Final Report: Novel Hempseed Oil-Based Bio-epoxy for the Manufacturing of Sporting Goods

EPA Contract Number: EPD17036
Title: Novel Hempseed Oil-Based Bio-epoxy for the Manufacturing of Sporting Goods
Investigators: Bouchier, Evan
Small Business: ZILA Works
EPA Contact: Manager, SBIR Program
Phase: I
Project Period: September 1, 2017 through February 28, 2018
Project Amount: $99,671
RFA: Small Business Innovation Research (SBIR) - Phase I (2017) RFA Text |  Recipients Lists
Research Category: Small Business Innovation Research (SBIR) , SBIR - Manufacturing

Description:

Epoxy resins are typically created using bisphenol A (BPA), an endocrine disrupting chemical. In addition, over 90% of plastics are derived from virgin fossil feedstocks, equivalent to ~6% of global oil consumption. The purpose of the research was to develop an innovative bio-epoxy resin based on the fatty acids of hempseed oil. The approach was to dismantle (by hydrolysis) the triglyceride structure and functionalize with epoxy groups to synthesize new epoxy functionalized monomers for use in formulations for the sporting goods industry.

Summary/Accomplishments (Outputs/Outcomes):

Research Objectives

  • Develop the synthetic pathway to functionalize commercially available hempseed oil (HO) with epoxy groups for use in a bio-epoxy resin formulation;

  • Complete lab scale-up on the multiple liter scale to demonstrate feasibility of the synthetic pathway for pilot and volume manufacturing;

  • Develop a formulation using the highest amount of bio-based epoxy resin possible, must be greater than 50% bio-based epoxy content to be competitive (commercially available bio-epoxy has 37% bio-based content);

  • Develop the resin and curing packaging (hardener and accelerator package) suitable for snowboard manufacturing (viscosity, work life, curing temperature/time); and

  • Use the bio-based epoxy resin formulation from the scale-up runs to build two snowboards. Test snowboards using industry standard testing protocols to demonstrate feasibility of the formulation approach to achieve the technical objectives.

 

Technical Approach

  • Optimize the synthetic pathway to convert commercially available hempseed oil into a Bio-based epoxy resin (HO-Bio EP) at liter quantities and fully characterize to quantify the conversion of starting materials to epoxy containing monomers;

  • Develop a formulation using HO-Bio EP to for use in the manufacturing of snowboards (epoxy/glass fabric composite used);

  • Develop a two-part resin system capable of mixing at room temperature, having at least 30 minute working time, and achieve an acceptable glass transition temperature, Tg (softening point), after a typical curing process used to make snowboards (95°C/30 minute cure cycle);

  • Benchmark with current commercially available bio-based epoxy from Entropy Resins (37% bio-based content);

  • Screen HO-Bio EP formulations to achieve optimal physical properties after typical in snowboard manufacturing curing cycle. Match or exceed the adhesion strength to Ultra High Molecular Weight Polyethylene (UHMWPE snowboard base material) compared with commercially available bio-based epoxy resins. Achieve suitable work life (how long the customer can use after mixing) allowing the application of the liquid resin to the glass fabric in the snowboard mold; and

  • Synthesize enough HO-Bio EP and other bio-based epoxies to have > 2 liters of formulated resin available for snowboard builds.

Conclusions:

Developed a synthetic pathway to use commercially available hempseed oil and functionalize with epoxy groups (termed HO-Bio EP). The synthetic process uses a novel approach to use the double bonds in hempseed oil as reaction sites to functionalize with epoxy groups. The hydrolysis reaction, conjugation, Diels Alder addition, and epoxy group addition were validated at the lab scale. Enough HO-Bio EP was synthesized near the end of the project to allow the fabrication of two commercial snowboards.

The team evaluated approximately 45 different formulations containing bio-based epoxy resins. The formulations were a two part resin system with Part A containing the bio-based resins and Part B was an amine curing agent. During the formulation work, extensive knowledge was acquired in understanding the role of the bio-epoxy molecular architecture, epoxy hardeners and accelerators and the importance of maximizing the cohesive strength of the epoxy matrix. Developed multiple screening methods to guide the formulation work. Using the screening techniques, at the end of evaluating 45 unique formulations, a formulation was identified that closely matched the physical properties and work life of a commercially available bio-based epoxy resin (Entropy Super SAP).

The ZILA Works formulation was used successfully to build two snowboards in a commercial snowboard manufacturing facility. Testing of the ZILA Works snowboard showed very promising results, passing most tests and overall the results were very positive for the first trial of the ZILA Works bio-epoxy resin.