In this work, epoxy acrylate resin (EA) based on the industrial-grade bisphenol A-based epoxy resin (Ep6) and acrylic acid (AA) has been synthesized in order to develop hybrid resin comprising both epoxide group and reactive, terminal unsaturation. Obtained epoxy acrylate prepolymer was employed to formulate photocurable coating compositions containing, besides the EA binder, also cationic or radical photoinitiators. Hence, when cationic photoinitiators were applied, polyether-type polymer chains with pending acrylate groups were formed. In the case of free radical polymerization, epoxy acrylates certainly formed a polyacrylate backbone with pending epoxy groups. Owing to the presence of both epoxy and double carbon–carbon pendant groups, the reaction product exhibits photocrosslinking via two distinct mechanisms: (i) cationic ring-opening polymerization and (ii) free radical polymerization. Therefore, photopolymerization behavior of synthetized hybrid resin with various photoinitiators was determined via photo-differential scanning calorimetry (photo-DSC) and real-time infrared spectroscopy (RT-IR) methods, and properties of cured coatings were investigated. The performance of the following type of photoinitiators was tested in the cationic photopolymerization: diaryliodonium cations or triarylsulfonium cations, and the following type of photoinitiators were used to induce free radical photopolymerization: α-hydroxyketones, acylphosphine oxides, and their mixtures. Lastly, the basic physicomechanical properties of cured coatings, such as tack-free time, hardness, adhesion, gloss, and yellowness index, were evaluated. Some structural factors and parameters of cationic and radical photoinitiators and photopolymerization mechanisms affecting the epoxy acrylate hybrid coatings performance are discussed.
In this work, a series of novel multifunctional epoxy (meth)acrylate resins based on a low-viscosity aliphatic triepoxide triglycidyl ether of trimethylolethane (TMETGE) and acrylic acid (AA) or methacrylic acid (MMA) have been synthesized. Thanks to the performed modification, the obtained prepolymers have both epoxides as well as carbon–carbon double bonds and differ in their amount. The obtained results indicate that the carboxyl-epoxide addition esterification occurs in the presence of a catalyst (triphenylphosphine) at a temperature of 90 °C, whilst the required degree of conversion can be achieved simply by varying both the reagents ratio and reaction time. The structure of synthesized copolymers was confirmed by spectroscopic analyses (FT-IR, 1H NMR, 13C NMR) and studied regarding its nonvolatile matter content (NV), acid value (PAVs), as well as its epoxy equivalent value (EE). Due to the presence of both epoxy and double carbon–carbon pendant groups, one can apply two distinct mechanisms: (i) cationic ring-opening polymerization or (ii) free-radical polymerization to crosslink polymer chains. Synthesized epoxy (meth)acrylate prepolymers were further employed to formulate photocurable coating compositions. Hence, when cationic photoinitiators were applied, polyether-type polymer chains with pending acrylate or methacrylate groups were formed. In the case of free-radical polymerization, epoxy (meth)acrylates certainly formed a poly(meth)acrylate backbone with pending epoxy groups. Further, photopolymerization behavior and properties of cured coatings were investigated regarding some structural factors and parameters. Moreover, reaction rate coefficients of photo-cross-linking by both cationic ring-opening and free-radical photopolymerization of the received epoxy (meth)acrylate resins were determined via real-time infrared spectroscopy (RT-IR). Lastly, basic physicomechanical properties, such as tack-free time, hardness, adhesion, gloss, and yellowness index of cured coatings, were evaluated.
Silicone pressure-sensitive adhesives (Si-PSA) exhibit unique properties, such as high Si-O-Si backbone flexibility, low intermolecular interactions, low surface tension, excellent thermal stability, and high UV transparency, which often explains why silicone PSAs have an impressive performance at high-and lowtemperature extremes, excellent electrical properties, chemical resistance, and outstanding weathering resistance turning them superior compared to organic PSAs. It is well known that due to their unique properties, silicone pressure-sensitive adhesives are materials for special applications. In the present study, we focus on changing the useful properties of the best compositions of silicone pressure-sensitive adhesives in time to verify the impact of aging on them. The influence of time on given silicone pressure-sensitive adhesive tapes and their useful properties is a very important factor for the description of the life-time of potential products based on such compositions. Aging of Si-PSA was carried out for 1 h, 24 h, 7 days, 31 days, and 92 days. The tests did include such properties like adhesion, cohesion (at 20 and 70°C), tack, and yellowness.
This study aimed to investigate the potential of photoreactive acrylate patches as systems for transdermal drug delivery, in particular, using more renewable alternatives and more environmentally friendly synthesis routes of transdermal patches. Therefore, the aim of this study was to develop a transdermal patch containing ibuprofen and investigate its performance in vitro through the pigskin. Transparent patches were prepared using four acrylate copolymers with an incorporated photoinitiator. Two types of transdermal patches based on the photocrosslinking acrylic prepolymers with isobornyl methacrylate as biocomponent and monomer increasing Tg (“hard”) were manufactured. The obtained patches were characterized for their adhesive properties and tested for permeability of the active substance. It turns out that patches whose adhesive matrix is photoreactive polyacrylate copolymers have a higher cohesion than patches from commercial adhesives, while the modification of the copolymers with isobornyl methacrylate resulted in an improvement in adhesion and tack. This study demonstrates the feasibility of developing photoreactive acrylic-based transdermal patches that contain biocomponents that can deliver a therapeutically relevant dose of ibuprofen.
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