Patent GB-880403-A (GB)
Title: Aminotriazine compounds, their production and use
IPC: C08G12/42
Filed: 1959-09-21
Abstract: The invention comprises ethers of condensation-products of formaldehyde with aminotriazines containing at least 2 amino groups, said ethers being formed by reacting a condensation product of formaldehyde with an aminotriazine containing at least two amino groups, the condensation product containing, per amino group of the aminotriazine, at least one methylol group or one methylol group etherified with a saturated aliphatic alcohol containing from 1 to 4 carbon atoms, with sufficient of an alcohol of the general formula HO-R-O-CH2-CR1 = CH-R2 in which R represents an organic radical, especially an aliphatic, cycloaliphatic, or araliphatic radical, or such a radical containing halogen substituents and/or interrupted by oxygen atoms, and R1 and R2 each represent a hydrogen atom or a methyl group, that at least one alcohol radical of the formula -O-R-O-CH2-CR1 = CH-R2 is present in the ether formed to each amino group of the aminotriazine.  As starting materials are specified methylol melamines with 3 to 6 methylol groups, methylol derivatives of N-substituted melamines, melam, melem, ammeline, ammelide, halogen- or allyloxy-substituted melamines, guanamines, diguanamines, specific compounds being listed.  Etherifying groups may be derived from low molecular weight saturated or unsaturated alcohols (e.g. allyl and methallyl alcohols and 2-buten-1-ol).  The alcohols of formula I are dior polyalcohols in which a hydroxyl group has been etherified with allyl or methallyl alcohol or with 2-butene-1-ol. They may be derived from glycol, 1:2- or 1:3-propanediol, 1:2:4-butanetriol, glycerol, 1:3- or 1:4- butanediol, 1:5- pentanediol, 3-chlorohexane -1:2-diol, phenylglycol, -diol, n-hexane-2:5-diol, 2-ethylhexane -1:3-diol, 2:4:6-hexane-triol, 2:21-dioxy-di-n-propyl ether, di- and tri-ethylene glycols, 1-chlorobutane-2:4-diol, 3-chloropentane-1:4-diol, glycerin-a -or b -monochlorhydrin, 3-chlorobutane -1:2-diol, 2-bromobutane-1:3-diol, 1-chloropentane-2:5 diol, 1-chlorohexane -2:6-diol, 2-bromo-hexane-3:6-diol, 3-chlorohexane -1:2-diol, phenylglycol, polyalcohols obtained by hydrolysis of polyglycidyl ethers (from epichlorohydrin and a diphenol or of cyclo-aliphatic polyepoxy compounds such as 6:61-dimethyl-3:4-epoxy-hexahydrobenzyl-31: 41-epoxyhexahydrobenzoate.  The alcohols can also be obtained by reacting an epoxide, e.g. styrene oxide or alkylene oxides with allyl alcohol, methallyl alcohol or 2-butene-1-ol. The products can be used in coating compositions alone or with air drying oils such as linseed, dehydrated castor, soya, bean and wood oils, alkyd resins, nitrocellulose, acetylcellulose, thylcellulose, polyvinyl acetate, polyvinyl acetals and polystyrenes, or in combination with other compounds polymerizable by peroxides such as styrene, vinyl esters, acrylic acid esters, acrylonitrile and a , b -unsaturated polyesters. The products of the invention can be modified by reaction with such alcohols as glycol, stearyl, myricyl and linseed oil alcohols, and incompletely etherified or esterified glycerol or by condensation with a , b -unsaturated compounds containing a group with which they react.  A number of a , b -unsaturated monocarboxylic acids, and their esters, mono- and poly-esters of a , b -unsaturated dicarboxylic acids, or a , b -unsaturated dicarboxylic acids and their reaction products with amines are listed.  The condensation may be effected by heating, e.g. in the presence of hydroquinone. Mixtures of the unsaturated ethers with the a , b -unsaturated compounds can also be used.  Methylene blue and copper salts increase the pot-life.  Drying and hardening are accelerated by adding waxy substances, Co-, Mg-, Ca-, Pb-, Fe-, Ni-, Zn- or A1-palmitate, steorate or montanate; and organic peroxides such ar benzoyl, di-tert-butyl or lauryl peroxide or hydroxy cycloboxylhydroperoxide. In Example (1) hexamethylol-melamine hexamethyl ether is transetherified in the presence of phthalic anhydride with ethylene glycol monoalkyl ether to give a drying lacquer with the addition of co-octoate in toluene.  In other examples the etherifying compound is (2) triethylene glycol mono-alkyl ether; (4) glycerin chlorohydrin allyl ether; (5) the reaction product of 1 mol. each of allyl alcohol and the diglycidyl ether of bis-(4-hydroxyphenyl)-dimethylmethane; (12) propylene glycol monoallyl ether; (13) propylene glycol monomethallyl ether; (14) a styrene oxide/allyl alcohol reaction product; (15) a propylene oxide/2-buten-1-ol reaction product.  In Example (6) the product of (3) is mixed with an unsaturated ester (from fumaric acid, phthalic anhydride, glycol and benzyl alcohol), styrene, cobalt octoate, and tertiary butyl hydroperoxide to give a drying lacquer.  Similar examples relate to compositions (7) of the resin of (3), styrene and a maleic anhydride/adipic acid/glycol polyester; (8) ingredients as in (6) but with the polyester prepared from die-hylene glycol (9) the polyester used in (6) with the transetherification product of (3), styrene, methylethyl ketone hydroperoxide and combinations of cobalt, aluminium and zinc stearates.