Synthesis and characterization of hydroxy-terminated [RS]-poly(3-hydroxybutyrate) and its utilization to block copolymerization with l-lactide to obtain a biodegradable thermoplastic elastomer

Hiki, Shigehiro; Miyamoto, Masatoshi; Kimura, Yoshiharu

doi:10.1016/s0032-3861(00)00086-0

Cited by 128 publications

(94 citation statements)

References 18 publications

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“…Blocks with different physical properties, for example, a soft, amorphous segment together with a hard semicrystalline one, can be used to modulate the thermal and mechanical material behaviour [4,[7][8][9]. The mechanical properties can be controlled by the hard/soft segment ratio [7] and copolymers with various morphologies such as solid, pasty and waxy states, can be obtained according to the monomer composition [6,10]. The soft phase provides elasticity and the degradation behaviour, whereas the rigid phase gives mechanical strength and also acts as a physical crosslinker [6].…”

Section: Introductionmentioning

confidence: 99%

“…The soft phase provides elasticity and the degradation behaviour, whereas the rigid phase gives mechanical strength and also acts as a physical crosslinker [6]. Polymerization of racemic monomer (R,S)-β-butyrolactone ((R,S)-BL) has given an atactic poly (R,S)-(β-butyrolactone) ((R,S)-PBL) with elastomeric properties because of its low crystallinity [7,11,12]. However, for its applications as biodegradable elastomer, it is necessary to decrease their creep behaviour.…”

Section: Introductionmentioning

confidence: 99%

“…However, for its applications as biodegradable elastomer, it is necessary to decrease their creep behaviour. This has been done by the introduction of a biodegradable hard segment, by means of the successive ring-opening polymerization of (R,S)-BL and L-lactide [7] or ε-caprolactone [8,13]. The resultant block copolymers, consisting of (R,S)-PBL as the soft segment and PLLA or PCL as the hard segment, could be the biodegradable thermoplastic elastomer.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, the choice of a proper initiator is another important parameter in the synthesis of polyesters. Many effective catalysts based on tincompounds, have been employed for this purpose [4,7,8,[13][14][15][16][17][18][19][20][21]. However, many are relatively toxic and impossible to remove completely from the synthesized material, this being undesirable for pharmaceutical or biomedical applications [2,6].…”

Section: Introductionmentioning

confidence: 99%

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Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Monsalve¹,

Contreras²,

Laredo³

et al. 2010

Express Polym. Lett.

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Abstract. Copolymers of racemic β-butyrolactone ((R,S)-BL) and ε-caprolactone (CL), were synthesized by ring-opening polymerization initiated by sodium hydride (NaH). The initiator exhibited a satisfactory catalytic activity, producing copolymers whose yields are greatly influenced by the feed monomer ratio, CL/BL. All polymers obtained were characterized by nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and wide angle X-rays scattering, WAXS. The molar composition of copolyesters determined by 1 H-NMR spectra, showed that the incorporation of CL is favoured over the incorporation of (R,S)-BL. Gel permeation chromatography and 13 C-NMR spectra indicated that CL/BL copolymers had block sequence distribution. The TGA analysis of copolymers showed that these copolymers are stable up to temperatures near 200°C, followed by a decomposition process in two steps; the first one is attributed to the (R,S)-BL block degradation and the second to the remaining PCL block. The crystallization process of these copolymers was studied by DSC and WAXS showing that the amorphous (R,S)-BL segments chains did not affect the crystallinity of the PCL blocks.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Monsalve¹,

Contreras²,

Laredo³

et al. 2010

Express Polym. Lett.

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“…This route uses the β-butyrolactone as reagent [23]. In this process, zinc and aluminum can be used as catalysts [32] and the polymer obtained shall possess chiral center in configuration in both R, as in S, being the last named PHB racemic compound [36]. Another method of obtaining is through natural plants and/or transgenic plants [11].…”

Section: Phb Synthesismentioning

confidence: 99%

From Obtaining to Degradation of PHB:Material Properties. Part I

et al. 2017

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This paper presents a review of the chemical, physical and morphological characteristics, as well as the existing applications and mechanisms for the production of poly (3-hydroxybutyrate). This biopolymer, which is obtained from renewable sources, degrades when exposed in biologically active environments and is biocompatible, that is, it is not rejected by the human body in health applications. However, in spite of presenting similar properties with some conventional plastics, the PHB exhibits fragile behavior and thermal instability when processed. The literature proposes the use of blends, the development of copolymers or the insertion of additives in an attempt to improve the mechanical and thermal properties of PHB. Key words: Biopolymers; polyhydroxyalkanoates (PHA); Polyhydroxybutyrate (PHB). Universidad EAFIT 269|From Obtaining to Degradation of PHB: Material Properties. Part I De la obtención a la degradación de PHB: Propiedades del material. Parte I ResumenEste artículo presenta una revisión de las características químicas, físicas y morfológicas, así como las aplicaciones y mecanismos existentes para la producción de poli(3-hidroxibutirato). Este biopolímero, que se obtiene a partir de fuentes renovables, se degrada cuando se expone en ambientes biológicamente activos y es biocompatible, es decir, no es rechazado por el cuerpo humano en aplicaciones de salud. Sin embargo, a pesar de presentar propiedades similares con algunos plásticos convencionales, el PHB exhibe comportamiento frágil e inestabilidad térmica cuando se procesa. La literatura propone el uso de mezclas, el desarrollo de copolímeros o la inserción de aditivos en un intento por mejorar las propiedades mecánicas y térmicas del PHB.Palabras clave: Biopolímeros; degradación de PHB; polihidroxialcanoato (PHA); polihidroxibutirato (PHB).

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Lipase-Catalyzed Transformation of Unnatural-Type Poly(3-hydroxybutanoate) into Reactive Cyclic Oligomer

Osanai¹,

Toshima²,

Yoshie³

et al. 2002

Macromol. Biosci.

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Synthesis and characterization of hydroxy-terminated [RS]-poly(3-hydroxybutyrate) and its utilization to block copolymerization with l-lactide to obtain a biodegradable thermoplastic elastomer

Cited by 128 publications

References 18 publications

Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

Ring-opening copolymerization of (R,S)-β-butyrolactone and ε-caprolactone using sodium hydride as initiator

From Obtaining to Degradation of PHB:Material Properties. Part I

Lipase-Catalyzed Transformation of Unnatural-Type Poly(3-hydroxybutanoate) into Reactive Cyclic Oligomer

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