nach oben

Journal of Coatings Technology and Research

Erschienen in:

08.01.2021

Ambient temperature and UV-cured hybrid coatings from acetoacetylated non-isocyanate polyurethanes

verfasst von: H. R. Asemani, V. Mannari

Erschienen in: Journal of Coatings Technology and Research | Ausgabe 2/2021

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

Preparation of ambient and UV curing non-isocyanate polyurethane (NIPU) coatings has been reported using a series of acetoacetylated non-isocyanate polyurethane (AA-NI-PUPO) oligomers. Synthesized oligomers were characterized using various techniques such as Fourier transform infrared and nuclear magnetic resonance spectroscopy. AA-NI-PUPOs showed significantly lower viscosity compared to their non-acetoacetylated counterparts. Ambient temperature-cured systems were formulated by mixing AA-NI-PUPOs and different primary amine compounds in stoichiometric proportions. Michael addition reaction of acrylates and AA-NI-PUPOs was initiated by UV curing using a photobase generator as the catalyst. NIPU coatings were studied for various thermo-mechanical properties and corrosion resistance. The selected UV-cured and ambient-cured samples showed instant and 1-h tack-free time, respectively. Results revealed that with proper selection of acetoacetylated resin and crosslinker type, coatings with properties comparable to conventional PU coatings could be formulated. Moreover, UV-curable coatings with up to 90 wt% solid could be formulated using conventional monomeric acrylates as a reactive diluent. The study demonstrates the feasibility of formulating solvent-free rapid ambient curing non-isocyanate polyurethane coatings.

Graphic abstract

Vorheriger Artikel Correlative studies on the properties of rubber seed and soybean oil-based alkyd resins and their blends

Nächster Artikel Rapid fabrication of large-scale structurally colored PS@SiO2 films with enhanced self-cleaning capability

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Huang, S, Liu, G, Zhang, K, Hu, H, Wang, J, Miao, L, Tabrizizadeh, T, “Water-Based Polyurethane Formulations for Robust Superhydrophobic Fabrics.” Chem. Eng. J., 360 445–451 (2019). https://doi.org/10.1016/j.cej.2018.11.220CrossRef

Lambourne, R, Strivens, TA, Paint and Surface Coatings: Theory and Practice. Woodhead Publishing, Cambridge (1999)CrossRef

Rossi, G, Fuchs, PFJ, Barnoud, J, Monticelli, L, “A Coarse-Grained MARTINI Model of Polyethylene Glycol and of Polyoxyethylene Alkyl Ether Surfactants.” J. Phys. Chem. B., 116 14353–14362 (2012). https://doi.org/10.1021/jp3095165CrossRef

Hirayama, T, Urban, MW, “Distribution of Melamine in Melamine/Polyester Coatings: FT-IR Spectroscopic Studies.” Prog. Org. Coat., 20 81–96 (1992). https://doi.org/10.1016/0033-0655(92)85006-HCrossRef

Kong, X, Liu, G, Curtis, JM, “Novel Polyurethane Produced from Canola Oil Based Poly(ether ester) Polyols: Synthesis, Characterization and Properties.” Eur. Polym. J., 48 2097–2106 (2012). https://doi.org/10.1016/j.eurpolymj.2012.08.012CrossRef

Greunz, T, Lowe, C, Bradt, E, Hild, S, Strauß, B, Stifter, D, “A Study on the Depth Distribution of Melamine in Polyester-Melamine Clear Coats.” Prog. Org. Coat., 115 130–137 (2018). https://doi.org/10.1016/j.porgcoat.2017.11.014CrossRef

Nelson, TJ, Masaki, B, Morseth, Z, Webster, DC, “Highly Functional Biobased Polyols and Their Use in Melamine–Formaldehyde Coatings.” J. Coat. Technol. Res., 10 757–767 (2013). https://doi.org/10.1007/s11998-013-9524-0CrossRef

Zamani, E, Yahyaei, H, Khosravi, A, Mohseni, M, Shaki, H, “Synthesis and Characterization of a Novel Self-colored Fluorescent Polycarbonate Urethane Based on the 1,8-Naphthalimide Group.” J. Macromol. Sci. Part B, 58 772–781 (2019). https://doi.org/10.1080/00222348.2019.1635726CrossRef

Mahmudzadeh, M, Yari, H, Ramezanzadeh, B, Mahdavian, M, “Urtica Dioica Extract as a Facile Green Reductant of Graphene Oxide for UV Resistant and Corrosion Protective Polyurethane Coating Fabrication.” J. Ind. Eng. Chem., 78 125–136 (2019). https://doi.org/10.1016/j.jiec.2019.06.026CrossRef

10.

Wexler, P, Anderson, BD, Encyclopedia of Toxicology. Elsevier Science Direct, Amsterdam (2005)

11.

Wang, P, Liu, S, Deng, Y, “Important Green Chemistry and Catalysis: Non-phosgene Syntheses of Isocyanates-Thermal Cracking Way.” Chin. J. Chem., 35 821–835 (2017). https://doi.org/10.1002/cjoc.201600745CrossRef

12.

Zhu, HD, Kneisel, AR, Mahdi, SZ, Saracsan, JW, “Low Volatile Isocyanate Monomer Containing Polyurethane Prepolymer and Adhesive System,” WO2006042305A1, 2006. https://patents.google.com/patent/WO2006042305A1/en.

13.

OSHA Announces New National Emphasis Program for Occupational Exposure to Isocyanates | Occupational Safety and Health Administration. https://www.osha.gov/news/newsreleases/trade/06252013.

14.

Deepa, P, Jayakannan, M, “Solvent-Free and Nonisocyanate Melt Transurethane Reaction for Aliphatic Polyurethanes and Mechanistic Aspects.” J. Polym. Sci. Part Polym. Chem., 46 2445–2458 (2008). https://doi.org/10.1002/pola.22578CrossRef

15.

Kušan, J, Keul, H, Höcker, H, “Cationic Ring-Opening Polymerization of Tetramethylene Urethane.” Macromolecules, 34 389–395 (2001). https://doi.org/10.1021/ma000535cCrossRef

16.

Kathalewar, MS, Joshi, PB, Sabnis, AS, Malshe, VC, “Non-isocyanate Polyurethanes: from Chemistry to Applications.” RSC Adv., 3 4110–4129 (2013). https://doi.org/10.1039/C2RA21938GCrossRef

17.

Figovsky, O, Leykin, A, “Synthesis and Application of Nonisocyanate Polyurethanes.” Chem. Chem. Technol., 10 553–559 (2016). https://doi.org/10.23939/chcht10.04si.553CrossRef

18.

Rokicki, G, Parzuchowski, PG, Mazurek, M, “Non-isocyanate Polyurethanes: Synthesis, Properties, and Applications.” Polym. Adv. Technol., 26 707–761 (2015). https://doi.org/10.1002/pat.3522CrossRef

19.

Blattmann, H, Fleischer, M, Bähr, M, Mülhaupt, R, “Isocyanate- and Phosgene-Free Routes to Polyfunctional Cyclic Carbonates and Green Polyurethanes by Fixation of Carbon Dioxide.” Macromol. Rapid Commun., 35 1238–1254 (2014). https://doi.org/10.1002/marc.201400209CrossRef

20.

Ghasemlou, M, Daver, F, Ivanova, EP, Adhikari, B, “Bio-based Routes to Synthesize Cyclic Carbonates and Polyamines Precursors of Non-Isocyanate Polyurethanes: A Review.” Eur. Polym. J., 118 668–684 (2019). https://doi.org/10.1016/j.eurpolymj.2019.06.032CrossRef

21.

Yu, AZ, Setien, RA, Sahouani, JM, Docken, J, Webster, DC, “Catalyzed Non-isocyanate Polyurethane (NIPU) Coatings from Bio-based Poly(cyclic carbonates).” J. Coat. Technol. Res., 16 41–57 (2019). https://doi.org/10.1007/s11998-018-0135-7CrossRef

22.

Wu, Z, Tang, L, Dai, J, Qu, J, “Synthesis and Properties of Fluorinated Non-isocyanate Polyurethanes Coatings with Good Hydrophobic and Oleophobic Properties.” J. Coat. Technol. Res., 16 1233–1241 (2019). https://doi.org/10.1007/s11998-019-00195-5CrossRef

23.

Aoyagi, N, Furusho, Y, Endo, T, “Effective Synthesis of Cyclic Carbonates from Carbon Dioxide and Epoxides by Phosphonium Iodides as Catalysts in Alcoholic Solvents.” Tetrahedron. Lett., 54 7031–7034 (2013). https://doi.org/10.1016/j.tetlet.2013.10.068CrossRef

24.

Wu, Y, Song, X, Li, S, Zhang, J, Yang, X, Shen, P, Gao, L, Wei, R, Zhang, J, Xiao, G, “3D-Monoclinic M-BTC MOF (M = Mn Co, Ni) as Highly Efficient Catalysts for Chemical Fixation of CO₂ into Cyclic Carbonates.” J. Ind. Eng. Chem., 58 296–303 (2018). https://doi.org/10.1016/j.jiec.2017.09.040CrossRef

25.

Figovsky, OL, Shapovalov, L, Leykin, A, Birukova, O, Potashnikova, R, “Progress in Elaboration of Nonisocyanate Polyurethanes Based on Cyclic Carbonates.” Int. Lett. Chem. Phys. Astron., 3 52–66 (2013). https://doi.org/10.18052/www.scipress.com/ILCPA.3.52CrossRef

26.

Wazarkar, K, Kathalewar, M, Sabnis, A, “Development of Epoxy-Urethane Hybrid Coatings Via Non-isocyanate Route.” Eur. Polym. J., 84 812–827 (2016). https://doi.org/10.1016/j.eurpolymj.2016.10.021CrossRef

27.

Byczyński, Ł, Dutkiewicz, M, Maciejewski, H, “Synthesis and Properties of High-solids Hybrid Materials Obtained from Epoxy Functional Urethanes and Siloxanes.” Prog. Org. Coat., 84 59–69 (2015). https://doi.org/10.1016/j.porgcoat.2015.02.017CrossRef

28.

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., 132 (2015) n/a-n/a. https://doi.org/10.1002/app.41391.

29.

Ecochard, Y, Leroux, J, Boutevin, B, Auvergne, R, Caillol, S, “From Multi-functional Siloxane-Based Cyclic Carbonates to Hybrid Polyhydroxyurethane Thermosets.” Eur. Polym. J., 120 109280 (2019). https://doi.org/10.1016/j.eurpolymj.2019.109280CrossRef

30.

Asemani, H, Zareanshahraki, F, Mannari, V, “Design of Hybrid Nonisocyanate Polyurethane Coatings for Advanced Ambient Temperature Curing Applications.” J. Appl. Polym. Sci., 136 47266 (2019). https://doi.org/10.1002/app.47266CrossRef

31.

Zareanshahraki, F, Asemani, HR, Skuza, J, Mannari, V, “Synthesis of Non-isocyanate Polyurethanes and Their Application in Radiation-Curable Aerospace Coatings.” Prog. Org. Coat., 138 105394 (2020). https://doi.org/10.1016/j.porgcoat.2019.105394CrossRef

32.

Asemani, HR, Mannari, V, “Synthesis and Evaluation of Non-isocyanate Polyurethane Polyols for Heat-cured Thermoset Coatings.” Prog. Org. Coat., 131 247–258 (2019). https://doi.org/10.1016/j.porgcoat.2019.02.036CrossRef

33.

Chattopadhyay, DK, Raju, KVSN, “Structural Engineering of Polyurethane Coatings for High Performance Applications.” Prog. Polym. Sci., 32 352–418 (2007). https://doi.org/10.1016/j.progpolymsci.2006.05.003CrossRef

34.

Noomen, A, “Applications of Michael Addition Chemistry in Coatings Technology.” Prog. Org. Coat., 32 137–142 (1997). https://doi.org/10.1016/S0300-9440(97)00070-2CrossRef

35.

Kuo, T, Grosso, PV, Spilman, GE, Clark, MD, “Fast-dry, High Solids Coating Compositions Based on Acetoacetate-Functionalized Alkyd Resins,” US6794049B2, 2004. https://patents.google.com/patent/US6794049/en.

36.

Narayan, R, Chattopadhyay, DK, Sreedhar, B, Raju, KVSN, “Cure, Viscoelastic and Mechanical Properties of Hydroxylated Polyester Melamine High Solids Coatings.” J. Mater. Sci., 37 4911–4918 (2002). https://doi.org/10.1023/A:1020834818562CrossRef

37.

Narayan, R, Raju, KVSN, “Properties of Acetoacetylated Hydroxylated Polyesters Based Polyurethane Coatings.” Prog. Org. Coat., 45 59–67 (2002). https://doi.org/10.1016/S0300-9440(02)00116-9CrossRef

38.

Paramarta, A, Webster, DC, “The Exploration of Michael-Addition Reaction Chemistry to Create High Performance, Ambient Cure Thermoset Coatings Based on Soybean Oil.” Prog. Org. Coat., 108 59–67 (2017). https://doi.org/10.1016/j.porgcoat.2017.04.004CrossRef

39.

Mohajeri, S, Burke, NAD, Stöver, HDH, “The Stability of Enamine Crosslinks Formed from Acetoacetate/Amine in Synthetic Hydrogels.” Polym. Degrad. Stab., 114 94–104 (2015). https://doi.org/10.1016/j.polymdegradstab.2015.01.027CrossRef

40.

Manchanda, H, Mannari, V, “Super Photo-base Initiated Organic–Inorganic Hybrid Coatings by Plural-cure Mechanisms.” Prog. Org. Coat., 127 222–230 (2019). https://doi.org/10.1016/j.porgcoat.2018.11.011CrossRef

41.

Pilehkouhi, M, Shaki, H, Khosravi, A, Khorasani, M, Zamani, E, “Synthesis and Characterization of a Fluorescent Water-Borne Polyurethane Based on a Novel Naphthalimide Dye.” J. Macromol. Sci. Part B., 57 151–167 (2018). https://doi.org/10.1080/00222348.2018.1435501CrossRef

42.

Krall, EM, Serum, EM, Sibi, MP, Webster, DC, “Catalyst-free Lignin Valorization by Acetoacetylation. Structural Elucidation by Comparison with Model Compounds.” Green Chem., 20 2959–2966 (2018). https://doi.org/10.1039/C8GC01071DCrossRef

43.

Cao, Z, Gao, F, Zhao, J, Wei, X, Cheng, Q, Zhong, J, Lin, C, Shu, J, Fu, C, Shen, L, “Bio-based Coating Materials Derived from Acetoacetylated Soybean Oil and Aromatic Dicarboxaldehydes.” Polymers, 11 1809 (2019). https://doi.org/10.3390/polym11111809CrossRef

44.

Tucker, HA, “Fast-curing, High Strength, Two-Part Sealants Using Acetoacetate-Amine Cure Chemistry,” EP0603716A1, 1994. https://patents.google.com/patent/EP0603716A1/en.

45.

Eastman t-BAA (Tertiary-Butyl acetoacetate) for the Synthesis of Acetoacetyl-Functional Resins. https://www.eastman.com/Literature_Center/N/N328.pdf.

46.

Konuray, AO, Ruiz, A, Morancho, JM, Salla, JM, Fernández-Francos, X, Serra, À, Ramis, X, “Sequential Dual Curing by Selective Michael Addition and Free Radical Polymerization of Acetoacetate-Acrylate-Methacrylate Mixtures.” Eur. Polym. J., 98 39–46 (2018). https://doi.org/10.1016/j.eurpolymj.2017.11.003CrossRef

47.

Urdl, K, Kandelbauer, A, Kern, W, Müller, U, Thebault, M, Zikulnig-Rusch, E, “Self-healing of Densely Crosslinked Thermoset Polymers—A Critical Review.” Prog. Org. Coat., 104 232–249 (2017). https://doi.org/10.1016/j.porgcoat.2016.11.010CrossRef

48.

Asemani, HR, Sarabi, AA, Eivaz Mohammadloo, H, Sarayloo, M, “Electrochemical and Morphological Properties of Zirconium Conversion Coating in the Presence of Nickel Ions on Galvanized Steel.” J. Coat. Technol. Res., 13 883–894 (2016). https://doi.org/10.1007/s11998-016-9800-xCrossRef

Titel: Ambient temperature and UV-cured hybrid coatings from acetoacetylated non-isocyanate polyurethanes
verfasst von: H. R. Asemani
V. Mannari
Publikationsdatum: 08.01.2021
Verlag: Springer US
Erschienen in: Journal of Coatings Technology and Research / Ausgabe 2/2021
Print ISSN: 1547-0091
Elektronische ISSN: 1935-3804
DOI: https://doi.org/10.1007/s11998-020-00425-1

Premium Partner

Marktübersichten

Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.

Zur Marktübersicht

Springer Professional

Abstract

Graphic abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 2/2021

Ag NPs deposited TiO2 coating material for superhydrophobic, antimicrobial and self-cleaning surface fabrication on fabric

Vapor phase assembly of benzotriazole and octadecylamine complex films on aluminum alloy surface

Characterization, coating and biological evaluation of polyol esters rosin derivatives as coating films

Bio-inspired fabrication of superhydrophilic and underwater superoleophobic alumina membranes for highly efficient oil/water separation

Simultaneous tracking of hardness, reactant conversion, solids concentration, and glass transition temperature in thermoset polyurethane coatings

Fabrication of graphene-coated poly(glycidyl methacrylate) microspheres by electrostatic interaction and their application in epoxy anticorrosion coatings

Premium Partner

Marktübersichten