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Fluorinated hydrogen abstraction polymer photoinitiator, preparation method and application thereof

A photoinitiator and polymer technology, applied in the field of fluorinated hydrogen abstraction polymer photoinitiator, can solve the problems of easy migration, poor stability, yellowing, etc.

Inactive Publication Date: 2016-03-30
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to address the deficiencies of the current prior art, to provide a fluorinated hydrogen abstraction polymer photoinitiator, a preparation method and its application. The fluorinated hydrogen abstraction polymer photoinitiator of the present invention has the following characteristics : (1) Overcoming the defects of traditional small molecule photoinitiators such as easy migration, yellowing, poor stability, and residue; (2) Since the photoinitiator molecule and the co-initiator amine are on the same polymer chain, it is beneficial energy transfer, thereby generating more free radical active species faster and improving photoinitiation efficiency; (3) fluorinated polymer photoinitiators, due to the ultra-low surface energy and ultra-low surface tension of fluorine atoms, they can Self-assembled on the surface to form a gradient self-assembled layer whose concentration gradually decreases from top to bottom; (4) The photoinitiator on the surface layer is enriched relative to the body layer, which can preferentially undergo photopolymerization to form a barrier to oxygen diffusion into the photopolymerization system The thin film layer has better anti-oxidation and polymerization inhibition effect

Method used

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  • Fluorinated hydrogen abstraction polymer photoinitiator, preparation method and application thereof
  • Fluorinated hydrogen abstraction polymer photoinitiator, preparation method and application thereof
  • Fluorinated hydrogen abstraction polymer photoinitiator, preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] A fluorinated hydrogen abstraction polymer photoinitiator P (F-TX-A-MMA), the structural formula is as follows:

[0040]

[0041] The preparation method is as follows:

[0042] (1) 1 mole of O-(thioxanthone-[2]-yl)-oxyacetic acid and 1.2 moles of 2-hydroxyethyl methacrylate are dissolved in dichloromethane, ice-water bath, and then add 0.1 mole 4-dimethylaminopyridine and 1 mole of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were used as catalyst and dehydrating agent respectively, stirred, and reacted for 24 hours at normal temperature, and used Precipitate with a large amount of deionized water, filter with suction, and dry in a constant temperature vacuum oven at 70°C to prepare acrylate containing photoinitiator thioxanthone;

[0043] (2) 1 mole of p-dimethylaminobenzoic acid and 1.2 moles of 2-hydroxyethyl methacrylate are dissolved in dichloromethane, then add 0.1 mole of 4-dimethylaminopyridine and 1 mole of 1-( 3-Dimethylaminopropyl)-3-ethyl...

Embodiment 2

[0048] A fluorinated hydrogen abstraction polymer photoinitiator P(F-BP-DEMA-S), the structural formula is as follows:

[0049]

[0050] The preparation method is as follows:

[0051] (1) 1.2 moles of 4-chloromethylstyrene and 1 mole of hydroxybenzophenone are dissolved in acetonitrile, 1 mole of anhydrous potassium carbonate and catalyst amount of potassium iodide are added, refluxed for 24 hours, deionized water precipitation, Filter with suction and dry in a constant temperature vacuum oven at 60°C to obtain 3-styrene methyl ether-benzophenone.

[0052] (2) 3-Styrene methyl ether-benzophenone, perfluorooctyl ethyl acrylate, N,N-dimethylaminoethyl methacrylate and styrene in azo The copolymerization reaction of diisobutyl nitrile occurs under thermal initiation at 60°C, reacts for 24 hours, precipitates in ether, and dries in a constant temperature vacuum oven at 40°C to obtain the target product.

[0053] Figure 4 It is the structural diagram of P(F-BP-DEMA-S) synthe...

Embodiment 3

[0055] A fluorinated hydrogen abstraction polymer photoinitiator P (F-TX-DEMA-MMA), the structural formula is as follows:

[0056]

[0057] The preparation method is as follows:

[0058] (1) 1 mole of O-(thioxanthone-[2]-yl)-oxyacetic acid and 1.2 moles of 2-hydroxyethyl methacrylate are dissolved in dichloromethane, ice-water bath, and then add 0.1 mole 4-dimethylaminopyridine and 1 mole of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride as catalyst and dehydrating agent, stirred, and reacted for 24 hours at normal temperature, using a large amount of Precipitate with deionized water, filter with suction, and dry in a constant temperature vacuum oven at 70°C to prepare acrylate containing photoinitiator thioxanthone;

[0059] (2) According to a certain feeding ratio (X:Y:Z:W=2:30:10:10), the photoinitiator-containing thioxanthone acrylate, the co-initiator-containing amine acrylate (methacrylic acid- N,N-Dimethylaminoethyl ester), methyl methacrylate and perf...

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Abstract

The invention discloses a fluorated hydrogen abstracting type macromolecular photoinitiator, and a preparation method and application thereof. The fluorated hydrogen abstracting type macromolecular photoinitiator is obtained by free radical copolymerization of a photoinitiator-containing alkylene monomer, a coinitiator-containing alkylene monomer, a fluorocarbon-chain-containing alkylene monomer and a common alkylene monomer. The fluorated hydrogen abstracting type macromolecular photoinitiator can connect micromolecular coinitiator amine and a photoinitiator to a macromolecular chain, the defects such as proneness to transfer, xanthochromia and poor stability of conventional micromolecular photoinitiators are overcome, and photo-initiation efficiency is improved; surface self-assembly of the fluorated macromolecular photoinitiator can be achieved through ultralow surface energy and ultralow surface tension of fluorine atoms to form a gradient self-assembly layer with concentration gradually reduced from top to bottom, the superficial photoinitiator is enriched relative to a bulk layer and can preferably have photopolymerization to form a film layer capable of preventing oxygen from diffusing to enter a photopolymerization system, and accordingly, good oxidation and polymerization resistance effect is achieved.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, in particular, the invention relates to a fluorinated hydrogen abstraction polymer photoinitiator, a preparation method and an application thereof. Background technique [0002] UV curing technology has been widely used in industrial fields such as coatings, photoresists, inks, electronic packaging materials, and adhesives due to its advantages of fast curing speed, energy saving and environmental protection, and solvent-free. In the photocuring system, the photoinitiator plays a vital role. It can absorb light energy to convert liquid monomers or oligomers and diluents into solid crosslinked polymers. Therefore, research on photoinitiators And development has always occupied a very important position. The traditional small molecule photoinitiator system is easy to volatilize and migrate due to poor compatibility with the photocuring system, which reduces the photopolymerization effici...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F2/48C08F220/22C08F222/24C08F222/22C08F220/14C08F212/08C08F212/32C08F220/34C08F214/18C08F220/56C08F222/20C08F214/06C08F220/30C08F220/18C08F220/44
Inventor 侯鸿浩姜学松印杰林鸿波于静张赛姚继元李瑾张林芝
Owner SHANGHAI JIAOTONG UNIV
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