Top

Journal of Coatings Technology and Research

Published in:

25-10-2019

Biodegradable polymer coating for controlled release of hydrophobic functional molecules from cotton fabrics

Authors: Coral Hartman, Yanay Popowski, Daniel Raichman, Elizabeth Amir

Published in: Journal of Coatings Technology and Research | Issue 3/2020

Activate our intelligent search to find suitable subject content or patents.

search-config

AI-assisted search

Off

Abstract

Despite major advances in polymer chemistry, cotton still remains the principal textile component in the global pharmaceutical industry owing to its intrinsic strength, thermal stability, biocompatibility, and pleasant texture. Nevertheless, the hydrophilic nature of cotton requires the development of strategies for the incorporation of hydrophobic functional molecules into the fabric for controlled-release applications. To address this issue, we designed biodegradable crosslinked poly(β-amino ester) (PBAE) coatings as reservoirs for the incorporation of small hydrophobic molecules and studied their release profiles under physiological conditions. Two PBAEs with different hydrophobic and degradation properties were prepared and crosslinked to cotton fabrics in the presence of azulene, which served as a model hydrophobic, active material. Optimization of the crosslinking process in terms of UV curing time and the amount of solvent revealed that curing time of 15 min using 0.5 mL of chloroform was the optimal crosslinking condition. The coatings were characterized by FTIR, XPS, and SEM as well as TGA and DSC analyses. Sustained release of azulene was observed, and there was a correlation between azulene delivery rates and the hydrophobicity of the coating. These results provide a potentially useful platform for the rational design of cotton-based controlled-release systems for bioactive molecule delivery applications.

Graphic abstract

previous article Fabrication of superhydrophobic cotton fabric treated with n-dodecyltrimethoxysilane/zirconium oxychloride for highly efficient oil/water separation

next article Intumescent coatings based on alkali-activated borosilicate inorganic polymers

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

inform now

Available only for authorised users

Nechifor, CD, Dorohoi, DO, Ciobanu, C, “The Influence of Gamma Radiations on Physico-chemical Properties of Some Polymer Membranes.” Rom. Rep. Phys., 54 (3–4) 349–359 (2009)

Anastas, PT, Kirchhoff, MM, “Origins, Current Status, and Future Challenges of Green Chemistry.” Acc. Chem. Res., 35 (9) 686–694 (2002)

Tahara, T, Shibata, T, Nakamura, M, Yamashita, H, Yoshioka, D, Okubo, M, Maruyama, N, Kamano, T, Kamiya, Y, Nakagawa, Y, Fujita, H, Nagasaka, M, Iwata, M, Takahama, K, Watanabe, M, Hirata, I, Arisawa, T, “Effect of MDR1 Gene Promoter Methylation in Patients with Ulcerative Colitis.” Int. J. Mol. Med., 23 (4) 521–527 (2009)

Cerempei, A, Guguianu, E, Muresan, I, Horhogea, C, Rîmbu, C, Borhan, O, “Antimicrobial Controlled Release Systems for the Knitted Cotton Fabrics Based on Natural Substances.” Fibers Polym., 16 (8) 1688–1695 (2015)

Abdel-Mohsen, AM, Aly, AS, Hrdina, R, Montaser, AS, Hebeish, A, “Biomedical Textiles Through Multifunctioalization of Cotton Fabrics Using Innovative Methoxypolyethylene Glycol-N-Chitosan Graft Copolymer.” J. Polym. Environ., 20 (1) 104–116 (2012)

Ye, W, Xin, JH, Li, P, Lee, KLD, Kwong, TL, “Durable Antibacterial Finish on Cotton Fabric by Using Chitosan-Based Polymeric Core–Shell Particles.” J. Appl. Polym. Sci., 102 (2) 1787–1793 (2006)

Wang, X, Du, Y, Fan, L, Liu, H, Hu, Y, “Chitosan–Metal Complexes as Antimicrobial Agent: Synthesis, Characterization and Structure-Activity Study.” Polym. Bull., 55 (1–2) 105–113 (2005)

Liu, Y, Ma, K, Li, R, Ren, X, Huang, TS, “Antibacterial Cotton Treated with N-Halamine and Quaternary Ammonium Salt.” Cellulose, 20 (6) 3123–3130 (2013)

Su, CH, Kumar, GV, Adhikary, S, Velusamy, P, Pandian, K, Anbu, P, “Preparation of Cotton Fabric Using Sodium Alginate-Coated Nanoparticles to Protect Against Nosocomial Pathogens.” Biochem. Eng. J., 117 28–35 (2017)

10.

Rehan, M, Zaghloul, S, Mahmoud, FA, Montaser, AS, Hebeish, A, “Design of Multi-functional Cotton Gauze with Antimicrobial and Drug Delivery Properties.” Mater. Sci. Eng. C, 80 29–37 (2017)

11.

Lee, HY, Park, HK, Lee, YM, Kim, K, Park, SB, “A Practical Procedure for Producing Silver Nanocoated Fabric and Its Antibacterial Evaluation for Biomedical Applications.” Chem. Commun., 28 2959–2961 (2007)

12.

Abramiuc, D, Ciobanu, L, Muresan, R, Chiosac, M, Muresan, A, “Antibacterial Finishing of Cotton Fabrics Using Biologically Active Natural Compounds.” Fibers Polym., 14 (11) 1826–1833 (2013)

13.

Cerkez, I, “Rapid Disinfection by N-Halamine Polyelectrolytes.” J. Bioact. Compat. Polym., 28 (1) 86–96 (2013)

14.

Cerkez, I, Kocer, HB, Worley, SD, Broughton, RM, Huang, TS, “N-Halamine Biocidal Coatings Via a Layer-by-Layer Assembly Technique.” Langmuir, 27 (7) 4091–4097 (2011)

15.

Zhao, Y, Xu, Z, Wang, X, Lin, T, “Superhydrophobic and UV-Blocking Cotton Fabrics Prepared by Layer-by-Layer Assembly of Organic UV Absorber Intercalated Layered Double Hydroxides.” Appl. Surf. Sci., 286 364–370 (2013)

16.

Wang, Q, Hauser, PJ, “Developing a Novel UV Protection Process for Cotton Based on Layer-by-Layer Self-Assembly.” Carbohydr. Polym., 81 (2) 491–496 (2010)

17.

Langer, R, Tirrell, DA, “Designing Materials for Biology and Medicine.” Nature, 428 (6982) 487–492 (2004)

18.

Granick, S, Kumar, SK, Amis, EJ, Antonietti, M, Balazs, AC, Chakraborty, AK, Grest, GS, Hawker, C, Janmey, P, Kramer, EJ, Nuzzo, R, Russell, TP, Safinya, CR, “Macromolecules at Surfaces: Research Challenges and Opportunities from Tribology to Biology.” J. Polym. Sci. Part B Polym. Phys., 41 (22) 2755–2793 (2003)

19.

Hu, J, “Controlled Release of Hydrogel Modified Textile Products.” J. Control. Release, 152 e31–e33 (2011)

20.

Hashemikia, S, Hemmatinejad, N, Ahmadi, E, Montazer, M, “A Novel Cotton Fabric with Anti-bacterial and Drug Delivery Properties Using SBA-15-NH2/Polysiloxane Hybrid Containing Tetracycline.” Mater. Sci. Eng. C, 59 429–437 (2016)

21.

Wu, Y, Yang, Y, Liu, H, Yao, X, Leng, F, Chen, Y, Tian, W, “Long-Term Antibacterial Protected Cotton Fabric Coating by Controlled Release of Chlorhexidine Gluconate from Halloysite Nanotubes.” RSC Adv., 7 (31) 18917–18925 (2017)

22.

Lynn, DM, Langer, R, “Degradable Poly(β-amino esters): Synthesis, Characterization, and Self-Assembly with Plasmid DNA.” J. Am. Chem. Soc., 122 (44) 10761–10768 (2000)

23.

Lakes, AL, Peyyala, R, Ebersole, JL, Puleo, DA, Hilt, JZ, Dziubla, TD, “Synthesis and Characterization of an Antibacterial Hydrogel Containing Covalently Bound Vancomycin.” Biomacromolecules, 15 (8) 3009–3018 (2014)

24.

Huang, S, Fu, X, “Naturally Derived Materials-Based Cell and Drug Delivery Systems in Skin Regeneration.” J. Control. Release, 142 (2) 149–159 (2010)

25.

Zhang, Y, Wang, R, Hua, Y, Baumgartner, R, Cheng, J, “Trigger-Responsive Poly(β-amino ester) Hydrogels.” ACS Macro Lett., 3 (7) 693–697 (2014)

26.

Chen, D, Wu, M, Chen, J, Zhang, C, Pan, T, Zhang, B, Tian, H, Chen, X, Sun, J, “Robust, Flexible, and Bioadhesive Free-Standing Films for the Co-delivery of Antibiotics and Growth Factors.” Langmuir, 30 (46) 13898–13906 (2014)

27.

Wood, KC, Boedicker, JQ, Lynn, DM, Hammond, PT, “Tunable Drug Release from Hydrolytically Degradable Layer-by-Layer thin Films.” Langmuir, 21 (4) 1603–1609 (2005)

28.

Feng, L, Wang, Y, Luo, Z, Huang, Z, Zhang, Y, Guo, K, Ye, D, “Dual Stimuli-Responsive Nanoparticles for Controlled Release of Anticancer and Anti-inflammatory Drugs Combination.” Chem. A Eur. J., 23 (39) 9397–9406 (2017)

29.

Hofmann, D, Entrialgo-Castaño, M, Kratz, K, Lendlein, A, “Knowledge-Based Approach Towards Hydrolytic Degradation of Polymer-Based Biomaterials.” Adv. Mater., 21 (32–33) 3237–3245 (2009)

30.

Das, D, Das, R, Ghosh, P, Dhara, S, Panda, AB, Pal, S, “Dextrin Cross Linked with Poly(HEMA): A Novel Hydrogel for Colon Specific Delivery of Ornidazole.” RSC Adv., 3 (47) 25340–25350 (2013)

31.

Mi, FL, Wu, YB, Shyu, SS, Schoung, JY, Huang, YB, Tsai, YH, Hao, JY, “Control of Wound Infections Using a Bilayer Chitosan Wound Dressing with Sustainable Antibiotic Delivery.” J. Biomed. Mater. Res., 59 (3) 438–449 (2002)

32.

Gomes, AP, Mano, JF, Queiroz, JA, Gouveia, IC, “Incorporation of Antimicrobial Peptides on Functionalized Cotton Gauzes for Medical Applications.” Carbohydr. Polym., 127 451–461 (2015)

33.

Pollini, M, Paladini, F, Sannino, A, Maffezzoli, A, “Development of Hybrid Cotton/Hydrogel Yarns with Improved Absorption Properties for Biomedical Applications.” Mater. Sci. Eng. C, 63 563–569 (2016)

34.

Chen, X, Prow, TW, Crichton, ML, Jenkins, DW, Roberts, MS, Frazer, IH, Fernando, GJ, Kendall, MA, “Dry-Coated Microprojection Array Patches for Targeted Delivery of Immunotherapeutics to the Skin.” J. Control. Release, 139 (3) 212–220 (2009)

35.

Matsumura, S, Hlil, AR, Lepiller, C, Gaudet, J, Guay, D, Shi, Z, Holdcroft, S, Hay, AS, “Ionomers for Proton Exchange Membrane Fuel Cells with Sulfonic Acid Groups on the End-Groups: Novel Branched Poly(Ether-Ketone)s.” Am. Chem. Soc. Polym. Prepr. Div. Polym. Chem., 49 (1) 511–512 (2008)

36.

Hagberg, EC, Malkoch, M, Ling, Y, Hawker, CJ, Carter, KR, “Effects of Modulus and Surface Chemistry of Thiol-Ene Photopolymers in Nanoimprinting.” Nano Lett., 7 (2) 233–237 (2007)

37.

Melnick, JL, “Advantages and Disadvantages of Killed and Live Poliomyelitis Vaccines.” Bull. World Health Organ., 56 (1) 21–38 (1978)

38.

Shoji, T, Ito, S, “Azulene-Based Donor-Acceptor Systems: Synthesis, Optical, and Electrochemical Properties.” Chem. A Eur. J., 23 (66) 16696–16709 (2017)

39.

Murai, M, Iba, S, Ota, H, Takai, K, “Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness.” Org. Lett., 19 (20) 5585–5588 (2017)

40.

Bui, QN, Li, Y, Jang, MS, Huynh, DP, Lee, JH, Lee, DS, “Redox- and pH-Sensitive Polymeric Micelles Based on Poly(β-amino ester)-Grafted Disulfide Methylene Oxide Poly(ethylene glycol) for Anticancer Drug Delivery.” Macromolecules, 48 (12) 4046–4054 (2015)

41.

Amir, E, Amir, RJ, Campos, LM, Hawker, CJ, “Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-Like Properties.” J. Am. Chem. Soc., 133 (26) 10046–10049 (2011)

42.

Amir, E, Murai, M, Amir, RJ, Cowart, JS, Jr, Chabinyc, ML, Hawker, CJ, “Conjugated Oligomers Incorporating Azulene Building Blocks: Seven- vs. Five-Membered Ring Connectivity.” Chem. Sci., 5 (11) 4483–4489 (2014)

43.

Uchida, R, Sato, T, Tanigawa, H, Uno, K, “Azulene Incorporation and Release by Hydrogel Containing Methacrylamide Propyltrimenthylammonium Chloride, and Its Application to Soft Contact Lens.” J. Control. Release, 92 (3) 259–264 (2003)

44.

Peet, J, Selyutina, A, Bredihhin, A, “Antiretroviral (HIV-1) Activity of Azulene Derivatives.” Bioorg. Med. Chem., 24 (8) 1653–1657 (2016)

45.

Chen, D, Yu, S, Van Ofwegen, L, Proksch, P, Lin, W, “Anthogorgienes A-O, New Guaiazulene-Derived Terpenoids from a Chinese Gorgonian Anthogorgia Species, and Their Antifouling and Antibiotic Activities.” J. Agric. Food Chem., 60 (1) 112–123 (2012)

46.

Nakamura, H, Sekido, M, Yamamoto, Y, “Synthesis of Carboranes Containing an Azulene Framework and In Vitro Evaluation as Boron Carriers.” J. Med. Chem., 40 (18) 2825–2830 (1997)

47.

Gosavi, PM, Moroz, YS, Korendovych, IV, “β-(1-Azulenyl)-l-alanine: A Functional Probe for Determination of pK_a of Histidine Residues.” Chem. Commun., 51 (25) 5347–5350 (2015)

48.

Pham, W, Weissleder, R, Tung, CH, “An Azulene Dimer as a Near-Infrared Quencher.” Angew. Chem. Int. Ed., 41 (19) 3659–3662 (2002)

49.

Yamane, C, Aoyagi, T, Ago, M, Sato, K, Okajima, K, Takahashi, T, “Two Different Surface Properties of Regenerated Cellulose due to Structural Anisotropy.” Polym. J., 38 (8) 819–826 (2006)

50.

Pascault, JP, Williams, RJJ, “Overview of Thermosets: Structure, Properties and Processing for Advanced Applications.” In: Guo, Q (ed.) Thermosets. Structure, Properties and Applications, pp. 3–27 (2012)

51.

Kelnar, I, Kratochvíl, J, Kaprálková, L, Zhigunov, A, Padovec, Z, Růžička, M, Nevoralová, M, “Antagonistic Effects on Mechanical Properties of Microfibrillar Composites with Dual Reinforcement: Explanation by FEA Model of Soft Interface.” J. Appl. Polym. Sci., 134 (20) 1–9 (2017)

52.

Zhang, J, Fredin, NJ, Janz, JF, Sun, B, Lynn, DM, “Structure/Property Relationships in Erodible Multilayered Films: Influence of Polycation Structure on Erosion Profiles and the Release Of Anionic Polyelectrolytes.” Langmuir, 22 (1) 239–245 (2006)

53.

Tang, S, Yin, Q, Zhang, Z, Gu, W, Chen, L, Yu, H, Huang, Y, Chen, X, Xu, M, Li, Y, “Co-delivery of Doxorubicin and RNA Using pH-Sensitive Poly(β-amino ester) Nanoparticles for Reversal of Multidrug Resistance of Breast Cancer.” Biomaterials, 35 (23) 6047–6059 (2014)

Title: Biodegradable polymer coating for controlled release of hydrophobic functional molecules from cotton fabrics
Authors: Coral Hartman
Yanay Popowski
Daniel Raichman
Elizabeth Amir
Publication date: 25-10-2019
Publisher: Springer US
Published in: Journal of Coatings Technology and Research / Issue 3/2020
Print ISSN: 1547-0091
Electronic ISSN: 1935-3804
DOI: https://doi.org/10.1007/s11998-019-00278-3

Springer Professional

Abstract

Graphic abstract

Please log in to get access to your license.

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Other articles of this Issue 3/2020

Photoinduced hydrophilicity and self-cleaning characteristics of silicone-modified soya alkyd/TiO2 nanocomposite coating

Synthesis and application of silver nanoparticles as biocidal agent in polyurethane coating

Wetting metamorphosis of hydrophobic fluoropolymer coatings submerged in water and ultrasonically vibrated

Improvement of the separation and antibiological fouling performance using layer-by-layer self-assembled nanofiltration membranes

UV-curable fluorinated polycarbonate polyurethane with improved surface properties

Epoxy-based multilayered coating containing carbon nanotube (CNT), silicon carbide (SiC), and carbonyl iron (CI) particles: as efficient microwave absorbing materials

Premium Partners