Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

Versace, Davy‐Louis; Chemtob, Abraham; Croutxé‐Barghorn, Céline; Rigolet, Séverinne

doi:10.1002/mame.200900318

Cited by 16 publications

(16 citation statements)

References 51 publications

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“…This relationship between the UV-generated photoacids and the resulting inorganic network has been developed extensively. Versace et al studied the relation between the sol-gel reaction and cationic polymerization by using epoxy cyclohexyltrimethoxysilane as a monomer 28, 29 . They investigated the formation of inorganic and organic polymers via the one-step simultaneous method by UV-light irradiation 28 or two separate and consecutive steps (sol-gel reaction and cationic photopolymerization) 29 .…”

Section: Introductionmentioning

confidence: 99%

“…Versace et al studied the relation between the sol-gel reaction and cationic polymerization by using epoxy cyclohexyltrimethoxysilane as a monomer 28, 29 . They investigated the formation of inorganic and organic polymers via the one-step simultaneous method by UV-light irradiation 28 or two separate and consecutive steps (sol-gel reaction and cationic photopolymerization) 29 . Our group investigated the polymerization behavior and mechanical properties of dental adhesive copolymers prepared by dual polymerization via visible-light irradiation 26 .…”

Section: Introductionmentioning

confidence: 99%

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Self-strengthening hybrid dental adhesive via visible-light irradiation triple polymerization

Song

et al. 2016

RSC Adv.

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A self-strengthening methacrylate-based dental adhesive system was developed by introducing an epoxy cyclohexyl trimethoxysilane (TS) which contains both epoxy and methoxysilyl functional groups. The experimental formulation, HEMA/BisGMA/TS (22.5/27.5/50, wt%), was polymerized by visible-light. Real-time Fourier transform infrared spectroscopy (FTIR) was used to investigate in situ the free radical polymerization of methacrylate, ring-opening cationic polymerization of epoxy, and photoacid-induced sol-gel reactions. Among the three simultaneous reactions, the reaction rate of the free radical polymerization was the highest and the hydrolysis/condensation rate was the lowest. With 40s-irradiation, the degrees of conversion of the double bond and epoxy groups at 600 s were 73.2±1.2%, 87.9±2.4%, respectively. Hydrolysis of the methoxysilyl group was initially <5%, and increased gradually to about 50% after 48 h dark storage. Photoacids generated through the visible-light-induced reaction were effective in catalyzing both epoxy ring-opening polymerization and methoxysilyl sol-gel reaction. The mechanical properties of copolymers made with TS concentrations from 5 to 35 wt% were obtained using dynamic mechanical analysis (DMA). In wet conditions, the storage moduli at 70 °C and glass transition temperature were significantly higher than that of the control (p<0.05); these properties increased with TS concentration and storage time. The post reaction of hydrolysis/condensation of alkoxysilane could provide persistent strengthening whether in a neutral or acidic environment and these characteristics could lead to enhanced mechanical properties in the oral environment. The cumulative amount of leached species decreased significantly in the TS-containing copolymers. These results provide valuable information for the development of dental adhesives with reduced leaching of methacrylate monomers and enhanced mechanical properties under the wet, oral environment.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self-strengthening hybrid dental adhesive via visible-light irradiation triple polymerization

Song

et al. 2016

RSC Adv.

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“…[1][2][3][4] Besides, they can fulfill the series of requirements imposed for functional applications of advanced materials such as thermal, humidity, UV-light resistance, and hydrophobicity. [5][6][7][8][9] Bridged silsesquioxanes are a particular class of organicinorganic hybrid materials synthesized by the hydrolytic condensation of typical precursors like (RO) 3 ÀSiÀR 0 ÀSiÀ(RO) 3 , where RO represents an alkoxy group and R 0 is an organic group.…”

Section: Introductionmentioning

confidence: 99%

Transparent Polysilsesquioxane Films Obtained from Bridged Ureasil Precursors: Tunable Photoluminescence Emission in the Visible Region and Filtering of UV‐Radiation

Gómez¹,

Fasce²,

Williams³

et al. 2010

Macro Materials & Eng

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Bridged ureasil precursors were synthesized by the reaction of either ethylenediamine (1 mol) or m‐xylylenediamine (1 mol) with isocyanatepropyltriethoxysilane (2 mol). Transparent polysilsesquioxane films were obtained by the hydrolytic condensation of the pure precursors or their co‐condensation in a 50:50 molar ratio. Films based on pure ureasil precursors showed a blue photoluminescent emission band assigned to the photoinduced proton‐transfer among H‐bonded urea groups and the subsequent radiative recombination of ionized groups. Films synthesized by the co‐condensation of both precursors exhibited a significant red‐shift of their absorption, excitation, and emission spectra, associated to de‐localization of H‐bonds, and a high absorption of UV‐radiation.

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“…[18][19][20] Two organoalkoxysilane monomers, 3-glycidoxypropyl-trimethoxysilane (GPTMS) and 2-(3,4-epoxy-cyclohexylethyl)ethyltrimethoxysilane (TRIMO), have attracted considerable interest for preparing cationic UV curable polysiloxanes. 21,22 However, both the hydrolysis and condensation of organoalkoxysilane are very slow in the absence of a catalyst. On the one hand, the basic catalyst such as amines should not be used as it probably neutralizes the Lewis acid produced by cationic photoinitiator and inhibits the cationic curing.…”

Section: Introductionmentioning

confidence: 99%

Cationic UV curing behavior and thermal properties of oxetane‐modified polysiloxane prepared from tetraethyl orthosilicate

Zhan

Xie

Shi

2011

J of Applied Polymer Sci

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The oxetane-modified polysiloxane (OxePSiO) was synthesized via the partial hydrolysis/condensation of tetraethyl orthosilicate (TEOS) and then transesterification reaction with 3-ethyl-3-(hydroxymethyl)oxetane (EHO), and characterized by FT-IR, 1 H NMR, 13 C NMR, and 29 Si NMR spectroscopy. Using the water/ TEOS molar ratios of 0.8-1.2, the number-average molecular weights and polydispersity indices were obtained by GPC to range from 1.013 to 2.716 g mol À1 and around 2.0, respectively. The viscosity of Oxe-PSiO prepared from the water/TEOS molar ratio of 1.2 sharply increased to 177,545 cps from 438 cps of that from the molar ratio of 0.8. A series of cationic UV-curable formulations were prepared by blending the Oxe-PSiO synthesized with the water/TEOS molar ratio of 1.0 into an commercial oxetane-based resin, 3,3 0 -[oxydi(methylene)]bis(3-ethyloxetane), in different weight ratios. The photopolymerization kinetics studied by photo-DSC in the presence of triphenylsulphonium hexafluoroantimonate as a cationic photoinitiator showed that both the maximum photopolymerization rate and final oxetane conversion in the cured film decreased with increasing Oxe-PSiO loading mainly due to the sharp increase in viscosity. The DMTA and DSC results both indicated the improvement in thermal stability, showing 12 and 13.4 C, respectively, higher T g for the cured film with 50 wt % Oxe-PSiO loading compared with the pure polymer. Moreover, the temperatures (T 10% and T 50% ) at the weight loss of 10 and 50% and final char yields measured by TGA increased with increasing Oxe-PSiO content. After adding 50 wt % Oxe-PSiO, compared with the pure polymer the T 10% increased from 349 to 361 C, while the T 50% increased from 409 to 424 C, and with a char yield increase of 8.2% at 800 C. In addition, its greatly increased crosslinking density due to the formation of silica network resulted in the enhancement in pencil hardness from B of the pure polymer to 2H grade.

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Synthesis of Organosilica Films Through Consecutive Sol/Gel Process and Cationic Photopolymerization

Cited by 16 publications

References 51 publications

Self-strengthening hybrid dental adhesive via visible-light irradiation triple polymerization

Self-strengthening hybrid dental adhesive via visible-light irradiation triple polymerization

Transparent Polysilsesquioxane Films Obtained from Bridged Ureasil Precursors: Tunable Photoluminescence Emission in the Visible Region and Filtering of UV‐Radiation

Cationic UV curing behavior and thermal properties of oxetane‐modified polysiloxane prepared from tetraethyl orthosilicate

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