Patent GB-512031-A (GB)
Title: Manufacture of acid wool dyestuffs of the anthraquinone series
IPC: C09B1/34
Filed: 1938-02-24
Abstract: 512,031. Dyes. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.). Feb. 24, 1938, No. 5872. [Class 2 (iii)] Acid wool dyestuffs of the anthraquinone series are made by condensing by means of sulphuric acid an anthraquinonylamino substituted diaryl ketone containing a sulpho group and, in o-position to the keto group linking the two aryl residues, a carboxy group (the aryl radicals being of the benzene series) with an aromatic hydrocarbon or a homologue or substitution product thereof. The products may, for instance, have the formula wherein X represents H or amino, R1 represents an aryl radical of the benzene series (which expression includes.radicals consisting of several benzene nuclei in a chain) and R2 represents the radical of an aromatic hydrocarbon or a homologue or substitution product thereof, and the starting materials may, for instance, have the formula wherein X is as above, and R1 represents an aryl radical of the benzene series. The condensation may be carried out by stirring the components for some hours in concentrated sulphuric acid at 0‹ C. to 25‹ C. The starting materials may be prepared by condensing one or two mols. of a halogenanthraquinone-sulphonic acid with an amino-o-benzoylbenzoic acid, which may contain the amino group in the benzoyl radical or in the benzoic acid radical or in both, and which may also contain further substituents. Halogenanthraquinone-sulphonic acids specified are 1-halogenanthraquinone-2 or 3-sulphonic acids, 1-amino-4-halogenanthraquinone-2-sulphonic acids, 1-aminoanthraquinone-4-halogen-2.6-disulphonic acids, and 1.4-dihalogenanthraquinone-6-sulphonic acids. These sulphonic acids may contain in the non-halogenated nucleus halogen, sulpho, amino, acylamino, or methoxy-acylamino groups. Aromatic hydrocarbons specified are benzene, phenyl chains of two or more benzene nuclei, homologues with straight or branched chains, naphthalene, or phenanthrene, and halogen, hydroxy, alkyl or aryloxy substitution products of such hydrocarbons are also specified. In examples, the condensation product from 1-amino-4-bromanthraquinone-2-sulphonic acid and 3<1>-amino-4<1>-methyl-o-benzoylbenzoic acid (cf. Specification No. 355,743) is condensed in sulphuric acid with (1) benzene, (2) toluene (or o-, m-, or p-xylene or mesitylene), (3) naphthalene in nitrobenzene, (4) n-dodecylbenzene or n-tetradecylbenzene, (5) anisole or the dimethyl ether of pyrocatechol, resorcinol, or hydroquinone, or (6) hydroquinone-di-n-butyl ether, giving blue wool dyestuffs in each case. Also in examples, toluene is condensed in sulphuric acid with the product from 31-amino- 4<1>-methoxy-o-benzoylbenzoic acid and (7) 1- amino-4-bromoanthraquinone-2-sulphonic acid, (8)1- amino - 4 - iodo - anthraquinone - 2.6 - disulphonic acid, (.10) 1-iodoanthraquinone-2-sulphonic acid, or 1-bromanthraquinone-3-sulphonic acid, giving blue and red wool dyes. In further examples toluene is condensed in sulphuric acid with (9) the product from 1- amino-4-bromanthraquinone-2-sulphonic acid and 4<11>-amino-4<1>-phenyl-o-benzoylbenzoic. acid (greenish-blue tints) and (11) the product from 1-bromanthraquinone-2-sulphonic acid and 3<1> 4<1>-diamino-o-benzoylbenzoic acid (cf. Specification No. 454,423) (brown tints).