Synthesis and characterization of high performance poly(thioether imide)s via aromatic nucleophilic substitution reaction of isomeric AB-type monomers

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• 作者：Jiangtao Liu ; Guofei Chen ; Xingzhong Fang
• 关键词：Isomeric AB ; type monomers ; Self ; condensation ; Isomeric poly(thioether imide)s ; Aromatic nucleophilic substitution reaction
• 刊名：Polymer Bulletin
• 出版年：2015
• 出版时间：December 2015
• 年：2015
• 卷：72
• 期：12
• 页码：3269-3282
• 全文大小：470 KB
• 参考文献：1.Sroog CE (1991) Polyimides. Prog Polym Sci 16(4):561-94CrossRef
  2.Wilson D, Stenzewberger HD, Hergenrother PM (1990) Polyimide. Chapman & Hall, New YorkCrossRef
  3.Doldey R (1992) Polyimides-materials, processing, and applications. Pergamon, Oxford
  4.Ghosh MK, Mittal KL (1996) Polyimide: fundamentals and application. Marcel Dekker, New York
  5.Hasegawa M, Horie K (2001) Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci 26(2):259-35CrossRef
  6.Sroog CE (1976) Polyimides. J Macromol Sci Polym Rev 11(1):161-08CrossRef
  7.Ding Y, Bikson B, Nelson JK (2002) Polyimide membranes derived from poly(amic acid) salt precursor polymers. 1. Synthesis and characterization. Macromolecules 35(3):905-11CrossRef
  8.Ding Y, Bikson B, Nelson JK (2002) Polyimide membranes derived from poly(amic acid) salt precursor polymers. 2. Composite membrane preparation. Macromolecules 35(3):912-16CrossRef
  9.Facinelli JV, Gardner SL, Dong L, Sensenich CL, Davis RM, Riffle JS (1996) Controlled molecular weight polyimides from poly(amic acid) salt precursors. Macromolecules 29(23):7342-350CrossRef
  10.Yamanaka K, Jikei M, Kakimoto M (2000) Preparation and properties of hyperbranched aromatic polyimides via polyamic acid methyl ester precursors. Macromolecules 33(19):6937-944CrossRef
  11.Lee HJ, Won J, Park HC, Lee H, Kang YS (2000) Effect of poly(amic acid) imidization on solution characteristics and membrane morphology. J Membrane Sci 178(1-):35-1CrossRef
  12.Williams FJ, Donahue PE (1977) Reactions of phenoxides with nitro- and halo-substituted phthalimides. J Org Chem 42(21):3414-419CrossRef
  13.Williams FJ, Donahue PE (1978) Reaction of thiophenoxides with nitro- and halo-substituted phthalic anhydrides. J Org Chem 43(2):255-58CrossRef
  14.Takekoshi T, Wirth JG, Heath DR, Kochanowski JE, Manello JS, Webber MJ (1980) Polymer syntheses via aromatic nitro displacement reaction. J Polym Sci Polym Chem Ed 18(10):3069-080CrossRef
  15.White DM, Takekoshi T, Williams FJ, Relles HM, Donahue PE, Klopfer HJ, Loucks GR, Manello JS, Matthews RO, Schluenz RW (1981) Polyetherimides via nitro-displacement polymerization monomer synthesis and 13C-NMR analysis of monomers and polymers. J Polym Sci Polym Chem Ed 19(7):1635-658CrossRef
  16.Williams FJ, Relles HM, Manello JS, Donahue PE (1977a) Reactions of Phenoxides with Nitro-Substituted Phthalate Esters. J Org Chem 42(21):3419-425
  17.Williams FJ, Relles HM, Donahue PE, Manello JS (1977b) A direct synthesis of phenoxy-substituted phthalic anhydrides by aromatic nucleophilic displacement. J Org Chem 42(21):3425-431
  18.Wei HB, Pei XL, Fang XZ (2011) Comparative study on polyimides from isomeric 3,3-, 3,4-, and 4,4-linked bis(thioether anhydride)s. J Polym Sci, Part A: Polym Chem 49(11):2484-494CrossRef
  19.Fang XZ, Wang Z, Yang ZH, Gao LX, Li QX, Ding MX (2003) Novel polyimides derived from 2,3,3-4-benzophenonetetracarboxylic dianhydride. Polymer 44(9):2641-646CrossRef
  20.Fang XZ, Li QX, Wang Z, Yang ZH, Gao LX, Ding MX (2004) Synthesis and properties of novel polyimides derived from 2,2-3,3-benzophenonetetracarboxylic dianhydride. J Polym Sci, Part A: Polym Chem 42(9):2130-144CrossRef
  21.Li QX, Fang XZ, Wang Z, Gao LX, Ding MX (2003) Polyimides from isomeric oxydiphthalic anhydrides. J Polym Sci, Part A: Polym Chem 41(21):3249-260CrossRef
  22.Wei HB, Fang XZ, Han Y, Hu BL, Yan Q (2010) Synthesis and characterization of poly(thioether ether sulfone imide)s derived from isomeric bis(chlorophthalimide)s and bis(4-mercaptophenyl) sulfone. Eur Polym J 46(2):246-53CrossRef
  23.Wei HB, Wu XS, Hu BL, Fang XZ (2011) Preparation, characterization, and properties of poly(thioether ether ketone imide)s from isomeric bis(chlorophthalimide)s. Polym Adv Technol 22(12):2488-495CrossRef
  24.Liu JT, Chen GF, Fang XZ (2014) Preparation, characterization, and properties of poly(thioether ether imide)s from isomeric bis(chlorophthalimide)s and 4,4-thiobisbenzenethiol. Polym Adv Technol 25(3):329-37CrossRef
  25.Pei XL, Chen GF, Hou YJ, Fang XZ (2013) Comparative study on polyimides derived from isomeric diphenylsulfonetetracarboxylic dianhydrides. High Perform Polym 25(3):312-23CrossRef
  26.Ding MX (2007) Isomeric polyimides. Prog Polym Sci 32(6):623-68CrossRef
  27.Williams FJ, Donahue PE (1978) Reaction of thiophenoxides with nitro- and halo-substituted phthalimide derivatives. J Org Chem 43(2):250-54CrossRef
  28.Vaganova TA, Shundrina IK, Kusov SZ, Karpova EV, Bagryanskaya IY, Malykhin EV (2012) Synthesis and characterization of the first perfluoroaromatic polyimide of the AB-type. J Fluor Chem 135:129-36CrossRef
  29.Theis J, Ritter H (2012) Microwave-assisted synthesis and bulk polymerization of 3-aminophthalic anhydride as an AB-type monomer for the formation of linear and cyclic polyimides. Polym Int 61(8):1238-244CrossRef
  30.Wang ZY, Qi Y, Bender TP, Gao JP (1997)
• 作者单位：Jiangtao Liu (1)
  Guofei Chen (1)
  Xingzhong Fang (1)
  
  1. Ningbo Key Laboratory of Polymer Materials, Ningbo Institute of Material Technology and Engineering, Chinese Academy of Sciences, Ningbo, 315201, Zhejiang, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Polymer Sciences
  Characterization and Evaluation Materials
  Soft Matter and Complex Fluids
  Physical Chemistry
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1436-2449

文摘

A series of isomeric poly(thioether imide)s (PTIs) containing thioether linkages were prepared by aromatic nucleophilic substitution reaction of isomeric N-(4-mercaptophenyl)-3-chlorophthalimide and/or N-(4-mercaptophenyl)-4-chlorophthalimide. The inherent viscosities of these polymers were in the range of 0.38-.42 dL/g. The glass transition temperature increased with increasing the content of 3-substituted phthalimide unit in the polymer backbone. The 5 % weight loss temperatures of isomeric PTIs (a-strong class="EmphasisTypeBold ">e) were 506-31 °C in nitrogen and 509-36 °C in air, respectively. The isomeric PTIs (b-strong class="EmphasisTypeBold ">d) films exhibited good mechanical properties with tensile strength of about 90 MPa, elongation at break of more than 6.0 %, and tensile moduli of more than 2.2 GPa. The storage moduli of PTIs (b-strong class="EmphasisTypeBold ">d) almost completely maintained at about 2.0 GPa before reaching the corresponding glass transition temperatures. It is noted that the minimum melt viscosity of these polymers decreased with increasing the content of unsymmetrical 3- and 4-substituted phthalimide unit. Keywords Isomeric AB-type monomers Self-condensation Isomeric poly(thioether imide)s Aromatic nucleophilic substitution reaction