Polybutylene succinate

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Polybutylene succinate
Names
Other names
Poly(tetramethylene succinate)
Identifiers
Abbreviations PBS
Properties
(C8H12O4)n
Density 1.26 g/cm3
Melting point 115 °C (239 °F; 388 K)
Insoluble
Solubility in chloroform Soluble
Related compounds
Related Monomers
 Succinic acid
Butanediol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Polybutylene succinate (PBS) (sometimes written polytetramethylene succinate) is a

aliphatic polyester with properties that are comparable to polypropylene
.

It may also be referred to by the brand names GsPLA or BioPBS (Mitsubishi Chemical).[1] PBS consists of polymerized units of butylene succinate, with repeating C8H12O4 units.

History

A. V. Lourenço
W. H. Carothers

The synthesis of succinic acid based polyesters was first performed in 1863. In that time the Portuguese professor Agostinho Vicente Lourenço described in his "Recherche sur les composés polyatomiques" (Research on polyatomic compounds), the reaction between succinic acid and ethylene glycol to form what he named "succino-ethylenic acid". He noticed that this acid was losing water when it was heated at high temperatures (300 °C) and that a crystalline mass when obtained after cooling.[2] Unfortunately, Lourenço did not study much the structure of the material he obtained.

Later Davidoff (1886),[3] and then Voländer (1894) prepared this same material by using different methods. This early work was pursued in the 1930s by Wallace Carothers (E.I. du Pont de Nemours and Co.), with a more systematic study of succinic acid based polyesters. In that time the purpose of such study was to find a synthetic alternative to natural silk fiber.

Carothers, by eliminating water in a continuous distillation process, obtained polymers with molar masses significantly higher than what was previously synthesized.

Nylon 6,6
.

Later Flory (1946) proposed an improved synthesis of aliphatic polyesters with diacid chloride.[5]

In the beginning of the 1990s, after being forgotten for more than 40 years, these polymers received a renewed interest due to the increasing demand on biodegradable and bio-based polymers.

Synthesis

Like other polyesters such as

diacid
. The direct esterification of
diacid to form PBS oligomers with elimination of water
.

Then, these oligomers are trans-esterified under vacuum to form a high molar mass polymer. This step requires an appropriate catalyst such as titanium, zirconium, tin or germanium derivatives.[6]

Biodegradability

Amycolatopsis sp. HT-6 and Penicillium sp. strain 14-3 can degrade PBS. Microbispora rosea, Excellospora japonica and E. viridilutea can consume samples of emulsified PBS.[7]

Applications

As PBS decomposes into

films, bags, or boxes, for both food and cosmetic packagings. Other applications of PBS could be found as disposable products such as tableware or medical articles. In agriculture, PBS finds interest in the fabrication of mulching films or delayed release materials for pesticide and fertilizer. PBS is also promise to find market shares in fishery (for fishing nets), forestry, civil engineering or other fields in which recovery and recycling of materials after use is problematic.[9] In the medical field, PBS could be used as biodegradable drug encapsulation systems,[10] and is also investigated for implants
.

Industrial production

In industry, the improvement of the PBS synthesis allowed the large scale production of this polymer. The Japanese company

diisocyanate.[12]
Much later, in April 2003, Mitsubishi Chemicals built a 3,000 tons/year capacity and launched to the market a PBS named GS Pla (Green and Sustainable Plastic). This polymer has high molar masses without the use of a chain extender. Since then, several PBS producers such as Hexing Chemical (Anhui, China), Xinfu Pharmaceutical (Hangzhou, China) or IRe Chemical (South Korea) appeared on the market. In 2010 Hexing Chemical became China's first large-scale PBS enterprise, with the annual capacity of 10,000 tons. The same year Xinfu Pharmaceutical announced the building up of the world's largest continuous PBS production line with an annual capacity of 20,000 tons. At the moment most of these polyalkylene succinates are synthesized from petrochemical precursors. Nevertheless most of the producers are evaluating or developing bio-based succinic acid for the synthesis of these polyesters. In 2016, Showa Denko announced termination of the production and sale of Bionolle, citing delay in permeation of environmental regulations on plastic shopping bags and a fall in market prices of biodegradable plastics.[13]

References

  1. ^ "Biodegradable Polymer "BioPBS" | Products".
  2. ^ Lourenço, A.V. (1863). "Recherches sur les composés polyatomiques". Ann. Chim. Phys. 67 (3).
  3. doi:10.1002/cber.18860190196
    .
  4. doi:10.1021/ja01383a042
    .
  5. ^ U.S. patent 2,589,687
  6. doi:10.1002/pola.25009
    .
  7. PMID 19865515
    .
  8. ISBN 978-3-642-03286-8
    .
  9. ISBN 978-3-642-03286-8
    .
  10. PMID 21376545
    .
  11. ISBN 978-3-642-03286-8
    .
  12. doi:10.1016/s0141-3910(97)00220-6
    .
  13. ^ "SDK to Terminate Production and Sale of Biodegradable Plastic | News Releases | SHOWA DENKO K.K." www.sdk.co.jp. Retrieved 2017-04-26.
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