GB494646A - Process for the production of azo dyestuffs - Google Patents
Process for the production of azo dyestuffsInfo
- Publication number
- GB494646A GB494646A GB8264/38A GB826438A GB494646A GB 494646 A GB494646 A GB 494646A GB 8264/38 A GB8264/38 A GB 8264/38A GB 826438 A GB826438 A GB 826438A GB 494646 A GB494646 A GB 494646A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- sulphonic acid
- acid
- diphenoxybenzene
- obtainable
- 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 abstract 3
- 239000000047 product Substances 0.000 abstract 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 3
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 abstract 3
- RPKWNMFDAOACCX-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 RPKWNMFDAOACCX-UHFFFAOYSA-N 0.000 abstract 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- VUQTXQKMXGTYCA-UHFFFAOYSA-N 2-amino-4-chloro-5-(2-methylphenoxy)benzenesulfonic acid Chemical compound NC1=C(C=C(C(=C1)Cl)OC1=C(C=CC=C1)C)S(=O)(=O)O VUQTXQKMXGTYCA-UHFFFAOYSA-N 0.000 abstract 1
- QFBPXKLBNLODEG-UHFFFAOYSA-N 2-amino-5-(4-methylphenoxy)benzenesulfonic acid Chemical compound NC1=C(C=C(C=C1)OC1=CC=C(C=C1)C)S(=O)(=O)O QFBPXKLBNLODEG-UHFFFAOYSA-N 0.000 abstract 1
- JIYZGGKWXQPXOF-UHFFFAOYSA-N 2-amino-5-phenoxybenzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC=C1OC1=CC=CC=C1 JIYZGGKWXQPXOF-UHFFFAOYSA-N 0.000 abstract 1
- QNYWPSVGLQPXIZ-UHFFFAOYSA-N 3-amino-4-phenoxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1OC1=CC=CC=C1 QNYWPSVGLQPXIZ-UHFFFAOYSA-N 0.000 abstract 1
- HMZGLFZBAKZORS-UHFFFAOYSA-N 5-amino-2-phenoxybenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1OC1=CC=CC=C1 HMZGLFZBAKZORS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- ONUTZSPPHDDIOF-UHFFFAOYSA-M potassium;2-methylphenolate Chemical compound [K+].CC1=CC=CC=C1[O-] ONUTZSPPHDDIOF-UHFFFAOYSA-M 0.000 abstract 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 238000006467 substitution reaction Methods 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azo dyestuffs are manufactured by coupling diazo compounds of unsubstituted or substituted amino-phenoxy- or -diphenoxybenzenesulphonic acids containing no nitro groups with hydroaromatic carbocyclic b -diketones containing an enolizable keto group. The products dye wool and silk, and may be used for the production of lakes by precipitation with alkaline-earth salts. Examples describe the production of the following dyestuffs: (1) 2 - amino - 1 - phenoxybenzene - 4-sulphonic acid --> dimethyldihydroresorcinol; the product dyes wool and silk in an acid bath greenish yellow shades; the diazo component may be replaced by isomers or homologues thereof or their substitution products, e.g. 4 - amino - 1 - phenoxybenzene - 2 - sulphonic acid or methyl or halogen derivatives thereof, or 2 - amino - 1 - (21 - methyl - 41 : 61-dichlorophenoxy) - benzene - 4 - sulphonic acid; (2) 4 - amino - 1 - phenoxybenzene - 3-sulphonic acid --> dimethyldihydroresorcinol (greenish yellow shades); the diazo component may be replaced by 4-amino-1-p-tolyloxybenzene-3-sulphonic acid or 4-amino-6-chloro-1-o-tolyloxybenzene-3-sulphonic acid; (3) 1 - amino - 2 : 4 - diphenoxybenzene - 5-sulphonic acid --> dimethyldihydroresorcinol (yellow shades); the diazo component may be replaced by its methyl and halogen derivatives, or by 21-amino-1 : 4-diphenoxybenzene-41-sulphonic acid; (4) 2 - amino - 1 - (31 : 51-dimethylphenoxy) - benzene - 4 - sulphonic acid --> cyclohexane-spiro-cyclohexane-3 : 5-dione (yellow shades); the diazo component may be replaced by any of those of examples (1) to (3). Specifications 461,884 and 461,965 are referred to. 2 - Amino - 1 - (21 - methyl - 41 : 61 - dichlorophenoxy) - benzene - 4 - sulphonic acid is obtainable by condensing 2 : 4-dichloro-6-methylphenol (sodium salt) with 3-nitro-4-chlorobenzenesulphonic acid and reducing the product. 4 - Amino - 6 - chloro - 1 - o -t olyloxybenzene-3 - sulphonic acid is obtainable by condensation of 3 : 4-dichloronitrobenzene with potassium o-cresolate, reduction and sulphonation. 1 - Amino - 2 : 4 - diphenoxybenzene - 5-sulphonic acid is obtainable by reduction of the condensation product of 2 : 4-dichloro-5-nitrobenzene-1-sulphonic acid with two molecular proportions of potassium phenolate. 21 - Amino - 1 : 4 - diphenoxybenzene - 41-sulphonic acid is obtainable by condensing 4-hydroxydiphenyl ether (potassium salt) with 3-nitro-4-chlorobenzenesulphonic acid and reducing the product.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH494646X | 1937-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB494646A true GB494646A (en) | 1938-10-28 |
Family
ID=4516708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8264/38A Expired GB494646A (en) | 1937-03-19 | 1938-03-17 | Process for the production of azo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB494646A (en) |
-
1938
- 1938-03-17 GB GB8264/38A patent/GB494646A/en not_active Expired
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