Patent GB-891231-A (GB)
Title: Pigment dyestuffs derived from urea and process for their manufacture
IPC: C09B69/00
Filed: 1959-01-13
Abstract: Pigment dyes of the formula A.N(R).CONH.B.NHCO(R)N.A, where A is the residue of an organic dye, B is a non-vattable organic residue and R is a hydrogen atom or an alkyl group, colour p  lacquers, synthetic resins, printing inks and spinning masses for artificial fibres.  The N(R) group may be attached to an aryl nucleus of A directly or via a bridge member such as an alkylene, alkyleneamino, imino, -CO- or -SO2- group.  Indicated dyes are of the anthraquinone and azo series, the latter being preferred.  Dis-, and especially mono-, azo dyes are mentioned and their metal, e.g. copper, nickel, chromium and cobalt, complexes. Benzene-azo-benzene, benzene-azopyrazolone and benzene-azo-naphthalene dyes are indicated, the latter being particularly preferred.  The azo dyes may contain substituents, indicated being halogen atoms and alkyl, trifluoromethyl, hydroxy, alkoxy, acylamino, arylamino, nitro, dialkylamino, carboxylic acid ester and cyano groups.  Anthraquinone dyes mentioned are 1- and 2-aminoanthraquinone and their substituted derivatives, e.g. 1-amino-4-benzoyl- and -phenyl-amino- and -methoxy-anthraquinones and 4-aminoanthraquinone-1(N):2-acridone. Dyes in which the diazo component is derived from anthraquinone are also mentioned.  Residue B may be derived from aliphatic or aromatic compounds, the latter being preferred, representative being hexamethylene diisocyanate, 2,5-dichlorophenylene diisocyanate, naphthylene-1,5-diisocyanate, 3,31-dimethoxydiphenyl-4,41-diisocyanate, di-(3-isocyanato-4-methylphenyl)-urea, benzene-1,11-azonaphthalene-4,41-diisocyanate, 4,41-diaminodiphenylsulphone, 3,31-diamino-4,41-dichlorodiphenyl ketone and 4,41-diamino-3,5,31, 51-tetrachlorodiphenylmethane.  For the preparation of the dyes see Group IV(c).  In examples the dyes are prepared and used to colour polyvinyl chloride, a nitrocellulose lacquer and an alkyd-melamine stoving varnish, which also contain titanium dioxide, and also in the preparation of two pigment compositions, which include dinaphthylmethane disulphonic acid in one, and acetylcellulose, ammonium chloride and methyl glycol in the other, and which are both added to cellulose acetate spinning masses from which filaments are formed.  Various colours are obtained.ALSO:The invention comprises dyes of formula AN(R)CONH-B-NHCO(R)NA where A is the residue of an organic dye, B is a non-vattable organic residue and R is H or Alk.  The dyes are made by treating an appropriate diisocyanate with an amino organic dye or an appropriate diamine with a dye containing an isocyanate group. Indicated dyes are of the anthraquinone and azo series, the latter being preferred.  Amino dyes may have the amino group directly attached to a nucleus of the dye molecule or attached via a bridge such as an alkylene, alkylene-amino, imino, -CO- or SO2 group, e.g. NHCH2CH2NH2, NHNH2, CONH2, CONHNH2 or SO2NH2.  Azo dyes indicated as starting-material are of the diazo and monoazo series, the latter being preferred.  They may be of the benzene-azo-benzene, benzene-azo-pyrazolone and especially benzene-azo-naphthalene series. Metal-free or metallised dyes, e.g. complex copper nickel, chromium and cobalt compounds, may be used.  The azo dyes may have such substituents as halogen atoms or alkyl trifluoromethyl, hydroxy, alkoxy, acyl-, aryl- and dialkyl-amino, nitro, cyano and carboxylic ester groups. Anthraquinone dyes mentioned are 1- and 2-aminoanthraquinone, 1-amino-4- or -5-benzoylamino- and 1-amino-4-methoxy-and -phenylamino-anthraquinones and 4-aminoanthraquinone-1(N),2-acridone.  Azo dyes containing an anthraquinone diazo component may also be used.  Representative of specified diisocyanates are hexamethylene diisocyanate, 2-nitro- and 2-methoxy-5-chlorophenyl-1,4-diisocyanate, naphthylene-1,5-diisocyanate diphenyl-4,41-diisocyanate, 3,31-dimethyl- and -dimethoxy-diphenyl-4,41-diisocyanate, di-(3-isocyanato-4-methylphenyl)-urea and 1,11-azobenzene-4,41-diisocyanate.  Typical of specified diamines are ethylene diamine, 1,4-diamino-2,5-dichloro- and dimethoxy - benzene, 1,5 - diaminonaphthalene, 4,41 - diamino - 3,31 - dichloro - diphenyl, 4,41 - diamino - 1, 11 - azobenzene, 3,31 - diamino - 4,41 - dimethoxy - diphenyl sulphone, 3,31 - diaminodiphenylketone and 3,31 - diaminodi - phenylmethane.  The products are pigment dyes and may be used in a dispersed form for colouring lacquers, plastic masses, especially P.V.C. and printing inks, and for spin dyeing artificial fibres, such as viscose.  Examples are provided of the preparation of the dyes and their use in a number of colouring processes to provide a variety of shades.