Development of biomaterials with primary amine surfaces is very important for the study of some cells of the immune systemuch as macrophages. Currently, the modification can be carried out by physical or chemical methods with several disadvantages due to the presence of additives or subproducts in the system. To overcome this problem, modified polypropylene (PP) films were synthesized by gamma radiation. In this work, radiation grafting of acryloyl chloride onto PP has been employed to form an acyl chloride. Then, the radiation-grafted films were reacted with ethylenediamine in several solvents to obtain the different concentration of the primary amine. The surface amine concentration was determined by derivatization with 4-trifluoromethyl benzaldehyde and characterized by x-ray photoelectron spectroscopy (N/C ratios), Fourier transform infrared spectroscopy with attenuated total reflection, contact angle, scanning electron microscopy, atomic force microscopy, and elementary analysis. The stability of the amines was measured up to 90 days, without the occurrence of aging as was found by plasma modification.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Tax calculation will be finalised during checkout.
P.L. Girard-Lauriault, F. Truica-Marasescu, A. Petit, H.T. Wang, P. Desjardins, J. Antoniou, F. Mwale, and M.R. Wertheimer: Adhesion of human U937 monocytes to nitrogen-rich organic thin films: novel insights into the mechanism of cellular adhesion. Macromol. Biosci. 9, 911 (2009).
M.A. Lan, C.A. Gersbach, K.E. Michael, B.G. Keselowsky, and A.J. García: Myoblast proliferation and differentiation on fibronectin-coated self assembled monolayers presenting different surface chemistries. Biomaterials 26, 4523 (2005).
J.M. Curran, R. Chen, and J.A. Hunt: Controlling the phenotype and function of mesenchymal stem cells in vitro by adhesion to silane-modified clean glass surfaces. Biomaterials 26, 7057 (2005).
J.M. Curran, R. Chen, and J.A. Hunt: The guidance of human mesenchy-mal stem cell differentiation in vitro by controlled modifications to the cell substrate. Biomaterials 27, 4783 (2006).
N.A. Bullett, D.P. Bullett, F.E. Truica-Marasescu, S. Lerouge, F. Mwale, and M.R. Wertheimer: Polymer surface micropatterning by plasma and VUV-photochemical modification for controlled cell culture. Appl. Surf. Sci. 235, 395 (2004).
P.L. Girard-Lauriault, F. Mwale, M. Iordanova, C. Demers, P. Desjardins, and M.R. Wertheimer: Atmospheric pressure deposition of micropat-terned nitrogen-rich plasma-polymer films for tissue engineering. Plasma Process. Polym. 2, 263 (2005).
L. Štrbková, A. Manakhov, L. Zajícková, A. Stoica, P. Veselý, and R. Chmelík: The adhesion of normal human dermal fibroblasts to the cyclo-propylamine plasma polymers studied by holographic microscopy. Surf. Coat. Technol. 295, 70 (2016).
P. Hamerli, T. Weigel, T. Groth, and D. Paul: Surface properties of and cell adhesion onto allylamine-plasma-coated polyethylenterephtalat membranes. Biomaterials 24, 3989 (2003).
R. Sridharan, A.R. Cameron, D.J. Kelly, C.J. Kearney, and F.J. O’Brien: Biomaterial based modulation of macrophage polarization: a review and suggested design principles. Mater. Today 18, 313 (2015).
J.C. Ruiz, A. St-Georges-Robillard, C. Thérésy, S. Lerouge, and M.R. Wertheimer: Fabrication and characterisation of amine-rich organic thin films: focus on stability. Plasma Process. Polym. 7, 737 (2010).
J.G. Terlingen, L.M. Brenneisen, H.T. Super, A.P. Pijpers, A.S. Hoffman, and J. Feijen: Introduction of amine groups on poly(ethylene) by plasma immobilization of a preadsorbed layer of decylamine hydrochloride. J. Biomater. Sci. Polym. Ed. 4, 165 (1993).
C.P. Klages, Z. Khosravi, and A. Hinze: Some remarks on chemical deri-vatization of polymer surfaces after exposure to nitrogen-containing plasmas. Plasma Process. Polym. 10, 307 (2013).
M. Pérez-Calixto, G. González-Pérez, N. Dionisio, E. Bucio, G. Burillo, and L. Garciá-Uriostegui: Surface functionalization of polypropylene and polyethylene films with allylamine by γ radiation. MRS Commun. 9, 264 (2019).
E. Rodríguez-alba, L. Huerta, A. Ortega, and G. Burillo: Surface modification of polypropylene with primary amines by acrylamide radiation grafting and Hofmann’s transposition reaction. ChemistrySelect 4, 7759 (2019).
P.L. Girard-Lauriault, P. Dietrich, T. Gross, and W.E.S. Unger: Is quantitative chemical derivatization XPS of plasma deposited organic coatings a valid analytical procedure? Surf. Interface Anal. 44, 1135 (2012).
E. Yegen, U. Zimmermann, W.E.S. Unger, and T. Braun: C-F bond cleavage during derivatization reactions of amino groups with TFBA and PFB at plasma-processed organic surfaces? Plasma Process. Polym. 6, 11 (2009).
E. Bucio, G. Burillo, M.D.P. Carreón-Castro, and T. Ogawa: Functionalization of polypropylene film by radiation grafting of acryloyl chloride and subsequent esterification with Disperse Red 1. J. Appl. Polym. Sci. 93, 172 (2004).
R. Aliev, M. Del Pilar Carreón-Castro, M. Rivera, and G. Burillo: Immobilization of disperse red 1 on to polydiethyleneglycol-bis-allylcarbonate (CR-39) radiation grafted with poly(acryloyl chloride). Polym. Bull. 52, 73 (2004).
A. Martínez-Cocoletzi, J.C. Ruiz, E. Kasparek, A. Ortega, L. Garcia-Uriostegui, P.L. Girard-Lauriault, and G. Burillo: Primary-amine surface functionalization of polytetrafluoroethylene films by radiation grafting of aminated polyacryloyl chloride. Radiat. Phys. Chem. 149, 65 (2018).
P.L. Girard-Lauriault, P.M. Dietrich, T. Gross, T. Wirth, and W.E.S. Unger: Chemical characterization of the long-term ageing of nitrogen-rich plasma polymer films under various ambient conditions. Plasma Process. Polym. 10, 388 (2013).
M.P. Stevens: Polymer Chemistry an Introduction, 3rd ed. (OXFORD University Press, New York, 1998).
A.J. Engler, L. Richert, J.Y. Wong, C. Picart, and D.E. Discher: Surface probe measurements of the elasticity of sectioned tissue, thin gels and polyelectrolyte multilayer films: Correlations between substrate stiffness and cell adhesion. Surf. Sci. 570, 142 (2004).
G. Beamson and D. Briggs: High Resolution XPS of Organic Polymers: The Scientia. The Scienta ESCA300 Database (Wiley & Son, Chichester, UK, 1992), pp. 56.
Y. Akishev, M. Grushin, N. Dyatko, I. Kochetov, A. Napartovich, N. Trushkin, T. Minh Duc, and S. Descours: Studies on cold plasma-polymer surface interaction by example of PP- and PET-films. J. Phys. D: Appl. Phys. 41 (2008).
R. Morent, N. De Geyter, C. Leys, L. Gengembre, and E. Payen: Comparison between XPS- And FTIR-analysis of plasma-treated polypropylene film surfaces. Surf. Interface Anal. 40, 597 (2008).
R. Dorai and M.J. Kushner: A model for plasma modification of polypropylene using atmospheric pressure discharges. J. Phys. D: Appl. Phys. 36, 666 (2003).
B. Couturaud, A.M. Bondia, C. Faye, L. Garrelly, A. Mas, and J.J. Robin: Grafting of poly-L-lysine dendrigrafts onto polypropylene surface using plasma activation for ATP immobilization - nanomaterial for potential applications in biotechnology. J. Colloid Interface Sci. 408, 242 (2013).
K.S. Siow, L. Britcher, S. Kumar, and H.J. Griesser: Plasma methods for the generation of chemically reactive surfaces for biomolecule immobilization and cell colonization - A review. Plasma Process. Polym. 3, 392 (2006).
The authors thank A. Ortega, F. Garcia, and B. Leal from ICN UNAM, A. Lopez-Vivas and A. Pompa from IIM-UNAM for technical support, and Yasab Ruiz Hernandez from LaNSBioDyT for supporting in measurements of AFM and DGAPA UNAM, Grant No. IN200116 for financial support.
The supplementary material for this article can be found at https://doi.org/10.1557/mrc.2019.133.
About this article
Cite this article
Pérez-Calixto, M., Huerta, L. & Burillo, G. Amine modifications of polypropylene films by gamma radiation to be applied in cell cultures. MRS Communications 9, 1323–1330 (2019). https://doi.org/10.1557/mrc.2019.133