Location via proxy:   [ UP ]  
[Report a bug]   [Manage cookies]                
Skip to main content
SpringerLink
Log in

Development of novel bioactive waterborne polyurethanes: Effect of polyurethane chemical structure on its properties

  • Original Paper
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

In this work, a family of bioactive waterborne polyurethanes (WPUs), based on glycerol ethoxylate (GE), hexamethylene diisocyanate (HDI) or isophorone diisocyanate (IPDI), with specific bioactivity on their chemical structures constituted by the amino acids: L-tyrosine (T), L-histidine (H) or L-glutamic acid (Glut), using a mass ratio of each component of 56/29/15%, respectively, was synthesized by a condensation reaction at 80 ºC for 3 h. In the GPC analysis, the P(HDI-T) shows the highest average molecular weight (Mn) (20,264 g mol−1), with a rod-like morphology, with a melting point of 240 ºC and with high resistance to endothermic degradation. IPDI-based WPUs exhibit a rough and amorphous structure, with a glass transition temperature around 120 ºC, regardless of the chemical structure of the amino acid present in their polymeric skeleton. The P(HDI-T) WPU it has the largest particle size. The in vitro biological evaluation reveals that the synthesized WPUs demonstrate to be non-hemolytic materials, benefiting the proliferation of important cells in the healing process such as monocytes and fibroblasts, and that they have antibacterial properties; evidencing that P(HDI-H) and P(IPDI-Glut) allow a 100% in vitro wound closure at 15 days. These novel bioactive synthetic polymers could be useful for the design of smart biomaterials as hydrogels made up of proteins using them as chemical crosslinker, taking advantage of the reactivity of the isocyanate groups.

Graphical Abstract

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

Data availability

Available upon request.

References

  1. Gogolewski S (1989) Leading Contribution. Selected topics in biomedical polyurethanes. Rev Colloid Polym Sci 267:757–785

    Article  CAS  Google Scholar 

  2. Mendoza-Novelo B, Mata-Mata JL, Vega-Gonzalez A, Cauich-Rodriguez JV, Marcos-Fernandez A (2014) Synthesis and characterization of protected oligourethanes as crosslinkers of collagen-based scaffolds. J Mater Chem B 2(19):2874–2882

    Article  CAS  PubMed  Google Scholar 

  3. Lara-Rico R, López-Badillo CM, Claudio-Rizo JA, Cabrera-Munguia DA, Becerra-Rodriguez JJ, Espinosa-Neira R, Cruz-Ortiz BR (2023) Smart hydrogels based on semi-interpenetrating polymeric networks of collagen-polyurethane-alginate for soft/hard tissue healing, drug delivery devices, and anticancer therapies. Biopolymers 114(6):e23538

    Article  CAS  PubMed  Google Scholar 

  4. León-Campos MI, Rodríguez-Fuentes N, Claudio-Rizo JA, Cabrera-Munguía DA, Becerra-Rodriguez JJ, Herrera-Guerrero A, Soriano-Corral F, Alcántara-Quintana LE (2023) Development and in vitro evaluation of a polymeric matrix of jellyfish collagen-human stem cell secretome- polyurethane for wound healing. J Mater Sci 58:8047–8060

    Article  Google Scholar 

  5. León-Campos MI, Claudio-Rizo JA, Rodríguez-Fuentes N, Cabrera-Munguía DA, Becerra-Rodríguez JJ, Herrera-Guerrero A, Sorial-Corral F (2021) Biocompatible interpenetrating polymeric networks in hydrogel state comprised from jellyfish collagen and polyurethane. J Polym Res 28(8):291

    Article  Google Scholar 

  6. Fuller MA, Koper I (2019) Biomedical applications of polyelectrolyte coated spherical gold nanoparticles. Nano convergence 6(1):11

    Article  PubMed  Google Scholar 

  7. Pratik Jagtap KP, Dhatrak P (2021) Polyelectrolyte Complex for Drug Delivery in Biomedical Applications: A Review. IOP Conf. Ser Mater Sci Eng. 1183:012007

    Article  Google Scholar 

  8. Movilli J, Huskens J (2020) Functionalized Polyelectrolytes for Bioengineered Interfaces and Biosensing Applications. Org Mater 2:78–107

    Article  CAS  Google Scholar 

  9. O’Bryan CS, Kabb CP, Sumerlin BS, Angelini TE (2019) Jammed Polyelectrolyte Microgels for 3D Cell Culture Applications: Rheological Behavior with Added Salts. ACS Appl Bio Mater 2(4):1509–1517

    Article  CAS  PubMed  Google Scholar 

  10. Arhebamen EP, Teodoro MT, Blonka AB, Matthew HWT (2023) Long-Term Culture Performance of a Polyelectrolyte Complex Microcapsule Platform for Hyaline Cartilage Repair. Bioengineering 10(4):467

    Article  CAS  PubMed  Google Scholar 

  11. Spalinger MR, McCole DF, Rogler G, Scharl M (2015) Role of protein tyrosine phosphatases in regulating the immune system: implications for chronic intestinal inflammation. Inflamm Bowel Dis 21(3):645–655

    Article  PubMed  Google Scholar 

  12. Kim Y, Kim E, Kim Y (2019) L-histidine and L-carnosine accelerate wound healing via regulation of corticosterone and PI3K/Akt phosphorylation in D-galactose-induced aging models in vitro and in vivo. J Funct Foods 58:227–237

    Article  CAS  Google Scholar 

  13. López-Colomé AM, Fragoso G (1995) Glycine Stimulation of Glutamate Binding to Chick Retinal Pigment Epithelium. Neurochem Res 20(8):887–894

    Article  PubMed  Google Scholar 

  14. Patkar S, Panzade P (2016) Fast and efficient method for molecular weight analysis of cellulose pulp, in-process and finished product. Anal Methods 8:3210–3215

    Article  CAS  Google Scholar 

  15. Hssaini L, Razouk R, Bouslihim Y (2022) Rapid Prediction of Fig Phenolic Acids and Flavonoids Using Mid-Infrared Spectroscopy Combined With Partial Least Square Regression. Front Plant Sci 13:782159

    Article  PubMed  Google Scholar 

  16. Kubota Y, Sohn J, Hatada S, Schurr M, Straehle J, Gour A, Neujahr R, Miki T, Mikula S, Kawaguchi Y (2018) A carbon nanotube tape for serial-section electron microscopy of brain ultrastructure. Nat Commun 9(1):437

    Article  PubMed  Google Scholar 

  17. Chi Y, Han Q, Li Z, Su X, Ren X (2024) The study of pesticide-fertilizer combination prepared with biochar and chlorantraniliprole and its effectiveness in controlling fall armyworms. Adv Agrochem 3(2):151–161

    Article  CAS  Google Scholar 

  18. Martinotti S, Ranzato E (2020) Scratch Wound Healing Assay. Methods Mol Biol 2109:225–229

    Article  CAS  PubMed  Google Scholar 

  19. Anandan P, Vetrivel S, Karthikeyan S, Jayavel R, Ravi G (2012) Crystal growth, spectral and thermal analyses of a semi organic nonlinear optical single crystal: L-tyrosine hydrochloride. Optoelectron Adv Mat 6(11–12):1128–1133

    CAS  Google Scholar 

  20. Kim H, Kang M, Knowles J, Gong M (2014) Synthesis of highly elastic biocompatible polyurethanes based on bio-based isosorbide and poly(tetramethylene glycol) and their properties. J Biomater Appl 29(3):454–464

    Article  PubMed  Google Scholar 

  21. Bialas N, Hocker H, Marschener M, Ritter W (1990) 13C NMR studies on the relative reactivity of isocyanate groups of isophorone diisocyanate isomers. Makromol Chem 191(8):1843–1852

    Article  CAS  Google Scholar 

  22. Hu F, Schmidt-Rohr K, Hong M (2013) NMR detection of pH-dependent histidine-water proton exchange reveals the conduction mechanism of a transmembrane proton channel. J Am Chem Soc 134(8):3703–3713

    Article  Google Scholar 

  23. Spyrou E, Metternich H, Franke R (2003) Isophorone diisocyanate in blocking agent free polyurethane powder coating hardeners: analysis, selectivity, quantumchemical calculations. Prog Org Coat 48(2):201–206

    Article  CAS  Google Scholar 

  24. Karmakar P, Ray S, Mandal A, Modal S, Mallick S, Bera B, Ghosh A (2013) Mechanistic and Kinetic Investigations on the Interaction of Model Platinum(II) Complex With Ligands of Biological Significance in Reference to the Antitumor Activity. Synth React Inorg, Met-Org, Nano-Met Chem 43(10):1563–1570

    Article  CAS  Google Scholar 

  25. Stern T (2023) Chemical Structure and Side Reactions in Polyurea Synthesized via the Water-Diisocyanate Synthesis Pathway. Polymers 15(17):3524

    Article  CAS  PubMed  Google Scholar 

  26. Somisetti V, Allauddin S, Narayan R, Raju K (2015) Synthesis of novel glycerol based B3-type monomer and its application in Hyperbranched polyester urethane-urea coating. RSC Adv 5:74003–74011

    Article  CAS  Google Scholar 

  27. Dong W, Li T, Xiang S, Ma P, Chen M (2013) Influence of Glutamic Acid on the Properties of Poly(xylitol glutamate sebacate) Bioelastomer. Polymers 5(4):1339–1351

    Article  Google Scholar 

  28. Trovati G, Sanchez EA, Claro Neto S, Mascarenhas YP, Chierice GO (2010) Characterization of Polyurethane Resins by FTIR, TGA, and XRD. J Appl Polym Sci 115:263–268

    Article  CAS  Google Scholar 

  29. Kumirska J, Czerwicka M, Kaczynski Z, Bychowska A, Brzozowski K, Thoming J, Stepnowski P (2010) Application of spectroscopic methods for structural analysis of chitin and chitosan. Mar Drugs 8(5):1567–1636

    Article  CAS  PubMed  Google Scholar 

  30. Ghobashy MM (2016) Radiation Crosslinking of Polyurethanes: Characterization by FTIR, TGA, SEM, XRD, and Raman Spectroscopy. J Polym 2016:9802514

    Google Scholar 

  31. Claudio-Rizo JA, Rangel-Argote M, Munoz-Gonzalez PU, Castellano LE, Delgado J, Gonzalez-Garcia G, Mata-Mata JL, Mendoza-Novelo B (2016) Improved properties of composite collagen hydrogels: protected oligourethanes and silica particles as modulators. J Mater Chem B 4(40):6497–6509

    Article  CAS  PubMed  Google Scholar 

  32. Varghese J, Subin T, Sudarsanakumar C (2019) L-Tyrosine functionalized ZnO for the fluorescence detection of phenol. AIP Conf Proc 2082:080003

    Article  Google Scholar 

  33. Jayaraman V, Thiran S, Madden DR (2000) Fourier Transform infrared spectroscopic characterization of a photolabile precursor of glutamate. FEBS Lett 475:278–282

    Article  CAS  PubMed  Google Scholar 

  34. Akram N, Usman M, Haider S, Akhtar MS, Gul K (2022) Impact of Diisocyanates on Morphological and In Vitro Biological Efficacy of Eco-Friendly Castor-Oil-Based Water-Borne Polyurethane Dispersions. Polymers 14(17):3701

    Article  CAS  PubMed  Google Scholar 

  35. Yang Y, Sun C, Zhou Y, Wang T, Zhang Y (2016) Optically active polyurethane based on tyrosine: synthesis, characterization and study of hydrogen bonding. Polym J 48:807–812

    Article  CAS  Google Scholar 

  36. Shakouri Z, Nazockdast H (2018) Microstructural development and mechanical performance of PLA/TPU blends containing geometrically different cellulose nanocrystals. Cellulose 25:7167–7188

    Article  CAS  Google Scholar 

  37. Lee SB, Yoo KS, Yoon KS, Jeong HM, Han YS, Kim BP, Kim JH (1994) Synthesis and properties of thermoplastic polyurethane elastomers modified by poly(7-methyI-L-glutamate ) segment. Polymer 35(17):3804–3806

    Article  CAS  Google Scholar 

  38. Vaes D, Puyvelde PV (2021) Semi-crystalline feedstock for filament-based 3D printing of polymers. Prog Polym Sci 118:101411

    Article  CAS  Google Scholar 

  39. Wendels S, Averous L (2021) Biobased polyurethanes for biomedical applications. Bioact Mater 6(4):1083–1106

    CAS  PubMed  Google Scholar 

  40. Shi X, Qian Q, Xu L, Zhu H, Xu L, Wuang Q (2018) Effects of hydrothermal sterilization on properties of biological coating fabricated by alkaline-heat treatment on titanium. Surf Coat Technol 342:69–75

    Article  CAS  Google Scholar 

  41. Fuensanta M, Martín-Martinez JM (2021) Structural and Viscoelastic Properties of Thermoplastic Polyurethanes Containing Mixed Soft Segments with Potential Application as Pressure Sensitive Adhesives. Polymers 13(18):3097

    Article  CAS  PubMed  Google Scholar 

  42. Veetil RE, Soundiraraju B, Mathew D (2022) End-Terminated Poly(urethane-urea) Hybrid Approach toward Nanoporous/Microfilament Morphology. ACS Omega. 7(7):6280–6291

    Article  CAS  PubMed  Google Scholar 

  43. Yang R, Wang B, Li M, Zhang X, Li J (2019) Preparation, characterization and thermal degradation behavior of rigid polyurethane foam using a malic acid based polyols. Ind Crops Prod 136:121–128

    Article  CAS  Google Scholar 

  44. Spence MW, Plehiers PM (2022) A brief overview of properties and reactions of diisocyanates. Toxicol Ind Health 38(9):495–499

    Article  PubMed  Google Scholar 

  45. Shi X, Xu L, Wang Q, Sunarso LXu (2017) Hydrothermal Sterilization Improves Initial Osteoblast Responses on Sandpaper-Polished Titanium. Materials 10(7):812

    Article  PubMed  Google Scholar 

  46. Holt B, Tripathi A, Morgan J (2008) Viscoelastic response of human skin to low magnitude physiologically relevant shear. J Biomech 41(12):2689–2695

    Article  PubMed  Google Scholar 

  47. Wilkinson HN, Hardman MJ (2020) Wound healing: cellular mechanisms and pathological outcomes. Open Biol 10(9):200223

    Article  CAS  PubMed  Google Scholar 

  48. Weber M, Steinle H, Golombek S, Hann L, Schlensak C, Wendel HP, Avci-Adali M (2018) Blood-Contacting Biomaterials: In Vitro Evaluation of the Hemocompatibility. Front Bioeng Biotechnol 6:99

    Article  PubMed  Google Scholar 

  49. Chiu S, Bharat A (2016) Role of monocytes and macrophages in regulating immune response following lung transplantation. Curr Opin Organ Transplant 21(3):239–245

    Article  CAS  PubMed  Google Scholar 

  50. Contard P, Jacobs L 2nd, Perlish JS, Fleischmajer R (1993) Collagen fibrillogenesis in a three-dimensional fibroblast cell culture system. Cell Tissue Res 273:571–575

    Article  CAS  PubMed  Google Scholar 

  51. Jakfar S, Lin TC, Chen ZY, Yang IH, Gani BA, Ningsih DS, Kusuma H, Chang CT, Lin FH (2022) A Polysaccharide Isolated from the Herb Bletilla striata Combined with Methylcellulose to Form a Hydrogel via Self-Assembly as a Wound Dressing. Int J Mol Sci 23(19):12019

    Article  CAS  PubMed  Google Scholar 

  52. Adib Y, Bensussan A, Michel L (2022) Cutaneous Wound Healing: A Review about Innate Immune Response and Current Therapeutic Applications. Mediators Inflamm 2022:5344085

    Article  PubMed  Google Scholar 

  53. Kołbuk D, Ciechomska M, Jeznach O, Sajkiewicz P (2022) Effect of crystallinity and related surface properties on gene expression of primary fibroblasts. RSC Adv 12(7):4016–4028

    Article  PubMed  Google Scholar 

  54. Bratosin D, Mitrofan L, Palii C, Estaquier J, Montreuil J (2005) Novel fluorescence assay using calcein-AM for the determination of human erythrocyte viability and aging. Cytometry A 66(1):78–84

    Article  PubMed  Google Scholar 

  55. Liang CC, Park AY, Guan JL (2007) In vitro scratch assay: a convenient and inexpensive method for analysis of cell migration in vitro. Nat Protoc 2(2):329–333

    Article  CAS  PubMed  Google Scholar 

  56. Ogwu AA, Okpalugo TI, Ali N, Maguire PD, McLaughlin JA (2008) Endothelial cell growth on silicon modified hydrogenated amorphous carbon thin films. J Biomed Mater Res B Appl Biomater 85(1):105–13

    Article  CAS  PubMed  Google Scholar 

  57. Jablónka-Trypúc A (2021) Human Cell Culture, a Pertinent In Vitro Model to Evaluate the Toxicity of Landfill Leachate/Sewage Sludge. Rev Environ 8:54

    Google Scholar 

  58. Balko S, Kerr E, Buchel E, Logsetty S, Raouf A (2023) A Robust and Standardized Approach to Quantify Wound Closure Using the Scratch Assay. Methods Protoc 6(5):87

    Article  PubMed  Google Scholar 

  59. Puca V, Marulli RZ, Grande R, Vitale I, Niro A, Molinaro G, Prezioso S, Muraro R, Di Giovanni P (2021) Microbial Species Isolated from Infected Wounds and Antimicrobial Resistance Analysis: Data Emerging from a Three-Years Retrospective Study. Antibiotics 10(10):1162

    Article  PubMed  Google Scholar 

  60. Yousefian F, Hesari R, Jensen T, Obagi S, Rgeai A, Damiani G, Bunick CG, Grada A (2023) Antimicrobial Wound Dressings: A Concise Review for Clinicians. Antibiotics 12(9):1434

    Article  CAS  PubMed  Google Scholar 

  61. Li W, Wang B, Zhang M, Wu Z, Wei J, Jiang Y, Sheng N, Liang K, Zhang D, Chen S (2020) All-natural injectable hydrogel with self-healing and antibacterial properties for wound dressing. Cellulose 27:2637–2650

    Article  CAS  Google Scholar 

  62. Kadam S, Shai S, Shahane A, Kaushik KS (2019) Recent Advances in Non-Conventional Antimicrobial Approaches for Chronic Wound Biofilms: Have We Found the “Chink in the Armor”? Biomedicines 7(2):35

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The authors thank to Consejo Nacional de Humanidades, Ciencia y Tecnología-México (CONAHCYT) for supporting the FORDECYT-PRONACES/6660/2020 project, and to M.C María de Lourdes Guillen Cisneros for technical support.

Author information

Authors and Affiliations

  1. Facultad de Ciencias Químicas, Universidad Autónoma de Coahuila, Ing. J. Cárdenas Valdez S/N, República, 25280, Saltillo, Coahuila, México

    María I. León‑Campos, Jesús A. Claudio‑Rizo, Denis A. Cabrera‑Munguía, Luis E. Cobos-Puc & Martín Caldera-Villalobos

  2. CONAHCYT-Centro de Investigación Científica de Yucatán, A.C., Calle 43 No. 130, Chuburná de Hidalgo, 97200, Mérida, Yucatán, México

    María O. González-Díaz

  3. Centro de Investigación en Química Aplicada, Enrique Reyna H., 140, San José de los Cerritos, 25294, Saltillo, Coahuila, México

    Francisco J. Enríquez-Medrano

Authors
  1. María I. León‑Campos
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jesús A. Claudio‑Rizo
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Denis A. Cabrera‑Munguía
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Luis E. Cobos-Puc
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Martín Caldera-Villalobos
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. María O. González-Díaz
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Francisco J. Enríquez-Medrano
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jesús A. Claudio‑Rizo.

Ethics declarations

Conflicts of interest

There are no conflicts to declare.

Data deposition information

No datasets have been used.

Permission to reproduce material from other sources

Available upon request.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1035 KB)

Supplementary file2 (PDF 400 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

León‑Campos, M.I., Claudio‑Rizo, J.A., Cabrera‑Munguía, D.A. et al. Development of novel bioactive waterborne polyurethanes: Effect of polyurethane chemical structure on its properties. J Polym Res 31, 213 (2024). https://doi.org/10.1007/s10965-024-04055-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-024-04055-8

Keywords

Search

Navigation