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Photoinitiator and preparation method thereof

A technology of photoinitiator and carbon atom, which is applied in the field of photoinitiator and its preparation, can solve the problems of low absorption capacity, poor performance of photoinitiator, and low efficiency of photosensitive free radicals, etc., to achieve strong absorption and high efficiency against the surface The effect of oxygen inhibition

Active Publication Date: 2017-11-28
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the field of photocuring, the performance of photoinitiators suitable for mainstream 385-395nm UV-LEDs is generally poor. The existing photoinitiators have low absorption capacity for ultraviolet light emitted by 385-395nm, and the efficiency of photosensitive generation of free radicals is not high. , still lead to serious surface oxygen inhibition, limiting the application of UV-LED in photocuring
And for photoinitiation systems containing tertiary amines, most of the tertiary amine anti-oxidation and polymerization inhibition components are only in the interior of the curing system, and the surface contains very little tertiary amines, and the problem of surface oxygen polymerization inhibition has not been well resolved.

Method used

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  • Photoinitiator and preparation method thereof
  • Photoinitiator and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A photoinitiator whose structure is shown in formula (M):

[0040]

[0041] (M)

[0042] Wherein, the substitution position on the thioxanthone aromatic ring is 2 and / or 4; R 1 and R 2 An alkyl group of 1 to 7 carbon atoms or a combination of the two into an n-alkylene group of 4 to 5 carbon atoms; X is —Z-S-CH 2 CH 2 —, where Z is an alkylene group with 2 to 6 carbon atoms, and the Z group is connected to the nitrogen atom of the quaternary ammonium salt; n in the fluorocarbon chain is 6 to 8; Y - is a nucleophilic anion.

[0043] Preferably, the Y- for PF 6 ¯, SbF 6 ¯ or Ph 4 B.

[0044] Preferably, the Y - for Ph 4 B.

Embodiment 2

[0046] The preparation method of above-mentioned photoinitiator, comprises the following steps:

[0047] S 1 . Preparation of fluorocarbon chain quaternary ammonium salt:

[0048] Using 20ml tetrahydrofuran as the medium, add 2g perfluorooctyl bromide, 0.73g N,N-diethylethanethiolamine, heat the reaction system to 60°C, add 0.3 g sodium hydroxide, perfluorooctyl The molar ratio of ethyl bromide, N,N-diethylethanethiolamine, and sodium hydroxide is 1.0:1.5~5:1.5~5, and the reaction system is reacted at 60°C for 48h; extracted with water, and the solvent is spin-dried , obtain 1.7g off-white liquid, productive rate 84.16%, product B 1 The structure of diethylaminoethyl-perfluorooctyl ethyl sulfide is as figure 2 As shown, the NMR data are: 1 H NMR (400 MHz, CDCl 3 ): δ2.71 (dd, J = 18.0, 9.4 Hz, 1H),2.66–2.54 (m, 2H), 2.50 (q, J = 7.1 Hz, 2H), 2.42-2.26 (m, 1H), 0.98 (t, J =7.1 Hz, 3H).

[0049] S 2 . Preparation of thioxanthone modified by fluorocarbon chain quate...

Embodiment 3

[0055] A kind of preparation method of photoinitiator, comprises the following steps:

[0056] S1. Preparation of fluorocarbon chain quaternary ammonium salt:

[0057] With 20ml tetrahydrofuran as the medium, add 2g perfluorooctyl bromide, 0.70g N,N-dimethylethanethiolamine, heat the reaction system to 60°C, add 0.3 g sodium hydroxide, perfluorooctyl The molar ratio of ethyl bromide, N,N-diethylethanethiolamine, and sodium hydroxide is 1.0:1.5~5:1.5~5, and the reaction system is reacted at 60°C for 48h; extracted with water, and the solvent is spin-dried , to obtain slightly beige liquid, yield 77.08%, product B 2 The structure of N,N-dimethylethylammonia-perfluorooctylethylsulfide is as follows Figure 5 As shown, the NMR data are 1 H NMR (400 MHz, CDCl 3 ) δ2.79 (t, J = 16.1, 8.2 Hz, 2H),2.73–2.64 (t, 2H), 2.53 (t, J = 14.8, 8.1 Hz, 2H), 2.40 (m, J = 30.9, 19.6,11.2 Hz, 2H), 2.33 (s, J = 38.0 Hz, 6H).

[0058] S 2 . Preparation of thioxanthone modified by fluo...

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Abstract

The invention relates to fields of photosensitive materials and photocuring and particularly relates to a photoinitiator and a preparation method thereof. The photoinitiator can absorb long waves based on a thioxanthone mother nucleus and can strongly absorb a 395nm UV LED light source. By introducing fluorine carbon chain so as to endow the photoinitiator with a low surface tension, the photoinitiator can float to the surface of a coating layer / ink layer in a formula system, namely that the photoinitiator can be enriched in the surface; and after light is absorbed, high-concentration free radicals are generated on the surface so as to confront against surface oxygen inhibition. The novel photoinitiator contains a quaternary ammonium group and is connected with a thioxanthone aromatic ring through a methylene, so that the structure has a photosensitive cracking property, is capable of generating tertiary amine with an oxygen inhibition prevention function through photolysis and can be simultaneously used as an initiation aid of thioxanthone for generating free radicals. All behaviors are generated on the surface of the coating layer / ink layer, so that the photoinitiator has the characteristic of being capable of efficiently confronting against surface oxygen inhibition.

Description

technical field [0001] The invention relates to the field of photosensitive materials and photocuring, in particular to a photoinitiator and a preparation method thereof. Background technique [0002] Photocuring refers to the technology of instantaneous polymerization, crosslinking and curing of organic formula material systems under ultraviolet light irradiation. drug field. The traditional free radical photoinitiator initiates the polymerization reaction. Although the curing speed is fast, due to the ubiquitous oxygen inhibition effect of the free radical polymerization reaction, there is always a non-negligible oxygen inhibition on the surface of the photo-cured coating, resulting in cross-polymerization of the coating surface. Insufficient connection, insufficient wear resistance of the surface, and even surface stickiness, back sticking and other disadvantages. [0003] On the other hand, traditional photocuring uses a medium-pressure mercury lamp as a radiation sour...

Claims

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Application Information

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IPC IPC(8): C07D335/16C08F2/48
CPCC07D335/16C08F2/48
Inventor 黄李江廖焕妍杨建文曾兆华
Owner SUN YAT SEN UNIV
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