含二苯甲酮的香豆素型光稳定剂的合成及应用
|
摘要
以对甲苯磺酸为酸性催化剂,使间苯二酚和乙酰乙酸乙酯发生脱水缩合反应,合成了具有紫外线吸收性能的7-羟基-4-甲基香豆素。通过三聚氯氰,将7-羟基-4-甲基香豆素和紫外线吸收剂2,4-二羟基-二苯甲酮引入同一分子中,再引入水溶性分子牛磺酸,合成了含二苯甲酮的香豆素型光稳定剂。采用红外光谱和核磁共振氢谱等手段对合成物质进行了结构表征,运用紫外光谱、荧光光谱测试其光学性质,并通过紫外光加速老化实验考察了合成产物对高得率浆纸张的抗紫外光老化效果。结果表明,在各自的最佳用量下,经48 h光老化处理,合成的香豆素型光稳定剂对纸张的光老化抑制效果优于单一的反应型紫外吸收剂及传统的荧光增白剂,白度分别少下降了2.14%ISO和3.13%ISO。
With p-toluenesulfonic acid as acidic catalyst,employing resorcinol and ethyl acetoacetate,7-hydroxy-4-methyl coumarin with UV absorption properties was synthesized through dehydration condensation reaction. A coumarin light stabilizer which contains the structure of benzophenone was synthesized by introducing 7-hydroxy-4-methyl coumarin,ultraviolet absorber 2,4-dihydroxybenzophenone and taurine into the same molecule through the medium of cyanuric chloride. The molecular structures were characterized by means of IR spectra and1HNMR,the optical properties were measured by UV spectra and fluorescence spectra,and,with the target product used as the surface sizing agent on handsheet of high yield pulps,the effect of anti-UV aging was evaluated using the ultraviolet aging apparatus. The results show that,with the optimal dosage,the coumarin light stabilizer was superior to reactive UV-stabilizer or the conventional fluorescent brighteners in terms of the effect of anti-UV aging,and the declining brightness of handsheet relative to them were 2. 14% ISO and 3. 13% ISO respectively.
With p-toluenesulfonic acid as acidic catalyst,employing resorcinol and ethyl acetoacetate,7-hydroxy-4-methyl coumarin with UV absorption properties was synthesized through dehydration condensation reaction. A coumarin light stabilizer which contains the structure of benzophenone was synthesized by introducing 7-hydroxy-4-methyl coumarin,ultraviolet absorber 2,4-dihydroxybenzophenone and taurine into the same molecule through the medium of cyanuric chloride. The molecular structures were characterized by means of IR spectra and1HNMR,the optical properties were measured by UV spectra and fluorescence spectra,and,with the target product used as the surface sizing agent on handsheet of high yield pulps,the effect of anti-UV aging was evaluated using the ultraviolet aging apparatus. The results show that,with the optimal dosage,the coumarin light stabilizer was superior to reactive UV-stabilizer or the conventional fluorescent brighteners in terms of the effect of anti-UV aging,and the declining brightness of handsheet relative to them were 2. 14% ISO and 3. 13% ISO respectively.
引文
[1]张光华,郭锦鸽,徐海龙,等.基于萘酰亚胺荧光增白剂的返黄抑制剂的合成及应用[J].中国造纸学报,2012,27(2):29-34.
[2]宋丹梅,郭媛,陆振欢,等.香豆素类荧光化合物的合成及表征[J].精细化工,2009,26(6):616-619.
[3]Maksim V Sednev,Christian A Wurm,Vladimir N Belov,et al.Carborhodol:a new hybrid fluorophore obtained by combination of fluorescein and carbopyronine dye cores[J].Bioconjugate Chem,2013,24(4):690-700.
[4]J Tyler Simmons,John R Allen,Deborah R Morris,et al.Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(Ⅱ)ions:thermodynamic and kinetic evaluations[J].Inorg Chem A April 26,2013,52(10):5838-5850..
[5]张光华,徐海龙,郭锦鸽,等.基于二苯乙烯荧光增白型返黄抑制剂的合成及应用[J].精细化工,2012,29(7):705-711.
[6]张跃华,张其平,石文艳,等.1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J].发光学报,2011,32(5):505-513.
[7]陈杰,贺英,潘照东,等.主链含萘酰亚胺的聚芳醚型聚合物的合成及其光电性能[J].发光学报,2012,33(3):705-711.
[8]唐小东,黄昆.7-羟基-4-甲基香豆素的合成工艺探究[D].达州:四川文理学院,2012.
[9]Atkins R L,Bliss D E.Substituted coumarins and azacoumarins.Synthesis and fluorescent properties[J].J Org Chem,1978,43(10):1974.
[10]赵义,淡宜.反应型紫外线吸收剂的制备及高分子化[J].高分子材料科学与工程,2006,22(5):74-77.
[11]董传明,舒雪桂,曾涛,等.受阻胺类光稳定剂Chimassorb2020的合成[J].精细化工,2005,22(6):468-471,474.
[12]昝帅,姜文凤,邵玉昌.三嗪型紫外线吸收剂的合成及性能[J].精细化工,2007,24(11):1106-1108.
[13]张红杰,胡惠仁,何志斌,等.利用荧光增白剂改善高得率浆的光学性能[J].中国造纸,2010,29(9):1-6.
[14]张锐.新型返黄抑制剂的合成及其在高得率竹浆中应用的研究[D].南宁:广西大学,2008.
[15]魏永巨,李娜,秦身钧.磺基水杨酸的荧光光谱与荧光量子产率[J].光谱学与光谱分析,2004,24(6):647-651.
[2]宋丹梅,郭媛,陆振欢,等.香豆素类荧光化合物的合成及表征[J].精细化工,2009,26(6):616-619.
[3]Maksim V Sednev,Christian A Wurm,Vladimir N Belov,et al.Carborhodol:a new hybrid fluorophore obtained by combination of fluorescein and carbopyronine dye cores[J].Bioconjugate Chem,2013,24(4):690-700.
[4]J Tyler Simmons,John R Allen,Deborah R Morris,et al.Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(Ⅱ)ions:thermodynamic and kinetic evaluations[J].Inorg Chem A April 26,2013,52(10):5838-5850..
[5]张光华,徐海龙,郭锦鸽,等.基于二苯乙烯荧光增白型返黄抑制剂的合成及应用[J].精细化工,2012,29(7):705-711.
[6]张跃华,张其平,石文艳,等.1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J].发光学报,2011,32(5):505-513.
[7]陈杰,贺英,潘照东,等.主链含萘酰亚胺的聚芳醚型聚合物的合成及其光电性能[J].发光学报,2012,33(3):705-711.
[8]唐小东,黄昆.7-羟基-4-甲基香豆素的合成工艺探究[D].达州:四川文理学院,2012.
[9]Atkins R L,Bliss D E.Substituted coumarins and azacoumarins.Synthesis and fluorescent properties[J].J Org Chem,1978,43(10):1974.
[10]赵义,淡宜.反应型紫外线吸收剂的制备及高分子化[J].高分子材料科学与工程,2006,22(5):74-77.
[11]董传明,舒雪桂,曾涛,等.受阻胺类光稳定剂Chimassorb2020的合成[J].精细化工,2005,22(6):468-471,474.
[12]昝帅,姜文凤,邵玉昌.三嗪型紫外线吸收剂的合成及性能[J].精细化工,2007,24(11):1106-1108.
[13]张红杰,胡惠仁,何志斌,等.利用荧光增白剂改善高得率浆的光学性能[J].中国造纸,2010,29(9):1-6.
[14]张锐.新型返黄抑制剂的合成及其在高得率竹浆中应用的研究[D].南宁:广西大学,2008.
[15]魏永巨,李娜,秦身钧.磺基水杨酸的荧光光谱与荧光量子产率[J].光谱学与光谱分析,2004,24(6):647-651.