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Nitrogen-containing polyfunctionality metacrylic acid ester monomer, preparation and use thereof

A methacrylate, multifunctional technology, applied in the preparation of cyanide reaction, chemical instruments and methods, and preparation of organic compounds, etc. Easy separation and purification of products, reduced stress shrinkage, mild reaction conditions

Inactive Publication Date: 2009-06-24
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are two defects in this method: one is that isocyanate has a pungent smell, which has a strong stimulating effect on the skin, eyes and respiratory tract, and has relatively large toxic and side effects
The second is that this synthesis method has more side reactions, and diols and isocyanates may undergo hydrolysis reactions.
Too much urea-based structure in the polymer will lead to excessive hydrogen bonds in the material, increased brittleness of the film layer, and decreased water resistance
In addition, the generated product contains N-H bonds, and there is a strong hydrogen bond interaction, so the viscosity of the product is generally large, which affects its application.

Method used

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  • Nitrogen-containing polyfunctionality metacrylic acid ester monomer, preparation and use thereof
  • Nitrogen-containing polyfunctionality metacrylic acid ester monomer, preparation and use thereof
  • Nitrogen-containing polyfunctionality metacrylic acid ester monomer, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Add 34ml of methacryloyl chloride dropwise to a solution of 200ml of dichloromethane containing 46.45g of hydroxyethyl acrylate and 80g of triethylamine, and react in an ice bath at 0-5°C. After 4 hours of reaction, stop stirring , let stand overnight. After standing overnight, the reaction was terminated, and unreacted substances and by-products were removed by washing successively with water, 1M hydrochloric acid, and 1M NaOH solution. After removing the solvent, 65 g of acryloyloxyethyl methacrylate was obtained;

[0034] (2) 65 g of acryloyloxyethyl methacrylate was dissolved in 50 ml of methanol, and 5.29 g of ethylenediamine was added dropwise at -10°C. After the dropwise addition, continue to stir for 2 hours, then raise the temperature to 20°C and continue to stir at a constant temperature until the infrared detection 1640 and 810cm -1 The left and right double bond absorption peaks disappear, the reaction is stopped, and solvent methanol is removed to obta...

Embodiment 2

[0041] (1) Add 43ml of methacryloyl chloride dropwise to 300ml of ethyl acetate solution containing 58.06g of hydroxyethyl acrylate and 110g of tripropylamine, and react in an ice bath at 0-5°C. After 4 hours of reaction, stop stirring, Let stand overnight. After standing overnight, the reaction was terminated, and unreacted substances and by-products were removed by washing successively with water, 1M hydrochloric acid, and 1M NaOH solution. After removing the solvent, 81.25 g of acryloyloxyethyl methacrylate was obtained;

[0042](2) 81.25 g of acryloyloxyethyl methacrylate was dissolved in 50 ml of methanol, and 9.10 g of diethylenetriamine was added dropwise at 0°C. After the dropwise addition, continue to stir for 2 hours, then raise the temperature to 25°C and continue to stir at a constant temperature until the infrared detection 1640 and 810cm -1 The left and right double bond absorption peaks disappeared, the reaction was stopped, and the solvent methanol was removed...

Embodiment 3

[0049] (1) Add 61ml of methacryloyl chloride dropwise to 500ml of n-hexane solution containing 81.28g of hydroxyethyl acrylate and 175g of tri-n-butylamine, and react in an ice bath at 0-5°C. After 4 hours of reaction, stop Stir and let stand overnight. After standing overnight, the reaction was terminated, and unreacted substances and by-products were removed by washing successively with water, 1M hydrochloric acid, and 1M NaOH solution. After removing the solvent, 113 g of acryloyloxyethyl methacrylate was obtained;

[0050] (2) 113 g of acryloyloxyethyl methacrylate was dissolved in 50 ml of methanol, and 16.60 g of tetraethylenepentamine was added dropwise at -10°C. After the dropwise addition, continue to stir for 2 hours, then raise the temperature to 50°C and continue to stir at a constant temperature until the infrared detection 1640 and 810cm -1 The left and right double bond absorption peaks disappeared, the reaction was stopped, and the solvent methanol was removed...

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Abstract

The invention relates to a nitrogenous poly-functionality methyl acrylate monomer and a preparation method and application thereof. The structure of the monomer is shown in general formula (I): R1, R2 are hydrogen or methyl, m is an integer ranging from 0 to 4, and n is an integer ranging from 0 to 5. The preparation method of the monomer includes that (methyl) acrylate compound with hydroxy and (methyl) acryloyl chloride react with each other to obtain an intermediate product with acrylate double-bond and methyl acrylate double-bond; the intermediate product is led to carry out Michael addition reaction with polyamine compound, so as to obtain the product. The method has the advantages of high conversion rate, mild reaction condition and easy separation and purification of the product, and provides a novel photopolymerization active compound system with excellent application prospect.

Description

technical field [0001] The invention belongs to the field of photosensitive polymer materials, and in particular relates to a series of nitrogen-containing polyfunctional methacrylate monomers, a preparation method thereof, and an application thereof in photocurable compositions. Background technique [0002] Any photocurable composition includes three main components: photoinitiator, monomer and oligomer (resin). Since the viscosity of the resin is usually high, it is necessary to add a diluent (monomer) to adjust the viscosity. The monomer containing 3 or more acrylate or methacrylate photoactive groups is a multifunctional monomer. Due to the increased content of functional groups, these monomers have the following characteristics: (1) fast photocuring speed; (2) high hardness of cured products; (3) low volatility due to the general molecular weight of multifunctional monomers; (4) can Adjust certain properties according to the requirements of use, such as accelerating ...

Claims

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Application Information

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IPC IPC(8): C07C229/16C07C227/10C08F290/00C08F222/22C08F220/34C08F2/50G03F7/027G03F7/028
Inventor 聂俊肖鸣王克敏
Owner BEIJING UNIV OF CHEM TECH
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