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Ultra-low viscosity simple function group carbamate monomer, and preparation and use thereof

A carbamate and monofunctional technology, applied in the field of photosensitive polymer materials, can solve the problems of eye and respiratory tract irritation, irritating odor, high product viscosity, etc., and achieve good dilution ability, less side reactions and high conversion rate Effect

Inactive Publication Date: 2009-08-12
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 the 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 other is that the generated product contains N-H bonds, which have strong hydrogen bonds. Therefore, the viscosity of the product is generally large, which affects its application

Method used

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  • Ultra-low viscosity simple function group carbamate monomer, and preparation and use thereof
  • Ultra-low viscosity simple function group carbamate monomer, and preparation and use thereof
  • Ultra-low viscosity simple function group carbamate monomer, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation and application of 2-(acryloyloxy)ethyl-dicyclohexyl carbamate

[0028] 1) Weigh 8.81g (0.1mol) of ethylene carbonate and dissolve it in 50ml of toluene, then add 18.13g (0.1mol) of dicyclohexylamine, heat to 90°C and stir at a constant temperature. After 5 hours of reaction, 1803cm in the infrared spectrum -1 The absorption peaks at the left and right disappeared, the reaction was stopped, and the solvent toluene was removed to obtain a colorless transparent sticky substance;

[0029] 2) After adding 27.12g of colorless transparent viscous material, 20g of triethylamine and 100ml of dichloromethane into a three-necked flask with a mechanical stirring device, the reaction temperature is -10°C, and 8.5ml of acryloyl chloride is measured. Drop it into a three-necked flask within 1 hour. After the dropwise addition, continue to stir for 2 hours, let it stand overnight, and filter with suction to obtain a dark red liquid. 3 After washing the dark red liquid wit...

Embodiment 2

[0035] Preparation and application of 2-(acryloyloxy)ethyl-diisopropyl carbamate

[0036] 1) Weigh 8.81g (0.1mol) of ethylene carbonate and dissolve it in 50ml of toluene, then add 10.12g (0.1mol) of diisopropylamine, heat to 30°C and stir at a constant temperature. After 10 hours of reaction, 1803cm in the infrared spectrum -1 The absorption peaks at the left and right disappeared, the reaction was stopped, and the solvent toluene was removed to obtain a colorless transparent sticky substance;

[0037] 2) After adding 18.93g of colorless and transparent viscous matter, 22g of tripropylamine and 100ml of ethyl acetate into a three-necked flask with a mechanical stirring device, the reaction temperature was 0°C, and 8.5ml of acryloyl chloride was After the dropwise addition, continue to stir for 2 hours, let it stand overnight, and filter with suction to obtain a dark red liquid, wash the dark red liquid with dilute hydrochloric acid solution (1M), NaOH solution and distilled w...

Embodiment 3

[0043] Preparation and application of 2-(acryloyloxy)ethyl-N,N-(methyl,phenyl)carbamate

[0044]1) Weigh 8.81g (0.1mol) of ethylene carbonate and dissolve it in 50ml of toluene, then add 10.72g (0.1mol) of N-methylaniline, heat to 120°C and stir at a constant temperature. After reacting for 1 hour, 1803cm in the infrared spectrum -1 The absorption peaks at the left and right disappeared, the reaction was stopped, and the solvent toluene was removed to obtain a colorless transparent sticky substance;

[0045] 2) After adding 19.53g of colorless and transparent viscous matter, 25g of tri-n-butylamine and 100ml of n-hexane into a three-necked flask with a mechanical stirring device, the reaction temperature was 10°C, and 8.5ml of acryloyl chloride was measured. Drop it into a three-necked flask within 1 hour. After the dropwise addition, continue to stir for 2 hours, let stand overnight, and filter with suction to obtain a dark red liquid. Use dilute hydrochloric acid solution (1...

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Abstract

The invention relates to an ultralow-viscosity single-functional-group carbamate monomer, preparation thereof, and application thereof in the photoreception polymer material field. When Isocyanate and a hydroxyl compound undergo addition reaction to prepare urethane acrylate, toxic and side effects exist and the product has high viscocity. The low-viscosity single-functional-group carbamate monomer provided by the invention has a structure indicated by a general formula I. In the formula, R1 is methyl, ethyl, isopropyl, phenyl or cyclohexyl; R2 is ethyl, isopropyl, phenyl or cyclohexyl; R3 is hydrogen atom or methyl; and R4 is hydrogen atom, methyl or ethyl. The invention obtains an amide-type intermediate product with hydroxyl by carrying out ring cleavage reaction onto cyclic carbonate and secondary amine; and the amide-type intermediate product with hydroxyl reacts with acyl chloride, thereby obtaining the ultralow-viscosity single-functional-group carbamate monomer. The monomer can be used as a reactive diluent to be used for preparing photo-curing coating materials. The method does not use isocyanate compound and has the advantages of low product viscosity and good photo-curing activity.

Description

technical field [0001] The invention belongs to the field of photosensitive polymer materials, and in particular relates to an ultra-low viscosity monofunctional carbamate monomer synthesized by a non-isocyanate method and its preparation and application. Background technique [0002] Urethane acrylates are widely used in light-curing coatings, inks, adhesives and other fields. At present, isocyanate is usually added to a compound with a hydroxyl group to prepare urethane acrylate. There are two defects in this method: one is that the 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 other is that the generated product contains N-H bonds, which have strong hydrogen bonds. Therefore, the viscosity of the product is generally large, which affects its application. Contents of the invention [0003] The object of the present invention is to solve the problems in ...

Claims

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Application Information

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IPC IPC(8): C07C271/24C07C271/12C07C271/28C07C269/06C07C269/04C09D7/12C09D133/04
Inventor 聂俊肖鸣李振风
Owner BEIJING UNIV OF CHEM TECH
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