Synthesis of Butyl Rubber Containing 4-Vinylphenyl Group by Using Suzuki-Miyaura Coupling Reaction

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  • Ｓｕｚｕｋｉ‐Ｍｉｙａｕｒａカップリングを用いた側鎖に４‐ビニルフェニル基を有するブチルゴムの合成
  • Suzuki-Miyauraカップリングを用いた側鎖に4-ビニルフェニル基を有するブチルゴムの合成
  • Suzuki Miyaura カップリング オ モチイタ ソクサ ニ 4 ビニルフェニルキ オ ユウスル ブチル ゴム ノ ゴウセイ

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Abstract

Suzuki-Miyaura coupling reaction of brominated butyl rubber (BIIR) with 4-vinylphenylboronic acid were carried out in THF using cyclopalladated complex as catalyst. The degree of 4-vinylphenyl group introduction was estimated from the ratio of RI and UV peak area in the size exclusion chromatogram (SEC) of modified butyl rubber (St-IIR). Considerable amount of 4-vinylphenyl group could be introduced to butyl rubber in the presence of small amount (Pd/Br≈1/1000) of Pd catalyst.<br>Quantitative analysis for the degree of 4-vinylphenyl group introduction was made by 1H-NMR. The exo methylene signals in BIIR decreased by the reaction whereas signals attributable to the viny protons of 4-vinylphenyl group increased with reaction time. When reaction was carried out in THF at reflux temperature for 12 h in the presence of 0.01 eq. of Pd catalyst, 4-vinylphenyl group was introduced quantitatively. The peroxide curing behavior of St-IIR was also examined.

Journal

  • NIPPON GOMU KYOKAISHI

    NIPPON GOMU KYOKAISHI 82 (6), 241-246, 2009

    THE SOCIRETY OF RUBBER SCIENCE AND TECHNOLOGYY, JAPAN

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