Skip to main content
SpringerLink
Log in

Degradable Polyesters based on Oxygenated Fatty Acid Monomer

  • Organic Materials
  • Published:
Journal of Wuhan University of Technology-Mater. Sci. Ed. Aims and scope Submit manuscript

Abstract

A series of degradable polyesters was synthesized via melt polymerization of 3,6-dioxaoctane-1,8-dioic acid and five different diols, catalyzed by antimony trioxide (Sb2O3). The polymers were characterized by FT-IR and 1H NMR spectroscopy, gel permeation chromatography (GPC) and differential scanning calorimetry (DSC) analysis. The polydispersity index (PDI = Mw/Mn) of the polyesters ranged from 1.55 to 1.99, the weight-average molecular weight (Mw) from 1.8 × 104 to 3.2 × 104 Da, the melting point from 63 to 123 °C, and the highest decomposition temperature observed was 363 °C. The influence of the structure of the polymer chain on hydrolytic degradability was investigated with tests performed at three different values of pH. The findings obtained provide useful insight for the molecular design and the synthesis of degradable polyesters.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Mancini SD, Zanin M. Consecutive Steps of PET Recycling by Injection: Evaluation of the Procedure and of the Mechanical Properties[J]. Journal of Applied Polymer Science, 2000, 76(2): 266–275

    Article  CAS  Google Scholar 

  2. Nisticò R. Polyethylene Terephthalate (PET) in the Packaging Industry[J]. Polymer Testing, 2020, 90: 106707

    Article  Google Scholar 

  3. Thuy TLB, Anh Nguyen D, Van Ho S, et al. Using Ionic Liquid Catalyst for Conversion of Waste Polyethylene Terephthalate and Soybean Oil to Polyester Polyol[J]. Journal of Applied Polymer Science, 2016, 133(37): 43920

    Google Scholar 

  4. Pham N TH, Nguyen VT. Morphological and Mechanical Properties of Poly(Butylene Terephthalate)/High-density Polyethylene Blends[J]. Advances in Materials Science and Engineering, 2020, 2020: 1–9

    Google Scholar 

  5. Bikiaris DN, Karayannidis GP. Thermomechanical Analysis of Chain-extended PET and PBT[J]. Journal of Applied Polymer Science, 1996, 60(1): 55–61

    Article  CAS  Google Scholar 

  6. Obruca S, Sedlacek P, Slaninova E, et al. Novel Unexpected Functions of PHA Granules[J]. Applied Microbiology and Biotechnology, 2020, 104(11): 4795–4810

    Article  CAS  Google Scholar 

  7. Malikmammadov E, Tanir TE, Kiziltay A, et al. PCL and PCL-based Materials in Biomedical Applications[J]. Journal of Biomaterials Science, Polymer Edition, 2018, 29(7–9): 863–893

    Article  CAS  Google Scholar 

  8. Ding M, Zhang M, Yang J, Qiu JH. Study on the Enzymatic Degradation of PBS and Its Alcohol Acid Modified Copolymer[J]. Biodegradation, 2012, 23(1): 127–132

    Article  CAS  Google Scholar 

  9. Watts A, Kurokawa N, Hillmyer MA. Strong, Resilient, and Sustainable Aliphatic Polyester Thermoplastic Elastomers[J]. Biomacromolecules, 2017, 18(6): 1845–1854

    Article  CAS  Google Scholar 

  10. Kwiecień M, Adamus G, Kowalczuk M. Selective Reduction of PHA Biopolyesters and Their Synthetic Analogues to Corresponding PHA Oligodiols Proved by Structural Studies[J]. Biomacromolecules, 2013, 14(4): 1181–1188

    Article  Google Scholar 

  11. Nawaz A, Hasan F, Shah AA. Degradation of Poly(ε-caprolactone) (PCL) by a Newly Isolated Brevundimonas sp. Strain MRL-AN1 from Soil[J]. FEMS Microbiology Letters, 2014, 362: 1–7

    Article  Google Scholar 

  12. Ding M, Zhang M, Yang J, Qiu J. Study on the Enzymatic Degradation of Aliphatic Polyester-PBS and Its Copolymers[J]. Journal of Applied Polymer Science, 2012, 124(4): 2902–2907

    Article  CAS  Google Scholar 

  13. Sheikholeslami SN, Rafizadeh M, Taromi FA, et al. Material Properties of Degradable Poly(Butylene Succinate-co-fumarate) Copolymer Networks Synthesized by Polycondensation of Pre-homopolyesters[J]. Polymer, 2016, 98: 70–79

    Article  CAS  Google Scholar 

  14. Terzopoulou Z, Papadopoulos L, Zamboulis A, et al. Tuning the Properties of Furandicarboxylic Acid-based Polyesters with Copolymerization: A Review[J]. Polymers, 2020, 12(6): 1209

    Article  CAS  Google Scholar 

  15. Jacquel N, Saint-Loup R, Pascault JP, et al. Bio-based Alternatives in the Synthesis of Aliphatic-aromatic Polyesters Dedicated to Biodegradable Film Applications[J]. Polymer, 2015, 59: 234–242

    Article  CAS  Google Scholar 

  16. Chan WL, Akashi M, Kimura Y, et al. Synthesis and Enzymatic Degradability of an Aliphatic/Aromatic Block Copolyester: Poly(Butylene Succinate)-Multi-poly(Butylene Terephthalate)[J]. Macromolecular Research, 2017, 25(1): 54–62

    Article  Google Scholar 

  17. Lesly DWD, Cheng Z, William MKS, et al. High Performance Sulfur-containing Copolyesters from Bio-sourced Aromatic Monomers[J]. Express Polymer Letters, 2022, 16(1): 102–114

    Article  Google Scholar 

  18. Qian ZY, Li S, He Y, et al. Synthesis and in vitro Degradation Study of poly(Ethylene Terephthalate)/poly(Ethylene Glycol) (PET/PEG) Multiblock Copolymer[J]. Polymer Degradation and Stability, 2004, 83(1): 93–100

    Article  CAS  Google Scholar 

  19. Zhou XM. Synthesis and Characterization of Polyester Copolymers Based on poly(Butylene Succinate) and poly(Ethylene Glycol)[J]. Materials Science and Engineering C: Materials for Biological Applications, 2012, 32(8): 2459–2463

    Article  CAS  Google Scholar 

  20. Cheng ZZ, Cheng JP, Chen J, et al. Synthesis and Characterization of poly(Terephthalic Acid-2,5-furandicarboxylic Acid-l,8-octanediol) Copolyester[J]. Journal of Wuhan University of Technology — Materials Science Edition, 2021, 36(4): 557–561

    Article  CAS  Google Scholar 

Download references

Funding

Funded by the Program (BG20190227001) of High-end Foreign Experts of the State Administration of Foreign Experts Affairs (SAFEA) and the Coal Conversion and New Carbon Materials Hubei Key Laboratory in Wuhan University of Science and Technology (WKDM201909)

Author information

Authors and Affiliations

  1. Research Institute of Fine Organic Chemicals & Organic Materials at School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan, 430081, China

    Zhengzai Cheng  (程正载), Yi Li, Lesly Dasilva Wandji Djouonkep, Sheng Zeng, Huan Wang, Linfeng Wang, Shuanpu Cai, Panpan Liu, Hai Hu, Yingao Yang, Jiaqi Li, Jisong Qin & Mario Gauthier

  2. Coal Conversion and New Carbon Materials Hubei Key Laboratory, Wuhan University of Science and Technology, Wuhan, 430081, China

    Zhengzai Cheng  (程正载)

  3. Department of Petroleum Engineering, Applied Chemistry in Oil and Gas Fields, Yangtze University, Wuhan, 43010, China

    Lesly Dasilva Wandji Djouonkep

  4. Department of Chemistry, University of Waterloo, 200 University Avenue West, Ontario, Waterloo, N2L 3G1, Canada

    Mario Gauthier

Authors
  1. Zhengzai Cheng  (程正载)
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yi Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lesly Dasilva Wandji Djouonkep
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sheng Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Huan Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Linfeng Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Shuanpu Cai
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Panpan Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Hai Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Yingao Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Jiaqi Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Jisong Qin
    View author publications

    You can also search for this author in PubMed Google Scholar

  13. Mario Gauthier
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhengzai Cheng  (程正载).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cheng, Z., Li, Y., Djouonkep, L.D.W. et al. Degradable Polyesters based on Oxygenated Fatty Acid Monomer. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 37, 753–759 (2022). https://doi.org/10.1007/s11595-022-2592-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11595-022-2592-1

Key words

Search

Navigation