Hyperbranched Polymeric Fluorosurfactants: Synthesis, Surface Activity and Their Application in Firefighting Foams

Dan-Ling Yang; Pei-Yao Chen; Yan Wang; Shuang Zhuang; Yu Chen; Hua-Ji Liu

doi:10.1007/s10118-023-2981-8

Your Location：

Home >

Browse articles >

Hyperbranched Polymeric Fluorosurfactants: Synthesis, Surface Activity and Their Application in Firefighting Foams

RESEARCH ARTICLE | Updated：2023-11-10

- Hyperbranched Polymeric Fluorosurfactants: Synthesis, Surface Activity and Their Application in Firefighting Foams
- Chinese Journal of Polymer Science Vol. 41, Issue 11, Pages: 1767-1777(2023)
- Affiliations：
  
  a.Department of Chemistry, School of Science, Tianjin University, Tianjin 300354, China
  b.Tianjin Fire Research Institute of MEM, Tianjin 300381, China
- Author bio：
  
  chenyu@tju.edu.cn (Y.C.)
  liuhuaji@tju.edu.cn (H.J.L.)
- Funds：
- DOI：10.1007/s10118-023-2981-8
  CLC：
- Received：13 February 2023，
  
  Revised：2023-3-19，
  
  Accepted：22 March 2023，
  
  Online First：07 May 2023，
  
  Published：01 November 2023
- Accepted：
Scan QR Code
Yang, D. L.; Chen, P. Y.; Wang, Y.; Zhuang, S.; Chen, Y.; Liu, H. J. Hyperbranched polymeric fluorosurfactants: synthesis, surface activity and their application in firefighting foams. Chinese J. Polym. Sci. 2023, 41, 1767–1777

Dan-Ling Yang, Pei-Yao Chen, Yan Wang, et al. Hyperbranched Polymeric Fluorosurfactants: Synthesis, Surface Activity and Their Application in Firefighting Foams[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1767-1777.
Yang, D. L.; Chen, P. Y.; Wang, Y.; Zhuang, S.; Chen, Y.; Liu, H. J. Hyperbranched polymeric fluorosurfactants: synthesis, surface activity and their application in firefighting foams. Chinese J. Polym. Sci. 2023, 41, 1767–1777 DOI： 10.1007/s10118-023-2981-8.

Dan-Ling Yang, Pei-Yao Chen, Yan Wang, et al. Hyperbranched Polymeric Fluorosurfactants: Synthesis, Surface Activity and Their Application in Firefighting Foams[J]. Chinese Journal of Polymer Science, 2023, 41(11): 1767-1777. DOI： 10.1007/s10118-023-2981-8.

摘要

Hyperbranched polymeric fluorosurfactants had a strong synergism with the small molecule fluorosurfactant C1157 in raising their surface activity

which favored their use for highly efficient fire-extinguishing towards flammable oils.

Abstract

Fluorosurfactants are the key ingredients in the formulations of aqueous film-forming foams (AFFFs) for extinguishing flammable liquids

thus developing high-efficient and low-toxic fluorosurfactants is desirable in AFFFs application. Herein

a series of hyperbranched polymeric fluorosurfactants (HPFs) were successfully synthesized through sequentially modifying hyperbranched polyethylenimine (PEI) with the hydrophilic poly(ethylene glycol) (PEG) chains and the hydrophobic C6/C4-based perfluoroalkyl chains

which were verified by FTIR

H- and

F-NMR. The surface tensions of all the HPFs in water were measured

and the corresponding physicochemical parameters were interpreted. It was found that the surface activities of HPFs could be tuned through adjusting the ratio of PEG to perfluoroalkyl chains

the length of perfluoroalkyl chains

the molecular weight of PEI core

but not the PEG chain length. In the binary mixture of HPFs with the commercial small molecule fluorosurfactant Capstone

1157 (C1157)

a strong synergism led to the elevation of surface activity

which was attributed to the efficient encapsulation of C1157 guests by the compact hyperbranched HPFs as the hosts. The utilization of HPF/C1157 as fluorosurfactant ingredients in AFFF formulations could realize much higher fire-extinguishing efficiency towards flammable oils than the control AFFFs prepared from the polymeric Capstone

1460 or the neat C1157.

关键词

Keywords

references

Kissa,E., Fluorinated surfactants: Synthesis, properties, and applications .MarcelDekker:NewYork, 1994 ..

Ranjbar,H.;Shahraki,B.H.Effectofaqueousfilm-formingfoamsontheevaporationrateofhydrocarbonfuels. Chem. Eng. Technol. 2013 , 36 ,295−299..

Peshoria,S.;Nandini,D.;Tanwar,R.K.;Narang,R.Short-chainandlong-chainfluorosurfactantsinfirefightingfoam:areview. Environ. Chem. Lett. 2020 , 18 ,1277−1300..

Moody,C.A.;Field,J.A.Perfluorinatedsurfactantsandtheenvironmentalimplicationsoftheiruseinfire-fightingfoams. Environ. Sci. Technol. 2000 , 34 ,3864−3870..

Hinnant,K.M.;Giles,S.L.;Smith,E.P.;Snow,A.W.;Ananth,R.Characterizingtheroleoffluorocarbonandhydrocarbonsurfactantsinfirefighting-foamformulationsforfire-suppression. Fire Technol. 2019 , 56 ,1413−1441..

Sheng,Y.;Jiang,N.;Lu,S.;Li,C.Fluorinatedandfluorine-freefirefightingfoamsspreadonheptanesurface. Colloids Surf. A 2018 , 552 ,1−8..

Hill,C.;Czajka,A.;Hazell,G.;Grillo,I.;Rogers,S.E.;Skoda,M.W.A.;Joslin,N.;Payne,J.;Eastoe,J.Surfaceandbulkpropertiesofsurfactantsusedinfire-fighting. J Colloid Interface Sci. 2018 , 530 ,686−694..

Yu,X.;Jiang,N.;Miao,X.;Li,F.;Wang,J.;Zong,R.;Lu,S.Comparativestudiesonfoamstability,oil-filminteractionandfireextinguishingperformanceforfluorine-freeandfluorinatedfoams. Process Saf. Environ. Prot. 2020 , 133 ,201−215..

Piekarski,D.J.;Diaz,K.R.;McNerney,M.W.Perfluoroalkylchemicalsinneurologicalhealthanddisease:humanconcernsandanimalmodels. Neurotoxicology 2020 , 77 ,155−168..

Wang,T.;Wang,Y.;Liao,C.;Cai,Y.;Jiang,G.Perspectivesontheinclusionofperfluorooctanesulfonateintothestockholmconventiononpersistentorganicpollutants. Environ. Sci. Technol. 2009 , 43 ,5171−5175..

D'Agostino,L.A.;Mabury,S.A.Identificationofnovelfluorinatedsurfactantsinaqueousfilmformingfoamsandcommercialsurfactantconcentrates. Environ. Sci. Technol. 2014 , 48 ,121−129..

Hagenaars,A.;Meyer,I.J.;Herzke,D.;Pardo,B.G.;Martinez,P.;Pabon,M.;DeCoen,W.;Knapen,D.Thesearchforalternativeaqueousfilmformingfoams(AFFF)withalowenvironmentalimpact:PhysiologicalandtranscriptomiceffectsoftwoForafac ® fluorosurfactantsinturbot. Aquat. Toxicol. 2011 , 104 ,168−176..

Hinnant,K.M.;Giles,S.L.;Snow,A.W.;Farley,J.P.;Fleming,J.W.;Ananth,R.Ananalyticallydefinedfire-suppressingfoamformulationforevaluationoffluorosurfactantreplacement. J. Surfact. Deterg. 2018 , 21 ,711−722..

Moe,M.K.;Huber,S.;Svenson,J.;Hagenaars,A.;Pabon,M.;Trumper,M.;Berger,U.;Knapen,D.;Herzke,D.ThestructureofthefirefightingfoamsurfactantForafac ® 1157anditsbiologicalandphotolytictransformationproducts. Chemosphere 2012 , 89 ,869−875..

Dubocq,F.;Wang,T.;Yeung,L.W.Y.;Sjoberg,V.;Karrman,A.Characterizationofthechemicalcontentsoffluorinatedandfluorine-freefirefightingfoamsusinganovelworkflowcombiningnontargetscreeningandtotalfluorineanalysis. Environ. Sci. Technol. 2020 , 54 ,245−254..

Weiner,B.;Yeung,L.W.Y.;Marchington,E.B.;D'Agostino,L.A.;Mabury,S.A.Organicfluorinecontentinaqueousfilmformingfoams(AFFFs)andbiodegradationofthefoamcomponent6:2fluorotelomermercaptoalkylamidosulfonate(6:2FTSAs). Environ. Chem. 2013 , 10 ,486−493..

Schultz,M.M.;Barofsky,D.F.;Field,J.A.Quantitativedeterminationoffluorotelomersulfonatesingroundwaterbylcms/ms. Environ. Sci. Technol. 2004 , 38 ,1828−1835..

Jia,X.;Luo,Y.;Huang,R.;Zhu,X.;Zhang,Y.;Liu,Q.Two-dimensionalspreadingpropertiesandsealingcharacteristicsoffluorocarbonsurfactantsonseveraltypicalhydrocarbonfuels. Sci. Rep. 2021 , 11 ,1148..

Jia,X.;Bo,H.;He,Y.Synthesisandcharacterizationofanovelsurfactantusedforaqueousfilm-formingfoamextinguishingagent. Chem. Pap. 2019 , 73 ,1777−1784..

Jia,X.;Luo,Y.;Huang,R.;Bo,H.;Liu,Q.;Zhu,X.Spreadingkineticsoffluorocarbonsurfactantsonseveralliquidfuelssurfaces. Colloids Surf. A 2020 , 589 ,124441..

Xu,C.;Wang,H.;Wang,D.;Zhu,X.;Zhu,Y.;Bai,X.;Yang,Q.Improvementoffoamingabilityofsurfactantsolutionsbywater-solublepolymers:experimentandmoleculardynamicssimulation. Polymers 2020 , 12 ,571..

Yu,X.;Jiang,N.;Miao,X.;Zong,R.;Sheng,Y.;Li,C.;Lu,S.Formationofstableaqueousfoamsontheethanollayer:synergisticstabilizationoffluorosurfactantandpolymers. Colloids Surf. A 2020 , 591 ,124545..

Carruette,M.L.;Pabon,M.NewadditiveforlowviscosityofAFFF/ARconcentrates—studyofthepotentialfireperformance. Fire Technol. 2004 , 40 ,367−384..

ThomasJoseph,M.;Li,M.Perfluoroalkylfunctionalizedpolyacrylamideforalcoholresistant-aqueousfilmformingfoam(AR-AFFF)formulation.WO2014/052369Al, 2014 .

Clark,K.P.Fireextinguishingorretardingmaterial.WO03/045505Al, 2003 .

Song,L.;Wang,R.;Niu,K.;Liu,Y.;Kou,J.;Song,H.;Zhang,J.;Wang,Q.Design,synthesis,characterization,andsurfaceactivitiesofcomb-likepolymericfluorinatedsurfactantswithshortfluoroalkylchains. Colloids Surf. A 2021 , 609 ,125666..

Mukharjee,I.;Moulik,S.P.;Rakshit,K.Tensiometricdeterminationofgibbssurfaceexcessandmicellepoint:acriticalrevisit. J. Colloid Interface Sci. 2013 , 394 ,329−336..

Rosen,M.J.;Aronson,S.Standardfreeenergiesofadsorptionofsurfactantsattheaqueoussolution/airinterfacefromsurfacetensiondatainthevicinityofthecriticalmicelleconcentration. Colloids Surface 1981 , 3 ,201−208..

Shen,Y.;Jin,Y.;Lai,S.;Shi,L.;Du,W.;Zhou,R.Synthesis,surfacepropertiesandcytotoxicityevaluationofnonionicurethanefluorinatedsurfactantswithdoubleshortfluoroalkylchains. J. Mol. Liq. 2019 , 296 ,111851..

Gaillard,T.;Roché,M.;Honorez,C.;Jumeau,M.;Balan,A.;Jedrzejczyk,C.;Drenckhan,W.Controlledfoamgenerationusingcyclicdiphasicflowsthroughaconstriction. Int. J. Multiphase Flow 2017 , 96 ,173−187..

Arsenault,G.;Chittim,B.;Gu,J.;McAlees,A.;McCrindle,R.;Robertson,V.Separationandfluorinenuclearmagneticresonancespectroscopic( 19 FNMR)analysisofindividualbranchedisomerspresentintechnicalperfluorooctanesulfonicacid(PFOS). Chemosphere 2008 , 73 ,S53−9..

Seacat,A.M.;Thomford,P.J.;Hansen,K.J.;Clemen,L.A.;Elridge,S.R.;Elcombe,C.R.;Butenhoff,J.L.Sub-chronicdietarytoxicityofpotassiumperfluorooctanesulfonateinrats. Toxicology 2003 , 183 ,117−131..

Liu,H.;Chen,Y.;Zhu,D.;Shen,Z.;Stiriba,S.E.Hyperbranchedpolyethyleniminesasversatileprecursorsforthepreparationofdifferenttypeofunimolecularmicelles. React. Funct. Polym. 2007 , 67 ,383−395..

Irfan,M.;Seiler,M.Encapsulationusinghyperbranchedpolymers:fromresearchandtechnologiestoemergingapplications. Ind. Eng. Chem. Res. 2010 , 49 ,1169−1196..

Harkins,W.D.;Feldman,A.Films:thespreadingofliquidsandthespreadingcoefficient. J. Am. Chem. Soc. 1922 , 44 ,2665−2685..

Tang,Q.;Cheng,F.;Lou,X.L.;Liu,H.J.;Chen,Y.Comparativestudyofthiol-freeamphiphilichyperbranchedandlinearpolymersforthestabilizationoflargegoldnanoparticlesinorganicsolvent. J. Colloid Interface Sci. 2009 , 337 ,485−491..

Percec,V.;Wilson,D.A.;Leowanawat,P.;Wilson,C.J.;Hughes,A.D.;Kaucher,M.S.;Hammer,D.A.;Levine,D.H.;Kim,A.J.;Bates,F.S.;Davis,K.P.;Lodge,T.P.;Klein,M.L.;DeVane,R.H.;Aqad,E.;Rosen,B.M.;Argintaru,A.O.;Sienkowska,M.J.;Rissanen,K.;Nummelin,S.;Ropponen,J.Self-assemblyofJanusdendrimersintouniformdendrimersomesandothercomplexarchitectures. Science 2010 , 328 ,1009−1014..

Views

814

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

Hyperbranched Poly(α-aminonitrile)s Constructed via Catalyst-Free Multicomponent Polymerization of Trialdehydes, Diamines and Trimethylsilyl Cyanide

Facile Fabrication of Hyperbranched Polyacetal Quaternary Ammonium with pH-Responsive Curcumin Release for Synergistic Antibacterial Activity

2026-9 Contents

Pyrimidoisoindigo-based Polymers for Ambipolar Charge Transport

Molecularly Engineered Polyimide Films with Switchable Cavitation for Bidirectional Passive Thermal Regulation

Related Author

Jia Wang

Tian-Yu Cheng

Jian-Qing Ding

Yu-Xin Tong

Jun-Guo Fang

De-Cheng Wu

Ya-Qiang Wang

Xing Wang

Related Institution

Songshan Lake Materials Laboratory

School of Chemical and Environmental Engineering, Anhui Polytechnic University

Department of Biomedical Engineering, Southern University of Science and Technology

University of Chinese Academy of Sciences

Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Polymer Physics & Chemistry, Institute of Chemistry, Chinese Academy of Sciences

⁰