Ring-opening precipitation polymerization of poly(D,L-lactide-co-glycolide) in supercritical carbon dioxide

Hile, David D.; Pishko, Michael V.

doi:10.1002/(sici)1521-3927(19991001)20:10<511::aid-marc511>3.0.co;2-q

Cited by 57 publications

(41 citation statements)

References 14 publications

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“…Moreover, the availability of CO 2 as a byproduct of many industrial processes, its possible recycling, and easily accessible critical parameters account for its steadily increasing use. [164,165] The lipase-catalyzed transesterifications of a diester and diol were carried out in scCO 2 and supercritical fluoroform by Chaudhary et al and they reported that the molecular weight of the resulting polymer could be controlled by changing the pressure. [164] Hile and Pishko synthesized poly(lactide-co-glycolide) by a ring-opening precipitation polymerization in scCO 2 using stannous octoate as an initiator.…”

Section: Solvents For Green Polymer Production and Recyclingmentioning

confidence: 99%

“…The weight-average molecular weight of the product was measured to be 3 400. [165] More recently, the ring-opening polymerization of CL initiated by dibutyltin dimethoxide was studied in scCO 2 at 40 8C at a pressure of 210-215 bar by Stassin et al [166] The molecular weight of the produced PCL was about 20 000.…”

Section: Solvents For Green Polymer Production and Recyclingmentioning

confidence: 99%

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Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Matsumura¹

2002

Macromol. Biosci.

113

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This article summarizes the enzyme‐catalyzed synthesis and chemical recycling of biodegradable aliphatic polyesters and poly(carbonate ester)s directed towards establishing green polymer chemistry. Lipase catalyzes the condensation polymerization of a hydroxy acid, diacid with diol, diacid anhydride with oxirane, and polyanhydride with diol, or the ring‐opening polymerization of lactones of small to large rings, and a cyclic diester to produce the corresponding polyesters. Also, lipase catalyzes the condensation polymerization of a dialkyl carbonate with diol, and the ring‐opening polymerization of a cyclic carbonate to produce the corresponding polycarbonates. These polyesters and polycarbonates were selectively degraded by lipase to produce repolymerizable oligomers. These chemical recycling systems using an enzyme will establish a novel methodology for sustainable polymer recycling. Finally, current trends in green polymer production using enzymes are discussed.

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Section: Solvents For Green Polymer Production and Recyclingmentioning

confidence: 99%

Section: Solvents For Green Polymer Production and Recyclingmentioning

confidence: 99%

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Matsumura¹

2002

Macromol. Biosci.

113

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“…The emulsion and precipitation syntheses of poly(D,L-lactide-co-glycolide) using a CO 2 soluble SB, poly(perfluoroocytyl), were reported by Hile and Pishko. 29,30 Bratton et al 31,32 used blocks of PCL with KrytoxFSL and PCL-perfluoropolyether-PCL as SBs in PLLA synthesis in scCO 2 . A series of fluorinated diblock and triblock copolymers of PCL and poly(heptadecafluorodecylacrylate) were synthesized as SBs by the ring-opening polymerization of e-CL and atom transfer radical polymerization of the acrylate by Grignard et al 33 They used these copolymers in the dispersion ringopening polymerization of e-CL in scCO 2 .…”

Section: Introductionmentioning

confidence: 99%

Ring-opening copolymerization of L-lactide and ɛ-caprolactone in supercritical carbon dioxide using triblock oligomers of caprolactone and PEG as stabilizers

Yılmaz

Eğri

Yıldız

et al. 2011

Polym J

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In this study, the use of triblock (A-B-A) oligomers of e-caprolactone (e-CL) (A) and PEG400 (B) as stabilizers (SB) for the copolymerization of L-lactide (LLA) and e-CL in supercritical carbon dioxide (scCO 2 ) was investigated. To determine the effect of CO 2 -philic and polymer-philic segments on copolymerization, oligomers with three different average molecular weights (M w ¼2000-6000 Da) were synthesized by changing the PEG400/e-CL ratio. Copolymerizations were confirmed by 1 H-nuclear magnetic resonance (NMR), 13 C-NMR and differential scanning calorimeter data. It was possible to copolymerize LLA and e-CL in scCO 2 without any SB; however, the polymerization yields and average molecular weights were low, and significant aggregate formations were detected. Recipes featuring only 5% SB were successfully applied to reach high polymerization yields of B85% and polymers with average molecular weights greater than 20 kDa. When the polymer-philic segment of the SB increased, both the yield and molecular weight of the copolymer also increased significantly, resulting in white powdery products.

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“…For medical applications, the presence of toxic substances from the production process in the final product is critical. For this reason, although polymerization can happen either in bulk or in solution media, the first one is desired for medical applications because of allowing to discard the presence of organic solvents traces in the polymer after reaction 4. Recently, there has been an interesting increase in the synthesis and the processing of these biomaterials using supercritical carbon dioxide (scCO 2 ) as reaction media 5.…”

Section: Introductionmentioning

confidence: 99%

“…This has allowed to study polymerizations of different monomers by a wide variety of mechanisms in supercritical solvents 6. However, few works have been devoted to the synthesis of PLGA in scCO 2 by ring‐opening polymerization (ROP),4, 5, 14 although homopolymerizations of lactide and other lactones, such as ε‐caprolactone, and their copolymerizations are described either in CO 2 or other supercritical fluids 15–22…”

Section: Introductionmentioning

confidence: 99%

Copolymerization of D,L‐lactide and glycolide in supercritical carbon dioxide with zinc octoate as catalyst

et al. 2007

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The objective of the study is the development of a new technique based on supercritical technology for the production of bioabsorbable polymeric microparticles containing pharmaceutical principles, for their use in the controlled release of medicines. For this purpose, the ring-opening copolymerization of D,L-lactide and glycolide in supercritical carbon dioxide, using zinc(II) 2-ethylhexanoate (ZnOct2) as catalyst, was studied. The polymer obtained with ZnOct2 has similar characteristics to that obtained with stannous octoate (SnOct2), the conventional catalyst used up to now for this kind of polymerization process. Experiments were performed at various reaction times, pressures, and stirring rates. The most outstanding result was found by varying the stirring rate, where particles forming agglomerates seem to be obtained at the greater agitation levels.

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Ring-opening precipitation polymerization of poly(D,L-lactide-co-glycolide) in supercritical carbon dioxide

Cited by 57 publications

References 14 publications

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Ring-opening copolymerization of L-lactide and ɛ-caprolactone in supercritical carbon dioxide using triblock oligomers of caprolactone and PEG as stabilizers

Copolymerization of D,L‐lactide and glycolide in supercritical carbon dioxide with zinc octoate as catalyst

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