公开(公告)号：WO1989003864A1

公开(公告)日：1989-05-05

申请号：PCT/US1987002901

申请日：1987-10-30

申请人： MIDWEST RESEARCH INSTITUTE

发明人： MIDWEST RESEARCH INSTITUTE ,  ENGEL, James, Francis ,  BYERLY, Thomas, James ,  CHRISTIE, Howard, Warren

IPC分类号： C09J03/14

CPC分类号： C07C265/00 ,  C07F7/10

摘要： alpha -Substituted acrylic acid esters, their polymers and adhesives therefrom, and methods of synthesizing these compounds. The compounds of the invention are useful as intermediates in the synthesis of isocyanato esters and can be polymerized to form an effective, non-toxic adhesive. The method of the invention encompasses utilizing the adhesive composition in biomedical applications such as joining live animal tissue. Other adhesive applications are contemplated for living tissue and inanimate objects. The compounds are also used as monomers which can be polymerized, used in conjunction with other monomers as adhesive compositions, cross-linking agents, dye acceptor additives to vinylic polymers and useful chemical intermediates. The method of the invention encompasses synthesizing the aforementioned monomers and intermediates. Methyl alpha -(ethoxycarbonamido)-acrylate is synthesized from either DL-serine or methyl pyruvate. For use as an intermediate, silyl substitution of the compound is accomplished by reacting the ester with trimethylchlorosilane. This alpha -substituted silated ester is used as an intermediate in the preparation of methyl alpha -isocyanatoacrylate, which can be polymerized with N-vinyl-2-pyrrolidone to produce a desirable adhesive. Analagous procedures, starting with L-ethyl serine and L-benzyl serine, respectively, are followed to arrive at the corresponding ethyl and benzyl esters.

摘要翻译： α-取代的丙烯酸酯，它们的聚合物和粘合剂，以及合成这些化合物的方法。 本发明的化合物可用作合成异氰酸酯的中间体，可以聚合形成有效的无毒粘合​​剂。 本发明的方法包括在生物医学应用中使用粘合剂组合物，例如连接活动物组织。 预期其他粘合剂应用于活组织和无生命物体。 该化合物也可以作为可以聚合的单体使用，与其它单体结合使用，作为粘合剂组合物，交联剂，染料受体添加剂到乙烯基聚合物和有用的化学中间体。 本发明的方法包括合成上述单体和中间体。 α-（乙氧基羰基酰氨基）丙烯酸甲酯由DL-丝氨酸或丙酮酸甲酯合成。 为了用作中间体，化合物的甲硅烷基取代是通过使酯与三甲基氯硅烷反应来实现的。 该α-取代的硅烷化酯用作制备α-异氰酸酯基丙烯酸甲酯的中间体，其可以与N-乙烯基-2-吡咯烷酮聚合以产生所需的粘合剂。 分别从L-乙基丝氨酸和L-苄基丝氨酸开始分析方法，得到相应的乙基和苄基酯。