乙烯基单体与环状单体“杂化共聚”的研究进展
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摘要
"杂化共聚"是将结构和活性差异很大的乙烯基单体与环状单体共聚合成新型聚合物的方法,是共聚物合成的一条新途径。文中介绍了"杂化共聚"的创新性成果,重点阐述了近5年来国内外乙烯基单体与环状单体的共聚反应及其机理,综述了"杂化共聚"2种催化剂膦腈碱(t-BuP_4)和B(C_6F_5)_3的应用及CF_3SO_3H/nBu4NI引发剂体系的应用,同时介绍了杂化共聚物的应用领域,最后展望了"杂化共聚"的发展前景。
"Hybrid Copolymerization" has opened up a new way for the synthesis of copolymers,which has important theoretical and practical significance.In this paper,innovative achievements of hybrid copolymerization were introduced.In addition,copolymerization reaction and its mechanism of vinyl monomer and cyclic monomer in the past five years were expounded.The application of two kinds of catalysts(t-BuP_4) and B(C_6F_5)_3 and the application of CF_3SO_3H/n Bu_4NI initiator system were reviewed.At the same time,the application field of the hybrid copolymer was introduced,and the development of the hybrid copolymer was prospected.
"Hybrid Copolymerization" has opened up a new way for the synthesis of copolymers,which has important theoretical and practical significance.In this paper,innovative achievements of hybrid copolymerization were introduced.In addition,copolymerization reaction and its mechanism of vinyl monomer and cyclic monomer in the past five years were expounded.The application of two kinds of catalysts(t-BuP_4) and B(C_6F_5)_3 and the application of CF_3SO_3H/n Bu_4NI initiator system were reviewed.At the same time,the application field of the hybrid copolymer was introduced,and the development of the hybrid copolymer was prospected.
引文
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[23]Sakata K,Fujimoto H.Quantum chemical study of B(C6F5)3catalyzed hydrosilylation of carbonyl group[J].J.Org.Chem.,2013,78:12505-12512.
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[26]Metal-free controlled ring-opening polymerization of 3-caprolactone in bulk using tris(pentafluorophenyl)borane as a catalyst[J].Polym.Chem.,2014,5:4726-4733.
[27]Kanazawa A,Kanaoka S,Aoshima S.Concurrent cationic vinyl-addition and ring-opening copolymerization using B(C6F5)3as a catalyst:copolymerization of vinyl ethers and isobutylene oxide via crossover propagation reactions[J].J.Am.Chem.Soc.,2013,135:9330-9333.
[28]Kanazawa A,Aoshima S.Concurrent cationic vinyl-addition and ring-opening copolymerization of vinyl ethers and oxiranes[J].Polym.J.,2016,48:679-687.
[29]Kanazawa A,Kanaoka S,Aoshima S.Rational design of oxirane monomers for efficient crossover reactions in concurrent cationic vinyl-addition and ring-opening copolymerization with vinyl ethers[J].Macromolecules,2014,47:6635-6644.
[30]Kanazawa A,Aoshima S.Frequency control of crossover reactions in concurrent cationic vinyl-addition and ring-opening copolymerization of vinyl ethers and oxiranes:specific roles of weak Lewis bases and solvent polarity[J].Polym.Chem.,2015,6:1-24.
[31]Kanazawa A,Aoshima S.Exclusive one-way cycle sequence control in cationic terpolymerization of general-purpose monomers via concurrent vinyl-addition,ring-opening,and carbonyl-addition mechanisms[J].ACS Macro Lett.,2015,4:783-787.
[32]Kanazawa A,Hashizume R,Kanaoka S,et al.Design of Benign initiator for living cationic polymerization of vinyl ethers:facile in situ generation of vinyl ether–hydrogen halide adducts and subsequent controlled polymerization without a Lewis acid catalyst[J].Macromolecules,2014,47:1578-1585.
[33]Kanazawa A,Kanda S,Kanaoka S,et al.Alkoxyoxirane,a unique cyclic monomer:controlled cationic homopolymerization mediated by long-lived species and copolymerization with vinyl ether via alkoxy group transfer[J].Macromolecules,2014,47:8531-8540.
[2]Nuyken O,Pask S.Ring-opening polymerization—an introductory review[J].Polymers,2013,5:361-403.
[3]Memeger W,Campbell G C,Davidson F.Poly(aminophosphazene)s and protophosphatranes mimic classical strong anionic base catalysts in the anionic ring-opening polymerization of lactams[J].Macromolecules.1996,29:6475-6480.
[4]Zhang L,Nederberg F,Pratt R C,et al.Phosphazene bases:a new category of organocatalysts for the living ring-opening polymerization of cyclic esters[J].Macromolecules,2007,40:4154-4158.
[5]De Winter J,Coulembier O,Gerbaux P,et al.High molecular weight poly(α,α',β-trisubstitutedβ-lactones)as generated by metalfree phosphazene catalysts.[J].Macromolecules,2010,43:10291-10296.
[6]Yan M,Yang H,Xing X.Synthesis and enzymatic degradation of poly(ε-caprolactone-co-ethylene carbonate-co-ethylene oxide)copolymer[J].Polym.Bull.,2013,70:467-478.
[7]Yang H,Yan M,Pispas S,et al.Synthesis of poly[(ethylene carbonate)-co-(ethylene oxide)]copolymer by phosphazene-catalyzed ROP[J].Macromol.Chem.Phys.,2011,212:2589-2593.
[8]Hu S,Dai G,Zhao J,et al.Ring-opening alternating copolymerization of epoxides and dihydrocoumarin catalyzed by a phosphazene superbase[J].Macromolecules,2016,49:4462-4472.
[9]Hu S,Zhao J,Zhang G.Noncopolymerization approach to copolymers via concurrent transesterification and ring-opening reactions[J].ACS Macro Lett.,2016,5:40-44.
[10]严满清,杨宏军,刑新明,等.无金属催化剂开环共聚己内酯和碳酸乙烯酯的合成[C].:大连:2011年全国高分子学术论文报告会,2011.
[11]张广照,许进宝,杨宏军.杂化聚合:一种合成聚合物的新反应[C].成都:2014年全国高分子材料科学与工程研讨会,2014.
[12]杨宏军.膦腈碱催化的聚合反应[D].合肥:中国科学技术大学,2012.Yang H J.Polymerization catalyzed by phosphazene[D〗Hefei:University of Science and Technology of China,2012.
[13]Yang H,Xu J,Pispas S,et al.Hybrid copolymerization ofε-caprolactone and methyl methacrylate[J].Macromolecules,2012,45:3312-3317.
[14]杨宏军,钱小磊,柏涛,等.己内酯与N-苯基马来酰亚胺的杂化共聚[J].高分子学报.2014(3):356-360.Yang H J,Qian X L,Bai T,et al.Hybrid copolymerization ofε-caprolactone and N-phenylmaleirnide[J].Acta Polymerica Sinica,2014(3):356-360.
[15]宋肄业,李静,柏涛,等.主链含酯键的基于聚甲基丙烯酸二甲氨基乙酯的共聚物合成与表征[J].高分子学报,2016(6):769-774.Song Y Y,Li J,Bai T,et al.Synthesis and characterization of main chain ester-containing poly(dimethylaminoethyl methacrylate)-based copolymers[J].Acta Polymerica Sinica,2016(6):769-774.
[16]Yang H,Xu J,Zhang G.Hybrid copolymerization of cyclic and vinyl monomers[J].Sci.China Chemi.,2013,56:1101-1104.
[17]杨宏军,许进宝,张广照.环状单体与乙烯基单体的杂化共聚[J].中国科学:化学.2013(8):1059-1062.Yang H J,Xu J B,Zhang G Z.Hybrid copolymerization of cyclic and vinyl monomers[J].Scientia Sinica Chimica,2013(8):1059-1062.
[18]Kiesewetter M K,Shin E J,Hedrick J L,et al.Organocatalysis:opportunities and challenges for polymer synthesis[J].Macromolecules,2010,43:2093-2107.
[19]Zhao J,Zhang G,Pispas S.Thermoresponsive brush copolymers with poly(propylene oxide-ran-ethylene oxide)side chains via metal-free anionic polymerization“grafting from”technique[J].J.Polym.Sci.Part A:Polym.Chem.,2010,48:2320-2328.
[20]严满清.聚己内酯的化学改性及其性能研究[D].合肥:中国科学技术大学,2013.Yan M Q.Studies on chemical modification and properties of poly(ε-caprolactoiie)[Z].Hefei:University of Science and Technology of China,2013.
[21]Yan M,Yang H,Zhang G.Synthesis and properties of antifouling poly(CL-co-z DMAEMA)zwitterionic copolymer by one-step hybrid copolymerization[J].Mater.Sci.Eng.,C,2015,51:189-195.
[22]Yang H,Bai T,Xue X,et al.A versatile strategy for synthesis of hyperbranched polymers with commercially available methacrylate inimer[J].RSC Adv.,2015,5:60401-60408.
[23]Sakata K,Fujimoto H.Quantum chemical study of B(C6F5)3catalyzed hydrosilylation of carbonyl group[J].J.Org.Chem.,2013,78:12505-12512.
[24]Asenjo-Sanz I,Veloso A,Miranda J I,et al.Zwitterionic ring-opening copolymerization of tetrahydrofuran and glycidyl phenyl ether with B(C6F5)3[J].Macromolecules.2015,48:1664-1672.
[25]Asenjo-Sanz I,Veloso A,Miranda J I,et al.Zwitterionic polymerization of glycidyl monomers to cyclic polyethers with B(C6F5)3[J].Polym.Chem.,2014,5:6905-6908.
[26]Metal-free controlled ring-opening polymerization of 3-caprolactone in bulk using tris(pentafluorophenyl)borane as a catalyst[J].Polym.Chem.,2014,5:4726-4733.
[27]Kanazawa A,Kanaoka S,Aoshima S.Concurrent cationic vinyl-addition and ring-opening copolymerization using B(C6F5)3as a catalyst:copolymerization of vinyl ethers and isobutylene oxide via crossover propagation reactions[J].J.Am.Chem.Soc.,2013,135:9330-9333.
[28]Kanazawa A,Aoshima S.Concurrent cationic vinyl-addition and ring-opening copolymerization of vinyl ethers and oxiranes[J].Polym.J.,2016,48:679-687.
[29]Kanazawa A,Kanaoka S,Aoshima S.Rational design of oxirane monomers for efficient crossover reactions in concurrent cationic vinyl-addition and ring-opening copolymerization with vinyl ethers[J].Macromolecules,2014,47:6635-6644.
[30]Kanazawa A,Aoshima S.Frequency control of crossover reactions in concurrent cationic vinyl-addition and ring-opening copolymerization of vinyl ethers and oxiranes:specific roles of weak Lewis bases and solvent polarity[J].Polym.Chem.,2015,6:1-24.
[31]Kanazawa A,Aoshima S.Exclusive one-way cycle sequence control in cationic terpolymerization of general-purpose monomers via concurrent vinyl-addition,ring-opening,and carbonyl-addition mechanisms[J].ACS Macro Lett.,2015,4:783-787.
[32]Kanazawa A,Hashizume R,Kanaoka S,et al.Design of Benign initiator for living cationic polymerization of vinyl ethers:facile in situ generation of vinyl ether–hydrogen halide adducts and subsequent controlled polymerization without a Lewis acid catalyst[J].Macromolecules,2014,47:1578-1585.
[33]Kanazawa A,Kanda S,Kanaoka S,et al.Alkoxyoxirane,a unique cyclic monomer:controlled cationic homopolymerization mediated by long-lived species and copolymerization with vinyl ether via alkoxy group transfer[J].Macromolecules,2014,47:8531-8540.