D-2,5-di-O-(carbamate ethylene methacrylate)-1,4:6,3-mannarodilactone | 1531591-63-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: D-2,5-di-O-(carbamate ethylene methacrylate)-1,4:6,3-mannarodilactone
• CAS: 1531591-63-5
• 化学式: C₂₀H₂₄N₂O₁₂
• 分子量: 484.417
• InChiKey: LBKUFWUOODBKNJ-XUXIUFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  181.86
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  甲基丙烯酸异氰基乙酯 、 D-mannaro-1,4:6,3-dilactone 在 二月桂酸二丁基锡 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以54%的产率得到D-2,5-di-O-(carbamate ethylene methacrylate)-1,4:6,3-mannarodilactone
  参考文献：
  名称：

  Degradable Thermosets from Sugar-Derived Dilactones

  摘要：

  Using the sugar derivatives glucarodilactone and mannarodilactone, two new dimethacrylate monomers (GDMA and MDMA) were synthesized by a tin-catalyzed alcohol-isocyanate coupling between the dilactones and isocyanatoethyl methacrylate. GDMA was polymerized using thermally initiated free radical polymerization at 135 degrees C in the presence of dicumyl peroxide as an initiator. The fractional conversion of methacrylate groups in PGDMA was determined by FT-IR to be 0.64, within the typical range of poly(dimethacrylates). Tensile testing of PGDMA demonstrated the stiff but brittle nature of this material and the modulus was shown to be similar to that reported for commercially available poly(dimethacrylates) from rigid monomers. The hydrolytic stability of PGDMA was investigated by submersing polymer samples in acidic, neutral, and basic aqueous environments. PGDMA degraded to water-soluble components after 17 days in 1 M NaOH but remained stable under acidic and neutral conditions. Solvent casting a mixture of GDMA, MDMA, and benzoyl peroxide followed by thermal curing at 95 C gave clear P(GDMA-co-MDMA) (3:2) coatings. These coatings showed similar hydrolytic stability to the bulk PGDMA material. GDMA and methyl methacrylate (MMA) were used to synthesize P(GDMA-co-MMA) microspheres by precipitation polymerization in THF. These particles were characterized by dynamic light scattering (DLS) in THF and in the dry state by scanning electron microscopy. Optimization of polymerization conditions yielded 730 nm diameter particles with a spherical morphology and low dispersity as determined by DLS.

  DOI：

  10.1021/ma401904x