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http://dx.doi.org/10.4047/jap.2015.7.5.386

The effect of 4,4'-bis(N,N-diethylamino)benzophenone on the degree of conversion in liquid photopolymer for dental 3D printing  

Lee, Du-Hyeong (Department of Prosthodontics, School of Dentistry, Kyungpook National University)
Mai, Hang Nga (Department of Prosthodontics, School of Dentistry, Kyungpook National University)
Yang, Jin-Chul (Department of Polymer Science & Engineering, School of Applied Chemical Engineering, Kyungpook National University)
Kwon, Tae-Yub (Department of Dental Biomaterials, School of Dentistry, Kyungpook National University)
Publication Information
The Journal of Advanced Prosthodontics / v.7, no.5, 2015 , pp. 386-391 More about this Journal
Abstract
PURPOSE. The purpose of this preliminary study was to investigate the effects of adding 4,4'-bis(N,N-diethylamino) benzophenone (DEABP) as a co-initiator to a binary photoinitiating system (camphorquinone-amine) to analyze on the degree of conversion (DC) of a light-cured resin for dental 3D printing. MATERIALS AND METHODS. Cylindrical specimens (N=60, n=30 per group, ${\phi}5mm{\times}1mm$) were fabricated using bisphenol A glycerolate dimethacrylate (BisGMA) both with and without DEABP. The freshly mixed resins were exposed to light in a custom-made closed chamber with nine light-emitting diode lamps (wavelength: 405 nm; power: $840mW/cm^2$) for polymerization at each incidence of light-irradiation at 10, 30, 60, 180, and 300 seconds, while five specimens at a time were evaluated at each given irradiation point. Fourier-transform infrared (FTIR) spectroscopy was used to measure the DC values of the resins. Two-way analysis of variance and the Duncan post hoc test were used to analyze statistically significant differences between the groups and given times (${\alpha}$=.05). RESULTS. In the DEABP-containing resin, the DC values were significantly higher at all points in time (P<.001), and also the initial polymerization velocity was faster than in the DEABP-free resin. CONCLUSION. The addition of DEABP significantly enhanced the DC values and, thus, could potentially become an efficient photoinitiator when combined with a camphorquinone-amine system and may be utilized as a more advanced photopolymerization system for dental 3D printing.
Keywords
Photopolymer; Photointiator; Degree of conversion, 4,4'-bis(N,N-diethylamino)benzophenone; 3D Printing;
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Times Cited By KSCI : 6  (Citation Analysis)
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1 Ely C, Schneider LF, Ogliari FA, Schmitt CC, Correa IC, Lima Gda S, Samuel SM, Piva E. Polymerization kinetics and reactivity of alternative initiators systems for use in light-activated dental resins. Dent Mater 2012;28:1199-206.   DOI
2 Erfan M, Jafarzadeh-Kashi TS, Ghadiri M, Rakhshan V. The effects of dentin bonding agent formulas on their polymerization quality, and together with tooth tissues on their microleakage and shear bond strength: an explorative 3-step experiment. J Adv Prosthodont 2014;6:333-45.   DOI
3 Bae EJ, Kim JH, Kim WC, Kim HY. Bond and fracture strength of metal-ceramic restorations formed by selective laser sintering. J Adv Prosthodont 2014;6:266-71.   DOI
4 Chandramohan D, Marimuthu K. Rapid prototyping/rapid tooling-a over view and its applications in orthopaedics. Int J Adv Eng Tech 2011;2:435-48.
5 Jardini AL, Larosa MA, Maciel Filho R, Zavaglia CA, Bernardes LF, Lambert CS, Calderoni DR, Kharmandayan P. Cranial reconstruction: 3D biomodel and custom-built implant created using additive manufacturing. J Craniomaxillofac Surg 2014;42:1877-84.   DOI
6 Roper DA, Good BL, McCauley R, Yarlagadda S, Smith J, Good A, Pa A, Mirotznik MS. Additive manufacturing of graded dielectrics. Smart Mater Struct 2014;23:045029.   DOI
7 Hull CW. Apparatus for production of three-dimensional objects by stereolithography. Google Patents US 45753330 A;1986.
8 Crivello JV, Reichmanis E. Photopolymer materials and pro-cesses for advanced technologies. Chem Mater 2014;26:533-48.   DOI
9 Tonetto MR, Pinto SC, Rastelli Ade N, Borges AH, Saad JR, Pedro FL, de Andrade MF, Bandeca MC. Degree of conversion of polymer-matrix composite assessed by FTIR analysis. J Contemp Dent Pract 2013;14:76-9.
10 Yoshida K, Greener EH. Effect of photoinitiator on degree of conversion of unfilled light-cured resin. J Dent 1994;22: 296-9.   DOI
11 Albuquerque PP, Moreira AD, Moraes RR, Cavalcante LM, Schneider LF. Color stability, conversion, water sorption and solubility of dental composites formulated with different photoinitiator systems. J Dent 2013;41:e67-72.   DOI
12 Sideridou I, Tserki V, Papanastasiou G. Effect of chemical structure on degree of conversion in light-cured dimethacrylate-based dental resins. Biomaterials 2002;23:1819-29.   DOI
13 Oliveira DC, Silva CB, Muniz BV, Volpato MC, Costa AR, Sinhoreti MA. Effect of 4-(N,N-dimethylamino)phenethyl alcohol on degree of conversion and cytotoxicity of photo-polymerized CQ-based resin composites. Braz Dent J 2014;25: 538-42.   DOI
14 Schneider LF, Pfeifer CS, Consani S, Prahl SA, Ferracane JL. Influence of photoinitiator type on the rate of polymerization, degree of conversion, hardness and yellowing of dental resin composites. Dent Mater 2008;24:1169-77.   DOI
15 Amintowlieh Y, Tzoganakis C, Hatzikiriakos SG, Penlidis A. Effects of processing variables on polypropylene degradation and long chain branching with UV irradiation. Polym Degrad Stab 2014;104:1-10.   DOI
16 Pongprueksa P, Miletic V, Janssens H, Van Landuyt KL, De Munck J, Godderis L, Van Meerbeek B. Degree of conversion and monomer elution of CQ/amine and TPO adhesives. Dent Mater 2014;30:695-701.   DOI
17 Schroeder WF, Asmussen SL, Cook WD, Vallo CI. Efficiency of 4,4'-bis(N,N-diethylamino) benzophenone for the polymerization of dimethacrylate resins in thick sections. Polym Int 2011;60:1362-9.
18 Oguri M, Yoshida Y, Yoshihara K, Miyauchi T, Nakamura Y, Shimoda S, Hanabusa M, Momoi Y, Van Meerbeek B. Effects of functional monomers and photo-initiators on the degree of conversion of a dental adhesive. Acta Biomater 2012;8: 1928-34.   DOI
19 Palin WM, Hadis MA, Leprince JG, Leloup G, Boland L, Fleming GJ, Krastl G, Watts DC. Reduced polymerization stress of MAPO-containing resin composites with increased curing speed, degree of conversion and mechanical properties. Dent Mater 2014;30:507-16.   DOI
20 Ikemura K, Ichizawa K, Yoshida M, Ito S, Endo T. UV-VIS spectra and photoinitiation behaviors of acylphosphine oxide and bisacylphosphine oxide derivatives in unfilled, light-cured dental resins. Dent Mater J 2008;27:765-74.   DOI
21 Sahin O, Ozdemir AK, Turgut M, Boztug A, Sumer Z. Investigation of flexural strength and cytotoxicity of acrylic resin copolymers by using different polymerization methods. J Adv Prosthodont 2015;7:98-107.   DOI
22 Hammond GS, Wamser CC, Chang CT, Baylor C Jr. Photoreaction of Michler's ketone with benzophenone. Triplet exciplex. J Am Chem Soc 1970;92:6362-3.   DOI
23 McGinniss VD, Provder T, Kuo C, Gallopo A. Polymerization of methyl methacrylate photoinitiated by 4,4'-bis(N,N-diethylamino) benzophenone. 1. Macromolecules 1978;11:393-404.   DOI
24 Santini A, McGuinness N, Nor NA. Degree of conversion of resin-based orthodontic bonding materials cured with single-wave or dual-wave LED light-curing units. J Orthod 2014;41:292-8.   DOI
25 Urapepon S. Degree of conversion of resin composite cured by light through a translucent fiber posts. J Adv Prosthodont 2014;6:194-9.   DOI
26 Moon HJ, Shin DH. Effect of CQ-amine ratio on the degree of conversion in resin monomers with binary and ternary photoinitiation systems. Restor Dent Endod 2012;37:95-102.
27 Moore BK, Platt JA, Borges G, Chu TM, Katsilieri I. Depth of cure of dental resin composites: ISO 4049 depth and microhardness of types of materials and shades. Oper Dent 2008;33:408-12.   DOI
28 Rueggeberg FA, Caughman WF, Curtis JW Jr. Effect of light intensity and exposure duration on cure of resin composite. Oper Dent 1994;19:26-32.
29 Vitale A, Sangermano M, Bongiovanni R, Burtscher P, Moszner N. Visible Light Curable Restorative Composites for Dental Applications Based on Epoxy Monomer. Materials 2014;7:554-62.   DOI
30 Flury S, Lussi A, Hickel R, Ilie N. Light curing through glass ceramics with a second- and a third-generation LED curing unit: effect of curing mode on the degree of conversion of dual-curing resin cements. Clin Oral Investig 2013;17:2127-37.   DOI
31 Kim MJ, Kim KH, Kim YK, Kwon TY. Degree of conversion of two dual-cured resin cements light-irradiated through zirconia ceramic disks. J Adv Prosthodont 2013;5:464-70.   DOI
32 Chen Y, Zhou C, Lao J. A layerless additive manufacturing process based on CNC accumulation. Rap Proto J 2011;17: 218-27.   DOI