Research Article
BibTex RIS Cite

Synthesis and application of soybean oil based photocurable polyurethane acrylates for aluminum coating

Year 2025, Volume: 5 Issue: 1, 273 - 283, 31.01.2025
https://doi.org/10.61112/jiens.1536513

Abstract

The aim of this work is to create a new bio-based photocurable oligomer by starting with soybean oil instead of petroleum-based chemicals. For this purpose, acrylic acid (AA) and epoxidized soybean oil (ESBO) were initially reacted. Then the obtained acrylated ESBO (AESBO) oligomer was reacted with the isocyanate groups of the 2,4-toluene diisocyanate - 2-hydroxyethyl methacrylate (TDI-HEMA) adduct. TDI was chosen as the isocyanate source since it is the most widely produced and used form of isocyanate in the global polyurethane industry. HEMA provided the hydroxyl and acrylate groups needed for UV curing and polyurethane production, respectively. Additionally, the oligomer is flexible due to the methyl side group of HEMA. The synthesized oligomer was characterized by Fourier transform infrared (FTIR) spectroscopy and differential scanning calorimetry (DSC) analysis. The coating compositions included the produced TDI-HEMA modified AESBO oligomer, as well as a variety of reactive diluents and a photoinitiator. Then formulations were applied on aluminum plates by spray coating and cured by UV light. The impact of the type of reactive diluent on the film forming and coating performance were all searched. Overall results proved that the inclusion of reactive diluents in the coating formulations helped to increase the coating quality and performance by adjusting the crosslinking density resulting in enhancement in adhesion.

Supporting Institution

TÜBİTAK IRA-SME

Project Number

This study was financially supported by TÜBITAK IRA-SME project with the grant number “122N399”.

Thanks

This study was financially supported by TÜBITAK IRA-SME project with the grant number “122N399”. The extended abstract of this study was orally presented in 14th International Fiber and Polymer Research Symposium (ULPAS), Bursa, Turkey, on 24-25th May, 2024.

References

  • Boisaubert P, et al (2020) Photo-crosslinked coatings from an acrylate terminated non-isocyanate polyurethane (NIPU) and reactive diluent. European Polymer Journal 138, 109961. https://doi.org/10.1016/j.eurpolymj.2020.109961
  • Choi WC, et al (2023) Study on Press Formability and Properties of UV-Curable Polyurethane Acrylate Coatings with Different Reactive Diluents. Polymers 15(4), 880. https://doi.org/10.3390/polym15040880
  • Wang X, Soucek MD (2013) Investigation of non-isocyanate urethane dimethacrylate reactive diluents for UV-curable polyurethane coatings. Progress in Organic Coatings 76(7-8):1057-1067. https://doi.org/10.1016/j.porgcoat.2013.03.001
  • Alam M, et al (2014) Vegetable oil based eco-friendly coating materials: A review article. Arabian Journal of Chemistry 7(4):469-479. https://doi.org/10.1016/j.arabjc.2013.12.023
  • Das A, and Mahanwar P (2020) A brief discussion on advances in polyurethane applications. Advanced Industrial and Engineering Polymer Research 3(3):93-101. https://doi.org/10.1016/j.aiepr.2020.07.002
  • Park JW, et al (2018) Evaluation of UV curing properties of mixture systems with differently sized monomers. Materials 11(4):509. https://doi.org/10.3390/ma11040509
  • Wang S, et al (2020) Making organic coatings greener: Renewable resource, solvent-free synthesis, UV curing and repairability. European Polymer Journal 123:109439. https://doi.org/10.1016/j.eurpolymj.2019.109439
  • Yan Z, et al (2013) Synthesis and properties of a novel UV-cured fluorinated siloxane graft copolymer for improved surface, dielectric and tribological properties of epoxy acrylate coating. Applied surface science 284:683-691. https://doi.org/10.1016/j.apsusc.2013.07.156
  • Wang SJ, et al (2012) Preparation of polyurethane-poly (butyl acrylate) hybrid latexes via miniemulsion polymerization. Applied Mechanics and Materials 204:3938-3941. https://doi.org/10.4028/www.scientific.net/AMM.204-208.3938
  • Eryilmaz O (2024) Revalorization of cellulosic fiber extracted from the waste stem of Brassica oleracea var. botrytis L. (cauliflower) by characterizing for potential composite applications. International Journal of Biological Macromolecules 266:131086. https://doi.org/10.1016/j.ijbiomac.2024.131086
  • Eryilmaz O, Kocak ED, and Sancak E (2023) Braided natural fiber preforms, In: Midani M (ed) Multiscale Textile Preforms and Structures for Natural Fiber Composites, Woodhead Publishing, Manchester UK, pp 221-237. https://doi.org/10.1016/B978-0-323-95329-0.00007-7
  • Eryilmaz O, et al (2020) Investigation of the Water–Based Ink Hold onto the Thermoplastic Composites Reinforced with Sisal Fibers. Journal of Textile Science Fashion Technology 5(3). https://dx.doi.org/10.33552/JTSFT.2020.05.000612
  • Eryılmaz O, and Ovalı S (2024) Investigation and Analysis of New Fiber from Allium fistulosum L. (Scallion) Plant’s Tassel and its Suitability for Fiber-Reinforced Composites. Uludağ University Journal of The Faculty of Engineering 29(1):51-66. https://doi.org/10.17482/uumfd.1410520
  • Ovalı S, and Eryılmaz O (2024) Physical and Chemical Properties of a New Cellulose Fiber Extracted from the Mentha pulegium L. (Pennyroyal) Plant’s Stem. Çukurova University Journal of The Faculty of Engineering 39(1):211-220. https://doi.org/10.21605/cukurovaumfd.1460444
  • Ovalı S, Eryılmaz O, and Uyanık S (2024) Exploring the potential of sustainable natural cellulosic fiber from Sorghum bicolor (Sorghum vulgare var. technicus) stem for textile and composite applications. Cellulose 31(5):3289-3302. https://doi.org/10.1007/s10570-024-05800-4
  • Yildiz Z, and Eryilmaz O (2023) Preimpregnated natural fiber preforms, In: Midani M (ed) Multiscale Textile Preforms and Structures for Natural Fiber Composites, Woodhead Publishing, Manchester, UK, pp 327-340. https://doi.org/10.1016/B978-0-323-95329-0.00003-X
  • Yildiz Z, et al (2024) Sustainable fabric printing by using pre-consumed cellulosic textile wastes: The effect of waste particle content. Journal of Cleaner Production 448:141635. https://doi.org/10.1016/j.jclepro.2024.141635
  • Islam MR, Beg MDH, and Jamari SS (2014) Development of vegetable‐oil‐based polymers. Journal of applied polymer science 131(18). https://doi.org/10.1002/app.40787
  • Yildiz Z (2022) Usage of UV-Curable Soybean Oil Based Coating Formulations for Pretreated Cotton Fabrics. Textile and Apparel 32(3):232-242. https://doi.org/10.32710/tekstilvekonfeksiyon.940434
  • Yildiz Z, et al (2018) Effects of NCO/OH ratio and reactive diluent type on the adhesion strength of polyurethane methacrylates for cord/rubber composites. Polymer-Plastics Technology and Engineering 57(10):935-944. https://doi.org/10.1080/03602559.2017.1364382
  • Yildiz Z, and Onen HA (2017) Dual-curable PVB based adhesive formulations for cord/rubber composites: The influence of reactive diluents. International Journal of Adhesion and Adhesives 78:38-44. https://doi.org/10.1016/j.ijadhadh.2017.06.004
  • Wang F, Hu J, and Tu W (2008) Study on microstructure of UV-curable polyurethane acrylate films. Progress in Organic Coatings 62(3):245-250. https://doi.org/10.1016/j.porgcoat.2007.12.005
  • Goswami A, Umarji A, and Madras G (2010) Degradation kinetics of poly (HDDA‐co‐MMA). Journal of applied polymer science 117(4):2444-2453. https://doi.org/10.1002/app.32122
  • Li Q, et al (2016) Thermal degradation kinetics of poly (acrylate/α-methyl styrene) copolymers. Polymer Degradation and Stability 128:158-164. https://doi.org/10.1016/j.polymdegradstab.2015.10.003
  • Dehmen OG, et al (2021) Synthesis and characterization of UV-curable cellulose acetate butyrate-based oligomers and their cotton fabric coatings. Journal of Coatings Technology and Research 18:1075-1085. https://doi.org/10.1007/s11998-021-00461-5
  • Goodarzi IM, et al (2014) Eco‐friendly, acrylic resin‐modified potassium silicate as water‐based vehicle for anticorrosive zinc‐rich primers. Journal of applied polymer science 131(12). https://doi.org/10.1002/app.40370

Alüminyum kaplama için soya fasulyesi yağı bazlı fotokürlenebilir poliüretan akrilatların sentezi ve uygulaması

Year 2025, Volume: 5 Issue: 1, 273 - 283, 31.01.2025
https://doi.org/10.61112/jiens.1536513

Abstract

Bu çalışmada, ilk olarak akrilik asit (AA) ve epoksitlenmiş soya fasulyesi yağı (ESBO) reaksiyona sokulmuştur. Daha sonra elde edilen akrillenmiş ESBO (AESBO) oligomeri, 2,4-toluen diizosiyanat - 2-hidroksietil metakrilat (TDI-HEMA) ara ürününün izosiyanat grupları ile reaksiyona sokulmuştur. TDI, küresel poliüretan endüstrisinde en yaygın olarak üretilen ve kullanılan izosiyanat formu olduğu için izosiyanat kaynağı olarak seçilmiştir. HEMA, sırasıyla UV kürleme ve poliüretan üretimi için gereken hidroksil ve akrilat gruplarını sağlamıştır. Ayrıca oligomer, HEMA'nın metil yan grubu nedeniyle esnektir. Kaplama formülasyonları, sentezlenen TDI-HEMA modifiye AESBO oligomerinin yanı sıra çeşitli reaktif seyrelticiler ve bir foto başlatıcı içermektedir. Hazırlanan formülasyonlar alüminyum plakalar üzerine sprey kaplama ile uygulanmış ve UV ışığı ile kürlenmiştir. Reaktif seyreltici türünün film oluşturma ve kaplama performansı üzerindeki etkisi araştırılmıştır.

Project Number

This study was financially supported by TÜBITAK IRA-SME project with the grant number “122N399”.

References

  • Boisaubert P, et al (2020) Photo-crosslinked coatings from an acrylate terminated non-isocyanate polyurethane (NIPU) and reactive diluent. European Polymer Journal 138, 109961. https://doi.org/10.1016/j.eurpolymj.2020.109961
  • Choi WC, et al (2023) Study on Press Formability and Properties of UV-Curable Polyurethane Acrylate Coatings with Different Reactive Diluents. Polymers 15(4), 880. https://doi.org/10.3390/polym15040880
  • Wang X, Soucek MD (2013) Investigation of non-isocyanate urethane dimethacrylate reactive diluents for UV-curable polyurethane coatings. Progress in Organic Coatings 76(7-8):1057-1067. https://doi.org/10.1016/j.porgcoat.2013.03.001
  • Alam M, et al (2014) Vegetable oil based eco-friendly coating materials: A review article. Arabian Journal of Chemistry 7(4):469-479. https://doi.org/10.1016/j.arabjc.2013.12.023
  • Das A, and Mahanwar P (2020) A brief discussion on advances in polyurethane applications. Advanced Industrial and Engineering Polymer Research 3(3):93-101. https://doi.org/10.1016/j.aiepr.2020.07.002
  • Park JW, et al (2018) Evaluation of UV curing properties of mixture systems with differently sized monomers. Materials 11(4):509. https://doi.org/10.3390/ma11040509
  • Wang S, et al (2020) Making organic coatings greener: Renewable resource, solvent-free synthesis, UV curing and repairability. European Polymer Journal 123:109439. https://doi.org/10.1016/j.eurpolymj.2019.109439
  • Yan Z, et al (2013) Synthesis and properties of a novel UV-cured fluorinated siloxane graft copolymer for improved surface, dielectric and tribological properties of epoxy acrylate coating. Applied surface science 284:683-691. https://doi.org/10.1016/j.apsusc.2013.07.156
  • Wang SJ, et al (2012) Preparation of polyurethane-poly (butyl acrylate) hybrid latexes via miniemulsion polymerization. Applied Mechanics and Materials 204:3938-3941. https://doi.org/10.4028/www.scientific.net/AMM.204-208.3938
  • Eryilmaz O (2024) Revalorization of cellulosic fiber extracted from the waste stem of Brassica oleracea var. botrytis L. (cauliflower) by characterizing for potential composite applications. International Journal of Biological Macromolecules 266:131086. https://doi.org/10.1016/j.ijbiomac.2024.131086
  • Eryilmaz O, Kocak ED, and Sancak E (2023) Braided natural fiber preforms, In: Midani M (ed) Multiscale Textile Preforms and Structures for Natural Fiber Composites, Woodhead Publishing, Manchester UK, pp 221-237. https://doi.org/10.1016/B978-0-323-95329-0.00007-7
  • Eryilmaz O, et al (2020) Investigation of the Water–Based Ink Hold onto the Thermoplastic Composites Reinforced with Sisal Fibers. Journal of Textile Science Fashion Technology 5(3). https://dx.doi.org/10.33552/JTSFT.2020.05.000612
  • Eryılmaz O, and Ovalı S (2024) Investigation and Analysis of New Fiber from Allium fistulosum L. (Scallion) Plant’s Tassel and its Suitability for Fiber-Reinforced Composites. Uludağ University Journal of The Faculty of Engineering 29(1):51-66. https://doi.org/10.17482/uumfd.1410520
  • Ovalı S, and Eryılmaz O (2024) Physical and Chemical Properties of a New Cellulose Fiber Extracted from the Mentha pulegium L. (Pennyroyal) Plant’s Stem. Çukurova University Journal of The Faculty of Engineering 39(1):211-220. https://doi.org/10.21605/cukurovaumfd.1460444
  • Ovalı S, Eryılmaz O, and Uyanık S (2024) Exploring the potential of sustainable natural cellulosic fiber from Sorghum bicolor (Sorghum vulgare var. technicus) stem for textile and composite applications. Cellulose 31(5):3289-3302. https://doi.org/10.1007/s10570-024-05800-4
  • Yildiz Z, and Eryilmaz O (2023) Preimpregnated natural fiber preforms, In: Midani M (ed) Multiscale Textile Preforms and Structures for Natural Fiber Composites, Woodhead Publishing, Manchester, UK, pp 327-340. https://doi.org/10.1016/B978-0-323-95329-0.00003-X
  • Yildiz Z, et al (2024) Sustainable fabric printing by using pre-consumed cellulosic textile wastes: The effect of waste particle content. Journal of Cleaner Production 448:141635. https://doi.org/10.1016/j.jclepro.2024.141635
  • Islam MR, Beg MDH, and Jamari SS (2014) Development of vegetable‐oil‐based polymers. Journal of applied polymer science 131(18). https://doi.org/10.1002/app.40787
  • Yildiz Z (2022) Usage of UV-Curable Soybean Oil Based Coating Formulations for Pretreated Cotton Fabrics. Textile and Apparel 32(3):232-242. https://doi.org/10.32710/tekstilvekonfeksiyon.940434
  • Yildiz Z, et al (2018) Effects of NCO/OH ratio and reactive diluent type on the adhesion strength of polyurethane methacrylates for cord/rubber composites. Polymer-Plastics Technology and Engineering 57(10):935-944. https://doi.org/10.1080/03602559.2017.1364382
  • Yildiz Z, and Onen HA (2017) Dual-curable PVB based adhesive formulations for cord/rubber composites: The influence of reactive diluents. International Journal of Adhesion and Adhesives 78:38-44. https://doi.org/10.1016/j.ijadhadh.2017.06.004
  • Wang F, Hu J, and Tu W (2008) Study on microstructure of UV-curable polyurethane acrylate films. Progress in Organic Coatings 62(3):245-250. https://doi.org/10.1016/j.porgcoat.2007.12.005
  • Goswami A, Umarji A, and Madras G (2010) Degradation kinetics of poly (HDDA‐co‐MMA). Journal of applied polymer science 117(4):2444-2453. https://doi.org/10.1002/app.32122
  • Li Q, et al (2016) Thermal degradation kinetics of poly (acrylate/α-methyl styrene) copolymers. Polymer Degradation and Stability 128:158-164. https://doi.org/10.1016/j.polymdegradstab.2015.10.003
  • Dehmen OG, et al (2021) Synthesis and characterization of UV-curable cellulose acetate butyrate-based oligomers and their cotton fabric coatings. Journal of Coatings Technology and Research 18:1075-1085. https://doi.org/10.1007/s11998-021-00461-5
  • Goodarzi IM, et al (2014) Eco‐friendly, acrylic resin‐modified potassium silicate as water‐based vehicle for anticorrosive zinc‐rich primers. Journal of applied polymer science 131(12). https://doi.org/10.1002/app.40370
There are 26 citations in total.

Details

Primary Language English
Subjects Polymer Science and Technologies
Journal Section Research Articles
Authors

Berivan Ozer 0000-0002-2822-7085

Betül Nur Kuş 0009-0005-9118-5585

Pelin Yetman 0009-0007-9919-3111

Müslüm Demircioğlu 0000-0003-0050-8819

Oğuz Eryılmaz 0000-0003-0005-1142

Erhan Sancak 0000-0003-1205-0323

Zehra Yıldız 0000-0002-1573-2074

Project Number This study was financially supported by TÜBITAK IRA-SME project with the grant number “122N399”.
Publication Date January 31, 2025
Submission Date August 21, 2024
Acceptance Date December 4, 2024
Published in Issue Year 2025 Volume: 5 Issue: 1

Cite

APA Ozer, B., Kuş, B. N., Yetman, P., Demircioğlu, M., et al. (2025). Synthesis and application of soybean oil based photocurable polyurethane acrylates for aluminum coating. Journal of Innovative Engineering and Natural Science, 5(1), 273-283. https://doi.org/10.61112/jiens.1536513


by.png
Journal of Innovative Engineering and Natural Science by İdris Karagöz is licensed under CC BY 4.0