A Spirocyclic Parabanic Acid Masked N-Heterocyclic Carbene as Thermally Latent Pre-Catalyst for Polyamide 6 Synthesis and Epoxide Curing.,Macromolecular Rapid Communications

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A Spirocyclic Parabanic Acid Masked N-Heterocyclic Carbene as Thermally Latent Pre-Catalyst for Polyamide 6 Synthesis and Epoxide Curing.
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2020-09-09 , DOI: 10.1002/marc.202000338
Hagen J Altmann ₁ , Wolfgang Frey ₂ , Michael R Buchmeiser ₁

Affiliation

1,3‐Dicyclcohexyl‐6,9‐dimethyl‐1,3,6,9‐tetraazaspiro[4.4]non‐7‐ene‐2,4‐dione, a spirocyclic parabanic acid derivative of N,N‐dimethylimidazole, is used as thermally latent, protected N‐heterocyclic carbene (NHC) in polymerizing anhydride‐cured epoxide resins, and azepan‐2‐one, respectively. The protected carbene is synthesized from 1,3‐dimethylimidazolium‐2‐carboxylate in the presence of two equivalents of cyclohexyl isocyanate. In the synthesis of epoxide resin thermosets, this class of latent NHC allows the production of fast and fully cured materials with high crosslinking content. Fast and complete conversion is found in the anionic ring opening polymerization (AROP) of azepan‐2‐one (ε‐caprolactam, CLA) with and without additional activators.

中文翻译：

螺环芳烃酸掩蔽的N-杂环卡宾作为潜在的聚酰胺6合成和环氧固化的热催化剂。

使用了1,3-二环己基-6,9-二甲基-1,3,6,9-四氮杂螺[4.4]非-7-烯-2,4-二酮，一种N，N-二甲基咪唑的螺环仲班酸衍生物作为热潜伏的，受保护的N杂环卡宾（NHC）分别用于聚合酸酐固化的环氧树脂和Azepan-2-one。受保护的卡宾由1，3-二甲基咪唑-2-羧酸在2当量的异氰酸环己酯存在下合成。在环氧树脂热固性树脂的合成中，这类潜在的NHC可以生产具有高交联含量的快速且完全固化的材料。快速和完全的转化可以在azepan-2-one（ε-己内酰胺，CLA）的阴离子开环聚合（AROP）中进行，无论有无其他活化剂。

更新日期：2020-10-19

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