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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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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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