A novel biodegradable poly(urethane ester) synthesized from poly(3-hydroxybutyrate) segments

Hori, Yoji; Suzuki, Motoki; Okeda, Yoshiki; Imai, Takashi; Sakaguchi, Minzo; Takahashi, Yōko; Yamaguchi, Akio; Akutagawa, Susumu

doi:10.1021/ma00045a046

Cited by 23 publications

(10 citation statements)

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“…The weak absorption at 720 cm −1 represents the -CH 2 -from HDI. With the PLA crystallization peak at 756 cm −1 , the peak strength weakened after the reaction [18]. Figure 3 shows the 1 H-NMR (500 MHz, TMS, CDCl 3 ) spectrum of the PLA prepolymer (Figure 3(a)) and the PLA chain extended with HDI (Figure 3(b)).…”

Section: Resultsmentioning

confidence: 99%

Preparation of Higher Molecular Weight Poly (L-lactic Acid) by Chain Extension

Liu

Jia

2013

International Journal of Polymer Science

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High molecular weight poly (lactic acid) (PLA) was obtained by chain extending with hexamethylene diisocyanate (HDI). The influences of the amount of chain extender, reaction time, and molecular weight changes of prepolymers on the poly(lactic acid) were investigated. PLA prepolymer with a viscosity, average molecular weight (Mη) of 2 × 104 g/mol was synthesized froml-lactide using stannous octoate as the catalyst. After 20 min of chain extension at 175°C, the resulting polymer hadMwof 20.3 × 104 g/mol andMnof 10.5 × 104 g/mol. Both FT-IR and1H-NMR verified that the structure of PLA did not change either before chain extending or after. The optically active characterized that the chain extending-product was left handed. DSC and XRD results showed that both theTgand the crystallinity of PLA were lowered by chain-extension reaction. The crystalline transformation happened in PLA after chain extending, crystallineα′form toαform.

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Section: Resultsmentioning

confidence: 99%

Preparation of Higher Molecular Weight Poly (L-lactic Acid) by Chain Extension

Liu

Jia

2013

International Journal of Polymer Science

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“…Natural polymers were also explored, e. g., collagen27) and poly(3-hydroxybutyric acid) (PHB) or poly[(3-hydroxybutyric acid)-co-(3-hydroxyvaleric acid)] (PHBIHV) [28][29][30][31][32][33][34][35][36][37][38]. Summarizing the reslts of these investigations, one is led to the conclusion that the plurality of demands on the implants cannot be met by the materials known to date39).…”

Section: Tab 1 Nentlymentioning

confidence: 99%

Synthesis of degradable, biocompatible, and tough block‐copolyesterurethanes

Hirt¹,

Neuenschwander²,

Suter³

1996

Macro Chemistry & Physics

117

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We describe the synthesis of micro-phase-segregated block-copolyesterurethanes from telechelic hydroxyterminated poly [ [(R)-3-hydroxybutyric acid]-co-[(R)-3-hydroxyvaleric acid]] (PHB-diol) as "hard segments" (i. e., crystallizable chain sections) and hydroxyterminated poly(ecapro1actone)-diethylene glycol-poly(8-caprolactone) (PCL-diol) or telechelic .hydroxyterminated pol y [(adipic acid)-alt-( 1,4-butanediol; diethylene glycol; ethylene glycol)] (Diorez") as "soft segments", with 2,2,4-triethylhexamethylene diisocyanate (TMDI) or methyl (S)-2,6-diisocyanatohexanoate (LDI). High molecular weights were obtained with or without catalyst, the properties of the polymers depending only slightly on the presence or absence of the catalyst. The materials thus obtained were investigated also with respect to their mechanical properties and it was found that Young's modulus directly depends on the fraction of crystallizable PHB-diol in the block copolymer while the type of non-crystallizable segment or diisocyanate had only a minor influence: Generally, the tensile strength increases and the elongation at break decreases with increasing content of PHB-diol. Around body temperature, these polymers exhibit only mild changes in their mechanical behavior. The chain length of the non-crystallizable segment indirectly influences the morphology and the mechanical properties of the polymers through changes in the phase-segregation behavior.

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“…When the shorter chain sequence of a prepolymer, especially the soft segment of the PVL sequence, is reacted with MDI, it produces a poly(urethane-ester) with a lower soft-segment composition. The lower soft segment is known to be resistant to decomposition through microorganisms, 24 and indeed the weight loss of poly(urethane-ester) synthesized from prepolymer with a VL/DP molar ratio of 10/1 was relatively low.…”

Section: Poly(urethane-ester)mentioning

confidence: 99%

The effect of the soft segment of prepolymers on properties of poly(urethane‐ester) and its biodegradability

Arcana

Bundjali

Hasan

et al. 2011

Polymer International

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The influence of soft‐segment prepolymers prepared through the polymerization of δ‐valerolactone (VL) and 2,2‐dimethyl‐1,3‐propandiol (DP) monomers on the structure and properties of poly(urethane‐ester) as well as its biodegradability were investigated. Poly(urethane‐ester) was prepared in two steps. The first step was the preparation of prepolymers with various chain lengths by polymerizing VL and DP monomers in the presence of a distannoxane catalyst at 100 °C under nitrogen atmosphere. The second step was the preparation of poly(urethane‐ester) by polymerizing 4,4′‐methylene‐bis(phenyl isocyanate) (MDI) and prepolymers with various chain lengths in the absence of catalysts. The poly(urethane‐ester) was characterized through an analysis of functional groups (FTIR), thermal properties (differential thermal analysis/TGA), mechanical properties (tensile tester), crystallinity (XRD) and biodegradability. An increased chain length of the prepolymer used in polymerization with MDI leads to an increase in the thermal properties and crystallinity of poly(urethane‐ester). However, the maximum biodegradability in the activated sludge was observed in the poly(urethane‐ester) prepared by polymerizing MDI and prepolymers with a molar VL/DP ratio of 20/1. The amorphous parts of polymers were more easily decomposed by microorganism enzymes than were the crystalline parts after an incubation period of 30 days. Copyright © 2011 Society of Chemical Industry

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A novel biodegradable poly(urethane ester) synthesized from poly(3-hydroxybutyrate) segments

Cited by 23 publications

References 1 publication

Preparation of Higher Molecular Weight Poly (L-lactic Acid) by Chain Extension

Preparation of Higher Molecular Weight Poly (L-lactic Acid) by Chain Extension

Synthesis of degradable, biocompatible, and tough block‐copolyesterurethanes

The effect of the soft segment of prepolymers on properties of poly(urethane‐ester) and its biodegradability

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