Research on the New Type of Thermal Resistance Resin Reforming by Oxazolidinones

恶唑烷酮类新型耐热树脂改性研究

• 批准号: 01850189
• 负责人: MATSUDA Haruo
• 金额: $ 2.69万
• 依托单位: Osaka University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research (B).
• 财政年份: 1989
• 资助国家: 日本
• 起止时间: 1989 至 1990
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-01850189/
• 关键词: Epoxy Resin; Thermal Resistance Resin; Stereospecific addition; Oxazolidinone; Organoantimony lodide; Organotin Iodide; イミノジオキソラン; マスクドイソシアナ-ト

This project aims the development of a new type of thermal resistance epoxy resin reforming by introduction of oxazolidinone ring. The selective formation of oxazolidinones from oxiranes and isocyanates, for this aim, is the most basic and important subject. So, we investigated on the effective catalyst for this cycloaffition.Following results are some advantages in this research.(1) Ph_4Sbl-Me_2Snl_2 and Ph_4Sbl-ZnCl_2 systems are the most effective catalysts, and in this catalyst systems little by-products such as iminodioxolanes and isocyanate-trimer were ditected.(2) The formation path of oxazolidinone was examined, and it was found that stereospecific cycloaddition of iminodioxolanes and oxiranes proceeded in the presence of catalytic amounts of AlCl_3.(3) The method mentioned above can produce the new types of oxazolidinones which have not obtained by the direct cycloaddition of oxiranes with isocyanates.(4) The epoxy resins produced by this catalysts have higher softening points (160 - 190 C) than conventional ones.

本项目旨在通过引入恶唑烷酮环来开发一种新型的耐热环氧树脂重整反应。以环氧乙烷和异氰酸酯为原料选择性合成恶唑烷酮是最基本也是最重要的研究课题。结果表明：(1)Ph_4Sbl-Me_2Snl_2和Ph_4Sbl-ZnCl2是最有效的催化剂，在该催化剂体系中，亚氨基二氧杂环戊烷和异氰酸酯-三聚体等副产物较少。研究发现，亚氨基二氧杂环戊烷和环氧杂环烷的立体定向环加成反应是在催化量的AlCl3存在下进行的。(3)上述方法可以合成环氧杂环芳烃与异氰酸酯直接环加成所得的新型恶唑烷酮类化合物。(4)用该催化剂合成的环氧树脂具有比传统环氧树脂更高的软化点(160-190℃)。

项目成果

馬場 章夫: "Stereospecific Cycloaddition of Heterocumulenes to Oxiranes Catalyzed by Organotin Halide Complexes" J.Heterocyclic Chem.27. 1925-1930 (1990)

Akio Baba：“由有机锡卤化物配合物催化的杂积烯与环氧乙烷的立体特异性环加成”J.Heterocyclo Chem.27 1925-1930 (1990)。

Akio Baba, Kenji Seki, Haruo Matsuda: "Stereospecific Cycloaddition of Heterocumulenes to Oxiranes catalyzed by Organotin Iodide Complexes" J. Heterocyclic Chem. 27. 1925-1930 (1990)

Akio Baba、Kenji Seki、Haruo Matsuda：“有机锡碘化物配合物催化的杂积烯与环氧乙烷的立体特异性环加成”J. Heterocycl Chem。

Akio Baba, Kenji Seki, Haruo Matsuda: "Stereocontrolled Oxazolidinone Formation by the Addition of 4, 5-Disubstituted Iminodioxolane to Oxirane via a Spiro Compounds" J. Org. Chem.(1991)

Akio Baba、Kenji Seki、Haruo Matsuda：“通过螺化合物将 4, 5-二取代亚氨基二氧戊环添加到环氧乙烷中形成立体控制的恶唑烷酮”J. Org。

Akio Baba: "Stereospecific Cycloaddition of Heterocumulenes to Oxiranes Catalyzed by Organotin Halide Complexes" J.Heterocyclic Chem.27. 1925-1930 (1990)

Akio Baba：“有机锡卤化物配合物催化的杂积烯与环氧乙烷的立体特异性环加成”J.Heterocycl Chem.27。

馬場 章夫: "Stereoーcontrolled Oxazolidinone Formation by the Addition of 4,5ーDisubsutituted Iminodioxolane to Oxirane via Spiroーcompound" J.Org. Chem.(1991)

Akio Baba：“通过螺环化合物将 4,5-二取代亚氨基二氧戊环添加到环氧乙烷中形成立体控制的恶唑烷酮”J.Org.(1991)