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Naphthalimide aryl sulfide type photoinitiator suitable for uv-led light curing, preparation method and application

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

Active Publication Date: 2022-04-12
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 sulfide type photoinitiator suitable for uv-led light curing, preparation method and application
  • Naphthalimide aryl sulfide type photoinitiator suitable for uv-led light curing, preparation method and application
  • Naphthalimide aryl sulfide type photoinitiator suitable for uv-led light curing, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Photoinitiator NAS1 has the following structural formula:

[0035]

[0036] Its preparation method comprises the following steps:

[0037] (a) 4-bromo-1,8-naphthalic anhydride (7.20g, 0.026mol), p-toluidine (27.86g, 0.26mol) and 100mL acetic acid were added to a 250mL single-necked flask, under nitrogen protection, Raise the temperature to 120°C and stir at constant temperature for 24 hours; after the reaction, the reaction solution was cooled to room temperature, the reaction solution was poured into 1000 mL of ice water, filtered, the filter cake was washed with deionized water for 3 times, and the crude product was obtained after vacuum drying. The crude product was recrystallized with acetic acid to obtain an intermediate product named MPNB;

[0038] (b) The intermediate product MPNB (732mg, 2mmol), iodobenzene (408mg, 2mmol), potassium thioacetate (228mg, 2mmol), bis(dibenzylideneacetone) palladium (115mg, 0.2mmol), 1,1 '-Bis(diphenylphosphino)ferrocene (155mg...

Embodiment 2

[0042] Photoinitiator NAS2 has the following structural formula:

[0043]

[0044] Its preparation method comprises the following steps:

[0045]The intermediate product MPNB (732mg, 2mmol) synthesized in Example 1, p-iodoacetophenone (492mg, 2mmol), potassium thioacetate (228mg, 2mmol), bis(dibenzylideneacetone) palladium (115mg, 0.2 mmol), 1,1'-bis(diphenylphosphino)ferrocene (155mg, 0.28mmol), anhydrous tripotassium phosphate (1.02g, 4.8mmol), 4mL toluene and 2mL acetone were added to a 25mL three-necked flask, Under the protection of nitrogen, the temperature was raised to 70° C., stirred at a constant temperature for 3 hours, and then the temperature was raised to 110° C., and stirred at a constant temperature for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was poured into 10 mL of saturated ammonium chloride aqueous solution, extracted 3 times with dichloromethane, the organic layers were com...

Embodiment 3

[0049] Photoinitiator NAS3 has the following structural formula:

[0050]

[0051] Its preparation method comprises the following steps:

[0052] The intermediate product MPNB (732mg, 2mmol) synthesized in Example 1, p-nitroiodobenzene (498mg, 2mmol), potassium thioacetate (228mg, 2mmol), bis(dibenzylideneacetone) palladium (115mg, 0.2 mmol), 1,1'-bis(diphenylphosphino)ferrocene (155mg, 0.28mmol), anhydrous tripotassium phosphate (1.02g, 4.8mmol), 4mL toluene and 2mL acetone were added to a 25mL three-necked flask, Under the protection of nitrogen, the temperature was raised to 70° C., stirred at a constant temperature for 3 hours, and then the temperature was raised to 110° C., and stirred at a constant temperature for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the reaction solution was poured into 10 mL of saturated ammonium chloride aqueous solution, extracted 3 times with dichloromethane, the organic layers were co...

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Abstract

The invention discloses a naphthalimide aryl sulfide photoinitiator suitable for UV-LED light curing, relates to the field of photosensitive polymers, and is based on the initiating performance of the existing photoinitiator under the irradiation of a UV-LED light source Poor problem and proposed, the general chemical structure formula of described 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 effect of the present invention is: 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 sulfide photoinitiator suitable for UV-LED light curing, a preparation method and application. Background technique [0002] UV curing technology is a process in which liquid substances with chemical reactivity using ultraviolet photoinitiators are rapidly transformed into solid substances. This technology has the characteristics of high efficiency, wide adaptability, economy, energy saving and environmental friendliness. It is widely used in the fields of printing plate making, stereolithography, ink, coating, adhesive, food packaging and medical biomaterials. [0003] Ultraviolet light-emitting diode (UV-LED) is a semiconductor electronic device. UV-LED equipment can convert electrical energy into chemical optical radiation. As a radiation equipment, UV-LED has been widely used in the fields of radiation curing and photopolymerization. Compared with ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C08F122/14C08F2/50
CPCC07D221/14C08F2/50C08F122/1006
Inventor 孙芳于佳聂俊
Owner 安庆北化大科技园有限公司
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