How to explain low molar masses in PolyHydroxyUrethanes (PHUs)

European Polymer Journal

Volumn 71, Issue , 2015, Pages 1-11

  Besse, Vincent ^a   Camara, Fatoumata ^a   Méchin, Francoise ^b   Fleury, Etienne ^b   Caillol, Sylvain ^a   Pascault, Jean Pierre ^b   Boutevin, Bernard ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b UNIVERSITÉ DE LYON   (France)

Author keywords

Carbonates; Molar masses; Oxazolidinone; PolyHydroxyUrethanes; Side reactions; Ureas

Indexed keywords

AMINES; CARBONATES; CARBONATION; CHROMATOGRAPHY; ETHERS; MANGANESE; METABOLISM; POLYMERS; SIZE EXCLUSION CHROMATOGRAPHY; UREA;

CYCLIC CARBONATES; GLYCEROL CARBONATE; MODEL REACTIONS; OXAZOLIDINONES; PHYSICOCHEMICAL PROPERTY; POLYHYDROXYURETHANES; RING OPENING REACTION; SIDE REACTIONS;

MOLAR MASS;

EID: 84938066113     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2015.07.020     Document Type: Article

References (40)

1. M.H. Karol, and J.A. Kramarik Phenyl isocyanate is a potent chemical sensitizer Toxicol. Lett. 89 1996 139 146
2. E. Delebecq, J.P. Pascault, B. Boutevin, and F. Ganachaud On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane. Chem. Rev. 113 2013 80 118
3. S. Ephraim, A.E. Woodward, and R.B. Mesrobian Kinetic studies of the reaction of phenyl isocyanate with alcohols in various solvents J. Am. Chem. Soc. 80 1958 1326 1328
4. J.M. Raquez, M. Deleglise, M.F. Lacrampe, and P. Krawczak Thermosetting (bio) materials derived from renewable resources: a critical review Prog. Polym. Sci. 35 2010 487 509
5. O.L. Figovski, and L.D. Shapovalov Features of reaction amino-cyclocarbonate for production of new type nonisocyanate polyurethane coatings Macromol. Symp. 187 2002 325 332
6. J. Guan, Y. Song, Y. Lin, X. Ying, M. Zuo, Y. Zhao, X. Tao, and Q. Zheng Progress in study of non-isocyanate polyurethane Ind. Eng. Chem. Res. 50 2011 6517 6527
7. M.S. Kathalewar, P.B. Joshi, A.S. Sabnis, and V.C. Malshe Non-isocyanate polyurethanes: from chemistry to applications RSC Adv. 3 2013 4110 4129
8. B. Nohra, L. Candy, J.F. Blanco, C. Guerin, Y. Raoul, and Z. Mouloungui From petrochemical polyurethanes to biobased polyhydroxyurethanes Macromolecules 46 2013 3771 3792
9. O. Kreye, H. Mutlu, and M.A.R. Meier Sustainable routes to polyurethane precursors Green Chem. 15 2013 1431 1455
10. N. Kihara, and T. Endo Synthesis and properties of poly(hydroxyurethane)s J. Polym. Sci. Part A: Polym. Chem. 31 1993 2765 2773
11. V. Besse, R. Auvergne, S. Carlotti, G. Boutevin, B. Otazaghine, S. Caillol, J.P. Pascault, and B. Boutevin Synthesis of isosorbide based polyurethanes: an isocyanate free method React. Funct. Polym. 73 2013 588 594
12. J.M. Whelan, M. Hill, R.J. Cotter, U.S. Patent 3,072,613, 1963.
13. G. Rokicki, and M. Lewandowski Epoxy resins modified by carbon dioxide Angew. Makromol. Chem. 148 1987 53 66
14. M. Fache, E. Darroman, V. Besse, R. Auvergne, S. Caillol, and B. Boutevin Vanillin, a promising biobased building-block for monomer synthesis Green Chem. 16 2014 1987 1998
15. M. Desroches, S. Benyahya, V. Besse, R. Auvergne, B. Boutevin, and S. Caillol Synthesis of bio-based building blocks from vegetable oils: a platform chemicals approach Lipid Technol. 26 2014 35 38
16. D.C. Webster Cyclic carbonate functional polymers and their applications Prog. Org. Coat. 47 2003 77 86
17. M. Fleischer, H. Blattmann, and R. Muelhaupt Glycerol-, pentaerythritol- and trimethylalpropane-based polyurethanes and their cellulose carbonate composites prepared via the non-isocyanate route with catalytic carbon dioxide fixation Green Chem. 15 2013 934 942
18. A. Boyer, E. Cloutet, T. Tassaing, B. Gadenne, C. Alfos, and H. Cramail Solubility in CO2 and carbonation studies of epoxidized fatty acid diesters: towards novel precursors for polyurethane synthesis Green Chem. 12 2010 2205 2213
19. L. Maisonneuve, A.S. More, S. Flotran, C. Alfos, F. Robert, Y. Landais, T. Tassaing, E. Grau, and H. Cramail Novel green fatty acid-based bis-cyclic carbonates for the synthesis of isocyanate-free poly(hydroxyurethane amide)s RSC Adv. 4 2014 25795 25803
20. N. Aoyagi, Y. Furusho, and T. Endo Convenient synthesis of cyclic carbonates from CO2 and epoxides by simple secondary and primary ammonium iodides as metal-free catalysts under mild conditions and its application to synthesis of polymer bearing cyclic carbonate moiety J. Polym. Sci. Part A: Polym. Chem. 51 2013 1230 1242
21. M. North, R. Pasquale, and C. Young Synthesis of cyclic carbonates from epoxides and CO2 Green Chem. 12 2010 1514 1539
22. H. Blattmann, M. Fleischer, M. Bähr, and R. Mülhaupt Isocyanate- and phosgene-free routes to polyfunctional cyclic carbonates and green polyurethanes by fixation of carbon dioxide Macromol. Rapid Commun. 35 2014 1238 1254
23. V. Besse, G. Foyer, R. Auvergne, S. Caillol, and B. Boutevin Access to nonisocyanate poly (thio) urethanes: A comparative study J. Polym. Sci. Part A: Polym. Chem. 51 2013 3284 3296
24. V. Besse, F. Camara, C. Voirin, R. Auvergne, S. Caillol, and B. Boutevin Synthesis and applications of unsaturated cyclocarbonates Polym. Chem. 14 2013 4545 4561
25. H. Tomita, S. Sanda, and T. Endo Polyaddition of bis(seven-membered cyclic carbonate) with diamines: a novel and efficient synthetic method for polyhydroxyurethanes J. Polym. Sci. Part A: Polym Chem. 39 2001 4091 4100
26. J.H. Clements Reactive applications of cyclic alkylene carbonates Ind. Eng. Chem. Res. 42 2003 663 674
27. J. Henkelmann, T. Rühl, Process for the preparation of 1,3-Disubstituted Imidazolidinones, U.S. Patent 5,783,706, 1998.
28. I. Vauthey, F. Valot, C. Gozzi, F. Fache, and M. Lemaire An environmentally benign access to carbamates and ureas Tetrahedron Lett. 41 2000 6347 6350
29. E. Dyer, and H. Scott The preparation of polymeric and cyclic urethanes and ureas from ethylene carbonate and amines J. Am. Chem. Soc. 79 1957 672 675
30. Q.L. Lu, T.R. Hoye, and C.W. Macosko Reactivity of common functional groups with urethanes: models for reactive compatibilization of thermoplastic polyurethane blends J. Polym. Sci. Part A: Polym. Chem. 40 2002 2310 2328
31. Y. Camberlin, J.P. Pascault, J.M. Letoffe, and P. Claudy Synthesis and DSC study of model hard segments from diphenyl methane diisocyanate and butane diol J. Polym. Sci., Polym. Chem. Ed. 20 1982 383 392
32. E. Degoue, Controle de la toxicite dans la synthese des polyurethanes: optimisation des reactions et nouvelles strategies de masquage par des composes à reactivite orthogonale, PhD Theses INSA-Lyon, 2010.
33. B. Nohra, L. Candy, J.L. Blanco, Y. Raoul, and Z. Mouloungui Synthesis of five and six-membered cyclic glycerilic carbonates bearing exocyclic urethane functions Lipid. Sci. Technol. 115 2013 111 122
34. I. Javni, D.P. Hong, and Z.S. Petrovic Soy-based polyurethane by nonisocyanate route J. Appl. Polym. Sci. 108 2008 3867 3875
35. I. Javni, D.P. Hong, and Z.S. Petrovic Polyurethanes from soybean oil, aromatic, and cycloaliphatic diamines by non-isocyanate route J. Appl. Polym. Sci. 128 2013 566 571
36. M. Kathalewar, A. Sabnis, and D. D'Mello Isocyanate free polyurethanes from new CNSL based bis-cyclic carbonate and its application in coatings Eur. Polym. J. 57 2014 99 108
37. L. Maisonneuve, A.L. Wirotius, C. Alfos, E. Grau, and H. Cramail Fatty acid-based (bis) 6-membered cyclic carbonates as efficient isocyanate free poly(hydroxyurethane) precursors Polym. Chem. 5 2014 6142
38. L. Annunziata, A.K. Diallo, S. Fouquay, G. Michaud, F. Simon, J.M. Brusson, and J.F. Carpentier Guillaume SM. α, ω-Di(glycerol carbonate) telechelic polyesters and polyolefins as precursors to polyhydroxyurethanes: an isocyanate-free approach Green Chem. 16 2014 1947 1956
39. R.H. Lambeth, and T.J. Henderson Organocatalytic synthesis of (poly) hydroxyurethanes from cyclic carbonates and amines Polymer 54 2013 5568 5573
40. C. Carre, L. Bonnet, and L. Averous Original biobased nonisocyanate polyurethanes: solvent- and catalyst-free synthesis, thermal properties and rheological behaviour RSC Adv. 4 2014 54018