颜料红2 | 6041-94-7

• 物质功能分类: 染料及颜料 - 颜料 - 有机颜料
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 颜料红2
• 中文别名: 萘酚红FRR；4-[(2,5-二氯苯基)偶氮]-3-羟基-N-苯基-2-萘甲酰胺；永固红B；永固红FRR；C.I.颜料红2；颜料红 2
• 英文名称: 4-(2,5-dichlorophenyl)azo-3-hydroxy-N-phenylnaphthalene-2-carboxamide
• 英文别名: C. I. Pigment Red 2；4-(2,5-dichloro-phenylazo)-3-hydroxy-[2]naphthoic acid anilide；4-(2,5-Dichlor-phenylazo)-3-hydroxy-[2]naphthoesaeure-anilid；4-[(2,5-dichlorophenyl)azo]-3-hydroxy-N-phenylnaphthalene-2-carboxamide；2,5-dichloranilin->3-hydroxy-2-naphthanilid；1-(2',5'-Dichlorphenylazo)-2-hydroxy-3-naphthoanilid；4-[(2,5-dichlorophenyl)diazenyl]-3-hydroxy-N-phenylnaphthalene-2-carboxamide
• CAS: 6041-94-7
• 化学式: C₂₃H₁₅Cl₂N₃O₂
• 分子量: 436.297
• InChiKey: HXJSTOXKASOAQW-UHFFFAOYSA-N

物化性质

• 熔点：
  310-311°C
• 沸点：
  595.2±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  20℃有机溶剂中的溶解度为8.63mg/L
• LogP：
  3.2 at 23℃
• 物理描述：
  Yellowish red solid with a tint of pink or dark red powder. (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品运输编号：
  25kgs
• 海关编码：
  3204170000

制备方法与用途

制备方法

2,5-二氯苯胺（大红色基GG）与盐酸和水搅拌溶解，冷却后，在液面下加入亚硝酸钠溶液进行重氮化反应，随后加入硅藻土，过滤备用。将色酚AS溶于氢氧化钠溶液中，然后在液面下将上述重氮盐溶液加入偶合反应，搅拌均匀后用乙酸（或盐酸）调节反应液呈弱酸性，再进行过滤、水洗和干燥，最终得到产品。

用途简介

该颜料呈现中性红色，略带黄色调，但其耐光牢度比C.I.颜料红112稍低0.5-1级。粒径较大，透明度较低。主要应用于胶版及包装印刷油墨、织物印染和粘胶纤维原浆着色，较少用于涂料着色。其耐罩光漆、高温灭菌以及耐溶剂性能也较C.I.颜料红112稍低。该产品主要用于水性墨、溶剂型油漆、水性漆、工业涂料、涂料印花及文教用品等领域。

反应信息

• 作为产物：
  描述：

  2,5-二氯苯胺 在 盐酸 、 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 生成 颜料红2
  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

• 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.