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Research on Chemical Intermediates

, Volume 42, Issue 4, pp 2909–2918 | Cite as

Synthesis, characterization, and crystal structure of modified benzophenone UV-absorber containing reactive group

  • Yun Shen
  • Jianhua Zhu
  • Hongxia Chen
  • Dan Huang
Article
  • 195 Downloads

Abstract

A modified benzophenone UV-absorber containing reactive group (4-(4,6-dichloro-1,3,5-triazin-2-yloxy)-2-hydroxyphenyl)phenyl)methanone (UV-DTHM) has been prepared in good yield from the nucleophilic substitution reaction of 2,4-dihydroxy benzophenone with 2,4,6-trichlorotriazine, catalyzed by 1.3 equiv. NaOH. The most favorable reaction conditions (the catalyst dosage, the mole ratio of the reactants, and reactive time) were selected. The compound was characterized by IR spectroscopy, 1H NMR, 13C NMR, mass spectrometry, elemental analysis, and single crystal X-ray diffraction. The crystal monoclinic, space group C c with the unit cell parameters a = 3.987(2), b = 30.688(16), c = 12.423(6) Å and α = 90.00, β = 92.117(15), γ = 90.00º, Z = 4, R = 0.0620. wR(F 2) = 0.1589. The crystal structure reveals that 2,4,6-trichlorotriazine is boned to 4-seat hydroxyl of 2,4-dihydroxy benzophenone and a intramolecular hydrogen bond is formed with hydrogen of 2-hydroxyl and oxygen of carbonyl group. Moreover, thermogravimetric analysis (TGA) of UV-DTHM was studied, showing two distinct endothermic peaks at temperatures of 281.5 and 358.5 °C. The molar absorption coefficient of UV-DTHM is 1.6 × 104 and 6.3 × 103 at 268 and 330 nm, respectively, and shows excellent ultraviolet absorption property.

Keywords

UV absorber Synthesis X-ray structure (4-(4,6-Dichloro-1,3,5-triazin-2-yloxy)-2-hydroxyphenyl)phenyl)methanone 

Notes

Acknowledgments

We are grateful for the support of the Open Project Program (KJS1007) of Key Lab. of Organic Synthesis (Soochow University) of Jiangsu Province.

Supplementary material

11164_2015_2186_MOESM1_ESM.pdf (42 kb)
Supplementary material 1 (PDF 41 kb)
11164_2015_2186_MOESM2_ESM.pdf (53 kb)
Supplementary material 2 (PDF 53 kb)

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Copyright information

© Springer Science+Business Media Dordrecht 2015

Authors and Affiliations

  • Yun Shen
    • 1
    • 4
  • Jianhua Zhu
    • 2
  • Hongxia Chen
    • 3
  • Dan Huang
    • 1
    • 4
  1. 1.Key Laboratory of Eco-Textile (Jiangnan University) of Ministry of EducationWuxiChina
  2. 2.Yancheng Institute of Health SciencesCollege of PharmaceuticalsYanchenChina
  3. 3.Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials ScienceSoochow UniversitySuzhouChina
  4. 4.College of Textiles and ClothingJiangnan UniversityWuxiChina

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