Patent GB-961624-A (GB)
Title: Improvements in or relating to isocyanurate compounds
Filed: 1962-05-04
Abstract: N-(b -hydroxyethyl), N, N1-di(b -hydroxyethyl) and N, N1, N11-tri (b -hydroxyethyl) derivatives of isocyanuric acid are prepared by treating a salt of cyanuric acid, e.g. an alkali-metal cyanurate, with an ethylene halohydrin in water or in an organic solvent. The preferred solvents are liquid aliphatic acid dialkylamides, e.g. dimethyl- or diethyl-formamide or dimethylacetamide, or dialkyl sulphoxides, e.g. dimethyl sulphoxide.  Other solvents are also specified. Alternatively, the reaction may be effected by passing a solution of a cyanurate through a column of an anion-exchange resin, e.g. a polystyrene quaternary-amine type resin, and then passing a solution of an ethylene halohydrin through the column.  When only one or two b -hydroxyethyl groups are introduced into the isocyanurate ring, the remaining nitrogen atom or atoms may be alkylated or aralkylated, e.g. by treatment with methyl iodide, allyl or methallyl chloride, chloromethyl-alkyl ethers in which the alkyl group has 1-20 carbon atoms, alkyl chloracetates or benzyl chloride. This reaction is preferably effected simultaneously with the hydroxyethylation. Examples are given of the preparation of mono-, di- and tri-(b -hydroxyethyl) isocyanurate, monoallyl-di-(b -hydroxyethyl) isocyanurate and diallyl-mono-(b -hydroxyethyl) isocyanurate.  The products containing two or three b -hydroxyethyl groups, e.g. di- or tri-(b -hydroxyethyl) isocyanurate or monoallyl-di-(b -hydroxyethyl) isocyanurate, yield polyester condensation products by reaction with dicarboxylic acids, e.g. succinic, adipic, phthalic, terephthalic, sebacic, 1,4-naphthalene dicarboxylic, azelaic, glutaric or 3-ethylsebacic acid (see Division C3).ALSO:N-(b -hydroxyethyl), N,N1-di(b -hydroxyethyl) and N,N1,N11-tri(b -hydroxyethyl) derivatives of isocyanuric acid are prepared by treating a salt of cyanuric acid, e.g. an alkali-metal cyanurate, with an ethylene halohydrin in water or in an organic solvent (see Division C2). When only one or two b -hydroxyethyl groups are introduced into the isocyanurate ring, the remaining nitrogen atom or atoms may be alkylated or aralkylated, e.g. by treatment with methyl iodide, allyl or methallyl chloride, chloromethyl-alkyl ethers in which the alkyl group has 1-20 carbon atoms, alkyl chloracetates or benzyl chloride. This reaction is preferably effected simultaneously with the hydroxyethylation. Examples are given of the preparation of mono-, di- and tri-(b -hydroxyethyl) isocyanurate, monoallyl-di-(b -hydroxyethyl) isocyanurate and diallyl-mono-(b -hydroxyethyl) isocyanurate.  The products containing two or three b -hydroxyethyl groups, e.g. di- or tri-(b -hydroxyethyl) isocyanurate, or monoallyl-di-(b -hdroxyethyl) isocyanurate, yield polyester condensation products by reaction with dicarboxylic acids, e.g. succinic adipic, phthalic, terephthalic, sebacic, 1,4-naphthalene dicarboxylic, azelaic, glutaric or 3-ethylsebacic acid.  Polyester resins are also obtainable from mixtures of di- or tri-(b -hydroxyethyl) isocyanurate and other diols, e.g. ethylene glycol, propylene glycol, hexamethylene glycol, neopentyl glycol, diethylene glycol, decamethylene glycol or 2,2-dimethyl-1, 3-propane diol. Such of the products as contain allyl groups may be condensed to form thermoset polymers, optionally with the addition of another monomer, e.g. styrene or triallyl isocyanurate. Diallylmono-(b -hydroxyethyl) isocyanurate is useful as a chain-length regulator when used in varying amounts in a polyester-forming reaction. Examples are given of the preparation of resins from (a) tri-(b -hydroxyethyl) isocyanurate and phthalic anhydride and (b) monoallyl-di-(b -hydroxyethyl) isocyanurate and adipic acid; the latter resin can be cured after admixture with styrene and a minor proportion of tert.-butyl perbenzoate.