A semiempirical study of CO2 elimination in cationic polymerization of cyclic carbonates

Journal of Polymer Research

Volumn 17, Issue 6, 2010, Pages 759-768

  Holder, Andrew J ^a   Liu, Yi ^a  

^a UNIVERSITY OF MISSOURI KANSAS CITY   (United States)

Author keywords

AM1; Carbon dioxide elimination; Cationic polymerization; Expanding monomer

Indexed keywords

[CARBONYL; AM1; CATIONIC RING OPENING POLYMERIZATION; CHAIN-ENDS; CYCLIC CARBONATES; EXPANDING MONOMERS; EXPERIMENTAL INVESTIGATIONS; MONOMER CONCENTRATION; REACTION PATHS; RING SUBSTITUENTS; SEMI-EMPIRICAL; SEMI-EMPIRICAL CALCULATION; SOLVENT POLARITY; SPECIES EVOLUTION; THEORETICAL CALCULATIONS;

CARBON DIOXIDE; CARBOXYLATION; ETHERS; FUNCTIONAL GROUPS; MONOMERS; OXYGEN; POLYMERS; RING OPENING POLYMERIZATION; SOLVENTS;

CATIONIC POLYMERIZATION;

EID: 78049529496     PISSN: 10229760     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10965-009-9367-7     Document Type: Article

References (44)

1. JL Ferracane 2005 Developing a more complete understanding of stresses produced in dental composites during polymerization Dent Mater 21 36 42 10.1016/j.dental.2004.10.004 1:CAS:528:DC%2BD2MXoslKitQ%3D%3D (Pubitemid 40135729)
2. RL Sakaguchi BD Wiltbank NC Shah 2004 Critical configuration analysis of four methods for measuring polymerization shrinkage strain of composites Dent Mater 20 4 388 396 10.1016/j.dental.2003.11.002 1:CAS:528:DC%2BD2cXhsleltbc%3D
3. T Endo T Takata F Sanda T Ariga H Nemoto 1997 Cyclic carbonates, novel expandable monomers in polymerization Macromol Rapid Commun 18 461 469 10.1002/marc.1997.030180602 (Pubitemid 127477304)
4. Y Shibasaki F Sanda T Endo 2000 Cationic ring-opening polymerization of seven-membered cyclic carbonate with water-hydrogen chloride through activated monomer process Macromolecules 33 10 3590 3593 10.1021/ma9917444 1:CAS:528:DC%2BD3cXjtFGlu78%3D
5. CS Pinzino CC Chappelow S-S Chen L Jeang JD Eick 2005 Cyclic carbonate reactivity / compatibility with a silorane-based matrix resin J Dent Res 84 SI A Abstract # 0172
6. G Rokicki 2000 Aliphatic cyclic carbonates and spiroorthocarbonates as monomers Prog Polym Sci 25 259 342 10.1016/S0079-6700(00)00006-X 1:CAS:528:DC%2BD3cXkt1aqsbg%3D
7. Sadhir RJ, Luck RM (1992) Expanding monomers: Synthesis, characterization, and applications. CRC, Boca Raton
8. Bowen RL (1962) Dental Filling material comprising vinyl silane treated fused silica and a binder consisting of the reaction product of bisphenol and glicidyl acrylate. US Patent Number: 3066122
9. RL Bowen 1965 Adhesive bonding of various materials to hard tooth tissues. II. Bonding to dentin promoted by a surface-active comonomer J Dent Res 44 5 895 902 1:CAS:528:DyaF2MXkvFOgs7Y%3D
10. F Millich L Jeang JD Eick CC Chappelow CS Pinzino 1998 Elements of light-cured epoxy-based dental polymer systems J. Dent. Res. 77 603 608 10.1177/00220345980770041301 1:CAS:528:DyaK1cXis1Cltrc%3D
11. R Guggenberger W Weinmann 2000 Exploring beyond meth-acrylates Am J Dent 13 82 84
12. JL Ferracane JC Mitchem 2003 Relationship between composite contraction stress and leakage in Class V cavities Am. J. Dent. 16 4 239 243
13. CL Davidson AJ Feilzer 1997 Polymerization shrinkage, curing contraction, shrinkage stress, stress relief, resin composites, glass polyalkenoate cements, review J Dent 25 435 440 10.1016/S0300-5712(96)00063-2 1:CAS:528: DyaK1cXnvVOqsQ%3D%3D
14. WJ Bailey 1973 Synthesis of monomers that expand on polymerization J Elastoplast 5 142 1:CAS:528:DyaE3sXkvFaru74%3D
15. Bailey WJ, Sun RLJ, Katsuki T, Endo T, Iwama H, Tsushima R, Saigou K, Bitritto MM (1977) Ring-opening polymerization with expansion in volume. In Ring-Opening Polymerization, ACS Symp. Ser. No.59, Vol. 41.Washington, D.C.
16. Bailey WJ, Katsuki H, Endo T (1974) Synthesis of spiro ortho carbonates. J. Am. Chem. Soc., Div. Polym. Chem. Prepr,155, 445
17. WJ Bailey 1975 Cationic polymerization with expansion in volume J Macromol Sci-Chem A9 5 864
18. CRC Handbook of Chemistry and Physics, 78th Edn. CRC, 1997-1998.
19. T Takata F Sanda T Ariga N Nemoto T Endo 1997 Cyclic carbonates, novel expandable monomers on polymerization Macromol Rapid Commun 18 461 469 10.1002/marc.1997.030180602 1:CAS:528:DyaK2sXkt1yqtbk%3D (Pubitemid 127477304)
20. H Keul R Bacher H Hocker 1986 Makromol Chem 187 2579 10.1002/macp.1986. 021871107 1:CAS:528:DyaL2sXjtlGnsA%3D%3D
21. M Murayama F Sanda T Endo 1998 Macromolecules 31 919 10.1021/ma970878j 1:CAS:528:DyaK1cXkvVamsg%3D%3D
22. G Rokicki 2000 Progress in polymer Science 25 2 259 342 1:CAS:528:DC%2BD3cXkt1aqsbg%3D
23. O Haba H Tomizuka T Endo 2005 Macromolecules 38 9 3562 3563 10.1021/ma0476745 1:CAS:528:DC%2BD2MXislertL0%3D (Pubitemid 40672480)
24. D Takeuchi T Aida T Endo 2000 Living ring-opening polymerization of cyclic carbonates mediated by bulky titanium bisphenolates Macromol Chem Phys 201 2267 2275 10.1002/1521-3935(20001101)201:17<2267::AID-MACP2267>3.0. CO;2-V 1:CAS:528:DC%2BD3MXis1Og
25. HR Kricheldorf J Jenssen 1989 Cationic polymerization of trimethylene carbonate and other cyclic carbonates J Macromol Sci-Chem A26 4 631 644 10.1080/00222338908051999 1:CAS:528:DyaL1MXksFyntrk%3D
26. A-C Albertsson M Sjoeling 1992 J Mol Sci, Pure Appl Chem A29 1 43 10.1080/10101329208054106
27. T Ariga T Takata T Endo 1997 Cationic ring-opening polymerization of cyclic carbonates with alkyl halides to yield polycarbonate without the ether unit by suppression of elimination of carbon dioxide Macromolecules 30 737 744 10.1021/ma9607325 1:CAS:528:DyaK2sXht1Oiu7o%3D
28. J Matsuo F Sanda T Endo 1998 Cationic ring-opening polymerization behavior of an aliphatic seven-membered cyclic carbonate, 1, 3-dioxepan-2-one Macromol Chem Phys 199 97 102 10.1002/(SICI)1521-3935(19980101)199:1<97::AID- MACP97>3.0.CO;2-D 1:CAS:528:DyaK1cXhtVKntbg%3D (Pubitemid 128477811)
29. F Sanda T Fueki T Endo 1999 Cationic ring-opening polymerization of an exomethylene group carrying cyclic carbonate. Pseudo-living polymerization of 5-methylene-1, 3-dioxan-2one by the assistance of the exomethylene group Macromolecules 32 4220 4224 10.1021/ma981947c 1:CAS:528:DyaK1MXjsFCquro%3D
30. N Nemoto F Sanda T Endo 2001 Cationic ring-opening polymerization of six-membered cyclic carbonates with ester groups J Polym Sci A: Polym Chem 39 1305 1317 10.1002/pola.1108 1:CAS:528:DC%2BD3MXislartb4%3D (Pubitemid 32425400)
31. MJS Dewar EG Zoebich EF Healy JJP Stewart 1985 J Am Chem Soc 107 3902 3909 10.1021/ja00299a024 1:CAS:528:DyaL2MXktFWlsLk%3D
32. G Alagona C Ghio Z Latajka J Tomasi 1990 Basis set superposition errors and counterpoise corrections for some basis sets evaluated for a few X-...M Dimers J Phys Chem 94 2367 10.1021/j100369a014
33. AJ Holder DA White CD Harris JD Eick CC Chappelow 2001 A semiempirical quantum mechanical study of the cationic homopolymerization of expanding and potentially expanding monomer systems J Mol Struct (Thoechem) 541 159 169 10.1016/S0166-1280(00)00763-6 1:CAS:528:DC%2BD3MXislGntLo%3D (Pubitemid 32397457)
34. MJS Dewar EG Zoebisch EF Healy JJP Stewart 1985 AM1: a new general purpose quantum mechanical molecular model J Am Chem Soc 107 3902 3909 10.1021/ja00299a024 1:CAS:528:DyaL2MXktFWlsLk%3D
35. AMPAC with Graphical User Interface, Ver. 8.0, Semichem: Shawnee Mission, KS, 2007
36. JW McIver A Komornicki 1971 Force rapid geometry optimization for semiempirical molecular orbital methods Chem Phys Lett 10 303 306 10.1016/0009-2614(71)80294-4 1:CAS:528:DyaE3MXltFaqurY%3D
37. JW McIver A Komornicki 1972 Structure of transition states in organic reactions. General theory and applications to the cyclobutene-butadiene isomerization using the semiempirical molecular orbital method J Am Chem Soc 94 2625 2633 10.1021/ja00763a011 1:CAS:528:DyaE38XhsFejt7s%3D
38. JL Schrenk MC Palazzotto KR Mann 1983 Inorg Chem 22 4047 4049 10.1021/ic00168a044 1:CAS:528:DyaL2cXmslyk
39. RG Parr W Yang 1984 J Am Chem Soc 106 4049 4050 10.1021/ja00326a036 1:CAS:528:DyaL2cXkt1ynsrc%3D
40. W Yang WJ Mortier 1986 J Am Chem Soc 108 5708 5711 10.1021/ja00279a008 1:CAS:528:DyaL28Xltlehtb8%3D
41. RS Mulliken 1955 J Chem Phys 23 1833 1840 10.1063/1.1740588 1:CAS:528:DyaG28Xnt1Kq
42. F Mendez JL Gazquez 1994 J Am Chem Soc 116 9298 9301 10.1021/ja00099a055 1:CAS:528:DyaK2cXntVShs7w%3D
43. F Gilardoni J Weber TR Ward 1998 J Phys Chem A 102 20 3607 3613 10.1021/jp980521x 1:CAS:528:DyaK1cXis12mu74%3D
44. Lin T (1998) Photo-cationic polymerization of cyclic carbonates and vinyl ethers. Thesis, University of Missouri Kansas City, Kansas City, MO