The present invention relates to a method for halogenating an isobutene-isoprene copolymer by using an organic hypochlorite. By using the method of the present invention, a hydrogen halide byproduct may be rapidly recycled into a halogenating agent and reused. As a result, a halogenated isobutene-isoprene copolymer having the high content of secondary allyl halogen functional groups may be prepared by increasing the participation ratio of the halogenating agent in reaction and suppressing the rearrangement of the secondary allyl halogen functional groups. The halogenated isobutene-isoprene copolymer prepared according to the present invention may be effectively used in the crosslinking reaction with other rubber, and is industrially useful.

Methods of post-polymerization modification of a polymer are provided herein. The present methods comprise the step of reacting a polymer with at least one nucleophile in a nucleophilic substitution reaction performed without a solvent to produce a functionalized polymer. The nucleophile can be selected from the group consisting of thioacetate, phenoxide, alkoxide, carboxylate, thiolate, thiocarboxylate, dithiocarboxylate, thiourea, thiocarbamate, dithiocarbamate, xanthate, thiocyanate. Nucleophilic substitution reaction can be performed in the presence of a phase transfer catalyst. Nucleophilic substitution reaction can also be performed via a two-step in-situ reactive mixing process with the initial formation of the polymer-amine ionomer (polymer-NR.sub.3.sup.+Br) which catalyzes the subsequent nucleophilic substitution with a second nucleophile to form a bi-functional polymer.

Methods of post-polymerization modification of a polymer are provided herein. The present methods comprise the step of reacting a polymer with at least one nucleophile in a nucleophilic substitution reaction performed without a solvent to produce a functionalized polymer. The nucleophile can be selected from the group consisting of thioacetate, phenoxide, alkoxide, carboxylate, thiolate, thiocarboxylate, dithiocarboxylate, thiourea, thiocarbamate, dithiocarbamate, xanthate, thiocyanate. Nucleophilic substitution reaction can be performed in the presence of a phase transfer catalyst. Nucleophilic substitution reaction can also be performed via a two-step in-situ reactive mixing process with the initial formation of the polymer-amine ionomer (polymer-NR.sub.3.sup.+Br) which catalyzes the subsequent nucleophilic substitution with a second nucleophile to form a bi-functional polymer.

The present invention is directed to a process for preparing epoxidized polymers. The process comprises reacting an unsaturated polymer with hydrogen peroxide in the presence of a polymer support having a sulfonic acid group. The present invention is also directed to an epoxidized halogenated-polymer which comprises repeating units derived from at least one isoolefin monomer and repeating units derived from at least one diolefinic monomer, and one or more allylic halide groups and one or more oxirane functional groups in the polymer backbone.

The present invention is directed to a process for preparing epoxidized polymers. The process comprises reacting an unsaturated polymer with hydrogen peroxide in the presence of a polymer support having a sulfonic acid group. The present invention is also directed to an epoxidized halogenated-polymer which comprises repeating units derived from at least one isoolefin monomer and repeating units derived from at least one diolefinic monomer, and one or more allylic halide groups and one or more oxirane functional groups in the polymer backbone.

A method of separating a polyisoolefin elastomer from non-polymeric components in an organic solvent involves ultrafiltration of a solution of the polyisoolefin elastomer and non-polymeric components in an organic solvent through a semipermeable membrane to substantially retain the polyisoolefin elastomer in a retentate and provide the non-polymeric components in a permeate. Advantageously, stabilizers for the polyisoolefin elastomer are retained in the retentate along with the polyisoolefin elastomer, permeate flux through the membrane is higher as concentration of the polyisoolefin elastomer in the solution increases up to a concentration limit, the separated polyisoolefin elastomer in the retentate has a molecular weight that can be substantially unchanged even when ultrafiltration is conducted at elevated temperature and the amount of polyisoolefin elastomer in the permeate is unmeasurable providing an oligomer-rich permeate uncontaminated by polyisoolefin elastomer. A process for curing a polyisoolefin copolymer involves reducing content of an oligomer to 900 ppm or less in a mixture of the oligomer and the polyisoolefin copolymer to produce an oligomer-depleted mixture, and adding a resin cure system to the oligomer-depleted mixture to cure the polyisoolefin copolymer.

A method of separating a polyisoolefin elastomer from non-polymeric components in an organic solvent involves ultrafiltration of a solution of the polyisoolefin elastomer and non-polymeric components in an organic solvent through a semipermeable membrane to substantially retain the polyisoolefin elastomer in a retentate and provide the non-polymeric components in a permeate. Advantageously, stabilizers for the polyisoolefin elastomer are retained in the retentate along with the polyisoolefin elastomer, permeate flux through the membrane is higher as concentration of the polyisoolefin elastomer in the solution increases up to a concentration limit, the separated polyisoolefin elastomer in the retentate has a molecular weight that can be substantially unchanged even when ultrafiltration is conducted at elevated temperature and the amount of polyisoolefin elastomer in the permeate is unmeasurable providing an oligomer-rich permeate uncontaminated by polyisoolefin elastomer. A process for curing a polyisoolefin copolymer involves reducing content of an oligomer to 900 ppm or less in a mixture of the oligomer and the polyisoolefin copolymer to produce an oligomer-depleted mixture, and adding a resin cure system to the oligomer-depleted mixture to cure the polyisoolefin copolymer.

A process for producing a halogenated isoolefin copolymer involves contacting an unsaturated isoolefin copolymer cement, the cement containing an unsaturated isoolefin copolymer dissolved in an organic solvent, under halogenation conditions with a halogenating agent and an aqueous solution of an organic peracid oxidant to form a two-phase reaction medium having an organic phase and an aqueous phase, the organic peracid oxidant capable of converting hydrogen halide to free halogen. The process leads to higher halogen utilization even when the cement contains significant amounts of water and without the use of an emulsifier.

A process for producing a halogenated isoolefin copolymer involves contacting an unsaturated isoolefin copolymer cement, the cement containing an unsaturated isoolefin copolymer dissolved in an organic solvent, under halogenation conditions with a halogenating agent and an aqueous solution of an organic peracid oxidant to form a two-phase reaction medium having an organic phase and an aqueous phase, the organic peracid oxidant capable of converting hydrogen halide to free halogen. The process leads to higher halogen utilization even when the cement contains significant amounts of water and without the use of an emulsifier.

A process for producing a halogenated isoolefin copolymer involves contacting an unsaturated isoolefin copolymer cement, the cement containing an unsaturated isoolefin copolymer dissolved in an organic solvent, under halogenation conditions with a halogenating agent and an aqueous solution of an organic peracid oxidant to form a two-phase reaction medium having an organic phase and an aqueous phase, the organic peracid oxidant capable of converting hydrogen halide to free halogen. The process leads to higher halogen utilization even when the cement contains significant amounts of water and without the use of an emulsifier.