Bio-Based Mono- and Difunctional Phthalonitrile Resin Foams
Caleb M. Bunton
ASEE Post-Doctoral Fellow, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Conceptualization (lead), Investigation (lead), Methodology (lead)
Search for more papers by this authorCorresponding Author
James D. Sitter
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Correspondence:
James D. Sitter ([email protected])
Contribution: Data curation (supporting), Investigation (supporting), Writing - original draft (equal), Writing - review & editing (supporting)
Search for more papers by this authorTyler J. Richardson
ASEE Post-Doctoral Fellow, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (equal), Formal analysis (supporting), Writing - review & editing (supporting)
Search for more papers by this authorJennifer L. Dysart
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorGrant C. Daniels
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (supporting)
Search for more papers by this authorOlufolasade F. Atoyebi
Nova Research Inc., Alexandria, Virginia, USA
Contribution: Data curation (supporting)
Search for more papers by this authorMatthew Laskoski
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Formal analysis (supporting), Funding acquisition (lead), Investigation (supporting), Writing - review & editing (supporting)
Search for more papers by this authorCaleb M. Bunton
ASEE Post-Doctoral Fellow, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Conceptualization (lead), Investigation (lead), Methodology (lead)
Search for more papers by this authorCorresponding Author
James D. Sitter
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Correspondence:
James D. Sitter ([email protected])
Contribution: Data curation (supporting), Investigation (supporting), Writing - original draft (equal), Writing - review & editing (supporting)
Search for more papers by this authorTyler J. Richardson
ASEE Post-Doctoral Fellow, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (equal), Formal analysis (supporting), Writing - review & editing (supporting)
Search for more papers by this authorJennifer L. Dysart
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (supporting), Formal analysis (supporting)
Search for more papers by this authorGrant C. Daniels
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Data curation (supporting)
Search for more papers by this authorOlufolasade F. Atoyebi
Nova Research Inc., Alexandria, Virginia, USA
Contribution: Data curation (supporting)
Search for more papers by this authorMatthew Laskoski
Federal Employee, Naval Research Laboratory of the United States, Washington, D.C, USA
Contribution: Formal analysis (supporting), Funding acquisition (lead), Investigation (supporting), Writing - review & editing (supporting)
Search for more papers by this authorFunding: This work was supported by US Naval Research Laboratory (NRL) and the Office of Naval Research (ONR).
ABSTRACT
The development of two new bio-based phthalonitrile (PN) resin foams with intrinsic blowing agents is reported. The resins were characterized via attenuated total reflectance-Fourier transform infrared spectroscopy (ATR-FTIR), nuclear magnetic resonance (NMR), pycnometry, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), rheometry, and compression testing. The porosity of 3-[4-(3,4-Dicyanophenoxy)phenyl]-2-propenoic acid-phthalonitrile CAPN and 3-[3,4-di(3,4-Dicyanophenoxy)phenyl]-2-propenoic acid-phthalonitrile CFPN were calculated to be 0.610 and 0.437 respectively. Thermal and thermooxidative stability was determined for both resins under nitrogen and air environments. CAPN and CFPN displayed final char yields of 67% and 69% under nitrogen environments while the T d,5% under air environments were 200°C and 360°C respectively. Finally, compression analysis shows the CAPN to be a stiffer material than the larger CFPN foam resin.
Conflicts of Interest
The authors declare no conflicts of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
Filename | Description |
---|---|
app56660-sup-0001-supinfo.docxWord 2007 document , 4.5 MB |
Data S1. |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1A. Badshah, M. R. Kessler, Z. Heng, and A. Hasan, “Synthesis and Characterization of Phthalonitrile Resins Fromortho-Linked Aromatic and Heterocyclic Monomers,” Polymer International 63 (2014): 465–469.
- 2C. Gao, H. B. Gu, A. Du, et al., “Polyaniline Facilitated Curing of Phthalonitrile Resin With Enhanced Processibility and Mechanical Property,” Polymer 219 (2021): 1–7.
- 3G. X. Wang, Y. Guo, Y. Han, et al., “Enhanced Properties of Phthalonitrile Resins Reinforced by Novel Phthalonitrile-Terminated Polyaryl Ether Nitrile Containing Fluorene Group,” High Performance Polymers 32 (2020): 3–11.
- 4Z. H. Weng, Y. Hu, Y. Qi, et al., “Enhanced Properties of Phthalonitrile Resins Under Lower Curing Temperature via Complex Curing Agent,” Polymers for Advanced Technologies 31 (2020): 233–239.
- 5C. A. Staples, “A Review of the Environmental Fate and Aquatic Effects of a Series of C4 and C8 Oxo-Process Chemicals,” Chemosphere 45 (2001): 339–346.
- 6M. Ike, M. Y. Chen, C. S. Jin, and M. Fujita, “Acute Toxicity, Mutagenicity, and Estrogenicity of Biodegradation Products of Bisphenol-A,” Environmental Toxicology 17 (2002): 457–461.
- 7M. Laskoski, J. S. Clarke, A. Neal, et al., “Sustainable High-Temperature Phthalonitrile Resins Derived From Resveratrol and Dihydroresveratrol,” ChemistrySelect 1 (2016): 3423–3427.
- 8M. Laskoski, A. R. Shepherd, W. Mahzabeen, J. S. Clarke, T. M. Keller, and U. Sorathia, “Sustainable, Fire-Resistant Phthalonitrile-Based Glass Fiber Composites,” Journal of Polymer Science Part A: Polymer Chemistry 56 (2018): 1128–1132.
- 9K. Pei, J. Ou, J. Huang, and S. Ou, “P-Coumaric Acid and Its Conjugates: Dietary Sources, Pharmacokinetic Properties and Biological Activities,” Journal of the Science of Food and Agriculture 96 (2016): 2952–2962.
- 10J. D. Sitter, T. Richardson, J. M. Wallace, C. Lusk, L. C. Brown, and M. Laskoski, “Vanillin Based Phthalonitrile and Acetylene Bifunctional Resins,” Journal of Applied Polymer Science 141 (2024): e55879.
- 11C. P. R. Nair, D. Mathew, and K. N. Ninan, New Polymerization Techniques and Synthetic Methodologies, eds. A. Abe, A. C. Albertsson, H. J. Cantow, et al. (Berlin: Springer, 2001).
10.1007/3-540-44473-4_1 Google Scholar
- 12M. O. Abdalla, D. Dean, and S. Campbell, “Viscoelastic and Mechanical Properties of Thermoset PMR-Type Polyimide–Clay Nanocomposites,” Polymer 43 (2002): 5887–5893.
- 13D. Dean, M. A. Abdalla, U. Vaidya, et al., “Processable PMR-Type Polyimides: Process-Property Relationships, Curing Kinetics, and Thermooxidative Stability,” High Performance Polymers 17 (2005): 497–514.
- 14S. Li, H.-X. Yan, Y. Jia, and T.-Y. Liu, “Phosphorus-Containing Polyhedral Oligomeric Silsesquioxane Designed For High-Performance Flame-Retardant Bismaleimide Resins,” Journal of Polymer Research 23 (2016): 1.
- 15M. Pellegrino, R. Giuseppe, R. Pietro, and L. Mascia, “Thermal-Oxidative Degradation of Epoxy and Epoxy-Bismaleimide Networks: Kinetics and Mechanism,” Macromolecular Chemistry and Physics 202, no. 18 (2001): 3445.
10.1002/1521-3935(20011201)202:18<3445::AID-MACP3445>3.0.CO;2-N Google Scholar
- 16H. Gou, Y. Bao, J. Huang, X. Fei, X. Li, and W. Wei, “Development of Molding Compounds Based on Epoxy Resin/Aromatic Amine/Benzoxazine for High-Temperature Electronic Packaging Applications,” Macromolecular Materials and Engineering 307 (2022): 2200351.
- 17P. Sharma and M. Hakkarainen, “Light Responsive Chemistry—A Design Strategy for Remodelling Benzoxazine Architectures Towards Room Temperature Processing,” Materials Today Chemistry 38 (2024): 102073.
- 18M. Laskoski, A. Neal, T. M. Keller, D. Dominguez, C. A. Klug, and A. P. Saab, “Improved Synthesis of Oligomeric Phthalonitriles and Studies Designed for Low Temperature Cure,” Journal of Polymer Science Part A: Polymer Chemistry 52 (2014): 1662–1668.
- 19L. J. Kasehagen, I. Haury, C. W. Macosko, and D. A. Shimp, “Hydrolysis and Blistering of Cyanate Ester Networks,” Journal of Applied Polymer Science 64 (1997): 107.
- 20J. T. Reams, A. J. Guenthner, K. R. Lamison, G. R. Yandek, D. D. Swanson, and J. M. Mabry, “Formulation and Physical Properties of Cyanate Ester Nanocomposites Based on Graphene,” Journal of Polymer Science Part B: Polymer Physics 52 (2014): 1061–1070.
- 21K. N. Shivakumar, H. Chen, and G. Holloway, “Effect of Thermal Fatigue on Tensile and Flexural Properties of Carbon/Cyanate Ester Pultruded Composite,” Journal of Reinforced Plastics and Composites 28 (2009): 675–689.
- 22B. A. Bulgakov, O. S. Morozov, I. A. Timoshkin, A. V. Babkin, and A. V. Kepman, “Bisphthalonitrile-Based Thermosets as Heat-Resistant Matrices for Fiber Reinforced Plastics,” Polymer Science, Series C 63 (2021): 64–101.
- 23S. B. Sastri and T. M. Keller, “Phthalonitrile Cure Reaction with Aromatic Diamines,” Journal of Polymer Science Part A: Polymer Chemistry 1998 (1885): 36.
- 24S. B. Sastri and T. M. Keller, “Phthalonitrile Polymers: Cure Behavior and Properties,” Journal of Polymer Science Part A: Polymer Chemistry 37 (1999): 2105–2111.
10.1002/(SICI)1099-0518(19990701)37:13<2105::AID-POLA25>3.0.CO;2-A CAS Web of Science® Google Scholar
- 25W. Liu, Q. Qiu, J. Wang, Z. Huo, and H. Sun, “Curing Kinetics and Properties of Epoxy Resin–Fluorenyl Diamine Systems,” Polymer 49 (2008): 4399–4405.
- 26B. Kiskan, N. N. Ghosh, and Y. Yagci, “Polybenzoxazine-Based Composites as High-Performance Materials,” Polymer International 60 (2011): 167–177.
- 27M. Laskoski, M. B. Schear, A. Neal, et al., “Improved Synthesis and Properties of Aryl Ether-Based Oligomeric Phthalonitrile Resins and Polymers,” Polymer 67 (2015): 185–191.
- 28M. Laskoski, A. Neal, M. B. Schear, T. M. Keller, H. L. Ricks-Laskoski, and A. P. Saab, “Oligomeric Aliphatic–Aromatic Ether Containing Phthalonitrile Resins,” Journal of Polymer Science Part A: Polymer Chemistry 53 (2015): 2186–2191.
- 29M. Laskoski, T. M. Keller, H. L. Ricks-Laskoski, C. B. Giller, and J. Hervey, “Improved Synthesis of Oligomeric Sulfone-Based Phthalonitriles,” Macromolecular Chemistry and Physics 2015 (1808): 216.
- 30M. Laskoski, D. D. Dominguez, and T. M. Keller, “Synthesis and Properties of a Bisphenol A Based Phthalonitrile Resin,” Journal of Polymer Science Part A: Polymer Chemistry 43 (2005): 4136–4143.
- 31M. Laskoski, D. D. Dominguez, and T. M. Keller, “Synthesis and Properties of Aromatic Ether Phosphine Oxide Containing Oligomeric Phthalonitrile Resins With Improved Oxidative Stability,” Polymer 48 (2007): 6234–6240.
- 32M. Laskoski, J. S. Clarke, A. Neal, H. L. Ricks-Laskoski, W. J. Hervey, and T. M. Keller, “Synthesis of Bisphenol A-Free Oligomeric Phthalonitrile Resins With Sulfone and Sulfone-Ketone Containing Backbones,” Journal of Polymer Science Part A: Polymer Chemistry 54 (2016): 1639–1646.
- 33M. Laskoski, J. S. Clarke, A. Neal, and T. M. Keller, “Phthalonitrile Blends: Simple Way to Improve Physical Properties by Increasing Crosslinking Density,” Macromolecular Chemistry and Physics 218 (2017): 218.
- 34C. Magnani, V. L. B. Isaac, M. A. Correa, and H. R. N. Salgado, “Caffeic Acid: A Review of Its Potential Use in Medications and Cosmetics,” Analytical Methods 6 (2014): 3203–3210.
- 35M. Cai, J. Liu, X. Song, et al., “21世纪以来我国外语教学研究主题可视化分析与反思,” Microbial Cell Factories 21 (2022): 1.
- 36E.-B. Gao, K. Kyere-Yeboah, J. Wu, and H. Qiu, “Photoautotrophic Production of p-Coumaric Acid Using Genetically Engineered Synechocystis Sp. Pasteur Culture Collection 6803,” Algal Research 54 (2021): 102180.
10.1016/j.algal.2020.102180 Google Scholar
- 37S. P. Ozkorucuklu, J. L. Beltrán, G. Fonrodona, D. Barrón, G. Alsancak, and J. Barbosa, “Determination of Dissociation Constants of Some Hydroxylated Benzoic and Cinnamic Acids in Water From Mobility and Spectroscopic Data Obtained by CE-DAD,” Journal of Chemical & Engineering Data 54 (2009): 807–811.
- 38A. E. Fazary and Y.-H. Ju, “Nonaqueous Solution Studies on the Protonation Equilibria of Some Phenolic Acids,” Journal of Solution Chemistry 37 (2008): 1305–1319.
- 39M. Xu, K. Jia, and X. Liu, “Self-Cured Phthalonitrile Resin via Multistage Polymerization Mediated by Allyl and Benzoxazine Functional Groups,” High Performance Polymers 28 (2016): 1161–1171.
- 40J. J. Cash, M. C. Davis, M. D. Ford, et al., “High Tg Thermosetting Resins From Resveratrol,” Polymer Chemistry 4 (2013): 3859.
- 41B. G. Harvey, A. J. Guenthner, W. W. Lai, et al., “Effects Ofo-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins,” Macromolecules 48 (2015): 3173–3179.
- 42B. G. Harvey, A. J. Guenthner, H. A. Meylemans, et al., “Renewable Thermosetting Resins and Thermoplastics From Vanillin,” Green Chemistry 17 (2015): 1249–1258.
- 43B. G. Harvey, C. M. Sahagun, A. J. Guenthner, et al., “A High-Performance Renewable Thermosetting Resin Derived From Eugenol,” ChemSusChem 2014 (1964): 7–1969.
- 44J. A. Muldoon, M. D. Garrison, M. A. Savolainen, and B. G. Harvey, “Ambient Temperature Cross-Linking of a Sustainable, Cardanol-Based Cyanate Esterviasynergistic Thiol–Ene Copolymerization,” Polymer Chemistry 13 (2022): 3091–3101.
- 45S. Gaidukov, U. Cabulis, K. Gromilova, V. Tupureina, and A. Grigalovica, “Preparation and Structural Properties of Free Films From Rapeseed Oil-Based Rigid Polyurethane-Montmorillonite Nanocomposites,” International Journal of Polymeric Science 2013 (2013): 1–8.
- 46G. G. Matlou, N. Kobayashi, M. Kimura, and T. Nyokong, “Synthesis and Photophysical Studies of Asymmetric Zinc Phthalocyanine–Magnetic Nanoparticle Conjugates,” New Journal of Chemistry 41 (2017): 12309–12318.
- 47J. Muller, G. Hakvoort, and J. Jansen, “DSC and TG Study of Water Adsorption and Desorption on Zeolite NA Powder and Attached as Layer on Metal,” Journal of Thermal Analysis and Calorimetry 53 (1998): 449–466.