JP2002527369A - 繊維を染色するための薬剤及び方法 - Google Patents
繊維を染色するための薬剤及び方法Info
- Publication number
- JP2002527369A JP2002527369A JP2000575472A JP2000575472A JP2002527369A JP 2002527369 A JP2002527369 A JP 2002527369A JP 2000575472 A JP2000575472 A JP 2000575472A JP 2000575472 A JP2000575472 A JP 2000575472A JP 2002527369 A JP2002527369 A JP 2002527369A
- Authority
- JP
- Japan
- Prior art keywords
- hair
- amino
- nitro
- methyl
- dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004043 dyeing Methods 0.000 title claims abstract description 27
- 239000000835 fiber Substances 0.000 title claims abstract description 17
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 229940079593 drug Drugs 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
- 210000004209 hair Anatomy 0.000 claims description 90
- 239000000975 dye Substances 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- 239000007800 oxidant agent Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- BFAJPHCGGOBRGE-UHFFFAOYSA-N n-(2-methoxyethyl)-2-methyl-4-nitroaniline Chemical compound COCCNC1=CC=C([N+]([O-])=O)C=C1C BFAJPHCGGOBRGE-UHFFFAOYSA-N 0.000 claims description 8
- 239000001005 nitro dye Substances 0.000 claims description 8
- CXYNKJVZMJLYSO-UHFFFAOYSA-N 4-nitro-n-(oxolan-2-ylmethyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NCC1OCCC1 CXYNKJVZMJLYSO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000982 direct dye Substances 0.000 claims description 5
- MSWZIQWDSQOYCJ-UHFFFAOYSA-N n-(2-methoxyethyl)-4-nitroaniline Chemical compound COCCNC1=CC=C([N+]([O-])=O)C=C1 MSWZIQWDSQOYCJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229920005615 natural polymer Polymers 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 4
- LQPUAYMERQENBC-UHFFFAOYSA-N 4-(2-methyl-4-nitrophenyl)morpholine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N1CCOCC1 LQPUAYMERQENBC-UHFFFAOYSA-N 0.000 claims description 3
- IAJDSUYFELYZCS-UHFFFAOYSA-N 4-(4-nitrophenyl)morpholine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCOCC1 IAJDSUYFELYZCS-UHFFFAOYSA-N 0.000 claims description 3
- JBTPRUMXWADORW-UHFFFAOYSA-N n-(3-methoxypropyl)-4-nitroaniline Chemical compound COCCCNC1=CC=C([N+]([O-])=O)C=C1 JBTPRUMXWADORW-UHFFFAOYSA-N 0.000 claims description 3
- VTJZKYAGHWZYQC-UHFFFAOYSA-N n-cyclopropyl-4-nitroaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1CC1 VTJZKYAGHWZYQC-UHFFFAOYSA-N 0.000 claims description 3
- 229920001059 synthetic polymer Polymers 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- PGHLPLFPEDIYDC-UHFFFAOYSA-N 2-methyl-4-nitro-n-(oxolan-2-ylmethyl)aniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NCC1OCCC1 PGHLPLFPEDIYDC-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- 239000002253 acid Substances 0.000 description 43
- 239000000118 hair dye Substances 0.000 description 43
- -1 phosphoric acid Chemical class 0.000 description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 30
- 239000007864 aqueous solution Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 230000002378 acidificating effect Effects 0.000 description 17
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- 239000004310 lactic acid Substances 0.000 description 15
- 235000014655 lactic acid Nutrition 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 238000004040 coloring Methods 0.000 description 7
- 239000006071 cream Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 210000004243 sweat Anatomy 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 235000010323 ascorbic acid Nutrition 0.000 description 6
- 239000011668 ascorbic acid Substances 0.000 description 6
- 229960005070 ascorbic acid Drugs 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 238000012545 processing Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- XUCYJGMIICONES-UHFFFAOYSA-N 1-fluoro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1F XUCYJGMIICONES-UHFFFAOYSA-N 0.000 description 5
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 5
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical compound CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 5
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-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
- 229940018563 3-aminophenol Drugs 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000000834 fixative Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 230000037308 hair color Effects 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- SBUMIGFDXJIPLE-UHFFFAOYSA-N 2-(3-amino-4-methoxyanilino)ethanol Chemical compound COC1=CC=C(NCCO)C=C1N SBUMIGFDXJIPLE-UHFFFAOYSA-N 0.000 description 4
- DBFYESDCPWWCHN-UHFFFAOYSA-N 5-amino-2-methylphenol Chemical compound CC1=CC=C(N)C=C1O DBFYESDCPWWCHN-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- UXEAWNJALIUYRH-UHFFFAOYSA-N [8-[(4-aminophenyl)hydrazinylidene]-7-oxonaphthalen-2-yl]-trimethylazanium;chloride Chemical compound [Cl-].C12=CC([N+](C)(C)C)=CC=C2C=CC(=O)\C1=N/NC1=CC=C(N)C=C1 UXEAWNJALIUYRH-UHFFFAOYSA-N 0.000 description 4
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 4
- 229960000541 cetyl alcohol Drugs 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
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- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- IYBVSTPLAWCNJD-UHFFFAOYSA-K trisodium 1H-pyrazole-5-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)c1ccn[nH]1.[O-]C(=O)c1ccn[nH]1.[O-]C(=O)c1ccn[nH]1 IYBVSTPLAWCNJD-UHFFFAOYSA-K 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—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
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)
- Coloring (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19847192A DE19847192A1 (de) | 1998-10-13 | 1998-10-13 | Mittel und Verfahren zur Färbung von Fasern |
| DE19847192.0 | 1998-10-13 | ||
| PCT/EP1999/006601 WO2000021496A1 (de) | 1998-10-13 | 1999-09-08 | Mittel und verfahren zur färbung von fasern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002527369A true JP2002527369A (ja) | 2002-08-27 |
| JP2002527369A5 JP2002527369A5 (enExample) | 2006-06-29 |
Family
ID=7884336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000575472A Pending JP2002527369A (ja) | 1998-10-13 | 1999-09-08 | 繊維を染色するための薬剤及び方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6379400B1 (enExample) |
| EP (1) | EP1037593B1 (enExample) |
| JP (1) | JP2002527369A (enExample) |
| AT (1) | ATE258782T1 (enExample) |
| BR (1) | BR9906871A (enExample) |
| DE (2) | DE19847192A1 (enExample) |
| ES (1) | ES2214882T3 (enExample) |
| WO (1) | WO2000021496A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100732262B1 (ko) | 1999-10-21 | 2007-06-25 | 알콘, 인코퍼레이티드 | 약물 전달 장치 |
| US7087095B2 (en) * | 2002-08-06 | 2006-08-08 | Hairmarker Llc | Hair coloring composition and method |
| US7306632B2 (en) * | 2000-05-11 | 2007-12-11 | Hairmarker Llc | Leave-in color conditioner |
| SE0001866D0 (sv) * | 2000-05-18 | 2000-05-18 | Astrazeneca Ab | A new process |
| US7041142B2 (en) * | 2004-10-12 | 2006-05-09 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Two step hair coloring compositions delivering deeper, long-lasting color |
| CN103755667B (zh) * | 2014-01-27 | 2016-01-20 | 苏州大学 | 一种手性3-（2-硝基乙基）四氢呋喃化合物及其制备方法 |
| JP6821167B2 (ja) * | 2016-05-25 | 2021-01-27 | ホーユー株式会社 | 毛髪化粧料組成物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA900490A (en) * | 1972-05-16 | Halasz Alexander | Substituted nitroparaphenylenediamine dyes and compositions containing the same | |
| GB1136659A (en) * | 1965-12-29 | 1968-12-11 | Clairol Inc | Dyeing process and composition |
| CH468188A (fr) * | 1966-02-15 | 1969-02-15 | Oreal | Procédé de teinture décolorante pour cheveux et composition tinctoriale pour la mise en oeuvre dudit procédé |
| US3950127A (en) * | 1972-12-26 | 1976-04-13 | Clairol Incorporated | Hair dye compositions containing nitrodiphenylamine dyes and method for dyeing hair therewith |
| FR2362112A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Nouvelles paraphenylenediamines et compositions tinctoriales pour fibres keratiniques les contenant |
| US5387295A (en) * | 1977-01-05 | 1995-02-07 | Hercules Incorporated | Stabilizers for cross-linked composite modified double base propellants |
| FR2395021A1 (fr) * | 1977-06-24 | 1979-01-19 | Oreal | Paraphenylene diamines et compositions tinctoriales les contenant |
| DE3402519A1 (de) * | 1984-01-26 | 1985-08-01 | Wella Ag, 6100 Darmstadt | Verwendung von p-ureidoalkylamino-nitrobenzolverbindungen in haarfaerbemitteln und neue p-ureidoalkylamino-nitrobenzolverbindungen |
| US5135543A (en) | 1989-12-29 | 1992-08-04 | Clairol Incorporated | Quaternized monoalkylenediamine nitrobenzene compounds and their use as dyes for keratinaceous fibers |
| US5000755A (en) * | 1990-07-19 | 1991-03-19 | Clairol Incorporated | Nitroso compounds as direct dyes |
| US5078749A (en) * | 1990-07-19 | 1992-01-07 | Clairol, Inc. | Nitroso compounds as direct dyes |
| DE4205329A1 (de) * | 1992-02-21 | 1993-08-26 | Henkel Kgaa | P-phenylendiaminderivate als oxidationsfarbstoffvorprodukte |
| DE4404563A1 (de) * | 1994-02-12 | 1995-08-17 | Henkel Kgaa | Neue N-Cyclopropyl-p-phenylendiamine und deren Verwendung in Oxidationsfärbemitteln |
| US5851237A (en) * | 1997-07-14 | 1998-12-22 | Anderson; James S. | Oxidative hair dye compositions and methods containing 1--(4-aminophenyl) pyrrolidines |
-
1998
- 1998-10-13 DE DE19847192A patent/DE19847192A1/de not_active Withdrawn
-
1999
- 1999-09-08 US US09/581,367 patent/US6379400B1/en not_active Expired - Lifetime
- 1999-09-08 AT AT99944624T patent/ATE258782T1/de not_active IP Right Cessation
- 1999-09-08 JP JP2000575472A patent/JP2002527369A/ja active Pending
- 1999-09-08 ES ES99944624T patent/ES2214882T3/es not_active Expired - Lifetime
- 1999-09-08 EP EP99944624A patent/EP1037593B1/de not_active Expired - Lifetime
- 1999-09-08 WO PCT/EP1999/006601 patent/WO2000021496A1/de not_active Ceased
- 1999-09-08 DE DE59908466T patent/DE59908466D1/de not_active Expired - Lifetime
- 1999-09-08 BR BR9906871-0A patent/BR9906871A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US6379400B1 (en) | 2002-04-30 |
| BR9906871A (pt) | 2000-10-17 |
| EP1037593B1 (de) | 2004-02-04 |
| DE19847192A1 (de) | 2000-04-27 |
| DE59908466D1 (de) | 2004-03-11 |
| WO2000021496A1 (de) | 2000-04-20 |
| ES2214882T3 (es) | 2004-09-16 |
| ATE258782T1 (de) | 2004-02-15 |
| EP1037593A1 (de) | 2000-09-27 |
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