Synthesis of functionalized polyisobutylenes

A method of forming a functional polyisobutylene having at least one terminal primary or secondary hydroxyl group comprising the steps of:

• providing a polymer mixture of butyl rubber and at least one polymer selected from the group consisting of:
• an olefin functional polyisobutylene, the olefin functional polyisobutylene optionally including at least one internal phenyl group, and having one or more terminal allyl groups;
• an olefin functional polyisobutylene having an endo carbon to carbon double bond, an exo carbon to carbon double bond, or a mixture thereof on at least one terminal end;
• and mixtures thereof;
• solubilizing the polymer in an organic solvent to form a polymer solution;
• subjecting the polymer solution to ozonation by bubbling ozone through the polymer at a temperature in the range of from +10° C. to a temperature that is greater than the freezing temperature of the polymer solution, optionally in the presence of a sulfide catalyst;
• and
• treating the product of step c) at a temperature from 0 to 100° C. in the presence of a reducing agent thereby forming a functional polyisobutylene having at least one terminal primary or secondary hydroxyl group.

A method of forming a functional polyisobutylene comprising the steps of:

• a) providing at least one polymer selected from:
• an olefin functional polyisobutylene, the olefin functional polyisobutylene optionally including at least one internal phenyl group;
• butyl rubber;
• and mixtures thereof;
• b) solubilizing the polymer in an organic solvent to form a polymer solution;
• c) subjecting the polymer solution to ozonation by bubbling ozone through the polymer at a temperature in the range of from +10° C. to a temperature that is greater than the freezing temperature of the polymer solution, optionally in the presence of a sulfide catalyst;
• d) treating the product of step c) at a temperature from 0 to 100° C. in the presence of a reducing agent thereby forming a functional polyisobutylene having at least one terminal primary or secondary hydroxyl group;
• e) forming a mixture comprising the functional polyisobutylene of step d), an organic solvent, a catalyst, and a C1 to C12 (meth)acrylate or acrolyl chloride or methacrylic anhydride and reacting the mixture at a temperature from 40 to 80° C. for a period of time to form a functional polyisobutylene having at least one (meth)acrylate terminal end.

A method of forming a functional polyisobutylene comprising the steps of:

• a) providing at least one polymer selected from:
• an olefin functional polyisobutylene, the olefin functional polyisobutylene optionally including at least one internal phenyl group;
• butyl rubber;
• and mixtures thereof;
• b) solubilizing the polymer in an organic solvent to form a polymer solution;
• c) subjecting the polymer solution to ozonation by bubbling ozone through the polymer at a temperature in the range of from +10° C. to a temperature that is greater than the freezing temperature of the polymer solution, optionally in the presence of a sulfide catalyst;
• d) treating the product of step c) at a temperature from 0 to 100° C. in the presence of a reducing agent thereby forming a functional polyisobutylene having at least one terminal primary or secondary hydroxyl group;
• e) reacting the functional polyisobutylene from step d) with at least one isocyanate in presence of a suitable catalyst to form a functional polyisobutylene having at least one terminal urethane end;
• and
• f) forming a mixture comprising the functional polyisobutylene of step e), an organic solvent, a catalyst, and a C1 to C12 (meth)acrylate or acrolyl chloride or methacrylic anhydride and reacting the mixture at a temperature from 40 to 80° C. for a period of time to form a functional polyisobutylene having at least one methacrylate capped urethane terminal end.

A method of forming a functional polyisobutylene comprising the steps of:

• a) providing at least one polymer selected from:
• an olefin functional polyisobutylene, the olefin functional polyisobutylene optionally including at least one internal phenyl group;
• butyl rubber;
• and mixtures thereof;
• b) solubilizing the polymer in an organic solvent to form a polymer solution;
• c) subjecting the polymer solution to ozonation by bubbling ozone through the polymer at a temperature in the range of from +10° C. to a temperature that is greater than the freezing temperature of the polymer solution, optionally in the presence of a sulfide catalyst;
• d) treating the product of step c) at a temperature from 0 to 100° C. in the presence of a reducing agent thereby forming a functional polyisobutylene having at least one terminal primary or secondary hydroxyl group;
• and
• e) reacting the functional polyisobutylene from step d) with at least one isocyanate containing a (meth)acrylate group in the presence of a suitable catalyst to form a (meth)acrylate functional polyisobutylene having at least one terminal urethane end.