1-异氰酸根-2-[(4-异氰酸根苯基)甲基]苯 | 5873-54-1

• 物质功能分类: 化学试剂 - 有机试剂 - 氰酸酯/异氰酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-异氰酸根-2-[(4-异氰酸根苯基)甲基]苯
• 中文别名: 1-异氰酸基-2-[(4-异氰酸基苯基)甲基]苯
• 英文名称: 2,4'-diisocyanatodiphenylmethane
• 英文别名: 2,4'-diisocyanato-1,1-methylenedibenzene；2,4'-methylene diphenyl diisocyanate；2,4'-diphenylmethane diisocyanate；2,4'-Diisocyantodiphenylmethane；2,4'-MDI；o-(p-isocyanatobenzyl)phenyl isocyanate；Benzene, 1-isocyanato-2-[(4-isocyanatophenyl)methyl]-；1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene
• CAS: 5873-54-1
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: LFSYUSUFCBOHGU-UHFFFAOYSA-N

物化性质

• 熔点：
  36-40 °C(lit.)
• 沸点：
  376.3±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)
• 闪点：
  110 °C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  Liquid

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36
• 危险类别码：
  R20/21/22,R36/37/38

制备方法与用途

应用

1-异氰酸根-2-[(4-异氰酸根苯基)甲基]苯可用于制备聚氨酯复膜胶。该复膜胶主要应用于食品、药品、洗涤剂等软包装上，具有柔软、透明和强粘接力的特点。通过灵活的配方设计与原料选择，可获得耐油、耐酸及耐高温等特殊性能，展现出很高的研究价值和实用价值。聚氨酯复膜胶的主要原料之一是MDI-50。

制备

粗MDI含有60%两环、10%三环、10%四环以及20%五环及以上混合物，在塔底温度为215℃、塔顶温度90℃及塔顶压力0.4kPa的条件下，通过真空分离塔进行分离。得到二苯基甲烷二异氰酸混合物A1和聚合MDI。

将含有2% 2,2-MDI、10% 2,4-MDI及88% 4,4-MDI的二苯基甲烷二异氰酸混合物A1引入精馏塔。通过调整各参数，如精馏塔釜温度控制在210℃、在线4,4-MDI采出段温度208℃以及在线4,4-MDI采出比例以进料异氰酸酯混合物重量为基准质量比控制在80%等，最终得到MDI-50产品。该产品的组成为：2,2-二苯基甲烷二异氰酸酯含量为0.8wt%，2,4-二苯基甲烷二异氰酸酯含量为5.2wt%，4,4-二苯基甲烷二异氰酸酯为94wt%。其游离氯含量为5ppm。

通过结晶装置浓缩游离氯，控制结晶终点温度在18℃，残液质量占原料质量比例达25%，最终得到MDI-50产品。该产品的组成为：2,2-二苯基甲烷二异氰酸酯含量为3.2wt%，2,4-二苯基甲烷二异氰酸酯含量为19.6wt%，4,4-二苯基甲烷二异氰酸酯为77.2wt%。其游离氯含量为17ppm。

最后，在500g中间品中加入500g 2,2-二苯基甲烷二异氰酸酯含量为1wt%，2,4-二苯基甲烷二异氰酸酯含量为80wt%，4,4-二苯基甲烷二异氰酸酯为19wt%，游离氯为1ppm的二苯基甲烷二异氰酸酯混合物D1，于45℃下搅拌2小时。最终得到MDI-50产品的组成为：2,2-二苯基甲烷二异氰酸酯含量为2.1wt%，2,4-二苯基甲烷二异氰酸酯含量为49.8wt%，4,4-二苯基甲烷二异氰酸酯为48.1wt%，游离氯为9ppm。

反应信息

• 作为反应物：
  描述：

  1-异氰酸根-2-[(4-异氰酸根苯基)甲基]苯 在 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.02h， 以0.3%的产率得到2-[(4-氨基苯)甲基]苯胺
  参考文献：
  名称：

  Chemical behaviour of seven aromatic diisocyanates (toluenediisocyanates and diphenylmethanediisocyanates) under in vitro conditions in relationship to their results in the Salmonella/microsome test

  摘要：

  There are conflicting results on the mutagenicity of toluenediisocyanate (TDI) and diphenylmethanediisocyanate (MDI). It was found that the organic solvent chosen to dissolve the compounds dictates the outcome of the bacterial tests. The Salmonella/microsome tests showed uniformly mutagenic effects for all the compounds that were predissolved in DMSO. Due to the instability of aromatic diisocyanates in DMSO this solvent was replaced by ethyleneglycoldimethylether (EGDE). TDI and MDI endured the dissolving and were therefore still available for the subsequent bacterial tests. Furthermore, no aromatic diamines (TDA or MDA) could be detected in EGDE prior to the start of the assays. The Salmonella/microsome tests, however, revealed unexpected differences between TDI and MDI. As previously published the four types of MDI showed negative results, whereas the data presented in this paper demonstrated mutagenic effects of all three types of TDI if EGDE is the solvent. To gain deeper insight into the chemical changes that occurred during the Salmonella/microsome test, the possible reactions were modelled in the laboratory by mixing predissolved diisocyanates with a defined surplus of water and monitoring the progress of the chemical reactions by analytical methods. Additionally, the quality of the model was checked by exposing solutions of 2,6-TDI and 4,4'-MDI to the real biological test environment. In both cases, the reaction patterns of TDI were different to those of MDI. Within 1 min, which is the maximum time needed to mix the predissolved compounds with water before they are poured onto the agar plate, the TDI content was reduced in favour of different ureas and TDA. In addition water was replaced by the complete set of test ingredients. While the TDA content remained more or less constant, the amount of residual TDI was reduced considerably. Reactions of MDI were markedly slower than those of TDI. More than 90% of the predissolved MDI remained intact when it was mixed with water. The biological test ingredients accelerated the reduction of the MDI content. Within 45 s, more than two thirds of the MDI disappeared. Evidently, the chemical reactions continue during incubation. It is assumed that the contrasting results of TDI and MDI in the Salmonella/microsome test are due to the different reaction patterns-and reaction products-of the predissolved diisocyanates created under the specific conditions of the test. These findings indicate that the chemical interactions between reactive test compounds and solvents or test media need to be considered in the interpretation of the relevance of test results.(C) 1999 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(98)00157-0
• 作为产物：
  描述：

  光气 、 2-[(4-氨基苯)甲基]苯胺 、 4,4'-二氨基二苯甲烷 以 氯苯 为溶剂， 反应 -5.0h， 生成 1-异氰酸根-2-[(4-异氰酸根苯基)甲基]苯 、 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
  参考文献：
  名称：

  PROCESS FOR PREPARING AROMATIC ISOCYANATES

  摘要：

  本发明涉及一种通过在液相中反应相应胺和光气制备异氰酸酯的方法，如有必要，在至少一种惰性介质的存在下进行。在此方法中，首先将胺和光气混合在混合室（1）中以形成反应混合物，然后将反应混合物送入反应器，其中通过同轴排列的小孔（3）加入胺，通过垂直于混合室（1）轴线（11）排列的至少两个平面（7，9）的进料小孔（5）加入光气，或者通过同轴排列的小孔（3）加入光气，通过垂直于混合室（1）轴线（11）排列的至少两个平面（7，9）的进料小孔（5）加入胺。至少一个平面（9）位于同轴排列的小孔（3）的主流方向上游，至少一个平面（7）位于同轴排列的小孔（3）的主流方向下游。反应混合物在混合室（1）中的平均停留时间不超过20毫秒。

  公开号：

  US20110251425A1

文献信息

• [EN] PHOTOCHROMIC THIENOCHROMENE COMPOUNDS<br/>[FR] COMPOSÉS THIÉNOCHROMÈNE PHOTOCHROMIQUES
  申请人：TRANSITIONS OPTICAL INC

  公开号：WO2016144324A1

  公开（公告）日：2016-09-15

  The present invention relates to photochromic compounds, such as thienochromene compounds represented by the following Formulas (la) and/or (lb). The present invention also relates to photochromic compositions and articles containing one or more such photochromic thienochromene compounds.

  本发明涉及光致变色化合物，例如由以下式（Ia）和/或（Ib）表示的噻吩基色烯化合物。本发明还涉及含有一种或多种此类光致变色噻吩基色烯化合物的光致变色组合物和制品。
• Polyether-modified polymers as leather auxiliaries
  申请人：Reiners Juergen

  公开号：US20050058619A1

  公开（公告）日：2005-03-17

  (Co)polymers which contain a) structural units of the general formula I in which W represents a trivalent radical from the group in which * indicates the orientation for the incorporation of the radical W into the formula I, and Z represents the radicals —OH, —O − M + or —N—R 1 R 2 , in which R 1 and R 2 , independently of one another, represent hydrogen, optionally substituted alkyl radicals, alkenyl radicals, aralkyl radicals or cycloalkyl radicals, which may be interrupted by 0 atoms, N atoms, Si atoms or amido, carbonate, urethane, urea, allophanate, biuret or isocyanurate groups or mixtures thereof, and M + represents H + or an alkali metal ion, an NH 4 ion or a primary, secondary, tertiary or quaternary aliphatic ammonium radical which preferably carries a C 1 -C 22 -alkyl or C 1 -C 22 -hydroxyalkyl group, b) at least 10 mol %, based on the units of the formula I, of structural units of the general formula Ia in which R 3 represents a hydrocarbon radical having C 1 -C 60 -atoms, preferably a saturated C 1 -C 60 -alkyl radical, in particular C 12 -C 30 -alkyl radical, and R 4 represents hydrogen or has the same meaning as R 3 , and e) polyether units having an average molecular weight of 200 - 6000 g/mol.

  聚合物包含a) 通式I的结构单元，其中W代表来自该组的三价基团，其中*表示将基团W合并到通式I中的取向，Z代表基团—OH，—O−M+或—N—R1R2，其中R1和R2独立地表示氢，可选择地取代的烷基基团，烯基基团，芳基烷基基团或环烷基基团，可以由0个原子，N原子，Si原子或酰胺，碳酸酯，脲，脲，异氰酸酯，双脲基或异氰酸酯基团或它们的混合物中断，并且M+表示H+或碱金属离子，NH4离子或一种一级，二级，三级或季铵基团，最好携带C1-C22-烷基或C1-C22-羟基烷基基团，b)至少占通式I单位的10摩尔％的通式Ia的结构单元，其中R3代表具有C1-C60原子的碳氢基团，优选为饱和的C1-C60烷基基团，特别是C12-C30烷基基团，和R4代表氢或具有与R3相同的含义，以及e) 平均分子量为200-6000g/mol的聚醚单元。
• COPOLYMERS AND COMPOSITIONS WITH ANTI-ADHESIVE AND ANTIMICROBIAL PROPERTIES
  申请人：BASF SE

  公开号：US20160235062A1

  公开（公告）日：2016-08-18

  The invention relates to a copolymer exhibiting both antimicrobial and anti-adhesive properties as well as to a hydrogel. Said hydrogel is obtained from the inventive copolymer and a substrate. Another part of the invention is a process for making the hydrogel, as well as different uses of the inventive copolymer as well as of the hydrogel.

  该发明涉及一种既具有抗菌和抗粘附性能的共聚物，又涉及一种水凝胶。所述水凝胶是由该创新共聚物和基质制得的。该发明的另一部分是制备水凝胶的方法，以及该创新共聚物和水凝胶的不同用途。
• Release sustaining composition and sustained release preparation
  申请人：Hayakawa Kazuhisa

  公开号：US20050147676A1

  公开（公告）日：2005-07-07

  A release sustaining composition comprising a polyalkylene polyol derivative comprising repeating units U-1 derived from a water-soluble polyalkylene polyol and a polyisocyanate and repeating units U-2 derived from a dihydroxy compound and a polyisocyanate in a molar ratio of U-1/U-2 between 0.5/0.5 and 0.99/0.01 and optionally a water-soluble cellulose ether is combined with an active ingredient to make a sustained release preparation.

  一种持续释放组合物，包括由可溶于水的聚烯烃聚醚和聚异氰酸酯衍生的重复单元U-1以及由二羟基化合物和聚异氰酸酯衍生的重复单元U-2，在U-1/U-2的摩尔比在0.5/0.5至0.99/0.01之间，可选地与可溶于水的纤维素醚结合，用于制备持续释放制剂。
• Biobased compositions
  申请人：EVOCO LIMITED

  公开号：US11072694B1

  公开（公告）日：2021-07-27

  A composition comprised of a component selected from the group consisting of a biobased bis-alkyl succinate and a biobased bis-alkyl sebacate, each derived, for example, from the esterification of biobased diacid such as succinic acid or sebacic acid, and a biobased alcohol and a biobased polyester.

  一种由从生物基双烷基琥酸盐和生物基双烷基硬脂酸盐组成的组分构成的组合物，每种组分例如均来源于生物基二酸（如琥酸或硬脂酸）的酯化反应产生的生物基醇和生物基聚酯。