5-[2-(2-Bicyclo[2.2.1]hept-5-enylmethylsulfanylmethyl)prop-2-enylsulfanylmethyl]bicyclo[2.2.1]hept-2-ene | 1385790-44-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-[2-(2-Bicyclo[2.2.1]hept-5-enylmethylsulfanylmethyl)prop-2-enylsulfanylmethyl]bicyclo[2.2.1]hept-2-ene
• 英文别名: 5-[2-(2-bicyclo[2.2.1]hept-5-enylmethylsulfanylmethyl)prop-2-enylsulfanylmethyl]bicyclo[2.2.1]hept-2-ene
• CAS: 1385790-44-2
• 化学式: C₂₀H₂₈S₂
• 分子量: 332.574
• InChiKey: LLBYJMANFXZWRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二聚环戊二烯 在 sodium 、 对苯二酚 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 5-[2-(2-Bicyclo[2.2.1]hept-5-enylmethylsulfanylmethyl)prop-2-enylsulfanylmethyl]bicyclo[2.2.1]hept-2-ene
  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 NORBORNYL GROUPS SUITABLE FOR DENTAL COMPOSITIONS
  申请人：Bowman Christopher N.

  公开号：US20120295227A1

  公开（公告）日：2012-11-22

  Dental compositions and disulfide monomers described. The disulfide monomer comprises a disulfide backbone group wherein each of the sulfur atoms are bonded to a group terminating with an ethylenically unsaturated norbornyl group; and at least one other monomer comprising at least two ethylenically unsaturated groups.
• US8431626B2
  申请人：——

  公开号：US8431626B2

  公开（公告）日：2013-04-30
• 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.