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Naphthalimide aryl benzyl sulfide type photoinitiator suitable for UV-LED light curing, preparation method and application

A naphthalimide arylbenzyl sulfide, UV-LED technology, applied in the field of photosensitive polymers, can solve problems such as poor initiation performance of photoinitiators, and achieve the effects of prolonged ultraviolet absorption wavelength and high photocuring efficiency

Active Publication Date: 2022-04-08
安庆北化大科技园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The problem to be solved by the present invention is that existing photoinitiators have poor initiating performance under the irradiation of UV-LED light source

Method used

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  • Naphthalimide aryl benzyl sulfide type photoinitiator suitable for UV-LED light curing, preparation method and application
  • Naphthalimide aryl benzyl sulfide type photoinitiator suitable for UV-LED light curing, preparation method and application
  • Naphthalimide aryl benzyl sulfide type photoinitiator suitable for UV-LED light curing, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The photoinitiator NABS1 has the following structural formula:

[0034]

[0035] Its preparation method comprises the following steps:

[0036] (a) Add 4-bromo-1,8-naphthalic anhydride (7.20g, 0.026mol), 2,6-diisopropylaniline (46.10g, 0.26mol) and 100mL acetic acid into a 250mL single-necked flask , under the protection of nitrogen, raise the temperature to 120°C, stir at constant temperature for 24 hours; after the reaction, wait for the reaction solution to cool to room temperature, pour the reaction solution into 1000mL ice water, filter, wash the filter cake with deionized water 3 times, and vacuum dry The crude product was obtained; the crude product was recrystallized with acetic acid to obtain an intermediate product named DPPNB;

[0037] (b) Add benzylmercaptan (2.49g, 0.02mol), acetic anhydride (4.08g, 0.04mol) and anhydrous nickel chloride (259mg, 2mmol) into a 50mL one-necked flask, and stir at room temperature for 4h. After the reaction, add 30mL deion...

Embodiment 2

[0042] The photoinitiator NABS2 has the following structural formula:

[0043]

[0044] Its preparation method comprises the following steps:

[0045] (a) Add p-methylbenzylmercaptan (2.76g, 0.02mol), acetic anhydride (4.08g, 0.04mol) and anhydrous nickel chloride (259mg, 2mmol) into a 50mL one-necked flask, and stir at room temperature for 4h. After the reaction, add 30mL deionized water to the reactor, extract 3 times with dichloromethane, combine the organic layers, wash the organic layer 3 times with 10% aqueous sodium bicarbonate solution and deionized water respectively, and wash the organic layer with anhydrous Na 2 SO 4 After drying, filter, and remove the solvent by distillation under reduced pressure to obtain a crude product, then, purify the crude product with column chromatography to obtain an intermediate product, which is named MBET; wherein the steps of distillation under reduced pressure and column chromatography purification can be carried out as long as...

Embodiment 3

[0050] The photoinitiator NABS3 has the following structural formula:

[0051]

[0052] Its preparation method comprises the following steps:

[0053] (a) Add p-methoxybenzylmercaptan (3.09g, 0.02mol), acetic anhydride (4.08g, 0.04mol) and anhydrous nickel chloride (259mg, 2mmol) into a 50mL one-necked flask, and stir at room temperature for 4h. After the reaction, add 30mL deionized water to the reactor, extract 3 times with dichloromethane, combine the organic layers, wash the organic layer 3 times with 10% aqueous sodium bicarbonate solution and deionized water respectively, and wash the organic layer with anhydrous Na 2 SO 4 After drying, filter, and remove the solvent by distillation under reduced pressure to obtain a crude product, then, purify the crude product with column chromatography to obtain an intermediate product, which is named as MOBET; wherein the steps of distillation under reduced pressure and column chromatography can be carried out as long as the pro...

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Abstract

The invention discloses a naphthalimide aryl benzyl sulfide type photoinitiator suitable for UV-LED photocuring, relates to the field of photosensitive polymers, and is based on the irradiation of an existing photoinitiator in a UV-LED light source The problem of poor triggering performance is proposed, and the general chemical structure formula of the photoinitiator is as follows: Wherein, R 1 Selected from C1‑C16 aliphatic hydrocarbon group, aralkyl group or phenyl group, R 2 Respectively independently selected from hydrogen, alkyl, alkoxy, acyl, halogen atom, nitro; the present invention also provides the preparation method of the above-mentioned photoinitiator and its application in photocuring system; the beneficial effects of the present invention are: the present invention The photoinitiator prepared by the invention has significantly extended ultraviolet absorption wavelength, and has higher photocuring efficiency under the action of UV-LED light source, which is conducive to the development of UV-LED photocuring industry.

Description

technical field [0001] The invention relates to the field of photosensitive polymers, in particular to a naphthalimide aryl benzyl sulfide photoinitiator suitable for UV-LED light curing, a preparation method and application. Background technique [0002] UV light curing technology is a new technology that came out in the middle of the 20th century. It uses ultraviolet light (wavelength 200-400nm) as the energy source to trigger the process of rapid transformation of chemically reactive liquid substances into solids. Compared with the traditional thermal curing technology, it has the advantages of fast speed, high efficiency, low pollution, excellent performance and low cost, and is a rapidly developing "green" new technology. UV light curing products are composed of three parts, namely light curing resin, diluent and photoinitiator. [0003] Ultraviolet light-emitting diode (UV-LED) is a semiconductor electronic device. UV-LED equipment can convert electrical energy into c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C08F122/14C08F2/48
CPCC07D221/14C08F2/48C08F122/14
Inventor 孙芳于佳聂俊
Owner 安庆北化大科技园有限公司
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