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High-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber and carboxyl-terminated polyethylene, and preparation method thereof

A technology for aldehyde-terminated polybutadiene and polybutadiene, which is applied in the field of preparing carboxyl-terminated polyethylene, can solve the problems of high raw material price, high application cost, difficult recovery and the like, and achieves good fluidity, low cost, high reaction mild conditions

Active Publication Date: 2018-08-14
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although ring-opening metathesis polymerization can better realize the functionalization of polar groups, its polymerized monomers are usually cycloolefins, and the raw material price is relatively high; Grubbs catalyst is also relatively expensive and difficult to recycle, so the application cost is relatively high

Method used

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  • High-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber and carboxyl-terminated polyethylene, and preparation method thereof
  • High-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber and carboxyl-terminated polyethylene, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of high cis-terminated aldehyde polybutadiene:

[0039] The preparation method refers to CN201410377717.8. The obtained high-cis-1,4 content aldehyde-terminated polybutadiene liquid rubber has a number average molecular weight of 500 g / mol and a molecular weight distribution of 1.9 as characterized by GPC.

[0040] Preparation of high cis-terminated carboxyl polybutadiene:

[0041] Take 2.00g of the above-mentioned high cis-1,4 content aldehyde-terminated polybutadiene liquid rubber, completely dissolve it in 10mL cyclohexane, then add 3.3mL acetone, so that the volume ratio of acetone / cyclohexane = 1 / 3, Keep the temperature at 30°C, add 1.5 mL of Jones reagent ([O] / [CHO]=4 / 1) dropwise, react for 4 hours, add a small amount of isopropanol to remove unreacted Jones reagent. After the solution is rotary evaporated, add n-hexane to dissolve again, filter and rotary steam to obtain high cis-1,4 content carboxyl-terminated polybutadiene liquid rubber, the number...

Embodiment 2

[0043] The preparation process of high cis-terminated aldehyde polybutadiene is the same as in Example 1;

[0044] Take 2.0 g of high cis-terminated polybutadiene with aldehyde groups, the cis-1,4 content is 95%, the number average molecular weight is 5100 g / mol, and the molecular weight distribution is 1.6. Completely dissolve in 10mL cyclohexane, then add acetone, make the volume ratio of acetone / cyclohexane=1 / 3, keep the temperature to 40°C, add the calculated amount of Jones reagent dropwise ([O] / [CHO]=4 / 1), react for 3 hours, add a small amount of isopropanol to remove unreacted Jones reagent. After the solution is rotary evaporated, add n-hexane to dissolve again, filter and rotary steam to obtain high cis-1,4 content carboxyl-terminated polybutadiene liquid rubber, the number average molecular weight is 5000 / mol and the molecular weight distribution is 1.6 as characterized by GPC ,through 1 H NMR and 13 The microstructure characterized by C NMR was cis-1,4 with 95% ...

Embodiment 3

[0046] The preparation process of high cis-terminated aldehyde polybutadiene is the same as in Example 1;

[0047] Take 2.0 g of high cis-terminated polybutadiene with aldehyde groups, the cis-1,4 content is 96%, the number average molecular weight is 3100 g / mol, and the molecular weight distribution is 1.9. Completely dissolve in 10mL cyclohexane, then add acetone, make the volume ratio of acetone / cyclohexane=1 / 3, keep the temperature to 25°C, add the calculated amount of Jones reagent dropwise ([O] / [CHO]=4 / 1), react for 5 hours, add a small amount of isopropanol to remove unreacted Jones reagent. After the solution is rotary evaporated, add n-hexane to dissolve again, filter and rotary steam to obtain high cis-1,4 content carboxyl-terminated polybutadiene liquid rubber, the number average molecular weight is 3000 / mol and the molecular weight distribution is 1.9 as characterized by GPC ,through 1 H NMR and 13 The microstructure characterized by C NMR was cis-1,4 content o...

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Abstract

The invention discloses a high-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber and a carboxyl-terminated polyethylene, and a preparation method thereof. The method concretely comprisesthe following steps: (1) oxidizing a high-cis-1,4 content aldehyde-terminated polybutadiene liquid rubber to prepare the high-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber; and (2)hydrogenating the high-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber to prepare the carboxyl-terminated polyethylene. The high-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber is prepared from cis-polybutadiene rubber, and has a cis-1,4 content reaching 95.0-99.0%, a number-average molecular weight adjustable in a range of 500-10000 g / mol, a molecular weight distribution of 1.2-3.0 and a functionality of 1.9-2.2. The carboxyl-terminated polyethylene prepared by hydrogenating the high-cis-1,4 content carboxyl-terminated polybutadiene liquid rubber has few branchchain structures, has a crystallinity of 57% and has a melting point reaching 125.0 DEG C. The preparation method provides a new idea for the production of high-added value products from the cis-polybutadiene rubber, and has great realistic significance.

Description

technical field [0001] The invention relates to a method for preparing high cis-1,4 carboxyl-terminated polybutadiene liquid rubber, and further preparing carboxyl-terminated polyethylene from high cis-1,4 carboxyl-terminated polybutadiene liquid rubber through reduction reaction Methods. The high-cis-carboxyl-terminated polybutadiene and polyethylene have a clear structure and excellent performance, and will have broad application prospects in the field of new materials. Background technique [0002] High-cis 1,4-polybutadiene rubber (butadiene rubber, BR) has particularly excellent cold resistance, wear resistance and elasticity, and also has good aging resistance; it is compatible with natural rubber, neoprene and butadiene rubber It is widely used in the production of rubber products such as tires, impact-resistant modified products, cold-resistant products, cushioning materials, tapes, and rubber shoes. It is the second largest general-purpose synthetic rubber in the w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08C19/04C08C19/02
Inventor 介素云李伯耿戴璐
Owner ZHEJIANG UNIV
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