Thiol-ene UV Curable Polyurethane Adhesive Based on Castor Oil

doi:10.7517/j.issn.1674-0475.2017.01.046

Abstract

Abstract:

Urethane acrylates were prepared via melt polycondensation method and esterification method respectively, using isophorone diisocyanate (IPDI), castor oil (CO), hydroxypropyl acrylate (HPA) as main raw materials. CO-based thiol monomer was prepared via melt polycondensation method using castor oil (CO) and 3-mercapto propionic acid (3-MPA).Urethane acrylates and the thiol-compounds were blended with addition of photo-initiator in certain proportions, and then polyurethane curing film was formed through thiol-ene couple reaction between double bond and thiol under UV irradiation. The structure and properties of the urethane acrylate, thiol compound and the polyurethane curing film were characterized by NMR, FT-IR, Pohot-DSC and TG. The results indicated that the ethylene linkages of urethane acrylates and the thiol-compounds were successfully inserted in the polyurethane molecular chain. The UV-cured films showed good mechanical properties and thermal stability with curing time 60 s.

Key words: castor oil, UV curable, adhesive, thiol-ene click chemistry

WANG Qing, CHEN Guangxue, YU Mingguang, CHEN Qifeng, TAI Jinglei. Thiol-ene UV Curable Polyurethane Adhesive Based on Castor Oil[J]. Imaging Science and Photochemistry, 2017, 35(1): 46-52.

References

[1] 魏杰, 金养智. 光固化涂料[M]. 北京:化学工业出版社, 2005. 4-5.Wei J, Jin Y Z. UV Curing Coatings[M]. Beijing:Chemical Industry Press, 2005. 4-5.
[2] Lgarashi S, Ltalura A, Kitajima M, Chifen A N, F rch R, Berger R. Surface stress control using ultraviolet light irradiation of plasma-polymerized thin films[J]. Applied Physics Letters, 2006,88(14):143119-1-143119-3.
[3] Hao Q L. Electrochemical polymerization and properties of poly (triphenylene),anexcellent blue-green-light emitter[J]. Journal of Physical Chemistry C, 2010,114(21):9608-9617.
[4] Bardi M A G, Machado L D B.Accompanying of parameters of color, gloss and hardness on polymeric films coated with pigmented inks cured by different radiation doses of ultraviolet light[J]. Radiation Physics and Chemistry, 2012,81(9):1332-1335.
[5] 刘红波, 刘恒权, 李荣先, 缪国元, 薛亚波. 混杂紫外光固化胶黏剂的研制[J]. 化工新型材料, 2006,34(7):81-84.Liu H B, Liu H Q, Li R X, Miao G Y, Xue Y B. Study and preparation of hybrid UV-curable adhesives[J]. New Chemical Materials, 2006,34(7):81-84.
[6] 周钢, 陈建山, 奚海, 吴宇雄. 紫外光固化光敏齐聚物体系的研究进展[J]. 精细化工中间体, 2003,33(1):5-13.Zhou G, Chen J S, Xi H, Wu Y X. Progress on UV-curing photosensitive oligomer[J]. Fine Chemical in Termediates, 2003,33(1):5-13.
[7] 刘红波, 林峰. 紫外光固化材料的研究热点[J]. 现代涂料与涂装, 2008,11(9):38-41.Liu H B, Lin F. Hotspots research in UV curable materials[J]. Modern Paint and Finishing, 2008,11(9):38-41.
[8] Li C Y, Chisham J, Andrews M, Mackenzie J D, Peyghambarian N. Sol-gel integrated optical coupler by ultraviolet light imprinting[J]. Electronics Letters,31(4):271-272.
[9] Tey J N, Soutar A M, Mhaisalkar S G, Yu H, Hew K M. Mechanical properties of UV-curable polyurethane acrylate used inpackaging of MEMS devices[J]. Thin Solid Films, 2006,504:384-390.
[10] Lundberg P, Hawker C J, Hult A, Malkoch M. Click assisted one-pot multi-step reactionsin polymer science:accelerated synthetic protocols[J]. Macromolecular Rapid Communications, 2008,29:998-1015.
[11] Wolfgang H B, Robert S. "Click" chemistry in polymer and materials science[J]. Macromolecular Rapid Communications, 2007,28:15-54.
[12] Okay O, Bowman C N. Kinetic modeling of thiol-ene reactions with both step and chain growth aspects[J]. Macromolecular Theory and Simulations, 2005,14:267-277.
[13] Morgan C R, Magnotta F, Ketley A D. Thiol/ene photocurable polymers[J]. Journal of Polymer Science:Polymer Chemistry Edition, 1977,15:627-645.
[14] Kolb H C, Sharpless K B, Finn M G. Click chemistry:diverse chemical function from a few good reactions[J]. Angewandte Chemie International Edition, 2001,40:2004-2021.
[15] Meldal M, Torn C W. Cu-catalyzed azide-alkyne cycloaddition[J]. Chemical Reviews, 2008,108:2952-3015.