Polylactic acid (PLA): Research, development and industrialization

Polylactide (PLA) is a biodegradable, aliphatic polyester derived from lactic acid. It has similar mechanical properties to polyethylene terephthalate, but has a significantly lower maximum continuous use temperature. PLA products can be recycled after use either by remelting and processing the material a second time or by hydrolyzing to lactic acid, the basic chemical. In this review, the technologies for polymerization of the lactic acid and the comparison of physical, thermal and mechanical properties, biodegradability, and biocompatibility of the PLA and copolymers with other similar polymers are described.

[1]  AjiokaMasanobu,et al.  Basic Properties of Polylactic Acid Produced by the Direct Condensation Polymerization of Lactic Acid , 2006 .

[2]  J. Gallucci,et al.  Coordination chemistry and reactivity of monomeric alkoxides and amides of magnesium and zinc supported by the diiminato ligand CH(CMeNC(6)H(3)-2,6-(i)Pr(2))(2). A comparative study. , 2002, Inorganic chemistry.

[3]  A. Södergård,et al.  Properties of lactic acid based polymers and their correlation with composition , 2002 .

[4]  P. Dubois,et al.  Macromolecular engineering of polylactones and polylactides , 1989 .

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

[6]  A. Janorkar,et al.  Poly(lactic acid) modifications , 2010 .

[7]  M. Doble,et al.  Biodegradation of aliphatic and aromatic polycarbonates. , 2008, Macromolecular bioscience.

[8]  Y. Ikada,et al.  Biodegradable polyesters for medical and ecological applications , 2000 .

[9]  S. M. Li,et al.  Bioresorbability and biocompatibility of aliphatic polyesters , 1992 .

[10]  Hideto Tsuji,et al.  Poly(lactide) stereocomplexes: formation, structure, properties, degradation, and applications. , 2005, Macromolecular bioscience.

[11]  David R. Moore,et al.  Polymerization of lactide with zinc and magnesium beta-diiminate complexes: stereocontrol and mechanism. , 2001, Journal of the American Chemical Society.

[12]  Susan Selke,et al.  An overview of polylactides as packaging materials. , 2004, Macromolecular bioscience.

[13]  David J. Williams,et al.  Remarkable stereocontrol in the polymerization of racemic lactide using aluminum initiators supported by tetradentate aminophenoxide ligands. , 2004, Journal of the American Chemical Society.

[14]  Thierry Roisnel,et al.  Ring-opening polymerization of lactide with group 3 metal complexes supported by dianionic alkoxy-amino-bisphenolate ligands: combining high activity, productivity, and selectivity. , 2005, Chemistry.

[15]  C. Chuck,et al.  A germanium alkoxide supported by a C3-symmetric ligand for the stereoselective synthesis of highly heterotactic polylactide under solvent-free conditions. , 2007, Angewandte Chemie.

[16]  Xuesi Chen,et al.  Stereoselective polymerization of rac-lactide using a monoethylaluminum Schiff base complex. , 2004, Biomacromolecules.

[17]  Dirk W. Grijpma,et al.  Lewis acid catalyzed polymerization of L-lactide. Kinetics and mechanism of the bulk polymerization , 1992 .

[18]  Yoshito Ikada,et al.  Stereocomplex formation between enantiomeric poly(lactic acid)s. XI. Mechanical properties and morphology of solution-cast films , 1999 .

[19]  K. Zhu,et al.  Synthesis, properties, and biodegradation of poly(1,3-trimethylene carbonate) , 1991 .

[20]  Манфред Степански,et al.  A process for preparing polyhydroxycarboxylic acid , 2011 .

[21]  Young Ha Kim,et al.  In vivo biocompatibilty and degradation behavior of elastic poly(l-lactide-co-ε-caprolactone) scaffolds , 2004 .

[22]  Jagjit Singh,et al.  Evaluation of oriented poly(lactide) polymers vs. existing PET and oriented PS for fresh food service containers , 2005 .

[23]  Xuesi Chen,et al.  Achiral Lanthanide Alkyl Complexes Bearing N,O Multidentate Ligands. Synthesis and Catalysis of Highly Heteroselective Ring-Opening Polymerization of rac-Lactide , 2007 .

[24]  W. Thielemans,et al.  Synthesis of polycaprolactone: a review. , 2009, Chemical Society reviews.

[25]  Ann-Christine Albertsson,et al.  Recent developments in ring opening polymerization of lactones for biomedical applications. , 2003, Biomacromolecules.

[26]  Young Ha Kim,et al.  In vivo biocompatibilty and degradation behavior of elastic poly(L-lactide-co-epsilon-caprolactone) scaffolds. , 2004, Biomaterials.

[27]  D. Sawyer.  Bioprocessing – no longer a field of dreams , 2003 .

[28]  J. Carpentier,et al.  Stereoselective ring-opening polymerization of racemic lactide using alkoxy-amino-bis(phenolate) group 3 metal complexes. , 2004, Chemical communications.

[29]  Xuesi Chen,et al.  Enolic schiff base aluminum complexes and their catalytic stereoselective polymerization of racemic lactide. , 2008, Chemistry.

[30]  S. Ray,et al.  Biodegradable Polylactide and Its Nanocomposites: Opening a New Dimension for Plastics and Composites , 2003 .

[31]  N. Washburn,et al.  Structure and mechanical properties of poly(?,?-lactic acid)/poly(ɛ-caprolactone) blends , 2003 .

[32]  G. Rafler,et al.  Biodegradable polymers. 6th comm. Polymerization of ϵ-caprolactone , 1992 .

[33]  P. Dubois,et al.  Macromolecular engineering of polylactones and polylactides. 4. Mechanism and kinetics of lactide homopolymerization by aluminum isopropoxide , 1991 .

[34]  M. Hillmyer,et al.  Zinc N-heterocyclic carbene complexes and their polymerization of d,l-lactide , 2005 .

[35]  G. Coates,et al.  Stereoselective Ring-Opening Polymerization of meso-Lactide: Synthesis of Syndiotactic Poly(lactic acid) , 1999 .

[36]  Hideto Tsuji,et al.  Poly(L-lactide). IX. Hydrolysis in acid media , 2002 .

[37]  N. Nomura,et al.  Stereoselective Bulk Polymerization of Racemic Lactide for Stereoblock Poly(racemic lactide) Using an Achiral Aluminum Complex , 2004 .

[38]  Pradip K. Roychoudhury,et al.  L (+) lactic acid fermentation and its product polymerization , 2004 .

[39]  L. Gianfreda,et al.  Biodegradation of poly(lactic acid)/starch/coir biocomposites under controlled composting conditions , 2008 .

[40]  L. Lim,et al.  Processing technologies for poly(lactic acid) , 2008 .

[41]  G. Coates,et al.  Stereochemistry of lactide polymerization with chiral catalysts: new opportunities for stereocontrol using polymer exchange mechanisms. , 2002, Journal of the American Chemical Society.

[42]  Zhaohui Tang,et al.  rac-Lactide polymerization using aluminum complexes bearing tetradentate phenoxy-amine ligands , 2007 .

[43]  Keigo Aoi,et al.  Stereoselective ring-opening polymerization of racemic lactide using aluminum-achiral ligand complexes: exploration of a chain-end control mechanism. , 2002, Journal of the American Chemical Society.

[44]  Xuesi Chen,et al.  Synthesis and characterization of a novel biodegradable, thermoplastic polyurethane elastomer , 2006 .

[45]  S. D. Vos,et al.  Microbial Lactic Acid, Its Polymer Poly(lactic acid), and Their Industrial Applications , 2010 .

[46]  V. Gewin.  Genetically Modified Corn— Environmental Benefits and Risks , 2003, PLoS Biology.

[47]  L. Palade,et al.  Polylactides: properties and prospects of an environmentally benign plastic from renewable resources , 2001 .

[48]  Yoshito Ikada,et al.  Stereocomplex formation between enantiomeric poly(lactic acid)s. 4. Differential scanning calorimetric studies on precipitates from mixed solutions of poly(D-lactic acid) and poly(L-lactic acid) , 1991 .

[49]  M. Hillmyer,et al.  Stereoelective polymerization of D,L-lactide using N-heterocyclic carbene based compounds. , 2004, Chemical communications.

[50]  N. Spassky,et al.  Highly stereoelective polymerization of rac‐(D,L)‐lactide with a chiral schiff's base/aluminium alkoxide initiator , 1996 .

[51]  Jincai Wu,et al.  Recent developments in main group metal complexes catalyzed/initiated polymerization of lactides and related cyclic esters , 2006 .

[52]  Geoffrey W. Coates,et al.  Stereoselective ring‐opening polymerization of rac‐lactide with a single‐site, racemic aluminum alkoxide catalyst: Synthesis of stereoblock poly(lactic acid) , 2000 .

[53]  A. Gupta,et al.  New emerging trends in synthetic biodegradable polymers – Polylactide: A critique , 2007 .

[54]  Yoshihiko Yamamoto,et al.  Stereoselective ring-opening polymerization of a racemic lactide by using achiral salen- and homosalen-aluminum complexes. , 2007, Chemistry.

[55]  P. Degée,et al.  Polylactide (PLA)—a new way of production , 1999 .

[56]  J. Feijen,et al.  [(salen)Al]-Mediated, controlled and stereoselective ring-opening polymerization of lactide in solution and without solvent: synthesis of highly isotactic polylactide stereocopolymers from racemic D,L-lactide. , 2002, Angewandte Chemie.

[57]  J. Hedrick,et al.  Stereoselective polymerization of rac- and meso-lactide catalyzed by sterically encumbered N-heterocyclic carbenes. , 2006, Chemical communications.

[58]  C. M. Agrawal,et al.  Sterilization, toxicity, biocompatibility and clinical applications of polylactic acid/polyglycolic acid copolymers. , 1996, Biomaterials.

[59]  S. Słomkowski,et al.  Structure of active species in the cationic polymerization of β‐propiolactone and ε‐caprolactone , 1984 .

[60]  Julian W. Hill.  STUDIES ON POLYMERIZATION AND RING FORMATION. XVII. FRIEDEL-CRAFTS SYNTHESES WITH THE POLYANHYDRIDES OF THE DIBASIC ACIDS , 1932 .

[61]  Gaurav Kale,et al.  Compostability of bioplastic packaging materials: an overview. , 2007, Macromolecular bioscience.

[62]  J. Gallucci,et al.  Well-defined calcium initiators for lactide polymerization. , 2004, Inorganic chemistry.

[63]  Kazuhiko Suzuki,et al.  Basic Properties of Polylactic Acid Produced by the Direct Condensation Polymerization of Lactic Acid , 1995 .

[64]  Michel Vert,et al.  More about the polymerization of lactides in the presence of stannous octoate , 1997 .

[65]  M. Chisholm,et al.  Conformational effects in β-diiminate ligated magnesium and zinc amides. Solution dynamics and lactide polymerization , 2003 .

[66]  A. Padías,et al.  The hydrolytic polymerization of ε-caprolactone by triphenyltin acetate , 1990 .

[67]  M. Okada.  Chemical syntheses of biodegradable polymers , 2002 .

[68]  N. Washburn,et al.  Structure and mechanical properties of poly(D,L-lactic acid)/poly(epsilon -caprolactone) blends. , 2003, Biomaterials.

[69]  Jay Singh,et al.  Performance Evaluation of PLA against Existing PET and PS Containers , 2006 .

[70]  N. Scharnagl,et al.  Poly(lactones). 9. Polymerization mechanism of metal alkoxide initiated polymerizations of lactide and various lactones , 1988 .

[71]  A A Poot,et al.  In vivo behavior of poly(1,3-trimethylene carbonate) and copolymers of 1,3-trimethylene carbonate with D,L-lactide or epsilon-caprolactone: Degradation and tissue response. , 2003, Journal of biomedical materials research. Part A.

[72]  M. Chisholm,et al.  Monomeric metal alkoxides and trialkyl siloxides: (BDI)Mg(OtBu)(THF) and (BDI)Zn(OSiPh3)(THF). Comments on single site catalysts for ring-opening polymerization of lactides , 2001 .

[73]  Donald Garlotta,et al.  A Literature Review of Poly(Lactic Acid) , 2001 .

[74]  Hideto Tsuji,et al.  Enhanced thermal stability of poly(lactide)s in the melt by enantiomeric polymer blending , 2003 .

[75]  Yutaka Tokiwa,et al.  Biodegradability and biodegradation of poly(lactide) , 2006, Applied Microbiology and Biotechnology.

[76]  Yoshito Ikada,et al.  Stereocomplex formation between enantiomeric poly(lactic acid)s. 6. Binary blends from copolymers , 1992 .

[77]  T. Karjalainen,et al.  Biodegradable lactone copolymers. I: Characterization and mechanical behavior of ε-caprolactone and lactide copolymers , 1996 .

[78]  J. Kasperczyk,et al.  Synthesis of block copolymers of ε-caprolactone and lactide in the presence of lithium t-butoxide , 1993 .

[79]  Xuesi Chen,et al.  Aluminum Schiff base catalysts derived from β‐diketone for the stereoselective polymerization of racemic lactides , 2005 .

[80]  P. Degée,et al.  Beneficial effect of triphenylphosphine on the bulk polymerization of L,L‐lactide promoted by 2‐ethylhexanoic acid tin (II) salt , 1999 .

[81]  J. Carpentier,et al.  Yttrium Complexes as Catalysts for Living and Immortal Polymerization of Lactide to Highly Heterotactic PLA , 2007 .

[82]  辻 秀人,et al.  Stereocomplex formation between enantiomeric poly(lactic acid)s , 1992 .

[83]  J. Feijen,et al.  Controlled and stereoselective polymerization of lactide: kinetics, selectivity, and microstructures. , 2003, Journal of the American Chemical Society.

[84]  P. Degée,et al.  Bulk polymerization of lactides initiated by aluminum isopropoxide. I. Mechanism and kinetics , 1997 .

[85]  P. Gruber,et al.  Polylactic Acid Technology , 2000 .

[86]  Hsuan‐Ying Chen,et al.  Ring-Opening Polymerization of Lactides Initiated by Zinc Alkoxides Derived from NNO-Tridentate Ligands , 2006 .