GB616523A - Manufacture of direct dyestuffs and intermediates - Google Patents
Manufacture of direct dyestuffs and intermediatesInfo
- Publication number
- GB616523A GB616523A GB16588/44A GB1658844A GB616523A GB 616523 A GB616523 A GB 616523A GB 16588/44 A GB16588/44 A GB 16588/44A GB 1658844 A GB1658844 A GB 1658844A GB 616523 A GB616523 A GB 616523A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- hydroxy
- azobenzene
- carboxybenzene
- 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.)
- Expired
Links
- 239000000543 intermediate Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 13
- 150000001412 amines Chemical class 0.000 abstract 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 8
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 230000008878 coupling Effects 0.000 abstract 5
- 238000010168 coupling process Methods 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 4
- -1 aminoazo compound Chemical class 0.000 abstract 4
- 229910021529 ammonia Inorganic materials 0.000 abstract 4
- 239000007859 condensation product Substances 0.000 abstract 4
- 239000000975 dye Substances 0.000 abstract 4
- 239000000835 fiber Substances 0.000 abstract 4
- MLPWLRUWQJVULT-UHFFFAOYSA-N 5-amino-2-hydroxy-3-sulfobenzoic acid Chemical compound NC1=CC(C(O)=O)=C(O)C(S(O)(=O)=O)=C1 MLPWLRUWQJVULT-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 3
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 abstract 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 abstract 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 229910006069 SO3H Inorganic materials 0.000 abstract 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 238000004043 dyeing Methods 0.000 abstract 2
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 abstract 2
- 238000001465 metallisation Methods 0.000 abstract 2
- 238000007127 saponification reaction Methods 0.000 abstract 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract 2
- 235000021286 stilbenes Nutrition 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 abstract 1
- HKOJYPPTIPJZAZ-UHFFFAOYSA-N 2-methoxy-6-methylaniline Chemical compound COC1=CC=CC(C)=C1N HKOJYPPTIPJZAZ-UHFFFAOYSA-N 0.000 abstract 1
- XETBTIXYDXFQJQ-UHFFFAOYSA-N 3-(2-chloroethyl)-2-hydroxybenzoic acid Chemical compound ClCCC=1C(=C(C=CC1)C(=O)O)O XETBTIXYDXFQJQ-UHFFFAOYSA-N 0.000 abstract 1
- ZYIWQQOVIPGGPG-UHFFFAOYSA-N 3-amino-5-sulfobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 ZYIWQQOVIPGGPG-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical class [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 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 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2459435X | 1943-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB616523A true GB616523A (en) | 1949-01-24 |
Family
ID=4569390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16588/44A Expired GB616523A (en) | 1943-09-01 | 1944-08-31 | Manufacture of direct dyestuffs and intermediates |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2459435A (en:Method) |
| DE (1) | DE853324C (en:Method) |
| FR (1) | FR906873A (en:Method) |
| GB (1) | GB616523A (en:Method) |
| NL (1) | NL118822B (en:Method) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5554734A (en) * | 1994-06-20 | 1996-09-10 | Ciba-Geigy Corporation | AZO dyes containing a bridge member based on stibene and morpholino-substituted triazine |
| US7166564B2 (en) * | 2003-08-21 | 2007-01-23 | Ciba Specialty Chemicals Corp. | Optical brighteners |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883515A (en) * | 1969-12-29 | 1975-05-13 | Ciba Geigy Corp | Adiabatic process for the production of 2,4-dichloro-6-amino-S-triazines |
| DE2800147C2 (de) * | 1978-01-03 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | Reaktivfarbstoffe |
| FR2518106B1 (fr) * | 1981-12-11 | 1986-12-05 | Sandoz Sa | Procede de teinture et d'impression de substrats organiques a l'aide de colorants directs bisazoiques |
| ES2092081T3 (es) * | 1991-12-20 | 1996-11-16 | Ciba Geigy Ag | Procedimiento para teñir o estampar materiales de fibra que contengan grupos hidroxilo. |
| CN107325584B (zh) * | 2017-07-03 | 2019-07-26 | 浙江名毅新能源股份有限公司 | 4,4’-二氨基二苯乙烯-2,2’-二磺酸化合物、其中间体、制备方法和应用 |
| CN111909536B (zh) * | 2020-09-01 | 2022-04-05 | 浙江闰土染料有限公司 | 黑色直接染料组合物、黑色直接染料及其制备方法和用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2195788A (en) * | 1940-04-02 | Complex metal compoijnds of azo | ||
| US2221362A (en) * | 1940-11-12 | Metal compounds of azo dyestijffs | ||
| US2221360A (en) * | 1940-11-12 | Metal compounds of azo dyestutfs | ||
| CH110678A (de) * | 1923-01-09 | 1925-06-16 | Chem Ind Basel | Verfahren zur Herstellung eines neuen Azofarbstoffes. |
| US2004250A (en) * | 1932-02-29 | 1935-06-11 | Gen Aniline Works Inc | Azo-dyestuffs, and process of making same |
| BE423789A (en:Method) * | 1936-10-03 | |||
| US2270478A (en) * | 1936-10-03 | 1942-01-20 | Soc Of Chemical Ind | Azo dyestuffs |
| US2283261A (en) * | 1939-07-12 | 1942-05-19 | Soc Of Chemical Ind | Yellow azo dyestuffs |
| CH242159A (de) * | 1942-03-06 | 1946-04-30 | Ciba Geigy | Verfahren zur Herstellung eines neuen Azofarbstoffes. |
| IT428783A (en:Method) * | 1943-02-10 |
-
1944
- 1944-08-28 US US551622A patent/US2459435A/en not_active Expired - Lifetime
- 1944-08-31 NL NL118822A patent/NL118822B/xx unknown
- 1944-08-31 FR FR906873D patent/FR906873A/fr not_active Expired
- 1944-08-31 GB GB16588/44A patent/GB616523A/en not_active Expired
- 1944-09-01 DE DEG2107D patent/DE853324C/de not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5554734A (en) * | 1994-06-20 | 1996-09-10 | Ciba-Geigy Corporation | AZO dyes containing a bridge member based on stibene and morpholino-substituted triazine |
| US7166564B2 (en) * | 2003-08-21 | 2007-01-23 | Ciba Specialty Chemicals Corp. | Optical brighteners |
Also Published As
| Publication number | Publication date |
|---|---|
| US2459435A (en) | 1949-01-18 |
| DE853324C (de) | 1952-10-23 |
| NL118822B (en:Method) | 1948-02-16 |
| FR906873A (fr) | 1946-02-22 |
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