Aliphatic polyesters : Abiotic and biotic degradation and degradation products

This paper reviews the degradation behavior of aliphatic polyesters of current interest, including polylactide, polycaprolactone, poly(3-hydroxybutyrate) and their copolymers. Special focus is given to degradation products formed in different abiotic and biotic environments. The influence of processing and processing additives on the properties and degradation behavior is also briefly discussed.

[1]  S. Huang,et al.  Polycaprolactone degradation by mixed and pure cultures of bacteria and a yeast , 1983 .

[2]  A. Albertsson,et al.  Influence of Processing Additives on the Degradation of Melt-Pressed Films of Poly(e-Caprolactone) and Poly(Lactic Acid) , 1998 .

[3]  E. Thomas,et al.  Biodegradable Polymers and Packaging , 1993 .

[4]  D. Jendrossek,et al.  Enzymatic Degradation of Bacterial Poly(3-hydroxybutyrate) by a Depolymerase from Pseudomonas lemoignei , 1996 .

[5]  A. Albertsson,et al.  Influence of Processing Parameters on the Mass Crystallinity of Poly(3‐hydroxybutyrate‐ co‐3‐hydroxyvalerate) , 1997 .

[6]  J. Sanders,et al.  Poly(hydroxybutyrate) in vivo: NMR and x-ray characterization of the elastomeric state , 1991 .

[7]  D. Grijpma,et al.  (CO)POLYMERS OF L-LACTIDE .1. SYNTHESIS, THERMAL-PROPERTIES AND HYDROLYTIC DEGRADATION , 1994 .

[8]  M. L. Focarete,et al.  Polymer Blends of Natural Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and a Synthetic Atactic Poly(3-hydroxybutyrate). Characterization and Biodegradation Studies , 1997 .

[9]  A. Albertsson,et al.  Synthesis and Characterization of Biodegradable Homopolymers and Block Copolymers Based on 1,5-Dioxepan-2-one , 1994 .

[10]  R. Lenz,et al.  Degradation of poly(β-hydroxyalkanoates) and polyolefin blends in a municipal wastewater treatment facility , 1993 .

[11]  R. Vinopal,et al.  Fusarium polycaprolactone depolymerase is cutinase , 1996, Applied and environmental microbiology.

[12]  Hideo Tanaka,et al.  Physical properties and biodegradability of blends containing poly(ε-caprolactone) and tropical starches , 1996 .

[13]  Robert Langer,et al.  Copolymerization and Degradation of Poly(lactic acid-co-lysine) , 1995 .

[14]  R. Barsacchi,et al.  The biodegradation of poly (ester-ether-ester) block copolymers in a cellular environmentin vitro , 1994 .

[15]  Y. Oda,et al.  Microbial degradation of poly(3-hydroxybutyrate) and polycaprolactone by filamentous fungi , 1995 .

[16]  Y. Doi,et al.  Production of copolyesters of 3-hydroxybutyrate and 3-hydroxyvalerate by Alcaligenes eutrophus from butyric and pentanoic acids , 1988, Applied Microbiology and Biotechnology.

[17]  Y. Ikada,et al.  Effects of residual monomer on the degradation of DL‐lactide polymer , 1998 .

[18]  Michel Vert,et al.  Structure-property relationships in the case of the degradation of massive poly(α-hydroxy acids) in aqueous media , 1990 .

[19]  R. Gross,et al.  Composting studies of poly (β-hydroxybutyrate-co-/gb-hydroxyvalerate) , 1996 .

[20]  A. Albertsson,et al.  Effect of abiotic factors on the degradation of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in simulated and natural composting environments , 1999 .

[21]  D. Jendrossek,et al.  1H NMR imaging study of enzymatic degradation in poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Evidence for preferential degradation of the amorphous phase by PHB depolymerase B from Pseudomonas lemoignei , 1997 .

[22]  Y. Doi,et al.  Hydrolytic degradation of microbial poly(3-hydroxybutyrate-co-3-hydroxyvalerate) fibers , 1990 .

[23]  A. Albertsson,et al.  Influence of low molecular weight lactic acid derivatives on degradability of polylactide , 2000 .

[24]  M. Vert,et al.  Structural characterization and hydrolytic degradation of solid copolymers of d,l-lactide-co-ε-caprolactone by Raman spectroscopy , 2000 .

[25]  Suming Li,et al.  Enzymatic degradation of stereocopolymers derived from L-, DL- and meso-lactides , 2000 .

[26]  J. Lunt Large-scale production, properties and commercial applications of polylactic acid polymers , 1998 .

[27]  C. Chu Hydrolytic degradation of polyglycolic acid: Tensile strength and crystallinity study , 1981 .

[28]  T. Saito,et al.  An extracellular poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis. , 1982, European journal of biochemistry.

[29]  A. Albertsson,et al.  Rapid (bio)degradation of polylactide by mixed culture of compost microorganisms—low molecular weight products and matrix changes , 2000 .

[30]  A. Albertsson,et al.  Influence of processing parameters on the molecular weight and mechanical properties of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) , 1997 .

[31]  A. Albertsson,et al.  Degradable high-molecular-weight random copolymers, based on ε-caprolactone and 1,5-dioxepan-2-one, with non-crystallizable units inserted in the crystalline structure , 1995 .

[32]  A. Albertsson,et al.  Trapping of volatile low molecular weight photoproducts in inert and enhanced degradable LDPE , 1998 .

[33]  M. Asano,et al.  Direct copolymerization of l-lactic acid with δ-valerolactone in the absence of catalysts , 1988 .

[34]  R. G. Sinclair The Case for Polylactic Acid as a Commodity Packaging Plastic , 1996 .

[35]  A. Pennings,et al.  Preparation and properties of absorbable fibres from l-lactide copolymers , 1993 .

[36]  M. Vert,et al.  Hydrolytic degradation of films prepared from blends of high and low molecular weight poly(DL-lactic acid)s. , 1996, Journal of biomedical materials research.

[37]  Yutaka Tokiwa,et al.  Degradation of polycaprolactone at 50 °C by a thermotolerant Aspergillus sp. , 2000, Biotechnology Letters.

[38]  S. Girois,et al.  Polym. Degrad. Stab. , 1996 .

[39]  Sung‐Kwon Hong,et al.  Effect of orientation on the biodegradability of uniaxially stretched aliphatic copolyester films , 1997 .

[40]  Y. Doi,et al.  ENZYMATIC DEGRADATION OF POLY(R)-3-HYDROXYBUTYRATE BY COMAMONAS TESTOSTERONI ATSU OF SOIL BACTERIUM , 1994 .

[41]  A. Albertsson,et al.  Properties of injection moulded starch/synthetic polymer blends—I. Effect of processing parameters on physical properties , 1996 .

[42]  A. Albertsson,et al.  Synthesis of copolymers of 1,3-dioxan-2-one and oxepan-2-one using coordination catalysts , 1994 .

[43]  Yoshiharu Doi,et al.  Thermal degradation of microbial copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate) , 1990 .

[44]  J. Mergaert,et al.  Microbial Degradation of Poly(3-Hydroxybutyrate) and Poly(3-Hydroxybutyrate-Co-3-Hydroxyvalerate) in Soils , 1994, Applied and environmental microbiology.

[45]  B. Kolb Multiple headspace extraction—A procedure for eliminating the influence of the sample matrix in quantitative headspace, gas chromatography , 1982 .

[46]  R. Lenz,et al.  Characterization and enzymatic degradation of a cross-linked bacterial polyester , 1994 .

[47]  P. Holmes,et al.  The thermal degradation of poly(-(d)-β-hydroxybutyric acid): Part 2—Changes in molecular weight , 1984 .

[48]  A. Albertsson,et al.  The influence of processing induced differences in molecular structure on the biological and non-biological degradation of poly-(3-hydroxybutyrate-co-3-hydroxyvalerate), P(3-HB-co-3-HV) , 1999 .

[49]  S. Perren,et al.  Tissue response and in vivo degradation of selected polyhydroxyacids: polylactides (PLA), poly(3-hydroxybutyrate) (PHB), and poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHB/VA). , 1993, Journal of biomedical materials research.

[50]  Michel Vert,et al.  Structure-property relationships in the case of the degradation of massive aliphatic poly-(α-hydroxy acids) in aqueous media , 1990 .

[51]  Y. Tokiwa,et al.  Confirmation of anaerobic poly(2-oxepanone) degrading microorganisms in environments , 1994 .

[52]  J. Ramsay,et al.  The Influence of Thermal History on the Properties of Pol y( 3- hydroxybutyrate-co- 1 20/0-3-hydroxyvaIerate) , 1996 .

[53]  P. Holmes,et al.  The thermal degradation of poly(-(d)-β-hydroxybutyric acid): Part 1—Identification and quantitative analysis of products , 1984 .

[54]  A. Albertsson,et al.  Solid phase microextraction (SPME) as an effective means to isolate degradation products in polymers , 1997 .

[55]  Y. Doi,et al.  Kinetics and mechanism of synthesis and degradation of poly(3-hydroxybutyrate) in alcaligenes eutrophus , 1992 .

[56]  M. Vert,et al.  Capillary zone electrophoresis to study the hydrolytic degradation of a novel gluconic/glycolic/lactic acid copolymer , 2000 .

[57]  T. Karjalainen,et al.  Biodegradable lactone copolymers. III. Mechanical properties of ε‐caprolactone and lactide copolymers after hydrolysis in vitro , 1996 .

[58]  A. Albertsson,et al.  Dicarboxylic Acids and Ketoacids Formed in Degradable Polyethylenes by Zip Depolymerization through a Cyclic Transition State , 1997 .

[59]  H. Okada,et al.  New method for analysis of biodegradable polyesters by high-performance liquid chromatography after alkali hydrolysis. , 1992, Biomaterials.

[60]  Suming Li,et al.  Poly(lactic acid) degradation in soil or under controlled conditions , 1996 .

[61]  Donnie F. Williams Enzymic Hydrolysis of Polylactic Acid , 1981 .

[62]  D. Grijpma,et al.  Synthesis and hydrolytic degradation behaviour of high-molecular-weight l-lactide and glycolide copolymers , 1990 .

[63]  A. Albertsson,et al.  Copolymers of 1,5-dioxepan-2-one and L- or D,L-dilactide: Hydrolytic degradation behavior , 1994 .

[64]  A. Albertsson,et al.  Identification by headspace gas chromatography-mass spectrometry of in vitro degradation products of homo-and copolymers of L- and D,L-lactide and 1,5-dioxepan-2-one , 1994 .

[65]  Ferdinand Rodriguez,et al.  Microbial degradation of polyesters: Polycaprolactone degraded by P. pullulans† , 1974 .

[66]  Y. Doi,et al.  Enzymatic Degradation and Adsorption on Poly[(R)-3-hydroxybutyrate] Single Crystals with Two Types of Extracellular PHB Depolymerases from Comamonas acidovorans YM1609 and Alcaligenes faecalis T1 , 1997 .

[67]  Susceptibility of starch-filled and starch-based LDPE to oxygen in water and air , 1997 .

[68]  P. Barham,et al.  The effect of water on the crystallization of thin films of poly(hydroxybutyrate) , 1997 .

[69]  Ross R. Muth,et al.  Biodegradable polymers for use in surgery—polyglycolic/poly(actic acid) homo- and copolymers: 1 , 1979 .

[70]  J. Seppälä,et al.  Modification of poly(L-lactides) by blending: Mechanical and hydrolytic behavior , 1996 .

[71]  X. Jing,et al.  Enzymatic degradation of poly(ε-caprolactone) film in phosphate buffer solution containing lipases , 1997 .

[72]  G. L. Woo,et al.  Synthesis and characterization of a novel biodegradable antimicrobial polymer. , 2000, Biomaterials.

[73]  E. Chiellini,et al.  Evaluation of biodegradability of poly(ε-caprolactone)/poly(ethylene terephthalate) blends , 1996 .

[74]  A. Albertsson,et al.  Influence of molecular structure on the degradation mechanism of degradable polymers: In vitro degradation of poly(trimethylene carbonate), poly(trimethylene carbonate-co-caprolactone), and poly(adipic anhydride) , 1995 .

[75]  A. Södergård,et al.  Hydrolytic degradation of peroxide modified poly(L-lactide) , 1996 .

[76]  R. M. Lafferty,et al.  A rapid gas chromatographic method for the determination of poly-β-hydroxybutyric acid in microbial biomass , 1978, European journal of applied microbiology and biotechnology.

[77]  S. Huang,et al.  The effects of primary structure on the degradation of poly(ɛ-caprolactone)/poly(l-lactide) block copolymers , 1998 .

[78]  Y. Ikada,et al.  Blends of aliphatic polyesters. III. Biodegradation of solution-cast blends from poly(L-lactide) and poly(ε-caprolactone) , 1998 .

[79]  Michel Vert,et al.  Complexity of the hydrolytic degradation of aliphatic polyesters , 1997 .

[80]  P A Holmes,et al.  Applications of PHB - a microbially produced biodegradable thermoplastic , 1985 .

[81]  A. Albertsson,et al.  Gas chromatographic, liquid chromatographic and gas chromatographic-mass spectrometric identification of degradation products in accelerated aged microbial polyhydroxyalkanoates , 1994 .

[82]  Y. Doi,et al.  Enzymatic degradation of poly(hydroxyalkanoates) by a marine bacterium , 1993 .

[83]  A. Albertsson,et al.  Controlled ring-opening polymerization of L-lactide and 1,5-dioxepan-2-one forming a triblock copolymer , 2000 .

[84]  E. Chiellini,et al.  Review : Biodegradability of Synthetic Polymers for Medical and Pharmaceutical Applications: Part 2—Backbone Hydrolysis , 1987 .

[85]  M. Kimura,et al.  Effects of soil conditions on biodegradation of plastics and responsible microorganisms , 1994 .

[86]  Suming Li,et al.  Hydrolytic degradation characteristics of aliphatic polyesters derived from lactic and glycolic acids. , 1999 .

[87]  T. Suortti,et al.  Microbial degradation of poly-(l-lactic acid) oligomers , 1998 .

[88]  Y. Doi Biodegradable Plastics and Polymers , 1994 .

[89]  K. Nakasaki,et al.  Effects of temperature and inoculum on the degradability of poly-ε-caprolactone during composting , 1998 .

[90]  H. Abe,et al.  Physical Properties and Enzymic Degradability of Copolymers of (R)-3-Hydroxybutyric and 6-Hydroxyhexanoic Acids , 1995 .

[91]  B. Tighe,et al.  Polymers for biodegradable medical devices. V. Hydroxybutyrate-hydroxyvalerate copolymers: effects of polymer processing on hydrolytic degradation. , 1990, Biomaterials.

[92]  C. Migliaresi,et al.  In vitro degradation of poly(L‐lactic acid) fibers produced by melt spinning , 1997 .

[93]  R. Gross,et al.  Enzymatic degradability of poly(lactide) : Effects of chain stereochemistry and material crystallinity , 1996 .

[94]  J. P. Bell,et al.  Fungal degradation of polycaprolactones , 1983 .

[95]  D. Pichora,et al.  An Investigation of Poly(lactic acid) Degradation , 1994 .

[96]  E. Schacht,et al.  Synthesis and environmental degradation of polyesters based on poly (ε-caprolactone) , 1996 .

[97]  H. Tanaka,et al.  Polylactide Degradation by an Amycolatopsis sp , 1997, Applied and environmental microbiology.

[98]  H. Abe,et al.  Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) , 1995 .

[99]  A. Albertsson,et al.  Solid-phase extraction and subsequent gas chromatography-mass spectrometry analysis for identification of complex mixtures of degradation products in starch-based polymers , 1996 .

[100]  T. Karjalainen,et al.  Biodegradable lactone copolymers.II.Hydrolytic study of e-caprolactone and lactide copolymers , 1996 .

[101]  C. Migliaresi,et al.  Dynamic mechanical and calorimetric analysis of compression-molded PLLA of different molecular weights : effect of thermal treatments , 1991 .

[102]  Michel Vert,et al.  STRUCTURE – PROPERTY RELATIONSHIP IN THE CASE OF THE DEGRADATION OF MASSIVE ALIPHATIC POLY – (-HYDROXY ACIDS) IN AQUEOUS MEDIA, PART 1: DEGRADATION OF LACTIDE - GLYCOLIDE COPOLYMERS: PLA 37.5 GA 25 AND PLA 75 GA 25 , 1990 .

[103]  S. Shalaby,et al.  Synthesis and some properties of isomorphic copolymers of ϵ‐caprolactone and 1,5‐dioxepan‐2‐one , 1989 .

[104]  P. Törmälä,et al.  Surgical applications of biodegradable polymers in human tissues , 1989 .

[105]  A. Cerutti,et al.  Physical state and biodegradation behavior of starch-polycaprolactone systems , 1995 .

[106]  A. Albertsson,et al.  Chemical and morphological changes of environmentally degradable polyethylene films exposed to thermo-oxidation , 1999 .

[107]  C. David,et al.  Biodegradation of polycaprolactone and its blends with poly(vinylalcohol) by micro-organisms from a compost of house-hold refuse , 1997 .

[108]  R. Gross,et al.  Citrate esters as plasticizers for poly(lactic acid) , 1997 .

[109]  A. Albertsson,et al.  Effect of processing additives on (bio)degradability of film-blown poly(ε-caprolactone) , 1998 .

[110]  J. Feijen,et al.  In vitro degradation of glycine/DL-lactic acid copolymers. , 1990, Journal of biomedical materials research.

[111]  Y. Doi,et al.  Biodegradation of microbial polyesters in the marine environment , 1992 .

[112]  Y. Doi,et al.  Structure of native poly(3-hydroxybutyrate) granules characterized by X-ray diffraction , 1990 .

[113]  Y. Tokiwa,et al.  Biological recycling of plastics containing ester bonds , 1992 .

[114]  M. Vert,et al.  Capillary electrophoresis to analyze water-soluble oligo(hydroxyacids) issued from degraded or biodegraded aliphatic polyesters , 1996 .

[115]  C. David,et al.  Biodegradation of polycaprolactone by micro-organisms from an industrial compost of household refuse , 1994 .

[116]  A. Albertsson,et al.  PY-GC/MS an effective technique to characterizing of degradation mechanism of poly (L-lactide) in the different environment , 2000 .

[117]  A. M. Reed,et al.  Biodegradable polymers for use in surgery — poly(glycolic)/poly(Iactic acid) homo and copolymers: 2. In vitro degradation , 1981 .

[118]  Hatem Fessi,et al.  In vitro degradation of nanospheres from poly(D,L-lactides) of different molecular weights and polydispersities , 1996 .

[119]  H. Abe,et al.  Synthesis and Characterization of Poly[(R,S)-3-hydroxybutyrate-b-6-hydroxyhexanoate] as a Compatibilizer for a Biodegradable Blend of Poly[(R)-3-hydroxybutyrate] and Poly(6-hydroxyhexanoate) , 1994 .

[120]  S. Jacobsson,et al.  Analysis of volatile organic compounds in polymers by dynamic headspace—multi-dimensional gas chromatography —mass spectrometry , 1987 .

[121]  Stephen P. McCarthy,et al.  Polylactide stereochemistry: effect on enzymic degradability , 1994 .

[122]  M. L. Focarete,et al.  Further Evidence of Crystallinity-Induced Biodegradation of Synthetic Atactic Poly(3-hydroxybutyrate) by PHB-Depolymerase A from Pseudomonas lemoignei. Blends of Atactic Poly(3-hydroxybutyrate) with Crystalline Polyesters , 1998 .

[123]  Stephen P. McCarthy,et al.  Effects of physical aging, crystallinity, and orientation on the enzymatic degradation of poly(lactic acid) , 1996 .

[124]  J. Pawliszyn,et al.  NEW SOLVENT-FREE SAMPLE PREPARATION TECHNIQUES : BASED ON FIBER AND POLYMER TECHNOLOGIES , 1994 .

[125]  J. P. Bell,et al.  Scanning electron microscopic visualization of biodegradation of polycaprolactones by fungi , 1981 .

[126]  Suming Li,et al.  Degradation of L- and DL-Lactic Acid Oligomers in the Presence of Fusarium moniliforme and Pseudomonas putida* , 1996 .

[127]  C. Pettigrew,et al.  Aerobic Biodegradation of Synthetic and Natural Polymeric Materials: A Component of Integrated Solid-Waste Management , 1995 .

[128]  Yong Xu,et al.  In vitro degradation of poly(caprolactone), poly(lactide) and their block copolymers: influence of composition, temperature and morphology , 1997 .

[129]  Y. Doi,et al.  Enzymatic degradation of microbial poly(3-hydroxyalkanoates) , 1994 .

[130]  A. Albertsson,et al.  The biodegradation of amorphous and crystalline regions in film-blown poly(ε-caprolactone) , 2000 .

[131]  M. Vert,et al.  Abiotic aging of water- soluble 3- hydroxybutyric acid oligomers as monitored by capillary zone electrophoresis , 1997, Journal of environmental polymer degradation.

[132]  A. Albertsson,et al.  Changes in chemical and thermal properties of the tri-block copolymer poly(L-lactide-b-1,5-dioxepan-2-one-b-L-lactide) during hydrolytic degradation , 2000 .

[133]  M. Asano,et al.  Synthesis of copoly(d,l-lactic acid) with relatively low molecular weight and in vitro degradation , 1989 .

[134]  M. Vert,et al.  Monitoring of the poly(d,l-lactic acid) degradation by-products by capillary zone electrophoresis , 1995 .

[135]  H. Mitomo,et al.  Enzymatic degradation of radiation crosslinked poly(ε–caprolactone) , 1998 .

[136]  A. Albertsson,et al.  Weight losses and molecular weight changes correlated with the evolution of hydroxyacids in simulated in vivo degradation of homo-and copolymers of PLA and PGA , 1996 .

[137]  P. Halling,et al.  Preparation and chromatographic analysis of poly(3-hydroxybutyrate) hydrolysis products , 1988 .

[138]  Y. Tokiwa,et al.  Hydrolysis of polycaprolactone fibers by lipase: Effects of draw ratio on enzymatic degradation , 1995 .

[139]  Suming Li,et al.  Hydrolytic degradation of devices based on poly(DL-lactic acid) size-dependence. , 1995, Biomaterials.

[140]  Y. Inoue,et al.  Kinetics of surface hydrolysis of poly[(R)-3-hydroxybutyrate] film by PHB depolymerase from Alcaligenes faecalis T1 , 1995 .

[141]  M. Vert,et al.  Capillary zone electrophoresis in normal or reverse polarity separation modes for the analysis of hydroxy acid oligomers in neutral phosphate buffer. , 1998, Journal of Chromatography B: Biomedical Sciences and Applications.

[142]  A. Albertsson,et al.  Random copolymers of 1,5-dioxepan-2-one , 1998 .

[143]  Y. Ikada,et al.  Degradation of high molecular weight poly(L-lactide) in alkaline medium. , 1995, Biomaterials.

[144]  B. Tighe,et al.  Polymers for biodegradable medical devices. II. Hydroxybutyrate-hydroxyvalerate copolymers: hydrolytic degradation studies. , 1987, Biomaterials.

[145]  A. Mikos,et al.  Degradation of polydispersed poly(L-lactic acid) to modulate lactic acid release. , 1995, Biomaterials.

[146]  S. Gogolewski,et al.  Enhancement of the mechanical properties of polylactides by solid-state extrusion. I. Poly(D-lactide). , 1996, Biomaterials.

[147]  H. Abe,et al.  Evaluation of biodegradabilities of biosynthetic and chemosynthetic polyesters in river water , 1996 .

[148]  B. Buchholz Analysis and characterization of resorbable dl-lactide-trimethylene carbonate copolyesters , 1993 .

[149]  A. Pennings,et al.  General crystallization behaviour of poly(l-lactic acid) , 1980 .