Patent GB-578196-A (GB)
Title: Improvements in and relating to synthetic resinous reaction products of aldehydes and triazine derivatives
IPC: C08G12/34
Filed: 1943-07-27
Abstract: Synthetic resinous condensation products are prepared by reacting under alkaline conditions an aldehyde and a -(diamino-s-triazinyl thioacetamido) - b  - (chloroacetamido) ethane.  The term aldehyde includes polymeric aldehydes and aldehyde addition products which yield aldehyde under the condition of the reaction.  Formaldehyde is preferred.  A list of other suitable aldehydes is given.  The reaction may be carried out at normal or elevated temperatures and at atmospheric, sub- or super-atmospheric pressure.  The condensation may be effected as described in Specification 569,413 in presence of a primary condensation catalyst which is preferably a nitrogen-containing basic material and a secondary condensation catalyst which is preferably a fixed alkali.  The reaction may be performed in presence of solvents, diluents, fillers or modifying reactants usual in this art.  The modifying reactants may be incorporated before, during or after the primary condensation in the general manner described in Specification 542,932. Thermoplastic products of the invention are valuable as plasticisers for other resins.  Thermosetting products may be mixed with dyes, pigments, plasticisers, mould lubricants, opacifiers and fillers such as wood flour, glass fibres, asbestos, mineral wool, mica, or cloth cuttings to form moulding compositions.  Liquid condensation products may be concentrated or diluted for use as coating compositions or casting resins.  The products have a wide variety of uses such as laminating varnishes, production of wire and baking enamels, for bonding mica, or abrasive grains, for making electrical resistors, for electrical insulation generally and for treating textiles.  Examples describe the alkaline condensation of the triazine derivative: (1) with formaldehyde under reflux, the product being mixed with a -cellulose and zinc stearate to form a moulding composition, chloracetamide being used as a curing catalyst; (2) with formaldehyde at room temperature, the product forming a flexible infusible sheet when bodied on a hot-plate at 140 DEG  C.; (3) with formaldehyde in presence of urea, a moulding powder being formed by mixing the product with a -cellulose and zinc stearate; (4) as in (3) with chloroacetamide present as a curing catalyst; (5) with formaldehyde in presence of urea to form an unfilled thermosetting resin; (6) with formaldehyde in presence of melamine, the product being mixed with the usual ingredients to form a moulding powder; (7) with formaldehyde in presence of dimethylol urea, the product being used for a moulding powder; (8) with formaldehyde in presence of trimethylol melamine, the product being used for a moulding powder; (9) with acrolein; (10) with furfural; (11) with formaldehyde in presence of butyl alcohol yielding a dehydrated syrup soluble in organic solvents such as dioxane, butyl alcohol, ethylene glycol, or ethylene glycol monoethyl ether to yield coating compositions; (12) with formaldehyde in presence of diethyl malonate; (13) with formaldehyde in presence of acetamide; (14) with formaldehyde in presence of glycerine; (15) with formaldehyde in presence of polyvinyl alcohol.  A list of curing catalysts which may be employed in place of chloroacetamide is given at the end of example (4).  a  - (Diamino - s - triazinyl thioacetamido) - b  - (chloroacetamido) ethane is prepared by reacting, in presence of aqueous or aqueous alcoholic sodium hydroxide, b  - (bis - chloroacetamido) ethane and thioammeline.  As open to inspection under Sect. 91 the Specification covers the use of triazine derivatives of the formula <FORM:0578196/IV/1> where n=1 or 2, Z=oxygen or sulphur, R=H, or a monovalent hydrocarbon or substituted hydrocarbon radical, R1= a divalent hydrocarbon or substituted hydrocarbon radical, and X = a halogen atom.  Long lists are given of radicals which R and R1 may represent and of triazine derivatives included in the scope of the invention.  The preparation of these starting materials is described in Application 2611/43 as open to public inspection.  It is stated that corresponding derivatives of asymmetrical triazines may be employed.  It is also stated that the reaction may be performed under neutral or acid conditions.  A list of acid materials which may be added to the reaction mixture is given.  Long lists of modifying reactants which may be present in the reaction mixture are also given, Specifications 542,934 and 1458/42 being referred to.  Many aldehydes and aldehyde addition products are also referred to as possible starting materials for the invention.  This subject-matter is not included in the Specification as accepted.