Patent GB-545996-A (GB)
Title: Process for the preparation of dyestuffs of the anthraquinone series
IPC: C09B1/32
Filed: 1940-12-18
Abstract: 545,996. Dyes. SANDOZ, Ltd. Dec. 18, 1940, No. 17836. Convention date, Dec. 20, 1939. [Classes 2 (iii) and 15 (ii)] Aminoanthraquinone derivatives are obtained by condensing a compound of the general formula wherein Z represents hydroxy, amino, alkylamino or halogen, V represents hydroxy or halogen and X represents H, halogen, alkyl, alkoxy or SO 3 H and wherein one or both positions 6, 7 is occupied by halogen, with a compound of the general formula wherein A represents methyl or ethyl, B represents methyl, ethyl, chlorine or bromine and D represents H or alkyl. The products so obtained may be sulphonated; e.g. by treatment with sulphuric acid monohydrate, oleum or chlorosulphonic acid or by replacement of a reactive atom or group such as a #-halogen atom by SO 3 H by treatment with a sulphite. The products containing no sulphonic acid groups are suitable for dyeing cellulose ester or ether materials or for colouring nitrocellulose lacquers and those containing such groups are suitable for dyeing wool or silk. In examples, (1) 6-chloro- or bromo-quinizarin and its leuco compound are stirred at 90-140C. with mesidine in glacial acetic acid containing boric acid to obtain 1 : 4-di-mesidino-6-chloro-anthraquinone, which may be sulphonated with weak oleum ; (2) 1 : 4 : 6-trichloroanthraquinone is stirred at 160-180C. with mesidine in presence of potassium acetate and copper powder ; the product may be sulphonated ; (3) 6 : 7-dichloroquinizarin or a 6-chloro-7-halogeno-, other than chloro-, quinizarin, together with the corresponding leuco compound, is stirred at 90-140C. with mesidine-in glacial acetic acid containing boric acid ; the products may be sulphonated ; the same products are obtainable from 1 : 4 : 6 :7 -tetrachloroanthraquinone or a 1 : 4 : 6-trichloro- 7-halogeno-, other than chloro-, anthraquinone by condensation with mesidine as in (2) ; (4) and (5) 6-chloroquizarin and its leuco compound are condensed with vic-m-xylidine and 1-amino-2 : 4-dimethyl-6-chlorobenzene respectively as in (1) ; the products may be sulphonated ; (6) 1-amino-2 : 4-dibromo-6- chloroanthraquinone is stirred at 90-160C. with mesidine in presence of potassium acetate and copper acetate ; the product may be converted into a water-soluble wool or silk dyestuff by treatment with a sulphate in phenol at 100-160C. and further sulphonated, if desired, with weak oleum. Specification 457,386 is referred to. 6- Chloroquinizarin is obtained by condensation of 4- chlorophthalic anhydride with pchlorophenol in sulphuric acid in presence of boric acid. 6- Bromoquinizarin is obtained by the action of sulphuric acid in presence of boric acid on the product of mono-chlorination of 1-hydroxy-6-bromoanthraquinone. 1 : 4 : 6 : 7-Tetrachloroanthraquinone is obtained by the action of sulphuric acid on the condensation product from 4 5-dichlorophthalic anhydride and 1 : 4-dichlorobenzene. 1- Amino - 2 : 4-dibromo - 6-chloroanthraquinone is obtained by dibromination of 1- amino-6-chloroanthraquinone. The Specification as open to inspection under Sect. 91 comprises also the manufacture of the dyes in which A and B represent alkyl in general and refers to the conversion of the products into diaryl, di- and tri-aryl-methane, pyrimidone and pyridone derivatives. This subject-matter does not appear in the Specification as accepted.