颜料红22 | 6448-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 颜料红22
• 中文别名: 耐晒亮红N；3-羟基-4-[(2-甲基-5-硝基苯基)偶氮]-N-苯基-2-萘甲酰胺；C.I.颜料红22；萘酚红；耐晒亮红GY；颜料红 22
• 英文名称: 4-(2-methyl-5-nitrophenyl)azo-3-hydroxy-N-phenylnaphthalene-2-carboxamide
• 英文别名: C. I. Pigment Red 22；3-hydroxy-4-(2-methyl-5-nitro-phenylazo)-[2]naphthoic acid anilide；3-Hydroxy-4-(2-methyl-5-nitro-phenylazo)-[2]naphthoesaeure-anilid；3-hydroxy-4-[(2-methyl-5-nitrophenyl)azo]-N-phenylnaphthalene-2-carboxamide；5-nitro-o-toluidin->3-hydroxy-2-naphthanilid；3-hydroxy-4-[(2-methyl-5-nitrophenyl)diazenyl]-N-phenylnaphthalene-2-carboxamide
• CAS: 6448-95-9
• 化学式: C₂₄H₁₈N₄O₄
• 分子量: 426.431
• InChiKey: XYZMEPHFXJHGIX-UHFFFAOYSA-N

物化性质

• 沸点：
  622.6±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)
• LogP：
  2.18 at 20℃ and pH5.3
• 物理描述：
  DryPowder

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

制备方法与用途

生物活性

Pigment Red 22 是一种染料，广泛应用于彩妆、保湿剂和皮肤护理产品等配制中。

用途

主要用作油墨、文教用品、涂料印花的着色。

反应信息

• 作为反应物：
  描述：

  颜料红22 在 sodium sulfide 作用下， 生成 4-(5-amino-2-methyl-phenylazo)-3-hydroxy-[2]naphthoic acid anilide
  参考文献：
  名称：

  Rowe; Allen, Journal of the Society of Dyers and Colourists, 1935, vol. 51, p. 314,315

  摘要：

  DOI：
• 作为产物：
  描述：

  萘酚 、 2-methyl-5-nitroaniline diazonium fluoroboric salt 在 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以61.7%的产率得到颜料红22
  参考文献：
  名称：

  Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions

  摘要：

  We studied two azonaphtharylamide pigments having arylamide groups at the 2- and 7-positions on the naphthol ring. Presence of the 7-substited amide group distinguishes the pigments from conventional azonaphtharylamide pigments derived from 3-hydroxy-2-naphthoic acid. The 7-substituent caused a hyperchromic effect but did not produce bathochromic shift in the optical absorption spectra in solution compared with the corresponding 7-unsubstituted counterparts. Molecular geometry optimizations through semi-empirical MO calculations showed that extent of the chromophore systems in the pigments with and without the 7-substituent is nearly the same, which is consistent with absence of the bathochromic shift. The MO calculations also showed that the MOs localized in the 7-substituents are involved in the electronic transitions in the longest wavelength bands of the pigments, which is responsible for the hyperchromic effect. The 7-substituted pigments exhibited better resistivity to light and heat than the 7-unsubstituted ones. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.12.011

文献信息

• Rowe; Levin, Journal of the Society of Dyers and Colourists, 1924, vol. 40, p. 218,222
  作者：Rowe、Levin

  DOI：——

  日期：——
• Rowe; Giles, Journal of the Society of Dyers and Colourists, 1935, vol. 51, p. 278,280
  作者：Rowe、Giles

  DOI：——

  日期：——
• Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions
  作者：Junji Otani、Takeshi Kikuchi、Suguru Higashida、Takashi Harada、Michio Matsumura

  DOI：10.1016/j.molstruc.2014.12.011

  日期：2015.3

  We studied two azonaphtharylamide pigments having arylamide groups at the 2- and 7-positions on the naphthol ring. Presence of the 7-substited amide group distinguishes the pigments from conventional azonaphtharylamide pigments derived from 3-hydroxy-2-naphthoic acid. The 7-substituent caused a hyperchromic effect but did not produce bathochromic shift in the optical absorption spectra in solution compared with the corresponding 7-unsubstituted counterparts. Molecular geometry optimizations through semi-empirical MO calculations showed that extent of the chromophore systems in the pigments with and without the 7-substituent is nearly the same, which is consistent with absence of the bathochromic shift. The MO calculations also showed that the MOs localized in the 7-substituents are involved in the electronic transitions in the longest wavelength bands of the pigments, which is responsible for the hyperchromic effect. The 7-substituted pigments exhibited better resistivity to light and heat than the 7-unsubstituted ones. (C) 2014 Elsevier B.V. All rights reserved.
• Rowe; Allen, Journal of the Society of Dyers and Colourists, 1935, vol. 51, p. 314,315
  作者：Rowe、Allen

  DOI：——

  日期：——