Patent GB-486519-A (GB)
Title: Manufacture of condensation products from aminotriazines
IPC: C08G12/42
Filed: 1936-10-28
Abstract: Condensation products are prepared by condensing an aminotriazine, a compound containing at least five carbon atoms and at least one alcoholic hydroxyl group, and an aldehyde or a substance yielding an aldehyde.  Reactants specified include, aminotriazines- 2 : 4 : 6-triamino-1 : 3 : 5-triazine (melamine), 2-amino-1 : 3 : 5-triazine, 2-amino-4-oxy-6-chloro-1 : 3 : 5-triazine, 2 - amino - 4 - oxy - 6 - phenyl - 1 : 3 : 5-triazine, 2 : 4-diamino-1 : 3 : 5-triazine, 2 : 4-diamino - 6 - p - oxyphenol - 1 : 3 : 5 - triazine, 2-methylamino-4-amino-6-chloro-1 : 3 : 5-triazine, 2 : 4-diamino-6-phenylamino-1 : 3 : 5-triazine, 2-amino-4 : 6-diphenylamino-1 : 3 : 5-triazine, 2 : 4 : 6-trimethylamino-1 : 3 : 5-triazine, 2 : 4 : 6-triphenylamino - 1 : 3 : 5 - triazine, 3 - amino-1 : 2 : 4-phentriazoxine, melam, melem and melone; alcoholsaliphatic, aromatic, hydroaromatic or heterocyclic alcohols which may also contain other substituents (such as aldehyde, keto, carbonyl or amino groups or halogen atoms) or substances which under reaction conditions are converted into alcohols (such as acetals, esters, and enolizable keto compounds) such as ethylbutanol, ethylhexanol, lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, mannitol, sorbitol, benzyl alcohol, terpineol, borneol, abietinol, wool fat alcohols, furfuryl alcohol, carbohydrates, glucose, cane sugar, trihexosane, dextrine, starches, gum arabic, gum tragacanth, ricinoleic acid, saccharic acid (or their esters), halogen alkyl alcohols, aminoalcohols, triethanolamine, glycerol monoethyl ether, glycerol diethyl, ether, cyclohexanone-glycerol, glycerol mono- or di-esters of fatty acids, and alkyd resins (glycerolphthalic acid, -sebacic acid or -adipic acid esters) containing free hydroxyl groups; aldehydesformaldehyde, paraformaldehyde, trioxymethylene, acetaldehyde, crotonaldehyde, acrolein, benzaldehyde or furfural. Further substances capable of reacting with an amino group or an alcohol group (such as acid chlorides or acid anhydrides) or with an aldehyde group (such as amines, aniline, amides, urea, thiourea, sulphamides or phenols) may be present during the reaction or caused to react with the condensation product.  Reactants containing other substituents (such as carboxyl, carbonyl, hydroxy or amino groups or halogen atoms) may be further reacted by virtue of the substituents with such substances as acid chlorides or anhydrides, alcoholates, salts of carboxylic acids, amines or amides.  The reactions may take place in any order, the use of all or part of the alcoholic component subsequent to the reaction between the aldehyde and azine being excluded and forming the subject-matter of Specification 486,577. The condensation products may be mixed with, condensed with, or made in the presence of artificial or natural resins, dyestuffs, fillers, softeners, dehydrating agents or waterproofing agents.  The products, which may be thermo-hardening or thermo-setting (the latter being convertible into the former by reaction with aldehyde), may be used in the manufacture of moulding powders, moulded articles, binding agents, for glueing wood, paper, textile fabrics, for the production of artificial cork, artificial wood, for brush cements, for fixing colouring materials, for the production of insecticides, for impregnating textile webs and forming laminated bodies therefrom, as lacquers and as addition to air-drying oils, for the manufacture of cast articles, and in the textile industry as finishes, non-creasing agents, for diminishing swelling capacity, as thickening, stiffening or softening agents, as agents for making fillers or finishes water-resistant and in the preparation or dyed or printed materials. In examples: (1) 2-amino-4 : 6-bis-phenylamino-1 : 3 : 5-triazine, paraformaldehyde and ethylbutanol are condensed in the presence of formic acid; (2) trimethylmelamine, paraformaldehyde and stearyl alcohol are condensed in the presence of ethyl alcohol and hydrochloric acid; (3) melamine is condensed with formaldehyde in the presence of mannitol, cane sugar or trihexosane and the product moulded; (4) melamine is condensed with formaldehyde in the presence of trihexosane and the product, mixed with ammonium sulphate, is dissolved in water and used as a glue in the preparation of plywood; (5) melamine is condensed with cane sugar in the presence of formaldehyde the product mixed with cellulose and ground to yield a moulding powder; (6) melamine is condensed with glucose in the presence of hydrochloric acid and the product condensed with formaldehyde to yield an aqueous solution that may be used as a thickening agent.  Specification 468,677 also is referred to.