有机磷腈碱催化环内酯开环聚合制备可降解聚酯研究进展

沈勇; 李志波

doi:10.11777/j.issn1000-3304.2020.20050

您当前的位置：

首页 >

文章列表页 >

有机磷腈碱催化环内酯开环聚合制备可降解聚酯研究进展

专论 | 更新时间：2021-01-26

- 有机磷腈碱催化环内酯开环聚合制备可降解聚酯研究进展
- Ring-opening Polymerization of Cyclic Esters by Utilizing Organophosphazene Bases toward Biodegradable Polyesters
- 高分子学报 2020年51卷第8期页码：777-790
- 作者机构：
  
  1.青岛科技大学化工学院　青岛 266042
  2.山东省高等学校生物基高分子材料重点实验室青岛科技大学高分子科学与工程学院　青岛 266042
- 作者简介：
  
  [ "李志波，男，1974年生. 1998年和2001年于中国科学技术大学高分子科学与工程系分别获得学士学位和硕士学位；2006年美国明尼苏达大学化学系获博士学位. 2006 ~ 2008年，美国加利福尼亚大学洛杉矶分校生物工程系博士后；2008年8月全职回国于中国科学院化学研究所高分子物理与化学实验室工作，任研究员、博士生导师；2014年12月至今任青岛科技大学高分子科学与工程学院教授. 主要从事可降解高分子材料的设计、合成与结构表征研究，致力于发展新的合成聚合方法和催化剂，制备高性能、高附加值的功能高分子新材料" ]
- 基金信息：
  
  国家自然科学基金(基金号 21801151)和山东省泰山学者优势特色学科团队计划(项目号 tsqn20161031)资助项目
- DOI：10.11777/j.issn1000-3304.2020.20050
  中图分类号：
- 纸质出版日期：2020-8，
  
  网络出版日期：2020-7-3，
  
  收稿日期：2020-4-2，
  
  修回日期：2020-4-12，
扫描看全文
沈勇, 李志波. 有机磷腈碱催化环内酯开环聚合制备可降解聚酯研究进展[J]. 高分子学报, 2020,51(8):777-790.

Yong Shen, Zhi-bo Li. Ring-opening Polymerization of Cyclic Esters by Utilizing Organophosphazene Bases toward Biodegradable Polyesters[J]. Acta Polymerica Sinica, 2020,51(8):777-790.
沈勇, 李志波. 有机磷腈碱催化环内酯开环聚合制备可降解聚酯研究进展[J]. 高分子学报, 2020,51(8):777-790. DOI： 10.11777/j.issn1000-3304.2020.20050.

Yong Shen, Zhi-bo Li. Ring-opening Polymerization of Cyclic Esters by Utilizing Organophosphazene Bases toward Biodegradable Polyesters[J]. Acta Polymerica Sinica, 2020,51(8):777-790. DOI： 10.11777/j.issn1000-3304.2020.20050.

摘要

脂肪族聚酯作为一类重要的高分子材料，具有优异的生物相容性和生物可降解性以及良好的力学性能，在可吸收手术缝合线、组织工程支架、食品包装等方面已经取得了广泛应用. 环内酯开环聚合是制备脂肪族聚酯材料的一种重要方法. 有机磷腈碱作为一类非离子型、非亲核性有机强碱，在催化环内酯开环聚合方面已经取得了巨大的成功. 本专论综述了有机磷腈碱在催化

-丁内酯及其衍生物、己内酯、戊内酯、丙交酯和大环内酯开环聚合方面的研究进展，对聚合机理进行了适当讨论，并对其未来发展方向作了展望.

Abstract

Given their great biocompatibility

biodegradability and good mechanical properties

aliphatic polyesters as important polymers have been widely used in many applications as absorbable sutures

tissue engineering scaffolds and food packing materials. Aliphatic polyesters can be synthesized by ring-opening polymerization (ROP) of cyclic lactones or lactides. Organophosphazene bases are a family of uncharged

non-nucleophilic organobases

which have achieved great success as organocatalysts for the ROP of cyclic lactones and lactides. This feature article reviewed the recent progresses for ROP of cyclic lactones and lactides by utilizing phosphazene bases as catalysts

including

-butyrolactone and its derivatives

-carprolactone

-valerolactone

lactide and macrolactones. The challenges and perspectives on the further development of phosphazene base catalyzed ROP were also discussed.

关键词

生态环境高分子开环聚合聚酯有机催化磷腈碱

Keywords

Eco-polymersRing-opening polymerizationPolyestersOrganocatalystsPhosphazene bases

references

Zhang X, Fevre M, Jones G O, Waymouth R M. Chem Rev , 2018 . 118 ( 2 ): 839 - 885 . DOI:10.1021/acs.chemrev.7b00329http://doi.org/10.1021/acs.chemrev.7b00329 .

Plastics – the Facts 2019. https://www.plasticseurope.org/en/resources/market-datahttps://www.plasticseurope.org/en/resources/market-data

Schneiderman D K, Hillmyer M A. Macromolecules , 2017 . 50 ( 10 ): 3733 - 3749 . DOI:10.1021/acs.macromol.7b00293http://doi.org/10.1021/acs.macromol.7b00293 .

Jambeck J R, Geyer R, Wilcox C, Siegler T R, Perryman M, Andrady A, Narayan R, Law K L. Science , 2015 . 347 ( 6223 ): 768 - 771 . DOI:10.1126/science.1260352http://doi.org/10.1126/science.1260352 .

The New Plastics Economy: Rethinking the future of plastics & catalysing action. ed. https://www.ellenmacarthurfoundation.org/publicationshttps://www.ellenmacarthurfoundation.org/publications: Ellen MacArthur Foundation 2017

An Zesheng(安泽胜), Chen Changle(陈昶乐), He Junpo(何军坡), Hong Chunyan(洪春雁), Li Zhibo(李志波),Li Zichen(李子臣), Liu Chao(刘超), Lv Xiaobing(吕小兵), Qin Anjun(秦安军), Qu Chengke(曲程科), Tang Benzhong(唐本忠), Tao Youhua(陶友华), Wan Xinhua(宛新华), Wang Guowei(王国伟), Wang Jia(王佳), Zheng Ke(郑轲),Zou Wenkai(邹文凯). Acta Polymerica Sinica(高分子学报) , 2019 . 50 ( 10 ): 1083 - 1132 . DOI:10.11777/j.issn1000-3304.2019.19136http://doi.org/10.11777/j.issn1000-3304.2019.19136 .

Chen Xuesi(陈学思), Chen Guoqiang(陈国强), Tao Youhua(陶友华), Wang Yuzhong(王玉忠), Lv Xiaobing(吕小兵), Zhang Liqun(张立群), Zhu Jin(朱锦), Zhang Jun(张军), Wang Xianhong(王献红). Acta Polymerica Sinica(高分子学报) , 2019 . 50 ( 10 ): 1068 - 1082 . DOI:10.11777/j.issn1000-3304.2019.19124http://doi.org/10.11777/j.issn1000-3304.2019.19124 .

Kamber N E, Jeong W, Waymouth R M, Pratt R C, Lohmeijer B G G, Hedrick J L. Chem Rev , 2007 . 107 ( 12 ): 5813 - 5840 . DOI:10.1021/cr068415bhttp://doi.org/10.1021/cr068415b .

Hu S, Zhao J, Zhang G, Schlaad H. Prog Polym Sci , 2017 . 74 34 - 77 . DOI:10.1016/j.progpolymsci.2017.07.002http://doi.org/10.1016/j.progpolymsci.2017.07.002 .

Herzberger J, Niederer K, Pohlit H, Seiwert J, Worm M, Wurm F R, Frey H. Chem Rev , 2016 . 116 ( 4 ): 2170 - 2243 . DOI:10.1021/acs.chemrev.5b00441http://doi.org/10.1021/acs.chemrev.5b00441 .

Zhang L, Nederberg F, Pratt R C, Waymouth R M, Hedrick J L, Wade C G. Macromolecules , 2007 . 40 ( 12 ): 4154 - 4158 . DOI:10.1021/ma070316shttp://doi.org/10.1021/ma070316s .

Shi J F, Zhao N, Xia S, Liu S F, Li Z B. Polym Chem , 2019 . 10 ( 17 ): 2126 - 2133 . DOI:10.1039/C9PY00247Bhttp://doi.org/10.1039/C9PY00247B .

Yang H, Zhao J, Yan M, Pispas S, Zhang G. Polym Chem , 2011 . 2 ( 12 ): 2888 - 2892 . DOI:10.1039/c1py00334hhttp://doi.org/10.1039/c1py00334h .

Helou M, Miserque O, Brusson J M, Carpentier J F, Guillaume S M. Chem--Eur J , 2010 . 16 ( 46 ): 13805 - 13813 . DOI:10.1002/chem.201001111http://doi.org/10.1002/chem.201001111 .

Kou X H, Li Y Z, Shen Y, Li Z B. Macromol Chem Phys , 2019 . 220 ( 24 ): 1900416 DOI:10.1002/macp.201900416http://doi.org/10.1002/macp.201900416 .

Zhao N, Ren C, Li H, Li Y, Liu S, Li Z. Angew Chem Int Ed , 2017 . 56 ( 42 ): 12987 - 12990 . DOI:10.1002/anie.201707122http://doi.org/10.1002/anie.201707122 .

Liu S, Ren C, Zhao N, Shen Y, Li Z. Macromol Rapid Commun , 2018 . 39 ( 24 ): 1800485 DOI:10.1002/marc.201800485http://doi.org/10.1002/marc.201800485 .

Schwesinger R, Schlemper H, Hasenfratz C, Willaredt J, Dambacher T, Breuer T, Ottaway C, Fletschinger M, Boele J, Fritz H, Putzas D, Rotter H W, Bordwell F G, Satish A V, Ji G Z, Peters E M, Peters K, von Schnering H G, Walz L. Liebigs Annalen , 1996 . ( 7 ): 1055 - 1081.

Schwesinger R, Willaredt J, Schlemper H, Keller M, Schmitt D, Fritz H. Chem Ber , 1994 . 127 ( 12 ): 2435 - 2454 . DOI:10.1002/cber.19941271215http://doi.org/10.1002/cber.19941271215 .

Bug T, Lemek T, Mayr H. J Org Chem , 2004 . 69 ( 22 ): 7565 - 7576 . DOI:10.1021/jo048773jhttp://doi.org/10.1021/jo048773j .

Boileau S, Illy N. Prog Polym Sci , 2011 . 36 ( 9 ): 1132 - 1151 . DOI:10.1016/j.progpolymsci.2011.05.005http://doi.org/10.1016/j.progpolymsci.2011.05.005 .

Martin D P, Williams S F. Biochem Eng J , 2003 . 16 ( 2 ): 97 - 105 . DOI:10.1016/S1369-703X(03)00040-8http://doi.org/10.1016/S1369-703X(03)00040-8 .

Williams S F, Rizk S, Martin D P. Biomed Tech (Berl) , 2013 . 58 ( 5 ): 439 - 452.

Hong M, Chen E Y X. Angew Chem Int Ed , 2016 . 55 ( 13 ): 4188 - 4193 . DOI:10.1002/anie.201601092http://doi.org/10.1002/anie.201601092 .

Shen Y, Zhao Z, Li Y, Liu S, Liu F, Li Z. Polym Chem , 2019 . 10 ( 10 ): 1231 - 1237 . DOI:10.1039/C8PY01812Jhttp://doi.org/10.1039/C8PY01812J .

Zhang C J, Hu L F, Wu H L, Cao X H, Zhang X H. Macromolecules , 2018 . 51 ( 21 ): 8705 - 8711 . DOI:10.1021/acs.macromol.8b01757http://doi.org/10.1021/acs.macromol.8b01757 .

Shen Y, Xiong W, Li Y, Zhao Z, Lu H, Li Z. CCS Chem , 2020 . 2 620 - 630 . DOI:10.31635/ccschem.020.202000232http://doi.org/10.31635/ccschem.020.202000232 .

Dharmaratne N U, Pothupitiya J U, Bannin T J, Kazakov O I, Kiesewetter M K. ACS Macro Lett , 2017 . 6 ( 4 ): 421 - 425 . DOI:10.1021/acsmacrolett.7b00111http://doi.org/10.1021/acsmacrolett.7b00111 .

Li Y X, Zhao N, Wei C Z, Sun A, Liu S F, Li Z B. Eur Polym J , 2019 . 111 11 - 19 . DOI:10.1016/j.eurpolymj.2018.12.012http://doi.org/10.1016/j.eurpolymj.2018.12.012 .

Alamri H, Zhao J, Pahovnik D, Hadjichristidis N. Polym Chem , 2014 . 5 ( 18 ): 5471 - 5478 . DOI:10.1039/C4PY00493Khttp://doi.org/10.1039/C4PY00493K .

Li H, Zhao N, Ren C, Liu S, Li Z. Polym Chem , 2017 . 8 ( 47 ): 7369 - 7374 . DOI:10.1039/C7PY01673Ehttp://doi.org/10.1039/C7PY01673E .

Zhao J, Pahovnik D, Gnanou Y, Hadjichristidis N. Macromolecules , 2014 . 47 ( 12 ): 3814 - 3822 . DOI:10.1021/ma500830vhttp://doi.org/10.1021/ma500830v .

Zhang L, Nederberg F, Messman J M, Pratt R C, Hedrick J L, Wade C G. J Am Chem Soc , 2007 . 129 ( 42 ): 12610 - 12611 . DOI:10.1021/ja074131chttp://doi.org/10.1021/ja074131c .

Liu S F, Li H K, Zhao N, Li Z B. ACS Macro Lett , 2018 . 7 ( 6 ): 624 - 628 . DOI:10.1021/acsmacrolett.8b00353http://doi.org/10.1021/acsmacrolett.8b00353 .

Ladelta V, Bilalis P, Gnanou Y, Hadjichristidis N. Polym Chem , 2017 . 8 ( 3 ): 511 - 515 . DOI:10.1039/C6PY01983Hhttp://doi.org/10.1039/C6PY01983H .

Zhao N, Ren C, Shen Y, Liu S, Li Z. Macromolecules , 2019 . 52 ( 3 ): 1083 - 1091 . DOI:10.1021/acs.macromol.8b02690http://doi.org/10.1021/acs.macromol.8b02690 .

Peoples O P, Sinskey A J. US patent, C12N, 5245023. 1993-09-14

Peoples O P, Sinskey A L. US patent, C12N, 5250430. 1993-10-05

Bozell J J, Petersen G R. Green Chem , 2010 . 12 ( 4 ): 539 - 554 . DOI:10.1039/b922014chttp://doi.org/10.1039/b922014c .

Aleman C, Betran O, Casanovas J, Houk K N, Hall H K, J r. J Org Chem , 2009 . 74 ( 16 ): 6237 - 6244 . DOI:10.1021/jo9010969http://doi.org/10.1021/jo9010969 .

Houk K N, Jabbari A, Hall H K, Aleman C. J Org Chem , 2008 . 73 ( 7 ): 2674 - 2678 . DOI:10.1021/jo702567vhttp://doi.org/10.1021/jo702567v .

Yamashita K, Yamamoto K, Kadokawa J-i. Chem Lett , 2014 . 43 ( 2 ): 213 - 215 . DOI:10.1246/cl.130952http://doi.org/10.1246/cl.130952 .

Hong M, Chen E Y. Nat Chem , 2016 . 8 ( 1 ): 42 - 49 . DOI:10.1038/nchem.2391http://doi.org/10.1038/nchem.2391 .

Yuan Pengjun(袁鹏俊), Hong Miao(洪缪). Acta Polymerica Sinica(高分子学报) , 2019 . 50 ( 4 ): 327 - 337 . DOI:10.11777/j.issn1000-3304.2018.18232http://doi.org/10.11777/j.issn1000-3304.2018.18232 .

Liu Shaofeng(刘绍峰), Luo Wenlong(罗文龙), Li Zhibo(李志波). CN patent, C08G, 107722250A. 2017-11-07

Lin L, Han D, Qin J, Wang S, Xiao M, Sun L, Meng Y. Macromolecules , 2018 . 51 ( 22 ): 9317 - 9322 . DOI:10.1021/acs.macromol.8b01860http://doi.org/10.1021/acs.macromol.8b01860 .

Hong M, Tang X, Newell B S, Chen E Y X. Macromolecules , 2017 . 50 ( 21 ): 8469 - 8479 . DOI:10.1021/acs.macromol.7b02174http://doi.org/10.1021/acs.macromol.7b02174 .

Shen Y, Zhang J, Zhao N, Liu F, Li Z. Polym Chem , 2018 . 9 ( 21 ): 2936 - 2941 . DOI:10.1039/C8PY00389Khttp://doi.org/10.1039/C8PY00389K .

Shen Y, Zhang J, Zhao Z, Zhao N, Liu F, Li Z. Biomacromolecules , 2019 . 20 ( 1 ): 141 - 148 . DOI:10.1021/acs.biomac.8b01239http://doi.org/10.1021/acs.biomac.8b01239 .

Trotta J T, Jin M, Stawiasz K J, Michaudel Q, Chen W L, Fors B P. J Polym Sci, Part A: Polym Chem , 2017 . 55 ( 17 ): 2730 - 2737 . DOI:10.1002/pola.28654http://doi.org/10.1002/pola.28654 .

Higaki Y, Okazaki R, Takahara A. ACS Macro Lett , 2012 . 1 ( 9 ): 1124 - 1127 . DOI:10.1021/mz3002148http://doi.org/10.1021/mz3002148 .

Ding K, John A, Shin J, Lee Y, Quinn T, Tolman W B, Hillmyer M A. Biomacromolecules , 2015 . 16 ( 8 ): 2537 - 2539 . DOI:10.1021/acs.biomac.5b00754http://doi.org/10.1021/acs.biomac.5b00754 .

Hillmyer M A, Tolman W B. Acc Chem Res , 2014 . 47 ( 8 ): 2390 - 2396 . DOI:10.1021/ar500121dhttp://doi.org/10.1021/ar500121d .

Bai Y, He J, Zhang Y. Angew Chem Int Ed , 2018 . 57 ( 52 ): 17230 - 17234 . DOI:10.1002/anie.201811946http://doi.org/10.1002/anie.201811946 .

Zhang Y, Miyake G M, Chen E Y X. Angew Chem Int Ed , 2010 . 49 ( 52 ): 10158 - 10162 . DOI:10.1002/anie.201005534http://doi.org/10.1002/anie.201005534 .

Tang X, Hong M, Falivene L, Caporaso L, Cavallo L, Chen E Y X. J Am Chem Soc , 2016 . 138 ( 43 ): 14326 - 14337 . DOI:10.1021/jacs.6b07974http://doi.org/10.1021/jacs.6b07974 .

Hong M, Chen E Y X. Macromolecules , 2014 . 47 ( 11 ): 3614 - 3624 . DOI:10.1021/ma5007717http://doi.org/10.1021/ma5007717 .

Zhao Z, Shen Y, Kou X, Shi J, Wang R, Liu F, Li Z. Macromolecules , 2020 . 53 ( 9 ): 3380 - 3389 . DOI:10.1021/acs.macromol.0c00684http://doi.org/10.1021/acs.macromol.0c00684 .

Zhu J B, Watson E M, Tang J, Chen E Y X. Science , 2018 . 360 ( 6387 ): 398 - 403 . DOI:10.1126/science.aar5498http://doi.org/10.1126/science.aar5498 .

Yuan J, Xiong W, Zhou X, Zhang Y, Shi D, Li Z, Lu H. J Am Chem Soc , 2019 . 141 ( 12 ): 4928 - 4935 . DOI:10.1021/jacs.9b00031http://doi.org/10.1021/jacs.9b00031 .

Ren C L, Zhu X, Zhao N, Shen Y, Chen L F, Liu S F, Li Z B. Eur Polym J , 2019 . 119 130 - 135 . DOI:10.1016/j.eurpolymj.2019.07.022http://doi.org/10.1016/j.eurpolymj.2019.07.022 .

Lin B, Waymouth R M. J Am Chem Soc , 2017 . 139 ( 4 ): 1645 - 1652 . DOI:10.1021/jacs.6b11864http://doi.org/10.1021/jacs.6b11864 .

Lin B H, Waymouth R M. Macromolecules , 2018 . 51 ( 8 ): 2932 - 2938 . DOI:10.1021/acs.macromol.8b00540http://doi.org/10.1021/acs.macromol.8b00540 .

Zhang X Y, Jones G O, Hedrick J L, Waymouth R M. Nat Chem , 2016 . 8 ( 11 ): 1047 - 1053 . DOI:10.1038/nchem.2574http://doi.org/10.1038/nchem.2574 .

Orhan B, Tschan M J L, Wirotius A L, Dove A P, Coulembier O, Taton D. ACS Macro Lett , 2018 . 7 ( 12 ): 1413 - 1419 . DOI:10.1021/acsmacrolett.8b00852http://doi.org/10.1021/acsmacrolett.8b00852 .

Strandman S, Gautrot J E, Zhu X X. Polym Chem , 2011 . 2 ( 4 ): 791 - 799 . DOI:10.1039/C0PY00328Jhttp://doi.org/10.1039/C0PY00328J .

Ladelta V, Kim J D, Bilalis P, Gnanou Y, Hadjichristidis N. Macromolecules , 2018 . 51 ( 7 ): 2428 - 2436 . DOI:10.1021/acs.macromol.8b00153http://doi.org/10.1021/acs.macromol.8b00153 .

Wang B, Pan L, Ma Z, Li Y. Macromolecules , 2018 . 51 ( 3 ): 836 - 845 . DOI:10.1021/acs.macromol.7b02378http://doi.org/10.1021/acs.macromol.7b02378 .

Zhang D, Boopathi S K, Hadjichristidis N, Gnanou Y, Feng X. J Am Chem Soc , 2016 . 138 ( 35 ): 11117 - 11120 . DOI:10.1021/jacs.6b06679http://doi.org/10.1021/jacs.6b06679 .

更多指标>

浏览量

263

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

稀土催化的开环聚合研究进展

生物基δ-己内酯与L-丙交酯顺序开环共聚制备热塑性弹性体及其性质研究

结晶性生物可降解聚羟基脂肪酸酯的化学合成

苯甲氧基氧杂环内酯的合成及开环聚合研究