Terminal alkyne-containing benzophenone derivative and preparation method and application thereof

A technology of dihydroxybenzophenone and benzophenone, which is applied in the field of benzophenone derivatives and its preparation, can solve problems such as limited applications, achieve enhanced light stability, good compatibility, and reduce mobility Effect

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

Due to its toxicity and easy migration, the traditional photoinitiator benzophenone has limited its application in food packaging and biomaterials. Therefore, through rational molecular design and research on the relationship between molecular structure and performance, a highly efficient Photoinitiators with low toxicity and low mobility have great application prospects

Method used

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  • Terminal alkyne-containing benzophenone derivative and preparation method and application thereof
  • Terminal alkyne-containing benzophenone derivative and preparation method and application thereof
  • Terminal alkyne-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 0.207g (1.5mmol) of potassium carbonate to the container, dissolve it with 3ml of N,N-dimethylformamide, and then add 0.205g ( 2 mmol) of 5-chloro-1-pentyne, stirred at 85°C for 12 hours. After the reaction, add water to the reaction solution and extract with ethyl acetate, collect the organic phase, wash with water, dry over anhydrous sodium sulfate, and remove the organic solvent by rotary evaporation; and use petroleum ether and ethyl acetate (volume ratio 4:1) as The eluent is separated by column chromatography to obtain the benzophenone derivative 1 containing the terminal alkyne and the benzophenone derivative 2 containing the terminal alkyne.

[0021] 2-Hydroxy-4-(pent-4-yne-1-oxyl)benzophenone (derivative 1): white solid, yield: 45%, m.p.25-27°C. 1 H NMR (600MHz, CDCl 3 )δ12.72–12.69(m,1H),7.68–7.63(m,2H),7.61–7.56(m,1H),7.54–7.49(m,3H),6.55(d,J=2.5Hz,1H) ,6.43(dt,J=10.2,5.1Hz,1H),4.19–4.14(m,2H),2.08–2.02(m...

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 50g of epoxy propylene carboxylic acid resin, 44g of 1,6-hexanediol diacrylate, 3g of photoinitiator (1173), 2g of triethanolamine, 2-hydroxy-4-(pentane) in the glass container equipped with stirrer - 1g of 4-alkyne-1-oxyl)benzophenone, stirred to make it dispersed uniformly and transparently, and stood still for 5-10 minutes to obtain a transparent 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 0.03g of 2,4-di(pent-4-yn-1-oxyl)benzophenone and 0.5g of modified epoxy acrylate (UV1005-65) into the glass container, 1, 0.45g of 6-hexanediol diacrylate (HDDA), 0.02g of triethanolamine, and stir evenly 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 terminal alkyne-containing benzophenone derivative and a preparation method and application thereof. preparation method of the derivative is as follows: taking 2,4- dihydroxybenzophenone as a raw material, reacting with 5- chloro- 1- pentyne reaction to rapidly synthesize two terminal alkyne-containing benzophenone derivatives 1 and 2. The method has the advantages of simple preparation, mild reaction conditions, high total yield and the like. The derivative 1 can effectively absorb ultraviolet light of 250-360 nm, not only can enhance the light stability of UV-curable coating materials and coatings, but also has the characteristics of good compatibility with resin or monomer, no odor, and the like, and is benefitical to the storage of the UV-curable coating materials. At the same time, the derivative 2 introduces linear terminal alkynyl on the basis of a benzophenone structural skeleton, which can promote the effective crosslinking bonding of the compound to the resin or the monomer, and reduce the mobility of a photolysis by-product. The derivatives synthesized by the preparation method can serve as a UV absorbers and A UV initiators respectively to be applied in photocurable compositions such as coating materials, inks, and adhesives.

Description

technical field [0001] The invention relates to the fields of ultraviolet curing coatings, inks, adhesives and the like, and specifically belongs to a benzophenone derivative containing an alkyne terminal group and a preparation method and application thereof. Background technique [0002] When the polymer material is used outdoors, it is easy to degrade the polymer material when exposed to sunlight, causing gloss reduction, embrittlement, cracking and other phenomena. For this reason, it is necessary to add ultraviolet absorbers to resist ultraviolet light degradation reactions, enhance weather resistance, and provide high More complete protective effect of molecular materials. In particular, UV-curable coatings, printing inks, adhesives, etc. are affected by ultraviolet rays in sunlight during the preparation process and need to be carried out under dark conditions, and the storage time cannot be long, which seriously restricts their development. Commonly used UV absorber...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/71C08F2/48C09D7/63C09D11/03C09D11/38C09J11/06
CPCC07C49/84C08F2/48C09D11/03C09D11/38C09J11/06C09D7/63
Inventor 张变香王晨
Owner SHANXI UNIV
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