Rubber-to-steel adhesives based on natural rubber grafted with poly(acetoacetoxyethyl methacrylate)
-
Rattanawadee Ninjan
,
Natinee Lopattananon
Abstract
The present study aimed to develop adhesives for bonding natural rubber (NR) to steel based on modified NR bearing grafted poly(acetoacetoxyethyl methacrylate), NR-g-PAAEM. Graft copolymers of NR-g-PAAEMs were prepared by emulsion polymerization at 50 °C. A significant increase in the polar component of NR from 1.62 to 6.84 mN/m was observed after grafting modification, indicating an increase in its hydrophilicity. After that, both one-coat and two-coat adhesives (or adhesive/cover-coat system) were then prepared, using polyisocyanate (poly‐HDI) as a bonding agent. The NR/steel joints were made by vulcanization bonding, using the NR-g-PAAEM adhesive in the presence or absence of cover-coat layer. The results reveal that the NR/steel joint bonded using the two-coat system exhibited higher peel strength than that bonded using the one-coat system. For the two-coat system, the peel strength of 874 N/m was attained when the NR-g-PAAEM adhesive was used in combination with the NR cover-coat. The replacement of the NR cover-coat by the NR-g-PAAEM20 cover-coat led to 49% increase in peel strength of the NR/steel joint. Moreover, the X-ray photoelectron spectroscopy analysis also indicated the formation of urethane-like bonding in this adhesive system, as a result of the reaction between the poly‐HDI and metal oxides on the steel surface.
Funding source: Prince of Songkla University
Award Identifier / Grant number: SAT581267S
Acknowledgments
The authors wish to thank BASF (Thai) Ltd. for providing the polyisocyanate.
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: This work was supported by the Research Fund of Prince of Songkla University, SAT581267S.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Cherian, S., Ryu, S. B., Cornish, K. Natural rubber biosynthesis in plants, the rubber transferase complex, and metabolic engineering progress and prospects. Plant Biotechnol. J. 2019, 17, 2041–2061. https://doi.org/10.1111/pbi.13181.Search in Google Scholar
2. Men, X., Wang, F., Chen, G. Q., Hai-Bo Zhang, H. B., Xian, M. Biosynthesis of natural rubber: current state and perspectives. Int. J. Mol. Sci. 2019, 20, 1–22.10.3390/ijms20010050Search in Google Scholar PubMed PubMed Central
3. Fukahori, Y. Use of natural rubber (NR) for vibration isolation and earthquake protection of structures. In Chemistry, Manufacture and Applications of Natural Rubber; Kohjiya, S., Ikeda, Y., Eds. Woodhead Publishing Limited: Cambridge, 2014; pp. 371–380.10.1533/9780857096913.2.371Search in Google Scholar
4. Menga, N., Bottiglione, F., Carbone, G. The nonlinear dynamic behavior of a rubber-layer roller bearing (RLRB) for vibration isolation. J. Sound Vib. 2019, 463, 1–12. https://doi.org/10.1016/j.jsv.2019.114952.Search in Google Scholar
5. Souid, A., Sarda, A., Deterre, R., Leroy, E. Influence of reversion on adhesion in the rubber-to-metal vulcanization-bonding process. Polym. Test. 2015, 41, 157–162. https://doi.org/10.1016/j.polymertesting.2014.11.007.Search in Google Scholar
6. Ebnesajjad, S. Adhesives Technology Handbook, 2nd ed.; William Andrew Inc: Norwich, 2009.Search in Google Scholar
7. Kuhn, L. B. Rubber to Metal Adhesive Comprising Dichlorobutadiene Resin and a Chlorinated Elastomer and Use thereof. U.S. Patent 2, 581, 920, January 8, 1952.Search in Google Scholar
8. Halladay, J. R., Warren, P. A. Rubber to metal bonding. In The Handbook of Rubber Bonding; Crowther, B., Ed. Revised edition; Rapra Technology Limited: Shawbury, 2003; pp. 57–77.Search in Google Scholar
9. Schollenberger, C. S. Polyurethane and isocyanate-based adhesive. In Handbook of Adhesives; Skeist, I., Ed.; Springer: Boston, 1990; pp. 359–380.10.1007/978-1-4613-0671-9_20Search in Google Scholar
10. Achary, P. S., Gouri, C., Ramaswamy, R. Reactive bonding of natural rubber to metal by a nitrile–phenolic adhesive. J. Appl. Polym. 2001, 81, 2597–2608.10.1002/app.1702Search in Google Scholar
11. Mowrey, D. H., Carney, B. P., Cowles, R. S., Agag, T. Adhesive Composition and Method for Bonding. U.S. Patent 2018/0244965 A1, Aug 30, 2018.Search in Google Scholar
12. Sensui, K., Tarui, T., Miyamae, T., Sato, C. Evidence of chemical-bond formation at the interface between an epoxy polymer and an isocyanate primer. Chem. Commun. 2019, 55, 14833–14836. https://doi.org/10.1039/c9cc05911c.Search in Google Scholar
13. Shimizu, K., Phanopoulos, C., Loenders, R., Abela, M. L., Wattsa, J. F. The characterization of the interfacial interaction between polymeric methylene diphenyl diisocyanate and aluminum: a ToF–SIMS and XPS study. Surf. Interface Anal. 2010, 42, 1432–1444. https://doi.org/10.1002/sia.3586.Search in Google Scholar
14. Tardio, S., Abel, M. L., Carr, R. H., Watts, J. F. The interfacial interaction between isocyanate and stainless steel. Int. J. Adhes. Adhes. 2019, 88, 1–10; https://doi.org/10.1016/j.ijadhadh.2018.10.008.Search in Google Scholar
15. Bernardini, J., Licursi, D., Anguillesi, I., Cinelli, P., Coltelli, M. B., Antonetti, C., Galletti, A. M. R., Lazzeri, A. Exploitation of Arundo donax L. hydrolysis residue for the green synthesis of flexible polyurethane foams. BioResources 2017, 12, 3630–3655. https://doi.org/10.15376/biores.12.2.3630-3655.Search in Google Scholar
16. Tillet, G., Boutevin, B., Ameduri, B. Chemical reactions of polymer crosslinking and post–crosslinking at room and medium temperature. Prog. Polym. Sci. 2011, 36, 191–217. https://doi.org/10.1016/j.progpolymsci.2010.08.003.Search in Google Scholar
17. Larson, G. R., Pusfhak, C. A., Smith, L. S., Wood, K. A. Waterborne Coating Composition. U.S. Patent 5,414,041, May 9, 1995.Search in Google Scholar
18. Rector, F., Blount, W. W., Leonard, D. R. Applications for acetoacetyl chemistry in thermoset coatings. J. Coat. Technol. Res. 1989, 61, 31–37.Search in Google Scholar
19. Ninjan, R., Thongnuanchan, B., Lopattananon, N., Thitithammawong, A., Nakason, C. Ambient curable latex films and adhesives based on natural rubber bearing acetoacetoxy functionality. Polym. Adv. Technol. 2019, 30, 598–607. https://doi.org/10.1002/pat.4496.Search in Google Scholar
20. Thongnuanchan, B., Ninjan, R., Kaesaman, A., Nakason, C. Synthesis of modified natural rubber with grafted poly(acetoacetoxyethyl methacrylate-co-methyl methacrylate) and performance of derived adhesives with GTA crosslinker. Polym. Eng. Sci. 2018, 58, 1610–1618. https://doi.org/10.1002/pen.24750.Search in Google Scholar
21. Samuel, B., Zhao, H., Law, K. Y. Study of wetting and adhesion interactions between water and various polymer and superhydrophobic surfaces. J. Phys. Chem. C 2011, 115, 14852–14861. https://doi.org/10.1021/jp2032466.Search in Google Scholar
22. Kulkarni, V. S., Shaw, C. Essential Chemistry for Formulators of Semisolid and Liquid Dosages; Academic Press: Waltham, 2016.Search in Google Scholar
23. Wu, S. Calculation of interfacial tension in polymer systems. J. Polym. Sci. C. 1971, 34, 19–30.10.1002/polc.5070340105Search in Google Scholar
24. Wu, S. Polymer Interface and Adhesion; Marcel Dekker Inc: New York, 1982.Search in Google Scholar
25. Jansen, R. J. J., van Bekkum, H. XPS of nitrogen-containing functional groups on activated carbon. Carbon 1955, 33, 1021–1027.10.1016/0008-6223(95)00030-HSearch in Google Scholar
26. Dillard, J. G. X-Ray photoelectron spectroscopy (XPS) and electron spectroscopy for chemical analysis (ESCA). In Characterization of Composite Materials; Ishida, H., Ed. Butterworth–Heinemann: Stoneham, 1994; pp. 1–23.10.1016/B978-0-7506-9386-8.50008-3Search in Google Scholar
27. Haverkamp, R. G., Siew, D. C. W., Barton, T. F. XPS study of the changes during the service life of polyester powder coatings. Surf. Interface Anal. 2002, 33, 330–334. https://doi.org/10.1002/sia.1215.Search in Google Scholar
28. Ederer, J., Janoš, P., Ecorchard, P., Tolasz, J., Štengl, V., Beneš, H., Perchaczc, M., Pop–Georgievskid, O. Determination of amino groups on functionalized graphene oxide for polyurethane nanomaterials: XPS quantitation vs. functional speciation. RSC Adv. 2017, 7, 12464–12473. https://doi.org/10.1039/c6ra28745j.Search in Google Scholar
© 2021 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Material properties
- Comparative study of conventional and microwave heating of polyacrylonitrile-based fibres
- Effects of Ru catalyst changes by atmospheric exposure days on the interfacial and impact properties of glass fiber/p-DCPD composites
- Rubber-to-steel adhesives based on natural rubber grafted with poly(acetoacetoxyethyl methacrylate)
- Preparation and assembly
- Preparation and swelling behavior of end-linked hydrogels prepared from linear poly(ethylene glycol) and dendrimer-star polymers
- Imidazolium functionalized polymers for effective electrochemical reduction of CO2
- Morphology optimization of poly(ethylene terephthalate)/polyamide blends compatibilized via extension-dominated twin-screw extrusion
- Engineering and processing
- Removal of 17β-estradiol from aqueous systems with hydrophobic microspheres
- Effect of fiber content on the layer structure formation of fibers inside injection-molded products using short glass fiber-reinforced materials
Articles in the same Issue
- Frontmatter
- Material properties
- Comparative study of conventional and microwave heating of polyacrylonitrile-based fibres
- Effects of Ru catalyst changes by atmospheric exposure days on the interfacial and impact properties of glass fiber/p-DCPD composites
- Rubber-to-steel adhesives based on natural rubber grafted with poly(acetoacetoxyethyl methacrylate)
- Preparation and assembly
- Preparation and swelling behavior of end-linked hydrogels prepared from linear poly(ethylene glycol) and dendrimer-star polymers
- Imidazolium functionalized polymers for effective electrochemical reduction of CO2
- Morphology optimization of poly(ethylene terephthalate)/polyamide blends compatibilized via extension-dominated twin-screw extrusion
- Engineering and processing
- Removal of 17β-estradiol from aqueous systems with hydrophobic microspheres
- Effect of fiber content on the layer structure formation of fibers inside injection-molded products using short glass fiber-reinforced materials
