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Cyclic olefin ring-opening polymer, hydride thereof, composition of the hydride, and tricyclopentadiene

A technology of tricyclopentadiene and cyclic olefin, which is applied in the field of cyclic olefin ring-opening polymers, can solve the problems of reduced solvent solubility and gel generation, and achieves excellent polymerization conversion rate, refractive index and Abbe number. high effect

Active Publication Date: 2015-05-13
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the tricyclopentadiene obtained by this method is 1,4,4a,4b,5,8,8a,9a-octahydro-1,4;5,8-di A bridge-1H-fluorene and 3a,4,4a,5,8,8a,9,9a-octahydro-4,9 represented by formula (5); 5,8-dimethyl bridge-1H-benzo[f ] isomer mixture of indene, wherein 1,4,4a,4b,5,8,8a,9a-octahydro-1,4; 5,8-dimethylbridge-1H-fluorene represented by formula (6) are as above As mentioned above, a crosslinking reaction is initiated during the polymerization reaction, so that the resulting polymer has a high molecular weight, which causes problems such as a decrease in the solubility of the solvent, or the generation of a gel.

Method used

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  • Cyclic olefin ring-opening polymer, hydride thereof, composition of the hydride, and tricyclopentadiene
  • Cyclic olefin ring-opening polymer, hydride thereof, composition of the hydride, and tricyclopentadiene
  • Cyclic olefin ring-opening polymer, hydride thereof, composition of the hydride, and tricyclopentadiene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0246] Add to toluene (275g) the compound represented by formula (2-1) containing 82% of its geometric isomers (including enantiomers, hereinafter, also referred to as compound (2- 1) TCP (71.9g, 363mmol, the content of geometric isomers other than compound (2-1) is 18%), 8-methyl-8-methoxycarbonyl-tetracyclo[4.4.0.1 2,5 .1 7,10 ] Dodec-3-ene (37.5g, 161mmol, hereinafter, also referred to as DNM), bicyclo[2.2.1] hept-2-ene (22.1g, 235mmol, hereinafter, also referred to as NB) and as a molecular weight regulator Add 1-butene (1.69g, 30.1mmol) as the solvent, and heat and stir at 105°C. Separately prepare to mix i-Bu at room temperature 3 Toluene solution (0.28 mL) of Al (75 μmol) and methanol (11 μmol) and WCl 6 (38 μmol) in toluene (0.75 mL). To the toluene solution of the above-mentioned monomers, add i-Bu in sequence 3 Mixed toluene solution of Al and methanol, WCl 6 solution in toluene to start the polymerization reaction. After 1 hour of polymerization, LiOH (228 mi...

Embodiment 2

[0249] As TCP, except for using a substance containing 90% of the compound (2-1) (including enantiomers) among its geometric isomers, the same operation as in Example 1 was carried out to obtain ring-opening copolymerization hydrogenation things [2]. pass 1 The hydrogenation rate analyzed by H-NMR was 99.9%. Tg = 139°C by DSC. As a result of GPC measurement, the weight average molecular weight (Mw) = 36000, and the molecular weight distribution (Mw / Mn) = 2.8. In addition, the refractive index n D =1.533, the Abbe value is 57. The results are shown in Table 1.

Embodiment 3

[0251] As TCP, except for using a substance containing 96% of compound (2-1) (including enantiomers) among its geometric isomers, the same operation as in Example 1 was carried out to obtain ring-opening copolymerization hydrogenation things [3]. pass 1 The hydrogenation rate analyzed by H-NMR was 99.9%. Tg = 139°C by DSC. As a result of GPC measurement, the weight average molecular weight (Mw) = 40000, and the molecular weight distribution (Mw / Mn) = 2.9. In addition, the refractive index n D =1.533, the Abbe value is 56. The results are shown in Table 1.

[0252] [Comparative Example 1]

[0253]As TCP, using a geometric isomer containing 50% of the compound (2-1) (including enantiomers), the same operation as in Example 1 was carried out to obtain a ring-opening copolymerization hydride [4]. pass 1 The hydrogenation rate analyzed by H-NMR was 99.9%. Tg = 140°C as measured by DSC. As a result of GPC measurement, the weight average molecular weight (Mw) = 39000, and t...

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Abstract

Disclosed are: a cyclic olefin ring-opening polymer which has high refractive index, high Abbe number and solubility in a solvent and is useful for applications as optical materials; a hydride of the cyclic olefin ring-opening polymer; and a composition of the hydride, in which a compounding ingredient as typified by a rubbery polymer can be dispersed. The cyclic olefin ring-opening polymer can be obtained by ring-opening copolymerization of a cyclic olefin monomer mixture that contains trimers to pentamers of cyclopentadiene, and the trimers to pentamers of cyclopentadiene contain 55% or more of compounds, which are obtained in cases where n = 1-3, as geometrical isomers (2).

Description

technical field [0001] The present invention relates to a cyclic olefin ring-opening polymer having a high refractive index and a high Abbe number, a hydrogenated product thereof, a hydrogenated product composition of the cyclic olefin ring-opening polymerization, and tricyclopentadiene, which are useful in optical materials. Background technique [0002] Cyclic olefin ring-opened polymers, especially hydrogenated cyclic olefin ring-opened polymers (hereinafter, cyclic olefin ring-opened polymers, hydrogenated cyclic olefin ring-opened polymers, and copolymers are also referred to as cyclic olefin ring-opened polymers. Cyclopolymer) is attracting attention as a thermoplastic transparent resin with excellent light transmittance and heat resistance. The polymer is widely used in the fields of optical materials such as optical lenses, optical fibers, and optical films. In addition, mobile devices such as mobile phones incorporating these optical lenses and the like have been d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/08C07C13/64C08L65/00
CPCC07C13/64C08G61/08C08G2261/3324C08G2261/418C08F8/04C08F32/00C08L65/00
Inventor 多田罗了嗣木村优糸见健神谷育代海津充孝丸山洋一郎铃木义信中村和洋柴田拓金山泰三菅原哲德
Owner JSR CORPORATIOON
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