Synthesis of hyperbranched poly(ester)s with pendant hydroxy groups by the polyaddition of bis(oxetane)s with 1,3,5-benzenetricarboxylic acid

Synthesis of hyperbranched poly(ester)s with pendant hydroxy groups by the polyaddition of bis(oxetane)s with 1,3,5-benzenetricarboxylic acid

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ABSTRACT Hyperbranched poly(ester)s with many pendant primary hydroxy groups were prepared in 21–84% yields by polyadditions of certain bis(oxetane)s such as 1,4-bis[(3-ethyl-3-oxetanylmethoxymethyl)]benzene (BEOB), 1,2-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,2-BEOMB), 1,3-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,3-BEOMB), 1,4-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,4-BEOMB), 4,4′-bis[(3-ethyl-3-oxetanyl)methoxy]biphenyl (4,4′-BEOBP), 3,3′,5,5′-tetramethyl-[4,4′-bis(3-ethyl-3-oxetanyl)methoxy]biphenyl (TM-BEOBP) with 1,3,5-benzenetricarboxylic acid (TMA) using tetraphenylphosphonium chloride (TPPC) as a catalyst in NMP at 140 °C for 12 h. Resulting polymers were insoluble in water; however, these polymers were soluble in 2.3% tetramethylammonium hydroxide aqueous solution. These polymers were also soluble in dioxane, THF, MEK, and aprotic polar solvents. The glass transition temperatures (_T_gs) of these polymers were 59–131 °C. SIMILAR CONTENT BEING VIEWED BY OTHERS PROTECTION-FREE ONE-POT SYNTHESIS OF ALCOHOL END-FUNCTIONALIZED POLY(3-HEXYLTHIOPHENE) Article 05 July 2021 CHEMOSELECTIVE TRANSESTERIFICATION AND POLYMER SYNTHESIS USING A ZINCATE COMPLEX Article 18 September 2020 SYNTHESIS OF FUNCTIONAL AND ARCHITECTURAL POLYETHERS VIA THE ANIONIC RING-OPENING POLYMERIZATION OF EPOXIDE MONOMERS USING A PHOSPHAZENE BASE CATALYST Article 15 April 2021 ARTICLE PDF REFERENCES * A. S. Pell and G. Pilchere, _Trans. Faraday Soc._, 61, 71 (1965). * S. Inoue and T. Aida, “Ring-Opening Polymerization,” K. J. Ivin and T. Saegusa, Ed., Elsevior Science Publishers, London, 1984, p 185. * A. Ueyama, M. Mizuno, S. Kanoh, and M. Motoi, _Polym. J._, 34, 944 (2002). * S. Kano, T. Nishimura, Y. Kita, H. Ogawa, M. Motoi, M. Takani, and T. Tanaka, _J. Org. Chem._, 65, 2253 (2000). * H. Ogawa, S. Kanoh, and M. Motoi, _Bull. Chem. Soc. Jpn._, 70, 1649 (1997). * T. Nishikubo and A. Kameyama, _Kagaku to Kogyo_, 57, 225 (2004). * T. Nishikubo and K. Sato, _Chem. Lett._, 697 (1991). * S. Minegishi, S. Tsuchida, M. Sasaki, A. Kameyama, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 40, 3835 (2002). * S. Minegishi, M. Ito, A. Kameyama, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 38, 2254 (2000). * T. Nishikubo, A. Kameyama, and A. Suzuki, _React. Funct. Polym._, 37, 19 (1998). * T. Nishikubo, A. Kameyama, M. Ito, T. Nakajima, and H. Miyazaki, _J. Polym. Sci., Part A: Polym. Chem._, 37, 2781 (1999). * Y. Konno, H. Suzuki, H. Kudo, A. Kameyama, and T. Nishikubo, _Polym. J._, 36, 114 (2004). * T. Nishikubo, A. Kameyama, M. Ito, and A. Suzuki, _J. Polym. Sci., Part A: Polym. Chem._, 36, 2873 (1998). * A. Kameyama, Y. Yamamoto, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 31, 1639 (1993). * A. Kameyama, Y. Yamamoto, and T. Nishikubo, _Macromol. Chem. Phys._, 197, 1147 (1996). * T. Nishikubo, A. Kameyama, and C. Izawa, _J. Polym. Sci., Part A: Polym. Chem._, 39, 368 (2001). * T. Yashiro, K. Matsushima, A. Kameyama, and T. Nishikubo, _Macromolecules_, 33, 7737 (2000). * H. Kudo, T. Kurakata, M. Sasaki, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 42, 1528 (2004). * T. Nishikubo, H. Kudo, M. Sasaki, K. Kuwamura, and C. Imataki, _Polym. J._, 36, 841 (2004). * H. Kudo, A. Morita, and T. Nishikubo, _Polym. J._, 35, 88 (2003). * A. Morita, H. Kudo, and T. Nishikubo, _Polym. J._, 36, 413 (2004). * A. Morita, H. Kudo, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 42, 3739 (2004). * A. Kameyama, K. Ueda, H. Kudo, and T. Nishikubo, _Macromolecules_, 35, 3792 (2002). * M. Okazaki, I. Washio, Y. Shibasaki, and M. Ueda, _J. Am. Chem. Soc._, 125, 8120 (2003). * K. Matyjaszewski, S. G. Gaynor, A. Kulfan, and M. Podwike, _Macromolecules_, 30, 5192 (1997). * A. Sunder, R. Hanselmann, H. Frey, and R. Mulhaupt, _Macromolecules_, 32, 4240 (1999). * J. Hao, M. Jikei, and M. Kakimoto, _Macromolecules_, 36, 3519 (2003). * S. Makita, H. Kudo, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 42, 3697 (2004). * T. Nishikubo, T. Iizawa, M. Shimojyo, T. Kato, and A. Shiina, _J. Org. Chem._, 55, 2536 (1990). * T. Nishikubo, T. Kato, Y. Sugimoto, M. Tomoi, and S. Ishigaki, _Macromolecules_, 23, 3406 (1990). * “Handbook of Solvents,” T. Asahara, N. Tokura, M. Okawara, J. Kumanotani, and M. Seno, Ed., Kodansha, Tokyo, 1976. Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221-8686, Japan Tadatomi Nishikubo, Hiroto Kudo & Takehiko Nakagami Authors * Tadatomi Nishikubo View author publications You can also search for this author inPubMed Google Scholar * Hiroto Kudo View author publications You can also search for this author inPubMed Google Scholar * Takehiko Nakagami View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Tadatomi Nishikubo. RIGHTS AND PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Nishikubo, T., Kudo, H. & Nakagami, T. Synthesis of Hyperbranched Poly(ester)s with Pendant Hydroxy Groups by the Polyaddition of Bis(oxetane)s with 1,3,5-Benzenetricarboxylic Acid. _Polym J_ 38, 145–152 (2006). https://doi.org/10.1295/polymj.38.145 Download citation * Received: 05 September 2005 * Accepted: 04 October 2005 * Published: 15 February 2006 * Issue Date: 01 February 2006 * DOI: https://doi.org/10.1295/polymj.38.145 SHARE THIS ARTICLE Anyone you share the following link with will be able to read this content: Get shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing initiative KEYWORDS * Synthesis of Hyperbranched Poly(ester) * Pendant Hydroxy Group * Polyaddition * Bis(oxetane) * 1,3,5-Benzenetricarboxylic Acid

ABSTRACT Hyperbranched poly(ester)s with many pendant primary hydroxy groups were prepared in 21–84% yields by polyadditions of certain bis(oxetane)s such as


1,4-bis[(3-ethyl-3-oxetanylmethoxymethyl)]benzene (BEOB), 1,2-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,2-BEOMB), 1,3-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,3-BEOMB),


1,4-bis[(3-ethy-3-oxetanyl)methoxy]benzene (1,4-BEOMB), 4,4′-bis[(3-ethyl-3-oxetanyl)methoxy]biphenyl (4,4′-BEOBP), 3,3′,5,5′-tetramethyl-[4,4′-bis(3-ethyl-3-oxetanyl)methoxy]biphenyl


(TM-BEOBP) with 1,3,5-benzenetricarboxylic acid (TMA) using tetraphenylphosphonium chloride (TPPC) as a catalyst in NMP at 140 °C for 12 h. Resulting polymers were insoluble in water;


however, these polymers were soluble in 2.3% tetramethylammonium hydroxide aqueous solution. These polymers were also soluble in dioxane, THF, MEK, and aprotic polar solvents. The glass


transition temperatures (_T_gs) of these polymers were 59–131 °C. SIMILAR CONTENT BEING VIEWED BY OTHERS PROTECTION-FREE ONE-POT SYNTHESIS OF ALCOHOL END-FUNCTIONALIZED


POLY(3-HEXYLTHIOPHENE) Article 05 July 2021 CHEMOSELECTIVE TRANSESTERIFICATION AND POLYMER SYNTHESIS USING A ZINCATE COMPLEX Article 18 September 2020 SYNTHESIS OF FUNCTIONAL AND


ARCHITECTURAL POLYETHERS VIA THE ANIONIC RING-OPENING POLYMERIZATION OF EPOXIDE MONOMERS USING A PHOSPHAZENE BASE CATALYST Article 15 April 2021 ARTICLE PDF REFERENCES * A. S. Pell and G.


Pilchere, _Trans. Faraday Soc._, 61, 71 (1965). * S. Inoue and T. Aida, “Ring-Opening Polymerization,” K. J. Ivin and T. Saegusa, Ed., Elsevior Science Publishers, London, 1984, p 185. * A.


Ueyama, M. Mizuno, S. Kanoh, and M. Motoi, _Polym. J._, 34, 944 (2002). * S. Kano, T. Nishimura, Y. Kita, H. Ogawa, M. Motoi, M. Takani, and T. Tanaka, _J. Org. Chem._, 65, 2253 (2000). * H.


Ogawa, S. Kanoh, and M. Motoi, _Bull. Chem. Soc. Jpn._, 70, 1649 (1997). * T. Nishikubo and A. Kameyama, _Kagaku to Kogyo_, 57, 225 (2004). * T. Nishikubo and K. Sato, _Chem. Lett._, 697


(1991). * S. Minegishi, S. Tsuchida, M. Sasaki, A. Kameyama, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 40, 3835 (2002). * S. Minegishi, M. Ito, A. Kameyama, and T. Nishikubo,


_J. Polym. Sci., Part A: Polym. Chem._, 38, 2254 (2000). * T. Nishikubo, A. Kameyama, and A. Suzuki, _React. Funct. Polym._, 37, 19 (1998). * T. Nishikubo, A. Kameyama, M. Ito, T. Nakajima,


and H. Miyazaki, _J. Polym. Sci., Part A: Polym. Chem._, 37, 2781 (1999). * Y. Konno, H. Suzuki, H. Kudo, A. Kameyama, and T. Nishikubo, _Polym. J._, 36, 114 (2004). * T. Nishikubo, A.


Kameyama, M. Ito, and A. Suzuki, _J. Polym. Sci., Part A: Polym. Chem._, 36, 2873 (1998). * A. Kameyama, Y. Yamamoto, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 31, 1639


(1993). * A. Kameyama, Y. Yamamoto, and T. Nishikubo, _Macromol. Chem. Phys._, 197, 1147 (1996). * T. Nishikubo, A. Kameyama, and C. Izawa, _J. Polym. Sci., Part A: Polym. Chem._, 39, 368


(2001). * T. Yashiro, K. Matsushima, A. Kameyama, and T. Nishikubo, _Macromolecules_, 33, 7737 (2000). * H. Kudo, T. Kurakata, M. Sasaki, and T. Nishikubo, _J. Polym. Sci., Part A: Polym.


Chem._, 42, 1528 (2004). * T. Nishikubo, H. Kudo, M. Sasaki, K. Kuwamura, and C. Imataki, _Polym. J._, 36, 841 (2004). * H. Kudo, A. Morita, and T. Nishikubo, _Polym. J._, 35, 88 (2003). *


A. Morita, H. Kudo, and T. Nishikubo, _Polym. J._, 36, 413 (2004). * A. Morita, H. Kudo, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 42, 3739 (2004). * A. Kameyama, K. Ueda, H.


Kudo, and T. Nishikubo, _Macromolecules_, 35, 3792 (2002). * M. Okazaki, I. Washio, Y. Shibasaki, and M. Ueda, _J. Am. Chem. Soc._, 125, 8120 (2003). * K. Matyjaszewski, S. G. Gaynor, A.


Kulfan, and M. Podwike, _Macromolecules_, 30, 5192 (1997). * A. Sunder, R. Hanselmann, H. Frey, and R. Mulhaupt, _Macromolecules_, 32, 4240 (1999). * J. Hao, M. Jikei, and M. Kakimoto,


_Macromolecules_, 36, 3519 (2003). * S. Makita, H. Kudo, and T. Nishikubo, _J. Polym. Sci., Part A: Polym. Chem._, 42, 3697 (2004). * T. Nishikubo, T. Iizawa, M. Shimojyo, T. Kato, and A.


Shiina, _J. Org. Chem._, 55, 2536 (1990). * T. Nishikubo, T. Kato, Y. Sugimoto, M. Tomoi, and S. Ishigaki, _Macromolecules_, 23, 3406 (1990). * “Handbook of Solvents,” T. Asahara, N. Tokura,


M. Okawara, J. Kumanotani, and M. Seno, Ed., Kodansha, Tokyo, 1976. Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Department of Applied Chemistry, Faculty of


Engineering, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama, 221-8686, Japan Tadatomi Nishikubo, Hiroto Kudo & Takehiko Nakagami Authors * Tadatomi Nishikubo View author


publications You can also search for this author inPubMed Google Scholar * Hiroto Kudo View author publications You can also search for this author inPubMed Google Scholar * Takehiko


Nakagami View author publications You can also search for this author inPubMed Google Scholar CORRESPONDING AUTHOR Correspondence to Tadatomi Nishikubo. RIGHTS AND PERMISSIONS Reprints and


permissions ABOUT THIS ARTICLE CITE THIS ARTICLE Nishikubo, T., Kudo, H. & Nakagami, T. Synthesis of Hyperbranched Poly(ester)s with Pendant Hydroxy Groups by the Polyaddition of


Bis(oxetane)s with 1,3,5-Benzenetricarboxylic Acid. _Polym J_ 38, 145–152 (2006). https://doi.org/10.1295/polymj.38.145 Download citation * Received: 05 September 2005 * Accepted: 04 October


2005 * Published: 15 February 2006 * Issue Date: 01 February 2006 * DOI: https://doi.org/10.1295/polymj.38.145 SHARE THIS ARTICLE Anyone you share the following link with will be able to


read this content: Get shareable link Sorry, a shareable link is not currently available for this article. Copy to clipboard Provided by the Springer Nature SharedIt content-sharing


initiative KEYWORDS * Synthesis of Hyperbranched Poly(ester) * Pendant Hydroxy Group * Polyaddition * Bis(oxetane) * 1,3,5-Benzenetricarboxylic Acid