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Published in: Journal of Coatings Technology and Research 3/2021

05-03-2021

Coal-derived, solid resins as economic raw materials for coatings

Authors: Stefan Holberg, Xinyan Wang, William C. Schaffers, David A. Bell, Jeramie J. Adams, Patrick A. Johnson

Published in: Journal of Coatings Technology and Research | Issue 3/2021

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Abstract

Solvent extraction of subbituminous coal at mild conditions (360°C) provides solid extracts that consist of numerous organic molecules that can be utilized in the synthesis of polymeric coatings. We describe the extraction process as well as the application of the resultant materials, which bear phenolic groups as the main reactive functionality, for the synthesis of polyurethane and epoxy coatings. The respective reactions of coal extract with isocyanates or epoxides were validated by 13C-NMR. By combining 50–67% coal extract with suitable, flexible co-reactants and co-resins, we formulated coatings with excellent wet adhesion to aluminum, flexibility, and corrosion protection with the same quality as reference coatings. The work is an advancement toward the goal of developing economic and resource-efficient routes from coal to polymers with attractive properties, where coal extracts can compete with petrochemically derived raw materials.

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Appendix
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Literature
4.
go back to reference Gagarin, H, Sridhar, S, Lange, I, Bazillian, MD, “Considering Non-power Generation Uses of Coal in the United States.” Renew. Sust. Energ. Rev., 124 109790 (2020)CrossRef Gagarin, H, Sridhar, S, Lange, I, Bazillian, MD, “Considering Non-power Generation Uses of Coal in the United States.” Renew. Sust. Energ. Rev., 124 109790 (2020)CrossRef
5.
go back to reference Mochida, I, Okuma, O, Yoon, S, “Chemicals from Direct Coal Liquefication.” Chem. Rev., 114 1637–1672 (2014)CrossRef Mochida, I, Okuma, O, Yoon, S, “Chemicals from Direct Coal Liquefication.” Chem. Rev., 114 1637–1672 (2014)CrossRef
6.
go back to reference Okuyama, N, Komatsu, N, Shigehisa, T, Kaneko, T, Tsuruya, S, “Hyper-Coal Process to Produce the Ash-Free Coal.” Fuel Process. Technol., 85 947–967 (2004)CrossRef Okuyama, N, Komatsu, N, Shigehisa, T, Kaneko, T, Tsuruya, S, “Hyper-Coal Process to Produce the Ash-Free Coal.” Fuel Process. Technol., 85 947–967 (2004)CrossRef
9.
go back to reference Li, B, Zhang, J, Wei, J, Zhang, Q, “Preparation and Sealing Performance of a New Coal Dust Polymer Composite Sealing Material.” Adv. Mater. Sci. Eng., 2018 8480913 (2018) Li, B, Zhang, J, Wei, J, Zhang, Q, “Preparation and Sealing Performance of a New Coal Dust Polymer Composite Sealing Material.” Adv. Mater. Sci. Eng., 2018 8480913 (2018)
10.
go back to reference Hu, G, Bian, Z, Xue, R, Huang, W, Komarmeni, S, “Polymer-Coal Composite as a Novel Plastic Material.” Mater. Lett., 197 31–34 (2017)CrossRef Hu, G, Bian, Z, Xue, R, Huang, W, Komarmeni, S, “Polymer-Coal Composite as a Novel Plastic Material.” Mater. Lett., 197 31–34 (2017)CrossRef
11.
go back to reference Tan, J, Cheng, H, Wei, L, Wei, C, Xing, Y, Gui, X, “Using Low-Rank Coal Slime as an Eco-Friendly Replacement for Carbon Black Filler in Styrene Butadiene Rubber.” J. Clean. Prod., 234 949–960 (2019)CrossRef Tan, J, Cheng, H, Wei, L, Wei, C, Xing, Y, Gui, X, “Using Low-Rank Coal Slime as an Eco-Friendly Replacement for Carbon Black Filler in Styrene Butadiene Rubber.” J. Clean. Prod., 234 949–960 (2019)CrossRef
13.
go back to reference Powell, C, Beall, GW, “Graphene Oxide and Graphene from Low Grade Coal: Synthesis, Characterization and Applications.” Curr. Opin. Colloid Interface Sci., 20 362–366 (2015)CrossRef Powell, C, Beall, GW, “Graphene Oxide and Graphene from Low Grade Coal: Synthesis, Characterization and Applications.” Curr. Opin. Colloid Interface Sci., 20 362–366 (2015)CrossRef
14.
go back to reference Savitskii, DP, “Preparation and Characterization of Colloidal Dispersions of Graphene-Like Structures from Different Ranks of Coals.” J. Fuel Chem. Technol., 45 897–907 (2017)CrossRef Savitskii, DP, “Preparation and Characterization of Colloidal Dispersions of Graphene-Like Structures from Different Ranks of Coals.” J. Fuel Chem. Technol., 45 897–907 (2017)CrossRef
15.
go back to reference Zhamu, A, Jang, BZ, “Direct Ultrasonication Production of Graphene Sheets from Coke or Coal.” US Patent 10,081,550 (2018) Zhamu, A, Jang, BZ, “Direct Ultrasonication Production of Graphene Sheets from Coke or Coal.” US Patent 10,081,550 (2018)
17.
go back to reference Orem, WH, Finkelman, RB, “Coal Formation and Geochemistry.” In: Mackenzie, FT, Holland, HD, Turekian, KK (eds.) Sediments, Diagenesis, and Sedimentary Rocks: Treatise on Geochemistry2nd, Vol. 7, pp. 191–222. Elsevier Science, Amsterdam (2003) Orem, WH, Finkelman, RB, “Coal Formation and Geochemistry.” In: Mackenzie, FT, Holland, HD, Turekian, KK (eds.) Sediments, Diagenesis, and Sedimentary Rocks: Treatise on Geochemistry2nd, Vol. 7, pp. 191–222. Elsevier Science, Amsterdam (2003)
18.
go back to reference Hatcher, PG, Clifford, DJ, “The Organic Geochemistry of Coal: From Plant Materials to Coal.” Org. Geochem., 27 251–274 (1997)CrossRef Hatcher, PG, Clifford, DJ, “The Organic Geochemistry of Coal: From Plant Materials to Coal.” Org. Geochem., 27 251–274 (1997)CrossRef
19.
go back to reference Hatcher, PG, “Chemical Structural Models for Coalified Wood (Vitrinite) in Low Rank Coals.” Org. Geochem., 16 959–968 (1990)CrossRef Hatcher, PG, “Chemical Structural Models for Coalified Wood (Vitrinite) in Low Rank Coals.” Org. Geochem., 16 959–968 (1990)CrossRef
20.
go back to reference Mathews, JP, Chaffee, AL, “The Molecular Representation of Coal—A Review.” Fuel, 96 1–14 (2012)CrossRef Mathews, JP, Chaffee, AL, “The Molecular Representation of Coal—A Review.” Fuel, 96 1–14 (2012)CrossRef
21.
go back to reference Shinn, JH, “Visualization of Complex Hydrocarbon Reaction Systems.” Am. Chem. Soc. Div. Fuel. Chem., 41 510–515 (1996) Shinn, JH, “Visualization of Complex Hydrocarbon Reaction Systems.” Am. Chem. Soc. Div. Fuel. Chem., 41 510–515 (1996)
22.
go back to reference Gunderson, TJ, Holberg, S, Bassham, ST, Wang, X, Downey, MR, Adams, JJ, Khambati, DP, Bell, DA, Ackerman, JF, Johnson, PA, “Polyurethanes Derived from Coal Extract.” J. Appl. Polym., 137 48776 (2019)CrossRef Gunderson, TJ, Holberg, S, Bassham, ST, Wang, X, Downey, MR, Adams, JJ, Khambati, DP, Bell, DA, Ackerman, JF, Johnson, PA, “Polyurethanes Derived from Coal Extract.” J. Appl. Polym., 137 48776 (2019)CrossRef
24.
go back to reference Gellerstedt, G, Li, J, Eide, I, Kleinert, M, Barth, T, “Chemical Structures Present in Biofuel Obtained from Lignin.” Energy Fuels, 22 4240–4244 (2008)CrossRef Gellerstedt, G, Li, J, Eide, I, Kleinert, M, Barth, T, “Chemical Structures Present in Biofuel Obtained from Lignin.” Energy Fuels, 22 4240–4244 (2008)CrossRef
26.
go back to reference Neavel, RC, “Exxon Donor Solvent Liquefaction Process.” Philos. Trans. R. Soc. Lond. A, 300 141–156 (1981)CrossRef Neavel, RC, “Exxon Donor Solvent Liquefaction Process.” Philos. Trans. R. Soc. Lond. A, 300 141–156 (1981)CrossRef
27.
go back to reference Ashida, R, Painter, P, Larsen, JW, “Kerogen Chemistry 4. Thermal Decarboxylation of Kerogens.” Energy Fuels, 19 1954–1961 (2005)CrossRef Ashida, R, Painter, P, Larsen, JW, “Kerogen Chemistry 4. Thermal Decarboxylation of Kerogens.” Energy Fuels, 19 1954–1961 (2005)CrossRef
28.
go back to reference Eskay, TP, Britt, PF, Buchanan, AC, III, “Does Decarboxylation Lead to Cross-Linking in Low-Rank Coals?” Energy Fuels, 10 1257–1261 (1996)CrossRef Eskay, TP, Britt, PF, Buchanan, AC, III, “Does Decarboxylation Lead to Cross-Linking in Low-Rank Coals?” Energy Fuels, 10 1257–1261 (1996)CrossRef
29.
go back to reference Massingill, JL, Jr, Bauer, RS, “Epoxy Resins.” In: Craver, CD, Carraher, CE, Jr (eds.) Applied Polymer Science: 21st Century, pp. 393–423. Elsevier Science, Oxford (2000)CrossRef Massingill, JL, Jr, Bauer, RS, “Epoxy Resins.” In: Craver, CD, Carraher, CE, Jr (eds.) Applied Polymer Science: 21st Century, pp. 393–423. Elsevier Science, Oxford (2000)CrossRef
30.
go back to reference Edward, MJ, “Phenolic Curing Agents for Epoxy Resins.” US patent 4767832 (1988) Edward, MJ, “Phenolic Curing Agents for Epoxy Resins.” US patent 4767832 (1988)
32.
go back to reference Sharmin, E, Zafar, F, “Polyurethane: An Introduction.” In: Zafar, F, Sharmin, E (eds.) Polyurethane. IntechOpen, Rijeka (2012) Sharmin, E, Zafar, F, “Polyurethane: An Introduction.” In: Zafar, F, Sharmin, E (eds.) Polyurethane. IntechOpen, Rijeka (2012)
33.
go back to reference Kothandaraman, H, Nasar, AS, “The Thermal Dissociation of Phenol-Blocked Toluene Diisocyanate Crosslinkers.” Polymer, 34 610–615 (1993)CrossRef Kothandaraman, H, Nasar, AS, “The Thermal Dissociation of Phenol-Blocked Toluene Diisocyanate Crosslinkers.” Polymer, 34 610–615 (1993)CrossRef
34.
go back to reference Chung, H, Washburn, NR, “Improved Lignin Polyurethane Properties with Lewis Acid Treatment.” ACS Appl. Mater. Interfaces, 4 2840–2846 (2012)CrossRef Chung, H, Washburn, NR, “Improved Lignin Polyurethane Properties with Lewis Acid Treatment.” ACS Appl. Mater. Interfaces, 4 2840–2846 (2012)CrossRef
35.
go back to reference Chauhan, M, Gupta, M, Singh, B, Singh, AK, Gupta, VK, “Effect of Functionalized Lignin on the Properties of Lignin-Isocyanate Prepolymer Blends and Composites.” Eur. Polym. J., 52 32–43 (2012)CrossRef Chauhan, M, Gupta, M, Singh, B, Singh, AK, Gupta, VK, “Effect of Functionalized Lignin on the Properties of Lignin-Isocyanate Prepolymer Blends and Composites.” Eur. Polym. J., 52 32–43 (2012)CrossRef
36.
go back to reference Lee, HG, Kim, MJ, Park, SE, Kim, JJ, Kim, BR, Lee, SG, Yoon, YJ, “Phenyl 4,5-Dichloro-6-Oxopyridazine-1(6H)-Carboxylate as Carbonyl Source: Facile and Selective Synthesis of Carbamates and Ureas Under Mild Conditions.” Synlett, 2009 2809–2814 (2009)CrossRef Lee, HG, Kim, MJ, Park, SE, Kim, JJ, Kim, BR, Lee, SG, Yoon, YJ, “Phenyl 4,5-Dichloro-6-Oxopyridazine-1(6H)-Carboxylate as Carbonyl Source: Facile and Selective Synthesis of Carbamates and Ureas Under Mild Conditions.” Synlett, 2009 2809–2814 (2009)CrossRef
37.
go back to reference Bantu, B, Pawar, GM, Decker, U, Wurst, K, Schmidt, AM, Buchmeiser, MR, “CO2 and SnII Adducts of N-Heterocyclic Carbenes as Delayed-Action Catalysts for Polyurethane Synthesis.” Chem. Eur. J., 15 3103–3109 (2009)CrossRef Bantu, B, Pawar, GM, Decker, U, Wurst, K, Schmidt, AM, Buchmeiser, MR, “CO2 and SnII Adducts of N-Heterocyclic Carbenes as Delayed-Action Catalysts for Polyurethane Synthesis.” Chem. Eur. J., 15 3103–3109 (2009)CrossRef
38.
go back to reference Gosh, R, Nethaji, M, Samuelson, AG, “Reversible Double Insertion of Aryl Isocyanates into the Ti–O Bond of Titanium(IV) Isopropoxide.” J. Organomet. Chem., 690 1282–1293 (2005)CrossRef Gosh, R, Nethaji, M, Samuelson, AG, “Reversible Double Insertion of Aryl Isocyanates into the Ti–O Bond of Titanium(IV) Isopropoxide.” J. Organomet. Chem., 690 1282–1293 (2005)CrossRef
39.
go back to reference Mrkvička, V, Lyčka, A, Vícha, R, Klásek, A, “Reaction of 3-Hydroxyquinoline-2,4-Diones with Isocyanates and Thermally Induced Transformation of the Reaction Products.” Helv. Chim. Acta, 94 78–91 (2011)CrossRef Mrkvička, V, Lyčka, A, Vícha, R, Klásek, A, “Reaction of 3-Hydroxyquinoline-2,4-Diones with Isocyanates and Thermally Induced Transformation of the Reaction Products.” Helv. Chim. Acta, 94 78–91 (2011)CrossRef
42.
go back to reference Wang, Z, Cui, YT, Xu, ZB, Qu, J, “Hot Water-Promoted Ring-Opening of Epoxides and Aziridines by Water and Other Nucleopliles.” J. Org. Chem., 73 2270–2274 (2008)CrossRef Wang, Z, Cui, YT, Xu, ZB, Qu, J, “Hot Water-Promoted Ring-Opening of Epoxides and Aziridines by Water and Other Nucleopliles.” J. Org. Chem., 73 2270–2274 (2008)CrossRef
43.
go back to reference Salehi, P, Dabiri, M, Zolfigol, A, Bodaghi Fard, A, “Silica Sulfuric Acid; An Efficient and Reusable Catalyst for Regioselective Ring Opening of Epoxides by Alcohols and Water.” Phosphorus Sulfur Silicon Relat. Elem., 179 1113–1121 (2004)CrossRef Salehi, P, Dabiri, M, Zolfigol, A, Bodaghi Fard, A, “Silica Sulfuric Acid; An Efficient and Reusable Catalyst for Regioselective Ring Opening of Epoxides by Alcohols and Water.” Phosphorus Sulfur Silicon Relat. Elem., 179 1113–1121 (2004)CrossRef
45.
go back to reference Knudsen, OØ, Forsgren, A, Corrosion Control Through Organic Coatings, 2nd ed. CRC Press, Boca Raton (2017)CrossRef Knudsen, OØ, Forsgren, A, Corrosion Control Through Organic Coatings, 2nd ed. CRC Press, Boca Raton (2017)CrossRef
Metadata
Title
Coal-derived, solid resins as economic raw materials for coatings
Authors
Stefan Holberg
Xinyan Wang
William C. Schaffers
David A. Bell
Jeramie J. Adams
Patrick A. Johnson
Publication date
05-03-2021
Publisher
Springer US
Published in
Journal of Coatings Technology and Research / Issue 3/2021
Print ISSN: 1547-0091
Electronic ISSN: 1935-3804
DOI
https://doi.org/10.1007/s11998-020-00457-7

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