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Synthesis and polymerization of isosorbide-based monomethacrylates

Gathergood, Nicholas ; Jannasch, Patric LU ; Matt, Livia ; Parve, Jaan ; Parve, Omar ; Pehk, Tõnis and Vares, Lauri (2019) WO2019202038A2
Abstract
Isosorbide-5-methacrylate was obtained by enzymatic catalysis with Lipozyme RM IM in a highly regioselective manner in up to 87% yield. The process uses readily available acyl donors (methacrylic anydride or vinyl methacrylate), is easily scalable and chromatography free. Simple extractive workup followed by decoloration and filtration affords the monomer with up to > 99% purity. In addition, the developed enzymatic strategy was applied for the synthesis of a series of isosorbide 5- and 2-methacrylate derivatives. All the sythesized isosorbide monomethacrylates were radically polymerized with AIBN. The properties of these polymers with different side groups in either endo or exo configuration in the isosorbide structure was examined.... (More)
Isosorbide-5-methacrylate was obtained by enzymatic catalysis with Lipozyme RM IM in a highly regioselective manner in up to 87% yield. The process uses readily available acyl donors (methacrylic anydride or vinyl methacrylate), is easily scalable and chromatography free. Simple extractive workup followed by decoloration and filtration affords the monomer with up to > 99% purity. In addition, the developed enzymatic strategy was applied for the synthesis of a series of isosorbide 5- and 2-methacrylate derivatives. All the sythesized isosorbide monomethacrylates were radically polymerized with AIBN. The properties of these polymers with different side groups in either endo or exo configuration in the isosorbide structure was examined. The methacrylic isosorbide derivatives with OH-group were found to have very high glass transition temperature (Tg = 167 °C) and good thermal stability (at 5% weight loss under N2, Td,95 = 240 °C). The highest molecular weight (Mn = 80.6 kg/mol) was determined for the polymethacrylate with Ac-substitute. (Less)
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organization
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Patent
publication status
published
subject
publisher
PCT International Applications
patent number
WO2019202038A2
language
English
LU publication?
yes
id
b21a15f6-1631-4dc7-9cac-b88bd495fa0e
alternative location
https://worldwide.espacenet.com/patent/search/family/066448506/publication/WO2019202038A2?q=WO2019202038A2&queryLang=en%3Ade%3Afr
date added to LUP
2019-12-16 16:26:30
date last changed
2020-01-20 16:45:00
@misc{b21a15f6-1631-4dc7-9cac-b88bd495fa0e,
  abstract     = {Isosorbide-5-methacrylate was obtained by enzymatic catalysis with Lipozyme RM IM in a highly regioselective manner in up to 87% yield. The process uses readily available acyl donors (methacrylic anydride or vinyl methacrylate), is easily scalable and chromatography free. Simple extractive workup followed by decoloration and filtration affords the monomer with up to > 99% purity. In addition, the developed enzymatic strategy was applied for the synthesis of a series of isosorbide 5- and 2-methacrylate derivatives. All the sythesized isosorbide monomethacrylates were radically polymerized with AIBN. The properties of these polymers with different side groups in either endo or exo configuration in the isosorbide structure was examined. The methacrylic isosorbide derivatives with OH-group were found to have very high glass transition temperature (Tg = 167 °C) and good thermal stability (at 5% weight loss under N2, Td,95 = 240 °C). The highest molecular weight (Mn = 80.6 kg/mol) was determined for the polymethacrylate with Ac-substitute.},
  author       = {Gathergood, Nicholas and Jannasch, Patric and Matt, Livia and Parve, Jaan and Parve, Omar and Pehk, Tõnis and Vares, Lauri},
  language     = {eng},
  note         = {Patent, Patent Number: WO2019202038A2},
  publisher    = {PCT International Applications},
  title        = {Synthesis and polymerization of isosorbide-based monomethacrylates},
  url          = {https://worldwide.espacenet.com/patent/search/family/066448506/publication/WO2019202038A2?q=WO2019202038A2&queryLang=en%3Ade%3Afr},
  year         = {2019},
}