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New monomers and polymers derived from alpha-hydroxymethyl methyl vinyl ketone

机译:衍生自α-羟甲基甲基乙烯基酮的新型单体和聚合物

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摘要

2-Hydroxymethyl-but-1-ene-3-one [alpha-hydroxymethyl methyl vinyl ketone (HMVK)] was synthesized from methyl vinyl ketone using paraformaldehyde and a tertiary amine catalyst. Free-radical polymerization of this monomer created transparent, tough polymers that were insoluble in organic solvents. HMVK was converted to trimethylsilyl, acetate, and chloride derivatives. When the hydroxyl group was thus protected or removed, all these monomers could be free radically polymerized in bulk to make soluble polymers. The chlorination reaction is complicated by the formation of 1,1-bischloromethylacetone, which dehydrohalogenated unexpectedly to the desired alpha-chloromethyl methyl vinyl ketone. HMVK will self-condense to an ether dimer in the presence of a catalytic acid. This reagent is capable of crosslinking many alkene monomers through hydrolytically stable ether bonds. (C) 2000 John Wiley & Sons, Inc. [References: 17]
机译:使用低聚甲醛和叔胺催化剂,由甲基乙烯基酮合成了2-羟基甲基丁-1-烯-3-酮[α-羟基甲基甲基乙烯基酮(HMVK)]。该单体的自由基聚合产生了不溶于有机溶剂的透明坚韧的聚合物。 HMVK转化为三甲基甲硅烷基,乙酸盐和氯化物衍生物。当羟基因此被保护或除去时,所有这些单体都可以大量自由基聚合成可溶的聚合物。氯化反应由于形成1,1-双氯甲基丙酮而变得复杂,该化合物意外地脱卤化氢为所需的α-氯甲基甲基乙烯基酮。 HMVK在催化酸的存在下会自动缩合为醚二聚体。该试剂能够通过水解稳定的醚键交联许多烯烃单体。 (C)2000 John Wiley&Sons,Inc. [参考:17]

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