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Cycloolefin-based ring-opening copolymer

A cycloolefin and copolymer technology, which is applied in the field of cycloolefin ring-opening copolymers, can solve the problems of unknown physical properties of ring-opening copolymers, and achieve low birefringence, low oxygen permeability, and excellent formability.

Active Publication Date: 2013-06-19
JSR CORPORATIOON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, the copolymers with cycloolefin monomers represented by the above formula (12) are not yet known, and the synthesis and physical properties of cycloolefin ring-opening copolymers obtained by hydrogenating these compounds are also unknown.

Method used

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  • Cycloolefin-based ring-opening copolymer
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  • Cycloolefin-based ring-opening copolymer

Examples

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example

[0137] Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited to these examples. In the following examples and comparative examples, various steps such as polymerization reaction and catalyst preparation were carried out under a nitrogen atmosphere.

[0138] In addition, each measurement and evaluation can be performed by the following methods.

[0139] Glass transition temperature (Tg):

[0140] Using a differential scanning calorimeter (manufactured by Seiko Instruments, trade name: DSC6200), the extrapolated glass transition initiation temperature was defined as the glass transition temperature (Tg) in accordance with Japanese Industrial Standard K7121.

[0141] Weight average molecular weight and molecular weight distribution:

[0142] Using gel permeation chromatography (GPC, manufactured by Tosoh Corporation, trade name HLC-8020), using tetrahydrofuran (THF) as a solvent, the weight average mol...

example 1

[0151] 5-phenyl-bicyclo[2.2.1]hept-2-ene (“phenylnorbornene” (represented as Ph-NB in ​​Table 1)) (13.5 g, 132 mmol ), Wuhuan [6.5.1.0 2，7 .1 3，6 .0 9，13 ]pentadeca-4,10-diene ("tricyclopentadiene" (indicated by TCP in Table 1)) (46.5g, 391mmol), 1-butene (0.37g, 6.59 mmol) was added to cyclohexane (107 g) and methylcyclohexane (19 g), and it heated and stirred at 100 degreeC. Separately, a solution obtained by adding a ruthenium carbene complex catalyst (0.684 mg, 1.046 μmol) represented by the following formula (11) to toluene (0.55 g) was prepared. To the aforementioned monomer solution, the ruthenium carbene complex catalyst solution was added to start the polymerization reaction. After 1 hour of polymerization, a toluene (0.55 g) solution of ethyl vinyl ether (0.0735 g, 1.046 μmol) was added as a reaction stopper to obtain a ring-opened copolymer solution. The conversion rate of the monomer was measured and found to be 99% by mass. A ring-opened copolymer was obtain...

example 2

[0157] Phenylnorbornene (expressed as Ph-NB in ​​Table 1) (18 g, 176 mmol), tricyclopentadiene (TCP) (42 g, 353 mmol) as a cycloolefin monomer, and as a molecular weight regulator The 1-butene (0.37g, 6.67mmol) of a reagent was added to cyclohexane (107g) and methylcyclohexane (19g), and it heated at 100 degreeC, and stirred. Separately, a solution obtained by adding the ruthenium carbene complex represented by the above formula (11) (0.416 mg, 0.635 μmol) to toluene (0.55 g) was prepared. To the aforementioned monomer solution, the ruthenium carbene complex catalyst solution was added to start the polymerization reaction. After 1 hour of polymerization, a toluene (0.55 g) solution of ethyl vinyl ether (0.046 mg, 0.635 μmol) was added as a reaction stopper to obtain a ring-opened copolymer solution. The conversion rate of the monomer was measured and found to be 99% by mass. A ring-opened copolymer was obtained by precipitating a part of it in a large amount of methanol and ...

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Abstract

The invention provides a cycloolefin-based ring-opening copolymer which realizes high optical properties (high refraction index, High abbe number and low birefringent fiber) and excellent resin processing property, low oxygen permeability and high mechanical strength. The cycloolefin-based ring-opening copolymer contains repeating units represented by formula (1) and formula (2), wherein m is an integer from 1 to 3, P and q are independent integrals from 0 to 2, R1 to R12 respectively represent any of the hydrogen atoms, halogen atoms and aliphatic hydrocarbyl being replaceable by halogen atoms and having 1 to 4 carbons.

Description

technical field [0001] The present invention relates to a cycloolefin-based ring-opening copolymer having high refractive index, high Abbe number, low birefringence, excellent resin processability, low oxygen permeability, and high mechanical strength. Background technique [0002] Ring-Opening Metathesis Polymerization (Ring-Opening Metathesis Polymerization, hereinafter referred to as ROMP) of cycloolefin monomers, followed by hydrogenation of the double bonds contained in the copolymer (hereinafter also referred to as ROMP-hydrogenation) Olefin-based ring-opening copolymers are thermoplastic transparent resins characterized by high light transmittance, high refractive index, and high heat resistance. [0003] In the field of optical materials such as optical lenses, optical fibers, and optical films that require the above-mentioned functions, the application of this thermoplastic transparent resin is expanding. Especially in the application of optical lenses, further hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/08G02B1/04
CPCA61L31/04C08F232/00C08G61/08C08L45/00C08L2201/10C08L2203/02G02B1/04
Inventor 神谷育代庄田良平凑裕二多田罗了嗣铃木理奈茂木武志丸山洋一郎
Owner JSR CORPORATIOON
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