Patent GB-1022756-A (GB)
Title: Substituted benzoyl chlorides and textile auxiliaries prepared therefrom
Inventor: FEEMAN JAMES F
IPC: C09B43/00
Filed: 1963-07-01
Abstract: Fibre-reactive dyes have the formula <FORM:1022756/C4-C5/1> wherein R is H, Me or Et and Z is in the n- or p-position and is <FORM:1022756/C4-C5/2> A being a dye attached through a functional group from which H has been displaced and B being the residue of a dye capable of forming a heterocyclic system upon condensation with a carbonyl chloride. The dyes are made by reacting compounds of the above formula in which Z is -COCl with dyes providing the residues A or B.  In examples, products have the following formulae <FORM:1022756/C4-C5/3> or are prepared by reacting the chloroethyl-sulphonylbenzoyl chloride with the copper complex of 2 - amino - 1 - phenol - 4 - sulphonic acid --> 6 - amino - 1 - naphtol - 3 - sulphonic acid, with a 3-nitro-4-chlorobenzenesulphonic acid/p-phenylenediamine condensate or with compounds of formulae <FORM:1022756/C4-C5/4> The acid chloride starting material may be reacted successively with two different dyes; a specified product is the copper complex of the compound of formula <FORM:1022756/C4-C5/5>ALSO:The invention comprises m- and p-compounds of formula <FORM:1022756/C2/1> wherein R is H, Me or Et.  In examples, the (m- and p-) 2-hydroxyethylmercaptobenzoic acids are respectively obtained from the mercaptobenzoic acids with ethylene chlorohydrin and oxidized with NaClO to the 2-hydroxyethylsulphonylbenzoic acids (a) which are reacted with thionyl chloride to give the 2-chloroethylsulphonylbenzoyl chlorides; the intermediates (a) are alternatively obtained by reacting sodium sulphonylbenzoic acids (from the reduction of chlorosulphonylbenzoic acids) with ethylene oxide or chlorohydrin and it is also stated that they may be converted to the 2-chloroethylsulphonylbenzoic acids with conc. HCl.  The compounds of the invention may be reacted with textile auxiliaries to replace the chlorocarbonyl groups by <FORM:1022756/C2/2> In examples, A is attached by NH derived from NH2 in 7-amino-1-naphthol-3-sulphonic acid, the 5-NH2 in 2,5-diaminobenzenesulphonic acid or NH2 in the optical brightener of formula <FORM:1022756/C2/3> while B is attached by <FORM:1022756/C2/4> derived from the two NH2 groups in 5,6-diamino-1-naphthol-3-sulphonic acid.ALSO:Textiles are dyed by a process in which azo-dyes are formed on the material, wherein a m- or pcompound of formula <FORM:1022756/D1-D2/1> in which R is H, Me or Et and A is the residue of an azo-dye intermediate, is reacted with the fibre to eliminate HCl and the dye developed with a suitable coupling agent.  In example 4, the fibre-reactive compound has the formula <FORM:1022756/D1-D2/2> and after impregnating spun rayon, it is developed with diazonium salts of metanilic acid, 4-methoxymetanilic acid or 5-amino-6-methoxynaphthalene-2-sulphonic acid.  In example 8, the fibre-reactive compound has the formula <FORM:1022756/D1-D2/3> and after impregnating spun rayon it is diazotised and coupled with barbituric acid, 3-methyl-1-p-sulphophenyl-2-pyrazol-5-one, resorcinol, 3-hydroxy-2-naphthanilide, 6-amino-1-naphthol-3-sulphonic acid or 8-amino-1-naphthol-3, 6-disulphonic acid.  <FORM:1022756/D1-D2/4> in which the NH2 is substituted by a p-2-chloroethylsulphonylbenzoyl group reacts ink cellulosic fibres such as cotton and viscose rayon, imparting optical brightness thereto.