Lactic acid polylactide from

Polylactide is the generaUy accepted term for highly polymeric poly(lactic acid)s. Such polymers are usuaUy produced by polymerization of dilactide the polymerization of lactic acid as such does not produce high molecular weight polymers. The polymers produced from the enantiomeric lactides are highly crystalline, whereas those from the meso lactide are generaUy amorphous. UsuaUy dilactide from L-lactic acid is preferred as a polymerization feedstock because of the avaUabUity of L-lactic acid by fermentation and for the desirable properties of the polymers for various appUcations (1,25). 

Polylactic acid, also known as polylactide, is prepared from the cycHc diester of lactic acid (lactide) by ring-opening addition polymerization, as shown below ... 

Carboxylic Acids Obtained by Fermentation of Carbohydrates Lactic (2-hydroxy-propionic) acid obtained by fermentation of glucose and polysaccharides is used by NatureWorks (Cargill/Dow LLC) to prepare polylactide (PLA), a biodegradable or recyclable polymer with a potential production of 140000 t a-1 (Scheme 3.4) [23], This and other potential useful reactions from lactic acid have been reviewed by Datta and Henry [24],... 

Much has been written about Cargill Dow LLC s polylactide (PLA) polymer, also known as NatureWorks PLA. PLA is a thermoplastic produced from biomass sugars by fermentation. The fermentation product, lactic acid, is converted into a lactide that is purified and polymerized using a special ring-opening process (18). 

Polylactide is a degradable polyester, formed by the ring-opening polymerization of lactide or the condensation polymerization of lactic acid. Lactide is produced from lactic acid, which derives from the fermentation of D-glucose, which is usually harvested from high-starch-content crops, such as com or sugar beet (Fig. 1). 

Due to the chiral nature of lactic acid, several distinct forms of polylactide exist poly-L-lactide (PLLA) is the product resulting from polymerization of L,L-lactide (also known as L-lactide). PLLA has a crystallinity around 37%, a glass transition... 

NatureWorks LLC has set up a 300 million plant at Blair, NE, which is capable of producing about 140,000-tons/year of poly-lactide polymers from com sugar. It employs a fermentation process to produce two chiral isomers of lactic acid from glucose, which are then cracked to form three lactide isomers. The isomers are subsequently polymerized to polylactide. 

Polylactides are made from lactic acid and are used for orthopedic repair materials. They can be absorbed by the body and are used for the treatment of porous bone fractures and joint reconstruction. Dextran is a substitute for blood plasma in medicine. It is produced by fermentation of saccharose by Leuconostoc mesenteroides microorganisms. After the fermentation is completed (about 24 h), the cell mass is separated and the dextran is precipitated by addition of ethanol to the liquid phase. 

Polylactides or lactic acid polymers are made from lactic acid, which is in turn made from lactose (or milk sugar) obtained from sugar beet, potatoes, wheat, maize, Polylactides are water resistant and can be formed by injection... 

Some of the com-derived glucose goes into various fermentation processes that lead to other chemical products. For example, large-scale production was recently announced for lactic acid and polylactide plastic derived from it. Citric acid and lysine are two other important fermentation products. 

Plackett D, Andersen TL, Pedersen WB, Nielsen L (2003) Biodegradable composites based on L-polylactide and jute fibres. Compos Sci Technol 63(9) 1287-1296 Sebastien F, Stephane G, Copinet A, Coma V (2006) Novel biodegradable films made from chitosan and poly(lactic acid) with antifungal properties against mycotoxinogen strains. Carbohydr Polym 65(2) 185-193... 

In the early 1970s, patents for polylactide/drug mixtures were awarded to DuPont [12, 13]. The first applications for controlled drug delivery involved the release of narcotic antagonists from pLA films [14, 15]. Poly(L(-l-)-lactic acid)... 

The doublet structure of the methyl signal at 17 ppm is caused by the stereochemistry. Polylactides, not yet described in any pharmacopoeias, are rather new biodegradable polyesters derived from the chiral lactic acid and used, e. g., in drug delivery systems. The stereochemistry of the polymer is important to the physical and chemical behavior, especially the polymer properties. Pure tactic polymerization can be differentiated from atactic or mixed polymers by simple comparison of the C NMR spectra (Figure 3-10) [4]. 

PLA is known both as poly(lactic acid) and as polylactide. It is currently the most used packaging plastic that is both biodegradable and biobased. PLA is a member of the polyester family, and is chemically synthesized from lactic acid that is derived from starch by fermentation. PLA has the following structure ... 

It is an aliphatic polyester derived from renewable resources, such as com starch, tapioca roots, chips or starch, or sugarcane. Polylactic acid or polylactide (PLA) can withstand temperatures up to 110 °C [69]. PLA is soluble in chlorinated solvents, hot benzene, tetrahydrofuran, and dioxane [70]. It can be processed like other thermoplastics into fiber (for example, using conventional melt spinning processes) and film. Due to the chiral nature of lactic acid, several distinct forms of polylactide exist ... 

Polylactide or Polylactic Acid (PLA) is a synthetic, aliphatic polyester from lactic acid (Figures 12.20 and 12.21). 

Figure 12.20 Ring opening polymerization of lactic acid dimer yielding polylactide (reproduced from Wikipedia Polylactic Acid).

Over the past several decades, polylactide - i.e. poly(lactic acid) (PLA) - and its copolymers have attracted significant attention in environmental, biomedical, and pharmaceutical applications as well as alternatives to petro-based polymers [1-18], Plant-derived carbohydrates such as glucose, which is derived from corn, are most frequently used as raw materials of PLA. Among their applications as alternatives to petro-based polymers, packaging applications are the primary ones. Poly(lactic acid)s can be synthesized either by direct polycondensation of lactic acid (lUPAC name 2-hydroxypropanoic acid) or by ring-opening polymerization (ROP) of lactide (LA) (lUPAC name 3,6-dimethyl-l,4-dioxane-2,5-dione). Lactic acid is optically active and has two enantiomeric forms, that is, L- and D- (S- and R-). Lactide is a cyclic dimer of lactic acid that has three possible stereoisomers (i) L-lactide (LLA), which is composed of two L-lactic acids, (ii) D-lactide (DLA), which is composed of two D-lactic acids, and (iii) meso-lactide (MLA), which is composed of an L-lactic acid and a D-lactic acid. Due to the two enantiomeric forms of lactic acids, their homopolymers are stereoisomeric and their crystallizability, physical properties, and processability depend on their tacticity, optical purity, and molecular weight the latter two are dominant factors. 

Figure 11.33. Tensile strength of oligomeric lactic acid plasticized polylactide. [Adapted, by permission, from Sinclair R Q T. Macromol. Sci. A, A33, No.5, 1996, p.585-97.]...

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