Patent GB-570569-A (GB)
Title: Resinous condensation products prepared from aldehydes and diazine derivatives
IPC: C08G12/28
Filed: 1942-12-21
Abstract: Resinous condensation products are prepared by reacting together under alkaline conditions an aldehyde and a diamino pyrimidyl hydroxyphenyl carbamyl alkyl sulphide of the general formula <FORM:0570569/IV/1> wherein n = 1 or 2, R = H or methyl and the hydroxyl group may be in the ortho or para position in the benzene nucleus.  The term aldehyde is defined as including polymeric aldehydes and aldehyde addition products which yield aldehyde under the conditions of the reaction.  Formaldehyde is prepared.  A list of other suitable materials is given.  The condensation may be carried out at normal or elevated temperature and at atmospheric, sub- or super-atmospheric pressures.  A list of substance suitable for making the reaction medium alkaline is given.  If desired, two substances may be employed, one a nitrogen containing boric compound and the other a fixed alkali.  Solvents, diluents, fillers, other natural or synthetic resinous bodies or other modifying bodies may be added to the reaction mixture before, during or after the condensation.  A list of suitable modifiers is given.  These bodies may be incorporated by any of the methods described in Specification 554,195.  In the examples, the following ingredients are condensed together in alkaline solution to form resins: (1) 4-6-diamino pyrimidyl-2 parahydroxyphenyl carbamyl methyl sulphide and formaldehyde; (2) 4-6-diamino pyrimidyl - 2 ortho-hydroxyphenyl carbamyl-methyl sulphide and formaldehyde; (3) 4,6-diamino pyrimidyl-2 ortho-hydroxyphenyl carbamyl methyl sulphide, urea, formaldehyde and chloroacetamide; (4) 4,6-diamino pyrimidyl-2 para-hydroxyphenyl carbamyl methyl sulphide, melamine and formaldehyde; (5) 4,6-diamino pyrimidyl-2 ortho hydroxyphenyl carbamyl methyl sulphide sulphanilanide and formaldehyde; (6) 4,6-diamino pyrimidyl-2 para-hydroxyphenyl-carbamyl-methyl sulphide, dimethylol urea and chloroacetamide; (7) 4,6-diamino-pyrimidyl-2-ortho - hydroxyphenyl - carbamyl - methyl sul - phide and trimethylol melamine; (8) 4,6-diamino pyrimidyl - 2 para - hydroxyphenyl - carbamyl-methyl sulphide, 1-carbamyl guanazole and formaldehyde; (9) 4,6 - diamino pyrimidyl - 2 ortho - hydroxyphenyl - carbamyl - methyl sulphide and furfural; (10) 4,6-diaminopyrimidyl - 2 para - hydroxyphenyl - carbamyl - methyl sulphide and acrolein; (11) 4,6-diaminopyrimidyl - 2 ortho - hydroxyphenyl - carbamyl - methyl sulphide, butyl alcohol and formaldehyde; (12) 4,6-diamino pyrimidyl-2 parahydroxyphenyl - carbamyl - methyl sulphide, acetamide and formaldehyde; (13) 4,6-diamino pyrimidyl - 2 ortho - hydroxyphenyl - carbamyl - methyl sulphide glycerine and formaldehyde; (14) 4,6-diamino pyrimidyl-2 ortho-hydroxyphenyl - carbamyl - methyl sulphide, diethyl malonate and formaldehyde; (15) 4,6-diaminopyrimidyl - 2 para - hydroxyphenyl - carbamyl - methyl sulphide, polyvinyl alcohol and formaldehyde; (16) 4,6-diamino pyrimidyl-2 parahydroxyphenyl-carbamyl-methyl sulphide and formaldehyde. Where chloroacetamide is not present at the beginning of the reaction, it, or some other curing catalyst, may be added to the partial condensation product.  Most of the examples show this feature and example (1) includes a list of materials suitable for use as curing catalysts.  Many of the examples describe the manufacture of moulding powders by impregnating a -cellulose in flock form with the partial condensation product mixed with a curing catalyst adding zinc stearate and drying and guiding the product.  Others describe the formation of films by heating the intermediate condensation products on a hot plate at 140 DEG  C.  The resins may be used as modifiers of other natural and synthetic resins, for coating or impregnating compositions, for electrical insulation, for bonding abrasive particles or mica.  Dyes, pigments, plasticizers, mould lithuates, opacifins, and fillers may be compounded with the resins in the usual manner.  The preparation of the diazine derivatives used in the examples from 2-mercapto, 4,6-diamino pyrimidine and o- or p-chloroacetamido phenol in alkaline solution is described. 2,6-Diamino pyrimidyl - 4 - para - hydroxyphenyl - carbamyl - methyl sulphide; 4,6-dimethylamino pyrimidyl-2 - para - hydroxyphenyl - carbamyl - methyl sul - phide and 4,6-diamino pyrimidyl-2-a  or b -(parahydroxyphenyl - carbamyl) ethyl sulphide are similarly prepared from appropriate starting materials.  Specifications 542,932, 569,413 and 9244/41 and 10917/41 (as open to inspection under Sect. 91) are referred to.  The Specification as open to inspection under Sect. 91 mentions many other diazine derivatives, many other aldehydes and many other modifying bodies as suitable starting materials and is not limited to a reaction performed under alkaline conditions.  It refers to Specification 1458/42 which is open to inspection. This subject-matter does not appear in the Specification as accepted.