1,2-Naphthochinon-1-(phenylhydrazon) | 93449-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-Naphthochinon-1-(phenylhydrazon)
• 英文别名: (1Z)-1-(phenylhydrazinylidene)naphthalen-2-one
• CAS: 93449-60-6
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: ZONYAPYTDIVJGG-VLGSPTGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2-Naphthochinon-1-(phenylhydrazon) 以 二氯甲烷-D2 为溶剂， 生成 sudan I
  参考文献：
  名称：

  1-（芳基偶氮）-2-萘酚的碳 13 NMR 和 X 射线结构测定。固态氮和氧原子之间的分子内质子转移

  摘要：

  涉及 1-(苯基偶氮)-2-萘酚及其 4{prime}-甲氧基、乙氧基和 N,N-二甲氨基衍生物中单质子转移的互变异构反应已用可变温度溶液和高分辨率固体进行了研究。状态{sup 13}C NMR光谱。母体未取代化合物和 4{prime}-N,N-二甲氨基衍生物的晶体结构已经确定。所有这些化合物在 NMR 时间尺度上在溶液和结晶相中的互变异构偶氮和腙形式之间进行快速质子交换。固体材料中的平衡组成类似于在溶液中测量的平衡组成。1-(苯基偶氮)-2-萘酚的晶体为单斜晶系，a = 27.875 (7), b = 6.028 (2), c = 14.928 (5) {埃}, {β} = 103.57 (2){度},空间群是 C2/c，Z = 8，在 1,082 次观察到的反射中，213 K 的结构被细化为 0.0414 的 R 因子。1-((4{prime}-(二甲氨基)苯基)偶氮)-2-萘酚的晶体为单斜晶系，a

  DOI：

  10.1021/ja00197a003
• 作为产物：
  描述：

  sudan I 以 四氯化碳 为溶剂， 生成 1,2-Naphthochinon-1-(phenylhydrazon)
  参考文献：
  名称：

  取代基和溶剂对苯胺和萘酚偶氮衍生物质子转移平衡的影响。多核核磁共振研究和理论计算

  摘要：

  摘要 在一系列 2-羟基萘-1-甲醛和 2-萘酚的偶氮衍生物中比较了由质子转移引起的互变异构平衡。尽管结构相似，但这些系统对溶液状态的质子转移特性具有不同的取代基影响。比较研究是在各种溶剂中使用 1 H、 13 C 和 15 N NMR 光谱进行的。Hartree-Fock ab initio 计算涉及互变异构体的相对稳定性和基态的完整几何优化，与实验观察结果一致。

  DOI：

  10.1016/s0022-2860(03)00208-4

文献信息

• Waste-Free Chemistry of Diazonium Salts and Benign Separation of Coupling Products in Solid Salt Reactions
  作者：Gerd Kaupp、Andreas Herrmann、Jens Schmeyers

  DOI：10.1002/1521-3765(20020315)8:6<1395::aid-chem1395>3.0.co;2-l

  日期：2002.3.15

  and anilines to give the triazenes. Azo couplings are achieved with quantitative yields by cautious co-grinding of solid diazonium salts with beta-naphthol and C-H acidic heterocycles, such as barbituric acids or pyrazolinones. Solid diazonium salts may be more easily applied in a stoichiometric ratio for couplings in solution. Co-grinding of solid diazonium salts with KI gives quantitative yields of

  气固和固固技术可在重氮盐化学过程中实现无浪费的定量合成。研究了用反应性气体NO（2），NO和NOCl重氮化的五种技术。两种类型通过原子力显微镜（AFM）进行了机械研究，并根据已知的晶体堆积进行了解释。相同的原理适用于由一步反应衍生的级联反应。固体重氮盐与固体二苯胺和苯胺定量偶合，得到三氮烯。偶氮偶联通过定量重磨固体重氮盐与β-萘酚和CH酸性杂环（如巴比妥酸或吡唑啉酮）而定量获得。固体重氮盐可以化学计量比更容易地用于溶液中的偶联。固体重氮盐与KI共同研磨可定量获得各种固体芳基碘化物。盐反应中不可避免的偶合产物以高度良性的方式从不溶性产物中完全分离出来。固态反应优于产生大量废料的类似溶液反应。用IR和NMR光谱及质谱法阐明了产物的结构，同时用B3LYP / 6-31G *和BLYP / 6-31G **水平的密度泛函计算研究了化合物的互变异构性质。固态反应优于产生大量废料的类似溶液反应。用IR
• [EN] NANOPIGMENTS<br/>[FR] NANOPIGMENTS
  申请人：NVA IP HOLDINGS PTY LTD

  公开号：WO2010054441A1

  公开（公告）日：2010-05-20

  The present invention relates to a dye monomer of general formula (I): A - X - R - O - C(O) - O - CH2- C(H) = CH2,wherein A is a dye molecule and both X and R are optional linkers. The present invention also relates to particles comprising a copolymer of said dye monomer and an ethylenically unsaturated monomer, to a method of producing said particles, to the use of said particles as nanopigments and to polymer dispersions comprising said particles as nanopigments.

  本发明涉及一种一般式(I)的染料单体：A - X - R - O - C(O) - O - CH2- C(H) = CH2，其中A是染料分子，X和R均为可选的连接物。本发明还涉及包含所述染料单体和乙烯基不饱和单体的共聚物的颗粒，以及制备所述颗粒的方法，以及将所述颗粒用作纳米颜料的用途，以及包含所述颗粒作为纳米颜料的聚合物分散体。
• The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4-Morpholino-2-naphthol
  作者：Stuart Aiken、Christopher D. Gabbutt、Lisa J. Gillie、Jonathan D. Heywood、Denis Jacquemin、Craig R. Rice、B. Mark Heron

  DOI：10.1002/ejoc.201301218

  日期：2013.12

  The syntheses of a series of new ketohydrazone dyes and pigment lakes with a unique structural motif derived from 4-morpholino-2-naphthol are described. The morpholine substituent is responsible for the hypsochromically shifted absorption maxima with significantly enhanced molar extinction coefficients of the new dyes; this conclusion is supported by time-dependent DFT (TD-DFT) simulations. The location

  描述了一系列新的酮腙染料和颜料色淀的合成，这些染料具有源自 4-morpholino-2-naphthol 的独特结构基序。吗啉取代基导致了新染料的最大吸光度偏移，并显着提高了摩尔消光系数；这一结论得到了瞬态 DFT (TD-DFT) 模拟的支持。吗啉取代基在颜料色淀中空间要求位点的位置阻碍了固态桥接磺酸盐基团的进一步配位，并阻止了其他颜料色淀常见的一维聚合物体系的形成。
• Process for preparing pigmented thermoplastic polymer compositions and
  申请人：Plasticolors, Inc.

  公开号：US05443775A1

  公开（公告）日：1995-08-22

  A process for preparing a pigmented thermoplastic polymer composition which is useful as a low profile additive composition for thermosetting resins comprises the steps of (A) selecting at least one thermoplastic polymer having a refractive index which is within about 0.06 units of the refractive index of the thermosetting resin; (B) preparing a mixture of said thermoplastic polymer and at least one color pigment, dye or mixture thereof under high shear in a high-intensity mixer; and (C) forming a slurry comprising said mixture obtained in step (B) in at least one liquid copolymerizable monomer containing at least one CH.sub.2 .dbd.C< group. In a preferred embodiment, at least one surfactant is included in the slurry obtained in step (C) in an amount sufficient to enhance the uniformity of the pigmentation of a cured composite produced from the thermosetting resin composition and a low profile additive composition. Additional pigment can be added to the slurry before the slurry is mixed with the thermosetting resin. The cured composites produced from the thermosetting resin composition and the low profile additive composition of the invention are characterized as having improved uniformity and intensity of color.

  一种用作热固性树脂低剖面添加剂组合物的有色热塑性聚合物组合物的制备方法，包括以下步骤：（A）选择至少一种具有与热固性树脂的折射率相差约0.06单位的折射率的热塑性聚合物；（B）在高强度混合器中高剪切下制备所述热塑性聚合物和至少一种颜色颜料、染料或其混合物的混合物；以及（C）在至少一种含有至少一种CH.sub.2.dbd.C<基团的液态共聚单体中形成含有步骤（B）中获得的所述混合物的浆料。在一种优选实施例中，在步骤（C）中获得的浆料中包含至少一种表面活性剂，其量足以提高从热固性树脂组合物和低剖面添加剂组合物制备的固化复合材料的着色均匀性。在将浆料与热固性树脂混合之前，还可以向浆料中添加额外的颜料。从该发明的热固性树脂组合物和低剖面添加剂组合物制备的固化复合材料的特点在于具有改善的颜色均匀性和强度。
• Method of preparing a cured pigmented thermosetting polymer composition
  申请人：Plasticolors, Inc.

  公开号：US05326516A1

  公开（公告）日：1994-07-05

  This invention relates to a process for preparing a pigmented thermoplastic polymer composition which is useful as a low profile additive composition for thermosetting resins. The process includes the steps of (A) selecting at least on thermoplastic polymer having a refractive index which is within about 0.06 units of the refractive index of the thermosetting resin; (B) preparing a mixture of said thermoplastic polymer and at least one color pigment, dye or mixture thereof under high shear in a high-intensity mixer; and (C) forming a slurry containing said mixture obtained in step (B) in at least one liquid copolymerizable monomer containing at least one CH.sub.2 .dbd.C<group. In a preferred embodiment, at least one surfactant is included in the slurry obtained in step (C) in an amount sufficient to enhance the uniformity of the pigmentation of a cured composite produced from the thermosetting resin composition and a low profile additive composition. Additional pigment can be added to the slurry before the slurry is mixed with the thermosetting resin. The cured composites produced from the thermosetting resin composition and the low profile additive composition of the invention are characterized has having improved uniformity and intensity of color.

  本发明涉及一种制备着色热塑性聚合物组合物的过程，该组合物可用作热固性树脂的低剖面添加剂组合物。该过程包括以下步骤：（A）选择至少一种热塑性聚合物，其折射率在热固性树脂的折射率内约0.06个单位；（B）在高强度混合器中高剪切下制备所述热塑性聚合物和至少一种颜色颜料、染料或其混合物的混合物；和（C）在至少一种含有至少一个CH.sub.2.dbd.C<group的液态共聚单体中形成含有步骤（B）中获得的混合物的浆料。在优选实施例中，在步骤（C）中获得的浆料中包含至少一种表面活性剂，其量足以增强从热固性树脂组合物和低剖面添加剂组合物制成的固化复合材料的着色均匀性。在将浆料与热固性树脂混合之前，可以向浆料中添加额外的颜料。从本发明的热固性树脂组合物和低剖面添加剂组合物制成的固化复合材料具有改善的均匀性和颜色强度。