Abstract
Polyester/cotton (PET/CO) fabrics usually burn more violently than single-component fabric due to significant differences of two components as well as “wick effect” during combustion process. Hence, it is very challenging to impart PET/CO fabrics excellent flame retardancy. In this work, a new monomer (ethoxy piperazine (phenyl) phosphoryl ethyl methacrylate, EPPEM) containing multiple unsaturated double bonds was synthesized. As EPPEM contained varied synergistic flame retardant components of phosphorus, nitrogen, and benzene ring, it was expected to form a dense cross-linked network structure on the surface of the fabrics by UV curing to prepare PET/CO fabrics with good flame retardancy and washing resistance. The limiting oxygen index (LOI) value of treated PET/CO fabrics increased up to 27.2% from 17.8% of control sample, which still reached 26.6% after 25 laundering cycles, indicating excellent flame retardancy and water-laundering resistance. Raman spectroscopy, thermogravimetric analysis coupled with Fourier transform infrared analysis and thermogravimetric mass spectrometry indicated that EPPEM promoted the production of more non-combustible compounds during pyrolysis process, such as H2O and CO2. Furthermore, EPPEM decomposed to produce acidic substances which promoted dehydration and coke formation of PET/CO fabrics, thereby preventing exchange of heat and combustible gas. On the basis of the results, a two-phase flame-retardant mechanism of EPPEM/UV-curable system for PET/CO fabrics was proposed.
Similar content being viewed by others
References
Abou-Okeil A, El-Sawy SM, Abdel-Mohdy FA (2013) Flame retardant cotton fabrics treated with organophosphorus polymer. Carbohydr Polym 92:2293–2298. https://doi.org/10.1016/j.carbpol.2012.12.008
Alongi J, Carosio F, Kiekens P (2016) Recent advances in the design of water based-flame retardant coatings for polyester and polyester-cotton blends. Polym-Basel 8:357. https://doi.org/10.3390/polym8100357
Atakan R, Bical A, Celebi E, Ozcan G, Soydan N, Sarac AS (2018) Development of a flame retardant chemical for finishing of cotton, polyester, and CO/PET blends. J Ind Text 49:141–161. https://doi.org/10.1177/1528083718772303
Atakan R, Özcan G, Er E, Öztürk T, Kardaş DG (2019) FR and non-slip finish in one step process for CO/PET fabrics. Tekst Konfeksiyon 29:50–57. https://doi.org/10.32710/tekstilvekonfeksiyon.448130
Baştürk E, Oktay B, Kahraman MV, Kayaman Apohan N (2013) UV cured thiol-ene flame retardant hybrid coatings. Prog Org Coat 76:936–943. https://doi.org/10.1016/j.porgcoat.2012.10.012
Carosio F, Di Blasio A, Cuttica F, Alongi J, Malucelli G (2014) Flame fetardancy of polyester and polyester-cotton blends treated with caseins. Ind Eng Chem Res 53:3917–3923. https://doi.org/10.1021/ie404089t
Casiraghi C, Robertson J, Ferrari AC (2007) Diamond-like carbon for data and beer storage. Mater Today 10:44–53. https://doi.org/10.1016/s1369-7021(06)71791-6
Chen T, Xiao X, Wang J, Guo N (2019) Fire, thermal and mechanical properties of TPE composites with systems containing piperazine pyrophosphate (PAPP), melamine phosphate (MPP) and titanium dioxide (TiO2). Plast Rubber Compos 48:149–159. https://doi.org/10.1080/14658011.2019.1582200
Chen H, Deng C, Zhao ZY, Wan L, Yang AH, Wang YZ (2020) Novel piperazine-containing oligomer as flame retardant and crystallization induction additive for thermoplastics polyurethane. Chem Eng J 400:125941. https://doi.org/10.1016/j.cej.2020.125941
Chiang WY, Ku YA (2002) The effect of maleic anhydride grafting on the flame retardation of plasma pretreated polyethylene. Polym Degrad Stab 76:281–290. https://doi.org/10.1016/s0141-3910(02)00025-3
Colleoni C, Massafra MR, Migani V, Rosace G (2011) Dendrimer finishing influence on CO/PES blended fabrics color assessment. J Appl Polym Sci 120:2122–2129. https://doi.org/10.1002/app.33387
Covaci A, Voorspoels S, Ramos L, Neels H, Blust R (2007) Recent developments in the analysis of brominated flame retardants and brominated natural compounds. J Chromatogr A 1153:145–171. https://doi.org/10.1016/j.chroma.2006.11.060
Edwards B, Rudolf S, Hauser P, El-Shafei A (2015) Preparation, polymerization, and performance evaluation of halogen-free radiation curable flame retardant monomers for cotton substrates. Ind Eng Chem Res 54:577–584. https://doi.org/10.1021/ie502915t
Fan DD, You F, Zhang Y, Huang Z (2018) Flame retardant effects of fabrics finished by hybrid nano-micro silica-based sols. Procedia Eng 211:160–168. https://doi.org/10.1016/j.proeng.2017.12.124
Follmann W, Wober J (2006) Investigation of cytotoxic, genotoxic, mutagenic, and estrogenic effects of the flame retardants tris-(2-chloroethyl)-phosphate (TCEP) and tris-(2-chloropropyl)-phosphate (TCPP) in vitro. Toxicol Lett 161:124–134. https://doi.org/10.1016/j.toxlet.2005.08.008
Fuente D, Lizama C, Urchueguía JF, Conejero JA (2018) Estimation of the light field inside photosynthetic microorganism cultures through Mittag-Leffler functions at depleted light conditions. J Quant Spectrosc Ra 204:23–26. https://doi.org/10.1016/j.jqsrt.2017.08.012
Guo X, Wang Y, Ren Y, Liu X (2021) Fabrication of flame retardant lyocell fibers based on carboxymethylation and aluminum ion chelation. Cellulose 28:6679–6698. https://doi.org/10.1007/s10570-021-03931-6
Haile M, Leistner M, Sarwar O, Toler CM, Henderson R, Grunlan JC (2016) A wash-durable polyelectrolyte complex that extinguishes flames on polyester-cotton fabric. RSC Adv 6:33998–34004. https://doi.org/10.1039/c6ra03637f
Horrocks AR (2011) Flame retardant challenges for textiles and fibres: new chemistry versus innovatory solutions. Polym Degrad Stab 96:377–392. https://doi.org/10.1016/j.polymdegradstab.2010.03.036
Jang JH, Jeong YK (2008) Synthesis and flame-retardancy of UV-curable methacryloyloxy ethyl phosphates. Fiber Polym 9:667–673. https://doi.org/10.1007/s12221-008-0105-2
Kandola BK, Horrocks AR, Price D, Coleman GV (1996) Flame-retardant treatments of cellulose and their influence on the mechanism of cellulose pyrolysis. J Macromol Sci: Polym Rev 36:721–794. https://doi.org/10.1080/15321799608014859
Letcher R (2003) The state-of-the-science and trends of brominated flame retardants in the environment: present knowledge and future directions. Environ Int 29:663–664. https://doi.org/10.1016/s0160-4120(03)00122-3
Lewin M (2005) Unsolved problems and unanswered questions in flame retardance of polymers. Polym Degrad Stab 88:13–19. https://doi.org/10.1016/j.polymdegradstab.2003.12.011
Li QL, Wang XL, Wang DY, Wang YZ, Feng XN, Zheng GH (2011) Durable flame retardant finishing of PET/Cotton blends using a novel PVA-based phosphorus-nitrogen polymer. J Appl Polym Sci 122:342–353. https://doi.org/10.1002/app.34182
Li XY, Gu XY, Zhang S, Li HF, Feng QL, Sun J, Zhao Q (2013) Improving the fire performance of nylon 6,6 fabric by chemical grafting with acrylamide. Ind Eng Chem Res 52:2290–2296. https://doi.org/10.1021/ie302452e
Li SN, Zhong L, Huang S, Wang DF, Zhang FX, Zhang GX (2019) A reactive fluorine-free, efficient superhydrophobic and flame-retardant finishing agent for cotton fabrics. Cellulose 26:6333–6347. https://doi.org/10.1007/s10570-019-02503-z
Liu W, Zhang S, Chen XS, Yu LH, Zhu XJ, Feng QL (2010) Thermal behavior and fire performance of nylon-6,6 fabric modified with acrylamide by photografting. Polym Degrad Stab 95:1842–1848. https://doi.org/10.1016/j.polymdegradstab.2010.04.023
Liu XH, Zhang QY, Cheng BW, Ren YL, Zhang YG, Ding C (2017) Durable flame retardant cellulosic fibers modified with novel, facile and efficient phytic acid-based finishing agent. Cellulose 25:799–811. https://doi.org/10.1007/s10570-017-1550-0
Liu XH, Zhang YG, Cheng BW, Ren YL, Zhang QY, Ding C, Peng B (2018) Preparation of durable and flame retardant lyocell fibers by a one-pot chemical treatment. Cellulose 25:6745–6758. https://doi.org/10.1007/s10570-018-2005-y
Liu Y, Zhou L, Ding F, Li SS, Li R, Li ZG, Huang D, Ren XH (2019) Flame-retardant cotton fabrics modified with phosphoramidate derivative via electron beam irradiation process. J Ind Text. https://doi.org/10.1177/1528083719881816
Liu J, Dong C, Zhang Z, Kong D, Sun H, Lu Z (2020a) Multifunctional flame-retarded and hydrophobic cotton fabrics modified with a cyclic phosphorus/polysiloxane copolymer. Cellulose 27:3531–3549. https://doi.org/10.1007/s10570-020-03016-w
Liu J, Dong C, Zhang Z, Sun H, Kong D, Lu Z (2020b) Durable flame retardant cotton fabrics modified with a novel silicon–phosphorus–nitrogen synergistic flame retardant. Cellulose 27:9027–9043. https://doi.org/10.1007/s10570-020-03370-9
Liu L, Xu Y, Di Y, Xu M, Pan Y, Li B (2020c) Simultaneously enhancing the fire retardancy and crystallization rate of biodegradable polylactic acid with piperazine-1,4-diylbis (diphenylphosphine oxide). Compos Part B-Eng 202:108407. https://doi.org/10.1016/j.compositesb.2020.108407
Liu LX, Pan Y, Zhao YY, Cai W, Gui Z, Hu Y, Wang X (2020d) Self-assembly of phosphonate-metal complex for superhydrophobic and durable flame-retardant polyester–cotton fabrics. Cellulose 27:6011–6025. https://doi.org/10.1007/s10570-020-03148-z
Liu XH, Zhang QY, Peng B, Ren YL, Cheng BW, Ding C, Su XW, He J, Lin SG (2020e) Flame retardant cellulosic fabrics via layer-by-layer self-assembly double coating with egg white protein and phytic acid. J Clean Prod 243:118641. https://doi.org/10.1016/j.jclepro.2019.118641
Liu YS, Guo YB, Ren YL, Wang Y, Guo X, Liu XH (2020f) Phosphorylation of sodium copper chlorophyll enables color-fasten and durable flame retardant wool fibers. Polym Degrad Stab 179:109286. https://doi.org/10.1016/j.polymdegradstab.2020.109286
Mali PP, Pawar NS, Sonawane NS, Patil V, Patil R (2020) UV curable flame retardant coating: a novel synthetic approach of trispiperazido phosphate based reactive diluent. Pigm Resin Technol 50:271–283. https://doi.org/10.1108/prt-06-2020-0058
Malucelli G (2016) Surface-engineered fire protective coatings for fabrics through sol-gel and layer-by-layer methods: an overview. Coatings 6:33. https://doi.org/10.3390/coatings6030033
Mayer-Gall T, Knittel D, Gutmann JS, Opwis K (2015) Permanent flame retardant finishing of textiles by allyl-functionalized polyphosphazenes. ACS Appl Mater Inter 7:9349–9363. https://doi.org/10.1021/acsami.5b02141
Mayer-Gall T, Plohl D, Derksen L, Lauer D, Neldner P, Ali W, Fuchs S, Gutmann JS, Opwis K (2019) A green water-soluble cyclophosphazene as a flame retardant finish for textiles. Molecules 24:118641. https://doi.org/10.3390/molecules24173100
Palaskar SS, Desai AN, Shukla SR (2016) Plasma induced nano-finish for multifunctional properties on cotton fabric. Indian J Fibre Text 41:325–330
Pan Y, Song L, Hu Y (2017) Effect of calcium ion crosslinked alginate based coating on flame retardancy of polyester-cotton fabric. Mater Sci Forum 909:145–150. https://doi.org/10.4028/www.scientific.net/MSF.909.145
Peng S, Wang YC, Lan YR, Shi XM, Zhang H, Qu HQ, Jz Xu (2020) Rational design of multifunctional superoleophobic/superhydrophilic, photocatalytic, and fire-retardant polyethylene terephthalate fabrics through layer-by-layer technique. Compos Part B-Eng 200:108264. https://doi.org/10.1016/j.compositesb.2020.108264
Qian XD, Song L, Hu Y, Yuen RKK, Chen LJ, Guo YQ, Hong NN, Jiang SH (2011) Combustion and thermal degradation mechanism of a novel intumescent flame retardant for epoxy acrylate containing phosphorus and nitrogen. Ind Eng Chem Res 50:1881–1892. https://doi.org/10.1021/ie102196k
Qu ZC, Wu K, Jiao EX, Chen WL, Hu ZR, Xu CA, Shi J, Wang S, Tan ZY (2020) Surface functionalization of few-layer black phosphorene and its flame retardancy in epoxy resin. Chem Eng J 382:122991. https://doi.org/10.1016/j.cej.2019.122991
Ren YL, Liu YS, Wang Y, Guo X, Liu XH (2020) Preparation of durable and flame retardant lyocell fabrics by using a biomass-based modifier derived from vitamin C. Cellulose 27:6677–6689. https://doi.org/10.1007/s10570-020-03218-2
Salmeia KA, Gaan S, Malucelli G (2016) Recent advances for flame retardancy of textiles based on phosphorus chemistry. Polymers-Basel 8:319. https://doi.org/10.3390/polym8090319
Simonetti P, Nazir R, Gooneie A, Lehner S, Jovic M, Salmeia KA, Hufenus R, Rippl A, Kaiser J-P, Hirsch C et al (2019) Michael addition in reactive extrusion: a facile sustainable route to developing phosphorus based flame retardant materials. Compos Part B-Eng 178:107470. https://doi.org/10.1016/j.compositesb.2019.107470
Sjodin A (2003) A review on human exposure to brominated flame retardants-particularly polybrominated diphenyl ethers. Environ Int 29:829–839. https://doi.org/10.1016/s0160-4120(03)00108-9
Su XW, Cheng CZ, Zheng YB, Liu XH, Ren YL, He J, Lin SG, Cheng BW (2021) A novel biomass vitamin B6-based flame retardant for lyocell fibers. Cellulose 28:3201–3214. https://doi.org/10.1007/s10570-021-03681-5
Sun CF, Gao M (2013) Effect of transition metal on the thermal degradation of cotton cellulose modified with THPC. Adv Mater Res 683:361–365. https://doi.org/10.4028/www.scientific.net/AMR.683.361
Thanamongkollit N, Miller KR, Soucek MD (2012) Synthesis of UV-curable tung oil and UV-curable tung oil based alkyd. Prog Org Coat 73:425–434. https://doi.org/10.1016/j.porgcoat.2011.02.003
Tsai KC, Kuan CF, Chen CH, Kuan HC, Hsu SW, Lee FM, Chiang CL (2013) Study on thermal degradation and flame retardant property of halogen-free polypropylene composites using XPS and cone calorimeter. J Appl Polym Sci 127:1084–1091. https://doi.org/10.1002/app.37700
Wang LN, Xu XL, Ren YL, Sui XY (2013) Graft copolymerization of acrylamide onto polyester-cotton blended fabric by using potassium permanganate redox system. Adv Textile Eng Mater 627:205–211. https://doi.org/10.4028/www.scientific.net/AMR.627.205
Wang S, Du X, Jiang Y, Xu J, Zhou M, Wang H, Cheng X, Du Z (2019) Synergetic enhancement of mechanical and fire-resistance performance of waterborne polyurethane by introducing two kinds of phosphorus-nitrogen flame retardant. J Colloid Interf Sci 537:197–205. https://doi.org/10.1016/j.jcis.2018.11.003
Wang J, Guo Y, Zhao S, Huang RY, Kong XJ (2019a) A novel intumescent flame retardant imparts high flame retardancy to epoxy resin. Polym Adv Technol 31:932–940. https://doi.org/10.1002/pat.4827
Wang B, Xu YJ, Li P, Zhang FQ, Liu Y, Zhu P (2020) Flame-retardant polyester/cotton blend with phosphorus/nitrogen/silicon-containing nano-coating by layer-by-layer assembly. Appl Surf Sci 509:145323. https://doi.org/10.1016/j.apsusc.2020.145323
Xing WY, Hu Y, Song L, Chen XL, Zhang P, Ni JX (2009) Thermal degradation and combustion of a novel UV curable coating containing phosphorus. Polym Degrad Stab 94:1176–1182. https://doi.org/10.1016/j.polymdegradstab.2009.02.014
Yu LH, Zhang S, Liu W, Zhu XJ, Chen XP, Chen XS (2010) Improving the flame retardancy of PET fabric by photo-induced grafting. Polym Degrad Stab 95:1934–1942. https://doi.org/10.1016/j.polymdegradstab.2010.04.005
Yuan B, Sun Y, Chen X, Shi Y, Dai H, He S (2018) Poorly-/well-dispersed graphene: abnormal influence on flammability and fire behavior of intumescent flame retardant. Compos Part A-Appl S 109:345–354. https://doi.org/10.1016/j.compositesa.2018.03.022
Zhang QY, Liu XH, Ren YL, Zhang YG, Cheng BW (2020a) Fabrication of a high phosphorus–nitrogen content modifier with star structure for effectively enhancing flame retardancy of lyocell fibers. Cellulose 27:8369–8383. https://doi.org/10.1007/s10570-020-03333-0
Zhang Z, Kong D, Sun H, Sun L, Dong C, Lu Z (2020b) Synthetic novel, convenient and eco-friendly Si/P/N synergistic treatment agent to improve the flame retardancy and thermal stability of cotton fabrics. Cellulose 27:10473–10487. https://doi.org/10.1007/s10570-020-03488-w
Zhu ZM, Wang LX, Dong LP (2019) Influence of a novel P/N-containing oligomer on flame retardancy and thermal degradation of intumescent flame-retardant epoxy resin. Polym Degrad Stab 162:129–137. https://doi.org/10.1016/j.polymdegradstab.2019.02.021
Acknowledgments
The authors are very grateful for financial supports provided by the National Key Research and Development Program of China (No. 2017YFB0309000) and Quanzhou Science and Technology Bureau (No. 2019C104).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Ethical approval
The authors have no statement about ethical approval as this research does not involve humans and animals.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Yang, X., Liu, X., Yang, X. et al. A phosphorous/nitrogen-containing flame retardant with UV-curing for polyester/cotton fabrics. Cellulose 29, 1263–1281 (2022). https://doi.org/10.1007/s10570-021-04346-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-021-04346-z