CH332482A - Verfahren zur Herstellung neuer Farbstoffe - Google Patents
Verfahren zur Herstellung neuer FarbstoffeInfo
- Publication number
- CH332482A CH332482A CH332482DA CH332482A CH 332482 A CH332482 A CH 332482A CH 332482D A CH332482D A CH 332482DA CH 332482 A CH332482 A CH 332482A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- sulfonic acid
- parts
- group
- amide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 title description 46
- -1 aliphatic radical Chemical group 0.000 claims description 26
- 230000008878 coupling Effects 0.000 claims description 18
- 238000010168 coupling process Methods 0.000 claims description 18
- 238000005859 coupling reaction Methods 0.000 claims description 18
- 230000007935 neutral effect Effects 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 12
- 150000008049 diazo compounds Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000003254 radicals Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical class O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 12
- 210000002268 wool Anatomy 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 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 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- JZEMWPDXKQPACX-UHFFFAOYSA-N 3-amino-N-(benzenesulfonyl)-4-chlorobenzenesulfonamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NS(=O)(=O)C=1C=C(C(=CC1)Cl)N JZEMWPDXKQPACX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- QRRXGUYBWCPMGI-UHFFFAOYSA-N 3-amino-n-(benzenesulfonyl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NS(=O)(=O)C=2C=CC=CC=2)=C1 QRRXGUYBWCPMGI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940059260 amidate Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- LUYAMNYBNTVQJG-UHFFFAOYSA-N 1-chloro-2-(2-chloroethylsulfonyl)ethane Chemical compound ClCCS(=O)(=O)CCCl LUYAMNYBNTVQJG-UHFFFAOYSA-N 0.000 description 1
- BOTOIHAKCFLTEG-UHFFFAOYSA-N 2-amino-n-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)NS(=O)(=O)C1=CC=CC=C1N BOTOIHAKCFLTEG-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- VELFHWVBFQVPRF-UHFFFAOYSA-N 4-amino-N-(3-chloropropyl)benzenesulfonamide Chemical compound ClCCCNS(=O)(=O)C1=CC=C(N)C=C1 VELFHWVBFQVPRF-UHFFFAOYSA-N 0.000 description 1
- TXWROWPXUQZXFZ-UHFFFAOYSA-N 4-amino-n-(benzenesulfonyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 TXWROWPXUQZXFZ-UHFFFAOYSA-N 0.000 description 1
- FLYUVWRKSUKMKH-UHFFFAOYSA-N 4-amino-n-ethylsulfonylbenzenesulfonamide Chemical compound CCS(=O)(=O)NS(=O)(=O)C1=CC=C(N)C=C1 FLYUVWRKSUKMKH-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- GTFKDHOLRKAAFH-UHFFFAOYSA-N 5-amino-n-(2-chloroethyl)-2-methylbenzenesulfonamide Chemical compound CC1=CC=C(N)C=C1S(=O)(=O)NCCCl GTFKDHOLRKAAFH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical group COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- UOLJOMSSSIYGCZ-UHFFFAOYSA-N N-(5-amino-2-methoxyphenyl)sulfonylbenzamide Chemical compound C(C1=CC=CC=C1)(=O)NS(=O)(=O)C=1C=C(C=CC1OC)N UOLJOMSSSIYGCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008430 aromatic amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical compound CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- 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
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
-
- 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/447—Azo dyes
- C09B62/45—Monoazo 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/62—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an ethylenimino or N—acylated ethylenimino group or a —CO—NH—CH2—CH2—X group, wherein X is a halogen atom, a quaternary ammonium group or O—acyl and acyl is derived from an organic or inorganic acid, or a beta—substituted ethylamine group
- C09B62/66—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH332482T | 1953-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH332482A true CH332482A (de) | 1958-09-15 |
Family
ID=4502453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH332482D CH332482A (de) | 1953-01-28 | 1953-01-28 | Verfahren zur Herstellung neuer Farbstoffe |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2773863A (d) |
| BE (1) | BE526035A (d) |
| CH (1) | CH332482A (d) |
| DE (1) | DE1001437C2 (d) |
| GB (1) | GB768241A (d) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB870948A (en) * | 1958-10-29 | 1961-06-21 | Ici Ltd | New anthraquinone dyestuffs |
| CA699092A (en) * | 1961-04-06 | 1964-12-01 | Polaroid Corporation | Photographic products, processes and compositions |
| US3218312A (en) * | 1962-10-12 | 1965-11-16 | Polaroid Corp | Hydroquinonylsulfonyl azo dye developers |
| US4166059A (en) * | 1971-04-02 | 1979-08-28 | Crompton & Knowles Corporation | Alkali-fast disazo disulfimide dyes |
| US4301068A (en) * | 1979-12-05 | 1981-11-17 | Eastman Kodak Company | Azo dyes from a 2-aminothiophene having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydrocyalkyl) carbamoyl groups on its ring |
| US4301071A (en) * | 1979-12-05 | 1981-11-17 | Eastman Kodak Company | Azo dyes from aniline having 1 or 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on its ring |
| US4302387A (en) * | 1979-12-05 | 1981-11-24 | Eastman Kodak Company | Azo dyes from 1,3,4-thiadiazol-2-yl and 1,2,4-thiadiazol-5-yl moieties bearing sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl)carbamoyl groups on their rings |
| US4302390A (en) * | 1979-12-05 | 1981-11-24 | Eastman Kodak Company | Azo dyes with sulfate groups on the diazotized 2-amino thiazol and 5-amino isothiazol moiety and with aniline, tetrahydroquinoline and benzomorpholine couplers |
| US4301070A (en) * | 1979-12-05 | 1981-11-17 | Eastman Kodak Company | Azo dyes from a 5-aminopyrazole bearing 1 to 2 sulfated hydroxyalkoxycarbonyl or N-(hydroxyalkyl) carbamoyl groups on its ring |
| US4374769A (en) * | 1981-06-17 | 1983-02-22 | Eastman Kodak Company | Water-soluble tris phenyl bisazo dyes for polyamide fibers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2261175A (en) * | 1939-07-01 | 1941-11-04 | Eastman Kodak Co | Azo compounds and material colored therewith |
| US2390113A (en) * | 1941-08-04 | 1945-12-04 | Eastman Kodak Co | Monoazo compounds |
| US2424493A (en) * | 1943-09-02 | 1947-07-22 | Chem Ind Basel | Pyrazolone monoazo dyes containing polybasic acid esters of alkylene sulfones |
| US2518078A (en) * | 1946-01-31 | 1950-08-08 | Geigy Ag J R | Monoazodyestuffs of the pyrazolone series free from sulfonic acid groups and a process of making same |
| US2606185A (en) * | 1948-02-12 | 1952-08-05 | Ciba Ltd | Monoazo-dyestuffs of the pyrazolone series |
| DE821977C (de) * | 1949-10-02 | 1951-11-22 | Basf Ag | Verfahren zur Herstellung von Azofarbstoffen |
-
0
- BE BE526035D patent/BE526035A/fr unknown
-
1953
- 1953-01-28 CH CH332482D patent/CH332482A/de unknown
-
1954
- 1954-01-21 DE DE1954C0008766 patent/DE1001437C2/de not_active Expired
- 1954-01-22 GB GB2043/54A patent/GB768241A/en not_active Expired
- 1954-01-25 US US406087A patent/US2773863A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB768241A (en) | 1957-02-13 |
| BE526035A (d) | |
| DE1001437B (de) | 1957-01-24 |
| DE1001437C2 (de) | 1957-07-04 |
| US2773863A (en) | 1956-12-11 |
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