CH679551A5 - - Google Patents

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Info

Publication number: CH679551A5
Authority: CH; Switzerland
Prior art keywords: amino; methyl; hydroxy; indole; composition
Prior art date: 1988-09-12

Application number

CH3213/89A

Other languages

English (en)

French (fr)

Inventor

Alex Junino

Gerard Lang

Jean-Jacques Vandenbossche

Original Assignee

Oreal

Priority date (The priority date 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 date listed.)

1988-09-12

Filing date

1989-09-05

Publication date

1992-03-13

1989-09-05 Application filed by Oreal filed Critical Oreal

1992-03-13 Publication of CH679551A5 publication Critical patent/CH679551A5/fr

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 98
239000000203 mixture Substances 0.000 claims description 89
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 49
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 49
239000000975 dye Substances 0.000 claims description 44
210000004209 hair Anatomy 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 23
238000007254 oxidation reaction Methods 0.000 claims description 22
239000002243 precursor Substances 0.000 claims description 22
-1 C1-C4 alkyl radical Chemical class 0.000 claims description 20
230000003647 oxidation Effects 0.000 claims description 20
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 18
239000000835 fiber Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 17
238000004043 dyeing Methods 0.000 claims description 16
102000011782 Keratins Human genes 0.000 claims description 12
108010076876 Keratins Proteins 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 7
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
230000001590 oxidative effect Effects 0.000 claims description 5
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 4
GPJJASIJVRXZFI-UHFFFAOYSA-N 4-methoxybenzene-1,3-diol Chemical compound COC1=CC=C(O)C=C1O GPJJASIJVRXZFI-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000005406 washing Methods 0.000 claims description 4
PSTUGXWVTKXNGK-UHFFFAOYSA-N 2-anilino-n-ethylacetamide Chemical compound CCNC(=O)CNC1=CC=CC=C1 PSTUGXWVTKXNGK-UHFFFAOYSA-N 0.000 claims description 3
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 3
239000002562 thickening agent Substances 0.000 claims description 3
OQWWMUWGSBRNMA-UHFFFAOYSA-N 1-(2,4-diaminophenoxy)ethanol Chemical compound CC(O)OC1=CC=C(N)C=C1N OQWWMUWGSBRNMA-UHFFFAOYSA-N 0.000 claims description 2
229940113489 2,4-diaminophenoxyethanol Drugs 0.000 claims description 2
MJAVQHPPPBDYAN-UHFFFAOYSA-N 2,6-dimethylbenzene-1,4-diamine Chemical compound CC1=CC(N)=CC(C)=C1N MJAVQHPPPBDYAN-UHFFFAOYSA-N 0.000 claims description 2
BVWOHFHLLLPJLH-UHFFFAOYSA-N 2-methoxy-3,5-dimethylbenzene-1,4-diamine Chemical compound COC1=C(C)C(N)=C(C)C=C1N BVWOHFHLLLPJLH-UHFFFAOYSA-N 0.000 claims description 2
KNRVAYVZVIKHHL-UHFFFAOYSA-N 2-methoxy-5-methylbenzene-1,4-diamine Chemical compound COC1=CC(N)=C(C)C=C1N KNRVAYVZVIKHHL-UHFFFAOYSA-N 0.000 claims description 2
UVUGDGRIYQQKIT-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazin-6-amine Chemical compound O1CCNC2=CC(N)=CC=C21 UVUGDGRIYQQKIT-UHFFFAOYSA-N 0.000 claims description 2
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 2
XRMTWJAJYBZYLZ-UHFFFAOYSA-N 4-(1-hydroxyethoxy)benzene-1,3-diol Chemical compound CC(O)OC1=CC=C(O)C=C1O XRMTWJAJYBZYLZ-UHFFFAOYSA-N 0.000 claims description 2
JSWVCUXQICMATE-UHFFFAOYSA-N 4-amino-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C=C1N JSWVCUXQICMATE-UHFFFAOYSA-N 0.000 claims description 2
OMVFXCQLSCPJNR-UHFFFAOYSA-N 4-amino-2,6-dimethylphenol Chemical compound CC1=CC(N)=CC(C)=C1O OMVFXCQLSCPJNR-UHFFFAOYSA-N 0.000 claims description 2
ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 claims description 2
MCNBYOWWTITHIG-UHFFFAOYSA-N 4-amino-2-methoxyphenol Chemical compound COC1=CC(N)=CC=C1O MCNBYOWWTITHIG-UHFFFAOYSA-N 0.000 claims description 2
HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 claims description 2
PNLPXABQLXSICH-UHFFFAOYSA-N 4-amino-3-chlorophenol Chemical compound NC1=CC=C(O)C=C1Cl PNLPXABQLXSICH-UHFFFAOYSA-N 0.000 claims description 2
GCWYXRHXGLFVFE-UHFFFAOYSA-N 4-hydroxy-2,6-dimethylaniline Chemical compound CC1=CC(O)=CC(C)=C1N GCWYXRHXGLFVFE-UHFFFAOYSA-N 0.000 claims description 2
IHWPTLPROWODBQ-UHFFFAOYSA-N 4-n-methoxybenzene-1,4-diamine Chemical compound CONC1=CC=C(N)C=C1 IHWPTLPROWODBQ-UHFFFAOYSA-N 0.000 claims description 2
DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
239000000443 aerosol Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000002280 amphoteric surfactant Substances 0.000 claims description 2
229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
239000000872 buffer Substances 0.000 claims description 2
125000002091 cationic group Chemical group 0.000 claims description 2
239000006071 cream Substances 0.000 claims description 2
239000000982 direct dye Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 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
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
230000035515 penetration Effects 0.000 claims description 2
239000002304 perfume Substances 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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
239000003380 propellant Substances 0.000 claims description 2
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
239000003352 sequestering agent Substances 0.000 claims description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 claims 1
BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 claims 1
YOJKEVXNAVNUGW-UHFFFAOYSA-N 4-n-chlorobenzene-1,4-diamine Chemical compound NC1=CC=C(NCl)C=C1 YOJKEVXNAVNUGW-UHFFFAOYSA-N 0.000 claims 1
TVOSOIXYPHKEAR-UHFFFAOYSA-N 4-piperidin-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCCCC1 TVOSOIXYPHKEAR-UHFFFAOYSA-N 0.000 claims 1
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
239000000499 gel Substances 0.000 claims 1
229940113083 morpholine Drugs 0.000 claims 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 9
229910021529 ammonia Inorganic materials 0.000 description 8
238000004040 coloring Methods 0.000 description 8
229960004337 hydroquinone Drugs 0.000 description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
235000019445 benzyl alcohol Nutrition 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
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 5
239000005642 Oleic acid Substances 0.000 description 5
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 5
229920006317 cationic polymer Polymers 0.000 description 5
229960001484 edetic acid Drugs 0.000 description 5
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229940001607 sodium bisulfite Drugs 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
229940001584 sodium metabisulfite Drugs 0.000 description 3
235000010262 sodium metabisulphite Nutrition 0.000 description 3
QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
SXJQUUPSLJTKKT-UHFFFAOYSA-N 4-hydroxy-2-methoxyaniline Natural products COC1=CC(O)=CC=C1N SXJQUUPSLJTKKT-UHFFFAOYSA-N 0.000 description 2
244000060011 Cocos nucifera Species 0.000 description 2
235000013162 Cocos nucifera Nutrition 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
229940054051 antipsychotic indole derivative Drugs 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002475 indoles Chemical class 0.000 description 2
239000003607 modifier Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229960003742 phenol Drugs 0.000 description 2
229960005323 phenoxyethanol Drugs 0.000 description 2
239000001294 propane Substances 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003871 sulfonates Chemical class 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
CKNOIIXFUKKRIC-HZJYTTRNSA-N (9z,12z)-n,n-bis(2-hydroxyethyl)octadeca-9,12-dienamide Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)N(CCO)CCO CKNOIIXFUKKRIC-HZJYTTRNSA-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
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical class CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
AEFUSISIFJGCHA-UHFFFAOYSA-N 1-methyl-6-phenylmethoxyindole Chemical compound C1=C2N(C)C=CC2=CC=C1OCC1=CC=CC=C1 AEFUSISIFJGCHA-UHFFFAOYSA-N 0.000 description 1
XAWPKHNOFIWWNZ-UHFFFAOYSA-N 1h-indol-6-ol Chemical compound OC1=CC=C2C=CNC2=C1 XAWPKHNOFIWWNZ-UHFFFAOYSA-N 0.000 description 1
PYHGMRPBEQFDEC-UHFFFAOYSA-N 2-(2-hydroxyethyl)benzonitrile Chemical compound OCCC1=CC=CC=C1C#N PYHGMRPBEQFDEC-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 1
ALQKEYVDQYGZDN-UHFFFAOYSA-N 2-amino-6-methylphenol Chemical compound CC1=CC=CC(N)=C1O ALQKEYVDQYGZDN-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 description 1
MTOPVKYBDZVSPP-UHFFFAOYSA-N 3-anilino-n-ethylpropanamide Chemical compound CCNC(=O)CCNC1=CC=CC=C1 MTOPVKYBDZVSPP-UHFFFAOYSA-N 0.000 description 1
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 1
AIMWCCSARFYZCK-UHFFFAOYSA-N 3-methyl-1h-indol-7-ol Chemical compound C1=CC=C2C(C)=CNC2=C1O AIMWCCSARFYZCK-UHFFFAOYSA-N 0.000 description 1
UBKPLLYABUUFCE-UHFFFAOYSA-N 4-amino-2,3-dimethylphenol Chemical compound CC1=C(C)C(O)=CC=C1N UBKPLLYABUUFCE-UHFFFAOYSA-N 0.000 description 1
OJIWRZBZQAKZSV-UHFFFAOYSA-N 4-amino-2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC(N)=C1O OJIWRZBZQAKZSV-UHFFFAOYSA-N 0.000 description 1
XCJRRZLPXALCIP-UHFFFAOYSA-N 4-n-(2-methoxyethyl)benzene-1,4-diamine Chemical compound COCCNC1=CC=C(N)C=C1 XCJRRZLPXALCIP-UHFFFAOYSA-N 0.000 description 1
GDOIKKMNCIMDAO-UHFFFAOYSA-N 5-amino-1h-pyridin-2-one Chemical compound NC1=CC=C(O)N=C1 GDOIKKMNCIMDAO-UHFFFAOYSA-N 0.000 description 1
HJUFFOMJRAXIRF-UHFFFAOYSA-N 6-hydroxy-1h-indole-2-carboxylic acid Chemical compound C1=C(O)C=C2NC(C(=O)O)=CC2=C1 HJUFFOMJRAXIRF-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Chemical class 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000158728 Meliaceae Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Chemical class 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
BMJXMAAIWXBKBD-UHFFFAOYSA-N aniline;dihydrochloride Chemical compound Cl.Cl.NC1=CC=CC=C1 BMJXMAAIWXBKBD-UHFFFAOYSA-N 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002610 basifying agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000001913 cellulose Chemical class 0.000 description 1
229920002678 cellulose Chemical class 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
JOYVJYNWIUYLLE-UHFFFAOYSA-N chloroform;2-propan-2-yloxypropane Chemical compound ClC(Cl)Cl.CC(C)OC(C)C JOYVJYNWIUYLLE-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000006083 mineral thickener Substances 0.000 description 1
150000004989 p-phenylenediamines Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229920000223 polyglycerol Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Birds (AREA)
Epidemiology (AREA)
Cosmetics (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH3213/89A 1988-09-12 1989-09-05 CH679551A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU87337A LU87337A1 (fr)	1988-09-12	1988-09-12	Compositions tinctoriales pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs indoliques et procedes de teinture mettant en oeuvre ces compositions

Publications (1)

Publication Number	Publication Date
CH679551A5 true CH679551A5 (de)	1992-03-13

Family

ID=19731089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3213/89A CH679551A5 (de)	1988-09-12	1989-09-05

Country Status (19)

Country	Link
JP (1)	JP2744080B2 (de)
KR (1)	KR0172112B1 (de)
AR (1)	AR245515A1 (de)
AT (1)	AT400672B (de)
AU (1)	AU626579B2 (de)
BE (1)	BE1002235A4 (de)
BR (1)	BR8904562A (de)
CA (1)	CA1341195C (de)
CH (1)	CH679551A5 (de)
DE (1)	DE3930473B4 (de)
ES (1)	ES2016162A6 (de)
FR (1)	FR2636236B1 (de)
GB (1)	GB2224518B (de)
GR (1)	GR1000461B (de)
IT (1)	IT1232920B (de)
LU (1)	LU87337A1 (de)
NL (1)	NL194230C (de)
PT (1)	PT91663B (de)
ZA (1)	ZA896845B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2659228B1 (fr) *	1990-03-08	1994-10-14	Oreal	Procede de teinture des fibres keratiniques avec des 6 ou 7-monohydroxy-indoles a ph acide et compositions mises en óoeuvre.
FR2689761B1 (fr) *	1992-04-09	1995-06-23	Oreal	Procede de teinture des fibres keratiniques en milieu alcalin mettant en óoeuvre des paraaminophenols substitues en position 2 en association avec le 6-ou 7-hydroxyindole et compositions mises en óoeuvre dans le procede.
CA2258728C (en)	1996-06-19	2011-09-27	Rhone Poulenc Rorer Limited	Substituted azabicylic compounds and their use as inhibitors of the production of tnf and cyclic amp phosphodiesterase
US8608810B2 (en)	2012-03-27	2013-12-17	The Procter & Gamble Company	Hair colorant compositions comprising 3-amino-2,6-dimethylphenol and 1,4-phenylenediamine-type developers, methods, and kits comprising the compositions
WO2013148805A2 (en)	2012-03-27	2013-10-03	The Procter & Gamble Company	Hair colorant compositions comprising 3- amino -2,6- dimethylphenol and 4- aminophenol-type developers, methods, and kits comprising the compositions

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU56102A1 (de) *	1968-05-17	1970-01-14
US4013404A (en) *	1970-12-06	1977-03-22	American Cyanamid Company	Method of dyeing hair with indolines, indoles and indazoles
US4776857A (en) *	1986-11-21	1988-10-11	Repligen Corporation	Use of hydroxylated indoles as dye precursors
LU86833A1 (fr) *	1987-04-02	1988-12-13	Oreal	Procede de teinture des fibres keratiniques avec le 5,6-dihydroxyindole associe a un iodure et une composition de peroxyde d'hydrogene a ph alcalin
LU86947A1 (fr) *	1987-07-17	1989-03-08	Oreal	Procede de teinture des fibres keratiniques,en particulier humaines,avec le 5-(hydroxy ou-methoxy)6-hydroxyindole

1988
- 1988-09-12 LU LU87337A patent/LU87337A1/fr unknown
1989
- 1989-09-05 CH CH3213/89A patent/CH679551A5/fr not_active IP Right Cessation
- 1989-09-07 AT AT0210089A patent/AT400672B/de not_active IP Right Cessation
- 1989-09-07 ZA ZA896845A patent/ZA896845B/xx unknown
- 1989-09-08 GR GR890100568A patent/GR1000461B/el not_active IP Right Cessation
- 1989-09-08 PT PT91663A patent/PT91663B/pt not_active IP Right Cessation
- 1989-09-11 AR AR89314892A patent/AR245515A1/es active
- 1989-09-11 IT IT8967751A patent/IT1232920B/it active
- 1989-09-11 BE BE8900961A patent/BE1002235A4/fr not_active IP Right Cessation
- 1989-09-11 ES ES8903090A patent/ES2016162A6/es not_active Expired - Lifetime
- 1989-09-11 FR FR8911815A patent/FR2636236B1/fr not_active Expired - Lifetime
- 1989-09-11 GB GB8920524A patent/GB2224518B/en not_active Expired - Lifetime
- 1989-09-11 BR BR898904562A patent/BR8904562A/pt not_active IP Right Cessation
- 1989-09-11 AU AU41207/89A patent/AU626579B2/en not_active Expired
- 1989-09-12 DE DE3930473A patent/DE3930473B4/de not_active Expired - Lifetime
- 1989-09-12 CA CA000611132A patent/CA1341195C/fr not_active Expired - Lifetime
- 1989-09-12 NL NL8902281A patent/NL194230C/nl not_active IP Right Cessation
- 1989-09-12 KR KR1019890013240A patent/KR0172112B1/ko not_active Expired - Lifetime
- 1989-09-12 JP JP1236768A patent/JP2744080B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR900004317A (ko)	1990-04-12
FR2636236B1 (fr)	1993-10-22
BE1002235A4 (fr)	1990-10-30
IT8967751A0 (it)	1989-09-11
ES2016162A6 (es)	1990-10-16
DE3930473B4 (de)	2006-04-27
JPH02121912A (ja)	1990-05-09
GR1000461B (el)	1992-07-30
JP2744080B2 (ja)	1998-04-28
FR2636236A1 (fr)	1990-03-16
LU87337A1 (fr)	1990-04-06
GB2224518B (en)	1992-07-22
IT1232920B (it)	1992-03-05
NL194230C (nl)	2001-10-02
NL8902281A (nl)	1990-04-02
KR0172112B1 (ko)	1999-02-01
AU4120789A (en)	1990-03-15
AR245515A1 (es)	1994-01-31
ATA210089A (de)	1995-07-15
PT91663A (pt)	1990-03-30
GR890100568A (en)	1990-10-31
BR8904562A (pt)	1990-05-01
GB8920524D0 (en)	1989-10-25
NL194230B (nl)	2001-06-01
PT91663B (pt)	1995-08-09
AU626579B2 (en)	1992-08-06
ZA896845B (en)	1991-05-29
AT400672B (de)	1996-02-26
CA1341195C (fr)	2001-02-27
GB2224518A (en)	1990-05-09
DE3930473A1 (de)	1990-03-15

Legal Events

Date	Code	Title	Description
2009-09-15	PL	Patent ceased

Publication	Publication Date	Title
EP0424261B1 (de)	1996-01-03	Färbemittel, das Oxydationsfarbvorstufen und Aminoindol-Kuppler enthält
EP0428441B1 (de)	1994-08-24	Färbemittel für keratinische Fasern, die Prekursoren von Oxidationsfarbstoffen und Derivaten des 4-Hydroxyindols als Kuppler enthalten und Färbungsverfahren unter deren Verwendung
EP0465339B1 (de)	1993-12-29	Verfahren zur keratinischen Faserfärbung mit 4-Hydroxyindolderivaten bei säurigem pH-Wert und Mittel
FR2699816A1 (fr)	1994-07-01	Compositions tinctoriales pour fibres kératiniques à base de paraphénylènediamines, de métaphénylènediamines et de dérivés du benzimidazole, et procédé de teinture les mettant en Óoeuvre.
EP0465340A1 (de)	1992-01-08	Verfahren zur keratinischen Färbung mit 4-Hydroxyindol bei säurigem pH-Wert und Mittel
EP0446132A1 (de)	1991-09-11	Verfahren zur Färbung von keratinischen Fasern mit 6- oder 7-Monohydroxyindolen unter säurischem pH und Zusammensetzungen
EP0652742B1 (de)	1997-08-27	Verwendung von 3-substituierten para-aminophenolen zum färben von keratinfasern und neue substituierte 3-para-aminophenole
EP0663814A1 (de)	1995-07-26	Verfahren zum Färben von Keratinfasern unter Verwendung eines Alkoxymetaphenylendiamins mit saurem pH-Wert und Zusammensetzung hierfür
EP0294669B1 (de)	1991-07-17	Metaphenylendiamine, Verfahren zu deren Herstellung, Zwischenprodukte und Verwendung dieser Metaphenylendiamine als Kuppler für die oxidative Färbung von Keratinfasern insbesondere von menschlichem Haar
EP0506549B1 (de)	1995-10-18	Färbemittel für Keratinfasern, das Oxydationsfarbstoffvorprodukte und Hydroxybenzofuran-Kuppler enthält, und Verfahren zur Färbung mit diesem Mittel
FR2675380A1 (fr)	1992-10-23	Procede de teinture des fibres keratiniques avec des aminoindoles, a ph basique, compositions mises en óoeuvre et nouveaux composes.
EP0599703B1 (de)	1997-09-17	Verwendung von 4-Hydroxy oder 4-Aminobenzimidazol oder Ihren Derivaten as wie Kuppler-substanzen in Oxidationsfärbungszusammensetzungen, sowie Zusammensetzungen und Verfahren zu deren Anwendung
EP0459900A1 (de)	1991-12-04	Verfahren zum Färben von Keratinfasern mit 2,4-Diamino-1,3-dimethoxybenzol in einem sauren Medium sowie Mittel zur Durchführung des Verfahrens
EP0295474B1 (de)	1991-07-17	Clorometaphenylendiamine, deren Verwendung als Kuppler für die oxidative Färbung von Keratinfasern, Haarfärbezusammensetzungen, die diese Verbindungen enthalten und Färbeverfahren mit diesen Zusammensetzungen
EP0586660B1 (de)	1997-01-29	Metaphenylendiamine mit schwefel in position 2 zur haarfärbung
FR2654336A1 (fr)	1991-05-17	Composition tinctoriale pour fibres keratiniques, contenant des precurseurs de colorants par oxydation et des coupleurs derives de 6- ou 7-hydroxyindole, et procede de teinture mettant en óoeuvre ces compositions.
EP0370880B1 (de)	1992-11-11	Trialkoxy-substituierte m-Phenylendiamine, Verfahren zu ihrer Herstellung und ihre Verwendung als Koppler beim Oxydationsfärben von keratinischen Fasern, besonders menschliche Haare
FR2579103A1 (fr)	1986-09-26	Utilisation de 4,5-methylenedioxyphenol halogene dans la teinture des fibres keratiniques
CA1341195C (fr)	2001-02-27	Compositions tinctoriales pour fibres keratiniques et procedes de teinture mettant en oeuvre ces compositions
CH675205A5 (de)	1990-09-14
EP0593711B1 (de)	1996-06-12	Verfahren zur färbung von keratinfasern in alkalischem milieu mit hilfe von 2-substituierten para-aminophenolen in kombination mit 6- oder 7- hydroxyindol, und entsprechende zusammensetzungen
CH675719A5 (de)	1990-10-31