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Acyl phosphine oxygen compound containing sulfydryl substituent group and photoinitiator containing compound

A technology of acyl phosphine oxide and compound, which is applied in the field of new UV light radiation free radical polymerization materials, and can solve the problems of poor surface curing effect, low activity of peroxide free radicals, and significant effect.

Inactive Publication Date: 2013-06-05
SHENZHEN UV-CHEMTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But, the defect of this type of compound is equally remarkable, and it is outstanding to reflect that its Surface-Curing (Surface-Curing) effect is generally not good enough, so often must and other types of photoinitiators, such as hydroxyketone type photoinitiators, in practical applications, compound use
Since the photoinitiator is a small molecular compound with considerable economic value, such a compound photoinitiator system not only increases the cost, but also significantly increases the total release of various photochemically cracked fragment molecules and volatile organic compounds (Volatile OrganicCompounds). Therefore, the hidden dangers of environmental and health risks are prominent, and the latter is what the new generation of light curing technology is trying to avoid, and is facing increasingly stringent laws and regulations
[0003] On the other hand, studies have shown that the phosphine oxide free radicals produced during the photocleavage process of acylphosphine oxide compounds are easily quenched by oxygen molecules to produce low-activity peroxide free radicals, so the adverse effect of oxygen resistance is significant

Method used

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  • Acyl phosphine oxygen compound containing sulfydryl substituent group and photoinitiator containing compound
  • Acyl phosphine oxygen compound containing sulfydryl substituent group and photoinitiator containing compound
  • Acyl phosphine oxygen compound containing sulfydryl substituent group and photoinitiator containing compound

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Experimental program
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Effect test

Embodiment 1

[0028] Embodiment 1 (synthetic method of building blocks containing mercapto groups):

[0029]

[0030] Under nitrogen protection, 4.2 grams of phenylethoxyphosphine chloride (prepared with reference to literature procedure Tetrahedron, 2009, 65, 9973-9982) was placed in 60 ml of freshly distilled tetrahydrofuran solvent, and 4.4 grams of acetic acid (2-hydroxyl phenylthioester) and 3.6 milliliters of dry triethylamine, the mixture was stirred at room temperature for 4 hours and then evaporated to remove most of the solvent, the residue was diluted with 100 milliliters of dichloromethane and washed once with equal volume of water and saturated brine, and the organic phase was Dry with sodium sulfate, filter, concentrate and remove the solvent, mix the residue with 100 ml of toluene, add 4.4 g of mesitluoyl chloride, the reaction releases methyl chloride gas, react for 8 hours and filter the reaction solution with diatomaceous earth, filter the cake with a small amount of Wa...

Embodiment 2

[0032] Embodiment two (mercapto substitution synthetic method):

[0033]

[0034] The first step: under nitrogen protection, 100 ml of ethylene glycol dimethyl ether solution containing 0.05 mole of bis-tritoluoyl sodium phosphide prepared by referring to the literature procedure (WO2006 / 056541A1) was cooled to zero degree, and 4.4 g of Propylene oxide and 50 ml of anhydrous N,N-dimethylformamide were sealed and heated at 60°C for 2 hours. The reaction solution was quenched with 8 milliliters of saturated ammonium chloride aqueous solution and then concentrated under reduced pressure. The residual yellow viscous liquid was mixed with 80 milliliters of toluene, and 25 milliliters of an aqueous solution with a pH of 2-3 was added, and then 7.5 milliliters of H 2 o 2 30% aqueous solution, after dripping, keep warm at 60 degrees Celsius for 2 hours. The reaction solution was poured into 250 ml of saturated brine, the organic phase was separated, dried over magnesium sulfate, ...

Embodiment 3

[0038] Prepare radiation curing test samples according to the following weight percentages: 30 parts: epoxy acrylate; 35 parts: polyester acrylate; 5 parts: hexanediol diacrylate; 3 parts: pentaerythritol triacrylate; 23 parts: titanium dioxide Pigment; 4 parts: Example photoinitiator compound.

[0039] Take part of the above mixture and grind it evenly, spray it on the white substrate, and form a coating of about 20 microns in the air. A 250W high-pressure mercury lamp was used as the light source to irradiate at a distance of 12 cm from the sample. Finger pressure scraping method to determine the complete curing of the coating. Compounds 1 and 2 of the above-mentioned examples both initiate the curing of the film layer completely, showing good photosensitive initiation performance.

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PUM

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Abstract

The invention relates to the technical field of ultraviolet (UV) optical radiation free radical polymerization new materials, in particular to an acyl phosphine oxygen compound containing a sulfydryl substituent group with a structural general formula (I) as follows. The acyl phosphine oxygen compound containing the sulfydryl substituent group serves as an unsaturated compound containing olefinic bonds system to carry out the functions of a UV free radical photopolymerization curing photoinitiator. The invention further relates to a UV free radical photopolymerization curing material system containing the compound. At least one of a R1 substituent group, a R2 substituent group and a R3 substituent group of the general formula (I) compound is necessary to contain at least one sulfydryl.

Description

【Technical field】 [0001] The present invention relates to the technical field of UV light radiation free radical polymerization new materials, in particular to the acyl phosphine oxide compound containing mercapto substituents as shown in the general structural formula (I), which is used as an ethylenically unsaturated compound system for UV free radical photopolymerization Use of the cured photoinitiator, and a UV radical photopolymerization curable material system containing the compound. R of the compound of general formula (I) 1 , R 2 , or R 3 At least one of the substituents must contain at least one mercapto group. 【Background technique】 [0002] Some acylphosphine oxide compounds are important photoinitiators in the field of UV and / or electron beam radiation curing, which have been quite abundantly disclosed in patent literature, such as US5218009, EP0615980A2, and CN1659175A, etc. This type of compound is characterized by long-wave light absorption and photobleac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/32C07F9/53C08F2/48C08F2/54C09D167/06C09D163/10C09D7/12
Inventor 王智刚王衍超宋怀海
Owner SHENZHEN UV-CHEMTECH CO LTD
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