Acrylic Monomers Derived from Plant Oils - Synthesis and Use in High Value Polymers (RFT-462)

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Invention Summary

Scientists at NDSU have developed an efficient and cost-effective one-step method to convert plant oils into acrylic monomers that substitute for petroleum-based monomers in the production of acrylic polymers.  This method can use essentially any plant oil, animal fat, or other fatty esters as the raw material.  The output is a combination of (meth) acrylic fatty monomers that can be used directly in the production of latexes, adhesives, surfactants, sizing agents, resins, binders, and other products that utilize acrylic polymers.  Additionally, the NDSU monomers contain two types of double bonds.  The one within the acrylic group is reactive in conventional addition free radical polymerization, which allows formation of linear polymers.  The double bonds within the fatty chain remain unaffected during free radical polymerization, so remain available for oxidative cross-linking and additional tuning of the polymer performance characteristics.  This is in contrast to existing plant oil based monomers, which produce non-linear branched and cross-linked polymers (because their fatty chain double bonds may react during the polymerization reaction).

Benefits

The performance attributes of the linear structure derived from the NDSU monomers provide significant benefits as compared with competing plant oil based polymers.

  • Simple, one step conversion of plant oils and other triglycerides into acrylic monomers
  • Plant oils can be chosen so as to enable specific post-polymerization strategies and functionalities (i.e. the lengths and degree of unsaturation of FA side chains from different plant oils leads to different controlled co-polymer properties)
  • Integrate monomers to hydrophobize polymers and polymeric materials
  • Enables production of specialty additive that can hydrophobize and plasticize the material at the same time
  • Provides internal plasticizing of polymeric material by softening the end product as desired by adjusting how much of the acrylic monomer is incorporated into the co-polymer
  • Monomers are direct substitutes for petroleum-based monomers in conventional synthesis, with no need to change the manufacturing process
  • Monomers contain two types of double bonds which aren’t present in petroleum-based monomers.  These double bonds enable production of linear polymers with additional sites for cross-linking, thereby enabling production of polymers with enhanced functionality

Stage of Development

Oils used to date are soybean, linseed, olive, and sunflower, which provides a wide range of FA side chain unsaturation, all of which have been converted into monomers, and subsequently into polymers and/or copolymers

Applications

  • Polymeric emulsions (e.g. latexes)
  • Resins
  • Paints and coatings
  • Plastics
  • Adhesives
  • Chemical binders

Technology

Triglycerides derived from plant oils and fats are difficult to convert into low molecular weight acrylic monomers.  Current production of fatty acrylates utilizes multistep synthesis.  For example, the production of a well-known fatty monomer, stearyl acrylate, includes saponification, neutralization, reduction, acylation, and other procedures which are quite expensive.  NDSU’s one-step method can be performed using a batch set-up designed for biodiesel production, providing a simple and well-understood path to substitute bio-based monomers for petroleum based monomers in production of existing and new acrylic polymers.

Patents

This technology is patent pending with fully preserved PCT patent rights and is available for licensing/partnering opportunities.

Contact

Henry Nowak, Technology Manager
hnowak@ndsurf.org
(701)231-8173

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