[en] Polyurethane (PU) adhesives and coatings are widely used to fabricate high-quality materials due to their excellent properties and their versatile nature, which stems from the wide range of commercially available polyisocyanate and polyol precursors. This polymer family has traditionally been used in a wide range of adhesive applications including the bonding of footwear soles, bonding of wood (flooring) to concrete (subflooring), in the automotive industry for adhering different car parts, and in rotor blades, in which large surfaces are required to be adhered. Moreover, PUs are also frequently applied as coatings/paints for automotive finishes and can be applied over a wide range of substrates such as wood, metal, plastic, and textiles. One of the major drawbacks of this polymer family lies in the use of toxic isocyanate-based starting materials. In the context of the REACH regulation, which places restrictions on the use of substances containing free isocyanates, it is now urgent to find greener routes to PUs. While non-isocyanate polyurethanes (NIPUs) based on the polyaddition of poly(cyclic carbonate)s to polyamines have emerged in the past decade as greener alternatives to conventional PUs, their industrial implementation is at an early stage of development. In this review article, recent advances in the application of NIPUs in the field of adhesives and coatings are summarized. The article also draws attention to the opportunities and challenges of implementing NIPUs at the industrial scale.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM), Belgium Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Belgium Fonds européen de développement régional ( FEDER) The Walloon Region of Belgium in the frame of the BIODEC project
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Gomez-Lopez, Alvaro; University of the Basque Country, POLYMAT, Donostia/SanSebastian, Spain
Panchireddy, Satyannarayana ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Grignard, Bruno ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Calvo, Ingo; ORIBAY Group Automotive S.L., R&D, Donostia/SanSebastian, Spain
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Sardon, Haritz; University of the Basque Country, POLYMAT, Donostia/SanSebastian, Spain
Language :
English
Title :
Poly(hydroxyurethane) adhesives and coatings: state-of-the-art and future directions
Publication date :
26 July 2021
Journal title :
ACS Sustainable Chemistry and Engineering
eISSN :
2168-0485
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
9
Issue :
28
Pages :
9541-9562
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen EOS - The Excellence Of Science Program
Bayer, O. Siefken, W. Rinke, H. Orthner, L. Schild, H. A Process for the Preparation of Polyurethanes or Polyureas. DRP 728981, 1937.
Szycher, M. Polyurethane Adhesives. In Szycher’s Handbook of Polyurethanes ; Szycher, M., Ed.; Taylor and Francis Group :, 2013 ; pp 393 - 416.
Karol, M. H. ; Kramarik, J. A. Phenyl Isocyanate Is a Potent Chemical Sensitizer. Toxicol. Lett. 1996, 89 (), 139 - 146, 10.1016/S0378-4274(96)03798-8
Bello, D. ; Herrick, C. A. ; Smith, T. J. ; Woskie, S. R. ; Streicher, R. P. ; Cullen, M. R. ; Liu, Y. ; Redlich, C. A. Skin Exposure to Isocyanates: Reasons for Concern. Environ. Health Perspect. 2007, 115 (), 328 - 335, 10.1289/ehp.9557
Barbhuiya, M. ; Bhunia, S. ; Kakkar, M. ; Shrivastava, B. ; Tiwari, P. ; Gupta, S. Fine Needle Aspiration Cytology of Lesions of Liver and Gallbladder: An Analysis of 400 Consecutive Aspirations. J. Cytol. 2014, 31 (), 20 - 24, 10.4103/0970-9371.130634
Slocombe, R. J. ; Hardy, E. E. ; Saunders, J. H. ; Jenkins, R. L. Phosgene Derivatives. The Preparation of Isocyanates, Carbamyl Chlorides and Cyanuric Acid1. J. Am. Chem. Soc. 1950, 72 (), 1888 - 1891, 10.1021/ja01161a009
Khatoon, H. ; Iqbal, S. ; Irfan, M. ; Darda, A. ; Rawat, N. K. A Review on the Production, Properties and Applications of Non-Isocyanate Polyurethane: A Greener Perspective. Prog. Org. Coat. 2021, 154, 106124, 10.1016/j.porgcoat.2020.106124
Maisonneuve, L. ; Lamarzelle, O. ; Rix, E. ; Grau, E. ; Cramail, H. Isocyanate-Free Routes to Polyurethanes and Poly(Hydroxy Urethane)S. Chem. Rev. 2015, 115 (), 12407 - 12439, 10.1021/acs.chemrev.5b00355
Grignard, B. ; Gennen, S. ; Jérôme, C. ; Kleij, A. W. ; Detrembleur, C. Advances in the Use of CO2 as a Renewable Feedstock for the Synthesis of Polymers. Chem. Soc. Rev. 2019, 48 (), 4466 - 4514, 10.1039/C9CS00047J
Alves, M. ; Grignard, B. ; Mereau, R. ; Jerome, C. ; Tassaing, T. ; Detrembleur, C. Organocatalyzed Coupling of Carbon Dioxide with Epoxides for the Synthesis of Cyclic Carbonates: Catalyst Design and Mechanistic Studies. Catal. Sci. Technol. 2017, 7 (), 2651 - 2684, 10.1039/C7CY00438A
Kamphuis, A. J. ; Picchioni, F. ; Pescarmona, P. P. CO2-Fixation into Cyclic and Polymeric Carbonates: Principles and Applications. Green Chem. 2019, 21 (), 406 - 448, 10.1039/C8GC03086C
Guo, L. ; Lamb, K. J. ; North, M. Recent Developments in Organocatalysed Transformations of Epoxides and Carbon Dioxide into Cyclic Carbonates. Green Chem. 2021, 23 (), 77 - 118, 10.1039/D0GC03465G
Aomchad, V. ; Cristòfol, À. ; Della Monica, F. ; Limburg, B. ; D’Elia, V. ; Kleij, A. W. Recent Progress in the Catalytic Transformation of Carbon Dioxide into Biosourced Organic Carbonates. Green Chem. 2021, 23 (), 1077 - 1113, 10.1039/D0GC03824E
Carré, C. ; Ecochard, Y. ; Caillol, S. ; Avérous, L. From the Synthesis of Biobased Cyclic Carbonate to Polyhydroxyurethanes: A Promising Route towards Renewable Non-Isocyanate Polyurethanes. ChemSusChem 2019, 12 (), 3410 - 3430, 10.1002/cssc.201900737
Llevot, A. ; Meier, M. Perspective: Green Polyurethane Synthesis for Coating Applications. Polym. Int. 2019, 68 (), 826 - 831, 10.1002/pi.5655
Sonnenschein, M. F. Polyurethane Adhesives and Coatings. Polyurethanes: Science, Technology, Markets, and Trends 2014, 336 - 374, 10.1002/9781118901274.ch10
Szycher, M. Structure-Property Relations in Polyurethanes. In Szycher’s Handbook of Polyurethanes ; Szycher, M., Ed.; Taylor and Francis Group :, 2013 ; pp 37 - 86.
Kim, B. K. ; Lee, Y. M. Aqueous Dispersion of Polyurethanes Containing Ionic and Nonionic Hydrophilic Segments. J. Appl. Polym. Sci. 1994, 54 (), 1809 - 1815, 10.1002/app.1994.070541204
Wang, H. ; Shen, Y. ; Fei, G. ; Li, X. ; Liang, Y. Micromorphology and Phase Behavior of Cationic Polyurethane Segmented Copolymer Modified with Hydroxysilane. J. Colloid Interface Sci. 2008, 324 (), 36 - 41, 10.1016/j.jcis.2008.04.068
Lee, H.-T. ; Wu, S.-Y. ; Jeng, R.-J. Effects of Sulfonated Polyol on the Properties of the Resultant Aqueous Polyurethane Dispersions. Colloids Surf., A 2006, 276 (), 176 - 185, 10.1016/j.colsurfa.2005.10.034
Chattopadhyay, D. K. ; Raju, K. V. S. N. Structural Engineering of Polyurethane Coatings for High Performance Applications. Prog. Polym. Sci. 2007, 32 (), 352 - 418, 10.1016/j.progpolymsci.2006.05.003
Chattopadhyay, D. K. ; Webster, D. C. Hybrid Coatings from Novel Silane-Modified Glycidyl Carbamate Resins and Amine Crosslinkers. Prog. Org. Coat. 2009, 66 (), 73 - 85, 10.1016/j.porgcoat.2009.06.004
Szycher, M. Waterborne Polyurethanes. In Szycher’s Handbook of Polyurethanes ; Szycher, M., Ed.; Taylor and Francis Group :, 2013 ; pp 417 - 448.
Szycher, M. Radiation-Curable Adhesives and Coatings. In Szycher’s Handbook of Polyurethanes ; Szycher, M., Ed.; Taylor and Francis Group :, 2013 ; pp 495 - 522.
Petrie, E. M. Adhesive Classification. In Handbook of adhesives and sealants ; Petrie, E. M., Ed.; McGraw-Hill :, 2000 ; pp 279 - 318.
Ebnesajjad, S. ; Landrock, A. H. Introduction and Adhesion Theories. Adhesives Technology Handbook 2015, 1 - 18, 10.1016/B978-0-323-35595-7.00001-2
Petrie, E. M. Surfaces and Surface Preparation. In Handbook of adhesives and sealants ; Petrie, E. M., Ed.; McGraw-Hill :, 2000 ; pp 197 - 252.
Duncan, B. Developments in Testing Adhesive Joints. In Advances in structural adhesive bonding ; Dillard, D. A., Ed.; Woodhead Publishing Limited :, 2010 ; pp 389 - 436.
Ebnesajjad, S. Characteristics of Adhesive Materials. In Handbook of adhesives and surface preparation ; Ebnesajjad, S., Ed.; Elsevier Ltd :, 2011 ; pp 137 - 183.
Ecochard, Y. ; Caillol, S. Hybrid Polyhydroxyurethanes: How to Overcome Limitations and Reach Cutting Edge Properties?. Eur. Polym. J. 2020, 137, 109915, 10.1016/j.eurpolymj.2020.109915
Leitsch, E. K. ; Beniah, G. ; Liu, K. ; Lan, T. ; Heath, W. H. ; Scheidt, K. A. ; Torkelson, J. M. Nonisocyanate Thermoplastic Polyhydroxyurethane Elastomers via Cyclic Carbonate Aminolysis: Critical Role of Hydroxyl Groups in Controlling Nanophase Separation. ACS Macro Lett. 2016, 5 (), 424 - 429, 10.1021/acsmacrolett.6b00102
Tomita, H. ; Sanda, F. ; Endo, T. Polyaddition Behavior of Bis(Five- and Six-Membered Cyclic Carbonate)s with Diamine. J. Polym. Sci., Part A: Polym. Chem. 2001, 39 (), 860 - 867, 10.1002/1099-0518(20010315)39:6<860::AID-POLA1059>3.0.CO;2-2
Schimpf, V. ; Heck, B. ; Reiter, G. ; Mülhaupt, R. Triple-Shape Memory Materials via Thermoresponsive Behavior of Nanocrystalline Non-Isocyanate Polyhydroxyurethanes. Macromolecules 2017, 50 (), 3598 - 3606, 10.1021/acs.macromol.7b00500
Cornille, A. ; Michaud, G. ; Simon, F. ; Fouquay, S. ; Auvergne, R. ; Boutevin, B. ; Caillol, S. Promising Mechanical and Adhesive Properties of Isocyanate-Free Poly(Hydroxyurethane). Eur. Polym. J. 2016, 84, 404 - 420, 10.1016/j.eurpolymj.2016.09.048
Panchireddy, S. ; Grignard, B. ; Thomassin, J.-M. ; Jerome, C. ; Detrembleur, C. Catechol Containing Polyhydroxyurethanes as High-Performance Coatings and Adhesives. ACS Sustainable Chem. Eng. 2018, 6 (), 14936 - 14944, 10.1021/acssuschemeng.8b03429
Tryznowski, M. ; Gołofit, T. ; Świderska, A. Poly(Hydroxyurethane)s with Diethyl Tartrate-Based Amide Backbone by an Isocyanate-Free Route: Use as Adhesives. Polymer 2018, 144, 1 - 6, 10.1016/j.polymer.2018.04.041
Tryznowski, M. ; Świderska, A. ; Gołofit, T. ; Zołek-Tryznowska, Z. Wood Adhesive Application of Poly(Hydroxyurethane)s Synthesized with a Dimethyl Succinate-Based Amide Backbone. RSC Adv. 2017, 7 (), 30385 - 30391, 10.1039/C7RA05455F
Xi, X. ; Pizzi, A. ; Delmotte, L. Isocyanate-Free Polyurethane Coatings and Adhesives from Mono- and Di-Saccharides. Polymers (Basel, Switz.) 2018, 10 (), 402, 10.3390/polym10040402
Xi, X. ; Wu, Z. ; Pizzi, A. ; Gerardin, C. ; Lei, H. ; Zhang, B. ; Du, G. Non-Isocyanate Polyurethane Adhesive from Sucrose Used for Particleboard. Wood Sci. Technol. 2019, 53 (), 393 - 405, 10.1007/s00226-019-01083-2
Sukumaran Nair, A. ; Cherian, S. ; Balachandran, N. ; Panicker, U. G. ; Kalamblayil Sankaranarayanan, S. K. Hybrid Poly(Hydroxy Urethane)s: Folded-Sheet Morphology and Thermoreversible Adhesion. ACS Omega 2019, 4 (), 13042 - 13051, 10.1021/acsomega.9b00789
China National Standard GB/T 17657-Test Methods for Evaluating the Properties of Wood-Based Panels and Surface Decorated Wood-Based Panels ; 1999.
Tanigawa, M. Kimura, K. Takahashi, K. Uruno, M. Muto, K. Hanada, K. Polyhydroxyurethane Resin, Polyhydroxyurethane Resin Composition Containing the Resin, and Adhesive. JP 6367769 B2, 2018.
Muto, K. Kimura, K. Takahashi, K. Uruno, M. Tanigawa, M. Minami, A. Method for Producing Polyhydroxyurethane Resin. JP 2017222760 A, 2017.
Muto, K. Kimura, K. Takahashi, K. Uruno, M. Tanigawa, M. Minami, A. Polyhydroxyurethane Resin, Hot Melt Adhesive Using the Resin, Molded Product and Laminate. JP 2020007406 A, 2020.
Figovsky, O. L. ; Shapovalov, L. D. Nonisocyanate Polyurethanes for Adhesives and Coatings. First Int. IEEE Conf. Polym. Adhes. Microelectron. Photonics Incoperating POLY, PEP Adhasives Electron. 2001, 257 - 264, 10.1109/POLYTR.2001.973291
Figovsky, O. ; Shapovalov, L. ; Birukova, O. ; Leykin, A. Modification of Epoxy Adhesives by Hydroxyurethane Components on the Basis of Renewable Raw Materials. Polym. Sci., Ser. D 2013, 6 (), 271 - 274, 10.1134/S1995421213040047
Stroganov, I. V. ; Stroganov, V. F. Peculiarities of Structurization and Properties of Nonisocyanate Epoxyurethane Polymers. Polym. Sci., Ser. C 2007, 49 (), 258 - 263, 10.1134/S1811238207030113
Lambeth, R. H. ; Rizvi, A. Mechanical and Adhesive Properties of Hybrid Epoxy-Polyhydroxyurethane Network Polymers. Polymer 2019, 183, 121881, 10.1016/j.polymer.2019.121881
Anitha, S. ; Vijayalakshmi, K. P. ; Unnikrishnan, G. ; Kumar, K. S. S. CO 2 Derived Hydrogen Bonding Spacer: Enhanced Toughness, Transparency, Elongation and Non-Covalent Interactions in Epoxy-Hydroxyurethane Networks. J. Mater. Chem. A 2017, 5 (), 24299 - 24313, 10.1039/C7TA08243F
Diakoumakos, C. D. Kotzev, D. L. Nanocomposites Based on Polyurethane or Polyurethane-Epoxy Hybrid Resins Prepared Avoiding Isocyanates. US 8143346 B2, 2012.
Figovsky, O. Shapovalov, L. D. Blank, N. Buslov, F. Method of Synthesis of Polyaminofunctional Hydroxyurethane Oligomers and Hybride Polymers Formed Therefrom. EP 1070733 A1, 2001.
Figovsky, O. Shapovalov, L. D. Blank, N. Buslov, F. Cyclocarbonate Groups Containing Hydroxyamine Oligomers From Epoxycyclocarbonates. US 6407198 B1, 2002.
Figovsky, O. Shapovalov, L. D. Preparation of Oligomeric Cyclocarbonates and Their Use in Nonisocyanate or Hybrid Nonisocyanate Polyurethanes. US 7232877 B2, 2007.
Birukov, O. Figovsky, O. Leykin, A. Shapovalov, L. D. Epoxy-Amine Composition Modified with Hydroxyalkylurethane. US 7898553 B2, 2011.
Lammerschop, O. Kinzelmann, H.-G. Two-Component Binder System with Cyclocarbonate and Epoxy Groups. US 10179871 B2, 2019.
Rossi de Aguiar, K. M. F. ; Ferreira-Neto, E. P. ; Blunk, S. ; Schneider, J. F. ; Picon, C. A. ; Lepienski, C. M. ; Rischka, K. ; Rodrigues-Filho, U. P. Hybrid Urethanesil Coatings for Inorganic Surfaces Produced by Isocyanate-Free and Sol-Gel Routes: Synthesis and Characterization. RSC Adv. 2016, 6 (), 19160 - 19172, 10.1039/C5RA24331A
Gomez-Lopez, A. ; Grignard, B. ; Calvo, I. ; Detrembleur, C. ; Sardon, H. Monocomponent Non-Isocyanate Polyurethane Adhesives Based on a Sol-Gel Process. ACS Appl. Polym. Mater. 2020, 2 (), 1839 - 1847, 10.1021/acsapm.0c00062
Gomez-Lopez, A. ; Grignard, B. ; Calvo, I. ; Detrembleur, C. ; Sardon, H. Synergetic Effect of Dopamine and Alkoxysilanes in Sustainable Non-Isocyanate Polyurethane Adhesives. Macromol. Rapid Commun. 2021, 42, 2000538, 10.1002/marc.202000538
Panchireddy, S. ; Thomassin, J. M. ; Grignard, B. ; Damblon, C. ; Tatton, A. ; Jerome, C. ; Detrembleur, C. Reinforced Poly(Hydroxyurethane) Thermosets as High Performance Adhesives for Aluminum Substrates. Polym. Chem. 2017, 8 (), 5897 - 5909, 10.1039/C7PY01209H
Panchireddy, S. ; Grignard, B. ; Thomassin, J.-M. M. ; Jerome, C. ; Detrembleur, C. Bio-Based Poly(Hydroxyurethane) Glues for Metal Substrates. Polym. Chem. 2018, 9 (), 2650 - 2659, 10.1039/C8PY00281A
Dijkstra, D. J. ; Brock, T. ; Wilde, H. W. PU Coatings. Polym. Int. 2019, 68 (), 823 - 825, 10.1002/pi.5805
Schimpf, V. ; Ritter, B. S. ; Weis, P. ; Parison, K. ; Mülhaupt, R. High Purity Limonene Dicarbonate as Versatile Building Block for Sustainable Non-Isocyanate Polyhydroxyurethane Thermosets and Thermoplastics. Macromolecules 2017, 50 (), 944 - 955, 10.1021/acs.macromol.6b02460
Schmidt, S. ; Ritter, B. S. ; Kratzert, D. ; Bruchmann, B. ; Mülhaupt, R. Isocyanate-Free Route to Poly(Carbohydrate-Urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock. Macromolecules 2016, 49 (), 7268 - 7276, 10.1021/acs.macromol.6b01485
Tryznowski, M. ; Izdebska-Podsiadły, J. ; Żołek-Tryznowska, Z. Wettability and Surface Free Energy of NIPU Coatings Based on Bis(2,3-Dihydroxypropyl)Ether Dicarbonate. Prog. Org. Coat. 2017, 109 (), 55 - 60, 10.1016/j.porgcoat.2017.04.011
Tryznowski, M. ; Żołek-Tryznowska, Z. Surface Properties of Poly(Hydroxyurethane)s Based on Five-Membered Bis-Cyclic Carbonate of Diglycidyl Ether of Bisphenol A. Materials 2020, 13 (), 5184, 10.3390/ma13225184
Wu, Z. ; Tang, L. ; Dai, J. ; Qu, J. Synthesis and Properties of Fluorinated Non-Isocyanate Polyurethanes Coatings with Good Hydrophobic and Oleophobic Properties. J. Coatings Technol. Res. 2019, 16 (), 1233 - 1241, 10.1007/s11998-019-00195-5
Kalinina, F. E. ; Mognonov, D. M. ; Radnaeva, L. D. Poly(Hydroxy Urethane) Coatings Prepared from Copolymers of 3-(2-Vinyloxyethoxy)-l,2-Propylene Carbonate and N-Phenylmaleimide. Russ. J. Appl. Chem. 2008, 81 (), 1302 - 1304, 10.1134/S1070427208070367
Webster, D. C. ; Crain, A. L. Synthesis and Applications of Cyclic Carbonate Functional Polymers in Thermosetting Coatings. Prog. Org. Coat. 2000, 40 (), 275 - 282, 10.1016/S0300-9440(00)00114-4
Morales-Cerrada, R. ; Boutevin, B. ; Caillol, S. Glycerol Carbonate Methacrylate: A Cross-Linking Agent for Hydroxyurethane-Acrylate Coatings. Prog. Org. Coat. 2021, 151, 106078, 10.1016/j.porgcoat.2020.106078
Kathalewar, M. ; Sabnis, A. ; D’Mello, D. Isocyanate Free Polyurethanes from New CNSL Based Bis-Cyclic Carbonate and Its Application in Coatings. Eur. Polym. J. 2014, 57, 99 - 108, 10.1016/j.eurpolymj.2014.05.008
Kathalewar, M. ; Sabnis, A. Preparation of Novel CNSL-Based Urethane Polyol via Nonisocyanate Route: Curing with Melamine-Formaldehyde Resin and Structure-Property Relationship. J. Appl. Polym. Sci. 2015, 132 (), 41391 - 41401, 10.1002/app.41391
Asemani, H. R. ; Mannari, V. Synthesis and Evaluation of Non-Isocyanate Polyurethane Polyols for Heat-Cured Thermoset Coatings. Prog. Org. Coat. 2019, 131, 247 - 258, 10.1016/j.porgcoat.2019.02.036
Wang, C. ; Wu, Z. ; Tang, L. ; Qu, J. Synthesis and Properties of Cyclic Carbonates and Non-Isocyanate Polyurethanes under Atmospheric Pressure. Prog. Org. Coat. 2019, 127, 359 - 365, 10.1016/j.porgcoat.2018.11.040
Yu, A. Z. ; Setien, R. A. ; Sahouani, J. M. ; Docken, J. ; Webster, D. C. Catalyzed Non-Isocyanate Polyurethane (NIPU) Coatings from Bio-Based Poly(Cyclic Carbonates). J. Coatings Technol. Res. 2019, 16 (), 41 - 57, 10.1007/s11998-018-0135-7
Pathak, R. ; Kathalewar, M. ; Wazarkar, K. ; Sabnis, A. Non-Isocyanate Polyurethane (NIPU) from Tris-2-Hydroxy Ethyl Isocyanurate Modified Fatty Acid for Coating Applications. Prog. Org. Coat. 2015, 89, 160 - 169, 10.1016/j.porgcoat.2015.08.015
Novi, C. ; Mourran, A. ; Keul, H. ; Möller, M. Ammonium-Functionalized Polydimethylsiloxanes: Synthesis and Properties. Macromol. Chem. Phys. 2006, 207 (), 273 - 286, 10.1002/macp.200500346
Pasquier, N. ; Keul, H. ; Heine, E. ; Moeller, M. From Multifunctionalized Poly(Ethylene Imine)s toward Antimicrobial Coatings. Biomacromolecules 2007, 8 (), 2874 - 2882, 10.1021/bm070353r
Pasquier, N. ; Keul, H. ; Moeller, M. Polymers with Specific Adhesion Properties for Surface Modification: Synthesis, Characterization and Applications. Des. Monomers Polym. 2005, 8 (), 679 - 703, 10.1163/156855505774597821
Epoxy Non-Isocyanate Polyurethane Insulation Varnish for Magnet Ring. CN 103360906 A, 2013.
Jadhav, A. Biobased Hydroxy-Urethanes as Reactive Diluents. US 2018/0312718 A1, 2018.
Sardon, H. ; Engler, A. C. ; Chan, J. M. W. ; Coady, D. J. ; O’Brien, J. M. ; Mecerreyes, D. ; Yang, Y. Y. ; Hedrick, J. L. Homogeneous Isocyanate- and Catalyst-Free Synthesis of Polyurethanes in Aqueous Media. Green Chem. 2013, 15 (), 1121 - 1126, 10.1039/c3gc40319j
Rix, E. ; Grau, E. ; Chollet, G. ; Cramail, H. Synthesis of Fatty Acid-Based Non-Isocyanate Polyurethanes, NIPUs, in Bulk and Mini-Emulsion. Eur. Polym. J. 2016, 84, 863 - 872, 10.1016/j.eurpolymj.2016.07.006
Bourguignon, M. ; Thomassin, J. M. ; Grignard, B. ; Jerome, C. ; Detrembleur, C. Fast and Facile One-Pot One-Step Preparation of Nonisocyanate Polyurethane Hydrogels in Water at Room Temperature. ACS Sustainable Chem. Eng. 2019, 7 (), 12601 - 12610, 10.1021/acssuschemeng.9b02624
Wu, Z. ; Tang, L. ; Dai, J. ; Qu, J. Synthesis and Properties of Aqueous Cyclic Carbonate Dispersion and Non-Isocyanate Polyurethanes under Atmospheric Pressure. Prog. Org. Coat. 2019, 136 (), 105209, 10.1016/j.porgcoat.2019.105209
Wu, Z. ; Dai, J. ; Tang, L. ; Qu, J. Sorbitol-Based Aqueous Cyclic Carbonate Dispersion for Waterborne Nonisocyanate Polyurethane Coatings via an Environment-Friendly Route. J. Coatings Technol. Res. 2019, 16 (), 721 - 732, 10.1007/s11998-018-0150-8
Zhang, C. ; Wang, H. ; Zhou, Q. Waterborne Isocyanate-Free Polyurethane Epoxy Hybrid Coatings Synthesized from Sustainable Fatty Acid Diamine. Green Chem. 2020, 22, 1329, 10.1039/C9GC03335A
Ma, Z. ; Li, C. ; Fan, H. ; Wan, J. ; Luo, Y. ; Li, B.-G. Polyhydroxyurethanes (PHUs) Derived from Diphenolic Acid and Carbon Dioxide and Their Application in Solvent- and Water-Borne PHU Coatings. Ind. Eng. Chem. Res. 2017, 56 (), 14089 - 14100, 10.1021/acs.iecr.7b04029
Jacobs, W. Blank, W. J. Water Based Hydroxyalkyl Carbamate-Containing Resins and Method of Making the Same. US 4897435, 1990.
Aoki, H. Harakawa, H. Nagai, S. Omoto, H. Saito, Y. Sugawara, T. Takanohashi, Y. Yamamoto, T. Method for Producing Polyhydroxyurethane and Aqueous Dispersion of Polyhydroxyurethane. JP 2007297544 A, 2007.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Minami, A. Carboxyl Group-Containing Polyhydroxyurethane Resin, Water Dispersion of Polyhydroxyurethane Resin, and Method for Producing Water Dispersion of Polyhydroxyurethane Resin. JP 2017193643 A, 2017.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Minami, A. Water Dispersion Composition of Clay Mineral-Containing Polyhydroxyurethane Resin, and Gas Barrier Coating Agent and Gas Barrier Resin Film Using Water Dispersion Composition. JP 2018070841 A, 2018.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Minami, A. Water Dispersion of Polyhydroxyurethane Resin, Method for Producing Water Dispersion, and Gas Barrier Resin Film Using Water Dispersion. JP 2018070840 A, 2018.
Uruno, M. Tanigawa, M. Polyhydroxyurethane Resin Composition, and Gas Barrier Coating Agent and Gas Barrier Film Using the Composition. JP 2019026799 A, 2019.
Figovsky, O. ; Shapovalov, L. ; Buslov, F. Ultraviolet and Thermostable Non-Isocyanate Polyurethane Coatings. Surf. Coat. Int., Part B 2005, 88, 67 - 71, 10.1007/BF02699710
Han, L. ; Dai, J. ; Zhang, L. ; Ma, S. ; Deng, J. ; Zhang, R. ; Zhu, J. Diisocyanate Free and Melt Polycondensation Preparation of Bio-Based Unsaturated Poly(Ester-Urethane)s and Their Properties as UV Curable Coating Materials. RSC Adv. 2014, 4 (), 49471 - 49477, 10.1039/C4RA08665A
Wang, X. ; Soucek, M. D. Investigation of Non-Isocyanate Urethane Dimethacrylate Reactive Diluents for UV-Curable Polyurethane Coatings. Prog. Org. Coat. 2013, 76 (), 1057 - 1067, 10.1016/j.porgcoat.2013.03.001
Boisaubert, P. ; Kébir, N. ; Schuller, A. S. ; Burel, F. Photo-Crosslinked Non-Isocyanate Polyurethane Acrylate (NIPUA) Coatings through a Transurethane Polycondensation Approach. Polymer 2020, 206 (), 122855, 10.1016/j.polymer.2020.122855
Boisaubert, P. ; Kébir, N. ; Schuller, A. S. ; Burel, F. Photo-Crosslinked Coatings from an Acrylate Terminated Non-Isocyanate Polyurethane (NIPU) and Reactive Diluent. Eur. Polym. J. 2020, 138 (), 109961, 10.1016/j.eurpolymj.2020.109961
Hwang, J.-Z. ; Wang, S.-C. ; Chen, P.-C. ; Huang, C.-Y. ; Yeh, J.-T. ; Chen, K.-N. A New UV-Curable PU Resin Obtained through a Nonisocyanate Process and Used as a Hydrophilic Textile Treatment. J. Polym. Res. 2012, 19 (), 9900 - 9910, 10.1007/s10965-012-9900-y
Zareanshahraki, F. ; Asemani, H. R. ; Skuza, J. ; Mannari, V. Synthesis of Non-Isocyanate Polyurethanes and Their Application in Radiation-Curable Aerospace Coatings. Prog. Org. Coat. 2020, 138, 105394, 10.1016/j.porgcoat.2019.105394
Uruno, M. Tanigawa, M. Minami, A. Takahashi, K. Kimura, K. Muto, K. Polyhydroxyurethane Resin, Gas Barrier Coating Agent Using the Same, and Gas Barrier Film Using the Same. JP 6636818 B2, 2019.
Figovsky, O. ; Shapovalov, L. ; Axenov, O. Advanced Coatings Based upon Non-Isocyanate Polyurethanes for Industrial Applications. Surf. Coat. Int., Part B 2004, 87 (), 83 - 90, 10.1007/BF02699601
Figovsky, O. ; Leykin, A. ; Shapovalov, L. Non-Isocyanate Polyurethanes - Yesterday, Today and Tomorrow. Al'tern. Energ. Ekol. 2016, 4 (), 95 - 108, 10.15518/isjaee.2016.03-04.009
Hosgor, Z. ; Kayaman-Apohan, N. ; Karatas, S. ; Gungor, A. ; Menceloglu, Y. Nonisocyanate Polyurethane/Silica Hybrid Coatings via a Sol-Gel Route. Adv. Polym. Technol. 2012, 31 (), 390 - 400, 10.1002/adv.20262
Gharibi, R. ; Yeganeh, H. ; Kazemi, S. Green and Non-Leaching Anti-Bacterial and Cytocompatible Coating with Build-in Quaternary Ammonium Salt Derived from Methoxysilane Functionalized Soybean Oil. Mater. Sci. Eng., C 2019, 99, 887 - 899, 10.1016/j.msec.2019.02.029
Asemani, H. ; Zareanshahraki, F. ; Mannari, V. Design of Hybrid Nonisocyanate Polyurethane Coatings for Advanced Ambient Temperature Curing Applications. J. Appl. Polym. Sci. 2019, 136 (), 47266, 10.1002/app.47266
Birukov, O. Beilin, D. Figovsky, O. Leykin, A. Shapovalov, L. Nanostructured Hybrid Oligomer Composition. US 7820779 B2, 2010.
Birukov, O. Beilin, D. Figovsky, O. Leykin, A. Shapovalov, L. Liquid Oligomer Composition Containing Hydroxyamine Adducts and Method of Manufacturing Thereo. US 2010/0144966 A1, 2010.
Birukov, O. Figovsky, O. Leykin, A. Potashnikov, R. Shapovalov, L. D. Method of Producing Hybrid Polyhydroxyurethane Network on a Base of Carbonated-Epoxidized Unsaturated Fatty Acid Triglycerides. US 9102829 B2, 2015.
Figovsky, O. Potashnikov, R. Leykin, A. Shapovalov, L. D. Birukov, O. Radiation-Curable Biobased Flooring Compositions With Nonreactive Additives. US 9487662 B1, 2016.
Birukov, O. Figovsky, O. Leykin, A. Potashnikov, R. Shapovalov, L. D. Method of Producing Hybrid Polyhydroxyurethane Network on a Base of Carbonated-Epoxidized Unsaturated Fatty Acid Triglycerides. CA 2767784 C, 2018.
Green Polyurethane Is The First Hybrid Polyurethane Manufactured Without Toxic Isocyanates..
Türünç, O. ; Kayaman-Apohan, N. ; Kahraman, M. V. ; Menceloğlu, Y. ; Güngör, A. Nonisocyanate Based Polyurethane/Silica Nanocomposites and Their Coating Performance. J. Sol-Gel Sci. Technol. 2008, 47 (), 290 - 299, 10.1007/s10971-008-1786-0
Liu, G. ; Wu, G. ; Chen, J. ; Kong, Z. Synthesis, Modification and Properties of Rosin-Based Non-Isocyanate Polyurethanes Coatings. Prog. Org. Coat. 2016, 101, 461 - 467, 10.1016/j.porgcoat.2016.09.019
Liu, G. ; Wu, G. ; Chen, J. ; Huo, S. ; Jin, C. ; Kong, Z. Synthesis and Properties of POSS-Containing Gallic Acid-Based Non-Isocyanate Polyurethanes Coatings. Polym. Degrad. Stab. 2015, 121, 247 - 252, 10.1016/j.polymdegradstab.2015.09.013
Blattmann, H. ; Mülhaupt, R. Multifunctional POSS Cyclic Carbonates and Non-Isocyanate Polyhydroxyurethane Hybrid Materials. Macromolecules 2016, 49 (), 742 - 751, 10.1021/acs.macromol.5b02560
Farid, M. E. ; El-Sockary, M. A. ; El-Saeed, A. M. ; Hashem, A. I. ; Abo Elenien, O. M. ; Selim, M. S. ; Park, S. E. An Eco-Friendly Non-Isocyanate Polyurethane Treated by CO2 as Flame Retardant Nanocomposite Coating/ZrO2@SiO2. Mater. Res. Express 2019, 6 (), 065042, 10.1088/2053-1591/ab0da3
Pössel, B. ; Mülhaupt, R. Lysine-Functionalized Gibbsite Nanoplatelet Dispersions for Nonisocyanate Polyhydroxyurethane Nanocomposites and Translucent Coatings. Macromol. Mater. Eng. 2020, 305 (), 2000217, 10.1002/mame.202000217
He, X. ; Xu, X. ; Bo, G. ; Yan, Y. Studies on the Effects of Different Multiwalled Carbon Nanotube Functionalization Techniques on the Properties of Bio-Based Hybrid Non-Isocyanate Polyurethane. RSC Adv. 2020, 10 (), 2180 - 2190, 10.1039/C9RA08695A
Kathalewar, M. ; Sabnis, A. ; Waghoo, G. Effect of Incorporation of Surface Treated Zinc Oxide on Non-Isocyanate Polyurethane Based Nano-Composite Coatings. Prog. Org. Coat. 2013, 76 (), 1215 - 1229, 10.1016/j.porgcoat.2013.03.027
Zhang, C. ; Huang, K. C. ; Wang, H. ; Zhou, Q. Anti-Corrosion Non-Isocyanate Polyurethane Polysiloxane Organic/Inorganic Hybrid Coatings. Prog. Org. Coat. 2020, 148 (), 105855, 10.1016/j.porgcoat.2020.105855
Haniffa, M. A. C. M. ; Chee, C. Y. ; Illias, H. A. ; Halil, A. ; Munawer, K. ; Sandu, V. ; Chuah, C. H. Preparation of Isocyanate-Free Composite Coating with Controlled Molecular Architecture: A New Convergent Approach to Functional Macromolecules. Prog. Org. Coat. 2021, 151, 106039, 10.1016/j.porgcoat.2020.106039
Haniffa, M. A. C. M. ; Illias, H. A. ; Chee, C. Y. ; Ibrahim, S. ; Sandu, V. ; Chuah, C. H. Nonisocyanate Poly(Hydroxyl Urethane)-Based Green Polymer Hybrid Coating Systems: Tailoring of Biomacromolecular Compound Architecture Using APTMS-ZnO/TEMPO-Oxidized Cellulose Nanoparticles. ACS Omega 2020, 5 (), 10315 - 10326, 10.1021/acsomega.9b04388
Mauer, D. Somers, A. Process for Preparing a Metal Wire With a Non-Isocyanate Polyurethane Coating. WO 2007/062812 A1, 2007.
Figovsky, O. L. Shapovalov, L. D. Birukov, O. Floor Coating Composition. SU 1754748 A1, 1992.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Hanada, K. Polyhydroxyurethane Aqueous Dispersion Composition, Gas Barrier Aqueous Coating Agent and Gas Barrier Film Comprising the Aqueous Dispersion Composition. JP 6298421 B2, 2018.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Hanada, K. Water Dispersion of Polyhydroxyurethane Resin, Method for Producing Water Dispersion, and Gas Barrier Film Using the Water Dispersion. JP 6563242 B2, 2019.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Tanigawa, M. Hanada, K. A Method for Producing the Water Dispersion, a Gas Barrier Resin Film Using the Water Dispersion, a Polyhydroxyurethane Resin Aqueous Dispersion Composition Containing Clay Minerals, a Gas Barrier Using the Composition, Casting Coating Agent and Gas Barri. KR 20190067252 A, 2019.
Kimura, K. Takahashi, K. Uruno, M. Muto, K. Hanada, K. Method for Producing Clay Mineral-Containing Polyhydroxyurethane Resin Composition, Clay Mineral-Containing Polyhydroxyurethane Resin Composition, and Gas Barrier Film Using the Composition. JP 6050726 B2, 2016.
Tomoo, T. Fukuoka, H. Kuraoka, K. Silica-Polyhydroxyurethane Resin Composition and Organic-Inorganic Hybrid Film. JP 6374236 B2, 2018.
Rossi De Aguiar, K. M. F. ; Specht, U. ; Maass, J. F. ; Salz, D. ; Picon, C. A. ; Noeske, P. L. M. ; Rischka, K. ; Rodrigues-Filho, U. P. Surface Modification by Physical Treatments on Biomedical Grade Metals to Improve Adhesion for Bonding Hybrid Non-Isocyanate Urethanes. RSC Adv. 2016, 6 (), 47203 - 47211, 10.1039/C6RA05397A
Cornille, A. ; Blain, M. ; Auvergne, R. ; Andrioletti, B. ; Boutevin, B. ; Caillol, S. A Study of Cyclic Carbonate Aminolysis at Room Temperature: Effect of Cyclic Carbonate Structures and Solvents on Polyhydroxyurethane Synthesis. Polym. Chem. 2017, 8 (), 592 - 604, 10.1039/C6PY01854H
Tomita, H. ; Sanda, F. ; Endo, T. Polyaddition of Bis(Seven-Membered Cyclic Carbonate) with Diamines: A Novel and Efficient Synthetic Method for Polyhydroxyurethanes. J. Polym. Sci., Part A: Polym. Chem. 2001, 39 (), 4091 - 4100, 10.1002/pola.10058
Yuen, A. ; Bossion, A. ; Gómez-Bengoa, E. ; Ruipérez, F. ; Isik, M. ; Hedrick, J. L. ; Mecerreyes, D. ; Yang, Y. Y. ; Sardon, H. Room Temperature Synthesis of Non-Isocyanate Polyurethanes (NIPUs) Using Highly Reactive N-Substituted 8-Membered Cyclic Carbonates. Polym. Chem. 2016, 7 (), 2105 - 2111, 10.1039/C6PY00264A
Gennen, S. ; Grignard, B. ; Tassaing, T. ; Jérôme, C. ; Detrembleur, C. CO2-Sourced α-Alkylidene Cyclic Carbonates: A Step Forward in the Quest for Functional Regioregular Poly(Urethane)s and Poly(Carbonate)S. Angew. Chem., Int. Ed. 2017, 56 (), 10394 - 10398, 10.1002/anie.201704467
Ouhib, F. ; Grignard, B. ; Van Den Broeck, E. ; Luxen, A. ; Robeyns, K. ; Van Speybroeck, V. ; Jerome, C. ; Detrembleur, C. A Switchable Domino Process for the Construction of Novel CO 2 -Sourced Sulfur-Containing Building Blocks and Polymers. Angew. Chem., Int. Ed. 2019, 58 (), 11768 - 11773, 10.1002/anie.201905969
Dabral, S. ; Licht, U. ; Rudolf, P. ; Bollmann, G. ; Hashmi, A. S. K. ; Schaub, T. Synthesis and Polymerisation of α-Alkylidene Cyclic Carbonates from Carbon Dioxide, Epoxides and the Primary Propargylic Alcohol 1,4-Butynediol. Green Chem. 2020, 22 (), 1553 - 1558, 10.1039/C9GC04320A
