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Block and Random Copolymers of 1,2-Cyclohexyl Cyclocarbonate and L-Lactide or Trimethylene Carbonate Synthesized by Ring-Opening Polymerization

Abstract : The sequential and random ring-opening polymns. (ROP) of racemic-trans-cyclohexene carbonate (rac-CHC) or enantiopure trans-(R,R)-cyclohexene carbonate ((R,R)-CHC) with L-lactide (LLA) or trimethylene carbonate (TMC) have been performed. Catalytic systems based on zinc diaminophenolate [(NNO)ZnEt] ((NNO)- = 2,4-di-tert-butyl-6-\[(2'-dimethylaminoethyl)methylamino]methyl\phenolate)) or tris[N,N-bis(trimethysilyl)amide]yttrium (Y[N(SiMe3)2]3) complexes, or a guanidine-type organocatalyst (1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD), combined to an alc. (BnOH or iPrOH) as initiator/chain-transfer agent were used. Well-defined diblock P(rac-CHC)-b-PLLA and P((R,R)-CHC)-b-PLLA and random P(rac-CHC)-co-PLLA and P(rac-CHC)-co-PTMC copolymers were thus synthesized with molar mass values up to Mn,NMR = ca. 34 000 g mol-1 and rather narrow dispersity values (DM = 1.2-1.7). 1H and 13C\1H\ NMR characterizations of the copolymers revealed the presence of -OBn or -OiPr chain-end groups, thereby supporting the active role of exogenous alc. as initiator. No decarboxylation reaction was ever obsd. during any copolymn., thus providing PCHC/PLLA and PCHC/PTMC copolymers void of ether defects. Thermal anal. of the copolymers assessed by DSC and TGA confirmed their block or random structure. The block PCHC-b-PLA and the random PCHC-co-PLLA and PCHC-co-PTMC copolymers represent the first examples of such copolymers synthesized by ring-opening copolymn. of the two comonomers. The latter PCHC-co-PTMC copolymers randomly combining CHC and TMC units are the first examples ever reported
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01156436
Contributor : Laurent Jonchère <>
Submitted on : Wednesday, May 27, 2015 - 1:25:11 PM
Last modification on : Friday, July 10, 2020 - 4:19:50 PM

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Abdou Khadri Diallo, William Guerin, Martine Slawinski, Jean-Michel Brusson, Jean-François Carpentier, et al.. Block and Random Copolymers of 1,2-Cyclohexyl Cyclocarbonate and L-Lactide or Trimethylene Carbonate Synthesized by Ring-Opening Polymerization. Macromolecules, American Chemical Society, 2015, 48 (10), pp.3247--3256. ⟨10.1021/acs.macromol.5b00548⟩. ⟨hal-01156436⟩

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