Patent GB-570956-A (GB)
Title: Improvements in and relating to resinous condensation products
IPC: C08G12/04
Filed: 1943-02-16
Abstract: Resinous condensation products are prepared by intercondensing with an acid curing thermosetting resin a divalent hydrocarbon derivative of the general formula <FORM:0570956/IV/1> (where X = chlorine or bromine and R = -CH2CH2- or -CH2CH2CH2-) or an aldehyde reaction product of such a derivative.  The hydrocarbon derivatives may be prepared by reacting chlor- or brom-acetyl chloride with ethylene diamine or trimethylene diamine.  Acid curing thermosetting resins are defined as partial condensation products formed under alkaline conditions of an aldehyde and a phenol, cresol, xylenol or an aldehyde reactable amino or amido compound such as melamine, guanazole, 2,4,6-triamino-pyramidine, aniline, acid amides, urea, thiourea or dicyandiamide.  The term an aldehyde includes polymeric aldehydes, hydroxy aldehydes and aldehyde addition products which yield aldehyde under the conditions of reaction.  A list of examples is given.  The hydrocarbon derivative or a water-soluble fusible aldehyde reaction product thereof may be added to an acid-curing thermosetting resin, or the hydrocarbon derivative may be added to the ingredients of the acidcuring thermosetting resin.  The resin syrups of this invention have good storage stability.  They may be converted to moulding powders which cure rapidly under heat or heat and pressure, but which have good storage stability.  Condensation between the reactants is carried out under alkaline conditions at normal or elevated temperatures up to the reflux temperature of the reactants and at reduced, atmospheric, or superatmospheric pressures. Examples describe the preparation of moulding compounds by refluxing ingredients under alkaline conditions, adding a ,b -bis-(chloroacetamido)-ethane, continuing the refluxing, mixing the resulting resinous syrup with a -cellulose and zinc stearate and drying and grinding the mixture.  The ingredients were as follows: (1) urea and formaldehyde; (2) melamine and formaldehyde; (3) melamine, thiourea and formaldehyde; (4) dimethylol urea and a ,b -bis-(diamino triazinyl thio-acetamido)-ethane; (6) phenol and formaldehyde.  In example (5) 1-phenyl guanazole, formaldehyde and a ,b -bis-(chloracetamido)-ethane were heated together in an open vessel under alkaline conditions and a moulding powder prepared from the product.  Examples (7), (8) describe the preparation of formaldehyde condensation products of a ,b -bis-(chloroacetamido)-ethane which may be used as curing catalysts in place of the a ,b -bis-(chloroacetamido)-ethane itself.  The proportion of aldehyde to hydrocarbon derivatives may vary widely. Generally, more aldehyde addition product is needed than simple aldehyde.  Similarly, more of the aldehyde reaction product of the hydrocarbon derivative is needed as a curing catalyst than of the hydrocarbon derivative itself. Specifications 564,576 and 570,520 are referred to.  According to the Specification as open to inspection under Sect. 91, the hydrocarbon derivative may be of the general formula <FORM:0570956/IV/2> where n is 1 or 2, Z = O or S, R = H or a monvalent hydrocarbon or substituted hydrocarbon radical, R1 = a divalent hydrocarbon or subsituted hydrocarbon radical and X = a halogen atom.  The reaction may be performed under neutral or acidic conditions, and some aldehyde addition products are mentioned which are not included in the Specification as accepted.  In this connection, reference is made to Specification 1458/42, as open to inspection under Sect. 91.  An example is included of the preparation of a resin from soya bean protein, 4,6-diamino-pyrimidyl-2-p-sulphamyl-phenyl-carbamyl-methyl sulphide, and formaldehyde in alkaline solution. a -b -bis-(chloroacetamido)-ethane is added as a curing catalyst. A moulding powder is prepared from the product by addition of a -cellulose and zinc stearate, drying and grinding.