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| موضوع: كتاب Handbook of Specialty Fluorinated Polymers - Preparation, Properties, and Applications الأربعاء 29 نوفمبر 2023, 1:08 am | |
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أخواني في الله أحضرت لكم كتاب Handbook of Specialty Fluorinated Polymers - Preparation, Properties, and Applications Edited by Susanta Banerjee
و المحتوى كما يلي :
Contributors ix 1 Introduction to Semifluorinated High-Performance Polymers . 1 Susanta Banerjee 1.1 General Introduction to High-Performance Polymers . 1 1.2 Uniqueness of Fluorine . 2 1.2.1 Structure and Bonding . 2 1.2.2 Effects of Fluorine/Perfluoroalkyl Groups on Chemical Reactivity 4 1.2.3 Role of Perfluoroalkyl Groups in the Aromatic Nucleophilic Displacement Reaction . 6 1.2.4 Role of Fluorine in Polymer Structure . 7 1.3 Summary . 8 References 8 2 Fluorinated Poly(Arylene Ether)s: Synthesis, Properties, and Applications . 11 Sipra Ghosh, Rajdeep Mukherjee, Anindita Ghosh, Aruna Kumar Mohanty, and Susanta Banerjee 2.1 Introduction . 11 2.2 Synthesis, Characterization, and Properties of the Polymers 12 2.2.1 Polymerization by –CF3-Activated Fluorine Displacement Reaction 13 2.2.2 Polymerization by –CF3-Activated Nitro-Displacement Reaction 13 2.2.3 Polymerization by –CF3-Activated Fluoro- and Nitro-Displacement Reaction . 18 2.3 Fluorinated PAEs . 18 2.3.1 Fluorinated PAEs with Terphenyl, Pyridinylidene, Thiophenylidene, and Quadriphenyl Moieties 19 2.3.2 Fluorinated PAEs with Anthracene and Fluorene Moieties . 22 2.3.3 Fluorinated PAEs with Phthalimidine Moiety . 25 2.3.4 Fluorinated PAEs with Naphthyl and Naphthyl-Imido Moiety . 25 2.3.5 Fluorinated PAEs with Cardo Cyclohexylidene Moiety 28 2.3.6 Fluorinated PAEs with Phenyl Phosphine Oxide Moiety 28 2.3.7 Fluorinated PAEs with Thioether Moiety 29 2.3.8 Fluorinated PAEs with Phthalazinone Moiety . 30 2.3.9 Branched FPPEs . 32 2.3.10 Fluorinated PAEs 39 2.4 Fluorinated PAEs for Membrane-Based Applications 40 2.4.1 Fluorinated PAEs in Gas Separation Application 41 2.4.2 Fluorinated PAEs in PV Application 54 2.4.3 Fluorinated Sulfonated PAEs as PEMs 56 2.5 Summary . 87 References 88 Contentsvi Contents 3 Fluorinated Polyimides: Synthesis, Properties, and Applications . 97 Anindita Ghosh, Ershad Ali Mistri, and Susanta Banerjee 3.1 Introduction . 97 3.2 Synthesis, Characterization, and Properties of Polymers 98 3.2.1 One-Step Polymerization . 98 3.2.2 Two-Step Polymerization . 98 3.2.3 Fluorinated Polyimides 106 3.2.4 Fluorinated Poly(Ether Imide)s 107 3.2.5 Polyimide Block Copolymer Aerogels 125 3.2.6 Fluorinated Poly(Imide Sulfone)s 125 3.3 Fluorinated Polyimides for Membrane-Based Applications . 125 3.3.1 Fluorinated Polyimides in Gas Separation . 127 3.3.2 Fluorinated Polyimides in Pervaporation . 146 3.3.3 Fluorinated Sulfonated Polyimides as PEMs . 152 3.4 Summary . 172 References 173 4 Fluorinated Polyamides: Synthesis, Properties, and Applications 187 Parthasarathi Bandyopadhyay, Debaditya Bera, and Susanta Banerjee 4.1 Introduction . 187 4.2 Synthesis, Characterization, and Properties of the Polymers 189 4.2.1 Low-Temperature Solution Polycondensation . 189 4.2.2 High-Temperature Phosphorylation Polycondensation 190 4.3 Selected Polyamide Structure and Properties 190 4.3.1 Fluorinated Polyamides 191 4.3.2 Fluorinated Poly(ether amide)s 191 4.3.3 Fluorinated Poly(ether amide sulfone)s . 207 4.4 Fluorinated Polyamides for Membrane-Based Applications . 208 4.4.1 Fluorinated Polyamides in Gas Separation Application 208 4.4.2 Fluorinated Polyamides in Pervaporation Application 217 4.4.3 Fluorinated Sulfonated Polyamides as PEM 220 4.5 Summary . 222 References 223 5 Fluorinated Polyazoles: Synthesis, Properties, and Applications 227 Debaditya Bera, Asheesh Singh, Soumendu Bisoi, and Susanta Banerjee 5.1 Introduction . 227 5.2 Synthesis, Characterization, and Properties of the Polybenzazoles 228 5.2.1 Fluorinated PBI 228 5.2.2 Fluorinated PBOs . 240 5.2.3 Fluorinated PBTs . 248 5.3 Fluorinated Heterocyclic Polymers for Membrane-Based Applications . 250 5.3.1 Fluorinated Heterocyclic Polymers in Gas Separation Application . 250 5.3.2 Fluorinated Heterocyclic Polymers in a Pervaporation Application 257 5.3.3 Fluorinated Heterocyclic Polymers as Proton Exchange Membranes . 258 5.4 Summary . 264 References 264Contents vii 6 Fluorosilicones and Other Fluoropolymers: Synthesis, Properties, and Applications 271 Ershad Ali Mistri, Anindita Ghosh, and Susanta Banerjee 6.1 Introduction . 271 6.2 Fluorosilicone Polymers 272 6.2.1 Fluorosilicone Elastomers 277 6.2.2 Fluorosilicone Urethanes . 279 6.2.3 Fluoroacrylates and Fluorosilicone Acrylates 283 6.2.4 Fluorosilicone Polyimides 286 6.3 Other Fluoropolymers . 292 6.3.1 Poly(tetrafluoroethylene) and Its Copolymers . 292 6.3.2 Perfluorocyclobutyl Aryl Ether Polymers 293 6.4 Applications of Fluorosilicones and Other Fluoropolymers . 295 6.4.1 Fluorosilicones for Gas Separation 295 6.4.2 Fluorosilicones in Pervaporation Application 299 6.4.3 Other Fluoropolymers as Proton Exchange Membranes . 301 6.4.4 Fluorosilicones and Fluoropolymers in Special Application . 308 6.5 Summary . 310 References 310 Index 319 319 A ABA triblock copolymers, 73f 1,3-adamantanedicarbonyl chloride (ADC), 246–247 AFCs. See Alkaline fuel cells AFM. See Atomic force microscopy AG. See Arborescent graft Alkaline fuel cells (AFCs), 56 α,α-bis(4-amino-3,5-difluorophenyl) phenylmethane (4FMA), 124 1,4-bis-(4-amino-2-trifluoromethylphenoxy)benzene (ATPB), 105–106 1,4-bis-(4-amino-2-trifluoromethylphenoxy)tetrafluorobenzene (ATPT), 105–106 1, 3–bis-(4-amino-2-trifluoromethylphenoxy) 4,6-dichlorobenzene (ATPD), 105–106 2,2-bis(3-amino-4-hydroxyphenyl)- 2-phenyl-l,l,1-trifluoroethane (3FAP), 245 2,2′-bis(3-amino-4-hydroxyphenyl) hexafluoropropane (APAF), 245–246 2,2′-bis(2-amino-4- trifluoromethylphenoxy)-1,1′- binaphthyl (AFPBN), 114–115 1,1-bis(3′-amino-4′-hydroxyphenyl)-1- (3′,5′-ditrifluoromethylphenyl)- 2,2,2-fluoroethane (9FAP), 247–248 2,2′-bis(4-aminophenoxy)hexafluoropropane (6FAP), 164–165 Aminopropyl-terminated polydimethylsiloxane (APPS), 287–288 Anionic ring opening polymerization (AROP), 277–278 Anthracene moiety, 22–24 APPS. See Aminopropyl-terminated polydimethylsiloxane; bis [4-(4-aminophenoxy) phenyl] sulfone Arborescent graft (AG), 303 Aromatic nucleophilic displacement reaction, 6, 6f Aromatic polyamides, 187, 188f, 196f Aromatic polyazoles, 227 Aromatic polyimides, 97 AROP. See Anionic ring opening polymerization Atom transfer radical polymerization (ATRP), 274–275 Atomic force microscopy (AFM), 70, 284–285 ATR, 170–171 ATRP. See Atom transfer radical polymerization B BA. See Butyl acrylate BDAF. See bis(4-[4-aminophenoxy] phenylhexafluoropropane) Bent’s rule, 4 Benzene-1,2,4,5-tetracarboxylic dianhydride (PMDA), 144–145 1,3,5-benzenetricarboxylic acid (BTA), 234–235 3,3′4,4′-benzophenone tetracarboxylic acid dianhydride (BTDA), 144–145, 157–159, 288–289 Benzophenone-3,3′,4,4′-tetracarboxylic dianhydride. See 3,3′4,4′- benzophenone tetracarboxylic acid dianhydride (BTDA) Biphenylene moiety, 205f 4,4′-binaphthyl-1,1′,8,8′-tetracarboxylic dianhydride (BTDA), 157–159 4,4′-biphenyl-dicarbonyl chloride (BPDC), 248 2,5-bis (tert-butylperoxy)-2,5-dimethylhexane (DBPMH), 278 2,4 bis-(4-fluoro-trifluoromethylphenyl) phenol, 34–35 2,2-bis(3-amino-4-hydroxyphenyl) hexafluoropropane (Bis-APAF), 248 Bis(3-aminopropyl)-terminated poly(dimethylsiloxane) (SIDA), 299 2,2′-bis(3-sulfobenzoyl) benzidine (2,2′-BSBB), 157–158 2,6-bis(3′,4′-diaminophenyl)-4- phenylpyridine (Py-TAB), 236 2,5-bis(4-aminophenoxy)benzenesulfonic acid (BAPBS), 159 2,2-bis(4-(4-amino-3-hydroxyphenoxy) phenyl)-hexafluoropropane (6FBAHPP), 248 9,9-bis(4-[4-amino-2-trifluoromethylphenoxy] phenyl)xanthenes (BATFPX), 114–115 2,5-bis(4-amino-2-trifluoromethylphenoxy) benzenesulfonic acid (BAFPBS), 159 2,2-bis(4-carbonyl chloride benzene)-l, l, l-3,3,3-hexafluoropropane (6FAC), 245 1,3-bis(4-fluorobenzoyl)benzene (1,3-BFBB), 58 4,4′-bis(4′-fluoro-3′-trifluoromethyl benzyl)biphenyl (QBF), 62–64 bis(o-aminophenol)s, 1,1-bis(3′-amino- 4′-hydroxyphenyl)-1-(3′- trifluoromethylphenyl)-2,2,2- trifluoroethane (6FAP), 247–248 2,2′-bis(trifluoromethyl)-4, 4′-biphenyldicarboxylic acid synthesis, 232f 2,5-bis(trifluoromethylphenylene) thiophene (6FPT), 42 2,6-bis(trifluoromethylphenylene) pyridine (6FPPr), 42 N,O-bis(trimetylsylil)acetamide (BSA), 247 2,2′-bis[2-(4-fluorophenyl) benzoxazol- 6-yl] hexafluoropropane (6BO), 263 2,5-bis[3′-trifluromethyl-4′(4″- aminobenzoxy)benzyl] thiophene (BATh), 138–144 Index Note: Page numbers followed by “f” and “t” indicate figures and tables respectively.320 Index 4,4-bis[3′-trifluoromethyl-4′(4″- aminobenzoxy)benzyl] biphenyl (BAQP), 138–144 2,6-bis[3′-trifluromethyl-4′(4″- aminobenzoxy)benzyl]pyridine (BAPy), 138–144 9,9-bis[4-(2-trifluoromethyl-4- aminophenoxy)phenyl]xanthenes (BTFAPX), 200 2, 2-bis[4-(3,4-dicarboxyphenoxy)phenyl] propane dianhydride (BPADA), 288 bis(4-[4-aminophenoxy] phenylhexafluoropropane) (BDAF), 158, 301 bis[4-(4-aminophenoxy) phenyl]sulfone (APPS), 132 2,2′-bis[4-(4-chlorobenzoyl)]phenoxyl perfluoropropane (BCPPF), 62 5-(1,1-bis[4-aminophenyl]-2,2,2- trifluoroethyl)-2-(4-sulfophenoxy) benzenesulfonic acid (BABSA), 158–159 Bisphenol A, 4,4′-(4,4′-isopropylidenediphenoxy)bis (phthalic anhydride), (BPA), 15, 35–37, 62–64 Bisphenol-A[diphthalic anhydride], 4,4′-(4,4′-isopropylidenediphenoxy) bis (phthalic anhydride), (BPADA), 97–98, 144–145, 288 5-(3,5-bistrifluoromethyl-phenoxy) isophthaloyl dichloride (6FPC), 201–202 BNTDA. See 4,4′-binaphthyl-1,1′,8,8′- tetracarboxylic dianhydrid (BTDA) Bovine serum albumin (BSA), 309–310 BP-PFCB. See Hydrophobic homopolymers biphenyl perfluorocyclobutyl BPADA. See Bisphenol-A[diphthalic anhydride], 4,4′-(4,4′- isopropylidenediphenoxy) bis (phthalic anhydride) Branched sulfonated fluorinated poly(aryl ether ketone) (Br-SPAEK), 81–83 Branched sulfonated poly(ether ether ketone) (Br-SPEEK), 82–83, 84f BSA. See Bovine serum albumin BTBP. See Poly[2,2′-[2,2′- bis(trifluoromethyl)- 4,4′-biphenylene]-5,5′- bibenzimidazole] BTDA. See 4,4′-binaphthyl-1,1′,8,8′- tetracarboxylic dianhydride Butyl acrylate (BA), 284 C Cargo groups, 192f C2F4 monomers. See Tetrafluoroethylene monomers C4F9C2H4SiCl3. See Trichloro-3,3,4,4,5, 5,6,6,6-nonafluorohexylsilane C8F17–CH2CH2–fluorosilicon. See Fluorosilicon with 3,3,4,4,5,5,6,6,7,7,8, 8,9,9,10,10,10- heptadecafluorodecyl groups Cardo cyclohexylidene moiety, 28 Cardo poly(aryl ether ketone) (PEK-C), 50 Cardo moiety, 51–52, 256, 256f Cardo moiety-based polyimide series, 146 Cardo groups, 192f Carrier transport model, 149, 149f Catalytic polymerization, 229 Cationic ring opening polymerization (CROP), 277–278 CED. See Cohesive energy density C–F bond, 101 –CF3 groups. See Trifluoromethyl groups CF3CH2CH2SiCl3. See Trichloro-3,3,3- trifluoropropylsilane CFBDH, 285–286, 286f –CH2CH2CF3. See 3,3,3-trifluoropropyl group (TFP group) –CH2–CH2–CF3. See 3,3,3-trifluoropropyl group (TFP group) Chemical imidization, 100–106, 102f 2-chloroethylvinylether (CEVE), 304 Chloroform (CHCl3), 287–288 Chlorotrifluoroethylene (CTFE), 279–280, 304 Coefficient of thermal expansion (CTE), 102–103 Cohesive energy density (CED), 50–51 Composite membrane, 170, 171f Cotton fabrics, 308 CROP. See Cationic ring opening polymerization CTE. See Coefficient of thermal expansion CTFE. See Chlorotrifluoroethylene CTHFA. See Dicarboxyl terminated poly(2,2,3,4,4,4-hexafluorobutyl acrylate) Cyclohexylidene moiety, 202f D DABA. See Diaminobenzoic acid DABS. See Diacids 2,4-diaminobenzenosulfonic acid DBP. See Dibutyl phthalate Decafluorobiphenyl (DFBP), 30–31 Decafluorodiphenyl sulfone (DFPSO), 40 Degree of polymerization (DP), 289 Degree of sulfonation (DS), 56, 157–158, 221, 235 Densely sulfonated fluorinated PAEs (SPAEK-xx), 72 DFBP. See Decafluorobiphenyl DFMA. See Dodecafluoroheptyl methacrylate DFPSO. See Decafluorodiphenyl sulfone DGEBA. See Diglycidyl ether of bisphenol A 3,6-di(3′,5′-bis[trifluoromethyl]phenyl) pyromelliticdianhydride (12FPMDA), 116 Diacids 2,4-diaminobenzenosulfonic acid (DABS), 221–222 3,5-diamino benzoic acid (DABA), 151 2,5-Diamino-1, 4-benzenedithioldihydrochloride (DABDT), 250 2,6-diamino toluene (DAT), 135–136 3,3′-diamino-4, 4′-dihydroxybiphenyl (mHAB), 255–256 4,4′-diamino-3,3′- dimethyldiphenylmethane (DMMDA), 150–151 3,3′-diaminobenzidinetetrahydrochloride (DAB), 229–230 3,5-diaminobenzoate-terminated polydimethylsiloxane (DBPDMS), 291–292 Diaminobenzoic acid (DABA), 133 4,4′-diaminodiphenylether-2,2′-disulfonic acid (ODADS), 158 Dibutyl phthalate (DBP), 236 Dicarboxyl terminated poly(2,2,3,4,4, 4-hexafluorobutyl acrylate) (CTHFA), 280–281 2,5-dichloro-3′-sulfobenzophenone (DCSB), 62 Dichloromethane (CH2Cl2), 28, 287–288 Dielectric constant, 12, 16, 22, 26, 38–39, 103 Differential scanning calorimetry (DSC), 17, 272–273 Diffusion coefficient, 129–130 Diffusivity selectivities, 298t Diglycidyl ether of bisphenol A (DGEBA), 281–283 3,3′-dihydroxybenzidine diamine (HAB), 257–258 3,3′-dihydroxybenzidine (pHAB), 255–256 N,N-dimethyl acetamide (DMAc), 12, 98–99, 188, 287–288 Dimethyl formamide (DMF), 286–287 Dimethyl sulfoxide (DMSO), 12, 28, 200–201, 206, 286–287 Dimethylaminoethyl methacrylate (DM), 285 Dimethylformamide (DMF), 98–99, 188, 287–288 Diphenyl phosphite (DPP), 190 Diphenylfluorene (FBP), 42 4′,4-diphenylmethane di-isocyanate (MDI), 281–283 Diphenylmethylene moiety, 198f Direct methanol fuel cell (DMFC), 57, 301–302Index 321 3,3′-disodiumsulfonyl-4,4′- dichlorodiphenylsulfone (SDCDPS), 62–64 3,3′-disodiumsulfonyl-4,4′- difluorobenzophenone (SDFBP), 81 3,3′-disulfonyl-4,4′-dicarboxydiphenyl sulfone (DSDCDPS), 235–236 Disperse Red 1 (DR1), 105–106 3,3′-disulfonated-4,4′-difluorodiphenyl sulfone (SDCDPS), 263 4,8-disulfonyl- 2, 6-naphthalenedicarboxylic acid (DSNDA), 235 DM. See Dimethylaminoethyl methacrylate DMA. See Dynamic mechanical analysis DMF. See Dimethyl formamide; Dimethylformamide DMFC. See Direct methanol fuel cell DMSO. See Dimethyl sulfoxide Dodecafluoroheptyl methacrylate (DFMA), 285 DP. See Degree of polymerization DPP. See Diphenyl phosphite DR1. See Disperse Red 1 DS. See Degree of sulfonation DSC. See Differential scanning calorimetry Dynamic mechanical analysis (DMA), 289 E EB. See Elongation at break EGDE. See Ethylene glycol diglycidyl ether EGR diaphragms. See Exhaust gas recirculating diaphragms Electronic polarization, 100–101 Electrospun nanofibers, 169–170 NTDA-BDSA-r-APPF, 171f Elongation at break (EB), 19–22 Epoxy methacrylate (EMA), 280–281 ETFE-PEM. See Poly(styrene sulfonic acid)-grafted poly(ethylenecotetrafluoroethylene)polymer electrolyte membrane Ethylene glycol diglycidyl ether (EGDE), 234–235 Exhaust gas recirculating diaphragms (EGR diaphragms), 277–278 F 6F. See Hexafluoroisopropylidene F-hb-PAE. See Fluorinated hb PAE F-hb-PAEPO. See Fluorinated hb-poly(arylene ether phosphine oxide) 14F-PBI. See Poly(2,2′- tetradecafluoroheptylene-5,5′- bibenzimidazole) 6FAP. See bis(o-aminophenol)s, 1,1-bis(3′- amino-4′-hydroxyphenyl)-1-(3′- trifluoromethylphenyl)-2,2,2- trifluoroethane FBP. See Diphenylfluorene 6FDA. See Hexafluoropropane dianhydride 6FDA-NDA/DABA polyimide, 152f FFV. See Fractional free volume Flexible siloxane segments, 286–287 FLS. See Fluorosilicon Fluorene moiety, 22–24, 203f 4,4′-(9-fluorenylidene) diphenol (FDP), 35–37 Fluorinated acrylate resin, 284, 285f Fluorinated diamines, 102–103, 104t Fluorinated dianhydrides, 102–103 Fluorinated hb PAE (F-hb-PAE), 34–35, 34f Fluorinated hb-poly(arylene ether phosphine oxide) (F-hb-PAEPO), 35 Fluorinated heterocyclic polymers in gas separation application, 250–257 for membrane-based applications, 250 as PEM, 258–264 in PV application, 257–258 Fluorinated PAE, 54–55. See also Fluorinated poly(arylene ether) permeation flux, 55 QPESs, 55, 55f Fluorinated PBI, 228 structural modification and effects, 229–240 amine-terminated hyperbranched PBIs, 235f fluorine-containing PBI copolymer, 238f PA-doped PBI membranes, 231t PBI/silica hybrid material synthesis, 239f PFCB–PBI, 231f polymerization solvent study, 232t sPBI-NF chemical structure, 235f synthesis procedure and properties, 228–229 synthesis route to microporous PBI, 233f Fluorinated PBO, 240, 243f, 247f, 254f procedure and properties, 240–241 6FAP, 246–247 fluorinated aromatic PBOs, 242 fluorinated poly(arylene ether benzoxazole)s, 244t, 246t by low-temperature solution polycondensation reaction, 247 PBI30OH-X-si and PBI30OH-X-d membranes, 241f trifluoroethane-based PBOs, 248f two-stage method, 242f–243f synthesis, 258f Fluorinated PBTs, 248 synthesis, 249f procedure and properties, 249–250 Fluorinated poly(ether imide), 107. See also Fluorinated sulfonated copolyimides fluorinated aromatic dianhydride, 115–116 diamine, 108–115, 109t–114t dianhydrides, 116f polyimide film, 115f polyimides and unit structures, 118t–122t semi-alicyclic polyimides, 115 perfluoroalkyl groups, 124–125 poly(ether imide), 117, 123 6FPPMDA, 116 unsymmetrical diamine, 108 Fluorinated poly(amide imide sulfone), 126f Fluorinated poly(aryl ether ketone), 26f Fluorinated poly(arylene ether ketone), 39f Fluorinated poly(arylene ether sulfide), 30f Fluorinated poly(arylene ether sulfone), 40f Fluorinated poly(arylene ether) (Fluorinated PAE), 12, 18–19, 39–40, 54–55 anthracene moiety, 22–24 branched FPPEs, 32–40 cardo cyclohexylidene moiety, 28 fluorene moiety, 22–24 for membrane-based applications, 40–41 fluorinated sulfonated PAEs as PEMs, 56–87 in gas separation application, 41–54 in PV application, 54–56 naphthyl, 25–27 naphthyl-imido moiety, 25–27 phenyl phosphine oxide moiety, 28–29 phthalazinone moiety, 30–32 phthalimidine moiety, 25 pyridinylidene moiety, 19–22 quadriphenyl moiety, 19–22 terphenyl moiety, 19–22 thioether moiety, 29–30 thiophenylidene moiety, 19–22 Fluorinated poly(ether amide sulfone), 207–208 Fluorinated poly(ether amide)s, 191–192 alicyclic diamine, 191–207 aromatic fluorinated diamines, 206 bis(phenylphenyl)fluorene moiety, 192–193 flexible ether linkages, 193 fluorinated PAs, 201–202 incorporation of–CF3 moiety, 204 methylene linkages, 193–197 soluble polyamides development, 197–198 xanthene, 198–200322 Index Fluorinated poly(ether imide)s, 107–125 Fluorinated poly(ether sulfone imide), 127f Fluorinated poly(imide sulfone), 125 Fluorinated poly(phthalazinone ether) (FPPE), 30–31, 31f branched FPPEs, 32 AB2 monomer, 34–35, 37–38 –CF3-substituted AB type monomer, 39 F-hb-PAE, 34–35, 34f F-hb-PAEPO, 35 hb PAEs synthesis, 33f, 36f–37f hb polymers physical properties, 38t high-molecular-weight products, 38 nitro displacement reaction, 32–34 transparent pale yellow films, 38–39 modified nucleophilic aromatic substitution, 31f Fluorinated polyamides, 191, 217 biphenylene moiety, 205f containing diphenylmethylene moiety, 198f containing indene moiety, 191f cyclohexylidene moiety, 202f fluorene moiety, 203f high carbon-containing alcohols, 218 ketone moiety, 206f for membrane-based applications, 208 fluorinated sulfonated polyamides as PEM, 220–222 in gas separation application, 208–217 PV application, 217–220 naphthalene moiety, 199f from noncoplanar 2,2′-dimethyl-4,4′- biphenylene units, 198f polyamides preparation, 217f PSI, 218–220 reaction scheme and structures, 191f on separation of benzene/cyclohexane, 219t–220t terphenyl moiety, 204f xanthene moiety, 199f Fluorinated polyazoles, 264. See also Polybenzoxazole (PBO); Polybenzimidazole (PBI); Polybenzothiazole (PBT) Fluorinated polyimides, 101–102, 106–107, 106f, 146, 299 mass transport, 148–149 for membrane-based applications, 125–127 fluorinated sulfonated polyimides as PEMs, 152–171 in gas separation, 127–146 in pervaporation, 146–152 non-cross-linked and cross-linked 6FDA-based copolyimides, 151f physical and pervaporation properties, 149–152 separation principles, 147–148 triptycene-based, 107f and unit structures, 118t–122t Fluorinated polymers, 284 Fluorinated sulfonated copolyimides, 155–156, 169–170 block/graft copolyimides, 164 6FDA-HABA-g-NTDA-BDSA, 166f 6FDA-HABA-g-NTDA-BSPB, 167f fluorinated block co-SPI, 164–165 polymer architecture, 167–169 solid-state NMR analysis, 169 sulfonated block copolyimides, 166f sulfonated co-SPIs, 168f water uptake and conductivity values of block co-SPIs, 165t on electrospun nanofibers, 169–171 multi-block co-SPI, 169f random copolyimides, 155–156 BABSA-based co-SPIs, 159f BTDA-based sulfonated copolyimides, 157f co-SPI and Nafion 117 membranes PEM properties, 164t DQN-XX copolymers, 162f DS on PEM properties, 158 fluorinated co-SPIs repeat unit structures, 161f fluorinated sulfonated copolymers, 156 hydrolytic-oxidative stability, 161 proton conductivity, 162–163 sulfonated diamine monomers, 159 synthetic route of sulfonated polynaphthalimides, 160f transmission electron spectroscopy, 161–162 Fluorinated sulfonated PAEs as PEM, 56 C–F bonds, 57 comb-shaped sulfonated fluorinated PAEs, 78–81 densely sulfonated fluorinated PAEs, 72–74 fluoroalkyl sulfonated PAEs, 83–87 high molecular weight, 56–57 sulfonated fluorinated block PAEs, 70–72 sulfonated fluorinated branched PAEs, 81–83 sulfonated fluorinated PAEs with side chain grafting, 74–78 sulfonated fluorinated random PAEs, 57–70 Fluorinated sulfonated polyamides as PEM, 220–222, 222f Fluorinated sulfonated polyimides as PEMs, 152–153 fluorinated sulfonated copolyimides, 155–171 fuel cell, 153f proton conduction mechanism, 154–155 proton transport Grotthus mechanism, 154–155, 154f vehicular mechanism, 155f SPI, 153–154 Fluorine effect, 2, 7, 127, 188 oxetane acetals hydrolysis, 5f perfluoroalkyl group in aromatic nucleophilic displacement reaction, 6 on chemical reactivity, 4–6 in polymer structure, 7 +R effect, 5f structure and bonding, 2 atom electronic configuration, 4 bond length, 4 chemistry, 3 elements bond energies, 3t elements electronegativity, 3t halogen, 2t non-bonding electron, 3 trifluoromethyl-substituted monomers and polymers, 8f 2-fluoro-2-perfluorobutyl-1,3-propanediol (7bCF-diol), 40 Fluoroacrylates, 283–286 Fluoroalkyl sulfonated PAEs, 83–87 Fluoroalkyloxypropylcyclosiloxanes, 276–277 Fluoroalkylsilsesquioxane polymers, 273–274 Fluoropolymers, 7 as PEMs, 301–302 blends of hydrophilic and hydrophobic PFCB polymers, 305 ETFE-PEMs, 307 ionic exchange capacity, 303f LG and AG membranes, 303–304 poly(vinylidene fluoride)-gpoly(styrene sulfonic acid) copolymers, 304f proton conductivity, 303f PVDF and SEBS thermoplastic elastomer, 301–302 RH of PVDF graft copolymer membranes, 304f sBP-PFCB, 305, 306f sBP-PFCB/SO2-PFCB, 305–306 side-chain sulfonated PFCB ionomer, 306, 307f sPEEK, 304–305 SPFS-X, 307–308, 308f PFCB aryl ethers, 293–295 PTFE, 292–293 in special application, 308–310 Fluorosilicon (FLS), 275–276 block copolyimides, 289 co-poly(imide siloxane), 290f DSC and DMA, 289 siloxane loading, 290–291 storage modulus, 289–290 T g of hard blocks, 291fIndex 323 graft copolyimides, 291–292 DBPDMS, 291–292 structure of polyimide, 291f–292f TFBB, 292 random copolyimides, 286–287 co-poly(imide siloxane), 287–289, 287f–289f poly(imide siloxane)s, 287–288 TFAA and APPS, 288–289 Fluorosilicon with 3,3,4,4,5,5,6,6,7,7,8,8, 9,9,10,10,10-heptadecafluorodecyl groups (C8F17–CH2CH2–fluorosilicon), 273–274 Fluorosilicone polymers, 272 C8F17CH2CH2CH2–Cl3Si–FLS, 274, 274f C8F17CH2CH2CH2–FLS, 274, 274f condensation chemistry, 272 condensation of dihalosilanes, 273f fluoroalkyloxypropylcyclosiloxanes, 276–277 fluoroalkylsilsesquioxane polymers, 273–274 PDMS-b-PHFBMA diblock copolymers, 275f PDMS-b-PMMA-b-PHFBMA triblock copolymer, 275, 276f polydimethylsiloxane macroinitiator, 274–275 PTFPMS synthesis anionic ring opening polymerization, 273f random copolymers, 272–273 reactivity of cyclosiloxane, 276 studies on polyacrylate and polystyrene containing fluoroalkyl side chains, 275–276 Fluorosilicone rubber (FSR), 271–272, 278 Fluorosilicone(s), 271, 277 acrylates, 283–286 elastomers, 277–278 application, 278 fluorinated chiral LCEs, 278–279, 279f MFSR, MSR and FSR, 278 optical textures of monomers, 279, 280f for gas separation diffusivity and solubility coefficients, 298–299 6FDA-based PIS membranes, 298f O2–N2 and H2–N2 separation factors, 295 effect of percent PIS, 299f permselectivity of PIS membranes, 299f PI-POSS nanocomposite membranes, 296–297 PIS membranes, 297–298 poly(amic acid) intermediate, 297f PTFPMS, 295, 295f PTFPMS 1100K, 295–296 PTFPMS 20K, 295–296 PTFPMS/PEI composite membrane, 296f thin polymer films, 295 materials, 271 in pervaporation application, 299 co-polyimide used for pervaporation, 302f permeation flux and permeation selectivity, 301, 301f SIDA-rich polyimides, 300 TCE, 300 polyimides, 286, 287f fluorosilicon block copolyimides, 289–291 fluorosilicon graft copolyimides, 291–292 fluorosilicon random copolyimides, 286–289 polysiloxane component, 286 in special application, 308–310 synthesis with long chain fluoroalkyloxypropyl group substitution, 277f urethanes, 279–280 CTHFA-PDMS graft-modified DGEBA, 281–283, 283f fluorinated siloxane star-like copolymer, 281–283 Vi-PFSi copolymer, 280–281, 282f 4FMA. See α,α-bis(4-amino-3,5- difluorophenyl)phenylmethane Fourier transform infrared spectroscopy, 170–171 FPPE. See Fluorinated poly(phthalazinone ether) Fractional free volume (FFV), 41–42, 106–107, 191–192, 251 Free volume (FV), 238–239 fractions, 103–105 FSR. See Fluorosilicone rubber Fuel cell, 153f FV. See Free volume G Gas diffusion coefficients, 298t Gas permeability, 188, 208 coefficients, 298t of PI-POSS nanocomposite membranes, 297t of polyamides, 209t–211t, 213t–216t Gas separation fluorinated polyimides, 127 gas transport mechanism, 128–129, 128f physical properties, 130–146 terminology in gas transport, 129–130 membrane-based, 128f Gas separation application fluorinated heterocyclic polymers, 250 PBI and gas transport properties, 251–253 PBI derivatives, 252f polybenzoxazoles and gas transport properties, 253–257 fluorinated PAEs, 41–42 aliphatic chain, 53–54 cardo cyclo aliphatic moiety, 53 –CF3-containing PAE, 42 CO2–CH4 selectivity vs. CO2 permeability coefficients, 54f gas permeation studies, 42 gas separations properties, 50–51 gas transport properties, 42, 50–51 meta-linked polymers, 51–52 O2–N2 selectivity vs. O2 permeability coefficients, 54f PAEs gas permeability coefficients and permselectivities values, 43t–49t 6F group-containing polymer, 50 fluorinated polyamides, 208 aromatic glassy polymers, 208 gas permeability coefficients, 209t–211t, 213t–216t gas transport properties, 210 packing disruptive groups, 212 pendent–CF3 groups, 209 TPA, 212–214 upper bound, 217 Gas transport mechanism fluorinated and non-fluorinated polyimide membranes, 131t ideal gas separation properties for CO2–CH4 gas pair, 142t–143t for O2–N2 gas pair, 140t–141t through membrane, 128–129, 128f permeability coefficient, 129 properties of fluorinated polyimides, 130 asymmetric polyimide membrane, 130–131 copolyimides reaction scheme, 137f DABA-containing copolyimides, 135f 6FDA-based polyimides, 132–133, 134t 6FDA-TMPDA/DAT copolyimides, 137t 6FDA-TMPDA/DAT polyimides, 138t 6FDA–APPS, 132 mixed gas separation, 133–134 poly(ether imide) series, 144f polyimides containing TPA-moiety, 139f polyimides with or without fluorinated side groups, 131f sulfonic acid groups, 134–135324 Index Gel permeation chromatography (GPC), 14–15, 292 Glass transition temperature (Tg), 229 GPC. See Gel permeation chromatography H HA. See Humic acid hb polymers. See Hyperbranched polymers HBPBI. See Hyperbranched polybenzimidazole (HPBI) 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11- heptadecafluoroundecylmethylsiloxane(–C8F17CH2CH2CH2(CH3) SiO) (HDFUSiO), 274 2,2,3,3,4,4,4-heptafluorobutyl methacrylate (HFBMA), 274–275 Hexafluorobenzene (HFB), 70–71, 263 4,4′-[(1,2,3,3,4,4-hexafluorocyclobutane- 1,2-diyl) bis(oxy)]dibenzoic acid (PFCB diacid), 231 Hexafluoroisopropylidene (6F), 1–2 hyperconjugative effect, 5f 4,4′-hexafluoroisopropylidene diphthalic anhydride (6FDA), 151, 229 4,4′-(hexafluoroisopropylidene) dianiline (HFA), 221–222 4,4′-(hexafluoroisopropylidene) dibenzoic acid (HFA), 229–230, 236 4,4′-(hexafluoroisopropylidene) diphenol (6F-BPA), 15 4,4′-(hexafluoroisopropylidene) diphthalic anhydride (6-FDA), 138–145, 257–258, 286–287 4,4′-(hexafluoroisopropylidene)bis(oaminophenol) (6FAP), 246–247 Hexafluoropropane (6FAP), 130–131, 250 Hexafluoropropane dianhydride (6FDA), 105–106, 125 Hexamethylphosphoramide (HMPA), 189 HFB. See Hexafluorobenzene High-performance polymers. See Aromatic polyamides High-temperature phosphorylation polycondensation, 190 HMPA. See Hexamethylphosphoramide Homopolymers, 16 HPA. See Hydroxyl polyamides HPBI. See Hyperbranched polybenzimidazole HPEI. See Poly(o-hydroxy imide) Humic acid (HA), 309–310 Hxf-T. See Poly(3,3,4,4,5,5,6,6,6- nonafluoro hexylsilsesquioxane) Hydrated proton (H3O+), 155 Hydrophobic homopolymers biphenyl perfluorocyclobutyl (BP-PFCB), 305 Hydroxyl polyamides (HPA), 243 2-hydroxyethyl methacrylate (HEMA), 280–281 3,3′-bis(4-hydroxyphenyl)-1-isobenzopyrrolidone (HPP), 76 4-(4′-hydroxyphenyl)phthalazin- 1(2H)-one (DHPZ), 30–31 o-hydroxypolyamide (HPA), 257 o-hydroxypolyimide (HPI), 255–256 2-hydroxypropyl acrylate (HpA), 285 Hyperbranched polybenzimidazole (HPBI), 229, 234–235 Hyperbranched polymers (hb polymers), 32 hb PAE synthesis, 33f physical properties, 38t I IC. See Integrated circuit; Isophthaloyl chloride Ideal separation factor, 130 IEC. See Ion exchange capacity IGA. See Isothermal gravimetric analysis ILD. See Interlayer dielectrics IMD. See Intermetal dielectrics Indene moiety, 191f Inherent viscosity (IV), 230 Integrated circuit (IC), 102–103 Interlayer dielectrics (ILD), 107 Intermediate membrane PBI (iPBI), 229 Intermetal dielectrics (IMD), 107 layers, 102–103 Ion exchange capacity (IEC), 56, 155–156, 221, 263–264, 303f IPA. See Isophthalic diacids iPBI. See intermediate membrane PBI IPC. See Isophthaloyl dichloride (3-isocyanatopropyl) triethoxysilane (ICTES), 237–238 Isophthalic diacids (IPA), 221–222 Isophthaloyl chloride (IC), 245–246 Isophthaloyl dichloride (IPC), 189 Isothermal gravimetric analysis (IGA), 291–292 IV. See Inherent viscosity K Kevlar, 187–188 Ketone moiety, 206f Kinked backbone, 205f Knudsen diffusion, 128 L Linear graft (LG), 303 Linear sulfonated poly(ether ether ketone) (L-SPEEK), 82–83 Liquid-crystalline elastomers (LCEs), 278–279, 279f Low temperature solution polycondensation, 189–190, 189f Low water absorption, 105–106 Mm -MMT. See Montmorillonite MMT m-phenylene diamine (MPD), 97–98, 189 MA. See Methacrylic acid Macromonomer, 79–81 MAM block copolymer. See Poly(methyl methacrylate-butyl acrylate-methyl methacrylate) block copolymer Mass transport in pervaporation, 148–149 Membrane electrode assembly (MEA), 152–153 Membrane preparation, 259 Membrane technologies, 125–127. See also Fluorinated polyimides Meta-aramid, 187 Methacrylic acid (MA), 284 Methanesulfonic acid (CH3SO3H), 227 Methanol (MeOH), 54–55 Methyl methacrylate (MMA), 284 Methyl tert-butyl ether (MTBE), 54–55 4,4′-methylene diamine (MDA), 150–151 Methylfluorosilicone rubber (MFSR), 278 Methylsilicone rubber (MSR), 278 MFSR. See Methylfluorosilicone rubber Microwave (MW), 190 MMA. See Methyl methacrylate Molecular weight (MW), 236 Montmorillonite MMT (m-MMT), 239 MPD. See m-phenylene diamine MSR. See Methylsilicone rubber MTBE. See Methyl tert-butyl ether MW. See Microwave; Molecular weight NN -methyl-2-pyrrolidone (NMP), 12, 188, 206, 229, 287–288 Na+-Montotrillonite (Na+-Mont), 239 Nafion, 301–302 Nanofiltration membrane (NF membrane), 309 1,5-naphthalene diamine (NDA), 151–152 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA), 158 Naphthyl-imido moiety, 25–27 Near-infrared (Near-IR wavelengths), 105 Near-IR wavelengths. See Near-infrared NF membrane. See Nanofiltration membrane NIPAAm. See Poly(N-isopropylacrylamide) NLO. See Nonlinear optical NMP. See N-methyl-2-pyrrolidone NMR. See Nuclear magnetic resonance 3,3,4,4,5,5,6,6,6-nonafluorohexyl groups (C4F9CH2CH2–FLS), 275–276 Nonlinear optical (NLO), 105–106 Nuclear magnetic resonance (NMR), 22, 274–275, 287–288Index 325 Nucleophile (Nu–), 4–5 Nucleophilic aromatic substitution reaction (SNAr), 32 Nucleophilic displacement, 12–13 polymerization reaction, 12 O Octa(aminophenyl)silsesquioxane (OAPS), 294–295 One-step polymerization, 98 Open circuit voltage (OCV), 62 Optical textures of monomers, 279, 280f Optical transparency, 188, 207–208 Organic solvents, 291–292 Organo-soluble polymer, 1–2 1,1′-oxybis(4-carbonyl chloride benzene) (ODB), 245 4,4′-oxydianiline (ODA), 125, 221, 290–291 4,4′-oxydiphthalic anhydride (ODPA), 144–145, 287–288 Pp -phenylenediamine (PPD), 189 PA. See Phosphoric acid; Phthalimidine PAAc. See Poly(amino amic acid) PAE. See Poly(arylene ether) PAEPO. See Poly(arylene ether phosphine oxide) PAFC. See Phosphoric acid fuel cell PAHA. See Polyhydroxyamide (PHA) PAI. See Polyaminoimide PAs. See Polyamides PBI. See Polybenzimidazole PBO. See Polybenzoxazole PBPO1. See Poly(biphenylene oxide) PBT. See Polybenzothiazole PDI. See Polydispersity index PDMS. See Poly(dimethylsiloxane); Polydimethylsiloxane PDMS-b-PHFBMA. See Poly(dimethylsiloxane)- block-poly(2,2,3,3,4,4,4- heptafluorobutyl methacrylate) PDMS-b-PHFBMA-b-PS triblock copolymers. See Poly(dimethylsiloxane)- b-poly(2,2,3,3,4,4,4- heptafluorobutyl) methacrylate-b-poly(styrene) triblock copolymers PDMS-b-PMMA-b-PHFBMA triblock copolymer. See Poly(dimethylsiloxane)-blockpoly(methyl methacrylate)-blockpoly(2,2,3,3,4,4,4-heptafluorobutyl methacrylate) triblock copolymers PEEK. See Poly(ether ether ketone) PEES. See Poly(ether ether sulfone) PEI membranes. See Poly(ether imide) membranes PEK. See Poly(aryl ether ketone) PEK-C. See Cardo poly(aryl ether ketone) PEM. See Proton exchange membrane PEMFC. See Polymer electrolyte membrane fuel cell; Proton exchange membrane fuel cell 4-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoyloxy)phenyl 4-(undec-10-enoyloxy)benzoate (PPUB), 278–279 2-(perfluoro-(1,1-bis-isopropyl)-2- propenyl)oxyethyl methacrylate (POMA), 284 1,1,6H,6H-perfluoro-1, 6-hexanediol (6CF-diol), 40 Perfluoroalkyl group in aromatic nucleophilic displacement reaction, 6, 6f on chemical reactivity, 4–6 Perfluoroazelaic acid (PFAA), 230–231 Perfluorocyclobutane-PBIs (PFCB–PBI), 231 Perfluorocyclobutyl aryl ethers (PFCB aryl ethers), 293 chemical, thermal, and oxidative stability, 294–295 polymer architecture functionalized with POSS, 295f TFVE monomer, 293 aryl TFVE dimethylchlorosilane condensation, 294 thermal [2 + 2] cyclodimerization, 294f Perfluorocyclobutyl polymer thin-film composite membranes (PFCB polymer thin-film composite membranes), 295 Perfluoropolymers, 2 Perfluoroterephthalic acid (PFTA), 230–231 2-(perfluorohexyl)ethyl-3,5-diamino benzoate (PFDAB), 130, 299 Permeability coefficient, 129 Permselectivities, 297t Pervaporation (PV), 41, 146, 146f, 188 fluorinated heterocyclic polymers, 257–258 PES. See Poly(arylene ether sulfone) PES-C. See Poly(aryl ether sulfone) with cardo moiety PFA macromonomer (PFAM), 283 PFA-b-PSiMAs. See Poly(perfluoroalkylethyl acrylate)- b-poly(3-[tris(trimethylsilyloxy)- silyl] propyl methacrylates) PFAA. See Perfluoroazelaic acid PFAM. See PFA macromonomer PFAM initiator (PFAMI), 283 PFCB aryl ethers. See Perfluorocyclobutyl aryl ethers PFCB polymer thin-film composite membranes. See Perfluorocyclobutyl polymer thin-film composite membranes PFCB–PBI. See Perfluorocyclobutane-PBIs PFHEA-b-PGMA. See Poly[2(perfluorohexyl)ethyl acrylate]-blockpoly(glycidyl methacrylate) PFHEA-b-PIPSMA. See Poly[2- (perfluorohexyl)ethyl acrylate]- block-poly[(tri-isopropyloxysilyl) propyl methacrylate] PFTA. See Perfluoroterephthalic acid PHA. See Polyhydroxyamide PHAA. See Poly(o-hydroxy amic acid) PHDFDMS. See Poly(1-,1-,2H, 2H-heptadecafluorodecyl)- methylsiloxyne Phenyl phosphine oxide moiety, 28–29 Phenylene ether moiety, 73 1,4-phenylene diisocyanate (1,4-PDI), 237–238 PHMS. See Poly(hydromethylsiloxane) Phosphoric acid (PA), 229 Phosphoric acid fuel cell (PAFC), 56 Phosphorus pentoxide/methanesulfonic acid (PPMA), 241 Phosphorylation method, 190f Phthalazinone moiety, 30–32 Phthalimidine (PA), 66 fluorinated PAEs with phthalimidine moiety, 25 PI. See Polyimide PIS membranes. See Poly(imide-siloxane) membranes PMDA. See Benzene-1,2,4,5-tetracarboxylic dianhydride PMDA/ODA. See Pyromellitic dianhydride/oxydianiline PMNFHS. See Poly(methyl- (3,3,4,4,5,5,6,6,6-nonafluorohexyl) siloxane) PMPI. See Poly(m-phenylene isophtalamide) PNFHMS. See Poly(3,3,4,4,5,5,6,6,6- nonafluorohexylmethylsiloxane) Polarized ATR Fourier transform infrared spectroscopy, 170–171 Polarized optical microscopy (POM), 279 Poly(1-,1-,2H,2H-heptadecafluorodecyl)- methylsiloxyne (PHDFDMS), 273–274326 Index Poly(2,2′-tetradecafluoroheptylene-5,5′- bibenzimidazole) (14F-PBI), 230–231 Poly(2,6-dimethyl phenylene oxide), polyphenylene oxide (PPO), 12, 16 Poly(3,3,3-trifluoropropyl methylsiloxane) (PTFPMS), 271–272 repeat unit structure, 272f Poly(3,3,3-trifluoropropylsilsesquioxane) (Prf-T), 273–274 Poly(3,3,4,4,5,5,6,6,6-nonafluoro hexylsilsesquioxane) (Hxf-T), 273–274 Poly(3,3,4,4,5,5,6,6,6-nonafluorohexylmethylsiloxane) (PNFHMS), 273 Poly(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctylmethylsiloxane) (PTDFOMS), 273 Poly(amic acid), 98–99 chemical imidization, 100, 102f polymer optical waveguides, 105 reaction pathway, 99f Poly(amino amic acid) (PAAc), 229, 232–233 Poly(aryl ether ketone) (PEK), 51 Poly(aryl ether sulfone) with cardo moiety (PES-C), 54–55 Poly(arylene ether phosphine oxide) (PAEPO), 28–29 Poly(arylene ether sulfone) (PES), 83–84, 84f Poly(arylene ether triphenylamine), 17 synthesized by–CF3-activated nitrodisplacement reaction, 17f Poly(arylene ether) (PAE), 11–12, 85, 85f. See also Fluorinated poly(arylene ether) (Fluorinated PAE) for gas separation application, 12 nucleophilic displacement polymerization reaction, 12 polymerization by–CF3-activated fluorine displacement reaction, 13 fluoro-and nitro-displacement reaction, 18 nitro-displacement reaction, 13–18 properties of–CF3-substituted, 20t–21t, 23t–25t, 28t–30t SNAr mechanism, 13f synthesis, characterization, and properties, 12 synthesis by perfluoro-activated fluoro displacement reaction, 13f Poly(biphenylene oxide) (PBPO1), 14–15, 15f Poly(dimethylsiloxane)-blockpoly(methyl methacrylate)-blockpoly(2,2,3,3,4,4,4-heptafluorobutyl methacrylate) triblock copolymers (PDMS-b-PMMA-bPHFBMA triblock copolymer), 275, 276f, 284 Poly(dimethylsiloxane) (PDMS), 271–273 Poly(dimethylsiloxane)-bpoly(2,2,3,3,4,4,4- heptafluorobutyl) methacrylate-b-poly(styrene) triblock copolymers (PDMSb-PHFBMA-b-PS triblock copolymers), 283, 284f Poly(dimethylsiloxane)-blockpoly(2,2,3,3,4,4,4-heptafluorobutyl methacrylate) (PDMS-b-PHFBMA), 274–275, 275f Poly(ether ether ketone) (PEEK), 85 Poly(ether ether sulfone) (PEES), 85 Poly(ether imide) membranes (PEI membranes), 295 Poly(hydromethylsiloxane) (PHMS), 273–274 Poly(imide-siloxane) membranes (PIS membranes), 287–288, 297–298 effect of percent PIS, 299f permselectivity, 299f physical and pervaporation properties, 302t Polymerization, 32 Poly(methyl methacrylate-butyl acrylate-methyl methacrylate) block copolymer (MAM block copolymer), 301–302 Poly(methyl-(3,3,4,4,5,5,6,6,6-nonafluorohexyl) siloxane) (PMNFHS), 273–274 Poly(methylsiloxane-cofluorosiloxane), 278 Poly(m-phenylene isophthalamide) (PMPI), 187–188, 188f Poly(N-isopropylacrylamide) (NIPAAm), 150, 150f Poly(o-hydroxy amic acid) (PHAA), 242 Poly(o-hydroxy amides), 242–243 Poly(o-hydroxy imide) (HPEI), 248 Poly(p-phenylene terephtalamide) (PPPT), 187–188, 188f Poly(perfluoroalkylethyl acrylate)-bpoly(3-[tris(trimethylsilyloxy)- silyl] propyl methacrylates) (PFA-b-PSiMAs), 283 Poly(phenylene ether), 85f Poly(styrene sulfonic acid)-grafted poly(ethylene-cotetrafluoroethylene)polymer electrolyte membrane (ETFE-PEM), 307 Poly(tetrafluoroethylene-co-vinyl acetateco-vinyl alcohol) (PTFE-co-VAcco-VA), 279–280 Poly(tetrafluoroethylene) (PTFE), 292–293 chemical structures, 294t repeat unit structure, 293f synthesis from C2F4 monomers, 293 uses in membrane processes, 293 Poly(vinylidene fluoride)-g-poly(styrene sulfonic acid) copolymers, 304f Poly[2-(perfluorohexyl)ethyl acrylate]- block-poly[(tri-isopropyloxysilyl) propyl methacrylate] (PFHEA-bPIPSMA), 308, 309f Poly[2,2′-[2,2′-bis(trifluoromethyl)- 4,4′-biphenylene]-5,5′- bibenzimidazole] (BTBP), 232 Poly[2(perfluorohexyl)ethyl acrylate]- blockpoly(glycidyl methacrylate) (PFHEA-b-PGMA), 308, 309f Polyamic acid, 99 chemical imidization, 100–106, 102f thermal imidization, 99–100, 101f Polyamides (PAs), 187–188, 220–222. See also Fluorinated polyamides from 3FPC and 6FPC, 201f catenation angle variation in aromatic, 196f containing adamantane substituted TPA, 216f phosphorylation method, 190f physical properties of, 194t–195t, 197t PPPT and PMPI, 188f structural variation, 196f structure and properties, 190–191 fluorinated poly(ether amide sulfone) s, 207–208 fluorinated poly(ether amide)s, 191–207 synthesis, characterization and properties, 189 high-temperature phosphorylation polycondensation, 190 low temperature solution polycondensation, 189–190, 189f Polyaminoimide (PAI), 229 Polyazoles, 227, 228f. See also Polybenzazoles Polybenzazoles fluorinated PBI, 228–240 PBOs, 240–248 PBTs, 248–250 synthesis, characterization, and properties, 228 Polybenzimidazole (PBI), 227. See also Fluorinated PBI PA doped, 259f as PEMs membrane preparation, 259 PA doping of membrane, 259 proton conductivity, 259–262 pyridine, 236f Polybenzimidazolimide (PPL), 232–233 Polybenzothiazole (PBT), 227 as PEMs, 263–264Index 327 Polybenzoxazole (PBO), 227, 247f. See also Fluorinated PBO as PEMs, 263 Polydimethylsiloxane (PDMS), 279–280 Polydispersity index (PDI), 161, 274–275 Polyhydroxyamide (PHA), 240–241, 246–248 Polyimides (PI), 97, 125–127, 152–171. See also Fluorinated polyimides block copolymer aerogels, 125, 126f –CF3-based aromatic, 98 synthesis, characterization, and properties, 98, 98f polyimide block copolymer aerogels, 125, 126f Polyimide-POSS nanocomposite membranes (PI-POSS nanocomposite membranes), 296–297, 297t–298t Polymer electrolyte membrane fuel cell (PEMFC), 56, 154, 220–221 Polyphosphoric acid (PPA), 228–229, 241 Polypyrrolone (PPL), 229, 232–233 Polysulfone (PSF), 50–51 Polyvinylidene fluoride (PVDF), 283 POM. See Polarized optical microscopy Pore-flow model, 148, 148f Potassium 1,1,2,2-tetrafluoro-2-(1,1,2,2- tetrafluoro-2- iodoethoxy)ethanesulfonate (PSA-K), 83–84 Potassium carbonate (K2CO3), 18–19 PPA. See Polyphosphoric acid PPD. See p-phenylenediamine PPL. See Polybenzimidazolimide; Polypyrrolone PPMA. See Phosphorus pentoxide/ methanesulfonic acid PPO. See Poly(2,6-dimethyl phenylene oxide), polyphenylene oxide PPPT. See Poly(p-phenylene terephtalamide) Pressure swing adsorption (PSA), 208 Prf-T. See Poly(3,3,3-trifluoropropylsilsesquioxane) Proton conductivity, 75, 259–262 Proton exchange membrane (PEM), 41, 125–127, 220–221, 227, 301–302 fluorinated heterocyclic polymers as, 258–259 fluorinated sulfonated PAEs, 56–87 fluoropolymers, 301–302 blends of hydrophilic and hydrophobic PFCB polymers, 305 ETFE-PEMs, 307 LG and AG membranes, 303–304 proton conductivity, 303f PVDF and SEBS thermoplastic elastomer, 301–302 RH of PVDF graft copolymer membranes, 304f sBP-PFCB, 305, 306f sBP-PFCB/SO2-PFCB, 305–306 side-chain sulfonated PFCB ionomer, 306, 307f sPEEK, 304–305 SPFS-X, 307–308, 308f PBI as membrane preparation, 259 PA doping of membrane, 259 proton conductivity, 259–262 PBO as, 263 PBT as, 263–264 proton conduction mechanism, 154–155 Proton exchange membrane fuel cell (PEMFC), 125–127, 41, 56, 258–2595, 301–302 Proton transport, 154f–155f PSA. See Pressure swing adsorption PSA-K. See Potassium 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2- iodoethoxy)ethanesulfonate PSF. See Polysulfone PSI. See PV separation index PTDFOMS. See Poly(3,3,4,4,5,5,6,6,7,7,8,8,8- tridecafluorooctylmethylsiloxane) PTFE. See Poly(tetrafluoroethylene) PTFE-co-VAc-co-VA. See Poly(tetrafluoroethylene-co-vinyl acetate-co-vinyl alcohol) PTFPMS. See Poly(3,3,3-trifluoropropyl methylsiloxane) PV. See Pervaporation PV separation index (PSI), 218–220 PVDF. See Polyvinylidene fluoride Py-PBI. See Pyridine bridge polybenzimidazole Pyridine bridge polybenzimidazole (Py-PBI), 236 Pyridinylidene moiety, 19–22 Pyromellitic dianhydride/oxydianiline (PMDA/ODA), 102–103 Q Quadriphenyl moiety, 19–22 Quadriphenyldiamine (QA), 160 Quarternized poly(arylene ether sulfone) (QPES), 55, 55f R Relative humidity (RH), 304–305 Repeat unit (RU), 260 Reversible additionfragmentation chain transfer (RAFT), 283 S sBP-PFCB with SO2-PFCB (sBP-PFCB/ SO2-PFCB), 305 Scanning electron microscopy (SEM), 39, 150–151, 236 SCBP. See Sulfonated dicarboxylic acid, 3,3′-Disulfonate-4,4′- dicarboxylbiphenyl SEBS. See Styrene-(ethylene-butylene)- styrene block copolymer Selectivity, 130 SEM. See Scanning electron microscopy Semifluorinated polymers, 7. See also Fluorine effect Separation, 148 Separation factor, 130 Separation technologies, 147–148 SFBDH, 285–286 SIDA. See Bis(3-aminopropyl)-terminated poly(dimethylsiloxane) Silicon, 272 Silicon dioxide (SiO2), 102–103 Silylation-polymerization, 189 SO2-PFCB. See Sulfonyl-bridged biphenyl perfluorocyclobutyl Sol–gel process, 237–238 Solubility coefficient, 129–130, 298t selectivity, 130, 298t Solution polymerization, 228–229 Solution–diffusion mechanism, 127–129, 208–209 model, 148, 148f SPA. See Sulfonated polyamide SPAE. See Sulfonated poly(arylene ether sulfone) SPAEK-6F. See Sulfonated fluorinated poly(aryl ether ketone) SPAEKBO-XX. See Sulfonated poly(benzoxazole ether ketone) sPBTs. See Sulfonated PBTs SPEA. See Sulfonated poly(ether amide) sPEEK. See Sulfonated poly(ether ether ketone) SPEEKK. See Sulfonated poly(aryl ether ether ketone ketone) SPES-C. See Sulfonated poly(aryl ether sulfone)with cardo moiety SPFS-X. See Sulfonated poly(fluoreneco-sulfone) ethers SPI. See Sulfonated polyimides SPMA. See Sulfopropyl methacrylate SPP-co-PAEK. See Sulfonated fluorinated poly(p-phenylene-co-aryl ether ketone) SPTESBO-XX. See Sulfonated poly(benzoxazole thioether sulfone) STA. See Sulfonated terephthalic acid Styrene-(ethylene-butylene)-styrene block copolymer (SEBS), 301–302328 Index Sulfonated dicarboxylic acid, 3,3′-Disulfonate-4,4′- dicarboxylbiphenyl (SCBP), 250 Sulfonated fluorinated block PAEs, 70 BPSH-6FK multiblock copolymers, 71f chain extender, 71–72 sulfonated fluorinated multiblock copolymers, 71f Sulfonated fluorinated PAEs branched PAEs, 81–83 comb-shaped, 78–79, 80f densely sulfonated fluorinated PAEs, 81, 81f macromonomer, 79–81 with side chain, 80f with side chain grafting, 74, 75f atomic force microscopy, 77–78 HPPQSH-30 PS copolymer proton conductivity, 78 HPPQSH-XX preparation, 76 HPPQSH-XX PS copolymers, 76–77, 76f proton conductivity, 75 protonic cross-linking in acid-form grafted copolymers, 77f sulfonated copolymers, 74–75 synthesis of copolymers, 82f Sulfonated fluorinated poly(aryl ether ketone) (SPAEK-6F), 57–58, 57f with cross-linking alkyne moiety, 60f with pendent phenyl rings, 61f Sulfonated fluorinated poly(arylene ether), 58f Sulfonated fluorinated poly(p-phenyleneco-aryl ether ketone) (SPP-coPAEK), 62, 62f fuel cell performance, 63f stress-strain curves, 63f Sulfonated fluorinated random PAEs, 57–70 BPAQSH-XX oxidative stability, 64–66 –CF3 groups, 58 6FBPAQSH-XX copolymer membranes, 69–70 membranes thermal stability, 60–61 by post-sulfonation, 61–62 proton conductivity and WU, 61 SPAEK-6F, 57–58, 57f SPEEKK, 58–60 SPP-co-PAEK copolymer in proton form, 62, 62f sulfonated membranes, 66–67 sulfonated polymers, 64 synthesized sulfonated fluorinated poly(arylene ether)s, 65t Sulfonated PBTs (sPBTs), 250 Sulfonated poly(aryl ether ether ketone ketone) (SPEEKK), 58–59 Sulfonated poly(aryl ether sulfone)with cardo moiety (SPES-C), 54–55 Sulfonated poly(arylene ether sulfone) (SPAE), 74 Sulfonated poly(benzoxazole ether ketone) (SPAEKBO-XX), 263 Sulfonated poly(benzoxazole thioether sulfone) (SPTESBO-XX), 263 Sulfonated poly(biphenylsulfone ketone) block copolymers, 70f Sulfonated poly(ether amide) (SPEA), 221 Sulfonated poly(ether ether ketone) (sPEEK), 304–305 Sulfonated poly(fluorene-co-sulfone) ethers (SPFS-X), 307–308, 308f Sulfonated poly(phthalazinone ether ketone), 60f Sulfonated polyamide (SPA), 208 for PEM, 222f Sulfonated polyimides (SPI), 153–154. See also Fluorinated sulfonated polyimides as PEMs Sulfonated terephthalic acid (STA), 221 Sulfonyl (SO2), 210 Sulfonyl-bridged biphenyl perfluorocyclobutyl (SO2-PFCB), 305 Sulfopropyl methacrylate (SPMA), 283 Sulfuric acid (H2SO4), 227 T TA. See Terephthalic acid TCE. See Trichloroethylene TDI. See Toluene 2,4- diisocyanate TEM. See Transmission electron microscopy TEOS. See Tetraethoxysilane Terephthaldehyde (TPA), 234–235 Terephthalic acid (TA), 221 Terphenyl moiety, 19–22 Tetraamine, 229 Tetraethoxysilane (TEOS), 237 3,3′,5,5′-tetrafluoro-4,4′- diaminodiphenylmethane (TFDAM), 124 Tetrafluoroethylene (TFE), 279–280 Tetrafluoroethylene monomers (C2F4 monomers), 293 Tetrahedral copper–cyano complex (Na3[Cu(CN)4]), 232 Tetrahydrofuran (THF), 200–201, 206, 272–273, 286–287 2,3,5,6-tetramethyl-1, 4-phenylene diamine (4MPD), 151 TFE. See Tetrafluoroethylene TFVE monomer. See Trifluorovinyl ether monomer TGA. See Thermogravimetric analysis Thermal imidization, 99–100, 101f Thermal stability, 97–98 Thermally rearranged PBI membrane (TR-PBI membrane), 229 Thermally rearranged PBO membrane (TR-PBO membrane), 253 Thermally rearranged polymer, 229 Thermogravimetric analysis (TGA), 274 THF. See Tetrahydrofuran Thin polymer films, 295 4,4′-thiobisbenzenethiol (TBBT), 263 Thioether moiety, 29–30 Thiophenylidene moiety, 19–22 TMC. See Total monomer concentration Toluene 2,4- diisocyanate (TDI), 280–281 Total monomer concentration (TMC), 236 TPA. See Terephthaldehyde; Triphenylamine TPP. See Triphenyl phosphate TR poly(benzoxazole-co-imide) (XTR-PBOI), 254 TR-PBI membrane. See Thermally rearranged PBI membrane TR-PBO membrane. See Thermally rearranged PBO membrane Transmission electron microscopy (TEM), 55–56 micrographs, 69 1,3,5-triaminophenoxybenzene (TAB), 125 Triblock membranes, 73–74 Trichloro-3,3,4,4,5,5,6,6,6-nonafluorohexylsilane (C4F9C2H4SiCl3), 273–274 Trichloro-3,3,3-trifluoropropylsilane (CF3CH2CH2SiCl3), 273–274 2,4′,6-trifluoro-benzophenone (TFBP), 81 Trichloroethylene (TCE), 299–300 4,4′-(2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethylidene)diphthalic anhydride (TFDA), 115–116 9,10-bis[3′-trifluoromethyl-4′ (4″- aminobenzoxy)benzyl] anthracene (TFAA), 288–289 4,4′-bis(3″-trifluoromethyl-paminobiphenyl ether)biphenyl (TFBB), 292 1-(3′,5′-bis[trifluoromethyl]-phenyl) pyromellitic dianhydride (6FPPMDA), 116 Trifluoromethyl groups (–CF3 groups), 1–2, 127, 286–288 polymerization by–CF3-activated fluorine displacement reaction, 13 fluoro-and nitro-displacement reaction, 18 polymerization by–CF3-activated nitrodisplacement reaction, 13 copolymerization precipitation, 16–17 crystalline characteristics, 17Index 329 DSC, 17 electron-donating amine, 17–18 nitro displacement activation, 16 poly(biphenylene oxide)s, 14–15 synthetic scheme for PBPO, 15 5-(4-trifluoromethylphenoxy)isophthaloyl dichloride (3FPC), 201–202 2-(4-trifluoromethylphenoxy)terephthaloyl chloride (TFTPC), 191 4,4′-(trifluoromethylphenylisopropylidene) diphenol (3FBPA), 39–40 3,3,3-trifluoropropyl group (TFP group), 272, 277–278 Trifluorovinyl ether monomer (TFVE monomer), 293 1,4-bis[3′-trifluromethyl-4′(4″- aminobenzoxy)benzyl]benzene (BATP), 138–144 2,4,6-trimethyl-1,3-phenylenediamine (TMPDA), 135–136 Triphenyl phosphate (TPP), 190, 229 Triphenylamine (TPA), 136–138, 212–214 Two-phase process, 189 Two-step polymerization, 98–106 electron affinity values for anhydrides, 100t rate constants for imidization, 99 U Ultem, 97–98 Ultraviolet (UV), 101–102 (3R,3aR,6S,6aR)-6-(undec-10-enoyloxy) hexahydrofuro[3, 2-b]furan-3- yl-4′-(4-(allyloxy) benzoyloxy) biphenyl-4-carboxylate (UHAB), 278–279 Urethane graft-co- (septadecafluorodecylacrylate)- tris(trimetylsiloxy silylpropyl acrylate) copolymers, 279–280, 281f V Vehicular mechanism of proton transport, 155, 155f Vinyl-terminated fluorinated siloxane copolymer (Vi-PFSi copolymer), 280–281 Volatile organic compound (VOC), 146, 299 W Water contact angle (WCA), 308 Water uptake (WU), 56, 68, 68f Wide-angle X-ray diffraction (WAXD), 17, 236, 239 X X-ray photoelectron spectroscopy (XPS), 280–281 XTR-PBOI. See TR poly(benzoxazole-co-imide)
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