Amphiphilic Poly(ε-caprolactone)–Poly(vinyl alcohol) Block Copolymer: Preparation from a Bifunctional Initiator

Zhou, Jin; Takasu, Akinori; Inai, Yoshihito; Hirabayashi, Tadamichi

doi:10.1295/polymj.36.182

Cited by 18 publications

(8 citation statements)

References 18 publications

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“…However, when the [ϵ‐CL]/[PHpr10] composition ratio was greater than 50, the block copolymers also exhibited a decreasing melting temperature ( T m ) in the range of 53–45 °C with the increasing length of the PCL block. T m of the copolymers was slightly lower than that of PCL ( T m = 60 °C),29 indicating that the presence of PHpr blocks decreased the crystallinity of the copolymer with respect to the PCL homopolymer. Similar results were observed in the macroinitiator PHpr30 system: T g was −47 and T m was 45 °C when the molar ratio of [ϵ‐CL]/[PHpr30] = 96/1 was used (copolymer PCL‐ b ‐PHpr10‐ b ‐PCL10).…”

Section: Resultsmentioning

confidence: 86%

Synthesis and characterization of biodegradable A–B–A triblock copolymers containing poly(ϵ‐caprolactone) A blocks and poly(trans‐4‐hydroxy‐L‐proline) B blocks

Lee¹,

Lin²,

Yang³

et al. 2006

J. Polym. Sci. A Polym. Chem.

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were synthesized by ring-opening polymerization from dihydroxyl-terminated macroinitiator poly(trans-4-hydroxy-N-benzyloxycarbonyl-L-proline) (PHpr) and e-caprolactone (e-CL) with stannous octoate as the catalyst. The molecular weights were characterized with gel permeation chromatography and matrix-assisted laser desorption/ionization timeof-flight mass spectrometry. With an increase in the contents of e-CL incorporated into the copolymers, a decrease in the glass-transition temperature (T g ) was observed. The T g values of copoly(4-phenyl-e-caprolactone) and copoly(4-methyl-e-caprolactone) were higher than T g of copoly(e-caprolactone). Their micellar characteristics in an aqueous phase were investigated with fluorescence spectroscopy, dynamic light scattering, and transmission electron microscopy. The block copolymers formed micelles in the aqueous phase with critical micelle concentrations in the range of 1.00-1.36 mg L À1 . With higher molecular weights and hydrophobic components in the copolymers, a higher critical micelle concentration was observed. As the feed weight ratio of antitriptyline hydrochloride (AM) to the polymer increased, the drug loading increased. The micelles exhibited a spherical shape, and the average size was less than 250 nm. The in vitro hydrolytic degradation and controlled drug release properties of the triblock copolymers were also investigated. V V C 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: [4268][4269][4270][4271][4272][4273][4274][4275][4276][4277][4278][4279][4280] 2006

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Section: Resultsmentioning

confidence: 86%

Synthesis and characterization of biodegradable A–B–A triblock copolymers containing poly(ϵ‐caprolactone) A blocks and poly(trans‐4‐hydroxy‐L‐proline) B blocks

Lee¹,

Lin²,

Yang³

et al. 2006

J. Polym. Sci. A Polym. Chem.

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show abstract

“…This is due to the fact that the copolymers have a higher molecular weight when larger amounts of ε‐CL are incorporated into the macromolecular backbone, causing a decrease in T g , and an increased in T m s. The existence of two melting temperature very close together might be the primary and secondary crystallization of PCL. However, the T m of the copolymers was slightly lower than that of the PCL ( T m = 58.3°C),31 indicating that the presence of MPEG 12 ‐ b ‐PBOCL blocks decreases the crystallinity of the copolymer with respect to the PCL homopolymer by reducing the PCL chain mobility. The crystallinity of PCL is suppressed when its molecular weight is too low for MPEG 12 ‐ b ‐PBOCL 27 ‐ b ‐PCL 8 .…”

Section: Resultsmentioning

confidence: 91%

Synthesis and characterization of poly(ethylene glycol)‐b‐poly(ε‐caprolactone) copolymers with functional side groups on the polyester block

Chen¹,

Hua²,

Lee³

2012

J of Applied Polymer Sci

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This study reports the successful synthesis of amphiphilic MPEG-b-PCL based-block copolymers bearing benzyloxy and hydroxyl side groups on the PCL block by ring-opening polymerization of 4-benzyloxy-e-caprolactone (4-BOCL) and e-caprolactone (e-CL) with methoxy PEG (550 g mol À1 ) as the initiator and Tin(II) 2-ethylhexanoate (SnOct 2 ) as the catalyst. These copolymers were characterized by differential scanning calorimetry (DSC), 1 H NMR, and gel permeation chromatography. The thermal properties (T g and T m s) of the block copolymers depend on the polymer composition. Incorporating a greater amount of 4-BOCL and/or e-CL was incorporated into the macromolecular backbone causes a decrease T g , and an increase in T m s. The micellar characteristics in the aqueous phase were investigated by fluorescence spectroscopy, transmission electron microscopy (TEM), and dynamic light scattering (DLS). A lower critical micelle concentration (CMC) was observed in MPEG 12 -b-PBOCL 12 -b-PCL series, which have higher hydrophobic components in the copolymers. However, contrasting results were observed for MPEG 12 -b-PBOCL 27 -b-PCL systems. The micelle exhibited a spindle shape, with an average size of less than 200 nm. A weak drug entrapment efficiency and drugloading ability of these micelles were observed.

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“…However, when the composition ratio of [3-CL]/[PHpr10] beyond 23, the block copolymers also exhibited a T m in the range 52-56 8C and a T c decreased from 36 to K11 8C with increasing the length of PCL block. The T m of the copolymers were slightly lower than the PCL (T m Z60 8C) [24], indicating that the presence of PHpr blocks decreased the crystallinity of the copolymer with respect to the PCL homopolymer. Fig.…”

Section: Synthesis and Characterization Of Phpr10-b-pcl Copolymersmentioning

confidence: 90%

Synthesis of biodegradable poly(trans-4-hydroxy-N-benzyloxycarbonyl-l-proline)-block-poly(ε-caprolactone) copolymers and micellar characterizations

Lee

Yang

et al. 2005

Polymer

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Amphiphilic Poly(ε-caprolactone)–Poly(vinyl alcohol) Block Copolymer: Preparation from a Bifunctional Initiator

Cited by 18 publications

References 18 publications

Synthesis and characterization of biodegradable A–B–A triblock copolymers containing poly(ϵ‐caprolactone) A blocks and poly(trans‐4‐hydroxy‐L‐proline) B blocks

Synthesis and characterization of biodegradable A–B–A triblock copolymers containing poly(ϵ‐caprolactone) A blocks and poly(trans‐4‐hydroxy‐L‐proline) B blocks

Synthesis and characterization of poly(ethylene glycol)‐b‐poly(ε‐caprolactone) copolymers with functional side groups on the polyester block

Synthesis of biodegradable poly(trans-4-hydroxy-N-benzyloxycarbonyl-l-proline)-block-poly(ε-caprolactone) copolymers and micellar characterizations

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