GB766407A - Improvements in the production of vat dyestuffs of the anthraquinone series - Google Patents
Improvements in the production of vat dyestuffs of the anthraquinone seriesInfo
- Publication number
- GB766407A GB766407A GB167/55A GB16755A GB766407A GB 766407 A GB766407 A GB 766407A GB 167/55 A GB167/55 A GB 167/55A GB 16755 A GB16755 A GB 16755A GB 766407 A GB766407 A GB 766407A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- carboxylic acid
- nitro
- group
- chloroanthraquinone
- 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 239000000975 dye Substances 0.000 abstract 3
- AWACQBFBMROGQC-UHFFFAOYSA-N 1-amino-4-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2N AWACQBFBMROGQC-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- BIZVHVKTTCPVPP-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2N BIZVHVKTTCPVPP-UHFFFAOYSA-N 0.000 abstract 1
- JOVXWCNPCIBTJQ-UHFFFAOYSA-N 1-chloro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C(=O)Cl)=CC=C3C(=O)C2=C1 JOVXWCNPCIBTJQ-UHFFFAOYSA-N 0.000 abstract 1
- NWFOTILLJRKQQH-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(Cl)=O)=C2[N+](=O)[O-] NWFOTILLJRKQQH-UHFFFAOYSA-N 0.000 abstract 1
- PMOCDYOEOUEPAN-UHFFFAOYSA-N 1-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(C(=O)O)=CC=C3C(=O)C2=C1 PMOCDYOEOUEPAN-UHFFFAOYSA-N 0.000 abstract 1
- -1 1-nitro-anthraquinone-2-carboxylic acid halide Chemical class 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Vat dyestuffs giving red dyeings are produced by reacting 1-amino-4-chloroanthraquinone with a 1-amino- or 1-halogen- or 1-nitro-anthraquinone-2-carboxylic acid halide or with a free carboxylic acid of the said kind in the presence of thionyl chloride and converting any halogen present in the acyl residue of the resultant dyestuff to an amino group. Any nitro group present in the acyl residue may also be converted into an amino group but if left intact is reduced to amino in the vat. In examples 1-amino-4-chloroanthraquinone is reacted with; (1) 1-aminoanthraquinone-2-carboxylic acid chloride; (2) 1-nitro-anthraquinone-2-carboxylic acid chloride, the nitro group being replaced by amino by passing ammonia into the reaction mixture, or alternatively the dyestuff is isolated and the nitro group converted into amino by vatting or by treatment with alkaline sodium sulphide; (3) 1-nitroanthraquinone-2-carboxylic acid and thionyl chloride, the nitro group being replaced by amino as in (2); (4) 1-chloroanthraquinone-2 carboxylic acid chloride, the chlorine atom in the acyl residue being replaced by an amino group by passing ammonia into the reaction mixture before the dyestuff is isolated. Specification 219,830 [Class 2(iii)] is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE335785X | 1954-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB766407A true GB766407A (en) | 1957-01-23 |
Family
ID=6219666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB167/55A Expired GB766407A (en) | 1954-01-28 | 1955-01-04 | Improvements in the production of vat dyestuffs of the anthraquinone series |
Country Status (3)
| Country | Link |
|---|---|
| CH (2) | CH335785A (en) |
| FR (1) | FR1117697A (en) |
| GB (1) | GB766407A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337553A (en) * | 1960-10-28 | 1967-08-22 | Ciba Ltd | Vat dyestuffs containing anthraquinone nuclei |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3802613A1 (en) * | 1988-01-29 | 1989-08-03 | Basf Ag | METHOD FOR PRODUCING ACYLAMINES OF THE ANTHRACHINONE RANGE |
-
1955
- 1955-01-04 GB GB167/55A patent/GB766407A/en not_active Expired
- 1955-01-12 CH CH335785D patent/CH335785A/en unknown
- 1955-01-12 CH CH336531D patent/CH336531A/en unknown
- 1955-01-13 FR FR1117697D patent/FR1117697A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337553A (en) * | 1960-10-28 | 1967-08-22 | Ciba Ltd | Vat dyestuffs containing anthraquinone nuclei |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1117697A (en) | 1956-05-25 |
| CH335785A (en) | 1959-01-31 |
| CH336531A (en) | 1959-02-28 |
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