2-methypropane-1,3-bis(2-hydroxyethyl sulfide) | 1385790-58-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-methypropane-1,3-bis(2-hydroxyethyl sulfide)
• 英文别名: 2-methylpropane-1,3-bis(2-hydroxyethyl sulfide)；2-[3-(2-Hydroxyethylsulfanyl)-2-methylpropyl]sulfanylethanol；2-[3-(2-hydroxyethylsulfanyl)-2-methylpropyl]sulfanylethanol
• CAS: 1385790-58-8
• 化学式: C₈H₁₈O₂S₂
• 分子量: 210.362
• InChiKey: WMVGSDLDNVZUNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基丙烯酸羟乙酯 、 丁二酸酐 、 2-methypropane-1,3-bis(2-hydroxyethyl sulfide) 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 2-methylpropane-1,3-bis(2-[2-methacryloyloxyethyl succinyl]ethyl sulfide)
  参考文献：
  名称：

  Stress Relaxation via Addition–Fragmentation Chain Transfer in High T_g, High Conversion Methacrylate-Based Systems

  摘要：

  To reduce shrinkage stress which arises during the polymerization of cross-linked polymers, allyl sulfide functional groups were incorporated into methacrylate polymerizations to determine their effect on stress relaxation via addition-fragmentation chain transfer (AFCT). Additionally, stoichiometrically balanced thiol and ally' sulfide-containing norbornene monomers were incorporated into the methacrylate resin to maximize the overall functional group conversion and promote AFCT while also enhancing the polymer's mechanical properties. Shrinkage stress and reaction kinetics for each of the various functional groups were measured by tensometry and Fourier-transform infrared (FTIR) spectroscopy, respectively. The glass transition temperature (T-g) and elastic moduli (E') were measured using dynamic mechanical analysis. When the ally' sulfide functional group was incorporated into dimethacrylates, the polymerization-induced shrinkage stress was not relieved as compared with analogous propyl sulfide-containing resins. These analogous propyl sulfide-containing monomers are incapable of undergoing AFCT while having similar chemical structure and cross-link density to the allyl sulfide-containing methacrylates. Here, a monomethacrylate monomer that also contains a cyclic ally] sulfide (PAS) was found to increase the cross-linking density nearly 20 times as compared to an analogous monomethacrylate in which the allyl sulfide was replaced with an ethyl sulfide. Despite the much higher cross-link density, the PAS formulation exhibited no concomitant increase in stress. Thiol norbornene resins were copolymerized in PAS to promote AFCT as well as to synergistically combine the ring-opening benefits associated with the thiol ene reaction. AFCT resulted in a 63% reduction of polymerization stress and a 45 degrees C enhancement of the glass transition temperature in the allyl sulfide-containing thiol- norbornene-methacrylate system compared with rubbery dimethacrylates. When compared with conventional glassy dimethacrylates, this combined system has less than 10% of the typical shrinkage stress level while having similarly excellent mechanical properties.

  DOI：

  10.1021/ma300228z
• 作为产物：
  描述：

  1-溴-3-氯-2-甲基丙烷 、 2-巯基乙醇 在 sodium 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 2-methypropane-1,3-bis(2-hydroxyethyl sulfide)
  参考文献：
  名称：

  Stress Relaxation via Addition–Fragmentation Chain Transfer in High T_g, High Conversion Methacrylate-Based Systems

  摘要：

  To reduce shrinkage stress which arises during the polymerization of cross-linked polymers, allyl sulfide functional groups were incorporated into methacrylate polymerizations to determine their effect on stress relaxation via addition-fragmentation chain transfer (AFCT). Additionally, stoichiometrically balanced thiol and ally' sulfide-containing norbornene monomers were incorporated into the methacrylate resin to maximize the overall functional group conversion and promote AFCT while also enhancing the polymer's mechanical properties. Shrinkage stress and reaction kinetics for each of the various functional groups were measured by tensometry and Fourier-transform infrared (FTIR) spectroscopy, respectively. The glass transition temperature (T-g) and elastic moduli (E') were measured using dynamic mechanical analysis. When the ally' sulfide functional group was incorporated into dimethacrylates, the polymerization-induced shrinkage stress was not relieved as compared with analogous propyl sulfide-containing resins. These analogous propyl sulfide-containing monomers are incapable of undergoing AFCT while having similar chemical structure and cross-link density to the allyl sulfide-containing methacrylates. Here, a monomethacrylate monomer that also contains a cyclic ally] sulfide (PAS) was found to increase the cross-linking density nearly 20 times as compared to an analogous monomethacrylate in which the allyl sulfide was replaced with an ethyl sulfide. Despite the much higher cross-link density, the PAS formulation exhibited no concomitant increase in stress. Thiol norbornene resins were copolymerized in PAS to promote AFCT as well as to synergistically combine the ring-opening benefits associated with the thiol ene reaction. AFCT resulted in a 63% reduction of polymerization stress and a 45 degrees C enhancement of the glass transition temperature in the allyl sulfide-containing thiol- norbornene-methacrylate system compared with rubbery dimethacrylates. When compared with conventional glassy dimethacrylates, this combined system has less than 10% of the typical shrinkage stress level while having similarly excellent mechanical properties.

  DOI：

  10.1021/ma300228z

文献信息

• DISULFIDE MONOMERS COMPRISING ETHYLENICALLY UNSATURATED GROUPS SUITABLE FOR DENTAL COMPOSITIONS
  申请人：Abuelyaman Ahmed S.

  公开号：US20120295228A1

  公开（公告）日：2012-11-22

  Dental compositions and disulfide monomers are described. The disulfide monomer comprise a disulfide backbone group wherein each of the sulfur atoms are bonded to an ethylenically unsaturated group via a divalent linking group and the linking group comprises at least one heteroatom; and at least one other monomer ethylenically unsaturated monomer.
• US8455565B2
  申请人：——

  公开号：US8455565B2

  公开（公告）日：2013-06-04
• Stress Relaxation via Addition–Fragmentation Chain Transfer in High <i>T</i>_g, High Conversion Methacrylate-Based Systems
  作者：Hee Young Park、Christopher J. Kloxin、Ahmed S. Abuelyaman、Joe D. Oxman、Christopher N. Bowman

  DOI：10.1021/ma300228z

  日期：2012.7.24

  To reduce shrinkage stress which arises during the polymerization of cross-linked polymers, allyl sulfide functional groups were incorporated into methacrylate polymerizations to determine their effect on stress relaxation via addition-fragmentation chain transfer (AFCT). Additionally, stoichiometrically balanced thiol and ally' sulfide-containing norbornene monomers were incorporated into the methacrylate resin to maximize the overall functional group conversion and promote AFCT while also enhancing the polymer's mechanical properties. Shrinkage stress and reaction kinetics for each of the various functional groups were measured by tensometry and Fourier-transform infrared (FTIR) spectroscopy, respectively. The glass transition temperature (T-g) and elastic moduli (E') were measured using dynamic mechanical analysis. When the ally' sulfide functional group was incorporated into dimethacrylates, the polymerization-induced shrinkage stress was not relieved as compared with analogous propyl sulfide-containing resins. These analogous propyl sulfide-containing monomers are incapable of undergoing AFCT while having similar chemical structure and cross-link density to the allyl sulfide-containing methacrylates. Here, a monomethacrylate monomer that also contains a cyclic ally] sulfide (PAS) was found to increase the cross-linking density nearly 20 times as compared to an analogous monomethacrylate in which the allyl sulfide was replaced with an ethyl sulfide. Despite the much higher cross-link density, the PAS formulation exhibited no concomitant increase in stress. Thiol norbornene resins were copolymerized in PAS to promote AFCT as well as to synergistically combine the ring-opening benefits associated with the thiol ene reaction. AFCT resulted in a 63% reduction of polymerization stress and a 45 degrees C enhancement of the glass transition temperature in the allyl sulfide-containing thiol- norbornene-methacrylate system compared with rubbery dimethacrylates. When compared with conventional glassy dimethacrylates, this combined system has less than 10% of the typical shrinkage stress level while having similarly excellent mechanical properties.