GB478514A - Process for the manufacture of azodyestuffs - Google Patents
Process for the manufacture of azodyestuffsInfo
- Publication number
- GB478514A GB478514A GB1989336A GB1989336A GB478514A GB 478514 A GB478514 A GB 478514A GB 1989336 A GB1989336 A GB 1989336A GB 1989336 A GB1989336 A GB 1989336A GB 478514 A GB478514 A GB 478514A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitroaniline
- propylene oxide
- methylphenylamino
- propyleneoxide
- dinitroaniline
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- -1 methylphenylamino Chemical group 0.000 abstract 2
- CEPHJMPOMIBBAT-UHFFFAOYSA-N 2-[(2-amino-4-methylsulfonylphenyl)methylsulfonylmethyl]-5-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC(=C(C=C1)CS(=O)(=O)CC1=C(C=C(C=C1)S(=O)(=O)C)N)N CEPHJMPOMIBBAT-UHFFFAOYSA-N 0.000 abstract 1
- FYXJXUMICYGRKV-UHFFFAOYSA-N 2-[(2-amino-5-nitrophenyl)methylsulfonylmethyl]-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1CS(=O)(=O)CC1=CC([N+]([O-])=O)=CC=C1N FYXJXUMICYGRKV-UHFFFAOYSA-N 0.000 abstract 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 abstract 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 abstract 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 abstract 1
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 229920002955 Art silk Polymers 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- OCJYIGYOJCODJL-UHFFFAOYSA-N Meclizine Chemical compound CC1=CC=CC(CN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OCJYIGYOJCODJL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- KYNFOMQIXZUKRK-UHFFFAOYSA-N bishydroxyethyldisulfide Natural products OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 159000000000 sodium salts Chemical class 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Azo dyes are made by coupling a diazotized aromatic amine in acid medium with a p-coupling monamine of the benzene series, in which one hydrogen atom of the amino group is substituted by an alkylene oxide group and the other hydrogen atom of the amino group may be substituted by a hydrocarbon radical, e.g. alkyl, alkenyl, hydroxyalkyl, alkoxyalkyl or aralkyl, the components being selected in such a manner that the molecule contains at most one salt-forming group. They colour cellulose esters, e.g. acetate artificial silk and mixed fabrics containing the same. In examples, the following dyes are described: (1) and (2) p-nitroaniline or o-chloro-p-nitroaniline --> methylphenylamino-1 : 2-propylene oxide (yellowish scarlet and bluish red); (3) p-nitroaniline --> ethyl-m-tolylamino-1 : 2-propylene oxide (bluish red); (4) 6-bromo-2 : 4-dinitroaniline or 2 : 4-dinitroaniline --> (3-methyl - 6 - methoxy) - n - butylamino - 1 : 2-propylene oxide (reddish blue and bluish violet); (5) 4-nitroaniline-2-sulphonic acid --> methylphenylamino - 1 : 2 - propyleneoxide (deep bordeaux when printed on tissue as sodium salt in a paste containing dithiodiglycol and gum solution); (6) aniline-3-sulphonic acid --> methylphenylamino - 1 : 2 - propyleneoxide (yellow from a bath containing ammonium chloride). The following additional components are also specified in a table: 2 : 6-dichloro-4-nitraniline, 6 - ethoxy - 2 - aminobenzothiazole, 5 - nitro - 2 - aminophenylmethyl - sulphone, 4 - methylsulphonyl - 2 - aminophenylmethylsulphone, p-aminobenzoic acid ethyl ester; ethylphenylamino- and n-butyl-m-tolylamino-1 : 2-propylene oxide. Specification 275,622, [Class 2 (iii)], is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1989336A GB478514A (en) | 1936-07-17 | 1936-07-17 | Process for the manufacture of azodyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1989336A GB478514A (en) | 1936-07-17 | 1936-07-17 | Process for the manufacture of azodyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB478514A true GB478514A (en) | 1938-01-17 |
Family
ID=10136916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1989336A Expired GB478514A (en) | 1936-07-17 | 1936-07-17 | Process for the manufacture of azodyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB478514A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3139438A (en) * | 1958-05-19 | 1964-06-30 | Ici Ltd | Copper phthalocyanine dyestuffs containing (3'-chloro-2'-hydroxypropoxyphenyl) sulfamyl groups |
-
1936
- 1936-07-17 GB GB1989336A patent/GB478514A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3139438A (en) * | 1958-05-19 | 1964-06-30 | Ici Ltd | Copper phthalocyanine dyestuffs containing (3'-chloro-2'-hydroxypropoxyphenyl) sulfamyl groups |
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