Abstract
A novel reactive flame retardant based on L-cysteines containing P, N and S flame retardant elements was synthesized, and using its good water solubility, different concentrations of flame retardant poplar wood powder were prepared, and using the hot pressing process method, flame retardant density boards were made and their flame retardancy was studied. The thermogravimetric infrared coupler (TG-FTIR) test and thermal cracking gas mass spectrometer (Py-GC–MS) test both revealed that the flame retardant modified the thermal decomposition pathway of the wood, forming many residues and producing only a small amount of combustible gas. The ultimate oxygen index (LOI) of poplar density board treated with 20% cysteine-based flame retardant was as high as 60.9%. Scanning electron microscopy (SEM) images revealed that the surface of the treated wood powder was rough and that the wood powder particles were interconnected by the flame retardant. This suggests that the flame-retardant molecules have a bridging effect on the inner structure of the density board. Moreover, the cone calorimetry (CONE) experiments showed that with the flame-retardant treatment, there was significant reduction of total heat release (THR) and heat release rate (HRR) of the density board. The outcomes demonstrated the excellent flame retardancy and catalytic carbon formation of the poplar density board treated with the flame retardant. These findings demonstrate the effectiveness of the cysteine-based flame retardant.
Similar content being viewed by others
Availability of data and materials
The data sets supporting the results of this article are included within the article and its additional files.
References
Alongi J, Ciobanu M, Malucelli G (2011) Sol–gel treatments for enhancing flame retardancy and thermal stability of cotton fabrics: optimisation of the process and evaluation of the durability. Cellulose 18:167–177. https://doi.org/10.1007/s10570-010-9470-2
Chen J, Liu Y, Zhang J et al (2021a) Synthesis of novel arginine-based flame retardant and its application in lyocell fabric. Molecules 26:3588. https://doi.org/10.3390/molecules26123588
Chen Y, Liu S, Wan C, Zhang G (2021b) Facile synthesis of a high efficiency and durability L-citrulline flame retardant for cotton. Int J Biol Macromol 166:1429–1438. https://doi.org/10.1016/j.ijbiomac.2020.11.022
Chen Y, Wan C, Liu S et al (2021c) A novel biomolecule and reactive flame retardant based on methionine for cotton fabrics. Cellulose 28:11665–11678. https://doi.org/10.1007/s10570-021-04255-1
Cho W, Shields JR, Dubrulle L et al (2022) Ion-complexed chitosan formulations as effective fire-retardant coatings for wood substrates. Polym Degrad Stab 197:109870. https://doi.org/10.1016/j.polymdegradstab.2022.109870
Cömert ED, Gökmen V (2019) A new procedure to measure cysteine equivalent methylglyoxal scavenging activity (CEMSA) of foods under simulated physiological conditions. J Funct Foods 63:103575. https://doi.org/10.1016/j.jff.2019.103575
Donmez Cavdar A (2014) Effect of various wood preservatives on limiting oxygen index levels of fir wood. Measurement 50:279–284. https://doi.org/10.1016/j.measurement.2014.01.009
Elvira-León JC, Chimenos JM, Isábal C et al (2016) Epsomite as flame retardant treatment for wood: preliminary study. Constr Build Mater 126:936–942. https://doi.org/10.1016/j.conbuildmat.2016.09.107
Gao M, Yang S, Yang R (2006) Flame retardant synergism of GUP and boric acid by cone calorimetry. J Appl Polym Sci 102:5522–5527. https://doi.org/10.1002/app.24505
Guan H, Meng J, Cheng Z, Wang X (2020) Processing natural wood into a high-performance flexible pressure sensor. ACS Appl Mater Interfaces 12:46357–46365. https://doi.org/10.1021/acsami.0c12561
Han F, Liu Q, Lai X et al (2014) Compatibilizing effect of β-cyclodextrin in RDP/phosphorus-containing polyacrylate composite emulsion and its synergism on the flame retardancy of the latex film. Prog Org Coat 77:975–980. https://doi.org/10.1016/j.porgcoat.2014.02.001
Harada M, Hayashi Y, Hayashi T et al (2005) Effect of moisture content of members on mechanical properties of timber joints. J Wood Sci 51:282–285. https://doi.org/10.1007/s10086-004-0656-9
He W, Song P, Yu B et al (2020) Flame retardant polymeric nanocomposites through the combination of nanomaterials and conventional flame retardants. Prog Mater Sci 114:100687. https://doi.org/10.1016/j.pmatsci.2020.100687
He T, Chen F, Zhu W, Yan N (2022) Functionalized lignin nanoparticles for producing mechanically strong and tough flame-retardant polyurethane elastomers. Int J Biol Macromol 209:1339–1351. https://doi.org/10.1016/j.ijbiomac.2022.04.089
Horrocks AR, Kandola BK, Davies PJ et al (2005) Developments in flame retardant textiles—a review. Polym Degrad Stab 88:3–12. https://doi.org/10.1016/j.polymdegradstab.2003.10.024
Huang S, Feng Y, Li S et al (2019) A novel high whiteness flame retardant for cotton. Polym Degrad Stab 164:157–166. https://doi.org/10.1016/j.polymdegradstab.2019.03.014
Jia C, Chen C, Kuang Y et al (2018a) From wood to textiles: top-down assembly of aligned cellulose nanofibers. Adv Mater 30:1801347. https://doi.org/10.1002/adma.201801347
Jia C, Jiang F, Hu P et al (2018b) Anisotropic, mesoporous microfluidic frameworks with scalable, aligned cellulose nanofibers. ACS Appl Mater Interfaces 10:7362–7370. https://doi.org/10.1021/acsami.7b17764
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
Kong L, Guan H, Wang X (2018) In situ polymerization of furfuryl alcohol with ammonium dihydrogen phosphate in poplar wood for improved dimensional stability and flame retardancy. ACS Sustain Chem Eng 6:3349–3357. https://doi.org/10.1021/acssuschemeng.7b03518
Kumar C, Leggate W (2022) An overview of bio-adhesives for engineered wood products. Int J Adhes Adhes 118:103187. https://doi.org/10.1016/j.ijadhadh.2022.103187
Leong WI, Lo OLI, Cheng FT et al (2021) Using recombinant adhesive proteins as durable and green flame-retardant coatings. Synth Syst Biotechnol 6:369–376. https://doi.org/10.1016/j.synbio.2021.10.005
Li B, Zhang X, Su R (2002) An investigation of thermal degradation and charring of larch lignin in the condensed phase: the effects of boric acid, guanyl urea phosphate, ammonium dihydrogen phosphate and ammonium polyphosphate. Polym Degrad Stab 75:35–44. https://doi.org/10.1016/S0141-3910(01)00202-6
Li S, Zhong L, Huang S et al (2019) A novel flame retardant with reactive ammonium phosphate groups and polymerizing ability for preparing durable flame retardant and stiff cotton fabric. Polym Degrad Stab 164:145–156. https://doi.org/10.1016/j.polymdegradstab.2019.04.009
Li W, Qi S, Liu Q et al (2020) Thermal degradation and flame retardant mechanism of sulfonated polyoxadiazole fibers modified by metal ions. J Polym Res 27:365. https://doi.org/10.1007/s10965-020-02336-6
Liao Y, Chen Y, Wan C et al (2021) An eco-friendly N P flame retardant for durable flame-retardant treatment of cotton fabric. Int J Biol Macromol 187:251–261. https://doi.org/10.1016/j.ijbiomac.2021.07.130
Liu X, Zhang Q, Cheng B et al (2018a) 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 Y, Wang Q-Q, Jiang Z-M et al (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 Pyrolysis 135:289–298. https://doi.org/10.1016/j.jaap.2018.08.024
Liu Q, Chai Y, Ni L, Lyu W (2020a) Flame retardant properties and thermal decomposition kinetics of wood treated with boric acid modified silica sol. Materials 13:4478. https://doi.org/10.3390/ma13204478
Liu X, Ding C, Peng B et al (2020b) Synthesis and application of a new, facile, and efficient sorbitol-based finishing agent for durable and flame retardant lyocell fibers. Cellulose 27:3427–3442. https://doi.org/10.1007/s10570-019-02894-z
Liu X, Zhang Q, Peng B et al (2020c) 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 Y, Wang X, Li Z et al (2022) Construction of biological flame retardant layer on cotton fabric via photografting of nucleotide/amino acid monomers. Cellulose 29:1205–1218. https://doi.org/10.1007/s10570-021-04317-4
Lu J, Huang Y, Jiang P et al (2022) Universal circulating impregnation method for the fabrication of durable flame-retardant plywood with low hygroscopicity and leaching resistance. Polym Degrad Stab 195:109799. https://doi.org/10.1016/j.polymdegradstab.2021.109799
Ma N, Fu Q, Hong Y et al (2020) Processing natural wood into an efficient and durable solar steam generation device. ACS Appl Mater Interfaces 12:18165–18173. https://doi.org/10.1021/acsami.0c02481
Makhlouf G (2022) Preparation of highly efficient chitosan-based flame retardant coatings with good antibacterial properties for cotton fabrics. Prog Org Coat 13:2
Mandlekar N, Malucelli G, Cayla A et al (2018) Fire retardant action of zinc phosphinate and polyamide 11 blend containing lignin as a carbon source. Polym Degrad Stab 153:63–74. https://doi.org/10.1016/j.polymdegradstab.2018.04.019
Mi R, Chen C, Keplinger T et al (2020) Scalable aesthetic transparent wood for energy efficient buildings. Nat Commun 11:3836. https://doi.org/10.1038/s41467-020-17513-w
Peng C, Zhong J, Ma X et al (2022) Transparent, hard-wearing and bio-based organic/silica hybrid coating for bamboo with enhanced flame retardant and antifungal properties. Prog Org Coat 167:106830. https://doi.org/10.1016/j.porgcoat.2022.106830
Qu Z, Wu K, Jiao E et al (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
Rosace G, Castellano A, Trovato V et al (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
Rostami M, Badiei A, Sorouri AM et al (2022) Cur-loaded magnetic ZnFe2O4@L-cysteine—Ox, N-rich mesoporous -gC3N4 nanocarriers as a targeted sonodynamic chemotherapeutic agent for enhanced tumor eradication. Surf Interfaces 30:101900. https://doi.org/10.1016/j.surfin.2022.101900
Samanta A, Höglund M, Samanta P et al (2022) Charge regulated diffusion of silica nanoparticles into wood for flame retardant transparent wood. Adv Sustain Syst 6:2100354. https://doi.org/10.1002/adsu.202100354
Schirp A, Su S (2016) Effectiveness of pre-treated wood particles and halogen-free flame retardants used in wood-plastic composites. Polym Degrad Stab 126:81–92. https://doi.org/10.1016/j.polymdegradstab.2016.01.016
Song K, Ganguly I, Eastin I, Dichiara A (2017) Lignin-modified carbon nanotube/graphene hybrid coating as efficient flame retardant. Int J Mol Sci 18:2368. https://doi.org/10.3390/ijms18112368
Song J, Chen C, Zhu S et al (2018) Processing bulk natural wood into a high-performance structural material. Nature 554:224–228. https://doi.org/10.1038/nature25476
Su X, Cheng C, Zheng Y et al (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
Vadenbo C, Tonini D, Burg V et al (2018) Environmental optimization of biomass use for energy under alternative future energy scenarios for Switzerland. Biomass Bioenergy 119:462–472. https://doi.org/10.1016/j.biombioe.2018.10.001
Wan J, Song J, Yang Z et al (2017) Highly anisotropic conductors. Adv Mater 29:1703331. https://doi.org/10.1002/adma.201703331
Wang Y (2022) Enhanced flame retardancy of modified β-cyclodextrin doped silica fume-based geopolymeric coating covered on plywood. Constr Build Mater 12:2
Wang YY, Tian M, Xu HX, Fan P (2014) Influence of moisture on mechanical properties of cellulose insulation paper. Int J Mod Phys B 28:1450051. https://doi.org/10.1142/S0217979214500519
Wang D, Mu X, Cai W et al (2018a) Constructing phosphorus, nitrogen, silicon-co-contained boron nitride nanosheets to reinforce flame retardant properties of unsaturated polyester resin. Compos Part Appl Sci Manuf 109:546–554. https://doi.org/10.1016/j.compositesa.2018.04.003
Wang P, Xia L, Jian R et al (2018b) Flame-retarding epoxy resin with an efficient P/N/S-containing flame retardant: preparation, thermal stability, and flame retardance. Polym Degrad Stab 149:69–77. https://doi.org/10.1016/j.polymdegradstab.2018.01.026
Wang T, Liu T, Ma T et al (2018c) Study on degradation of phosphorus and nitrogen composite UV-cured flame retardant coating on wood surface. Prog Org Coat 124:240–248. https://doi.org/10.1016/j.porgcoat.2018.08.017
Wang B, Li P, Xu Y-J et al (2020) Bio-based, nontoxic and flame-retardant cotton/alginate blended fibres as filling materials: thermal degradation properties, flammability and flame-retardant mechanism. Compos Part B Eng 194:108038. https://doi.org/10.1016/j.compositesb.2020.108038
Wang Y, Jin Z, Zhang X, Li J (2022) Enhancing CO2 separation performance of mixed matrix membranes by incorporation of L-cysteine-functionalized MoS2. Sep Purif Technol 297:121560. https://doi.org/10.1016/j.seppur.2022.121560
Wei S, Wan C, Zhang L et al (2022) N-doped and oxygen vacancy-rich NiCo2O4 nanograss for supercapacitor electrode. Chem Eng J 429:132242. https://doi.org/10.1016/j.cej.2021.132242
Wu X, Gou T, Zhao Q et al (2022) High-efficiency durable flame retardant with ammonium phosphate ester and phosphine oxide groups for cotton cellulose biomacromolecule. Int J Biol Macromol 194:945–953. https://doi.org/10.1016/j.ijbiomac.2021.11.149
Xiao Y, Pu X, Lu F et al (2022) L-cysteine as sustainable and effective sulfur source in the synthesis of diaryl sulfides and heteroarenethiols. Arab J Chem 15:103896. https://doi.org/10.1016/j.arabjc.2022.103896
Xu F, Zhong L, Xu Y et al (2019a) Highly efficient flame-retardant and soft cotton fabric prepared by a novel reactive flame retardant. Cellulose 26:4225–4240. https://doi.org/10.1007/s10570-019-02374-4
Xu F, Zhong L, Xu Y et al (2019b) Synthesis of three novel amino acids-based flame retardants with multiple reactive groups for cotton fabrics. Cellulose 26:7537–7552. https://doi.org/10.1007/s10570-019-02599-3
Xu F, Zhong L, Xu Y et al (2019c) Highly efficient flame-retardant kraft paper. J Mater Sci 54:1884–1897. https://doi.org/10.1007/s10853-018-2911-2
Xu L, Zhang H, Xu F, Zheng C (2022) The construction of hybrid wettability surface of bamboo based on parenchyma and sclerenchyma cells difference. J Coat Technol Res 19:1859–1869. https://doi.org/10.1007/s11998-022-00657-3
Yan D, Chen D, Tan J et al (2023) Synergistic flame retardant effect of a new N-P flame retardant on poplar wood density board. Polym Degrad Stab 211:110331. https://doi.org/10.1016/j.polymdegradstab.2023.110331
Yuan B, Zhang J, Yu J et al (2016) Transparent and flame retardant cellulose/aluminum hydroxide nanocomposite aerogels. Sci China Chem 59:1335–1341. https://doi.org/10.1007/s11426-016-0188-0
Zeng S-L, Xing C-Y, Chen L et al (2020) Green flame-retardant flexible polyurethane foam based on cyclodextrin. Polym Degrad Stab 178:109171. https://doi.org/10.1016/j.polymdegradstab.2020.109171
Zhang W, Wang M, Guan J-P et al (2019) Casein phosphopeptide-metal salts combination: a novel route for imparting the durable flame retardancy to silk. J Taiwan Inst Chem Eng 101:1–7. https://doi.org/10.1016/j.jtice.2019.04.038
Zhang T, Wu M, Kuga S et al (2020) Cellulose nanofibril-based flame retardant and its application to paper. ACS Sustain Chem Eng 8:10222–10229. https://doi.org/10.1021/acssuschemeng.0c02892
Zhang L, Xu J, Shen H et al (2021) Montmorillonite-catalyzed furfurylated wood for flame retardancy. Fire Saf J 121:103297. https://doi.org/10.1016/j.firesaf.2021.103297
Zhang S, Chu F, Xu Z et al (2022) The improvement of fire safety performance of flexible polyurethane foam by Highly-efficient P-N-S elemental hybrid synergistic flame retardant. J Colloid Interface Sci 606:768–783. https://doi.org/10.1016/j.jcis.2021.08.069
Zhang H, Xu F, Xu L, Zheng C (2023) The effect of delignification ratio on the PMMA occupation in poplar wood cell wall by the macro and micro comparative study. J Wood Sci 69:10. https://doi.org/10.1186/s10086-023-02082-5
Zhao P, Guo C, Li L (2018) Exploring the effect of melamine pyrophosphate and aluminum hypophosphite on flame retardant wood flour/polypropylene composites. Constr Build Mater 170:193–199. https://doi.org/10.1016/j.conbuildmat.2018.03.074
Zou J, Duan H, Chen Y et al (2020) A P/N/S-containing high-efficiency flame retardant endowing epoxy resin with excellent flame retardance, mechanical properties and heat resistance. Compos Part B Eng 199:108228. https://doi.org/10.1016/j.compositesb.2020.108228
Acknowledgements
Thanks to all research partners in this project for their cooperation and collaboration. The authors thank Prof. C.T. Au for editing and helpful suggestions.
Funding
This work was supported by the Natural Science Foundation Project of Changsha (Grant No. kq2202285), the Hunan Provincial Natural Science Joint Fund (Grant No. 2021JJ50030), the Hunan Provincial Science and Technology Tackling Project (Grant No. 2020GK2061) and the Excellent Youth Fund Project of Hunan Provincial Education Department (Grant No. 20B137).
Author information
Authors and Affiliations
Contributions
DY: Resources, Investigation, Methodology, Formal analysis, Writing-original draft, Validation. JT and DC: Project administration. LY, ZH and DZ: Funding acquisition, Formal analysis, Data curation. DP and LS: Visualization, Software. QT, ZT and JD: Funding acquisition, Formal analysis, Writing-review & editing. YH: conceptualization, methodology, funding acquisition, formal analysis, supervision, writing—original draft, writing-review & editing. All authors reviewed the manuscript.
Corresponding author
Ethics declarations
Conflict of interest
All authors declare that there are no conflicts of interest and approved to submit to your journal.
Ethics approval and consent to participate
Not applicable.
Consent for publication
Written informed consent for publication was obtained from all participants.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Yan, D., Tan, J., Chen, D. et al. A novel cysteine-based flame retardant for biomass poplar wood density board. Eur. J. Wood Prod. 82, 175–187 (2024). https://doi.org/10.1007/s00107-023-01984-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00107-023-01984-x