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Benzophenone type derivative photoinitiator and preparation method thereof

A technology of benzophenone and photoinitiator is applied in the field of benzophenone derivative photoinitiator and its preparation, which can solve the problems of short absorption wavelength of photoinitiator, and achieves improvement of short absorption wavelength and reaction Mild conditions and enhanced light absorption

Inactive Publication Date: 2019-01-29
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is: in order to solve the problem that photoinitiator BP absorbs shorter wavelength in UV absorption spectrum, the present invention provides a kind of benzophenone derivative photoinitiator, has introduced in molecular structure The alkyl chain containing unsaturated bonds makes its maximum absorption wavelength red shift to a certain extent relative to benzophenone (BP), and its light absorption ability is greatly enhanced, and the efficiency of initiating oligomers is higher than that of traditional benzophenone. Improvement also means that it is a good photoinitiator, and effectively improves the problem that the absorption wavelength of BP photoinitiator is shorter

Method used

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  • Benzophenone type derivative photoinitiator and preparation method thereof
  • Benzophenone type derivative photoinitiator and preparation method thereof
  • Benzophenone type derivative photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The structural formula of compound 1 is:

[0028]

[0029] 9.91g (50mmol) of 4-hydroxybenzophenone, 3.46g (25mmol) of potassium carbonate, and 80ml of carbon tetrachloride were added together into a 250ml three-necked bottle equipped with a magnetic stirrer and a thermometer, and heated and stirred with nitrogen gas. Mix 9.25g (75mmol) of 3-bromopropene and 154g (1mol) of carbon tetrachloride in a constant pressure funnel, then slowly add the mixed solution into a three-necked flask, heat up to 60°C and reflux for 24h. After the reaction, Remove solid impurities by filtration, wash with water and separate liquid for 3 times to remove salts, remove the solvent by rotary evaporation, and then recrystallize to obtain white powder crystals, 4.76g.

[0030] Add 4.76g (about 0.02mol) of the white powder obtained above and 100ml of absolute ethanol (dried to remove water) into a 250ml three-necked bottle equipped with a reflux condenser and a magnetic stirrer, blow nitrogen...

Embodiment 2

[0033] The structural formula of compound 2

[0034]

[0035] Add 9.91g (50mmol) of 4,4'-dihydroxybenzophenone, 3.46g (25mmol) of potassium carbonate, and 100ml of acetone into a 250ml three-necked bottle equipped with a magnetic stirrer and a thermometer, blow nitrogen gas, and heat and stir. Mix 6.15g (51mmol) of 3-bromopropene and 60g (1mol) of acetone in a constant pressure funnel, and then slowly add the mixed solution into a three-necked flask, heat up to 60°C and reflux for 24h. After the reaction, filter to remove the solid Impurities were washed with water and separated three times to remove salts, and the solvent was removed by rotary evaporation, and recrystallized to obtain white powder crystals, 5.13 g.

[0036] Add 5.13g (about 0.02mol) of the white powder obtained above and 100ml of absolute ethanol (dried to remove water) into a 250ml three-necked bottle equipped with a reflux condenser and a magnetic stirrer, blow nitrogen gas, stir for about 1h, and remove...

Embodiment 3

[0039] The structural formula of compound 3 is:

[0040]

[0041] 9.91g (50mmol) of 4-hydroxybenzophenone, 7.92g (50mmol) of potassium carbonate, and 120ml of carbon tetrachloride were added together into a 250ml three-necked bottle equipped with a magnetic stirrer and a thermometer, and heated and stirred with nitrogen gas. Mix 12.30 g (100 mmol) of 3-bromopropene and 144 g (2 mol) of tetrahydrofuran in a constant pressure funnel, then slowly add the mixture into a three-necked flask, heat up to 60°C and reflux for 24 hours. After the reaction is complete, filter to remove the solid Impurities were washed with water and liquid-separated three times to remove salts, and the solvent was removed by rotary evaporation, and recrystallized to obtain white powder crystals, 5.78g.

[0042] Add 5.78g (about 0.02mol) of the white powder obtained above and 100ml of absolute ethanol (dried to remove water) into a 250ml three-necked bottle equipped with a reflux condenser and a magneti...

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Abstract

The invention belongs to the field of photosensitive high polymer materials. After a hydrogen abstraction type photoinitiator absorbs light energy, the photoinitiator produces a bimolecular action with an auxiliary initiator in an excited state to generate a living free radical and initiate monomer polymerization. A one-component hydrogen abstraction type photoinitiator introducing a benzophenonestructure containing an unsaturated bond alkyl chain in a molecular structure is synthesized by using 4-hydroxybenzophenone and allyl bromide as raw materials. The invention provides a preparation method of a benzophenone type derivative photoinitiator; a reaction process is simple, and a reaction condition is mild; the maximum absorption wavelength of a product has a certain degree of red shift relative to that of benzophenone (BP), and the light absorption capacity of the photoinitiator is greatly enhanced; compared with that of traditional benzophenone, the efficiency of initiating oligomers is improved to a certain extent; and all performance is superior to that of the benzophenone, the photoinitiator can replace the benzophenone and has wide application prospects in the field of ultraviolet light curing.

Description

technical field [0001] The invention belongs to the field of photosensitive polymer materials, and relates to a benzophenone derivative photoinitiator and a preparation method thereof. Background technique [0002] Photopolymerization has the advantages of mild reaction conditions, fast reaction speed, less damage to the substrate, no discharge of three wastes, and no pollution to the environment. Has a wide range of applications. Generally speaking, the photocuring system contains oligomers, monomers, photoinitiators and auxiliary agents, and although the photoinitiator accounts for a small amount, it plays a vital role in the whole system, because the initiator can Under the irradiation of ultraviolet light with a wavelength, the absorbed light can generate active species, free radicals or ions, thereby initiating the polymerization of monomers. [0003] Benzophenone (BP) is a type-II photoinitiator that is easy to synthesize, low in price, has a long triplet lifetime in...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C49/84C08F2/48
CPCC07C45/67C07C45/64C07C49/84C08F2/48
Inventor 杨金梁郝亚娟王磊聂俊
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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