一种新型光稳定剂的合成及应用
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摘要
采用Pechmann法,乙酰乙酸乙酯和间苯二酚在酸性条件下发生脱水缩合反应生成了7-羟基-4-甲基香豆素荧光增白剂。再以三聚氯氰为交联单体,经过亲核取代反应将7-羟基-4-甲基香豆素荧光增白剂、紫外线吸收剂2,4-二羟基二苯甲酮以及自由基捕获剂2,2’,6,6’-四甲基哌啶胺依次引入到同一分子中,合成了7-羟基-4-甲基香豆素类新型光稳定剂。采用红外光谱对其结构进行表征,采用紫外光谱、荧光光谱分析方法对其光学性质进行了初步分析,并通过紫外光加速老化实验考察了新型光稳定剂对纸张的返黄抑制效果。结果表明,合成的新型光稳定剂具有较好的返黄抑制效果,其返黄抑制作用优于单独使用7-羟基-4-甲基香豆素荧光增白剂的。
The 7-hydroxy-4-methyl coumarin fluorescent brightener was prepared based on the Pechmann method,a new 7-hydroxy-4-methyl coumarin light-induced yellowing prohibitor was synthesized by introducing 2,4-dihydroxy-benzophenone( an ultraviolet absorber) and 4-amion-2,2',6,6'-tetramentylniperidine( a free radicals capturer) into the molecule of 7-hydroxy-4-methyl coumarin fluorescent brightener,using cyanuric chloride as the cross-linking monomer.The structure of the new compound was characterized by FT-IR,UV-vis and photoluminescence( PL) spectrum-meters,its brightness-stabilizing effect on paper was evaluated by means of the ultraviolet aging apparatus.Results showed that,the new synthesized Light-induced Yellowing Prohibitor was more effective on yellowing-inhibition comparing with 7-hydroxy-4-methyl coumarin fluorescent brightener.
The 7-hydroxy-4-methyl coumarin fluorescent brightener was prepared based on the Pechmann method,a new 7-hydroxy-4-methyl coumarin light-induced yellowing prohibitor was synthesized by introducing 2,4-dihydroxy-benzophenone( an ultraviolet absorber) and 4-amion-2,2',6,6'-tetramentylniperidine( a free radicals capturer) into the molecule of 7-hydroxy-4-methyl coumarin fluorescent brightener,using cyanuric chloride as the cross-linking monomer.The structure of the new compound was characterized by FT-IR,UV-vis and photoluminescence( PL) spectrum-meters,its brightness-stabilizing effect on paper was evaluated by means of the ultraviolet aging apparatus.Results showed that,the new synthesized Light-induced Yellowing Prohibitor was more effective on yellowing-inhibition comparing with 7-hydroxy-4-methyl coumarin fluorescent brightener.
引文
[1]Lu Yan-hua.Development and application of high yield pulping technology[J].Hei Longjiang Pulp&Paper,2006(2):38.陆燕华.高得率制浆技术的发展与应用[J].黑龙江造纸,2006(2):38.
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[5]ZHANG Hong-jie,HU Hui-ren,HE Zhi-bin.New Advances on the Brightening Efficiency of Optical Brightening Agent(OBA)in HYPcontaining Fine Papers[J].China Pulp&Paper,2010,29(6):62.张红杰,胡惠仁,何志斌.含高得率浆高级纸中荧光增白剂增白效率的研究进展[J].中国造纸,2010,29(6):62.
[6]Ding Zhu-ming,Liu Li-xiang,Zhou Shu-jing.Research progress on ultraviolet stabilizers[J].Fine and Specialty Chemicals,2005,13(13):5.丁著明,刘丽湘,周淑静.紫外线吸收剂的研究进展[J].精细与专用化学品,2005,13(13):5.
[7]Zhao Yi,Dan Yi.Synthesis of a reactive UV-stabilizer and its application in styrenic polymers[J].Polymer Materials Science and Engineering,2006,22(5):74.赵义,淡宜.反应型紫外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.
[8]Tan Bing-da,Song Hai-long,Wang Shuang-fei.Synthesis of novel hindered amine photo-yellowing inhibitor and its application in bambusa chungii BCTMP pulp[J].Transactions of China Pulp and Paper,2009,24(3):67.覃炳达,宋海农,王双飞.新型受阻胺类光返黄抑制剂的合成及在竹子化机浆中的应用[J].中国造纸学报,2009,24(3):67.
[9]GUO Jin-ge,ZHANG Guang-hua,XU Hai-long.Study on Synergistic Use of Water-Soluble UVA and Naphthalimide Fluorescent Brighteners in Inhibition of Yellowing[J].China Pulp&Paper,2012,31(10):24.郭锦鸽,张光华,徐海龙.水溶性紫外线吸收剂与萘酰亚胺荧光增白剂协同使用的抑制返黄研究[J].中国造纸,2012,31(10):24.
[10]Ding Xin-yu.The synthesis of 7-hydroxy-4-methyl coumarin[J].Shanghai Chemical Industry,2004(11):26.丁欣宇.7-羟基-4-甲基香豆素的合成[J].上海化工,2004(11):26.
[11]Chen Wen-qi.Study on synthesis of 7-hydroxy-4-methyl coumarin[J].Chemical Industry Times,2011,25(6):18.陈闻起.7-羟基-4-甲基香豆素的合成研究[J].化工时刊,2011,25(6):18.
[12]Atkins R L,Bliss D E.Substituted coumarins and azacoumarins.Synthesis and fluorescent properties[J].J.Org.Chem.,1978,43(10):1974.
[13]Zhao Yu-lin,Fang Gui-gan,Wu Ding-xin.Studies on brightnessstability improvement of popler APMP with additives combinations[J].Transactions of China Pulp and Paper,2001,16(1):32.赵玉林,房桂干,吴定新.不同助剂组合对黑杨APMP浆白度稳定性的影响[J].中国造纸学报,2001,16(1):32.
[14]Fang Gui-gan,CASTELLAN Alain,Shen Zhao-bang.Brightness stabilizing effect of UV-absorbers and radical trapper on poplar APMP pulps[J].Chemistry and Industry of Forest Products,2000,20(1):33.
[15]Zhang Guang-hua,Xu Hai-long,Guo Jin-ge,et al.Synthesis and properties of new yellowing inhibitor with fluorescent whitening[J].CIESC Journal,2012,63(10):3358.张光华,徐海龙,郭锦鸽,等.具有荧光增白作用的新型返黄抑制剂的合成及性能[J].化工学报,2012,63(10):3358.
[16]Du Zhao-mei.Study on the inhbiting yellowing technique and mechanism of bambusa chungii APMP pulp[D].Guangxi:Guangxi University,2007.杜召梅.粉单竹APMP浆返黄抑制技术的研究及其机理的初步探索[D].广西:广西大学,2007.
[17]Tan Bing-da.Study on novel hindered amine photo-yellowing inhibitor for chem-me chanical pulp[D].Guangxi:Guangxi University,2008.覃炳达.新型受阻胺类化机浆光返黄抑制剂的研究[D].广西:广西大学,2008.
[2]ZHOU Ya-jun,ZHANG Dong-ji,LI Gan-lin.An Overview of BCTMP:Process,Development,Pulp Quality and Utilization[J].China Pulp&Paper,2005,24(5):51.周亚军,张栋基,李甘霖.漂白高得率化学机械浆综述[J].中国造纸,2005,24(5):51.
[3]Zhang Hong-jie,Hu Hui-ren.New advances on improving the optical stability of high yield pulps[J].Transactions of China Pulp and Paper,2008,23(2):109.张红杰,胡惠仁.提高高得率浆光学稳定性研究的新进展[J].中国造纸学报,2008,23(2):109.
[4]Lin Ben-ping,Wang Shuang-fei.Research progress in the mechanism of light-induced yellowing of high yield pulps[J].Transactions of China Pulp and Paper,2007,22(1):92.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.
[5]ZHANG Hong-jie,HU Hui-ren,HE Zhi-bin.New Advances on the Brightening Efficiency of Optical Brightening Agent(OBA)in HYPcontaining Fine Papers[J].China Pulp&Paper,2010,29(6):62.张红杰,胡惠仁,何志斌.含高得率浆高级纸中荧光增白剂增白效率的研究进展[J].中国造纸,2010,29(6):62.
[6]Ding Zhu-ming,Liu Li-xiang,Zhou Shu-jing.Research progress on ultraviolet stabilizers[J].Fine and Specialty Chemicals,2005,13(13):5.丁著明,刘丽湘,周淑静.紫外线吸收剂的研究进展[J].精细与专用化学品,2005,13(13):5.
[7]Zhao Yi,Dan Yi.Synthesis of a reactive UV-stabilizer and its application in styrenic polymers[J].Polymer Materials Science and Engineering,2006,22(5):74.赵义,淡宜.反应型紫外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.
[8]Tan Bing-da,Song Hai-long,Wang Shuang-fei.Synthesis of novel hindered amine photo-yellowing inhibitor and its application in bambusa chungii BCTMP pulp[J].Transactions of China Pulp and Paper,2009,24(3):67.覃炳达,宋海农,王双飞.新型受阻胺类光返黄抑制剂的合成及在竹子化机浆中的应用[J].中国造纸学报,2009,24(3):67.
[9]GUO Jin-ge,ZHANG Guang-hua,XU Hai-long.Study on Synergistic Use of Water-Soluble UVA and Naphthalimide Fluorescent Brighteners in Inhibition of Yellowing[J].China Pulp&Paper,2012,31(10):24.郭锦鸽,张光华,徐海龙.水溶性紫外线吸收剂与萘酰亚胺荧光增白剂协同使用的抑制返黄研究[J].中国造纸,2012,31(10):24.
[10]Ding Xin-yu.The synthesis of 7-hydroxy-4-methyl coumarin[J].Shanghai Chemical Industry,2004(11):26.丁欣宇.7-羟基-4-甲基香豆素的合成[J].上海化工,2004(11):26.
[11]Chen Wen-qi.Study on synthesis of 7-hydroxy-4-methyl coumarin[J].Chemical Industry Times,2011,25(6):18.陈闻起.7-羟基-4-甲基香豆素的合成研究[J].化工时刊,2011,25(6):18.
[12]Atkins R L,Bliss D E.Substituted coumarins and azacoumarins.Synthesis and fluorescent properties[J].J.Org.Chem.,1978,43(10):1974.
[13]Zhao Yu-lin,Fang Gui-gan,Wu Ding-xin.Studies on brightnessstability improvement of popler APMP with additives combinations[J].Transactions of China Pulp and Paper,2001,16(1):32.赵玉林,房桂干,吴定新.不同助剂组合对黑杨APMP浆白度稳定性的影响[J].中国造纸学报,2001,16(1):32.
[14]Fang Gui-gan,CASTELLAN Alain,Shen Zhao-bang.Brightness stabilizing effect of UV-absorbers and radical trapper on poplar APMP pulps[J].Chemistry and Industry of Forest Products,2000,20(1):33.
[15]Zhang Guang-hua,Xu Hai-long,Guo Jin-ge,et al.Synthesis and properties of new yellowing inhibitor with fluorescent whitening[J].CIESC Journal,2012,63(10):3358.张光华,徐海龙,郭锦鸽,等.具有荧光增白作用的新型返黄抑制剂的合成及性能[J].化工学报,2012,63(10):3358.
[16]Du Zhao-mei.Study on the inhbiting yellowing technique and mechanism of bambusa chungii APMP pulp[D].Guangxi:Guangxi University,2007.杜召梅.粉单竹APMP浆返黄抑制技术的研究及其机理的初步探索[D].广西:广西大学,2007.
[17]Tan Bing-da.Study on novel hindered amine photo-yellowing inhibitor for chem-me chanical pulp[D].Guangxi:Guangxi University,2008.覃炳达.新型受阻胺类化机浆光返黄抑制剂的研究[D].广西:广西大学,2008.