Incorporation of l-lactide random copolymers with Japanese cypress oil (α-pinene) using supercritical carbon dioxide

Tsutsumi, Chikara; Hara, Teruyuki; Fukukawa, Naohisa; Oro, Kazuyuki; Hata, Kunihiko; Nakayama, Yuushou; Shiono, Takeshi

doi:10.1039/c2gc16546e

Cited by 15 publications

(12 citation statements)

References 30 publications

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“…Natu et al have shown that timolol maleate which is a hydrophilic drug is more impregnated in poly(ε-caprolactone) PCL blended with poly(oxyethylene-b-oxypropylene-b-oxyethylene) (PCL/POE) copolymer than in PCL blended with poly(ethylene-co-vinyl acetate) (PCL/ PEVA) copolymer because of the higher hydrophilicity of the first copolymer [44]. On the contrary is noticed for hydrophobic compounds that prefer polymers with long alkyl-chains and presenting a strong hydrophobicity [36,85,86]. For example, hydrophobic extracts from juca fruits were found to be more loaded into N-carboxybutyl chitosan than into two other commercial dressings due to its higher hydrophobicity and to favorable interactions, thus increasing the partitioning coefficient of the molecules in this matrix [36].…”

Section: {Polymer + Api}: Affinitymentioning

confidence: 91%

Drug loading of polymer implants by supercritical CO 2 assisted impregnation: A review

Champeau

Thomassin

Tassaing

et al. 2015

Journal of Controlled Release

211

137

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Section: {Polymer + Api}: Affinitymentioning

confidence: 91%

Drug loading of polymer implants by supercritical CO 2 assisted impregnation: A review

Champeau

Thomassin

Tassaing

et al. 2015

Journal of Controlled Release

211

137

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“…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: 94%

“…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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Effects of supercritical carbon dioxide treatment on the morphology of poly(l‐lactide)

Tsutsumi

Watanabe

Tokumaru

et al. 2016

J of Applied Polymer Sci

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Synthetic l‐lactide random copolymers can be employed as controlled release materials when prepared using supercritical carbon dioxide (scCO2), since they are biodegradable via hydrolysis. To determine the effects of thermal properties on polymer performance following scCO2 processing, three types of poly(l‐lactide) having different properties were assessed. The Tm of one poly(l‐lactide) sample (H‐100) was found to be approximately 170 °C over the processing pressure range from 8 to 18 MPa, while a second sample (H‐440) also showed a constant value of approximately 152 °C. In contrast, the poly(l‐lactide) REVODE exhibited a Tm of 146 °C prior to processing but a higher value of 147 °C following treatment at 8 MPa. Unlike the H‐100 and H‐440, the Tm value of the REVODE tended to decrease with increasing pressure. The Tg values increased greatly under mild conditions of 8 MPa pressure and a temperature of 40 °C. In particular, the Tg values for the H‐440 and REVODE increased by 4 °C and 5 °C, respectively. All Tg values were lowest at 12 MPa and increased with increasing processing pressure, although the effect of processing temperature was minimal. The Χc DSC of the H‐100 was 18% initially but increased to 20% upon scCO2 processing at 40 °C and 14 MPa, and showed further increases at higher processing temperatures. Although the relationship between processing temperature and Χc DSC values for the H‐440 showed the same trend as observed with the H‐100, a different trend was seen for the REVODE. The Χc XRD values obtained from the XRD analyses differed from the values generated by DSC analysis, and showed a maximum degree of crystallinity following processing at 80 °C both with and without scCO2 treatment. ATR FT‐IR analyses identified peaks due to semicrystalline regions in poly(l‐lactide) samples treated with scCO2, even when applying low temperatures. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 44006.

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Incorporation of l-lactide random copolymers with Japanese cypress oil (α-pinene) using supercritical carbon dioxide

Cited by 15 publications

References 30 publications

Drug loading of polymer implants by supercritical CO 2 assisted impregnation: A review

Drug loading of polymer implants by supercritical CO 2 assisted impregnation: A review

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

Effects of supercritical carbon dioxide treatment on the morphology of poly(l‐lactide)

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