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Ethylene glycol diglycidyl ether dimethacrylate organic phosphate and synthetic method thereof

A technology of bis-methacrylate phosphate and bis-methacrylate, applied in the direction of phosphorus organic compounds, can solve the problems of resin tolerance, strong corrosion, harsh production conditions, etc., to improve adhesion and adhesion. Strong, environmentally friendly effect

Inactive Publication Date: 2013-06-12
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The phosphoric acid ester produced by this method has high diester content, low acid value, and the resulting product is of good quality, but the above method has the following problems. The first: many production processes, low yield, and high production cost. Second: In the reaction, a large amount of by-product HCl is produced, which is very polluting and needs to be post-treated. Third: Phosphorus trichloride is a fuming liquid, and its gas is toxic, irritating and highly corrosive, and the production conditions are harsh.
Several other synthetic methods use phosphorus oxychloride, phosphorus pentoxide, polyphosphoric acid, pyrophosphoric acid, etc. as phosphoric acid esterification reagents to carry out esterification reaction with hydroxyethyl methacrylate, but the resulting products all have C=C double bonds. The content of functional groups is low, the acid value is high, and the photocuring speed is slow and the tolerance of the resin is affected during the photocuring process of the resin.

Method used

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  • Ethylene glycol diglycidyl ether dimethacrylate organic phosphate and synthetic method thereof
  • Ethylene glycol diglycidyl ether dimethacrylate organic phosphate and synthetic method thereof
  • Ethylene glycol diglycidyl ether dimethacrylate organic phosphate and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 100g of ethylene glycol diglycidyl ether, 1.6g of triphenylphosphine, and 0.6g of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring, and slowly add 95g of methacrylic acid at a temperature below 50°C After the addition, the temperature was raised, and the reaction temperature was controlled at 100-110° C. after 6 hours of reaction. After the reaction, the product is cooled to below 30°C to obtain ethylene glycol diglycidyl ether dimethacrylate. Slowly add 26g of phosphorus pentoxide into the reaction kettle, control the temperature below 50°C, raise the temperature after the addition, control the reaction temperature at 75-90°C for 6 hours, cool down after the reaction to obtain the product. The product is light yellow, with a kinematic viscosity (25°C) of 280 mPa·s, a tetrafunctional content of over 62%, and an acid value of 130 mgKOH / g.

Embodiment 2

[0025] Add 100g of ethylene glycol diglycidyl ether, 1.8g of N,N-dimethylbenzylamine, and 0.6g of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring, and slowly Add 90 g of methacrylic acid, heat up after the addition, and control the reaction temperature at 100-110° C. for 8 hours. After the reaction, the product is cooled to below 30°C to obtain ethylene glycol diglycidyl ether dimethacrylate. Slowly add 25g of phosphorus pentoxide into the reaction kettle, control the temperature below 50°C, raise the temperature after the addition, control the reaction temperature at 75-90°C for 6 hours, cool down after the reaction to obtain the product. The product is light yellow, with a kinematic viscosity (25°C) of 270 mPa·s, a four-functionality content of over 60%, and an acid value of 128 mgKOH / g.

Embodiment 3

[0027] Add 60Kg of ethylene glycol diglycidyl ether, 1Kg of triphenylphosphine, and 0.5Kg of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring. Slowly add 57Kg of methacrylic acid at a temperature below 50°C. After the addition, the temperature was raised, and the reaction temperature was controlled at 100-110° C. after 7 hours of reaction. After the reaction, the product is cooled to below 30°C to obtain ethylene glycol diglycidyl ether dimethacrylate. Then slowly add 16Kg of phosphorus pentoxide into the reaction kettle, control the temperature below 50°C, raise the temperature after the addition, control the reaction temperature at 75-90°C for 6 hours, cool down after the reaction to obtain the product. The product is light yellow, with a kinematic viscosity (25°C) of 275 mPa·s, a four-functionality content of over 61%, and an acid value of 135 mgKOH / g.

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Abstract

The invention discloses ethylene glycol diglycidyl ether dimethacrylate organic phosphate and a synthetic method thereof, wherein the ethylene glycol diglycidyl ether dimethacrylate organic phosphate is used for an ultraviolet (UV) photocureable coating adhesion promoter. Ethylene glycol diglycidyl ether is added into a reaction kettle provided with a cooling device, a heating device and a mechanical agitation device, a ring-opening addition reaction between the ethylene glycol diglycidyl ether and methacrylic acid is conducted on the conditions of methacrylic acid rapid agitation and the existence of catalyzers and polymerization inhibitors to generate ethylene glycol diglycidyl ether dimethacrylate, and an esterification reaction between the ethylene glycol diglycidyl ether dimethacrylate and phosphorus pentoxide is conducted to generate the ethylene glycol diglycidyl ether dimethacrylate organic phosphate. A generated target product is light in color, low in acid value and good in adhesive force, also has four functional groups, can be used as an addictive used for production of UV photocureable coatings, dissolves well in universal (methyl) crylic acid activated monomers and (methyl) acrylic resin, can increase adhesive force, on base materials such as metal, glass, plastics, acrylonitrile butadiene styrene(ABS), of resin and the UV photocureable speed of the resin.

Description

technical field [0001] The invention belongs to the technical field of synthesizing environment-friendly photosensitive polymer compounds, and relates to a method for synthesizing UV-curable phosphate ester acrylate, in particular to an adhesion promoter on the surface of metal, glass and other substrates such as ethylene glycol di Synthesis method of glycidyl ether dimethacrylate phosphate. Background technique [0002] Compared with traditional coatings, UV-curable coatings do not contain any organic solvents or inert diluents, and do not require heating during curing. They have the characteristics of environmental friendliness, low energy consumption, high efficiency, good chemical stability, and good applicability. A "5E" coating (Economy, Efficiency, Ecology, Energy-saving, Enabling), which is widely recognized by industry insiders, has been widely used in various fields. With the development and application of various photosensitive coatings, one of the keys to the fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 李本祥罗启枚凌立志刘登友
Owner HUNAN AGRICULTURAL UNIV
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