Patent GB-1016835-A (GB)
Title: Diene-adducts and process for their manufacture
Inventor: BRACHEL HANSWILLI VON
IPC: C08G69/26
Filed: 1963-12-18
Abstract: Di- and polycarboxylic acids (obtainable by adding acrylic acid to sorbic acid esters of glycols, polyalcohols or their oxalkylation products, polymethylene glycols, polyethylene-polypropylene- and polybutylene-glycol ethers) may be reacted with di- and polyisocyanates to give soluble and cross-linked polyamides, with di- and polyepoxides to yield soluble and cross-linked polyesters, and with ureas and urethanes of ethyleneimine containing at least 2 ethyleneimine groups to give polyurea-polyesters or polyurethane-polyesters.  Di- and polycarboxylic acid amides (obtained by addition of amides of a ,b -unsaturated acids to butadienecarboxylic acid esters) may be reacted with formaldehyde to give soluble or cross-linked polymethylene-imides.  Di- and polyanhydrides (obtained by adding maleic anhydride and its substitution products to the esters of butadiene-carboxylic acid with glycols, polyalkyline glycols and the like, as mentioned for sorbic acid) may be reacted with mono-, di- or polyepoxides, aliphatic, cycloaliphatic and aromatic di- and polyamines, and the mono-, di- and polyamides deriving from ethyleneimine (such as the N,N-ethylene imides of phosphoric and phosphonic acids, sulphonic, di- and polysulphonic acids and mono-, di- and polycarboxylic acids) and with mono-, di- and polyureas and -urethanes.  Examples describe the reaction of products (obtained from sorbic acid esters and maleic anhydride or acrylic acid) with commercial epoxide resins such as that based on diphenylolpropane and epichlorohydrin.ALSO:New diene adducts are produced by adding, at an elevated temperature, a ,b -ethylenically unsaturated aliphatic monocarboxylic or dicarboxylic acids or their homologs and substitution products or the functional derivatives of these acids to the esters or amides obtainable from optionally substituted butadiene-carboxylic acids and polyhydroxy compounds or polyamines, or to the ester amides of butadiene-carboxylic acids or to N,N1-di-butadiene-carboxylic acid hydrazides. The reactants are generally heated at temperatures of 80-180 DEG  C. in stoichiometric proportions and in the presence of a polymerization inhibitor, in an inert gas atmosphere, and optionally in the presence of an inert solvent.  The diene components may be derived from butadiene carboxylic acid, sorbic acid, methyl-, ethyl-, heptyl- or chloro-sorbic acid, or cyclohexyl or phenyl-butadiene-carboxylic acid.  The polyhydroxy compounds include diols, triols and their oxyalkylation products, polyethers, polyesters or polyamides containing OH groups.  The amides or esteramides are made from diamines or alkanolamines. Examples describe the formation of diene adducts from various sorbic acid esters and maleic anhydride or acrylic acid.  The preparation is also described of the sorbic esters of ethylene glycol, triethylene glycol, trimethylol propane, oxethylated diols and triols, and a complex ester formed by reacting together phthalic anhydride, adipic acid, trimethylol propane and ethylene glycol and reacting the product with sorbic acid.