Nitrogenous polyfunctional acrylic ester monomer, preparation and use thereof

A multi-functionality, acrylate technology, applied in the preparation of cyanide reaction, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of isocyanates with irritating odor, skin irritation, and many hydrogen bonds, and achieve product Easy separation and purification, high photopolymerization activity, and mild reaction conditions

Inactive Publication Date: 2009-07-08
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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  • Nitrogenous polyfunctional acrylic ester monomer, preparation and use thereof
  • Nitrogenous polyfunctional acrylic ester monomer, preparation and use thereof
  • Nitrogenous polyfunctional acrylic ester monomer, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Dissolve 46.45g (0.4mol) of hydroxyethyl acrylate in 50ml of methanol, and add 6.01g (0.1mol) of ethylenediamine 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 disappeared, the reaction was stopped, and the solvent methanol was removed to obtain 49.85 g of N, N, N', N'-tetrahydroxyethylcarboxyethyl-ethane-1,2 diamine;

[0033] (2) Add 34ml of acryloyl chloride dropwise to 200ml of dichloromethane solution containing 49.85g of N,N,N',N'-tetrahydroxyethylcarboxyethyl-ethane-1,2 diamine and 80g of triethylamine In , the reaction was carried out in an ice bath at 0-5° C. After 4 hours of reaction, the stirring was stopped and left standing overnight. After standing overnight, the reaction was terminated, washed with water, 1M hydrochloric acid, and 1M NaOH solution...

Embodiment 2

[0040] (1) 58.06g (0.5mol) of hydroxyethyl acrylate was dissolved in 50ml of methanol, and 10.32g (0.1mol) 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 to obtain 64.97g N 1 , N 1 , N2 , N 3 , N 3 - Pentahydroxyethylcarboxyethyl-diethylenetriamine;

[0041] (2) Add 43ml of acryloyl chloride dropwise to the 1 , N 1 , N 2 , N 3 , N 3 -Pentahydroxyethylcarboxyethyl-diethylenetriamine 64.97g and tripropylamine 110g in ethyl acetate 300ml solution, react in an ice bath at 0-5°C, after reacting for 4 hours, stop stirring and let stand overnight. After standing overnight, the reaction was terminated, washed with water, 1M hydrochloric acid, and 1M NaOH solution succ...

Embodiment 3

[0048] (1) 81.28g (0.7mol) of hydroxyethyl acrylate was dissolved in 50ml of methanol, and 18.93g (0.1mol) 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 to obtain 95.20g N 1 , N 1 , N 2 , N 3 , N 4 , N 5 , N 5 - Heptahydroxyethylcarboxyethyl-tetraethylenepentamine;

[0049] (2) Add 60ml of acryloyl chloride dropwise to the 1 , N 1 , N 2 , N 3 , N 4 , N 5 , N 5 -Heptahydroxyethyl carboxyethyl-tetraethylenepentamine 95.20g and tri-n-butylamine 175g in n-hexane 500ml solution, react in an ice bath at 0-5°C, after reacting for 4 hours, stop stirring and let stand overnight. After standing overnight, the reaction was terminated, washed with water, 1M hy...

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Abstract

The invention relates to nitrogen-containing multi-functionality acrylic ester monomers and a preparation method and application thereof. The structure of the monomers is as shown in a general formula (I), wherein R refers to a right formula (1) or a right formula (2); R1 and R2 refer to hydrogen or methyl; m refers to an integer between 0 and 4; and n refers to an integer between 0 and 5. The method for preparing the monomers comprises: firstly, performing Michael addition on polyamine compounds and acrylic ester compounds provided with hydroxyl groups, and obtaining amine compounds provided with the hydroxyl groups; and secondly, making the amine compounds provided with the hydroxyl groups react with acyl chloride to generate products. The method has the advantages of high conversion rate, mild reaction conditions, small number of byproducts, easy separation and purification of products, etc., and the nitrogen-containing multi-functionality acrylic ester monomers are a novel photopolymerisable active compound system with good 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 acrylate monomers, a preparation method thereof and an application thereof in photocurable compositions. Background technique [0002] Radiation curing refers to the process of cross-linking and polymerizing liquid oligomers (including monomers) to form solid products under the action of light (including ultraviolet and visible light) or high-energy rays (mainly electron beams). Radiation curing technology has the advantages of fast curing speed (and thus high production efficiency), less pollution, energy saving, and excellent performance of cured products. It is an environmentally friendly green technology. Any photocurable composition includes three main components: photoinitiator, monomer and oligomer (resin). [0003] The monomers in the photocuring system generally contain polymerizable functional gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/16C07C227/16C08L101/00C08L33/02C08L33/08C08L33/10
Inventor 聂俊肖鸣王克敏
Owner BEIJING UNIV OF CHEM TECH
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