Top

Hint

Swipe to navigate through the articles of this issue

Published in:

11-07-2022

Preparation and properties of a novel coating based on bismaleimides via Michael addition reaction

Authors: Jiajian He, Kai Cheng, Ruijun Lin, Qiuping Su, Yong Li, Zhiping Ma, Shaoshun Wang, Yuxin Gu, Xiaofeng Lin, Wenjing Lin, Guobin Yi

Published in: Journal of Coatings Technology and Research | Issue 6/2022

Abstract

In this work, a malonate polyester suitable for Michael addition reaction was prepared by melting polycondensation of neopentyl glycol, terephthalic acid, and diethyl malonate, and its structure was characterized by Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (NMR). Then, Michael addition reaction between malonate polyester and diphenylmethane bismaleimide (BDM), catalyzed by 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU)/benzoic acid salt, was carried out to prepare the films with different contents of curing agent. The thermal and mechanical properties of the films were characterized by dynamic thermomechanical analysis, thermogravimetric analysis, and differential scanning calorimetry. We found that glass transition temperature (T_g) of the films increased with the increase in BDM amount. The T_g could reach up to 80°C, which indicated that the fabricated films show excellent thermal stability.

previous article Novel multilayer structural epoxy composite coating containing graphene oxide and silanized chromium carbide for the protection of steel structures

next article Preparation, mechanical and thermal properties of polydimethylsiloxane coating for synthetic leathers

To get access to this content you need the following product:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

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

über 69.000 Bücher
über 500 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 90 Tage mit der neuen Mini-Lizenz testen!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 50.000 Bücher
über 380 Zeitschriften

aus folgenden Fachgebieten:

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

Jetzt 90 Tage mit der neuen Mini-Lizenz testen!

inform now

Available only for authorised users

Wang, T, Han, Y, Bai, Y, Zhu, Q, Quan, D, Liu, X, “Poly(Ether-Carbonate) Based Hydrogel with Tunable Mechanical Strength and Enhanced Bioactivity Prepared by Michael Addition.” Polymer, 188 122115 (2020) CrossRef

Wang, ZC, Xu, XD, Chen, CS, Yun, L, Song, JC, Zhang, XZ, Zhuo, RX, “In Situ Formation of Thermosensitive PNIPAAm-Based Hydrogels by Michael-Type Addition Reaction.” ACS Appl. Mater. Interfaces, 2 (4) 1009–1018 (2010) CrossRef

Fang, L, Zhang, H, Li, Z, Zhang, Y, Zhang, Y, Zhang, H, “Synthesis of Reactive Azobenzene Main-Chain Liquid Crystalline Polymers via Michael Addition Polymerization and Photomechanical Effects of Their Supramolecular Hydrogen-Bonded Fibers.” Macromolecules, 46 (19) 7650–7660 (2013) CrossRef

Baruah, R, Kumar, A, Ujjwal, RR, Kedia, S, Ranjan, A, Ojha, U, “Recyclable Thermosets Based on Dynamic Amidation and Aza-Michael Addition Chemistry.” Macromolecules, 49 (20) 7814–7824 (2016) CrossRef

Arimitsu, K, Fuse, S, Kudo, K, Furutani, M, “Imidazole Derivatives as Latent Curing Agents for Epoxy Thermosetting Resins.” Mater. Lett., 161 408–410 (2015) CrossRef

Gigot, A, Sangermano, M, Capozzi, LC, Dietliker, K, “In-Situ Synthesis of Organic–Inorganic Coatings via a Photolatent Base Catalyzed Michael-Addition Reaction.” Polymer, 68 195–201 (2015) CrossRef

Williams, SR, Miller, KM, Long, TE, “Michael Addition Reaction Kinetics of Acetoacetates and Acrylates for the Formation of Polymeric Networks.” Prog. React. Kinet. Mech., 32 (4) 165–194 (2019) CrossRef

Metters, A, Hubbell, J, “Network Formation and Degradation Behavior of Hydrogels Formed by Michael-Type Addition Reactions.” Biomacromolecules, 6 290–301 (2005) CrossRef

Mather, BD, Viswanathan, K, Miller, KM, Long, TE, “Michael Addition Reactions in Macromolecular Design for Emerging Technologies.” Prog. Polym. Sci., 31 (5) 487–531 (2006) CrossRef

10.

Ozturk, G, Long, TE, “Michael Addition for Crosslinking of Poly(Caprolactone)s.” J. Polym. Sci. Part A Polym. Chem., 47 (20) 5437–5447 (2009) CrossRef

11.

Noomen, A, “Applications of Michael Addition Chemistry in Coatings Technology.” Prog. Org. Coat., 32 137–142 (1997) CrossRef

12.

Xu, L, Chu, Z, Wang, H, Cai, L, Tu, Z, Liu, H, Zhu, C, Shi, H, Pan, D, Pan, J, Fei, X, “Electrostatically Assembled Multilayered Films of Biopolymer Enhanced Nanocapsules for On-Demand Drug Release.” ACS Appl. Bio Mater., 2 (8) 3429–3438 (2019) CrossRef

13.

Xu, L, Zhang, X, Chu, Z, Wang, H, Li, Y, Shen, X, Cai, L, Shi, H, Zhu, C, Pan, J, Pan, D, “Temperature-Responsive Multilayer Films Based on Block Copolymer-Coated Silica Nanoparticles for Long-Term Release of Favipiravir.” ACS Appl. Nano Mater., 4 (12) 14014–14025 (2021) CrossRef

14.

Xu, L, Wang, H, Chu, Z, Cai, L, Shi, H, Zhu, C, Pan, D, Pan, J, Fei, X, Lei, Y, “Temperature-Responsive Multilayer Films of Micelle-Based Composites for Controlled Release of a Third-Generation EGFR Inhibitor.” ACS Appl. Polym. Mater., 2 (2) 741–750 (2020) CrossRef

15.

Wang, T, Wang, J, He, X, Cao, Z, Xu, D, Gao, F, Zhong, J, Shen, L, “An Ambient Curable Coating Material Based on the Michael Addition Reaction of Acetoacetylated Castor Oil and Multifunctional Acrylate.” Coatings, 9 (1) 37 (2019) CrossRef

16.

Zuo, H, Cao, Z, Shu, J, Xu, D, Zhong, J, Zhao, J, Wang, T, Chen, Y, Gao, F, Shen, L, “Effect of Structure on the Properties of Ambient-Cured Coating Films Prepared via a Michael Addition Reaction Based on an Acetoacetate-Modified Castor Oil Prepared by Thiol-Ene Coupling.” Prog. Org. Coat., 135 27–33 (2019) CrossRef

17.

Li, Q, Guo, L, Qiu, T, Xiao, W, Du, D, Li, X, “Synthesis of Waterborne Polyurethane Containing Alkoxysilane Side Groups and the Properties of the Hybrid Coating Films.” Appl. Surf. Sci., 377 66–74 (2016) CrossRef

18.

Stenzenberger, HK, König, P, “Bis[3-(2-Allylphenoxy) Phthalimides]: A New Class of Comonomers for Bismaleimides.” High Perform. Polym., 1 133–144 (1989) CrossRef

19.

Xu, D, Cao, Z, Wang, T, Zhao, J, Zhong, J, Xiong, P, Wang, J, Gao, F, Shen, L, “Effect of the Ratio of Acetylacetate Groups on the Properties of a Novel Plant-Based Dual-Cure Coating System.” ACS Omega, 4 (6) 11173–11179 (2019) CrossRef

20.

Sun, B, Liang, G, Gu, A, Yuan, L, “High Performance Miscible Polyetherimide/Bismaleimide Resins with Simultaneously Improved Integrated Properties Based on a Novel Hyperbranched Polysiloxane Having a High Degree of Branching.” Ind. Eng. Chem. Res., 52 (14) 5054–5065 (2013) CrossRef

21.

Mandhakini, M, Devaraju, S, Venkatesan, MR, Alagar, M, “Linseed Vinyl Ester Fatty Amide Toughened Unsaturated Polyester-Bismaleimide Composites.” High Perform. Polym., 24 (3) 237–244 (2012) CrossRef

22.

Mehta, B, Watt, P, Soucek, MD, Pugh, C, “Moderate Temperature Curing of Plant Oils with Bismaleimides via the Ene Reaction.” Ind. Eng. Chem. Res., 55 (45) 11727–11735 (2016) CrossRef

23.

Ionescu, M, Radojčić, D, Wan, X, Shrestha, ML, Petrović, ZS, Upshaw, TA, “Highly Functional Polyols from Castor Oil for Rigid Polyurethanes.” Eur. Polym. J., 84 736–749 (2016) CrossRef

24.

Feng, Y, Liang, H, Yang, Z, Yuan, T, Luo, Y, Li, P, Yang, Z, Zhang, C, “A Solvent-Free and Scalable Method to Prepare Soybean-Oil-Based Polyols by Thiol-Ene Photo-Click Reaction and Biobased Polyurethanes Therefrom.” ACS Sustain. Chem. Eng., 5 (8) 7365–7373 (2017) CrossRef

25.

Jena, KK, Raju, KVSN, “Synthesis and Characterization of Hyperbranched Polyurethane Hybrids Using Tetraethoxysilane (TEOS) as Cross-Linker.” Ind. Eng. Chem. Res., 47 9214–9224 (2008) CrossRef

26.

Ni, H, Skaja, AD, Soucek, MD, “Acid-Catalyzed Moisture-Curing Polyurea/Polysiloxane Ceramer Coatings.” Prog. Org. Coat., 40 175–184 (2000) CrossRef

27.

Zhang, Y, Yuan, L, Guan, Q, Liang, G, Gu, A, “Developing Self-healable and Antibacterial Polyacrylate Coatings with High Mechanical Strength Through Crosslinking by Multi-amine Hyperbranched Polysiloxane via Dynamic Vinylogous Urethane.” J. Mater. Chem. A, 5 (32) 16889–16897 (2017) CrossRef

Title: Preparation and properties of a novel coating based on bismaleimides via Michael addition reaction
Authors: Jiajian He
Kai Cheng
Ruijun Lin
Qiuping Su
Yong Li
Zhiping Ma
Shaoshun Wang
Yuxin Gu
Xiaofeng Lin
Wenjing Lin
Guobin Yi
Publication date: 11-07-2022
Publisher: Springer US
Published in: Journal of Coatings Technology and Research / Issue 6/2022
Print ISSN: 1547-0091
Electronic ISSN: 1935-3804
DOI: https://doi.org/10.1007/s11998-022-00644-8

Springer Professional

Hint

Swipe to navigate through the articles of this issue

Abstract

Please log in to get access to this content

To get access to this content you need the following product:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 6/2022

Effect of plasma treatment on the tribological and adhesion performance of a polymer coating deposited on different metallic substrates

Impact of enzymatically synthesized aliphatic–aromatic polyesters with increased hydroxyl group content on coating properties

Nano-silica-containing acrylic polyurethane and acrylic-polyester hybrid polyurethane coatings for direct-to-metal (DTM) coating applications – a comparative study

Preparation, mechanical and thermal properties of polydimethylsiloxane coating for synthetic leathers

Photocured polyacrylate coatings modified by polybutadiene derivatives with multiunsaturated reactive bonds

Synthesis of novel one-component photoinitiators based on thioxanthone derivatives

Premium Partners