Squaric acid dye/hexaarylbiimidazole complex capable of being used for visible photosensitive system

A technology of hexaarylbisimidazole and compound, which is applied in the field of new compound initiators for visible photosensitive polymerization, and achieves the effect of high reaction efficiency

Inactive Publication Date: 2010-02-10
ANHUI XOANONS CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, HABI has strong absorption in the ultraviolet region of 255nm to 275nm, and weak absorption in the region above 300nm. Therefore, the decomposition of this compound requires ultraviolet light irradiation. If there is no suitable photosensitizer, it is impossible to generate free radicals under the irradiation of visible light. initiate monomer polymerization

Method used

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  • Squaric acid dye/hexaarylbiimidazole complex capable of being used for visible photosensitive system
  • Squaric acid dye/hexaarylbiimidazole complex capable of being used for visible photosensitive system
  • Squaric acid dye/hexaarylbiimidazole complex capable of being used for visible photosensitive system

Examples

Experimental program
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Effect test

Embodiment 1

[0058] Synthesis of squarylium dye SQ-1 (1,3 bis(p-N,N-trimethylaniline)) squarylium

[0059] N,N-Dimethylaniline 10g (83mmol) squaraine 5g (44mmol) n-butanol 200ml, toluene 200ml reflux dehydration, reacted for 6 hours to produce a blue lake, after drying the product 4.5g yield 31%. The product is identified by infrared spectrum, ultraviolet spectrum, hydrogen nuclear magnetic resonance spectrum and mass spectrum.

Embodiment 2

[0061] Synthesis of squaraine dye SQ-7 (1,3 bis((1-methyl-2,3,3 trimethylindoline)-methylene) squaraine

[0062] (1) Synthesis of 2,3,3-trimethylindoline

[0063] Add 10ml of phenylhydrazine and 11ml of methyl isopropyl ketone, 150ml of absolute ethanol and 10ml of concentrated sulfuric acid in a 250ml three-necked flask, stir and reflux for 10 hours under nitrogen protection, after removing ethanol, the residue is neutralized with sodium carbonate solution, Separate the organic layer, extract the aqueous layer three times with 30ml ether, combine with the organic layer, dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation, and distill under reduced pressure under the protection of nitrogen to collect the fraction at 88-92°C / 3mmHg. Yield 50%.

[0064] (2) Synthesis of 2,3,3-trimethylindoline methyl iodide salt

[0065] Add 4g of 2,3,3-trimethylindoline, 4ml of methyl iodide and 10ml of chloroform into a 100ml three-necked flask, stir and reflux for ...

Embodiment 3

[0069] Synthesis of squaraine dye SQ-8 (1,3 bis((1-methyl-benzothiazolyl)-methylene) squaraine

[0070] (1) Synthesis of N-methylbenzothiazole iodine salt

[0071] In a 100ml round bottom flask, add 12.7ml of benzothiazole, 12.5ml of iodomethane, 20ml of ethanol, install a condenser, stir in an oil bath, and reflux for 7 hours (oil bath temperature 65-70°C). The reaction was stopped and cooled to room temperature, filtered and dried to obtain 12.5 g of white powder with a yield of 45%.

[0072] (2) Synthesis of SQ-8

[0073] In a 250ml round bottom flask, add 1.0g of squaraine, 6g of N-methylbenzothiazole iodine salt, 96ml of n-butanol, 24ml of benzene, 3ml of quinoline, install a water separator, and put it on the water separator to condense Tube, oil bath, stirring, reflux (oil bath temperature 110-120° C.), and maintain the reaction for 15 hours. After the reaction was stopped, it was cooled to room temperature, left to stand overnight and then filtered. The product was ...

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Abstract

The invention belongs to the field of photosensitive polymer materials, in particular relates to a squaric acid dye (I) hexaarylbiimidazole (II) complex as a novel composite initiator for visible photosensitive polymerization and applications thereof. The complex is formed by electrostatic interaction and dipolar interaction of the squaric acid dye (I) and the hexaarylbiimidazole (II) in a solventunder the condition that the weight of the hexaarylbiimidazole is 1-10 times of the weight of the squaric acid dye. The squaric acid dye / hexaarylbiimidazole complex can be used as an initiator of visible light polymerization for vinyl monomers, or can be used as an initiator of visible light curing for light-curing coating materials, photoetching materials, light imaging materials, hologram recording materials, optical materials and three-dimensional molding materials.

Description

Technical field: [0001] The invention belongs to the field of photosensitive polymer materials, and in particular relates to a novel composite initiator for visible photosensitive polymerization, which is composed of squarylium dye / hexaaryl bis-imidazole composite. Background technique: [0002] In recent years, with the rapid development and wide application of laser technology, the development of polymer materials sensitive to visible light has become an important research field, and the research on high-efficiency and high-stability photosensitive trigger systems for visible light has become the key. At present, the dye sensitization system is a promising research object, and there have been many patent reports. But to achieve the goal of high efficiency and practicality, there are still some important problems to be solved. [0003] Squaric acid dyes are an important class of functional dyes with many excellent properties. First of all, like merocyanine dyes, it has ve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F2/48C08F2/50G03F7/028
Inventor 戈国平
Owner ANHUI XOANONS CHEM
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