Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)

Min Lu; Xiang Zhu; Xiao-hong Li; Xiao-ming Yang; Ying-feng Tu

doi:10.1007/s10118-017-1951-4

Your Location：

Home >

Browse articles >

Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)

Papers | Updated：2021-02-18

- Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)
- Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)
- Chinese Journal of Polymer Science 2017年35卷第9期页码：1051-1060
- Affiliations：
  
  Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China
- Author bio：
  
  Ying-feng Tu (屠迎锋), E-mail:tuyingfeng@suda.edu.cn
- Funds：
  
  the National Natural Science Foundation of China(21474067);the Priority Academic Program Development of Jiangsu Higher Education Institutions
- DOI：10.1007/s10118-017-1951-4
  中图分类号：
- 收稿：2017-03-08，
  
  修回：2017-4-5，
  
  录用：2017-4-6，
  
  纸质出版：2017-09-05
- Accepted：
Scan QR Code
Min Lu, Xiang Zhu, Xiao-hong Li, 等. Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)[J]. Chinese Journal of Polymer Science, 2017,35(9):1051-1060.

Min Lu, Xiang Zhu, Xiao-hong Li, et al. Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)[J]. Chinese Journal of Polymer Science, 2017, 35(9): 1051-1060.
Min Lu, Xiang Zhu, Xiao-hong Li, 等. Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)[J]. Chinese Journal of Polymer Science, 2017,35(9):1051-1060. DOI： 10.1007/s10118-017-1951-4.

Min Lu, Xiang Zhu, Xiao-hong Li, et al. Synthesis of Cyclic Oligo(ethylene adipate)s and Their Melt Polymerization to Poly(ethylene adipate)[J]. Chinese Journal of Polymer Science, 2017, 35(9): 1051-1060. DOI： 10.1007/s10118-017-1951-4.

摘要

Abstract

We present here the first synthesis of cyclic oligo(ethylene adipate)s (COEAs)

via

pseudo-high dilution condensation reaction of adipoyl chloride with ethylene glycol

and the synthesis of corresponding poly(ethylene adipate) (PEA)

via

the melt polymerization of COEAs. The structure of COEAs was characterized and proved by

H-NMR and MALDI-TOF mass measurements. The effects of organic base

reaction temperature and the ratio of adipoyl chloride to ethylene glycol on the yield of COEAs were studied

and the optimum reaction condition was revealed. PEA

a diacid and diol based semi-crystalline green aliphatic polyester

was synthesized by the melt polymerization of COEAs using Ti(

-C

as catalyst and 1

10-decanediol as initiator at 200℃

which follows the polycondensation-coupling ring-opening polymerization method. Our strategy should be applicable to the synthesis of versatile aliphatic polyesters based on diacid and diol monomers

which have potential applications as biocompatible and biodegradable materials.

关键词

Keywords

references

S.S. Bari , A. Chatterjee , S. Mishra . Polym. Rev. , 2016 . 56 ( 2 ): 287 DOI: 10.1080/15583724.2015.1118123 http://doi.org/10.1080/15583724.2015.1118123 .

L. Lu , M.J. Yaszemski , A.G. Mikos . Biomaterials , 2001 . 22 ( 24 ): 3345 DOI: 10.1016/S0142-9612(01)00172-7 http://doi.org/10.1016/S0142-9612(01)00172-7 .

S.T. Lim , Y.H. Hyun , H.J. Choi , M.S. Jhon . Chem. Mater. , 2002 . 14 ( 4 ): 1839 DOI: 10.1021/cm010377j http://doi.org/10.1021/cm010377j .

B. Surnar , M. Jayakannan . Biomacromolecules , 2016 . 17 ( 12 ): 4075 DOI: 10.1021/acs.biomac.6b01608 http://doi.org/10.1021/acs.biomac.6b01608 .

K.I. Kasuya , K.I. Takagi , S.I. Ishiwatari , Y. Yoshida , Y. Doi . Polym. Degrad. Stab. , 1998 . 59 ( 1-3 ): 327 DOI: 10.1016/S0141-3910(97)00155-9 http://doi.org/10.1016/S0141-3910(97)00155-9 .

Y.S. He , J.B. Zeng , S.L. Li , Y.Z. Wang . Thermochim. Acta , 2012 . 529 80 DOI: 10.1016/j.tca.2011.11.031 http://doi.org/10.1016/j.tca.2011.11.031 .

S. Qiu , Z. Su , Z. Qiu . Ind. Eng. Chem. Res. , 2016 . 55 ( 39 ): 10286 DOI: 10.1021/acs.iecr.6b02654 http://doi.org/10.1021/acs.iecr.6b02654 .

A. Lv , Y. Cui , F.S. Du , Z.C. Li . Macromolecules , 2016 . 49 ( 22 ): 8449 DOI: 10.1021/acs.macromol.6b01325 http://doi.org/10.1021/acs.macromol.6b01325 .

N. Kuhl , M. Abend , S. Bode , U.S. Schubert , M.D. Hager . J. Appl. Polym. Sci. , 2016 . 133 ( 44 ): 44168 .

M. Vandesteene , N. Jacquel , R. Saint-Loup , N. Boucard , C. Carrot , A. Rousseau , F. Fenouillot . Chinese J. Polym. Sci. , 2016 . 34 ( 7 ): 873 DOI: 10.1007/s10118-016-1805-5 http://doi.org/10.1007/s10118-016-1805-5 .

A. Diaz , R. Katsarava , J. Puiggali . Int. J. Mol. Sci. , 2014 . 15 ( 5 ): 7064 DOI: 10.3390/ijms15057064 http://doi.org/10.3390/ijms15057064 .

J.B. Zhao , X.F. Wu , W.T. Yang . J. Appl. Polym. Sci. , 2004 . 92 ( 5 ): 3333 DOI: 10.1002/(ISSN)1097-4628 http://doi.org/10.1002/(ISSN)1097-4628 .

C.Q. Huang , S.Y. Luo , S.Y. Xu , J.B. Zhao , S.L. Jiang , W.T. Yang . J. Appl. Polym. Sci. , 2009 . 115 ( 3 ): 1555 .

S.Y. Xu , Y.H. Shi , J.B. Zhao , S.L. Jiang , W.T. Yang . Polym. Adv. Technol. , 2011 . 22 ( 12 ): 2360 DOI: 10.1002/pat.v22.12 http://doi.org/10.1002/pat.v22.12 .

J.C. Morales-Huerta , de Ilarduya A. Martínez , S. Muñoz-Guerra . ACS Sustainable Chem. Eng. , 2016 . 4 ( 9 ): 4965 DOI: 10.1021/acssuschemeng.6b01302 http://doi.org/10.1021/acssuschemeng.6b01302 .

D.J. Brunelle , J.E. Bradt , J. Serth-Guzzo , T. Takekoshi , T.L. Evans , E.J. Pearce , P.R. Wilson . Macromolecules , 1998 . 31 ( 15 ): 4782 DOI: 10.1021/ma971491j http://doi.org/10.1021/ma971491j .

J.H. Youk , R.P. Kambour , W.J. MacKnight . Macromolecules , 2000 . 33 ( 10 ): 3594 DOI: 10.1021/ma991838d http://doi.org/10.1021/ma991838d .

M.P.F. Pepels , F. van der Sanden , E. Gubbels , R. Duchateau . Macromolecules , 2016 . 49 ( 12 ): 4441 DOI: 10.1021/acs.macromol.6b00744 http://doi.org/10.1021/acs.macromol.6b00744 .

Q.Z. Xu , J.Y. Chen , W.C. Huang , T.G. Qu , X.H. Li , Y. Li , X.M. Yang , Y.F. Tu . Macromolecules , 2013 . 48 ( 18 ): 7274 .

J.Y. Chen , D.X. Chen , W.C. Huang , X.M. Yang , X.H. Li , Y.F. Tu , X.L. Zhu . Polymer , 2016 . 107 29 DOI: 10.1016/j.polymer.2016.11.001 http://doi.org/10.1016/j.polymer.2016.11.001 .

X. Zhu , J.L. Gu , X.H. Li , X.M. Yang , L. Wang , Y.J. Li , H. Li , Y.F. Tu . Polym. Chem. , 2017 . 8 1953 DOI: 10.1039/C7PY00068E http://doi.org/10.1039/C7PY00068E .

C. Dell'Olio , S. Leonard , B. Dao , R.J. Varley , K. Pingkarawat . J. Mater. Sci. , 2015 . 50 ( 24 ): 8073 DOI: 10.1007/s10853-015-9375-4 http://doi.org/10.1007/s10853-015-9375-4 .

J.C. Morales-Huerta , de Ilarduya A. Martínez , S. Muñoz-Guerra . Polymer , 2016 . 87 148 DOI: 10.1016/j.polymer.2016.02.003 http://doi.org/10.1016/j.polymer.2016.02.003 .

Y. Nakayama , K. Sakaguchi , R. Tanaka , Z. Cai , T. Shiono . Macromol. Symp. , 2015 . 350 ( 1 ): 7 DOI: 10.1002/masy.v350.1 http://doi.org/10.1002/masy.v350.1 .

D. Zhang , M.A. Hillmyer , W.B. Tolman . Macromolecules , 2004 . 37 ( 22 ): 8198 DOI: 10.1021/ma048092q http://doi.org/10.1021/ma048092q .

I. Goodman , B.F. Nesbitt . Polymer , 1960 . 1 384 DOI: 10.1016/0032-3861(60)90048-3 http://doi.org/10.1016/0032-3861(60)90048-3 .

P. Siriphannon , P. Monvisade . Bull. Mater. Sci. , 2013 . 36 ( 1 ): 121 DOI: 10.1007/s12034-013-0427-6 http://doi.org/10.1007/s12034-013-0427-6 .

P. Monvisade , P. Loungvanidprapa . Eur. Polym. J. , 2007 . 43 ( 8 ): 3408 DOI: 10.1016/j.eurpolymj.2007.05.009 http://doi.org/10.1016/j.eurpolymj.2007.05.009 .

W.J. Choi , S.H. Kim , Y.J. Kim , S.C. Kim . Polymer , 2004 . 45 ( 17 ): 6045 DOI: 10.1016/j.polymer.2004.06.033 http://doi.org/10.1016/j.polymer.2004.06.033 .

H.J. Wang , H.P. Feng , X.C. Wang , Q.C. Du , C. Yan . Chinese J. Polym. Sci. , 2015 . 33 ( 6 ): 823 DOI: 10.1007/s10118-015-1627-x http://doi.org/10.1007/s10118-015-1627-x .

A.E. Taggi , H. Wack , A.M. Hafez , S. France , T. Lectka . Org. Lett. , 2002 . 4 ( 4 ): 627 DOI: 10.1021/ol0172525 http://doi.org/10.1021/ol0172525 .

D.H. Paull , A. Weatherwax , T. Lectka . Tetrahedron , 2009 . 65 ( 34 ): 6771 DOI: 10.1016/j.tet.2009.05.079 http://doi.org/10.1016/j.tet.2009.05.079 .

Hyatt, J. A. and Raynolds, P. W. , "Organic reactions", John Wiley & Sons, 1994, p. 159

J. Wu , T.G. Qu , L.F. Gao , X.M. Yang , X.H. Li , Y.F. Tu , X.L. Zhu . Chinese J. Polym. Sci. , 2015 . 33 ( 8 ): 1069 DOI: 10.1007/s10118-015-1675-2 http://doi.org/10.1007/s10118-015-1675-2 .

D.X. Chen , L.F. Gao , X.H. Li , Y.F. Tu . Chinese J. Polym. Sci. , 2017 . 35 ( 5 ): 681 DOI: 10.1007/s10118-017-1919-4 http://doi.org/10.1007/s10118-017-1919-4 .

H. Wu , Z. Qiu . Ind. Eng. Chem. Res. , 2012 . 51 ( 40 ): 13323 DOI: 10.1021/ie301968f http://doi.org/10.1021/ie301968f .

G. Lugito , E.M. Woo . Soft matter , 2015 . 11 ( 5 ): 908 DOI: 10.1039/C4SM02489C http://doi.org/10.1039/C4SM02489C .

D. Rohindra , K. Kuboyama , T. Ougizawa . Eur. Polym. J. , 2012 . 48 ( 10 ): 1768 DOI: 10.1016/j.eurpolymj.2012.07.013 http://doi.org/10.1016/j.eurpolymj.2012.07.013 .

R. Liang , Y.C. Chen , C.Q. Zhang , J. Yin , X.L. Liu , L.K. Wang , J.J. Yang . Chinese J. Polym. Sci. , 2017 . 35 ( 4 ): 558 DOI: 10.1007/s10118-017-1917-6 http://doi.org/10.1007/s10118-017-1917-6 .

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Thermodynamics of Aromatic Cyclic Ester Polymerization in Bulk

End-to-End Neuron-inspired Signal Transduction Using Organic Electrochemical Transistors

Sliding Dynamics of Ring Chain on a Rod-Coil Block Copolymer in Rotaxane

Molecularly Engineered Polyimide Films with Switchable Cavitation for Bidirectional Passive Thermal Regulation

On-demand Peelable UV-curable Adhesives with Superior Bonding Strength: Rational Molecular Engineering of Cohesion-adhesion Synergy