Polymerization kinetics of phosphonic acids and esters using an iodonium initiator

Besse, Vincent; Pluart, Loïc Le; Cook, Wayne D.; Pham, Thi Nhàn; Madec, Pierre‐Jean

doi:10.1002/pola.26935

Cited by 9 publications

(11 citation statements)

References 50 publications

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“…It should be noted that the impact of the iodonium salt on the polymerization reaction depends on the type of monomers present in the system. It was found that the iodonium salt failed to enhance the photopolymerization in the presence of methacrylate phosphonic acid monomers . From the range of intensities studied here, the appropriate light intensity to obtain substantial DC with good polymerization efficiency for hydrophilic 2PI resin is in the range 229−679 mW/cm 2 .…”

Section: Discussionmentioning

confidence: 82%

“…It was found that the iodonium salt failed to enhance the photopolymerization in the presence of methacrylate phosphonic acid monomers. 37 From the range of intensities studied here, the appropriate light intensity to obtain substantial DC with good polymerization efficiency for hydrophilic 2PI resin is in the range 2292679 mW/cm 2 . Both the hydrophobic resins and hydrophilic 3PI resin yield substantial DC with good efficiency at all of the light intensities studied here.…”

Section: Discussionmentioning

confidence: 94%

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Impact of light intensity on the polymerization kinetics and network structure of model hydrophobic and hydrophilic methacrylate based dental adhesive resin

Abedin

Camarda

et al. 2015

J Biomed Mater Res

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The impact of light intensity on the degree of conversion (DC), rate of polymerization and network structure was investigated for hydrophobic and hydrophilic dental adhesive resins. Two and three component photoinitiating (PI) systems were used in this study. Low light intensities had a negative impact on the polymerization efficiency for the hydrophilic resin with 2 component PI system. Incorporation of iodonium salt in the hydrophilic resin significantly improved the polymerization efficiency of the HEMA/BisGMA system and led to a substantial DC, even at low light intensities. The results suggested that shorter polymer chains were formed in the presence of iodonium salt. It appears that there is little or no impact of light intensity on the polymer structure of the 2 component PI system. Light intensity has subtle impact on the polymer structure of the 3 component PI system. In the case of the hydrophobic resin, the polymer is so highly cross-linked that the presence of shorter chains for the 3 component PI system does not cause a decrease in the glass transition temperature (Tg) when compared to the 2 component PI system. For the hydrophilic resin, the presence of shorter polymer chains in the 3 component PI system reduces the Tg when compared with the corresponding 2 component PI system.

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Section: Discussionmentioning

confidence: 82%

Section: Discussionmentioning

confidence: 94%

Impact of light intensity on the polymerization kinetics and network structure of model hydrophobic and hydrophilic methacrylate based dental adhesive resin

Abedin

Camarda

et al. 2015

J Biomed Mater Res

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“…This assumption is supported by the findings of Besse et al . which reported that the addition of phosphonic acids enhances the rate of homopolymerization of acryl monomers …”

Section: Resultsmentioning

confidence: 99%

Enhancing the stability of UV‐curable thiol/vinyl carbonate resins

Edler

Mostegel

Roth

et al. 2017

J of Applied Polymer Sci

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In this study, the effect of various stabilizer systems on low‐cytotoxic thiol/vinyl carbonate formulations was evaluated with the aim to inhibit premature dark polymerization reactions. The addition of hydroxybenzene‐based radical scavengers such as pyrogallol (PyG), hydroquinone monomethyl ether (MEHQ), or butylated hydroxytoluene (BHT) resulted in a significantly decelerated increase in viscosity compared to formulations without stabilizers during a defined storage period at 50 °C. The usage of bicomponent stabilization systems in appropriate concentrations further reduced the viscosity increase for nonpigmented formulations. The most effective heterosynergistic stabilization system based on PyG and diisoctyl phosphonic acid (9 mM/90 mM) exerts only a minor influence on the polymerization performance, which was shown by photo‐DSC measurements. The herein presented stabilization of vinyl carbonate/thiol resins exhibits a significant contribution to bringing these low‐toxic building blocks into industrial applications. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44934.

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“…Another study by Besse et al showed that the addition of iodonium salt does not always result in higher polymerization efficiency. For example, in the case of methacrylate phosphonic acids, the iodonium salt had a reverse effect [17]. …”

Section: Introductionmentioning

confidence: 99%

Effect of Partition of Photo-Initiator Components and Addition of Iodonium Salt on the Photopolymerization of Phase-Separated Dental Adhesive

Abedin

Song

et al. 2016

JOM

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The polymerization kinetics of physically separated hydrophobic- and hydrophilic-rich phases of a model dental adhesive have been investigated. The two phases were prepared from neat resin containing 2-hydroxyethyl methacrylate (HEMA) and bisphenol A glycerolate dimethacrylate (BisGMA) in the ratio of 45:55 (wt/wt). Neat resins containing various combinations of popular photo-initiating compounds, e.g., camphoquinone (CQ), ethyl 4-(dimethylamino)benzoate (EDMAB), 2-(dimethylamino)ethyl methacrylate (DMAEMA) and diphenyliodonium hexafluorophosphate (DPIHP) were prepared. To obtain the two phases 33 wt% of deuterium oxide (D2O) was added to the neat resins. This amount of D2O exceeded the miscibility limit for the resins. The concentration of each component of the photo-initiating system in the two phases was quantified by HPLC. When combined with CQ, DMAEMA is less efficient as a co-initiator compared to EDMAB. The addition of DPIHP as the third component into either CQ/EDMAB or CQ/DMAEMA photo-initiating systems leads to comparable performance in both the hydrophobic- and hydrophilic-rich phases. The addition of the iodonium salt significantly improved the photopolymerization of the hydrophilic-rich phase; the hydrophilic-rich phase exhibited extremely poor polymerization when the iodonium salt was not included in the formulation. The partition concentration of EDMAB in the hydrophilic-rich phase was significantly lower than that of DMAEMA or DPIHP. This study indicates the need for a combination of hydrophobic/hydrophilic photosensitizer and addition of iodonium salt to improve polymerization within the hydrophilic-rich phase of the dental adhesive.

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Polymerization kinetics of phosphonic acids and esters using an iodonium initiator

Cited by 9 publications

References 50 publications

Impact of light intensity on the polymerization kinetics and network structure of model hydrophobic and hydrophilic methacrylate based dental adhesive resin

Impact of light intensity on the polymerization kinetics and network structure of model hydrophobic and hydrophilic methacrylate based dental adhesive resin

Enhancing the stability of UV‐curable thiol/vinyl carbonate resins

Effect of Partition of Photo-Initiator Components and Addition of Iodonium Salt on the Photopolymerization of Phase-Separated Dental Adhesive

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