硅氧烷改性香豆素荧光增白剂的合成与性能
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摘要
采用Pechmann法,以间苯二酚和乙酰乙酸乙酯为原料合成7-羟基-4-甲基香豆素,在三聚氯氰的交联作用下,通过亲核取代反应将7-羟基-4-甲基香豆素、牛磺酸与3-氨基丙基三甲氧基硅烷(KH540)引入到同一分子中,经水解得到新型硅氧烷改性香豆素荧光增白剂.采用红外光谱与XPS分析对产物进行结构表征,通过紫外光谱和荧光光谱对其光学性能进行分析,并通过紫外加速老化实验考察合成产物对纸张的返黄抑制效果.结果表明,纸张涂布在相同用量为0.8%,初始白度比经过传统7-羟基-4-甲基香豆素处理的纸张增加了7.83%ISO,且经过36h的紫外光照射后,发现目标产物有更好的抑制纸张返黄的作用.
The 7-hydroxy-4-methylcoumarin was synthesized from resorcinol and ethyl acetoacetate under the Pechmann method.Then with cyanuric chloride as a crosslinking monomer,7-hydroxy-4-methylcoumarin,3-aminopropyltrimethoxysilane(KH540)and taurine were introduced into the same molecule by nucleophilic substitution method.A new silicone modified coumarin fluorescent brightener was obtained by hydrolysis.The molecular structures were characterized by IR spectra and XPS analysis.The analysis of optical properties was studied by UV-vis spectra and fluorescence spectroscopy,and its anti-yellowing effect was evaluated by ultraviolet accelerated aging experiment.The results show that the paper was coated at the same amount of 0.8%,and the initial whiteness was increased by 7.83%ISO compared with the paper treated with the traditional 7-hydroxy-4-methylcoumarin.After aging for 36 h,it was found that the target product has a better effect of inhibiting the yellowing of paper.
The 7-hydroxy-4-methylcoumarin was synthesized from resorcinol and ethyl acetoacetate under the Pechmann method.Then with cyanuric chloride as a crosslinking monomer,7-hydroxy-4-methylcoumarin,3-aminopropyltrimethoxysilane(KH540)and taurine were introduced into the same molecule by nucleophilic substitution method.A new silicone modified coumarin fluorescent brightener was obtained by hydrolysis.The molecular structures were characterized by IR spectra and XPS analysis.The analysis of optical properties was studied by UV-vis spectra and fluorescence spectroscopy,and its anti-yellowing effect was evaluated by ultraviolet accelerated aging experiment.The results show that the paper was coated at the same amount of 0.8%,and the initial whiteness was increased by 7.83%ISO compared with the paper treated with the traditional 7-hydroxy-4-methylcoumarin.After aging for 36 h,it was found that the target product has a better effect of inhibiting the yellowing of paper.
引文
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[2]林本平,王双飞.高得率浆光诱导返黄机理及其抑制技术的研究进展[J].中国造纸学报,2007,22(1):92-98.
[3]Ni Yonghao,He Zhibin,Zhang Hongjie,et al.Characteristics of high yield pulp and its effect on some typical wetend issues[J].Journal of Biobased Materials&Bioenergy,2011,5(2):181-186.
[4]房桂干,沈兆邦,黄德裕.发展高得率浆生产是保证我国造纸工业可持续发展的重要途径之一[J].林产化工通讯,2000,34(4):29-31.
[5]张红杰,胡惠仁.高得率浆光致返黄及荧光增白剂对返黄的抑制作用[J].纸和造纸,2007,26(6):50-53.
[6]Christie R M.Pigments,dyes and fluorescent brightening agents for plastics:An overview[J].Polymer International,2010,34(4):351-361.
[7]Murray S G.Dyes and fluorescent whitening agents for paper[M].Berlin:Springer Netherlands,1991:132-161.
[8]梁晓燕,霍景沛,胡晓洪,等.二苯乙烯苯型荧光增白剂的研究进展[J].化学推进剂与高分子材料,2018,16(2):14-20.
[9]赵同丰,赵德丰,于华云,等.1,8-萘酰亚胺类荧光材料的进展[J].染料工业,1997,34(1):10-17.
[10]韩文强.罗丹明和香豆素类金属离子荧光探针的合成及光谱性能研究[D].南昌:南昌大学,2017.
[11]扈靖.香豆素类金属离子探针的设计、合成及性能研究[D].天津:天津大学,2008.
[12]郑玲,赵挺,孙立新.香豆素类化合物的药理活性和药代动力学研究进展[J].时珍国医国药,2013,24(3):714-717.
[13]史晨燕.香豆素类化合物的合成及其抗菌活性[D].杨凌:西北农林科技大学,2018.
[14]王鹏,张光华,付小龙,等.基于香豆素型荧光增白剂的返黄抑制剂的合成与性能[J].精细化工,2013,30(3):333-338.
[15]Yu Tianzhi,Zhang Peng,Zhao Yuling,et al.Synthesis,characterization and high-efficiency blue electroluminescence based on coumarin derivatives of 7-diethylaminocoumarin-3-carboxamide[J].Organic Electronics,2009,10(4):653-660.
[16]Xu Longhe,Zhang Yanying,Wang Xinliang,et al.Synthesis of styryl coumarins from coumarin diazonium salts and studies on their spectra characteristics[J].Dyes&Pigments,2004,62(3):283-289.
[17]郭明媛,张光华,王子儒.香豆素修饰的碳量子点光稳定剂的制备与性能[J].精细化工,2018,35(11):1 948-1 955,1973.
[18]Zhang Guanghua,Zheng Hua,Guo Mingyuan,et al.Synthesis of polymeric fluorescent brightener based on coumarin and its performances on paper as light stabilizer,fluorescent brightener and surface sizing agent[J].Applied Surface Science,2016,367:167-173.
[19]陈珂然,杨扬,李萍,等.氨基硅烷偶联剂强化纸质文物研究[J].广东化工,2017,44(1):11-13,22.