Abstract
We successfully synthesized acetyl group-containing phenolic resins as novel reactive polymers. The addition-condensation of 2,4,6-trimethoxyacetophenone (1) with an equimolar amount of formaldehyde catalyzed by 12mol/L HCl aq. proceeded homogeneously without side reactions to give polymer 3 (Mn 4800, Mw/Mn 1.3) in 32% yield. The FT-IR, 1H NMR and 13C NMR spectra of 3 revealed that it had arylene-methylene units on the polymer backbones. The terpolymerization from 1, 1,3,5-trimethoxybenzene (2) and formaldehyde was also carried out. When the feed ratio of 1 to 2 was 1:1, the content of 1 in the obtained polymer, 4, was found to be 25% by the 1H NMR spectrum; hence, the reactivity of 1 was lower than that of 2. The reactions of 4 with Grignard reagents were carried out to evaluate the reactivity of acetyl groups in the obtained polymers. Their reactions proceeded at some parts of acetyl groups, so 4 can be applied as novel reactive phenolic resins. From thermogravimetric analyses, thermal stabilities of the functionalized polymers (6a-6d) are similar to that of 4, so it is expected that 4 have characters not only of the phenolic resins but also of the reactive polymers.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
A. Knop and L. A. Pilato, “Phenolic Resins.” Springer-verlag, Berlin, 1985.
G. Konishi, J. Syn. Org. Chem. Jpn., 66, 705 (2008).
D. Crespy, M. Bozonnet, and M. Meier, Angew. Chem., Int. Ed., 47, 3322 (2008).
T. Takeichi, T. Kawauchi, and T. Agag, Polym. J., 40, 1121 (2008).
J. Kadota, T. Fukuoka, H. Uyama, K. Hasegawa, and S. Kobayashi, Macromol. Rapid Commun., 25, 441 (2004).
T. Nemoto, I. Amir, and G. Konishi, Polym. J., 41, 338 (2009).
J. Cui, Y. Yan, J. Liu, and Q. Wu, Polym. J., 40, 1067 (2008).
B. S. Kaith and S. Kalia, Polym. J., 39, 1319 (2007).
G. Pan, Z. Du, C. Zhang, C. Li, X. Yang, and H. Li, Polym. J., 39, 478 (2007).
K. Suzuki, H. Matsumoto, M. Minagawa, M. Kimura, and A. Tanioka, Polym. J., 39, 1128 (2007).
D.-M. Shin, N. Ozeki, Y. Nakamoto, and G. Konishi, Macromol. Res., 14, 255 (2006).
T. Kimura, Y. Nakamoto, and G. Konishi, Polym. J., 38, 606 (2006).
T. Nemoto, T. Ueno, M. Nishi, D.-M. Shin, Y. Nakamoto, and G. Konishi, Polym. J., 38, 1278 (2006).
J. Jeerupan, G. Konishi, T. Nemoto, D. M. Shin, and Y. Nakamoto, Polym. J., 39, 762 (2007).
A. Kobayashi and G. Konishi, Polym. J., 40, 590 (2008).
T. Nemoto and G. Konishi, Polym. J., 40, 651 (2008).
T. Nemoto, G. Konishi, T. Arai, and T. Takata, Polym. J., 40, 622 (2008).
S. Sugawara, M. Tomoi, and T. Oyama, Polym. J., 39, 129 (2007).
K. Tsuchiya, Y. Shibasaki, and M. Ueda, Polym. J., 39, 442 (2007).
T. Nishikubo, H. Kudo, and H. Nomura, Polym. J., 40, 310 (2008).
Y. Chujo, I. Tomita, Y. Higashiguchi, and T. Saegusa, Macromolecules, 24, 3010 (1991).
H. Ritter and R. Sperber, Macromolecules, 27, 5919 (1994).
T. F. Scott, A. D. Schneider, W. D. Cook, and C. N. Bowman, Science, 308, 1615 (2005).
N. N. Ghosh, B. Kiskan, and Y. Yagci, Prog. Polym. Sci., 32, 1344 (2007).
K. Mizoguchi and M. Ueda, Polym. J., 40, 645 (2008).
N. Matsumi and Y. Chujo, Polym. J., 40, 77 (2008).
T. Nemoto, I. Amir, and G. Konishi, Polym. J., 41, 389 (2009).
T. Fukuoka, H. Uyama, and S. Kobayashi, Macromolecules, 36, 8213 (2003).
T. Yamagishi, R. Takahashi, D. Nagata, G. Konishi, and Y. Nakamoto, Kobunshi Ronbunshu, 60, 200 (2003).
S. Ishida, T. Kitagawa, Y. Nakamoto, and K. Kaneko, Polym. Bull., 10, 533 (1983).
K. Kamide and Y. Miyakawa, Makromol. Chem., 179, 359 (1978).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nemoto, T., Amir, I. & Konishi, Gi. Synthesis of Alkoxylated Phenolic Resins Containing an Acetyl Group and Their Functionalization by Grignard Reaction. Polym J 41, 395–401 (2009). https://doi.org/10.1295/polymj.PJ2008321
Received:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1295/polymj.PJ2008321
Keywords
This article is cited by
-
Preparation of high-refractive-index trimethoxybenzene novolac-titania hybrid
Macromolecular Research (2011)
-
Direct synthesis of functional novolacs and their polymer reactions
Polymer Journal (2010)
-
Development of lignin as a transparent resin: evaluation of thermal and optical properties of alkoxylated lignophenols
Polymer Journal (2010)
-
New class of reactive novolac: synthesis of bisphenol A-based novolac with methylol groups
Polymer Journal (2010)
