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Composition, resin material, and method for producing same

A technology of composition and compound, which is applied in the field of resin material and its preparation and composition, can solve problems such as difficulty in popularization and use, poor process adaptability, inability to realize continuous automatic production, etc.

Active Publication Date: 2021-04-16
SHANGHAI ZHONGHUA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing ruthenium catalytic system cannot realize continuous automatic production for the following reasons:
[0005] 1. Short storage period: The existing commercialized ruthenium carbene catalytic system can only be stored at low temperature and in a solid state for a long time. When it is dissolved in a common solvent to prepare a solution, it will decompose quickly and it is difficult to store for a long time. It can only be prepared now. It is currently used and cannot be used in continuous production lines, otherwise there will be problems such as deactivation and unable to cure reaction or severe reaction to block equipment
[0006] 2. Disparity in ratio: the existing commercial ruthenium catalyst system can be prepared and used immediately after being liquefied with a solvent, but other components cannot be added (dissolution or poisoning will cause the catalyst to be deactivated), resulting in a ratio of dicyclopentadiene to the liquid catalyst Usually more than 100:1, while the two-component ratio with controllable metering accuracy of existing glue injection equipment should be controlled within 10:1, so the existing system cannot meet the needs of online production
[0007] 3. Poor compatibility: The existing commercialized ruthenium carbene catalyst system polydicyclopentadiene and other resin systems such as epoxy compound products have obvious phase separation, hard and brittle products, low strength, obvious defects, and are difficult to promote and use
However, its catalytic system is metal carbene complexes such as tungsten, molybdenum and tantalum. During the reaction, the two-component feed solution needs to undergo ring-opening polymerization reaction under anhydrous and oxygen-free conditions. The molding conditions are harsh, the process adaptability is poor, and it is difficult to achieve high content The addition of fillers or modifying additives limits the application of this type of technology

Method used

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  • Composition, resin material, and method for producing same
  • Composition, resin material, and method for producing same
  • Composition, resin material, and method for producing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Embodiment 1: Catalyst 1,3-bis(2,4,6-trimethylphenyl)-2-(4,5-dibutylimidazolidinylidene) (dichlorobenzylidene) containing butyl substituent base) (tricyclohexylphosphine) ruthenium (I-1) synthesis

[0127] The synthesis of butyl substituent catalyst I-1 comprises the following steps:

[0128] 1) Preparation of N,N'-bis(2,4,6-trimethyl)phenylethylenediimine (9)

[0129]

[0130] Add 3.73 mL of glyoxal (8) aqueous solution (40%) and 80 mL of methanol successively into a 500 mL three-neck flask equipped with a dropping funnel, and stir to dissolve the glyoxal. Add 9.12 mL of m-trimethylaniline (7) and 10 mL of methanol to the dropping funnel, and slowly drop them into the flask. The temperature of the reaction solution was controlled at about 22° C., and stirred for 12 hours. During this process, a bright yellow precipitate slowly precipitated from the reaction solution. After the reaction, the reaction liquid was filtered to obtain a yellow solid, which was washed ...

Embodiment 2

[0140] Embodiment 2: Containing hexyl substituent catalyst 1,3-bis(2,4,6-trimethylphenyl)-2-(4,5-dihexyl imidazolidinylidene) (dichlorobenzylidene) Synthesis of (Tricyclohexylphosphine)ruthenium(I-2)

[0141] Containing the synthesis of hexyl substituent catalyst 1-2 comprises the following steps:

[0142] 1) Preparation of N,N'-bis(2,4,6-trimethyl)phenylethylenediimine (9)

[0143]

[0144] Add 3.73 mL of glyoxal (8) aqueous solution (40%) and 80 mL of methanol successively into a 500 mL three-neck flask equipped with a dropping funnel, and stir to dissolve the glyoxal. Add 9.12 mL of m-trimethylaniline (7) and 10 mL of methanol to the dropping funnel, and slowly drop them into the flask. The temperature of the reaction solution was controlled at about 22° C., and stirred for 12 hours. During this process, a bright yellow precipitate slowly precipitated from the reaction solution. After the reaction, the reaction liquid was filtered to obtain a yellow solid, which was ...

Embodiment 3

[0154] Example 3: 4-butyl-5-hexyl-1,3-bis(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(benzylidene)(tricyclohexyl Preparation of phosphine) ruthenium(I-3) dichloride

[0155] 1.1) Preparation of N,N'-bis(2,4,6trimethylphenyl)dodecane-5,6-diamine (14)

[0156]

[0157] Under nitrogen protection, add 2.92g N,N'-bis(2,4,6-trimethyl)phenylethylenediimine (9) (Mw: 292.46g / mol; 10.0 mmol), 100mL tetrahydrofuran was stirred to dissolve it. Then, the ampoule was placed in an ethanol cold bath at -78°C, stirred and cooled. After the reaction solution was fully cooled, 4.17 mL (10.0 mmol) of hexyllithium (2.4 M solution in toluene) was slowly added dropwise with a syringe. The reaction solution was cooled to -78°C again, and 6.25 mL (10.0 mmol) of butyllithium (1.6 M hexane solution) solution was slowly added dropwise with a syringe. After the addition was complete, the reaction mixture was slowly raised to room temperature with stirring, and continued to stir for 0.5 h. Then,...

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Abstract

The invention discloses a composition, a resin material and a preparation method thereof. The invention particularly discloses a composition which comprises the following components in parts by weight: 60-100 parts of dicyclopentadiene and 0.01-35 parts of a catalyst composition, wherein the catalyst composition comprises a ruthenium carbene compound as shown in a formula I or a salt thereof, and chlorinated paraffin, the chlorine content of the chlorinated paraffin is 5%-65%, and the chlorine content is the percentage of the mass of chlorine atoms in the mass of the chlorinated paraffin. The composition disclosed by the invention can be stored for a long time, the resin material prepared from the composition has good mechanical properties such as tensile strength, tensile modulus and elongation at break, and in addition, the preparation process of the resin material is simple and is suitable for industrial continuous production.

Description

technical field [0001] The invention relates to a composition, a resin material and a preparation method thereof. Background technique [0002] It is well known that metal carbene complexes such as ruthenium, molybdenum, and tungsten can catalyze olefin metathesis reactions. In the preparation process of polydicyclopentadiene polymer, two-component tungsten-molybdenum catalyst system or ruthenium metal carbene catalyst system are often used to realize the cutting and recombination of olefin carbon-carbon double bonds to form a cross-linked network structure. This type of thermosetting resin material has excellent properties such as light weight, high strength, impact resistance, and corrosion resistance, and has been successfully used in many fields such as construction machinery, lightweight vehicles, and chlor-alkali industry. [0003] At present, the polydicyclopentadiene composite materials prepared based on the tungsten-molybdenum catalyst system, the resin system is m...

Claims

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Application Information

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IPC IPC(8): C08F32/08C08F4/80C08L45/00C08L63/00
CPCY02P20/52
Inventor 杨鲜锋张建民毕淑梦汪贵平
Owner SHANGHAI ZHONGHUA TECH CO LTD
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