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

A technology of hydroxyl-terminated polybutadiene and aldehyde-terminated polybutadiene is applied in the field of high cis-1,4 content hydroxyl-terminated polybutadiene liquid rubber and its preparation, and can solve the problem that it is difficult to achieve hydroxyl-terminated polybutadiene. Butadiene microstructure, inability to prepare and other problems, to achieve the effect of high reaction efficiency and broad industrial application prospects

Active Publication Date: 2014-12-17
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the microstructure of hydroxyl-terminated polybutadiene obtained by traditional free radical polymerization or anionic polymerization is generally: the ratio of trans-1,4 / cis-1,4 / 1,2-vinyl is 0.6 / 0.2 / 0.2, mainly depends on the reaction solvent and reaction temperature, it is difficult to precisely control the microstructure of hydroxyl-terminated polybutadiene (Journal of Macromolecular Science, Part A: Pure and Applied Chemistry 2013,50,128–138)
Therefore, high cis-1,4 content hydroxyl-terminated polybutadiene cannot be prepared by conventional radical polymerization or anionic polymerization

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Take 5.00g of nickel-based butadiene rubber (BR 9000), dissolve it completely in 100mL of tetrahydrofuran, the rubber concentration is 50g / L, keep the temperature at 30°C, add m-chloroperoxybenzoic acid under vigorous stirring, the amount of m-chloroperoxybenzoic acid It is 2% of the butadiene structural unit in nickel-based butadiene rubber (BR 9000), the reaction time is 6 hours, and the product is precipitated with a large amount of ethanol and dried in vacuum. product by 1 H NMR showed that the epoxy content was 2.2%.

[0052] Take 4.00g of the above-mentioned epoxidized butadiene rubber, completely dissolve it in 100mL of tetrahydrofuran, the rubber concentration is 40g / L, keep the temperature at 30°C, add periodic acid under vigorous stirring, the molar ratio of periodic acid to epoxy group is 1 : 1, reacted for 30 minutes. The product can be filtered to obtain polybutadiene liquid rubber with high cis-1,4 content and terminal aldehyde group.

[0053] Take 3.00...

Embodiment 2

[0055] Take 5.00g of cobalt-based butadiene rubber (Taipol), dissolve it completely in 200mL of cyclohexane, the rubber concentration is 25g / L, keep the temperature at 50°C, and add m-chloroperoxybenzoic acid and m-chloroperoxybenzoic acid under vigorous stirring. The dosage is 4% of the butadiene structural unit in cobalt-based butadiene rubber (Taipol), the reaction time is 4 hours, and the product is precipitated with a large amount of ethanol and dried in vacuum. product by 1 H NMR showed that the epoxy content was 4.1%.

[0056] Take 4.00g of the above epoxidized butadiene rubber, completely dissolve it in 100mL cyclohexane, the rubber concentration is 40g / L, keep the temperature at 50°C, add periodic acid under vigorous stirring, the molar ratio of periodic acid to epoxy group The ratio is 1:1, and the reaction time is 40 minutes. The product can be filtered to obtain polybutadiene liquid rubber with high cis-1,4 content and terminal aldehyde group.

[0057] Take 3.00...

Embodiment 3

[0059] Take 5.00g of neodymium-based butadiene rubber (BR 9100), dissolve it completely in 100mL of toluene, the rubber concentration is 50g / L, keep the temperature at 70°C, and add (1S,2S)-(+)-[1,2 -Cyclohexanediamine nitrogen-N,N'-bis(3,5-di-tert-butyl salicylidene)] manganese(III) chloride 0.005g, the amount of sodium hypochlorite is neodymium-based butadiene rubber (BR 9100 ) in butadiene structural unit 8%, the reaction time is 2 hours, the product is precipitated with a large amount of ethanol and vacuum-dried. product by 1 H NMR showed that the epoxy content was 8.1%.

[0060] Take 4.00g of the above epoxidized butadiene rubber, completely dissolve it in 100mL of toluene, the rubber concentration is 40g / L, keep the temperature at 50°C, add periodic acid under vigorous stirring, the molar ratio of periodic acid to epoxy group is 1 : 1, reacted for 50 minutes. The product can be filtered to obtain polybutadiene liquid rubber with high cis-1,4 content and terminal aldehyd...

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Abstract

The invention discloses a high-cis-1,4-content hydroxyl-terminated polybutadiene liquid rubber and a preparation method thereof. The method includes following steps: (1) preparing epoxidized butadiene rubber from butadiene rubber; (2) preparing high-cis-1,4-content aldehyde group-terminated polybutadiene liquid rubber from the epoxidized butadiene rubber; (3) preparing high-cis-1,4-content aldehyde group-terminated polybutadiene liquid rubber from the butadiene rubber in a one-pot manner; (4) reducing the high-cis-1,4-content aldehyde group-terminated polybutadiene liquid rubber to prepare the high-cis-1,4-content hydroxyl-terminated polybutadiene liquid rubber. In the method, the high-cis-1,4-content hydroxyl-terminated polybutadiene liquid rubber is prepared from the butadiene rubber and the content of cis-1,4 can reach 95.0-99.0%. A number-average molecular weight of the high-cis-1,4-content hydroxyl-terminated polybutadiene liquid rubber can be regulated between 2000 g / mol and 10000 g / mol. A molecular weight distribution is 1.2-3.0 and a degree of functionality is 1.9-2.2. On the basis of excessive supply in raw rubber of butadiene rubber and increased tensing situation of petroleum sources, by means of the method, the high-cis-1,4-content hydroxyl-terminated polybutadiene liquid rubber can be prepared through oxidative pyrolysis of the butadiene rubber, so that the method has a quite important practical significance.

Description

technical field [0001] The invention relates to a method for preparing high cis-1,4 content hydroxyl-terminated polybutadiene liquid rubber from butadiene rubber, in particular to a method for preparing high cis-1,4 content aldehyde group-terminated polybutadiene liquid rubber through a one-pot method. A method for butadiene liquid rubber, and further preparing high cis-1,4 content hydroxyl-terminated polybutadiene liquid rubber. Background technique [0002] The polymerization methods of 1,3-butadiene include 1,4-polymerization and 1,2-polymerization to generate cis-1,4, trans-1,4 or 1,2-vinyl polybutadiene ( PBDs), whose performance mainly depends on the microstructure of the polymer. Among these different isomers, high cis-1,4 polybutadiene has become an important industrial product because of its excellent rubber properties, that is, butadiene rubber. High-cis 1,4-polybutadiene rubber (butadiene rubber, BR) has particularly excellent cold resistance, wear resistance an...

Claims

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Application Information

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IPC IPC(8): C08C19/06C08C19/08C08F36/06
Inventor 介素云李伯耿周勤灼
Owner ZHEJIANG UNIV
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