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Polymerizable thioxanthone water-based photoinitiator as well as preparation method and application thereof

A thioxanthone water-based and xanthone-based water-based technology is applied in the field of thioxanthone water-based photoinitiators and their preparation, which can solve the problems of low curing efficiency and high cost of raw materials, achieve high curing degree and overcome oxygen inhibition of polymerization. , the effect of high light-induced efficiency

Active Publication Date: 2022-05-31
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing water-based photoinitiators generally only play the role of light-induced free radical polymerization in the process of initiating the polymerization of acrylate monomers, so in the first stage, amines need to be specially added as nucleophiles and bases, and in the second stage Adding PI in stages, not only the cost of raw materials is high, but also the curing efficiency is low

Method used

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  • Polymerizable thioxanthone water-based photoinitiator as well as preparation method and application thereof
  • Polymerizable thioxanthone water-based photoinitiator as well as preparation method and application thereof
  • Polymerizable thioxanthone water-based photoinitiator as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A kind of preparation method of thioxanthone aqueous photoinitiator comprises the steps:

[0063] (1) Mix N,N'-methylenebisacrylamide (2.6mmol) and 1,4-diaminobutane (2.9mmol), N,N'-methylenebisacrylamide and 1,4-bisacrylamide The molar ratio of aminobutane was 1:1.1, dissolved in methanol (1.5 mL), and stirred at 40°C for 12 hours. The pure polymer is then isolated by precipitation into diethyl ether and filtered and dried under vacuum to yield the polyaminoamine.

[0064] (2) Polyaminoamine (0.1g, 0.02mmol) and acrylate-functionalized thioxanthone (TXA) (0.028g, 0.01mmol) were dissolved in methanol (2.5mL), stirred at 70°C under nitrogen for 48 Hour. When the reacted solution was added to 10 mL of diethyl ether, the pure polymer was isolated as an orange solid with a yield of 50%.

[0065] (3) The product of step (2) (0.015 g, 0.055 mmol) and tetraethyl vinylidene diphosphonate (0.05 g, 0.166 mmol) were stirred in chloroform (0.5 mL) for 48 h at room temperature. ...

Embodiment 2

[0070] A preparation method of thioxanthone aqueous photoinitiator, the difference from Example 1 is: increase the molar weight of 1,4-diaminobutane to 3.4mmol, so that N,N'-methylene bis The molar ratio of acrylamide and 1,4-diaminobutane becomes 1:1.3.

[0071] Specifically include the following steps:

[0072] (1) N,N'-methylenebisacrylamide (2.6 mmol) and 1,4-diaminobutane (3.4 mmol) were dissolved in methanol (1.5 mL), and stirred at 40° C. for 12 hours. The pure polymer is then isolated by precipitation into diethyl ether and filtered and dried under vacuum to yield the polyaminoamine.

[0073] (2) Polyaminoamine (0.1g, 0.02mmol) and acrylate-functionalized thioxanthone (TXA) (0.028g, 0.01mmol) were dissolved in methanol (2.5mL), stirred at 70°C under nitrogen for 48 Hour. When this solution was added to excess diethyl ether, the pure polymer was isolated as an orange solid in 50% yield.

[0074] (3) The product of step (2) (0.015 g, 0.055 mmol) and tetraethyl vinyli...

Embodiment 3

[0076] A preparation method of a thioxanthone aqueous photoinitiator, the difference from Example 1 is: N, N'-methylenebisacrylamide is replaced by 1,6-hexanediol diol in an equimolar amount Acrylate.

[0077] Specifically include the following steps:

[0078] (1) 1,6-Hexanediol diacrylate (2.6 mmol) and 1,4-diaminobutane (2.9 mmol) were dissolved in methanol (1.5 mL), and stirred at 40° C. for 12 hours. The pure polymer is then isolated by precipitation into diethyl ether and filtered and dried under vacuum to yield the polyaminoamine.

[0079] (2) Polyaminoamine (0.1g, 0.02mmol) and acrylate-functionalized thioxanthone (TXA) (0.028g, 0.01mmol) were dissolved in methanol (2.5mL), stirred at 70°C under nitrogen for 48 Hour. When this solution was added to excess diethyl ether, the pure polymer was isolated as an orange solid in 50% yield.

[0080] (3) The product of step (2) (0.015 g, 0.055 mmol) and tetraethyl vinylidene diphosphonate (0.05 g, 0.166 mmol) were stirred in ...

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Abstract

The invention belongs to the technical field of high polymer materials, and particularly relates to a polymerizable thioxanthone water-based photoinitiator and a preparation method and application thereof, and the polymerizable thioxanthone water-based photoinitiator contains a polyaminoamine structural unit, a thioxanthone structural unit and a phosphoric acid structural unit, the thioxanthone structural unit and the phosphoric acid structural unit are randomly connected with N in the polyaminoamine structural unit. According to the thioxanthone water-based photoinitiator, linear polyaminoamine serves as a macromolecular main chain, linear polyamide, a phosphate group, thioxanthone and an amine structure are contained on the macromolecular main chain at the same time, the number of curing sites is larger, and the curing degree is higher. Moreover, the thioxanthone water-based photoinitiator can participate in two stages of a one-pot dual-curing process in an acrylic acid group / methacrylic acid group UV photocuring system, not only can be used as a nucleophilic reagent and alkali in a first-stage reaction, but also can induce free radical polymerization in a second-stage reaction.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a polymerizable thioxanthone aqueous photoinitiator and its preparation method and application. Background technique [0002] Photoinitiators (PI) play an important role in photopolymerization. For traditional small-molecule PIs, photolytic fragments or residual PIs easily migrate to the surface of final products, causing odor or toxicity issues, which limit their applications in food packaging and biomedical materials. Polymeric photoinitiators are attracting attention due to some advantages brought about by their macromolecular nature, in particular, polymeric photoinitiators can reduce the migration of the film surface, thereby reducing the tendency of yellowing, and reducing odor and toxicity problems . These advantages arise from the fact that the production / release of easily migratory molecules is minimized. Since water is a green solvent with no emissions of v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C08F2/48C08F283/06C08F220/20C09J151/08
CPCC08G73/02C08F2/48C08F283/065C09J151/08C08F220/20
Inventor 冯一凡张倩芝卓文珊王小妹冯瑞琪
Owner SUN YAT SEN UNIV
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