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Erschienen in: Cellulose 12/2019

01.07.2019 | Original Research

Synthesis of three novel amino acids-based flame retardants with multiple reactive groups for cotton fabrics

verfasst von: Fang Xu, Ling Zhong, Yuan Xu, Cheng Zhang, Peng Wang, Fengxiu Zhang, Guangxian Zhang

Erschienen in: Cellulose | Ausgabe 12/2019

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Abstract

Three novel high efficient, halogen-free and formaldehyde-free flame retardants containing –P=O(ONH4+)2 and –COONH4+ multiple reactive groups, ammonium salt of N,N-bis(phosphonomethyl) glycine (FR-G), ammonium salt of N,N-bis(phosphonomethyl) aspartic acid (FR-A) and ammonium salt of N,N,N,N-tetra(phosphonomethyl) lysine (FR-L), were synthesized for cotton fabric based on glycine, aspartic acid and lysine. The flame retardant properties and thermal stabilities of treated cotton fabrics were evaluated by limiting oxygen index (LOI), vertical flammability test, cone calorimetry test and thermogravimetric analysis (TG). The modifications and flame retardant mechanisms were investigated by TG-IR, FTIR, SEM, EDX. The comparison of three flame retardants was also investigated. The results reveal that flame retardants could graft on cotton fabric by the formation of P–O–C and C–O–C covalent bonds, the LOI value of cotton fabric treated by 30% FR-L could achieve 42.1%, which remained well after 40 laundering cycles with a LOI value of 27.1%. Vertical flammability test and cone calorimetry test also show that the flame retardancy of modified cotton fabrics was greatly improved. The results indicate that cellulose was phosphorylated by these flame retardants to prevent the formation of levoglucosan and promote the dehydration and charring. Moreover, the physical properties of treated cotton fabrics were maintained well.

Graphic abstract

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Literatur
Zurück zum Zitat Abou-Okeil A, Ei-Sawy SM, Abdel-Mohdy FA (2013) Flame retardant cotton fabrics treated with organophosphorus polymer. Carbohydr Polym 92:2293–2298CrossRefPubMed Abou-Okeil A, Ei-Sawy SM, Abdel-Mohdy FA (2013) Flame retardant cotton fabrics treated with organophosphorus polymer. Carbohydr Polym 92:2293–2298CrossRefPubMed
Zurück zum Zitat Alongi J, Ciobanu M, Malucelli G (2011) Novel flame retardant finishing systems for cotton fabrics based on phosphorus-containing compounds and silica derived from sol-gel processes. Carbohydr Polym 85:599–608CrossRef Alongi J, Ciobanu M, Malucelli G (2011) Novel flame retardant finishing systems for cotton fabrics based on phosphorus-containing compounds and silica derived from sol-gel processes. Carbohydr Polym 85:599–608CrossRef
Zurück zum Zitat Alongi J, Carletto RA, Blasio AD, Carosio F, Bosco F, Malucelli G (2013a) DNA: a novel, green, natural flame retardant and suppressant for cotton. J Mater Chem A 1:4779–4785CrossRef Alongi J, Carletto RA, Blasio AD, Carosio F, Bosco F, Malucelli G (2013a) DNA: a novel, green, natural flame retardant and suppressant for cotton. J Mater Chem A 1:4779–4785CrossRef
Zurück zum Zitat Alongi J, Colleoni C, Rosace G, Malucelli G (2013b) The role of prehydrolysis on multi step sol-gel processes for enhancing the flame retardancy of cotton. Cellulose 20:525–535CrossRef Alongi J, Colleoni C, Rosace G, Malucelli G (2013b) The role of prehydrolysis on multi step sol-gel processes for enhancing the flame retardancy of cotton. Cellulose 20:525–535CrossRef
Zurück zum Zitat Alongi J, Carletto RA, Bosco F, Carosio F, Blasio AD, Cuttica F, Antonucci V, Giordano M, Malucelli G (2014a) Caseins and hydrophobins as novel green flame retardants for cotton fabrics. Polym Degrad Stab 99:111–117CrossRef Alongi J, Carletto RA, Bosco F, Carosio F, Blasio AD, Cuttica F, Antonucci V, Giordano M, Malucelli G (2014a) Caseins and hydrophobins as novel green flame retardants for cotton fabrics. Polym Degrad Stab 99:111–117CrossRef
Zurück zum Zitat Alongi J, Carosio F, Malucelli G (2014b) Current emerging techniques to impart flame retardancy to fabrics: an over-view. Polym Degrad Stab 106:138–149CrossRef Alongi J, Carosio F, Malucelli G (2014b) Current emerging techniques to impart flame retardancy to fabrics: an over-view. Polym Degrad Stab 106:138–149CrossRef
Zurück zum Zitat Alongi J, Cuttica F, Blasio AD, Carosio F, Malucelli G (2014c) Intumescent features of nucleic acids and proteins. Thermochim Acta 591:31–39CrossRef Alongi J, Cuttica F, Blasio AD, Carosio F, Malucelli G (2014c) Intumescent features of nucleic acids and proteins. Thermochim Acta 591:31–39CrossRef
Zurück zum Zitat Bosco F, Carletto RA, Alongi J, Marmo L, Blasio AD, Malucelli G (2013) Thermal stability and flame resistance of cotton fabrics treated with whey proteins. Carbohydr Polym 94:372–377CrossRefPubMed Bosco F, Carletto RA, Alongi J, Marmo L, Blasio AD, Malucelli G (2013) Thermal stability and flame resistance of cotton fabrics treated with whey proteins. Carbohydr Polym 94:372–377CrossRefPubMed
Zurück zum Zitat Bosco F, Casale A, Mollea C, Terlizzi ME, Gribauso G, Alongi J, Malucelli G (2015) DNA coatings on cotton fabrics: effect of molecular size and pH on flame retardancy. Surf Coat Technol 272:86–95CrossRef Bosco F, Casale A, Mollea C, Terlizzi ME, Gribauso G, Alongi J, Malucelli G (2015) DNA coatings on cotton fabrics: effect of molecular size and pH on flame retardancy. Surf Coat Technol 272:86–95CrossRef
Zurück zum Zitat Carosio F, Blasio AD, Alongi J, Malucelli G (2013) Green DNA-based flame retardant coatings assembled through layer by layer. Polymer 54:5148–5153CrossRef Carosio F, Blasio AD, Alongi J, Malucelli G (2013) Green DNA-based flame retardant coatings assembled through layer by layer. Polymer 54:5148–5153CrossRef
Zurück zum Zitat Carosio F, Blasio AD, Cuttica F, Alongi J, Malucelli G (2014) Flame retardancy of polyester and polyester-cotton blends treated with caseins. Ind Eng Chem Res 53:3917–3923CrossRef Carosio F, Blasio AD, Cuttica F, Alongi J, Malucelli G (2014) Flame retardancy of polyester and polyester-cotton blends treated with caseins. Ind Eng Chem Res 53:3917–3923CrossRef
Zurück zum Zitat Dong C, Liu Z, Zhang F, Zhu P, Wang P, Che Y, Sui S (2016) Combustion behaviors of cotton fabrics treated by a novel nitrogen- and phosphorus-containing polysiloxane flame retardant. J Therm Anal Calorim 123(1):535–544CrossRef Dong C, Liu Z, Zhang F, Zhu P, Wang P, Che Y, Sui S (2016) Combustion behaviors of cotton fabrics treated by a novel nitrogen- and phosphorus-containing polysiloxane flame retardant. J Therm Anal Calorim 123(1):535–544CrossRef
Zurück zum Zitat 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 148:10–18CrossRef 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 148:10–18CrossRef
Zurück zum Zitat Feng YJ, Zhou Y, Li DK, He S, Zhang F, Zhang GX (2017) A plant-based reactive ammonium phytate for use as a flame-retardant for cotton fabric. Carbohydr Polym 175:636–644CrossRefPubMed Feng YJ, Zhou Y, Li DK, He S, Zhang F, Zhang GX (2017) A plant-based reactive ammonium phytate for use as a flame-retardant for cotton fabric. Carbohydr Polym 175:636–644CrossRefPubMed
Zurück zum Zitat Gao WW, Zhang GX, Zhang FX (2015) Enhancement of flame retardancy of cotton fabrics by grafting a novel organic phosphorous-based flame retardant. Cellulose 22:2787–2796CrossRef Gao WW, Zhang GX, Zhang FX (2015) Enhancement of flame retardancy of cotton fabrics by grafting a novel organic phosphorous-based flame retardant. Cellulose 22:2787–2796CrossRef
Zurück zum Zitat Harifi T, Montazer M (2012) Past, present and future prospects of cotton cross-linking: new insight into nanoparticles. Carbohydr Polym 88:1125–1140CrossRef Harifi T, Montazer M (2012) Past, present and future prospects of cotton cross-linking: new insight into nanoparticles. Carbohydr Polym 88:1125–1140CrossRef
Zurück zum Zitat Inderjeet K, Sanjeev KV (2010) Living radical polymerization and grafting of diethyl (acryloyloxy) ethylthiophosphoramidate onto cotton fabric to impart flame retardnacy. Surf Coat Thechnol 205:2082–2090CrossRef Inderjeet K, Sanjeev KV (2010) Living radical polymerization and grafting of diethyl (acryloyloxy) ethylthiophosphoramidate onto cotton fabric to impart flame retardnacy. Surf Coat Thechnol 205:2082–2090CrossRef
Zurück zum Zitat 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 5:9970–9981CrossRef 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 5:9970–9981CrossRef
Zurück zum Zitat Jiang DW, Sun CY, Zhou YN, Wang H, Yan XR, He QL, Guo J, Guo ZH (2015) Enhanced flame retardancy of cotton fabrics with a novel intumescent flame-retardant finishing system. Fibers Polym 16:388–396CrossRef Jiang DW, Sun CY, Zhou YN, Wang H, Yan XR, He QL, Guo J, Guo ZH (2015) Enhanced flame retardancy of cotton fabrics with a novel intumescent flame-retardant finishing system. Fibers Polym 16:388–396CrossRef
Zurück zum Zitat Lecoeur E, Vroman I, Bourbigot S, Lam TM, Delobel R (2001) Flame retardant formations for cotton. Polym Degrad Stab 74:487–492CrossRef Lecoeur E, Vroman I, Bourbigot S, Lam TM, Delobel R (2001) Flame retardant formations for cotton. Polym Degrad Stab 74:487–492CrossRef
Zurück zum Zitat Liu W, Chen L, Wang YZ (2012) A novel phosphorus-containing flame retardant for the formaldehyde-free treatment of cotton fabrics. Polym Degrad Stab 97:2487–2491CrossRef Liu W, Chen L, Wang YZ (2012) A novel phosphorus-containing flame retardant for the formaldehyde-free treatment of cotton fabrics. Polym Degrad Stab 97:2487–2491CrossRef
Zurück zum Zitat 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 24:4069–4081CrossRef 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 24:4069–4081CrossRef
Zurück zum Zitat Malucelli G, Bosco F, Alongi J, Carosio F, Blasio AD, Mollea C, Fabio C, Casale A (2014) Biomacromolecules as novel green flame retardant systems for textiles: an overview. RSC Adv 4:46024–46039CrossRef Malucelli G, Bosco F, Alongi J, Carosio F, Blasio AD, Mollea C, Fabio C, Casale A (2014) Biomacromolecules as novel green flame retardant systems for textiles: an overview. RSC Adv 4:46024–46039CrossRef
Zurück zum Zitat Mettler MS, Paulsen AD, Vlachos DG, Dauenhauer PJ (2012) The chain length effect in pyrolysis: bridging the gap between glucose and cellulose. Green Chem 14:1284–1288CrossRef Mettler MS, Paulsen AD, Vlachos DG, Dauenhauer PJ (2012) The chain length effect in pyrolysis: bridging the gap between glucose and cellulose. Green Chem 14:1284–1288CrossRef
Zurück zum Zitat Ortelli S, Malucelli G, Cuttica F, Blosi M, Zanoni I, Costa AL (2018) Coatings made of proteins adsorbed on TiO2 nanoparticles: a new flame retardant approach for cotton fabrics. Cellulose 25:2755–2765CrossRef Ortelli S, Malucelli G, Cuttica F, Blosi M, Zanoni I, Costa AL (2018) Coatings made of proteins adsorbed on TiO2 nanoparticles: a new flame retardant approach for cotton fabrics. Cellulose 25:2755–2765CrossRef
Zurück zum Zitat Patwardhan PR, Satrio JA, Brown RC, Shanks GH (2009) Product distribution from fast pyrolysis of glucose-based carbohydrates. J Anal Appl Pyrol 86:323–330CrossRef Patwardhan PR, Satrio JA, Brown RC, Shanks GH (2009) Product distribution from fast pyrolysis of glucose-based carbohydrates. J Anal Appl Pyrol 86:323–330CrossRef
Zurück zum Zitat Poon CK, Kan CW (2015) Effects of TiO2 and curing temperatures on flame retardant finishing of cotton. Carbohydr Polym 121:457–467CrossRefPubMed Poon CK, Kan CW (2015) Effects of TiO2 and curing temperatures on flame retardant finishing of cotton. Carbohydr Polym 121:457–467CrossRefPubMed
Zurück zum Zitat Rosace G, Castellano A, Trovato V, Iacono G, Malucelli G (2018) Thermal and flame retardant behavior of cotton fabrics treated with a novel nitrogen-containing carboxyl-functionalized organophosphorus system. Carbohydr Polym 196:348–358CrossRefPubMed Rosace G, Castellano A, Trovato V, Iacono G, Malucelli G (2018) Thermal and flame retardant behavior of cotton fabrics treated with a novel nitrogen-containing carboxyl-functionalized organophosphorus system. Carbohydr Polym 196:348–358CrossRefPubMed
Zurück zum Zitat Salmeia KA, Gaan S, Malucelli G (2016) Recent advances for flame retardancy of textiles based on phosphorus chemistry. Polymers 8:391CrossRef Salmeia KA, Gaan S, Malucelli G (2016) Recent advances for flame retardancy of textiles based on phosphorus chemistry. Polymers 8:391CrossRef
Zurück zum Zitat Santanu B, Wazed AS (2016) Sustainable fire retardancy of textiles using bio-macromolecules. Polym Degrad Stab 133:47–64CrossRef Santanu B, Wazed AS (2016) Sustainable fire retardancy of textiles using bio-macromolecules. Polym Degrad Stab 133:47–64CrossRef
Zurück zum Zitat Schramm C, Binder WH, Tessadri R (2004) Durable press finishing of cotton fabric with 1,2,3,4-butanetetracarboxylic acid and TEO/GPTMS. J Sol Gel Sci Technol 29:155–165CrossRef Schramm C, Binder WH, Tessadri R (2004) Durable press finishing of cotton fabric with 1,2,3,4-butanetetracarboxylic acid and TEO/GPTMS. J Sol Gel Sci Technol 29:155–165CrossRef
Zurück zum Zitat Shariatinia Z, Javeri N, Shekarriz S (2015) Flame retardant cotton fibers produced using novel synthesized halogen-free phosphoramide nanoparticles. Carbohydr Polym 118:183–198CrossRefPubMed Shariatinia Z, Javeri N, Shekarriz S (2015) Flame retardant cotton fibers produced using novel synthesized halogen-free phosphoramide nanoparticles. Carbohydr Polym 118:183–198CrossRefPubMed
Zurück zum Zitat Steplewski W, Kazimierczak J, Wawro D (2010) Novel method of preparing flame retardant cellulose-silicate fibres. Fiber Text East Europe 18:24–31 Steplewski W, Kazimierczak J, Wawro D (2010) Novel method of preparing flame retardant cellulose-silicate fibres. Fiber Text East Europe 18:24–31
Zurück zum Zitat Wang XY, Lu CQ, Chen CX (2014) Effect of chicken-feather protein-based flame retardant on flame retarding performance of cotton fabric. J Appl Polym Sci 15:40584 Wang XY, Lu CQ, Chen CX (2014) Effect of chicken-feather protein-based flame retardant on flame retarding performance of cotton fabric. J Appl Polym Sci 15:40584
Zurück zum Zitat Wang N, Liu YS, Liu Y, Wang Q (2017a) Properties and mechanisms of different guanidine flame retardant wood pulp paper. J Anal Appl Pyrol 128:224–231CrossRef Wang N, Liu YS, Liu Y, Wang Q (2017a) Properties and mechanisms of different guanidine flame retardant wood pulp paper. J Anal Appl Pyrol 128:224–231CrossRef
Zurück zum Zitat Wang N, Liu YS, Xu C, Liu Y, Wang Q (2017b) Acid-base synergistic flame retardant wood pulp paper with high thermal stability. Carbohydr Polym 178:123–130CrossRefPubMed Wang N, Liu YS, Xu C, Liu Y, Wang Q (2017b) Acid-base synergistic flame retardant wood pulp paper with high thermal stability. Carbohydr Polym 178:123–130CrossRefPubMed
Zurück zum Zitat Xu F, Yang YL, Zhang GX, Zhang FX, Zhang YS (2015) A self-stiffness finishing for cotton fabric with N-methylmorpholine-N-oxide. Cellulose 22:2837–2844CrossRef Xu F, Yang YL, Zhang GX, Zhang FX, Zhang YS (2015) A self-stiffness finishing for cotton fabric with N-methylmorpholine-N-oxide. Cellulose 22:2837–2844CrossRef
Zurück zum Zitat Xu LJ, Wang W, Yu D (2017a) Durable flame retardant finishing of cotton fabrics with halogen-free organophosphonate by UV photoinitiated thiol-ene click chemistry. Carbohydr Polym 172:275–283CrossRefPubMed Xu LJ, Wang W, Yu D (2017a) Durable flame retardant finishing of cotton fabrics with halogen-free organophosphonate by UV photoinitiated thiol-ene click chemistry. Carbohydr Polym 172:275–283CrossRefPubMed
Zurück zum Zitat Xu L, Wang W, Yu D (2017b) Preparation of a reactive flame retardant and its finishing on cotton fabrics based on click chemistry. RSC Adv 7:2044–2050CrossRef Xu L, Wang W, Yu D (2017b) Preparation of a reactive flame retardant and its finishing on cotton fabrics based on click chemistry. RSC Adv 7:2044–2050CrossRef
Zurück zum Zitat Xu F, Zhong L, Xu Y, Zhang C, Zhang FX, Zhang GX (2019) Highly efficient flame-retardant kraft paper. J Mater Sci 54:1884–1897CrossRef Xu F, Zhong L, Xu Y, Zhang C, Zhang FX, Zhang GX (2019) Highly efficient flame-retardant kraft paper. J Mater Sci 54:1884–1897CrossRef
Zurück zum Zitat Yang JC, Liao W, Deng SB, Jie ZJ, Wang YZ (2016) Flame retardantion of cellulose-rich fabrics via a simplified layer-by-layer assembly. Carbohydr Polym 151:434–440CrossRefPubMed Yang JC, Liao W, Deng SB, Jie ZJ, Wang YZ (2016) Flame retardantion of cellulose-rich fabrics via a simplified layer-by-layer assembly. Carbohydr Polym 151:434–440CrossRefPubMed
Metadaten
Titel
Synthesis of three novel amino acids-based flame retardants with multiple reactive groups for cotton fabrics
verfasst von
Fang Xu
Ling Zhong
Yuan Xu
Cheng Zhang
Peng Wang
Fengxiu Zhang
Guangxian Zhang
Publikationsdatum
01.07.2019
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 12/2019
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-019-02599-3

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