INDEX

Acetic anhydride Acrylic acid cyclodehydration agent, 220 biomer activity, 309 Acetoamides Acrylonitrile synthesis, 277 purification, 409 Acetone sodium naphthalene polymerized, polyanhydride solvent, 193 410 Acetone cyanohydrin N-Acryloyl-a-aminoisobutyrate azlactone raw material, 225 synthesis, 225 a-Acetoxypropionic acid N-Acryloylmethylalanine ring closure to lactone, 443 ethyl chloroformate reaction, 206 Acetyl acetone, 464 Activation energy manganese decarbonyl coordi• styrene anoinic dispersion nating agent, 300 polymerization, 392, 296 Acetyl chloride a-Acylamino-a-aminopropionic acid coumalic acid reaction, 61 conversion to a-lactone, 445 polystyrene living particle N-Acylurea, 307 reaction, 400 Adhesives, hot melt Acetylene carbonyls synthesis concept, 480 condensations, 276 Adipic acid, 192 Acrolein Adipic acid, metal salts formation, 62, 74 phosphorus acid chloride Acrylamide condensation, 195 hydrophilic grafts on , 293 anionic polymerization, 322 functionalized oligomers, 205, 211, 215-217 triazolinedione ene reaction, 2 ORTEP plots, 212 Alkenyl azalactone purification, 308 amine oligomer reaction, 208, telechelic oligomers, 203 210, 211 Acrylamides, bis type 2-Alkenyl-2-oxazoline-5-ones amine reaction, 215 amine reactions, 205, 211 Acrylamides, telechelic Alkoxides characterization, 208 catalyst for oxazolidone synthesis from azlactones, formation, 252 219, 221 Alkoxides, polymeric Acrylates, oxide polymerization, anionic polymerization, 327 330 alkali metal alkoxides Alkyl polymerization, 327 cycloaddition reaction, 1 group transfer polymerization, Alkyllithium 327 anionic polymerization initiator, Acrylates, perfluoroalkyl 335 methacryloyl polystyrene Alkyllithium, anionic initiators macromer copolymerization, copolymerization reactivity 463 ratios, 335

517 Allyl chloride Azlactones N-(2-hydroxyethyl) alkenyl oligomers, 203 reaction, 240 amine oligomer reactions, 203 Allyltrimethylsilane triazoline• amine reactions, 217, 219 dione reaction, 2 bis-thio reaction, 225 Aluminum chloride n-butylamine reaction, 231 -sulfur reaction 2-cyanoethyl methylamine catalyst, 176 reaction, 231 Friedel-Crafts catalysts, mercaptan reactions, 219 159-162, 164, 166, 167 nucleophilic attack, 231 Aluminum trichloride ring-opening, zwitterionic S-propiolactone polymerization reaction, 205 catalyst, 450, 451 synthesis, 225 , N-halo derivative Azlactones, alkenyl polymer halogenation agents, 295 amine oligomer reaction, 221 1, 2-ethanediol addition reaction, acetylene carbonyl reaction, 276 221, 222 1, 3-dicarbonyl reaction, 276 ethylene-bis (3-mercaptopro- Amines, primary pionate) reaction, 221 benzoxazine synthesis, 27, 28, Jeffamine reaction, 229, 230 48 Michael addition reaction, 229 Amines, titration Mercaptan reaction, 229 perchloric acid/glacial acetic Nucleophilic reactions, 219, 232 acid method, 206, 207, 208 polymerization reactions, 232 Amino acids polythiol reaction, 223, 224 alkaloids preparation, 425 synthesis procedure, 221 diacid chloride reaction, 220 Azalactones, isopropenyl substituted optically active enantiomers, nucleophilic reaction, 219 resolution, 425, 438 Azalactones, multifunctional Aminoalkylation applications, 232 phenols, 29, 48 characterization, 224 p-Aminobenzoic acid curing mechanism, 232 polyphosphonamide monomer, 190 expansion polymerization, 232 polyamino acid monomer, 190 Michael addition, 232 Antibiotics Nucleophilic addition, 219, 220, polypeptide containing, 419 232 Aromatic polymers ring opening polymerization, 231, interfacial polymerization 232 production procedure, 54, synthesis, 221, 223, 224 59 Azalactones, vinyl substituted Arrhenius equation amine reaction, 229, 230 benzoxazine polymerization, 41 bis-mercaptan reaction product Arrhenius plot identification, 226 methyl methacrylate radical characterization, 227, 228 polymerization, 511 mercaptan Michael addult, 226-229 styrene anionic dispersion nucleophilic reactions, 219 polymerization, 392, 396 Azobisisobutyromitrile Arsenic pentafluoride radical polymerization catalyst, PPS dopant, 182 507-511, 514 Arsenic trifluoride PPS dopant, 182 Benzene Arterial prosthesis iron trichloride catalyzed poly(-urethane) based, 309 sulfur monochloride (-)-Asparagine reaction, 177 conversion to optically active sulfur-aluminum chloride S-propiolactone, 445 polymerized, 160, 170 Aspergillus flavus, 277 sulfur reaction, 159-162, 164, Aspergillus niger, 277 170, 171

518 Benzenesulfonamide-a-propiolac• Benzoyl peroxide tones, a-(p-substituted) radical polymerization optically active monomer initiator, 510, 511 synthesis, 445 Benzyl bromide Benzophenone N-(2-hydroxyetnyl) amide photosensitizer, 125 reaction, 240 Benzoxazines Bernoullian statistics amine containing phenolic poly (a-propiolactones), 453 resins, 48 poly (a-trichloromethyl antioxidant uses, 48 a-propiolactone), 447 applications, 47 a-substituted poly bulk polymerization, 29 (a-propiolactones), 447 C14 labeled, 48 Biomer substrate grafting, 29, 48 bromination, 310-312 characteristics, 27, 29, 48 chlorination, 310-312 complexing agents, 48 REMA grafted, 313 2,4-dimethylphenol reaction, 32 REMA palmitate grafting, 2,6-dimethylphenol reaction, 32 313-315 2,4-ditert-butylphenol polymeri- methyl methacrylate grafted, 313 zation rate, 39-41, 43 prosthesis materials, 309-311 2,6-ditert-butylphenol reaction, vinyl monomer grafting, 315 31 Biopolymers epoxy resin crosslinker, 47 cellulosic type, 405 fiber reinforced laminate uses, protein type, 405 47 starch type, 405 oligomer applications, 47, 48 Biphenols oligomerization reactions, 47, 48 bisphenate complex, 115 ortho and para substituted, 48 bisphenate synthesis, 114, 115 phenol activation energy, 30-32 dihaloalkane polyetherification, phenol initiated polymerization, 143 33-37, 47, 48 etherification mechanism, 143 phenol reaction, 28-31, 33, 34, Schotten-Baumann reaction, 189 48 4,4'-Biphenol phenol reaction rate constants, polyether synthesis, 98, 99, 30, 31, 33 101, 105, 108, 109 phenolic resin uses, 47 purification, 97 polymerization activation Biphenols, sodium salts energy, 41 aryl halide reactions, 114-116 polymerization kinetics, 35-37, N,N'-Bis(acetacetyl)-1,4-piperazine 48 p-n-butylamine model compound, polymerization mechanism, 37-39 283, 285 polymerization rate constants, p-N-butylaniline reaction, 280 40, 41 1,10-decamethylenediamine polymerization rate equation, condensation, 282 37-39 diamine reaction product polymerization routes, 35 characterization 281, 284 polymer molecular weights, 37, Jeffamine polycondensation, 286 38, 47 p-phenylenediamine condensation, polymer structure, 35 282 ring opening polymerization, poly(amide enamine) monomer, 279 27-29, 33-36, 48 synthesis, 280 synthesis, 28, 48 m-xylxylenediamine condensation, thermal initiated 282 polymerization, 34, 42, 43 Bis(acetylacetone) ethylenediamine thermal polymerization kinetics, tautomeric forms, 276 43-47 Bis-acetylacetylarenes thermal polymerization diamine polycondensation, 278 mechanism, 45 thermal properties, 31, 34

519 2,2-Bis(4-amino cyclohexyl) propane Bis(methylurethane) polyamide monomer 59, 60, 65-70, reaction, 265 80-83, 85-88 Bisoxazoline purification, 72 dicarboxylic acid Bisazlactones copolymeriztion, 236 applications, 220, 221 ring opening polycondensations, diamine polymerization, 220 235 epoxy resin alternative, 231 Bis(phenylthio)benzene resin alternative, 231 synthesis, 169 Michael-type reaction mechanism, Bis-triazolinediones 223 copolymerization, 19 oligomeric materials, 229 copolymer thermal properties, 23 polyamine reactions, 231, 232 B-dicarbonyl compound reactions, polymerization rates, 231 2 polyols reaction, 231 Diels-Alder Copolymerizations, 19 synthesis procedure, 220 Diels-Alder reaction, 1 1,4-Bis(3-p-n-butylanilino-2- Diene reactions, 2 butenoyl) piperzine identification, 18, 19 synthesis, 280 ene reaction, 1 1,2-Bis-(4-carboxyphenoxy) ethane synthesis, 18, 19 dibasic acid chloride Bisurethanes condensation, 188 diepoxides polymerization, 256 monomer for polyester, 188 Boron trifluoride, diethyl etherate 1,3-Bis(4-carboxyphenoxy) propane, oxazoline polymerization 192 catalyst, 238, 239 Bis(1,3-diketone) -azlactone reaction diamine condensations, 278 catalyst, 229 Bis(dimethylamino benzophenone) B-Bromobutyric acid anionic living polystyrene D-(+)-B-butyrolactone reaction, 401 conversion, 445 1,8-Bis-(dimethylamino)naphthalene, 1-Bromopentane, 136 69, 87 polyether terminator, 145, 146 1,6-Bis-(3,5-dioxo-1,2,4- N-Bromosuccinimide triazoline-4-yl)hexane poly(aryl ether ) synthesis, 8, 10, 18 bromination, 118 Bis-(p-3,5-dioxo-1,2,4-triazoline- 2-Bromoterephthalic acid, 192 4-yl-phenyl)methane 4-Bromothiophenol copolymerization reaction, 13 PPS intermediate, 175 synthesis, 10, 11, 18 copper salt/ 2,2-Bis[p-(2,3-epoxypropyl)• polymerized, 175 phenyl j propane Brucine 2,4-toluene diisocyanate amino acid resolving agent, 425, reaction, 252 427 2, 2-Bis (4-hydroxyphenyl) propane chiral base, 446 4,4'-dichlorodiphenyl sulfone Butadiene reaction, 239 anionic polymerization polyarylate monomer, 94, 95 polystyryl anion, 322, 347 polyether monomer, 94-96 s-butyllithium polymerization, polyester comonomer, 54, 59, 60, 333, 334 65-68, 70, 79-81, 83, 88 diphenylethylene dilithium purification, 72 polymerized, 325 tetramethyl derivative, 113 isoprene copolymerization, 336 Bis-ketoesters isoprene stereospecific diamine polycondensations, 276 copolymerization, 483 Bis-(methyl-4-N-phenylene polymerization mechanism, 502 ) methane 1,4-Butanediol N,N-diglycidylaniline reaction, polyester monomer, 53, 56 258 diisocyanate copolymerization, 265

520 n-Butoxylithium Carbon black epoxide-isocyanate reaction benzoxazine grafting, 29, 48 catalyst, 252 Carbon dioxide Butyl acrylate carbonation of carbanionic methacryloyl polystyrene polymers, 327-329 macromer copolymerization, Carbon tetrachloride 463 metal redox reaction, 294 p-n-Butylaniline, 279 N-Carbobenzoxy-trans-3-ethylproline N,N'-bis(acetacetyl)-1,4- brucine resolution, 427 piperazine reaction, 280 quinine resolution, 427 Butyl lithium N-Carbobenzoxy-2-methyl pipe colic anioinc polymerization initiator, acid 322, 325, 382, 383, 396, quinine resolution, 427 464, 467 N-Carbobenzoxy-2-methylproline s-Butyl lithium quinine resolution, 427 s-butyl methacrylate anioinc a-Carboxy-o-anisic acid, 192 polymeriztion, 352 N-Carboxyanhydrides diamine complexes for polymer ring opening polymerization, metalation reactions, 336 428, 429 diphenylethylene adduct 325, triethylamine polymerization, 348, 349 428, 429 oxazolinium triflate salt 5-(6-Carboxyhexyl)-1-(3-cyclo• reaction, 248 hexyl-3-hydroxypropyl)• polystyryl monocarbanion hydantoin synthesis, 410 attachment to poly(ether- n-Butyl lithium urethane), 295, 267 diphenylmethane reaction, 367 bioactivity, 305 styrene polymerization, 464, esterification reaction, 301 467, 468 mass spectrum analysis, 302, iso-Butyl methacrylate 303, 305 anionic polymerization, 352 methacrylic acid reaction, 296 s-Butyl methacrylate methacrylate ester grafting, 297 high conversion polymerization, NMR characterization, 304, 305 513 trichloroethylester character- t-Butyl methacrylate ization, 305, 306 anionic polymerization, 347, 351 tritium labeled, 296 t-Butyl peroxypivalate vinyl ester bioactivity, 318 radical polymerization vinyl ester characterization, initiator, 506 305, 307 n-Butylphosphorodichloridate, 192 vinyl ester platelet aggregation D-(+)-~-Butyrolactone prevention, 317, 318 synthesis procedure, 445 chlorides t-Butylstyrene a-amino acid reaction, 220 styrene diblock copolymeriza• p-Carboxyphenoxyacetic acid, 192 tion, 382, 383 Catalysts 1,4-Butynediol ethylimidazole, 259 polyester monomer, 53 hydrogenation of dienes, 335 lanthanide coordination type, 483 Calcium chloride tetraethylammonium bromide, 259 methyl methacrylate Catalysts, organometallic purification, 356 anionic initiators, 327 Calcium hydride Catalysts, phase transfer type, methyl methacrylate 189, 190, 195, 240, 242, purification, 356 243 monomer drying agent, 348 etherification reaction, 134 Camphor Cellulosates, alkali metal amino acid resolution agent, 427 anionic polymerization initiator, 407

521 Cellulose 6-Chloropropionaldehyde diethyl acetic anhydride reaction, 409 acetal (continued) acetylation procedure, 409 sodium cyanide reaction, 62, 74 anionic living polymer reaction, synthesis procedure, 62, 74 407, 408 6-Chloropropionic acid electrophilic group ring closure to lactone, 443 modification, 408, 410 Cinchonidine free radical monomer grafting, optically active acid 406 resolution, 444 graft polymerization, 406, 408 Citraconic acid, 192 grafting anionic prepared living Coatings, powder polymers, 416 bisazlactones use, 220 leaving group attachment, 408 Cobalt octoate oxidation method, 409 diene hydrogenation catalyst, polystyrene grafted, 405 335 polystyrene grafted, Composites characterization, 411 biopolymer containing, 405 rubber grafted, 405 grafted cellulose reinforcement, sodium metaperiodate oxidation, 406 410 grafted synthetic polymer triacetate synthesis, 413 containing, 405 vinyl monomers anionic grafting Copolyesterification polymerization, 407 mesogens with various spacers, Cellulose acetate 146 characterization, 414, 415 Copolyesters graft copolymer crystallization-induced characterization, 413 reactions, 134 grafting procedure, 409 isotropization temperature, 146 living polymer grafting, 410 linear random type, 153 polyacrylonitrile grafted, 413 liquid crystalline type, 148 polystyrene grafted, 413 mesogenic phases, 146 synthesis procedure, 409 microstructure, 134 Cellulose, oxidized reorganization, 134 grafting reactions, 408 smectic mesomorphism exhibiting, Cellulose, polystyrene grafted 153 thermal properties, 411 thermal behavior, 146, 147 Chelates thermotropic type, 153 enamine carbonyl based, 275 Copolyetherification Chloral 4,4'-dihydroxybiphenyl, 154 ketene reaction to lactone. 446 Copolyethers Chloroacetone characterization, 144, 152, 153 phenol condensation, 135 4,4-dihydroxy-a-methylstilbene Chlorobenzene, 149 contining, 138-147 2-Chlorobutadiene liquid crystalline properties, Diels-Alder reaction, 1 146, 148, 149 Chloroform synthesis, 138, 139, 144, 152 polyamide solvent, 69 thermotropic type, 133 Chloromethylsilane Copolyethers, liquid crystalline coupling to polydienes, 338 4,4'-dihydroxybiphenyl based, l-Chloronaphthalene, 168 152, 154 PPS solvent, 179 Copolymerization 4-Chlorophenyl phosphoro• anionic methods, 338, 339 dichloridate, 192 cationic methods, 339 Chloroprene, 502 Diels-Alder mechanism, 12 6-Chloropropionaldehyde diethyl free radical methods, 339 acetal mesogenic monomers, 134 conversion to 4,4'-diethoxy• Copolymerization, anionic butyronitrile, 62, 74 butadiene-isoprene reactivity ratios, 335, 335

522 Copolymerization, anionic Copolymers, block (continued) (continued) styrene-butadiene-styrene, 93 butadiene-styrene rate Copolymers, branched constants, 335 synthesis methods, 331 butadiene-styrene reactivity Copolymers, comb-type ratios, 335, 336 synthesis procedures, 336 macromer grafting reaction, 463 tailor made synthetic polymers, styrene-t-butylstyrene 407 reactivity ratios, 336 Copolymers, diblock styrene-p-methylstyrene styrene-t-butylstyrene reactivity ratios, 336 containing, 382 Copolymerization, anionic grafting Copolymers, graft initiation site synthesis, 336 amphiphilic type, 407 Copolymerization, cationic anionic polymerization methods, oxazolines mixed 239 335-337 Copolymerization, coordination cellulosic type, 405 macromer grafting reaction, 463 comb-type synthesis, 335, 339 Copolymerization, radical emulsifying properties, 480 macromer grafting reaction, 463 ethylene oxide-polystyrene epoxy Copolymers ether copolymerization, alternating segmented synthesis, 465, 470, 471-475 93, 94, 96, 104-108, 139 hydrophilic linked polymer, 407 block type 93-96 macromonomer synthesis method, electrophilic functionalities 342 grafting, 337 mechanisms for grafting, 406, 408 hydrophilic-hydrophobic grafts, model polymerization methods, 342 463, 478 2-oxazoline derived, 235, 238 morphologies, 93-96 radical polymerization methods, polysulfone-terephthalate type, 336 109 synthesis procedure 236, 238, random block type, 94, 96, 106 239, 339 stereoblock type tacticities, 364 N-vinylpyrrolidone-hydroxyethyl triblock type, 139 methacrylates, 316 Copolymers, AB block N-vinylpyrrolidone-methacrylate poly(methyl methacrylate), 375- on Pellethane, 313, 315 378 water absorbing properties, 480 sequential anionic Copolymers, hydrophobic polymerization, 366 hydrophilic polymer grafted, 407 Copolymers, ABA block Copolymers, segmented anionic initiator mechanical properties, 108, III use, 366 thermal properties, 108-110 styrene-butadiene-styrene, 93 Copolymers, triblock type, 134 Copolymers, alternating, 1-3, 134 Cotton, 405 bis-triazolinedione containing, Coumalic acid 19 acid chloride synthesis, 60 Copolymers, amphiphilic grafted diazomethane reaction, 61 synthesis procedures, 407 methylation reaction, 61 Copolymers, block synthesis procedure, 60, 61, 72, alkyl methacrylates mixed, 358 73 amphipathic graft type, 381 Coumalyl chloride anionic polymerization, 322, 353 production procedure, 61 living anionic polymerization m-Cresol, 279 method 342, 351, 353 polyamide solvent, 69, 70 methacrylate containing, 326, 361 15-Crown-5 ether mixed methacrylate synthesis, 361 phase transfer catalysts, 197 model polymerization methods, 342 18-Crown-6 ether 2-oxazoline derived, 235 phase transfer catalysts, 197, poly(styrene-co-ethylene oxide), 199, 200 478 polyetherification catalyst, 143

523 Cyanoacrylates, alkyl a,~-Di(bromoalkoxy)copolyethers anionic polymerization, 322, 327 (continued) tertiary amine polymerization, synthesis procedure, 137 327 a,w-Di(bromoalkoxy)polyethers phosphine polymerization, 327 4,4'-dihydroxybiphenyl polymerization inhibitors, 327 containing, 137 Cyclodepsipeptide synthesis procedure, 136 roseotoxin B, 420 Dibromo-bis(triphenylphosphine) 1,3-Cyclohexadiene nickel lithium naphthalene polymerized, catalyst for PPS synthesis, 178 325 1,4-Dibromobutane Cyclohexane polyetherification, 143 styrene polymerization solvent, 1,2-Dibromoethane, 143 392 polyethermonomer, 139 Cyclohexene 1,7-Dibromoheptane Diels-Alder reaction, 1 4,4'-dihydroxybiphenyl reaction, Cyclohexylphosphonic dichloride, 138 192 polyether monomer, 136-138 144, 147, 151-154 DABCO 1,9-Dibromononane triethylene diamine, 267-269, 4,4-dihydroxybiphenyl reaction, 271, 272 138, 152-154 Dacron 1,5-Dibromopentane vascular grafts modification, 292 polyether monomers, 136-138, 147 1,10-Decamethylenediamine, 279 1,3-Dibromopropane N,N'-bis(acetacetyl)-1,4- polyether monomer, 141 piperazine condensation, polyetherification, 143 280, 282 Dibromoxylene Decamethylenedioxydianiline, 279, carbanionic polymer reaction, 282 332, 333 Dental impression materials a,a'-Dibromo-p-xylene triazolinedione containing, 3 diphenol reaction, 239 Diallyldimethyl silane Dibutyl magnesium triazolinedione reaction, 2 hydrocarbon monomer purification Diamides agent, 247, 248 diepoxide reactions, 254 monomer drying agent, 348 Diamines water reaction, 347 bis-ketoester reactions, 276 Di-t-butyl Diazetidine chain transfer agent, 514, 515 synthesis, 2 degradative chain transfer Dibenzoyl tartaric acid effects, 515 amino acid resolution agent, 427 1,3-Dicarbonyls Dibenzoyltartaric acid, (+) or (-) amine polycondensations, 276, 288 ethyl 2-ethyl-2-phenyl-3-amino• Dicarboxylic acids propionate diastereo• bisoxazoline copolymerization, isomeric salts, 444 236 Dibenzoyl-D-tartaric acid, (+) Dicarboxylic acids, salts isomer organophosphorus dichloride 3-ethylproline optical isomers reactions, 192 resolution, 438 o-Dichlorobenzene, 149, 258 a,w-Dibromoakanes isocyanate-epoxide reaction biphenol etherifications, 134, solvent, 252 136-138 polyetherification solvent, 136, 4,4'-Dihydroxybiphenyl reaction, 137 138 polymerization solvent, 139 a,w-Di (bromoalkoxy) copolyethers 1,4-Dichlorobenzene 4,4'-dihydroxybiphenyl arylene sulfide polymer containing, 138 intermediate 175, 176 4,4'-dihydroxy-a-methyl stilbene reaction with sulfur, 175, 176 containing, 137 sodium sulfide reaction, 173

524 1,4-Dichloro-2-butene, cis isomer Diethyl 3,4-thiophene dicarboxylate diphenol rea~tion, 239 hexamethylene diamine Dichlorodiphenyl sulfone polycondensation, 57 bisphenate reaction, 114 Diethyl zinc, water cocatalyst, 451 chlorine hydrolysis, 114 B-propiolactone polymerization 4,4-Dichlorodiphenyl sulfone catalyst, 451 diphenol reaction, 239 1,6-Diethoxy-l,5-hexadiene-3,4-dione polyether formation, 98 dianiline reaction, 278 purification, 97 4,4-Diethoxybutyronitrile B-l,I-Dichloroethyl-B-propiolactone ethyl oxalate reaction, 63 chiral europium salt complex synthesis procedure, 62, 63, 74 resolution, 447 Difluorobenzophenone Dichloromethane, 225 bisphenate reaction, 114 B-Dichloromethyl-B-propiolactone, Diglycidyl aniline, 257 racemic Diglycidyl ether bisphenol A, 257 enantiomeric excess assay, 448 4,4'-diisocyanatodiphenyl enantiomers separation, 448 methane reaction, 258, 1,4-Dicyanobutane 259, 265-269 polymerization solvent, 69, 86 4,4'-diamodiphenylene methane Dicyclohexyl carbodiimide cured, 271 N-acryloyl-a-aminoisobutyrate Diglycolic acid, 192 cyclodehydration, 225, 226 2H-3,4-Dihydro-l,3-benzoxazine esterification agent, 301 production raw materials, 48 N-methacryloylmethylalanine structure, 27 reaction, 206 synthesis, 27, 48 Diels-Alder reaction 4,4'-Dihydroxybiphenyl bis-triazolinediones, 1,2, 15, copolyethers synthesis, 149 17, 18, 20 a,w-dibromoalkane reaction, 134, 1,3-Dienes 137, 138 anionic polymerization, 321, polyethers synthesis, 148, 149, 322, 324, 333 151 dibutyl magnesium water removal, polyether thermodynamic data, 150 348 4,4'-Dihydroxy-a-methylstilbene polymerization mechanism, 502 copolyethers contianing, 146-148 stereospecific polymerization, a,w-dibromoalkane reaction, 483, 484 134-138, 144 Dienophiles, 1 polyethers containing, 138, Diepoxides 146-149, 153 diisocyanates copolymerization, synthesis, 135 265 a,w-Di(hydroxyphenyl)polyether diisocyanate reaction products, synthesis procedure, 136 254 Diisocyanates Diethylaluminum chloride allophanate reaction, 204, 205 porphyrin adduct B-propiolactone diepoxide reaction products, polymerization, 451 254, 265 Diethyl N-benzyloxycarbonylamino• oligomeric diol reaciton, 204 malonate 4,4'-Diisocyanatodiphenylene 2-pentenal reaction adduct, 420 methane synthesis route, 420, 421, 438 bis(methyl urethane), 265 Diethylene glycol dimethacrylate, diglycidyl ether bisphenol A 301 polymerization, 264 Diethyl ethoxymethylene malonate phenyl glycidyl ether reaction, diamine reaction, 277 257-259, 261, 262 Diethyl 3,4-Furan dicarboxylate trimerization reaction, 263 hexamethylene diamine Diketene, 279 polycondensation, 57 diamine polycondensation, 277 Diethyl methylmalonate Jeffamine polycondensation, 282, ethyl iodide coupline, 444 286, 287

525 Dilithium naphthalene Dimethyl 3,5-pyrazole dicarboxylate synthesis procedure, 325 ethylene glycol polyester, 52 a,w-Dilithiumpolyisoprene Dimethylsiloxane cyclic trimer ethylene oxide reaction, 329 trimethylsiloxylithium N,N-Dimethylacetamide polymerized, 462 bromine solution for Dimethyl halogenation, 298 polyanhydride solvent, 193 4-Dimethylaminopyridine polymerization solvent, 143 esterification catalyst, 301 polysulfone synthesis solvent, N,N-Dimethylaniline, 464 115 polyanhydride solvent, 193 Dimethyl terephthalate tri-isobutyl aluminum catalyst 1,4-butanediol polyester, 53 modifier, 472 copolyester synthesis, 53 2,2-Dimethylbutane ethylene glycol polyester, 53 dispersion polymerization Dimethyl terephthalic acid solvent, 386, 296 triethylamine salt, 194 2,3-Dimethyl-1,3-butadiene Dimethyl 2,5-thiophene carboxylate lanthanide stereoregular ethylene glycol polyester, 52 polymerization, 483, 484, 1, 1 '-(3,4-Dioxo-1,5-hexadienylene) 495 di-2-pyrrolidone polymerization mechanism, 502 dianiline reaction, 278 Dimethyldichlorosilane a,w-Di(pentoxy) polyether carbanionic polymer reaction, 332 synthesis procedure, 136 3,6-Dimethyl-3,4-dihydro-2H-1,3- Dipeptides benzoxazine synthesis, 190 polymerization kinetics, 34, 35 Diphenic acid, 192 N,N-Dimethyl formamide a,w-Diphenols bromine solution for bromobenzyl functionalized, 240 halogenation, 298 cis-1,4-dichloro-2-butene polyamide solvent, 69 reaction, 239 Dimethyl 2,5-furan dicarboxylate methylene chloride catalysts for transesterifica• etherification, 243 tions, 53 a,w-Di[2-(p-phenoxy)-2-oxazoline] ethylene glycol melt transester• characterization, 242 ification, 52, 53 N,N'-Diphenylbenzidine ethylene glycol polyester, 52 1,2,5-thiadiazole dicarbonyl hexamethylene diamine poly• chloride copolymerization, condensation, 55 56 hexamethylene glycol polyester, 1,4-Diphenylbutadiene, 502 53 Diphenyl terephthalic copolyester, 53 synthesis, 160, 162, 169, 170, tetramethylene glycol polyester, 177 53 1,1-Diphenylethane trimethylene glycol polyester, 53 lithium metal reaction, 367 2,5-Dimethyl-2,4-hexadiene, 502 Diphenyl ether, 161 2,4-Dimethyl-1,3-pentadiene, 502 sulfur dichloride reaction, 178 2,4-Dimethylphenol Diphenylethylene benzoxazine reaction, 32 butyllithium adduct, 325 2,6-Dimethylphenol s-butyllithium reaction, 348, benzoxazine reaction, 32 349, 352 biphenol conversion, 119 living polymer capping, 461 2,5-Dimethylpiperazine Diphenylethylene dilithium polyamides with thiofuran rings, anionic polymerization 55, 56 initiator, 32~ 2,5-Dimethylpiperazine, trans Diphenylhexyl lithium 3,4-furan dicarbonyl chloride anionic polymerization polymerization, 56 initiator, 347, 355, 359, 360

526 Diphenylhexyl lithium (continued) Ditriethylammonium adipate anionic polymerization (continued) initiator, 347, 355, 359, phosphorus acid chloride 360 condensation, 200 ethyl methacrylate Ditriethylammonium terephthalate polymerization, 353 phenylphosphonic dichloride synthesis procedure, 348, 349, reaction product, 194 352 phosphorus acid chloride conden• Diphenylmethane sation, 195-197, 199 n-butyllithium adduct formation, Diurethanes 367 diepoxide reactions, 254 4,4'-Diphenylmethane-bis• Divinylbenzene semicarbazide anionic prepared polystyrene synthesis, 10 dispersion crosslinker, 4,4'-Diphenylmethane diisocyanate 400 ethyl carbazate reaction, 10 living anionic polymer reaction, 4,4'-(4,4'-Diphenyl methylene)• 332 bis-urazole 1,12-Dodecanediol synthesis, 11 hydroxyalkyl methacrylate Diphenylmethyllithium synthesis, 301 preparation procedure, 367 Dow process Diphenylmethyl methacrylate PPS synthesis, 175 anionic homopolymerization• monofunctional initiator, Elastomers 371 rubber grafted cellulose as anionic polymerization, 364, 368 reinforcement, 405 diphenylmethyllithium polystyrene dispersion polymer polymerized, 371 reinforcement, 400, 401 purification, 367 Elastomers, thermoplastic, 2 sequential anionic segmented copolymers, 93 copolymerization, 368 synthesis concept, 480 trityl methacrylate anionic Emulsifying agent copolymerization, 373-377 polystyrene macromer - ethylene N,N'-Diphenyl-1,4-phenylene diamine oxide copolymer, 463 polyamides produces from, 56 Enamine carbonyls Diphenyl sulfide electrophilic compound synthesis, 160, 162, 169-171, 177 chelation, 275 4,4'-Diphenyl sulfone synthesis methods, 276 poly(aryl ether sulfone) tautomeric equilibria, 276 monomer, 121, 122 structure, 276 Diphenyl trisulfide Ene reaction synthesis, 162, 171 bis-triazolinediones, 1,2-Dipiperidinoethane 1, 2, 18, 20 anionic polymerization modifier, triazolinediones, 2 334 Enophiles, 1 Dispersing agents Epichlorohydrin diblock polymers, 382, 383, 387 polystyrene anion reaction, 2,4-Ditertbutylphenol 463-465, 467-470, 480 benzoxazine polymerization initiator, 35-37, 39, anionic polymerization, 321, 41, 42 322 benzoxazine reaction, 34-39 homopolymerization, 252 3,6,8-trimethyl-3,4-dihydro-2H- lithium bases polymerized, 330 1,3-benzoxazine reaction, nucleophilic reactions, 217 34, 35 Epoxy resins, 219, 231 2,6-Ditert-butylphenol 2,2-Bis (4-hydroxyphenyl) benzoxazine reaction, 31-33 propane containing, 59 Ditriethylammonium adipate cured with , 266 phenylphosphonic dichloride curing process, 251 reaction product, 194 diisocyanate reaction, 259

527 Epoxy resins (continued) Ethylene glycol dimethacrylate isocyanate reaction, 251, 256 crosslinking agent, 301 MY750 type 258, 271, 272 Ethylene oxide oxazolidone conversion, 251 living carbonionic polymer properties, 251 terminator, 329 Epoxy resins, cured living polymer macromer crosslink density, 267 production, 461 oxazolidone ring containing phenoxy anion polymerized, 238 254, 266 polystyrene anion Ethane sulfonic acid polymerization, 478 azlactone-thio reaction polystyrene macromer catalyst, 223, 224, 227, polymerization, 463 228 purification, 464 Etherification 2-Ethyl mercaptoethyl methacrylate phase transfer catalyzed, 134 methyl methacrylate Ethylazodicarboxylate copolymerization, 514 Diels-alden reaction, 1 Ethyl methacrylate Ethyl-3-carbonyl-2-furan carboxy• anionic polymerization,352, 358 late characterization, 358 conversion to 2,3-furan• living anionic polymerization, dicarboxylic acid, 63, 76 358 synthesis procedure, 63, 76 Ethyl 2-methyl-2-ethylmalonic acid Ethyl carbazate bromoacid synthesis, 444 1,6 - hexane diisocyanate cinchonidine resolution, 444 reation, 8 lactone transformation, 444, 445 isocyanate reaction, 10 quinine resolution, 444 Ethyl chloroformate, 229 2-Ethyl-4-methylimidazole, 257 N-acryloylmethylalanine oxazolidone formation catalyst reaction, 206 258, 259, 261-265 cyclodehydration agent with a-Ethyl-a-methyl-a-propiolactone triethylamine, 223 optically active monomer Ethyl 2-ethyl-2-phenyl-3- resolution, 445 aminopropionate Ethyl 2-oxo-3-cyano-5,5- optical resolution D, L diethoxypentantoate mixture, 444 synthesis procedure, 63, 75, 76 3-Ethyl-5-hydroxy-N-benzyloxy• Ethyl-2-phenyl-2- cyanoacetate pyrrolidine ethyl bromide alkylation, 443 hydrogenolysis, 420 ethyl bromide adduct synthesis procedure, 420 hydrogenation, 443 Ethyl imidazole a-Ethyl-a-phenyl-a-propiolactone isocyanate trimerization optically pure monomer catalyst, 266-268, synthesis, 443 271, 272 3-Ethylproline N-carboxyanhydride, Ethylene trans potassium alcoholate racemic mixture polymerization, polymerization, 462 429 Ethylene azidohydrin 3-Ethylproline-N-carboxyanhydride, reaction, 237 trans D (+) and L (-) Ethylene-bis (3-mercaptopropionate) polymerization with azlactone addition reaction triethylamine, 429 221, 223 polymer characterization, 430 synthesis, 223 sodium methoxide polymerization, 1,2-Ethylenediamine, 279 429 ., N,N'- (acetacetyl)-I, 5-Ethylproline, cis isomer 4-piperazine reaction, 280 L-(+)-tartaric acid resolution, 4,4'-(Ethylenedioxy) dibenzoic 427 acid, 192 5-Ethylproline, cis and trans Ethylene glycol NMR characterization, 426 2,5-furancarboxylic acid polyester, 52, 53, 56

528 3-Ethylpyroline, cis and trans Formamidines isomers isocyanate-DMR reaction product, diastereoisomers separation, 423 266 diastereoisomers stereochemical Formic Acid assignments, 423 polyamide solvent, 69 methyl ester isomers, 422 Friedel-Crafts Catalysts polymerization, 419 aluminum chloride, 159-161 synthesis and separation, 419, Friedel Crafts reaction 421, 438 benzene with sulfur, 176 5-Ethylproline, trans isomer Fumaric acid, 192 L-(+)-tartaric acid resolution, Fur an 427 , 57 3-Ethylproline ethyl ester, reactivity, 57 (D) or (L) 2,3-Furan dicarbonyl chloride optically active hydorchloride anilino reaction, 78, 85 salt, 427 diamine polymerization reactions, 3-Ethylproline, ethyl ester, trans 86-88 isomer diphenol polymerization D(-) and L (+)-tartanic acid reactions, 86, 87 resolution, 427, 438 2,4-Furan dicarbonyl chloride 3-Ethylproline hydrochloride, aniline reaction, 78 cis- and trans• diamine reactions, 85 dibenzoyl tartaric acid diphenol reactions, 84 resolution, 428 intercarbonyl distance, 71 synthesis method, 422 phosphorus pentochloride 3-Ethylproline, trans (D) and (L) reaction, 64 enantiomers optical purity, 428 polyamide monomer, 69, 71, 85 ring opening polymerization, 428 synthesis procedure, 64, 77 tris-[3-(heptafluoropropyl- 2,5-Furan dicarbonyl chloride hydroxy-methylene)-d• 2,2-bis(4-hydroxyphenyl) propane campohorato] europhium III interfacial resolution, 428 copolymerization, 55, 59 3-Ethylproline, trans D(+) and decamethylene diamine interfacial L(-) -- polycondensation, 55 optical isomers resolution, 438 diamine reaction, 80, 81 3-Ethylproline, trans isomer diphenol polyesterification, N-carboxyanhydride 79, 80, 83 polymerization, 429 glycol interfacial polymerization, (-)-dibenzoyl-L-tartaric acid 54, 59 resolution, 427, 438 hexamethylene diamine interfacial optical resolution, 425, 438 polycondensation, 55 phosgene conversion to octamethylenediamine interfacial N-carboxyanhydride, 428 polycondensation, 55 3-Ethylproline, trans D (+) isomer Furan Dicarboxylic Acids resolution method, 426 polyamide monomers, 51, 52 3-Ethylproline, trans L (-) isomer polyester monomers, 51, 52 resolution method, 426 2,3-Furan dicarboxylic acid Eugenol acid chloride synthesis, 64, 76, vanillin reaction, 13, 14 78 Europhium salt, chiral crystallographic dimensions, 58, optically active a-propiolactone 71 resolution, 444, 445, 447, ester derivative, 51 448 intercarbonyl distance, 71 phosphorus pentachloride Flory-Huggins theory reaction, 60, 64, 78 optically active polymers synthesis procedure, 62, 63, 76 application, 455 2,4-Furan dicarboxylic acid Formaldehyde acid chloride synthesis, 60, 64, benzoxazine synthesis, 27, 28, 77 48

529 2,4-Furan dicarboxylic acid Glass transition temperatures (continued) (continued) crystallographic dimensions, 58, polystyrene living polymer, 388, 71 389 ester derivatives, 51 segmented polysulfone,• n,w-glycol polyesterification, polyarylates, 109, 110, 53 118 production reactions, 60 Glycidyl methacrylate synthesis procedure, 61, 74 oligomers prepared from, 203 2,5-Furan dicarboxylic acid Grafting acid chloride synthesis, 60, 64, antiplatelet agents on polymers, 78 291-293 crystallographic dimensions, 58 manganese de carbonyl reaction 71 mechanism, 300 dehydromucic acid, 60 photochemical initiated, 299, ester derivatives, 51 300 ethylene glycol polyester, 52 thermal initiated, 299 hexamethylene-diammonium salt polycondensation, 55 4-Halophenol hexamethylene glycol polyesters, polymerization with metal salts, 53 178 intercarbonyl distance, 71 4-Halothiophenol phosphorus pentachloride alkali metal salt polymerized, reaction, 64 175 synthesis procedure, 72 Heparin terephthalic acid-ethylene grafted on poly (ether glycol copolyester, 54 urethanes), 293 tetromethylene glycol Heptane polyesters, 53 dispersion polymerization trimethylene glycol polyesters, solvent, 386 53 HEXA 3,4-Furan dicarboxylic acid polyoxazolidone synthesis acid chloride synthesis, 60, 64 catalyst, 267-269, 271, 272 77 2,4-Hexadiene, trans, trans crystallographic dimensions, 58, cobalt catalyst polymerized, 494 71 lanthanide stereospecific ester derivative, 51 polymerization, 483, 491, intercarbonyl distance, 71 503 phosphorous pentachloride polymerization mechanism, 502 reaction, 64 sterical hinderance, 503 physical properties, 62 titanium catalyst polymerized, 2,5-Furan dicarbonyl chloride 494 polyamide formation, 80,81 Hexafluoroisoprapanol synthesis procedure, 76 isotatic poly(B-propiolactones) 3,4-Furandicarbonyl chloride solvent, 451 diamine reactions, 82, 83 polyamide solvent, 70 diphenol polyesterification, Hexamethylphosphoramide 81,82 polyanhydride solvent, 193 polyamides produced from, 56, 71 Hexamethylene diamine synthesis procedure, 64, 77 polyamide monomer, 57 purification, 72 Glass transition temperatures Hexamethylene glycol poly (alkyl methacrylates), 359, 2,5-furandicarboxylic acid 360, 363, 506-509, 512, polyester, 53 513, 516 Hexamethylene tetramine polyethers, 135, 138, 144-147 oxazolidone formation catalyst, polyoxazolidones, 270, 271 259 poly (1,3-pentadiene), 485, 490, Hexane 491, 495, 500 dispersion polymerization poly (B-propiolactones), 453 solvent, 386, 396

530 1,6-Hexane-bis-semicarbazide, 8 p-Hydroxyphenyl-2-oxazoline 1,6-Hexane-bis-urazole (continued) synthesis, 8, 9 polyformal end capping monomer, 1,6-Hexane diisocyanate, 8 243, 244 Hormones synthesis procedure, 237, 248 polypeptide based, 419 p-Hydroxyphenyl-2-oxazoline, Hydrogen sulfide di-salts PPS synthesis biproduct, 160-162, ring opening polymerization, 249 164 synthesis procedure, 248 Hydroquinone p-Hydroxyphenyl-2-oxazoline, polyether monomer, 94, 96-99, lithium salt 108 epoxide polymerization segmeted copolymer momomer, 109 initiaton, 238 Hydroxy alkyl methacrylate p-Hydroxyphenyl-2-oxazoline, vinyl oligomers produced from, 204 benzyl p-Hydroxybenzaldehyde NMR characterization, 244, 245 ethylene azidohydrin reaction, polymer characterization, 244 1 237 1 radical polymerization, 244 p, P -Hydroxy-2, 2 -dimethyl 3-Hydroxy proline, 424 benzalazine B-Hydroxypropionic acid liquid crystalline polymer ring closure to lactone, 443 segment, 133 12-Hydroxysteric acid, 307 N-(2-hydroxyethyl) amides Hydroquinone oxazoline hydrolysis product, 240 polyester monomer, 54 N-(2-Hydroxyethyl)-p-hydroxy• benzamide p-hydroxyphenyl-2-oxazoline structure, 276 hydrolysis product, 238, Iminoamines, 1,3 244 crystallographic data, 276 thionyl chloride cyclization, 238 IR characterization, 276 2-Hydroxylethyl methacrylate Imino-l,3-dioxolane, N-substituted esterification with hydantoin isomerization to oxazolidone, acid derivative, 301 253 esterification reaction, 307 2-Imino-l,3-dioxolane, phenyl grafting on Pellethane, 315 substituted methacryloyl polystyrene isomerization to oxazolidone, macromer copolymerization, 253 463 Initiators, electrophilic 5-Hydroxymethyl-2-furoic acid 2-oxazoline polymerization, 235 polyesters, 54 Initiators, radical polymerization Hydroxynapthones kinetics influence, 508 tautomeric forms, 276 Iodine-thiosulfate m-Hydroxyphenyl-2-oxazoline titration of polystryrene chlorohydrate product, 237, 238 peroxide, 400 disalt synthesis, 248, 249 Ionophores hydrolysis, 238 polypeptide based, 419 synthesis procedure, 237, 238 Isobutylene p-Hydroxyphenyl-2-oxazoline cationic polymerization, 462 chlorohydrate product, 237, 238 inifer polymerization method, chloromethylstyrene 462 etherification, 244 Isoeugenol a,w-di(electrophilic) polyether bis-triazolinedione reaction, sulfone reaction, 240 14 etherification with methylene methyl isocyanate reaction, chloride, 243 5, 14 hydrolysis, 238 Isoprene lithia ted with butyllithium, 238 anionic polymerization, 347 methyl trifluoromethane s-butyllithium polymerization, sulfonate reaction, 248 333, 334 phenoxy anion product, 238

531 butadiene stereospecific Kemamine copolymerization, 483 36-carbon diamine, 208 dilithium initiator Ketenes polymerization, 347 carbonyl compound reaction, polymerization mechanism, 502 443, 445, 457 Isothianthrene chloral conversion to lactone, synthesis, 162 446 Isocyanates, 219, 231 enamine derivative, 275 reaction, 266 epoxide reaction to oxazolidone, Lactones 251, 259 anionic polymerization, 321, 322, formation reaction, 261 441, 447 nucleophilic reaction, 217 cationic polymerization, 441, 447 trimerization, 254, 259, 266 coordination polymerization, 441, Isocyanurates 447 isocyanate trimerization, 254, ring opening polymerization, 441 259, 261, 262 8-Lactones kinetics of formation, 264 diastereoisomer complex Isophthalic acid resolution, 446 crystallographic dimensions, 58 optically active chiral base a,w-glycol polyesterification, synthesis, 446 53, 56 racemic mixtures, 446 polyamide monomers, 57 Lactones, bicyclic polyester monomer, 53, 56, 58-60 tetrahydrofuran ring containing, Isophthaloyl chloride 54 1 ,2-bis-(4-carboxyphenoxy) ethane Lanthanides polycondensation, 188 coordination capabilities, 483 copolyamides, 60 rare earth metal catalysts, 483, diamine polycondenation, 60 502 polyarylate synthesis, 94-96 Lanthanides, catalysts purification, 97 classification types, 484 4,4-sulponyldiphenol polyester, diene polymerization catalysts, 59, 60 483 - 503 2-Isopropenyl-4, 4-dimethylazalac- organic chemical complex tone catalysts, 483 Jeffamine reaction, 212 Lauroyl peroxide ORTEP plots, 211 polystyrene macromer synthesis procedure,206 polymerization, 463 2-Isopropenyl-2-oxazoline Lead oxide free radical polymerization, 237 esterification catalyst, 53 ISOX Lekutherm isocyanurate-oxazolidone N,N-diglycidylanilin, 258 containing polymers, 256 epoxide resin, 265 oxazolidone resins, 272 Lewis acid, 191 tetrahydrofuran anionic Jeffamines, 279, 282, 286 polymerization modifier, alkenyl azlactone reaction, 211, 396 212, 215 Lewis bases, 191, 192, 194, 195 N,N'-bis(acetacetyl)-1,4-piper• anionic polymerization modifier, azine condensation, 280 333-335 diketene reaction, 282 radical anion stabilizers, 323 polyoxyalkylene oligomers, 206, Linoleic acid 207, 211 clay catalyzed dimerization, 208 reaction, 207, 208 Diels-Alder reaction, 208 Lithium alkoxides Kelley-Bueche equation epoxide polymerization, 330 methyl methacrylate Lithium but oxide polymerization catalyst for oxazolidone application, 512 formation, 252

532 Lithium but oxide (continued) Macromonomers isocyanate-epoxide reaction copolymerization, 339 catalyst, 264 grafting onto polymers, 336 polyoxazolidone synthesis methacrylate terminated catalyst, 267 oligomers, 339, 340 Lithium chloride oligomers with polymerizable oxazolidone formation catalyst, end-group, 339 265 polymerizable oligomers, 339 Lithium naphthalene polymerizations, 335 styrene reaction, 324 reactivity ratios, 339, 340 Lithium triflate synthesis procedures, 339-341 oxazolinium di-salt Macromonomers, poly (4-bromosytrene) polymerization biproduct, vinyl styrene terminated, 341 249 Mac romonomers, poly (ethylene oxide) 2,6-Lutidine, 428 methacrylate terminated, 340 a-methylstyryl terminated, 340 Macallum Polymerization oxazoline terminated, 238, 340, dichlorobenzene-sulfur reaction, 341 175, 176 p-vinylstyryl terminated, 341 Macromers Macromonomers, poly (methyl copolymerization to graft methacrylate) copolymers, 463 a-methylstyryl terminated, 341 epoxy ether terminated Macromonomer, oxazoline terminated polystyrenes, 463-469 cationic ring opening graft copolymerization polymerization, 238, 239 efficiency, 471, 472, Macromonomers, polystyrene 474-476, 478 anionic living polymerization graft copolymer use, 461 synthesis, 340 homopolymerization, 463 p-vinylstyryl terminated methacryloyl terminated Macromonomers, poly(vinyl pyridine) polytetrahydrofurans, 463 methacrylate terminated, 341 poly (dimethyl siloxane) based, p-a-methylstyryl terminated, 341 462 MacTomonomers, siloxane polyisobutylene based, 462 methacrylate terminated, 341 polymerizable macromolecular p-vinylstyryl terminated, 341 monomer, 461 Maleic anhydride polyoxyethylene type, 462 Diels-Alder reaction, 1 poly (methyl methacrylate) based, Malic acid 462 conc. sulfuric acid reaction, 60 polystyrene based, 462 fuming sulfuric acid reaction, 60 synthetic techniques, 134 Manganese decacarbonyl p-vinylbenzyl capped grafting catalyst, 299, 300 polystyrene, 461 purification, 308 Macromer, epoxy ether terminated Mayo-Lewis equation ethylene oxide copolymerization, applied to macromonomers, 339 480 Mercaptans synthesis procedures, 461 alkenyl azlactone ractions, 224 Macromers, methacryloyl terminated vinyl azlactone reaction, 227-229 polyoxyethylene based, 462 3-Mercaptopropionic acid Macromers, polystyrene ethylene glycol esterification, epoxy ether terminated, 461 223 Macromers, production Mesogens anionic polymerization method, conjugated electron donor type, 462 134 cationic polymerization method, Methacrylamide 462 functionalized oligomers, 205, radical polymerization method, 210, 211 462 Methacrylates, alkyl alkali metal alkoxides polymenization, 327

533 Methacrylates, alkyl (continued) Methyl coumalate anionic polymerization, 321, 322, pyridinium bromide perbromide 347, 348 reaction, 61 carbonyl side reactions-anionic Methylene chloride polyerization, 347 p-Hydroxyphenyl-2-oxazoline dibutyl magnesium polymerization, reaction, 243 348 Methylenedianiline, 279 diphenylethylene anionic diethyl ethoxymethylene malonate initiators, 351, 352 polycondensation, 277 group transfer polymerization, a-Methyl-a-ethyl-S-propiolactone 327 optically active monomer high conversion polymerization, synthesis, 444 50S, 512-514 a-Methyl-a-ethyl-S-propiothiolactone molar volumes, 513 optically active monomer photoinitiation polymerization, proparation, 445 354 a-Methyl-a-m-propyl-S-propiolactone polymerization kinetics, 50S, chiraal initiator polymerization, 506, 508-513 443 polymerization kinetics, model Methyl m-hydroxybenzoate 509, 510, 516 ethanolamine reaction, 238 purification procedures, 358, Methyl isocyanate 361, 367 isoeugenol reaction, 5 radical polymerization, 50S, 512 Methyl 3-mercaptopropionate sequential anionic vinyl azlactone reaction, 227, 228 polymerization, 366 Methyl methacrylate trialkyl aluminum purification, acetone-cyanohydrin process, 355 348, 350, 354 alcohol doped purification, 352 Methacrylonitrile anionic bifunctional initiator anionic polymerization, 322 polymerized, 373 Methacryloyl hexafluorantimonate anionic polymerization, 323, tetrahydrofuran polymerization to 325-327, 347, 352,360-362, macromer, 462 372, 373, 462 N-Methacryloylmethylalanine anionic tactic polymerization, N, N-dicyclohexyl carbodiimide 365 reaction, 206 butyl lithium polymerized, 326 p-Methoxyphenol celing temperature, 507 methacrylate stablizier, 305 chain transfer polymerization, 2-Methoxy-4-propenylphenyl 514 methyl-carbamate 14 C labeled, 308 bis-triazolinedione raction, 19 diffusion hindered 1,6-Bis-(3,5-dioxo-l,2,4,• polymerization 508-510 triazoline-4-yl) hexane diphenyl hexyl lithium reation, 12 polymerization, 355 copolymerization reaction, 13 diphenylmethyllithium Diels-Alder derivative, IS polymerized, 371 2-Methoxy-4-propenylphenol 2-ethyl mercaptoethyl methyl isocyanate reaction,S, 14 methacrylate copolymeri• methyl triazolinedione reaction, zation, 514 14 grafting on Pellethane, 315 4-methyl-l,2,4-triazoline-3,5- high conversion polymerization dione reaction, 6 kinetics, 506-510, 516 synthesis, 5 initiator influence on Methyl bromocoumalate polymerization, 508, 511 synthesis procedure, 61, 74 isothermal polymerization, 508 Methyl 3-bromo-2-oxopyran-5 methoxide anion polymerization, carboxylate 327, 328 synthesis procedure, 61, 73, 74 polymerization kinetics, 508-516 Methyl coumalate polymerization solvent effects, bromonation reaction, 61 360 production procedure, 60, 61, 73

534 Methyl methacrylate (continued) Molybdenum hexacarbonyl polymerization temperature grafting catalyst, 229 influence 507 Monomers purification, 367 dinelectrophilic, 138 radical polymerized, 507-510 dinucleophilic, 138 termination rate constant, 509 radio-labelled, 308 transesterification, 348 Monomers, mesogenic trialkyl aluminum alcohol copolymerization, 134 removal, 355 Monomers, optically active trialkyl aluminum purification, enantiomeric excess measurement, 348, 355, 356 446-448 2-Methyl-2-oxazoline Monomers, polar hydroxyphenyl-2-oxazolinium salt polymerization, 325, 326, 342, 347 polymerized, 248 Monomers, vinyl hydrophilic Methyl 2-oxopyran-5-carboxylate biomer effects, 309 production procedure, 60, 73 Monomers, vinyl 4-Methyl-1,3-pentadienes, 502 cellulose grafting methods, 407, 2-Methyl-1,3-pentadiene, trans 408 Lanthanide sterospecific grafting on poly polymerization, 484, 500 (ether-urethanes), 299 polymerization mechanism, 502 Mucic acid 3-Methylproline, 424 fuming hydrobromic acid realtion, 3-Methyl-L-proline, cis isomer 60, 72 isolation from bottromycin MY 750 antibiotic peptide, 420 epoxide resin, 258, 259 synthesis routes, 420 Myrcene, 502 5-Methylproline, cis and trans mixture Nitrobenzene, 136-138, 149 L-(+)-tartaric acid resolution, Nitroterephthatic acid, 192 427 3-Methyl-L-proline, trans isomer Oligomers isolation from mycotoxin, benzene-sulfur containing, roseotoxin B, 420 169,171, 175, 177 synthesis route, 420 crosslinking reactions, 205 Methane sulfonic acid a,w-dielectrophilic chain ends, polyamide solvent, 69 139 Methyl triazolinedione functionalized for crosslinking, synthesis, 14 203 4-Methyl-1,2,4-triazoline-3,5-dione hydrogen bonding chain ends, 138 allyltrimethylsilane reaction, 2 macromonomers with reactive Diels-Alder reaction, 1, 15 end-groups, 339 2-methoxy-4-propenylphenylmethyl methacnylate functionalized, 203, carbamate reaction, 6 204 N-Methylpyrrolidone, 279 reactive macromonomers, 339 polyamide solvent, 69 synthesis procedures, 339, 340 polyether synthesis solvent, 143 unsaturated, 204 PPS production solvent, 173 Oligomers, acrylamide terminated polysulfone synthesis solvent, synthesis from azlactones, 213, 115, 116 217, 219, 232 Methyl trifluoromethane sulfonate characterization, 209-211, 213, oxazoline triflate formation 215, 216 reaction, 248 Oligomers, amine terminated, 206, Michael addition reaction 207 aklenyl azlactones, 210, 215, 217 alkenyl azlactone reactions, Amines, 215 217, 221 2-pentenal-substituted diethyl azalactone reaction, 203, 205, malonate, 420, 438 211, 217, 219 thio-acrylates, 222-224 urea reaction, 207, 208 thio-acrylamides, 222, 223 Oligomers, azlactone terminated synthesis, 225, 232

535 Oligomers, bromobenzyl substituted 2-0xazoline-5-ones etherification with phenolic ring opening reactions, 219 oxazolines, 243 Nucleophilic reactions, 219 Oligomers, a,w-di (bromobenzyl) 2-0xazolines substituted boron trifluoride polymerized, characterization, 241 238, 239 Oligomers,a,w-di(electrophilic) cationic polymerization, 235, substituted 236, 238, 248 macromonomer starting materials, carboxylic acid ring openings 239 reaction, 235 Oligomers, a,w-diphenol substituted hydrolysis to amides, 240, 242 characterization, 241 phenol ring opening reactions, Oligomers, hydroxy terminated 235, 236 alkenyl azlactone reaction, 221 thiophenol ring opening reaction, Oligomers, liquid 235 azlactone functionalized, 232 2-0xazolines, m-hydroxyphenyl Oligomers, oxazoline terminated substituted characterization, 242, 243 polymers produced from 235, 237 poly(phenylene sulfide) based, 2-0xazolines, p-hydroxyphenyl 237 substituted synthesis, 241-243 polymers produced from 235, 237 thermally reactive, 248 2-0xazolines, phenoxy substituted Oligomers, polyether NMR characterization, 242 hydroxyphenyl terminated, 145 2-0xazolines, vinyl substituted Oligomers, polyether sulfone radical polymerization, 237 oxazoline terminated, 240 Oxazolinium triflates Oligomers, telechelic oxazoline polymerization agents, azlactone functionalized, 232 248 Organometallic dihalides Oxiranes dicarboxylic acid condensation, chiral initiator polymerization, 195 442 dicarboxylic acid polymerization, 2-0xopyran-5-carboxylic acid 187, 189, 195 coumalic acid, 60 Organophosphorus dichlorides production method, 60 p-aminobenzoic acid condensation, 2-0xopyran-5-carboxylic acid 190 synthesis procedures, 72, 73 amino acid reactions, 190 Oxycellulose dicarboxylic acid polystyryldicarbanion grafting, polycondensation, 189 410, 411 polypeptide reaction, 191 synthesis procedures, 409 Organophosphorus (v) polyesters, 192 4,4'-(2,2'-Oxydiethoxy)-dibenzoic Oxazolidone acid, 192 catalyst for formation, 261, 262 epoxide-isocyanate reaction Palmitic acid, 307 product, 263 hydroxyethyl methacrylate formation kinetic parameters, 264 derivative, 307 formation reaction t.ritiated, 307 characterization, 262,-263 Pelle thane formation study by DSC, 267, 268 BEMA palmitate ester heat of formation, 263 photografting, 314 isocyanate-epoxide reaction poly (ether-urethane) mechanism, 253 bromination, homogeneous, mechanism of formation, 252, 253 298, 310, 311 ring isomers, 254 vinyl monomer grafting, 315 2-0xazolidones N-vinylpyrrolidone-methacrylate N-subtituted iminc-2,3-dixolane ester grafted, 316 isomerization product, 253 1,3-Pentadiene, cis, 485, 503 Oxazolidone resins 1,3-Pentadiene, trans isomer isocyanurate containing, 266 lanthanide stereospecific thermal properties, 266 polymerization, 484, 485

536 1,3-Pentadiene, trans isomer Phenyltriazolinedione (continued) synthesis, 74 polymerization mechanism, 484, 502 4-Phenyl-1,2,4-triazoline-3,5- Pentane dione, 1 dispersion polymerization Diels-Alder adduct, 15 solvent, 386, 396 2-methoxy-4-propenylphenylmethyl 1,5-Pentanediol carbamate reaction, 7 hydroxy alkyl methacrylate olefin reaction, 7 synthesis, 301 Phosphorus acid chloride 2-Pentenal diamine polymerization, 189 diethyl N-benzyloxycarbonyl• diphenol polymerization, 189 aminomalonate adduct, 420, hydrolysis, 189, 195 438 Phosphorus anhydrides synthesis method 420, 422 synthesis, 190 Peroxides, polymeric Phosphorus pentachloride, 76 synthesis procedure, 331 Phosphotungstic acid Phenol sulfided hydrogenation catalyst, benzoxazine condensation 161 mechanism, 32-35 Phthalic acid benzoxazine reaction rate crystallographic dimensions, 58 constant, 33 polyamide monomers, 57 benzoxazine synthesis, 27, 28, polyester monomer, 60 48 PIO potassium cargonate oxazolidone containing resins, neutralization, 116 256 Phenol-formaldehyde resins Piperazine, 279 phenolic monomers, 59 diketene reaction, 280 Phenolic resins Piperlene, trans synthesis route, 27, 28, 48 lanthanide stereospecific N-(4-Phenylbenzyloxycarbonyl-cis- polymerization, 483 6-methyl pipecolic acid Plastics, engineering quinine resolution, 427 poly(phenylene sulfide), 173 2,2'-p-Phenylene-bis-(4-ethoxy• Polyacetylene methylene-5-oxazolone) chemical doping, 182 dianiline reaction, 278 Poly(N-acetyl-ethyleneimine)s p-Phenylenediamine phenolic hydroxyl terminated, 248 N,N'-bis(acetaacetyl)-1,4-piper• telechelic materials, 248 azine condensation, 282 Polyacrylonitrile, 414 a-Phenylethyl potassium Polyacrylonitrile, carbanion ethylene oxide polymerization grafting to cellulose acetate, catalyst, 478 413 a-Phenyl-a-ethyl-S-propiolactone Poly(acrylonitrile), "living" enantiomeric resolution, 444 polymer chiral europium salt resolution, synthesis procedure, 410 444, 445 Poly(N-acylethyleneimine)s Phenyl glycidyl ether, 257 2-oxazoline derived, 235 diisocyanate reaction, 259 reactions on polymer, 235 4,4'diisocyanatodiphenyl methane synthesis procedure, 240 reaction, 258, 259, 266-268 Poly-alcanoates diisocyanate reaction liquid crystalline polymers, 133 characterization, 259-262 Poly(alkyl methacrylate) Phenylisocyanate anionic copolymeriza'tion, 348 trimerization, 263 anionic polymerization, 348, 349 Phenylphosphonic dichloride, 192 anionic polymerized molecular polyamide prepared from, 194 weights, 366 Phenylphosphonothioic dichloride, bulk polymer production, 505, 516 192 casting processes, 505 Phenylphosphoro dichloridate, 192 characterization, 350, 352, 353 Phenylthiothianthrene controlled anionic synthesis, 162, 169 polymerization, 358

537 Poly(alkyl methacrylate) Polyamides, metalated (continued) ethylene oxide grafting, 337 controlled molecular weight, 361 ethylene sulfide grafting, 337 isotactic polymer synthesis, 348 Polyamides, phosphorus containing physical properties, 363 synthesis procedure, 192 purification method, 350, 351 Polyamines, antimony containing synthesis conditions, 347, 351 synthesis procedure, 189 synthesis of controlled Polyanhydrides molecular weight, 348 phosphorus containing, 187, 189, synthesis using pure monomer, 361 190, 194, 195 Poly(Alkyl methacrylate), tactic synthesis procedures, 187-190, copolymer, 347 194, 195 physical association, 363, 365 Polyanhydrides, phosphorus synthesis, 347, 363-366 containing stereocomplex network amide modified, 190 structures, 365 characterization, 193, 194 Poly(alkyl methacrylate), living synthesis conditions, 193 polymer Polyarylesters termination with acetic bisphenol-A based, 94, 95 acid/methanol, 350 Poly(aryl ethers) Poly(amide-enamines), 275 characterization, 118 biodegradable polymers, 275, 277 cyano group terminated, 118, 119 N,N'-bis(acetacetyl)-1,4-piper• engineering materials, 113 azine based, 279 modified, 118, 119 piperazine containing, 288 physical and chemical properties, synthesis, 277 113, 118 Poly(amide enamine ether) synthesis procedures, 118 adhesive potential, 286 Poly(arylene ether ketones) characterization, 286, 287 synthesis procedures, 113 metal chelating ability, 286-289 Poly(aryl ethers), methyl synthesis method, 280, 282 substituted Poly(amide-ester)s crosslinking reactions, 119, 122 synthesis procedure, 236 Poly(aryl ether ) Poly(amide-ether) bromination reaction, 118 lithium phenoxide-oxazolinium characterization, 102-104, salt terminated, 249 106-109 Polyamides hydroxyl terminated oligomers, acidic proton reaction, 337 114 furan dicarboxylic acid structures, 113, 114, 117-119, containing, 51, 52, 64-69 122 furan ring containing, 55, 59 synthesis procedures, 96, 97, halogenation reaction, 295 100, 104, 107, 113-117, 122 head-to-tail type, 220 thermal properties, 118 heteroaromatic ring containing, Poly(arylene ether sulfone)-poly- 57, 58, 60 (arylene terephthalate) heterogeneous halogenation, 298 characteristics, 95, 96, 106-111 metalated with sodium, 337 random block type, 94 mixed amide type, 59, 60 segmented copolymer synthesis, phenolic hydroxyl terminated, 249 93, 95, 97, 107-111 phosphorus containing, 192 Poly(L-azetidine-2-carboxylic acid) redox oxidation initiated poly(L-proline) comparison, 438 grafting, 292, 293 Polyazomethines tail-to-tail, 220 liquid crystalline polymers, 133 vinyl monomer grafting, 295 Poly (N-benzoylethyleneimine) Polyamides, furan containing poly(ethylene oxide) grafted, intrinsic viscosities, 70 238, 239 properties, 56, 57, 68, 69, 71 Poly[I,4-bis(3-decanamino-2- solvents, 69 butenoyl)]piperazine synthesis procedure, 80-82, 84, synthesis method, 280, 282 85 thermal properties, 70, 71

538 Poly[I,4-bis(3-ethylenamino-2- Poly(cellulose acetate-a-poly• butenoyl)]piperazine acrylonitrile) synthesis method, 280 characterization, 414, 415 Poly[I,4-bis(3-p-phenylenediamino- Poly (cellulose-a-polyacrylonitrile) 2-butenoyl)]piperazine synthesis procedure, 410, 413, synthesis method, 282 414 Poly[I,4-bis(3-m-xylylamino-2- Poly(cellulose acetate-a-poly• butenoyl)]piperazine styrene) characterization, 284-286 characterization, 415 synthesis method, 282 synthesis procedure, 413-415 Polybutadiene Poly(cis-5-ethylproline) alkyl dilithium initiated, 323 conformational energy, 420 chloromethylsilane grafting, 338 conformational forms, 420 cis-l,4-microstructure Poly (cis-5-ethyl-D-proline) modification, 333, 334 conformational forms, 420 dilithio derivative, 323 Poly (3 ,4-dehydro-L-proline) high cis content, 483 helices stability, 438 metalated with alkyllithium- Polydienes diamine complexes, 336 bis-triazolinedione polymer microstructure, 502 crosslinking, 3 synthesis procedure, 334 hydrogenated products, 334 Polybutadiene, chloromethylsilane living anionic polymerization grafted method, 342 poly (a-methylstyryl) lithium microstructure, 323, 333, 334 coupling, 338 synthesis, 2, 3 poly(styryl)lithium coupling, 338 Polydienes, branched Polybutadiene, living polymer carbanionic end-linking macromer formation, 461 reactions, 332 Poly (butadienyl) lithium Poly(2,3-dimethyl-l,3-butadiene) anionic polymerization emulsion produced polymer, 495 initiator, 334 IR characterization, 498 Poly(butadiene-co-ethylene oxide) NMR characterization, 497, 499 water absorbing property, 479 polymer microstructure, 502 Poly (butadiene-co-isoprene) polymer properties, 495, 499, 500 high cis content, 483 thermal properties, 496 Poly (butadiene-b-isoprene• x-ray diffraction, 498, 499 butadiene) Poly(2,6-dimethyl-l,4-Phenylene selective hydrogenation, 335 oxide) Poly (butadiene-a-polystyrene) bromination reaction, 244 synthesis procedure, 338 bromomethyl group substituted, Poly{m-butyl methacrylate) 246 purification, 351 p-hydroxyphenyl-2-oxazoline Poly(s-butyl methacrylate) reaction, 246 characterization, 352 oxazoline substituted, 246 Poly(t-butyl methacrylate) Poly(dimethyl siloxane) purification, 351 macromer synthesis, 462 Poly (t-butylstyrene-b-styrene) Poly(diphenylmethyl methacrylate) dispersion agent power, 388, 389 hydrolysis with esterification, polymeric dispersion agent, 382, 365, 366 383 syndiotactic polymer synthesis, polystyrene dispersion agent, 364 387-389 Poly(diphenylmethyl methacrylate• Poly(t-butyl thiirane) co-trityl methacrylate) chiral stereocomplex blends, 457 ABA stereoblock synthesis, 379 Poly(a-butyrolactams) Poly(diphenylmethyl methacrylate), physical properties, 453 tactic Polycarbonates, conversion to poly(methyl monomers, 59 methacrylate), 371

539 Poly (enamines) Polyethers liquid crystalline polymers, allyl ether side chains, 141, 143 133, 134 bromoalkoxy terminated, 145 thermooxidative stability, 134 bromopentane, chain ends, 143 Poly(enamine ) carboxylic acid terminated, 145, synthesis procedure, 276 148 Poly(enamine ketones) characterization, 141, 142, synthesis, 277, 278 144-149 Poly(ester-amides) crystalline, 149 synthesis procedure, 52 4,4'-dihydroxybiphenyl Polyesters containing, 151, 152 aromatic heterocycle containing, 4,4'-dihydroxy-a-methylstilbene 52, 59 containing, 138-140 aromatic phenolic monomers, 59, diketene-Jeffamine based, 287, 60 288 characterization, 141, 142 glass transition temperature, crystalline structures, 56 138, 139 4,4'-dihydroxybiphenyl hydroxyphenyl terminated, 144-146 containing, 151 liquid crystalline type, 140 furan dicarboxylic acid mesogenic biphenol containing, containing, 51, 52, 64, 68 141 heteroaromatic ring containing, mesomorphic behavior, 144 57-60 phase transfer catalyzed, 143 hydrolytic stability, 134 phenol terminated, 136 interfacial polymerization physical properties, 134 synthesis, 188-192 synthesis procedure, 136, 138, isotropizaton temperature, 134 144 liquid crystalline type, 140 thermal transitions, 151 mesogenic biphenol containing, thermotropic type, 133 141 Polyethers, liquid crystalline, 134 metal containing, 195 characterization, 134 mixed aromatic ring type, 60 thermal properties, 154 polydimethylsiloxane modified, Poly(ether-urethanes) 148 acrylamide grafted, 293 thermotropic type, 149, 150 antiplatelet action, 309 properties of heteroaromatic antiplatelet agent grafted, 291, containing, 59 295, 296 reduction, 54 aprotic base treated, 293, 294 structure-aromatic type, 56 biomer evaluation, 309 thermal transitions, 151 brominated Polyesters, furan containing hydantoin monomers grafting, intrinsic viscosities, 70 312 properties, 69, 71 hydrophilic monomers grafting, solubility characteristics, 69, 312 70 photografting vinyl monomers, synthesis procedure, 79-83 313 thermal properties, 70, 71 bromination reaction, 298 Polyesters, hydroxy terminated chemical modification, 291-293 bislactone chain extension, 221 free radical grafting, 294 Polyesters, liquid crystalline functionalization reactions, carboxylic acid terminated, 145 293, 294 characterization, 134 grafted thermal properties, 154 arterial prosthesis evaluation, Polyetherification 309 4,4'-dihydroxybiphenyl, 154 bioactivities, 301 kinetics, 143 grafting reactions, 292, 295, phase transfer catalyzed, 134, 298-300, 308, 312 136, 138, 139 swelling behavior, 309 reaction mechanism, 144 halogenated characterization, 298

540 Poly (ether-urethanes) (continued) Polyformals molybdenum carbonyl reaction, aromatic containing, 139 299 characterization, 140 potassium iodide treated, 298 4,4'-dihydroxy-a-methylstilbene production procedures, 310, 311 containing, 136, 140 halogenation reaction, 295, 298, synthesis, 140 300, 308, 310-312 Polyformals, aromatic heparin grafted, 293 p-hydroxyphenyl-2-oxazoline end hydantoin methacrylate grafted, capping, 243 299 Polyformals, oxazoline terminated irradiation with monomer, 292 synthesis procedure, 243 isocyana~e treated, 293 Poly(2,3-furandiylcarbonylimino- long chain alkyl halide grafted, 1,4-cyclohexylenedimethyl 293, 294 methylene-l,4-cyclo• methacrylates grafting, 297 hexyleneimino carbonyl) photografting method, 308 synthesis procedure, 87 physical properties, 310 Poly(2,3-furandiylcarbonylimino- potassium hypobromite treatment, 1,4-cyclohexylenemethylene- 298 1,4-cyclohexyleneimino• properties, 291 carbonyl) prosthesis uses, 291 synthesis procedure, 87 redox reactions, 294 Poly(2,3-furandiylcarbonyloxy-l,4- mechanism of grafting, 294, 295 phenylenedimethylmethylene- segmented type, 291 1,4-phenyleneoxycarbonyl) sodium hypochlorite treatment, synthesis procedure, 85 298 Poly(2,3-furandiylcarbonyloxy-l,4- tritiated palmitic ester phenylenedioxothio-l,4- grafted, 307 phenyleneoxycarbonyl) vinyl monomer grafted, 294, 295 synthesis procedure, 86 Poly(ether sulfones), aromatic Poly(2,3-furandiylcarbonyloxy-l,4- a,w-di(bromobenzyl) substituted, phenylenethio-l,4- 239 phenyleneoxycarbonyl) a,w-di(chloroallyl) substituted, synthesis procedure, 87 239 Poly (2, 4-furandiylcarbonylimino- oxazoline terminated, 239 1,4-cyclohexylene-di• synthesis procedure, 239 methYlene-l,4-cyclo• Poly(ethyl methacrylate) hexyleneiminocarbonyl) characterization 353, 358 structure, 67 living anionic polymer, 358 synthesis and properties, 69 purification, 351 Poly (2, 4-furandiylcarbonylimino- Polyethylene 1,4-cyclohexylenedimethyl• hydrogenated polybutadiene, 335 methylene-l,4-cyclo• Polyethylene glycol hexyleneiminocarbonyl) bis(mercaptoacetate) derivative, synthesis procedure, 85 225 Poly(2,4-furandiylcarbonylimino- bis(mercaptopropionate) deriva• 1,4-cyclohexylenemethylene- tive, 225 1,4-cyclohexyleneimino• thio derivatives, 228, 229 carbonyl) Poly(ethylene oxide) structure, 67 oxazoline terminated, 238, 239 synthesis and properties, 69, 85 Poly(ethylene oxide-~-polystyrene) Poly(2,4-furandiylcarbonyloxy-l,4- polymer characterization, 476 phenylenedioxothio-l,4- polymer properties, 478 phenyleneoxycarbonyl) synthesis procedure, 465-475 synthesis procedure, 84 water absorbency, 478 Poly(2,4-furandiylcarbonyloxy-l,4- Poly(ethylene-co-propylene) phenylenedimethylmethylene- synthesis procedure, 335 1,4-phenyleneoxycarbonyl) Poly(ethylene terephthalate) synthesis procedure, 83 crystallinity, 179 properties, 54

541 Poly(2,4-furandiylcarbonyloxy-l,4- Poly (2, 4-hexadiene) phenylenethio-l,4-phenyl• IR characterization, 493 eneoxycarbonyl) NMR characterization, 492 synthesis procedure, 84 physical properties, 491, 494 Poly(2,5-furandiylcarbonylimino- polymer microstructure, 491, 502 1,4-cyclohexylenedimethyl• x-ray diffraction characteriza- methylene-l,4-cyclohexyl• tion, 493, 494 eneiminocarbonyl) threo and erythro configurations, synthesis procedure, 80 494 Poly (2, 5-furandiylcarbonylimino- thermal properties, 496 1,4-cyclohexylenemethylene- Poly (S-hydroxybutyrate) 1,4-cyclohexyleneimino• optically active, 445 carbonyl) synthesis procedure, 445 synthesis procedure, 81 Poly (4-hydroxy-L-proline) Poly(2,5-furandiylcarbonyloxy• ordered conformation disruption, ethyleneoxycarbonyl) 438 synthesis conditions, 52 Poly(iso-butyl methacrylate) Poly(2,5-furandiylcarbonyloxy-l,4- glass transition temperature, 359 phenylenedimethylmethylene- isotactic stereochemistry, 359 1,4-phenyleneoxycarbonyl) polymerization solvents, 359 polymerization techniques, 55 purification, 351 properties, 55 syndiotactic stereochemistry, 359 Poly(2,5-furandiylcarbonyloxy-l,4- thermal properties, 359 phenylenedimethylmethylene- Polyisocyanates, 231 1,4-phenyleneoxycarbonyl) Poly (isocyanurate-oxazolidone) synthesis procedure, 79 resin properties, 256 Poly(2,5-furandiylcarbonyloxy-l,4- Polyisoprene phenylenedioxothio-l,4- cis-1,4-microstructure, 333, 334 phenyleneoxycarbonyl) high cis content, 483 synthesis procedure, 79 metalated with alkyllithium- Poly(2,5-furandiylcarbonyloxy-l,4- diamine complexes, 336 phenylenethio-l,4-phenyl• polymer microstructure, 502 eneoxycarbonyl) Polyisoprene, block copolymer synthesis procedure, 79 hydrogenation, 335 Poly(3,4-furandiylcarbonylimino- Polyisoprene, grafting 1,4-cyclohexylenedimethyl• polystyrene branches, 337 methylene-l,4-cyclohexyl• Polyisoprene, living polymer eneiminocarbonyl) macromer formation, 461 synthesis procedure, 82 Poly(isoprene-i-styrene) Poly (3, 4-furandiylcarbonylimino- synthesis procedure by metalation 1,4-cyclohexylene• reaction, 336, 337 methylene-l,4-cyclohexyl• Poly (isoprenyl) lithium eneiminocarbonyl) aldimine trimethylsilyl synthesis procedure, 83 reaction, 330 Poly(3,4-furandiylcarbonyloxy-l,4- anionic polymerization phenylenedimethylmethyl• initiator, 334 ene-1,4-phenyleneoxy• carbon dioxide reaction, 329 carbonyl) Poly(lactide), 442 synthesis procedure, 81 Poly (DL-lactide) Poly(3,4-furandiylcarbonyloxy-l,4- crystallinity, 442 phenylenedioxothio-1,4- Poly(L-lactide) phenyleneoxycarbonyl) crystallinity, 442 synthesis procedure, 82 Poly (L-lactide-co-D-lactide) Poly(3,4-furandiylcarbonyloxy-l,4- crystallinity, 442 phenylenethio-l,4-phenyl• Poly(lactones) eneoxycarbonyl) high optical purity polymers, 442 synthesis procedure, 82 optically active synthesis, 441 Poly (p-halomethylstyrene) Polymer, blends poly(styryl)lithium coupling, 338 anionic prepared polymers as component, 342

542 Polymer, blends (continued) Polymerization, dispersion, compatiblizer synthesis, 463 (continued) tactic poly(methyl methacrylate), kinetics for anionic, 390-392 363, 364 solvent effects, 386 Polymerization Polymerization, emulsion, 831 amphi-ionic type, 248 2,3-dimethyl-1,3-butadiene, 495 anionic type, 321, 322, 327, 462 Polymerization, grafting benzene with sulfur, 159, 171 methods available, 406, 408 cationic method, 462 synthetic biopolymers, 405 chain termination, 321, 322 Polymerization, interfacial chain transfer, 321, 322 dicarboxylic acid salts-organo• group transfer method, 327 metallic halides, 187, high temperature melt method, 191 188, 191, 192, 194 inifer method, 462 polyamides production, 56 living ionic method, 339 polyarylates production, 97, 105 optically active S-propio- polyester production, 54, 64 lactones, 449 polysulfones synthesis, 97, 101, particle producing type, 381 104 radical procedure, 462 Polymerization, living anionic ring opening type, 27, 28, 33, 48 styrene-t-butylstyrene diblock, stereospecific type, 323 382, 383 Polymerization, anionic, 381 Polymerization, radical alkyllithium initiators, 382, 383 dispersion type, 382 butadiene, 347 macromers, 463 controlled method, 325, 361 polystyrene macromer production, dienes, 333-335 462 dispersion type kinetics, 390-396 Polymerization, step-growth ethylene oxide-polystyrene epoxy anchimeric assisted, 143 ether macromer, 465, Polymerization, stereospecific 470-475 1,3-dienes, 483-485 isoprene, 347 Polymerization, suspension, 381 lactones, 441, 447, 450 Polymers methacrylate molecular weight acid terminated, 328, 329 control, 361 amine terminated, 330 methacrylates, alkyl, 347 anionic chain ends, 321 methacryloyl terminated anionic grafting, 336, 337 polystyrenes, 463 anionic produced, 321, 322 polar solvent effects, 360 antiplatelet grafted, 291 polymer grafting tool, 406 benzene-sulfur containing, poly(a-methylstyryl) lithium, 338 14 159-161, 163-168, 170 poly(styryl) lithium, 338 c labeling, 295 styrene, 347 carbanionic chain ends, 323 styrene dispersion, 381-388, carbonation reaction, 328, 329 391, 392 chain end functionalization, 328 styrene rate constants, 392-395 diene containing, 483-503 vinyl monomers grafting, 407 difunctional growing ends, 324 Polymerization, cationic drug carrier, 293 lactones, 441, 447, 450 electrical properties, 134 macromer production, 462 electrophilic functionality macromonomer initiators, 239 grafting sites, 337, 338 tetrahydrofuran, 462 enamine carbonyl-ring Polymerization, coordination containing, 388 lactones, 441, 447, 450 flocculation prevention, 381 Polymerization, dispersion, functional telechelic, 203 381-383, 387, 389, 392 grafting from, 336, 406-408 anionic dispersion polymeriza• grafting onto, 336, 406-408 tion mechanism, 384, 385, greese thickeners, 382, 401 394, 395 hydroxyl terminated, 329, 330 diblock copolymer uses, 382, network type, 236 383, 389 organic fillers, 382

543 Polymers (continued) Polymers, liquid crystalline oxazolidone containing, 251, 254 (continued) oxazoline pendent groups, 236, microstructure, 134 237 physical properties, 134 oxazoline terminal groups, 236 poly(azomethines) type, 133 pigments use, 382, 401 polyenamine type, 133, 134 radical generation on surface, polyester type, 133 295 spacer groups, 134 surface active particle uses, 382 thermal characterization, 135 surface radicals containing, thermotropic type synthesis, 292, 293 133, 148, 158, 275, 278, thrombogenicity, 292 types, 134 vinyl monomer grafting by redox Polymers, living anionic formed radicals, 293, 299 aId trimethylsilyl reaction, Polymers, anionic 330 functionalization reactions, divinylbenzene end linking 327-329 reaction, 332 Polymers, carbanionic Polymers, living carbanionic coupling reactions, 332 ethylene oxide termination, 329 linking reactions, 332 Polymers, living type Polymers, carbanionic chain ended anionic synthesis methods, 408 electrophilic reagent reactions, carbanionic chain ended, 326 328, 329 grafting to anionic sites, 407 Polymers, comb-like Polymers, methacrylate poly(ethylene oxide) branches, anionic synthesis methods, 347 238, 239 Polymers, optically active Polymers, compatiblizers poly(8-propiolactones), 450-455 polystyrene macromer-ethylene 8-propiolactone polymers, 450 oxide copolymer, 463 stereocomplex blends, 455 Polymers, cyclic Polymers, a,w-2-oxazoline sub• formation reaction, 332, 333 stituted Polymers, dianion terminated synthesis procedures, 243 dibromoxylene reaction, 332, 333 Polymers, phase separated dichlorodimethylsilane reaction, anionic prepared polymers as 332 component, 342 Polymers, a,w-dilithium substituted Polymers, preformed ethylene oxide reaction, 329 coupling reactions, 337 Polymers, epoxide functionalized Polymers, radical derivatives poly(styryl)lithium coupling, 338 mechanism for reaction, 299 Polymers, functional Polymers, stereoblock oxazoline based, 235 isotactic-atactic-isotactic, 364 oxazoline chain ended, 238, 239, molecular complexes, 364 244 poly(methyl methacrylate) inter- oxazoline reactive groups, 236 molecular association, 364 Polymers, grafted properties, 364 bioactivity, 318 segmented molecular weights, 371 polymeric carbanion use, 338 syndiotactic-atactic-syndio- Polymers, halogenated tactic, 364 grafting attempts, 338 tacticities differences, 364, 369 transition metal reaction, 299 Polymers, stereocomplexes Polymers, hydroxy substituted tactic methacrylate thermal bisazlactone crosslinking, 220 properties, 363 Polymers, liquid crystalline Polymers, sulfur containing engineering properties, 134 characterization, 165, 166, 170, glass transition temperature, 135 171 isotropization temperature, 135 sulfonation, 165 lyotropic type, 275 thermal properties, 165, 171 main chain type, 133 Polymers, tactic mesogenic units, 133, 275 stereocomplex formation, 363, 364 mesomorphic properties, 148 helix blends, 363, 364

544 Polymers, telechelic Poly(methyl methacrylate) functional oligomers, 219 (continued) phenolic hydroxyl terminated, 248 syndiotactic polymer, 365 preparation methods, 324 synthesized from diphenylmethyl Poly (N-methyl-L-alanine) methacrylate, 372 cis- and trans-amide helices, 438 synthesized from trityl Poly(a-methylbenzyl methacrylate) methacrylate, 372 chiral stereocomplex blends, 457 radical polymerization method, Poly (a-methyl-a-ethyl-S-propio- 360 lac tones) tactic polymer complexes glass Bernouillian statistics, 447 transition temperature, 363 crystal structure-unit cell, thermal properties, 360 451-453, 455 time conversion plots,511 isotactic polymer, 447 Poly(methyl methacrylate-b-butadi• isotactic polymer stereo• ene-b-methyl methacrylate) complexes, 455-457 synthesis procedure, 323 physical properties, 451-453, Poly(methyl methacrylate-co-trityl 455-458 methacrylate) racemate polymer blends, 455-457 AB stereoblock synthesis, 377, stereocomplex blends physical 378 properties, 455-458 Poly(methyl methacryla~e), A-B triad sequence distribution, 447 stereoblock Poly(methacrylic acid), isotactic defined isotactic-syndiotactic diazomethane reaction, 368 segments, 364 trityl methacrylate polymer Poly(methyl methacrylate), atactic hydrolysis, 368 synthesis, 375 Poly(methyl methacrylate) Poly(methyl methacrylate), ABA stereoblock polymer, 378, 379 isotactic syndiotactic anionic polymerization, poly(methyl methacrylate) syndiotactic content, 365 stereocomplexes, 363, 364 atactic form, 363 synthesis from trityl meth• bifunctional initiator formed, acrylate, 365, 366 373 Poly(methyl methacrylate), syndio• characterization, 358 tactic glass transition temperature, isotactic poly(methyl meth• 360, 361, 363, 508 acrylate) intermolecular Grignard tactic segments, 364 association, 364 halogen terminated, 462 synthesis from diphenylmethyl high conversion polymer, methacrylate, 365, 366 506-510, 514 Poly(methyl methacrylate), tactic homopolymer stereoblock type, 364 diphenylmethyl methacrylate hydrolysis with esterification, polymer conversion, 371 365, 366 synthesis path molecular weight isotactic glass transition, 363 variations, 372 methyl methacrylate dispersions, tacticity stability analysis, 371 388 tacticity variation evaluation, macromer synthesis, 462 371 molecular weight studies, 369, trityl methacrylate polymer 370 conversion, 371 NMR stereochemistry study, 369 Poly(2-methyl-1,3-pentadiene) polymer tacticity, 372, 373 NMR characterization, 501 purification, 351 polymer microstructure, 500, 502 standard characterization, 357 polymer properties, 500 stereoblock polymer characteri- tacticity, 500 zation, 363 Poly(S-methyl-S-propiolactone) stereoblock polymer synthesis, synthesis procedure, 445 363 Poly (a-methyl-a-m-propyl-S-propio• stereochemistry, 373 lactone) syndiotactic glass transition, polymer optical purity, 443 363

545 Poly(a-methylstyryl) lithium Polypeptides (continued) chloromethylsilanated polymer molecular weight, 428 coupling, 338 mutarotation, 438 Poly (2-methylproline) oligomers synthesis, 190 disordering transition vinyl monomer grafting, 295 mechanism, 438 Poly(p-phenoxy-phenyl sulfide) substitution, 420 synthesis procedure, 177, 178 solution properties, 437 Polyphenylene Poly (2-methyl-L-proline) chemical doping, 182 helices stability, 438 Poly(phenylene sulfide) Poly (oxazolidones) benzene-sulfur monochloride branchin~ during formation, 254 reaction path, 177 catalysts for synthesis, 271 chemical resistance, 182, 183 characterization, 254-256 chlorobenzene-sulfur reaction crosslinking, 254 product, 175, 176 epoxide-isocyanate reaction crystallinity, 179 product, 254 engineering plastic, 173 film preparation, 258 flow and solution properties, 179 glass transition temperature 270, hydrogenation, 161, 167 271 infrared spectrum, 165, 166 IR characterization 266, 269, 270 molecular weight, 179, 180 linear polymer synthesis, 258, oxazoline terminated oligomers, 259, 263 237 properties, 267 Phillips process, 178, 179 synthesis conditions, 252, 267, Schmidt polymerization method, 271, 272 175 Poly(oxazolidones), linear sulfur-aluminum chloride properties, 264, 265 treatment, 167, 178 synthesis, 265 synthesis conditions, 159, 161, Poly(oxycellulose-~-polystyrene) 171, 177 characterization, 411, 412, 415 thermal properties, 178, 179, 181 Polyoxyethylenes properties, 183 methacryloyl terminated Poly (a-phenyl-a-ethyl macromers, 462 B-propiolactone) polymer extraction, 465, 475 isotactic physical properties, Polyoxyethylene, graft copolymer 451 emulsifying property, 465 racemic physical properties, 451 mechanical properties, 465 Polyphosphate amides water-absorbing property, 465 synthesis procedure, 188, 192 Polyoxyethylene, macromer grafted Polyphosphate esters characterization, 475 synthesis procedure, 188 emulsifying property, 478 uses, 190 purification method, 475 Polyphosphonamides water absorbing property, 478 synthesis, 190, 192 Polyoxyethylene, polystyrene Polyphosphonoanhydrides grafted synthesis from dicarboxylic emulsifying property, 480 acids, 195-200 microphase separation, 480 Polyphosphonates water absorbing property, 480 synthesis, 188 Poly(1,3-pentadiene) uses, 190 cis, trans-content, 485 Poly(L-pipecolic acid) characterization, 485, 489, 490 poly(L-proline) comparison, 438 polymer microstructure, 485, Polypiperylene 489, 502 IR characterization, 486 Polypeptides NMR characterization, 487, 488 circular dichroism physical properties, 489, 490 characterization, 420, 438 Polyproline conformational behavior, 419, 438 conformational structure, 419 degree of polymerization, 429 ordered conformation, 419 halogenation reaction, 295

546 Poly (L-proline) Polystyrene (continued) circular dichroism living polymer synthesis, 383, characterization, 430, 433 386, 388 cis and trans forms, 419 macromer grafting effici.ency, helices stability, 438 471-474 mutarotation, 420 methacryloyl terminated ordered conformation disruption, macromer~, 339, 340, 462, 439 463, 465, 470 Poly(B-propiolactones) molecular weight standards, 134 isotactic polymers, 442 peracetate functionalized, 400 optically active polymer, 441, peroxide formation, 331 442, 445 polymer properties, 398 racemic, 441 polystyrene grafted cellulose synthesis, 441 reinforced, 405 thermal properties, 442 prostacyclin grafted, 293 Poly(B-propiolactones), vinyl macromer synthesis, 461 Ct.-substituted Polystyrene, branched physical properties, 451-453 synthesis procedure, 332 Poly(B-propiolactones), Ct.-disub• Polystyrene, carbanion stituted, 442 grafting to cellulose, 410, 411, crystallization properties, 453, 413 454 Polystryrene, dilithium derivative Poly(B-propiolactones), Ct.- and B• methoxyamine/methyl lithium substituted, 442 reaction, 331 optically active polymer perparative procedure, 324 synthesis, 457 Polystyrene, physical properties, 457 synthesis procedure, 331 Polyproylene, isotactic Poly(styrene-B-butadiene-B-styrene) properties, 499 thermoplastic elastomer Polystyrene, 5, 410 synthesis, 322, 323 amine terminated synthesis, 330, Poly(styrene-b-t-butylstyrene) 331 diblock copolymer synthesis, anionic dispersion polymer 382, 383 characterization, 398, Poly(styrene-co-ethylene oxide) 399, 403 synthesis procedure, 478 anionic dispersion polymers as water absorbing property, 478 elastomer reinforcement, Poly(styrene-b-isoprenyl) lithium 400 carbon dioxIde reaction, 329 anionic dispersion polymer Poly(styryl) lithium rheological properties, 399 aId imine trimethylsilyl anionic polymerized particle reaction, 330 analysis, 397, 398 anionic polymerization applications dispersion polymer, initiator, 334 398-401, 403 carbon dioxide reaction, 329 dimer formation reaction, 331 chloromethylsilanated polymer dispersion flocculation coupling, 338 prevention, 387, 388 ketone dimer formation, 329 dispersion prepared molecular methoxyamine/methyllithium weights, 386 reaction, 330, 331 epoxy ether terminated, 461, molecular oxygen reaction, 331 464-469, 480 N,N,N',N'-tetramethylethylene• ethylbenzene diffusion diamine complex oxidation constants, 516 reaction, 331 glass transition temperatures, Polystyrene, epoxy ether terminated 390 epichlorohydrin copolymerization, grafting on cellulose, 405 480 living anionic polymerization ethylene oxide copolymerization, method, 342 463-466, 470-475, 478 living dispersion polymer macromers production, 463, particles, 398 466-469

547 Polystyrene, epoxy ether terminated Polytetrahydrofuran, methacryloyl propylene oxide copolymerization, terminated 480 radical homopolymerization, 463 Polystyrene, living polymer Poly(tetramethyl bisphenol A-ether active chain ends, 389 ketone) acetyl chloride reaction, 400 crosslinking reaction, 123 bis(dirnethylamino benzophenone) crosslinking mechanism, 130 capping reaction, 401 synthesis procedure, 122 crosslinked lithium stearate Poly(tetramethyl bisphenol A greese additive, 401, 403 sulfone) diisocyanate capping reaction, crosslinking reaction, 124-128 401, 403 Poly(thianthrylene sulfide) 1,1-diphenylethylene reaction, synthesis, 171, 177 470 Poly(trans-3-ethylproline) dispersion polymerization rotational isomerism, 420 mechanism, 403 Poly (D-trans-3-ethylproline) epichlorohydrin reaction, synthesis procedure, 428 463-470, 480 Poly(L-trans-3-ethylproline) ethylene oxide termination, 463, synthesis procedure, 428 470, 480 Poly(trans-3-ethyl-D-proline) hydroperoxide conversion, 400 circular dichroism leuco dye/pigment conversion, characterization, 430-437 401, 402 conformational studies, 419 macromer formation, 461 helices stability, 438 oxygen termination, 400 mutarotation, 437 reactive chain ends synthesis procedure, 419, 438 availability, 403 Poly(trans-3-ethyl-L-proline) synthesis procedure, 410 synthesis, 438 telechelic dispersion particles, Poly (trans-5-ethylproline) 399, 403 helices stability, 438 trimethyl chlorosilane Poly (trans-5-ethyl-D-proline) terminating agent, 388 conformational forms, 420 p-vinylbenzyl chloride reaction, Poly(trityl methacrylate) 461 conversion to poly(methyl Polystyrene, macromer methacrylate), 372 epoxy group terminated, 480 high molecular weight polymer, Polystyrene, metacryloyl terminated 372 butyl acrylate copolymerization, hydrolysis to acid polymer, 372 463 isotactic polymer synthesis, 2-hydroxyethyl methacrylate 364-366 copolymerization, 463 Poly(trityl methacrylate), Polysulfone isotactic oligomers, 108 hydrolysis, 368 synthesis, 96, 97, 106 Poly(trityl methacrylate), tactic Poly(sulfone-ester) conversion to poly(methyl characterization, 102, 103, methacrylate), 371 106-108 Poly(trity] methacrylate-co-di• segmented copolymer synthesis, phenyl methyl methacrylate) 99-109 AB stereoblock synthesis, 376, Polysulfone, oligomers 377 characterization, 98-103, 106 synthesis, 373-375 hydroxy terminated, 96, 97, stereochemistry, 374-377 101-103, 105-109 Poly(S-trichloromethyl segmented copolymers, 108, 109 S-propiolactone) synthesis, 97, 98, 100-105, 109 crystallization properties, 454 terephthaloyl chloride reaction, optically active polymer, 451 99, 100, 106-108 thermal properties, 454 Polytetrahydrofuran macromer use, 462

548 Poly (6-trifluoromethyl-6-methyl 6-Propiolactones, mono- and di• 6-propiolactone) substituted crystallization properties, 454 enantiomeric excess assay, 446 thermal properties, 454 6-Propiolactones, optically active Polyurethanes anionic polymerization, 450 acidic proton reactions, 337 ring opening polymerization, metalated with sodium, 337 449, 450 momomers, 59 6-Propiolactones, a- and 6- Polyurethanes, metalated substituted ethylene oxide grafting, 337 chiral europium salt complexes, ethylene sulfide grafting, 337 447 Poly(vinyl acetate) high pruity monomer synthesis, vinyl acetate dispersions, 388 442-447 Poly(vinyl alcohol) 6-Propiolactones, 6-substituted polymeric suspending agent, 381 polymerization with configura• Porphyrin tion retention, 450 diethylaluminum chloride adduct racemization polymerization, 450 catalyst, 451 ring opening polymerization Potassium acetate mechanisms, 450 Crown ether cocatalyst, 451 synthesis procedures, 457 PPO Propionyl hexafluoroantimonate bromomethylated product, 246 tetrahydrofuran polymerization NMR characterization, 247 to macromer, 462 oxazoline group substituted, 246 Prostacyclin thermal characterization, 247 grafted on polystyrene, 293 PPS synthesis, 293 compounding, 180 Prostaglandin, analogue Dow process, 175 platelet aggregation inhibitor, electrical properties, 181, 182 296 Macallum polymer, 175 Proteins mechanical properties, 180-182 halogenation reaction, 295 molecular weights, 174 macromolecule interactions, 419 poly(phenylene sulfide), 160, redox oxidation initiated 162, 167 grafting, 294 preparation from 4-halophenol, vinyl monomer grafting, 295 178 Pyridine properties, 174 anionic polymerization modifier, Schmidt, polymers, 175 360 synthesis routes, 174 anionic polymer coordinating uses, 174 agent, 326 L-Proline carbanionic species interaction, protein structure contribution, 326 419 polyanhydride synthesis 6-Propiolactones catalyst, 188 anionic ring opening polymeriza• Pyridinium bromide perbromide tion, 457 methyl coumalate reaction, 61, 73 cationic polymerization, 457 Pyridine dicarboxylic acid coordination catalyst polymeri• polyester monomers, 52 zation, 457 Pyrocatechol ketene-carbonyl reaction polyester monomer, 54 product, 445 Pyrrole dicarboxylic acids synthesis routes, 443 polyester monomers, 52 6-Propiolactones, enantiomer mixture Quaternary ammonium halides enantioelective polymerization, isocyanate-epoxide reaction 442 catalyst, 252 stereoelective polymerization, Quinidine 442 amino acid resolving agent, 425 chiral base, 446

549 Quinine Sodium naphthalene amino acid resolving agent, 425, polymer metalation reaction, 337 427 polystyryl dicarbanion synthesis optically active acid agent, 410 resolution, 444 Sodium sulfide hydrate, 173 Styrene Rayon, 405 alkyllithium polymerized, 326 Reaction injection molding anionic copolymerization, 335 azlactone oligomers, 232 anionic dispersion polymeriza- Reactivity ratios tion, 381-392 butadiene-styrene monomers, 336 anionic dispersion polymeriza• butyllithium copolymerizations, tion kinetics, 390-396 336 anionic dispersion polymeriza• styrene-t-butylstyrene monomers, tion rate constants, 384, 336 392, 394 styrene-p-methylstyrene monomers, anionic polymerization rates, 336 390-396 Redox oxidation systems anionic solution polymerization, polymers with mobile protons, 321, 322, 326, 347, 392, 292, 293 394 Resorcinol bis-triazolinedione reaction, I, polyester monomer, 54 2 Rhenium decacarbonyl butyllithium polymerized, 322, grafting catalyst, 299 323 purification, 308 s-butyllithium polymerized, 410 Reseotoxin B t-butylstyrene copolymerization, cycloclepsipeptide mycotoxin, 420 335 Ryton t-butylstyrene diblock copolymer• aluminum chloride degraded, 168 ization, 382, 383 poly(phenylene sulfide), 167, dibutyl magnesium water removal, 168, 173 348 properties, 179 living polymerization, 322, 323 p-methylstyrene copolymerization, SBR 335 polystyrene dispersion polymer purification, 408, 464 reinforcement, 400, 401 sodium naphthalene polymerized, Schotten-Baumann reaction 410 acid chloride-phenol reaction, sodium napthalene reaction, 324 189 Styryl hydroperoxide Siloxanes lithium salt, 400 anionic polymerization, 322 synthesis procedures, 400 Silver methacrylate Subtilisin trityl chloride reaction, 367 enzyme catalyst, 277 Sodium 4,4'-Sulfonyl diphenol liquid ammonium polymer polyester comonomer, 59, 65-68, metalation, 337 80, 82, 84, 86, 88 Sodium acetate purification, 72 B-propiolactone polymerization catalyst, 451 Tartaric Acid Sodium benzil amino acids resolution agent, 427 methyl methacrylate Tartaric acid, L-(+) isomer purification,354 amino acid resolution agent, 427 Sodium ethoxide Telechelics Michael addition catalyst, 420 synthetic techniques, 134 Sodium hydride 1,2,5-Thiadiazole-3,4-dicarbonyl polymer metalation reaction, 337 dichloride Sodium methylsulfinyl carbanion polyamides produced from, 55, 56 polymer metalation reagent, 337 Thianthrene benzene-sulfur reaction intermediate, 170, 177

550 Thianthrene (continued) Tetraethylammonium bromide phenylene sulfide biproduct, (continued) 159-162, 169, 170 isocyanate trimerization PPS synthesis intermediate, 175 catalyst, 266, 267 Thiiranes oxazolidone formation catalyst, chiral initiators polymerization, 258 442 Tetraethyleneglycol dimeth• 4,4'-Thiodiphenol acrylate, 301 polyester comonomer, 59, 65, Tetrafluoroethylene 67-70, 79, 82, 84, 87, 88 glow d1.scharge medium, 292 purification, 72 Tetrahydrofuran, 139 3,4-Thiofurazan dicarbonyl anionic Lewis base modifier, dichloride 335, 396 polyamide monomer, 55 anionic polymerization solvent, Thionyl chloride, 72 329, 464, 468 Thiophenol cationic polymerization, 462 PPS production intermediate, Lewis base, 324 176, 177 polymerization solvent, 324, 325 synthesis, 160, 162, 170, 171 Tetrahydrofuroic acid thionyl chloride condensation, polyesters, 54 177 1,3,4-Tetrahydrooxadiazine ring 2,4-Thiophene dicarboxylic acid synthesis, 1 polyester monomers, 52 Tetrakis-(triphenylphosphine) Terephthalic acid, 192, 194 palladium adipoyl chloride copolymeriza• catalyst for PPS synthesis, 178 tion, 188 Tetramethyl bisphenol A crystallographic dimensions, 58 IR analysis, 120 a,w-glycol polyesterification, NMR analysis, 120 53, 56 mass spectrum, 121 polyamide monomers, 57 poly(arylether) monomer, 188 polyester monomer, 53, 56, 58-60 synthesis procedure, 119 sebacyl chloride copolymeriza- Tetramethylbisphenol A, ketone, 125 tion, 188 N,N,N',N'-Tetramethylethylene• Terephthalic acid, metal salts diamine phosphorus acid chloride alkyllithium complexes for condensation, 195 polymer methalation, 336, Terephthaloyl chloride 337 copolyamides, 60 anionic polymerization modifier, diamine polycondensation, 60 334 dicarboxylic acid polyisoprene microstructure polymerization, 188 modifier, 334 polyarylate synthesis, 94-96, N,N,N',N'-Tetramethylethylene• 99-101, 106-109 diamine complex purification, 97 poly(styryl)lithium oxidation 4,4'-sulfonyldiphenol polyester, agent, 331, 336 59, 60 Tetramethylene glycol Tetrabutylammonium hydrogen sulfate 2,5-furandicarboxylic acid phase transfer catalyst, 136-138 polyester, 53 Tetrabutylammonium iodide 1,1,4,4-Tetraphenylbutane, lithium cyanoacrylates initiator, 327 dianion Tetracyanoethylene anionic bifunctional initiator, Diels-Alder reaction, 1 373, 379 2,2,3,3-Tetrachloro-l,4-butanediol synthesis procedure, 367 polyester monomer, 53 Tetraphenyl porphyrin 1,1,2,2-Tetrachloroethane, 97, 246 diethylaluminum chloride complex polyamide solvent, 69, 70 lactone polymerization, 450 Tetraethylammonium bromide, 257, 2,4-Toluene diisocyanate 261, 264, 265 anionic living polystyrene isocyanate epoxide reaction reaction, 401 catalyst, 259, 262 epoxide reaction, 252

551 p-Toluenesulfonic acid Triethylaluminum hydrate bisazlactone reaction catalyst. B-propiolactone polymerization 220. 227 catalyst. 450 catalyst. 280 Triethylamine. 69. 71. 225 monohydrate. 279. 282 N-carboxyanhydrides polymeriza• p-toluene sulfonylhydrazide tion catalyst. 428 diene hydrogenation catalyst. 335 B-propiolactone polymerization N-(p-Toluene sulfonyl)-cis-3- catalyst. 451 ethylproline. methyl ester Triethylenediamine base saponification. 438 isocyanate-epoxide reaction NMR characterization. 424. 425 catalyst. 267-269 N-(p-Toluenesulfonyl)-3-ethyl• oxazolidone formation catalyst. proline. cis and trans. 270-272 methyl esters Triethyloxonium tetrafluoroborate NMR characterization. 424-426 tetrahydrofuran polymerization separation procedure. 423 catalyst. 462 N-(p-Toluenesulfonyl)-trans-3- Triethylphosphate ethyl-proline. methyl ester polyanhydride solvent. 193 base saponification. 438 Triethylphosphine brucine resolution. 427 cyanoacrylates initiator. 327 quinine resolution. 427 Trifluoroacetic acid. 279 NMR characterization. 424. 425 3-ethylproline polymer solvent. Toxins 429. 430, 433. 436. 437 polypeptides. 419 isotactic poly(B-propiolactone) Trialkyl aluminum solvent, 451 alcohol reactions. 355 polyamide solvent, 69 methacrylate monomer s-2,2.2-Trifluoro-(anthryl-9)-1- purification. 361 ethanol methyl methacrylate complex. B-lactone diastereoisomer 354. 355 complex resolution, 446 monomer purification reagent. 326 2. 2. 2-Trifluoroethanol rare earth chloride complex 3-ethylproline polymer solvent, catalysts. 483. 484 429, 430. 434. 437 Triazolinedione isotactic poly(B-propiolactone) ene reaction. 2 solvent. 451 B-Dicarbonyl compound adducts. 2 Trifluoromethanesulfonic acid hydroxyl group reaction. 14 cyanoacrylate polymerization chain extenders. 3. 13 inhibitor, 327 crosslinking agent. 3. 13 Triisobutyl aluminum, 464. 470-472 reactions. 3 active hydrogen scavenger, 473 solvents. 2 epoxide polymerization catalyst, styrene reaction. 1 465, 470. 471 vinyl ether reactions. 1 Trimethyl aluminum 1.2.4-Trichlorobenzene. 161. 163. inifer polymerization catalyst, 164. 167. 168. 170. 171 462 PPS trifunctional comonomer. 174 Trimethylchlorosilane polydiene solvent. 495 anionic living polymer B-Trichloromethyl-B-propiolactone terminating agent, 388 optically active monomer 3,6,8-Trimethyl-3.4-dihydro-2H-1,3- preparation. 446 benzoxazine polymer produced from. 447 phenol reactions, 29 polymerization to optically 2.4-ditert-butylphenol reaction, active polymer. 451 34, 35 Triethyl aluminum Trimethylene glycol alkyl methacrylate treatment 2,5-furanedicarboxylic acid agent. 350 polyester, 53, 56 B-propiolactone polymerization. Trimethylsiloxy lithium 450. 451 cyclic siloxane polymerization methacrylate monomer catalyst. 462 purification. 354. 356-358

552 Tri-n-octyl aluminum m-Vinylbenzyl ether alkyl methacrylate treatment p-hydroxyphenyl-2-oxazoline agent, 350 substituted, 244 methyl methacrylate purification p-Vinylbenzyl ether agent. 355. 357 p-hydroxyphenyl-2-oxazoline Tripeptides substituted. 244 synthesis. 190 2-Vinyl-4.4-dimethylazlactone Triphenyl phosphite. 72 Jeffamine reaction. 213-216 Tris-[3-hepta fluoropropyl)hydroxy• ORTEP plots. 211 methylene)-d- synthesis procedure, 206 camphorato] europium III Vinyl esters substituted a-propiolactone bis-triazolinedione reaction. 2 optical resolution. 447 triazolinedione reactions. 2 Trityl methacrylate Vinyl ethers anionic polymerization. 364. triazolinediones reaction. 1 368, 371-373 Vinyllithium diphenylmethyllithium polymerization initiator. 461 polymerized, 371 polystyrene catalyst. 461 diphenylmethyl methacrylene 2-Vinyl-2-oxazoline anionic copolymerization. free radical polymerization. 237 373-377 Vinyl pyridine purification. 367 anionic polymerization, 322. silver methacrylate reaction, 367 326. 327 sequential polymerization. 366, N-Vinylpyrrolidone. 307 368 grafting on Pellethane, 315 synthesis procedure. 367 hydroxyethyl methacrylate co• Trommsdorff effect polymerization details. methacrylates polymerization, 506 316 polymerization with haloesters, Vandenberg catalyst 17 bimetallic-oxo-alkoxides, 480 Vrentas-Duda free volume theory Van der Walls radii methyl methacrylate t-. 388 polymerization system, 515 Vanillin manufacture. 14 Williamson reaction Vinylazlactone etherification of phenol substi• bismercaptane product tuted oxazoline. 242. 243 characterization, 226 Michael addition reaction. 224 m-Xylylenediamine, 279. 282, 284 synthesis, 225 Vinylbenzyl chloride Zwitterionic molecules, 1 p-hydroxyphenyl-2-oxazoline etherification, 244

553