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

Tsutsumi, Chikara; Fukukawa, Naohisa; Sakafuji, Jun; Oro, Kazuyuki; Hata, Kunihiko; Nakayama, Yuushou; Shiono, Takeshi

doi:10.1002/app.33646

Cited by 14 publications

(13 citation statements)

References 36 publications

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“…The cause is thought to be that T m and ΔH m of poly(L-LA-ran-TEMC) are lower than that of poly (L-LA-ran-CL). In a previous study, it has reported that T m and ΔH m affect the maintenance of form and content [21] [22]. The above results showed that the differences in oil content in poly(L-LA-ran-CL) and poly(L-LA-ran-TEMC) resulted from the effect of pressure.…”

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

confidence: 64%

“…Although T m and -ΔH m of poly(L-LA) were 169.3˚C and 32.0 J/g before processing, respectively, T m and −ΔH m decreased with an extension of processing time and were 166.7˚C and 27.1 J/g, respectively, for 3 h. T m (166.0˚C) of the [34]. In our pre-vious report, in order to evaluate the relationship between T m or ΔH m and content, we synthesized various L-LA copolymers with different T m and ΔH m , and investigated the difference in content [21] [22]. In the previous work, it appeared that the content of poly(L-LA-ran-TEMC) (81/19) (T m 97.9˚C and -ΔH m 5.1 J/g), which was lower than T m and -ΔH m (157.0˚C and 36.0 J/g) of poly(L-LA-ran-CL) (85/15), was higher than that of poly(L-LAran-CL).…”

Section: Effect Of Processing Time On Impregnation Of Poly(l-la) Randmentioning

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%

See 2 more Smart Citations

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 Copomentioning

confidence: 64%

Section: Effect Of Processing Time On Impregnation Of Poly(l-la) Randmentioning

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

Self Cite

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“…Tsutsumi et al [60] reported results on the synthesis of biodegradable copolymer Poly(L-lactide-ran-cyclic carbonate) and its impregnation with d-limonene as an antibacterial agent. Outstanding controlled release materials were developed with statistical random copolymers of L-lactide (L-LA) with cyclic carbonate (CC) (2,2-dimethyltrimethylene carbonate (2,2-DTMC) or tetramethylene carbonate (TEMC)).…”

Section: Impregnation Of Polymeric Forms Other Than Textiles and Fibersmentioning

confidence: 99%

Supercritical Fluid Applications in the Design of Novel Antimicrobial Materials

Žižović

2020

Molecules

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Bacterial resistance to antibiotics is one of the biggest problems in the modern world. The prevention of bacterial spreading from hospitals to the community and vice versa is an issue we have to deal with. This review presents a vast potential of contemporary high-pressure techniques in the design of materials with antimicrobial activity. Scientists from all over the world came up with ideas on how to exploit extraordinary properties of supercritical fluids in the production of advantageous materials in an environmentally friendly way. The review summarizes reported methods and results.

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“…Controlled‐release materials can be obtained by impregnating biodegradable polymers, using scCO 2 to soften the polymers at low temperatures . CO 2 has a critical temperature of 31.1°C and a critical pressure of 7.38 MPa, such that scCO 2 can be readily generated for the processing of polymers .…”

Section: Introductionmentioning

confidence: 99%

Changes in the morphology of poly( l ‐lactide‐ ran ‐δ‐valerolactone) following supercritical carbon dioxide processing

Tsutsumi

Ishikawa

Takahashi

et al. 2019

Polymer Crystallization

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Biodegradable polymers can be employed as controlled‐release materials when processed with supercritical carbon dioxide (scCO2), and l‐lactide (L‐LA) random copolymers are useful in such applications. In the present work, poly(l‐lactide‐ran‐δ‐valerolactone) (poly(L‐LA‐ran‐VL)) copolymers, which do not melt during scCO2 processing above 80°C, were synthesized. The thermal properties, crystallinity, and polymer chain structures of these materials were evaluated before and after processing at temperatures from 60°C to 120°C and 14 MPa. An efficient one‐pot process (termed azeotropic‐combined one‐pot polymerization or ACOP) produced poly(L‐LA‐ran‐VL) or poly(L‐LA) in good yields and high molecular weights, and poly(L‐LA) with an Mn of 8.20 × 104 was obtained without the use of an inert gas. Poly(L‐LA‐ran‐VL) composed a 73/27 ratio of L‐LA and VL had a relatively high molecular weight despite its lower L‐LA content, and its Tm and ΔHm were decreased only slightly compared to that of poly(L‐LA). Both ΔHm and crystallinity were found to increase with increases in the scCO2 processing temperature, especially at 120°C. Although the degree of crystallinity increased with increasing L‐LA content, the ΔHm of the 83/17 specimen (which had the lowest Mn) was higher than that of the 91/9 sample. Before processing, the 73/27 copolymer had the highest haze value while the 91/9 specimen had the lowest, and there was a linear relationship between the haze and crystallinity of each copolymer after processing at all temperatures. The infrared spectrum of the 73/27 copolymer prior to scCO2 processing exhibited a maximum absorbance at 1756 cm−1, and this peak was shifted to higher wavenumber with increases in the processing temperature. Thus, infrared spectroscopy could be used to assess increases in crystallinity following scCO2 processing.

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

Cited by 14 publications

References 36 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

Supercritical Fluid Applications in the Design of Novel Antimicrobial Materials

Changes in the morphology of poly( l ‐lactide‐ ran ‐δ‐valerolactone) following supercritical carbon dioxide processing

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