4-(3-hydroxyphenoxy)phthalonitrile | 343982-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-hydroxyphenoxy)phthalonitrile
• 英文别名: 4-(3-hydroxyphenoxy)benzene-1,2-dicarbonitrile
• CAS: 343982-47-8
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: LYWFSUDTBIKKKK-UHFFFAOYSA-N

物化性质

• 沸点：
  464.9±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-hydroxyphenoxy)phthalonitrile 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到tris(3-(3,4-dicyanophenoxy)phenyl) phosphate
  参考文献：
  名称：

  三官能邻苯二甲腈单体作为增硬添加剂，用于易加工的高性能树脂

  摘要：

  摘要首次合成了一种新的三官能邻苯二甲腈单体三（3-（3,4-二氰基苯氧基）苯基）磷酸酯（TPP），并进行了表征，以提高邻苯二甲腈树脂的交联速率。通过将TTP和双官能邻苯二甲腈与芳族二胺易于加工的配方（η450°C，T5％> 500°C，TOS5％> 500°C，Yc在900°C> 80％）结合使用。TPP（引入的单体）可以与普通的双官能邻苯二甲腈一起使用，并可以用作提高刚度的添加剂，并且易于加工的配方可用于经济高效的复合材料制造技术。

  DOI：

  10.1016/j.reactfunctpolym.2019.104409
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 间苯二酚 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 生成 4-(3-hydroxyphenoxy)phthalonitrile 、 1,3-双(3,4-二氰基苯氧基)苯
  参考文献：
  名称：

  Preparation of self-promoted hydroxy-containing phthalonitrile resins by an in situ reaction

  摘要：

  通过一锅法进行了羟基与邻苯二腈体系的原位反应，制备的聚合物表现出优异的热稳定性、高模量和高玻璃化转变温度。

  DOI：

  10.1039/c5ra18472j

文献信息

• Phthalonitrile Monomer Modified with Organophosphorus Fragments, a Method of Producing thereof, a Binder Based Thereon, and a Prepreg
  申请人：Joint Stock Company Scientific and Production Association “UNICHIMTEK” (JSC PSA “UNICHIMTEK”)

  公开号：US20190218235A1

  公开（公告）日：2019-07-18

  A method of obtaining modified phthalonitriles comprising organophosphorus fragments, binding agents based thereon, and products produced with the use thereof, can be used in a variety of fields—from aircraft and automobile manufacturing to producing polymer composite materials. The method makes it possible to produce phthalonitrile monomers comprising organophosphorus fragments from simpler and cheaper reagents and to obtain them as individual substances, simplifying the process of synthesis, reducing the glass transition temperature of monomers and increasing the thermal oxidation stability of hardened polymers. The phthalonitrile monomer modified with organophosphorus fragments is characterized by the following general formula: wherein R is a radical selected from the group comprising aryl, alkyl, aryloxy or alkyloxy substituents; and X is a divalent aryl substituent selected from a group comprising phenylenes and naphthylenes. Also disclosed is a method of obtaining the modified phthalonitrile monomer, a binder, and a prepreg based on the same.

  一种获得含有有机磷基团的改性邻二氰酸酯的方法，以及基于该方法的结合剂和使用它们生产的产品，可以用于各种领域——从飞机和汽车制造到生产聚合物复合材料。该方法使得从更简单和更便宜的试剂中获得含有有机磷基团的邻二氰酸酯单体成为可能，并将它们作为单独物质获得，简化了合成过程，降低了单体的玻璃转变温度，并提高了硬化聚合物的热氧化稳定性。含有有机磷基团改性的邻二氰酸酯单体的一般式如下：其中R是从苯基，烷基，芳氧基或烷氧基取代基组成的基团；X是从苯基和萘基组成的二价芳基取代基。还公开了一种获得改性邻二氰酸酯单体、粘合剂和基于其的预浸料的方法。
• Trifunctional thermosetting monomer with propargyl and phthalonitrile groups
  作者：M. V. Yakovlev、O. S. Morozov、E. S. Afanaseva、B. A. Bulgakov、A. V. Babkin、A. V. Kepman、V. V. Avdeev

  DOI：10.1007/s11172-020-3020-3

  日期：2020.11

  A new monomer containing thermosetting groups of two types, namely, propargyl ether and phthalonitrile, in the structure of the molecule was synthesized and studied. It was found that thermal polymerization was accompanied by the degradation of the monomer with propargyl ether decomposition. This problem can be solved using catalysts based on Cu(i) favoring the polymerization at both the propargyl group and phthalonitrile fragments. The cured monomer has a non-porous structure and high thermal properties (Vicat softening temperature 395 °C, T5% 451 °C). The low viscosity of the melt (<200 mPa s at 120 °C) and low glass-transition temperature (9 °C) of the monomer make it possible to use it for the formation of composite materials by vacuum infusion or injection into a mold.

  合成并研究了一种分子结构中含有两种热固性基团（丙炔醚和邻苯二腈）的新型单体。研究发现，热聚合伴随着丙炔醚分解的单体降解。使用基于 Cu(i) 的催化剂可以解决这个问题，这种催化剂有利于丙炔基团和邻苯二腈片段的聚合。固化后的单体具有无孔结构和较高的热性能（维卡软化温度 395 °C，T5% 451 °C）。这种单体的熔体粘度低（120 °C 时为 200 mPa s），玻璃化转变温度低（9 °C），因此可以通过真空灌注或注入模具的方式制成复合材料。
• PHTHALONITRILES DERIVED FROM POLYPHENOLS
  申请人：The Government of the United States of America, as represented by the Secretary of the Navy

  公开号：US20160311976A1

  公开（公告）日：2016-10-27

  A method of making an organic salt comprising: reacting a polyphenol with a base and optionally a dihaloaromatic compound. The polyphenol is resveratrol; dihydroresveratrol; 4,4′-(but-2-ene-1,4-diyl)bis-2-methoxyphenol; 4,4′-(1,4-butane-diyl)bis-2-methoxyphenol; 1-ethyl-2-methyl-3-(4-hydroxyphenyl)-5-hydroxyindane; 4,4′-(ethane-1,1-diyl)diphenol; 5,5′-methylenebis(2-methoxy-4-methylphenol); 4,4′-methylenebis(5-isopropyl-2-methylphenol); 4,4′-(1-ethyl-2-methyl-1,3-propanediyl)bisphenol; or 5,5′-(ethane-1,1-diyl)bis(2-methoxy-4-methylphenol. The dihaloaromatic compound if present comprises a carbonyl group, a sulfonyl group, a sulfinyl group, or a phosphoryl group. There is a molar excess of the hydroxy groups of the polyphenol relative to halo groups of the dihaloaromatic compound if present. The corresponding phthalonitrile monomers and thermosets made from the organic salts are disclosed.

  一种制备有机盐的方法，包括：将多酚与碱反应，可选地与二卤芳烃化合物反应。多酚是白藜芦醇；二氢白藜芦醇；4,4'-(丁-2-烯-1,4-二基)双-2-甲氧基苯酚；4,4'-(1,4-丁二基)双-2-甲氧基苯酚；1-乙基-2-甲基-3-(4-羟基苯基)-5-羟基吲哚；4,4'-(乙烷-1,1-二基)二酚；5,5'-亚甲基双(2-甲氧基-4-甲基苯酚)；4,4'-亚甲基双(5-异丙基-2-甲基苯酚)；4,4'-(1-乙基-2-甲基-1,3-丙二基)双酚；或5,5'-(乙烷-1,1-二基)双(2-甲氧基-4-甲基苯酚)。如果存在二卤芳烃化合物，则其包括羰基基团、磺酰基、亚磺酰基或磷酰基。相对于二卤芳烃化合物的卤素基团，多酚的羟基存在摩尔过量。还公开了相应的邻苯二腈单体和由有机盐制成的热固性材料。
• Synthesis of Novel Covalently Linked Dimeric Phthalocyanines
  作者：Aleksey Lyubimtsev、Sergej Vagin、Sergej Syrbu、Michael Hanack

  DOI：10.1002/ejoc.200600733

  日期：2007.4

  We report the syntheses of the dimeric homonuclear Pcs 9a and 9b and of the dimeric heteronuclear Pc 9c, starting from the unsymmetrical phthalocyanines 7a and 7b, each containing a phenolic OH group in one of its substituents. Compounds 9a and 9b were obtained by single-step alkylations of 7a and 7b with 1,6-dibromohexane or, in better yields, by coupling of Pcs 7a and 7b with the bromoalkyl-derivatized

  我们报告了二聚同核 Pcs 9a 和 9b 以及二聚异核 Pc 9c 的合成，从不对称的酞菁 7a 和 7b 开始，每一种都在其取代基之一中包含一个酚类 OH 基团。化合物 9a 和 9b 是通过 7a 和 7b 与 1,6-二溴己烷的一步烷基化获得的，或者通过将 Pcs 7a 和 7b 与溴代烷基衍生的 Pcs 8a 和 8b 偶联以更高的收率获得，而 9c 是通过处理制备的8a 与 Pc-Ni 配合物 7b。二聚体 Pcs 9a-9c 在溶液中显示出强烈的共面分子内缔合。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• PHTHALONITRILE MONOMER MODIFIED WITH ORGANOSILICON FRAGMENTS
  申请人：Joint Stock Company Scientific and Production Association "Unichimtek" (JSC PSA "Unichimtek)

  公开号：EP3211023A1

  公开（公告）日：2017-08-30

  This invention relates to the field of organic chemistry, more particularly, to a method of obtaining modified phtalonitriles comprising organosilicon fragments and binding agents based thereon, and can be used in a variety of technical fields, for example, in aircraft and automobile manufacturing to produce polymer composite materials. The phtalonitrile monomer modified with organosilicon fragments in accordance with this invention is characterized by the general formula where X is a bivalent aromatic radical, and Y is an organosilicon fragment. The method of obtaining a modified phtalonitrile monomer includes the obtaining of hydroxyl-containing phtalonitrile and subsequent synthesis of phtalonitrile monomer from said hydroxyl-containing phtalonitrile. Such phtalonitrile combines the properties of conventional phtalonitrile types, e.g. their high thermal resistance, with the advantages of organosilicon polymers, which possess good solubility, thermal stability, and low glass transition temperature ensuring their physical state at ambient temperatures as a viscous liquid or semi-solid substance. A binder and a prepreg based on the modified phtalonitrile monomer according to this invention are also disclosed.

  本发明涉及有机化学领域，更具体地说，涉及一种获得包含有机硅片段和以其为基础的结合剂的改性酞腈的方法，可用于各种技术领域，例如飞机和汽车制造领域，以生产聚合物复合材料。根据本发明，用有机硅片段改性的酞腈单体的通式为 其中 X 为二价芳香基，Y 为有机硅片段。获得改性邻苯二腈单体的方法包括获得含羟基的邻苯二腈，然后用所述含羟基的邻苯二腈合成邻苯二腈单体。这种聚对苯二甲腈结合了传统聚对苯二甲腈的特性（如高耐热性）和有机硅聚合物的优点，有机硅聚合物具有良好的溶解性、热稳定性和低玻璃化转变温度，确保其在环境温度下的物理状态为粘稠液体或半固体物质。本发明还公开了一种基于改性聚苯腈单体的粘合剂和预浸料。