4-isocyanate-4-(3,3-dimethyl-2,4-dioxo-azetidine)diphenyl methane | 102196-11-2

• 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-isocyanate-4-(3,3-dimethyl-2,4-dioxo-azetidine)diphenyl methane
• 英文别名: 4-isocyanato-4'-(3,3-dimethyl-2,4-dioxo-acetidino)diphenylmethane；4-isocyanato-4'-(3,3-dimethyl-2,4-dioxoazetidino)diphenylmethane；4-isocyanato-4-(3,3-dimethyl-2,4-dioxo-acetidino)diphenylmethane；IDD；1-[4-[(4-Isocyanatophenyl)methyl]phenyl]-3,3-dimethylazetidine-2,4-dione
• CAS: 102196-11-2
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: WYQDSVOXDZYLLA-UHFFFAOYSA-N

物化性质

• 沸点：
  457.5±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-isocyanate-4-(3,3-dimethyl-2,4-dioxo-azetidine)diphenyl methane 、 二乙醇胺 以 四氢呋喃 为溶剂， 反应 2.0h， 以86.7%的产率得到octadecyl N-[4-[[4-(3,3-dimethyl-2,4-dioxoazetidin-1-yl)phenyl]methyl]phenyl]carbamate
  参考文献：
  名称：

  Honeycomb-like polymeric films from dendritic polymers presenting reactive pendent moieties

  摘要：

  In this paper we describe the fabrication of honeycomb-shaped polyurethane films from dendritic side-chain polymers presenting reactive pendent units. Two novel functional polyurethanes, poly(urethane-co-acylurea) (PU-PACY) and polyurethane-co-azetidine-2,4-dione containing polyurethane (PU-PAZ), were synthesized. The waxy dendrons featured focal urea/malonamide linkages favorable for hydrogen bonding and peripheral alkyl chains. These intermolecular forces caused two functional PUs to undergo phase separation and self-assembly. This resulted in honeycomb-like films with well-controlled surface roughness characterized in terms of the ratio of rim width (W) to the pore size (D), i.e. W/D. The PU-PAZ film had a higher contact angle (CA) and a lower value of W/D than did the PU-PACY analogue, due to the presence of relatively more hydrophobic azetidine-2, 4-dione functionalities in the former film. Subsequent chemical modification of the PU-PAZ films through reaction with a hydrophobic poly(oxyalkylene) amine enhanced the CA from 113 to 134 degrees. Further physical modification through a peeling-off process rendered the film surface with a three-dimensional (3D) rod-co-valley-structure having feature dimensions on a submicrometer scale. The 3D rod-co-valley like film exhibited superhydrophobicity with a CA of 151 degrees. The films also displayed excellent solvent-resistance after crosslinking with a diamine. Through hydrophobic or hydrophilic chemical modification, we could readily manipulate the surface properties of these honeycomb-like films with controllable surface roughnesses and reactive functionalities. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2014.01.032
• 作为产物：
  描述：

  异丁酰氯 、 4,4'-二苯甲烷二异氰酸酯、2,4'-二苯甲烷二异氰酸酯和2,2'-二苯甲烷二异氰酸酯的混合物 在 三乙胺 作用下， 以 xylene 为溶剂， 反应 7.0h， 以33%的产率得到4-isocyanate-4-(3,3-dimethyl-2,4-dioxo-azetidine)diphenyl methane
  参考文献：
  名称：

  Synthesis and montmorillonite-intercalated behavior of dendritic surfactants

  摘要：

  我们采用聚合法合成了一系列新型树枝状化合物，可用作蒙脱石（MMT）表面改性的表面活性剂。所制备树枝状化合物的最大特点是外围的烷基链很长。这无疑会带来良好的溶解性、高产量和易提纯性。通过简单地酸化树枝状化合物上的 "头部基团"，然后用 Na+-MMT 进行离子交换，可以大大增加层状硅酸盐之间的层间距离。通过热重分析（TGA）测定的有机/无机比率在 60%-91% 之间。这也证实了 Na+-MMT 发生了树枝状离子交换。透射电子显微镜（TEM）显示了树枝膦改性 MMT 的插层和剥离形态。在这项工作中，使用分子量（Mw）= 2887.5 的第二代树枝状表面活性剂（G2）进行改性实现了剥离形态。

  DOI：

  10.1039/b600544f

文献信息

• Side chain dendritic polyurethanes with shape-memory effect
  作者：Cheng-Che Tsai、Chia-Cheng Chang、Ching-Shiang Yu、Shenghong A. Dai、Tzong-Ming Wu、Wen-Chiung Su、Chang-Nan Chen、Franklin M. C. Chen、Ru-Jong Jeng

  DOI：10.1039/b910614f

  日期：——

  In this study, thermally reversible polyurethanes (PUs) with shape memory effect were developed by using hydrogen bonding to enhance physical interactions. Two different types of PUs were synthesized: (1) a linear PU whose hard segment consists of methylene di-para-phenyl isocyanate (MDI) and di(ethylene glycol) (DEG); its soft segment is made of Tone 0260 polyol, a polyester polyol; (2) a side-chain dendritic PU which replaces DEG with different generations of dendritic chain extenders. By incorporation of the dendritic structure with peripheral long alkyl chains (strong van der Waals forces), the miscibility between hard and soft segments can be significantly improved. Consequently, the hydrogen bonding reinforced hard segments (malonamide linkages) of side chain dendritic PUs result in greatly enhanced mechanical properties and shape memory effect. During cyclic shape memory tests, one of the series can effortlessly achieve complete recovery in less than 10 second without any deficiency.

  本研究利用氢键增强物理相互作用，开发出了具有形状记忆效应的热可逆聚氨酯（PUs）。研究人员合成了两种不同类型的聚氨酯：（1）线性聚氨酯，其硬段由二对苯二甲异氰酸酯（MDI）和二乙二醇（DEG）组成，软段由聚酯多元醇 Tone 0260 多元醇制成；（2）侧链树枝状聚氨酯，用不同代树枝状链延伸剂取代二乙二醇。通过在树枝状结构中加入外围长烷基链（范德华力很强），可显著提高软硬片段之间的相溶性。因此，侧链树枝状聚氨酯的氢键强化硬段（丙二酰胺连接）可大大提高机械性能和形状记忆效果。在循环形状记忆测试中，其中一个系列可以毫不费力地在不到 10 秒的时间内实现完全恢复，而不会出现任何缺陷。
• Novel dendritic-poly(urethane-urea) hybrid thin films from hydrogen bond rich dendrons
  作者：Aravindaraj G. Kannan、Namita Roy Choudhury、Naba K. Dutta

  DOI：10.1016/j.polymer.2014.08.017

  日期：2014.9

  Hydrogen bond rich segmented poly(urethane-urea) was synthesized from methylene diphenylisocyanate (MDI) and three generations of polyurea-malonamide dendrons as hard segment and polycaprolactone diol as soft segment for thin film applications. The prepared polymers were characterized using spectroscopic, microscopic and thermal analyses. The formation of urethane linkage during the prepolymer reaction and the urea linkage between prepolymer and the dendrons is confirmed by Fourier transform infrared (FTIR) spectroscopy and H-1 nuclear magnetic resonance (NMR) spectroscopy. FTIR shows the presence of hydrogen bonding of -NH groups with both urethane carbonyl group from hard segment and the ether group from the soft segment. However, the phase mixing of hard and soft segments decreases with the higher generation dendrons, as evidenced from FUR. This observation was confirmed by phase images of the atomic force microscopy (AFM). The coating when applied to clean steel substrates via dip coating reveals uniform, dense and essentially defect free morphology. The work demonstrates that the mechanical properties of the hybrid thin films are dependent on the generation of the dendrons and provides a platform for surface engineering with tunable elastic modulus. (C) 2014 Elsevier Ltd. All rights reserved.
• DEVELOPMENT OF A NOVEL CROSS-LINKED EPOXY RESIN WITH FLAME-RETARDANT PROPERTIES
  申请人：SU WEN-CHIUNG

  公开号：US20100130698A1

  公开（公告）日：2010-05-27

  The invention discloses a novel cross-linked epoxy resin with flame-retardant properties and method for producing the same. The polymeric material of the invention includes an epoxy resin, a curing agent and a modification agent. Particularly, the modification agent is a derivative of 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide (DOPO). Moreover, the curing agent is 4,4′-diaminodiphenyl methane (DDM), or tris(4-aminephenyl)amine (NNH).
• DEVELOPMENT OF A CROSS-LINKED EPOXY RESIN WITH FLAME-RETARDANT PROPERTIES
  申请人：SU WEN-CHIUNG

  公开号：US20110118423A1

  公开（公告）日：2011-05-19

  The invention discloses a cross-linked epoxy resin with flame-retardant properties and method for producing the same. The polymeric material of the invention includes an epoxy resin, a curing agent and a modification agent. Particularly, the modification agent is a derivative of 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO). Moreover, the curing agent is 4,4′-diaminodiphenyl methane (DDM), or tris(4-aminophenyl)amine (NNH).
• US20140343224A1
  申请人：——

  公开号：US20140343224A1

  公开（公告）日：2014-11-20