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Ring-opening polymer of cyclopentene and method for producing same

A manufacturing method and technology of cyclopentene, applied in tire parts, transportation and packaging, special tires, etc., can solve the problems of low heat generation, low Mooney viscosity, poor rubber properties, etc., and achieve excellent rubber properties and low heat generation Excellent properties and excellent Mooney viscosity

Active Publication Date: 2012-11-14
ZEON CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although such a cyclopentene ring-opened polymer with a high trans ratio has excellent green strength and abrasion resistance, it has the following problems due to its high crystallinity: poor rubber properties at low temperatures, Various rubbers that cannot be used at low temperatures, such as rubber materials for tires, etc.
However, the cyclopentene ring-opening polymer disclosed in Non-Patent Document 1 has low dispersibility to fillers such as silica and carbon black. Therefore, although the characteristics at low temperatures can be improved, there are still disadvantages. The problem of fever
In addition, the cyclopentene ring-opened polymer disclosed in Non-Patent Document 1 has problems of difficult kneading at high temperatures and poor processability due to its low Mooney viscosity.

Method used

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  • Ring-opening polymer of cyclopentene and method for producing same
  • Ring-opening polymer of cyclopentene and method for producing same
  • Ring-opening polymer of cyclopentene and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0155] Add 1.0 wt% WCl to a glass container with a stirrer under nitrogen atmosphere 6 8.7 parts / toluene solution and 4.3 parts of 2.5 weight% diisobutylmono(n-hexyloxide)aluminum / toluene solution prepared in Reference Example 1 were stirred for 15 minutes to obtain a catalyst solution. In addition, under a nitrogen atmosphere, add 150 parts of cyclopentene and 0.22 parts of allyltriethoxysilane into a pressure-resistant glass reaction vessel with a stirrer, and add 13 parts of the catalyst solution prepared above to it, and put it at 25 ° C Polymerization was carried out for 6 hours. After 6 hours of polymerization, add excess isopropanol to the pressure-resistant glass reaction vessel to stop the polymerization, and then inject the solution in the pressure-resistant glass reaction vessel into the solution containing 2,6-di-tert-butyl-p-cresol (BHT) in an apparent excess of isopropanol. Next, the precipitated polymer was recovered, washed with isopropanol, and vacuum-dried ...

Embodiment 2

[0159] 30 parts of cyclopentene ring-opening polymers obtained in the same manner as in Example 1 were dissolved in 150 parts of tetrahydrofuran, 2.5 parts of 1 equivalent aqueous hydrochloric acid were added, and stirred at 80° C. for 4 hours to carry out the hydrolysis reaction ( A hydrolysis reaction in which a triethoxysilyl group is reacted to obtain a trihydroxysilyl group). After the hydrolysis reaction is complete, a significant excess of isopropanol containing 2,6-di-tert-butyl-p-cresol (BHT) is injected. Next, the precipitated polymer was recovered, washed with isopropanol, and vacuum-dried at 40° C. for 3 days to obtain 30 parts of a cyclopentene ring-opened polymer. Wherein, carried out for the gained cyclopentene ring-opening polymer 1 In H-NMR measurement, the following results were confirmed: the peak derived from the ethyl group of the triethoxysilyl group almost disappeared, and more than 99% of the triethoxysilyl group was hydrolyzed to be converted into a t...

Embodiment 3

[0161] Add 1.0 wt% WCl to a glass container with a stirrer under nitrogen atmosphere 6 8.7 parts / toluene solution and 4.3 parts of 2.5% by weight diisobutyl mono(n-butoxide)aluminum / toluene solution prepared in Reference Example 2, after stirring for 10 minutes, add 0.039 parts of ethyl acetate and carry out 10 minutes By stirring, a catalyst solution was obtained. In addition, under a nitrogen atmosphere, 150 parts of cyclopentene and 0.29 parts of 2-styrylethyltrimethoxysilane were added to a pressure-resistant glass reaction vessel with a stirrer, and 13 parts of the catalyst solution prepared above were added thereto, Polymerization was carried out at 25°C for 6 hours. After 6 hours of polymerization, add excess isopropanol to the pressure-resistant glass reaction vessel to stop the polymerization, and then inject the solution in the pressure-resistant glass reaction vessel into the solution containing 2,6-di-tert-butyl p-cresol (BHT) in a large excess of isopropanol. N...

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Abstract

Provided is a ring-opening polymer of cyclopentene which is characterized by having a cis ratio of the cyclopentene-origin structural units of 30% or greater and a weight-average molecular weight (Mw) of 100,000-1,000,000 and carrying an oxysilyl group at an end of the polymer chain. The ring-opening polymer of cyclopentene can be produced by ring-opening polymerizing cyclopentene in the presence of, for example, a compound of a transition metal belonging to group 6 in the periodic table, an organoaluminum compound represented by general formula (1) and an oxysilyl group-containing olefinic unsaturated hydrocarbon. (R1)3-xAl(OR2)x (1)In general formula (1), R1 and R2 represent a C1-20 hydrocarbon group; and x satisfies the requirement 0<x<3.

Description

technical field [0001] The present invention relates to a cyclopentene ring-opened polymer and a method for producing the same. Specifically, it relates to a cyclopentene ring-opened polymer excellent in rubber properties at low temperatures, low heat generation, and processability, and a method for producing the same. In addition, the present invention also relates to a rubber composition obtained by using the cyclopentene ring-opened polymer. Background technique [0002] Usually, by making cyclopentene in WCl 6 、MoCl 5 Metathesis polymerization and ring-opening polymerization in the presence of a so-called Ziegler-Natta catalyst composed of a transition metal compound of Group 6 of the periodic table and an organometallic activator such as triisobutylaluminum, diethylaluminum chloride, and tetrabutyltin , unsaturated linear ring-opened polymers can be obtained. [0003] Conventionally, as a cyclopentene ring-opening polymer obtained in this way, a cyclopentene ring-ope...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/08B60C1/00C08K3/04C08K3/36C08L65/00
CPCB60C1/00C08F110/14C08K3/36C08L65/00C08F10/14C08F210/14C08G2261/3321C08G2261/418C08G61/08C08K3/04C08C19/25
Inventor 角替靖男武山庆久
Owner ZEON CORP
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