GB923530A - Improvements relating to anthraquinone dyestuffs and their use - Google Patents
Improvements relating to anthraquinone dyestuffs and their useInfo
- Publication number
- GB923530A GB923530A GB4332660A GB4332660A GB923530A GB 923530 A GB923530 A GB 923530A GB 4332660 A GB4332660 A GB 4332660A GB 4332660 A GB4332660 A GB 4332660A GB 923530 A GB923530 A GB 923530A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- fluoroisophthalic
- dichloride
- prepared
- mono
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 2
- AUIOTTUHAZONIC-UHFFFAOYSA-N 5-fluorobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(F)=CC(C(O)=O)=C1 AUIOTTUHAZONIC-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RDGGAROGFSWMOU-UHFFFAOYSA-N 5-fluorobenzene-1,3-dicarbonyl chloride Chemical compound FC1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 RDGGAROGFSWMOU-UHFFFAOYSA-N 0.000 abstract 1
- DGEQGSHWQUKNMP-UHFFFAOYSA-N C(C)OC(C1=CC(C(=O)OCC)=CC(=C1)F)=O Chemical compound C(C)OC(C1=CC(C(=O)OCC)=CC(=C1)F)=O DGEQGSHWQUKNMP-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 238000006350 Schiemann fluorination reaction Methods 0.000 abstract 1
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- 230000001588 bifunctional effect Effects 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- VQRVPAXIXNQFHI-UHFFFAOYSA-N diethyl 5-aminobenzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC(N)=CC(C(=O)OCC)=C1 VQRVPAXIXNQFHI-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C09B1/43—Dicarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
5-Fluoroisophthalic acid and dichloride are prepared by nitrating isophthalic acid, esterifying with ethanol, reducing the nitro group, subjecting the 5-amino-isophthalic acid diethyl ester to the Schiemann reaction to give 5-fluoroisophthalic acid diethyl ester which is saponified to the acid and the 5-fluoroisophthalic acid is treated with thionyl chloride. Fluoroterephthali acid dichloride is prepared analogously.ALSO:The invention comprises anthraquinone dyes of formula A1-NH-CO-B-CO-NH-A2 wherein A1 and A2 are identical or different radicals of the anthraquinone series which contain substituents which do not dissociate acid in neutral water and B is a mono- or di-fluorophenylene radical bound to the carbonyl groups in m- or pposition. They are prepared by condensing 1 mol. of a mono- or di-fluoro-iso- or -tere-phthalic acid or a bifunctional derivative thereof with 2 mols. of one or two aminoanthraquinones. The dyes give yellow orange and brown shades on cotton. In an example 1-aminoanthraquinone and 5-fluoroisophthalic acid dichloride are mixed and boiled in 1:2-dichlorobenzene and the dye is filtered off. Many similar examples are specified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8202459A CH382891A (en) | 1959-12-18 | 1959-12-18 | Process for the preparation of anthraquinone dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB923530A true GB923530A (en) | 1963-04-10 |
Family
ID=4539369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4332660A Expired GB923530A (en) | 1959-12-18 | 1960-12-16 | Improvements relating to anthraquinone dyestuffs and their use |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH382891A (en) |
| DE (1) | DE1155204B (en) |
| GB (1) | GB923530A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098793A (en) * | 1976-09-27 | 1978-07-04 | Montedison S.P.A. | Anthraquinone compounds and process for preparing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR807939A (en) * | 1935-06-07 | 1937-01-25 | Ig Farbenindustrie Ag | New vat dyes |
-
1959
- 1959-12-18 CH CH8202459A patent/CH382891A/en unknown
-
1960
- 1960-12-16 GB GB4332660A patent/GB923530A/en not_active Expired
- 1960-12-16 DE DEG31174A patent/DE1155204B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098793A (en) * | 1976-09-27 | 1978-07-04 | Montedison S.P.A. | Anthraquinone compounds and process for preparing same |
Also Published As
| Publication number | Publication date |
|---|---|
| CH382891A (en) | 1964-10-15 |
| DE1155204B (en) | 1963-10-03 |
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