Ring-opening copolymerization of ε-caprolactone with 2,2-dimethyltrimethylene carbonate using N-heterocyclic carbene organocatalysts

Polymer Bulletin

Volumn 70, Issue 4, 2013, Pages 1289-1301

  Zhang, Rui ^a   Zhang, Lifang ^a   Wang, Junwen ^a   Guo, Xingna ^a  

^a SHANXI NORMAL UNIVERSITY   (China)

Author keywords

Caprolactone; 2,2 dimethyltrimethylene carbonate; Imidazol 2 ylidene; Ring opening copolymerization

Indexed keywords

2 ,2-DIMETHYLTRIMETHYLENE CARBONATES; ACTIVATED MONOMER MECHANISM; CAPROLACTONE; CONTROLLED MOLECULAR WEIGHT; IMIDAZOL-2-YLIDENE; INITIATOR CONCENTRATION; POLYMERIZATION MECHANISMS; RING OPENING COPOLYMERIZATION;

CARBONATION; CATALYSTS; COPOLYMERIZATION; COPOLYMERS; MONOMERS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EID: 84876461491     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-012-0854-3     Document Type: Article

References (29)

1. Thompson MS, Vadala TP, Vadala ML, Lin Y, Riffle JS (2008) Synthesis and applications of heterobifunctional poly(ethylene oxide) oligomers. Polymer 49:345-373
2. Rokicki G (2000) Aliphatic cyclic carbonates and spiroorthocarbonates as monomers. Prog Polym Sci 25:259-342
3. Yasuda H (2000) Organo transitionmetal initiated living polymerizations. Prog Polym Sci 25:573-626
4. Okada M (2002) Chemical syntheses of biodegradable polymers. Prog Polym Sci 27:87-133
5. Gerhard-Abozari E, Keul H, Hocker H (1994) Copolymers with soft and hard segments based on 2,2-dimethyltrimethylene carbonate and ε-caprolactone. Macromol Chem Phys 195:2371-2380
6. Hovestadt W, Keul H, Hocker H (1992) Tetraphenylporphyrin-aluminium compounds as initiators for the ring-opening polymerization of 2,2-dimethyltrimethylene carbonate: synthesis of homopolymers and copolymers with ε-caprolactone, ethylene oxide and propylene oxide. Polymer 33:1941-1948
7. Baiardo M, Alfonso GC (2001) Thermal and mechanical properties of diblock copolymers based on 2,2-dimethyltrimethylene carbonate and ε-caprolactone. Macromol Chem Phys 202:2509-2517
8. Akatsuka M, Aida T, Inoue S (1995) Alcohol/methylaluminum diphenolate systems as novel, versatile initiators for synthesis of narrow molecular weight distribution polyester and polycarbonate. Macromolecules 28:1320-1322
9. Kuhling S, Keul H, Hocker H (1992) Copolymerization of 2,2-dimethyltrimethylene carbonate with 2-allyloxymethyl-2-ethyltrimethylene carbonate and with ε-caprolactone using initiators on the basis of Li, Al, Zn and Sn. Macromol Chem Phys 193:1207-1217
10. Albertsson AC, Eklund MJ (1994) Synthesis of copolymers of 1,3-dioxan-2-one and oxepan-2-one using coordination catalysts. Polym Sci A 32:265-279
11. Kricheldorf HR, Stricker A (1999) Polylactones, 47. A-B-A triblock copolyesters and random copolyesters of trimethylene carbonate and various lactones via macrocyclic polymerization. Macromol Chem Phys 200:1726-1733
12. Joziasse CAP, Grablowitz H, Pennings AJ (2000) Star-shaped poly[(trimethylene carbonate)-co-(ε-capro-lactone)] and its block copolymers with lactide/glycolide: synthesis, characterization and properties. Macromol Chem Phys 201:107-112
13. Gupta AP, Kumar V (2007) New emerging trends in syntheticbiodegradable polymers - Polylactide: Acritique. Eur Polym J 43:4053-4074
14. Arduengo AJ, Dais RL, Harlow R, Kline M (1991) A stable crystalline carbine. J Am Chem Soc 113:361-363
15. Arduengo AJ, Dais RL, Harlow R, Kline M (1992) Mono(cclopentadienyl) titanium polymerization of ε-caprolactone. J Am Chem Soc 114:5530-5534
16. Arduengo AJ, Bertrand G (2009) Carbenes introduction. Chem Rev 109:3209-3210 (for an Editorial on Carbenes)
17. Bourissou D, Guerret O, Gabbai FP, Bertrand G (2000) Stable carbenes. Chem Rev 100:39-92 (for an Editorial on Carbenes)
18. Enders D, Niemeier O, Henseler A (2007) Organocatalysis by N-Heterocyclic carbenes. Chem Rev 107:5606-5655
19. Marion N, Díez-González S, Nolan SP (2007) N-Heterocyclic carbenes as organocatalysts. Angew Chem Int Ed 46:2988-3000
20. Hahn FE, Jahnke MC (2008) Heterocyclic carbenes: synthesis and coordination chemistry. Angew Chem Int Ed 47:3122-3172
21. Díez-González S, Marion N, Nolan SP (2009) N-Heterocyclic carbenes in late-transition metals catalysis. Chem Rev 109:3612-3676
22. Christmann M (2005) New developments in the asymmetric stetter reaction. Angew Chem Int Ed 44:2632-2634
23. Zeitler K (2005) Extending mechanistic routes in heterazolium catalysis-promising concepts for versatile synthetic methods. Angew Chem Int Ed 44:7506-7510
24. Sarel S, Pohoryles LA (1958) The stereochemistry and mechanism of reversible polymerization of 2,2-disubstituted 1,3-propanedil carbonates. J Am Chem Soc 80:4596-4599
25. Arduengo AJ, Krafczyk R, Schmutzler R, Craig HA, Goerlich JR, Marshall WJ, Unverzagt M (1999) Imidazolylidenes, imidazolinylidenes and imidazolidines. Tetrahedron 55:14523-14534
26. Kuhn N, Kratz T (1993) Synthesis of imidazol-2-ylidenes by reduction of imidazole-2(3H)-thiones. Synthesis 561-562
27. Bonhôte P, Dias A, Papageorgiou N, Kalyanasundaram K, Grätzel M (1996) Hydrophobic, highly conductive ambient-temperature molten salts. Inorg Chem 35:1168-1178
28. Samantaray MK, Katiyar V, Pang KL, Nanavati H, Ghosh P (2007) Silver N-heterocyclic carbene complexes as initiators for bulk ring-opening polymerization (ROP) of l-lactides. Chem. 692:1672-1682
29. Thomas F, Mehran Y, John PR (2003) A structure-permeability study of small drug-like molecules. Bioorg Med Chem Lett 13:719-722