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Dimethyl acrylic acid glyceride phosphate and synthetic method thereof

A technology of glyceryl dimethacrylate phosphate and glyceryl dimethacrylate, which is applied in the direction of phosphorus organic compounds, can solve the problems of resin tolerance, strong corrosion, harsh production conditions, etc., and achieve improved adhesion , strong adhesion, environment-friendly effect

Inactive Publication Date: 2013-07-03
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 obtained 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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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 100g of glycidyl methacrylate, 1.5g of triphenylphosphine, and 0.4g of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring. 63g of methacrylic acid, the temperature was raised after the feeding was completed, and the reaction temperature was controlled at 90-100° C. after 6 hours of reaction. After the reaction, the product is cooled to below 30°C to obtain glycerol dimethacrylate. Then slowly add 33 g 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 330mPa·s, a tetrafunctional content of over 62%, and an acid value of 201mgKOH / g.

Embodiment 2

[0027] Add 100g of glycidyl methacrylate, 1.7g of N,N-dimethylbenzylamine, and 0.5g of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring, and slowly add them at a temperature below 50°C Add 63g of methacrylic acid, and heat up after the feeding is complete, and the reaction temperature is controlled at 90-100°C for 6 hours. After the reaction, the product is cooled to below 30°C to obtain glycerol dimethacrylate. Then slowly add 35g 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 340mPa·s, a tetrafunctional content of over 64%, and an acid value of 198mgKOH / g.

Embodiment 3

[0029] Add 60Kg of ethylene glycol diglycidyl ether, 1Kg of triphenylphosphine, and 0.3Kg of p-hydroxyanisole into a reaction kettle equipped with cooling and heating devices and mechanical stirring. 38Kg of methacrylic acid, the temperature was raised after the feeding was completed, and the reaction temperature was controlled at 90-100° C. after 7 hours of reaction. After the reaction, the product is cooled to below 30°C to obtain glycerol dimethacrylate. Then slowly add 21Kg of phosphorus pentoxide into the reaction kettle, control the temperature below 50°C, raise the temperature after the addition, control the reaction temperature at 80-90°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 328mPa·s, a tetrafunctional content of over 61%, and an acid value of 201mgKOH / g.

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Abstract

The invention discloses a dimethyl acrylic acid glyceride phosphate being taken as UV photocureable coating adhesion promoter and a synthetic method thereof. A synthetic process is that glycidyl methacrylate is added in a mechanical stirring reaction kettle equipped with a cooling and heating device, and conducts ring-opening addition reaction with methacrylic acid under the quick stirring and a condition that catalyst and polymerization inhibitor exist to generate dimethyl acrylic acid glyceride; the dimethyl acrylic acid glyceride and phosphorus pentoxide conduct esterification reaction to generate dimethyl acrylic acid glyceride phosphate. The generated target product has light color, low acid value, good adhesion and four functional groups, can be taken as additive to be used for UV photocureable coating, has good solubleness in universal (methyl) crylic acid activated monomer and (methyl) crylic acid resin, and can improve adhesion of resin to metal, glass and other base materials and the UVcuring speed of 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 phosphoric ester acrylates, in particular to a metallic glass adhesion promoter dimethacrylate glyceryl phosphate and its resolve resolution. 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 formulation design of UV-curable coatings is how to improve its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 刘登友李本祥凌立志
Owner HUNAN AGRICULTURAL UNIV
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