Patent GB-596309-A (GB)
Title: Improvements in synthetic resinous reaction products of an aldehyde and a triazine derivative
IPC: C08G12/32
Filed: 1945-01-17
Abstract: Synthetic resinous compounds are prepared by reacting an aldehyde with 2,4,6-tri-(parasulphonamidophenylaminomethyl) melamine under alkaline conditions.  The melamine may be prepared by reacting symmetrical trimethylol melamine with sulphanilamide and the preferred aldehyde is formaldehyde, but other aldehydes, such as acetaldehyde, propionaldehyde, butyraldehyde, heptaldehyde, octaldehyde, acrolein, methacrolein, crotonaldehyde, benzaldehyde, furfural, hydroxyaldehydes and mixtures thereof or mixtures with formaldehyde may be employed.  Modifying agents, such as monohydric alcohols and polyhydric alcohols, dyes, pigments, plasticisers, mould lubricants, opacifiers and fillers such as wood flour, glass fibres, asbestos, mineral wool, mica and cloth cuttings may be incorporated. A curing catalyst may be added to the potentially heat-curable syrup, which may be mono-, di- or tri-chloroacetamide, chloracetonitriles, a - or b -dichloropropionamide, a - or b -dibromopropionitrile, aminoacetamide hydrochloride, aminoacetonitrile hydrochloride, ethylene diamine monohydrochloride, diethanolamine hydrochloride, nitro urea, chloroacetyl urea, chloroacetone, glycine, sulphamic acid, citric diamide or phenacyl chloride, or a direct catalyst such as citric acid, phthalic anhydride, malonic acid or oxalic acid or a latent curing catalyst such as sodium chloracetate and glycine ethyl ester hydrochloride may be added.  In the examples, a resinous condensation product is prepared from tri-(para-sulphonamidophenylaminomethyl) melamine and (2) aqueous formaldehyde; (3) urea and aqueous formaldehyde; (4) melamine and aqueous formaldehyde; (5) furfural; (6) acrolein; (7) butyl alcohol and aqueous formaldehyde; (8) acetamide and aqueous formaldehyde; (9) diethyl malonate and aqueous formaldehyde; (10) glycerine and aqueous formaldehyde; and (11) polyvinyl alcohol and aqueous formaldehyde. In the Specification as open to inspection under Sect. 91, synthetic materials are prepared by effecting reaction between ingredients including an aldehyde and a compound corresponding to the general formula <FORM:0596309/IV/1> where n represents an integer which is at least 1 but not more than 3, Z represents a divalent aromatic radical, and R represents hydrogen or a monovalent hydrocarbon radical.  The radical Z may be divalent aromatic, such as phenylene, xenylene or naphthylene, divalent aliphaticsubstituted aromatic, such as 2,4-tolylene, ethyl 2,5-phenylene, alkyl 2,5-phenylene, isopropyl 3,4-phenylene, 1-butyl 2,4-naphthylene and their homologues, divalent aromatic with one or more hydrogen atoms in the aromatic nucleus replaced by substituents other than hydrocarbon radicals such as acyl, hydroxy, alkoxy, aryloxy, carboalkoxy, amino, halogeno and substituted sulphonamido, specific examples of the radical Z being chlorophenylene, bromphenylene, chloroxenylene, chloronaphthylene, chlorotolylene, bromotolylene, ethoxyphenylene, acetophenylene, carbomethoxyphenylene, acetoxyphenylene, aminophenylene, hydroxyphenylene, phenoxyphenylene, methylphenylene and alkylphenylene, but preferably, Z is phenylene or tolylene.  The radical R may be aliphatic such as methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, butenyl, pentyl, isopentyl, hexyl, octyl, allyl or methallyl and including cyclo-aliphatic such as cyclopentyl, cyclopentenyl, cyclohexenyl or cycloheptyl, aryl such as phenyl, diphenyl or xenyl, aliphatic substituted aryl such as tolyl, xylyl, ethylphenyl, allylphenyl, 2-butenylphenyl, propylphenyl or isopropylphenyl and aryl-substituted aliphatic, such as benzyl, phenylethyl, phenylpropyl or cinnamyl, but preferably R is hydrogen. The triazine derivative may be para-sulphamylphenylaminomethyl melamine, di - (para - sul - phamylphenylaminomethyl) melamine, mono-, di- or tri-(ortho-sulphamylphenylaminomethyl) melamine, mono-, di- or tri-(meta-sulphamylphenylaminomethyl) melamine, mono-, di- or tri - [para - (phenylsulphanyl) phenylamino - methyl] melamine, mono-, di- or tri-[para(methylsulphamyl) phenylaminomethyl] melamine, mono-, di- or tri-[ortho-(ethylsulphamyl) phenylaminomethyl] melamine, mono-, di- or tri-(sulphamylnaphthylaminomethyl) melamine, mono-, di- or tri-(sulphamyltolylaminomethyl) melamine, mono-, di- or tri - [sulphamyl - (dimethyl) - phenylaminomethyl] melamine, mono-, di- or tri-[sulphamyl (ethyl) phenylaminomethyl] melamine, mono-, di- or tri-[sulphamyl (propyl) phenylaminomethyl] melamine, mono-, di- or tri-(methylsulphamylnaphthylaminomethyl) melamine, mono-, di- or tri-(cyclohexyl-sulphamyl tolylaminomethyl) melamine, mono-, di- and tri-[sulphamyl-(chloro) - phenylaminomethyl] melamine or mono-, di- or tri - [sulphamyl - (methoxy) - phenylaminomethyl] melamine.  Other materials which can react with the aldehyde or triazine derivative may be present, such as urea, thiourea, melamine, ammeline, phenol, cresol or butyl alcohol.  This subject-matter does not appear in the Specification as accepted.  Specifications 554,195 and 565,059 are referred to.