Abstract
Poly(eugenyl-2-hydroxypropyl methacrylate) (PEUGMA), poly(methyl methacrylate) (PMMA) and poly(eugenyl-2-hydroxypropyl methacrylate-co-methyl methacrylate) (PEUGMA-co-MMA) were synthesized by a free radical polymerization route in the presence of azobisisobutyronitrile. EUGMA was synthesized by etherification of the eugenol phenolic hydroxyl group with glycidyl methacrylate. Polymers and copolymers were characterized using size exclusion chromatography, Fourier transform infrared, and nuclear magnetic resonance. The effects of the encumbering substituent on the thermal behavior of the polymers and copolymers were studied by differential scanning calorimetry, thermogravimetry (TG) and direct analysis, using real-time, time-of-flight mass spectroscopy (DART-ToF-MS) methods. The results obtained revealed that for PEUGMA, the average molecular weight was 1.08 × 105, and increased slowly with the decrease in the EUGMA content in the copolymer. The order of the distribution of dyads comonomer units in the copolymer chains estimated by the Igarashi method based on the reactivity ratio does reveal a random distribution with a tendency toward alternation. The glass transition temperature of PEUGMA (46 °C) increased with the MMA content in the copolymer, and those of the copolymer fit well with the Johnston’s linearized expression. The TG analysis of pure PEUGMA revealed a significantly high thermal stability compared to that of PMMA. During its degradation, the preliminary decomposition was at 340 °C, and decreased as the MMA units increased in the copolymer. The DART-ToF-MS analysis revealed that the isothermal decomposition of PEUGMA led to a regeneration of raw materials such as EUGMA, GMA and EUG, in which the maximum amount was achieved at 450 °C.
Highlights
Methacrylate polymers containing epoxyl groups have attracted several researchers in different domains
Poly(eugenyl-2-hydroxypropyl methacrylate) (PEUGMA), poly(methyl methacrylate) (PMMA) homopolymers, and PEUGMA-co-MMA copolymers were synthesized under a nitrogen gas atmosphere via the free radical polymerization route in 1,4-dioxan using under a nitrogen gas atmosphere via the free radical polymerization route in 1,4-dioxan using azobisisobutyronitrile (AIBN) as initiator at 70 ◦ C
Cm−1, the Eugenyl-2-Hydroxypropyl Methacrylate (EUGMA) spectrum reveals the total disappearance of theand absorption band centered at absorption
Summary
Methacrylate polymers containing epoxyl groups have attracted several researchers in different domains. Polymers 2020, 12, 160 methacrylate, and the epoxy functional groups can improve the performance of the resulting materials through crosslinking reactions. Based on this principle, poly(glycidyl methacrylate) (PGMA) is utilized the most in this family, and has been the subject of a large number of applications; these are used in surface modification [1,2,3,4,5,6], adhesives [7,8], compatibilizers for polymer blends [9,10,11,12], electrolytes [13]. The influence of the bulky substituent on the molecular weight and microstructure of the obtained polymers and copolymers were investigated To reach this goal, different parameters were studied, such as the reactivity ratios and the order of distribution of dyads comonomer units in the copolymer chains were undertaken, using nuclear magnetic resonance (NMR). A direct analysis in real time (DART) was employed for the first time to study the isothermal decomposition of the synthesized polymers and copolymers
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