Production
There are several industrial routes to usable (i.e. high molecular weight) PLA. Two main monomers are used: lactic acid, and the cyclic di-ester, lactide. The most common route to PLA is the ring-opening polymerization of lactide with various metal catalysts (typically tin octoate) in solution, in the melt, or as a suspension. The metal-catalyzed reaction tends to cause racemization of the PLA, reducing its stereoregularity compared to the starting material.
Another route to PLA is the direct condensation of lactic acid monomers. This process needs to be carried out at less than 200 °C; above that temperature, the entropically favored lactide monomer is generated. This reaction generates one equivalent of water for every condensation (esterification) step, and that is undesirable because water causes chain-transfer leading to low molecular weight material. The direct condensation is thus performed in a stepwise fashion, where lactic acid is first oligomerized to PLA oligomers. Thereafter, polycondensation is done in the melt or as a solution, where short oligomeric units are combined to give a high molecular weight polymer strand. Water removal by application of a vacuum or by azeotropic distillation is crucial to favor polycondensation over transesterification. Molecular weights of 130 kDa can be obtained this way. Even higher molecular weights can be attained by carefully crystallizing the crude polymer from the melt. Carboxylic acid and alcohol end groups are thus concentrated in the amorphous region of the solid polymer, and so they can react. Molecular weights of 128-152 kDa are obtainable thus.
Polymerization of a racemic mixture of L- and D-lactides usually leads to the synthesis of poly-DL-lactide (PDLLA), which is amorphous. Use of stereospecific catalysts can lead to heterotactic PLA which has been found to show crystallinity. The degree of crystallinity, and hence many important properties, is largely controlled by the ratio of D to L enantiomers used, and to a lesser extent on the type of catalyst used. Apart from lactic acid and lactide, lactic acid O-carboxyanhydride ("lac-OCA"), a five-membered cyclic compound has been used academically as well. This compound is more reactive than lactide, because its polymerization is driven by the loss of one equivalent of carbon dioxide per equivalent of lactic acid. Water is not a co-product.
The direct biosynthesis of PLA similar to the poly(hydroxyalkanoate)s has been reported as well.
Read more about this topic: PLA Film
Famous quotes containing the word production:
“An art whose limits depend on a moving image, mass audience, and industrial production is bound to differ from an art whose limits depend on language, a limited audience, and individual creation. In short, the filmed novel, in spite of certain resemblances, will inevitably become a different artistic entity from the novel on which it is based.”
—George Bluestone, U.S. educator, critic. “The Limits of the Novel and the Limits of the Film,” Novels Into Film, Johns Hopkins Press (1957)
“... this dream that men shall cease to waste strength in competition and shall come to pool their powers of production is coming to pass all over the earth.”
—Jane Addams (1860–1935)
“The growing of food and the growing of children are both vital to the family’s survival.... Who would dare make the judgment that holding your youngest baby on your lap is less important than weeding a few more yards in the maize field? Yet this is the judgment our society makes constantly. Production of autos, canned soup, advertising copy is important. Housework—cleaning, feeding, and caring—is unimportant.”
—Debbie Taylor (20th century)