2-(dodecylthiocarbonothioylthio)-2-methylpropanoic acid 2-phenoxyethyl ester | 1334532-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(dodecylthiocarbonothioylthio)-2-methylpropanoic acid 2-phenoxyethyl ester
• 英文别名: 2-Phenoxyethyl 2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoate；2-phenoxyethyl 2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoate
• CAS: 1334532-10-3
• 化学式: C₂₅H₄₀O₃S₃
• 分子量: 484.789
• InChiKey: FMGZXHKBSDRMIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  31
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  己二酸,聚合2,2-二甲基-1,3-丙二醇和2,5-呋喃二酮,苯酸酯 、 2-[十二烷硫基(硫代羰基)硫基]-2-甲基丙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以75%的产率得到2-(dodecylthiocarbonothioylthio)-2-methylpropanoic acid 2-phenoxyethyl ester
  参考文献：
  名称：

  Synthesis of Sterically-Stabilized Polystyrene Latexes Using Well-Defined Thermoresponsive Poly(N-isopropylacrylamide) Macromonomers

  摘要：

  A series of well-defined thermo-responsive poly(N-isopropylacrylamide) (PNIPAM) macromonomers was prepared by reversible addition fragmentation chain transfer (RAFT) polymerization followed by aminolysis and nucleophilic Michael addition. 2-(Dodecylthiocarbonothioylthio)-2-methylpropanoic-2-phenoxyethyl ester (CTA) was used as the RAFT chain transfer agent to prepare six PNIPAM-CTA precursors with target degrees of polymerization of 20, 30, 40, 50, 60, and 75. These NIPAM polymerizations were conducted in 1,4-dioxane and proceeded with good control and low polydispersities (M-w/M-n < 1.10) up to more than 90% conversion. The PNIPAM trithiocarbonate end-groups were then converted to methacrylate end-groups by combining (i) aminolysis and (ii) nucleophilic Michael addition using the bifunctional reagent, 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA), in a one pot reaction. The resulting PNIPAM macromonomers were evaluated as reactive steric stabilizers for latex syntheses. Near-monodisperse submicrometer-sized latexes were obtained by alcoholic dispersion polymerization of styrene in methanol, as judged by scanning electron microscopy (SEM) and dynamic light scattering (DLS). In contrast, a latex synthesized in the presence of a PNLPAM-CTA had a bimodal size distribution, while thiol-capped PNIPAM chains produced ill defined nonspherical particles and styrene polymerization conducted in the absence of any stabilizer led to macroscopic precipitation. These control experiments confirm that using the methacrylate-capped macromonomers is essential for successful latex syntheses. H-1 NMR analysis confirm the presence of PNIPAM chains in the latex particles and XPS measurements indicate that the stabilizer is located on the particle surface, as expected. The well-known thermo-responsive nature of the stabilizer was successfully transferred to these latexes, which exhibit reversible flocculation upon heating above the LCST of the PNIPAM chains.

  DOI：

  10.1021/ma2016584

文献信息

• Synthesis of Sterically-Stabilized Polystyrene Latexes Using Well-Defined Thermoresponsive Poly(<i>N</i>-isopropylacrylamide) Macromonomers
  作者：J. R. McKee、V. Ladmiral、J. Niskanen、H. Tenhu、S. P. Armes

  DOI：10.1021/ma2016584

  日期：2011.10.11

  A series of well-defined thermo-responsive poly(N-isopropylacrylamide) (PNIPAM) macromonomers was prepared by reversible addition fragmentation chain transfer (RAFT) polymerization followed by aminolysis and nucleophilic Michael addition. 2-(Dodecylthiocarbonothioylthio)-2-methylpropanoic-2-phenoxyethyl ester (CTA) was used as the RAFT chain transfer agent to prepare six PNIPAM-CTA precursors with target degrees of polymerization of 20, 30, 40, 50, 60, and 75. These NIPAM polymerizations were conducted in 1,4-dioxane and proceeded with good control and low polydispersities (M-w/M-n < 1.10) up to more than 90% conversion. The PNIPAM trithiocarbonate end-groups were then converted to methacrylate end-groups by combining (i) aminolysis and (ii) nucleophilic Michael addition using the bifunctional reagent, 3-(acryloyloxy)-2-hydroxypropyl methacrylate (AHPMA), in a one pot reaction. The resulting PNIPAM macromonomers were evaluated as reactive steric stabilizers for latex syntheses. Near-monodisperse submicrometer-sized latexes were obtained by alcoholic dispersion polymerization of styrene in methanol, as judged by scanning electron microscopy (SEM) and dynamic light scattering (DLS). In contrast, a latex synthesized in the presence of a PNLPAM-CTA had a bimodal size distribution, while thiol-capped PNIPAM chains produced ill defined nonspherical particles and styrene polymerization conducted in the absence of any stabilizer led to macroscopic precipitation. These control experiments confirm that using the methacrylate-capped macromonomers is essential for successful latex syntheses. H-1 NMR analysis confirm the presence of PNIPAM chains in the latex particles and XPS measurements indicate that the stabilizer is located on the particle surface, as expected. The well-known thermo-responsive nature of the stabilizer was successfully transferred to these latexes, which exhibit reversible flocculation upon heating above the LCST of the PNIPAM chains.