CH677873A5 - - Google Patents
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- Publication number
- CH677873A5 CH677873A5 CH4637/88A CH463788A CH677873A5 CH 677873 A5 CH677873 A5 CH 677873A5 CH 4637/88 A CH4637/88 A CH 4637/88A CH 463788 A CH463788 A CH 463788A CH 677873 A5 CH677873 A5 CH 677873A5
- Authority
- CH
- Switzerland
- Prior art keywords
- composition
- group
- dyeing
- amino
- hydrogen peroxide
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 164
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 86
- 239000000975 dye Substances 0.000 claims description 60
- 210000004209 hair Anatomy 0.000 claims description 51
- 230000003647 oxidation Effects 0.000 claims description 51
- 238000007254 oxidation reaction Methods 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 42
- -1 amine salts Chemical class 0.000 claims description 35
- 238000004043 dyeing Methods 0.000 claims description 35
- 239000000835 fiber Substances 0.000 claims description 27
- 239000002609 medium Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 102000011782 Keratins Human genes 0.000 claims description 18
- 108010076876 Keratins Proteins 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 17
- 239000003755 preservative agent Substances 0.000 claims description 15
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000002475 indoles Chemical class 0.000 claims description 14
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 11
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 229940018563 3-aminophenol Drugs 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- ILDXSRFKXABMHH-UHFFFAOYSA-N 2-(2-aminophenyl)ethanol Chemical compound NC1=CC=CC=C1CCO ILDXSRFKXABMHH-UHFFFAOYSA-N 0.000 claims description 5
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 4
- QAOUFMMMANSOSS-UHFFFAOYSA-N 2-amino-3-(2-hydroxyethyl)phenol Chemical compound NC1=C(O)C=CC=C1CCO QAOUFMMMANSOSS-UHFFFAOYSA-N 0.000 claims description 4
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 4
- LPYUENQFPVNPHY-UHFFFAOYSA-N 3-methoxycatechol Chemical compound COC1=CC=CC(O)=C1O LPYUENQFPVNPHY-UHFFFAOYSA-N 0.000 claims description 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 4
- MDKWXZDIFPHNPS-UHFFFAOYSA-N 2-(2,3-diaminophenyl)ethanol Chemical compound NC1=CC=CC(CCO)=C1N MDKWXZDIFPHNPS-UHFFFAOYSA-N 0.000 claims description 3
- MGBKJKDRMRAZKC-UHFFFAOYSA-N 3-aminobenzene-1,2-diol Chemical class NC1=CC=CC(O)=C1O MGBKJKDRMRAZKC-UHFFFAOYSA-N 0.000 claims description 3
- BKYQHRSVSLQLLQ-UHFFFAOYSA-N 6-methoxy-1,3-benzodioxol-5-amine Chemical compound C1=C(N)C(OC)=CC2=C1OCO2 BKYQHRSVSLQLLQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 150000004694 iodide salts Chemical class 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 2
- PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical class NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 claims description 2
- QKGQHTCUNGPCIA-UHFFFAOYSA-N 2,4,5-Trihydroxytoluene Chemical compound CC1=CC(O)=C(O)C=C1O QKGQHTCUNGPCIA-UHFFFAOYSA-N 0.000 claims description 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 claims description 2
- MJMRSGYLARBUDK-UHFFFAOYSA-N 2,4-dimethoxybenzene-1,3-diamine Chemical compound COC1=CC=C(N)C(OC)=C1N MJMRSGYLARBUDK-UHFFFAOYSA-N 0.000 claims description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical class COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 claims description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-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
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical class C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 claims description 2
- YFTGOBNOJKXZJC-UHFFFAOYSA-N 5,6-dihydroxyindole-2-carboxylic acid Chemical compound OC1=C(O)C=C2NC(C(=O)O)=CC2=C1 YFTGOBNOJKXZJC-UHFFFAOYSA-N 0.000 claims description 2
- CQPLGGXOAHSQBD-UHFFFAOYSA-N 5-amino-2,4-dimethoxyphenol Chemical compound COC1=CC(OC)=C(O)C=C1N CQPLGGXOAHSQBD-UHFFFAOYSA-N 0.000 claims description 2
- BLQFHJKRTDIZLX-UHFFFAOYSA-N 5-amino-2-methoxyphenol Chemical compound COC1=CC=C(N)C=C1O BLQFHJKRTDIZLX-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- SBXKRBZKPQBLOD-UHFFFAOYSA-N aminohydroquinone Chemical compound NC1=CC(O)=CC=C1O SBXKRBZKPQBLOD-UHFFFAOYSA-N 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 230000003750 conditioning effect Effects 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 150000002193 fatty amides Chemical class 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 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
- 230000008961 swelling Effects 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- SBYDCEZCBVBMSI-UHFFFAOYSA-N 1,2-diamino-1-phenoxyethanol Chemical compound NCC(N)(O)OC1=CC=CC=C1 SBYDCEZCBVBMSI-UHFFFAOYSA-N 0.000 claims 1
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 claims 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- PBDBPADWXQFEIN-UHFFFAOYSA-N 2,5-diamino-4-methoxyphenol Chemical compound COC1=CC(N)=C(O)C=C1N PBDBPADWXQFEIN-UHFFFAOYSA-N 0.000 claims 1
- IMCITHBRDBCOLO-UHFFFAOYSA-N 2-(diethylamino)benzene-1,4-diol Chemical compound CCN(CC)C1=CC(O)=CC=C1O IMCITHBRDBCOLO-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QGJCWKNNWOVPTJ-UHFFFAOYSA-N 2-methyl-1h-indole-5,6-diol Chemical compound OC1=C(O)C=C2NC(C)=CC2=C1 QGJCWKNNWOVPTJ-UHFFFAOYSA-N 0.000 claims 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims 1
- XSBKXUJEVYHSNO-UHFFFAOYSA-N 3-amino-2,6-dimethylphenol Chemical compound CC1=CC=C(N)C(C)=C1O XSBKXUJEVYHSNO-UHFFFAOYSA-N 0.000 claims 1
- HEAHXMOKYXTEID-UHFFFAOYSA-N 3-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C=C1N HEAHXMOKYXTEID-UHFFFAOYSA-N 0.000 claims 1
- RRIMNXYWOCQLCF-UHFFFAOYSA-N 4,6-dimethoxybenzene-1,3-diamine Chemical compound COC1=CC(OC)=C(N)C=C1N RRIMNXYWOCQLCF-UHFFFAOYSA-N 0.000 claims 1
- ROCVGJLXIARCAC-UHFFFAOYSA-N 4-aminobenzene-1,3-diol Chemical compound NC1=CC=C(O)C=C1O ROCVGJLXIARCAC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002978 peroxides Chemical group 0.000 claims 1
- 229940098465 tincture Drugs 0.000 claims 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 32
- 229920013806 TRITON CG-110 Polymers 0.000 description 13
- 229930182470 glycoside Natural products 0.000 description 13
- 229920002907 Guar gum Polymers 0.000 description 12
- 239000000665 guar gum Substances 0.000 description 12
- 235000010417 guar gum Nutrition 0.000 description 12
- 229960002154 guar gum Drugs 0.000 description 12
- 229920013683 Celanese Polymers 0.000 description 11
- 238000004040 coloring Methods 0.000 description 11
- 230000002335 preservative effect Effects 0.000 description 10
- 239000002453 shampoo Substances 0.000 description 10
- 150000002338 glycosides Chemical class 0.000 description 9
- 230000002269 spontaneous effect Effects 0.000 description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
- 229940006461 iodide ion Drugs 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000000230 xanthan gum Substances 0.000 description 4
- 235000010493 xanthan gum Nutrition 0.000 description 4
- 229920001285 xanthan gum Polymers 0.000 description 4
- 229940082509 xanthan gum Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- ZCSHACFHMFHFKK-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;2,4,6-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)C1NC([N+]([O-])=O)NC([N+]([O-])=O)N1.CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZCSHACFHMFHFKK-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 241000158728 Meliaceae Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 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 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- HMTUVSJLXALWIU-UHFFFAOYSA-N 2,3-dimethyl-1h-indole-5,6-diol Chemical compound OC1=C(O)C=C2C(C)=C(C)NC2=C1 HMTUVSJLXALWIU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OCRZWHWVTPLTRF-UHFFFAOYSA-N 2-(2-amino-5-methoxyphenyl)ethanol Chemical compound COC1=CC=C(N)C(CCO)=C1 OCRZWHWVTPLTRF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- ZUTZCXDHPIACCR-UHFFFAOYSA-N 3-methyl-1h-indole-5,6-diol Chemical compound OC1=C(O)C=C2C(C)=CNC2=C1 ZUTZCXDHPIACCR-UHFFFAOYSA-N 0.000 description 1
- RWEBZZKCIMKUTO-UHFFFAOYSA-N 5-methoxy-1h-indol-6-ol Chemical compound C1=C(O)C(OC)=CC2=C1NC=C2 RWEBZZKCIMKUTO-UHFFFAOYSA-N 0.000 description 1
- KVHHMYZBFBSVDI-UHFFFAOYSA-N 8-aminonaphthalen-2-ol Chemical compound C1=C(O)C=C2C(N)=CC=CC2=C1 KVHHMYZBFBSVDI-UHFFFAOYSA-N 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000282372 Panthera onca Species 0.000 description 1
- 229920002305 Schizophyllan Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011054 acetic acid Nutrition 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- PRKQVKDSMLBJBJ-UHFFFAOYSA-N ammonium carbonate Chemical class N.N.OC(O)=O PRKQVKDSMLBJBJ-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000011162 ammonium carbonates Nutrition 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 239000012298 atmosphere Substances 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
- 229920001222 biopolymer Polymers 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 230000037308 hair color Effects 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940037201 oris Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/20—Halogens; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87086A LU87086A1 (fr) | 1987-12-18 | 1987-12-18 | Procede de teinture des fibres keratiniques avec des colorants d'oxydation associes au 5,6-dihydroxyindole et a un iodure et composition tinctoriale mise en oeuvre |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH677873A5 true CH677873A5 (enrdf_load_stackoverflow) | 1991-07-15 |
Family
ID=19731001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH4637/88A CH677873A5 (enrdf_load_stackoverflow) | 1987-12-18 | 1988-12-15 |
Country Status (13)
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2659552B2 (fr) * | 1989-10-20 | 1994-11-04 | Oreal | Procede de teinture des fibres keratiniques avec des aminoindoles, composition et dispositif de mise en óoeuvre. |
| DE3935128A1 (de) * | 1989-10-21 | 1991-04-25 | Henkel Kgaa | Oxidationsfaerbemittel, dessen herstellung und anwendung |
| FR2654336B1 (fr) * | 1989-11-10 | 1994-06-03 | Oreal | 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. |
| 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. |
| FR2663651B1 (fr) * | 1990-06-21 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec des composes indoliques, compositions et dispositifs de mises en óoeuvre. |
| FR2664304B1 (fr) * | 1990-07-05 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec le 4-hydroxyindole a ph acide et compositions mises en óoeuvre. |
| FR2664305B1 (fr) * | 1990-07-05 | 1992-10-09 | Oreal | Procede de teinture des fibres keratiniques avec des derives du 4-hydroxyindole a ph acide et compositions mise en óoeuvre. |
| FR2671722B1 (fr) * | 1991-01-21 | 1993-04-16 | Oreal | Utilisation de derives indoliques a titre de coupleurs dans la teinture des fibres keratiniques. |
| FR2678263B1 (fr) * | 1991-06-26 | 1995-03-03 | Oreal | Meta-aminophenols, leur utilisation en tant que coupleurs pour la teinture d'oxydation des fibres keratiniques, compositions et procede de teinture. |
| US5273550A (en) * | 1991-09-26 | 1993-12-28 | Clairol Incorporated | Process and kit for dyeing hair |
| US5279618A (en) * | 1991-09-26 | 1994-01-18 | Clairol Incorporated | Process and kit for dyeing hair |
| US6569211B2 (en) | 1991-11-19 | 2003-05-27 | Henkel Kommanditgesellschaft Auf Aktien | 5,6-dihydroxyindolines as additives for hair dyeing preparations |
| FR2692782B1 (fr) * | 1992-06-25 | 1995-06-23 | Oreal | Procede de teinture des fibres keratiniques avec des derives indoliques ou indoliniques, du peroxyde d'hydrogene et une peroxydase. |
| DE19732975A1 (de) * | 1997-07-31 | 1999-02-04 | Henkel Kgaa | Färbemittel |
| ATE258421T1 (de) | 1998-06-23 | 2004-02-15 | Henkel Kgaa | Färbemittel zum färben von keratinfasern |
| FR2786092B1 (fr) | 1998-11-20 | 2002-11-29 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| FR2786094B1 (fr) | 1998-11-20 | 2001-01-12 | Oreal | Composition de teinture d'oxydation des fibres keratiniques et procede de teinture mettant en oeuvre cette composition |
| DE102005043187A1 (de) * | 2005-09-09 | 2007-03-15 | Henkel Kgaa | Polymere mit kleiner Molmasse |
| EP2332516A1 (en) * | 2009-12-09 | 2011-06-15 | KPSS-Kao Professional Salon Services GmbH | Process for oxidative colouring keratin fibres |
| EP2338470A1 (en) * | 2009-12-22 | 2011-06-29 | KPSS-Kao Professional Salon Services GmbH | Process for oxidative colouring keratin fibers |
| WO2013148804A2 (en) | 2012-03-27 | 2013-10-03 | The Procter & Gamble Company | Hair colorant compositions comprising 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 |
| JP7104954B2 (ja) * | 2016-04-28 | 2022-07-22 | ホーユー株式会社 | 酸化染毛剤組成物 |
| JP6792767B2 (ja) * | 2016-04-28 | 2020-12-02 | ホーユー株式会社 | 酸化染毛剤組成物 |
| CN115990116A (zh) * | 2016-04-28 | 2023-04-21 | 朋友株式会社 | 氧化染发剂组合物 |
| TW202118477A (zh) * | 2019-10-31 | 2021-05-16 | 日商朋友股份有限公司 | 氧化染髮劑 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2421606A1 (fr) * | 1978-04-06 | 1979-11-02 | Oreal | Procede de teinture de fibres keratiniques en deux temps |
| DE3031709A1 (de) * | 1980-08-22 | 1982-04-22 | Wella Ag, 6100 Darmstadt | Mittel und verfahren zur oxidativen faerbung von haaren |
| LU86256A1 (fr) * | 1986-01-20 | 1988-01-20 | Oreal | Procede de teinture des fibres keratiniques avec du 5,6-dihydroxyindole associe avec un iodure |
| 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 |
| LU86899A1 (fr) * | 1987-05-25 | 1989-01-19 | Oreal | Procede de teinture des fibres keratiniques avec des colorants d'oxydation associes a un iodure et composition tinctoriale mise en oeuvre |
| 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 |
| US4860735A (en) * | 1988-08-08 | 1989-08-29 | The General Hospital Corporation | Drill alignment guide for osteoplastic surgery |
-
1987
- 1987-12-18 LU LU87086A patent/LU87086A1/fr unknown
-
1988
- 1988-12-13 GR GR880100834A patent/GR1000167B/el unknown
- 1988-12-15 NL NL8803075A patent/NL8803075A/nl not_active Application Discontinuation
- 1988-12-15 CH CH4637/88A patent/CH677873A5/fr not_active IP Right Cessation
- 1988-12-16 PT PT89238A patent/PT89238B/pt not_active IP Right Cessation
- 1988-12-16 JP JP63318311A patent/JP2595076B2/ja not_active Expired - Lifetime
- 1988-12-16 DE DE3842508A patent/DE3842508A1/de not_active Withdrawn
- 1988-12-16 BE BE8801412A patent/BE1001329A3/fr not_active IP Right Cessation
- 1988-12-16 IT IT68119/88A patent/IT1224001B/it active
- 1988-12-16 FR FR8816685A patent/FR2624730B1/fr not_active Expired - Fee Related
- 1988-12-19 ZA ZA889447A patent/ZA889447B/xx unknown
- 1988-12-19 AU AU27026/88A patent/AU622878B2/en not_active Expired - Fee Related
- 1988-12-19 GB GB8829595A patent/GB2211517B/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GR1000167B (el) | 1991-10-10 |
| JPH01199906A (ja) | 1989-08-11 |
| LU87086A1 (fr) | 1989-07-07 |
| GB2211517A (en) | 1989-07-05 |
| JP2595076B2 (ja) | 1997-03-26 |
| AU2702688A (en) | 1989-07-13 |
| DE3842508A1 (de) | 1989-07-13 |
| IT1224001B (it) | 1990-09-26 |
| GB2211517B (en) | 1992-04-15 |
| FR2624730B1 (fr) | 1993-10-22 |
| NL8803075A (nl) | 1989-07-17 |
| AU622878B2 (en) | 1992-04-30 |
| FR2624730A1 (fr) | 1989-06-23 |
| PT89238A (pt) | 1989-12-29 |
| GB8829595D0 (en) | 1989-02-08 |
| BE1001329A3 (fr) | 1989-09-26 |
| PT89238B (pt) | 1993-07-30 |
| ZA889447B (en) | 1990-08-29 |
| IT8868119A0 (it) | 1988-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |