GB468686A - Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series - Google Patents
Improvements in the manufacture and production of vat dyestuffs of the anthraquinone seriesInfo
- Publication number
- GB468686A GB468686A GB3385935A GB3385935A GB468686A GB 468686 A GB468686 A GB 468686A GB 3385935 A GB3385935 A GB 3385935A GB 3385935 A GB3385935 A GB 3385935A GB 468686 A GB468686 A GB 468686A
- Authority
- GB
- United Kingdom
- Prior art keywords
- product
- vat
- aminoanthracene
- shades
- anthraquinone
- 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 abstract 3
- 150000004056 anthraquinones Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 3
- 229920000742 Cotton Polymers 0.000 abstract 5
- YCSBALJAGZKWFF-UHFFFAOYSA-N anthracen-2-amine Chemical compound C1=CC=CC2=CC3=CC(N)=CC=C3C=C21 YCSBALJAGZKWFF-UHFFFAOYSA-N 0.000 abstract 5
- 239000000975 dye Substances 0.000 abstract 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- DGJNWQJOASAMHY-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carbonyl chloride Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)Cl)=CC=C3C(=O)C2=C1 DGJNWQJOASAMHY-UHFFFAOYSA-N 0.000 abstract 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 229940117975 chromium trioxide Drugs 0.000 abstract 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- -1 disazo compound Chemical class 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000003839 salts 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
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 235000013311 vegetables Nutrition 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/30—1,2 azoles of the anthracene series
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Vat dyestuffs of the triazoloanthraquinone series, of the general formula <FORM:0468686/IV/1> where R is a cyclic radicle having up to two isocyclic non-hydrogenated rings and A is a radicle capable of being vatted which may be attached to R by an atomic bridge, and in which the anthraquinone nucleus shown may contain any substituents, are manufactured by coupling the diazo compound of an amine NH2--R--A with a 2-aminoanthracene and oxidizing the resulting o-aminoazo compound, or, when A is a second triazoloanthraquinone radicle, by coupling 1 molecular proportion of a tetrazonium salt with 2 molecular proportions of a 2-aminoanthracene and oxidizing the resulting disazo compound. The oxidation may be effected in a single operation, or in two stages with intermediate production of a triazoloanthracene. In examples: (1) tetrazotized 4 : 4<1>-diaminodiphenyl is coupled with 2-aminoanthracene and the product is oxidized with chromium trioxide in the presence of nitrobenzene and glacial acetic acid; the product dyes vegetable fibres yellow shades from a hot vat; (2) 4 : 4<1>-diaminodiphenylurea is tetrazotized and coupled with 2-aminoanthracene, and the product is oxidized as in (1); the product dyes cotton reddish yellow-brown shades; the tetrazo component may be replaced by 4 : 4<1>-diaminodiphenyl ketone, the product dyeing cotton brown shades from a black-green vat; (3) anthraquinone-2-carboxylic acid chloride is condensed with p-nitraniline, the nitro group is reduced by means of sodium sulphide solution, the amine is diazotized and coupled with 2-aminoanthracene, and the product is oxidized as in (1); the product dyes cotton yellow shades from a violet vat. Samples have been furnished under Sect. 2 (5) of dyestuffs prepared as follows: (A) anthraquinone - 1(N) : 2 : 2<1>(N) : 1<1> - acridone - 5<1> - carboxylic acid chloride is condensed with p-nitraniline and the product is reduced, diazotized, coupled and oxidized as in (3) above; the product dyes cotton from a violet vat orange shades; (B) anthraquinone-2(S) : 1 : 1<1>(S) : 2<1>-thioxanthone-6<1>-carboxylic acid chloride is similarly reacted; the product dyes cotton from a violet vat yellow shades.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3385935A GB468686A (en) | 1935-12-06 | 1935-12-06 | Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3385935A GB468686A (en) | 1935-12-06 | 1935-12-06 | Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB468686A true GB468686A (en) | 1937-07-06 |
Family
ID=10358362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3385935A Expired GB468686A (en) | 1935-12-06 | 1935-12-06 | Improvements in the manufacture and production of vat dyestuffs of the anthraquinone series |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB468686A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666062A (en) * | 1954-01-12 | Optical bleaching agents containing | ||
| US5772226A (en) * | 1994-03-18 | 1998-06-30 | International Diffusion Consommateurs - I.D.C. | Lifting device for a stand-up wheelchair, and a wheelchair using the same |
-
1935
- 1935-12-06 GB GB3385935A patent/GB468686A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666062A (en) * | 1954-01-12 | Optical bleaching agents containing | ||
| US5772226A (en) * | 1994-03-18 | 1998-06-30 | International Diffusion Consommateurs - I.D.C. | Lifting device for a stand-up wheelchair, and a wheelchair using the same |
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