2,4-十九碳二炔酸 | 174063-97-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,4-十九碳二炔酸
• 英文名称: 6,8-nonadecadiynoic acid
• 英文别名: Nonadeca-6,8-diynoic acid
• CAS: 174063-97-9
• 化学式: C₁₉H₃₀O₂
• 分子量: 290.446
• InChiKey: STCGDIJOEZNVHP-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59 °C
• 沸点：
  449.7±28.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916190090

反应信息

• 作为反应物：
  描述：

  2,4-十九碳二炔酸 、 乙二胺 在 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 49.0h， 以46%的产率得到N,N'-ethylenebis(nonadeca-6,8-diynamide)
  参考文献：
  名称：

  Tuning Down of Color Transition Temperature of Thermochromically Reversible Bisdiynamide Polydiacetylenes

  摘要：

  A series of bisdiynamide lipids containing various lengths of methylene spacer (m = 2, 3 and 4) between the diynes and the diamide headgroup and number of methylene units (n = 6 and 9) in their hydrophobic tails are synthesized. All six lipids synthesized can be dispersed in water and photopolymerized by UV irradiation to give the corresponding polydiacetylene (PDA) sols. The color transitions from blue to red during heating-cooling cycles of the PDA sols are photographically recorded and monitored by UV-vis absorption spectroscopy. The bisdiynamide PDAs exhibit excellent thermochromic reversibility and the color transition temperature can be tuned between ca. 25-55 degrees C by the variation of m and n values. Temperature indicators can be obtained by applying a screen printing ink formulated from the bisdiynamide monomer on plastic substrates followed by UV irradiation to generate desired patterns of thermochromically reversible PDAs.

  DOI：

  10.1021/ma101264k
• 作为产物：
  描述：

  1-十二炔 在 四氢吡咯 、 吗啉 、 copper(l) iodide 、 碘 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 2,4-十九碳二炔酸
  参考文献：
  名称：

  Tuning Down of Color Transition Temperature of Thermochromically Reversible Bisdiynamide Polydiacetylenes

  摘要：

  A series of bisdiynamide lipids containing various lengths of methylene spacer (m = 2, 3 and 4) between the diynes and the diamide headgroup and number of methylene units (n = 6 and 9) in their hydrophobic tails are synthesized. All six lipids synthesized can be dispersed in water and photopolymerized by UV irradiation to give the corresponding polydiacetylene (PDA) sols. The color transitions from blue to red during heating-cooling cycles of the PDA sols are photographically recorded and monitored by UV-vis absorption spectroscopy. The bisdiynamide PDAs exhibit excellent thermochromic reversibility and the color transition temperature can be tuned between ca. 25-55 degrees C by the variation of m and n values. Temperature indicators can be obtained by applying a screen printing ink formulated from the bisdiynamide monomer on plastic substrates followed by UV irradiation to generate desired patterns of thermochromically reversible PDAs.

  DOI：

  10.1021/ma101264k

文献信息

• Polydiacetylene paper-based colorimetric sensor array for vapor phase detection and identification of volatile organic compounds
  作者：Thichamporn Eaidkong、Radeemada Mungkarndee、Chaiwat Phollookin、Gamonwarn Tumcharern、Mongkol Sukwattanasinitt、Sumrit Wacharasindhu

  DOI：10.1039/c2jm16273c

  日期：——

  Detection and identification of VOCs in their vapor phase is essential for safety and quality assessment. In this work, a novel platform of a paper-based polydiacetylene (PDA) colorimetric sensor array is prepared from eight diacetylene monomers, six of which are amphiphilic and the other two are bolaamphiphilic. To fabricate the sensors, monomers are coated onto a filter paper surface using the drop-casting technique and converted to PDAs by UV irradiation. The PDA sensors show solvent induced irreversible color transition upon exposure to VOC vapors. When combined into a sensing array, the color change pattern as measured by RGB values and statistically analyzed by principal component analysis (PCA) is capable of distinguishing 18 distinct VOCs in the vapor phase. The PCA score and loading plots also allow the reduction of the sensing elements in the array from eight to three PDAs that are capable of classifying 18 VOCs. Utilizing an array containing only two PDAs, various types of automotive fuels including gasoline, gasohol and diesel are successfully classified.

  检测和识别气相中的挥发性有机化合物对于安全和质量评估至关重要。本研究利用八种双乙炔单体制备了一种新型纸基聚二乙炔（PDA）比色传感器阵列平台，其中六种为双亲性单体，另外两种为双亲性单体。为了制造传感器，使用滴铸技术将单体涂覆在滤纸表面，然后通过紫外线照射将其转化为 PDA。PDA 传感器在暴露于挥发性有机化合物蒸汽时会出现溶剂诱导的不可逆颜色转换。当组合成传感阵列时，通过 RGB 值测量和主成分分析 (PCA) 统计分析的颜色变化模式能够区分气相中 18 种不同的挥发性有机化合物。PCA 分数和载荷图还允许将阵列中的传感元件从八个减少到三个 PDA，从而能够对 18 种挥发性有机化合物进行分类。利用仅包含两个 PDA 的阵列，成功地对汽油、汽油醇和柴油等各种汽车燃料进行了分类。
• COLOR CHANGING INK JET INK WITH TUNABLE TRANSITION STIMULI
  申请人：Xerox Corporation

  公开号：EP3670616A1

  公开（公告）日：2020-06-24

  A composition including a molecule comprising (1) a diacetylene moiety or diacetylene precursor; and (2) an alkyl additive; water; an optional co-solvent; an optional surfactant; an optional stabilizer; wherein the composition has the characteristic of color change after application of a stimulus. A process for preparing the composition. A process for preparing a product by printing the composition.

  一种组合物，包括由以下成分组成的分子：(1) 二乙炔分子或二乙炔前体；(2) 烷基添加剂；水；任选助溶剂；任选表面活性剂；任选稳定剂；其中该组合物在施加刺激后具有颜色变化的特性。一种制备该组合物的工艺。一种通过印刷该组合物制备产品的工艺。
• COLOR-CHANGING PARTICULATE COMPOSITIONS FOR ADDITIVE MANUFACTURING AND METHODS ASSOCIATED THEREWITH
  申请人：Xerox Corporation

  公开号：EP3992234A1

  公开（公告）日：2022-05-04

  Additive manufacturing processes, such as powder bed fusion of thermoplastic particulates, may be employed to form printed objects in a range of shapes. Formation of printed objects having various colors may sometimes be desirable. Thermoplastic particulates incorporating a color-changing material capable of forming different colors under specified activation conditions may impart different colors to a printed object. Such particulate compositions may comprise a plurality of thermoplastic particulates comprising a thermoplastic polymer and a color-changing material associated with the thermoplastic particulates, wherein the color-changing material is photochromic and thermochromic. Conjugated diynes, such as 10,12-pentacosadiynoic acid or a derivative thereof, may be particularly suitable color-changing materials having photochromic and thermochromic properties for forming a range of colors upon a printed object. Nanoparticles, particularly silica nanoparticles, associated with an outer surface of the thermoplastic particulates may enhance the brightness of the color obtained under various activation conditions and afford coloration permanence.

  快速成型制造工艺，如热塑性颗粒的粉末床熔融，可用于形成各种形状的印刷物体。有时可能需要形成具有各种颜色的印刷物体。含有变色材料的热塑性微粒能够在特定的活化条件下形成不同的颜色，从而为印刷物体赋予不同的颜色。这种微粒组合物可以由多个热塑性微粒组成，热塑性微粒包括热塑性聚合物和与热塑性微粒相关的变色材料，其中变色材料具有光致变色和热致变色功能。共轭二炔，如 10,12-五聚二炔酸或其衍生物，可能是特别合适的变色材料，具有光致变色和热致变色特性，可在印刷物体上形成一系列颜色。与热塑性微粒外表面相关联的纳米颗粒，特别是二氧化硅纳米颗粒，可以提高在各种活化条件下获得的颜色的亮度，并提供着色持久性。
• Plastics colouration
  申请人：Jarvis Anthony

  公开号：US10246562B2

  公开（公告）日：2019-04-02

  A method of imparting color to a plastic substrate comprising applying to the substrate, or incorporating within the substrate, a diacetylene compound of general formula (I) wherein n=1 to 20; R1=an optionally substituted C1-20 alkyl group which may contain heteroatoms; T=H, an optionally substituted C1-20 alkyl group which may contain heteroatoms or —(CH2)m—C(═O)-Q2R2; Q1=NH, CO, NHCONH, OCONH, COS, NHCSNH or NR3, wherein m, Q2 and R2 are independently selected from the same groups as n, Q1 and R1 respectively; R3 is an optionally substituted C1-20 alkyl group which may contain heteroatoms; and irradiating the substrate to impart color to the substrate is described.

  一种使塑料基材着色的方法，包括将通式(I)的二乙炔化合物涂敷于基材上或掺入基材中，其中n=1至20；R1=可含有杂原子的任选取代的C1-20烷基；T=H、可含有杂原子的任选取代的C1-20烷基或-(CH2)m-C(═O)-Q2R2；Q1=NH、CO、NHCONH、OCONH、COS、NHCSNH 或 NR3，其中 m、Q2 和 R2 分别独立地选自与 n、Q1 和 R1 相同的基团；R3 是可含有杂原子的任选取代的 C1-20 烷基；以及辐照底物以赋予底物颜色的描述。
• Reversible Color Changes in Lamella Hybrids of Poly(diacetylenecarboxylates) Incorporated in Layered Double Hydroxide Nanosheets
  作者：Toshio Itoh、Tetsuya Shichi、Tatsuto Yui、Hiroki Takahashi、Yoshihisa Inui、Katsuhiko Takagi

  DOI：10.1021/jp045410e

  日期：2005.3.1

  The present study is an investigation of a reversible thermal color change induced in lamella hybrids of poly(diacetylenecarboxylates) incorporated in layered double hydroxide (LDH) nanosheets. These poly-[m,n]/ LDH hybrids prepared by the photo- or gamma-ray-induced polymerization of diacetylenecarboxylates, i.e., CH3-(CH2)(m-1) CdropC-CdropC(CH2)(n-1)CO2- (mono-[m,n]), and intercalated in LDH lamella sheets, were observed to develop colors ranging from yellow to blue. The change in color was found to depend greatly on the alkyl carbon numbers of the mono-[m,n] (m,n = 10, 11; 5,11; 10,5; 16, 1) values. Moreover, the conformational alignment of the mono-[m,n] within the LDH was observed to be a crucial factor in color development, which was greatly affected by the intercalation degrees and extent of poly(ene-yne) linkage elongation of the polymers. For the poly-[m,n]/LDH hybrids investigated, a reversible color change was found to occur repeatedly and remarkably for the poly- [10,11]/LDH hybrid. This color change occurred at temperatures between ca. 20 and 80 degreesC back and forth from purple red to bright orange, in stark contrast to the irreversible color change for poly-[10,11] without LDH. Moreover, DSC and Raman spectroscopic studies of the LDH hybrids showed that the thermochromic temperature corresponded to the phase transition temperature of 80 degreesC. XRD analysis also indicated that the poly-[m,n]/LDH hybrid could retain its lamella structure during such thermochromic color changes, enabling conformational recovery in the polymer chains by a cooling down of the hybrids to temperatures lower than the transition temperature, while the nonhybrid poly-[10,11] powders exhibited an irreversible color change at 60 degreesC, above which the polymer powder turned amorphous.