Structural Effect of Thiol-Compounds on the Thiol-Ene Based UV Curable Adhesive

Abstract:

Three thiol-compounds with different functionalities were synthesized through esterification reaction which was prepared by 1, 4-butanediol, trimethylolpropane, and pentaerythritol and 3-mercapto propionic acid respectively. Thiol-compounds and polyurethane-acrylate prepolymer were blended with addition of photo-initiator in certain proportions in order to form polyurethane curing film under UV irradiation. The structure and properties of the thiol-compounds and the polyurethane curing film were characterized by NMR, FT-IR, and TG. The results showed that the thiol-ene addition reaction between the urethane acrylates and the thiol-compounds was preceeded. With the increase of functionality of mercaptopropionic acid ester, the thermal stability improved, and the T-peel strength enhanced. When the moral ratio of urethane acrylates and trimethylolpropane-3-mercapto propionic acid ester was 1:1, the adhesive showed the best mechanical properties and thermal stability with curing time 40s, T-peel strength 88N/m and 50 % mass loss at 369°C, respectively.

• Periodical: Applied Mechanics and Materials (Volume 469)
• Pages: 162-166
• DOI: https://doi.org/10.4028/www.scientific.net/AMM.469.162
• Online since: November 2013
• Authors: Qing Wang, Guang Xue Chen*, Jing Lei Tai, Qi Feng Chen
• Keywords: Thiol-Compounds, Thiol-ene, UV Curable Adhesive

References

[1] W. Peng, Q. B. Jiang: Packaging Engineering Vol. 3, No. 2 (2012), pp.30-33.

[2] J. W. Wu, Y Y Zhao, H Q Zhao: Chemistry and adhesion Vol. 27 (2005), pp.96-100.

[3] J.N. Tey, A.M. Soutar: Thin Solid Films Vol. 504 (2006), p.384.

[4] H. D. Kim, T. W. Kim: Journal of Applied Polymer Science, Vol. 67(1998), p.2153.

[5] Q. Y. Qu, G. W. Xu: Anhui Chemical Industry, Vol. 6 (2006), p.19.

[6] J. Zhou, Q. Y. Zhang: Journal of Functional Materials Vol. 43 (2012), p.1494.

[7] Z. P. Wang, X. J. Chen: Chemical Engineer No. 6 (2004), p.10.

[8] F. Sun, X. K. Liu: Industrial and Engineering Chemistry Research Vol. 52 (2012), p.240.

[9] C.E. Hoyle, N. Bowman: Polymer Chemistry Vol. 49 (2010), p.1540.

[10] A.D. Angew: Chem. Int. Ed. Vol. 6 (2008) pp.8995-8997.

[11] U. Mansfeld, C. Pietsch, R. Hoogenboom: Polym. Chem. Vol. 1 (2010), pp.1560-1598.

[12] A. E. Rydholm, C N. Bowman, K S. Anseth: Biomaterials Vol. 26 (2005), pp.4495-4506.

[13] A. B. Lowe: Polymer Chemistry Vol. 1 (2010), p.17.

[14] C. E. Hoyle, T. Y. Lee, T. Roper: Journal of Polymer Science Vol. 42 (2004), p.5301.

[15] H. C. Kolb, K. B. Sharpless: Drug Discovery Today Vol. 8 (2003), p.1128.

[16] H. C. Kolb, M. G. Finn, K. B. Sharpless: Chem. Int. Ed. Vol. 5 (2001), p.2004-(2021).

[17] M. J. Kade, D. J. Burke, C.J. Hawker: J. Polym. SCI. Part A: Polym, Chem Vol. 48(2010), p.743.

[18] C. E. Hoyle, T. Y. Lee, T. Ropers: Journal of polymer science part a-polymer chemistry Vol. 42 (2004), p.5306.

[19] E. Hoyle, N. Bowman: Polymer Chemistry Vol. 49 (2010), p.1540.