Abstract
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.
Highlights
The ultraviolet (UV)-curing technique has received enormous interest in modern industrial areas such as coatings, inks, and adhesives due to its distinct advantages, including being efficient, energy-saving, enabling, economical, eco-friendly, etc. [1,2,3,4,5,6]
Plant oils have the features of environmentally benign, abundance, biodegradability, and triglyceride structures; they have been used as an ideal substitute to prepare bio-based prepolymers for UV-curable coatings [10,11,12,13,14,15,16,17,18,19]
All the results indicated that the MAAMA modification of epoxidized plant oils was much more effective to achieve high-performance plant oil-based epoxy acrylate (EA) resins than the common acrylic acid (AA) modification
Summary
The ultraviolet (UV)-curing technique has received enormous interest in modern industrial areas such as coatings, inks, and adhesives due to its distinct advantages, including being efficient, energy-saving, enabling, economical, eco-friendly, etc. [1,2,3,4,5,6]. Polymers 2020, 12, 2165 available in the global market are from non-renewable, environmentally polluting petroleum-based fossil resources. Plant oils have the features of environmentally benign, abundance, biodegradability, and triglyceride structures; they have been used as an ideal substitute to prepare bio-based prepolymers for UV-curable coatings [10,11,12,13,14,15,16,17,18,19]. Plant-oil-based epoxy acrylate (EA) is one of the common UV-curable prepolymers, which is usually prepared through the ring-opening reaction of epoxidized plant oils with acrylic acid (AA) or its derivatives. Acrylated epoxidized soybean oil (AESO), perhaps the most often bio-based UV-curable prepolymer, has been proverbially employed in the fields of coatings and adhesives [7,15,20,21,22].
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