Cyclic carbonyl containing polymers

Abstract

The present invention relates to novel polymers which are adducts of an unsaturated hydrocarbon, wherein the novel polymers are produced by contacting cyclic carbonyl monomers with an unsaturated hydrocarbon to form novel cyclic carbonyl polymers having an Mn of about 500 to about 10 7 .

What is claimed is: 
     
       1. An adduct of a substituted or unsubstituted, unsaturated olefinic or polymeric hydrocarbon and a cyclic, ene-reactive carbonyl-containing monomer, said adduct having a number average molecular weight in the range of about 500 to 10,000,000, said adduct .[.prepared by heating a mixture.]. .Iadd.comprising the reaction product .Iaddend.of said unsaturated hydrocarbon and a cyclic, ene-reactive carbonyl-containing monomer characterized by the structures A, B or mixtures of A and B: ##STR6## wherein Q is selected from the group consisting of H 2  O, MeOH, EtOH, and BuOH; n is 0, 1 or greater than 1; X and Y are independently selected from the group consisting of CH 2 , C═O and C═NOH; U, V and W are independently selected from the group consisting CH 2 , C═O, C═NH, C═N-alkyl, O, NH, N-alkyl, S, C-═S, CMe 2 , CH-phenyl and .[.CHCHOH--CH 0  OH.].,  .Iadd.CHCHOH--CH 2  OH .Iaddend.wherein said alkyl group has from 1 to about 18 carbon atoms; and wherein U+V may be 1,2-phenylene, 1,8-naphthalene-diyl, and 1,2-dihydroxyethylene-1,2-diyl. 
     
     
       2. The adduct of claim 1 wherein said unsaturated hydrocarbon is an olefin. 
     
     
       3. The adduct according to claim 2 wherein said olefin contains substituents selected from the group consisting of CN, HO, HO(CH 2  CH 2  O) x , wherein (x=1-10), alkoxy, Cl, and ##STR7## wherein G=C, N; J=O, S, SO 2  ; and and L is selected from the group consisting of OH; --OR 1 , NR 1  R 2  ; wherein R 1  about 1 to about 18 carbon atoms. ##STR8## wherein R 2  is any alkyl and has about 1 to about 18 carbon atoms, --NR 3  R 4  wherein R 3  and and R 4  has about 1 to about 18 carbon atoms, OR 5  wherein R 5  is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, --COOR 6  wherein R 6  is hydrogen or an alkyl group having about 1 to about 18 carbon atoms, and --SR 7 , wherein R 7  is an alkyl group having about 1 to about 18 carbon atoms. 
     
     
       4. The adduct of claim 1 wherein said olefin is 1-octadecene. 
     
     
       5. The adduct of claim 1 wherein said unsaturated hydrocarbon is a polymer selected from the group consisting of polyethylene, polypropylene, ethylene/propylene copolymers, ethylene/propylene/diene terpolymers, polyisoprene, polybutadiene, butyl rubber, styrene-butadiene and styrene-isoprene random or block copolymers, polybutenes and polyisobutylene. 
     
     
       6. The adduct of claim 5 wherein said polymer is polyisobutylene. 
     
     
       7. The adduct of claim 5 wherein said polymer is a terpolymer of ethylene, propylene and diene. 
     
     
       8. The adduct of claim 7 wherein said diene is ethylidene norbornene. 
     
     
       9. The adduct of claim 1 wherein said carbonyl-containing monomer is selected from the group consisting of alloxan, indantrione, tetralintrione, dehydroascorbic acid, rhodizonic acid, croconic acid, triquinoyl, .[.leuconcic.]. .Iadd.leuconic .Iaddend.acid and keto-Meldrum's acid. 
     
     
       10. The adduct of claim 9 wherein said carbonyl-containing .[.member.]. .Iadd.monomer .Iaddend.is alloxan. 
     
     
       11. The adduct of claim 1 prepared by heating .[.said.]. .Iadd.a .Iaddend.mixture .Iadd.comprising said hydrocarbon and said monomer .Iaddend.at a temperature in the range of abut 40° to about 140° C. 
     
     
       12. The adduct of claim 1 prepared by heating a solution of .[.said.]. .Iadd.a .Iaddend.mixture .Iadd.comprising said hydrocarbon and said monomer .Iaddend.in organic solvent at a temperature in the range of about 40° to about 140° C. 
     
     
       13. The adduct of claim 12 wherein said heating is conducted for a period of from about 4 to about 40 hours. 
     
     
       14. The adduct of claim 11 wherein said heating is conducted in the presence of an acid catalyst. 
     
     
       15. A process for preparing the adduct of claim 1 comprising .[.heating a mixture of.]. .Iadd.contacting .Iaddend.said unsaturated hydrocarbon and said cyclic, ene-reactive carbonyl-containing monomer at a temperature .[.in the range of from about 40° C..]. .Iadd.of about 20° C. .Iaddend.for a period of time sufficient to form said adduct.