Patent GB-569413-A (GB)
Title: Resinous condensation products prepared from aldehydes and triazine derivatives
IPC: C08G12/34
Filed: 1942-12-14
Abstract: Resinous condensation products are produced by reacting together under alkaline conditions an aldehyde or an aldehyde addition product which produces aldehyde under the conditions of the reaction and a diamino s-triazinyl hydroxy-carbocyclic-carbamyl methyl or ethyl sulphide corresponding to the general formula <FORM:0569413/IV/1> wherein n = 1 or 2, Y = phenylene or tolylene and R represents H or a methyl or ethyl radical.  Suitable aldehydes or equivalent materials mentioned are formaldehyde or its homologues, methacrolein, crotonaldehyde, benzaldehyde, furfural, glycollic aldehyde, glyceraldehyde and the mono- and poly-N-methylol derivatives of urea, thiourea, melamine, aminotriazoles, aminodiazines, or mixtures thereof.  The alkaline reaction conditions may be produced by addition of any alkali.  If desired, ammonia or an amine may be added to produce the basic reaction conditions and a smaller quantity of a fixed alkali to neutralize formic acid present in the aldehyde. Solvents, fillers, diluents or modifying reactants may be added in the well-known manner. Some suitable materials are listed in the Specification.  The ingredients of the reaction mixture may be mixed in the manner described in Specification 554,195.  The resinous products may be compounded in the usual way with dyes, fillers, plasticizers, mould lubricants, pigments, curing agents or similar materials. In examples: (1) 4,6 - diamino - s - triazinyl - 2 - parahydroxyphenyl carbamyl methyl sulphide is condensed by refluxing in presence of alkali with formaldehyde, melamine and formaldehyde or dimethylol urea to produce products which after addition of monochloroacetamide as curing catalyst may be used to impregnate fillers such as a -cellulose in flock form to produce, after addition of mould lubricants, such as zinc stearate, moulding compositions; (2) similar moulding compositions are produced from condensation products of 4 - 6 - diamino - s - triazinyl - 2 -orthohydroxyphenyl-carbamyl-methyl sulphide with formaldehyde, urea and formaldehyde, sulphanilamide and formaldehyde, or trimethylolmelamine.  Instead of chloroacetamide, other curing agents may be used, e.g. any of the bodies mentioned in Specifications 9244/41 and 10917/41, as open to inspection under Sect. 91; (3) 4,6 - diamino - s - triazinyl - 2 - orthohydroxyphenyl carbamyl methyl sulphide is condensed by refluxing under alkaline conditions with furfural, acrolein, or acetamide and formaldehyde, to yield syrups which set when heated to 140 DEG  C. on a hot-plate and which cure rapidly when similarly heated with a curing agent.  A similar product is obtained from the corresponding parahydroxy body and furfural; (4) 4,6-diamino - s - triazinyl - 2 - parahydroxyphenyl - carbamyl-methyl sulphide condensed with butyl alcohol and formaldehyde or with glycerine and formaldehyde yields products which on dehydration are soluble in solvents such as ethyl alcohol, glycol, benzyl alcohol, or dioxane and which applied to a glass plate and baked yield, specially in presence of curing agents, hard, durable films; (5) 4,6-diamino-s-triazinylorthohydroxyphenyl carbamyl methyl sulphide yields a soft thermoplastic resin when condensed with diethyl malonate and formaldehyde, and a product suitable for drawing into fibres or for forming hard, smooth, water-resistant films when condensed with polyvinyl alcohol and formaldehyde.  The products of the invention may be used for moulding compositions, in the manufacture of laminated materials, enamels, resin-bonded abrasive articles or for bonding together mica flakes.  They may also be employed for treating textiles, as impregnants for electrical coils and for other electrically-insulating uses.  The Specification as open to inspection under Sect. 91 covers the use of many derivatives of the substituted triazines mentioned above, or of their sulphur analogues, and mentions and gives lists of other suitable aldehyde addition products and of other modifying reactants which may be used in the reaction.  In connection with the list of aldehydic materials, it contains a reference to Specification 1458/42 as open to inspection under Sect. 91, and in connection with the list of modifying agents to Specifications 542,932 and 8941/42 as open to inspection under Sect. 91.  It also contemplates the carrying out of the reaction under acid conditions.  This subject-matter does not appear in the Specification as accepted.