Study of impregnation of poly(l-lactide-ran-ε-caprolactone) copolymers with useful compounds in supercritical carbon dioxide

Tsutsumi, Chikara; Sakafuji, Jun; Okada, Mai; Oro, Kazuyuki; Hata, Kunihiko

doi:10.1007/s10853-009-3477-9

Cited by 16 publications

(29 citation statements)

References 29 publications

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“…This shows that the effect of pressure is barely seen over 17 MPa. It is clear that the oil content increases with an increase of CL content in poly(L-LA-ran-CL) in conventional experiments at 20 MPa and 40˚C for 3 h [22]; the same result was also expected in this work. It is known that the density of scCO 2 increases with the rise of pressure and the solubility of a compound will also increase in connection with it.…”

Section: Effect Of Pressure On Impregnation Of Poly(l-la) Random Coposupporting

confidence: 89%

“…Although the impregnation Figure 1. Effect of pressure on impregnation of L-LA copolymer films with essential oil using scCO 2 at 40˚C for 3 h. experiment was only conducted at 20 MPa in previous experiments [20]- [22], in this work, pressure greatly affected the content of essential oil.…”

Section: Effect Of Pressure On Impregnation Of Poly(l-la) Random Copomentioning

confidence: 92%

“…We previously reported on a study of the impregnation of poly(L-LA-ran-lactone), poly(L-LA-ran-cyclic carbonate), and poly(L-LA-ran-cyclic ester-ether) with d-limonene, hinokitiol, trans-2-hexenal, and α-pinene using supercritical carbon dioxide (scCO 2 ) [20]- [22]. In this work, essential bark oil from Thujopsis dolabrata var.…”

Section: Synthesis Of Poly(l-la-ran-7-membered Cyclic Monomer)mentioning

confidence: 99%

“…We have carried out research made to impregnate a volatile compound to biodegradable polymer using CO 2 [20]- [22]. In this work, the experiment made to impregnate essential bark oil from Thujopsis dolabrata var.…”

Section: Introductionmentioning

confidence: 99%

“…Three kinds of copolymers of L-LA with CL (ε-caprolactone) [20]- [24], TEMC (tetramethylene carbonate) [21] [22] [25]- [27], or DXO (1,5-dioxepan-2-one) [22] [28] were used in this work.…”

Section: Introductionmentioning

confidence: 99%

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Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Tsutsumi

Hara²,

Ueno³

et al. 2014

JBNB

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In order to develop a novel controlled-release material, we previously attempted to impregnate poly(L-lactide) (poly(L-LA)), poly(L-LA-ran-CL) (CL: ε-caprolactone) or poly(L-LA-ran-TEMC) (TEMC: tetramethylene carbonate) with low boiling point, organic useful compounds using supercritical carbon dioxide (scCO2) as the solvent. In this work, the factors influencing impregnation of poly (L-LA) random copolymers with useful compounds were investigated under scCO2 using the copolymers previously used. The influence of temperature, pressure, and time on the impregnation contents of the useful compounds on the copolymers was evaluated. The polymer used, which is a base of this material, was poly(L-LA-ran-CL), poly(L-LA-ran-TEMC), or poly(L-LA-ran-DXO) (DXO: 1,5-dioxepan-2-one). Statistical random copolymers of L-LA with CL, TEMC, or DXO were synthesized using Sn(oct)2 as a catalyst at 150˚C for 24 h without solvent. Preparation of the controlled-release materials was carried out using essential bark oil from Thujopsis dolabrata var. hondae and synthetic L-LA random copolymers as a base material under scCO2. The impregnation experiment, which investigated the influence of pressure, was conducted in the range of 10 to 20 MPa. The influence of temperature on impregnation was carried out at 40˚C to 100˚C. Impregnation time was varied from 1 to 5 h.

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Section: Effect Of Pressure On Impregnation Of Poly(l-la) Random Coposupporting

confidence: 89%

Section: Effect Of Pressure On Impregnation Of Poly(l-la) Random Copomentioning

confidence: 92%

Section: Synthesis Of Poly(l-la-ran-7-membered Cyclic Monomer)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Three kinds of copolymers of L-LA with CL (ε-caprolactone) [20]- [24], TEMC (tetramethylene carbonate) [21] [22] [25]- [27], or DXO (1,5-dioxepan-2-one) [22] [28] were used in this work.…”

Section: Introductionmentioning

confidence: 99%

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Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Tsutsumi

Hara²,

Ueno³

et al. 2014

JBNB

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Microstructure and thermal behavior of polylactide/clay nanocomposites melt compounded under supercritical CO₂

Jiang¹,

Huang²,

Chen³

2011

Adv Polym Technol

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Supercritical carbon dioxide (Sc-CO 2 ) is a good plasticizer to improve the compatibility for nanocomposites or polymer blends. In this work, polylactide (PLA)/clay nanocomposites were compounded using a twin-screw extruder. Two extrusion methods were used, one with Sc-CO 2 and another without Sc-CO 2 . Microstructures of nanocomposites and their mechanical properties were investigated. Their thermal behavior was analyzed using differential scanning calorimeter (DSC) and thermogravimetry analyzer. Results show that the layer spacing of clay in the nanocomposites was improved. Observed from transmission electron microscopy photomicrographs, it was shown that the clay was dispersed more homogeneously in the nanocomposites MICROSTRUCTURE AND THEREHAVIOR OF POLYLACTIDE/CLAY NANOCOMPOSITEScompounded with Sc-CO 2 . DSC traces show that cold crystallization appeared for nanocomposites, indicating that clay could act as a nucleating agent. Sc-CO 2 was helpful in improving the thermal stability of nanocomposites. In addition, there existed a yielding phenomenon for nanocomposites during the tensile property measurement. With the preparation of Sc-CO 2 , the elongation at break and tensile strength for nanocomposites were increased. C

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Impregnation of poly(L‐lactide‐ran‐cyclic carbonate) copolymers with useful compounds with supercritical carbon dioxide

Tsutsumi

Fukukawa

Sakafuji

et al. 2011

J of Applied Polymer Sci

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In this article, we cover the development of L-lactide (L-LA) random copolymers into which useful compounds, such as repellents and antibacterial agents, were impregnated by high concentration. Outstanding controlled release materials were developed with statistical random copolymers of L-LA with cyclic carbonate (CC) [2,2-dimethyltrimethylene carbonate (2,2-DTMC) or tetramethylene carbonate (TEMC)] with tin 2-ethyL-hexanoate as a catalyst at 150 C (2,2-DTMC) or 120 C (TEMC) for 24 h without solvent. The preparation of improved controlled release materials was performed with useful organic compounds with low boiling points and synthetic L-LA random copolymers containing CCs as base materials under supercritical carbon dioxide (scCO 2 ). Low-boiling-point compounds, such as d-limonene and hinokitiol, were used. In impregnation experiments with scCO 2 , the amounts of low-boiling-point compounds increased with increasings L-LA content. The compound content impregnated into poly(L-lactide-ran-cyclic carbonate) [poly(L-LAran-CC)] was greater than that of the experiment with poly(L-lactide-ran-e-caprolactone) previously studied. When the enzymatic degradation of poly(L-LA-ran-CC) was performed with proteinase K, copolymers with a greater L-LA content degraded more rapidly than did copolymers with a greater CC content. In a controlled release experiment with poly(L-lactide-ran-2,2-dimethyltrimethylene carbonate) (76/24) or poly(L-lactide-ran-tetramethylene carbonate) (81/19), the rate of polymer degradation and the rate of impregnated compound release were almost the same.

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Study of impregnation of poly(l-lactide-ran-ε-caprolactone) copolymers with useful compounds in supercritical carbon dioxide

Cited by 16 publications

References 29 publications

Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Microstructure and thermal behavior of polylactide/clay nanocomposites melt compounded under supercritical CO₂

Impregnation of poly(L‐lactide‐ran‐cyclic carbonate) copolymers with useful compounds with supercritical carbon dioxide

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Study of impregnation of poly(l-lactide-ran-ε-caprolactone) copolymers with useful compounds in supercritical carbon dioxide

Cited by 16 publications

References 29 publications

Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Supercritical Fluid Impregnation of Essential Bark Oil in Copolymers of L-Lactide with 7-Membered Cyclic Compounds

Microstructure and thermal behavior of polylactide/clay nanocomposites melt compounded under supercritical CO2

Impregnation of poly(L‐lactide‐ran‐cyclic carbonate) copolymers with useful compounds with supercritical carbon dioxide

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Microstructure and thermal behavior of polylactide/clay nanocomposites melt compounded under supercritical CO₂