Patent GB-325222-A (GB)
Title: An improved process for the manufacture and production of derivatives of monoaminodibenzopyrenequinones
IPC: C09B3/54
Filed: 1928-10-08
Abstract: 325,222. Johnson, J. Y., (I. G. Farbenindustrie Akt.-Ges.). Oct. 8, 1928. Divided on 324,964. Dibenzpyrenequinone derivatives.-Vat dyes are obtained by condensing monoamino-3 : 4 : 8 : 9- dibenzpyrene-5 : 10-quinones with organic compounds containing negative substituents, preferably in an organic medium and if desired in the presence of an acid-fixing agent and a catalyst. As organic compounds containing negative substituents, halogen and nitro compounds and carboxylic acids of aliphatic, cycloaliphatic, aromatic and heterocyclic compounds may be used, the negative substituents being either attached to the nucleus, as in chlorbenzene, alpha- or #-chloranthraquinone, or alpha-nitronaphthalene, or to a side chain, as in benzyl chloride, benzol chloride, benzotrichloride or naphthalene carboxylic acid halides. By employing aliphatic compounds containing a negative substituent, such as methyl iodide, ethyl chloride, ethylene bromide, or the alkyl esters of toluenesulphonic acid, alkylamino derivatives of 3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone are obtained. Organic compounds containing several negative substituents may be used, and may be condensed with several molecular proportions of the aminodibenzpyrenequinones, thus two molecular proportions of the latter may be condensed with one molecular proportion of terephthalyl chloride, ethylene bromide or p-dichlorbenzene, or three molecular proportions of monoamino- 3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone may be condensed with one molecular proportion of cyanuryl chloride. Negatively substituted derivatives of anthraquinone, dibenzanthrone, anthanthrone, pyranthrone, dibenzpyrenequinones, anthraquinone-acridones, and indigo are also specified. Alkali metal carbonates and acetates may be used as acid-fixing agents, and copper, mercury, aluminium or compounds thereof, such as their oxides and carbonates, are specified as condensing catalysts. The production of acylamines takes place readily in the absence of any catalyst, organic bases, such as pyridine, dimethylaniline, quinoline and collidine being preferably employed as acid-fixing agents. In examples, (1) monoamino - 3 : 4 : 8 : 9 - dibenzpyrene-5 : 10-quinone (obtained by reduction of the nitro compound obtained by nitrating the dibenzpyrenequinone in nitrobenzene) is treated with benzoyl chloride in nitrobenzene; the product dyes cotton in fast orange-red shades, while the corresponding product from m-methoxybenzoyl chloride dyes in somewhat redder shades, (2) monoamino - 3 : 4 : 8 : 9-dibenzpyrene-5 : 10- quinone is heated with 1-chloranthraquinone-2- carboxylic chloride in nitrobenzene; the product dyes cotton in orange shades, (3) monoamino- 3: 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is heated with 1-chloranthraquinone in nitrobenzene in the presence of copper oxide and sodium acetate; the product dyes cotton in orange-brown shades, (4) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone. is similarly condensed with cvanuryl chloride; the product, which may be purified by treating with oxidizing agents, such as a hypochlorite solution, dyes cotton in red-brown shades, while similar dyes may be obtained with 2 : 4-dichlorquinazoline or other heterocyclic compounds having negative substituents, (5) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is condensed with 1 amino- (or 1-nitro-) anthraquinone-2-carboxylic chloride; the product dyes cotton in brick-red shades, (6) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is treated with the dichloride of oxalic acid in nitrobenzene; the product, which may be purified by treating with a hypochlorite, dyes cotton in yellow shades; other chlorides such as' those of malonic or succinic acids or thiophosgene, react in a similar manner, (7) dibrommonoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone (made by brominating the amino compoud in oleum) is treated with p-chlorbenzoyl chloride in nitrobenzene; the product gives orange-red dyeings, (8) dichlormonoamino-3- : 4 : 8 : 9-dibenzpyrene- 5 : 10-quinone (made by chlorinating the amino compound with sulphuryl chloride in nitrobenzene) is heated with perchlormethylmercaptan in nitrobenzene; the product dyes cotton in brownish-violet shades, while instead of the parent materials specified, monoalkylamino derivatives and phosgene may be employed, (9) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is condensed with mononitro- or monobrom-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone (obtained by replacing the amino group by bromine by the diazo reaction) in nitrobenzene in the presence of copper oxide and sodium acetate; the product dyes cotton in brown shades, (10) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is heated with monobrombenzene in the presence of sodium acetate under pressure: the product gives olive dyeings, (11) monoamino-3 : 4 : 8 : 9-dibenzpyrene-5 : 10- quinone is heated with octobromcyclohexane (made bv brominating cyclohexane under pressure) and pyridine under pressure; the product dyes cotton in green-grey shades, (12) monoamino - 3 : 4 : 8 : 9-dibenzpyrene-5 : 10-quinone is condensed with trichloranthraquinone-2: 1-benzacridone (made by chlorinating anthraquinone-2 : 1-benzacridone with sulphuryl chloride) in nitrobenzene in the presence of copper oxide and sodium carbonate; the product gives brown dyeings, (13) monoamino-3 : 4 : 8 : 9-dibenzpyrene- 5 : 10-quinone is heated with benzotrichloride in the presence of sulphur; the product dyes cotton in orange shades, (14) monoamino-3: 4: 8: 9-dibenzpyrene-5 : 10-quinone is heated with methyl iodide; the methylamino derivative obtained dyes cotton in green-grey shades, and (15) monoamino- 3 : 4 : 8 : 9 - dibenzpyrene-5 : 10 - quinone is condensed (a) with tetrabromindigo, (b) with dibromanthanthrone (made by brommating anthanthrone in oleum), (c) with mononitropyranthrone (made by nitrating pyranthrone in nitrobenzene), and (d) with mononitrodibenzanthrone (made by nitrating pure dibenzanthrone in nitrobenzene); the products dye cotton in brown or grey shades. Specifications 285,502 and 318,180 are referred to.