AT386742B - Mittel und verfahren zur faerbung keratinischer fasern - Google Patents
Mittel und verfahren zur faerbung keratinischer fasernInfo
- Publication number
- AT386742B AT386742B AT0443781A AT443781A AT386742B AT 386742 B AT386742 B AT 386742B AT 0443781 A AT0443781 A AT 0443781A AT 443781 A AT443781 A AT 443781A AT 386742 B AT386742 B AT 386742B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- methyl
- nitro
- amino
- water
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 42
- 239000000835 fiber Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 9
- 238000004040 coloring Methods 0.000 title description 11
- 239000000203 mixture Substances 0.000 claims description 82
- 239000003086 colorant Substances 0.000 claims description 49
- -1 alkyl radical Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000004043 dyeing Methods 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000217 alkyl group Polymers 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000002537 cosmetic Substances 0.000 claims description 8
- 102000011782 Keratins Human genes 0.000 claims description 7
- 108010076876 Keratins Proteins 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
- 239000000047 product Substances 0.000 description 37
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- 238000002360 preparation method Methods 0.000 description 32
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- 239000011541 reaction mixture Substances 0.000 description 28
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- 238000003756 stirring Methods 0.000 description 24
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- 229910021529 ammonia Inorganic materials 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
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- 238000012360 testing method Methods 0.000 description 16
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- 238000001953 recrystallisation Methods 0.000 description 15
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 13
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- 239000000126 substance Substances 0.000 description 11
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 8
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 8
- 239000005639 Lauric acid Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 239000001768 carboxy methyl cellulose Substances 0.000 description 8
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 8
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 8
- ALSTYHKOOCGGFT-UHFFFAOYSA-N cis-oleyl alcohol Natural products CCCCCCCCC=CCCCCCCCCO ALSTYHKOOCGGFT-UHFFFAOYSA-N 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- HQHZFBHHZQINAK-UHFFFAOYSA-N 1,2,3,4-tetraaminoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(N)=C(N)C(N)=C3C(=O)C2=C1 HQHZFBHHZQINAK-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
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- 235000012255 calcium oxide Nutrition 0.000 description 7
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical class NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 7
- 229960005323 phenoxyethanol Drugs 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PJRDJHIRYREDHP-UHFFFAOYSA-N 2-methyl-5-nitrobenzene-1,4-diamine Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1N PJRDJHIRYREDHP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 6
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical class CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 6
- KCBKRIFITFLPAS-UHFFFAOYSA-N 1-n,2-dimethyl-5-nitrobenzene-1,4-diamine Chemical compound CNC1=CC([N+]([O-])=O)=C(N)C=C1C KCBKRIFITFLPAS-UHFFFAOYSA-N 0.000 description 5
- WCVCNOIOYNODPL-UHFFFAOYSA-N 2-methyl-5-nitro-1-n-propylbenzene-1,4-diamine Chemical compound CCCNC1=CC([N+]([O-])=O)=C(N)C=C1C WCVCNOIOYNODPL-UHFFFAOYSA-N 0.000 description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 5
- GZYBSURBYCLNSM-UHFFFAOYSA-N 3-anilinopropan-1-ol Chemical compound OCCCNC1=CC=CC=C1 GZYBSURBYCLNSM-UHFFFAOYSA-N 0.000 description 5
- 241001070941 Castanea Species 0.000 description 5
- 235000014036 Castanea Nutrition 0.000 description 5
- TYZUBICZHUYZQW-UHFFFAOYSA-N N-(4-amino-5-methyl-2-nitrophenyl)-4-methylbenzenesulfonamide Chemical compound CC=1C=C(NS(=O)(=O)C2=CC=C(C)C=C2)C(=CC=1N)[N+](=O)[O-] TYZUBICZHUYZQW-UHFFFAOYSA-N 0.000 description 5
- BTBJBAZGXNKLQC-UHFFFAOYSA-N ammonium lauryl sulfate Chemical compound [NH4+].CCCCCCCCCCCCOS([O-])(=O)=O BTBJBAZGXNKLQC-UHFFFAOYSA-N 0.000 description 5
- 229940063953 ammonium lauryl sulfate Drugs 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000000982 direct dye Substances 0.000 description 5
- WOUSLYQPVFAPBG-UHFFFAOYSA-N 1-n-ethyl-2-methyl-5-nitrobenzene-1,4-diamine Chemical compound CCNC1=CC([N+]([O-])=O)=C(N)C=C1C WOUSLYQPVFAPBG-UHFFFAOYSA-N 0.000 description 4
- JUWPZSZAIJPEFR-UHFFFAOYSA-N 2-ethyl-1-n-methyl-5-nitrobenzene-1,4-diamine Chemical compound CCC1=CC(N)=C([N+]([O-])=O)C=C1NC JUWPZSZAIJPEFR-UHFFFAOYSA-N 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
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- 238000004090 dissolution Methods 0.000 description 4
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- 229930195729 fatty acid Natural products 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- UENRCAFKOCYSLM-UHFFFAOYSA-N hexadecyl-(2-hydroxyethyl)-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CCO UENRCAFKOCYSLM-UHFFFAOYSA-N 0.000 description 1
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000006083 mineral thickener Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- RFUORPICHNGUJN-UHFFFAOYSA-N n-(3-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(O)=C1 RFUORPICHNGUJN-UHFFFAOYSA-N 0.000 description 1
- SADKHSORWAKDKY-UHFFFAOYSA-N n-(4-amino-2-nitrophenyl)-n,4-dimethylbenzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(C)C1=CC=C(N)C=C1[N+]([O-])=O SADKHSORWAKDKY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 229960003330 pentetic acid Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
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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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/418—Amines containing nitro groups
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B53/00—Quinone imides
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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU82861A LU82861A1 (fr) | 1980-10-16 | 1980-10-16 | Nouvelles nitro-paraphenylenediamines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
| LU83315A LU83315A1 (fr) | 1981-04-24 | 1981-04-24 | Nouvelles nitro-paraphenylenediamines,leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA443781A ATA443781A (de) | 1985-03-15 |
| AT386742B true AT386742B (de) | 1988-10-10 |
Family
ID=26640273
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0443781A AT386742B (de) | 1980-10-16 | 1981-10-15 | Mittel und verfahren zur faerbung keratinischer fasern |
| AT0234884A AT407112B (de) | 1980-10-16 | 1984-07-19 | Verwendung von 3-nitro-4-n-beta-hydroxyäthylamino-phenyl-beta, -dihydroxypropyläther als direktfarbstoff zum färben keratinischer fasern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0234884A AT407112B (de) | 1980-10-16 | 1984-07-19 | Verwendung von 3-nitro-4-n-beta-hydroxyäthylamino-phenyl-beta, -dihydroxypropyläther als direktfarbstoff zum färben keratinischer fasern |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4470826A (en, 2012) |
| JP (1) | JPH0372449A (en, 2012) |
| AR (2) | AR229594A1 (en, 2012) |
| AT (2) | AT386742B (en, 2012) |
| AU (1) | AU551179B2 (en, 2012) |
| BR (1) | BR8106657A (en, 2012) |
| CA (1) | CA1211756A (en, 2012) |
| CH (2) | CH651542A5 (en, 2012) |
| DE (2) | DE3141019A1 (en, 2012) |
| ES (1) | ES8301201A1 (en, 2012) |
| FR (1) | FR2492370A1 (en, 2012) |
| GB (2) | GB2086408B (en, 2012) |
| IT (1) | IT1144834B (en, 2012) |
| MX (1) | MX153835A (en, 2012) |
| NL (1) | NL8104684A (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2086408B (en) * | 1980-10-16 | 1985-10-09 | Oreal | New nitro-derivatives of the benzene series the process for their preparation and their use in the dyeing of keratin fibres |
| LU83686A1 (fr) * | 1981-10-08 | 1983-06-08 | Oreal | Composition tinctoriale pour fibres keratiniques a base de colorants nitres benzeniques |
| LU84875A1 (fr) * | 1983-06-27 | 1985-03-29 | Oreal | Compositions tinctoriales pour fibres keratiniques a base de colorants directs et de gomme de xanthane |
| DE3323207A1 (de) * | 1983-06-28 | 1985-01-03 | Wella Ag, 6100 Darmstadt | 1,4-diamino-5-chlor-2-nitrobenzolderivate, verfahren zu ihrer herstellung und mittel zur faerbung von haaren |
| FR2551748B1 (fr) * | 1983-09-08 | 1985-11-22 | Oreal | Nouvelles nitroparaphenylenediamines dimethylees, leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
| EP0145513B1 (fr) * | 1983-09-08 | 1988-03-23 | L'oreal | Nouveaux dérivés diméthylés de nitro-3 amino-4 aniline, leur procédé de préparation et leur utilisation en teinture des fibres kératiniques |
| FR2569401B1 (fr) * | 1984-08-23 | 1989-01-20 | Oreal | Nouveaux derives dimethyles de nitro-3 amino-4 aniline, leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
| LU85450A1 (fr) * | 1984-07-05 | Oreal | Procede de coloration a chaud avec des solutions sursaturees a froid | |
| FR2571364B1 (fr) * | 1984-10-09 | 1987-07-17 | Oreal | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede |
| US4727192A (en) * | 1984-12-13 | 1988-02-23 | L'oreal | 2,4-dinitro- or 2-amino-4-nitro- or 2-nitro-4-amino-6-hydroxyalkylanilines, the process for preparation thereof and their use in dyeing keratinous fibers, and especially human hair |
| LU85704A1 (fr) * | 1984-12-21 | 1986-07-17 | Oreal | Composition tinctoriale contenant la 5-nitrovanilline et son utilisation en teinture de fibres keratiniques,et en particulier des cheveux humains |
| LU85853A1 (fr) * | 1985-04-16 | 1986-11-05 | Oreal | Nouveaux nitroaminophenols,leur procede de preparation et leur utilisation en teinture des fibres keratiniques,nouveaux nitroaminobenzenes intermediaires et leur utilisation en teinture des fibres keratiniques |
| DE3519304A1 (de) * | 1985-05-30 | 1986-12-04 | Wella Ag, 6100 Darmstadt | Nitro-p-phenylendiaminderivate, verfahren zu ihrer herstellung sowie haarfaerbemittel mit einem gehalt an diesen verbindungen |
| US4764174A (en) * | 1986-01-30 | 1988-08-16 | Helene Curtis, Inc. | Nitrophenylenediamine dye composition having improved deposition on human hair and wool |
| DE3917114C3 (de) * | 1989-05-26 | 1996-08-14 | Schwarzkopf Gmbh Hans | Neue Nitro-p-phenylendiaminderivate, Verfahren zu ihrer Herstellung sowie Färbemittel für keratinische Fasern, die diese enthalten |
| DE3917113A1 (de) * | 1989-05-26 | 1990-11-29 | Schwarzkopf Gmbh Hans | Verfahren zur selektiven herstellung von n(pfeil hoch)4(pfeil hoch)-substituierten 1,4-diamino-2-nitrobenzolen |
| DE3943545A1 (de) * | 1989-09-23 | 1991-04-04 | Schwarzkopf Gmbh Hans | N(pfeil hoch)1(pfeil hoch)-substituierte nitro-p-phenylendiamin-zwischenprodukte |
| US5144957A (en) * | 1990-01-24 | 1992-09-08 | Zetachron | Cutaneous therapeutic devices |
| WO1991011135A1 (en) * | 1990-01-24 | 1991-08-08 | Zetachron, Inc. | Cutaneous therapeutic devices |
| US6074438A (en) * | 1998-03-03 | 2000-06-13 | Bristol-Myers Squibb Co. | Hair dyeing compositions containing 2-chloro- and 2,6-dichloro-4-aminophenol and phenylpyrazolones |
| DE60129956T2 (de) * | 2000-06-12 | 2008-05-08 | Kao Corp. | Blondiermittel oder haarfärbemittel |
| EP1813254B1 (en) * | 2000-12-28 | 2009-08-26 | Kao Corporation | Hair bleach composition and hair dye composition |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2750326A (en) * | 1951-02-07 | 1956-06-12 | Lever Brothers Ltd | Process and composition for dyeing hair |
| CH355567A (fr) * | 1955-11-29 | 1961-07-15 | Oreal | Composition aqueuse pour la teinture des cheveux et autres fibres non textiles à base de kératine |
| AT217161B (de) * | 1959-04-23 | 1961-09-11 | Oreal | Haarfärbemittel |
| AT275048B (de) * | 1964-11-19 | 1969-10-10 | Oreal | Färbemittel für Haare |
| AT276636B (de) * | 1965-04-26 | 1969-11-25 | Oreal | Verfahren zum Färben von Haaren und Mittel zur Durchführung desselben |
| DE1492207A1 (de) * | 1964-04-14 | 1969-12-04 | Unilever Nv | Haarfaerbemittel |
| DE1444216B2 (de) * | 1962-10-18 | 1973-09-20 | Clairol Inc., New York, N.Y. (V.St.A.) | Stabilisiertes Haarfärbemittel |
| DE1924249C3 (de) * | 1968-05-13 | 1979-01-25 | Bristol-Myers Co., New York, N.Y. (V.St.A.) | Nitro-p-phenylendiamine, Verfahren zur N-Monomethylierung von Nitroanilinen und Nitro-p-phenylendiaminen und Verwendung der N-Monomethylnitroaniline zum Färben von Haaren |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2750327A (en) * | 1953-06-01 | 1956-06-12 | Lever Brothers Ltd | Process of dyeing animal fibers and dyes and dyeing compositions therefor |
| GB741334A (en) * | 1953-06-01 | 1955-11-30 | Unilever Ltd | Improvements in or relating to hair dyes |
| GB812211A (en) * | 1955-11-29 | 1959-04-22 | Oreal | Nitro-phenylene diamines and their use in dyeing animal fibres |
| NL240434A (en, 2012) * | 1959-04-23 | |||
| GB1008844A (en) * | 1961-04-12 | 1965-11-03 | Oreal | New nitrophenylenediamine derivatives and their use in dyeing animal fibres |
| LU49990A1 (en, 2012) * | 1965-12-03 | 1967-06-05 | ||
| US3904690A (en) * | 1965-12-03 | 1975-09-09 | Oreal | 2-Nitro-meta-phenylenediamines |
| US3632582A (en) * | 1967-11-02 | 1972-01-04 | Clairol Inc | Process for preparing nitro-p-phenylene-diamines |
| NL7115348A (en, 2012) * | 1970-11-25 | 1972-05-29 | ||
| US3925424A (en) * | 1972-03-08 | 1975-12-09 | Paul Riegger | Process for preparing 4-chloroformyl phthalic acid anhydride |
| FR2290186A1 (fr) * | 1974-11-05 | 1976-06-04 | Oreal | Compositions tinctoriales pour cheveux humains et nouveaux etheroxydes entrant dans ces compositions |
| GR74343B (en, 2012) | 1980-08-08 | 1984-06-26 | Oreal | |
| GB2086408B (en) * | 1980-10-16 | 1985-10-09 | Oreal | New nitro-derivatives of the benzene series the process for their preparation and their use in the dyeing of keratin fibres |
-
1981
- 1981-10-14 GB GB8130942A patent/GB2086408B/en not_active Expired
- 1981-10-15 US US06/311,905 patent/US4470826A/en not_active Expired - Lifetime
- 1981-10-15 CH CH6608/81A patent/CH651542A5/fr not_active IP Right Cessation
- 1981-10-15 ES ES506258A patent/ES8301201A1/es not_active Expired
- 1981-10-15 AT AT0443781A patent/AT386742B/de not_active IP Right Cessation
- 1981-10-15 DE DE19813141019 patent/DE3141019A1/de active Granted
- 1981-10-15 DE DE3153423A patent/DE3153423C2/de not_active Expired - Lifetime
- 1981-10-15 NL NL8104684A patent/NL8104684A/nl not_active Application Discontinuation
- 1981-10-15 CA CA000387988A patent/CA1211756A/fr not_active Expired
- 1981-10-15 AR AR287095A patent/AR229594A1/es active
- 1981-10-15 AU AU76360/81A patent/AU551179B2/en not_active Expired
- 1981-10-15 CH CH109/85A patent/CH657607A5/fr not_active IP Right Cessation
- 1981-10-15 IT IT68339/81A patent/IT1144834B/it active
- 1981-10-15 BR BR8106657A patent/BR8106657A/pt not_active IP Right Cessation
- 1981-10-15 FR FR8119393A patent/FR2492370A1/fr active Granted
- 1981-10-16 MX MX189691A patent/MX153835A/es unknown
-
1982
- 1982-09-28 AR AR290782A patent/AR228921A1/es active
-
1984
- 1984-05-29 GB GB08413642A patent/GB2153377B/en not_active Expired
- 1984-07-19 AT AT0234884A patent/AT407112B/de not_active IP Right Cessation
-
1990
- 1990-07-23 JP JP2194679A patent/JPH0372449A/ja active Granted
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2750326A (en) * | 1951-02-07 | 1956-06-12 | Lever Brothers Ltd | Process and composition for dyeing hair |
| CH355567A (fr) * | 1955-11-29 | 1961-07-15 | Oreal | Composition aqueuse pour la teinture des cheveux et autres fibres non textiles à base de kératine |
| AT217161B (de) * | 1959-04-23 | 1961-09-11 | Oreal | Haarfärbemittel |
| DE1444216B2 (de) * | 1962-10-18 | 1973-09-20 | Clairol Inc., New York, N.Y. (V.St.A.) | Stabilisiertes Haarfärbemittel |
| DE1492207A1 (de) * | 1964-04-14 | 1969-12-04 | Unilever Nv | Haarfaerbemittel |
| AT275048B (de) * | 1964-11-19 | 1969-10-10 | Oreal | Färbemittel für Haare |
| AT276636B (de) * | 1965-04-26 | 1969-11-25 | Oreal | Verfahren zum Färben von Haaren und Mittel zur Durchführung desselben |
| DE1924249C3 (de) * | 1968-05-13 | 1979-01-25 | Bristol-Myers Co., New York, N.Y. (V.St.A.) | Nitro-p-phenylendiamine, Verfahren zur N-Monomethylierung von Nitroanilinen und Nitro-p-phenylendiaminen und Verwendung der N-Monomethylnitroaniline zum Färben von Haaren |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA234884A (de) | 2000-05-15 |
| DE3153423C2 (en, 2012) | 1990-10-11 |
| MX153835A (es) | 1987-01-19 |
| NL8104684A (nl) | 1982-05-17 |
| IT1144834B (it) | 1986-10-29 |
| DE3141019A1 (de) | 1982-06-03 |
| FR2492370A1 (fr) | 1982-04-23 |
| JPH0372449A (ja) | 1991-03-27 |
| US4470826A (en) | 1984-09-11 |
| GB2153377B (en) | 1986-01-29 |
| AU7636081A (en) | 1982-04-22 |
| CH657607A5 (fr) | 1986-09-15 |
| GB2086408B (en) | 1985-10-09 |
| ES506258A0 (es) | 1982-11-16 |
| FR2492370B1 (en, 2012) | 1984-11-30 |
| GB2086408A (en) | 1982-05-12 |
| AU551179B2 (en) | 1986-04-17 |
| JPH0446944B2 (en, 2012) | 1992-07-31 |
| AR228921A1 (es) | 1983-04-29 |
| AT407112B (de) | 2000-12-27 |
| GB8413642D0 (en) | 1984-07-04 |
| GB2153377A (en) | 1985-08-21 |
| IT8168339A0 (it) | 1981-10-15 |
| ES8301201A1 (es) | 1982-11-16 |
| BR8106657A (pt) | 1982-06-29 |
| AR229594A1 (es) | 1983-09-30 |
| CA1211756A (fr) | 1986-09-23 |
| ATA443781A (de) | 1985-03-15 |
| DE3141019C2 (en, 2012) | 1991-06-20 |
| CH651542A5 (fr) | 1985-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELA | Expired due to lapse of time |