Patent GB-722367-A (GB)
Title: Improvement in 1:5-dihydroxy-8-nitro-4-aminoanthraquinone compounds
Filed: 1952-08-13
Abstract: The invention comprises dyestuffs of the formula <FORM:0722367/IV (c)/1> wherein X represents a monohydroxyalkyl group of 1-3 carbon atoms, a dihydroxyalkyl group of 2-3 carbon atoms, or a -(OCH2CH2)n-O-R group where n is 1, 2, 3 or 4 and R is hydrogen or an alkyl group of 1-2 carbon atoms and Y is hydrogen, chlorine, hydroxy, methoxy, or methyl.  They are made by condensing 1.5-dihydroxy-4.8-dinitroanthraquinone with a primary arylamine of the formula <FORM:0722367/IV (c)/2> The reaction may be carried out in an excess of the amine, in water, or in an organic solvent such as a phenol, a monohydric alcohol, a glycol or glycol ether, an N,N-diallyl fatty acid amide, or a nitrogen compound such as nitrobenzene or pyridine. The products dye cellulose esters (e.g. acetate, propionate, butyrate, acetate-propionate, or acetate-butyrate), and may be applied as a dispersion made by grinding to a paste in presence of a sulphonated oil, soap, sodium lignin sulphonate, or other dispersing agent.  In examples, 1.5-dihydroxy-4.8-dinitroanthraquinone is reacted with (1) o- or p-aminophenyl ethyl alcohol or a mixture thereof, (2) o-, m- or p-(b -hydroxyethoxyethoxyethoxy)-aniline; (3) o-, m-, or p-(g -hydroxypropyl) aniline or a mixture of the o-and p-bodies; (4) m-aminophenylmethyl alcohol; (5) m-aminophenylmethylcarbinol; (6) m - amino - benzyl alcohol; (7) p - (a b  - dihydroxyethyl) - aniline; (8) 2-methyl-3-(b -hydroxyethyl)-aniline; (9) 2-hydroxy-5-(b -hydroxyethyl)-aniline; (10) 4-chloro-(2- or 3-)-aminophenylethyl alcohol; (11) 3-amino-2-methylphenylmethylcarbinol; (12) 3 - amino - 4 - methoxyphenylmethyl - carbinol; (13) o- or p-(b -hydroxyethoxyethoxyethoxyethoxy)-aniline; (14) p-(b -ethoxyethoxyethoxyethoxy) - aniline; (15) o - (b  - methoxy - ethoxyethoxy) - aniline; (16) m - or p - (b  - hydroxyethoxyethoxy) - aniline; (17) p - (hydroxyethoxy) - aniline; (18) a mixture of o - and p - (b  - hydroxypropyl) - aniline; (19) a mixture of o - and p - aminophenyl - 2 - propanol - 1; (20) p - or a mixture of o - and p - (a ,g  - dihydroxypropyl) - aniline; (21) 2 - methoxy - 5 - (g  - hydroxypropyl) - aniline; (22) a mixture of o- and p-(b ,g -dihydroxypropyl)-aniline; (23) m- or a mixture of o- and p-(a  - hydroxypropyl) - aniline; 24) o - amino - phenyl - dimethyl carbinol; (25) 3 - (2 - and/or 4 - amino - 3 - chlorophenyl) - 1 - pro - panol; (26) a mixture of o - and p - (a ,b  - dihydroxypropyl) - aniline; (27) a mixture o - and p - (sym - dihydroxypropyl) - aniline; (28) a mixture of o-, m-, and p-aminobenzyl alcohol; (29) m-(b -ethoxyethoxyethoxy)-aniline. Specifications 646,459 and 716,937 are referred to.ALSO:A mixture of o-, m, and p-aminobenzyl alcohols is prepared by nitrating benzaldehyde and reducing the mixture obtained with hydrogen in presence of Raney nickel.  A mixture of o- and p-aminophenylethyl alcohols is obtained by nitrating phenylethyl acetate, hydrolysing the acetate group and reduction.  2 and/or 3-Amino-4-chlorphenylethyl alcohol is obtained by Sandmeyer reaction from p-aminophenylethyl alcohol, followed by nitration and reduction. m-Aminophenylethylalcohol is prepared by two-stage reduction from m-nitrophenylacetic acid, i.e. first with Raney nickel and then with lithium aluminium hydride.  Other matter appears which is identical with matter described in Specification 716,937. Specification 646,459, [Group IV (c)], also is referred to.