Struktura i reaktywność związków alkoksy-cynkowych jako inicjatorów/katalizatorów polimeryzacji estrów cynicznych

• Autorzy: Petrus Rafał , Utko Józef , Sobota Piotr

Warianty tytułu

EN

Structure and reactivity of alkoxy-zinc compounds as initiators/catalysts in the polymerization of cyclic esters

• Języki publikacji: PL

Abstrakty

EN

This review focuses on advances in the synthesis and structural chemistry of zinc alkoxide compounds for use in the catalytic ring-opening polymerization (ROP) of lactides (LAs). This route was used for the preparation of lactic acid based polymers - referred to as polylactides (PLAs). These polyesters have ecofriendly properties such as renewability, biocompatibility, and biodegradability, and are therefore among the most promising green polymers. PLAs have found numerous specialty applications in the biomedical industry, such as biodegradable screws and sutures, scaffolds for tissue engineering, matrices for controlled drug delivery systems, and environmentally friendly food-packaging materials. In industry, PLAs were synthesized by bulk polymerization of LA using tin(II) alkoxides synthesized in situ from tin(II) 2-ethylhexanoate. The toxicity associated with most tin compounds is a considerable drawback in the case of biomedical applications. There has therefore been much research devoted to finding well- defined complexes of high activity containing biologically benign metals. In this context, zinc alkoxides are very attractive non-toxic initiators for the synthesis of polymers that could be used in medical and environmental fields. The most broadly applied representations of zinc initiators for ROP of LA are zinc carboxylates, ß-diketonates, ß-diketiminates, phenolates and bisphenolates, trispyrazolyl- and trisindazolyl-borates, heteroscorpionates, aminophenolates, Schiff base, and iminealkoxylates. The mentioned above initiators were classified and analyzed in the context of their coordination chemistry and revealed catalytic activity in the ROP of LA. The review contains only pioneering/groundbreaking works that allowed for setting new research paths for each of the described groups of initiators, showing how this theme has changed over the last several decades.

Słowa kluczowe

PL

związki alkoksylowe cynku; polilaktyd; polimeryzacja; laktyd; kwas mlekowy

EN

zinc alkoxides; polylactide; polymerization; lactide; lactic acid

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2021
• Tom: [Z] 75, 3-4
• Strony: 343--373
• Opis fizyczny: Bibliogr. 136 poz., rys., schem., tab.

Twórcy

autor

Petrus Rafał

• Politechnika Wrocławska, Wydział Chemiczny, ul. Smoluchowskiego 23, 50-370 Wrocław

• https://orcid.org/0000-0001-7572-3252

autor

Utko Józef

• Uniwersytet Wrocławski, Wydział Chemii, ul. Joliot-Curie 14, 50-383 Wrocław

• https://orcid.org/0000-0001-5218-3564

autor

Sobota Piotr

• Sieć Badawcza Łukasiewicz — PORT Polski Ośrodek Rozwoju Technologii, ul. Stabłowicka 147, 54-066 Wrocław

• https://orcid.org/0000-0002-4364-2957

Bibliografia

• [1] T. Yu, W. Su, W. Li, Z. Hong, R. Hua, B. Li, Thin Solid Films, 2007, 515, 4080.
• [2] N. S. Norberg, D. R. Gamelin, J. Phys. Chem. B, 2005, 109, 20810.
• [3] P. Petrova, R. Tomova, R. Stoycheva-Topalova (2011). Organic Light Emitting Diodes Based on Novel Zn and Al Complexes, Organic Light Emitting Diode - Material, Process and Devices, Ed. S. Hwan Ko, InTech.
• [4] Z. Li, A. Dellali, J. Malik, M. Motevalli, R. M. Nix, T. Olukoya, Y. Peng, H. Ye, W. P. Gillin, I. Hernández, P. B. Wyatt, Inorg. Chem. 2013, 52, 1379.
• [5] N. Poulter, M. Donaldson, G. Mulley, L. Duque, N. Waterfield, A. G. Shard, S. Spencer, A. Tobias A. Jenkins, A. L. Johnson, New J. Chem., 2011, 35, 1477
• [6] A. Tarushi, J. Kljun, I. Turel, A. A. Pantazaki, G. Psomas, D.P. Kessissoglou, New J. Chem., 2013, 37, 342.
• [7] N.L. Reeder, J. Xu, R.S. Youngquist, J.R. Schwartz, R.C. Rust, C.W. Saunders, Br. J. Dermatol., 2011, 165, 9.
• [8] R.S. Joseyphus, M.S. Nair, Mycobiology, 2008, 36, 93.
• [9] Y. DeAngelis, E. MacDonald, K. Kramp, R. Bacon, D.J. Kaufman, J.R. Schwartz, T.L. Dawson, Procter & Gamble Company, Cincinnati, Ohio, http://www.pgbeautyscience.com/en_UK/pdf/poster_2DeAngelis2004.pdf
• [10] D. Desbouis, I.P. Troitsky, M.J. Belousoff L. Spiccia, B. Graham, Coord. Chem. Rev., 2012, 256, 897.
• [11] O. Bistri, B. Colasson, O. Reinaud, Chem. Sci., 2012, 3, 811.
• [12] T. Nakanishi, E. Ando, M. Furuta, E. Kinoshita, E. Kinoshita-Kikuta, T. Koike, S. Tsunasawa, O. Nishimura, J. Biomol. Tech. 2007, 18, 278.
• [13] M. Kawase, N. Kagaya, S. Akamatsu, A. Kamiyoshi, S. Muto, Y. Tagawa, K. Yagi, Exp. Anim., 2004, 53, 1.
• [14] H. Sakurai, A. Katoh, T. Kiss, T. Jakusch, M. Hattori, Metallomics, 2010, 2, 670.
• [15] J.M. Grévy, (2011). Zinc: Organometallic Chemistry. Encyclopedia of Inorganic Chemistry, 2nd ed. New York: John Wiley & Sons.
• [16] H. Pińkowska, Polimery, 2006, 51, 836.
• [17] H.J. Gay-Lussac, H. Pelouze, Ann. Phys., 1833, 105, 108.
• [18] P. Gruber, M. O'Brien, Polylactides “NatureWorks® PLA”, w: Biopolymers in 10 volumes, Volume 4, Polyesters Ш, Applications and Commercial Products. Y. Doi, A. Steinbüchel (ed.), 235-249. Wiley-VCH, Weinheim, Germany (2002).
• [19] C.A. Bischoff, P. Walden, Justus Liebigs Ann. Chem., 1894, 279, 71.
• [20] W. Carothers, G.L. Dorouganhd, F. J. Van Natta, J. Am. Chem. Soc., 1932, 54, 761.
• [21] R.E. Drumright, P.R. Gruber, D.E. Henton, Adv. Mater., 2000, 12, 1841.
• [22] J.C. Middleton, A.J. Tipton, Biomaterials, 2000, 21, 2335.
• [23] P.I.J.M. Wuisman, T.H. Smit, Eur. Spine. J., 2006, 15, 133.
• [24] I. Sirbu, Optics & Mecatronics, 2007, 32, 925.
• [25] SBM, LIGAFIX ®, http://www.s-b-m.fr/fr/produits/images/Radiosa3moiseta1anlig60.jpg.
• [26] MAST Biosurgery, Inc., OrthoWrapTM, Bioresorbable Protective Sheet, http: //www.mastbio.com/USA/images/orthowrap2.jpg.
• [27] R. Auras, B. Harte, S. Selke, Macromol. Biosci., 2004, 4, 835.
• [28] J. Gołębiewski, E. Gibas, R. Malinowski, Polimery 2008, 53, 799.
• [29] Green Technology, NatureWorks Compostable PLA Plastic, http://www.natureworks llc.com/product-andapplications/~/media/Images/general/AllSegmentGrouping_400x262px_jpg.ashx.
• [30] N. Narayanan, P.K. Roychoudhury, A. Srivastava, Electron. J. Biotechn., 2004, 7, 167.
• [31] Y.-J. Wee, J.-N. Kim, H.-W. Ryu, Food Technol. Biotechnol., 2006, 44, 163-172.
• [32] E.T.H Virik, K.R. Rábago, D.A. Glassner, B. Springs, R.P. O'Connor, J. Kolstad, P R. Gruber, Macromol. Biosci., 2004, 4, 551.
• [33] Z. Floijańczyk, M. Dębowski, E. Chwojnowska, K. Lokaj, J. Ostrowską Polimery, 2009, 54, 609.
• [34] A.P. Gupta, V. Kumar, Eur. Polym. J., 2007, 43, 4053.
• [35] L.-T. Lim, R. Auras, M. Rubino, Prog. Polym. Sci., 2008, 33, 820.
• [36] A. Duda, Przemysł Chemiczny 2003, 82, 905.
• [37] A. Duda, A. Kowalski, Polimery, 2007, 52, 485.
• [38] O. Dechy-Cabaret, B. Martin-Vaca, D. Bourissou, Chem. Rev., 2004, 104, 6147.
• [39] A. Södegard, M. Stolt, Prog. Polym. Sei., 2002, 27, 1123.
• [40] D. Garlotta, J. Polym. Environ., 2001, 9, 63.
• [41] A. Duda, S. Penczek, Polimery, 2003, 48, 16.
• [42] R. H. Platel, L. M. Hodgson, C. K. Williams, Polym. Rev., 2008, 48, 11.
• [43] J. Lewiński, P. Horeglad, K. Wójcik, I. Justyniak, Organometallics, 2005, 24, 4588.
• [44] M.H. Chisholm, J.C. Gallucci, H. Yin, Dalton Trans., 2007, 4811.
• [45] J.W. Leenslag, A.J. Pennings, Makromol. Chem., 1987, 188, 1809.
• [46] D.E. Henton, P. Gruber, J. Lunt, J. Randall, 2005. Polylactic acid technology, str. 527-577 w Natural fibers, biopolymers, and their biocomposites, ed. A.K. Moharty, M. Mishra, L.T. Drzal, CRC Press, Boca Raton, FL.
• [47] A. Kowalski, A. Duda, S. Penczek, Macromolecules, 2000, 33, 7359.
• [48] A. Duda, A. Kowalski, S. Penczek, H. Uyama, S. Kobayashi, Macromolecules, 2002, 35, 4266.
• [49] G. Schwach, J. Coudane, R. Engel, M. Vert, Polym. Bull., 1996, 37, 771.
• [50] C.A. Wheaton, P.G. Hayes, B.J. Ireland, Dalton Trans., 2009, 4832.
• [51] J. Wu, T.-L. Yu, C.-T. Chen, C.-C. Lin, Coord. Chem. Rev. 2006, 250, 602.
• [52] M.J. Stanford, A.P. Dove, Chem. Soc. Rev., 2010, 39, 486.
• [53] T.M. Ovitt, G.W. Coates, J. Am. Chem. Soc. 1999, 121, 4072.
• [54] T.M. Ovitt, G.W. Coates, J. Am. Chem. Soc. 2002, 124, 1316.
• [55] N. Spassky, M. Wisniewski, C. Pluta, A. Le Borgne, Macromol. Chem. Phys. 1996, 197, 2627.
• [56] Z. Zhong, P. J. Dijkstra, J. Feijen, Angew. Chem., Int. Ed. 2002, 41, 4510.
• [57] N. Nomura, R. Ishii, M. Akakura, K. Aoi, J. Am. Chem. Soc. 2002, 124, 5938.
• [58] M. Cheng, A.B. Attygalle, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc. 1999, 121, 11583.
• [59] J. Ahmed, S.K. Varshney, Int. J. Food Prop., 2011, 14, 37.
• [60] R. Mehta, V. Kumar, H. Bhunia, S.N. Upadhyay, J. Macromol. Sci. Polymer Rev., 2005, 45, 325.
• [61] R.A. Auras, L.-T. Lim, S.E.M. Selke, H. Tsuji, Poly(Lactic Acid): Synthesis, Structures, Properties, Processing, and Applications, New Jersey: John Wiley & Sons, 2010,
• [62] Purac, http://www.purac.com/_sana_/handlers/getfile.ashx/47df134e-d8ed-4801-b9cf-9497ed44b93b/Coffee-Cups—2012—for-website.jpg
• [63] G. Schwach, J. Coudane, R. Engel, M.Vert, Polym. Bull., 1994, 32, 617.
• [64] H.R. Kricheldorf, A. Serra, PolyM. Bull. 1985, 14, 497.
• [65] H.R. Kricheldorf, J.M. Jonté, M. Berl, Polylactones 3: Makromol. Chem., 1985, 12, 25.
• [66] H.R. Kricheldorf, D.-O. Damrau, Polylactones, 37: Macromol. Chem. Phys., 1997, 198, 1753.
• [67] M. Bero, J. Kasperczyk, Z. J. Jedliński, Makromol. Chem., 1990, 191, 2287.
• [68] H.R. Kricheldorf, D.O. Damrau, Polylactones, 43: Macromol. Chem. Phys., 1998, 199, 1747.
• [69] H.R. Kricheldorf, C. Boettcher, J. Macromol. Sci., Pure Appl. Chem. 1993, 30, 441.
• [70] R. Mazarro, I. Gracia, J. F. Rodriguez, G. Storti, M. Morbidelli, Polym. Int., 2012, 61, 265.
• [71] R.R. Gowda, D. Chakraborty, J. Mol. Catal. A: Chem., 2010, 333, 167.
• [72] I. Kreiser-Saunders, H. R. Kricheldorf, Polylactones, 39: Macromol. Chem. Phys., 1998, 199,1081.
• [73] Y. Han, X. Jin, J. Yang, Z. Fan, Z. Lu, Y. Zhang, S. Li, Polym. Eng. Sci., 2012, 52, 741.
• [74] G. Schwach, J. Coudane, R. Engel, M. Vert, Polym. Int., 1998, 46, 177.
• [75] M. Vert, J. Coudane, G. Schwach, O. J. Huet, Patent FR2745005 A1, 1997.
• [76] M. Müller, Patent EP0261572 A1, 1988.
• [77] J. Börner, U. Flörke, A. Döring, D. Kuckling, M. D. Jones, S. Heires-Pawlis, Sustainability, 2009, 1, 1226.
• [78] A.J. Nijenhuis, D.W. Grijpma, A.J. Pennings, Polym. Bull., 1991, 26, 71.
• [79] A.J. Nijenhuis, D.W. Grijpma, A.J. Pennings, Macromolecules, 1992, 25, 6419.
• [80] N. Iwasa, K. Miura, Y. Furukawa, Patent US20110313127 A1, 2011.
• [81] J. Libiszowski, A. Kowalski, A. Duda, S. Penczek, Macromol. Chem. Phys., 2002, 203, 1694.
• [82] Y. Hata, Y. Igari, Patent US6756472 B1, 2004.
• [83] I. Barakat, P. Dubois, R. Jerome, P. Teyssie, Macromolecules, 1991, 24, 6542.
• [84] J. G. Noltes, F Verbeek, H. G. J. Overmars, J. Boersma, J. Organomet. Chem., 1970, 24, 257.
• [85] M. Bero, J. Kasperczyk, G. Adamus, Makromol. Chem., 1993, 194, 907.
• [86] G. Bertrand, M.-V. Blanca, D. Bourissou, J.-B. Cazaux, A. Dumitrescu, H. Gornitzka, Patent US20040110912 A1, 2004.
• [87] R. Han, G. Parkin, Organometallics, 1991, 10, 1010.
• [88] R. Han, G. Parkin, J. Am. Chem. Soc., 1992, 114, 748.
• [89] M.H. Chisholm, N.W. Eilerts, Chem. Commun., 1996, 853.
• [90] M.H. Chisholm, N.W. Eilerts, J. C. Huffman, S. S. Iyer, M. Pacold, K. Phomphrai, J. Am. Chem. Soc., 2000, 122, 11845.
• [91] M.H. Chisholm, J. Gallucci, K. Phomphrai, Chem. Commun., 2003, 48.
• [92] A. Garcés, L.F. Sánchez-Barba, C. Alonso-Moreno, M. Fajardo, J. Fernández-Baeza, A. Otero, A. Lara-Stachez, I. López-Solera, A.M. Rodriguez, Inorg Chem., 2010, 15, 2859.
• [93] A. Otero, J. Fernández-Baeza, L.F. Sánchez-Barba, J. Tejeda, M. Honrado, A. Garcés, A. Lara-Sánchez, A. M. Rodriguez, Organometallics, 2012, 31, 4191.
• [94] M. Honrado, A. Otero, J. Fernández-Baeza, L.F. Sánchez-Barba, A. Lara-Sánchez, J. Tejeda, M. P. Camón, J. Martínez-Ferrer, A.Garcés, A. M. Rodríguez, Organometallics, 2013, 32, 3437.
• [95] B. Lian, C.M. Thomas, O.L. Casagrande, Jr., C.W. Lehmann, T. Roisnel, J.-F. Carpentier, Inorg. Chem., 2007, 46, 328.
• [96] M. Cheng, A.B. Attygalle, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc., 1999, 121, 11583.
• [97] A.P. Dove, V.C. Gibson, E.L. Marshall, A.J.P. White, D.J. Williams, Dalton Trans., 2004, 570.
• [98] M.H. Chisholm, K. Phomphrai, Inorg. Chim. Acta, 2003, 350, 121.
• [99] L.R. Rieth, D.R. Moore, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc., 2002, 124, 15239.
• [100] F. Drouin, P.O. Oguadinma, T.J.J. Whitehome, R.E. Prud’homme, F. Schaper, Organometallics, 2010, 29, 2139.
• [101] B.M. Chamberlain, M. Cheng, D.R. Moore, T.M. Ovitt, E.B. Lobkovsky, G.W. Coates, J. Am. Chem. Soc., 2001, 123, 3229.
• [102] M.H. Chisholm, J. Gallucci, K. Phomphrai, Inorg. Chem., 2002, 41, 2785.
• [103] B.J. O’Keefe, M.A. Hillmyer, W.B. Tolman, J. Chem. Soc., Dalton Trans., 2001, 2215.
• [104] H.-Y. Chen, Y.-L. Peng, T.-H. Huang, A.K. Sutar, S.A. Miller, C.-C. Lin, J. Mol. Catal. A: Chem., 2011, 339, 61.
• [105] H.-Y. Chen, B.-H. Huang, C.-C. Lin, Macromolecules, 2005, 38, 5400.
• [106] M.S. Hill, P.B. Hitchcock, Dalton Trans., 2002, 4694.
• [107] T.K. Panda, P.W. Roesky, Chem. Soc. Rev., 2009, 38, 2782.
• [108] N.M. Rezayee, K.A. Gerling, A.L. Rheingold, J. M. Fritsch, Dalton Trans., 2013, 42, 5573.
• [109] X. Lei, D.P. Spence, Patent US0008345 A1, 2013.
• [110] X.-F. Yu, C. Zhang, Z.-X. Wang, Organometallics, 2013, 32, 3262.
• [111] E. Grunova, T. Roisnel, J.-F. Carpentier, Dalton Trans., 2009, 9010.
• [112] C.K. Williams, L.E. Breyfogle, S.K. Choi, W. Nam, V.G. Young, Jr., M.A. Hillmyer, W.B. Tolman, J. Am. Chem. Soc., 2003, 125, 11350.
• [113] C.K. Williams, N.R. Brooks, M.A. Hillmyer, W.B. Tolman, Chem. Commun., 2002, 2132.
• [114] L.E. Breyfogle, C.K. Williams, V.G. Young, M.A. Hillmyer, W.B., Tolman, Dalton Trans., 2006, 928.
• [115] V. Poirier, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Dalton Trans., 2009, 9820.
• [116] J. Ejfler, S. Szafert, K. Mierzwicki, L. B. Jerzykiewicz, Piotr Sobota, Dalton Trans., 2008, 6556.
• [117] D. Jędrzkiewicz, J. Ejfler, N. Gulia, Ł. John, S. Szafert, Dalton Trans., 2015, 44, 13700.
• [118] M.H. Chisholm, J.C. Gallucci, H.S. Zhen, Inorg. Chem., 2001, 40, 5051.
• [119] H.-Y. Chen, H.-Y. Tang, C.-C. Lin, Macromolecules, 2006, 39, 3745.
• [120] W.-C. Hung, Y. Huang, C.-C. Lin, J. Polym. Sci. Part A: Polym. Chem., 2008, 46, 6466.
• [121] L. Yao, L. Wang, J. Zhang, N. Tang, J. Wu, J. Mol. Catal. A: Chem., 2012, 352, 57.
• [122] D. J. Darensbourg, O. Karroonnirun, Inorg. Chem., 2010, 49, 2360.
• [123] J.-C. Wu, B.-H. Huang, M.-L. Hsueh, S.-L. Lai, C.-C. Lin, Polymer, 2005, 46, 9784.
• [124] M.H. Chisholm, C.-C. Lin, J.C. Gallucci, B.T. Ko, Dalton Trans., 2003, 406.
• [125] E. Bukhaltsev, L. Frish, Y. Cohen, A. Vigalok, Org. Lett., 2005, 7, 5123.
• [126] B.-H. Huang, C.-N. Lin, M.-L. Hsueh, T. Athar, C.-C. Lin, Polymer, 2006, 47, 6622.
• [127] Y. Huang, W. Wang, C.-C. Lin, M. P. Blake, L.Clark, A. D. Schwarz, P. Mountford, Dalton Trans., 2013, 42, 9313.
• [128] T.K. Sen, A. Mukherjee, A. Modak, S.K. Mandal, D. Koley, Dalton Trans., 2013, 42, 1893.
• [129] K.V. Raman, A.M. Kamerbeek, A. Mukherjee, N. Atodiresei, T.K. Sen, P. Łazić, V. Caciuc, R. Michel, D. Stalke, S.K. Mandal, S. Blügel, M. Münzenberg, J. S. Moodera, Nature 2013, 493, 509.
• [130] E.F. Connor, G. W. Nyce, M. Myers, A. Mock, J.L. Hedrick, J. Am. Chem. Soc., 2002, 124, 914-915.
• [131] W. Jeong, J.L. Hedrick, R.M. Waymouth, J. Am. Chem. Soc., 2007, 129, 8414.
• [132] D.A. Culkin, W. Jeong, S.Csihony, E.D. Gomez, N.P. Balsara, J.L. Hedrick, R.M. Waymouth, Angew. Chem. Int. Ed., 2007, 46, 2627.
• [133] T.R. Jensen, L. Breyfogle, M. Hillmyer, W.B. Tolman, Chem. Commun., 2004, 2504.
• [134] T.R. Jensen, C.P. Schaller, M.A. Hillmyer, W.B. Tolman, J. Organomet. Chem., 2005, 690, 5881.
• [135] P.L. Arnold, I.J. Casely, Z.R. Turner, R. Bellabarba, R.B. Tooze, Dalton Trans., 2009, 7236.
• [136] Z. Liu, W. Gao, J. Zhang, D. Cui, Q. Wu, Y. Mu, Organometallics, 2010, 29, 5783.

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).