An Ambient Curable Coating Material Based on the Michael Addition Reaction of Acetoacetylated Castor Oil and Multifunctional Acrylate
Source abstract
Abstract
In this work a novel ambient curable coating was synthesized based on the Michael addition reaction of acetoacetylated castor oil and a multifunctional acrylate. In the research, we used hexamethylene diacrylate as crosslinker to optimize the reaction conditions and found that a ratio of acetoacetylated castor oil to acrylate groups of 1:1.5 and a catalyst (DBU) loading of 2 wt % provided an appropriate curing time. The acetoacetylated castor oil was characterized by 1H NMR and 13C NMR spectroscopy and the obtained coating characterized by FTIR to confirm the functionalization reaction. The tensile strength, cross linking density, and thermal properties of the resulting thermosets were investigated by dynamic mechanical analysis (DMA), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). Results demonstrated that the glass transition temperatures, tensile strength, and thermal degradation were significantly improved with higher cross-linking density. Moreover, we prepared films with different multifunctional acrylate cross-linkers and found that with the increase of cross-linking density, the swelling of the film rate decreased. Overall, thermosets made from Michael crosslinking technology provided a highly bio-based coating system.
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Research context
OpenAlex topics: Polymer composites and self-healing · Photopolymerization techniques and applications · Epoxy Resin Curing Processes
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Polymer and Coating, Jiangxi Science & Technology Normal University, Nanchang 330013, China
Jiangxi Engineering Laboratory of Waterborne Coating, Nanchang 330013, China
Funding
NSFC of China,the Science Funds of Jiangxi Province,Science Funds of the Education Office of Jiangxi Province
References (28)
Show source-provided references
1. Synthesis and properties of full bio-based thermosetting resins from rosin acid and soybean oil: The role of rosin acid derivatives10.1039/c3gc00095h ↗
2. Synthesis of reactive soybean oils for use as a biobased thermoset resins in structural natural fiber composites10.1002/app.31411 ↗
3. Synthesis and characterization of unsaturated lactic acid based thermoset bio-resins10.1016/j.eurpolymj.2014.11.045 ↗
4. A highly active bio-based epoxy resin with multi-functional group: Synthesis, characterization, curing and properties10.1007/s10853-017-1797-8 ↗
5. Modification of cottonseed oil for amine cured epoxy resin: Studies on thermo-mechanical, physico-chemical, morphological and antimicrobial properties10.1016/j.porgcoat.2015.07.015 ↗
6. Castor oil as a renewable resource for the chemical industry10.1002/ejlt.200900138 ↗
7. Preparation and properties of waterborne bio-based polyurethane/siloxane cross-linked films by an in situ sol–gel process10.1016/j.porgcoat.2015.02.008 ↗
8. Preparation and properties of castor oil/pentaerythritol triacrylate-based UV curable waterborne polyurethane acrylate10.1016/j.porgcoat.2014.09.012 ↗
9. Properties of alkyl esters base on castor oil
10. Improving the toughness and flame retardancy of cured epoxy resin with brominated castor oil10.1002/app.11097 ↗
11. Michael addition reactions in macromolecular design for emerging technologies10.1016/j.progpolymsci.2006.03.001 ↗
12. Michael addition reaction kinetics of acetoacetates and acrylates for the formation of polymeric networks10.3184/146867807X247730 ↗
13. Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions10.1021/bm049607o ↗
14. Imidazole derivatives as latent curing agents for epoxy thermosetting resins10.1016/j.matlet.2015.08.141 ↗
15. In-situ synthesis of organic–inorganic coatings via a photolatent base catalyzed Michael-addition reaction10.1016/j.polymer.2015.05.019 ↗
16. Applications of Michael addition chemistry in coatings technology10.1016/S0300-9440(97)00070-2 ↗
17. Acetoacetylated castor oil in coatings applications10.1016/S0300-9440(01)00223-5 ↗
18. Novel biobased dual-cure coating system10.1016/j.porgcoat.2010.11.020 ↗
19. The exploration of Michael-addition reaction chemistry to create high performance, ambient cure thermoset coatings based on soybean oil10.1016/j.porgcoat.2017.04.004 ↗
20. Liu, Z., Shao, P., Huang, Z., Liu, B., Chen, T., and Qin, J. (2008). Two-photon absorption enhancement induced by aggregation due to intermolecular hydrogen bonding in V-shaped 2-hydroxypyrimidine derivatives. Chem. Commun., 2260–2262.10.1039/b718147g ↗
21. Crosslinked imidazolium-containing polyester networks containing a pendant imidazolium group: Swelling studies and thermal properties10.1016/j.polymer.2014.01.038 ↗
22. Synthesis and thermal analysis of crosslinked imidazolium-containing polyester networks prepared by Michael addition polymerization10.1016/j.polymer.2012.10.040 ↗
23. Synthesis and characterization of hyperbranched polyurethane hybrids using tetraethoxysilane (TEOS) as cross-linker10.1021/ie800884y ↗
24. Acid-catalyzed moisture-curing polyurea/polysiloxane ceramer coatings10.1016/S0300-9440(00)00116-8 ↗
25. Emulsion-templated porous polymers prepared by thiol-ene and thiol-yne photopolymerisation using multifunctional acrylate and non-acrylate monomers10.1016/j.polymer.2017.04.021 ↗
26. Dynamic mechanical studies of the glass transition temperature of photopolymerized multifunctional acrylates10.1007/BF00329970 ↗
27. Synthesis and physical properties of lipid-based poly(ester-urethane)s, I: Effect of varying polyester segment length10.1016/j.polymer.2012.06.011 ↗
28. New polyisobutylene-based UV-curable flexible coatings10.1007/BF00261978 ↗