The photopolymerization of acrylates and methacrylates containing silicon

Davidson, R. S.; Ellis, Richard J.; Tudor, Stephen; Wilkinson, Susan A.

doi:10.1016/0032-3861(92)90091-a

Cited by 22 publications

(8 citation statements)

References 7 publications

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“…The conventional sol−gel process has several disadvantages including a large volume shrinkage resulting from the removal of solvents and small molecular byproducts of the hydrolysis and polycondensation reactions such as water and alcohol. Recently a number of researchers have addressed this problem − by replacing the solvent-based alkoxides, such as methoxy and ethoxy, with polymerizable alkoxide groups. Because this process involves the polymerization of the hydroxyl monomer, the volume shrinkage can be considerably reduced or eliminated.…”

Section: Introductionmentioning

confidence: 99%

Photopolymerization Kinetics and Dynamic Mechanical Properties of Silanes Hydrolyzed without Evolution of Byproducts. Tetrakis[(methacryloyloxy)ethoxy]silane−Diethylene Glycol Dimethacrylate

et al. 2011

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The temperature dependence of photopolymerization kinetics of tetrakis[(methacryloyloxy)ethoxy]silane (TetMESi) was compared with an analogue, diethylene glycol dimethacrylate and their copolymers. In all cases, the kinetics are controlled by the temperature dependence of the propagation step, the effect of diffusion on radical termination, the effect of rising glass transition during cure, and topological restraint on complete conversion. The glass transition regions of these polymers were very broad, suggesting their use in high temperature applications. NMR of the TetMESi monomer, and FTIR and water sorption measurements during exposure to water of the TetMESi-based polymers showed that the Si−O−C bond was slowly hydrolyzed, resulting in water-swollen polymers containing poly(hydroxyethyl methacrylate) which reduced the glass transition temperature and narrowed the glass transition region. UV−vis spectroscopic studies showed that during exposure to water, SiO2 nanoparticles or nanostructures were formed from the condensation of the silanol groups formed during the hydrolysis of TetMESi.

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Section: Introductionmentioning

confidence: 99%

Photopolymerization Kinetics and Dynamic Mechanical Properties of Silanes Hydrolyzed without Evolution of Byproducts. Tetrakis[(methacryloyloxy)ethoxy]silane−Diethylene Glycol Dimethacrylate

et al. 2011

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“…Silyl ether–containing acrylates and thiols were synthesized through substitution reactions of methyltrichlorosilane and phenyltrichlorosilane (Scheme ). ,− …”

Section: Resultsmentioning

confidence: 99%

“…Monomers A1 – A2 and T1 – T2 were synthesized using known methods. ,− To synthesize the model compound DG1 , 2-mercaptoethanol (3.3 g, 43 mmol) and 2-hydroxyethyl acrylate (4.9 g, 43 mmol) were mixed together and 1-hexylamine (0.039 g, 0.38 mmol) was added as a catalyst. The reaction proceeded for 12 h at room temperature, after which any unreacted starting materials were removed under a reduced pressure (yield 90%).…”

Section: Experimental Sectionmentioning

confidence: 99%

Degradable Silyl Ether–Containing Networks from Trifunctional Thiols and Acrylates

et al. 2020

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The purpose of this study was the synthesis of novel degradable polymer-based devices capable of releasing an encapsulated agent in a controlled manner with specific interest for use as drug delivery materials. Base-catalyzed thiol Michael additions between trithiols and triacrylates containing silyl ether groups were exploited to prepare a series of degradable cross-linked networks. Disodium fluorescein was loaded as a hydrophilic drug surrogate inside the networks, and the degradation of the networks and the release of dye were monitored. The networks were characterized by Fourier transform infrared spectroscopy, and their thermal and mechanical properties were investigated through thermogravimetric analysis and dynamic mechanical analysis. The effects of the monomer structure on degradation, release behavior, and thermal properties were investigated. The networks prepared from more sterically hindered silyl ether monomers exhibited decreased rates of degradation and correspondingly slower release of encapsulated disodium fluorescein dye. The results suggest that the characteristics of the networks can be fine-tuned by manipulation of the group attached to the Si atom in the silyl ether monomers.

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“…Many silicon‐containing monomers have already been synthesized, investigated, and applied in different fields 12, 13. A number of diacrylates and triacrylates and methacrylates containing silicon have been prepared,14, 15 but the surface free energies of monomers with only one silicon atom are not low enough to obtain good releasability and antifouling properties. However, to the best of our knowledge, there is no published work addressing the synthesis and investigation of (meth)acrylate monomers with more than one silicon atom.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and UV‐curing properties of silicon‐containing (Meth)acrylate monomers

Wang

Zou

2013

J of Applied Polymer Sci

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Eight different silicon-containing (meth)acrylate monomers are synthesized by the substitution reaction of chlorosiloxanes with 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate. Their molecular structures are confirmed by IR, 1 H-NMR, and 13 C-NMR spectroscopic analyses. The effects of silicon content on the UV-curing behavior, physical, surface, and thermal properties are investigated. The UV-curing behavior is analyzed by photo differential scanning calorimetry. The surface free energy of the UV-cured film is calculated from contact angles measured using the Lewis acid-base three liquids method. The silicon-containing (meth)acrylate monomers perform much better than traditional (meth)acrylate monomers on UV-curing. The silicon-containing monomers have higher final conversions and fast UV-curing rates in photopolymerization. The surface free energy decreases with increasing silicon content, because silicon in the soft segment is transferred to the surface, producing a UV-cured film; this is confirmed by X-ray photoelectron spectroscopy measurements. All these advantageous properties enable these synthetic silicon-containing monomers to perform better in applications.

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The photopolymerization of acrylates and methacrylates containing silicon

Cited by 22 publications

References 7 publications

Photopolymerization Kinetics and Dynamic Mechanical Properties of Silanes Hydrolyzed without Evolution of Byproducts. Tetrakis[(methacryloyloxy)ethoxy]silane−Diethylene Glycol Dimethacrylate

Photopolymerization Kinetics and Dynamic Mechanical Properties of Silanes Hydrolyzed without Evolution of Byproducts. Tetrakis[(methacryloyloxy)ethoxy]silane−Diethylene Glycol Dimethacrylate

Degradable Silyl Ether–Containing Networks from Trifunctional Thiols and Acrylates

Synthesis, characterization, and UV‐curing properties of silicon‐containing (Meth)acrylate monomers

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