Patent GB-687734-A (GB)
Title: Hardenable condensation products and a process of producing the same
IPC: C08G12/20
Filed: 1950-07-26
Abstract: Hardenable resinous condensation products are made by heating 1 molecular proportion of a diprimary alcohol free from groups capable of reacting with urea other than hydroxyl groups and 2 molecular proportions of urea at temperatures at which ammonia is evolved until an amount of ammonia is evolved which corresponds to the formation of about 40 to 70 per cent of the theoretically possible quantity of the diurethane, and reacting the resulting product with formaldehyde in amount, for example, of 1 to 3 mols. for each urethane group formed. Diprimary alcohols specified are ethylene glycol, propane diol-1.3, butane diol-1,4, pentane diol-1.5, hexane diol-1.6, diethylene glycol, triethylene glycol, tetraethylene glycol, dihydroxydibutyl ether, dihydroxydiethylsulphide and mixtures thereof.  In modifications, polyalcohols such as 1.2.4-butane triol may be added before or during fusion of the diprimary alcohols with urea, and alcohols such as butanol, and compounds capable of reacting with formaldehyde to form resins, e.g. phenols, ureas, melamine, cyanamide, dicyanodiamide or mixtures thereof, or amino or phenol-aldehyde condensation products may be added before or during the reaction of the diurethane product with formaldehyde. The alcohol(s) and urea are preferably fused under reduced pressure and at 130-200 DEG  C. and the melt while still hot is reacted with aqueous formaldehyde by heating under reflux.  The condensation may be effected in acid, alkaline or neutral medium. The products are soluble in water and low molecular weight aliphatic alcohols and ketones, and may be used with or without acid hardening agents, such as aluminium chloride, zinc chloride, ammonium nitrate or weak acids, as textile and dyeing assistants, adhesives or for producing moulded articles.  In examples: (1) the solution obtained by reacting 1.4-butane diol with urea and formaldehyde was suitable, after addition thereto of acid hardening agents, for crease-proofing textiles, impregnating paper, as a binding agent for floor coverings and for moulded articles; the solution prepared in example (1) was distilled to remove some water and formalin and heated with butanol in the presence of sulphuric acid; after neutralization with caustic soda, water was removed by distillation and the resulting solution was diluted with (2) butanol, toluene or other solvent to give a lacquer; (3) ethyl alcohol to give, after addition of acid hardeners, a solution for use as a water-stable and flexible finish for fabrics impregnated with synthetic materials; (4) the product obtained from reaction of 1.6-hexane diol with urea and formaldehyde was reacted with butanol; (5) the product of diethyleneglycol, urea and formaldehyde was suitable for preserving and embedding animals and plants for zoological and botanical purposes; (6) the product of (5) when reacted with butanol gave a solution suitable for pigment printing; (7) the fused product of urea and 1.4-butane diol was reacted with formaldehyde in the presence of caustic soda; (8) 1.4-butane diol and 1.2.4-butane-triol were reacted with urea and formaldehyde; (9) the product obtained by reacting 1.4-butane diol, urea and formaldehyde was reacted with a urea-formaldehyde resin to give a product suitable for crease-proofing and sizing textiles; resins from phenol, melamine or dicyanodiamide and formalin may be used instead of the ureaaldehyde resin; (10) the product of 1.4-butane diol and urea was reacted with formalin and urea to give a product suitable for use as a binder for floor coverings; melamine or dicyanodiamide may be used instead of the urea with the formaldehyde or initial stage condensation products from urea and formalin may be used instead of urea and formalin separately.