N-(甲基取代苯基)-N-′(2-羟基-3-萘甲酰基)脲的合成研究

以2-羟基-3-萘甲酸和二氯亚砜为原料合成2-羟基-3-萘甲酰氯,再与甲基取代的苯脲化合物反应得到N-(甲基取代苯基)-N′-(2-羟基-3-萘甲酰基)脲。重点研究了N-(3-甲基苯基)-N-(′2-羟基-3-萘甲酰基)脲的合成工艺条件对产品收率的影响,确定了最佳合成工艺,即以苯为溶剂、三乙胺为缚酸剂,n(间甲基苯脲)∶n(2-羟基-3-萘甲酰氯)∶n(苯)=1∶3∶33,回流温度下反应4 h,产品质量分数97.40%,收率71.5%。在相同条件下合成了N-(2-甲基苯基)-N′-(2-羟基-3-萘甲酰基)脲、N-(4-甲基苯基)-N-(′2-羟基-3-萘甲酰基)脲和N-(3,5-二甲基苯基)-N-′(2-羟基-3-萘甲酰基)脲,质量分数分别为95.72%、97.69%和99.44%,收率分别为47.1%、71.5%和59.7%。通过紫外吸收光谱、红外吸收光谱和质谱等对化合物进行了表征,证明产品结构正确。

Synthesis and photoconductivities of bisazo charge generation materials

Six bisazo compounds were synthesized by coupling 2-(49-aminophenyl)-6-aminobenzoxazole as diazo component with N-phenyl-N9-(2-hydroxy-3-naphthoyl)urea derivatives,and characterized by ultraviolet and visible spectroscopy(UV-Vis),Fourier transform infrared spectroscopy(FT-IR)and elemental analysis(EA).Using these bisazo compounds as charge generation materials and CT-191(2-methyl-4-(N,N-dibenzyl)aminobenzoaldehyde-1,1-diphenylhydrazone)as charge transportation material,organic photoconductive devices were prepared.The result from photoconductivity measurement of the devices shows that the bisazo compound from N-(2-methylphenyl)-N9-(2-hydroxy-3-naphthoyl)urea has the best xerographic performance,V_(0)=600 V,V_(R)=30 V,R_(d)=15 V·s^(-1),E_(1/2)=3.5 lx·s.