Preparation method of polyaspartic acid ester

A technology for aspartate and dibasic acid ester, which is applied in the field of preparation of polyaspartate, can solve problems such as adverse effects of downstream applications, unsatisfactory catalytic effect, etc., and achieves excellent chromaticity and easy removal. , the effect of high catalytic activity

Active Publication Date: 2018-03-16
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the catalysts reported in these literatures have unsatisfactory catalytic effects, and the residues in the product are no...

Method used

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  • Preparation method of polyaspartic acid ester
  • Preparation method of polyaspartic acid ester
  • Preparation method of polyaspartic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) 174.31g (1.5mol) 2-methylpentanediamine and 0.137g (1.5mmol) tetramethylammonium hydroxide catalyst are added to be equipped with mechanical stirring paddle, thermometer, constant pressure dropping funnel, connected with N 2 In the 1L three-necked flask of the gas line and bubbler, 516.54g (3.0mol) diethyl maleate was added in the constant pressure dropping funnel, and N was passed into the system. 2 For 20 minutes, the air in the system was replaced; diethyl maleate was slowly added dropwise under stirring at 25°C, and after the drop was completed, the temperature was raised to 40°C for 2 hours to stop the reaction.

[0039] (2) Heating to 90°C, nitrogen flow, water pump extraction under 0.001MPa pressure for 20 minutes to remove tetramethylammonium hydroxide catalyst, and obtain polyaspartic acid ester PAE-1, its structure is shown in the following formula:

[0040]

[0041] (3) Characterization analysis results, diethyl maleate conversion rate 99.7%, Hazen chro...

Embodiment 2

[0043] (1) Add 174.31g (1.5mol) of 2-methylpentanediamine and 0.044g (0.075mmol) of 25% tetraethylammonium hydroxide aqueous solution and add a mechanical stirring paddle, a thermometer, a constant pressure dropping funnel, and a N 2 In the 1L three-necked flask of the gas line and bubbler, 516.54g (3.0 mol) diethyl maleate was added to the constant pressure dropping funnel, and N was introduced into the system. 2 After 10 minutes, the air in the system was replaced; diethyl maleate was slowly added dropwise under the condition of stirring at 10°C, and after the drop was completed, the temperature was raised to 30°C for 6 hours to stop the reaction.

[0044] (2) Heating to 130°C, nitrogen flow, water pump extraction under 0.02MPa pressure for 40 minutes to remove tetraethylammonium hydroxide catalyst and moisture, and obtain polyaspartic acid ester PAE-1.

[0045] (3) Characterization analysis results, diethyl maleate conversion rate 99%, Hazen chromaticity 28, gel time 4min...

Embodiment 3

[0047] (1) 174.31g (1.5mol) 2-methylpentanediamine and 0.685g (7.5mmol) tetramethylammonium hydroxide catalyst are added to be equipped with mechanical stirring paddle, thermometer, constant pressure dropping funnel, connected with N 2 In the 1L three-necked flask of the gas line and bubbler, 516.54g (3.0mol) diethyl fumarate was added in the constant pressure dropping funnel, and N was passed into the system. 2 After 15 minutes, the air in the system was replaced; diethyl fumarate was slowly added dropwise under stirring at 40°C, and after the drop was completed, the temperature was raised to 70°C for 1 hour to stop the reaction.

[0048] (2) Heating to 120°C, nitrogen flow, water pump extraction under 0.01MPa pressure for 30min to remove tetramethylammonium hydroxide catalyst, and obtain polyaspartic acid ester PAE-1.

[0049] (3) Characterization and analysis results, the conversion rate of diethyl fumarate is 98.5%, the Hazen color is 29, the gel time is 4min, X is 2-meth...

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Abstract

The invention provides a preparation method of polyaspartic acid ester. Tetraalkylammonium hydroxide is adopted as the catalyst, and organic primary amine reacts with unsaturated dibasic acid ester toobtain the product. As organic strong base, tetraalkylammonium hydroxide can obviously improve the Michael addition reaction activity of the primary amine and butene diacid ester, and at the end of the reaction, the catalyst can be removed completely through simple heating, and no adverse effect can be generated on downstream application of the product. The method provided by the invention has the advantages of high catalytic activity, high primary amine conversion rate, low product colority, no catalyst residue and the like.

Description

technical field [0001] The invention relates to a preparation method of polyaspartic acid ester, in particular to a method for synthesizing polyaspartic acid ester with high efficiency under the catalysis of tetraalkyl ammonium hydroxide. Background technique [0002] Polyaspartic Ester (Polyaspartic Ester, PAE) is a special type of hindered secondary amine. Due to the steric hindrance and inductive effect of the ester group, the gel time with the low-viscosity isocyanate curing agent can range from a few minutes to a few minutes. Adjust between hours. [0003] [0004] Formula 1 Synthetic reaction scheme of PAE [0005] PAE is synthesized by the Michael addition reaction of organic primary diamines and butenedioic acid diesters. Since PAE is a medium-low viscosity liquid with a boiling point above 500°C, it cannot be purified by rectification or crystallization; if there is too much residual butenedioic acid diester in the product, it will cause a strong odor of volati...

Claims

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Application Information

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IPC IPC(8): C07C227/08C07C229/24C08G65/332
CPCC07C227/08C08G65/3322C07C229/24
Inventor 郑超何光文崔乾唐彦群王鹏从鑫董科黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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