JPS5974163A - ジスアゾ化合物及びそれを使用する染色法 - Google Patents
ジスアゾ化合物及びそれを使用する染色法Info
- Publication number
- JPS5974163A JPS5974163A JP57184638A JP18463882A JPS5974163A JP S5974163 A JPS5974163 A JP S5974163A JP 57184638 A JP57184638 A JP 57184638A JP 18463882 A JP18463882 A JP 18463882A JP S5974163 A JPS5974163 A JP S5974163A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- acid
- cotton
- dyeing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Disazo compound Chemical class 0.000 title claims abstract description 24
- 238000004043 dyeing Methods 0.000 title claims description 31
- 229920003043 Cellulose fiber Polymers 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 abstract description 28
- 239000000975 dye Substances 0.000 abstract description 23
- 239000000835 fiber Substances 0.000 abstract description 13
- 239000004627 regenerated cellulose Substances 0.000 abstract description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract description 4
- 229910006069 SO3H Inorganic materials 0.000 abstract description 3
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 235000019646 color tone Nutrition 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000986 disperse dye Substances 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000982 direct dye Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- BCGQKHORGCDDRI-UHFFFAOYSA-N heptadeca-2,4-diyn-1-ol Chemical compound CCCCCCCCCCCCC#CC#CCO BCGQKHORGCDDRI-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- RDRRVDWNUVOYMG-UHFFFAOYSA-N 2-amino-1h-naphthalene-1,2,3-trisulfonic acid Chemical compound C1=CC=C2C=C(S(O)(=O)=O)C(N)(S(O)(=O)=O)C(S(O)(=O)=O)C2=C1 RDRRVDWNUVOYMG-UHFFFAOYSA-N 0.000 description 1
- DVLOIGSXYNRCNP-UHFFFAOYSA-N 2-amino-1h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)C(N)(S(O)(=O)=O)C=CC2=C1 DVLOIGSXYNRCNP-UHFFFAOYSA-N 0.000 description 1
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- GYFZMCLUPHXUDV-UHFFFAOYSA-N 2-ethoxy-5-methylaniline Chemical compound CCOC1=CC=C(C)C=C1N GYFZMCLUPHXUDV-UHFFFAOYSA-N 0.000 description 1
- ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 3-amino-2-hydroxy-5-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(C(O)=O)=C1O ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 0.000 description 1
- XJQRCFRVWZHIPN-UHFFFAOYSA-N 3-amino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1Cl XJQRCFRVWZHIPN-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 1
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
- QTYQPEBQHHUSIK-UHFFFAOYSA-N 4-amino-2,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(C)C=C1N QTYQPEBQHHUSIK-UHFFFAOYSA-N 0.000 description 1
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- LKRKPOYQGXPTAO-UHFFFAOYSA-N 6-aminonaphthalene-1,2,4-trisulfonic acid Chemical compound OS(=O)(=O)C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 LKRKPOYQGXPTAO-UHFFFAOYSA-N 0.000 description 1
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
- GWRBRKFJOOUBPB-UHFFFAOYSA-N CC(N)=O.NC1=CC=CC=C1 Chemical compound CC(N)=O.NC1=CC=CC=C1 GWRBRKFJOOUBPB-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical class CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ITUDPMUZMSYEHE-UHFFFAOYSA-M sodium acetate hexahydrate Chemical compound C(C)(=O)[O-].[Na+].O.O.O.O.O.O ITUDPMUZMSYEHE-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
Classifications
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
- C09B29/0803—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls containing SO3H, OSO3H
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57184638A JPS5974163A (ja) | 1982-10-22 | 1982-10-22 | ジスアゾ化合物及びそれを使用する染色法 |
| GB08326662A GB2131824B (en) | 1982-10-22 | 1983-10-05 | Water-soluble disazo compounds |
| US06/539,746 US4542208A (en) | 1982-10-22 | 1983-10-06 | Disazo compounds for dyeing cellulosic fibers |
| DE19833337799 DE3337799A1 (de) | 1982-10-22 | 1983-10-18 | Disazoverbindungen, verfahren zu ihrer herstellung und verwendung derselben in einem faerbeverfahren |
| CH5723/83A CH653357A5 (de) | 1982-10-22 | 1983-10-20 | Disazoverbindungen. |
| KR1019830004992A KR840006815A (ko) | 1982-10-22 | 1983-10-21 | 디아조 화합물과 그 제법 및 그것을 사용하는 염색법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57184638A JPS5974163A (ja) | 1982-10-22 | 1982-10-22 | ジスアゾ化合物及びそれを使用する染色法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5974163A true JPS5974163A (ja) | 1984-04-26 |
| JPH0157148B2 JPH0157148B2 (en, 2012) | 1989-12-04 |
Family
ID=16156730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57184638A Granted JPS5974163A (ja) | 1982-10-22 | 1982-10-22 | ジスアゾ化合物及びそれを使用する染色法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4542208A (en, 2012) |
| JP (1) | JPS5974163A (en, 2012) |
| KR (1) | KR840006815A (en, 2012) |
| CH (1) | CH653357A5 (en, 2012) |
| DE (1) | DE3337799A1 (en, 2012) |
| GB (1) | GB2131824B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61190561A (ja) * | 1985-02-19 | 1986-08-25 | Mitsubishi Chem Ind Ltd | ジスアゾ系反応性染料 |
| JP2007099880A (ja) * | 2005-10-04 | 2007-04-19 | Nippon Kayaku Co Ltd | 染料水溶液、インク組成物、インクジェット記録方法及び着色体 |
| JP2008031475A (ja) * | 2006-07-27 | 2008-02-14 | Ilford Imaging Switzerland Gmbh | ジアゾ染料及びその製造方法及び使用方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8801486D0 (en) * | 1988-01-22 | 1988-02-24 | Ici Plc | Water-soluble dye |
| ES2062091T3 (es) * | 1988-06-21 | 1994-12-16 | Ciba Geigy Ag | Colorantes azoicos. |
| US5644040A (en) * | 1994-12-02 | 1997-07-01 | Ciba-Geigy Corporation | Azo dyes having two monoazo-chromophores bound to a halotriazinyl radical processes for their preparation and their use |
| GB9619573D0 (en) * | 1996-09-19 | 1996-10-30 | Zeneca Ltd | Monoazo inkjet dyes |
| US7704309B2 (en) * | 2005-03-31 | 2010-04-27 | Fujifilm Imaging Colorants Limited | Disazodyes for ink-jet printing |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4960332A (en, 2012) * | 1972-10-16 | 1974-06-12 | ||
| JPS4980373A (en, 2012) * | 1972-12-06 | 1974-08-02 | ||
| JPS5150326A (ja) * | 1974-10-30 | 1976-05-01 | Nippon Kayaku Kk | Shinkijisuazosenryono seizoho |
| JPS5284233A (en) * | 1976-01-01 | 1977-07-13 | Sandoz Ag | Disazo compounds and process for producing same and dyeing method |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH606321A5 (en, 2012) * | 1974-12-20 | 1978-10-31 | Sandoz Ag | |
| DE2847912A1 (de) * | 1978-11-04 | 1980-05-22 | Bayer Ag | Azofarbstoffe |
-
1982
- 1982-10-22 JP JP57184638A patent/JPS5974163A/ja active Granted
-
1983
- 1983-10-05 GB GB08326662A patent/GB2131824B/en not_active Expired
- 1983-10-06 US US06/539,746 patent/US4542208A/en not_active Expired - Fee Related
- 1983-10-18 DE DE19833337799 patent/DE3337799A1/de not_active Ceased
- 1983-10-20 CH CH5723/83A patent/CH653357A5/de not_active IP Right Cessation
- 1983-10-21 KR KR1019830004992A patent/KR840006815A/ko not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4960332A (en, 2012) * | 1972-10-16 | 1974-06-12 | ||
| JPS4980373A (en, 2012) * | 1972-12-06 | 1974-08-02 | ||
| JPS5150326A (ja) * | 1974-10-30 | 1976-05-01 | Nippon Kayaku Kk | Shinkijisuazosenryono seizoho |
| JPS5284233A (en) * | 1976-01-01 | 1977-07-13 | Sandoz Ag | Disazo compounds and process for producing same and dyeing method |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61190561A (ja) * | 1985-02-19 | 1986-08-25 | Mitsubishi Chem Ind Ltd | ジスアゾ系反応性染料 |
| JP2007099880A (ja) * | 2005-10-04 | 2007-04-19 | Nippon Kayaku Co Ltd | 染料水溶液、インク組成物、インクジェット記録方法及び着色体 |
| JP2008031475A (ja) * | 2006-07-27 | 2008-02-14 | Ilford Imaging Switzerland Gmbh | ジアゾ染料及びその製造方法及び使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2131824A (en) | 1984-06-27 |
| GB8326662D0 (en) | 1983-11-09 |
| DE3337799A1 (de) | 1984-04-26 |
| CH653357A5 (de) | 1985-12-31 |
| US4542208A (en) | 1985-09-17 |
| KR840006815A (ko) | 1984-12-03 |
| JPH0157148B2 (en, 2012) | 1989-12-04 |
| GB2131824B (en) | 1986-02-12 |
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