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Polymer Bulletin
Erschienen in: Polymer Bulletin 11/2018

27.03.2018 | Original Paper

Kinetics, mechanisms and polymer property studies of ring-opening polymerization of ɛ-caprolactone and lactides initiated by (benzimidazolylmethyl)amino Zn(II) alkoxides

verfasst von: Ekemini D. Akpan, Bernard Omondi, Stephen O. Ojwach

Erschienen in: Polymer Bulletin | Ausgabe 11/2018

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Abstract

The reactions of substituted (benzimidazolylmethyl)amines ligands (L1–L3) with ZnEt2 in the presence of either BnOH or t-BuOH afforded the corresponding Zn(II) metal alkoxides [Zn(L1)(OBn)]2 (1), [(Zn(L2)(OBn)]2 (2), [Zn(L3)(OBn)]2 (3), [Zn(L2)(t-BuO)]2 (4), respectively. Complexes 1–4 formed effective initiators in the ring-opening polymerization (ROP) reactions of ɛ-caprolactone (ɛ-CL), D,L-lactide (D,L-LA) and L-lactide (L-LA). The ROP reactions followed pseudo-first-order kinetics with respect to monomer. Moderate molecular weight polymers of 10,650 g mol−1 exhibiting relatively narrow molecular weight distributions (1.16–1.54) were obtained. Predominantly crystalline isotactic poly(L-LA) and heterotactic poly(D,L-LA) were produced, respectively. Thermal analyses of PLA also supported the formation of isotactic poly(L-LA) with decomposition temperature of 298 °C.
Vorheriger Artikel Highly stable double crosslinked membrane based on poly(vinylbenzyl chloride) for anion exchange membrane fuel cell
Nächster Artikel Preparation, characterization, and bioactivity of the polyester and tea waste green composites

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Literatur
1.
Albertsson A-C, Varma IK (2003) Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromol 4:1466–1486CrossRef
2.
Amass W, Amass A, Tighe B (1998) A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies. Polym Int 47:89–144CrossRef
3.
Kasirajan S, Ngouajio M (2012) Polyethylene and biodegradable mulches for agricultural applications: a review. Agron Sustain Dev 32:501–529CrossRef
4.
Yuan Y, Jing X, Xiao H, Chen X, Huang Y (2011) Zinc-based catalyst for the ring-opening polymerization of cyclic esters. J Appl Polym Sci 121:2378–2385CrossRef
5.
Tsai C-Y, Du H-C, Chang J-C, Huang B-H, Ko B-T, Lin C-C (2014) Ring-opening polymerization of cyclic esters initiated by zirconium, titanium and yttrium complexes. RSC Adv 4:14527–14537CrossRef
6.
Huang Y, Hung W-C, Liao M-Y, Tsai T-E, Peng Y-L, Lin C-C (2009) Ring-opening polymerization of lactides initiated by magnesium and zinc complexes based on NNO-tridentate ketiminate ligands: activity and stereoselectivity studies. J Polym Sci Part A Polym Chem 47:2318–2329CrossRef
7.
Inoue S (2000) Immortal polymerization: the outset, development, and application. J Polym Sci Part A Polym Chem 38:2861–2871CrossRef
8.
Song S, Zhang X, Ma H, Yang Y (2012) Zinc complexes supported by claw-type aminophenolate ligands: synthesis, characterization and catalysis in the ring-opening polymerization of rac-lactide. Dalton Trans 41:3266–3277CrossRefPubMed
9.
Gowda RR, Chakraborty D (2010) Zinc acetate as a catalyst for the bulk ring opening polymerization of cyclic esters and lactide. J Mol Catal A Chem 333:167–172CrossRef
10.
Liu Z, Gao W, Zhang J, Cui D, Wu Q, Mu Y (2010) Bis(imino)aryl NCN pincer aluminum and zinc complexes: synthesis, characterization, and catalysis on l-Lactide polymerization. Organometallics 29:5783–5790CrossRef
11.
Ikpo N, Saunders LN, Walsh JL, Smith JMB, Dawe LN, Kerton FM (2011) Zinc complexes of piperazinyl-derived aminephenolate ligands: synthesis, characterization and ring-opening polymerization activity. Eur J Inorg Chem 2011:5347–5359CrossRef
12.
Wu J, Yu T-L, Chen C-T, Lin C-C (2006) Recent developments in main group metal complexes catalyzed/initiated polymerization of lactides and related cyclic esters. Coord Chem Rev 250:602–626CrossRef
13.
Sutar AK, Maharana T, Dutta S, Chen C-T, Lin C-C (2010) Ring-opening polymerization by lithium catalysts: an overview. Chem Soc Rev 39:1724–1746CrossRefPubMed
14.
Fliedel C, Rosa V, Alves FM, Martins AM, Aviles T, Dagorne S (2015) P, O-Phosphinophenolate zinc(ii) species: synthesis, structure and use in the ring-opening polymerization (ROP) of lactide, caprolactone and trimethylene carbonate. Dalton Trans 44:12376–12387CrossRefPubMed
15.
Fliedel C, Mameri S, Dagorne S, Avilés T (2014) Controlled ring-opening polymerization of trimethylene carbonate and access to PTMC-PLA block copolymers mediated by well-defined N-heterocyclic carbene zinc alkoxides. Appl Organomet Chem 28:504–511CrossRef
16.
Fliedel C, Vila-Viçosa D, Calhorda MJ, Dagorne S, Avilés T (2014) Dinuclear zinc–N-heterocyclic carbene complexes for either the controlled ring-opening polymerization of lactide or the controlled degradation of polylactide under mild conditions. ChemCatChem 6:1357–1367CrossRef
17.
Inoue S, Koinuma H, Tsuruta T (1969) Copolymerization of carbon dioxide and epoxide. J Polym Sci Part B Polym Lett 7:287–292CrossRef
18.
Romain C, Rosa V, Fliedel C, Bier F, Hild F, Welter R, Dagorne S, Aviles T (2012) Highly active zinc alkyl cations for the controlled and immortal ring-opening polymerization of ε-caprolactone. Dalton Trans 41:3377–3379CrossRefPubMed
19.
Platel RH, Hodgson LM, Williams CK (2008) Biocompatible initiators for lactide polymerization. Polym Rev 48:11–63CrossRef
20.
Stanford MJ, Dove AP (2010) Stereocontrolled ring-opening polymerisation of lactide. Chem Soc Rev 39:486–494CrossRefPubMed
21.
Thomas CM (2010) Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures. Chem Soc Rev 39:165–173CrossRefPubMed
22.
23.
Attandoh NW, Ojwach SO, Munro OQ (2014) (Benzimidazolylmethyl)amine Zn-II and Cu-II carboxylate complexes: structural, mechanistic and kinetic studies of polymerisation reactions of epsilon-caprolactone. Eur J Inorg Chem 3053–3064
24.
Hao P, Zhang S, Sun W-H, Shi Q, Adewuyi S, Lu X, Li P (2007) Synthesis, characterization and ethylene oligomerization studies of nickel complexes bearing 2-benzimidazolylpyridine derivatives. Organometallics 26:2439–2446CrossRef
25.
Achar KCS, Hosamani KM, Seetharamareddy HR (2010) In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. Eur J Med Chem 45:2048–2054CrossRefPubMed
26.
Campos-Vallette MM, Figueroa KA, Latorre R, Manriquez V, Diaz G, Costamagna J, Otero M (1992) Vib Spectrosc 4
27.
Save M, Schappacher M, Soum A (2002) Controlled ring-opening polymerization of lactones and lactides initiated by lanthanum isopropoxide, 1. General aspects and kinetics. Macromol Chem Phys 203:889–899CrossRef
28.
Wu J-C, Huang B-H, Hsueh M-L, Lai S-L, Lin C-C (2005) Ring-opening polymerization of lactide initiated by magnesium and zinc alkoxides. Polymer 46:9784–9792CrossRef
29.
Wang C-H, Li C-Y, Huang B-H, Lin C-C, Ko B-T (2013) Synthesis and structural determination of zinc complexes based on an anilido-aldimine ligand containing an O-donor pendant arm: zinc alkoxide derivative as an efficient initiator for ring-opening polymerization of cyclic esters. Dalton Trans 42:10875–10884CrossRefPubMed
30.
O’Keefe BJ, Breyfogle LE, Hillmyer MA, Tolman WB (2002) Mechanistic comparison of cyclic ester polymerizations by novel Iron(III)—alkoxide complexes: single vs multiple site catalysis. J Am Chem Soc 124:4384–4393CrossRefPubMed
31.
Hodgson LM, Platel RH, White AJP, Williams CK (2008) A series of bis(thiophosphinic amido)yttrium initiators for lactide ring-opening polymerization. Macromolecules 41:8603–8607CrossRef
32.
Bhunora S, Mugo J, Bhaw-Luximon A, Mapolie S, Van Wyk J, Darkwa J, Nordlander E (2011) The use of Cu and Zn salicylaldimine complexes as catalyst precursors in ring opening polymerization of lactides: ligand effects on polymer characteristics. Appl Organomet Chem 25:133–145CrossRef
33.
Duda A, Kowalski A (2009) Thermodynamics and kinetics of ring-opening polymerization. Handbook of ring-opening polymerization. Wiley, Amsterdam, pp 1–51
34.
Akpan ED, Ojwach SO, Omondi B, Nyamori VO (2016) Structural and kinetic studies of the ring-opening polymerization of cyclic esters using N,N′diarylformamidines Zn(II) complexes. Polyhedron 110:63–72CrossRef
35.
Buffet J-C, Davin JP, Spaniol TP, Okuda J (2011) Alkaline earth metal amide complexes containing a cyclen-derived (NNNN) macrocyclic ligand: synthesis, structure, and ring-opening polymerization activity towards lactide monomers. New J Chem 35:2253–2257CrossRef
36.
Chisholm MH, Gallucci JC, Krempner C (2007) Ring-opening polymerization of l-lactide by organotin(IV)alkoxides, R2Sn(OPri)2: estimation of the activation parameters. Polyhedron 26:4436–4444CrossRef
37.
Hild F, Haquette P, Brelot L, Dagorne S (2010) Synthesis and structural characterization of well-defined anionic aluminium alkoxide complexes supported by NON-type diamido ether tridentate ligands and their use for the controlled ROP of lactide. Dalton Trans 39:533–540CrossRef
38.
Sung C-Y, Li C-Y, Su J-K, Chen T-Y, Lin C-H, Ko B-T (2012) Zinc and magnesium complexes incorporated by bis(amine) benzotriazole phenoxide ligand: synthesis, characterization, photoluminescent properties and catalysis for ring-opening polymerization of lactide. Dalton Trans 41:953–961CrossRefPubMed
39.
40.
Chen H-Y, Huang B-H, Lin C-C (2005) A Highly efficient initiator for the ring-opening polymerization of lactides and ε-caprolactone: a kinetic study. Macromolecules 38:5400–5405CrossRef
41.
Attandoh NW, Ojwach SO, Munro OQ (2014) (Benzimidazolylmethyl)amine ZnII and CuII carboxylate complexes: structural, mechanistic and kinetic studies of polymerisation reactions of ε-caprolactone. Eur J Inorg Chem pp 3053–3064
42.
Appavoo D, Omondi B, Guzei IA, van Wyk JL, Zinyemba O, Darkwa J (2014) Bis(3,5-dimethylpyrazole) copper(II) and zinc(II) complexes as efficient initiators for the ring opening polymerization of epsilon-caprolactone and D,L-lactide. Polyhedron 69:55–60CrossRef
43.
Ouhadi T, Hamitou A, Jerome R, Teyssie P (1976) Soluble bimetallic μ-Oxo-alkoxides. 8. Structure and kinetic behavior of the catalytic species in unsubstituted lactone ring-opening polymerization. Macromolecules 9:927–931CrossRef
44.
Duda A (1996) Polymerization of ε-caprolactone initiated by aluminum isopropoxide carried out in the presence of alcohols and diols. Kinetics and mechanism. Macromolecules 29:1399–1406CrossRef
45.
Kong W-L, Chai Z-Y, Wang Z-X (2014) Synthesis of N,N,O-chelate zinc and aluminum complexes and their catalysis in the ring-opening polymerization of epsilon-caprolactone and rac-lactide. Dalton Trans 43:14470–14480CrossRefPubMed
46.
Kong W-L, Wang Z-X (2014) Dinuclear magnesium, zinc and aluminum complexes supported by bis(iminopyrrolide) ligands: synthesis, structures, and catalysis toward the ring-opening polymerization of [varepsilon]-caprolactone and rac-lactide. Dalton Trans 43:9126–9135CrossRefPubMed
47.
Collins S (2011) Polymerization catalysis with transition metal amidinate and related complexes. Coord Chem Rev 255:118–138CrossRef
48.
Kamber NE, Jeong W, Waymouth RM, Pratt RC, Lohmeijer BGG, Hedrick JL (2007) Organocatalytic ring-opening polymerization. Chem Rev 107:5813–5840CrossRefPubMed
49.
Wang J, Yao Y, Zhang Y, Shen Q (2009) Bridged bis(amidinate) ytterbium alkoxide and phenoxide: syntheses, structures, and their high activity for controlled polymerization of l-lactide and ε-caprolactone. Inorg Chem 48:744–751CrossRefPubMed
50.
Dubois P, Dubois P, Coulembier O, Raquez JM (2009) Handbook of ring-opening polymerization. Wiley, AmsterdamCrossRef
51.
Dubois P, Jacobs C, Jerome R, Teyssie P (1991) Macromolecular engineering of polylactones and polylactides. 4. Mechanism and kinetics of lactide homopolymerization by aluminum isopropoxide. Macromolecules 24:2266–2270CrossRef
52.
Chamberlain BM, Cheng M, Moore DR, Ovitt TM, Lobkovsky EB, Coates GW (2001) Polymerization of lactide with zinc and magnesium β-diiminate complexes: stereocontrol and mechanism. J Am Chem Soc 123:3229–3238CrossRefPubMed
53.
Thakur KAM, Kean RT, Hall ES, Kolstad JJ, Lindgren TA, Doscotch MA, Siepmann JI, Munson EJ (1997) High-resolution 13C and 1H solution NMR study of poly(lactide). Macromolecules 30:2422–2428CrossRef
54.
Kim Y, Jnaneshwara GK, Verkade JG (2003) Titanium Alkoxides as initiators for the controlled polymerization of lactide. Inorg Chem 42:1437–1447CrossRefPubMed
55.
Dove AP, Gibson VC, Marshall EL, White AJP, Williams DJ (2001) A well defined tin(ii) initiator for the living polymerisation of lactide. Chem Commun pp 283–284
56.
Cheng M, Attygalle AB, Lobkovsky EB, Coates GW (1999) Single-site catalysts for ring-opening polymerization: synthesis of heterotactic poly(lactic acid) from rac-lactide. J Am Chem Soc 121:11583–11584CrossRef
57.
Zhang Y, Gao A, Zhang Y, Xu Z, Yao W (2016) Aluminum complexes with benzoxazolphenolate ligands: synthesis, characterization and catalytic properties for ring-opening polymerization of cyclic esters. Polyhedron 112:27–33CrossRef
58.
Kremer AB, Osten KM, Yu I, Ebrahimi T, Aluthge DC, Mehrkhodavandi P (2016) Dinucleating ligand platforms supporting indium and zinc catalysts for cyclic ester polymerization. Inorg Chem 55:5365–5374CrossRefPubMed
59.
Petrus R, Sobota P (2012) Zinc complexes supported by maltolato ligands: synthesis, structure, solution behavior, and application in ring-opening polymerization of lactides. Organometallics 31:4755–4762CrossRef
60.
Jamshidi K, Hyon S-H, Ikada Y (1988) Thermal characterization of polylactides. Polymer 29:2229–2234CrossRef
61.
Labet M, Thielemans W (2009) Synthesis of polycaprolactone: a review. Chem Soc Rev 38:3484–3504CrossRefPubMed
Metadaten
Titel
Kinetics, mechanisms and polymer property studies of ring-opening polymerization of ɛ-caprolactone and lactides initiated by (benzimidazolylmethyl)amino Zn(II) alkoxides
verfasst von
Ekemini D. Akpan
Bernard Omondi
Stephen O. Ojwach
Publikationsdatum
27.03.2018
Verlag
Springer Berlin Heidelberg
Erschienen in
Polymer Bulletin / Ausgabe 11/2018
Print ISSN: 0170-0839
Elektronische ISSN: 1436-2449
DOI
https://doi.org/10.1007/s00289-018-2321-2

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