Patent GB-1011553-A (GB)
Title: Water-soluble epoxy-containing prepolymers and method for preparing them
IPC: C07D303/42
Filed: 1962-08-17
Abstract: Aqueous coating compositions comprise a fatty compound containing at least one epoxy ring and containing aliphatic hydrocarbon radicals having 10-22 carbon atoms substituted at least once and not more than four times along said radicals on adjacent carbon atoms with ester groups and hydroxy groups, so as to contain the structure <FORM:1011553/C4-C5/1> , where X is an unsubstituted or substituted C1-C10 aliphatic or alicyclic hydrocarbon radical or an unsubstituted or substituted phenylene or benzenoid radical, said radical containing one or more carboxyl groups which have been reacted with ammonia or an amino compound boiling at not more than 175 DEG  C. (see Division C2).  Colouring agents and other inert materials may be present.ALSO:The invention comprises water-soluble prepolymer compositions comprising a fatty compound containing at least one epoxy ring and containing aliphatic hydrocarbon radicals having 10-22 carbon atoms substituted at least once and not more than four times along said radicals on adjacent carbon atoms with ester groups and hydroxy groups, so as to contain the structure <FORM:1011553/C2/1> where X is an unsubstituted or substituted C1- 10 aliphatic or alicyclic hydrocarbon radical or an unsubstituted or substituted phenylene or benzenoid radical, said radical containing one or more carboxyl groups which have been reacted with ammonia or an amino compound boiling at not more than 175 DEG  C.; and their production by reacting a suitable compound containing more than one epoxy ring with a dibasic or polybasic carboxylic acid (or anhydride thereof together with water) until one carboxyl group has reacted with an epoxy ring, but leaving at least one epoxy group and at least one carboxyl group unreacted; and adding ammonia or an amino compound boiling at not more than 175 DEG  C.  Solvents may be employed. Suitable oxirane compounds are acids, esters (including glycerides), alcohols, amides, hydrazides and ketones, and many reactants are specified. Suitable carboxyl-group supplying agents specified are malonic, adipic, maleic, fumaric, citric, tartaric, aconitic, itaconic, phthalic, isophthalic, terephthalic, prehnitic, mellophanic, trimesic, mellitic, hemimellitic, trimellitic and pyromellitic acids, and maleic, phthalic, tetrachlorophthalic, tetrahydrophthalic, 1,3 - cyclopentanedicarboxylic, citraconic, pyromellitic, trimellitic, 1,4,5,6, 7, 7-hexachlorobicyclo(2,2,1) - 5 - heptene - 2,3 - dicarboxylic, endo - cis - bicyclo(2,2,1) - 5 - heptene - 2,3 - dicarboxylic and chlorendic anhydrides. Specified amines are trimethylamine, triethylamine, tripropylamine, trimethylenediamine, morpholine, N-methylmorpholine, and dimethylaniline.  Examples employ epoxidized linseed oil, together with: (1) fumaric acid and ammonia; (2) maleic acid and ammonia; (3) maleic acid and morpholine; (4) tartaric acid and morpholine; (5) pyromellitic acid and ammonia; (6) trimellitic anhydride, water and ammonia; and (7) citric acid and ammonia.  Monoepoxy compounds may be present in the reaction.  The products form coatings (see Division B2).ALSO:Aqueous coating compositions comprise a fatty compound containing at least one epoxy ring and containing aliphatic hydrocarbon radicals having 10-22 carbon atoms substituted at least once and not more than four times along said radicals on adjacent carbon atoms with ester groups and hydroxy groups, so as to contain the structure <FORM:1011553/B1-B2/1> where X is an unsubstituted or substituted C1-10 aliphatic or alicyclic hydrocarbon radical or an unsubstituted or substituted phenylene or benzenoid radical, said radical containing one or more carboxyl groups which have been reacted with ammonia or an amino compound boiling at not more than 175  DEG C. (see Division C2).  Colouring agents and other inert materials may be present.  The compositions may be applied to fibres, films, sheets, pieces or granules by spraying, dipping, roller-coating or brush-coating, and are cured by heat and/or cure accelerators. Metals and glass are specified as substrates.