Biodegradable Polyesters Based on cis-1,4-Butenediol

Summary: Homopolyesters based on cis-1,4-butenediol (cBeD) and aliphatic dicarboxylic acids (ADAs) were prepared by three different methods. First, cBeD was polycondensed with the dimethyl esters of ADAs in bulk. Regardless of the catalyst, only low-molar-mass polyesters were obtained. Second, polycondensations of cBeD with ADA dichlorides catalyzed by pyridine yielded polyesters with in the range of 8 000–13 500 Da. around 20 000 Da were achieved when the ADA dichlorides were polycondensed with DSDEN. These ring-opening polycondensations were optimized by a broad variation of the reaction conditions. Under optimized conditions a high molar fraction of cyclic polyesters was formed. All polyesters proved to be crystalline with melting temperatures (Tm) in the range of 55–120 °C. Polycondensations of cBeD.

[1]  K. Chrissafis,et al.  Effect of molecular weight on thermal degradation mechanism of the biodegradable polyester poly(ethylene succinate) , 2006 .

[2]  H. Kricheldorf,et al.  Telechelic polyesters of ethane diol and adipic or sebacic acid by means of bismuth carboxylates as non-toxic catalysts , 2005 .

[3]  H. Kricheldorf,et al.  Telechelic Poly(butylene terephthalate)s by Means of Bismuth Catalysts , 2005 .

[4]  Jin‐San Yoon,et al.  Synthesis and Chain Extension of Poly(L-lactic acid-co- succinic acid-co-1,4-butene diol) , 2005 .

[5]  T. McKenna,et al.  The Solid State Postcondensation of PET, 1 , 2004 .

[6]  H. Kricheldorf,et al.  Macrocycles 25. Cyclic poly(ether sulfone)s derived from 4-tert-butylcatechol , 2003 .

[7]  H. Kricheldorf,et al.  Cyclic polymers by kinetically controlled step-growth polymerization , 2003 .

[8]  R. Krüger,et al.  Macrocycles. 18. The role of cyclization in syntheses of Poly(ether-sulfone)s , 2001 .

[9]  H. Kricheldorf,et al.  Polylactones, 50: The reactivity of cyclic and noncyclic dibutyltin bisalkoxides as initiators in the polymerization of lactones , 2001 .

[10]  M. Maskos,et al.  Macrocycles. 15. The Role of Cyclization in Kinetically Controlled Polycondensations. 1. Polyester Syntheses , 2001 .

[11]  S. Oprea,et al.  Polyesters based on unsaturated diols , 2000 .

[12]  H. Kricheldorf,et al.  Polylactones 48. SnOct2-Initiated polymerizations of lactide : A mechanistic study , 2000 .

[13]  Shiro Kobayashi,et al.  Lipase-catalyzed polycondensation of dicarboxylic acid–divinyl esters and glycols to aliphatic polyesters , 1999 .

[14]  Manfred Schmidt,et al.  Macrocycles. 10. Macrocyclic poly(1,4-butanediol-ester)s by polycondensation of 2-stanna-1,3-dioxepane with dicarboxylic acid chlorides , 1999 .

[15]  S. Im,et al.  Degradation and Physical Properties of Aliphatic Copolyesters Derived from Mixed Diols , 1998 .

[16]  A. Pourjavadi,et al.  A new homologous series of linear aliphatic unsaturated hydroxypolyesters a polyol soft segments for polyurethanes: Synthesis and characterization , 1998 .

[17]  A. Duda,et al.  Polymerization of l,l-Lactide Initiated by Aluminum Isopropoxide Trimer or Tetramer , 1998 .

[18]  H. Kricheldorf,et al.  Macrocycles 2 Living macrocyclic polymerization of ε-caprolactone with 2,2-dibutyl-2-stanna-1,3-dioxepane as initiator , 1998 .

[19]  H. Pasch,et al.  Use of matrix-assisted laser desorption/ionization mass spectrometry for molar mass-sensitive detection in liquid chromatography of polymers , 1995 .

[20]  P. Sivasamy,et al.  Studies on hexolic anhydride based polyesters, 1. Characterization and sequence determination in hexolic based copolyesters by 1H- and 13C-NMR , 1991 .

[21]  A. Duda,et al.  Thermodynamics of L-lactide polymerization. Equilibrium monomer concentration , 1990 .

[22]  S. Huang,et al.  Synthesis and Characterization of Crosslinked Polymers for Biomedical Composites , 1988 .

[23]  A. Schindler,et al.  Aliphatic Polyesters. III. Molecular Weight and Molecular Weight Distribution in Alcohol- Initiated Polymerizations of e-Caprolactone , 1982 .

[24]  N. Ogata,et al.  Phosphonylation of an unsaturated polyester , 1979 .