General approach to prepare polymers bearing pendant isocyanate groups,Polymer Chemistry

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General approach to prepare polymers bearing pendant isocyanate groups
Polymer Chemistry ( IF 4.1 ) Pub Date : 2020-07-28 , DOI: 10.1039/d0py00989j
Rodrigo Navarro _{1,

2,

3} , Carolina García _{1,

2,

3} , Juan Rodríguez-Hernández _{1,

2,

3} , Carlos Elvira _{1,

2,

3} , Angel Marcos-Fernández _{1,

2,

3} , Alberto Gallardo _{1,

2,

3} , Helmut Reinecke _{1,

2,

3}

Affiliation

A versatile synthetic approach for the easy preparation, under smooth reaction conditions, of diverse classes of linear polymers bearing aliphatic or aromatic isocyanate groups in the side chains is described. The procedure consists in the transformation of primary amine groups present in the polymer into isocyanates using equimolar amounts of diphosgene or triphosgene and a soluble tertiary amine as the acid scavenger. The transformation of all amine groups takes place quasi-simultaneously and instantaneously as shown by the invariability of the chain length of the polymer and the absence of crosslinked products. The number of isocyanate groups per molecule that can be achieved by this approach corresponds to the number of primary amine groups of the starting polymer and is up to three orders of magnitude higher than in any other non-crosslinked molecule described so far. The isocyanate functionalized polymers can be used to anchor a large variety of molecules to the polymer chains. The approach is in detail demonstrated with poly(vinyl chloride) (PVC) carrying aromatic amine groups but has also been confirmed by using a number of other polymer types bearing both aromatic and aliphatic primary amines. Furthermore, it has been used to prepare a novel low molecular weight compound, tris(2-cyanatoethyl)amine.

中文翻译：

制备带有异氰酸酯侧基的聚合物的一般方法

描述了一种通用的合成方法，该方法可在平滑反应条件下轻松制备侧链中带有脂族或芳族异氰酸酯基的各种线性聚合物。该方法包括使用等摩尔量的双光气或三光气和可溶性叔胺作为除酸剂，将聚合物中存在的伯胺基团转变为异氰酸酯。如聚合物链长的不变性和不存在交联产物所示，所有胺基团的转化都同时和瞬间发生。通过该方法可以实现的每个分子中的异氰酸酯基团的数量对应于起始聚合物的伯胺基团的数量，并且比迄今为止描述的任何其他非交联分子高多达三个数量级。异氰酸酯官能化的聚合物可用于将多种分子锚定到聚合物链上。该方法已通过带有芳族胺基的聚氯乙烯（PVC）进行了详细说明，但也已通过使用多种同时带有芳族和脂族伯胺的其他聚合物类型得到证实。此外，已将其用于制备新型低分子量化合物三（2-氰基乙基）胺。用带有芳族胺基团的聚（氯乙烯）（PVC）已详细证明了该方法，但也已通过使用多种同时带有芳族和脂族伯胺的其他聚合物类型得到证实。此外，已将其用于制备新型低分子量化合物三（2-氰基乙基）胺。用带有芳族胺基团的聚（氯乙烯）（PVC）已详细证明了该方法，但也已通过使用多种同时带有芳族和脂族伯胺的其他聚合物类型得到证实。此外，已将其用于制备新型低分子量化合物三（2-氰基乙基）胺。

更新日期：2020-08-18

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