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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 the problems of polymerization yield and molecular weight reduction

Inactive Publication Date: 2006-10-25
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, according to the report of Sen et al., if the polar group is directly attached to the norbornene ring, the polymerization yield and molecular weight decrease even more (Organometallics, 2001, Vol. 20, 2802-2812)

Method used

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  • Nobonene-ester based addition polymer and method for preparing the same
  • Nobonene-ester based addition polymer and method for preparing the same
  • Nobonene-ester based addition polymer and method for preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[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 at 600MHz or 300MHz, 13 CNMR was measured at 150MHz and 75MHz. For definite analysis of NMR signals, 2-dimensional assays such as COSY 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 performed using a TA instrument (TGA2050; heating rate = 10 K / min).

[0131] Toluene was purified by distillation in potassium / benzophenone, CH 2 Cl 2 by CaH 2 purified by distillation.

Embodiment 1

[0136] Example 1: Preparation of exo-rich norbornene carboxylate methyl ester (180°C, 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 2 L 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 completed, 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 exo-isomer to 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 (m, 2H). ...

Embodiment 2

[0140] Example 2: Preparation of exo-rich norbornene carboxylate butyl ester (190°C, 5 hours, reaction coefficient = 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 2 L 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 completed, 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 exo-isomer to 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); Appearance: δ6.09 (m, 2H), 4.05 (t, 2H), 2.98(b, 1H), 2.86(b, 1H), 2.20(m, 1H), 1.88(m, 1H), ...

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Abstract

The present invention relates to norbornene-based addition polymers, and more particularly to addition polymers of norbornene-based monomers containing ester groups. The present invention provides a norbornene-ester-based addition polymer with a molecular weight (Mn) greater than 20,000 and a norbornene-ester-based monomer containing more than 50 mol% of an exo-norbornene-ester monomer as a repeating unit. The method of the norbornene-ester addition polymer, and the optically anisotropic film containing the norbornene-ester addition polymer. The norbornene-ester-based addition polymers of the present invention are transparent, have low permittivity, have good thermal stability and strength, do not leave undesired materials when attached to metals or other polymers, and have Good adhesion, so the norbornene-ester-based addition polymer can be used in optical films, retardation films, plastic matrix materials, transparent polymers such as POF or PCB, insulating materials or insulating electronic equipment such as PCB or insulating Material.

Description

technical field [0001] The present invention relates to norbornene-based addition polymers, and more particularly, to addition polymers of norbornene-based monomers containing ester groups. Background technique [0002] Currently, PMMA (polymethyl methacrylate) or PC (polycarbonate) or the like is widely used as a transparent polymer. Although PMMA has good transparency, its dimensional stability is poor due to its high hygroscopicity. Therefore, it is not suitable as a material for precision optical equipment or displays. [0003] Until now, inorganic substances such as silicon dioxide or silicon nitride have been mainly used as insulating materials. However, as the need for small and efficient devices increases, new high-functionality materials are required. [0004] In this regard, polymers with low permittivity, low hygroscopicity, excellent metal adhesion, strength, thermal stability and transparency, and high glass transition temperatures (Tg>250°C) have attracte...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/06C08F232/08C08F210/00G02B5/30C07C67/347C07C67/62C07C69/753C08F4/70C08F32/04C08F32/08C08J5/18G02F1/1362
CPCC08G61/06C08F32/08G02F1/136227
Inventor 全成浩金源国尹性澈林兑宣金宪金敬勋李贞旼白京林安相斗
Owner LG CHEM LTD
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