Patent GB-879957-A (GB)
Title: Improvements relating to the hardening of epoxides
Inventor: GARNISH EDWARD WILLIAM
IPC: C08G59/54
Filed: 1958-09-22
Abstract: A hardenable composition comprises an epoxide compound containing n-epoxide groups calculated on the average molecular weight of the epoxide compound, where n is a whole or a fractional number greater than 1, and as a hardener therefore at least one condensation product of a hydroxycarboxylic acid, a lactone thereof or an ester thereof with a monohydric aliphatic alcohol containing not more than 5 carbon atoms and a polyamine of the general formula H2N(CH2CH2NH)p-CH2CH2NH2\t wherein p is an integer.  Specified polyamines are diethylenetriamine, triethylentetramine and tetraethylenepentamine.  Specified hydroxycarboxylic acids are glycollic acid, b -hydroxy-butyric acid, #s-hydroxy-hexoic acid, gluconic acid, tartronic acid, malic acid, saccharic acid, citric acid, m-hydroxybenzoic acid, p-hydroxybenzoic acid, gallic acid, mandelic acid, 2, 3-hydroxynaphthoic acid, lactic acid, tartaric acid and salicyclic acid, which acids may be partially replaced by mono-carboxylic acids, e.g. acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, capric acid and 2-ethyl hexoic acid.  Many epoxides are specified, examples being butadiene dioxide, methyl-9, 10, 12, 13-diepoxy stearate, diethylene glycol bis-(3, 4-epoxy cyclohexane carboxylate), the reaction products of primary or secondary aliphatic or aromatic diamines with epichlorohydrin, polyglycidyl esters and polyglycidyl ethers.  The Specification describes the preparation of hardening agents from diethylene triamine and lactic acid, tartaric acid and a mixture of tartaric acid and acetic acid and triethylene tetramine and lactic acid, ethyl lactate, butyrolactone, salicylic acid, a mixture of salicylic acid and ethylhexoic acid, a mixture of malic acid and butyric acid, a mixture of butyric acid and salicylic acid, mandelic acid and p-hydroxybenzoic acid.  The examples describe the use of the above specified hardeners with bis-phenol-A-epichlorohydrin reaction products.ALSO:The Specification describes condensation products made by reacting a hydroxy carboxylic acid, a lactone thereof or an ester thereof with a monohydric aliphatic alcohol containing not more than five carbon atoms and a polyamine of the general formula H2N-(CH2CH2NH)p-CH2 -CH2NH2 where p is an integer.  Specified polyamines are diethylene triamine, triethylene tetramine and tetraethylene pentamine.  Specified hydroxycarboxylic acids are glycollic acid, b -hydroxybutyric acid, 6-hydroxyhexoic acid, gluconic acid, tartronic acid, malic acid, saccharic acid, citric acid, m-hydroxybenzoic acid, gallic acid, mandelic acid, 2,3-hydroxynaphthoic acid, lactic acid, tartaric acid and salicylic acid, which acids may be partially replaced by monocarboxylic acids e.g. acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, capric acid and 2-ethylhexoic acid.  The Specification describes the reaction between:- (I) diethylene triamine and lactic acid; (II) and (III) triethylene tetramine and lactic acid; (IV) methylene tetramine and ethyl lactate; (V) methylene tetramine and butyrolactone; (VI) and (VII) triethylene tetramine and salicylic acid; (VIII) triethylene tetramine, salicylic acid and acetic acid; (IX) and (X) triethylene tetramine, salicylic acid and mixed fatty acids; (XI) triethylene tetramine, salicylic acid and 2-ethylhexoic acid; (XII) diethylene triamine, tartaric acid and acetic acid; (XIII) triethylene tetramine, malic acid and butyric acid; (XIV) methylene tetramine, salicylic acid and butyric acid; (XV) triethylene tetramine and p-hydroxybenzoic acid and (XVI) triethylene tetramine and mandelic acid.