Rapid formation of regulated methacrylate networks yielding tough materials for lithography-based 3D printing (original) (raw)

Abstract

Vinyl sulfone esters are described as a new class of AFCT reagents for methacrylate-based photopolymerization without the drawback of retardation but good regulation of network architecture. Resulting materials show low shrinkage stress and increased toughness. This paves the way for vinyl sulfone esters in lithography-based 3D printing.

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References (40)

  1. T. Wohlers, Wohlers Report 2015: 3D printing and additive manufacturing state of industry.
  2. L. E. Murr, E. Martinez, K. N. Amato, S. M. Gaytan, J. Hernandez, D. A. Ramirez, P. W. Shindo, F. Medina and R. B. Wicker, J. Mater. Res. Technol., 2012, 1, 42-54.
  3. D. L. Bourell, H. L. Marcus, J. W. Barlow and J. J. Beaman, Int. J. Powder Metall., 1992, 28, 369-381.
  4. A. Zocca, P. Colombo, C. M. Gomes and J. Guenster, J. Am. Ceram. Soc., 2015, 98, 1983-2001.
  5. L. Novakova-Marcincinova and J. Novak-Marcincin, Appl. Mech. Mater., 2013, 309, 133-140.
  6. R. D. Goodridge, C. J. Tuck and R. J. M. Hague, Prog. Mater. Sci., 2012, 57, 229-267.
  7. R. Liska, M. Schuster, R. Infuehr, C. Turecek, C. Fritscher, B. Seidl, V. Schmidt, L. Kuna, A. Haase, F. Varga, H. Lichtenegger and J. Stampfl, J. Coat. Technol. Res., 2007, 4, 505-510.
  8. Fig. 5 DLP set up (a) and 3D structures fabricated with formulation C (20 db% EVS, b).
  9. P. Tesavibul, R. Felzmann, S. Gruber, R. Liska, I. Thompson, A. R. Boccaccini and J. Stampfl, Mater. Lett., 2012, 74, 81-84.
  10. M. Schwentenwein and J. Homa, Int. J. Appl. Ceram. Technol., 2015, 12, 1-7.
  11. J. R. Tumbleston, D. Shirvanyants, N. Ermoshkin, R. Janusziewicz, A. R. Johnson, D. Kelly, K. Chen, R. Pinschmidt, J. P. Rolland, A. Ermoshkin, E. T. Samulski and J. M. DeSimone, Science, 2015, 347, 1349-1352.
  12. S. C. Ligon-Auer, M. Schwentenwein, C. Gorsche, J. Stampfl and R. Liska, Polym. Chem., 2016, 7, 257-286.
  13. S. Tielens, H. Declercq, T. Gorski, E. Lippens, E. Schacht and M. Cornelissen, Biomacromolecules, 2007, 8, 825-832.
  14. A. Tiwari, J. J. Grailer, S. Pilla, D. A. Steeber and S. Gong, Acta Biomater., 2009, 5, 3441-3452.
  15. H. Wang, Y. Feng, B. An, W. Zhang, M. Sun, Z. Fang, W. Yuan and M. Khan, J. Mater. Sci.: Mater. Med., 2012, 23, 1499-1510.
  16. Y. Zuo, X. Liu, D. Wei, J. Sun, W. Xiao, H. Zhao, L. Guo, Q. Wei, H. Fan and X. Zhang, ACS Appl. Mater. Interfaces, 2015, 7, 10386-10394.
  17. N. Moszner and U. Salz, Macromol. Mater. Eng., 2007, 292, 245-271.
  18. N. Moszner and T. Hirt, J. Polym. Sci., Part A: Polym. Chem., 2012, 50, 4369-4402.
  19. Y. Hirai, T. Yoshikawa, N. Takagi, S. Yoshida and K. Yamamoto, J. Photopolym. Sci. Technol., 2003, 16, 615-620.
  20. D. Matsukawa, H. Wakayama, K. Mitsukura, H. Okamura, Y. Hirai and M. Shirai, J. Mater. Chem., 2009, 19, 4085-4087.
  21. J. E. Fleischer, Mod. Paint Coat., 2001, 91, 21-22.
  22. Y. Abe, DIC Tech. Rev., 2005, 11, 1-20.
  23. C. E. Hoyle and C. N. Bowman, Angew. Chem., Int. Ed., 2010, 49, 1540-1573.
  24. P. Esfandiari, S. C. Ligon, J. J. Lagref, R. Frantz, Z. Cherkaoui and R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2013, 51, 4261-4266.
  25. N. Moszner, P. Burtscher, U. K. Fischer, H. Ritter, M. Tabatabai and A. Utterodt, Dental materials on the basis of low-odor thiols, WO 2015124797A1, 2015.
  26. A. Mautner, X. Qin, H. Wutzel, S. C. Ligon, B. Kapeller, D. Moser, G. Russmueller, J. Stampfl and R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2013, 51, 203-212.
  27. D. Karalekas and A. Aggelopoulos, J. Mater. Process. Technol, 2003, 136, 146-150.
  28. H. Y. Park, C. J. Kloxin, A. S. Abuelyaman, J. D. Oxman and C. N. Bowman, Macromolecules, 2012, 45, 5640-5646.
  29. C. Gorsche, M. Griesser, G. Gescheidt, N. Moszner and R. Liska, Macromolecules, 2014, 47, 7327-7336.
  30. C. Gorsche, T. Koch, N. Moszner and R. Liska, Polym. Chem., 2015, 6, 2038-2047.
  31. S. C. Ligon, K. Seidler, C. Gorsche, M. Griesser, N. Moszner and R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2016, 54, 394-406.
  32. P. Gauss, S. C. Ligon, M. Griesser, C. Gorsche, H. Svajdlenkova, T. Koch, N. Moszner and R. Liska, J. Polym. Sci., Part A: Polym. Chem., 2015, ahead of print.
  33. T. Sato, M. Seno, M. Kobayashi, T. Kohno and H. Tanaka, Eur. Polym. J., 1995, 31, 29-34.
  34. L. Lecamp, F. Houllier, B. Youssef and C. Bunel, Polymer, 2001, 42, 2727-2736.
  35. G. Moad, E. Rizzardo and S. H. Thang, Polymer, 2008, 49, 1079-1131.
  36. Y. Yagci and I. Reetz, React. Funct. Polym., 1999, 42, 255- 264.
  37. G. F. Meijs and E. Rizzardo, Makromol. Chem., 1990, 191, 1545-1553.
  38. E. Rizzardo, G. F. Meijs and S. H. Thang, Free radical chain transfer polymerization processes, US 5932675A, 1999.
  39. D. H. R. Barton, C.-Y. Chern and J. C. Jaszberenyi, Tetra- hedron, 1995, 51, 1867-1886.
  40. N. Moszner, F. Zeuner, I. Lamparth and U. K. Fischer, Macromol. Mater. Eng., 2009, 294, 877-886.