Patent GB-953422-A (GB)
Title: Improvements in or relating to the preparation of prepolymers from epoxidized fatty acid esters
Inventor: FINDLEY THOMAS WAGNER
IPC: C08G59/34
Filed: 1961-05-03
Abstract: A prepolymer is produced by heating at a temperature of 25-120 DEG C. an epoxidized fatty acid ester having an oxirane content above 6% with a poly primary or secondary amino compound having at least one carbon between nitrogen, until the reaction products are soluble in dilute aqueous acid, and are not yet substantially cross-linked.  The reaction may be halted by quick cooling in an ice or cold water bath. A suitable catalyst for the reaction is sodium methoxide.  Suitable epoxides are epoxidized soybean, linseed, rapeseed or safflower oil. Epoxidized perilla, menhaden, seal, sardine and herring oils are also mentioned, and epoxidized esters of unsaturated fatty acids with monohydric alcohols, glycols, triols, tetritols or pentitols. Suitable polyamines are ethylene diamine; 1,2- or 1,3-diaminopropane; 1,2-butylene diamine; diethylene triamine; triethylene tetramine; tetraethylene pentamine; pentamethylene diamine; hexamethylene diamine; 3,31-iminobis propylamine; 3-methylaminopropylamine 3-isopropylamino propylamine; 3,31-methylimino-bis-propylamine; piperazine; guanidine; 1,8-diamino menthane; N-b -aminoethylethanolamine; N-(2-hydroxypropyl)-ethylene diamine; N,N1-bis-2 hydroxypropylethylene diamine; o, m, and p-phenylenediamine; o-tolidine; diphenyl guanidine; phenyl biguanide; o-tolyl biguanide; thiourea.  In Example (1) epoxidized linseed oil was heated at 80 DEG C. for four hours with tetraethylene pentamine. A number of other generally similar examples are given in the Specification.  Specification 939,689 is referred to.ALSO:A prepolymer is produced by heating at a temperature of 25-120 DEG C. an epoxidized fatty acid ester having an oxirane content above 6% with a primary or secondary amino compound having at least one carbon between nitrogens, until the reaction products are soluble in dilute aqueous acid, and are not yet substantially crosslinked. The reaction may be halted by quick cooling in an ice or cold water bath.  A suitable catalyst for the reaction is sodium methoxide.  Suitable epoxides are epoxidized soybean, linseed, rapeseed or safflower oil. Epoxidized perilla, menhaden, seal, sardine and herring oils are also mentioned, and epoxidized esters of unsaturated fatty acids with monohydric alcohols, glycols, triols, tetritols or pentitols. Suitable polyamines are ethylene diamine; 1,2- or 1,3-diaminopropane; 1,2-butylene diamine; diethylene triamine; triethylene tetramine; tetraethylene pentamine; pentamethylene diamine; hexamethylene diamine; 3,31-iminobis propylamine; 3-methylaminopropylamine; 3-isopropylamino propylamine;3, 31-methylimino-bis-propylamine piperazine; guanidine; 1, 8-diamino menthane; N-b -aminoethylethanolamine; N-(2-hydroxypropyl)- ethylene diamine; N,N1-bis-2-hydroxypropyl-ethylene diamine; o, m, and p-phenylenediamine; o-tolidine; diphenyl guanidine; phenyl biguamide; o-tolyl biguamide; thiourea.  Dilute aqueous acid solutions of the prepolymers may be applied to substrata and cured by heating to form resin coatings. The prepolymers may also be used as solutions in alcohols, ketones, ethers or aromatic hydrocarbons.  In Example (1) Epoxidized linseed oil was heated at 80 DEG C. for four hours with tetraethylene pentamine.  A solution of the product in 1% acetic acid deposited on glass and heated gave a hard film.  A number of other generally similar examples are given in the Specification. Specification 939,689 is referred to.