Aliphatic ditopic nitrile N-oxide crosslinker: Synthesis, chemical stability, and catalyst-free crosslinking reactions

POLYMER

卷:213

Article

Sogawa, Hiromitsu^1,2  Wang, Chen-Gang^1,5  Monjiyama, Shunsuke¹  Akae, Yosuke^1,4  Takata, Toshikazu^1,3 

[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, 2-12-1 O Okayama, Tokyo 1528552, Japan

[2] Kansai Univ, Fac Chem Mat & Bioengn, Dept Chem & Mat Engn, Suita, Osaka 5648680, Japan

[3] Hiroshima Univ, Grad Sch Adv Sci & Engn, Hiroshima 7398527, Japan

[4] Shinshu Univ, Fac Text Sci & Technol, G507,Ueda Campus,3-15-1 Tokida, Ueda, Nagano 3868567, Japan

[5] ASTAR, Inst Mat Res & Engn, 2 Fusionopolis Way,Innovis 08-03, Singapore 138634, Singapore

关键词: Nitrile N-oxide;    1,3-dipolar cycloaddition;    Crosslinking reaction;   

DOI  :  10.1016/j.polymer.2020.123291

来源: Elsevier

【 摘 要 】

Nitrile N-oxides are useful reagents and crosslinkers for catalyst- and byproduct-free 1,3-dipolar cycloaddition reactions. The stability of nitrile N-oxides can be enhanced by introducing bulky substituents, whereas their reactivity decreases concomitantly. Herein, an isolatable aliphatic ditopic nitrile N-oxide was synthesized and applied to catalyst-free crosslinking of unsaturated bond-containing polymers. By decreasing the steric hindrance around the nitrile N-oxide moiety compared with a related crosslinker previously developed in our group, the operating temperature of the crosslinking reaction could be lowered. Efficient crosslinking of natural rubber (NR) was achieved at 40 degrees C in chloroform to give crosslinked NR without formation of byproducts. Furthermore, polyacrylonitrile and nitrile butadiene rubber can be used as the scaffolds for efficient catalyst- and solvent-free crosslinking reactions.

【 授权许可】

Free