Patent GB-716937-A (GB)
Title: Improvement in 1:8-dihydroxy-5-nitro-4-anilinoanthraquinone compounds
IPC: C09B1/514
Filed: 1952-08-13
Abstract: A number of aminophenyl propanols or propanediols are prepared by nitration, reduction and hydrolysis of the corresponding phenylpropanol or phenylpropanediol acetates or diacetates. Products specified are 3-(aminophenyl) - propanol - 1, 1- or 2-(aminophenyl)-propanol - 2, 1 - (aminophenyl) - 1,3 -, 2,3-, or 1.2-dihydroxypropane, 2-(aminophenyl)-1,3-dihydroxypropane, and 2-(aminophenyl)-propanol-1.  m - (g  - hydroxypropyl) aniline and 2 - methoxy - 5 - (g  - hydroxypropyl) aniline are obtained from m-nitrobenzaldehyde and 3-nitro-4-methoxy-benzaldehyde respectively by Perkins reaction to give the corresponding cinnamic acid substitution products, which are reduced with Raney nickel to the m-aminophenylpropionic acids, and reducing further with lithium aluminium hydride.  3 - (2 - and/or 4 - amino - 3 - chlorphenyl) - propanol-1 is obtained from m-(g -hydroxypropyl) aniline by replacing the amino group by chlorine (Sandmeyer), acetylating, nitrating, reducing, and hydrolysing.  The diacetate of 1-phenyl-2,3-propanediol-1 is obtained by phenylmagnesium bromide with epichlorhydrin and acetylating first with potassium acetate in acetic acid followed by acetic anhydride.  Specification 646,459, [Group IV (c)], is referred to.ALSO:The invention comprises dyes of the formula: <FORM:0716937/IV(c)/1> where X represents a mono-b - or g - hydroxyalkyl group or dihydroxyalkyl group of three carbon atoms, a -(OCH2 CH2)n-OH group where n is 1, 2, 3, or 4 or a -(OCH2 CH2)m OR group where m is 1, 2, or 3, and R is alkyl of 1 or 2 carbon atoms, and Y is hydrogen, chlorine, hydroxy, methoxy, or methyl.  They are made by condensing 1.8-dihydroxy-4.5-dinitroanthraquinone with a primary arylamine of the formula: <FORM:0716937/IV(c)/2> The reaction may be carried out in an excess of the amine, in presence of water, or in an organic solvent such as an alcohol, a phenol, a glycol or glycol ether, an N.N-dialkyl fatty acid amide, or a nitrogen compound such as nitrobenzene, pyridine, or quinoline.  The products dye cellulose esters (e.g. acetate, propionate, butyrate, acetate-propionate, and 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, 1.8-dihydroxy-4.5-dinitroanthraquinone is reacted with (1) p-(b -hydroxyethoxy) aniline, (2) o- or m-(b -hydroxyethoxyethoxy) aniline, (3) o-, m-, or p-(b -hydroxyethoxyethoxyethoxy)-aniline, (4) o- or p-(b -hydroxyethoxyethoxyethoxyethoxy)-aniline, (5) m- or p-( -ethoxyethoxyethoxy)-aniline, (6) p-(b -ethoxyethoxyethoxyethoxy) aniline, (7) o-(b -methoxyethoxyethoxy)-aniline, (8) o-, m-, or p-(g -hydroxypropyl) aniline, or mixtures of them, (9) 2-(o- and p-aminophenyl) propanol-1, (10) 1-(o- and p-aminophenyl)-propanol-2, (11) 1-(aminophenyl),-1.3-dihydroxypropane, (13) 2-(aminophenyl)-propanol-2, (14) 1-(aminophenyl)-2.3-dihydroxypropane, (15) 2-methoxy-5-(g -hydroxypropyl)-anilene, (16) 3-(2- and/or 4-amino-3-chlorophenyl)-1-propanol, (17) a mixture of o- and p-(a b -dihydroxypropyl) aniline, (18) a mixture of o- and p-(sym.-dihydroxyisopropyl) aniline.  Specification 646,459 is referred to.