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Preparation method of borate with polymerizable double bonds

A boric acid ester and boronic acid technology, applied in the field of organic boronate compounds, can solve the problems of insufficient application performance of coupling agents, reduce nucleophilic attack rate constants and other problems, and achieve the effect of good compatibility

Inactive Publication Date: 2020-06-09
LIAONING JINGHUA NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Triethanolamine borate is a kind of borate ester with N-B internal coordination structure, in which the electron-rich amino group can not only be an organophilic polymer, but also form an internal coordination structure with the electron-deficient boron atom, filling the empty P of boron Orbital, reducing the nucleophilic attack rate constant of water molecules on boron, greatly improving the hydrolytic stability of the borate coupling agent, but its polymerizable bonds are less, the application performance of the coupling agent is still insufficient, and needs to be improved

Method used

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  • Preparation method of borate with polymerizable double bonds
  • Preparation method of borate with polymerizable double bonds
  • Preparation method of borate with polymerizable double bonds

Examples

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Effect test

Embodiment 1

[0028] 1. Preparation of borate esters with polymerizable double bonds

[0029] In the first step, add 0.1 mol of boric acid and 0.3 mol of triethanolamine to a three-necked flask equipped with a stirrer and a water separator, then add 100 mL of toluene, stir and heat at an oil bath temperature of 130 ° C, and use a water separator to separate water, react until anhydrous is produced, and after cooling, there is a light yellow solid insoluble in toluene, and the toluene is filtered to obtain a solid, washed with a small amount of dimethylformamide for 2 to 3 times, and then washed with absolute ethanol for 2 to 3 times, and then Recrystallize in absolute ethanol, vacuum-dry the crystallized product at 60°C, and finally obtain triethanolamine borate with smooth surface and granular form as shown in structural formula (I). In the second step, 0.1 mol of triethanolamine borate synthesized in the first step was dissolved in N,N-dimethylformamide, and 0.3 mol of butadienedioic acid...

Embodiment 2

[0033] The preparation process is the same as in Example 1, wherein toluene is replaced by chloroform. The yield was 84.3%.

Embodiment 3

[0035] The preparation process is the same as in Example 1, the temperature of the oil bath in the first step is 120°C, and the heating temperature in the second step is 80°C. The yield was 83.2%.

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Abstract

The invention relates to the field of organic borate compounds, in particular to a preparation method of borate with polymerizable double bonds. The preparation method is characterized by comprising the following steps: 1, subjecting boric acid and triethanolamine to an esterification reaction in an organic solvent I by using a solvent method to generate triethanolamine borate; and 2, dissolving the triethanolamine borate synthesized in the step 1 in an organic solvent II, and carrying out an acylation reaction on the triethanolamine borate and butadiene diacid to obtain the borate with the polymerizable double bonds. Compared with the prior art, the method has the advantages that through design of a molecular structure, triethanolamine borate is further subjected to the acylation reactionin the solvent on the basis of generation of triethanolamine borate; two elements including a boron element and a nitrogen element and active groups such as carboxyl groups, unsaturated double bondsand amide bonds are introduced into the same molecule so as to achieve good coupling agent application performance, so the problem that the borate is easily hydrolyzed is solved; and the borate is allowed to have good compatibility with polymers due to the containing of amino groups and the double bonds.

Description

technical field [0001] The invention relates to the field of organic borate compounds, in particular to a method for preparing borates with polymerizable double bonds. Background technique [0002] Borate coupling agent is a new type of coupling agent developed in the 1980s. It is an effective coupling agent for plastic fillers. It has traditional coupling agents such as silane coupling agents and titanate coupling agents. It has excellent characteristics not found in coupling agents, and its molecular structure has a boron-oxygen skeleton, which can produce good physical adsorption with inorganic fillers. The production raw materials of boric acid ester coupling agent are mainly boric acid and long-chain fatty alcohol. The production process is relatively simple and the production cost is low. Fine chemical products. Compared with traditional coupling agents such as silane coupling agents and titanate coupling agents, it has excellent anti-wear lubrication, antistatic, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C08L23/12C08K9/04C08K3/34
CPCC07F5/04C08K9/04C08K3/34C08L23/12
Inventor 杨国聪梁兵杨雪
Owner LIAONING JINGHUA NEW MATERIAL CO LTD
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