Polymers from macrolactones: From pheromones to functional materials
Tài liệu tham khảo
Albertsson, 2003, Recent developments in ring opening polymerization of lactones for biomedical applications, Biomacromolecules, 4, 1466, 10.1021/bm034247a
Place, 2009, Synthetic polymer scaffolds for tissue engineering, Chem Soc Rev, 38, 1139, 10.1039/b811392k
Uhrich, 1999, Polymeric systems for controlled drug release, Chem Rev, 99, 3181, 10.1021/cr940351u
Yevstropov, 1983, Thermodynamics of pentadecalactone, of the process of its polymerization and of formed polypentadecalactone in the 0-k-400-k region, Vysokomol Soedin Ser A, 25, 1679
Lebedev, 1984, Thermodynamic properties of polylactones, Makromol Chem-Macromol Chem Phys, 185, 1235, 10.1002/macp.1984.021850617
Nomura, 1994, Anionic ring-opening polymerization of macrocyclic esters, Macromolecules, 27, 620, 10.1021/ma00080a046
Jedlinski, 1996, Anionic polymerization of pentadecanolide. A new route to a potentially biodegradable aliphatic polyester, Macromol Chem Phys, 197, 2923, 10.1002/macp.1996.021970925
Williams, 1999, The synthesis of macrocyclic musks, Synthesis, 1707, 10.1055/s-1999-3581
Kraft, 2000, Odds and trends: recent developments in the chemistry of odorants, Angew Chem Int Ed, 39, 2980, 10.1002/1521-3773(20000901)39:17<2980::AID-ANIE2980>3.0.CO;2-#
Witt, 2013, Large-ring lactones from plant oils, Green Chem, 15, 2361, 10.1039/c3gc40905h
Kerschbaum, 1927, Large lactone rings - the carriers of the musky vegetable aroma, Ber Dtsch Chem Ges, 60, 902, 10.1002/cber.19270600411
Parenty, 2013, Update 1 of: macrolactonizations in the total synthesis of natural products, Chem Rev, 113, 10.1021/cr300129n
McGinty, 2011, Fragrance material review on α-pentadecalactone, Food Chem Toxicol, 49, S193, 10.1016/j.fct.2011.07.026
Grammer, 1993, 5-α-androst-16en-3α-on: a male pheromone? A brief report, Ethol Sociobiol, 14, 201, 10.1016/0162-3095(93)90006-4
Amoore, 1977, Specific anosmias To 5-α-androst-16-En-3-one and ω-pentadecalactone - urinous and musky primary odors, Chem Sens Flav, 2, 401, 10.1093/chemse/2.4.401
Skoglund, 1998, Thermophysical properties of polypentadecanolactone, Polymer, 39, 1899, 10.1016/S0032-3861(97)00473-4
Skoglund, 1998, Crystallization kinetics of polytridecanolactone and polypentadecanolactone, Polymer, 39, 3143, 10.1016/S0032-3861(97)10023-4
Focarete, 2001, Physical characterization of poly(omega-pentadecalactone) synthesized by lipase-catalyzed ring-opening polymerization, J Polym Sci Part B Polym Phys, 39, 1721, 10.1002/polb.1145
Cai, 2010, Effects of molecular weight on poly(ω-pentadecalactone) mechanical and thermal properties, Polymer, 51, 1088, 10.1016/j.polymer.2010.01.007
Flory, 1946, Fundamental principles of condensation polymerization, Chem Rev, 39, 137, 10.1021/cr60122a003
Quinzler, 2010, Linear semicrystalline polyesters from fatty acids by complete feedstock molecule utilization, Angew Chem Int Ed, 49, 4306, 10.1002/anie.201001510
Liu, 2011, Polymers from fatty acids: poly(ω-hydroxyl tetradecanoic acid) synthesis and physico-mechanical studies, Biomacromolecules, 12, 3291, 10.1021/bm2007554
Stempfle, 2011, Long-chain linear C-19 and C-23 monomers and polycondensates from unsaturated fatty acid esters, Macromolecules, 44, 4159, 10.1021/ma200627e
Vilela, 2012, Meier MAR. Plant oil-based long-chain C-26 monomers and their polymers, Macromol Chem Phys, 213, 2220, 10.1002/macp.201200332
Mutlu, 2013, Self-metathesis of fatty acid methyl esters: full conversion by choosing the appropriate plant oil, RSC Adv, 3, 4927, 10.1039/c3ra40330k
Rybak, 2008, Acyclic diene metathesis with a monomer from renewable resources: control of molecular weight and one-step preparation of block copolymers, ChemSusChem, 1, 542, 10.1002/cssc.200800047
Fokou, 2010, Studying and suppressing olefin isomerization side reactions during ADMET polymerizations, Macromol Rapid Commun, 31, 368, 10.1002/marc.200900678
Trzaskowski, 2011, Aliphatic long-chain C-20 polyesters from olefin metathesis, Macromol Rapid Commun, 32, 1352, 10.1002/marc.201100319
Turunc, 2011, Renewable polyethylene mimics derived from Castor oil, Macromol Rapid Commun, 32, 1357, 10.1002/marc.201100280
Kreye, 2011, Introducing multicomponent reactions to polymer science: Passerini reactions of renewable monomers, J Am Chem Soc, 133, 1790, 10.1021/ja1113003
de Espinosa, 2011, Plant oils: the perfect renewable resource for polymer science?, Eur Polym J, 47, 837, 10.1016/j.eurpolymj.2010.11.020
Akintayo, 2012, Acyclic triene metathesis polymerization of Plukenetia conophora oil: branched polymers by direct polymerization of renewable resources, Macromol Chem Phys, 213, 87, 10.1002/macp.201100539
Pepels, 2013, From polyethylene to polyester: influence of ester groups on the physical properties, Macromolecules, 46, 7668, 10.1021/ma401403x
Turunc, 2011, Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers, Green Chem, 13, 314, 10.1039/c0gc00773k
Dubois, 2009
Dove, 2008, Controlled ring-opening polymerization of cyclic esters: polymer blocks in self-assembled nanostructures, Chem Commun, 122, 6446, 10.1039/b813059k
Pepels, 2014, Theoretical and experimental approach to accurately predict the complex molecular weight distribution in the polymerization of strainless cyclic esters, Macromolecules, 47, 5542, 10.1021/ma5015353
Kobayashi, 2001, Enzymatic polymerization, Chem Rev, 101, 3793, 10.1021/cr990121l
Champagne, 2016, Recent developments and optimization of lipase-catalyzed lactone formation and ring-opening polymerization, Macromol Rapid Commun, 37, 1986, 10.1002/marc.201600494
Uyama, 1993, Enzymatic ring-opening polymerization of lactones catalyzed by lipase, Chem Lett, 1149, 10.1246/cl.1993.1149
Knani, 1993, Enzymatic polyesterification in organic media. Enzyme-catalyzed synthesis of linear polyesters. I. Condensation polymerization of linear hydroxyesters. II. Ring-opening polymerization of ε-caprolactone, J Polym Sci Part A Polym Chem, 31, 1221, 10.1002/pola.1993.080310518
MacDonald, 1995, Enzyme-catalyzed ε-Caprolactone ring-opening polymerization, Macromolecules, 28, 73, 10.1021/ma00105a008
Uyama, 1993, Synthesis of polyesters by enzymatic ring-opening copolymerization using lipase catalyst, P Jpn Acad B Phys, 69, 203, 10.2183/pjab.69.203
Uyama, 1995, Lipase-catalyzed ring-opening polymerization of 12-Dodecanolide, Macromolecules, 28, 7046, 10.1021/ma00125a002
Uyama, 1995, Enzymatic ring-opening polymerization of lactones to polyesters by lipase catalyst - unusually high reactivity of Macrolides, Bull Chem Soc Jpn, 68, 56, 10.1246/bcsj.68.56
Uyama, 1996, Lipase-catalyzed ring-opening polymerization and copolymerization of 15-pentadecanolide, Acta Polym, 47, 357, 10.1002/actp.1996.010470807
Noda, 1997, Enzymatic polymerization catalyzed by surfactant-coated lipases in organic media, Biotechnol Lett, 19, 307, 10.1023/A:1018334430266
Uyama, 2002, High-performance immobilized lipase catalyst for polyester synthesis, Polym J, 34, 970, 10.1295/polymj.34.970
Bisht, 1997, Enzyme-catalyzed ring-opening polymerization of ω-Pentadecalactone, Macromolecules, 30, 2705, 10.1021/ma961869y
Kundys, 2018, Candida antarctica Lipase B as Catalyst for Cyclic Esters Synthesis, Their Polymerization and Degradation of Aliphatic Polyesters, J Polym Environ, 26, 396, 10.1007/s10924-017-0945-1
Polloni, 2018, Polyesters from macrolactones using commercial lipase NS 88011 and novozym 435 as biocatalysts, Appl Biochem Biotechnol, 184, 659, 10.1007/s12010-017-2583-4
Hunsen, 2007, A cutinase with polyester synthesis activity, Macromolecules, 40, 148, 10.1021/ma062095g
Hunsen, 2008, Humicola insolens cutinase-catalyzed lactone ring-opening Polymerizations: kinetic and mechanistic studies, Biomacromolecules, 9, 518, 10.1021/bm701269p
Herrera-Kao, 2015, Effect of reaction temperature on the physicochemical properties of poly(pentadecanolide) obtained by enzyme-catalyzed ring-opening polymerization, Polym Bull, 72, 441, 10.1007/s00289-014-1288-x
Matsumoto, 1999, Kinetics of ring-opening polymerization of lactones by lipase, Biochem Eng J, 4, 73, 10.1016/S1369-703X(99)00017-0
Hedfors, 2010, Lipase chemoselectivity towards alcohol and thiol acyl acceptors in a transacylation reaction, J Mol Catal, B Enzym, 66, 120, 10.1016/j.molcatb.2010.04.005
Nakane, 2008, Blends of poly(L-lactic acid) with poly(ω-pentadecalactone) synthesized by enzyme-catalyzed polymerization, J Appl Polym Sci, 108, 2139, 10.1002/app.27838
Kumar, 2000, Efficient ring-opening polymerization and copolymerization of ε-caprolactone and ω-pentadecalactone catalyzed by Candida antartica lipase B, Macromolecules, 33, 6303, 10.1021/ma000344+
Varma, 2005, Enzyme catalyzed synthesis of polyesters, Prog Polym Sci, 30, 949, 10.1016/j.progpolymsci.2005.06.010
Mei, 2003, Kinetics and mechanism of Candida antarctica lipase B catalyzed solution polymerization of ε-Caprolactone, Macromolecules, 36, 5530, 10.1021/ma025741u
Albertsson, 2008, Recent developments in enzyme-catalyzed ring-opening polymerization, Adv Drug Deliv Rev, 60, 1077, 10.1016/j.addr.2008.02.007
Kobayashi, 2010, Lipase-catalyzed polyester synthesis – a green polymer chemistry, P Jpn Acad B Phys, 86, 338, 10.2183/pjab.86.338
Kobayashi, 1998, In vitro biosynthesis of polyesters with isolated enzymes in aqueous systems and organic solvents, Polym Degrad Stabil, 59, 195, 10.1016/S0141-3910(97)00178-X
Namekawa, 1998, Lipase-catalyzed ring-opening polymerization of 16-hexadecanolide, P Jpn Acad B Phys, 74, 65, 10.2183/pjab.74.65
Namekawa, 1999, Lipase-catalyzed ring-opening polymerization of lactones to polyesters and its mechanistic aspects, Int J Biol Macromol, 25, 145, 10.1016/S0141-8130(99)00028-8
Duda, 2002, Kinetics of the ring-opening polymerization of 6-, 7-, 9-, 12-, 13-, 16-, and 17-membered lactones. Comparison of chemical and enzymatic polymerizations, Macromolecules, 35, 4266, 10.1021/ma012207y
van der Mee, 2006, Investigation of lipase-catalyzed ring-opening polymerizations of Lactones with various ring sizes: kinetic evaluation, Macromolecules, 39, 5021, 10.1021/ma060668j
Witt, 2017, No strain, no gain? Enzymatic ring‐opening polymerization of strainless aliphatic macrolactones, Macromol Rapid Commun, 38, 10.1002/marc.201600638
Kikuchi, 2002, Lipase-catalyzed ring-opening polymerization of substituted lactones, Polym J, 34, 835, 10.1295/polymj.34.835
Taden, 2003, Enzymatic polymerization towards biodegradable polyester nanoparticles, Macromol Rapid Commun, 24, 512, 10.1002/marc.200390079
Målberg, 2010, The environmental influence in enzymatic polymerization of aliphatic polyesters in bulk and aqueous mini-emulsion, Polymer, 51, 5318, 10.1016/j.polymer.2010.09.016
Panlawan, 2013, Lipase-catalyzed interfacial polymerization of ω-pentadecalactone in aqueous biphasic medium: a mechanistic study, J Mol Catal, B Enzym, 88, 69, 10.1016/j.molcatb.2012.11.008
Chiaradia, 2018, Polyester nanoparticles from macrolactones via miniemulsion enzymatic ring-opening polymerization, Colloid Polym Sci, 296, 861, 10.1007/s00396-018-4306-y
Spinella, 2015, Enzymatic reactive extrusion: moving towards continuous enzyme-catalysed polyester polymerization and processing, Green Chem, 17, 4146, 10.1039/C5GC00992H
Wosnick, 2010, Enzymatic ring-opening polymerization in a continuous-flow system, Abstr Pap Am Chem Soc, 240
Polloni, 2017, Enzymatic ring opening polymerization of ω-Pentadecalactone in different solvents in a variable-volume view reactor, J Polym SciPart A Polym Chem, 55, 1219, 10.1002/pola.28486
Rebelatto, 2018, High-pressure phase equilibrium data for systems containing carbon dioxide, ω-pentadecalactone, chloroform and water, J Chem Thermodyn, 122, 125, 10.1016/j.jct.2018.03.008
Polloni, 2017, Enzymatic ring opening polymerization of ω-pentadecalactone using supercritical carbon dioxide, J Supercrit Fluids, 119, 221, 10.1016/j.supflu.2016.09.019
Guindani, 2017, Enzymatic ring opening copolymerization of globalide and ε-caprolactone under supercritical conditions, J Supercrit Fluids, 128, 404, 10.1016/j.supflu.2017.06.008
Gualandi, 2010, Scaffold for tissue engineering fabricated by non-isothermal supercritical carbon dioxide foaming of a highly crystalline polyester, Acta Biomater, 6, 130, 10.1016/j.actbio.2009.07.020
Hunley, 2013, Microstructure analysis and model discrimination of enzyme-catalyzed copolyesters, ACS Macro Lett, 2, 375, 10.1021/mz300659h
Kumar, 2000, Candida antarctica lipase B-Catalyzed transesterification: new synthetic routes to copolyesters, J Am Chem Soc, 122, 11767, 10.1021/ja002915j
Zhong, 2000, Controlled ring-opening polymerization of ω-pentadecalactone with yttrium isopropoxide as an initiator, Macromol Chem Phys, 201, 1329, 10.1002/1521-3935(20000801)201:12<1329::AID-MACP1329>3.0.CO;2-8
Slivniak, 2005, Macrolactones and polyesters from ricinoleic acid, Biomacromolecules, 6, 1679, 10.1021/bm049194r
Wang, 2005, Ring-opening polymerization of cyclic monomers with aluminum triflate, Macromol Symp, 224, 193, 10.1002/masy.200550617
Nakayama, 2011, High activity of rare earth tetrahydroborates for ring-opening polymerization of ω-pentadecalactone, J Appl Polym Sci, 121, 2098, 10.1002/app.33834
Kumar, 2001, Copolymerizations of ω-Pentadecalactone and trimethylene carbonate by chemical and lipase catalysis, Macromolecules, 34, 3527, 10.1021/ma0100246
Wilson, 2014, ’Immortal’ ring-opening polymerization of ω-pentadecalactone by Mg (BHT)2(THF)2, Polym Chem, 5, 2691, 10.1039/C4PY00034J
Wilson, 2015, Synthesis of ω-Pentadecalactone copolymers with independently tunable thermal and degradation behavior, Macromolecules, 48, 950, 10.1021/ma5022049
Wilson, 2015, Synthesis and postpolymerization modification of one-pot ω-Pentadecalactone block-like copolymers, Biomacromolecules, 16, 3191, 10.1021/acs.biomac.5b00862
Wilson, 2016, Dependence of copolymer sequencing based on lactone ring size and ε-Substitution, ACS Macro Lett, 5, 346, 10.1021/acsmacrolett.5b00940
Nifant’ev, 2016, Monomeric and dimeric magnesium mono-BHT complexes as effective ROP catalysts, Catal Commun, 87, 106, 10.1016/j.catcom.2016.09.018
Bouyahyi, 2014, Metal-based catalysts for controlled ring-opening polymerization of macrolactones: high molecular weight and well-defined copolymer architectures, Macromolecules, 47, 517, 10.1021/ma402072t
Jasinska-Walc, 2015, Synthetic principles determining local organization of copolyesters prepared from Lactones and macrolactones, Macromolecules, 48, 502, 10.1021/ma502262e
van der Meulen, 2011, Catalytic ring-opening polymerization of renewable macrolactones to high molecular weight polyethylene-like polymers, Macromolecules, 44, 4301, 10.1021/ma200685u
Pepels, 2013, Kinetic investigation on the catalytic ring-opening (Co)Polymerization of (Macro)lactones using aluminum salen catalysts, Macromolecules, 46, 4324, 10.1021/ma400731c
Pepels, 2015, Mimicking (Linear) low-density polyethylenes using modified polymacrolactones, Macromolecules, 48, 4779, 10.1021/acs.macromol.5b00820
Pepels, 2015, Influence of the main-chain configuration on the mechanical properties of linear aliphatic polyesters, Macromolecules, 48, 5845, 10.1021/acs.macromol.5b01089
Pepels, 2015, Block copolymers of "PE-Like" Poly(pentadecalactone) and Poly(L-lactide): synthesis, properties, and compatibilization of polyethylene/Poly(L-lactide) blends, Macromolecules, 48, 6909, 10.1021/acs.macromol.5b01620
Pepels, 2016, Molecular structure–catalytic activity relationship in the ring-opening polymerization of (Macro)lactones, Macromolecules, 49, 796, 10.1021/acs.macromol.5b02391
Rutkowski, 2017, Toward polyethylene-polyester block and graft copolymers with tunable polarity, Macromolecules, 50, 107, 10.1021/acs.macromol.6b02341
Fuoco, 2015, Ring-opening polymerization of ω-6-hexadecenlactone by a salicylaldiminato aluminum complex: a route to semicrystalline and functional poly(ester)s, Polym Chem, 6, 1727, 10.1039/C4PY01445F
Hori, 1999, Ring-opening copolymerization of (R)-β-butyrolactone with macrolide: a new series of poly(hydroxyalkanoate)s, Macromolecules, 32, 3537, 10.1021/ma981846e
Zotzmann, 2010, Copolymer networks based on Poly(ω-pentadecalactone) and Poly(ε-caprolactone)Segments as a Versatile Triple-Shape Polymer System, Adv Funct Mater, 20, 3583, 10.1002/adfm.201000478
Zotzmann, 2010, Reversible triple-shape effect of polymer networks containing polypentadecalactone- and poly(ε-caprolactone)-Segments, Adv Mater, 22, 3424, 10.1002/adma.200904202
Zotzmann, 2011, Upscaling the synthesis of biodegradable multiblock copolymers capable of a shape-memory effect, J Mater Sci Mater Med, 22, 2147, 10.1007/s10856-011-4404-6
Behl, 2011, One-way and reversible dual-shape effect of polymer networks based on polypentadecalactone segments, J Artif Organs, 34, 231, 10.5301/IJAO.2011.6424
Balk, 2012, Shape-memory hydrogels with switching segments based on oligo(ω-pentadecalactone), Macromol Mater Eng, 297, 1184, 10.1002/mame.201200232
Kratz, 2012, Temperature-memory effect of copolyesterurethanes and their application potential in minimally invasive medical technologies, Adv Funct Mater, 22, 3057, 10.1002/adfm.201200211
Razzaq, 2012, Oligo(ω-pentadecalactone) decorated magnetic nanoparticles, J Mater Chem, 22, 9237, 10.1039/c2jm16146j
Matsumoto, 2012, Shape-memory properties of electrospun non-woven fabrics prepared from degradable polyesterurethanes containing poly(ω-pentadecalactone) hard segments, Eur Polym J, 48, 1866, 10.1016/j.eurpolymj.2012.07.008
Razzaq, 2013, Multifunctional hybrid nanocomposites with magnetically controlled reversible shape–memory effect, Adv Mater, 25, 5730, 10.1002/adma.201302485
Razzaq, 2014, Magnetically controlled shape-memory effects of hybrid nanocomposites from oligo(ω-pentadecalactone) and covalently integrated magnetite nanoparticles, Polymer, 55, 5953, 10.1016/j.polymer.2014.07.025
Schone, 2014, Characterization of langmuir films prepared from copolyesterurethanes based on oligo(ω-pentadecalactone) and oligo(ε-caprolactone) segments, Macromol Chem Phys, 215, 2437, 10.1002/macp.201400377
Wischke, 2014, Method for preparation, programming, and characterization of miniaturized particulate shape-memory polymer matrices, Langmuir, 30, 2820, 10.1021/la4025926
Wang, 2015, Characterization of bi-layered magnetic nanoparticles synthesized via two-step surface-initiated ring-opening polymerization, Pure Appl Chem, 87, 1085, 10.1515/pac-2015-0607
Fang, 2016, Programming structural functions in phase-segregated polymers by implementing a defined thermomechanical history, Polymer, 102, 54, 10.1016/j.polymer.2016.08.105
Schone, 2016, The relevance of hydrophobic segments in multiblock copolyesterurethanes for their enzymatic degradation at the air-water interface, Polymer, 102, 92, 10.1016/j.polymer.2016.09.001
Fernández, 2015, Synthesis and characterization of ω-pentadecalactone-co-ε-decalactone copolymers: evaluation of thermal, mechanical and biodegradation properties, Polymer, 81, 12, 10.1016/j.polymer.2015.11.001
Fernandez, 2016, Synthesis and properties of ω-pentadecalactone-co-δ-hexalactone copolymers: a biodegradable thermoplastic elastomer as an alternative to poly(ε-caprolactone), RSC Adv, 6, 3137, 10.1039/C5RA23404B
Fernandez, 2016, Ethylene brassylate-co-δ-hexalactone biobased polymers for application in the medical field: synthesis, characterization and cell culture studies, RSC Adv, 6, 22121, 10.1039/C6RA01065B
Fernandez, 2016, Effect of molecular weight on the physical properties of poly(ethylene brassylate) homopolymers, J Mech Behav Biomed Mater, 64, 209, 10.1016/j.jmbbm.2016.07.031
Jin, 2018, Copolymerization of ethylene brassylate with δ-valerolactone towards isodimorphic random copolyesters with continuously tunable mechanical properties, Eur Polym J, 102, 90, 10.1016/j.eurpolymj.2018.03.018
Fernandez, 2017, Ethylene brassylate: searching for new comonomers that enhance the ductility and biodegradability of polylactides, Polym Degrad Stabil, 137, 23, 10.1016/j.polymdegradstab.2017.01.001
Jasinska-Walc, 2014, Topological behavior mimicking ethylene - hexene copolymers using branched lactones and macrolactones, Polym Chem, 5, 3306, 10.1039/C3PY01754K
Chang, 2015, Synthesis and characterization of poly(ω-pentadecalactone) for its industrial-scale production, Chem Res Chin Univ, 31, 640, 10.1007/s40242-015-5092-4
Myers, 2017, Ring opening polymerization of macrolactones: high conversions and activities using an yttrium catalyst, Polym Chem, 8, 5780, 10.1039/C7PY00985B
Guillaume, 2012, Recent advances in metallo/organo-catalyzed immortal ring-opening polymerization of cyclic carbonates, Catal Sci Technol, 2, 898, 10.1039/c2cy00507g
Asano, 1985, ’Immortal’ polymerization. Polymerization of epoxide catalysed by an aluminium porphyrin-alcohol system, J Chem SocChem Commun, 1148, 10.1039/C39850001148
Endo, 1987, Immortal polymerization of ε-caprolactone initiated by aluminum porphyrin in the presence of alcohol, Macromolecules, 20, 2982, 10.1021/ma00178a005
Dove, 2012, Organic catalysis for ring-opening polymerization, ACS Macro Lett, 1, 1409, 10.1021/mz3005956
Nederberg, 2001, New paradigms for organic catalysts: the first organocatalytic living polymerization, Angew Chem Int Ed, 40, 2712, 10.1002/1521-3773(20010716)40:14<2712::AID-ANIE2712>3.0.CO;2-Z
Pascual, 2014, Organocatalyzed synthesis of aliphatic polyesters from ethylene brassy late: a cheap and renewable macrolactone, ACS Macro Lett, 3, 849, 10.1021/mz500401u
Kamber, 2007, Organocatalytic ring-opening polymerization, Chem Rev, 107, 5813, 10.1021/cr068415b
Todd, 2015, Poly(ω-pentadecalactone)-b-poly(l-lactide) block copolymers via organic-catalyzed ring opening polymerization and potential applications, ACS Macro Lett, 4, 408, 10.1021/acsmacrolett.5b00021
Bouyahyi, 2012, Ω-pentandecalactone polymerization and ω-Pentadecalactone/ε-Caprolactone copolymerization reactions using organic catalysts, Macromolecules, 45, 3356, 10.1021/ma3001675
Ladelta, 2017, Ring-opening polymerization of ω-pentadecalactone catalyzed by phosphazene superbases, Polym Chem, 8, 511, 10.1039/C6PY01983H
Naumann, 2016, Highly polarized Alkenes as organocatalysts for the polymerization of lactones and trimethylene carbonate, ACS Macro Lett, 5, 134, 10.1021/acsmacrolett.5b00873
Naumann, 2015, Dual catalysis for selective ring-opening polymerization of lactones: evolution toward simplicity, J Am Chem Soc, 137, 14439, 10.1021/jacs.5b09502
Walther, 2017, N-heterocyclic olefin-based (Co)polymerization of a challenging monomer: homopolymerization of ω-Pentadecalactone and its Copolymers with γ-Butyrolactone, δ-Valerolactone, and ε-Caprolactone, Macromolecules, 50, 8406, 10.1021/acs.macromol.7b01678
Wang, 2018, Ring-opening polymerization with lewis pairs and subsequent nucleophilic substitution: a promising strategy to well-defined polyethylene-like polyesters without transesterification, Macromolecules, 51, 836, 10.1021/acs.macromol.7b02378
Pascual, 2013, Acid catalyzed polymerization of macrolactones in bulk and aqueous miniemulsion: ring opening vs. condensation, Eur Polym J, 49, 1601, 10.1016/j.eurpolymj.2013.02.009
Barrère, 2003, Polyester synthesis in aqueous miniemulsion, Polymer, 44, 2833, 10.1016/S0032-3861(03)00151-4
Delgove, 2017, Increasing the solubility range of polyesters by tuning their microstructure with comonomers, Polym Chem, 8, 4696, 10.1039/C7PY00976C
Ladelta, 2018, Block copolymers of Macrolactones/Small lactones by a “Catalyst-Switch” organocatalytic strategy. Thermal properties and phase behavior, Macromolecules, 51, 2428, 10.1021/acs.macromol.8b00153
Ravichandran, 2012, Advances in polymeric systems for tissue engineering and biomedical applications, Macromol Biosci, 12, 286, 10.1002/mabi.201100325
Sokolsky-Papkov, 2007, Polymer carriers for drug delivery in tissue engineering, Adv Drug Delivery Rev, 59, 187, 10.1016/j.addr.2007.04.001
Saralidze, 2010, Polymeric microspheres for medical applications, Materials, 3, 3537, 10.3390/ma3063537
Plikk, 2009, Design of resorbable porous tubular copolyester scaffolds for use in nerve regeneration, Biomacromolecules, 10, 1259, 10.1021/bm900093r
Jain, 1998, Controlled drug delivery by biodegradable poly(Ester) devices: different preparative approaches, Drug Dev Ind Pharm, 24, 703, 10.3109/03639049809082719
Jiao, 2007, Surface modification of polyester biomaterials for tissue engineering, Biomed Mater, 2, R24, 10.1088/1748-6041/2/4/R02
Goddard, 2007, Polymer surface modification for the attachment of bioactive compounds, Prog Polym Sci, 32, 698, 10.1016/j.progpolymsci.2007.04.002
Uyama, 1998, Enzymatic synthesis of terminal-functionalized polyesters by initiator method, Acta Polym Sin, 49, 700, 10.1002/(SICI)1521-4044(199812)49:12<700::AID-APOL700>3.0.CO;2-C
Descour, 2015, In situ compatibilization of alkenyl-terminated polymer blends using cross metathesis, RSC Adv, 5, 9658, 10.1039/C4RA11056K
Kalra, 2004, Chemoenzymatic synthesis of new brush copolymers comprising poly(ω-pentadecalactone) with unusual thermal and crystalline properties, Macromolecules, 37, 1243, 10.1021/ma035083t
Takwa, 2008, Lipase catalyzed HEMA initiated ring-opening polymerization: in situ formation of mixed polyester methacrylates by transesterification, Biomacromolecules, 9, 704, 10.1021/bm7010449
Xiao, 2009, Systematic comparison of HEA and HEMA as initiators in enzymatic ring-opening polymerizations, Macromol Biosci, 9, 713, 10.1002/mabi.200800290
Uyama, 1995, One-shot synthesis of polyester macromonomer by enzymatic ring-opening polymerization of lactone in the presence of vinyl ester, Chem Lett, 1047, 10.1246/cl.1995.1047
Uyama, 1997, Single-step acylation of polyester terminals by enzymatic ring-opening polymerization of 12-dodecanolide in the presence of acyclic vinyl esters, Bull Chem Soc Jpn, 70, 1691, 10.1246/bcsj.70.1691
Korzhikov, 2013, Enzyme-mediated ring-opening polymerization of Pentadecalactone to obtain biodegradable polymer for fabrication of scaffolds for bone tissue engineering, Int J Polym Sci, 2013, 10.1155/2013/476748
Takwa, 2006, One-pot difunctionalization of poly(ω-pentadecalactone) with thiol-Thiol or thiol-acrylate groups, Catalyzed by Candida antarctica Lipase B, Macromol Rapid Commun, 27, 1932, 10.1002/marc.200600527
Takwa, 2008, Single-step, solvent-free enzymatic route to α,ω-functionalized polypentadecalactone macromonomers, Macromolecules, 41, 5230, 10.1021/ma800074a
Simpson, 2008, Thiol-functionalized poly(ω-pentadecalactone) telechelics for semicrystalline polymer networks, Macromolecules, 41, 3613, 10.1021/ma702419m
Kumar, 2002, Recognition by lipases of ω-Hydroxyl macroinitiators for diblock copolymer synthesis, Macromolecules, 35, 7606, 10.1021/ma020060k
Chen, 2015, Amphiphilic poly(ethylene glycol)-b-poly(ethylene brassylate) copolymers: one-pot synthesis, self-assembly, and controlled drug release, Chin Chem Lett, 26, 1319, 10.1016/j.cclet.2015.05.050
Bansal, 2015, New biomaterials from renewable resources - amphiphilic block copolymers from δ-decalactone, Polym Chem, 6, 7196, 10.1039/C5PY01203A
Bansal, 2018, Renewable poly(δ-decalactone) based block copolymer micelles as drug delivery vehicle: in vitro and in vivo evaluation, Saudi Pharm J, 26, 358, 10.1016/j.jsps.2018.01.006
Pflughaupt, 2016, Synthesis of poly(ω-pentadecalactone)-b-poly(acrylate) diblock copolymers via a combination of enzymatic ring-opening and RAFT polymerization techniques, J Polym SciPart A Polym Chem, 54, 3326, 10.1002/pola.28221
Chen, 2016, Synthesis and self-assembly of four-armed star copolymer based on poly(ethylene brassylate) hydrophobic block as potential drug carries, J Nanopart Res, 18, 10.1007/s11051-016-3446-6
Arnebold, 2016, Fast switchable, epoxy based shape-memory polymers with high strength and toughness, Polymer, 83, 40, 10.1016/j.polymer.2015.12.007
Pilate, 2018, Poly(ε-caprolactone) and poly(ω-pentadecalactone)-Based networks with two-way shape-memory effect through 2+2 cycloaddition reactions, Macromol Chem Phys, 219
Jérôme, 2008, Recent advances in the synthesis of aliphatic polyesters by ring-opening polymerization, Adv Drug Deliv Rev, 60, 1056, 10.1016/j.addr.2008.02.008
Vaida, 2011, Tailor-made polyesters based on pentadecalactone via enzymatic catalysis, Green Chem, 13, 889, 10.1039/c1gc15044h
van der Meulen, 2008, Polymers from functional macrolactones as potential biomaterials: enzymatic ring opening polymerization, biodegradation, and biocompatibility, Biomacromolecules, 9, 3404, 10.1021/bm800898c
van der Meulen, 2011, Copolymers from unsaturated macrolactones: toward the design of cross-linked biodegradable polyesters, Biomacromolecules, 12, 837, 10.1021/bm200084y
Van Der Mee, 2006, Oxo-crown-ethers as comonomers for tuning polyester properties, J Polym SciPart A Polym Chem, 44, 2166, 10.1002/pola.21329
Illy, 2013, Synthesis and anionic ring-opening polymerization of crown-ether-like macrocyclic dilactones: an alternative route to peg-containing polyesters PEG-containing polyesters and related networks, Eur Polym J, 49, 4087, 10.1016/j.eurpolymj.2013.09.014
Manzini, 2010, Entropically-driven ring-opening polymerization of macrocyclic esters with up to 84-membered rings catalysed by polymer-supported Candida antarctica lipase B, Polym Chem, 1, 339, 10.1039/B9PY00350A
Jiang, 2007, Lipase-catalyzed copolymerization of ω-pentadecalactone with p-dioxanone and characterization of copolymer thermal and crystalline properties, Biomacromolecules, 8, 2262, 10.1021/bm070138a
Liu, 2011, Biodegradation, biocompatibility, and drug delivery in poly(ω-pentadecalactone-co-p-dioxanone) copolyesters, Biomaterials, 32, 6646, 10.1016/j.biomaterials.2011.05.046
Magusin, 2005, Novel biodegradable poly(pentadecalactone-co-oxo-crown ether) studied with solid-state 1H and 13C NMR, Macromol Symp, 230, 126, 10.1002/masy.200551151
Pepels, 2016, Catalytic ring-opening (Co)polymerization of semiaromatic and aliphatic (Macro)lactones, Macromolecules, 49, 4441, 10.1021/acs.macromol.6b00744
Wisse, 2007, Poly(caprolactone-co-oxo-crown ether)-based poly(urethane)urea for soft tissue engineering applications, Biomacromolecules, 8, 2739, 10.1021/bm070375d
Focarete, 2002, Copolymers of ω-Pentadecalactone and trimethylene carbonate from lipase catalysis: influence of microstructure on solid-state properties, Macromolecules, 35, 8066, 10.1021/ma0205966
Veld, 2007, Selective polymerization of functional monomers with novozym 435, J Polym Sci Part A Polym Chem, 45, 5968, 10.1002/pola.22350
Uyama, 2001, Chemoselective ring-opening polymerization of a lactone having exo-methylene group with lipase catalysis, Macromolecules, 34, 6554, 10.1021/ma010893v
Habaue, 2003, Chemospecific ring-opening polymerization of α-methylenemacrolides, Polymer, 44, 5195, 10.1016/S0032-3861(03)00491-9
Habaue, 2002, Stereospecific anionic polymerization of α-(alkoxymethyl)acrylate derivatives affording novel vinyl polymers with macrocyclic side chains, Polymer, 43, 3469, 10.1016/S0032-3861(02)00045-9
Habaue, 2002, Anionic polymerization of macrocyclic α-(alkoxymethyl)acrylates leading to novel vinyl polymer with crown ether type side chain, Macromolecules, 35, 2432, 10.1021/ma0116452
Ates, 2011, Side-chain functionalization of unsaturated polyesters from ring-opening polymerization of macrolactones by thiol-ene click chemistry, Polym Chem, 2, 309, 10.1039/C0PY00294A
Ates, 2014, Functional films from unsaturated poly(macrolactones) by thiol-ene cross-linking and functionalization, Polym Chem, 5, 2936, 10.1039/c3py01679j
Ates, 2014, Functional brush-decorated poly(globalide) films by ARGET-ATRP for bioconjugation, Macromol Biosci, 14, 1600, 10.1002/mabi.201400282
de Oliveira, 2017, Direct UV-Triggered thiol–ene cross-linking of electrospun polyester fibers from unsaturated poly(macrolactone)s and their drug loading by solvent swelling, Biomacromolecules, 18, 4292, 10.1021/acs.biomac.7b01335
Claudino, 2012, Photoinduced thiol-ene crosslinking of globalide/ε-caprolactone copolymers: curing performance and resulting thermoset properties, J Polym Sci Part A Polym Chem, 50, 16, 10.1002/pola.24940
Wang, 2017, Two-way reversible shape memory polymers made of cross-linked cocrystallizable random copolymers with tunable actuation temperatures, Macromolecules, 50, 8570, 10.1021/acs.macromol.7b01815
Yu, 2012, Lipase/esterase-catalyzed synthesis of aliphatic polyesters via polycondensation: a review, Process Biochem, 47, 1027, 10.1016/j.procbio.2012.04.006
Namekawa, 2000, Enzymatic synthesis of polyesters from Lactones, dicarboxylic acid divinyl esters, and glycols through combination of ring-opening polymerization and polycondensation, Biomacromolecules, 1, 335, 10.1021/bm000030u
Thompson, 2007, Evaluation of ibuprofen-loaded microspheres prepared from novel copolyesters, Int J Pharm, 329, 53, 10.1016/j.ijpharm.2006.08.019
Gaskell, 2008, Encapsulation and release of α-chymotrypsin from poly(glycerol adipate-co-ω-pentadecalactone) microparticles, J Microencapsulation, 25, 187, 10.1080/02652040701848775
Thompson, 2008, Synthesis and evaluation of novel polyester-ibuprofen conjugates for modified drug release, Drug Dev Ind Pharm, 34, 877, 10.1080/03639040801929075
Thompson, 2009, Preparation and evaluation of microspheres prepared from novel polyester-ibuprofen conjugates blended with non-conjugated ibuprofen, J Microencapsulation, 26, 676, 10.3109/02652040802656333
Tawfeek, 2011, Poly(Glycerol Adipate-co-ω-Pentadecalactone) spray-dried microparticles as sustained release carriers for pulmonary delivery, Pharm Res, 28, 2086, 10.1007/s11095-011-0433-6
Jan, 2013, Synthesis, conjugation and evaluation of some novel polymers and their micro particles for sustained release drug formulations, Pak J Pharm Sci, 26, 741
Tawfeek, 2014, Evaluation of biodegradable polyester-co-lactone microparticles for protein delivery, Drug Dev Ind Pharm, 40, 1213, 10.3109/03639045.2013.814060
Alfagih, 2015, Pulmonary delivery of proteins using nanocomposite microcarriers, J Pharm Sci, 104, 4386, 10.1002/jps.24681
Kunda, 2015, Bovine serum albumin adsorbed PGA-co-PDL nanocarriers for vaccine delivery via dry powder inhalation, Pharm Res, 32, 1341, 10.1007/s11095-014-1538-5
Tawfeek, 2017, Colonic delivery of indometacin loaded PGA-co-PDL microparticles coated with Eudragit L100-55 from fast disintegrating tablets, Int J Pharm, 531, 80, 10.1016/j.ijpharm.2017.08.069
Rodrigues, 2018, Mucosal immunization with PspA (Pneumococcal surface protein A)-adsorbed nanoparticles targeting the lungs for protection against pneumococcal infection, PLoS One, 13, 10.1371/journal.pone.0191692
Tawfeek, 2013, Dry powder inhalation of macromolecules using novel PEG-co-polyester microparticle carriers, Int J Pharm, 441, 611, 10.1016/j.ijpharm.2012.10.036
Tawfeek, 2013, Evaluation of PEG and mPEG-co-(PGA-co-PDL) microparticles loaded with sodium diclofenac, Saudi Pharm J, 21, 387, 10.1016/j.jsps.2012.11.006
Jiang, 2008, Lipase-catalyzed synthesis of aliphatic polyesters via copolymerization of lactone, dialkyl diester, and diol, Biomacromolecules, 9, 3246, 10.1021/bm800814m
Mazzocchetti, 2009, Enzymatic synthesis and structural and thermal properties of poly(ω-pentadecalactone-co-butylene-co-succinate), Macromolecules, 42, 7811, 10.1021/ma901338v
Liu, 2009, Poly(ω-pentadecalactone-co-butylene-co-succinate) nanoparticles as biodegradable carriers for camptothecin delivery, Biomaterials, 30, 5707, 10.1016/j.biomaterials.2009.06.061
Mazzocchetti, 2011, Copolymers of ethyl glycolate and ω–pentadecalactone: enzymatic synthesis and solid-state characterization, Eur Polym J, 47, 942, 10.1016/j.eurpolymj.2011.01.003
Voevodina, 2014, Exploring the solid state properties of enzymatic poly(amine-co-ester) terpolymers to expand their applications in gene transfection, RSC Adv, 4, 8953, 10.1039/c3ra46918b
Zhou, 2011, Biodegradable poly(amine-co-ester) terpolymers for targeted gene delivery, Nat Mater, 11, 82, 10.1038/nmat3187
Liu, 2015, Enzymatic synthesis of poly(ω-pentadecalactone-co-butylene-co-3,3’ -dithiodipropionate) copolyesters and self-assembly of the PEGylated copolymer micelles as redox-responsive nanocarriers for doxorubicin delivery, Polym Chem, 6, 1997, 10.1039/C4PY01321B
Jiang, 2011, Lipase-Catalyzed Copolymerization of Dialkyl Carbonate with 1,4-Butanediol and ω-Pentadecalactone: Synthesis of Poly(ω-pentadecalactone-co-butylene-co-carbonate), Biomacromolecules, 12, 1912, 10.1021/bm2002522
Mazzocchetti, 2012, Random copolymerization with a large lactone enhances aliphatic polycarbonate crystallinity, Eur Polym J, 48, 1883, 10.1016/j.eurpolymj.2012.08.010
Martino, 2012, Enzymatic synthesis, thermal and crystalline properties of a poly(β–amino ester) and poly(lactone-co-β–amino ester) copolymers, Polymer, 53, 1839, 10.1016/j.polymer.2012.03.005
Hua, 2018, Exploiting ring-opening aminolysis-condensation as a polymerization pathway to structurally diverse biobased polyamides, Biomacromolecules, 19, 1573, 10.1021/acs.biomac.8b00322
Zhang, 2014, Micelles of enzymatically synthesized PEG-poly(amine-co-ester) block copolymers as pH-responsive nanocarriers for docetaxel delivery, Colloids Surf B, 115, 349, 10.1016/j.colsurfb.2013.12.029
Zhang, 2014, PEGylated poly(amine-co-ester) micelles as biodegradable non-viral gene vectors with enhanced stability, reduced toxicity and higher in vivo transfection efficacy, J Mater Chem B, 2, 4034, 10.1039/c4tb00439f
Chen, 2017, Enzymatic PEG-Poly(amine-co-disulfide ester) nanoparticles as pH-and redox-responsive drug nanocarriers for efficient antitumor treatment, ACS Appl Mater Interfaces, 9, 30519, 10.1021/acsami.7b10148
Chen, 2016, Enzymatic PEGylated poly(lactone-co-β-amino ester) nanoparticles as biodegradable, biocompatible and stable vectors for gene delivery, ACS Appl Mater Interfaces, 8, 490, 10.1021/acsami.5b09437
Eriksson, 2009, Enzymatic One-Pot Route to Telechelic Polypentadecalactone Epoxide: Synthesis, UV Curing, and Characterization, Biomacromolecules, 10, 3108, 10.1021/bm9007925
Seyednejad, 2011, Functional aliphatic polyesters for biomedical and pharmaceutical applications, J Control Release, 152, 168, 10.1016/j.jconrel.2010.12.016
Amass, 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, 10.1002/(SICI)1097-0126(1998100)47:2<89::AID-PI86>3.0.CO;2-F
Vert, 2005, Aliphatic polyesters: great degradable polymers that cannot do everything, Biomacromolecules, 6, 538, 10.1021/bm0494702
Gazzano, 2003, Crystal structure of poly(ω-pentadecalactone), J Polym Sci Part B Polym Phys, 41, 1009, 10.1002/polb.10419
Cai, 2009, Polypentadecalactone prepared by lipase catalysis: crystallization kinetics and morphology, Polym Int, 58, 944, 10.1002/pi.2624
de Geus, 2010, Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications, Polym Chem, 1, 525, 10.1039/b9py00360f
Cai, 2011, Real-time structure changes during uniaxial stretching of poly (ω-pentadecalactone) by in situ synchrotron WAXD/SAXS techniques, Macromolecules, 44, 3874, 10.1021/ma102949h
Jeremic, 2014
Wilsens, 2016, Improving stiffness, strength, and toughness of poly(ω-pentadecalactone) fibers through in situ reinforcement with a vanillic acid-based thermotropic liquid crystalline Polyester, Macromolecules, 49, 2228, 10.1021/acs.macromol.5b02419
Ye, 2017, Supernucleating role of poly(ω-pentadecalactone) during the crystallization of poly(ε-caprolactone) composites, Ind Eng Chem Res, 56, 13725, 10.1021/acs.iecr.7b03322
Ulery, 2011, Biomedical applications of biodegradable polymers, J Polym Sci Part B Polym Phys, 49, 832, 10.1002/polb.22259
Azevedo, 2005, Understanding the enzymatic degradation of biodegradable polymers and strategies to control their degradation rate, 177
Ceccorulli, 2005, Cocrystallization of random copolymers of ω-pentadecalactone and ε-caprolactone synthesized by lipase catalysis, Biomacromolecules, 6, 902, 10.1021/bm0493279
Focarete, 2010, Electrospun scaffolds of a polyhydroxyalkanoate consisting of ω-Hydroxylpentadecanoate repeat units: fabrication and in vitro biocompatibility studies, J Biomater SciPolym Ed, 21, 1283, 10.1163/092050609X12517190417597
Ziemba, 2018, Poly-l-lactic acid-co-poly(pentadecalactone) electrospun fibers result in greater neurite outgrowth of chick dorsal root ganglia in vitro compared to Poly-L-lactic acid fibers, ACS Biomater Sci Eng, 4, 1491
Albertsson, 2002, Aliphatic polyesters: synthesis, properties and applications. Degradable aliphatic polyesters, Adv Polym Sci, 157, 1, 10.1007/3-540-45734-8_1