Cationic photopolymerization of epoxynorbornane linseed oils: The effect of diluents

Zong, Zhen; Soucek, Mark D.; Liu, Yubiao; Hu, Jun

doi:10.1002/pola.10942

Cited by 46 publications

(56 citation statements)

References 22 publications

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“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Wang¹,

Schuman²

2013

Express Polym. Lett.

155

118

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Abstract. Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been synthesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxidized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF 3 catalyst or anhydride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

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Section: Introductionmentioning

confidence: 99%

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

Wang¹,

Schuman²

2013

Express Polym. Lett.

155

118

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“…Recently our group has reported the improved reactivity of epoxidized seed oil by introducing cyclohexyl and norbornyl structures to the backbone of seed oil. [23,25,26] However, compared to the high reactivity of short chain cycloaliphatic epoxide, the reactivities of epoxidized derivatized cyclohexene linseed oil (ECLO) and the epoxynorbornene linseed oil (ENLO) were still low. Reactive diluents were used to improve the reactivity of ENLO by decreasing the viscosity of ENLO.…”

Section: Resultsmentioning

confidence: 99%

“…[16][17][18] Recently, utilizing UV-light to cure hybrid coatings via a sol-gel process has been reported, but kinetic data on these types of materials are limited. [18][19][20] The steps of the photopolymerization of ECLO are depicted in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

UV‐Curable Organic‐Inorganic Hybrid Film Coatings Based on Epoxidized Cyclohexene Derivatized Linseed Oil

Zou

Soucek

2004

Macro Chemistry & Physics

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Summary: Organic‐inorganic hybrid films based on epoxidized cyclohexene derivatized linseed oil (ECLO) and tetraethylorthosilicate (TEOS) oligomers were prepared via a UV‐curing process. The kinetics of the hybrid materials were studied by photo‐differential scanning calorimetry (DSC). In addition to the kinetics, the tensile properties, pencil hardness, pull‐off adhesion, reverse impact resistance, solvent resistance and abrasion resistance of the hybrid coatings were evaluated. Both dynamic mechanical thermal analysis (DMTA) and thermogravimetric analysis (TGA) were used to investigate the viscoelastic and thermal properties of the hybrid films. The morphology of the hybrid film was characterized by atomic force microscopy (AFM). Based on the results from the aforementioned evaluation of the coatings, the hybrid films exhibited higher pencil hardness, tensile strength, tensile modulus, fracture toughness, abrasion resistance, cross‐link density and thermal stability compared to the ECLO organic film. The Photo‐DSC data showed that the photo‐curing speed of the hybrid materials increased with TEOS oligomers content. It was postulated that the TEOS oligomers were reactive diluents.Structure of ECLO.magnified imageStructure of ECLO.

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“…Based on the fact that the resin is cured via photoinitiated cationic polymerisation, it has been established 53,54 that Brønsted acid sites 55 play a key role in accelerating rate of cross-linking, and, in order to explore the above hypothesis, we have carried out some initial tests with zeolites, 13 C NMR spectra recorded at 600 MHz (14.1 Tesla) using a ramped cross polarization sequence, sample spinning at 10 kHz (red -normal UV-polymerized solid resin that was cured for 3 h with no treatment; green and blue: the solid resin subjected to hygrothermal ageing in 3.5% NaCl for 6 weeks and in distilled water for 7 weeks respectively).…”

Section: Resin Modicationmentioning

confidence: 99%

Spectroscopic chemical insights leading to the design of versatile sustainable composites for enhanced marine application

et al. 2015

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The viability of a novel sustainable polymeric composite material, based on photocurable linseed oil resin was explored, with a view to exploiting its potential in marine environments. The study focused on a UV-curable resin subjected to setting through photoinitiated cationic polymerisation. Deployment of heterogeneous solid catalysts, containing isolated Brønsted acid centres, further improved the efficiency of cationic polymerisation, leading to enhanced thermal stability and water resistance. These features are highly desirable in the design of composite resins for marine applications. A wide range of spectroscopic, calorimetric and thermogravimetric methods as well as computational simulations have been employed to study the physico-chemical characteristics of the resin and its resistance to black and grey waste, UV resistance and hygrothermal ageing. The findings have revealed that, unlike conventional epoxy resins, the ELO resin demonstrated no decrease in glass transition temperature, T g , despite having been exposed to different methods of ageing. In addition, the water molecules that are absorbed by the resin during hygrothermal ageing have been found to be structurally-bound through hydrogen bonding, which is supported by initial computational studies. The structure-property correlations that have been derived help to better understand the ageing process, which could be beneficial in predicting the lifetimes of these sustainable polymeric composite materials and consequently developing novel chemical methods for improving their durability and stability.

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Cationic photopolymerization of epoxynorbornane linseed oils: The effect of diluents

Cited by 46 publications

References 22 publications

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

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

UV‐Curable Organic‐Inorganic Hybrid Film Coatings Based on Epoxidized Cyclohexene Derivatized Linseed Oil

Spectroscopic chemical insights leading to the design of versatile sustainable composites for enhanced marine application

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