Patent GB-952619-A (GB)
Title: New pyrimidine dyestuffs
Inventor: ANDERSON GEORGE DE WINTER
IPC: C09B62/20
Filed: 1960-06-24
Abstract: The invention comprises dyes which have at least one group of formula -N(R)T, where R is H or a substituted or unsubstituted alkyl or cycloalkyl radicle, T is a pyrimidine ring attached to N via a carbon atom of the ring and has at least one group of formula -O-A which is attached to a carbon of the pyrimidine ring, where A is a sulphonated aryl radicle which may have further substituents.  The dyes may be made by treating corresponding halopyrimidine dyes with compounds of formula W-O-A, where W is H or a metal atom or by treating a dye containing at least one NHR group with an appropriate halopyrimidine. Azo dyes may also be made by conventional diazotization and coupling process.  The -N(R)T groups are attached to carbon atoms of the dye molecule. The carbon atom may be part of an aryl residue or of an alkyl chain which is attached directly to an aryl residue or via a bridging atom or group.  Mono- and poly-azo, nitro, anthraquinone and phthalocyanine dyes are preferred and preferably have at least one water-solubilizing group, e.g. alkylsulphone, sulphamyl, carboxylic acid and especially sulphonic acid groups.  Metal complexes e.g. of copper, chromium and cobalt, may also be prepared.  Indicated for A are sulphophenyl, sulphonaphthyl and disulpho-naphthyl which may contain chlorine and bromine substituents. Amongst specified values for R are methyl, butyl and cyclohexyl.  Specified substituents for R are hydroxy and methoxy groups. Chlorine and bromine are specified halogens. Compounds containing more than one O-A group are made especially from pyrimidines containing a negative substituent, e.g. chlorine, bromine, cyano, carboxy or carboalkoxy groups, in the 5-position. Indicated as linking atoms and groups are O, S, NH, N-alkyl, SO2, SO2NH, CONH and SO2N-alkyl.  Indicated dues from which the products may be derived are those of formula <FORM:0952619/C3/1> where D1 is a mono- or di-cyclic aryl radicle, free from azo and NHR groups, the NHR group is preferably in the 6, 7 or 8 position and there may be a sulphonic acid group in the 5- or 6-position; indicated for D1 are stilbene, diphenyl, benzthiazolylphenyl and diphenylamine residues preferred, being phenyl or naphthyl residues with a sulpho group ortho to the azo link, and which includes dyes where the group NHR is attached to a benzoylamino or anilino group which is in the 6-, 7- or 8-position; other specified substituents for D1 being chlorine, methyl, acetylamino and methoxy; disazo dyes where D1, above, is of the azobenzene, azonaphthalene or phenylazonaphthalene series; of formula <FORM:0952619/C3/2> where D1 is as above, preferably a disulphonaphthyl or stilbene residue, and the benzene residue may contain halogen atoms, alkyl, alkoxy, carboxy and acylamino groups; mono-or dis-azo compounds of formula H-N(R)-D1-N=N-K where D1 is an arylene radicle, e.g. of the azobenzene, azonaphthalene or phenylazonaphthalene series, but preferably is a benzene or naphthalene residue, especially a sulphophenyl group, and K is a naphthol sulphonic acid or enolized ketomethylene residue; those of formula D1-N=N-K2-NHR where D1 is as in the first two classes above and K2 is an enolized ketomethylene residue with OH a  to the azo group; metal complexes of ths above dyes which contain metallizable groupe ortho to the azo group; those of formula <FORM:0952619/C3/3> where SO3H may be in the 5, 6, 7 or 8 position and Y is a bridging group, preferably a divalent benzene residue, e.g. phenylene, diphenylene, 4,41-stilbene or azobenzene, and preferably has one SO3H group for each benzene ring present; those of formula (SO2-w)n-Pc-(SO2NH-Y-NHR)m where Pc is preferably a copper phthalocyanine residue, w is OH and/or an amino group which may be substituted, Y is a bridging group, preferably aliphatic, cycloaliphatic or aromatic; n and m are 1, 2 or 3 but n+m must not be greater than 4 and those of formula NO2-A-NH-B-NHR where A and B are monocyclic aryl nuclei with the nitro group ortho to the NH group. Dyes made by diazotization and coupling processes are preferably derived from phenyl or naphthyl amines, which may contain an arylazo group, and acylacetarylide, 5-pyrazolone, phenol, naphthol or arylamine coupling components.  Preferred classes of dyes are those which have at least one water-solubilizing group, preferably SO3H, and which have at least one or two groups of formula N(R)-T1(OA)(Hlg)n, where R and A are as above, T1 is a pyrimidine ring, Hlg is Cl or Br and n is 1 or 2, and those which have at least one water-solubilizing group, preferably SO3H, and which have one or two groups of formula <FORM:0952619/C3/4> where R and A are as above, n is 1 or 2, m is 0 or 1, but m+n must be 2 and X is H or Hlg, e.g. Cl or Br.  The dyes colour natural and artificial textile materials, e.g. cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile, modified polyacrylonitrile and aromatic polyester fibres. Dyes containing water-solubilizing groups are especially of use for colouring cellulosic materials, particularly when used in conjunction with an acid-binding agent. Nitrogenous materials are coloured from a mildly alkaline, neutral or acid dyebath.  The dyes may also be applied to textiles in conjunction with a treatment with a resin-forming composition and an acid-catalyst.  Examples are provided of the preparation of the dyes and their use in colouring processes to provide a variety of colours. Specification 822,047 and 822,948 are referred to.