新型无定形全氟二氧杂环戊烷聚合物的研究进展
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摘要
阐述了常见的无定形全氟二氧杂环戊烷聚合物的研究进展,其中主要涉及环状单体的制备、聚合物的结构和性能以及聚合物在塑料光导纤维、气体分离膜、全氟磺酸质子交换膜等领域的应用。最后展望了该类聚合物今后的研究发展方向。
The research progress of common amorphous perfluorodioxolane polymers was reviewed,mainly including preparation of cyclic monomers,structure and properties of polymers.Also,the application development of polymers in plastics optical fibers,gas separation membrane and perfluorosulfonic proton exchange membrane were also summarized.Finally,the development trends were proposed as well.
The research progress of common amorphous perfluorodioxolane polymers was reviewed,mainly including preparation of cyclic monomers,structure and properties of polymers.Also,the application development of polymers in plastics optical fibers,gas separation membrane and perfluorosulfonic proton exchange membrane were also summarized.Finally,the development trends were proposed as well.
引文
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[29]Fang M,Okamoto Y,Koike Y,et al.Gas separation membranes prepared with copolymers of perfluoro(2-methylene-4,5-dimethyl-1,3-dioxlane)and chlorotrifluoroethylene[J].Journal of Fluorine Chemistry,2016,188:18-22.
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[31]Koike Y,Ishigure T,Murofushi H,et al.Plastic optical fiber:US7058271[P].2006-06-06.
[32]Ujihara H,Hayashi N,Minakawa K,et al.Polymer optical fiber tapering without the use of external heat source and its application to refractive index sensing[J].Applied Physics Express,2015,8(7):072501.
[33]Tiwari R R,Smith Z P,Lin H,et al.Gas permeation in thin films of“high free-volume”glassy perfluoropolymers:PartⅠ.Physical aging[J].Polymer,2014,61(22):5788-5800.
[34]Lokhandwala K A,Pinnau I,He Z J,et al.Membrane separation of nitrogen from natural gas:a case study from membrane synthesis to commercial deployment[J].Journal of Membrane Science,2010,346(2):270-279.
[35]Ahn J,Chung W J,Pinnau I,et al.Polysulfone/silica nanoparticle mixed-matrix membranes for gas separation[J].Journal of Membrane Science,2008,314(1):123-133.
[2]Zhang H,Weber S G.Teflon?AF materials[J].Topics in Current Chemistry,2012,308:307-337.
[3]Nakamura M,Kaneko I,Oharu K,et al.Novel fluorine-containing cyclic polymer:EP0303298[P].1990-01-30.
[4]Milani A,Tommasini M,Castiglioni C,et al.Spectroscopic studies and first-principles modelling of 2,2,4-trifluoro-5-trifluoromethoxy-1,3-dioxole(TTD)and TTD-TFE copolymers(Hyflon?;AD)[J].Polymer,2008,49(7):1812-1822.
[5]Yampolskii Y P.Amorphous perfluorinated membrane materials:structure,properties and application[J].Russian Journal of General Chemistry,2009,79(3):657-665.
[6]Resnick P R.Fluorinated dioxoles:US3865845[P].1975-02-11.
[7]Navarrini W,Tortelli V,Russo A,et al.Organic hypofluorites and their new role in industrial fluorine chemistry[J].Journal of Fluorine Chemistry,1999,95(40):27-39.
[8]Navarrini W,Tortelli V,Colaianna P,et al.Perfluorodioxoles,the preparation process thereof,and homopolymers and copolymers therefrom:US5646223[P].1997-07-08.
[9]Liu W H,Mike2F,Guo Y Z,et al.Free-radical polymerization of dioxolane and dioxane derivatives:effect of fluorine substituents on the ring opening polymerization[J].Journal of Polymer Science Part A:Polymer Chemistry,2004,42(20):5180-5188.
[10]Mikes F,Teng H X,Kostov G,et al.Synthesis and characterization of perfluoro-3-methylene-2,4-dioxabicyclo[3,3,0]octane:homo-and copolymerization with fluorovinyl monomers[J].Journal of Polymer Science Part A:Polymer Chemistry,2009,47(23):6571-6578.
[11]Yang Y,Mike2F,Yang L,et al.Investigation of homopolymerization rate of perfluoro-4,5-substituted-2-methylene-1,3-dioxolane derivatives and properties of the polymers[J].Journal of Fluorine Chemistry,2006,127(2):277-281.
[12]Zhang B,Li L L,Mike2F,et al.Multidimensional NMR characterization of perfluorinated monomer and its precursors[J].Journal of Fluorine Chemistry,2013,147(147):40-48.
[13]Resnick P R.Polymers of fluorinated dioxoles:US3978030[P].1976-08-31.
[14]Resnick P R,Buck W H.Modern fluoroplastics[M].Chichester,UK:Scheirs J,1997,397.
[15]Wood C D,Michel U,Rolland J P,et al.New fluoropolymer materials[J].Journal of Fluorine Chemistry,2004,125(11):1671-1676.
[16]Colaianna P,Brinati G,Arcella V.Amorphous perfluoropolymers:US5883177[P].1999-03-16.
[17]Prabhakar R S,Freeman B D,Roman I.Gas and vapor sorption and permeation in poly(2,2,4-trifluoro-5-trifluoromethoxy-1,3-dioxole-co-tetrafluoroethylene)[J].Macromolecules,2004,37(20):7688-7697.
[18]Avataneo M,Veneorini A.Amorphous fluorinated polymer:EP2722350[P].2014-04-23.
[19]Russo A,Navarrini W.Perfluoro-4-methyl-1,3-dioxole:a new monomer for high-Tgamorphous fluoropolymers[J].Journal of Fluorine Chemistry,2004,125(18):73-78.
[20]Watakabe A,Eriguchi T,Tanuma T,et al.Solid polymer electrolyte material,liquid composition,solid polymer fuel cell and fluoropolymer:US7220508[P].2007-05-22.
[21]Perry R L,Roelofs M G,Wheland R C,et al.Ionomers and ionically conductive composition:US20130245219[P].2013-09-19.
[22]Yoshitake M,Watakabe A.Perfluorinated ionic polymers for PEFCs(Including supported PFSA)[M].Berlin Heidelberg:Springer,2008,127-155.
[23]Mike2F,Yang Y,Teraoka I,et al.Synthesis and characterization of an amorphous perfluoropolymer:poly(perfluoro-2-methylene-4-methyl-1,3-dioxolane)[J].Macromolecules,2005,38(10):4237-4245.
[24]Okamoto Y,Mike2F,Yang Y,et al.The effect of fluorine substituents on the polymerization mechanism of 2-methylene-1,3-dioxolane and properties of the polymer products[J].Journal of Fluorine Chemistry,2007,128(3):202-206.
[25]Mike2F,Baldrian J,Teng H X,et al.Characterization and properties of semicrystalline and amorphous perfluoropolymer:poly(perfluoro-2-methylene-1,3-dioxolane)[J].Polymers for Advanced Technologies,2011,22(22):1272-1277.
[26]Liu W H,Koike Y,Okamoto Y.Synthesis and radical polymerization ofperfluoro-2-methylene-1,3-dioxolanes[J].Macromolecules,2005,38(23):9466-9473.
[27]Koike K,Mike2F,Zhang H,et al.Synthesis and characterization of copolymers of perfluoro(2-methylene-4,5-dimethyl-1,3-dioxolane)and perfluoro(2-methylene-1,3-dioxolane)[J].Journal of Fluorine Chemistry,2013,156(12):198-202.
[28]Okamoto Y,Zhang H,Mike2F,et al.New perfluoro-dioxolane-based membranes for gas separations[J].Journal of Membrane Science,2014,471(6):412-419.
[29]Fang M,Okamoto Y,Koike Y,et al.Gas separation membranes prepared with copolymers of perfluoro(2-methylene-4,5-dimethyl-1,3-dioxlane)and chlorotrifluoroethylene[J].Journal of Fluorine Chemistry,2016,188:18-22.
[30]Yang Y,Mike2F,Yang L,et al.Novel amorphous perfluorocopolymeric system:copolymers of perfluoro-2-methylene-1,3-dioxolane derivatives[J].Journal of Polymer Science:Part A:Polymer Chemistry,2006,44(5):1613-1618.
[31]Koike Y,Ishigure T,Murofushi H,et al.Plastic optical fiber:US7058271[P].2006-06-06.
[32]Ujihara H,Hayashi N,Minakawa K,et al.Polymer optical fiber tapering without the use of external heat source and its application to refractive index sensing[J].Applied Physics Express,2015,8(7):072501.
[33]Tiwari R R,Smith Z P,Lin H,et al.Gas permeation in thin films of“high free-volume”glassy perfluoropolymers:PartⅠ.Physical aging[J].Polymer,2014,61(22):5788-5800.
[34]Lokhandwala K A,Pinnau I,He Z J,et al.Membrane separation of nitrogen from natural gas:a case study from membrane synthesis to commercial deployment[J].Journal of Membrane Science,2010,346(2):270-279.
[35]Ahn J,Chung W J,Pinnau I,et al.Polysulfone/silica nanoparticle mixed-matrix membranes for gas separation[J].Journal of Membrane Science,2008,314(1):123-133.