Advances in Materials
Volume 9, Issue 1, March 2020, Pages: 8-14
Received: Feb. 24, 2020;
Accepted: Mar. 10, 2020;
Published: Mar. 23, 2020
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Chunfu Chen, Henkel Technology Center – Asia Pacific, Henkel Japan Ltd., Yokohama, Japan
Dayong Sun, Analytical Solution Group – Adhesive Technologies, Henkel Corporation, Bridgewater, USA
Masao Kanari, Henkel Technology Center – Asia Pacific, Henkel Japan Ltd., Yokohama, Japan
Daoqiang Lu, Henkel Adhesive Innovation Center, Henkel China Co., Ltd, Shanghai, China
An UPLC-Q-TOF-MS method is developed for cure degree measurement and cure behavior analysis on a novel photocurable adhesive material which is composed of specially designed acrylate oligomers, acrylate monomers, photo-initiators and additives such as ultra-violet absorbent, antioxidant stabilizer, optical stabilizer, etc. The photocurable adhesive material, in both cured and uncured state, were separated by Ultra-Performance Liquid Chromatography (UPLC) and the low molecular weight components were detected and determined quantitatively by high resolution Quadrupole Time-Of-Flight mass spectrometry (Q-TOF-MS) under Atmosphere Pressure Chemical Ionization (APCI) mode. Cure behaviors of all photo-reactive components in the photocurable adhesive material such as acrylate monomers and photo-initiators were studied by quantitatively measuring the amount of each reactive components in different stages of curing. Both the conversion of each acrylate monomers and photo-initiators at different curing energy conditions were calculated and discussed. Nearly full cure was obtained at cure energy of 200 mJ/cm2 for 4-hydroxybutyl acrylate and acryloyl morphine, as well as the two bifunctional monomers, 1,6-hexandiol diacrylate and dimethylol tricyclodecane diacrylate. Only 42.7% and 85.0% conversion were achieved for benzyl acrylate and isobornyl acrylate, respectively while consumption of TPO, a photo-initiator, was 38.0% at this cure energy. The results showed that a minimum 2000 mJ/cm2 energy condition is needed to achieve full cure of all acrylate monomers and enough decomposition of photo-initiator. This study indicated that UPLC-Q-TOF-MS is an effective and precise analytical method for cure degree measurement and cure behavior analysis on the photocurable materials.
Study on the Cure Behavior of a Novel Photocurable Material Using UPLC-Q-TOF-MS, Advances in Materials.
Vol. 9, No. 1,
2020, pp. 8-14.
J. Woods (1992), “Radiation Curable Adhesives” In Radiation Curing Science and Technology, 1st ed., S. Pappas, Eds. Springer Science: New York, pp 333-398.
C. Dekker (2006), “UV-Radiation Curing of Adhesives” In Handbook of Adhesives and Sealants, P. Cognard, Eds. Elsevier: Tokyo, pp 303-353.
C. F. Chen, S. Iwasaki, M. Kanari, B. Li, C. Wang, D. Q. Lu (2017), “High performance UV and thermal cure hybrid epoxy adhesive.” IOP Conf. Series: Material Science and Engineering, 213, 012032.
F. N. Jones, M. N. Nichols, S. P. Pappas (2017), “Radiation curing coatings” In: Organic Coatings: Science and Technology, 4th ed., F. N. Jones, M. N. Nichols, S. P. Pappas, Eds. John Wiley & Sons: New York, pp 403-418.
P. Glockner, T. Jung, S. Struck, K. Studer (2008), “Radiation curing coatings and printing inks”, Vincents Network: Hannover.
W. Schrof, K. Menzel (2006), “Formulation” In: UV Coatings, Basics, Recent Developments and New Applications, R. Schwalm, Eds. Elsvier Science: New York, pp 140-159.
A. Soyano (2012), Application of polymers to photoresist materials. Nippon Gomu Kyoukaishi, 2, pp 33-39.
K. Nakamura (2015), Photopolymers: Photoresist materials, Process and Applications. CRC Press: New York.
S. Y. Moon, J. M. Kim (2007), “Chemistry of photolithographic imaging materials based on the chemical amplification concept” J. Photochemistry And Photobiology C: Photochemstry Reviews, 8, pp 157-173.
K. Koseki, M. Uno, Y. Toyokawa, K. Suzuki (2006), “Photopolymerization and adhesion properties of UV curable jet ink.” Journal of Japan Printing Science and Technology, 43 (4), pp 272-278.
A. Tomotake (2010), “Technology and feature of UV curable injet ink.” Journal of the Imaging Society of Japan, 49 (5), pp 412-416.
S. Seipel, J. Yu, A. P. Periyasamy, M. Vikova, M. Vik, V. A. Nierstrasz (2018), “Inkjet printing and UV-LED curing of photochromic dyes for functional and smart textile applications”. RSC Advances, 8, pp 28395-28404.
S. C. Ligon, R. Liska, J. Stampfl, M. Gurr, R. Mulhaupt (2017), “Polymers for 3D printing and customized additive manufacturing.” Chemical Reviews, 117 (15), pp 10212-10290.
V. Babaei, J. Ramos, Y. Lu, G. Webster, W. F. Matusik (2017), “Fabricating phopolymer objects by mold 3D printing and UV curing.” Computational Design and Fabrication, pp 34-42.
J. R. Laurence, F. T. O’Nell, J. T. Sheridan (2001), “Photopolymer holography recording materials.” International Journal for Light and Electron Optics, 112 (10), pp 449-463.
M. Ortuno, E. Fernandez, S. Gallego, A. Belendes, I. Pascual (2007), “New photopolymer holographic recording material with sustanble design.” Optics Express, 15 (19), pp 12425-12435.
M. W. Tibbitt, J. A. Shadish, C. A. DeForest (2016), “Photopolymers for multiphoton lithography in biomaterials and hydrogels.” In: Multiphoton Lithography: Techniques, Materials and Applications, J. Stampfl, R. Liska, A. Ovsianikov]] Eds. Weley VCH: New York, pp 183-220.
J. Stampfl, S. Baudis, C. Heller, R. Liska, A. Neumester, R. Kling, A. Ostendorf (2008), “Spitsbart. Photopolymers with tunable mechanical properties processed by laser based high resolution stereolithography.” Journal of Micromechanics and Microengineering, 18, 125014 (9pp).
B. Chiou, S. Kahn (1997), “Real-time FT-IR and in situ rheological studies on the UV curing kinetics of thiol-ene polymers.” Macromolecules, 30, pp 7322-7328.
T. Scherzer, U. Dekker (2000), “The effect of temperature on the kinetics of diacrylate photopolymerization studied by real-time FTIR spectroscopy.” Polymers, 41, pp 7681-7690.
D. Kunwong, N. Sumanochitraporn, S. Kaewpirom (2011), “Curing behavior of a UV curable coating based on urethane acrylate oligomer: the influence of reactive monomers.” Songklanakarin J. Sci. Technol., 33 (2), pp 201-207.
G. M. Allen, K. F. Drain (1990), “Comparison of thermal, mechanical, and spectroscopic techniques for characterization radiation-cured adhesives.” ACS Symposium Series, 417 (18), pp 242-257.
P. I. Mathias, T. H. Connor, C. B’Hymer (2017), “A review of high performance liquid chromatographic-mass spectrometric urinary methods for anticancer drug exposure of healthcare workers.” J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 1060, pp 316-324.
M. Li., X. Hou, J. Zhang, S. Wang, Q. Fu, L. He (2011), “Application of HPLC/MS in the analysis of traditional Chinese medicines.” J. Pharm. Anal., 1 (2), pp 81-91.
B. Rochart (2019), “Quantitative and qualitative LC-high- resolution-MS.” In: Recent Advances in Analytical Chemistry. M. Ince, Eds. IntechOpen: London, pp 1-18.
N. Y. Pidpruzhnykov, V. E. Sabko, V. V. Lurchenko, I. A. Zupanets (2012), “UPLC-MS/MS method for bioequivalence study of oral drugs of meldonium.” Biomedical Chromatography, 26, pp 599-605.
M. Otoukesh, C. Nerín, M. Aznar, A. Kabir, K. G Furton,] Z. Es’haghi (2019), “Determination of adhesive acrylates in recycled polyethyleneterephthalate by fabric phase sorptive extraction coupled to ultraperformance liquid chromatography - mass spectrometry.” Journal of Chromatography A, 1602, pp 56–63.
J. Sawanobori, C. Chen, M. Kanari (2018), “Light curable resin composition”. United States Patent 10100236.
H. Wang, C. Chen, D. Lu, M. Li, Y. Yuan (2019), “Photocurable adhesive composition preparation and use thereof.” Japan Patent 6545251.