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Cycloaliphatic epoxy (meth)acrylate and preparation method thereof

An epoxy group, carboxylate technology, applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of poor solubility of organic solvents, inability to obtain corrosion resistance, difficult operation and other problems

Active Publication Date: 2013-02-13
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the (meth)acrylate in which the organic ring hydrocarbon group is directly bonded to the oxygen atom of the ester has a very large group adjacent to the ester group, so the synthesis of the monomer is often difficult. In addition, for organic The solubility of the solvent is poor, and the operation during the polymerization reaction is difficult
In addition, since the polarity of the (meth)acrylate in which the organic ring hydrocarbon group is directly bonded to the oxygen atom of the ester is very low, when it is copolymerized with a highly polar unsaturated carboxylic acid or a monomer containing an epoxy group, Inhomogeneity occurs in the monomer composition of the polymer, and a uniform polymer cannot be obtained, so the desired anti-corrosion performance may not be obtained.

Method used

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  • Cycloaliphatic epoxy (meth)acrylate and preparation method thereof
  • Cycloaliphatic epoxy (meth)acrylate and preparation method thereof
  • Cycloaliphatic epoxy (meth)acrylate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] 100 g of tricyclo[5.2.1.02,6]dec-3-enyl acrylate (manufactured by Hitachi Chemical Industries; trade name "FA-511A"; molecular weight 204.3) was charged in a 1-liter flask with a cannula, and 100g ethyl acetate, make the temperature in the reaction system be 50 ℃ while blowing into air, add the ethyl acetate solution of 156g peracetic acid dropwise (peracetic acid concentration: 29.6%, moisture content: 0.2% ). After the dropwise addition of peracetic acid was completed, aging was carried out at 50° C. for 4 hours to complete the reaction. Then wash the crude reaction solution with water at 50°C, and carry out the operation of removing low boiling point substances at 70°C / 10mmHg to obtain acrylic acid 3,4-epoxytricyclo[5.2.1.0 2，6 ] Decyl ester 91.8g. Its properties are: the oxygen concentration of ethylene oxide is 6.74%, the viscosity is 61cP / 25°C, measured 1 In H-NMR, the peaks from internal double bonds at δ5.5-5.8ppm observed in the spectrum of Figure 1 almost d...

Embodiment 2

[0148] In a 1 liter flask with a cannula, charge 100 g tricycline [5.2.1.0 2，6 ] Dec-3-enyl acrylate (manufactured by Hitachi Chemical Industries; trade name "FA-511A"; molecular weight 204.3), 100 g of toluene, 0.24 g of phosphoric acid, 4.65 g of trimethyloctyl ammonium chloride, 6.60 g of sodium tungstate , blowing in air, the temperature in the reaction system was set to 30° C., and 83.5 g of 30% hydrogen peroxide was added dropwise over about 1 hour. After completion of the hydrogen peroxide dropwise addition, aging was carried out at 40° C. for 2 hours to complete the reaction. Then wash the crude reaction solution with water at 40°C, and carry out the operation of removing low boiling point substances at 70°C / 10mmHg to obtain acrylic acid 3,4-epoxytricyclo[5.2.1.0 2，6 ] Decyl ester 91.6g. Its properties are: the oxygen concentration of ethylene oxide is 6.62%, and the viscosity is 103cP / 25°C. 1 In H-NMR, the peaks from internal double bonds at δ5.5-5.8ppm observed in...

Embodiment 3

[0150] 100 g of methacrylic acid 2-(tricyclo[5.2.1.0 2，6 ]dec-3-enyl)oxyethyl ester (manufactured by Hitachi Chemical Industries; trade name "FA-512MT"; molecular weight 262), and 20 g of ethyl acetate, and the temperature in the reaction system was 50° C. while blowing in air, An ethyl acetate solution of 106.4 g of peracetic acid (concentration of peracetic acid: 29.6%, water content: 0.2%) was added dropwise over about 1 hour. After the dropwise addition of peracetic acid was completed, aging was carried out at 50° C. for 4 hours to complete the reaction. Then at 50°C, the reaction crude liquid was washed with water, and the operation of removing low boiling point substances was carried out at 70°C / 10mmHg to obtain methacrylic acid 2-(3,4-epoxytricyclo[5.2.1.0 2，6 ] Decyloxy) ethyl ester 96.0g. Its properties are: the oxygen concentration of ethylene oxide is 5.20%, and the viscosity is 144cP / 25°C. 1 In H-NMR, the peaks from internal double bonds at δ5.5-5.8ppm observed ...

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Abstract

Novel compounds each having a 3,4-epoxytricyclo[5.2.1.0<2,6>]- decane skeleton and a polymerizable unsaturated bond; a process for the production thereof; and a copolymer composed of (A) units derived from a monomer having an alkali-soluble group, (B) units derived from an epoxy-containing polymerizable unsaturated compound and, if necessary, (C) units derived from an epoxy-free polymerizable unsaturated compound such as N-substituted maleimide, characterized in that the units (B) account for 40 to 90 wt% of the whole of the units of the copolymer and the units derived from a specific monomer having a 3,4-epoxy- tricyclo[5.2.1.0<2,6>]decane skeleton account for at least 30 wt% of the whole of the units (B). The copolymer can give film excellent in heat resistance and so on and the resin compositions containing the copolymer are extremely excellent in storage stability, while the copolymer is easy of synthesis.

Description

technical field [0001] The present invention relates to alicyclic epoxy unsaturated carboxylic acid esters such as alicyclic epoxy (meth)acrylates with epoxy groups in the structure (with 3,4-epoxy tricyclic [5.2.1.0 2，6 ] unsaturated carboxylic acid ester of decane skeleton) and production method thereof. The alicyclic epoxy (meth)acrylate, etc. and resins obtained from the alicyclic epoxy (meth)acrylate, etc. are used as coating agents, inks, adhesives, sealants, resist materials, transparent Raw materials such as tablets are useful. The present invention also relates to a compound containing 3,4-epoxy tricyclic [5.2.1.0 2，6 ] Copolymer of structural unit of decane skeleton and production method thereof. In more detail, it relates to a compound containing a 3,4-epoxytricyclic [5.2.1.0 2，6 Copolymer of a structural unit of a decane ring and a method for producing the radiation-sensitive resin in photolithography using active light rays such as far-infrared rays, electron ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/32C07D301/06C07D301/12C07D301/19C08F220/26C08F220/10C08F212/08C08F222/40C07B61/00
Inventor 高井英行伊吉就三二十轩年彦森三佐雄
Owner DAICEL CHEM IND LTD
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