Skip to main content
Erschienen in: Cellulose 1/2015

01.02.2015 | Original Paper

Preparation and flame retardancy of 3-(hydroxyphenylphosphinyl)-propanoic acid esters of cellulose and their fibers

verfasst von: Yunbo Zheng, Jun Song, Bowen Cheng, Xiaolin Fang, Ya Yuan

Erschienen in: Cellulose | Ausgabe 1/2015

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

New 3-(hydroxyphenylphosphinyl)-propanoic acid (3-HPP) esters of cellulose were synthesized in N, N-dimethylacetamide/LiCl homogeneously by the method of in situ activation with p-toluenesulfonyl chloride. Chemical structure and thermal properties of the cellulose esters were investigated by FTIR, 13C-NMR, TGA, RT-IR and Py–GC/MS, and their flame retardancy was studied by limiting oxygen index (LOI) test and vertical flammability test. It was found that the degree of substitution (DS) of cellulose esters, in the range from 0.62 to 1.42, had an obvious effect on solubility of cellulose esters. According to the FT-IR and Py–GC/MS results, flame retardant 3-HPP reacting with cellulose could accelerate dehydration action and decrease flammable released products. Besides, ESEM observation also confirmed that flame retardant cellulose (FRC) fibers with 3 wt% cellulose acetate prepared by dry-wet spinning technique possessed good flame resistance.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
Zurück zum Zitat Alongi J et al (2014a) Caseins and hydrophobins as novel green flame retardants for cotton fabrics. Polym Degrad Stab 99:111–117CrossRef Alongi J et al (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 overview. Polym Degrad Stab 106:138–149 Alongi J, Carosio F, Malucelli G (2014b) Current emerging techniques to impart flame retardancy to fabrics: an overview. Polym Degrad Stab 106:138–149
Zurück zum Zitat Bell KD, Graveson I, Ollerenshaw TJ (1997) Fiber production process. U.S. Patent No. 5,690,874 Bell KD, Graveson I, Ollerenshaw TJ (1997) Fiber production process. U.S. Patent No. 5,690,874
Zurück zum Zitat Cao Y, Li H, Zhang J (2011) Homogeneous synthesis and characterization of cellulose acetate butyrate (CAB) in 1-allyl-3-methylimidazolium chloride (AmimCl) ionic liquid. Ind Eng Chem Res 50:7808–7814CrossRef Cao Y, Li H, Zhang J (2011) Homogeneous synthesis and characterization of cellulose acetate butyrate (CAB) in 1-allyl-3-methylimidazolium chloride (AmimCl) ionic liquid. Ind Eng Chem Res 50:7808–7814CrossRef
Zurück zum Zitat Chang S, Slopek RP, Condon B, Grunlan JC (2014) Surface coating for flame-retardant behavior of cotton fabric using a continuous layer-by-layer process. Ind Eng Chem Res 53:3805–3812CrossRef Chang S, Slopek RP, Condon B, Grunlan JC (2014) Surface coating for flame-retardant behavior of cotton fabric using a continuous layer-by-layer process. Ind Eng Chem Res 53:3805–3812CrossRef
Zurück zum Zitat Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201CrossRef Gräbner D, Liebert T, Heinze T (2002) Synthesis of novel adamantoyl cellulose using differently activated carboxylic acid derivatives. Cellulose 9:193–201CrossRef
Zurück zum Zitat Hasani MM, Westman G (2007) New coupling reagents for homogeneous esterification of cellulose. Cellulose 14:347–356CrossRef Hasani MM, Westman G (2007) New coupling reagents for homogeneous esterification of cellulose. Cellulose 14:347–356CrossRef
Zurück zum Zitat Liebert T Cellulose solvents-remarkable history, bright future. In: ACS symposium series, 2010. Oxford University Press, pp 3-54 Liebert T Cellulose solvents-remarkable history, bright future. In: ACS symposium series, 2010. Oxford University Press, pp 3-54
Zurück zum Zitat Hong KH, Liu N, Sun G (2009) UV-induced graft polymerization of acrylamide on cellulose by using immobilized benzophenone as a photo-initiator. Eur Polym J 45:2443–2449CrossRef Hong KH, Liu N, Sun G (2009) UV-induced graft polymerization of acrylamide on cellulose by using immobilized benzophenone as a photo-initiator. Eur Polym J 45:2443–2449CrossRef
Zurück zum Zitat Horrocks AR (2011) Flame retardant challenges for textiles and fibres: new chemistry versus innovatory solutions. Polym Degrad Stab 96:377–392CrossRef Horrocks AR (2011) Flame retardant challenges for textiles and fibres: new chemistry versus innovatory solutions. Polym Degrad Stab 96:377–392CrossRef
Zurück zum Zitat Horrocks A, Kandola B, Davies P, Zhang S, Padbury S (2005) Developments in flame retardant textiles—a review. Polym Degrad Stab 88:3–12CrossRef Horrocks A, Kandola B, Davies P, Zhang S, Padbury S (2005) Developments in flame retardant textiles—a review. Polym Degrad Stab 88:3–12CrossRef
Zurück zum Zitat Huang G, Liang H, Wang X, Gao J (2012) Poly (acrylic acid)/clay thin films assembled by layer-by-layer deposition for improving the flame retardancy properties of cotton. Ind Eng Chem Res 51:12299–12309 Huang G, Liang H, Wang X, Gao J (2012) Poly (acrylic acid)/clay thin films assembled by layer-by-layer deposition for improving the flame retardancy properties of cotton. Ind Eng Chem Res 51:12299–12309
Zurück zum Zitat Hussain MA, Liebert T, Heinze T (2004) Acylation of cellulose with N, N′-carbonyldiimidazo-activated acids in the Novel solvent dimethyl sulfoxide/tetrabutylammonium fluoride. Macromol Rapid Commun 25:916–920CrossRef Hussain MA, Liebert T, Heinze T (2004) Acylation of cellulose with N, N′-carbonyldiimidazo-activated acids in the Novel solvent dimethyl sulfoxide/tetrabutylammonium fluoride. Macromol Rapid Commun 25:916–920CrossRef
Zurück zum Zitat Köhler S, Heinze T (2007) Efficient synthesis of cellulose furoates in 1-N-butyl-3-methylimidazolium chloride. Cellulose 14:489–495CrossRef Köhler S, Heinze T (2007) Efficient synthesis of cellulose furoates in 1-N-butyl-3-methylimidazolium chloride. Cellulose 14:489–495CrossRef
Zurück zum Zitat Lewin M (2010) Handbook of fiber chemistry. CRC Press, Boca Raton Lewin M (2010) Handbook of fiber chemistry. CRC Press, Boca Raton
Zurück zum Zitat Liang SY, Neisius NM, Gaan S (2013) Recent developments in flame retardant polymeric coatings. Prog Org Coat 76:1642–1665CrossRef Liang SY, Neisius NM, Gaan S (2013) Recent developments in flame retardant polymeric coatings. Prog Org Coat 76:1642–1665CrossRef
Zurück zum Zitat Liebert TF, Heinze T (2005) Tailored cellulose esters: synthesis and structure determination. Biomacromolecules 6:333–340CrossRef Liebert TF, Heinze T (2005) Tailored cellulose esters: synthesis and structure determination. Biomacromolecules 6:333–340CrossRef
Zurück zum Zitat Liu W, Chen L, Wang Y-Z (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 Y-Z (2012) A novel phosphorus-containing flame retardant for the formaldehyde-free treatment of cotton fabrics. Polym Degrad Stab 97:2487–2491CrossRef
Zurück zum Zitat Lu S-Y, Hamerton I (2002) Recent developments in the chemistry of halogen-free flame retardant polymers. Prog Polym Sci 27:1661–1712CrossRef Lu S-Y, Hamerton I (2002) Recent developments in the chemistry of halogen-free flame retardant polymers. Prog Polym Sci 27:1661–1712CrossRef
Zurück zum Zitat Lu F, Cheng B, Song J, Liang Y (2012) Rheological characterization of concentrated cellulose solutions in 1‐allyl‐3‐methylimidazolium chloride. J Appl Polym Sci 124:3419–3425 Lu F, Cheng B, Song J, Liang Y (2012) Rheological characterization of concentrated cellulose solutions in 1‐allyl‐3‐methylimidazolium chloride. J Appl Polym Sci 124:3419–3425
Zurück zum Zitat Lu F, Wang L, Ji X, Cheng B, Song J, Gou X (2014) Flow behavior and linear viscoelasticity of cellulose 1-allyl-3-methylimidazolium formate solutions. Carbohydr Polym 99:132–139 Lu F, Wang L, Ji X, Cheng B, Song J, Gou X (2014) Flow behavior and linear viscoelasticity of cellulose 1-allyl-3-methylimidazolium formate solutions. Carbohydr Polym 99:132–139
Zurück zum Zitat Martin C, Ronda J, Cadiz V (2006) Boron-containing novolac resins as flame retardant materials. Polym Degrad Stabil 91:747–754CrossRef Martin C, Ronda J, Cadiz V (2006) Boron-containing novolac resins as flame retardant materials. Polym Degrad Stabil 91:747–754CrossRef
Zurück zum Zitat Masuko F, Mitani C, Sakamoto M (2002) Pyrolysis and limiting oxygen indices of cotton fabrics. graft copolymerized with oligomeric vinyl phosphonate and/or N-methylolacrylamide. Fire Mater 26:225–234CrossRef Masuko F, Mitani C, Sakamoto M (2002) Pyrolysis and limiting oxygen indices of cotton fabrics. graft copolymerized with oligomeric vinyl phosphonate and/or N-methylolacrylamide. Fire Mater 26:225–234CrossRef
Zurück zum Zitat Muralidhara K, Sreenivasan S (2010) Thermal degradation and burning behaviour of cellulose based and cellulose-silk blended upholstery fabrics. J Sci Ind Res 69:879 Muralidhara K, Sreenivasan S (2010) Thermal degradation and burning behaviour of cellulose based and cellulose-silk blended upholstery fabrics. J Sci Ind Res 69:879
Zurück zum Zitat Nguyen TM, Chang SC, Condon B, Slopek R, Graves E, Yoshioka-Tarver M (2013) Structural effect of phosphoramidate derivatives on the thermal and flame retardant behaviors of treated cotton cellulose. Ind Eng Chem Res 52:4715–4724CrossRef Nguyen TM, Chang SC, Condon B, Slopek R, Graves E, Yoshioka-Tarver M (2013) Structural effect of phosphoramidate derivatives on the thermal and flame retardant behaviors of treated cotton cellulose. Ind Eng Chem Res 52:4715–4724CrossRef
Zurück zum Zitat Qian X et al (2011) Combustion and thermal degradation mechanism of a novel intumescent flame retardant for epoxy acrylate containing phosphorus and nitrogen. Ind Eng Chem Res 50:1881–1892CrossRef Qian X et al (2011) Combustion and thermal degradation mechanism of a novel intumescent flame retardant for epoxy acrylate containing phosphorus and nitrogen. Ind Eng Chem Res 50:1881–1892CrossRef
Zurück zum Zitat Raus V et al (2012) Activation of cellulose by 1, 4-dioxane for dissolution in N, N-dimethylacetamide/LiCl. Cellulose 19:1893–1906CrossRef Raus V et al (2012) Activation of cellulose by 1, 4-dioxane for dissolution in N, N-dimethylacetamide/LiCl. Cellulose 19:1893–1906CrossRef
Zurück zum Zitat Reddy PRS, Agathian G, Kumar A (2005) Ionizing radiation graft polymerized and modified flame retardant cotton fabric. Radiat Phys Chem 72:511–516CrossRef Reddy PRS, Agathian G, Kumar A (2005) Ionizing radiation graft polymerized and modified flame retardant cotton fabric. Radiat Phys Chem 72:511–516CrossRef
Zurück zum Zitat Rüf H, Kroner G, Dobson P, Männer J, Schrempf C (2010) Flame-retardant lyocell fibers and use thereof in flame barriers. U.S. Patent Application 13/501,684 Rüf H, Kroner G, Dobson P, Männer J, Schrempf C (2010) Flame-retardant lyocell fibers and use thereof in flame barriers. U.S. Patent Application 13/501,684
Zurück zum Zitat Rupper P, Gaan S, Salimova V, Heuberger M (2010) Characterization of chars obtained from cellulose treated with phosphoramidate flame retardants. J Anal Appl Pyrolysis 87:93–98CrossRef Rupper P, Gaan S, Salimova V, Heuberger M (2010) Characterization of chars obtained from cellulose treated with phosphoramidate flame retardants. J Anal Appl Pyrolysis 87:93–98CrossRef
Zurück zum Zitat Schnipper A, Smith-hansen L, Thomsen ES (1995) Reduced combustion efficiency of chlorinated compounds, resulting in higher yields of carbon monoxide. Fire Mater 19:61–64CrossRef Schnipper A, Smith-hansen L, Thomsen ES (1995) Reduced combustion efficiency of chlorinated compounds, resulting in higher yields of carbon monoxide. Fire Mater 19:61–64CrossRef
Zurück zum Zitat Shafizadeh F, Fu Y (1973) Pyrolysis of cellulose. Carbohydr Res 29:113–122CrossRef Shafizadeh F, Fu Y (1973) Pyrolysis of cellulose. Carbohydr Res 29:113–122CrossRef
Zurück zum Zitat Shahidi S (2014) Novel method for ultraviolet protection and flame retardancy of cotton fabrics by low-temperature plasma. Cellulose 21:757–768CrossRef Shahidi S (2014) Novel method for ultraviolet protection and flame retardancy of cotton fabrics by low-temperature plasma. Cellulose 21:757–768CrossRef
Zurück zum Zitat Shahidi S, Ghoranneviss M (2014) Effect of plasma pretreatment followed by nanoclay loading on flame retardant properties of cotton fabric. J Fusion Energy 33:88–95CrossRef Shahidi S, Ghoranneviss M (2014) Effect of plasma pretreatment followed by nanoclay loading on flame retardant properties of cotton fabric. J Fusion Energy 33:88–95CrossRef
Zurück zum Zitat Siriviriyanun A, O’Rear EA, Yanumet N (2008) Improvement in the flame retardancy of cotton fabric by admicellar polymerization of 2-acryloyloxyethyl diethyl phosphate using an anionic surfactant. J Appl Polym Sci 109:3859–3866CrossRef Siriviriyanun A, O’Rear EA, Yanumet N (2008) Improvement in the flame retardancy of cotton fabric by admicellar polymerization of 2-acryloyloxyethyl diethyl phosphate using an anionic surfactant. J Appl Polym Sci 109:3859–3866CrossRef
Zurück zum Zitat S-r Wang, Liu Q, Luo Z-y, Wen L, Cen K (2006) Mechanism study of cellulose pyrolysis using thermogravimetric analysis coupled with infrared spectroscopy. J Zhejiang Univ Eng Sci 40:1154 S-r Wang, Liu Q, Luo Z-y, Wen L, Cen K (2006) Mechanism study of cellulose pyrolysis using thermogravimetric analysis coupled with infrared spectroscopy. J Zhejiang Univ Eng Sci 40:1154
Zurück zum Zitat Strlič M, Kolar J (2003) Size exclusion chromatography of cellulose in LiCl/N, N-dimethylacetamide. J Biochem Biophys Methods 56:265–279CrossRef Strlič M, Kolar J (2003) Size exclusion chromatography of cellulose in LiCl/N, N-dimethylacetamide. J Biochem Biophys Methods 56:265–279CrossRef
Zurück zum Zitat Sui X et al (2008) Synthesis of cellulose-graft-poly (N, N-dimethylamino-2-ethyl methacrylate) copolymers via homogeneous ATRP and their aggregates in aqueous media. Biomacromolecules 9:2615–2620CrossRef Sui X et al (2008) Synthesis of cellulose-graft-poly (N, N-dimethylamino-2-ethyl methacrylate) copolymers via homogeneous ATRP and their aggregates in aqueous media. Biomacromolecules 9:2615–2620CrossRef
Zurück zum Zitat Tsvetkov N et al (2013) Conformational and optical properties of macromolecules of some aliphatic-substituted cellulose esters. Cellulose 20:1057–1071CrossRef Tsvetkov N et al (2013) Conformational and optical properties of macromolecules of some aliphatic-substituted cellulose esters. Cellulose 20:1057–1071CrossRef
Zurück zum Zitat Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–268CrossRef Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–268CrossRef
Zurück zum Zitat Yang H, Yang CQ (2008) Flame retardant finishing of nylon/cotton blend fabrics using a hydroxy functional organophosphorus oligomer. Ind Eng Chem Res 47:2160–2165CrossRef Yang H, Yang CQ (2008) Flame retardant finishing of nylon/cotton blend fabrics using a hydroxy functional organophosphorus oligomer. Ind Eng Chem Res 47:2160–2165CrossRef
Zurück zum Zitat Yoshioka-Tarver M et al (2012) Enhanced flame retardant property of fiber reactive halogen-free organophosphonate. Ind Eng Chem Res 51:11031–11037CrossRef Yoshioka-Tarver M et al (2012) Enhanced flame retardant property of fiber reactive halogen-free organophosphonate. Ind Eng Chem Res 51:11031–11037CrossRef
Zurück zum Zitat Yuan B, Bao C, Guo Y, Song L, Liew KM, Hu Y (2012a) Preparation and characterization of flame-retardant aluminum hypophosphite/poly (vinyl alcohol) composite. Ind Eng Chem Res 51:14065–14075CrossRef Yuan B, Bao C, Guo Y, Song L, Liew KM, Hu Y (2012a) Preparation and characterization of flame-retardant aluminum hypophosphite/poly (vinyl alcohol) composite. Ind Eng Chem Res 51:14065–14075CrossRef
Zurück zum Zitat Yuan H, Xing W, Zhang P, Song L, Hu Y (2012b) Functionalization of cotton with UV-cured flame retardant coatings. Ind Eng Chem Res 51:5394–5401CrossRef Yuan H, Xing W, Zhang P, Song L, Hu Y (2012b) Functionalization of cotton with UV-cured flame retardant coatings. Ind Eng Chem Res 51:5394–5401CrossRef
Zurück zum Zitat Zhu S, Shi W (2003) Thermal degradation of a new flame retardant phosphate methacrylate polymer. Polym Degrad Stab 80:217–222CrossRef Zhu S, Shi W (2003) Thermal degradation of a new flame retardant phosphate methacrylate polymer. Polym Degrad Stab 80:217–222CrossRef
Zurück zum Zitat Zhu P, Sui S, Wang B, Sun K, Sun G (2004) A study of pyrolysis and pyrolysis products of flame-retardant cotton fabrics by DSC, TGA, and PY–GC–MS. J Anal Appl Pyrolsis 71:645–655CrossRef Zhu P, Sui S, Wang B, Sun K, Sun G (2004) A study of pyrolysis and pyrolysis products of flame-retardant cotton fabrics by DSC, TGA, and PY–GC–MS. J Anal Appl Pyrolsis 71:645–655CrossRef
Metadaten
Titel
Preparation and flame retardancy of 3-(hydroxyphenylphosphinyl)-propanoic acid esters of cellulose and their fibers
verfasst von
Yunbo Zheng
Jun Song
Bowen Cheng
Xiaolin Fang
Ya Yuan
Publikationsdatum
01.02.2015
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 1/2015
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-014-0486-x

Weitere Artikel der Ausgabe 1/2015

Cellulose 1/2015 Zur Ausgabe