Re-workable Polyhydroxyurethane Films with Reversible Acetal Networks Obtained from Multi-functional Six-membered Cyclic Carbonates,Journal of the American Chemical Society

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Re-workable Polyhydroxyurethane Films with Reversible Acetal Networks Obtained from Multi-functional Six-membered Cyclic Carbonates
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-01-16 , DOI: 10.1021/jacs.7b11824
Hiroyuki Matsukizono ₁ , Takeshi Endo ₁

Affiliation

Multifunctional 6-membered cyclic carbonates (6-CCs) comprising acetal structures have been synthesized via phosgene-free routes and utilized for the fabrication of reworkable networked poly(acetal-hydroxyurethane) (PAHU) films. Dibenzoyl-protected di(trimethylolpropane) (DTMP) reacts with multifunctional aldehydes derived from nonexpensive alcohols to afford protected multifunctional DTMPs. After deprotection, the multifunctional DTMPs can react with diphenyl carbonate to efficiently form multifunctional 6-CCs. The polyaddition of the 6-CCs and diamines effectively proceeds in DMF to give networked PAHU films with good transparency and flexibility. These films possess the reworkability based on acid-catalyzed reversibility of acetal linkages. In particular, the film fabricated using large amounts of hexa-functional 6-CCs can reform reproducibly with maintaining to some degree its mechanical properties.

中文翻译：

从多功能六元环状碳酸酯获得具有可逆缩醛网络的可再加工聚羟基聚氨酯薄膜

包含缩醛结构的多功能 6 元环状碳酸酯 (6-CC) 已通过无光气路线合成，并用于制造可再加工的网络聚（缩醛-羟基氨基甲酸酯）（PAHU）薄膜。二苯甲酰基保护的二(三羟甲基丙烷) (DTMP) 与衍生自廉价醇的多功能醛反应，得到受保护的多功能 DTMP。去保护后，多功能 DTMP 可以与碳酸二苯酯反应，有效地形成多功能 6-CC。6-CCs 和二胺的加聚在 DMF 中有效地进行，得到具有良好透明度和柔韧性的网络 PAHU 薄膜。这些薄膜具有基于酸催化的缩醛键可逆性的可再加工性。特别是，

更新日期：2018-01-16

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