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Synthesis and characterization of UV-curable cellulose acetate butyrate-based oligomers and their cotton fabric coatings

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Abstract

In order to improve the thermal stability and flexibility, cellulose acetate butyrate (CAB) was modified with toluene diisocyanate–hydroxyethyl methacrylate (TDI–HEMA) adduct in various molar ratios. The obtained oligomer was characterized by proton nuclear magnetic resonance (1H NMR) and Fourier transform infrared (FTIR) spectroscopies. Gloss, cross-hatch, contact angle, and Taber abrasion tests were all used to investigate the film forming performance of the modified CAB oligomers on glass plates. The UV-cured free films of the synthesized oligomers were examined in terms of the mechanical tests. By using the synthesized CAB oligomers, coating formulations were prepared and applied onto cotton fabrics in order to make the cotton fabrics more durable in outdoor environments. The existence of the coating layer on the fabric surfaces was investigated by scanning electron microscopy (SEM). The coated UV-cured fabrics were evaluated separately in terms of abrasion, thermal conductivity, and air and water vapor permeability properties. Results proved that the oligomer (50%-CAB) in which 50% of the hydroxyl groups of CAB were reacted with TDI–HEMA adduct showed the best mechanical properties with the highest tensile strength and modulus values. Considering the coated fabrics, the least deformation against abrasion, the highest air/water vapor permeability, and the best thermal conductivity were all recorded in 50%-CAB coated sample.

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References

  1. Cao, Y, Li, H, Zhang, J, “Homogeneous Synthesis and Characterization of Cellulose Acetate Butyrate (CAB) in 1-Allyl-3-Methylimidazolium Chloride (AmimCl) Ionic Liquid.” Ind. Eng. Chem. Res., 50 (13) 7808–7814 (2011)

    Article  CAS  Google Scholar 

  2. El-Sakhawy, M, Kamel, S, Salama, A, Sarhan, H-A, “Carboxymethyl Cellulose Acetate Butyrate: A Review of the Preparations, Properties, and Applications.” J. Drug Deliv., 2014 1–6 (2014)

    Article  Google Scholar 

  3. Hou, A, Zhou, M, Wang, X, “Preparation and Characterization of Durable Antibacterial Cellulose Biomaterials Modified with Triazine Derivatives.” Carbohydr., Polym. 75 (2) 328–332 (2009)

    Article  CAS  Google Scholar 

  4. Wang, X, Huang, S, Wang, Y, Wei, P, Chen, Y, Xia, Y, Wang, Y, “Eco-Friendly Cellulose Acetate Butyrate/Poly (Butylene Succinate) Blends: Crystallization, Miscibility, Thermostability, Rheological and Mechanical Properties.” J. Polym. Res., 24 (2) 16 (2017)

    Article  Google Scholar 

  5. Çakmakçı, E, Güngör, A, Kayaman-Apohan, N, Kuruca, SE, Çetin, MB, Dar, KA, “Cell Growth on In Situ Photo-Cross-Linked Electrospun Acrylated Cellulose Acetate Butyrate.” J. Biomater. Sci. Polym. Ed., 23 (7) 887–899 (2012)

    Article  Google Scholar 

  6. Kayaman-Apohan, N, Amanoel, A, Arsu, N, Güngör, A, “Synthesis and Characterization of UV-Curable Vinyl Ether Functionalized Urethane Oligomers.” Prog. Org. Coat., 49 (1) 23–32 (2004)

    Article  CAS  Google Scholar 

  7. Xie, J, Zhang, N, Guers, M, Varadan, VK, “Ultraviolet-Curable Polymers with Chemically Bonded Carbon Nanotubes for Microelectromechanical System Applications.” Smart Mater. Struct., 11 (4) 575 (2002)

    Article  CAS  Google Scholar 

  8. Yildiz, Z, Onen, HA, “Dual-Curable PVB Based Adhesive Formulations for Cord/Rubber Composites: The Influence of Reactive Diluents.” Int. J. Adhes. Adhes., 78 38–44 (2017)

    Article  CAS  Google Scholar 

  9. Barszczewska-Rybarek, IM, “Characterization of Urethane-Dimethacrylate Derivatives as Alternative Monomers for the Restorative Composite Matrix.” Dent. Mater., 30 (12) 1336–1344 (2014)

    Article  CAS  Google Scholar 

  10. Liu, X-D, Sheng, D-K, Gao, X-M, Li, T-B, Yang, Y-M, “UV-Assisted Surface Modification of PET Fiber for Adhesion Improvement.” Appl. Surf. Sci., 264 61–69 (2013)

    Article  CAS  Google Scholar 

  11. Wang, F, Hu, J, Tu, W, “Study on Microstructure of UV-Curable Polyurethane Acrylate Films.” Prog. Org. Coat., 62 (3) 245–250 (2008)

    Article  CAS  Google Scholar 

  12. Wang, SJ, Wang, YL, Yang, PF, Li, TD, “In Preparation of Polyurethane-Poly (Butyl Acrylate) Hybrid Latexes via Miniemulsion Polymerization.” In: Applied Mechanics and Materials, pp. 3938–3941. Trans Tech Publications (2012)

  13. El-Molla, M, “Synthesis of Polyurethane Acrylate Oligomers as Aqueous UV-Curable Binder for Inks of Ink Jet in Textile Printing and Pigment Dyeing.” Dyes Pigm., 74 (2) 371–379 (2007)

    Article  CAS  Google Scholar 

  14. Dehmen, OG, Onen, HA, Yildiz, Z, Gungor, A, “Chemical, Mechanical, and Thermal Properties of UV-Curable Cellulose Acetate Butyrate-Based Oligomers and Their Electrospun Fibrous Mats.” J. Coat. Technol. Res., 17 1043–1052 (2020)

    Article  CAS  Google Scholar 

  15. Pitchaimari, G, Sarma, K, Varshney, L, Vijayakumar, C, “Influence of the Reactive Diluent on Electron Beam Curable Funtionalized N-(4-Hydroxyl Phenyl) Maleimide Derivatives–Studies on Thermal Degradation Kinetics Using Model Free Approach.” Thermochim. Acta, 597 8–18 (2014)

    Article  CAS  Google Scholar 

  16. ISO/CD 5470-2: Rubber- or Plastics-Coated Fabrics—Determination of Abrasion Resistance—Part 2: Martindale Abrader, 2003

  17. EN ISO 9237:1996, TEXTILES. Determination of Permeability of Fabrics to Air, 1996

  18. ISO 11092:2014 Textiles, Physiological Effects, Measurement of Thermal and Water-Vapour Resistance Under Steady-State Conditions (Sweating Guarded-Hotplate Test), 2014

  19. Engin, A, Nuray, ÖC, Abdurrahim, Y, Adnan, M, “Investigating the Thermal Comfort Properties of Men’s Jacket as Single and Multiple Layered Material.” Ind. Text., 68 (6) 458–463 (2017)

    Article  Google Scholar 

  20. Naeem, J, Akcagun, E, Mazari, A, Havelka, A, Kus, Z, “Analysis of Thermal Properties, Water Vapor Resistance and Radiant Heat Transmission Through Different Combinations of Firefighter Protective Clothing.” Ind. Text., 69 (6) 458 (2018)

    Google Scholar 

  21. Akcagun, E, Bogusławska-Bączek, M, Hes, L, “Thermal Insulation and Thermal Contact Properties of Wool and Wool/PES Fabrics in Wet State.” J. Nat. Fibers, 16 (2) 199–208 (2019)

    Article  CAS  Google Scholar 

  22. Grepinet, B, Pla, F, Hobbes, P, Swaels, P, Monge, T, “Modeling and Simulation of Urethane Acrylates Synthesis. I. Kinetics of Uncatalyzed Reaction of Toluene Diisocyanate with a Monoalcohol.” J. Appl. Polym. Sci., 75 (5) 705–712 (2000)

    Article  CAS  Google Scholar 

  23. Liao, F, Zeng, X-R, Li, H-Q, Lai, X-J, Zhao, F-C, “Synthesis and Properties of UV Curable Polyurethane Acrylates Based on Two Different Hydroxyethyl Acrylates.” J. Cent. South Univ., 19 (4) 911–917 (2012)

    Article  CAS  Google Scholar 

  24. Tan, SZ, Wang, Y, Zhang, YF, Zhou, WL, “In Preparation of a Novel Prepolymer of Polyurethane Acrylate.” In: Advanced Materials Research, pp. 153–156. Trans Tech Publications (2012)

  25. Dong, Y, Mosquera-Giraldo, LI, Troutman, J, Skogstad, B, Taylor, LS, Edgar, KJ, “Amphiphilic Hydroxyalkyl Cellulose Derivatives for Amorphous Solid Dispersion Prepared by Olefin Cross-Metathesis.” Polym. Chem., 7 (30) 4953–4963 (2016)

    Article  CAS  Google Scholar 

  26. Kunwong, D, Sumanochitraporn, N, Kaewpirom, S, “Curing Behavior of a UV-Curable Coating Based on Urethane Acrylate Oligomer: The Influence of Reactive Monomers.” Sonklanakarin J. Sci. Technol., 33 (2) 201 (2011)

    CAS  Google Scholar 

  27. Dong, Y, Edgar, KJ, “Imparting Functional Variety to Cellulose Ethers via Olefin Cross-Metathesis.” Polym. Chem., 6 (20) 3816–3827 (2015)

    Article  CAS  Google Scholar 

  28. Hébert, M, Emmel, P, Hersch, RD, “In A Prediction Model for Reflection on Varnished Metallic Plates.” In: Conference on Colour in Graphics, Imaging, and Vision, pp. 453–458. Society for Imaging Science and Technology, (2002)

  29. Kahraman, MV, Bayramoğlu, G, Boztoprak, Y, Güngör, A, Kayaman-Apohan, N, “Synthesis of Fluorinated/Methacrylated Epoxy Based Oligomers and Investigation of Its Performance in the UV Curable Hybrid Coatings.” Prog. Org. Coat., 66 (1) 52–58 (2009)

    Article  CAS  Google Scholar 

  30. Li, F, Larock, RC, “New Soybean Oil–Styrene–Divinylbenzene Thermosetting Copolymers. III. Tensile Stress–Strain Behavior.” J. Polym. Sci., Part B: Polym. Phys., 39 (1) 60–77 (2001)

    Article  CAS  Google Scholar 

  31. Yang, S-L, Wu, Z-H, Yang, W, Yang, M-B, “Thermal and Mechanical Properties of Chemical Crosslinked Polylactide (PLA).” Polym. Test., 27 (8) 957–963 (2008)

    Article  CAS  Google Scholar 

  32. Yang, S, Fan, H, Jiao, Y, Cai, Z, Zhang, P, Li, Y, “Improvement in Mechanical Properties of NBR/LiClO4/POSS Nanocomposites by Constructing a Novel Network Structure.” Compos. Sci. Technol., 138, 161–168 (2017)

    Article  CAS  Google Scholar 

  33. Scholes, CA, Freeman, BD, Kentish, SE, “Water Vapor Permeability and Competitive Sorption in Thermally Rearranged (TR) Membranes.” J. Membr. Sci., 470, 132–137 (2014)

    Article  CAS  Google Scholar 

  34. Van den Bergh, J, Zhu, W, Gascon, J, Moulijn, J, Kapteijn, F, “Separation and Permeation Characteristics of a DD3R Zeolite Membrane.” J. Membr. Sci., 316 (1–2) 35–45 (2008)

    Article  Google Scholar 

Download references

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Correspondence to Hacer Aysen Onen.

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Dehmen, O.G., Onen, H.A., Yildiz, Z. et al. Synthesis and characterization of UV-curable cellulose acetate butyrate-based oligomers and their cotton fabric coatings. J Coat Technol Res 18, 1075–1085 (2021). https://doi.org/10.1007/s11998-021-00461-5

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