Synthesis and Properties of a Novel Ultraviolet Absorber 1, 4-Diaryl-1, 3-butadiyne

doi:10.7517/issn.1674-0475.181206

Abstract

Abstract: In this paper, aryl sulfide containing terminal alkyne was used as raw material, (diacetoxyiodo)benzene was used as oxidant, cuprous chloride was used as catalyst, and 1,4-bis(2-arylthiophenyl)-1,3-butadiyne was synthesized by reaction at room temperature for 30 minutes. The 1,3-butadiyne compound was characterized by ¹HNMR, ¹³CNMR, etc., and its optical properties and application as an ultraviolet absorber in UV-curable coatings were investigated. The results show that the compound can effectively absorb ultraviolet light from 270 nm to 360 nm and has strong absorption intensity and low degree of UV degradation. It has good compatibility with resin, monomer and no odor. At the same time, it does not participate in the curing of free radical systems, which enhances the light stability of coatings and cured coatings, and is beneficial to the storage of UV-curable coatings. It is a kind of ultraviolet light absorber with promising prospects.

Key words: UV absorber, arylthio, 1, 4-diaryl-1, 3-butadiyne, terminal alkyne

WANG Chen, ZHAO Ziren, SHI Heping, TIAN Wenjuan, ZHANG Bianxiang. Synthesis and Properties of a Novel Ultraviolet Absorber 1, 4-Diaryl-1, 3-butadiyne[J]. Imaging Science and Photochemistry, 2019, 37(2): 118-126.

References

[1] Nowicki M, Richter A, Wolf B, Kaczmarek H. Nanoscale mechanical properties of polymers irradiated by UV[J]. Polymer, 2003, 44(21):6599-6606.
[2] Diepens M M, GiJsman P P. Photodegradation of bisphenol a polycarbonate[J]. Polymer Degradation & Stability, 2007, 92(3):397-406.
[3] Calvo M E, Castro Smirnov José R, Míguez Hernán. Novel approaches to flexible visible transparent hybrid films for ultraviolet protection[J]. Journal of Polymer Science Part B:Polymer Physics, 2012, 50(14):945-956.
[4] 万震, 刘嵩, 李克让. 防紫外线织物的最新研究进展[J].印染, 2001, 27(1):42-44. Wan Z, Liu S, Li K R. The latest research progress of UV protection fabrics[J]. Dyeing & Finishing, 2001, 27(1):42-44.
[5] Maria D S, Claramunt R M., Bobosik V, Torralba M C, Torres M R, Alkorta I, Elguero J. Synthesis and structural study of 2-arylbenzotriazoles related to tinuvins[J]. Tetrahedron, 2013, 69(14):3027-3038.
[6] Matsumoto S, Kumasaka R, Yagi M, Kikuchi A. Triplet-triplet energy transfer between UV absorbers in solutions at room temperature[J]. Journal of Photochemistry & Photobiology A:Chemistry, 2017, 346:396-400.
[7] Hao J J, Yang Y. Exploring the ESIPT dynamical processes of two novel chromophores:symmetrical structure CHC and asymmetric structure CHN[J]. Organic Chemistry Frontiers, 2018, 5(8):1330-1341.
[8] Wang X D, Xu Y L, Yang L, Lu X, Zou H, Yang W Q, Zhang Y Y, Li Z C, Ma M L. Synthesis, spectra, and theoretical investigations of 1,3,5-triazines compounds as ultraviolet rays absorber based on time-dependent density functional calculations and three-dimensional quantitative structure-property relationship[J]. Journal of Fluorescence, 2018, 28(2):707-723.
[9] González M. T, Fumagalli F, Benevenuto C. G, Da Silva Emery F, Gaspar L. R. Novel benzophenone-3 derivatives with promising potential as UV filters:relationship between structure, photoprotective potential and phototoxicity[J]. European Journal of Pharmaceutical Sciences, 2017, 101:200-210.
[10] Broniowska Zaneta, Pomierny B, Smaga I, Filip M, Budziszewska B. The effect of UV-filters on the viability of neuroblastoma (SH-SY5Y) cell line[J]. Neuro Toxicology, 2016, 54:44-52.
[11] Wnuk A, Rzemieniec J, Staron J, Litwa E, Lason W, BoJarski A, KaJta M. Prenatal exposure to benzophenone-3 impairs autophagy, disrupts RXRs/PPA rgamma signaling, and alters epigenetic and post-translational statuses in brain neurons[J]. Molecular Neurobiology(In printing).
[12] Nagayoshi H, Kakimoto K, Takagi S, Konishi Y, KaJimura K, Matsuda T. Benzotriazole ultraviolet stabilizers show potent activities as human aryl hydrocarbon receptor ligands[J]. Environmental Science & Technology, 2014, 49(1):578-587.
[13] Chen Y, Ye J S, Li C S, Zhou P L, Liu J, Ou H S. Degradation of 1H-benzotriazole by UV/H₂O₂ and UV/TiO₂:kinetics, mechanisms, products and toxicology[J]. Environmental Science Water Research & Technology, 2018, 4(9):1282-1294.
[14] Chai R D, Chen S J, Zhang J. Combined effect of hindered amine light stabilizer and antioxidants on photodegradation of poly (vinyl chloride)[J]. Journal of Thermoplastic Composite Materials, 2012, 25(7):879-894.
[15] Braveenth R, Ahn D H, Han J H, Moon J S, Kim S W, Lee H, Qiong W, Kwon J H, Chai K Y. Utilizing triazine/pyrimidine acceptor and carbazole-triphenylamine donor based bipolar novel host materials for highly luminescent green phosphorescent OLEDs with lower efficiency roll-off[J]. Dyes and Pigments, 2018, 157:377-384.
[16] 杨坤, 陈鸣才, 许凯, 徐社阳. 含双硫键结构的苯并三唑紫外吸收剂的合成及应用[J]. 精细化工, 2014, 31(8):1005-1008. Yang K, Chen M C, Xu K, Xu S Y. Synthesis and application of UV absorber of benzotriazole compound containing a disulfide bond[J]. Fine Chemicals, 2014, 31(8):1005-1008.
[17] Shun A L K S, Tykwinski R R. Synthesis of naturally occurring polyynes[J]. Angewandte Chemie, 2010, 45(7):1034-1057.
[18] Feng R K, Ning H Q, Su H, Gao Y, Yin H T, Wang Y D, Yang Z, Qi C Z. Selective synthesis of alkynylated isoquinolines and biisoquinolines via Rh(Ⅲ) catalyzed C-H activation/1,3-diyne strategy[J]. The Journal of Organic Chemistry, 2017, 82(19):10408-10417.
[19] Zhang K, Zhang C, He Z H, Huang J, Du X, Wang L, Wei S P, Pu L, Wang Q. Highly enantioselective synthesis and anticancer activities of chiral conjugated diynols[J]. ChemBioChem, 2018, 19(21):2293-2299.
[20] Kitamura T, Zhang B X, FuJiwara Y. Novel[4+2] -cycloaddition of 1-phenyl-1-benzothiophenium salts with dienes. Experimental evidence for a lack of aromaticity in the thiophene ring[J]. Journal of Organic Chemistry, 2003, 68(3):731-735.