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Hydrogen donor-containing thioether naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring

A UV-LED and naphthalimide technology, which is applied in the field of photosensitive polymers, can solve the problems of limiting the development and promotion of UV-LED photocuring technology, poor triggering performance, and poor absorption of light energy, and achieve UV absorption wavelength extension, Effect of low mobility and performance improvement

Active Publication Date: 2021-11-23
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the reported or commercialized photoinitiators have poor absorption wavelength above 365nm, and under the irradiation of UV-LED light source, the initiation performance of these photoinitiators is poor
In addition, these commercial photoinitiators are sensitive to oxygen and must be strictly deoxygenated during use. These two points severely limit the development and promotion of UV-LED light curing technology.

Method used

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  • Hydrogen donor-containing thioether naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring
  • Hydrogen donor-containing thioether naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring
  • Hydrogen donor-containing thioether naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Photoinitiator NABS-HD-1 has the following structural formula:

[0049]

[0050] Its preparation method comprises the following steps:

[0051] (a) 4-bromo-1,8-naphthalic anhydride (7.20g, 0.026mol), diglycolamine (13.67g, 0.13mol) and 100mL absolute ethanol were added to a 250mL single-necked flask, under nitrogen protection After the reaction, the reaction liquid was cooled to room temperature and filtered to obtain the crude product. The filter residue was washed with absolute ethanol several times, and the intermediate product was obtained after vacuum drying, which was named BHBD.

[0052] (b) BHBD (5.83g, 16mmol), triethylamine (6.48g, 64mmol) and 150mL of anhydrous dichloromethane synthesized in Example 1 were added to a 250mL single-necked flask, and acetyl chloride (3.77g, 48mmol) was dissolved in 20mL of anhydrous dichloromethane, added dropwise into a single-necked flask in an ice-water bath at 0°C, and stirred for 6h; after the reaction was completed, th...

Embodiment 2

[0058] The photoinitiator NABS-HD-2 has the following structural formula:

[0059]

[0060] Its preparation method comprises the following steps:

[0061](a) BHBD (5.83g, 16mmol), triethylamine (6.48g, 64mmol) and 150mL of anhydrous dichloromethane synthesized in Example 1 were added to a 250mL single-necked flask, and acryloyl chloride (4.35g, 48mmol) was dissolved in 20mL of anhydrous dichloromethane, added dropwise into a single-necked flask in an ice-water bath at 0°C, and stirred for 6h; after the reaction was completed, the solvent was distilled off under reduced pressure to obtain a crude product, which was then purified by a chromatographic column , to obtain an intermediate product named BDBIEB.

[0062] (b) BDBIEB (836.90mg, 2mmol), MOBET (1.18g g, 6mmol), bis(dibenzylideneacetone)palladium (690.60mg, 1.2mmol), 1,1'-bis (Diphenylphosphino)ferrocene (98.70mg, 0.024mmol), anhydrous tripotassium phosphate (1.02g, 4.8mmol), 8mL toluene and 4mL acetone were added to ...

Embodiment 3-8

[0066] The purpose of embodiment 3-8 is to illustrate that the photoinitiator containing hydrogen donor sulfide type naphthalimide derivatives prepared in embodiment 1-2 can be effective in the environment where oxygen exists under the irradiation of UV-LED light source. Initiate the polymerization of monomer 1,6-hexanediol diacrylate (HDDA); the initiation activity is higher than that of existing photoinitiators 2959, 184, and 1173.

[0067] (1) prepare photosensitive resin composition: its proportioning is:

[0068] A: 1,6-hexanediol diacrylate (99.5 or 98 parts by mass)

[0069] B: Photoinitiator (0.5 parts by mass)

[0070] C: Photoinitiator (2.0 parts by mass)

[0071] Table 1 is the composition proportioning in each embodiment:

[0072]

[0073] (2) Polymerization performance test

[0074] Test method: After stirring the above composition in the dark, apply it evenly on the potassium bromide salt sheet with a capillary tube to form a coating film of about 30 μm, a...

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Abstract

The invention discloses a hydrogen donor-containing thioether naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring, relates to the field of photosensitive macromolecules, and aims to solve the problem that the existing photoinitiator has poor initiation performance under the irradiation of a UV-LED light source in the presence of oxygen. The invention prepares a hydrogen donor-containing thioether naphthalimide derivative photoinitiator, and provides a preparation method of the hydrogen donor-containing thioether naphthalimide derivative photoinitiator and application of the hydrogen donor-containing thioether naphthalimide derivative photoinitiator in a photocuring system. The beneficial effects are that (1) the ultraviolet absorption wavelength of the prepared photoinitiator is obviously prolonged, and the photoinitiator has better ultraviolet absorption capacity in the wavelength range of an LED light source; (2) the photoinitiator prepared by the invention has an obvious anti-oxygen polymerization inhibition effect; and (3) the migration stability of the prepared photoinitiator is obviously improved.

Description

technical field [0001] The invention relates to the field of photosensitive polymers, in particular to a preparation method and application of a hydrogen donor-containing sulfide-type naphthalimide derivative photoinitiator suitable for UV-LED aerobic photocuring. 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 (with a wavelength of 200-400nm) as the energy source to trigger the 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, less pollution and low cost, and is a rapidly developing "green" new technology. UV photocurable products are composed of three parts, namely photoinitiator, photocurable resin and monomer (also known as reactive diluent). [0003] Ultraviolet light-emitting diode (UV-LED) is a semiconductor electronic device. UV-L...

Claims

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Application Information

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IPC IPC(8): C08F2/48C07D221/14
CPCC08F2/48C07D221/14
Inventor 孙芳胡修远
Owner BEIJING UNIV OF CHEM TECH
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