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Naphthalimide aromatic sulfide photoinitiator for UV-LED photocuring and preparation method and application thereof

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: 2019-03-01
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 aromatic sulfide photoinitiator for UV-LED photocuring and preparation method and application thereof
  • Naphthalimide aromatic sulfide photoinitiator for UV-LED photocuring and preparation method and application thereof
  • Naphthalimide aromatic sulfide photoinitiator for UV-LED photocuring and preparation method and application thereof

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 liquid was cooled to room temperature, and the reaction liquid was poured into 1000 mL of ice water, filtered, and 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 (...

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 aromatic sulfide photoinitiator for UV-LED photocuring and relates to the field of light-sensing polymers. The photoinitiator herein is provided based on the problem that an existing photoinitiator has poor initiating property under irradiation of an UV-LED light source and has a chemical structural formula shown in the description, wherein R1 is selected from C1-C16 aliphatic hydrocarbon group, aralkyl or phenyl; R2 is selected independently from hydrogen, alkyl, alkoxy, acyl, halogen atom, and nitryl. The invention also provides a preparation method ofthe photoinitiator herein and application of the photoinitiator in a photocuring system. The photoinitiator herein and its preparation method and application have the advantages that ultraviolet absorption wavelength of the photoinitiator prepared herein is evidently extended, the photoinitiator has high photocuring efficiency under the action of a UV-LED light source, and the photoinitiator is helpful for 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 Applications(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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