Catalyst composition, method for producing norbornene copolymer using catalyst composition, norbornene copolymer, and heat resistant film using copolymer
A technology of norbornene and a composition is applied in the field of catalyst compositions for preparing catalysts, which can solve the problems of reduced catalytic activity, reduced catalytic activity of catalysts, etc., and achieves the effects of excellent electrical insulation, excellent transparency, and excellent low hygroscopicity.
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[0132] The present invention is explained in more detail below with reference to Examples and Comparative Examples, but the present invention is not limited to these explanations.
[0133] The weight average molecular weight (Mw), number average molecular weight (Mn) and molecular weight distribution (Mw / Mn) of the polymers obtained in each example were measured by gel permeation chromatography (GPC) using polystyrene as a standard. In addition, the composition ratio of norbornene and 2-acetoxymethyl-5-norbornene contained in the copolymer is given by 1 The peak obtained by H-NMR [δ: 3.5-4.5ppm, "-COOCH of 2-acetoxymethyl-5-norbornene 2 -" unit and δ: 0.5-3.0 ("-CH of norbornene and 2-acetoxymethyl-5-norbornene 3 COO-", "-CH 2 -" and "-CH=" unit)] integral ratio is determined.
[0134] Various physical properties of the substances synthesized in Examples were measured in the following manner.
[0135] 1. 1 H-NMR and 13 C-NMR:
[0136] Type of equipment used: JEOL EX-400...
Synthetic example 1
[0169] Synthesis Example 1: Synthesis of 2-Acetoxymethyl-5-Norbornene
[0170]Dicyclopentadiene (165.00 g, 1.248 mol, manufactured by Wako Pure Chemical Industries, Ltd.), allyl acetate (312.40 g, 3.120 mol, Tokyo Chemical Industry Co. , Ltd.) and hydroquinone (0.50 g, 0.0045 mol, manufactured by Wako Pure Chemical Industries, Ltd.). After replacing the system with nitrogen, the autoclave was heated to 180° C. while stirring at 400 rpm to react the mixture for 5 hours. After the reaction was completed, the autoclave was cooled to room temperature, the contents were transferred to a distillation apparatus and distilled under reduced pressure to obtain 207.56 g of a colorless transparent liquid, which was a fraction at 0.9 MPa at 38°C.
[0171] Measurement of the liquid thus obtained 1 H-NMR, confirming that it is the target 2-acetoxymethyl-5-norbornene. In addition, the molar ratio of the exo isomer to the endo isomer of 2-acetoxymethyl-5-norbornene was exo / endo=80 / 20.
Embodiment 1
[0173] Under a nitrogen atmosphere, norbornene (4.7 g, 0.05 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) and 2-acetoxymethyl-5-norbornene (8.3 g, 0.05 mol) were dissolved in 200 mL of glass The resulting polymerization bottle was mixed to prepare the monomer solution. On the other hand, bisindenyl nickel (5.9 mg, 20 μmol), tris(pentafluorophenyl)borane [B(C 6 f 5 ) 3 ] (30.7 mg, 6 μmol) and trimethylaluminum (2.0 M toluene solution, 0.05 ml, 100 μmol, manufactured by Sigma-Aldrich Japan K.K.) were charged into a 10 mL glass ampoule, and they were dissolved in 5 mL of dehydrated toluene. The ampoule was immediately removed from the glove box, and its entire amount was added to the polymerization bottle to start the polymerization. Polymerization was carried out at room temperature for 3 hours, and the reaction was quenched by adding the reaction liquid to a large amount of methanol to precipitate the polymer. The polymer was isolated by filtration and washed, and...
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