Nobonene-ester based addition polymer and method for preparing the same
A norbornene and polymer technology, applied in the field of norbornene-based addition polymers, can solve problems such as reduction in polymerization yield and molecular weight
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[0130] All procedures for handling air- and light-sensitive compounds were performed by standard Schlenk techniques or using drying boxes. Nuclear magnetic resonance (NMR) spectra were obtained using a Bruker 600 spectrometer and a Bruker 300 spectrometer. 1 H NMR measured at 600MHz or 300MHz, 13 CNMR was measured at 150 MHz and 75 MHz. For definite analysis of NMR signals, 2-dimensional experiments such as COZY and HMBC were performed. The molecular weight and molecular weight distribution of the polymers were determined by GPC (Gel Permeation Chromatography) using polystyrene samples as standards. Thermal analysis, such as TGA and DSC, was carried out using a TA instrument (TGA2050; heating rate=10K / min).
[0131] Toluene was purified by distillation in potassium / benzophenone, CH 2 Cl 2 by CaH 2 Purified by distillation.
Embodiment 1
[0136] Embodiment 1: the preparation of rich exo-norbornene carboxylate methyl ester (180 ℃, 6 hours, reaction coefficient ＝84，993)
[0137] DCPD (Aldrich, 256.5 mL, 1.9 mol), methacrylate (Aldrich, 405 mL, 4.5 mol) and hydroquinone (3.2 g, 0.03 mol) were placed in a 2L autoclave. After heating to 180° C., the autoclave was stirred at 300 rpm to allow the reaction to proceed for 6 hours. After the reaction was complete, the reaction mixture was cooled and then transferred to a distillation apparatus. The reaction mixture was distilled at 50° C. under 1 Torr using a vacuum pump to obtain the product (yield: 86%). The molar ratio (mol%) of the exo isomer to the endo isomer of the product was 52:48.
[0138] 1 H-NMR (600MHz, CDCl 3 ), endotype: δ6.17(dd, 1H), 5.91(dd, 1H), 3.60(s, 3H), 3.17(b, 1H), 2.91(m, 1H), 2.88(b, 1H), 1.90 (m, 1H), 1.42(m, 2H), 1.28(m, 1H); appearance: δ6.09(m, 2H), 3.67(s, 3H), 3.01(b, 1H), 2.88(b, 1H), 2.20(m, 1H), 1.88(m, 1H), 1.51(d, 1H), 1.34(...
Embodiment 2
[0140] Embodiment 2: the preparation (190 ℃, 5 hours, reaction system Number = 89,424)
[0141] DCPD (Aldrich, 180 mL, 1.34 mol), butyl acrylate (Junsei, 500 mL, 3.49 mol) and hydroquinone (2.7 g, 0.025 mol) were placed in a 2L autoclave. After heating to 190° C., the autoclave was stirred at 300 rpm to allow the reaction to proceed for 5 hours. After the reaction was complete, the reaction mixture was cooled and then transferred to a distillation apparatus. The reaction mixture was distilled at 80° C. under 1 Torr using a vacuum pump to obtain the product (yield: 78%). The molar ratio (mol%) of the exo isomer to the endo isomer of the product was 56.2:43.8.
[0142] 1 H-NMR (600MHz, CDCl 3 ), endotype: δ6.17(dd, 1H), 5.86(dd, 1H), 3.97(t, 2H), 3.15(b, 1H), 2.88(m, 1H), 2.85(b, 1H), 1.86 (m, 1H), 1.57(m, 2H), 1.35(m, 4H), 1.21(m, 1H), 0.89(t, 3H); shape: δ 6.09(m, 2H), 4.05(t, 2H ), 2.98(b, 1H), 2.86(b, 1H), 2.20(m, 1H), 1.88(m, 1H), 1.58(m, 2H), 1.50(d, 1H), 1.34(m,...
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