Abstract
A novel reactive N–P flame retardant ammonium salt of guanidine acetate tetramethylenephosphonic acid (AGATMPA) with good solubility was synthesized under mild conditions. AGATMPA was combined with cotton cellulose through P–O–C and C–O–C covalent bonds. The molecular structure of AGATMPA was characterized by 1H NMR, 13C NMR, and 31P NMR. The control cotton and treated cotton were characterized by FT-IR, SEM, and EDX to verify that the flame retardant was successfully grafted onto the cotton fabric. The LOI and vertical flammability tests indicated that the AGATMPA-treated cotton showed outstanding flame retardance with LOI of 45.5% and durability with LOI of 29.5% after 50 laundering cycles, respectively. TG analysis showed that treated cotton exhibits favorable thermal and thermal oxidation stability, and the carbon residual can reach 42.26% in nitrogen and 12.55% in air at 700 °C. Cone calorimetry suggested that the PHRR and THR values of treated cotton decreased by 95.18% and 70.07%, respectively. TG-IR results revealed that the amount of thermally-degraded volatiles of treated cotton decreased and no new types of toxic gases were produced, compared with control cotton. XRD results showed little change in the crystalline region of the cotton fabric before and after treatment with AGATMPA. The flame retardant finishing process has some effect on the physical properties of cotton fabric while only slightly influencing its application.
Graphic abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Akech SRO, Harrison O, Saha A (2018) Removal of a potentially hazardous chemical, tetrakis (hydroxymethyl) phosphonium chloride from water using biochar as a medium of adsorption. Environ Technol Innov 12:196–210. https://doi.org/10.1016/j.eti.2018.09.002
Annalisa C, Francesca B, Giulio M, Chiara M, Monica P (2016) DNA-chitosan cross-linking and photografting to cotton fabrics to improve washing fastness of the fire-resistant finishing. Cellulose 23:3963–3984. https://doi.org/10.1007/s10570-016-1067-y
Braun U et al (2006) Influence of the oxidation state of phosphorus on the decomposition and fire behaviour of flame-retarded epoxy resin composites. Polymer 47:8495–8508. https://doi.org/10.1016/j.polymer.2006.10.022
Castellano A, Colleoni C, Iacono G, Mezzi A, Plutino MR, Malucelli G, Rosace G (2019) Synthesis and characterization of a phosphorous/nitrogen based sol-gel coating as a novel halogen- and formaldehyde-free flame retardant finishing for cotton fabric. Polym Degrad Stab 162:148–159. https://doi.org/10.1016/j.polymdegradstab.2019.02.006
Chen X, Huo L, Jiao C, Li S (2013) TG–FTIR characterization of volatile compounds from flame retardant polyurethane foams materials. J Anal Appl Pyrol 100:186–191. https://doi.org/10.1016/j.jaap.2012.12.017
Chen YC, Sun B, Zhang HX, Zhou XD (2016) Synthesis and application of a sulfur-containing phosphoric amide flame retardant for nylon fabric. Fire Mater 40:959–972. https://doi.org/10.1002/fam.2354
Chen RJ, Huang XY, Zheng RZ, Xie DL, Mei Y, Zou RQ (2020) Flame-retardancy and thermal properties of a novel phosphorus-modified PCM for thermal energy storage. Chem Eng J. https://doi.org/10.1016/j.cej.2019.122500
Dehabadi VA, Buschmann HJ, Gutmann JS (2013) Durable press finishing of cotton fabrics: an overview. Text Res J 83:1974–1995. https://doi.org/10.1177/0040517513483857
Dutkiewicz M, Przybylak M, Januszewski R, Maciejewski H (2018) Synthesis and flame retardant efficacy of hexakis(3-(triethoxysilyl)propyloxy)cyclotriphosphazene/silica coatings for cotton fabrics. Polym Degrad Stab 148:10–18. https://doi.org/10.1016/j.polymdegradstab.2017.11.018
Feng YJ, Zhou Y, Li DK, He S, Zhang FX, Zhang GX (2017) A plant-based reactive ammonium phytate for use as a flame-retardant for cotton fabric. Carbohydr Polym 175:636–644. https://doi.org/10.1016/j.carbpol.2017.06.129
French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896. https://doi.org/10.1007/s10570-013-0030-4
Fu J, Yang FC, Chen GP, Zhang GF, Huang C, Guo ZG (2019) A facile coating with water-repellent and flame-retardant properties on cotton fabric. New J Chem 43:10183–10189. https://doi.org/10.1039/c9nj02240f
Huang S, Zhong L, Li S, Liu M, Zhang Z, Zhang F, Zhang G (2019) A novel monosodium-glutamate-based flame retardant containing phosphorus for cotton fabrics. Cellulose 26:2715–2728. https://doi.org/10.1007/s10570-018-02241-8
Jatoi AW, Khatri Z, Ahmed F, Memon MH (2015) Effect of silicone nano, nano/micro and nano/macro-emulsion softeners on color yield and physical characteristics of dyed cotton fabric. J Surfactants Deterg 18:205–211. https://doi.org/10.1007/s11743-014-1647-5
Jia YL, Lu Y, Zhang GX, Liang YJ, Zhang FX (2017) Facile synthesis of an eco-friendly nitrogen-phosphorus ammonium salt to enhance the durability and flame retardancy of cotton. J Mater Chem A 5:9970–9981. https://doi.org/10.1039/c7ta01106g
Jiang X, Gu J, Tian XZ (2012) Modification of cellulose for high glucose generation. Abstracts of papers of the American Chemical Society, p 243
Jiang ZM, Li H, He YW, Liu Y, Dong CH, Zhu P (2019) Flame retardancy and thermal behavior of cotton fabrics based on a novel phosphorus-containing siloxane. Appl Surf Sci 479:765–775. https://doi.org/10.1016/j.apsusc.2019.02.159
Khakran G, Chamani M, Foroudi F, Sadeghi AA, Afshar MA (2018) Effect of guanidine acetic acid addition to corn-soybean meal based diets on productive performance, blood biochemical parameters and reproductive hormones of laying hens. Kafkas Universitesi Veteriner Fakultesi Dergisi 24:99–105. https://doi.org/10.9775/kvfd.2017.18407
Kim SJ, Jang J (2017) Synergistic UV-curable flame-retardant finish of cotton using comonomers of vinylphosphonic acid and acrylamide. Fibers Polym 18:2328–2333. https://doi.org/10.1007/s12221-017-7628-3
Li Q-L, Huang F-Q, Wei Y-J, Wu J-Z, Zhou Z, Liu G (2018a) A phosphorus–nitrogen flame-retardant: synthesis and application in cotton fabrics. Mater Sci. https://doi.org/10.5755/j01.ms.24.4.18606
Li Y et al (2018b) Durable flame retardant and antibacterial finishing on cotton fabrics with cyclotriphosphazene/polydopamine/silver nanoparticles hybrid coatings. Appl Surf Sci 435:1337–1343. https://doi.org/10.1016/j.apsusc.2017.11.269
Li S, Zhong L, Huang S, Wang D, Zhang F, Zhang G (2019a) 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
Li SS, Lin XH, Li ZG, Ren XH (2019b) Hybrid organic-inorganic hydrophobic and intumescent flame-retardant coating for cotton fabrics. Compos Commun 14:15–20. https://doi.org/10.1016/j.coco.2019.05.005
Liu ZY, Xu MJ, Wang Q, Li B (2017) A novel durable flame retardant cotton fabric produced by surface chemical grafting of phosphorus- and nitrogen-containing compounds. Cellulose 24:4069–4081. https://doi.org/10.1007/s10570-017-1391-x
Liu XH, Zhang YG, Cheng BW, Ren YL, Zhang QY, Ding C, Peng B (2018a) 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, Wang QQ, Jiang ZM, Zhang CJ, Li ZF, Chen HQ, Zhu P (2018b) Effect of chitosan on the fire retardancy and thermal degradation properties of coated cotton fabrics with sodium phytate and APTES by LBL assembly. J Anal Appl Pyrol 135:289–298. https://doi.org/10.1016/j.jaap.2018.08.024
Manfredi A, Carosio F, Ferruti P, Alongi J, Ranucci E (2018) Disulfide-containing polyamidoamines with remarkable flame retardant activity for cotton fabrics. Polym Degrad Stab 156:1–13. https://doi.org/10.1016/j.polymdegradstab.2018.07.028
Mohsin M, Quatab HG, Sarwar N, Ramzan N, Ahmad SW (2017) Synthesis of halogen and formaldehyde free bio based fire retardant for cotton. Ind Text 68:221–225
Nakanishi S, Masuko F, Hashimoto T (1999) Durable flame-retardant finished cotton fabrics characterized by thermal degradation behaviors. J Appl Polym Sci 71:975–987. https://doi.org/10.1002/(sici)1097-4628(19990207)71:6%3c975:aid-app13%3e3.0.co;2-s
Rosace G, Castellano A, Trovato V, Iacono G, Malucelli G (2018) Thermal and flame retardant behaviour of cotton fabrics treated with a novel nitrogen-containing carboxyl-functionalized organophosphorus system. Carbohydr Polym 196:348–358. https://doi.org/10.1016/j.carbpol.2018.05.012
Simkovic I (2012) TG/DTG/DTA evaluation of flame retarded cotton fabrics and comparison to cone calorimeter data. Carbohydr Polym 90:976–981. https://doi.org/10.1016/j.carbpol.2012.06.030
Taherkhani A, Hasanzadeh M (2018) Durable flame retardant finishing of cotton fabrics with poly(amidoamine) dendrimer using citric acid. Mater Chem Phys 219:425–432. https://doi.org/10.1016/j.matchemphys.2018.08.058
Wu K, Song L, Hu Y, Lu HD, Kandola BK, Kandare E (2009) Synthesis and characterization of a functional polyhedral oligomeric silsesquioxane and its flame retardancy in epoxy resin. Prog Org Coat 65:490–497. https://doi.org/10.1016/j.porgcoat.2009.04.008
Wyss M, Kaddurah-Daouk R (2000) Creatine and creatinine metabolism. Physiol Rev 80:1107–1213
Yang CQ, He QL (2011) Applications of micro-scale combustion calorimetry to the studies of cotton and nylon fabrics treated with organophosphorus flame retardants. J Anal Appl Pyrol 91:125–133. https://doi.org/10.1016/j.jaap.2011.01.012
Yang ZY, Fei B, Wang XW, Xin JH (2012a) A novel halogen-free and formaldehyde-free flame retardant for cotton fabrics. Fire Mater 36:31–39. https://doi.org/10.1002/fam.1082
Yang ZY, Wang XW, Lei DP, Fei B, Xin JH (2012b) A durable flame retardant for cellulosic fabrics. Polym Degrad Stab 97:2467–2472. https://doi.org/10.1016/j.polymdegradstab.2012.05.023
Zhang D et al (2017) Flame retardant and hydrophobic coatings on cotton fabrics via sol-gel and self-assembly techniques. J Colloid Interface Sci 505:892–899. https://doi.org/10.1016/j.jcis.2017.06.087
Zhang FX, Gao WW, Jia YL, Lu Y, Zhang GX (2018) A concise water-solvent synthesis of highly effective, durable, and eco-friendly flame-retardant coating on cotton fabrics. Carbohydr Polym 199:256–265. https://doi.org/10.1016/j.carbpol.2018.05.085
Acknowledgments
The research was supported by Chongqing postgraduate education and teaching reform major project (No: yjg152022), and Chongqing natural science foundation of key projects in China (Grant No: CSTC 2014 yy kfB50002).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wan, C., Zhang, G. & Zhang, F. A novel guanidine ammonium phosphate for preparation of a reactive durable flame retardant for cotton fabric. Cellulose 27, 3469–3483 (2020). https://doi.org/10.1007/s10570-020-03003-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10570-020-03003-1