Patent GB-1063797-A (GB)
Title: Bis-oxazolyl-stilbene compounds and process for their manufacture
IPC: D06L4/657
Filed: 1964-11-02
Abstract: Bis-oxazolyl-stilbene compounds of the general formula <FORM:1063797/C4-C5/1> in which W represents a stilbene residue linked with the oxazole rings in positions 4 and 41, and A1 and A2 are alike or different and each represents a naphthalene or benzene nucleus, which may carry substituents, are used as optical brightening agents in combination with detergents, e.g. soaps, salts of sulphonate detergents, non-ionic detergents such as polyglycol ethers derived from ethylene oxide, and higher fatty alcohols, alkyl phenols or fatty amines. In an example (No. 39) cotton is washed in a detergent containing anhydrous sodium carbonate, sodium pyrophosphate, sodium perborate, magnesium silicate and a stilbene derivative of the above formulaALSO:The invention comprises bis-oxazolylstilbene compounds of the general formula <FORM:1063797/C2/1> in which W represents a stilbene residue linked with the oxazole rings in positions 4 and 41 and A1 and A2 are identical or different and each represents a naphthalene or benzene residue, which may be substituted, joined to the oxazole ring in the manner indicated.  Substituents on the naphthalene or benzene nucleus may be, for example, hydrocarbon groups, halogen atoms, carboxylic or carboxylic ester groups, acid chloride groups, acid amide groups (including those in which the nitrogen atom forms part of a heterocyclic ring), which may be N-substituted by hydrocarbon groups or hydroxy-alkyl groups, alkoxy groups, sulphonyl chloride groups, sulphonamido groups and sulphonic acid groups.  A preferred class of compounds are those of formula <FORM:1063797/C2/2> in which X1 and X3 are the same or different and each represents a hydrogen or halogen atom, an alkenyl or alkoxy group containing up to 6 carbon atoms, a saturated non-aromatic hydrocarbon residue containing up to 12 carbon atoms, an aryl or aralkyl radical or a residue of the formula -(alkylene)n- Y in which n is 0 or 1, the alkylene group contains 1-6 carbon atoms, and Y represents a free or etherified hydroxyl group, a free or neutralized carboxyl group or a functionally modified carboxylic group, at X2 and X4 are hydrogen, C1-C6 alkyl or C1-C4 alkoxy.  The new compounds may be prepared by one of the following methods: (a) by reacting a suitable o -hydroxyamino compound with a stilbene dicarboxylic acid or a functional derivative thereof, e.g. an acid chloride, in one or two stages in the presence of a catalyst such as boric acid and an organic solvent, if desired; (b) by heating a mixture of sulphur and a 2-(p-methylphenyl)-benzoxazole or -naphthoxazole; (c) by reacting an aldehyde of formula <FORM:1063797/C2/3> with a 2-(p-methylphenyl)-benzoxazole or naphthoxazole of formula <FORM:1063797/C2/4> the starting aldehydes in this method may be obtained by reacting a suitable derivative of the p-carboxyl benzaldehyde with an o -hydroxyamino compound or from a 2-(p-methylphenyl)-benzoxazole or -naphthoxazole by oxidation or by dihalogenation and subsequent hydrolysis; or (d) by treating a compound of formula <FORM:1063797/C2/5> with a dehydrogenating agent, e.g. sulphur or palladium and air; the starting material in this method may be obtained by condensing a dibenzyl -4,41-dicarboxylic acid dichloride with an o-hydroxyamino compound of the benzene or naphthalene series.  A large number of detailed examples is given. Acid chlorides used as starting materials in some of the examples may be obtained by converting the stilbene-4,41-dicarboxylic acid diethyl ester to the mono-carboxylic acid mono-ester, treating this with thionyl chloride to produce the mono-acid chloride; reacting this with an o -hydroxyamine of the benzene or naphthalene series to give a mono-oxazole compound, e.g. of formula <FORM:1063797/C2/6> which is hydrolysed to the acid and converted to the acid chloride by treatment with thionyl chloride.ALSO:Bis - oxazolyl - stilbene compounds of the general formula <FORM:1063797/C3/1> in which W is a stilbene residue linked with the oxazole rings in positions 4 and 41, and A1 and A2 are alike or different and each represents a naphthalene or benzene nucleus, which may be substituted, are used as optical brightening agents. They may be used, for example, in brightening alkyd resin lacquers, acrylic resin lacquers and cellulose ester lacquers, synthetic fibres, films, foils & c. made from cellulose esters, polyamides, polyesters, polyolefines and films, foils, tapes and mouldings made from polystyrene, polyvinylchloride, polyvinylidene chloride, polyvinyl alcohol and polyvinyl esters. Examples are given of the use of the stilbene derivatives in the brightening of (a) Nylon 66 and TiO2 in chip form (Ex. 33); (b) a polyester granulate from polyterephthalic acid ethylene glycol ester (Ex. 34); (c) polyvinyl chloride fibres (Ex. 35); (d) polyvinyl chloride foil (Ex. 36); (e) polyethylene foil (Ex. 37); and Nylon 6 and TiO2 in chip form (Ex. 38).ALSO:Bis-oxazolyl - stilbene compounds of the <F\1> in which W is a stilbene residue linked with the oxazole rings in position 4 and 4\sv, and A1 and A2 are alike or different and each represents a benzene or naphthalene residue which may carry substituents, are used as optical brightening agents for synthetic fibres, e.g. those made from polyamides such as nylon, polyesters and polyolefines, and also natural fibres such as cotton and wool. The fibres may be in the form of staple fibres, monofils, hanks or woven fabrics and are preferably treated in an aqueous medium in which the brightening agent in suspended.  The treatment may be carried out in the presence of a dispersant. Examples are given of the use of the stilbene derivatives in the treatment of (a) polyvinyl chloride fibres (Ex. 35), (b) cotton (Ex. 39) and (c) a bleached fabric from polyamide staple fibre (Ex. 40).