Sequential thiol click reactions: Formation of ternary thiourethane/thiol- ene networks with enhanced thermal and mechanical properties

ACS Applied Materials and Interfaces

Volumn 6, Issue 9, 2014, Pages 6088-6097

  McNair, Olivia D ^a   Brent, Davis P ^a   Sparks, Bradley J ^a   Patton, Derek L ^a   Savin, Daniel A ^a  

^a University of Southern Mississippi   (United States)

Author keywords

click chemistry; dual network; glass transition temperature; thiol ene; thiol isocyanate

Indexed keywords

ESTERS; GLASS TRANSITION; MECHANICAL PROPERTIES; MECHANICAL TESTING; PHYSICAL PROPERTIES;

CLICK CHEMISTRY; COMPLEMENTARY TECHNIQUES; CROSS-LINK DENSITIES; FACILE MODIFICATIONS; MACROSCALE PROPERTIES; THERMAL AND MECHANICAL PROPERTIES; THIOL-ENES; THIOL-ISOCYANATE;

MORPHOLOGY;

EID: 84900869717     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am405138e     Document Type: Conference Paper

References (35)

1. Chen, Z.; Chisholm, B. J.; Patani, R.; Wu, J. F.; Fernando, S.; Jogodzinski, K.; Webster, D. C. Soy-based UV-curable thiol-ene coatings J. Coat. Technol. 2010, 1-11
2. Midgley, T., Jr; Henne, A. L.; Shepard, A. F. Natural and Synthetic Rubber. XII. Reversible Vulcanization, By Organo-Metallic Derivatives J. Am. Chem. Soc. 1934, 56 (5) 1156-1157
3. Hoyle, C. E.; Bowman, C. N. Thiol-ene Click Chemistry Angew. Chem., Int. Ed. 2010, 49 (9) 1540-1573
4. Hoyle, C. E.; Gould, T.; Piland, S.; Wei, H.; Phillips, B.; Nazarenko, S.; Askim, F.; Cole, M. Photocurable materials for mouthguards Radtech Rep. 2006, 12-17
5. Senyurt, A. F.; Wei, H. Y.; Hoyle, C. E.; Piland, S. G.; Gould, T. E. Ternary Thiol-ene/Acrylate Photopolymers: Effect of Acrylate Structure on Mechanical Properties Macromolecules 2007, 40 (14) 4901-4909
6. Wei, H. Y.; Senyurt, A. F.; Jonsson, S.; Hoyle, C. E. Photopolymerization of Ternary Thiol-ene/Acrylate Systems: Film and Network Properties J. Polym. Sci., Part. A: Polym. Chem. 2007, 45 (5) 822-829
7. Campos, L. M.; Meinel, I.; Guino, R. G.; Schierhorn, M.; Gupta, N.; Stucky, G. D.; Hawker, C. J. Highly Versatile and Robust Materials for Soft Imprint Lithography Based on Thiol-ene Click Chemistry Adv. Mater. 2008, 20 (19) 3728-3733
8. Gould, T. E.; Piland, S. G.; Shin, J.; Hoyle, C. E.; Nazarenko, S. Characterization of Mouthguard Materials: Physical and Mechanical Properties of Commercialized Products Dent. Mater. 2009, 25 (6) 771-780
9. Gould, T. E.; Piland, S. G.; Shin, J.; McNair, O.; Hoyle, C. E.; Nazarenko, S. Characterization of Mouthguard Materials: Thermal Properties of Commercialized Products. Dent. Mater. 2009, 25 (12) 1593-1602
10. Clark, T. S.; Hoyle, C. E.; Nazarenko, S. Kinetics Analysis and Physical Properties of Photocured Silicate-Based Thiol-ene Nanocomposites: The Effects of Vinyl POSS ene on the Polymerization Kinetics and Physical Properties of Thiol-triallyl Ether Networks J. Coat. Technol. 2008, 5 (3) 345-351
11. Phillips, J. P.; Mackey, N. M.; Confait, B. S.; Heaps, D. T.; Deng, X.; Todd, M. L.; Stevenson, S.; Zhou, H.; Hoyle, C. E. Dispersion of Gold Nanoparticles in UV-Cured, Thiol-ene Films by Precomplexation of Gold-Thiol Chem. Mater. 2008, 20 (16) 5240-5245
12. Owusu-Adom, K.; Schall, J.; Guymon, C. A. Photopolymerization Behavior of Thiol-Acrylate Monomers in Clay Nanocomposites Macromolecules 2009, 42 (9) 3275-3284
13. Cramer, N. B.; Couch, C. L.; Schreck, K. M.; Boulden, J. E.; Wydra, R.; Stansbury, J. W.; Bowman, C. N. Properties of Methacrylate-thiol-ene Formulations As Dental Restorative Materials Dent. Mater. 2010, 26 (8) 799-806
14. Cramer, N. B.; Couch, C. L.; Schreck, K. M.; Carioscia, J. A.; Boulden, J. E.; Stansbury, J. W.; Bowman, C. N. Investigation of Thiol-ene and Thiol-ene-methacrylate Based Resins As Dental Restorative Materials Dent. Mater. 2010, 26 (1) 21-28
15. McNair, O. D.; Gould, T. E.; Piland, S. G.; Savin, D. A. Characterization of Mouthguard Materials: A Comparison of a Commercial Material to a Novel Thiolene Family J. Appl. Polym. Sci. 2014, ASAP (10.1002/app.40402).
16. Hoyle, C. E.; Lee, T. Y.; Roper, T. Thiol-enes: Chemistry of the Past with Promise for the Future J. Polym. Sci., Part. A: Polym. Chem. 2004, 42 (21) 5301-5338
17. Cramer, N. B.; Reddy, S. K.; Cole, M.; Hoyle, C.; Bowman, C. N. Initiation and Kinetics of Thiol-ene Photopolymerizations without Photoinitiators J. Polym. Sci., Part. A: Polym. Chem. 2004, 42 (22) 5817-5826
18. Chiou, B. S.; Khan, S. A. Real-Time FTIR and in Situ Rheological Studies on the UV Curing Kinetics of Thiol-ene Polymers Macromolecules 1997, 30 (23) 7322-7328
19. Hoyle, C. E.; Hensel, R. D.; Grubb, M. B. Laser-Initiated Polymerization of a Thiol-ene System Polym. Photochem. 1984, 4 (1) 69-80
20. Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Thiol-Click Chemistry: A Multifaceted Toolbox for Small Molecule and Polymer Synthesis Chem. Soc. Rev. 2010, 39 (4) 1355-1387
21. Li, Q.; Zhou, H.; Hoyle, C. E. The Effect of Thiol and Ene Structures on Thiol-ene Networks: Photopolymerization, Physical, Mechanical, and Optical Properties Polymer 2009, 50 (10) 2237-2245
22. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions Angew. Chem., Int. Ed. 2001, 40 (11) 2004-2021
23. Service, R. F. Chemistry: Click Chemistry Clicks along Science 2008, 320 (5878) 868-869
24. Cramer, N. B.; Bowman, C. N. Kinetics of Thiol-ene and Thiol-Acrylate Photopolymerizations with Real-Time Fourier Transform Infrared J. Polym. Sci., Part. A: Polym. Chem. 2001, 39 (19) 3311-3319
25. Senyurt, A. F.; Hoyle, C. E.; Wei, H.; Piland, S. G.; Gould, T. E. Thermal and Mechanical Properties of Cross-Linked Photopolymers Based on Multifunctional Thiol-urethane Ene Monomers Macromolecules 2007, 40 (9) 3174-3182
26. Yang, Z.; Wicks, D. A.; Hoyle, C. E.; Pu, H.; Yuan, J.; Wan, D.; Liu, Y. Newly UV-Curable Polyurethane Coatings Prepared by Multifunctional Thiol- and Ene-Terminated Polyurethane Aqueous Dispersions Mixtures: Preparation and Characterization Polymer 2009, 50 (7) 1717-1722
27. Shin, J.; Matsushima, H.; Chan, J. W.; Hoyle, C. E. Segmented Polythiourethane Elastomers through Sequential Thiol-ene and Thiol-isocyanate Reactions Macromolecules 2009, 42 (9) 3294-3301
28. Shin, J.; Matsushima, H.; Comer, C. M.; Bowman, C. N.; Hoyle, C. E. Thiol-isocyanate-ene Ternary Networks by Sequential and Simultaneous Thiol Click Reactions Chem. Mater. 2010, 22 (8) 2616-2625
29. Li, Q.; Zhou, H.; Wicks, D. A.; Hoyle, C. E. Thiourethane-Based Thiol-ene High Tg Networks: Preparation, Thermal, Mechanical, and Physical Properties J. Polym. Sci., Part. A: Polym. Chem. 2007, 45 (22) 5103-5111
30. Senyurt, A. F.; Wei, H.; Phillips, B.; Cole, M.; Nazarenko, S.; Hoyle, C. E.; Piland, S. G.; Gould, T. E. Physical and Mechanical Properties of Photopolymerized Thiol-ene/Acrylates Macromolecules 2006, 39 (19) 6315-6317
31. Lee, T. Y.; Carioscia, J.; Smith, Z.; Bowman, C. N. Thiol-Allyl Ether-methacrylate Ternary Systems. Evolution Mechanism of Polymerization- Induced Shrinkage Stress and Mechanical Properties Macromolecules 2007, 40 (5) 1473-1479
32. Jian, Y.; He, Y.; Sun, Y.; Yang, H.; Yang, W.; Nie, J. Thiol-epoxy/Thiol-Acrylate Hybrid Materials Synthesized by Photopolymerization J. Mater. Chem. C 2013, 1 (29) 4481-4489
33. McNair, O. D.; Sparks, B. J.; Janisse, A. P.; Brent, D. P.; Patton, D. L.; Savin, D. A. Highly Tunable Thiol-ene Networks via Dual Thiol Addition Macromolecules 2013, 46 (14) 5614-5621
34. Peeterbroeck, S.; Alexandre, M.; Jérôme, R.; Dubois, P. Poly(ethylene-co-vinyl acetate)/Clay Nanocomposites: Effect of Clay Nature and Organic Modifiers on Morphology, Mechanical, and Thermal Properties Polym. Degrad. Stab. 2005, 90 (2) 288-294
35. McNair, O. D.; Janisse, A. P.; Krzeminski, D. E.; Brent, D. E.; Gould, T. E.; Rawlins, J. W.; Savin, D. A. Impact Properties of Thiol-ene Networks ACS Appl. Mater. Interfaces 2013, 5 (21) 11004-11013