PL77592B1 - - Google Patents
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- Publication number
- PL77592B1 PL77592B1 PL1971148815A PL14881571A PL77592B1 PL 77592 B1 PL77592 B1 PL 77592B1 PL 1971148815 A PL1971148815 A PL 1971148815A PL 14881571 A PL14881571 A PL 14881571A PL 77592 B1 PL77592 B1 PL 77592B1
- Authority
- PL
- Poland
- Prior art keywords
- aniline
- group
- radical
- general formula
- parts
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 26
- -1 dichloropyrimidylamino group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- GEMYPJWUMFLPSQ-UHFFFAOYSA-N (2-methylphenyl)sulfamic acid Chemical compound CC1=CC=CC=C1NS(O)(=O)=O GEMYPJWUMFLPSQ-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- UONBCMCTTMKOMD-UHFFFAOYSA-N methyl(phenyl)sulfamic acid Chemical compound OS(=O)(=O)N(C)C1=CC=CC=C1 UONBCMCTTMKOMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- QYUCKACWAKFMHL-UHFFFAOYSA-N phenyl(sulfo)carbamic acid Chemical compound OC(=O)N(S(O)(=O)=O)C1=CC=CC=C1 QYUCKACWAKFMHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- SUOBRLXXRACDFP-UHFFFAOYSA-N n-chloro-1,3,5-triazin-2-amine Chemical compound ClNC1=NC=NC=N1 SUOBRLXXRACDFP-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000004043 dyeing Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229920002678 cellulose Chemical group 0.000 description 7
- 239000001913 cellulose Chemical group 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VUFQEUMIZLWUQA-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(NC(C)=O)C1=O Chemical compound CCN1C(O)=CC(C)=C(NC(C)=O)C1=O VUFQEUMIZLWUQA-UHFFFAOYSA-N 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NMWUEMCXIDXQED-UHFFFAOYSA-N N#CN(C(C(NC(N1)=O)=C1N1)=O)C1=O.Cl Chemical compound N#CN(C(C(NC(N1)=O)=C1N1)=O)C1=O.Cl NMWUEMCXIDXQED-UHFFFAOYSA-N 0.000 description 1
- JDVCHHKIPMGJBG-UHFFFAOYSA-N N-(2-chlorophenyl)-N-nitronitramide Chemical compound [O-][N+](=O)N(C1=C(Cl)C=CC=C1)[N+]([O-])=O JDVCHHKIPMGJBG-UHFFFAOYSA-N 0.000 description 1
- GYLPWXBFGDCXSN-UHFFFAOYSA-N NC1=CC(=CC=C1)[N+](=O)[O-].NC1=C(C=CC=C1)[N+](=O)[O-] Chemical compound NC1=CC(=CC=C1)[N+](=O)[O-].NC1=C(C=CC=C1)[N+](=O)[O-] GYLPWXBFGDCXSN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- VSANMHWDSONVEE-UHFFFAOYSA-N carbyl sulfate Chemical compound O=S1(=O)CCOS(=O)(=O)O1 VSANMHWDSONVEE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002803 maceration Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0067—Azodyes with heterocyclic compound as coupling component
-
- 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
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
- C09B31/153—Heterocyclic components containing a six-membered ring with one nitrogen atom as the only ring hetero-atom
-
- 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/025—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups of azo-pyridone series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3363470 | 1970-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL77592B1 true PL77592B1 (en, 2012) | 1975-04-30 |
Family
ID=10355444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971148815A PL77592B1 (en, 2012) | 1970-07-10 | 1971-06-15 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3725383A (en, 2012) |
| BR (1) | BR7104354D0 (en, 2012) |
| CH (2) | CH602892A5 (en, 2012) |
| CS (1) | CS166774B2 (en, 2012) |
| DE (1) | DE2134453A1 (en, 2012) |
| ES (3) | ES393158A1 (en, 2012) |
| FR (1) | FR2098329B1 (en, 2012) |
| GB (1) | GB1350602A (en, 2012) |
| NL (1) | NL7109505A (en, 2012) |
| PL (1) | PL77592B1 (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001205A (en) * | 1968-07-15 | 1977-01-04 | Ciba-Geigy Ag | Water-soluble, fiber-reactive phenylazodihydroxy, methyl, cyanopyridine dyestuffs |
| US3905950A (en) * | 1968-12-09 | 1975-09-16 | Ici Ltd | Reactive disazo dyestuffs containing 1-aminoalkyl-6-hydroxypyrid-6-one and monochlorotriazinyl groupings |
| US3936436A (en) * | 1969-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals |
| US4067864A (en) * | 1970-05-15 | 1978-01-10 | Ciba-Geigy Ag | Fiber-reactive 2-hydroxy-pyrid-6-on-(3)-yl azo dyestuffs |
| US4017477A (en) * | 1970-08-19 | 1977-04-12 | Ciba-Geigy Ag | 3-Halogeno-6-hydroxy-pyridone-(2) azo dyestuffs |
| US4039523A (en) * | 1970-12-22 | 1977-08-02 | Ciba-Geigy Ag | 3-Sulfoalkyl-6-hydroxy-pyrid-(2)-one-containing azo dyestuffs |
| US3966706A (en) * | 1971-01-27 | 1976-06-29 | Ciba-Geigy Ag | 2,6-Dihydroxy-3-cyano-4-methylpyridine containing azo dyes which contain a functional amino group |
| DE2117753C3 (de) * | 1971-04-10 | 1980-12-11 | Cassella Ag, 6000 Frankfurt | Hydroxy-pyridon-monosulfonsäuren und Verfahren zu ihrer Herstellung |
| US3957747A (en) * | 1971-05-18 | 1976-05-18 | Imperial Chemical Industries Limited | 6-hydroxypyrid-2-one azo dyestuffs |
| BE786727A (fr) * | 1971-07-27 | 1973-01-26 | Ciba Geigy | Composes azoiques, leur preparation et leur emploi en teinture |
| DE2222099A1 (de) * | 1972-05-05 | 1973-11-22 | Hoechst Ag | Basische azofarbstoffe, ihre herstellung und verwendung |
| GB1441096A (en) * | 1972-12-27 | 1976-06-30 | Ici Ltd | Hydroxy pyridone azo dyestuffs |
| DE2300940A1 (de) * | 1973-01-10 | 1974-07-18 | Basf Ag | Azopigmente |
| DE2307168A1 (de) * | 1973-02-14 | 1974-08-22 | Bayer Ag | Azofarbstoffe |
| CH606298A5 (en, 2012) * | 1974-02-26 | 1978-10-31 | Ciba Geigy Ag | |
| US3974123A (en) * | 1974-03-01 | 1976-08-10 | Basf Aktiengesellschaft | Dyes for thermoplastics |
| US4066637A (en) * | 1974-06-18 | 1978-01-03 | Ciba-Geigy Corporation | Basic diaminopyridine-(3)-azo dyestuffs |
| AR207988A1 (es) | 1974-07-16 | 1976-11-22 | Ciba Geigy Ag | Complejos de cobre niquel cromo y cobalto de colorantes azoicos y azometinicos y procedimiento para su obtencion |
| CH614968A5 (en, 2012) * | 1975-04-16 | 1979-12-28 | Ciba Geigy Ag | |
| DE68923527D1 (de) * | 1988-10-20 | 1995-08-24 | Sandoz Ag | Faserreaktive Azofarbstoffe. |
| US5580980A (en) * | 1991-05-03 | 1996-12-03 | Basf Aktiengesellschaft | N-aminopyridone dyes |
| US8092890B2 (en) * | 2007-04-13 | 2012-01-10 | Fujifilm Corporation | Optical information recording medium, method of recording information, and azo metal complex dye |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL128672C (en, 2012) * | 1964-08-08 |
-
1970
- 1970-07-10 GB GB3363470A patent/GB1350602A/en not_active Expired
-
1971
- 1971-05-20 US US00145505A patent/US3725383A/en not_active Expired - Lifetime
- 1971-06-15 PL PL1971148815A patent/PL77592B1/pl unknown
- 1971-07-08 CH CH649774A patent/CH602892A5/xx not_active IP Right Cessation
- 1971-07-08 CH CH1004671A patent/CH565837A5/xx not_active IP Right Cessation
- 1971-07-09 CS CS5086A patent/CS166774B2/cs unknown
- 1971-07-09 NL NL7109505A patent/NL7109505A/xx unknown
- 1971-07-09 FR FR7125361A patent/FR2098329B1/fr not_active Expired
- 1971-07-09 DE DE19712134453 patent/DE2134453A1/de active Pending
- 1971-07-09 BR BR4354/71A patent/BR7104354D0/pt unknown
- 1971-07-10 ES ES393158A patent/ES393158A1/es not_active Expired
- 1971-10-02 ES ES395636A patent/ES395636A1/es not_active Expired
- 1971-10-02 ES ES395637A patent/ES395637A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2098329B1 (en, 2012) | 1975-06-06 |
| US3725383A (en) | 1973-04-03 |
| ES395636A1 (es) | 1974-10-16 |
| DE2134453A1 (de) | 1972-01-20 |
| CH602892A5 (en, 2012) | 1978-08-15 |
| ES395637A1 (es) | 1973-11-16 |
| CH565837A5 (en, 2012) | 1975-08-29 |
| NL7109505A (en, 2012) | 1972-01-12 |
| FR2098329A1 (en, 2012) | 1972-03-10 |
| BR7104354D0 (pt) | 1973-05-03 |
| ES393158A1 (es) | 1973-11-16 |
| CS166774B2 (en, 2012) | 1976-03-29 |
| GB1350602A (en) | 1974-04-18 |
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