Patent GB-429176-A (GB)
Title: Manufacture of dyestuffs
IPC: C09B25/00
Filed: 1933-11-20
Abstract: Dyestuffs of the quinoline series are manufactured by condensing a quinaldine, containing in the 3-position a hydroxy group, with the anhydride or imide of an unsubstituted or substituted dicarboxylic acid, the product being, if required, sulphonated or, if desired, halogenated, or both sulphonated and halogenated in either order. The sulphonation may be effected in known manner, e.g. by the action of fuming sulphuric acid below 15 DEG  C.  Suitable quinaldines are 3-hydroxy-2-methylquinoline or its substitution products containing, for instance, a sulphonic group, or containing, e.g. in the 4-position, an amino-group, which may be acylated or arylated. Suitable dicarboxylic acid anhydrides are phthalic anhydride and its substitution products, e.g. 3-chloro- or 3 : 6-dichlorophthalic anhydride, also polycarboxylic acid anhydrides, such as tetracarboxylic acid anhydrides, e.g. pyromellitic acid anhydride, also naphthalene-1 : 2 : 5 : 6-tetracarboxylic acid anhydride or mellitic acid anhydride.  The products are acid wool dyestuffs, whilst those from polycarboxylic acid anhydrides, when sulphonated, also dye cotton.  In examples: (1) 2 - methyl - 3 - hydroxyquinoline is fused with phthalic anhydride to produce 3-hydroxyquinophthalone, which is sulphonated; the product dyes wool yellow tints; (2) the condensation of (1) is effected at a lower temperature in the presence of zinc chloride; (3) 3-hydroxyquinophthalone is brominated in boiling acetic acid solution, yielding a monobromocompound which is sulphonated; the product dyes wool yellow tints; (4) phthalic anhydride is fused with 3-hydroxyquinaldinesulphonic acid (obtainable by sulphonating 3-hydroxyquinaldine); the product dyes wool light yellow tints; (5) 4-benzoylamino-3-hydroxy-2-methylquinoline (obtainable by coupling 3-hydroxyquinaldine with diazotized aniline, reducing and splitting the azo-dyestuff and reacting the product with benzoyl chloride) is fused with phthalic anhydride and the product is sulphonated; the product dyes wool greenish-yellow tints; if the benzoyl chloride is replaced by 1 - hydroxy - 2 - carboxy - benzene - 4 - sulphonic acid chloride the dyestuff contains groups capable of being chromed; (6) b -hydroxyquinaldine is fused with 3-chlorophthalic anhydride and the product is sulphonated; the product dyes wool yellow tints; (7) the 3-chlorophthalic anhydride of (6) is replaced by 3 : 6-dichlorophthalic anhydride; the product dyes wool yellow tints; (8) pyromellitic acid anhydride is boiled with 3-hydroxyquinaldine and trichlorobenzene and the product is sulphonated; the product dyes wool and cotton yellow tints; (9) aliphatic or alicyclic dicarboxylic acid anhydrides may be employed in the foregoing examples.  Samples have been furnished under Sect. 2 (5) of products prepared as follows: (a) 2-methyl-3-hydroxyquinoline-4-carboxylic acid is heated with phthalic anhydride, yielding a product identical with the unsulphonated product of (1); it may be used as a pigment dyestuff or for colouring lakes and benzine; (b) the product of (a) is sulphonated to yield a product identical with the sulphonated product of (1); (c) 4-acetylamino - 3 - hydroxy - 2 - methylquinoline (obtainable by coupling 3-hydroxy-2-methylquinoline with diazotized sulphanilic acd reducing and splitting the azo-dyestuff and boiling the product with acetic anhydride in chlorobenzene) is heated with phthalic anhydride; (d) the product of (c) is sulphonated, yielding a dyestuff which dyes wool yellow tints.