Effect of CQ-amine ratio on the degree of conversion in resin monomers with binary and ternary photoinitiation systems

Moon, Ho Jin; Shin, Dong Hoon

doi:10.5395/rde.2012.37.2.96

Cited by 7 publications

(4 citation statements)

References 33 publications

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“…The initial polymerization rate was significantly improved by increasing light intensity using CQ, mainly because the lower molar extinction coefficient of CQ requires higher light intensity to effectively generate radicals without the presence of excess amine as a co-initiator. 58 It must be noted that at 75 mW cm −2 , a 5 °C temperature increase was observed, due to the heat generated at the higher light intensity. The small increase in temperature also serves to accelerate the CuAAC polymerization, though not enough to significantly increase conversion.…”

Section: Resultsmentioning

confidence: 93%

Kinetics of bulk photo-initiated copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerizations

2016

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Photoinitiation of polymerizations based on the copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction enables spatio-temporal control and the formation of mechanically robust, highly glassy photopolymers. Here, we investigated several critical factors influencing photo-CuAAC polymerization kinetics via systematic variation of reaction conditions such as the physicochemical nature of the monomers; the copper salt and photoinitiator types and concentrations; light intensity; exposure time and solvent content. Real time Fourier transform infrared spectroscopy (FTIR) was used to monitor the polymerization kinetics in situ. Six different di-functional azide monomers and four different tri-functional alkyne monomers containing either aliphatic, aromatic, ether and/or carbamate substituents were synthesized and polymerized. Replacing carbamate structures with ether moieties in the monomers enabled an increase in conversion from 65% to 90% under similar irradiation conditions. The carbamate results in stiffer monomers and higher viscosity mixtures indicating that chain mobility and diffusion are key factors that determine the CuAAC network formation kinetics. Photoinitiation rates were manipulated by altering various aspects of the photo-reduction step; ultimately, a loading above 3 mol% per functional group for both the copper catalyst and the photoinitiator showed little or no rate dependence on concentration while a loading below 3 mol% exhibited 1st order rate dependence. Furthermore, a photoinitiating system consisting of camphorquinone resulted in 60% conversion in the dark after only 1 minute of 75 mW cm−2 light exposure at 400–500 nm, highlighting a unique characteristic of the CuAAC photopolymerization enabled by the combination of the copper(i)’s catalytic lifetime and the nature of the step-growth polymerization.

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Section: Resultsmentioning

confidence: 93%

Kinetics of bulk photo-initiated copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerizations

2016

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“…Thus, the null hypothesis that the DEABP-containing resin possesses similar DC values to that of the DEABP-free resin was rejected. In a previous study, 26 the addition of the p -octyloxy-phenyl-phenyl iodonium hexafluoroantimonate (OPPI) photoinitiator increased the DC of a CQ-DMAEMA containing resin by 3.29% after 300 seconds of light irradiation. Another study concerning the behaviors of acylphosphine oxide (APO) and bisacylphosphine (BAPO) derivatives in light-cured dental resins found that although the BAPO photoinitiator exhibited greater reactivity than did the CQ-amine system, there were no significant differences in the DC values of these systems.…”

Section: Discussionmentioning

confidence: 97%

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

et al. 2015

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PURPOSEThe 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 METHODSCylindrical specimens (N=60, n=30 per group, ø5 mm × 1 mm) 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: 840 mW/cm2) 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 (α=.05).RESULTSIn 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.CONCLUSIONThe 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.

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“…37 Inadequate polymerization of adhesive resin-based restorations has been related to clinical failures due to a greater chance of fracture, secondary caries, and/or premature wear. 35,38,39 Overall, DoC is evaluated according to ISO 4049 standard, but comparing the ISO standard with hardness profile, it was found that there is an overestimation in relation to the DoC. 40,41 In this way, the use of Knoop or Vickers hardness profile would be recommended for adequate DoC characterization of resin composites, avoiding future clinical problems.…”

Section: Discussionmentioning

confidence: 99%

Mechanical Properties of Experimental Composites with Different Photoinitiator

et al. 2021

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Objective The effect of different photoinitiators on mechanical properties of experimental composites was evaluated. Materials and Methods Resin composites were formulated by using a blend of bisphenol A-glycidyl and triethylene glycol (50/50 wt%) dimethacrylate monomers, and 65 wt% of barium aluminium silicate and silica filler particles. Photoinitiators used were 0.2% camphorquinone (CQ) and 0.8% co-initiator (DMAEMA); 0.2% phenyl-propanedione and 0.8% DMAEMA; 0.1% CQ + 0.1% phenyl propanedione and 0.8% DMAEMA; 0.42% mono(acyl)phosphine oxide (MAPO); and 0.5% bis(acyl)phosphine oxide (BAPO). Specimens (n = 10) were light cured by using a multiple-emission peak light-emitting diode for 20 seconds at 1,200 mW/cm2 of irradiance and Knoop hardness and plasticization, depth of cure, flexural strength, and elastic modulus were evaluated. Data were statiscally analyzed at significance level of α = 5%. Results Experimental composites containing MAPO and BAPO photoinitiators showed the highest values of flexural strength, elastic modulus, top surface hardness, and lower hardness reduction caused by alcohol compared with CQ. Composites containing CQ and PPD showed similar results, except for depth of cure and hardness of bottom surface. Conclusion BAPO and MAPO showed higher flexural strength, elastic modulus, hardness on top surface, and lower polymer plasticization to CQ.

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Effect of CQ-amine ratio on the degree of conversion in resin monomers with binary and ternary photoinitiation systems

Cited by 7 publications

References 33 publications

Kinetics of bulk photo-initiated copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerizations

Kinetics of bulk photo-initiated copper(i)-catalyzed azide–alkyne cycloaddition (CuAAC) polymerizations

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

Mechanical Properties of Experimental Composites with Different Photoinitiator

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