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Biorenewable Alternative to Polyacrylates

Technology #20170023

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Polyacrylate AlternativePolymer Precursor
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Researchers
Thomas R. Hoye, PhD
Professor, Department of Chemistry
External Link (chem.umn.edu)
Nicolas Ball-Jones, PhD
Postdoctoral Associate, Department of Chemistry
Grant W. Fahnhorst
Research Associate, Department of Chemistry
Managed By
Larry Micek
Technology Licensing Officer 612-624-9568
Patent Protection

US Patent Pending
Publications
Poly(isoprenecarboxylates) from Glucose via Anhydromevalonolactone
ACS Macro Letters, 2016, 5 (10), pp 1128–1131

Polymers from Glucose

An environmentally friendly process has been developed for the synthesis of isoprenecarboxylic esters and their corresponding polymers from a fermentation product of glucose:  mevalonolactone. In this method, bio-renewable mevalonate is used to synthesize mevalonolactone, which can then be converted to anhydromevalonolactone. An eliminative opening of anhydromevalonolactone using a base like tert-butoxide creates the precursor to isoprenecarboxylic esters (e.g., methyl, ethyl, n-butyl, and t-butyl derivatives) with different sizes of the ester alkyl moiety. The final step is radical polymerization of these esters or the precursor acid, using AIBN as initiator, which leads to the ultimate poly(isoprenecarboxylate) product. The varying alkyl ester moiety changes the polymer’s properties creating the possibility of polymers suited for a variety of applications.

“Acrylate-like” Polymers for Hydrogels and Adhesives

Acrylates are commodity chemicals used to make hydrogels and adhesives found in a wide variety of consumer products, but few bio-derived “acrylate-like” monomers are currently available. Like acrylates, this versatile technology can be used to make polymers ranging from soft, tacky polymers to brittle hard plastics. These polymers can be water-resistant or water absorbing depending on the starting monomer used. By using bio-renewable materials, this method offers potential sustainable alternatives to poly(acrylates).

BENEFITS AND FEATURES:

  • Environmentally friendly, “green” process
  • Uses glucose as a starting material
  • Adjustable polymer properties: the same technology can make soft and tacky materials to hard and brittle or hydrophilic or hydrophobic materials

APPLICATIONS:

  • Hydrogels for:
    • Thickening agents
    • Super absorbent materials
    • Disposable diapers
    • Feminine products
    • Hair gels
    • Shampoo/cosmetics

  • Pressure sensitive adhesives

Phase of Development - Proof of Concept