Jump to main content or area navigation.

Contact Us

Extramural Research

Final Report: Composite Resins and Adhesives from Plants

EPA Grant Number: R829576
Title: Composite Resins and Adhesives from Plants
Investigators: Wool, R. P.
Institution: University of Delaware
EPA Project Officer: Richards, April
Project Period: January 1, 2002 through December 31, 2004
Project Amount: $325,000
RFA: Technology for a Sustainable Environment (2001)
Research Category: Pollution Prevention/Sustainable Development

Description:

Objective:

The objective of this research is to develop the fundamental science and engineering to support recent technology breakthroughs in the field of high-performance, low-cost composite resins and adhesives from plant oils for new liquid molding and adhesion applications. These materials will replace petroleum-based plastics, following the demise of the oil industry in the next 25 years. They also are highly integrated into the biofuels and biorefinery national research programs. Professor Wool’s research focuses on (1) determination of the optimal fatty acid distribution (FAD) function of chemically functionalized plant oils (e.g., soy, corn, linseed, olive, sunflower) using simulation, vector percolation theory, and experiments to minimize the properties of crosslinked triglyceride networks in the matrix; (2) development of a natural and glass fiber sizing or coupling agent using difunctionalized high oleic genetically engineered oils, applied in situ in the liquid molding manufacturing step (resin transfer molding and vacuum-assisted resin transfer molding [VARTM]) to tailor the fiber-matrix interface strength; (3) development of a rubber toughening particle (low glass transition temperature [Tg]) using the new water-based pressure sensitive adhesive (PSA) micro-latex particle technology, applied during liquid molding to enhance impact strength and promote self-healing of damage, using high energy ion-cluster surfaces developed for sheet molding compound; (4) development of interfacial and matrix toughening (high Tg) agent using chemically modified lignin; (5) development of a natural fiber preform binder using a highly branched structure of the PSA latex particles (linear chains); and (6) VARTM manufacture of the first large structures using natural fiber preforms and the optimized bio-based resins in support of the shaped engineered wood substitute materials proposed for new housing construction and civil infrastructure. Such applications of Professor Wool’s new materials include low-cost, hurricane-resistant roofs and tsunami shelter houses.

Summary/Accomplishments (Outputs/Outcomes):

Bio-based Resins

The results of the research on soy-based materials are summarized in a new book, Bio-Based Polymers and Composites, by R.P. Wool and X.S. Sun (Burlington, MA: Elsevier), to be published July 15, 2005. Considerable progress was made in understanding the fundamental relationship between the FAD function, level of functionalization, and extent of reaction on the strength and modulus of the bio-based composite resins derived from plant oils. The results have been published in the Journal of Polymer Science, Part B: Polymer Physics edition. This has lead to the development of a new universal theory of fracture of polymers, entitled the “Rigidity Percolation Model of Fracture of Polymers.” In addition, the thermal properties, particularly the Tg, have been analyzed for thin films and the bulk, using gradient percolation theory of finite size lattices. The resulting new theory of the glass transition is in excellent agreement with the experiment and was presented at the American Chemical Society (ACS) Annual Meeting in Philadelphia, August 2004. The rigidity percolation (RP) fracture model also is used to design new high-performance resins, which can be used in automotive and agricultural equipment (e.g., John Deere tractors), as presented to Congress in support of the Green Chemistry Bill. The Principal Investigator (PI) is working with the Dow Chemical Company to mass-produce the resin. The fundamental relations for the properties of Professor Wool’s bio-based resins were supported by Computer Simulations, in collaboration with Sandia National Laboratories.

Elastomers

The first biobased elastomers were synthesized from genetically engineered high-oleic oils and were found to have useful properties. These unique materials also were compatible with nanoclays and could be used to make crosslinked elastomers. They also have the potential to act as self-healing nanobeams because of the unique control of the extent of exfoliation, permitting the reversible opening and closing of intercalated nanobeams. Such materials could have considerable impact resistance and, unlike current rubber-toughened plastics, also would have the ability to heal the impact damage. The initial results were presented at the ACS Annual Meeting in Philadelphia, August 2004.

Lignin

The addition of lignin to bio- and petroleum-based resins resulted in significant improvements in mechanical properties. We found a chemical method to solubilize lignin in the biobased resins with considerable improvement in properties. The RP model of fracture predicts that for highly crosslinked resins, the existence of free radical traps would increase the fracture energy to a maximum value at a concentration of lignin c* equivalent to the crosslink density. We found that about c* equal to 2 percent lignin resulted in a 300 percent increase in fracture energy. This mechanism can be optimized in future studies. Two papers have been accepted for publication.

Hurricane-Resistant Houses

A hurricane-resistant roof was built from recycled paper and soybeans using a uniquely designed monolithic roof. This application is potentially the highest volume application of bio-based composite materials derived from low-cost, environmentally friendly, renewable resources. Its foam-core engineered structure also imparts huge thermal energy savings in addition to the safety factor of the storm-resistant design. The results were shown in Newsweek, October 2003, the Architectural Record, November 2003 issue, and will be featured in the RIBA Journal, the official magazine of the Royal Institute of Building Architects, in September 2004. It also was presented to Congress in support of the Green Chemistry Bill. The bio-based materials design was expanded further to create new emergency tsunami houses, which would be suited to survivors of flood, earthquake, tsunami, hurricane, and weapons of mass destruction disasters.

Printed Circuit Boards

Intel Corporation has expressed interest in the new, low-dielectric constant composites suited to electronic materials applications, which were made from chicken feather fibers and soy resin. The results were featured in Discover Magazine in July 2003. Pyrolysis of the chicken feathers also resulted in a new, high modulus reinforcement material, which needs further study. Several papers have been accepted for publication, and a patent application is pending. The chicken feather chip was presented to Congress during testimony in support of the Green Chemistry Bill. If funding is available, Professor Wool will make the first commercial chicken feather printed circuit boards in collaboration with Hunter Technology Corporation of Silicon Valley and Intel Corporation.

Carbon Nanotubes

Soybean oils were found to be solvents for carbon nanotubes. This opens several new opportunities for environmentally friendly processing of these highly valuable materials. The phase diagram for any solvent with carbon nanotubes has been calculated, and this will be significant in self-assembly of nanostructures, nanotube fiber processing, selective deposition in electronic materials, and successful dispersal to make improved composite materials.

Biocompatibility

The biobased materials made from soy oil triglycerides by Professor Wool’s group at the University of Delaware include composite resins, foams, elastomers, PSAs, and coatings. These were tested recently by Dr. Catherine Klapperich at Boston University. They all were found to be biocompatible with tissue and cell cultures, which opens some very exciting possibilities for a whole new class of biocompatible materials. This added bonus makes the current generation of Professor Wool’s green materials more human friendly as well as environmentally friendly.

Green Engineering Teaching

The PI developed a new course at the University of Delaware entitled Green Engineering that is in concert with the Principles of Green Engineering developed by the U.S. Environmental Protection Agency in collaboration with several investigators. The text for the course was written by Allen and Shonard. Twenty-five senior chemical engineering students and three industrial engineers took the course.


Journal Articles on this Report : 19 Displayed | Download in RIS Format

Other project views: All 44 publications 26 publications in selected types All 19 journal articles

Type Citation Project Document Sources
Journal Article Bunker SP, Wool RP. Synthesis and characterization of monomers and polymers for adhesives from methyl oleate. Journal of Polymer Science Part A: Polymer Chemistry 2002;40(4):451-458. R829576 (Final)
not available
Journal Article Can E, Kusefoglu S, Wool RP. Rigid thermosetting liquid molding resins from renewable resources. II. Copolymers of soybean oil monoglyceride maleates with neopentyl glycol and bisphenol A maleates. Journal of Applied Polymer Science 2002;83(5):972-980. R829576 (Final)
not available
Journal Article Dweib MA, Hu B, O'Donnell A, et al. All natural composite sandwich beams for structural applications. Composite Structures 2004;63(2):147-157. R829576 (Final)
not available
Journal Article Esen HY, Kusefoglu SH, Wool RP. Photolytic and free radical polymerization of epoxidized plant oil triglycerides. Abstracts of Papers of the American Chemical Society 2004;228:U391-U391 439-POLY Part 2. R829576 (Final)
not available
Journal Article Hong CK, Wool RP. Development of a bio-based composite material from soybean oil and keratin fibers. Journal of Applied Polymer Science 2005;95(6):1524-1538. R829576 (Final)
not available
Journal Article La Scala J, Wool RP. Effect of FA composition on epoxidation kinetics of TAG. Journal of the American Oil Chemists Society 2002;79(4):373-378. R829576 (Final)
not available
Journal Article La Scala J, Wool RP. The effect of fatty acid composition on the acrylation kinetics of epoxidized triacylglycerols. Journal of the American Oil Chemists Society 2002;79(1):59-63. R829576 (Final)
not available
Journal Article La Scala J, Wool RP. Property analysis of triglyceride-based thermosets. Polymer 2005;46(1):61-69. R829576 (Final)
not available
Journal Article La Scala J, Wool RP. Rheology of chemically modified triglycerides. Journal of Applied Polymer Science 2005;95(3):774-783. R829576 (Final)
not available
Journal Article Lorenz CD, Stevens MJ, Wool RP. Fracture behavior of triglyceride-based adhesives. Journal of Polymer Science Part B: Polymer Physics 2004;42(18):3333-3343. R829576 (Final)
not available
Journal Article Lu J, Wool RP. Synthesis and characterization of soyoil-based SMC resins. Abstracts of Papers of the American Chemical Society 2002;223(IEC Pt 1):320 R829576 (Final)
not available
Journal Article Lu J, Hong CK, Wool RP. Bio-based nanocomposites from functionalized plant oils and layered silicate. Journal of Polymer Science Part B-Polymer Physics 2004;42(8):1441-1450 R829576 (2003)
R829576 (Final)
not available
Journal Article Lu J, Khot S, Wool RP. New sheet molding compound resins from soybean oil. I. Synthesis and characterization. Polymer 2005;46(1):71-80. R829576 (Final)
not available
Journal Article McAninch IM, Thielemans W, Wool RP. Fracture properties of CNT-soy oil based composites. Abstracts of Papers of the American Chemical Society 2004;228(COLL Pt 1):34 R829576 (Final)
not available
Journal Article Wool RP. Composites and plastics from plant oils and natural fibers. Abstracts of Papers of the American Chemical Society 2002;223(PMSE Pt 2):82 R829576 (Final)
not available
Journal Article Wool RP. Green tractors and houses from soybeans. Abstracts of Papers of the American Chemical Society 2004;228:U770-U770 065-IEC Part 1. R829576 (Final)
not available
Journal Article Wool RP. Rigidity percolation model of polymer fracture. Journal of Polymer Science Part B: Polymer Physics 2005;43(2):168-183. R829576 (Final)
not available
Journal Article Zhu L, Wool RP. Nanoclay filled bio-based elastomers: synthesis and characterization. Abstracts of Papers of the American Chemical Society 2004;228:U459-U459 055-COLL Part 1. R829576 (Final)
not available
Journal Article Zhu L, Wool RP. Elastomer from renewable resources: synthesis and characterization. Abstracts of Papers of the American Chemical Society 228:U766-U766 042-IEC Part 1. R829576 (Final)
not available
Supplemental Keywords:

polymers, composites, biobased plastics, plant oils, biobased resins, renewable resources, green engineering, biobased adhesives, RFA, Scientific Discipline, Sustainable Industry/Business, cleaner production/pollution prevention, Sustainable Environment, Technology for Sustainable Environment, New/Innovative technologies, Chemistry and Materials Science, Engineering, binder, triglyceride oil, alternative materials, plant oils, carbon dioxide, composites, pollution prevention, adhesives, composite resins, resins

Progress and Final Reports:
Original Abstract
2002 Progress Report
2003 Progress Report

Top of Page

The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Conclusions drawn by the principal investigators have not been reviewed by the Agency.

Jump to main content.