Patent GB-612311-A (GB)
Title: Improvements in or relating to the production of polymerisable esters
IPC: H01B3/44
Filed: 1945-04-17
Abstract: Allyl or 2-methyl allyl alcohol esters of a mono-substituted succinic acid or anhydride in which the substituent is an organic radicle containing not less than three carbon atoms are polymerized to oils or soft resins.  The substituted succinic acid or anhydride may be produced by the addition reaction of maleic anhydride with a non-conjugated poly-unsaturated organic compound such as a non-conjugated terpene or a drying oil fatty acid or an ester thereof, or with an aromatic hydrocarbon having a saturated aliphatic or carbocyclic side chain, e.g. with toluene which yields benzyl succinic acid.  The substituent may also be unsaturated, e.g. an alkenyl radicle.  Polymerization catalysts, e.g. benzoyl peroxide may be present.  The products may be used in bonding, electrical insulating, impregnating and surface coating compositions. Fabricated products such as brake linings or plywood may be produced by using the polymerized esters as bonding agents.  In examples (2) and (4) the addition products obtained by heating maleic anhydride with dipentene and raw linseed oil respectively are esterified with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid and polymerised in the presence of benzoyl peroxide at 130 DEG -140 DEG  C.; (3) a mixture of monoalkenyl substituted succinic anhydrides containing alkenyl groups with from 8 to 10 carbon atoms is refluxed with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid and polymerised at 140 DEG C. in the presence of benzoyl peroxide.  Specifications 500,348, 552,095, 612,312 and German Specification 607,380 are referred to. The Provisional Specification refers also to Specification 552,228.ALSO:Polymerizable esters are prepared by esterifying with allyl or 2-methyl allyl alcohol, a mono-substituted succinic acid or anhydride in which the substituent is an organic radicle containing not less than three carbon atoms or by effecting an alcoholysis reaction between a lower alkyl ester of said substituted succinic acid and allyl or methallyl alcohol.  The substituted succinic acid or anhydride may be produced by the addition reaction of maleic anhydride with a non-conjugated poly-unsaturated organic compound such as a non-conjugated terpene or a drying oil fatty acid or an ester thereof, or with an aromatic hydrocarbon having a saturated aliphatic or carbocyclic side chain, e.g. with toluene which yields benzyl succinic acid. The substituent may also be unsaturated, e.g. an alkenyl radicle. The products vary from oils to soft resins of the character of balsams and can be used in bonding compositions, electrical insulating compositions and in varnish impregnating and surface coating compositions.  Fabricated products such as brake linings or plywood may be produced by using the polymerized esters as bonding agents.  In examples: (1) allyl alcohol is added to the adduct obtained by heating dimethyl maleate and the methyl esters of linseed oil fatty acids, the diallyl ester of the maleate adduct being produced by alcoholysis, (2) and (4) the addition products obtained by heating maleic anhydride with dipentene and raw linseed oil respectively are esterified with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid; (3) a mixture of mono-alkenyl substituted succinic anhydrides containing alkenyl groups with from 8 to 10 carbon atoms is refluxed with allyl alcohol in the presence of a small amount of p-toluene sulphonic acid.  The purified ester is a light yellow oil. Specifications 500,348, 552,095, 612,312 and German Specification 607,380 are referred to. The Provisional Specification refers also to Specification 552,228.