Polímeros: Ciência e Tecnologia
https://www.revistapolimeros.org.br/article/doi/10.1590/0104-1428.03218
Polímeros: Ciência e Tecnologia
Original Article

Thermal radical polymerization of Bis(methacrylamide)s

Rodrigues, Stéfani Becker; Collares, Fabrício Mezzomo; Gamba, Douglas; Leitune, Vicente Castelo Branco; Petzhold, Cesar Liberato

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Abstract

Methacrylamides monomers for dental applications were synthesized using a one-step procedure starting from methacrylic anhydride and the respective diamine: N,N’-(propane-1,3-diyl)-bis(N-ethyl-2-methylacrylamide) (1), N,N’-(butane-1,4-diyl)-bis(2-methacrylamide) (2), N,N’-(octane-1,8-diyl-)bis(2-methylacrylamide) (3) and N,N’-(1,4-phenylene)-bis(2-methylacrylamide) (4). The structures were confirmed by 1H NMR, 13C NMR, FTIR-ATR and UHPLC-QTOF-MS. Thermal polymerization kinetics was investigated by modulated DSC for monomers (2), (3) and (4) using heating rates of 1, 2, 3 and 5 °C min-1. All IR spectra showed the C=C axial deformation at 1610 cm-1, in 1H NMR spectra the olefinic hydrogens were observed at 5.3 an 5.8 ppm and in 13C NMR, the vinylic carbons at 120 and 140 ppm. The exact m/z values were: 267.2068, 225.1595, 281.2222 and 245.1283 for monomers (1), (2), (3) and (4), respectively. The activation energy was: -182.7; -165.8 and -156.7 kJ mol-1 for monomers (2), (3) and (4), respectively. Monomers are promising candidates for use as hydrolytic stable adhesive systems for dental applications.

Keywords

adhesives; monomers; kinetics; differential scanning calorimetry (DSC); synthesis.

References

1 Van Landuyt, K. L., Snauwaert, J., De Munck, J., Peumans, M., Yoshida, Y., Poitevin, A., Coutinho, E., Suzuki, K., Lambrechts, P., & Van Meerbeek, B. (2007). Systematic review of the chemical composition of contemporary dental adhesives. Biomaterials28(26), 3757-3785. http://dx.doi.org/10.1016/j.biomaterials.2007.04.044. PMid:17543382. 

2 Pfeifer, C. S., Shelton, Z. R., Braga, R. R., Windmoller, D., Machado, J. C., & Stansbury, J. W. (2011). Characterization of dimethacrylate polymeric networks: a study of the crosslinked structure formed by monomers used in dental composites. European Polymer Journal47(2), 162-170. http://dx.doi.org/10.1016/j.eurpolymj.2010.11.007. PMid:21499538. 

3 Dickens, S. H., Stansbury, J. W., Choi, K. M., & Floyd, C. J. (2003). Photopolymerization kinetics of methacrylate dental resins. Macromolecules36(16), 6043-6053. http://dx.doi.org/10.1021/ma021675k

4 Collares, F. M., Ogliari, F. A., Zanchi, C. H., Petzhold, C. L., Piva, E., & Samuel, S. M. W. (2011). Influence of 2-hydroxyethyl methacrylate concentration on polymer network of adhesive resin. The Journal of Adhesive Dentistry13(2), 125-129. http://dx.doi.org/10.3290/j.jad.a18781. PMid:21594225. 

5 Ferracane, J. L. (2006). Hygroscopic and hydrolytic effects in dental polymer networks. Dental Materials22(3), 211-222. http://dx.doi.org/10.1016/j.dental.2005.05.005. PMid:16087225. 

6 De Munck, J., Van Landuyt, K., Peumans, M., Poitevin, A., Lambrechts, P., Braem, M., & Van Meerbeek, B. (2005). A critical review of the durability of adhesion to tooth tissue: methods and results. Journal of Dental Research84(2), 118-132. http://dx.doi.org/10.1177/154405910508400204. PMid:15668328. 

7 Nishiyama, N., Suzuki, K., Yoshida, H., Teshima, H., & Nemoto, K. (2004). Hydrolytic stability of methacrylamide in acidic aqueous solution. Biomaterials25(6), 965-969. http://dx.doi.org/10.1016/S0142-9612(03)00616-1. PMid:14615160. 

8 Ma, S. (2010). Development of a self-etching primer with higher shelf life and greater dentin bond stability. Dental Materials Journal29(1), 59-67. http://dx.doi.org/10.4012/dmj.2009-078. PMid:20379014. 

9 Catel, Y., Degrande, M., Le Pluart, L., Madec, P., Pham, T., & Picton, L. (2008). Synthesis, photopolymerization and adhesive properties of new hydrolytically stable phosphonic acids for dental applications. Journal of Polymer Science. Part A, Polymer Chemistry47(21), 5258-5271. http://dx.doi.org/10.1002/pola.23013

10 Liu, Y., Tjäderhane, L., Breschi, L., Mazzoni, A., Li, N., Mao, J., Pashley, D. H., & Tay, F. R. (2011). Limitations in bonding to dentin and experimental strategies to prevent bond degradation. Journal of Dental Research90(8), 953-968. http://dx.doi.org/10.1177/0022034510391799. PMid:21220360. 

11 Nishiyama, N., Asakura, T., Suzuki, K., Komatsu, K., & Nemoto, K. (2000). Bond strength of resin to acid-etched dentin studied by 13C NMR: interaction between N-methacryloyl-ω-amino acid primer and dentinal collagen. Journal of Dental Research79(3), 806-811. http://dx.doi.org/10.1177/00220345000790030401. PMid:10765952. 

12 Nishiyama, N., Suzuki, K., Asakura, T., Komatsu, K., & Nemoto, K. (2001). Adhesion of N-methacryloyl-omega-amino acid primers to collagen analyzed by 13C NMR. Journal of Dental Research80(3), 855-859. http://dx.doi.org/10.1177/00220345010800030201. PMid:11379884. 

13 Torii, Y., Itou, K., Nishitani, Y., Yoshiyama, M., Ishikawa, K., & Suzuki, K. (2003). Effect of self-etching primer containing N-acryloyl aspartic acid on enamel adhesion. Dental Materials19(4), 253-258. http://dx.doi.org/10.1016/S0109-5641(02)00028-3. PMid:12686287. 

14 Derbanne, M. A., Besse, V., Le Goff, S., Sadoun, M., & Pham, T.-N. (2013). Hydrolytically stable acidic monomers used in two steps self-etch adhesives. Polymer Degradation & Stability98(9), 1688-1698. http://dx.doi.org/10.1016/j.polymdegradstab.2013.06.006

15 Klee, J. E., & Lehmann, U. (2009). N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides - new adhesive monomers for self-etching self-priming one part dental adhesive. Beilstein Journal of Organic Chemistry5(72), 1-9. http://dx.doi.org/10.3762/bjoc.5.72. PMid:20300456. 

16 Moszner, N., Zeuner, F., Angermann, J., Fischer, U., & Rheinberger, V. (2003). Monomers for adhesive polymers, 4: synthesis and radical polymerization of hydrolytically stable crosslinking monomers. Macromolecular Materials and Engineering288(8), 621-628. http://dx.doi.org/10.1002/mame.200350003

17 Lichkus, A. M., Jin, X., Renn, C., Elsner, O., Szillat, F., Klee, J. E., Weber, C., Walz, U., & Scheufler, C. A. (2017). EP Patent No 3.231.411. Paris: European Patent Office. 

18 Moszner, N., Lamparth, I., Bock, T., Fischer, U. K., Salz, U., Rheinberger, V., & Liska, R. (2013). International Patent No 2.013.034.777 A2. Hamburg: Patent Cooperation Treaty. 

19 Gong, C., Wong, K.-L., & Lam, M. H. W. (2008). Photoresponsive molecularly imprinted hydrogels for the photoregulated release and uptake of pharmaceuticals in the aqueous media. Chemistry of Materials20(4), 1353-1358. http://dx.doi.org/10.1021/cm7019526

20 Azodi-Deilami, S., Abdouss, M., Kordestani, D., & Shariatinia, Z. (2014). Preparation of N,N-p-phenylene bismethacryl amide as a novel cross-link agent for synthesis and characterization of the core–shell magnetic molecularly imprinted polymer nanoparticles. Journal of Materials Science. Materials in Medicine25(3), 645-656. http://dx.doi.org/10.1007/s10856-013-5118-8. PMid:24338334. 

21 Salz, U., Zimmermann, J., Zeuner, F., & Moszner, N. (2005). Hydrolytic stability of self-etching adhesive systems. The Journal of Adhesive Dentistry7(2), 107-116. http://dx.doi.org/10.3290/j.jad.a10282. PMid:16052759. 

22 Tauscher, S., Angermann, J., Catel, Y., & Moszner, N. (2017). Evaluation of alternative monomers to HEMA for dental applications. Dental Materials33(7), 857-865. http://dx.doi.org/10.1016/j.dental.2017.04.023. PMid:28528931.

23 Rodrigues, S. B., Collares, F. M., Leitune, V. C., Schneider, L. F., Ogliari, F. A., Petzhold, C. L., & Samuel, S. M. W. (2016). Influence of hydroxyethyl acrylamide addition to dental adhesive resin. Dental Materials31(12), 1579-1586. http://dx.doi.org/10.1016/j.dental.2015.10.005. PMid:26549355.

24 Huang, C., Mei, X., Cheng, Y., Li, Y., & Zhu, X. (2014). A model-free method for evaluating theoretical error of Kissinger equation. Journal of Thermal Analysis and Calorimetry116(3), 1153-1157. http://dx.doi.org/10.1007/s10973-013-3624-z

25 Otsu, T., Inoue, M., Yamada, B., & Mori, T. (1975). Structure and reactivity of vinyl monomers: radical reactivities of N-substituted acrylamides and methacrylamides. Journal of Polymer Science. Part C, Polymer Letters13(8), 505-510. http://dx.doi.org/10.1002/pol.1975.130130811

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