RADIATION TREATMENT OF HALOGEN CONTAINING OLEFINICALLY UNSATURATED ESTERS

1,226,657. Coating. BADISCHE ANILIN- & SODA-FABRIK A.G. 10 July, 1968 [11 July, 1967], No. 32871/68. Heading B2E. [Also in Division C3] Coatings are produced on substrates, e.g. metal articles, by coating the article with a mixture of olefinically unsaturated monomers containing 10-90% by weight of at least one ester derived from an α, #-olefinically unsaturated monocarboxylic acid and a chlorinated and/or brominated monohydric alcohol, and polymerising the coating by irradiating with high-energy radiation at atmospheric pressure. Preferably, polymerisation is effected in the absence of solvents. The substrate can be coated by spraying, brushing, pouring, rolling, knife-coating, flooding or dipping. The specified ester monomer is preferably a chloro (or bromo) alkyl ester of acrylic, methacrylic, crotonic or cinnamic acid; the alcohol moiety may additionally contain a double bond or nitro group and the acid moiety may be halosubstituted (including, e.g. bromoundecenoic acid). The other component(s) of the monomer mixture may be, for example, (meth)acrylate esters, vinylbenzenes, unsaturated nitriles; vinyl esters, olefins, halogen-containing compounds such as halogen-containing unsaturated acids, unsaturated acyl halides and halogen-containing unsaturated amides, and compounds containing two or more polymerisable double bonds. The polymerisable system may optionally include molecular weight regulators, e.g. mercaptans, acetoacetic esters, haloparaffins or aldehydes, pigments, dyes, optical brighteners, plasticisers, flow or gloss promoting agents, polymerisation initiators, aging retardants, and natural or synthetic resins. Irradiation can be effected with electron rays, X-rays or gammarays. In the Examples the following monomer systems are polymerised (1) and (2) 2, 3- dibromopropyl acrylate and N, N', N", N"'- tetra (allyloxymethyl)-acetylene-diurea; (3) 3a, 4, 5, 6, 7, 7a-hexahydro-4, 7-methanoindenyl acrylate-(5) and 2, 3-dichloropropyl acrylate; (4) 2, 3-dibromopropyl α-chloroacrylate, triethylene glycol diacrylate and the diurea derivative of (1) and (2); (5) the indenyl acrylate derivative of (3), 2, 3-dichloro-3-bromoacrylic acid and 2-chloroallyl acrylate; (6) 2- chlorocrotonyl chloride, 2, 3-dichloropropyl acrylate and trialllyl cyanurate.