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Polymerizable photoinitiator and preparation method thereof

A polymerization photoinitiator and synthesis method technology, applied in the direction of organic chemistry, can solve the problems of easy hydrolysis, moisture and acid-base sensitivity, and achieve the effect of reducing migration and volatilization and increasing compatibility

Inactive Publication Date: 2012-01-25
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The ester group, ether bond, amide group and other groups contained in the above-mentioned initiators are sensitive to moisture and acid and alkali, and are easy to hydrolyze

Method used

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  • Polymerizable photoinitiator and preparation method thereof
  • Polymerizable photoinitiator and preparation method thereof
  • Polymerizable photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 4

[0034]Dissolve 0.1 mole (13.71g) of 3,4-methylenedioxyaniline in 50mL of tetrahydrofuran and slowly drop into 0.1 mole (13.0g) of methyl fumaric acid in 60mL of tetrahydrofuran solution, pass through Nitrogen, when the color of the solution turns light yellow, add 0.16 moles (21.33g) of aluminum trichloride and continue to stir for 1h, then raise the temperature to 30°C, dissolve 0.2 moles (32.3g) of hexamethyldisilazane in 40mL Add dropwise into tetrahydrofuran, add dropwise for 3 hours, and reflux while adding dropwise. After the dropwise addition, cool to room temperature, filter the reactant, evaporate the solvent from the filtrate, and purify the residue with a silica gel column, the eluent is 70% cyclohexane / 30% ethyl acetate, evaporate the eluent under reduced pressure, vacuum After drying, the polymerizable photoinitiator N-3,4-methylenedioxyphenyl-2-methylmaleimide is obtained. The structure is shown in structural formula 4: 1H NMR (250MHz) in CDCl3: δ1.93ppm (3H, CH...

Embodiment 5

[0038] Dissolve 0.1 mole (13.71 g) of 3,4-methylenedioxyaniline in 50 mL of tetrahydrofuran and slowly drop into 0.3 mole (29.4 g) of maleic anhydride in 60 mL of tetrahydrofuran solution, and blow in argon, When the color of the solution turns light yellow, add 0.2 mol (27.2g) of zinc chloride and continue stirring for 0.5h, then raise the temperature to 45°C, and dissolve 0.1 mol (16.1g) of hexamethyldisilazane in 50mL of tetrahydrofuran Add dropwise, dropwise adding time 1.5h, reflux while adding dropwise. After the dropwise addition, cool to room temperature, filter the reactant, evaporate the solvent from the filtrate, and purify the residue with a silica gel column, the eluent is 70% cyclohexane / 30% ethyl acetate, evaporate the eluent under reduced pressure, vacuum After drying, the polymerizable photoinitiator N-3,4-methylenedioxyphenylmaleimide was obtained. The structure is shown in structural formula 1: 1H NMR (250MHz) in CDCl3: δ4.74-5.90ppm (4H, CH 2 ), 6.46-6.54...

Embodiment 6

[0042] Dissolve 0.1 mole (13.71g) of 3,4-methylenedioxyaniline in 40mL of tetrahydrofuran and slowly drop into 0.2 mole (26.0g) of methylene succinic acid in 60mL of tetrahydrofuran solution, blow nitrogen, When the color of the solution turns light yellow, add 0.12 moles (16.0g) of aluminum trichloride and continue to stir for 1.5h, then raise the temperature to 50°C, and dissolve 0.2 moles (32.2g) of hexamethyldisilazane in 90mL of tetrahydrofuran Add dropwise, add dropwise for 3 hours, and reflux while adding dropwise. After the dropwise addition, cool to room temperature, filter the reactant, evaporate the solvent from the filtrate, and purify the residue with a silica gel column, the eluent is 70% cyclohexane / 30% ethyl acetate, evaporate the eluent under reduced pressure, vacuum After drying, the polymerizable photoinitiator N-3,4-methylenedioxyphenyl-2-methylmaleimide is obtained. The structure is shown in structural formula 1: 1H NMR (250MHz) in CDCl3: δ1.93ppm (3H, CH...

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Abstract

The invention discloses a polymerizable photoinitiator shown in a formula in the specification and a preparation method thereof. The preparation method comprises the following steps of: carrying out reaction on unsaturated diacid or unsaturated dianhydride and 3,4-methylenedioxy aniline used as raw materials under the protection of nitrogen or argon to generate amide containing unsaturated anhydride, and then reacting in the presence of Lewis acid and hexamethyl disilazane to generate the polymerizable photoinitiator. The polymerizable photoinitiator has the characteristics that: because of the existence of the unsaturated alkene amide group, the compatibility between the photoinitiator and an initiation system is improved, and the surface migration of the photoinitiator is greatly reduced; and due to the existence of unsaturated double bonds, the photoinitiator can also be used as a monomer for synthesizing a high-molecular-weight photoinitiator, and has wide application in ultraviolet curing and other fields. In the formula, R is equal to H or CH3.

Description

technical field [0001] The invention belongs to a photoinitiator and its preparation method, in particular to a polymerizable photoinitiator and its preparation method. Background technique [0002] Photocuring technology is a new green technology that came out in the 1960s. It refers to the process in which liquid monomers and oligomers undergo polymerization and crosslinking reactions to form solid products under the action of light (ultraviolet or visible light). Compared with other curing technologies such as thermal curing, light curing has many advantages: such as low energy consumption, no solvent volatilization during curing, low pollution, fast and complete curing at room temperature, and excellent physical and chemical properties of Weihua coating. Therefore, it has been widely used in industrial fields such as photoresists, photocurable coatings, electronic packaging materials, photocurable inks, adhesives, and printing materials. Photopolymerization systems usua...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07D405/06
Inventor 马贵平聂俊路健徐帅
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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