Journal of Polymers and the Environment

, Volume 26, Issue 11, pp 4201–4210 | Cite as

A Novel Bio-based Polyaspartic Acid Copolymer: Synthesis, Structure and Performance of Degradation

  • Xiao-mei Wang
  • Hao-hao Ren
  • Yong-gang YanEmail author
  • Mi-zhi Ji
Original Paper


A novel bio-based polyaspartic acid copolymer, as a multifunctional polymer was fabricated via in-site melting polymerization method using l-aspartic acid, γ-aminobutyric acid, l-phenylalanine and l-alanine as raw materials. The synthetic conditions were studied in detail, and the structure and degradation assays of these copolymers were investigated by FT-IR, XRD, weight loss rate, pH values, intrinsic viscosity and SEM. According to the results, all of the copolymers were found to have similar structure and excellent degradability. Additionally, the optimized copolymer C7 [l-aspartic acid (0.45 mol), γ-aminobutyric acid (0.35 mol), l-phenylalanine (0.05 mol) and l-alanine (0.15 mol)] exhibited the highest weight loss rate among all the copolymers. The weight loss rates on the 28th day in aqueous medium, phosphate buffered saline solution, 5.0 wt% trypsin solution and soil culture medium reached up to 44.74 wt%, 99.75 wt%, 90.67 wt% and 83.58 wt%, respectively. And the appropriate introduction of bio-based amino acids could control the degradation of polyaspartic acid distinctly. All of these results indicated that the bio-based polyaspartic acid copolymer could be used for reference as a good understanding of description the degradation of other environmentally friendly bio-based polymers.


l-aspartic acid Bio-based Weight loss rate Copolymer Degradation 



This work has been funded by the National Natural Science Foundation of China (No. 51773123).

Compliance with Ethical Standards

Conflict of interest

The authors declare no competing financial interest in this work.


  1. 1.
    Shayan M, Azizi H, Ghasemi I al (2015) Effect of modified starch and nanoclay particles on biodegradability and mechanical properties of cross-linked polylactic acid. Carbohyd Polym 124:237–244CrossRefGoogle Scholar
  2. 2.
    Leejarkpai T, Suwanmanee U, Rudeekit Y et al (2011) Biodegradable kinetics of plastics under controlled composting conditions. Waste Manag 31:1153–1161CrossRefPubMedCentralPubMedGoogle Scholar
  3. 3.
    Arrieta MP, Samper MD, López J et al (2014) Combined effect of Poly (hydroxybutyrate) and plasticizers on polylactic acid properties for film intended for food packaging. J Polym Environ 22:460–470CrossRefGoogle Scholar
  4. 4.
    Polyák P, Szemerszki D, Vörös G et al (2017) Mechanism and kinetics of the hydrolytic degradation of amorphous poly (3-hydroxybutyrate). Polym Degrad Stab 140:1–8CrossRefGoogle Scholar
  5. 5.
    Kucharczyk P, Pavelková A, Stloukal P et al (2016) Degradation behavior of PLA-based polyesterurethanes under abiotic and biotic environments. Polym Degrad Stab 129:222–230CrossRefGoogle Scholar
  6. 6.
    Kim HS, Kim HJ, Lee JW et al (2006) Biodegradability of bio-flour filled biodegradable poly (butylene succinate) bio-composites in natural and compost soil. Polym Degrad Stab 91:1117–1127CrossRefGoogle Scholar
  7. 7.
    Mouhmid B, Imad A, Benseddiq N et al (2006) A study of the mechanical behavior of a glass fiber reinforced polyamide 6, 6: experimental investigation. Polym Test 25:544–552CrossRefGoogle Scholar
  8. 8.
    Sudhakar M, Priyadarshini C, Doble M et al (2007) Marine bacteria mediated degradation of nylon 66 and 6. Int Biodeterior Biodegrad 60:144–151CrossRefGoogle Scholar
  9. 9.
    Mohanty AK, Misra M, Drzal LT (2002) Sustainable bio-composites from renewable resources: opportunities and challenges in the green materials world. J Polym Environ 10:19–26CrossRefGoogle Scholar
  10. 10.
    Koller M (2017) Advances in polyhydroxyalkanoate (PHA) production. Bioengineering 4(4):88CrossRefGoogle Scholar
  11. 11.
    Vandamme EJ, Baets SD, Steinbuchel (2010) Biopolymers, volume 6, polysaccharides ii: polysaccharides from eukaryotes. Wiley-VCH, WeinheimGoogle Scholar
  12. 12.
    Berezina N, Martelli SM (2014) Bio-based polymers and materials. RSC Green Chem 27:1–28Google Scholar
  13. 13.
    Pagacz J, Raftopoulos KN, Leszczyńska A et al (2016) Bio-polyamides based on renewable raw materials. J Therm Anal Calorim 123:1225–1237CrossRefGoogle Scholar
  14. 14.
    Kolb N, Winkler M, Syldatk C, Meier MAR (2014) Long-chainpolyesters and polyamides from biochemically derived fatty acids. Eur Polym J 51:159–166CrossRefGoogle Scholar
  15. 15.
    Gandini A, Lacerda TM (2015) From monomers to polymers from renewable resources: recent advances. Prog Polym Sci 48:1–39CrossRefGoogle Scholar
  16. 16.
    Espinosa LMD, Meier MAR (2011) Plant oils: the perfect renewable resource for polymer science. Eur Polymer J 47(5):837–852CrossRefGoogle Scholar
  17. 17.
    Babu RP, O’Connor K, Seeram R (2013) Current progress on bio-based polymers and their future trends. Prog Biomater 2(1):8–12CrossRefPubMedCentralPubMedGoogle Scholar
  18. 18.
    Wu J, Wang P, Jiang D et al (2017) In vitro and in vivo characterization of strontium-containing calcium sulfate/poly (amino acid) composite as a novel bioactive graft for bone regeneration. RSC Adv 7:54306–54312CrossRefGoogle Scholar
  19. 19.
    Zhao ZH, Quan ZX, Jiang DM et al (2013) In vitro and in vivo biological characterizations of a new poly (amino acids)/calcium sulfate composite material for bone regeneration. J Mater Sci 48:2022–2029CrossRefGoogle Scholar
  20. 20.
    Sharma S, Dua A, Malik A (2014) Polyaspartic acid based superabsorbent polymers. Eur Polym J 59:363–376CrossRefGoogle Scholar
  21. 21.
    Shi S, Wu Y, Wang Y et al (2017) Synthesis and characterization of a biodegradable polyaspartic acid/2-amino-2-methyl-1-propanol graft copolymer and evaluation of its scale and corrosion inhibition performance. RSC Adv 7:36714–36721CrossRefGoogle Scholar
  22. 22.
    Yan MF, Liu ZF, Wu XL et al (2010) Research on preparation and performance of environmentally friendly scale inhibition and dispersion agent. The 4th ICBBE, pp 1–3Google Scholar
  23. 23.
    Zhang YL, Hu ZG, Wang JL et al (2016) Biodegradation of poly (aspartic acid-lysine) copolymers by mixed bacteria from natural water. Polym Degrad Stab 128:134–140CrossRefGoogle Scholar
  24. 24.
    Kim JH, Chang MS, Jeon YS et al (2011) Synthesis and characterization of poly (aspartic acid) derivatives conjugated with various amino acids. J Polym Res 18:881–890CrossRefGoogle Scholar
  25. 25.
    Hayashi T, Iwatsuki M (2010) Biodegradation of copoly (L-aspartic acid/L-glutamic acid) in vitro. Biopolymers 29:549–557CrossRefGoogle Scholar
  26. 26.
    Zhang Y, Wei H, Jiang Y et al (2017) Biodegradation of poly(aspartic acid-itaconic acid) copolymers by miscellaneous microbes from natural water. J Polym Environ 26:1–6Google Scholar
  27. 27.
    Wang P, Liu P, Xu F, Fan X, Yuan H, Li H et al (2016) Controlling the degradation of dicalcium phosphate/calcium sulfate/poly (amino acid) biocomposites for bone regeneration. Polym Compos 39:E122–E131Google Scholar
  28. 28.
    Fan XX (2016) In vitro and in vivo evaluation of poly (aminoacid) /hydroxyapatite/calcium sulfate composite for load-bearing bone repair. PhD Dissertation, Sichuan UniversityGoogle Scholar
  29. 29.
    Zheng H, Li H, Xiong Y et al (2016) Studies on the trypsin degradation of /PAA composite. Chem Eng Equip 11:1–3Google Scholar
  30. 30.
    Zhang M, Wang XX, Liu BJ et al (2008) Study on biodegradable behavior of polyesters in the soil of Shanxi local. Polym Mater Sci Eng 24:91–97Google Scholar
  31. 31.
    Zhang M, Huang J-t, Cui CN, Songs J et al (2010) Biodegradability of PBS/PHB Blends. Polym Mater Sci Eng 26:43–46Google Scholar
  32. 32.
    Liu JP, Zheng RB (2005) Experiments on polymer science and materials engineering. Chemical Industry Press, BeijingGoogle Scholar
  33. 33.
    Thombre S, Sarwade B (2005) Synthesis and biodegradability of polyaspartic acid: a critical review. J Macromol Sci A 42:1299–1315CrossRefGoogle Scholar
  34. 34.
    Wang P (2017) Research on controllable degradation biocomposites of dicalcium phosphate/calcium sulfate/poly (amino acid) for orthopedic tissue engineering. PhD Dissertation, Sichuan UniversityGoogle Scholar
  35. 35.
    Little U, Buchanan F, Harkin-Jones E et al (2009) Accelerated degradation behavior of poly (ɛ-caprolactone) via melt blending with poly (aspartic acid-co-lactide) (PAL). Polym Degrad Stab 94:213–220CrossRefGoogle Scholar
  36. 36.
    Ebata M, Morita K (2008) Hydrolysis of ε-amincaproyl compounds by trypsin. J Biochem 46:407–416CrossRefGoogle Scholar
  37. 37.
    Huang J, Cui C, Yan G, Zhang M (2016) A study on degradation of composite material PBS/PCL. Polym Polym Compos 24:143–146CrossRefGoogle Scholar
  38. 38.
    Tokiwa Y, Calabia BP, Ugwu CU et al (2009) Biodegradability of plastics. Int J Mol Sci 10:3722–3733CrossRefPubMedCentralPubMedGoogle Scholar
  39. 39.
    Hideto T, Kazumasa N, Kensaku I (2001) High-temperature hydrolysis of poly (L-lactide) films with different crystallinities and crystalline thicknesses in phosphate-buffered solution. Macromol Mater Eng 286:398–406CrossRefGoogle Scholar
  40. 40.
    Zhou W, Wang X, Yang B et al (2013) Synthesis, physical properties and enzymatic degradation of bio-based poly (butylene adipate-co-butylene furandicarboxylate) copolyesters. Polym Degrad Stab 98:2177–2183CrossRefGoogle Scholar
  41. 41.
    Tao H, Huang JL, Yang SL et al (2004) Researches on biodegradability of polyaspartic acid in aqueous medium. J Harbin Inst Technol 36:1659–1662Google Scholar
  42. 42.
    Vey E, Roger C, Meehan L et al (2008) Degradation mechanism of poly (lactic-co-glycolic) acid block copolymer cast films in phosphate buffer solution. Polym Degrad Stab 93:1869–1876CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Xiao-mei Wang
    • 1
  • Hao-hao Ren
    • 2
  • Yong-gang Yan
    • 1
    Email author
  • Mi-zhi Ji
    • 1
  1. 1.College of Physical Science and TechnologySichuan UniversityChengduChina
  2. 2.Sichuan National Nano Technology Co., LtdChengduChina

Personalised recommendations