2025
Soybean oil-based non-isocyanate polyurethanes for commercial applications
Contributor/Checkoff:
Category:
Industrial
Keywords:
AdhesivesCoatingsIndustrial UsesSoy mealSustainability
Lead Principal Investigator:
Ram Gupta, Pittsburg State University
Co-Principal Investigators:
Project Code:
2508
Contributing Organization (Checkoff):
Institution Funded:
Brief Project Summary:
The main objective of this proposal is to provide value-added applications of soybean oil for polyurethane industries, particularly for coatings, sealants, and adhesives. Polyurethanes are of great interest since they represent one of the largest categories of plastics by demand, with applications ranging from construction to the automotive and furniture industries. The global polyurethane market size was valued at USD 72.82 billion in 2021 and is expected to expand at a compound annual growth rate (CAGR) of 4.3% from 2022 to 2030. Over 24 million metric tons of polyurethane were used globally in 2021. Utilizing soybean oil for such a huge industry will generate a demand of ~ 15 million metric tons of soybean oil (over 3 billion soybean bushels) per year.
Information And Results
Project Summary

Polyurethanes are an important class of polymers because of their wide industrial applications in automobiles, construction, household appliances, medicine, packaging, furniture, thermal, and electrical/vibration insulations. There is a global effort to replace petrochemicals with compounds from renewable resources. We propose to use soybean oil for the preparation of non-isocyanate polyurethanes using a cost-effective method that can be used for consumer as well as industrial applications. We plan to synthesize non-isocyanate polyurethanes using soybean oil-based compounds as a substitute for petrochemical-based polyols. Soybean oil-based non-isocyanate polyurethanes will be used for foams, coatings, and adhesives industries.

Project Objectives

Traditional polyurethane synthesis stems from the polyaddition reaction of diisocyanates and diols, both of which are largely derived from fossil fuel sources. The isocyanates are produced from hazardous and toxic phosgene gas by the phosgenation process. Phosgene is an extremely toxic gas. Additionally, the isocyanates are toxic and moisture-sensitive and cannot be prepared without sophisticated safety devices, thus posing serious environmental and human health risks. Consequently, a strong thrust has been directed to polyurethanes that avoid diisocyanates and have a reduced carbon footprint.
This proposal provides a solution to both problems. We propose to synthesize non-isocyanate polyurethanes using soybean oil-based compounds as a substitute for petrochemical-based polyols. We will also use carbon dioxide during the synthesis of non-isocyanate polyurethanes which is a global warming gas. The conversion of carbon dioxide into value-added and safe chemicals is very attractive to industries and environmental protection agencies. Non-isocyanate polyurethane-based foams, coatings, and adhesives will be developed for industrial applications.

Project Deliverables

There has been increased demand for the utilization of renewable materials for industrial applications. Soybean oil will be applied for value-added applications in polyurethanes, coating, and adhesive industries. The global polyurethane market size was estimated at over $72 billion in 2021, exhibiting a CAGR of 4.3% over the forecast period of 2022-2030. The market is driven by the presence of stringent environmental regulations designed by various regulatory bodies. Environmental concerns are likely to continue playing a key role in the formulation and use of these materials. The proposed research on soybean oil-based value-added materials will provide new pathways to utilize a large quantity of soybean oil providing greater value for the soybean farmers. The initial seed money from the Kansas Soybean Commission will help us to develop technology for commercialization. The societal impact of this project is significant as this proposal provides an opportunity for students to be involved in research, education, and product development. The outcome of this research will be used for business development, which will provide economic development to the State of Kansas. We expect to have a patent, two graduate thesis, and three peer-reviewed publications. The outcome of the project will be presented in seminars at Pittsburg State University and at conferences (after protecting intellectual properties). These seminars will be opened to the public to enhance community involvement in science and education. This will be a great platform to create public awareness regarding the value-added applications of soybean oil.

Progress Of Work

Updated January 9, 2025:
We started by creating a special type of soybean oil called carbonated soybean oil (CSBO) from regular soybean oil (SBO). This involved two steps and some testing to ensure it worked. We checked the results with tools like FT-IR (a way to analyze chemical bonds) and measured how thick the liquid was at room temperature. Later, we used a method called 1H NMR to confirm that the CSBO was successfully made. Once we had the CSBO, we experimented with adding certain chemicals called diamines and triamines to see how they affected its ability to act as an adhesive. These included isophorone diamine (IPDA), meta-xylylenediamine (m-XDA), and tris(2-aminoethyl)amine (TAA). We wanted to understand how reaction time, temperature, and the amount of these chemicals would influence the adhesive’s strength.

Initially, we mixed CSBO with IPDA in a 1:3.5 ratio and tested it at various temperatures—room temperature, 30°C, 50°C, 70°C, and 80°C—for 24 hours. We used FT-IR to monitor how the chemical reaction progressed, which showed a decrease in a particular bond (carbonate carbonyl peak) as the temperature went up. We then tested how strong the adhesive was on wood and found that curing it at 70°C gave better strength than curing it at 50°C. However, even at 70°C, some of the original chemical bonds didn’t fully react. Next, we changed the ratio of CSBO to IPDA to 1:4 and 1:2.5, trying different curing temperatures again (50°C, 70°C, and 90°C). We found that at a 1:4 ratio and 70°C, the chemical bonds completely reacted. But when we increased the temperature to 90°C, some bonds reappeared, and the adhesive became weaker. This suggested that too high a temperature might reverse part of the reaction. We also studied the adhesive's thermal properties. Using a method called DSC, we found that the material changed from rigid to soft at around 31°C (its glass transition temperature). We also used TGA to see how it reacted to heat in an oxygen-free environment.

To explore how reducing the amount of IPDA would affect the adhesive, we tested a 1:2.5 ratio at various temperatures. The results showed that the best adhesive strength occurred with a ratio of 3.5–4.0 parts IPDA to 1 part CSBO, cured at 70°C for 24 hours. This was consistent with our earlier findings. We then repeated similar tests with another chemical, m-XDA. Using a 1:2.5 and 1:3.0 ratio of CSBO to m-XDA, we monitored the reactions at 50°C, 70°C, and 90°C, over different times ranging from 1 to 24 hours. We discovered that at 70°C, the 1:2.5 mixture needed about 20 hours to mostly complete the reaction, while the 1:3.0 mixture needed only 16 hours. Both ratios showed good progress in reducing the carbonate carbonyl peak.

Afterward, we increased the m-XDA ratio to 1:3.5 and tested the adhesive strength at 70°C for 12, 16, and 24 hours. We found that curing for 16 hours gave the highest strength, at nearly 5 MPa (a measure of pressure or strength). Interestingly, increasing the curing time to 24 hours didn’t make much difference, and raising the m-XDA ratio further to 1:4 actually reduced the adhesive's strength. We studied the thermal properties of the adhesive made with the 1:3.5 ratio of m-XDA. It softened at around 19°C and showed stability at higher temperatures when tested in an oxygen-free environment. However, when we increased the m-XDA ratio to 1:4, the adhesive became weaker, likely because of incomplete reactions or disruptions in the structure. Finally, we tried a third chemical, TAA, combining it with CSBO in ratios of 1:2.0, 1:2.5, and 1:3.0. We tested these mixtures at 50°C, 70°C, and 90°C, for times ranging from 1 to 5 hours. The FT-IR analysis showed that a 1:2.5 ratio cured at 70°C for 3 hours was the most effective. Unfortunately, when we tested the adhesive on wood, it failed, likely because of poor bonding or improper curing conditions.

In summary, we found that the best adhesive results were achieved using specific conditions: for IPDA, a 1:3.5–4.0 ratio of CSBO to diamine cured at 70°C for 24 hours, and for m-XDA, a 1:3.5 ratio cured at 70°C for 16 hours. The attempts with TAA were less successful, and further work is needed to improve those results. Throughout, we used careful monitoring and testing to optimize the reactions and understand how each factor affected the final adhesive properties.

View uploaded report PDF file

Final Project Results

Updated September 18, 2025:
In this stage of the project, we continued our evaluation of NIPU (Non-Isocyanate Polyurethane) coatings by moving beyond the earlier phase, where we had already assessed their thermal stability, resistance to water, and hardness, and we aimed to understand how these coatings behave under fire exposure, how robust and interconnected their internal structure is, how resistant they are to corrosive environments, and whether they can stop common stains like ink from sticking to surfaces, which means that our progress report now provides a full picture of how far we have come in testing these novel materials; starting with fire testing, we compared plain uncoated wood to wood coated with three different NIPU formulations known as CSBO_CYS, CSBO_DETA, and CSBO_TETA, and what we discovered was that uncoated wood ignited almost instantly at around three seconds and burned for about a minute and a half with about seven percent of its mass lost, while the coated samples delayed ignition to between four and five seconds, burned for much shorter times, and showed greatly reduced weight loss, with CSBO_DETA in particular standing out by catching fire only after about five seconds, burning for just thirty-eight seconds, and losing only about one and a half percent of its mass, while the other two coatings also offered good protection but with slightly higher burning times and weight loss, so the progress here clearly demonstrates that the NIPU coatings provide an effective barrier to flames; moving next to the gel content tests, which measure how “cross-linked” or interconnected the internal network of the coating is, we immersed the materials in both water and toluene for twenty-four hours and then checked how much of the structure remained intact, and we found that all three coatings maintained more than ninety-five percent of their original structure, meaning they are very strongly cross-linked and do not break down easily, though in water their performance dipped slightly due to the hydrophilic or water-loving parts of their chemistry, but overall the result shows strong durability, which is key progress because cross-linking is directly tied to how tough and long-lasting a material will be; in terms of chemical resistance, our progress involved applying these coatings to stainless steel coupons and exposing them to saltwater, a strong acid (sulfuric acid), and a strong base (sodium hydroxide), and when checked after one hour, all coated surfaces held up against saltwater and base while uncoated surfaces stained in acid, but after twenty-four hours, both coated and uncoated surfaces showed corrosion in acid, saltwater remained harmless, and in base the uncoated steel stained while CSBO_CYS and CSBO_TETA stayed intact and CSBO_DETA began corroding, which means that the coatings generally resist salt and base environments but acids remain too aggressive, an important progress checkpoint that highlights both strengths and limits; finally, our ink repellence testing showed that while uncoated wood absorbed oil-based marker ink permanently, all coated surfaces allowed the ink to be wiped away completely with a tissue, leaving no trace, which is notable progress since it demonstrates an unexpected benefit of cleanliness and easy maintenance; taken together, the progress we report is that NIPU coatings have advanced from being only theoretically promising to being practically tested across multiple conditions, and the accumulated evidence shows that they significantly improve fire resistance, structural integrity, resistance to salt and alkaline chemicals, and prevent ink staining, though acid resistance still remains an area for improvement, and as part of ongoing progress, we are now exploring variations in the formulation, particularly by adjusting the amount of diamine cross-linker used, which may further improve fire protection and other performance aspects, and thus the progress so far strongly supports the potential of NIPU coatings for real-world applications in industries such as construction, furniture, and protective finishes, where surfaces need to resist fire, chemicals, and stains while remaining strong and durable over time.

View uploaded report PDF file

The final results of this project clearly show that NIPU (Non-Isocyanate Polyurethane) coatings deliver multiple layers of protection to wood and metal surfaces and can be considered highly effective in several key areas, because when we analyze all the experiments as a whole, the coatings consistently perform better than uncoated surfaces, and in some cases, dramatically so; the flammability tests provide some of the most striking results, since uncoated wood ignites almost immediately within about three seconds, burns for a prolonged ninety seconds, and loses around seven percent of its material, while wood protected with the three NIPU coatings consistently resists ignition longer, burns for much shorter periods, and suffers far less weight loss, with the CSBO_DETA variant delivering the best result by delaying ignition to five seconds, burning for only thirty-eight seconds, and losing just one and a half percent of its weight, while CSBO_TETA and CSBO_CYS also cut burning times down to forty and fifty-four seconds respectively with proportionally lower mass loss, which means that in terms of fire safety, the final result is unambiguous: these coatings make wood safer and more resistant to fire damage; looking at gel content as a measure of cross-linking and structural robustness, all three coatings maintained more than ninety-five percent of their integrity after being soaked in both water and toluene, which demonstrates a very high level of internal stability, and although they performed slightly less well in water due to hydrophilic components in their chemistry, the overall takeaway is that the final results confirm these coatings are strongly bonded materials that will not easily fall apart or dissolve, making them reliable for long-term use; when we assess chemical resistance, the final results show a nuanced picture, since in saltwater all coatings completely protected the underlying steel even after twenty-four hours, and in sodium hydroxide, CSBO_CYS and CSBO_TETA remained intact while CSBO_DETA began to show signs of corrosion, and in sulfuric acid, both coated and uncoated surfaces corroded over time, which proves that while the coatings are effective against salt and alkaline environments, acids are still too strong for them, so the final outcome is positive but with a known limitation; the ink repellence testing provides another clear and practical result, as uncoated wood absorbed ink permanently while all coated wood allowed marker lines to be wiped away cleanly with a tissue, leaving no stains, showing that the coatings can keep surfaces clean and easy to maintain, which is a valuable property for everyday use; therefore, the final consolidated results across all tests demonstrate that NIPU coatings make wood significantly more fire-resistant, give the material a highly stable and cross-linked structure, provide excellent resistance to salt and alkaline chemical damage, and add a layer of protection against ink stains, though they cannot fully resist strong acids, and together these results point to the conclusion that NIPU coatings are practical, multifunctional materials with applications in construction, furniture, and protective coatings, where they can improve safety, durability, and cleanliness, and importantly, the project’s final results also suggest clear pathways for further improvement by adjusting the formulation—particularly the amount of diamine cross-linker used—which may boost flame resistance and chemical durability even more, so overall the final results are both encouraging and conclusive, showing that NIPU coatings are not just a laboratory success but a material with real-world potential ready for the next steps of industrial application and refinement.

Benefit To Soybean Farmers

Polyurethanes are used in the production of flexible foams (39%), rigid foams (26%), coatings (13%), binders (4%), elastomers, and adhesives. The global polyurethane market size was valued at USD 72.82 billion in 2021 and is expected to expand at a compound annual growth rate (CAGR) of 4.3% from 2022 to 2030. Over 24 million metric tons of polyurethane were used globally in 2021. Utilizing soybean oil for such a huge industry will generate a demand of ~ 15 million metric tons of soybean oil (over 3 billion soybean bushels) per year. Kansas ranked 10th in soybean production among US states. Soybeans will provide a good source of raw material for the polyurethane industry. Creating advanced materials and technologies using soybean oil will provide financial benefits to soybean growers.

The United Soybean Research Retention policy will display final reports with the project once completed but working files will be purged after three years. And financial information after seven years. All pertinent information is in the final report or if you want more information, please contact the project lead at your state soybean organization or principal investigator listed on the project.