Synthesis of graft copolymer derivatives of brominated poly(isobutylene-co-isoprene) |
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Authors: | J Keith McLean J Scott Parent Ralph A Whitney |
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Institution: | a Department of Chemical Engineering, Queen’s University, Kingston, Ontario, Canada K7L 3N6 b Department of Chemistry, Queen’s University, Kingston, Ontario, Canada K7L 3N6 c LANXESS Inc., Sarnia, Ontario, Canada N7T 7M2 |
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Abstract: | Strategies for preparing graft copolymers from brominated poly(isobutylene-co-isoprene) (BIIR) are demonstrated. Selective dehydrohalogenation of the allylic bromide functionality within BIIR to give an exo-conjugated diene is described, along with subsequent cycloadditions of maleic anhydride (MAn) and its mono-ester and di-ester derivatives. Alcoholysis of the bicyclic anhydride product of BIIR dehydrobromination/MAn cycloaddition is used to produce an IIR-g-PE copolymer in low yield. An alternate approach involving bromide displacement from BIIR by the salts of maleate half-esters is shown to be an efficient means of generating isobutylene-rich copolymers containing polyethylene, polyethylene oxide and polycaprolactone grafts. |
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Keywords: | Butyl rubber Graft copolymer synthesis Nucleophilic substitution Cycloaddition |
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