后过渡金属配合物催化烯烃-极性单体共聚

doi:10.6023/cjoc202009008

摘要/Abstract

在非极性聚烯烃链中引入少量极性基团可明显改善聚烯烃材料性能. 依据配合物种类全面综述了2010年以来后过渡金属配合物催化烯烃-极性单体共聚研究进展. 从α-二亚胺、膦酚和水杨醛亚胺型配合物到酮胺、膦磺酸、膦-氧化膦和N-杂环卡宾型等多种新型骨架结构配合物, 总结了这些催化剂对催化活性、共聚物分子量、极性基团插入率、共聚物微观结构和材料性能的有效调控. 尽管取得了许多重要进展, 这一领域产业化和商业化应用依然面临诸多限制和挑战. 展望了应对这些挑战需要关注的问题.

关键词: 催化剂, 聚合, 配合物, 烯烃, 极性单体, 后过渡金属

Incorporation of small amounts of polar functional groups into non-polar polyolefins can dramatically improve properties of polyolefins. The development of late transition metal complexes for olefin copolymerization with polar monomers according to different types of complexes in the last decade is reviewed. With regard to α-diimine, phosphino-phenolate, salicylaldimine, ketoamine, phosphine-sulfonate, bisphospnine monoxide, N-heterocyclic carbene complexes and more emerging catalysts, fine modulation of key copolymerization parameters (activity, molecular weight, polar monemer incorporation, etc.) and material properties of polyolefins in a controlled way are described in detail. Despite many recent advances and enticing characteristics of these catalysts, there still remains challenges for industrial and commercial application due to a variety of limitations. To overcome some of these challenges, a brief outlook on the future of issues should be focused on is provided.

Key words: catalyst, polymerization, complex, olefin, polar monomer, late transition metal

引用此文

李永清, 王凡, 曹育才. 后过渡金属配合物催化烯烃-极性单体共聚[J]. 有机化学, 2021, 41(4): 1396-1433.

Yongqing Li, Fan Wang, Yucai Cao. Late Transition Metal Complexes for Olefin Copolymerization with Polar Monomers[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1396-1433.

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图/表 20

图式1. 在聚烯烃中引入极性基团的方法

Scheme 1. Approaches for synthesis of polyolefins containing polar group

图式2. 后过渡金属催化乙烯-极性单体共聚及“链行走”的一般机理

Scheme 2. General mechanism for late transition metal catalyzed ethylene copolymerization with polar monomer and “chain walking”

图1. 不同骨架的烯烃-极性单体共聚后过渡金属催化剂

Figure 1. Late transition metal catalysts with various backbones for olefin copolymerization with polar monomers

图式3. 极性单体问题

Scheme 3. Polar monomer problem

图2. 乙烯型极性单体

Figure 2. Polar vinyl monomers

图3. 烯丙基型及长链阻隔型极性单体

Figure 3. Polar allyl monomers and monomers with methylene spacers

图4. 降冰片烯型极性单体

Figure 4. Polar norbornyl monomers

图式4. 7催化共聚机理

Scheme 4. Mechanism for copolymerization catalyzed by 7

图式5. 可能的乙烯-丙烯酸烯丙基酯共聚机理

Scheme 5. Possibile mechanism for copolymerization of ethylene and allyl acrylate

图式6. 可能的乙烯-丙烯酸酐共聚机理

Scheme 6. Possibile mechanism for copolymerization of ethylene and acrylic anhydride

图5. 商业化极性共聚物

Figure 5. Commercial polar copolymers

图6. 具有不同微观结构的后过渡金属催化乙烯-极性单体共聚物

Figure 6. Copolymers of ethylene and polar monomers with different microstructures

图式7. 乙烯与极性单体直接共聚制备极性聚乙烯弹性体

Scheme 7. Polar-substituted polyethylene elastomers from ethylene copolymerization with polar monomers

图7. 共聚物十次300%拉伸回弹测试应力-应变曲线图

Figure 7. Plots of hysteresis experiments of ten cycles at a strain of 300% for copolymer samples Reprinted (adapted) with permission from Ref. [200]. Copyright (2020) American Chemical Society

图8. 52和241催化的聚乙烯和乙烯共聚物应力-应变曲线图

Figure 8. Stress vs strain curves for the polymer and copolymer products generated using 52 and 241 (a~c)241, (d) 52. Reprinted (adapted) with permission from Ref. [65]. Copyright (2018) American Chemical Society

图9. 52和241催化的聚乙烯和乙烯共聚物的水接触角

Figure 9. Water contact angles of the polyethylene and copolymer products generated using 52 and 241 (a) 52, (b) 241. Reprinted (adapted) with permission from Ref. [65]. Copyright (2018) American Chemical Society

图式8. 乙烯共聚使用的极性单体

Scheme 8. Comonomers used in the copolymerization of ethylene

图10. 热重分析(TGA)曲线和热释放速率(HRR)曲线

Figure 10. Thermal gravimetric analysis (TGA) curves and heat release rate (HRR) curves TGA curves of the copolymers (a) and terpolymers (b), HRR curves of copolymers (c) and terpolymers (d). Reproduced from Ref. [7c] with permission from The Royal Society of Chemistry.

图11. 共混材料扫描电镜(SEM)图

Figure 11. Scanning electron microscope (SEM) images (a) PE/APP (m∶m=70∶30) and (b) PE/poly(E-co-O1)/APP (m∶m∶m=60∶10∶30) composites. Reproduced from Ref. [7c] with permission from The Royal Society of Chemistry.

图12. 通过ENB插入率、氢键、Fe3+交联、硫化交联调节材料性能

Figure 12. Modulation of material properties through ENB incorporation, hydrogen bonding, Fe3+-induced crosslinking and sulfur-induced vulcanization

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