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Cation light-cured alicyclic epoxy compound and preparation method thereof

A cycloaliphatic epoxy and compound technology, which is applied in the field of cationic photocuring and photocuring, can solve the problem of single variety of cycloaliphatic epoxy compounds, and achieve the effect of various types

Inactive Publication Date: 2012-06-20
江苏三木化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purpose of the present invention is to provide a general method for the preparation of cycloaliphatic epoxy compounds, to overcome the single defect of cycloaliphatic epoxy compounds, the present invention uses abundant raw materials, simple synthesis reaction, easy to control

Method used

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  • Cation light-cured alicyclic epoxy compound and preparation method thereof
  • Cation light-cured alicyclic epoxy compound and preparation method thereof
  • Cation light-cured alicyclic epoxy compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of Cationic Photocurable Cycloaliphatic Epoxy Compound Based on 1,6-Hexanediol Diacrylate (HDDA):

[0027] Add 169.5 g of 1,6-hexanediol diacrylate (0.75 mol) and 99.2 g of cyclopentadiene (1.5 mol) into a 500 mL three-necked flask equipped with a reflux condenser, drying tube and mechanical stirring, and stir at room temperature After 72 hours, the intermediate HDN can be obtained through its addition reaction;

[0028] Add 60.8 g (0.30 mol) of m-chloroperoxybenzoic acid and 600 mL of dichloromethane into a 1000 ml three-neck flask equipped with a reflux condenser, a drying tube, and a magnetic stirrer, cool to 0°C in an ice-salt bath, and slowly add Add dropwise a mixed solution of 35.8g (0.100 mol) of intermediate HDN and 100 mL of dichloromethane for 2 hours. After the dropwise addition, keep stirring at room temperature for 24 hours, then cool the mixture to below 0°C, and filter the precipitated White crystals, the filtrate was washed with ...

Embodiment 2

[0030] Example 2: Preparation of Cationic Photocurable Alicyclic Epoxy Compound Based on Trimethylolpropane Triacrylate (TMPTA):

[0031] Add 148.1 g of trimethylolpropane triacrylate (0.50 mol) and 99.2 g of cyclopentadiene (1.5 mol) into a 500 mL three-necked flask equipped with a reflux condenser, drying tube and mechanical stirring, and stir at room temperature for 72 hours , through its addition reaction, the intermediate TAN can be obtained;

[0032] Add 41.7 g (0.24 mol) m-chloroperoxybenzoic acid and 500 mL butyl acetate into a 1000 ml three-neck flask equipped with a reflux condenser, a drying tube and a magnetic stirrer, cool to 0°C in an ice-salt bath, and slowly add Add dropwise a mixed solution of 33.1g (0.067 mol) intermediate TAN and 100 mL of dichloromethane for 3 hours. After the dropwise addition, keep stirring at room temperature for 24 hours, then cool the mixture to below 0°C, and filter the precipitated White crystals, the filtrate was washed with 20% so...

Embodiment 3

[0034] Embodiment 3: Preparation of cationic photocurable cycloaliphatic epoxy compound based on acrylate compound TAEP:

[0035] Add 100 mL of dichloromethane, 19.2 g of TAEP (0.05 mol) and 11.9 g of cyclopentadiene (0.18 mol) into a 250 mL three-necked flask equipped with a reflux condenser, drying tube and mechanical stirring, and stir the reaction at room temperature for 72 h, Distilled under reduced pressure to obtain a colorless liquid intermediate TNP.

[0036] Add 41.7 g (0.24 mol) of m-chloroperoxybenzoic acid and 500 mL of ethyl acetate into a 1000 ml three-neck flask equipped with a reflux condenser, a drying tube, and a magnetic stirrer, cool to 0°C in an ice-salt bath, and slowly add Add dropwise a mixed solution of 39.5g (0.067 mol) intermediate TNP and 100 mL of dichloromethane for 2.5 hours. After the dropwise addition, keep stirring at room temperature for 24 hours, then cool the mixture to below 0°C and filter out white crystals, the filtrate was washed with...

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Abstract

A cation light-cured alicyclic epoxy compound. R1 is a polymer main chain which can be an alkyl chain, a polyether chain, a polyester chain, and a mixed type of the above, and has a molecular weight of 15 to 5000; R2 is CH3 or H; the preparation method comprises two steps of reactions; firstly, a Diels-Alder reaction of an acrylate compound or a methacrylate compound with a diene compound is performed to prepare an unsaturated intermediate; then, through an organic peracid epoxidation reaction, the unsaturated intermediate is dropwisely added into a solution containing an epoxidation reagent (that is an organic peracid); the molar ratio of the double bonds in the unsaturated intermediate and the organic peracid is 1:1-3, preferably 1:1.2; the reaction time is 2-24 hours; the reaction temperature is -5 to 25 DEG C, preferably 0-5 DEG C, and finally the alicyclic epoxy compound of the invention is prepared. The purpose of the invention is to provide a general method for preparing an alicyclic epoxy compound so as to overcome the defect of single variety of alicyclic epoxy compounds; the method of the invention adopts abundant raw materials, is simple in synthetic reaction, and is easy to control.

Description

technical field [0001] The invention relates to the technical field of photocuring, in particular to the technical field of cationic photocuring. Background technique [0002] With the enhancement of people's awareness of environmental protection, UV-curable materials are gradually replacing traditional solvent-based materials due to their advantages such as no solvent or low solvent, fast curing speed, low organic volatiles, low emissions, low operating temperature and high coating quality. coating. Among them, cationic photocuring, as a new technology, has the advantages of small volume shrinkage, no polymerization inhibition by oxygen, difficult termination of reaction, good adhesion of cured film, etc., and is widely used in high-end adhesives, metal coatings, inks and other fields . [0003] Epoxy compounds are prone to cationic polymerization under the action of super-strong protonic acid or Lewis acid to form a polyether main chain. It is the most important resin an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/40C07D301/14C07F9/655C09D163/00
Inventor 王海龙薛飞薛中群惠正权杨树民
Owner 江苏三木化工股份有限公司
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