethylamine or triethylamine, alkanolamines such as mono-, di- or triethanolamine, alkylalkanolamines such as methyldiethanolamine, sodium hydroxide or potassium hydroxide and sodium carbonate, potassium carbonate or ammonium carbonate. Amongst the acidifying agents which can be used, there may be mentioned lactic acid, acetic acid, tartaric acid and phosphoric acid.
The cosmetically acceptable carrier which is associated with the base(s), coupler(s) and, if appropriate, direct dyestuff(s) of the composition can comprise, apart from water, surface-active agents, organic solvents, thickening products, antioxidants, penetrating agents, foaming agents, sequestering agents, film-forming products, treating agents and perfumes, for example.
Anionic, cationic, non-ionic and amphoteric surface-active agents, or a mixture thereof, can be included in the composition according to the invention. Amongst the surface-active agents which can be used in particular, there may be mentioned alkylbenzenesulphonates, alkylnaphthalenesulphonates, the sulphates, ether-sulphates and sulphonates of fatty alcohols, quaternary ammonium salts such as trimethylcetylammonium bromide and cetylpyridinium bromide, fatty acid diethanolamines, polyoxyethyleneated or polyglycerolated acids and alcohols and polyoxyethyleneated or polyglyerolated alkylphenols. Preferably, the surface-active agents are present in the composition according to the invention in an amount of 0.5 to 55% by weight and advantageously 4 to 40% by weight, relative to the total weight of the composition.
Organic solvents can also be included in the composition according to the invention in order to solubilise compounds which would not otherwise be sufficiently soluble in water. Amongst the solvents which can advantageously be used, there may be mentioned ethanol, isopropanol, glycerol, glycols and their ethers, such as 2-butoxyethanol, ethylene glycol, propylene glycol and diethylene glycol monoethyl ether and monomethyl ether. The solvents are advantageously present in the composition in an amount from 1 to 40% by weight and preferably of 5 to 30% by weight, relative to the total weight of the composition.
The thickening products from which can be included in the composition according to the invention include sodium alginate, gum arabic, cellulose derivatives such as methyl cellulose, hydroxycellulose, hydroxypropylmethylcellulose and the sodium salt of carboxymethylcellulose, and acrylic acid polymers; it is also possible to use inorganic thickeners such as bentonite. Preferably, the thickeners are present in an amount from 0.5 to 5% by weight, relative to the total weight of the composition, and advantageously from 0.5 to 3% by weight.
The antioxidants which can be included in the composition according to the invention is advantageously sodium sulphite, thioglycolic acid, mercaptosuccinic acid, sodium bisulphite, ascorbic acid or hydroquinone. These antioxidants are suitably present in the composition in an amount of 0.05 to 1.5% by weight, relative to the total weight of the composition.
The dyeing composition according to the invention generally contains, at the time of use, oxidising agents such as hydrogen peroxide, urea peroxide or per-salts, for example ammonium persulphate.
The dyeing composition according to the invention is suitably in the form of a liquid, a cream, a gel or an aerosol or in any other form suitable for dyeing keratin fibres.
The present invention also provides a hair-dyeing process which is characterised in that a composition according to the invention is mixed with an oxidising agent, in that the said mixture is applied to the hair, in that the mixture is left to act on the hair for a period of, say, 5 to 45 minutes, and in that the hair is rinsed, optionally shampooed and rinsed again, and dried.
The following Examples further illustrate the present invention.
EXAMPLE 1
Preparation of 2,4-diaminophenyl , -hydroxyethoxy)-ethyl ether dihydrochloride
The compound prepared has the following formula:
First stage:
Second stage:
Third stage:
Fourth stage:
First step: Preparation of the potassium salt of 2-acetylamino-4-nitrophenol 2,1 50 ml of ethanol, containing, in solution, 1.89 mols of 80% strength potassium hydroxide solution (133 g), are cooled to -1 00C; 1.89 mols (371 g) of 2-acetylamino-4-nitrophenol are then added gradual!y, whilst stirring and at the same time keeping the temperature below 50C. The potassium salt precipitates. The product is filtered off, washed-with ethanol and dried in vacuo at 50"C.
Second step: Preparation of 2-acetylamino-4-nitrophenyl ,B-(,ss'-hydroxyethoxy)-ethyl ether
0.5 mol (117 g) of the potassium salt of 2-acetylamino-4-nitrophenol is introduced into 500 ml of dimethylformamide; 0.6 mol (64 ml) of diethylene glycol monochlorohydrin is then added, whilst stirring. The mixture is stirred for 8 hours at a temperature of the order of 1 000C and then poured into two litres of ice-cooled water. The crude product is filtered off; it is washed with water, then with an icecooled normal sodium carbonate solution and finally with water. After drying in vacuo and recrystallisation from ethanol, the expected product melts at 1 52 OC.
Analysis of the product obtained gives the following results:
Analysis Calculated for CIzHl6Nz06 Found C % 50.70 50.88 H % 5.67 5.64 N % 9.86 9.74 O% 33.77 33.90 Third step:Preparation of2-acetylamino-4-aminophenyl -('-hydrnxyethoxy)-ethyl ether monohydrochloride
400 ml of ethanol (960 strength), to which 75 ml of water, 10 g of ammonium chloride and 200 g of zinc powder have been added, are heated to the reflux temperature, whilst stirring; 0.32 mol (91 g) or 2-acetylamino-4-nitrophenyi ,B-(p'-hydroxyethoxy)-ethyl ether is then added gradually, whilst at the same time continuing the stirring. After each addition, the reaction medium is decolorised very rapidly.
When the addition of the nitro derivative has ended, the heating is maintained for about ten minutes and the reaction medium is then filtered, the filtrate being collected in 30 ml of ethanol (960 strength) to which 34 ml of 36% strength hydrochloric acid have been added, and which have been cooled beforehand with the aid of a solid carbon dioxide/ethanol mixture. The expected product crystallises in the form of the hydrochloride. it is filtered off, washed with a small amount of absolute ethanol cooled to -1 00C beforehand, and then dried in vacuo at 550C.
Analysis of the product obtained gives the following results:
Analysis Calculated for CI2H1,N204.HC Found C % 49.57 49.56 H % 6.58 6.50 N % 9.63 9.48 O % 22.01 21.83 Cl % 12.19 12.30 Fourth step: Preparation of 2,4-diaminophenyl P-(P'-hydroxyethoxy)-ethyl ether di hydrochloride 0.25 mol (70.9 g) of 2-acetylamino-4-aminophenyl ss-(ss'-hydroxyethoxy)-ethyl ether monohydrochloride is heated to the reflux temperature, whilst stirring, in 210 ml of absolute ethanol saturated with hydrogen chloride.After heating for 10 minutes, dissolution is total and the expected dihydrochloride then starts to precipitate after about half an hour. The heating is maintained for one hour in total and the reaction medium is then cooled to OOC. The dihydrochloride is filtered off, washed with a small amount of absolute ethanol at OOC and then dried in vacuo at 55 C. It melts with decomposition between 180 and 1 850C.
Analysis of the product obtained gives the following results:
Analysis Calculated for CloHl6N20l.2HCl- Found C % 42.12 42.24 H % 6.36 6.39 N % 9.82 9.73 O % 16.83 17.07 Cl % 24.87 24.90-24.94 EXAMPLE 2
Preparation of 2,4-diaminophenyl P,y-dihydroxypropyl ether dihydrochioride
First stage:
Second stage:
Third stage:
First step:Preparation of 2-acetylamino-4-nitrophenyl P,y-dihydroxypropyl ether
0.2 mol (46.8 g) of the potassium salt of 2-acetylamino-4-nitrophenol is introduced into 100 ml of 1 -chloropropane-2,3-diol to which 20 ml of water have been added. The mixture is heated for 1 0 hours in a boiling water-bath. 0.1 mol (13.8 g) of potassium carbonate is added and the heating is then continued for six hours. After cooling and removal of the inorganic salts by filtration, 250 ml of ethanol (960 strength) are added to the filtrate and the mixture is then cooled overnight at OOC. The expected product crystallises. It is filtered off and washed with ethanol, then with a normal sodium carbonate solution and then with water.
After two recrystallisations from ethanol and drying in vacuo at 550C, the product melts at 1 420C.
Analysis of the product obtained gives the following results
Analysis Calculated for CllHl4N.06 Found C % 48.89 48.77 H H % 5.22 5.15 N % 10.37 10.44 0 % 35.52 35.32-35.46 Second step:Preparation of 2-acetylamino-4-aminophenyl ,y-dihyoroxyprnpyl ether hydrochloride 1 7 ml of ethanol (960 strength), to which 2.5 ml of water, 0.4 g of ammonium chloride and 8 g of zinc powder have been added, are heated to the reflux temperature, whilst stirring: 1.35 x 10-2 mols (3.6 g) of 2-acetylamino-4-nitrophenyl ,y-dihydrnxyprnpyl ether are then added gradually, whilst at the same time maintaining the stirring. When the addition has ended and the reaction medium is decolorised, the latter is filtered, the filtrate being collected in 1.5 ml of ethanol (960 strength) to which 1.5 ml of 36% strength hydrochloric acid have been added, cooling being carried out with the aid of an ethanol/solid carbon dioxide mixture. In the cooled filtrate, the expected product crystallises in the form of the hydrochloride. It is filtered off, washed with a small amount of absolute ethanol cooled beforehand, and then dried in vacuo at 550C.
Analysis of the product obtained gives the following results:
Analysis Calculated for C11H16Np4. HCl Found C % 47.74 47.86 H % 6.19 6.26 N % 10.12 10.16 O % 23.13 23.08 Cl % 12.81 12.90 Third step:Preparation of 2,4-diaminophenyl ss,γ-dihydroxypropyl ether dihydrochloride
0.195 mol (54 g) of 2-acetylamino-4-aminophenyl ss,γ-dihydroxypropyl ether hydrochloride is introduced into 270 ml of absolute ethanol saturated to with hydrogen chloride, to which 54 ml of-i 2-N hydrochloric acid have been added. The reaction mixture is heated for one hour in the region of 1000C, whilst stirring. The expected dihydrochloride, which is insoluble in the hot reaction medium, is filtered off. The product is washed with a small amount of absolute ethanol saturated with hydrogen chloride, and then washed with acetone. After drying in vacuo at 550C, it melts with decomposition between 210 and 2150C.
Analysis of the product obtained gives the following results:
Analysis Calculated for C9Hl4N < O3. 2HCI Found C % 39.86 39.96 H % 5.95 6.04 N % 10.33 10.28 O % 17.70 17-64 CI % 1 26.15 26.23 EXAMPLE 3
The following dyeing composition is prepared::
Compound of Example 1 2.85 g
Para-phenylenediamine 1.08 g
Oxyethyleneated nonylphenol containing four moles of ethylene oxide,
sold under the name "CEMULSOL NP4" by "RHONE POULENC" 21 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "CEMULSOL NP9" by "RHONE POULENC" 24 g Oleicacid 4 g
2-Butoxyethanol 3 g
Ethanol (960 strength) 10 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold
under the name "MASQUOL DTPA" 2.5 g
Thioglycolic acid 0.6 g
Ammonia solution (2208 strength) 10 g
Water q.s.p. 100 g
The pH of the composition is equal to 9.7.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 25 minutes at 280C, this mixture imparts to the hair, after rinsing and shampooing, a blue-black coloration.
EXAMPLE 4
The following dyeing composition is prepared:
Compound of Example 2 0.0067 g
Para-phenylenediamine 0.0027 g
2-Butoxyethanol 8 g
Carboxymethylcellulose 2 g
Ammonium lauryl-sulphate 5 g
Ammonium acetate 1 g
Propylene glycol 8 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under
the name "MASQUOL DTPA" 2 g
Thioglycolic acid 0.4 g
Ammonia solution (220B strength) 5 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.1.
50 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 30 minutes at 280C to hair which has been bleached white beforehand, this mixture imparts to the hair, after rinsing and shampooing, a bluish light silver coloration.
EXAMPLE 5
The following dyeing composition is prepared:
Compound of Example 2 0.542 g
Para-aminophenol 0.218 g
Acrylic acid polymer having a molecular weight of 2 to 3 million, sold
under the name "CARBOPOL 934" by "GOODRICH CHEMICAL CO" 1.5 g
Ethanol 11 g
2-Butoxyethanol 5 g
Trimethylcetylammonium bromide 1 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.1 g
Ammonium solution (220B strength) 10 g
Thioglycolic acid 0.2 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.2.
80 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 25 minutes at 280C, this mixture imparts to the hair, after rinsing and shampooing, a dark red coloration.
EXAMPLE 6
The following dyeing composition is prepared:
Compound of Example 1 1.42 g
Para-aminophenol 0.55 g
2-Butoxyethanol 8 g
Propylene glycol 8 g
Carboxymethylcellulose 2 g
Ammonium lauryl-suiphate 5 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under
the name "MASQUOL DTPA" 2 g
Thioglycolic acid 0.4 g
Ammonium solution (220B strength) 10 g
Water Q.S.P. 100 g
The pH of the composition is equal to 10.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 30 minutes at 250C, this mixture imparts to the
hair, after rinsing and shampooing, a coppery-red coloration.
EXAMPLE 7
The following dyeing composition is prepared:
Compound of Example 2 0.271 g 4-[N-(p-Methoxyethyl)-amino]-aniline dihydrochloride 0.239 g
Oxyethyleneated nonylphenol containing four mols of ethylene oxide, sold
under the name "CEMULSOL NP4" by "RHONE POULENC" 12 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "CEMULSOL NP9" by "RHONE POULENC" 15 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide, sold
under the name "CEMULSOL NP9" by "RHONE POULENC" 15 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 1.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 1.5 g
Propylene glycol 6 9
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.12 g
Ammonia solution (220B strength) 11 g
Thioglycolic acid 0.6 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.4.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 20 minutes at 250C, this mixture imparts to the hair, after rinsing and shampooing, a pure blue coloration.
EXAMPLE 8
The following dyeing composition is prepared:
Compound of Example 1 0.285 g 2,6-Dimethyl-para-phenylenediamine dihydrochloride 0.209 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 4.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 4.5 g
Oxyethyleneated oleylamine containing twelve mols of ethylene oxide,
sold under the name "ETHOMEEN TO12,, by "ARMOUR HESS" 4.5 g
Diethanolamides of copra fatty acids 9 g
Propylene glycol 4 g
2-Butoxyethanol 8 g
Ethanol (960 strength) 6 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under the
name "MASQUOL DTPA" 2 g
Hydroquinone 0.15 g
Sodium bisulphite solution (350B strength) 1.3 g
Ammonia solution (220B strength) 5 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 30 minutes at 280C to hair which has been bleached white beforehand, this mixture imparts to the hair, after rinsing and shampooing, a slightly purple, intense blue coloration.
EXAMPLE 9
The following dyeing composition is prepared
Compound of Example 1 0.012 g
Para-phenyienediamine 0.108 g
2,6-Dimethyl-para-phenylenediamine dihydrochloride 0.0502 g
Para-aminophenol 0.155 g
2-Methylresorcinol 0.19 g
Meta-aminophenol 0.12 g 1-Phenyl-3-methylpyrazol-5-one 0.09 g 3-(N-Methylamino)-4-nitrophenoxyethanol 0.2 g
Oxyethyleneated nonylphenol containing four mols of ethylene oxide,
sold under the name "CEMULSOL NP4" by "RHONE POULENC" 12 9
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "CEMULSOL NP9" by "RHONE POULENC" 1 5 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 1.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 1.5 g
Propylene glycol 6 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.12 g
Ammonia solution (220B strength). 11 g
Mercaptosuccinic acid 0.2 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.4.
75 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 25 minutes at 300C to hair which has been bleached white beforehand, this mixture imparts to the hair, after rinsing and shampooing, a golden sandy coloration.
EXAMPLE 10
The following dyeing composition is prepared:
Compound of Example 2 0.065 g
Para-phenylenediamine 0.2 g
Para-aminophenol 0,4 g
N-Methyl-para-aminophenol sulphate 0.31 g
2-Methylresorcinol 0.3 g
Meta-aminophenol 0.405 g 2-Methyl-5-[N-(p-hydroxyethyl)-amino]-phenol 0.08 g
3-(N-Methylamino)-4-nitrophenoxy-ethanol 0.5 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 4.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 4.5 g
Oxyethyleneated oleylamine containing two mols of ethylene oxide, sold
under the name "ETHOMEEN TO12,, by "ARMOUR HESS" 4.5 g
Diethanolamides of copra fatty acids 9 g
Propylene glycol 4 g
2-Butoxyethanol 8 g Ethanol (960 strength) 6 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under
the name "MASQUOL DTPA" 2 g
Hydroquinone 0.15 g
Sodium bisulphite solution (350B strength) 1.3 g
Ammonia solution (220B strength) 8 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.5.
80 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 35 minutes at 300C to hair which has been bleached straw blond beforehand, this mixture imparts to the hair, after rinsing and shampooing, a medium chestnut coloration with a coppery sheen.
EXAMPLE 11
The following dyeing composition is prepared:
Compound of Example 1 0.52 g
Para-phenylenediamine 0.6 g
Para-aminophenol 0.8 g 4-IN,N-Di-(P-hydroxyethyl)-amino]-anilin dihydrochloride 1 g
Meta-aminophenol 0.5 g
Resorcinol 1.54 g
3-Nitro-4-aminophenol 0.6 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 4.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 4.5 g
Oxyethyleneated oleylamine containing twelve mols of ethylene oxide, sold
under the name "ETHOMEEN TO12,, by "ARMOUR PRESS" 4.5 g
Diethanolamine of copra fatty acids 9 g
Propylene glycol 4 g
2-Butoxyethanol 8 g
Ethanol (960 strength) 6 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under the
name "MASQUOL DTPA" 2 g
Thioglycolic acid 0.5 g
Ammonia solution (220B strength) 10 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.3.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 30 minutes at 280C to hair which has been bleached deep blond, this mixture imparts to the hair, after rinsing and shampooing, a brown coloration.
EXAMPLE 12
The following dyeing composition is prepared:
Compound of Example 2 0.04 g
Para-phenylenediamine 0.955 g
Ortho-aminophenol 0.375 g
Resorcinol 0.09 g
Meta-aminophenol 0.155 g 2-Methyl-5-[N-(,e-hydroxyethyl)-amino]-phenol 1.12 g
Cetyl/stearyl alcohol sold under the name "ALFOLC16/18 E" by !'CONDEA" 19 g 2-Octyidodecanol sold under the name "EUTANOL G" by "HENKEL" 4.5 g
Cetyl/stearyl alcohol containing fifteen mols of ethylene oxide, sold
under the name "MERGITAL CS 1 5/E" by "HENKEL" 2.5 g
Ammonium lauryl-sulphate containing 30% of active ingredient 12 g
Polymer based on repeat units of the formula
4 9 Benzyl alcohol 2 g
Ammonia solution (220B strength) 11 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 1 g
Sodium bisulphite solution (d = 1.3) 1.2 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.2.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 20 minutes at 25"C to hair which has been bleached straw yellow, this mixture imparts to the hair, after rinsing and shampooing, a purple-black coloration.
EXAMPLE 13
The following dyeing composition is prepared:
Compound of Example 1 0.1 g
Para-phenylenediamine 0.31 g
Para-aminophenol 0.4 g
4-(N-Methylamino)-phenyl sulphate 0.4 g
Resorcinol 0.5 g
Meta-aminophenol 0.3 9 2-Methyl-5-[N-(p-hydroxyethyl)-aminoJ-phenol 0.41 g
2-lsopropyl-6-nitroaniline 0.81 g
Cetyl/stearyl alcohol sold under the name "ALFOL Cm 6/18 E" by
"CONDEA" 8 g
Sodium cetyl-/stearyl-sulphate sold under the name "LANETTE WAX E" byHENKEL" 0.5 9
Oxyethyleneated castor oil sold under the name "CEMULSOL B" by
"RHONE POULENC" 1 g
Oleyl diethanolamide 1.5 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under the
name 'MASQUOL DTPA" 2.5 9 Thioglycolic acid 0.5 g
Hydroquinone 0.15 9
Ammonia solution (220B strength) 11 9
Water q.s.p. 100 g
The pH of the composition is equal to 10.4.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 30 minutes at 300C to hair which has been bleached white, this mixture imparts to the hair, after rinsing and shampooing, a coppery medium chestnut coloration.
EXAMPLE 14
The following dyeing composition is prepared:
Compound of Example 1 0.0143 g 4-[N-(P-Methoxyethyl)-amino]-aniline dihydrochloride 0.0120 g
Acrylic acid polymer having a molecular weight of 2 to 3 million, sold
under the name "CARBOPOL 934" by "GOODRICH CHEMICAL CO" 1.5 g
Ethanol (960 strength) 11 g
2-Butoxyethanol 5 g
Trimethylcetylammonium bromide 1 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.1 g
Ammonia solution (220B strength) 10 g
Thioglycolic acid 0.2 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.2.
20 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 30 minutes at 300C to hair which has been bleached white, this mixture imparts to the hair, after rinsing and shampooing, a silvery light turquoise-blue coloration.
EXAMPLE 15
The following dyeing composition is prepared:
Compound of Example 1 0.055 g
Para-phenylenediamine 0.058 g
Para-aminophenol 0.5 g
Resorcinol 0.4 g
Meta-aminophenol 0.103 g 2-Methyl-5-N-(-hydroxyethyl)-amino}-phenol 0.05 g 3-Nitro-4-(N-methylamino)-N,N-di-(,B-hydroxyethyl)-aniline 0.31 g
Oxyethyleneated nonylphenol containing four mols of ethylene oxide, sold
under the name "REMCOPAL 334" by "GERLAND" 12 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "REMCOPAL 349" by "GERLAND" 15 g
Oxyethyleneated oleyl alcohol containing two mols of ethylene oxide 1.5 g
Oxyethyleneated oleyl alcohol containing four mols of ethylene oxide 1.5 g
Propylene glycol 6 g
Sodium bisulphite solution (350B strength) 1.2 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.12 g
Triethanolamine pH 8.5
Water q.s.p. 100 g
70 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 25 minutes at 280C to hair which has been bleached white, this mixture imparts to the hair, after rinsing and shampooing, a hazel coloration.
EXAMPLE 1 6 The following dyeing composition is prepared:
Compound of Example 1 1.3 g
Para-phenylenediamine 1.81 g
Para-aminophenol 0.8 g
2,4-Diaminophenoxy-ethanol dihydrochloride 0.2 g 2-Methyl-5-[N-(P-hydroxyethyl )-a mino]-phenol 0.803 g
Rescorcinol 0.81 g
Meta-aminophenol 0.9 g
Oxyethyleneated nonyiphenol containing four mo!s of ethylene oxide,
sold under the name "CEMULSOL NP4" by "RHONE POULENC" 21 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "CEMULSOL NP9" by "RHONE POULENC" 24 g
Oleic acid 4 g
2-Butoxyethanol 3 g
Ethanol (960 strength) 10 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under
the name "MASQUOL DTPA" 2.5 g
Thioglycolic acid 0.6 g
Ammonia solution (220B strength) 10 g
Water q.s.p. 100 g
The pH of the composition is equal to 9.5.
120 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied for 25 minutes at 280C to hair which has been bleached straw yellow, this mixture imparts to the hair, after rinsing and shampooing, a raven black coloration.
EXAMPLE 17
The following dyeing composition is prepared:
Compound of Example 1 0.252 g 4-[N-(P-Methoxyethyl)-a mino]-anilinedihydroch loride 0.6 g
2,6-Dimethyl-para-phenylenediamine dihydrochloride 0.2 g
Para-aminophenol 0.6 g
Resorcinol 0.905 9 Meta-aminophenol 0.435 g 2-Methyl-5-[N-(P-hydroxyethyl)-a mino]-phenol 0.2 g
6-Hydroxybenzomorpholine 0.435 g
2-Methyl-4-amino-5-nitrophenol 0.703 g
Oxyethyleneated nonylphenol containing four mols of ethylene oxide,
sold under the name "CEMULSOL NP4" by "RHONE POULENC" 12 g
Oxyethyleneated nonylphenol containing nine mols of ethylene oxide,
sold under the name "CEMULSOL NP9" by "RHONE POULENC" 1 5 g
Oleyl alcohol containing two mols of ethylene oxide 1.5 g
Oleyl alcohol containing four mols of ethylene oxide 1.5 g
Propylene glycol 6 g
Ethylenediaminetetraacetic acid sold under the name "TRILON B" 0.12 g
Ammonia solution (220B strength) 11 g
Thioglycolic acid 0.6 g
Water q.s.p. 100 g
The pH of the composition is equal to 9.9.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 30 minutes at 300C, this mixture imparts to the hair, after rinsing and shampooing, a coppery light chestnut coloration.
EXAMPLE 18
The following dyeing composition is prepared:
Compound of Example 1 0.306 g
Para-phenylenediamine 0.307 g 4-[N-(P-Methoxyethyl)-amino]-aniline dihydrochloride 0.15 g
2-Methylresorcinol 0.405 g 2-Methyl-5-[N-(P-hydroxyethyl)-am ino]-phenol 0.115 g
2,4-Diaminophenoxy-ethanol dihydrochloride 0.106 g
2-Amino-3-nitrophenol 0.203 g
Cetyl/stearyl alcohol sold under the name "ALFOL Cm 6/18 E" by
"CONDEA" 8 g
Sodium cetyl-/stearyl-sulphate sold under the name "LANETTE WAX E"
by "HENKEL" 0.5 g
Oxyethyleneated castor oil sold under the name "CEMULSOL B" by
"RHONE POULENC" 1 g
Oleyl diethanolamide 1.5 g
Pentasodium salt of diethylenetriaminepentaacetic acid, sold under the
name "MASQUOL DTPA" 2.5 g
Thioglycolic acid 0.5 g
Hydroquinone 0.15 g
Ammonia solution (220B strength) 11 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.3.
90 g of hydrogen peroxide of 20 volumess strength are added at the time of use.
When applied to 90% naturally white hair for 25 minutes at 250C, this mixture imparts to the hair, after rinsing and shampooing, a charcoal grey coloration.
EXAMPLE 19
The following dyeing composition is prepared:
Compound of Example 2 1.5 g
Compound of Example 1 0.42 g
Para-phenylenediamine 0.62 g 4-[N,N-Di-(,-hydroxyethyl)-amino]-aniline dihydrochloride 0.42 g
Para-aminophenol 0.705 g
Resorcinol 0.81 g 2-Methyl-5-[N-(,B-hydroxyethyl)-amino]-phenol 0.21 g
2-Amino-3-nitrophenoi 6.61 9 Cetyl/stearyl alcohol sold under the name "ALFOL C16/18 E" by
"CONDEA" 8 g
Sodium cetyl-/stearyl-sulphate sold under the name 'LANETTE WAX E" by
"HENKEL" 0.5 g
Oxyethyieneated castor oil sold under the name "CEMULSOL" by "RHONE
POULENC" 1 g
Oleyl diethanolamide 1.5 g
Pentasodium salt of diethylenetria minepentaacetic acid, sold under
the name "MASQUOL DTPA" 2.5 g
Thioglycolic acid 0.5 g
Hydroquinone 0.15 g
Ammonia solution (220B strength) 11 g
Water q.s.p. 100 g
The pH of the composition is equal to 10.1.
100 g of hydrogen peroxide of 20 volumes strength are added at the time of use.
When applied to 90% naturally white hair for 20 minutes at 280C, this mixture imparts to the hair, after rinsing and shampooing, a very dark brown coloration.
Claims (40)
1. A compound of the general formula:
in which formula Z represents either a polyhydroxyalkyl radical in which the alkyl group contains from 3 to 6 carbon atoms, the said radical containing 2 or 3 hydroxyl groups, or an alkyl radical containing at least one chain hetero-atom and at least one hydroxyl group, the said alkyl radical containing from 4 to 8 carbon atoms, or an acid salt thereof.
2. A compound according to claim 1 in which Z represents an alkyl radical containing at least one chain hetero-atom, said hetero-atom or atoms being oxygen:
3. A compound according to claim 1 in which Z represents a p '-hydroxyethoxy)-ethyl radical.
4. A compound according to claim 1 in which Z represents a ,y-dihydrnxyprnpyl radical.
5. A compound according to any one of claims 1 to 4 in the form of a hydrpchloride.
6. Process for the preparation of a compound as claimed in any one of claimss 1 to 5 which comprises reacting a halogen derivative of the formula X-Z, X being a halogen and Z being as defined in claim 1 with an alkali metal salt of 2-acetylamino-4-nitrophenol so as to condense the radical Z onto the nucleus, reducing the nitro group of the product obtained and then deacetylating the resulting product.
7. Process according to claim 6 in which X is chlorine and the alkali metal salt is a potassium salt.
8. Process according to claim 6 or 7 in which the reduction of the nitro group is carried out in alcoholic solution, under reflux, using zinc powder in the presence of ammonium chloride.
9. Process according to claim 6 substantially as described in Example 1 or 2.
10. A compound as defined in claim 1 whenever prepared by a process as claimed in any one of claims 6 to 9.
1 A composition suitable for dyeig keratin fibres which contains at least one oxidation base, in a cosmetically acceptable carrier, and, as a coupler, at least one compound of formula (I) or acid salt thereof as claimed in any one of claims 1 to 5, in an acceptable carrier.
12. A composition according to claim 11 suitable for dyeing human hair.
13. A composition according to claim 11 or 12 in which the compound of formula (I) is present in an amount from 0.001 to 2.5% by weight, relative to the total weight of the composition.
14. A composition according to any one of claims 11 to 13 whicn contains, as the oxidation base, at least one para-phenylenediamine of the general formula
or an acid salt thereof, in which formula R1, R2 and R3 are identical or different and represent a hydrogen atom, an alkyl radical having from 1 to 4 carbon atoms or an alkoxy having 1 or 3 carbon atoms, and R4 and R5 are identical or different and represent a hydrogen atom, an alkyl or hydroxyalkyl radical, an alkoxyalkyl radical in which the alkoxy group contains 1 or 2 carbon atoms, or a carbamylalkyl, mesyiaminoalkyl, acetylaminoalkyl, ureidoalkyl, carbethoxyaminoalkyl, aminoalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, piperidinoalkyl or morpholinoalkyl radical, the alkyl groups in R4 and R5 having from 1 to 4 carbon atoms, or alternatively R4 and R5 form a piperidino or morpholino group together and with the nitrogen atom to which they are attached, with the proviso that R, and R3 represent a hydrogen atom if R4 and R5 do not represent a hydrogen atom.
1 5. A composition according to any one of claims 11 to 14 which contains, as the oxidation base, at least one para-aminophenol of the general formula (it1):
or an acid salt thereof in which formula R6 represents a hydrogen atom, an alkyl radical containing from 1 to 4 carbon atoms or a halogen atom.
1 6. A composition according to any one of claims 11 to 1 5 which contains at least one
heterocyclic base as the oxidation base.
17. A composition according to claim 1 6 which contains, as the oxidation base, at least one of 2,5-diaminopyridine, 3-methyl-7-aminobenzomorpholine and 5-aminoindole.
1 8. A composition according to any one of claims 11 to 1 7 which contains at least one coupler which is resorcinol, 2-methyl-resorcinol, meta-aminophenol, 2-methyl-5-aminophenol, 2-methyl-5-[N- (p-hydroxyethyl)-amino]-phenol,6-hydroxybenzomorpholine,2,6-dimethyl-3-acetylaminophenol,2- methyl-5-carbethoxyaminophenol, 2-methoxy-5-carbethoxyaminophenol, 2-methyl-5-ureidophenol or
1 -phenyl-3-methylpyrazol-5-one.
1 9. A composition according to any one of claims 11 to 1 8 which contains ortho-diphenol or at
least one ortho-phenylenediamine or at least one orthoaminophenol, which is optionally substituted on
the nucleus or on the amine group.
20. A composition according to any one of claims 11 to 1 9 which contains at least one dyestuff
precursor of the benzene series, containing, on the nucieus, at least three substituents which are
hydroxyl, methoxy or amino groups.
21. A composition according to any one of claims 11 to 20 which contains at least one dyestuff precursor of the naphthalene series.
22. A composition according to any one of claims 11 to 21 which contains at least one leucoderivative of indoaniline, of indophenol or of indamine.
23. A composition according to any one of claims 11 to 22*which contains at least one direct dyestuff.
24. A composition according to any one of claims 11 to 23 which has a pH from 8 to 11.5.
25. A composition according to claim 24 which contains, as alkalising agent, at least one of ammonia, an alkylamine, alkanolamine, alkylalkanolamine, sodium hydroxide or potassium hydroxide or an alkali metal carbonate.
26. A composition according to claim 24 which contains at least one acidifying agent which is lactic acid, acetic acid, tartaric acid or phosphoric acid.
27. A composition according to any one of claims 11 to 26 which contains water and at least one surface-active agent, organic solvent, thickening product, antioxidant, penetrating agent, foaming agent, sequestering agent, film-forming product, treating agent or perfume.
28. A composition according to claim 27 which contains at least one surface-active agent which is an alkylbenzenesulphonate, alkylnaphthalenesulphonate, sulphate, ether-sulphate or sulphonate of a fatty alcohol, a quaternary ammonium salt, fatty acid diethanolamine, polyoxyethyleneated or polyglycerolated acid or alcohol or a polyoxyethyleneated or polyglycerolated alkylphenol.
29. A composition according to claim 27 or 28 which contains from 0.5 to 55% by weight of surface-active agent, relative to the total weight of the composition.
30. A composition according to claim 27 which contains at least one organic solvent which is
ethanol, isopropanol, glycerol, a glycol or an ether thereof or diethylene glycol or an ether thereof.
31. A composition according to any one of claims 27 to 30 which contains from 1 to 40% by
weight of organic solvent(s), relative to the total weight of the composition.
32. A composition according to any one of claims 27 to 31 which contains at least one
thickening product which is sodium alginate, gum arabic, a cellulose derivative, an acrylic acid polymer or bentonite.
33. A composition according to any one of claims 27 to 32 which contains 0.5 to 5% by weight of thickener(s), relative to the total weight of the composition.
34. A composition according to any one of claims 27 to 33 which contains at least one antioxidant which is sodium sulphite, thioglycolic acid, mercaptosuccinic acid, sodium bisulphite, ascorbic acid, or
hydroquinone.
35. A composition according to any one of claims 27 to 34 which contains 0.05 to 1.5% of
antioxidant(s), relative to the total weight of the composition.
36. A composition according to claim 11 substantially as described in any one of Examples 3 to 19.
37. A process for dyeing hair which comprises mixing a composition as claimed in any one of claims 11 to 36 with an oxidising agent, applying the mixture to the hair, and allowing it to remain on the hair for 5 to 45 minutes, rinsing the hair, optionally shampooing and rinsing it again, and drying the hair.
38. A process according to claim 37 in which the oxidising agent is hydrogen peroxide, urea peroxide or a per-salt.
39. A process according to claim 37 or 38 in which the composition is in the form of a liquid, a cream, a gel or an aerosol.
40. A process according to claim 37 substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8014661A FR2486075A1 (en) | 1980-07-01 | 1980-07-01 | METHAPHENYLENEDIAMINES AND METHOD FOR THE PRODUCTION THEREOF, TINCTORIAL COMPOSITIONS CONTAINING SAME, AND METHOD FOR DYING THE SAME |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2078747A true GB2078747A (en) | 1982-01-13 |
| GB2078747B GB2078747B (en) | 1986-01-22 |
Family
ID=9243730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8120127A Expired GB2078747B (en) | 1980-07-01 | 1981-06-30 | Meta-phenylenediamine dye couplers |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5744669A (en) |
| AR (1) | AR227050A1 (en) |
| AT (1) | AT380683B (en) |
| AU (1) | AU543206B2 (en) |
| BE (1) | BE889449A (en) |
| BR (1) | BR8104162A (en) |
| CA (1) | CA1168266A (en) |
| CH (1) | CH650246A5 (en) |
| DE (1) | DE3125705A1 (en) |
| DK (1) | DK150540C (en) |
| ES (2) | ES503491A0 (en) |
| FR (1) | FR2486075A1 (en) |
| GB (1) | GB2078747B (en) |
| IT (1) | IT1144738B (en) |
| MX (1) | MX155064A (en) |
| NL (1) | NL8103150A (en) |
| PT (1) | PT73269B (en) |
| SE (1) | SE460787B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2547300A1 (en) * | 1983-06-13 | 1984-12-14 | Oreal | NOVEL SUBSTITUTED METAAMINOPHENOLS, PROCESS FOR THEIR PREPARATION, TINCTORIAL COMPOSITIONS FOR HAIR CONTAINING THEM AND CORRESPONDING HAIR DYEING METHOD |
| US4863481A (en) * | 1982-01-05 | 1989-09-05 | L'oreal | Dyeing compositions based on oxidation dyestuff precursors and on n-substituted ortho-nitroanilines and comprising an alkanolamine and bisulphite, and their use in the dyeing of keratin fibres |
| FR2715296A1 (en) * | 1994-01-24 | 1995-07-28 | Oreal | Keratin fiber oxidation dyeing composition comprising a paraphenylenediamine, a metalphenylenediamine and a para-aminophenol or a meta-aminophenol, and dyeing process using such a composition. |
| EP0684035A1 (en) * | 1994-05-26 | 1995-11-29 | L'oreal | Keratineous fibres oxidation dyeing composition containing a derivative of paraphenylenediamine and a 6-hydroxy 1,4-benzoxazine |
| US5690696A (en) * | 1995-01-19 | 1997-11-25 | L'oreal | Combinations of two para-phenylenediamine oxidation bases and a meta-phenylenediamine coupler for the oxidation dyeing of keratinous fibers |
| WO1999065865A1 (en) * | 1998-06-13 | 1999-12-23 | Hans Schwarzkopf Gmbh & Co. Kg | Novel 3,4-diaminophenol derivatives and their use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0825858B2 (en) * | 1991-06-04 | 1996-03-13 | ホーユー株式会社 | Hair dye composition |
| FR2707487B1 (en) † | 1993-07-13 | 1995-09-08 | Oreal | A keratin fiber oxidation dye composition comprising a para-aminophenol, a meta-aminophenol and a metaphenylenediamine, and a dyeing process using such a composition. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1670969A (en) * | 1926-12-13 | 1928-05-22 | Firm Chemical Works Formerly S | 2-amino-4-nitrophenoxypropandiol and process of producing same |
| FR2362116A1 (en) * | 1976-08-20 | 1978-03-17 | Oreal | METAPHENYLENEDIAMINES AND TINCTORIAL COMPOSITIONS CONTAINING THEM |
-
1980
- 1980-07-01 FR FR8014661A patent/FR2486075A1/en active Granted
-
1981
- 1981-06-22 AT AT0274181A patent/AT380683B/en not_active IP Right Cessation
- 1981-06-26 PT PT73269A patent/PT73269B/en not_active IP Right Cessation
- 1981-06-29 AR AR285896A patent/AR227050A1/en active
- 1981-06-29 ES ES503491A patent/ES503491A0/en active Granted
- 1981-06-29 DK DK287681A patent/DK150540C/en not_active IP Right Cessation
- 1981-06-29 CH CH4277/81A patent/CH650246A5/en not_active IP Right Cessation
- 1981-06-30 BE BE0/205266A patent/BE889449A/en not_active IP Right Cessation
- 1981-06-30 CA CA000380936A patent/CA1168266A/en not_active Expired
- 1981-06-30 BR BR8104162A patent/BR8104162A/en unknown
- 1981-06-30 AU AU72363/81A patent/AU543206B2/en not_active Expired
- 1981-06-30 GB GB8120127A patent/GB2078747B/en not_active Expired
- 1981-06-30 IT IT67905/81A patent/IT1144738B/en active
- 1981-06-30 SE SE8104072A patent/SE460787B/en not_active IP Right Cessation
- 1981-06-30 NL NL8103150A patent/NL8103150A/en not_active Application Discontinuation
- 1981-06-30 DE DE3125705A patent/DE3125705A1/en not_active Withdrawn
- 1981-06-30 MX MX188102A patent/MX155064A/en unknown
- 1981-07-01 JP JP56101396A patent/JPS5744669A/en active Pending
- 1981-10-28 ES ES506626A patent/ES506626A0/en active Granted
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863481A (en) * | 1982-01-05 | 1989-09-05 | L'oreal | Dyeing compositions based on oxidation dyestuff precursors and on n-substituted ortho-nitroanilines and comprising an alkanolamine and bisulphite, and their use in the dyeing of keratin fibres |
| FR2547300A1 (en) * | 1983-06-13 | 1984-12-14 | Oreal | NOVEL SUBSTITUTED METAAMINOPHENOLS, PROCESS FOR THEIR PREPARATION, TINCTORIAL COMPOSITIONS FOR HAIR CONTAINING THEM AND CORRESPONDING HAIR DYEING METHOD |
| US4863480A (en) * | 1983-06-13 | 1989-09-05 | The French Joint Stock Company "L'oreal" | Substituted metaaminophenols, a process for their preparation, hair dyeing compositions containing them and a hair-dyeing process |
| US5863300A (en) * | 1994-01-24 | 1999-01-26 | L'oreal | Composition for the oxidation dyeing of keratinous fibres comprising a para-phenylenediamine, a meta-phenylenediamine and a para-aminophenol or a meta-aminophenol, and dyeing process |
| EP0667143A1 (en) * | 1994-01-24 | 1995-08-16 | L'oreal | Keratinous fiber oxidation dyeing composition containing a paraphenylenediamine, a metaphenylenediamine and a paraaminophenol or a metaaminophenol |
| FR2715296A1 (en) * | 1994-01-24 | 1995-07-28 | Oreal | Keratin fiber oxidation dyeing composition comprising a paraphenylenediamine, a metalphenylenediamine and a para-aminophenol or a meta-aminophenol, and dyeing process using such a composition. |
| US6022382A (en) * | 1994-01-24 | 2000-02-08 | L'oreal | Processes and kits for dyeing keratinous fibers with a para-phenylenediamine containing a primary, secondary or tertiary amine function, a meta-phenylenediamine, and a para-aminophenol or a meta-aminophenol |
| CN1060036C (en) * | 1994-01-24 | 2001-01-03 | 莱雅公司 | Composition forthe oxidation dyeingof keratinous fiberes comprising a para-phenylenediamine containinga primary, secondary or tertiary amine function, a meta-phenylenediamine and a para-aminopheno.... |
| EP0684035A1 (en) * | 1994-05-26 | 1995-11-29 | L'oreal | Keratineous fibres oxidation dyeing composition containing a derivative of paraphenylenediamine and a 6-hydroxy 1,4-benzoxazine |
| FR2720275A1 (en) * | 1994-05-26 | 1995-12-01 | Oreal | An oxidation dyeing composition of keratinous fibers comprising a paraphenylenediamine derivative and a 6-hydroxy 1,4-benzoxazine, and a dyeing method using such a composition. |
| US5690695A (en) * | 1994-05-26 | 1997-11-25 | L'oreal | Composition for the oxidation dyeing of keratinous fibres, comprising a para-phenylenediamine derivative and a 6-hydroxy-1, 4-benzomorpholine and dyeing process using such a composition |
| US5868800A (en) * | 1994-05-26 | 1999-02-09 | L'oreal | Composition for the oxidation dyeing of keratinous fibres, comprising a para-phenylenediamine derivative and a 6-hydroxy-1, 4-benzomorpholine and dyeing process using such a composition |
| US5690696A (en) * | 1995-01-19 | 1997-11-25 | L'oreal | Combinations of two para-phenylenediamine oxidation bases and a meta-phenylenediamine coupler for the oxidation dyeing of keratinous fibers |
| WO1999065865A1 (en) * | 1998-06-13 | 1999-12-23 | Hans Schwarzkopf Gmbh & Co. Kg | Novel 3,4-diaminophenol derivatives and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| AT380683B (en) | 1986-06-25 |
| BE889449A (en) | 1981-12-30 |
| MX155064A (en) | 1988-01-22 |
| DK150540B (en) | 1987-03-23 |
| BR8104162A (en) | 1982-03-16 |
| ATA274181A (en) | 1985-11-15 |
| SE8104072L (en) | 1982-01-02 |
| ES8205393A1 (en) | 1982-06-01 |
| DE3125705A1 (en) | 1982-03-18 |
| PT73269B (en) | 1982-09-23 |
| DK287681A (en) | 1982-01-02 |
| CH650246A5 (en) | 1985-07-15 |
| ES8301889A1 (en) | 1982-12-16 |
| CA1168266A (en) | 1984-05-29 |
| IT8167905A0 (en) | 1981-06-30 |
| DK150540C (en) | 1988-01-11 |
| ES503491A0 (en) | 1982-06-01 |
| ES506626A0 (en) | 1982-12-16 |
| NL8103150A (en) | 1982-02-01 |
| GB2078747B (en) | 1986-01-22 |
| SE460787B (en) | 1989-11-20 |
| FR2486075A1 (en) | 1982-01-08 |
| JPS5744669A (en) | 1982-03-13 |
| AU7236381A (en) | 1982-09-16 |
| AU543206B2 (en) | 1985-04-04 |
| FR2486075B1 (en) | 1983-03-11 |
| PT73269A (en) | 1981-07-01 |
| AR227050A1 (en) | 1982-09-15 |
| IT1144738B (en) | 1986-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PE20 | Patent expired after termination of 20 years |
Effective date: 20010629 |