Preparation and Properties of Plant-Oil-Based Epoxy Acrylate-Like Resins for UV-Curable Coatings

Novel oil-based epoxy acrylate (EA)-like prepolymers were synthesized via the ring-opening reaction of epoxidized plant oils with a new unsaturated carboxyl acid precursor (MAAMA) synthesized by reacting maleic anhydride (MA) with methallyl alcohol (MAA). Since the employed epoxidized oils including epoxidized soybean oil (ESO), epoxidized rubber seed oil (ERSO), and epoxidized wilsoniana seed oil (EWSO) possessed epoxy values of 7.34–4.38%, the obtained epoxy acrylate (EA)-like prepolymers (MMESO, MMERSO, and MMEWSO) indicated a C=C functionality of 7.81–4.40 per triglyceride. Furthermore, effects of the C=C functionality and the addition of hydroxyethyl methacrylate (HEMA) diluent on the ultimate properties of the resulting UV-cured EA-like materials were investigated and compared with those of commercially available acrylated ESO (AESO) resins. As the C=C functionality increased, the storage modulus at 25 °C (E’25), glass transition temperature (Tg), 5% weight–loss temperature (T5), tensile strength and modulus (σ and E), and hardness of the coating for both the pure EA and EA/HEMA resins increased significantly as well. These properties indicated similar trends when comparing the EA materials with 30% of HEMA with those pure EA materials. Specially, although ERSO had a clearly lower epoxy value that ESO, both the UV-cured pure MMERSO and MMERSO/HEMA materials showed much better E’25, Tg, σ, and E than their AESO counterparts, indicating that the MAAMA modification of epoxidized plant oils was much more effective than the modification of acrylic acid to achieve high-performance oil-based epoxy acrylate resins.

The Synthesis and Characterization of a Novel Cationic Asphalt Emulsifier

A new cationic asphalt emulsifier of N,N-dimethyl-N-(3-(N',N'-dimethyl amido)-2-hydroxy propyl)- coconut oil amide propyl-1-ammonium chloride was synthesized by two steps reaction of coconut oil acyl propyl dimethyl tertiary amine (PKO), epoxy chloropropane and dimethylamine. The chemical structure of the key intermediate of N,N-dimethyl-N-(ethylene oxide-2-methylene)-coconut oil amide propyl-1-ammonium chloride was confirmed by FTIR, 1H NMR and elemental analysis. The optimum reaction condition of first step was obtained by single factor analysis: reaction time 5 h, reaction temperature 50 °C, feedstock mole ratio of epoxy chloropropane to PKO 1.05. The reaction yield is 82.15% and the epoxy value is 40.39% at the optimum conditions. The critical micelle concentration (CMC) of the asphalt emulsifier is 7.80×10-2 mol/L. The surface tension at CMC is 24.57 mN/m. The emulsifier showed excellent emulsification effect for the asphalt. The prepared bituminous emulsion had higher storage stability. The emulsifier belongs to medium-set asphalt emulsifier.

Synthesis of Lignin-Based Epoxy Resin in Ionic Liquid [BMIm]Cl

Industrial alkali lignin (LG) was used as raw material and ionic liquid 1-butyl 3-methylimidazolium chloride ([BMIm]Cl) was used as solvent. Alkali lignin was dissolved into the [BMIm]Cl and modified as propyl ether lignin(HLG). Then the HLG modified lignin was used to synthesizing the lignin-based epoxy resin (LGEP) with epoxy chloropropane. The structure of LG, HLG and LGEP were characterized with FT-IR, the results indicated that the propyl group was introduced to the LG and the reaction activity was improved. The expoxy value analysis results showed that the optimum synthesis temperature was 80°C and the epoxy value was 0.218.

Study on the Regeneration of Quaternary Ammonium Heteropolyphosphatotungstate Catalyst

The quaternary ammonium heteropolyphosphatetungstate compound is proved as a promising catalyst to accelerate the synthesis of epoxidized soybean oil (ESO). As to enhance the efficiency of the catalyst, this paper investigated the process of regeneration of deactivated catalyst (DC) from reaction system of ESO. The single factor experiments were carried out to optimize the regeneration conditions and the optimize process conditions were as follows: acid solution at pH 3, m (deactivated catalyst):m (H2O2):m (H3PO4):m (cetylpyridiniumammonium chloride)=10:5:1:1,and stirred via mechanical and ultrasound agitation . Under above conditions, the epoxy value (≥6.0 %) of ESO which were catalyzed by generated catalyst and yield (≥92 %) were achieved.The results indicate that the activity of regenerated catalysts remain the same as that of the fresh catalysts and certify the economic feasibility of the process.

Modification of Epoxy Resin with Silicone for Electronic Encapsulation Application

The reaction was carried out with a solventless (hot-melt) method using epoxy resin (E-20) as a base material and dihydroxydiphenylsilane (DHDPS) or polymethyltriethoxysilane (PTS) as a modifier. IR spectrum, epoxy value of modified epoxy resins indicated that DHDPS and PTS were incorporated into epoxy resin respectively. The influences of silicone contents on softening point and thermal resistance of cured silicone modified epoxy resin systems were studied. The thermal stability was investigated by thermogravimetic analysis (TGA). Effects of the viscosity of packaging slurry on the performance of encapsulated electronic elements were also investigated. In contrast to ED-20 cured system, the thermal resistance, toughness, humidity resistance of ETS-20 cured systems improved more obvious. And ETS-20 has exhibited excellent resistance to the thermal shock cycling test. It indicated that ETS-20 can be applicated for electronic encapsulation. The viscosity of packaging slurry was most appropriate when it was 170~200 mPas.

Study on Synthesis of Epoxy Resin Modified with Polysiloxane

With allyl glycidyl ether and terminal hydrogen silicone oil, in certain conditions, the silicone-modified epoxy resin synthesized by the hydrosilylation reaction. This study discuss the effect of the structure and properties on the synthesized product, such as the catalyst, reaction time, reaction temperature and the C = C/Si-H molar ratio of allyl glycidyl ether and terminal hydrogen silicone oil. Infrared spectroscopy, gel permeation chromatography (GPC), epoxy value and hydrolysis chlorine of the polysiloxane-modified epoxy resin were characterized and analysized. The results show that the terminal hydrogen silicone oil-modified epoxy resin has balanced epoxy value, molecular weight and molecular weight distribution, the conversion of reactive hydrogen is the highest when the dosage of H2PtCl66H2O is 0.01% to 0.02% of reactant in weight, the molar ratio of C=C /Si-H in AGE (allyl glycidyl ether) and the terminal of hydrogen silicone oil is 4.28:1, the reaction temperature is 80°C to 85°C, reaction time is controlled in 6 hours.