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Benzophenone macromolecular photoinitiator and preparation method thereof

A technology of benzophenones and photoinitiators, which is applied in the field of benzophenone macromolecular photoinitiators and their preparation, can solve the problems of easy volatilization and migration, reduced initiation efficiency, poor compatibility, etc., and achieves easy Realization, the effect of simple preparation method and good compatibility

Inactive Publication Date: 2014-01-01
CHANGZHOU GAOTE TAIKE NEW MATERIAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor compatibility of traditional small molecules with the curing system, they are easy to volatilize and migrate after curing. On the one hand, the initiation efficiency is reduced, and on the other hand, it will produce odor and toxicity

Method used

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  • Benzophenone macromolecular photoinitiator and preparation method thereof
  • Benzophenone macromolecular photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] (a) Dissolve 1 part of 4.4'-dihydroxybenzophenone derivatives, 4.5 parts of paraformaldehyde, and 2 parts of diglycolamine in 50 parts of 1,4-dioxane, and stir until completely dissolve. Slowly heat to reflux at a heating rate of 5°C / min, keep the reflux reaction for 8 hours, stop heating and cool to room temperature, distill off the solvent under reduced pressure, add chloroform to dissolve, wash 5 times with 0.1N sodium hydroxide aqueous solution, deionize Wash with water 5 times. Then the organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was evaporated to remove the solvent, and the intermediate product (BZOH) was obtained after vacuum drying.

[0022] (b) Dissolve 1 part of BZOH obtained in 50 parts of dry chloroform, dissolve 0.9 parts of diisocyanate in 20 parts of dry chloroform and add it to a constant pressure dropping funnel, control the dropping speed of 4-5s / drop, and magnetically After stirring for 24 hours, the organic lay...

Embodiment 2

[0024] (a) 1 part of 4,4'-dihydroxybenzophenone derivative, 4.2 parts of paraformaldehyde, and 2 parts of diglycolamine were dissolved in 50 parts of toluene, and mechanically stirred until completely dissolved. Slowly heat to reflux at a heating rate of 5°C / min, keep the reflux reaction for 6 hours, stop heating and cool to room temperature, distill off the solvent under reduced pressure, add chloroform to dissolve, wash 5 times with 01N sodium hydroxide aqueous solution, deionized water Wash 5 times. Then the organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was evaporated to remove the solvent, and the intermediate product (BZOH) was obtained after vacuum drying.

[0025] (b) Dissolve 1 part of BZOH obtained in 50 parts of dry THF, dissolve 0.7 parts of diisocyanate in 20 parts of dry THF and add it to a constant pressure dropping funnel, control the dropping speed of 4-5s / drop, and magnetically After stirring for 24 hours, the organic layer...

Embodiment 3

[0027] (a) 1 part of 4,4'-dihydroxybenzophenone derivatives, 4.5 parts of paraformaldehyde, and 2 parts of diglycolamine were dissolved in 50 parts of xylene, and mechanically stirred until completely dissolved. Slowly heat to reflux at a heating rate of 5°C / min, keep the reflux reaction for 6 hours, stop heating and cool to room temperature, distill off the solvent under reduced pressure, add chloroform to dissolve, wash 5 times with 0.1N sodium hydroxide aqueous solution, deionize Wash with water 5 times. Then the organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was evaporated to remove the solvent, and the intermediate product (BZOH) was obtained after vacuum drying.

[0028] (b) Dissolve 1 part of BZOH obtained in 50 parts of dry DMSO, dissolve 0.8 parts of diisocyanate in 20 parts of the above-mentioned DMSO and add it to the constant pressure dropping funnel, control the dropping speed of 4-5s / drop, at room temperature After magnetically...

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Abstract

The invention relates to a benzophenone macromolecular photoinitiator and a preparation method thereof. The structural formula of the photoinitiator is shown in the specification. According to the method, an intermediate product (BZOH) is synthesized from 4,4'-dihydroxy benzophenone, paraformaldehyde and diglycolamine as raw materials through a Mannich reaction, and a target product is prepared through reacting BZOH with diisocyanate. According to the macromolecular photoinitiator prepared by the method, the same molecular chain simultaneously contains benzophenone and tertiary amine structures, so that the active species generation efficiency of photosensitive decomposition can be increased; the macromolecular photoinitiator is polyurethane containing a benzoxazine structure, so that the compatibility with an initiating system is improved, the surface migration of the photoinitiator is lowered greatly, and the macromolecular photoinitiator can also serve as a functional material and is believed that the macromolecular photoinitiator can have wide application in the fields of ultraviolet curing and the like. In the structural formula, R1 and R2 are H, CH3 or CH2Cl independently, and at least one of ortho positions of phenol-OH of a 4,4'-dihydroxy benzophenone derivative can not have substituents.

Description

technical field [0001] The invention relates to a benzophenone macromolecular photoinitiator and a preparation method thereof. Background technique [0002] UV curing technology is a representative start in the development of coatings, adhesives and inks. It is a new green technology that came out in the 1960s. It uses light (ultraviolet or visible light) or electron beams as energy sources to trigger The rapid transformation of a chemically reactive liquid substance into a solid state. Compared with traditional solution molding, UV curing molding has many unique advantages, such as faster curing speed, excellent chemical resistance, better weather resistance and the possibility of reducing environmental pollution. Photocuring systems usually include reactive monomers, prepolymers and photoinitiators. Under ultraviolet radiation, the photolysis reaction of the photoinitiator generates active species to initiate the polymerization of monomers and prepolymers. With the cont...

Claims

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Application Information

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IPC IPC(8): C08G18/32C08F2/48
CPCC08G18/3844C08F2/48
Inventor 时劲松肖鸣王祥春王欢
Owner CHANGZHOU GAOTE TAIKE NEW MATERIAL SCI & TECH
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