UV‐Curable Cycloaliphatic Epoxide Based on Modified Linseed Oil: Synthesis, Characterization and Kinetics

Abstract

Summary: Linseed oil was derivitized with 1,3‐butadiene via a Diels‐Alder reaction. The cycloaddition adduct was then epoxidized using a hydrogen peroxide/quaternary ammonium tetrakis(diperoxotungsto) phosphate system. The cyclohexene derivitized linseed oil (CLO) and the epoxidized cyclohexene derivatized linseed oil (ECLO) were characterized by 1H NMR, 13C NMR, and FT‐IR. In addition, 2D NMR measurements (COSY) were performed on CLO and ECLO to identify the cyclohexyl structures. Molecular weight was determined by ESI‐MS and GPC. The ECLO was photo‐polymerized using UV‐light, and the kinetics of the photo‐curing reactions was evaluated by real‐time FT‐IR and photo‐DSC. All the characterizations supported the successful introduction of cyclohexyl structure to the backbone of linseed oil directly and indirectly. Real‐time FT‐IR and photo‐DSC indicated the slightly improved reactivity of ECLO.Ideal structure of cyclohexene linseed oil (CLO).imageIdeal structure of cyclohexene linseed oil (CLO).

Polyurethane-silica hybrid foam by sol–gel approach: Chemical and functional properties

“…For the preparation of polysiloxane domains (A in Fig. 1) we followed the procedure proposed by K. Zou et al [26]. A mixture of TEOS 48.6%, ethanol 43.0%, water 8.4% by weight and 9.73$10 À4 mL of HCl per solution gram were mechanically mixed at room temperature for 24 h. During this stage, the TEOS hydrolyzes in silanols, which condense to siloxane adducts according to the well-established reactions of hydrolysis and condensation [27].…”

“…In particular, primary polysiloxane particles aggregate to form coarse fractal structures. The primary particle diameter, as evaluated according to Guinier's relation [26,28,29] from the gyration radius, R g , is equal to 0.7e0.8 nm, slightly increasing with the polysiloxane content. The slope of the Porod region is in the range 2.8e3 for all the polysiloxane structures.…”

“…Spectra of pristine PUR and hybrid PUR (HPUR-1.5, HPUR-3, HPUR-5, HPUR-7) were collected for 10 min. All scattering data were dark current and background subtracted, and normalized for the primary beam intensity [26,28,29]. …”

The unique activity of catalyst in the epoxidation of soybean oil and following reaction of epoxidized product with bisphenol A

“…Oxirane rings, introduced into the triglyceride structure, comparable with epoxy groups included in epoxies, are able to react with typical hardening agents in the crosslinking process, resulting in the internal plastification effect (Czub, 2008a,b). Epoxy resins flexibilization, alike decreasing of their fragility, is essential in a case of their application e.g., as coating materials (Zou and Soucek, 2005). The very important group of such materials are high-molecularweight epoxy resins, widely used in powder coating, and obtained via reaction of bisphenols and low-or average-molecular-weight epoxy resins.…”

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

“…Some applications may be hampered by their high viscosities. Modified ELO synthesized through Diels-Alder reaction of dicyclopentadiene [40] or 1,3-butadiene [41] with linseed oil have been reported. The modified ELO resins still possessed internal oxirane and thus are more suitable for cationic cure.…”