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

Abstract

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.

Influence of a long‐side‐chain‐containing reactive diluent on the structure and mechanical properties of UV‐cured films

“…Apparently, the introduction of HEMA‐DDSA was propitious to improve the crosslink density of the films, for higher gel content values were obtained. It is probably the decreased viscosity of compositions with more diluent (HEMA‐DDSA) that makes molecules diffuse more easily, thus resulting in a higher degree of crosslinking . The unsaturation concentration (3.94 mmol g −1 ) of HEMA‐DDSA is relatively low, compared with that of BFA (3.95 mmol g −1 ) or TMPTA (10.14 mmol g −1 ).…”

“…It is probably the decreased viscosity of compositions with more diluent (HEMA-DDSA) that makes molecules diffuse more easily, thus resulting in a higher degree of crosslinking. 30 The unsaturation concentration (3.94 mmol g −1 ) of HEMA-DDSA is relatively low, compared with that of BFA (3.95 mmol g −1 ) or TMPTA (10.14 mmol g −1 ). Since the amount of crosslink bonds per unit volume decreases slightly with more diluent HEMA-DDSA, as listed in Table 1, the crosslink density will be reduced.…”

Synthesis and ultraviolet‐curing behaviors of vinyl ether functionalized polyurethane oligomers

“…According to the UV‐curing mechanism, UV‐curing technology can be divided into free‐radical, cationic, and radical–cationic hybrid curing processes. Currently, most UV‐curable resins are primarily based on the free‐radical polymerization of high reactive (meth)acrylate monomers . Although (meth)acrylates exhibit good chemical resistance and rapid curing, they also exhibit certain inevitable disadvantages, including health hazards, detrimental coating shrinkage, and inhibition by oxygen .…”

“…Currently, most UV-curable resins are primarily based on the free-radical polymerization of high reactive (meth)acrylate monomers. [8][9][10][11][12] Although (meth)acrylates exhibit good chemical resistance and rapid curing, they also exhibit certain inevitable disadvantages, including health hazards, detrimental coating shrinkage, and inhibition by oxygen. [10][11][12][13][14][15] There are also several disadvantages associated with the free-radical photopolymerization process, including (1) it is severely inhibited by oxygen, which normally causes unsatisfactory surface curing, and (2) it leads to a contraction in the reaction volume.…”

Synthesis and cationic photopolymerization of fluorine‐containing vinyl ether monomers for the hydrophobic films

“…Organic silicones are commonly used due to their excellent high temperature performance, but a high silicon content is required to achieve low surface energy. In addition, organic silicone films possess a weak anti‐scratch property . Many organic fluorocarbons have been studied due to their satisfactory properties such as water repellence, chemical resistance, thermal stability, anti‐fingerprint, and anti‐scratch, that allow for their application in fluorocarbon coatings .…”