Urethane compound and synthesis and application thereof

An ester compound and compound technology, which is applied in the preparation of organic compounds, the preparation of carbamate derivatives, organic chemistry, etc., can solve problems such as unsatisfactory mechanical properties, and achieve the goal of being suitable for large-scale production, the preparation method is simple and the reaction process is simple. Highly active effect

Active Publication Date: 2018-05-29
HUAZHONG UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0005] In view of the above defects or improvement needs of the prior art, the object of the present invention is to provide a kind of urethane compound and its synthesis and application, wherein through its key molecular structure, the overall flow process design of the synthesis method, and the design of each step Parameters and conditions (such as reaction temperature and time, specific types and proportions of raw materials, reaction atmosphere requirements, etc.) are improved, the synthesis method has high yield, the synthesis method is simple, and the cost is low. During the synthesis process, CO 2 As raw material, it can solve CO 2 Greenhouse effect; Simultaneously, the compound price that the present invention makes is cheap, joins in polypropylene carbonate and can reduce cost; The glycidyl methacrylate urethane compound that makes can be effectively applied to polypropylene carbonate In the strengthening and toughening modification of methacrylic acid glycidyl urethane compounds with structures such as -NHCOO-, -OH, the compatibility with polypropylene carbonate is better, and compared with the prior art It can effectively solve the problems of unsatisfactory mechanical properties of modified polypropylene carbonate

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  • Urethane compound and synthesis and application thereof
  • Urethane compound and synthesis and application thereof
  • Urethane compound and synthesis and application thereof

Examples

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preparation example Construction

[0041] The synthetic route of the preparation method of the glycidyl methacrylate urethane compound is shown in Figure 1, and the synthetic process may include the following steps:

[0042] (1) Glycidyl methacrylate and phase transfer catalyst are added to the reactor, and then CO 2 Carry out chemical reaction, obtain glycidyl methacrylate base cyclic carbonate intermediate after reaction finishes;

[0043] (2) Then, the glycidyl methacrylate-based cyclic carbonate intermediate obtained in step (1) is dissolved and then reacted with an amine compound to obtain a glycidyl methacrylate-based urethane compound.

[0044] The phase transfer catalyst described in the step (1) is a quaternary ammonium salt (formula (3)) or a quaternary phosphonium salt (formula (4)). The reaction temperature is between 80 and 120 °C, and the reaction pressure is preferably between 2 and 6 MPa (that is, CO is introduced into the reactor before the reaction 2 A high-pressure environment of 2-6 MPa is...

Embodiment 1

[0055] Add 200mmol of glycidyl methacrylate and 10mmol of tetrabutylammonium bromide into the autoclave, and fill the autoclave with CO 2 , so that the pressure of the autoclave is 6.0 MPa. Then the autoclave is placed in a constant temperature oil bath of 120° C. After 4 hours of reaction, the pressure in the autoclave no longer decreases, and the reaction is stopped (of course, the present invention can also directly use time as a judgment indicator for the termination of the reaction, even if the pressure is still is decreasing). After the reaction, the autoclave was cooled to room temperature, and then the carbon dioxide was slowly removed. The crude product obtained by the reaction was separated and purified by column chromatography, and the catalyst tetrabutylammonium bromide was removed by using dichloromethane as an eluent to obtain a glycidyl methacrylate-based cyclic carbonate. That 1 H-NMR analysis results show (as attached figure 2 Shown), the conversion rate ...

Embodiment 2

[0059] Add 200mmol of glycidyl methacrylate and 6mmol of tetraethylammonium nitrate into the autoclave, and fill the autoclave with CO 2 , the pressure of the autoclave was raised to 6.0MPa, and then the autoclave was placed in a constant temperature oil bath of 80°C. After 18 hours of reaction, the pressure in the autoclave no longer decreased, and the reaction was stopped. Then the autoclave was cooled to room temperature, and carbon dioxide was slowly removed. The crude product obtained by the reaction was separated and purified by column chromatography, and the catalyst tetraethylammonium nitrate was removed by using dichloromethane as an eluent to obtain glycidyl methacrylate-based cyclic carbonate.

[0060] Add 100 mmol of glycidyl methacrylate-based cyclic carbonate synthesized above and 100 mmol of 2-amino-1-ethanol into the reactor, and add 20 mL of dichloromethane as a solvent into the reactor at the same time, at 20 ° C, nitrogen The reaction was carried out under ...

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Abstract

The invention discloses a urethane compound and synthesis and application thereof. The urethane compound adopts the structure shown as a formula (1) or a formula (II); a synthesis method thereof comprises the following steps: synthesizing a cyclic carbonate intermediate from glycidyl methacrylate and CO2 as raw materials, and then performing a ring-opening reaction on the cyclic carbonate intermediate and a monoamino compound to obtain the urethane compound. Through improvement on a key molecular structure thereof, the overall process design of the synthesis method, and parameters and conditions of each step, the method is simple, the yield is high, the prepared urethane compound can be effectively applied to reinforcing and toughening modification of polypropylene carbonate, and the problems of unsatisfactory mechanical properties of the modified polypropylene carbonate and the like can be effectively solved.

Description

technical field [0001] The invention belongs to the field of polymer materials, and more specifically relates to a urethane compound and its synthesis and application, so that the synthesized urethane compound can be especially applied to the reinforcement and toughening modification of polypropylene carbonate. Background technique [0002] Polypropylene carbonate is CO 2 The biodegradable polymer obtained by copolymerization with propylene oxide can solve the widespread "white pollution" problem from the source. Moreover, the synthesis of polypropylene carbonate requires CO 2 as raw material, which can alleviate CO 2 resulting in the greenhouse effect. In addition, polypropylene carbonate has a strong barrier effect on water and oxygen, and has broad application potential in food packaging, medical materials, composite materials and other fields. However, the molecular chain flexibility of polypropylene carbonate and the small intermolecular force lead to its poor mecha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/16C07C271/12C07C271/20C07C271/22C07C271/14C07C269/04C08K5/205C08L69/00
CPCC07C271/12C07C271/14C07C271/16C07C271/20C07C271/22C08K5/205C08L69/00
Inventor 解孝林李凯王勇周兴平
Owner HUAZHONG UNIV OF SCI & TECH
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