On the thermal degradation of poly‐ε‐caprolactone

Iwabuchi, Susumu; Jaacks, V.; Kern, Werner

doi:10.1002/macp.1976.021770910

Cited by 33 publications

(24 citation statements)

References 5 publications

(1 reference statement)

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“…Several groups investigated the thermal stability of PCL in the high temperature region by using various analytical techniques, although there is no consistency in the mechanism. [57][58][59][60][61][62] We also prepared PCL (M n ¼ 113 000, M w =M n ¼ 1.6) by a ring-opening polymerization of e-CL in the presence of Zn(CH 2 CH 3 ) 2 /H 2 O catalyst. [62] Figure 12 shows the TGA and DTG curves of purified PCL at a heating rate of 10 8C Á min À1 under nitrogen atmosphere.…”

Section: Thermal Degradation Processes Of Poly(e-caprolactone)mentioning

confidence: 99%

Thermal Degradation of Environmentally Degradable Poly(hydroxyalkanoic acid)s

Abe

2006

Macromolecular Bioscience

104

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Aliphatic polyesters have attracted industrial attention as environmentally degradable thermoplastics to be used for a wide range of applications. Besides intensive studies on the biodegradability of aliphatic polyesters, understanding of the thermal stability has importance for processing, application, and recycling. The details of thermal degradation processes of five types of aliphatic polyesters; namely, poly(L-lactide), poly(3-hydroxybutyric acid), poly(4-hydroxybutyric acid), poly(delta-valerolactone), and poly(epsilon-caprolactone), were investigated by means of several thermoanalytical techniques under both isothermal and non-isothermal conditions. In this feature article, the thermal degradation behaviors of aliphatic polyesters with different numbers of carbon atoms in the main chain of the monomeric unit are reviewed. In addition, the effects of chain-end structure and residual metal compounds on the thermal degradation processes of aliphatic polyesters consisting of hydroxyalkanoic acid monomeric units are presented. Schemes of thermal degradation reaction of poly(hydroxyalkanoic acid)s.

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Section: Thermal Degradation Processes Of Poly(e-caprolactone)mentioning

confidence: 99%

Thermal Degradation of Environmentally Degradable Poly(hydroxyalkanoic acid)s

Abe

2006

Macromolecular Bioscience

104

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“…Thermal degradation of poly(caprolactone) at 220°C was recently investigated (23). It proceeds by a zippingoff mechanism yielding monomeric caprolactone without change in reduced viscosity up to a weight loss of 53%.…”

Section: Poly(e-caprolactone)mentioning

confidence: 99%

Biodegradable Polymers for Sustained Drug Delivery

Schindler

Jeffcoat

Kimmel

et al. 1977

Contemporary Topics in Polymer Science

180

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SYNOPSISMost studies of the sustained release of drugs from subdermally implanted polymer devices have centered on the use of silicone rubber. However, the use of this polymer has serious limitations because of its nonbiodegradability. The depleted capsule has to be surgically removed if one is to eliminate potential problems associated with non-degradable foreign substances remaining in the body for an indefinite length of time. The development of polymer systems which combine the release properties of silicone rubber with biodegradability will represent a significant advance in the technique of controlled release of contraceptives. The polymer system selected for Dur investigations were polyesters comprising homo and copolymers of glycolide, dilactide, s-caprolactone, and s-decalactone. These polymers were found to undergo random hydrolytic degradation under in vitro and in vivo conditions. The polymers were characterized by their rates of biodegradation and their release parameters for contraceptive steroids. Long time release rates of steroids from monolithic and reservoir devices were determined. Especially poly(scaprolactone) was found to come close to meeting the requirements of a biodegradable reservoir device for controlled drug delivery, with a useful lifespan approaching one year. Copolymers of s-caprolactone and racemic dilactide are more permeable than poly(s-caprolactone) and are of value for biodegradable devices with shorter than one year lifespan.

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“…The family of aliphatic polyesters including PHB (31), poly-P-propiolactone (38), and poly-a-methyl-P-propiolactone (31) and the aromatic polyesters such as poly(ethy1ene terephthalate) (39) strate a typical ester-pyrolysis mechanism (or intramolecular cis-elimination) (40) in which a cyclic transition state (I) is involved followed by synchronous breakage of the C(a)-0 and C(P)-H bonds. Because of the similarity in chemical structures between PHB and HV-HB heteropolymer one can expect that this heteropolymer undergoes the same pyrolysis mechanism as proposed for these polyesters.…”

Section: Pyrolysis Mechanismsmentioning

confidence: 99%

Pyrolysis of bacterial polyalkanoates

Morikawa¹,

Marchessault²

1981

Can. J. Chem.

141

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HIROMICHI MORIKAWA and ROBERT H. MARCHESSAULT. Can. J. Chem. 59,2306(1981. Pyrolysis products from bacterial polyesters, poly-P-hydroxybutyrate (PHB), and froma heteropolyester(P-hydroxyvalerate and P-hydroxybutyrate) were identified. Different physical forms of PHB were studied: PHB purified by dissolution in chloroform, native granules of PHB, and PHB in bacterial cells. The products were characterized by gc, ms, and nmr analysis. The yield of crotonic acid obtained by the pyrolysis of purified PHB was 60 to 65%. Pyrolysis of PHB native granules yielded crotonic acid as well as oligomers of PHB with a terminal crotonate. Upon direct pyrolysis of dry bacterial cells, the yield of crotonic acid was 20 to 25% of the PHB in the cells. From the heteropolymer, 2-pentenoic acid and terminally unsaturated oligomers of polyhydroxyvalerate were obtained. The usefulness of the pyrolysis method for obtaining vinyl compounds from bacterial cultures containing polyalkanoates is discussed.HIROMICHI MORIKAWA et ROBERT H. MARCHESSAULT. Can. J. Chem. 59,2306(1981. On a identifie les produits provenant de la pyrolyse des polyesters bactiriens poly-P-hydroxybutyrate (PHB) et du polyester heterogene (P-hydroxyvalirate e t P-hydroxybutyrate). On a Ctudie les differentes formes physiques du PHB: le PHB purifie par dissolution dans le chloroforme, les granules naturels de PHB et le PHB des cellules bacteriennes. On acaracterise les produits par chromatographie en phase gazeuse, par spectrometrie de masse et par la rmn. Le rendement en acide crotonique provenant de la pyrolyse du PHB purifie est de 60 a 65%. L a pyrolyse des granules naturels de PHB conduit aussi bien 5 I'acide crotonique qu'a des oligomkres du PHB avec un crotonate terminal. La pyrolyse directe des cellules bacteriennes s6ches conduit a un rendement en acide crotonique qui represente 20 a 25% du PHB contenu dans les cellules. On a obtenu du polymere hkterogkne I'acide penten-2 I oique et des oligomkres du polyhydroxyvalerate insaturk en position terminale. On discute de I'utilite de la methode de pyrolyse en I vue d'obtenir des composes vinyliques a partir des cultures bacteriennes contenant des polyalcanoates.

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On the thermal degradation of poly‐ε‐caprolactone

Cited by 33 publications

References 5 publications

Thermal Degradation of Environmentally Degradable Poly(hydroxyalkanoic acid)s

Thermal Degradation of Environmentally Degradable Poly(hydroxyalkanoic acid)s

Biodegradable Polymers for Sustained Drug Delivery

Pyrolysis of bacterial polyalkanoates

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