GB718524A - Manufacture of vat dyestuffs of the anthraquinone series - Google Patents
Manufacture of vat dyestuffs of the anthraquinone seriesInfo
- Publication number
- GB718524A GB718524A GB27358/51A GB2735851A GB718524A GB 718524 A GB718524 A GB 718524A GB 27358/51 A GB27358/51 A GB 27358/51A GB 2735851 A GB2735851 A GB 2735851A GB 718524 A GB718524 A GB 718524A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthraquinone
- fluoro
- chloro
- acid
- dicarboxylic
- 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
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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1 - Fluoro - 2 - methyl - 4 - or 5 - chlorobenzene may be made by treating the corresponding 1-amino compound with hydrofluoric acid and sodium nitrite or with hydrofluoboric acid. 2 - Fluoro - 4 - or 5 - chlorobenzoic acid may be made by oxidizing the corresponding 1-methyl derivative, e.g. with potassium permanganate, or hydrolysing the corresponding 1-trichloromethyl derivative. 2 - Fluoro - 4 - or 5 - chlorobenzoyl chloride is obtained from the corresponding acid on treatment with thionyl chloride. Specification 555,055 is referred to.ALSO:The invention comprises dyestuffs of formula:- <FORM:0718524/IV(c)/1> where n is 1 or 2. X is the residue of a carboxylic acid of n carboxyl groups and R is a benzene residue containing in ortho position to the -CO-group a fluorine atom and in para position with respect to one of these substituents a chlorine atom. They may be made by treating 1, 5-diaminoanthraquinone or a 1-amino-5-acylaminoanthraquinone with an acylating agent chosen so that the final product contains the requisite groupings and orientations. Thus 1, 5-diaminoanthraquinone may be treated with two mols of 2-fluoro-4- or -5-chlorobenzoic acid or its acid chloride to yield a product similar to that obtained by acylating 1-amino-5-(21-fluoro-41- or -51-chlorobenzoylamino)-anthraquinone with the same chlorobenzoic acid. Alternatively the latter anthraquinone may be acylated with a monohalogen benzene carboxylic acid and is advantageously acylated with agents derived from dicarboxylic acids such as oxalic, iso and tere-phthalic, naphthalene-2, 6-dicarboxylic, fluoranthene-4, 11-dicarboxylic or thianthrene dicarboxylic acids. When the 1-amino-5-acylaminoanthraquinone does not contain the desired fluoro, chloro acyl residue it is acylated with a 2-fluoro-4-or -5-chloro-benzoic acid. Advantageously the dyestuffs do not contain more than three halogen atoms per anthraquinone residue. Acylation is preferably effected by means of reactive functional derivatives of the acids concerned. Solvents or dispersing media may be present especially those of high boiling point e.g. mono-, di- or tri-chlorobenzene, nitrobenzene or naphthalene, reaction being effected at about 100 DEG C. to the boiling point of the acylation mixture. The products dye and print animal and especially vegetable fibres, artificial silk or regenerated cellulose and superpolyamide fibres. In examples (1) 1-amino-5-(41- or 51-chloro - 21 - fluorobenzoylamino) anthraquinone is treated with 4-chlorobenzoyl chloride, the anthraquinone being made by the partial acylation of 1, 5 - diaminoanthraquinone with 2 - fluoro - 4 - or 5 - chlorobenzoyl chloride or from 1-chloro-5-(41- or 51-chloro-21-fluorobenzoylamino)-anthraquinone by replacing the Cl. atom by a toluene sulphonamide residue and splitting off a sulphonic acid residue, and 1-amino-5-(41-chloro - 21 - fluorobenzoylamino)-anthraquinone is treated with (2) oxalyl chloride, (3) tere phthalic acid dichloride and (4) thianthrene dicarboxylic acid dichloride. Representative of other acids listed for reaction with the anthraquinone of (2) (preferably as their dichlorides) are diphenyl-4, 41-dicarboxylic and azobenzene-4, 41-dicarboxylic acids and for reaction with the 51-chloroisomer of the above anthraquinone representative are isophthalic, thianthrene dicarboxylic, diphenyl - 4, 41 - dicarboxylic and azodiphenyldicarboxylic acids. 1 - amino - 5 - (41 - chloro - 21 - fluoro - benzoylamino)-anthraquinone may be made by the partial acylation of 1, 5-diaminoanthraquinone with 2-fluoro-4-chlorobenzoyl chloride or from 1-chloro-5 - (41 - chloro - 21 - fluorobenzoylamino) - anthraquinone by replacing the chlorine atom by a toluene sulphonamide group followed by the removal of the sulphonic acid residue. 1-amino-5-(51 - chloro - 21 - fluorobenzoylamino) - anthraquinone may be made in a similar way. Specification 555,055 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH718524X | 1950-11-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB718524A true GB718524A (en) | 1954-11-17 |
Family
ID=4531331
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27358/51A Expired GB718524A (en) | 1950-11-24 | 1951-11-21 | Manufacture of vat dyestuffs of the anthraquinone series |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB718524A (en) |
-
1951
- 1951-11-21 GB GB27358/51A patent/GB718524A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2356618A (en) | Stabilized diazo printing paste | |
GB1000206A (en) | New vat dyestuffs and process for their manufacture and use | |
GB718524A (en) | Manufacture of vat dyestuffs of the anthraquinone series | |
US3585219A (en) | Process for the production of sulfonated primary aminoanthraquinone by conversion of an n-cyclohexyl-aminoanthraquinone | |
US2995584A (en) | Anthraquinonyl sulfones and production thereof | |
GB954410A (en) | New anthraquinone vat dyestuffs and process for their manufacture | |
GB549640A (en) | New anthraquinone vat dyes | |
GB658722A (en) | Process for the manufacture of vat dyestuffs of the anthraquinone series | |
US2647127A (en) | Process for preparing metal phthalocyanines | |
GB877487A (en) | New vat dyestuffs of the acedianthrone series and process for their manufacture | |
US2195289A (en) | 2- and 2:7-di-alkylarylcarbamylfluorenes and fluorene-2- and 2:7-di-carboxylic acids and a process of making them | |
GB771347A (en) | Vat dyestuffs of the anthraquinone series | |
US3829452A (en) | Anthraquinone dyestuffs | |
GB762752A (en) | Manufacture of anthraquinone vat dyestuffs | |
US2505744A (en) | Green pigment composition | |
GB737016A (en) | Manufacture of vat dyestuffs of the anthraquinone series | |
US2415937A (en) | Oxazole compounds of the anthraquinone series | |
GB934583A (en) | New anthraquinone vat dyestuffs and process for their manufacture | |
GB473884A (en) | Process for the manufacture of acid wool dyestuffs of the anthraquinone series | |
GB790921A (en) | New nitro-dyestuffs and process for making them | |
GB719282A (en) | Improvements in the production of vat dyestuffs of the anthraquinone series | |
GB605701A (en) | Manufacture of vat dyestuffs | |
GB750969A (en) | Improvements in or relating to pigment dyestuffs of the anthraquinone series | |
US2270170A (en) | Process for preparing tetrabromoindigo | |
US1099039A (en) | Sulfur dyes and process of making same. |