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High CIS-1,4 conjugated diene polymer with double bonds on side arm and preparation method thereof as well as high CIS-1,4 conjugated diene polymer with functional groups on side arm and preparation method thereof

A diolefin and polymer technology, which is applied in the field of high cis-1,4 conjugated diolefin polymers with functional groups in side arms and the preparation method, can solve the problems of inability to obtain high stereoregularity conjugated diolefin polymers and the like

Active Publication Date: 2016-05-04
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The present invention aims to solve the technical problem that the prior art cannot obtain conjugated diene polymers containing polar functional groups with high tacticity, and provides a high cis-1,4 conjugated diene polymer with double bonds in side arms and its preparation Method, high cis-1,4 conjugated diene polymer with side arm functional group and its preparation method

Method used

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  • High CIS-1,4 conjugated diene polymer with double bonds on side arm and preparation method thereof as well as high CIS-1,4 conjugated diene polymer with functional groups on side arm and preparation method thereof
  • High CIS-1,4 conjugated diene polymer with double bonds on side arm and preparation method thereof as well as high CIS-1,4 conjugated diene polymer with functional groups on side arm and preparation method thereof
  • High CIS-1,4 conjugated diene polymer with double bonds on side arm and preparation method thereof as well as high CIS-1,4 conjugated diene polymer with functional groups on side arm and preparation method thereof

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preparation example Construction

[0042] A method for preparing a side arm with a double bond high cis-1,4 conjugated diene polymer, comprising the following steps:

[0043] Under the action of catalyst and co-catalyst, the side arm with double bond high cis- 1,4 conjugated diene polymer;

[0044]

[0045] where z=0,1,2,3 or 4.

[0046] The catalyst is a tridentate carbazole-based rare earth complex shown in formula (III), and its structural formula is as follows:

[0047]

[0048] Among them, R 2 is hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, phenyl or benzyl; R 3 is methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, phenyl, benzyl or cyclohexyl; Ln is rare earth metal Y, Lu, Sc, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Ho, Er, Tm or Yb.

[0049] The cocatalyst is organoboron salt [Ph 3 C][B(C 6 f 5 ) 4 ], [PhNMe 2 H][B(C 6 f 5 ) 4 ], [Ph 3 C][BPh 4 ], [PhNMe 2 H][BPh 4 ] or B(C 6 f 5 ) 3 .

[0050] During the preparation of the high cis-1,4 conjugated diene polymers with doub...

Embodiment 1

[0071] Under the protection of nitrogen, add 2.5mL of anhydrous toluene and 2.5mmol of 2-methylene-1,6-heptadiene to the dry polymerization reactor successively, then put it into a constant temperature device at 25°C, and add 10μmol of catalyst Tridentate carbazolyl rare earth complexes (R 2 is tert-butyl, R 3 is phenyl, Ln metal Y) and 10 μmol cocatalyst organoboron salt ([Ph 3 C][B(C 6 f 5 ) 4 ])) to initiate the reaction, and after 5 minutes of reaction, the reaction solution was poured into an ethanol solution containing 10% (V / V) hydrochloric acid, and a white polymer was precipitated. The filtered product was washed with ethanol for 3 times, and then dried in a vacuum oven at 50° C. for 24 to 36 hours to obtain 0.27 g of a high cis-1,4 conjugated diene homopolymer with double bonds in side arms. The number average molecular weight (M n ) is 32.9kg / mol, molecular weight distribution (M w / M n ) is 1.12, and the polymer glass transition temperature (T g ) is -82.3...

Embodiment 2

[0073] Change the added anhydrous toluene and 2-methylene-1,6-heptadiene in Example 1 to 10mL and 10mL respectively, change the reaction time to 60min, and keep other conditions unchanged, and finally obtain the side arm with a double bond High cis-1,4 conjugated diene homopolymer 1.08g. The number average molecular weight (M n ) is 121kg / mol, molecular weight distribution (M w / M n ) is 1.08, and the polymer glass transition temperature (T g ) is -81.9°C. pass 1 H and 13 CNMR spectrum analysis calculates the tacticity of the polymer to be cis-1,4 content of 98.5%.

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Abstract

The invention relates to a high CIS-1,4 conjugated diene polymer with double bonds on a side arm and a preparation method thereof as well as a high CIS-1,4 conjugated diene polymer with functional groups on a side arm and a preparation method thereof, belongs to the field of conjugated diene polymers and solves the technical problem in the prior art that a high-stereo-tacticity conjugated diene polymer containing polar functional groups cannot be obtained. The invention first provides the high CIS-1,4 conjugated diene polymer with the double bonds on the side arm and the preparation method thereof, and based on the polymer, a functional high CIS-1,4 conjugated diene polymer is synthesized. The high CIS-1,4 conjugated diene polymer with the double bonds on the side arm is prepared by homopolymerization of a conjugated diene monomer with double bonds on the side arm or copolymerization of the conjugated diene monomer with the double bonds on the side arm and non-functional conjugated diene under catalytic action of a catalytic system formed by a tridentate carbazolyl rare earth complex and organic boron salt, so that the polymer prepared by adopting the method is controllable in both molecular structure and relative molecular mass. The polymer with the double bonds on the side arm reacts with various sulfhydryl compounds to obtain the high CIS-1,4 conjugated diene polymer with the functional groups on the side arm.

Description

technical field [0001] The invention relates to the field of conjugated diene polymers, in particular to a high cis-1,4 conjugated diene polymer with double bonds on the side arm and its preparation method, and a high cis-1,4 conjugated diene polymer with functional groups on the side arm Polymers and methods of preparation. Background technique [0002] Functionalization is an important way to realize the high performance of polymer materials. Introducing polar functional groups such as carboxyl, hydroxyl, and alkoxysilyl groups into the chain unit of conjugated diene polymer can significantly improve its performance as a synthetic rubber material and other polar polymers (such as polyimide or polyester) Or the compatibility of organic and inorganic fillers (such as carbon black or white carbon black), to obtain tire raw materials with excellent properties such as high adhesion, tear resistance, heat resistance and aging resistance. There are generally two ways to introdu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F136/04C08F4/54C08F4/52C08F236/08C08F236/04C08F8/42C08F8/34
CPCC08F8/34C08F8/42C08F136/045C08F236/045C08F236/08C08F4/545
Inventor 崔冬梅李磊李世辉
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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