2-[2-羟基-4- (2-羟基-3-烷氧基)丙氧基苯基]- (5-氯-)2H-苯并三唑紫外线吸收剂的合成及表征
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Synthesis and Characterization of 2-[2 -hydroxy-4 -(2-hydroxy-3-alkoxy)propylphenyl]-(5-chloro-)2H-benzotriazole UV Absorbers
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    摘要:

    摘要 以环氧氯丙烷为原料,分别与正丁醇、异辛醇、正十二醇,在三氟化硼乙醚催化作用下,反应制备了3个(2-羟基-3-氯)丙基烷氧基醚(Ia,Ib,Ic)。再分别以2-(2,4-二羟基苯基)-2H-苯并三唑,2-(2,4-二羟基苯基)-5-氯-2H-苯并三唑为原料,在弱碱性条件下,分别与上述合成的3个开环产物进行烷基化反应,制备了6个间苯二酚衍生物类型苯并三唑化合物:2-[2-羟基-4- (2-羟基-3-烷氧基)丙氧基苯基]- (5-氯-)2H-苯并三唑(IIa,IIb,IIc,IIIa,IIIb,IIIc),收率分别为83%,79%,78%,85%,74%,77%。对目标产物进行了FTIR和MS表征,并测定了紫外吸收光谱,该6个化合物在250~400nm波长范围内均有范围宽,强度大的吸收峰,最大摩尔消光系数εmax分别为23190.1Lmol-1cm-1(λmax=338.5nm),22018.4Lmol-1cm-1(λmax=341.5nm),23895.1 Lmol-1cm-1(λmax=339nm),24368.0 Lmol-1cm-1(λmax=346.5nm),,22522.6 Lmol-1cm-1(λmax=346.5nm), 25104.5 Lmol-1cm-1(λmax=347nm),与传统的市售商品紫外线吸收剂UV-P(εmax=16177.7Lmol-1cm-1,λmax=338.5nm)相比,是一类更为高效的紫外线吸收剂。

    Abstract:

    Abstract: Three (2-hydroxy-3-chloro)propylalkoxy ether compounds were prepared by the reactions of epichlorohydrin with n-butanol,iso-octanol, n-dodecanol respectively,and borontrifluorideethercomplex as catalyst.Then,using the three compounds we prapared , respectively reacted with 2 - (2,4-dihydroxyphenyl)-2H-benzotriazole or 2 - (2,4-dihydroxyphenyl) -5 - chloro-2H-benzotriazole,six 2-[2 -hydroxy-4 -(2-hydroxy-3-alkoxy)propylphenyl]-(5-chloro-)2H-benzotriazole compounds(IIa,IIb,IIc,IIIa,IIIb,IIIc) were synthesized as type of resorcinol derivative,the yields were 83%,79%,78%,85%,74%and 77% respectively. The target products were characterized by IR and MS,and tested by ultraviolet absorption spectrum ,all the six compounds have relatively strong absorption peak in 250 ~ 400 nm wavelength range.Maximum molar extinction coefficient(εmax) of compounds IIa,IIb,IIc,IIIa,IIIb and IIIc) was 23190.1Lmol-1cm-1(λmax=338.5nm),23016.3Lmol-1cm-1(λmax=341.5nm),23895.1 Lmol-1cm-1(λmax=339nm),24368.0 Lmol-1cm-1(λmax=346.5nm),22522.6 Lmol-1cm-1(λmax=346.5nm) and 25104.5 Lmol-1cm-1(λmax=347nm) .They were a kind of more efficient UV absorbers ,compared with the traditional UV absorber UV-P(εmax=16177.7 Lmol-1cm-1,λmax=338.5nm) .

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赵文武.2-[2-羟基-4- (2-羟基-3-烷氧基)丙氧基苯基]- (5-氯-)2H-苯并三唑紫外线吸收剂的合成及表征[J].精细化工,2014,31(2):

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  • 收稿日期:2013-10-21
  • 最后修改日期:2013-12-01
  • 录用日期:2013-12-06
  • 在线发布日期: 2014-02-08
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