Patent GB-929588-A (GB)
Title: Water-soluble dyes of the anthraquinone and perylene tetracarboxylic acid diimide series
Inventor: WEISSAUER HERMANN
IPC: C09B62/44
Filed: 1961-02-24
Abstract: The g -methane sulphonate and g -p-toluene sulphonate esters of 5-(b :g -dihydroxy-propoxy-)-2-methyl-aniline are made by reacting 2-methyl- 5-(b :g -epoxypropoxy)- formanilide with methane sulphonic acid and p-toluene sulphonic acid respectively.  p-(b -hydroxy-g -sulphatopropoxy)-aniline is made by esterifying with sulphuric acid, p-(b :g -dihydroxy-propoxy) aniline which is prepared by hydrolysis of the corresponding acetanilide.  m-(b -hydroxy-g -sulphatopropoxy) aniline is made by reacting m-(b :g -dihydroxy-propoxy)-aniline or formanilide with sulphuric acid.  2-Methyl- 5-epoxypropoxyformanilide is made by condensing 2-methyl-5-hydroxyformanilide with epichlorhydrin.ALSO:The invention comprises water-soluble dyes of the anthraquinone or perylene tetracarboxylic acid diimide series containing at least one ionic water-solubilizing group and at least one aromatic radical linked on the one hand to the radical of an anthraquinone or perylene tetracarboxylic acid diimide dye via an oxygen or nitrogen atom and on the other hand to a b :g -dihydroxypropyl radical esterified in g -position with sulphuric acid or an organic sulphonic acid, via an oxygen or sulphur atom or an amino, sulphonamido or sulphone group.  Anthraquinone dyes include those of the benzanthrone, dibenzanthrone, isodibenzanthrone, pyranthrone, pyrazolanthrone, benzacridone, anthrapyridone and anthrapyrimidine series.  The dyes are made by reacting with sulphuric acid, chlorsulphuric acid, acid sulphates or pyrosulphates or an organic sulphonic acid, halide or anhydride, an appropriate dye containing a b :g -dihydroxypropyl or a b :g -epoxypropyl radical or a phenol or primary or secondary amine containing such radicals and then, in the latter case, reacting the amine or phenol with a dye containing a reactive chlorine or bromine atom, a sulphonic or carboxylic acid halide group or a carboxylic anhydride, carboxylic acid imide or dihalotriazinyl group.  The starting dyes containing a b :g -dihydroxypropyl or b :g -epoxypropyl radical are made by reacting an appropriate dye containing an aromatic radical attached via an oxygen or nitrogen atom and substituted by a sulphinic acid, sulphhydryl or acylatable hydroxy or amino group with glycidol or a 1-halo-2:3-dihydroxypropane, or with a halohydrin of glycerol or an epihalohydrin and converting the halohydrins to epoxy compounds from which the dihydroxy derivatives may be obtained.  The starting dyes may also be made by reacting dyes containing reactive halogen atoms, sulphonic acid or carboxylic acid halide, halomethyl, carboxylic acid anhydride, carboxylic acid imide or dihalotriazinyl groups with phenols or primary or secondary aromatic amines containing b :g -dihydroxy-propyl or b :g -epoxypropyl groups.  Examples are given. The dyes dye and print leather, wool, silk, polycaprolactams and adipic acid-hexamethylene diamine condensation products from an acid bath, and cellulose materials in conjunction with a treatment with an alkaline agent.