苯并噁唑双偶氮化合物的合成及敏化工艺研究
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摘要
双偶氮化合物作为电荷产生材料具有优越的光敏性、较宽的光谱响应范围和低廉的制造成本,是有机光导材料中一类很好的电荷产生材料。其中,苯并噁唑类偶氮电荷产生材料具有光稳定性高、防潮性和耐久性好的优点。
本文以2-(4'-硝基苯基)-6-硝基苯并噁唑为原料,经铁粉还原制备2-(4'-氨基苯基)-6-氨基苯并噁唑,研究了盐酸用量和反应时间对产品收率的影响,确定适宜的反应条件为:硝基化合物、浓盐酸和铁粉的摩尔比为1:6:9,在95~100℃下还原8h,产品质量百分数为98.6%,产率为59.2%。以2-(4'-氨基苯基)-6-氨基苯并噁唑为重氮组分、分别以3-羟基-2-萘甲酰替邻氯苯胺、色酚AS和色酚AS-D为偶合组分经重氮化、偶合反应合成了三种双偶氮化合物,产品收率分别为76.5%、61.4%和65.2%。通过熔点测定、紫外可见吸收光谱、红外吸收光谱和高效液相色谱等对产物进行了分析和结构鉴定。
采用索氏提取的方法对合成的双偶氮化合物进行敏化,研究了提取剂的种类、回流次数对双偶氮化合物光电性能的影响,确定了适宜的敏化条件为以二氯甲烷为提取剂单次索氏提取,回流180次。
探讨了功能膜制备条件对光导体性能的影响,确定适宜的工艺条件为以四氢呋喃为产生层分散介质,球磨2h所得的双偶氮电荷产生材料的光电性能最佳。通过粒径分析仪测定产生层分散液中双偶氮化合物的粒径在0.4μm以下,原子力显微镜测定产生层表面最高处与最低处的落差为800nm。
The disazo compounds have high sensitivity, low dark decay, excellent photoelectrical stability, wide spectral range and low cost. They were widely used as charge generation materials (CGM) in organic photoconductors (OPC). The disazo compounds containing benzoxazole moiety, that have also high stability, good water resistance, and wonderful durability, were studied in this paper.
Firstly, 2-(4'-amidophenyl)-6-amidobenzoxazole was prepared through the reduction of 2-(4'-nitrophenyl)-6-nitrobenzoxazole using Fe power as reductant. The effects of the dosage of hydrochloric acid and reaction time on the reaction were investigated. The optimal technical conditions was: n(2-(4'-nitrophenyl)-6-nitrobenz-oxazole):n(hydrochloric acid):n(Fe) = 1:9:6, reaction 8 hours under 95~100℃. The purity and yield of obtained product was 98.6% and 59.2% respectively. Three disazocompounds were synthesized through diazotization and coupling reaction with 2-(4'-amidophenyl)-6-amidobenzoxazole as disazo component, and naphthol and its analogues as the coupling component. The yields of the three compounds were 76.5%, 61.4% and 65.2%. The structures and purities of the synthesized compounds were confirmed by IR, UV and HPLC. The synthesized disazo compounds were sensitized by Soxhlet extraction.
The technical conditions, such as solvents and circumfluence time were studied. The sample, which was Soxhlet extracted with chloromethane as solvent and circumfusing time of 180, had most excellent photoconductivity.
The relationship between applied charatersitics of OPC and its preparation conditions was studied. The idealing photoconductivity was obtained when using tetrahydrofuran as dispersant of CGM and mills time of 2 hours. The appearance of charge generation layer (CGL) was measured by particle size distribution NG and AFM. The results showed that, the particle size of CGM was smaller than 0.4μm, and the height of CGL surface is lower than 800nm.
本文以2-(4'-硝基苯基)-6-硝基苯并噁唑为原料,经铁粉还原制备2-(4'-氨基苯基)-6-氨基苯并噁唑,研究了盐酸用量和反应时间对产品收率的影响,确定适宜的反应条件为:硝基化合物、浓盐酸和铁粉的摩尔比为1:6:9,在95~100℃下还原8h,产品质量百分数为98.6%,产率为59.2%。以2-(4'-氨基苯基)-6-氨基苯并噁唑为重氮组分、分别以3-羟基-2-萘甲酰替邻氯苯胺、色酚AS和色酚AS-D为偶合组分经重氮化、偶合反应合成了三种双偶氮化合物,产品收率分别为76.5%、61.4%和65.2%。通过熔点测定、紫外可见吸收光谱、红外吸收光谱和高效液相色谱等对产物进行了分析和结构鉴定。
采用索氏提取的方法对合成的双偶氮化合物进行敏化,研究了提取剂的种类、回流次数对双偶氮化合物光电性能的影响,确定了适宜的敏化条件为以二氯甲烷为提取剂单次索氏提取,回流180次。
探讨了功能膜制备条件对光导体性能的影响,确定适宜的工艺条件为以四氢呋喃为产生层分散介质,球磨2h所得的双偶氮电荷产生材料的光电性能最佳。通过粒径分析仪测定产生层分散液中双偶氮化合物的粒径在0.4μm以下,原子力显微镜测定产生层表面最高处与最低处的落差为800nm。
The disazo compounds have high sensitivity, low dark decay, excellent photoelectrical stability, wide spectral range and low cost. They were widely used as charge generation materials (CGM) in organic photoconductors (OPC). The disazo compounds containing benzoxazole moiety, that have also high stability, good water resistance, and wonderful durability, were studied in this paper.
Firstly, 2-(4'-amidophenyl)-6-amidobenzoxazole was prepared through the reduction of 2-(4'-nitrophenyl)-6-nitrobenzoxazole using Fe power as reductant. The effects of the dosage of hydrochloric acid and reaction time on the reaction were investigated. The optimal technical conditions was: n(2-(4'-nitrophenyl)-6-nitrobenz-oxazole):n(hydrochloric acid):n(Fe) = 1:9:6, reaction 8 hours under 95~100℃. The purity and yield of obtained product was 98.6% and 59.2% respectively. Three disazocompounds were synthesized through diazotization and coupling reaction with 2-(4'-amidophenyl)-6-amidobenzoxazole as disazo component, and naphthol and its analogues as the coupling component. The yields of the three compounds were 76.5%, 61.4% and 65.2%. The structures and purities of the synthesized compounds were confirmed by IR, UV and HPLC. The synthesized disazo compounds were sensitized by Soxhlet extraction.
The technical conditions, such as solvents and circumfluence time were studied. The sample, which was Soxhlet extracted with chloromethane as solvent and circumfusing time of 180, had most excellent photoconductivity.
The relationship between applied charatersitics of OPC and its preparation conditions was studied. The idealing photoconductivity was obtained when using tetrahydrofuran as dispersant of CGM and mills time of 2 hours. The appearance of charge generation layer (CGL) was measured by particle size distribution NG and AFM. The results showed that, the particle size of CGM was smaller than 0.4μm, and the height of CGL surface is lower than 800nm.
引文
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[4] Albert J. Cherry, Robert R. Neiman, Meredith D. Shattuck et al, Electro- photographic plate, US: 3791826, 1974-02-12
[5]蒲嘉陵,张伟民,近红外高感光度有机光导体——Y-氧钛酞菁的研究,感光科学与光学,1988,l 16(4):338~342
[6] Liu Dongzhi,et al, Syntheses and photoelectric properties of perylene red pigments,Transactions of tianjin University, 1997,3(2):154~158
[7]刘东志,赵锦花,李祥高,苝环结构修饰的丙烯酰胺聚合物的合成及性能,应用化学,1998,15(5):52~55
[8] Law Kock-Yee, Tarnawskyj Ihor W. ,Popovic Zoran D., Azo pigments and their intermediaries. A study of the struvture-sensitivity relationship of photogenerating bisazo pigments in bilayer xerographic devices, Journal of Imaging Science and Technology, 1994, 38(2):118~124
[9] Law Kock- Yee, Effect of dye aggregation on the photogeneration efficiency of organic photoconductors, Journal of Phys Chem, 1988,92: 4226
[10] Takano S, Mimura Y, Matsui N, et al. Characteristic of titanium oxide phthalocyanine polymorphs used as organic photoreceptors. J Imaging Technol, 1990,17: 46
[11] Rau H.B., Organic photoconductive materials: Recent trends and development. Phys. Chem., 1969, 73:810~819
[12] Champ. R. B., Shattuck. M. D., Electrophotographic processes using disazo pigments. US: 3898084, 1975-08-05
[13] Scki K,Suzuki Y,Yamanami H.The Fifth International Congress on Advances in Non-Impact Printing Technologies.SPSE,Proceedings,1990,60
[14] Law Kock-Yee. Organic photoconductive materials: recent trends and developments. Chem. Rev., 1993, 93:449~486
[15]彭必先,林童,功能性染料在有机光受体上的应用及研究进展,科学通报,1999, 44(13): 1355~1368
[16]张玉红,赵华绒,俞庆森,含蒽醌基单偶氮染料光电导性质构效研究,化学学报, 2002, 60(8): 1513~1516
[17] P.Juvvik.B.Sundby,and G.Rills.Dyes&Pigm .1973,27:l0
[18] J.Kelemen.G.Kormany,and G.Rihs.Dyes& Pigm .1982,3:249
[19] P.Ba11.C.H.Nicho11.Dyes&Pigm .1982.3:5
[20] Matsunaga,Y.;Miyaj ima,N.Diffuse reflection spectra offilter papers dyed withl-arylazo 2 naphthol s BuI1.Chem.Soc.Jpn.1971.4 :36l
[21] Kuder.J.E.HMO consideration of factors affecting trantornerism in hydroxy arylazo compounds.Tetrahcdron.1972,28:1973
[22]王艳乔,丁瑞松,蒋克健等.高性能静电复印有机光导材料的研究.高技术通讯.2000,7:93
[23]周玉香,机能分离型有机光导材料,复印,1993(3):51~59
[24]邹春燕李亚明张华,偶氮类有机光导体的发展趋势,染料与染色,2005,4:13~16
[25] Kashizaki Yoshi, Suzuki Koicho, Electrophotographic photosensitive member and electrophotographic apparatus and facsimile machine which uses the electrophotographic photosensitive member, EP:480821, 1992-04-15
[26] Nagamura Hideki, Ito Akira, Electrophotographic photoreceptor, JP:8262764,1996-10-11
[27] Nagamura Hideki , Kodera Taksuya, Electrophotographic photoreptor , JP:93l1478, 1997-12-02
[28]张玉红俞庆森,含蒽醌基单偶氮染料吸收光谱研究,浙江大学学报(理学版),2002,1:73~76
[29]阮剑利(杭州电化集团有限公司杭州),偶氮染料的光敏性研究,染料与染色,2003, 40(2): 75~77
[30]丁瑞松王艳乔等,静电复印用双偶氮颜料的研究,化学通报,2001,1:53~55
[31]那强,李亚明,张华等.用于有机光导材料的三偶氮颜料的合成研究.感光科学与光化学.2003,21:4
[32]宋继武,冯文,周玉香,李兴民,李祥高,三偶氮颜料的合成及光电性能研究,复印,1999(1):17~19
[33] James C. Fleming, Michael D. Shea, Disazotype compositions and photographic precesses, US:3761263,1973-09-25
[34] Umehara Shoji, Kashizaki Yoshio, Electrophotographic photosensitive membercomprising aromatic azo pigment containing cyclic amino group, U.S.Patent,4868080, 1989-09-19
[35] Miyamoto Eiichi, Hanatani Yasuyuki, Electrophotographic sensitive body, JP :5142831, l993-06-11
[36] Miyamoto Eiichi, Hanatani Yasuyuki, Electrophotographic sensitive body, JP:5142834, 1993-06-11
[37]施敏敏陈红征潘超汪茫,芴酮基偶氮单层有机光导鼓制备工艺研究,浙江大学学报(工学版)2006,9:1578~1582
[38] Kock-Yee Law, Fairport; Ihor W. Tarnawskyj, Rochester, both of N.Y., Disazo photoconductive imaging members, US:4797337, 1989-01-10
[39] Rorbert Bruce Champ, Meredith David Shattuck, Electrophotographic processes using disazo pigments, US: 3898084, 1975-08-05
[40] Masafumi Ohta, Susan, Disazo triphenylamine compounds, US: 4663442, 1987-05-05
[41] Katagiri Kazuharu, Watanabe Katsunori, Ishikawa Shozo et al, Electrophotographic disazo photosensitive member, U.S.Patent, 4471040, 1984-09-11
[42]那强李亚明张华万相见赵文娟,4,4',4''-三氨基三苯胺的合成,染料与染色,2003,8:225~226
[43] Masataka Yamashita, Hajime Miyazaki, Takao Takiguchi, Masakazu Matsumoto, Masaaki Hiro, Shozo Ishkawa, Electrophotographic member comprising a disazo pigment, GB: 2176021, 1986-12-10
[44] Yamada Yasuyuki Mitsui Toatsu, Itoh Hisato Mitsui Toatsu Apaa, NishizawaTsutomu et al, Electrophotographic photoreceptor, EP: 259099, 1988-03-09
[45] Sakai Kiyoshi, Electrophotographic sensitive body, JP: 63175865, 1988-07-20
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