Reactivity and regio-selectivity of renewable building blocks for the synthesis of water-dispersible polyurethane prepolymers

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 4, 2014, Pages 788-797

  Li, Yingyuan ^a,b   Noordover, Bart A J ^a   Van Benthem, Rolf A T M ^a,c   Koning, Cor E ^a,d  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b DUTCH POLYMER INSTITUTE DPI   (Netherlands)

^c DSM RESOLVE   (Netherlands)

^d DSM Ahead Performance Materials BV ^*  (Netherlands)

Author keywords

Ethyl ester lysine diisocyanate; Isosorbide; Kinetic study; Polyurethane dispersions; Polyurethanes

Indexed keywords

AMINO ACIDS; CHAINS; DIMERS; DISPERSIONS; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; REACTION RATES;

DIMETHYLOL PROPIONIC ACID; ISOSORBIDE; KINETIC STUDY; LYSINE DIISOCYANATE; POLYURETHANE DISPERSIONS; POLYURETHANE PREPOLYMERS; SMALL PARTICLE SIZE; WATERBORNE POLYURETHANE;

POLYURETHANES;

EID: 84898006507     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400459q     Document Type: Article

References (51)

1. Kim, B. K. Aqueous polyurethane dispersions Colloid Polym. Sci. 1996, 274, 599-611
2. Dieterich, D. Aqueous emulsions, dispersions and solutions of polyurethanes: Synthesis and properties Prog. Org. Coat. 1981, 9, 281-340
3. Li, C.-Y.; Chiu, W.-Y.; Don, T.-M. Preparation of polyurethane dispersions by miniemulsion polymerization J. Polym. Sci., Polym. Chem. 2005, 43, 4870-4881
4. Rahman, M. M.; Kim, H.-D. Synthesis and characterization of waterborne polyurethane adhesives containing different amount of ionic groups (I) J. Appl. Polym. Sci. 2006, 102, 5684-5691
5. Lu, M.-G.; Lee, J.-Y.; Shim, M.-J.; Kim, S.-W. Synthesis and properties of anionic aqueous polyurethane dispersions J. Appl. Polym. Sci. 2002, 86, 3461-3465
6. Madbouly, S. A.; Otaigbe, J. U. Recent advances in synthesis, characterization and rheological properties of polyurethanes and POSS/polyurethane nanocomposites dispersions and films Prog. Polym. Sci. 2009, 34, 1283-1332
7. Wicks, Z. W.; Wicks, D. A.; Rosthauser, J. W. Two package waterborne urethane systems Prog. Org. Coat. 2002, 44, 161-183
8. Kim, B. K.; Lee, J. C. Waterborne polyurethanes and their properties J. Polym. Sci., Part A: Polym. Chem. 1996, 34, 1095-1104
9. Sardon, H.; Irusta, L.; Fernández-Berridi, M. J. Synthesis of isophorone diisocyanate (IPDI) based waterborne polyurethanes: Comparison between zirconium and tin catalysts in the polymerization process Prog. Org. Coat. 2009, 66, 291-295
10. Polus, I. Synthesis of polyurethane coating components with IPDI and TMDI Holz Roh- Werkst. 2003, 61, 238-240
11. Noble, K. L. Waterborne polyurethanes Prog. Org. Coat. 1997, 32, 131-136
12. Sugano, S.; Chinwanitcharoen, C.; Kanoh, S.; Yamada, T.; Hayashi, S.; Tada, K. Preparation of aqueous polyurethane dispersions using aromatic diisocyanate Macromol. Symp. 2006, 239, 51-57
13. Cunliffe, A. V.; Davis, A.; Farey, M.; Wright, J. The kinetics of the reaction of isophorone diisocyanate with mono-alcohols Polymer 1985, 26, 301-306
14. Rochery, M.; Vroman, I.; Lam, T. Kinetic model for the reaction of IPDI and macrodiols: Study on the relative reactivity of isocyanate groups J. Macromol. Sci.-Pure Appl. Chem. 2000, 37, 259-275
15. 13C NMR studies on the relative reactivity of isocyanate groups of isophorone diisocyanate isomers Makromol. Chem. 1990, 191, 1843-1852
16. 13C NMR assignments for isocyanate carbons of isophorone diisocyanate and reactivity of isocyanate groups in Z-stereoisomer and E-stereoisomer J. Polym. Sci., Polym. Chem. 1990, 28, 3019-3027
17. Prabhakar, A.; Chattopadhyay, D. K.; Jagadeesh, B.; Raju, K. Structural investigations of polypropylene glycol (PPG) and isophorone diisocyanate (IPDI)-based polyurethane prepolyrner by 1D and 2D NMR spectroscopy J. Polym. Sci., Polym. Chem. 2005, 43, 1196-1209
18. van Haveren, J.; Scott, E. L.; Sanders, J. Bulk chemicals from biomass Biofuels Bioprod. Bioref. 2008, 2, 41-57
19. Donnelly, M. J.; Stanford, J. L.; Still, R. H. Polyurethanes from renewable resources 0.1. Properties of polymers derived from glucose and xylose based polyols Polym. Int. 1993, 32, 197-203
20. Abraham, G. A.; Marcos-Fernández, A.; Román, J. S. Bioresorbable poly(ester-ether urethane)s from L-lysine diisocyanate and triblock copolymers with different hydrophilic character J. Biomed. Mater. Res. 2006, 76A, 729-736
21. Thiem, J.; Luders, H. Synthesis and properties of polyurethanes derived from diaminodianhydroalditols Makromol. Chem. 1986, 187, 2775-2785
22. Braun, D.; Bergmann, M. 1,4:3,6-Dianhydrohexite als bausteine für polymere J. Prak. Chem.-Chem. Ztg 1992, 334, 298-310
23. Kricheldorf, H. R. "Sugar diols" as building blocks of polycondensates J. Macromol. Sci., Rev. Macromol. Chem. Phys. 1997, C37, 599-631
24. Beldi, M.; Medimagh, R.; Chatti, S.; Marque, S.; Prim, D.; Loupy, A.; Delolme, F. Characterization of cyclic and non-cyclic poly-(ether-urethane)s bio-based sugar diols by a combination of MALDI-TOF and NMR Eur. Polym. J. 2007, 43, 3415-3433
25. Dirlikov, S. K.; Schneider, C.J. US 4,443,563, 1984.
26. Varkey, E. C.; Sreekumar, K. Isosorbide based chiral polyurethanes: optical and thermal studies J. Mater. Sci. 2010, 45, 1912-1920
27. Noordover, B. A. J.; van Staalduinen, V. G.; Duchateau, R.; Koning, C. E.; van Benthem, R.; Mak, M.; Heise, A.; Frissen, A. E.; van Haveren, J. Co- and terpolyesters based on isosorbide and succinic acid for coating applications: Synthesis and characterization Biomacromolecules 2006, 7, 3406-3416
28. Fenouillot, F.; Rousseau, A.; Colomines, G.; Saint-Loup, R.; Pascault, J. P. Polymers from renewable 1,4:3,6-dianhydrohexitols (isosorbide, isomannide and isoidide): A review Prog. Polym. Sci. 2010, 35, 578-622
29. Cognet-georjon, E.; Méchin, F.; Pascault, J. P. New polyurethanes based on diphenylmethane diisocyanate and 1,4:3,6-dianhydrosorbitol 0.1. Model kinetic-studies and characterization of the hard segment Macromol. Chem. Phys. 1995, 196, 3733-3751
30. 13 NMR spectroscopy confirms configurational inversion in chloride displacement of methanesulfonate in isomannide and isosorbide derivatives Carbohydr. Res. 1980, 79, 133-141
31. Zhu, Y.; Durand, M.; Molinier, V.; Aubry, J. M. Isosorbide as a novel polar head derived from renewable resources. Application to the design of short-chain amphiphiles with hydrotropic properties Green Chem. 2008, 10, 532-540
32. Zhu, Y.; Molinier, V.; Durand, M.; Lavergne, A.; Aubry, J. M. Amphiphilic properties of hydrotropes derived from isosorbide: Endo/exo isomeric effects and temperature dependence Langmuir 2009, 25, 13419-13425
33. Abenhaïm, D.; Loupy, A.; Munnier, L.; Tamion, R.; Marsais, F.; Quéguiner, G. Selective alkylations of 1,4:3,6-dianhydro-D-glucitol (isosorbide) Carbohydr. Res. 1994, 261, 255-266
34. Jiang, L.; Xu, Q.; Hu, C.-P. Preparation and characterization of waterborne polyurethaneurea composed of dimer fatty acid polyester polyol J. Nanomater. 2006, 1-10
35. Lu, Y.-S.; Larock, R. C. Soybean-oil-based waterborne polyurethane dispersions: Effects of polyol functionality and hard segment content on properties Biomacromolecules 2008, 9, 3332-3340
36. Sanda, F.; Takata, T.; Endo, T. Synthesis of a novel optically active nylon-1 polymer: Anionic polymerization of L-leucine methyl-ester isocyanate J. Polym. Sci., Polym. Chem. 1995, 33, 2353-2358
37. Chatti, S.; Schwarz, G.; Kricheldorf, H. R. Cyclic and noncyclic polycarbonates of isosorbide (1,4:3,6-dianhydro-D-glucitol) Macromolecules 2006, 39, 9064-9070
38. Claffey, D. J.; Casey, M. F.; Finan, P. A. Glycosylation of 1,4:3,6-dianhydro-D-glucitol (isosorbide) Carbohydr. Res. 2004, 339, 2433-2440
39. Marín, R.; Alla, A.; de Ilarduya, A. M.; Muñoz-Guerra, S. Carbohydrate-based polyurethanes: A comparative study of polymers made from isosorbide and 1,4-butanediol J. Appl. Polym. Sci. 2012, 123, 986-994
40. Noordover, B. A. J.; Heise, A.; Malanowski, P.; Senatore, D.; Mak, M.; Molhoek, L.; Duchateau, R.; Koning, C. E.; van Benthem, R. Biobased step-growth polymers in powder coating applications Prog. Org. Coat. 2009, 65, 187-196
41. Cordeiro, N.; Belgacem, M. N.; Gandini, A.; Neto, C. P. Urethanes and polyurethanes from suberin 0.1. Kinetic study Ind. Crop. Prod. 1997, 6, 163-167
42. de Lima, V.; Pelissoli, N. D.; Dullius, J.; Ligabue, R.; Einloft, S. Kinetic study of polyurethane synthesis using different catalytic systems of Fe, Cu, Sn, and Cr J. Appl. Polym. Sci. 2010, 115, 1797-1802
43. Belgacem, M. N.; Quillerou, J.; Gandini, A.; Rivero, J.; Roux, G. Urethanes and polyurethanes bearing furan moieties-2. comparative kinetics and mechanism of the formation of furanic and other monourethanes Eur. Polym. J. 1989, 25, 1125-1130
44. Belgacem, M. N.; Quillerou, J.; Gandini, A. Urethanes and polyurethanes bearing furan moieties-3. Synthesis, characterization and comparative kinetics of the formation of diurethanes Eur. Polym. J. 1993, 29, 1217-1224
45. Boufi, S.; Belgacem, M. N.; Quillerou, J.; Gandini, A. Urethanes and polyurethanes bearing furan moieties. 4. Synthesis, kinetics and characterization of linear polymers Macromolecules 1993, 26, 6706-6717
46. Zhang, S.-B.; Miao, W.; Zhou, Y. Reaction study of water-borne polyurethanes based on isophorone diisocyanate, dimethylol propionic acid, and poly(hexane neopentyl adipate glycol) J. Appl. Polym. Sci. 2004, 92, 161-164
47. Nanda, A. K.; Wicks, D. A.; Madbouly, S. A.; Otaigbe, J. U. Effect of ionic content, solid content, degree of neutralization, and chain extension on aqueous polyurethane dispersions prepared by prepolymer method J. Appl. Polym. Sci. 2005, 98, 2514-2520
48. Nanda, A. K.; Wicks, D. A. The influence of the ionic concentration, concentration of the polymer, degree of neutralization and chain extension on aqueous polyurethane dispersions prepared by the acetone process Polymer 2006, 47, 1805-1811
49. Madbouly, S. A.; Otaigbe, J. U.; Nanda, A. K.; Wicks, D. A. Rheological behavior of aqueous polyurethane dispersions: Effects of solid content, degree of neutralization, chain extension, and temperature Macromolecules 2005, 38, 4014-4023
50. Kwak, Y.-S.; Kim, E.-Y.; Yoo, B.-H.; Kim, H.-D. Preparation and properties of waterborne poly(urethane urea)s for adhesives: The effects of the 2,2-bis(hydroxylmethyl)propionic acid content on the properties J. Appl. Polym. Sci. 2004, 94, 1743-1751
51. Lee, S.-K.; Kim, B.-K. High solid and high stability waterborne polyurethanes via ionic groups in soft segments and chain termini J. Colloid Interface Sci. 2009, 336, 208-214