Recent advances in the synthesis and applications of poly(1,4-dioxan-2-one)based copolymers

J.-M. Raquez; O. Coulembier; A. Duda; R. Narayan; P. Dubois

Published : 2009-03-15

Vol. 54 No. 3 (2009)

Recent advances in the synthesis and applications of poly(1,4-dioxan-2-one)based copolymers

J.-M. Raquez O. Coulembier A. Duda R. Narayan P. Dubois

Abstract

The review provides the recent advances in the synthesis, properties and applications of poly(1,4-dioxan-2-one) (PPDX). PPDX represents a promising candidate as a biodegradable substitute, because of its interesting thermomechanical properties such as a melting temperature of 110°C. This poly(ester-alt-ether) copolymer can be useful materials not only for medical use, but also for general uses as films, molded products, laminates, foams, nonwoven materials, adhesives and coatings for temporary more universal uses. However, little attention has been paid to the synthesis and properties of PPDX. The main reasons are that its monomer, 1,4-dioxan-2-one, was not commercially available in the past, but also the low ceiling temperature of PPDX (265°C) favors the unzipping depolymerization reactions in the molten state. Hence, the recent improvements in terms of activity and productivity will be discussed according to the key-parameters governing the synthesis and melt-processing of PPDX. Besides, the properties and applications of PPDX are given.

Keywords

polimery biodegradowane ; kopolimery ; poliestry rozgałęzione ; polimeryzacja kontrolowana ; 1,4-dioksan-2-on ; poli(l,4-dioksan-2-on) ; przetwórstwo polimerów ; termodynamika polimeryzacji biodegradable polymers ; copolymers ; branched polyesters ; controlled polymerization ; 1,4-dioxan-2-one ; poly(1,4-dioxan-2-one) ; polymer processing ; thermodynamics of polymerization

Details

References

Statistics

Authors

Download files

PDF

Zasady cytowania

Raquez, J.-M., Coulembier, O., Duda, A., Narayan, R., & Dubois, P. (2009). Recent advances in the synthesis and applications of poly(1,4-dioxan-2-one)based copolymers. Polimery, 54(3), 163–178. Retrieved from https://ichp.vot.pl/index.php/p/article/view/1187

References

Karlsson S., Albertsson A.: Polym. Eng. Sci. 1998, 38,1251.

[2] Reddy C., Ghai R., Rashmi V.: Bioresour. Technol. 2003, 87,137.

[3] Omichi H.: "Handbook of polymer degradation", Dekker, New York, 1992, p. 335.

[4] Lynd L., Wyman C., Gerngross T.: Biotechnol. Próg. 1999, 15, 777.

[5] Ray J. A., Dodd N., Regular D., Williams J. A., Mel Yerger A.: Surge Gynecology Obstetric 1981,153, 497.

[6] Von Fraunhofer J. A., Storey R. S., Stone L K., Master-son B. J.: /. Biomed. Mater. Res. 1985,19,595.

[7] Langer R., Peppas N. A.: AIChE J. 2003, 49, 2990.

[8] Krasowska K., Brzeska J., Rutkowska M., Dacko R, Sobota M., Kowalczuk M.: Polimery 2008, 53, 730.

[9] Niekraszewicz A., Ciechańska D., Wiśniewska-Wrona M., Strobin G., Pospieszny H., Orlikowski L. B.: Polimery 2007, 52, 217.

[10] Libiszowski J., Kowalski A., Bielą T., Duda A.: Polimery 2004, 49, 690.

[11] Jagur-Grodzinski J.: Polym. Adv. Technol 2006,17, 395.

[12] Nair L., Laurencin C.: Prog. Polym. Sci. 2007, 32, 762.

[13] Ikada Y., Tsuji H.: Macromol. Rapid Commun. 2000, 21, 117.

[14] Kapłan D. L.: "Biopolymers from re-newable resources", Springer, New York 1998.

[15] Gross R. A., Scholz C.: "Biopolymers from polysaccharides and agroproteins.", American Chemical Society, Washington D. C. 2001.

[16] Dodds D. R., Gross R. A.: Science 2007, 318, 1250.

[17] Gross R. A., Kalra B.: Science 2002, 297, 803.

[18] Gupta A. R, Kumar V.: Eur. Polym. J. 2007, 43, 4053.

[19] Brodę G., Koleske J.: J. Macromol. Sci.-Chem. 1972, A6,1109.

[20] USA Pat. 4 052 988 (1977).

[21] Nishida H., Yamashita M., Endo T., Tokiwa Y: Macromolecules 2000, 33, 6982.

[22] Kricheldorf H., Dam-rau D.: Macromol. Chem. Phys. 1998,199,1089.

[23] LISA Pat. 5 310 945 (1992).

[24] Johns D., Lenz R., Luecke A.: "Ring-Opening Polymerization", vol. l, Elsevier Science, New York 1984, p. 464.

[25] Mecerreyes D., Jeróme R., Dubois R: Adv. Polym. Sci. 1999, 147, 1.

[26] Yang K., Wang X., Wang Y. Z.: /. Macromol. Sci. 2002, C42,373.

[27] Albertsson A., Varma L: Adv. Polym. Sci. 2002,157,1.

[28] Lebedev V., Evstropov A.: Doki. Akad. Nauk SSSR (Phys. Chem.) 1982, 264, 102.

[29] Duda A., Kowalski A., Penczek S., Uyama H., Kobayashi S.: Macromolecules 2002, 35, 4266.

[30] Ito K., Hashizuka Y, Yamashita Y: Macromolecules 1977,10, 821.

[31] Jedlinski Z., Walach W., Kurcok P., Adamus G.: Makromol Chem. 1991,192, 2051.

[32] Kricheldorf H. R., Berl M., Scharnagl N.: Macromolecules 1988, 21, 286.

[33] Baran J., Duda A., Kowalski A., Szymanski R., Penczek S.: Macromol. Rapid Commun. 1997, 18, 325.

[34] Nishida H., Yamashita M., Nagashima M., Endo T., Tokiwa Y: /. Polym. Sci., Part A: Polym. Chem. 2000, 38,1560.

[35] USA Pat. 3 063 967 (1962).

[36] Dainton R S., Ivin K. J.: Q. Rev. Chem. Soc. 1958,12, 61.

[37] Sawada H.: Polym. Rev. 1970, 5,151.

[38] Raquez J-M, Degee P., Narayan R., Dubois P.: Macromolecules 2001, 34, 8419.

[39] Lebedev B., Bykova T., Kiparisova E., Belen'kaya B., Filatova V.: /. Polym. Sci., Part. A: Polym. Chem. 1995, 37, 187.

[40] Shinno K., Migamoto M., Kimura Y, Hirai Y, Yoshitome H.: Macromolecules 1997, 30, 6438.

[41] Esteves L. M., Marquez L., Muller A. J.: /. Appl. Polym. Sci. 2005, 97, 659.

[42] Libiszowski J., Kowalski A., Szymanski R., Duda A., Raquez J-M., Degee P., Dubois P.: Macromolecules 2004, 37, 52.

[43] Mecerreyes D., Jerome R.: Macromol. Chem. Phys. 1999, 200, 2581.

[44] Jacobs C., Dubois P., Jerome R., Teyssie P.: Macro-molecules 1991, 24, 3027.

[45] Dubois P., Jerome R., Teyssie P.: Polym. Bull. 1989, 22, 475.

[46] Barakat L, Dubois P., Jerome R., Teyssie P.: /. Polym. Sci., Part A: Polym. Chem. 1993, 31, 505.

[47] Penczek S., Duda A., Kowalski A., Libiszowski J., Majerska K., Biela T.: Macromol. Symp. 2000,157,61.

[48] Raquez J-M., Degee P., Narayan R., Dubois P.: Macromol. Rapid Comm. 2000, 21,1063.

[49] Ropson N., Dubois P., Jerome R., Teyssie P.: Macromolecules 1993, 26, 6378.

[50] Barakat L, Dubois P., Grandfils C., Jerome R.: /. Polym. Sci, Part A: Polym. Chem. 2001, 39,294.

[51] Raquez J-M., Degee P., Dubois P., Balakrishnan Sv Narayan R.: Polym. Eng. Sci. 2005,45, 622.

[52] Raquez J-M., Degee P., Dubois P., Nabar Y, Narayan R.: C. R. Chimie 2006,9,1370.

[53] Raquez J-M., Degee P., Narayan R., Dubois P.: Polym. Deg. Stab. 2004, 86, 159.

[54] Du Y, Lemstra P., Nijenhuis A., Van Aert H., Bastiaansen C.: Macromolecules 1995, 28, 2124.

[55] Kricheldorf H., Kreiser-Saunders I., Boettcher C.: Polymer 1995, 36,1253.

[56] Vert M.: Macromol. Symp. 2000,153, 333.

[57] Majerska K., Duda A., Penczek S.: Macromol. Rapid Commun. 2000,21,1327.

[58] Libiszowski J., Kowalski A., Duda A., Penczek S.: Macromol. Chem. Phys. 2002, 203, 1694.

[59] Kowalski A., Duda A., Penczek S.: Macromolecules 2000, 33, 689.

[60] Li Y, Wang X. L., Yang K. K., Wang Y. Z.: Polym. Bull. 2006, 57, 873.

[61] Correa R., Gonzalez G., Dougar V: Polymer 1998, 39,1471.

[62] Porto A. E, Sadicoff B. L., Amorim M. C. V, de Mattos M. C. S.: Polym. Test. 2002,21,145.

[63] Keki S., Bodnar L, Borda J., Deak G., Zsuga M.: Macromol. Rapid Commun. 2001, 22, 1063.

[64] Velmathi S., Nagahata R., Sugiyama J., Takeuchi K.: Macromol. Rapid Commun. 2005,26,1163.

[65] Xu W. L., Bao J. J., Zhang J. C., Shi M. W.: /. Appl. Polym. Sci. 1998, 70, 2343.

[66] Liu L., Li Y, Fang Y, Chen L. X.: Carbohydr. Polym. 2005, 60, 351.

[67] Albert P., Wasth H., Muelhalpt R., Janda R.: Macromol. Chem. Phys. 1996, 197, 1633.

[68] Fang X. M., Hutcheon R., Scola D. A.: /. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1379.

[69] Barbier-Baudry D., Brachais C. H., Cretu A., Loupy A., Stuerga D.: Macromol. Rapid Commun. 2002, 23, 200.

[70] Zhang X. L., Hayward D. O., Mingos D. M. P.: Chem. Commun. 1999,11, 975.

[71] Chen Y. Y, Wu G., Qiu Z. C., Wang X. L., Zhang Y, Fang L., Wang Y Z.: /. Polym. Sci, Part A: Polym. Chem. 2008, 46, 3207.

[72] Biela T., Duda A., Penczek S.: Macromol. Symp. 2002,183,1.

[73] Wang H., Dong J. H., Qiu K. Y, Gu Z. W.: /. Appl. Polym. Sci. 1998, 68, 2121.

[74] Yang K. K., Zheng L., Wang Y Z., Zeng J. B., Wang X. L., Chen S. C., Zeng Q., Li B.: J. Appl. Polym. Sci. 2006,102, 1092.

[75] Bahadur R., Aryal S., Bhattarai S. R., Khil M. S., Kim H. Y: /. Appl. Polym. Sci. 2007,103, 2695.

[76] Zhou Y E, Yang K. K., Wang Y Z., Wang X. L.: Polym. Bull. 2006, 57, 151.

[77] Hong J. T., Cho N. S., Yoon H. S., Kim T. H., Lee D. H., Kim W. G,: /. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2790.

[78] Bahadur R., Bhattarai S. R., Aryal S., Khil M. S., Dharmaraj N., Kim H. Y: Colloids Surf. A 2007,292, 69.

[79] Bhattarai S. R., Yi H, K., Bhattarai N., Hwang P. H., Kim H. Y: Acta Biomat. 2006, A2, 207.

[80] Bhattarai S. R., Yi H. K., Bhattarai N., Hwang P. H., Kim H. Y: Pharm. Res. 2003,20,2021.

[81] Huang H. X., Yang K. K., Wang Y Z., Wang X.L., Li J.: /. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1245.

[82] Yu X. H., Feng J., Zhuo R. X.: Macromolecules 2005, 38, 6244.

[83] Parzuchowski P. G., Grabowska M., Tryznowski M., Rokicki G.: Macromolecules 2006, 39, 7181.

[84] Yoon K, Rv Koh Y J., Choi I. S.: Macromol. Rapid Commun. 2003, 24, 207.

[85] Yoon K. R., Kim W. J., Choi I. S.: Macromol. Chem, Phys. 2004, 205,1218.

[86] Yoon K. R., Kim W. J., Choi I. S.: /. Polym. Res. 2004, 11, 265.

[87] Gross R. A., Kumar A., Kalra B.: Chem, Rev. 2001, 101, 2097.

[88] Matsumura S.: Adv. Polym. Sci. 2006, 194, 95.

[89] He E, Jia H. L., Liu G., Wang Y P., Feng J., Zhuo R. X.: Biomacromolecules 2006, 7, 2269.

[90] Jiang Z., Azim H., Gross R., Focarete M. L., Scandola M.: Biomacromolecules 2007, 8, 2262.

[91] Grablowitz H., Lendlein A.: /. Mater. Chem. 2007, 17, 4050.

[92] Nishida H,, Yamashita M., Endo T.: Polym. Degrad. Stab. 2002, 78, 129.

[93] Nishida H., Yamashita M., Hattori N., Endo T., Tokiwa Y: Polym. Degrad. Stab. 2000,70,485.

[94] Yang K. K., Wang X. L., Wang Y Z., Wu B., Jin Y. D., Yang B.: Eur. Polym. J. 2003, 39, 1567.

[95] USA Pat. 5 652 331 (1997).

[96] Ding S. D., Wang Y Z.: Polym. Degrad. Stab. 2006, 91, 2465.

[97] Huang F. Y, Wang Y. Z., Wang X. L., Yang K. K., Zhou Q., Ding S. D.: /. Polym. Sci., Part A: Polym. Chem. 2005, 43, 2298.

[98] Bezwada R., Jamiolkowski D., Cooper K.: "Handbook of Biodegradable Polymers", Harwood Academic Publishers, London 1997, p. 29.

[99] Sabino M. A., Gonzalez S., Marquez L., Feijoo J. L.: Polym. Degrad. Stab. 2000, 69, 209.

[100] Sabino M. A., Albuerne J., Muller A. J., Brisson J., Prud'homme R. E.: Biomacromolecules 2004, 5, 358.

[101] Nishida H., Yamashita M., Nagashima M., Hattori N., Endo T., Tokiwa Y: Macromolecules 2000,33,6595. 1/5

[102] Albuerne J., Marquez L., Muller A. J., Raquez J. M., Degee P., Dubois P.: Macromol Chem. Phys. 2005,206,903.

[103] Lin H. L., Chu C. C, Grubb D.: /. Biomed. Mater. Res. 1993, 27, 153.

[104] Sabino M. A., Sabater L., Ronca G., Muller A. J.: Polym. Bull. 2002, 48, 291.

[105] Pekkin A. P. T., Duek E. A. R.: Polym. Degrad. Stab. 2002, 78, 405.

[106] Yang K. K., Wang X. L., Wang Y. Z., Huang H. X.: Mater. Chem. Phys. 2004, 87, 218.

[107] Chen S. C., Zhou Z. X., Wang Y. Z., Wang X. L., Yang K. K.: Polymer 2006, 47,32.

[108] Nishida H., Konno M., Tokiwa Y: Polym. Degrad. Stab. 2000, 68, 271.

[109] Nishida H., Konno M., Tokiwa Y: Polym. Degrad. Stab. 2000, 68, 205.

[110] Sabino M. A., Feijoo J. L., Nunez O., Ajami D.: /. Mater. Sci. 2002,37,35.

[111] Wang H., Dong J. H., Qiu K. Y, Gu Z. W.: /. Polym. ScL, Part A: Polym. Chem. 1998, 36, 1301.

[112] Lendlein A., Langer R.: Science 2002, 296, 1673.

[113] Coulembier O., Degee P., Hedrick J. L., Dubois P.: Prog. Polym. Sci. 2006,31, 723.

Google Scholar

Altmetric indicators

Citing articles via

Statistics

Total abstract views : 0

PDF Downloads : 0

J.-M. Raquez jean-marie.raquez@umh.ac.be

Affiliation
University of Mons-Hainaut, Center of Innovation and Research in Materials & Polymers, Laboratory of Polymer and Composite Materials, Place du Parc 20, B-7000 Mons

O. Coulembier

A. Duda

R. Narayan

P. Dubois