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Fluorine-containing benzophenone derivative and preparation method and application thereof

A technology of benzophenone and dihydroxybenzophenone, applied in the field of fluorine-containing benzophenone derivatives and its preparation, can solve problems such as easy yellowing of cured film, achieve inhibition of oxygen inhibition, enhance Good photostability and compatibility

Inactive Publication Date: 2019-09-27
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, during the curing process, the phenomenon of oxygen inhibition is obvious, and there are easy-to-migrate curing by-derivatives, and the cured film is easy to yellow.

Method used

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  • Fluorine-containing benzophenone derivative and preparation method and application thereof
  • Fluorine-containing benzophenone derivative and preparation method and application thereof
  • Fluorine-containing benzophenone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 0.214g (1mmol) of 2,4-dihydroxybenzophenone and 0.150g (1.5mmol) of triethylamine to the container, dissolve it with 3ml of dichloromethane, and slowly add 0.388g (2mmol) under ice-water bath conditions. ) of 3,4,5-trifluorobenzoyl chloride, stirred for 12 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, wash with water after collecting the organic phase, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether and ethyl acetate (volume ratio 5:1) as The eluent is separated by a chromatographic silica gel column to obtain derivative 1 and derivative 2.

[0021] 2-Hydroxy-4-(3,4,5-trifluorobenzoyloxy)benzophenone (derivative 1): white solid, yield: 45%, m.p.25-27°C. 1 H NMR (600MHz, CDCl 3 )δ12.33(s,1H),7.88(t,J=7.0Hz,2H),7.75–7.69(m,3H),7.64(t,J=7.5Hz,1H),7.55(t,J=7.7 Hz,2H),6.97(d,J=2.3Hz,1H),6.78(dd,J=8.8,2.3Hz,1H). 13 C NMR (151MHz, CDCl 3 )δ200.78,164.86,161...

Embodiment 2

[0025] Embodiment 2: Derivative 1 is used in the performance evaluation of ultraviolet absorber

[0026] Experimental recipe:

[0027]

[0028] Working conditions:

[0029] Add epoxy propylene carboxylic acid resin 50g, 1,6-hexanediol diacrylate 44g, photoinitiator (1173) 3g, triethanolamine 2g, 2-hydroxyl-4-(3) in the glass container that stirrer is housed , 1g of 4,5-trifluorobenzoyloxy)benzophenone, stirred to make it dispersed evenly and transparently, and stood still for 5-10 minutes to obtain a transparent free radical photocurable coating. The paint is divided into three parts, one part is put into a transparent glass bottle and covered for daily indoor storage; the other part is put into a transparent glass bottle and covered with a cover for indoor dark storage; one part is coated on a glass plate with a brush, and the film The thickness is 75 μm, and then cured by a UV curing instrument at a speed of 5 meters per minute (about 5 seconds of light time).

Embodiment 3

[0054] Embodiment 3: Applied performance evaluation of derivative 2

[0055] Experimental formula:

[0056]

[0057] working conditions

[0058] Under the condition of avoiding light, add 20.03g of 2,4-bis(3,4,5-trifluorobenzoyloxy)benzophenone and 0.5g of modified epoxy acrylate (UV1005-65) into the glass container , 0.45g of 1,6-hexanediol diacrylate (HDDA), 0.02g of triethanolamine, stir well until the coating liquid becomes transparent. The mixture was coated on a glass plate with an applicator to form a film with a film thickness of 75um. It was irradiated and cured in a medium-pressure mercury lamp, and the power of the mercury lamp was 400W.

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Abstract

The invention provides a fluorine-containing benzophenone derivative and a preparation method and application thereof. preparation method of the derivative is as follows: taking 2,4- Dihydroxybenzophenone as raw material with 3,4,5-Two fluorine-containing benzophenone derivatives 1 and 2 were synthesized by the reaction of trifluorobenzoyl chloride. The invention has the advantages of simple preparation, mild reaction and high yield. Derivative 1 can effectively absorb ultraviolet light of 250-360nm, which not only enhances the light stability of UV-curable coatings and coatings, but also has good compatibility with resin or monomer, and has no odor. It is also beneficial to ultraviolet light. Storage of cured coatings. The derivative 2 introduces a fluorine atom on the basis of the benzophenone structural skeleton, and can utilize low surface chemical energy of the fluorine atom to enrich the compound to a surface and accelerate surface polymerization, thereby suppressing an oxygen inhibition phenomenon. The two derivatives synthesized by the present invention can be used as an ultraviolet light absorber and an ultraviolet light initiator, respectively, in the field of photocurable compositions such as paints, inks, adhesives and the like.

Description

technical field [0001] The invention relates to a benzophenone derivative, in particular to a fluorine-containing benzophenone derivative and a preparation method and application thereof. Background technique [0002] When daily decorative materials such as organic films, paints, and plastic products are used outdoors, these polymer materials are likely to be degraded by sunlight, resulting in reduced gloss, brittleness, and cracks. Therefore, it is necessary to add UV absorbers to reduce UV rays. Deterioration reaction, enhanced weather resistance, and provide more complete protection performance. The ultraviolet absorber is mainly composed of a structure containing a π-conjugated system in the molecule. It uses its specific structure to absorb ultraviolet rays and release or consume the energy in the form of heat or harmless low-energy radiation. Commonly used ultraviolet absorbers include benzophenone, Benzotriazoles and triazines are classified into three categories. B...

Claims

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Application Information

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IPC IPC(8): C07C69/76C07C67/14C09D5/32C08F2/48
CPCC07C69/76C09D5/32C08F2/48
Inventor 张变香王晨闫光红
Owner SHANXI UNIV
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