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

A technology of hydroxyl-terminated polybutadiene and aldehyde-terminated polybutadiene, which is applied in the field of epoxidized hydroxyl-terminated polybutadiene liquid rubber with high cis-1,4 content and its preparation, can solve the problem that is difficult to achieve The microstructure of hydroxyl-terminated polybutadiene, the inability to prepare, and the inability to prepare high-cis forms have achieved the effects of simple and efficient process, wide industrial application prospects, and high reaction efficiency.

Active Publication Date: 2015-03-25
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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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, it is impossible to prepare high cis-1,4 content hydroxyl-terminated polybutadiene by traditional free radical polymerization or anionic polymerization, and it is also impossible to prepare high cis-1,4 content epoxidized hydroxyl-terminated polybutadiene liquid rubber

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 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), and the reaction time is 6 hours. 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 2.0%.

[0051] 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 :2, reacted for 30 minutes. The product can be filtered to obtain high cis-1,4 content epoxidized terminal aldehyde polybutadiene liquid rubber, and the product is passe...

Embodiment 2

[0054] 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, 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 4.0%.

[0055] Take 4.00g of the above-mentioned 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 1:4, and the reaction time is 40 minutes. The product can be filtered to obtain high cis-1,4 content epoxidized aldehyde-terminated polybutadiene liquid rubber, and the epoxy rate...

Embodiment 3

[0058] 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-butylsalicylidene)]manganese(III) chloride 0.005g, the amount of sodium hypochlorite is neodymium-based butadiene rubber (BR 9100) 8% of the structural unit of butadiene, the reaction time is 2 hours, the product is precipitated with a large amount of ethanol and dried in vacuum. product by 1 H NMR showed that the epoxy rate was 8.0%.

[0059] 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 :8, reacted in 50 minutes. The product can be filtered to obtain high cis-1,4 content epoxidized terminal aldehyde polybutadiene liquid...

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Abstract

The invention discloses high cis-1,4 content epoxy hydroxyl-terminated polybutadiene liquid rubber and a preparation method thereof. The method comprises the following steps: (1) preparing epoxy butadiene rubber from butadiene rubber; (2) preparing high cis-1,4 content epoxy aldehyde-terminated polybutadiene liquid rubber; (3) preparing high cis-1,4 content epoxy aldehyde-terminated polybutadiene liquid rubber by using a one-pot method; and (4) performing reduction preparation, thereby obtaining high cis-1,4 content epoxy hydroxyl-terminated polybutadiene liquid rubber. According to the preparation method, the high cis-1,4 content epoxy hydroxyl-terminated polybutadiene liquid rubber is prepared from butadiene rubber, the content of cis-1,4 can be up to 70.0-98.0%, the epoxy rate can be within 1-30%, the number-average molecular weight can be within 2000-13000g / mol, the molecular weight distribution is within 1.2-3.0, and the functionality degree is within 1.9-2.2. Under the background that the butadiene rubber supply is beyond the requirements and the petroleum resources are short day by day, the preparation of high cis-1,4 content epoxy hydroxyl-terminated polybutadiene liquid rubber from butadiene rubber by using an oxidation cracking method has very significant practical meanings.

Description

technical field [0001] The invention relates to a method for preparing high cis-1,4 content epoxidized hydroxyl-terminated polybutadiene liquid rubber from butadiene rubber, in particular to a method for preparing high cis-1,4 content cyclic polybutadiene through a one-pot method A method for oxidizing aldehyde-terminated polybutadiene liquid rubber, and further preparing epoxidized hydroxyl-terminated polybutadiene liquid rubber with high cis-1,4 content. 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 res...

Claims

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Application Information

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IPC IPC(8): C08C19/02C08C19/06C08C19/04
Inventor 介素云李伯耿周勤灼
Owner ZHEJIANG UNIV
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