Synthesis and properties of new poly(ether-esters containing aliphatic diol based on isosorbide. Effects of the microwave-assisted polycondensation

被引:31
作者
Chatti, S
Bortolussi, M
Bogdal, D
Blais, JC
Loupy, A
机构
[1] Inst Natl Rech Anal Physicochim, Ariana 2020, Tunisia
[2] Univ Paris Sud, CNRS, UMR 8615, ICMMO,Lab React Select Supports, F-91405 Orsay, France
[3] Politech Krakowska, Dept Chem, PL-31155 Krakow, Poland
[4] Univ Paris 06, CNRS, UMR 7613, Lab Chim Struct Organ & Biol, F-75252 Paris 5, France
关键词
polycondensation; isosorbide; poly(ether-ester)s; microwave activation; MALDI-TOF mass spectrometry;
D O I
10.1016/j.eurpolymj.2005.08.009
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Microwave irradiation was applied to synthesize to the bulk synthesis of novel poly(ether-ester)s based on diol-ether of isosorbide (1) and adipoyl chloride (2) or terephthaloyl chloride (3). Thus, the poly(ether-ester)s (4 and 5) consist partially of isosorbide. In order to check the influence of microwaves and possible specific non-thermal microwave effects, the reactions were comparatively performed inside a thermostated oil bath under similar conditions. The reaction conditions were varied to optimize both yields and molecular weights of poly(ether-esters. The reaction proceeded roughly five times faster under microwave irradiation, the polycondensation being almost completed (yields upto approximately 95%) within 5 min to afford a series of novel poly(ether-esters based with relatively high average molecular weights (M,, upto approximately 8000). The resulting poly(ether-esters were characterized by NMR (H-1 and C-13), FT-IR spectrometry, SEC measurements and MALDI-TOF mass spectrometry. Thermal properties of the poly(ether-esters (4 and 5) were investigated by means of differential scanning calorimetry (DSC). (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:410 / 424
页数:15
相关论文
共 37 条
[1]   SELECTIVE ALKYLATIONS OF 1,4/3,6-DIANHYDRO-D-GLUCITOL (ISOSORBIDE) [J].
ABENHAIM, D ;
LOUPY, A ;
MUNNIER, L ;
TAMION, R ;
MARSAIS, F ;
QUEGUINER, G .
CARBOHYDRATE RESEARCH, 1994, 261 (02) :255-266
[2]  
BACKMANN F, 1998, J MACROMOL RAPID COM, V19, P21
[3]   MASS-SPECTROMETRY OF SYNTHETIC-POLYMERS BY UV MATRIX-ASSISTED LASER DESORPTION IONIZATION [J].
BAHR, U ;
DEPPE, A ;
KARAS, M ;
HILLENKAMP, F ;
GIESSMANN, U .
ANALYTICAL CHEMISTRY, 1992, 64 (22) :2866-2869
[4]   Microwave assisted synthesis, crosslinking, and processing of polymeric materials [J].
Bogdal, D ;
Penczek, P ;
Pielichowski, J ;
Prociak, A .
LIQUID CHROMATOGRAPHY FTIR MICROSPECTROSCOPY MICROWAVE ASSISTED SYNTHESIS, 2003, 163 :193-263
[5]   POLYMERS FROM 1,4/3,6-DIANHYDROSORBITOL [J].
BRAUN, D ;
BERGMANN, M .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1992, 334 (04) :298-310
[6]   Microwave-assisted polycondensation of aliphatic diols of isosorbide with aliphatic disulphonylesters via phase-transfer catalysis [J].
Chatti, S ;
Bortolussi, M ;
Bogdal, D ;
Blais, JC ;
Loupy, A .
EUROPEAN POLYMER JOURNAL, 2004, 40 (03) :561-577
[7]   Synthesis of new polyethers derived from isoidide under phase-transfer catalysis: Reactivity and selectivity under microwaves and classical heating [J].
Chatti, S ;
Bortolussi, M ;
Loupy, A ;
Blais, JC ;
Bogdal, D ;
Roger, P .
JOURNAL OF APPLIED POLYMER SCIENCE, 2003, 90 (05) :1255-1266
[8]   Efficient synthesis of polyethers from isosorbide by microwave-assisted phase transfer catalysis [J].
Chatti, S ;
Bortolussi, M ;
Loupy, A ;
Blais, JC ;
Bogdal, D ;
Majdoub, M .
EUROPEAN POLYMER JOURNAL, 2002, 38 (09) :1851-1861
[9]   Synthesis of new diols derived from dianhydrohexitols ethers under microwave-assisted phase transfer catalysis [J].
Chatti, S ;
Bortolussi, M ;
Loupy, A .
TETRAHEDRON, 2000, 56 (32) :5877-5883
[10]   Cation and leaving group effects in isosorbide alkylation under microwave in phase transfer catalysis [J].
Chatti, S ;
Bortolussi, M ;
Loupy, A .
TETRAHEDRON, 2001, 57 (20) :4365-4370