ABES. See Automated Bonding Evaluation System Ablatives, 271

Index

A Addition cure ABES. See Automated bonding evaluation allyl, 84 system catalyst free, 84 Ablatives, 271 hydrophobic, 84 carbon-phenolic composites, 279 Additive, mechanical recycling, 518 nozzles, 280 Adhesives, 160 rayon, 279 AFM. See Atomic force microscopy reusable solid rocket motors (RSRMs), Aircraft brakes 279, 280 carbon vapor deposition (CVD), 278 rocket nozzles, 279, 280 polyacrylonitrile fabric, 279 Space Shuttle, 279 pre-form, 279 Abrasive cloth, heavy duty grinding, 341 Aircraft friction, 271, 277–279 Abrasive paper carbon–carbon, 263 kraft paper, 342 Aircraft interiors, 271–273, 294 waterproof ﬁnishing, 342 core crush, 272 wood sanding, 342 crush core, 271 Abrasive products ﬂat panels, 271 1 abrasive tools, 308 Nomex , 271 cutting tools, 308 products, 272 Abrasives requirements, 272 bonded abrasives, 307 sandwiching, 271 coated abrasives, 307 Aldehyde monomers grinding wheels, 307 acetaldehyde, 373 Abrasive tool hydroxy benzaldehyde, 372 grains, 308 Aldehydes, 26, 39 work material, 308 Aliphatic aldehydes, 26 Acceleration, 172, 174 Alkali, 52 Acetic acid, 16 Alkaline metal hydroxides, 52 Acetone, 9, 11, 13, 14, 17, 18, 20–22 Alkylphenols, 10, 13, 19–20 Acetophenone, 16 Alumina Acetylsalicylic acid, 11 A, 313 Acid, p-toluenesulfonic, 473 HA, 313 Acid curing, 203 PA, 313

529 530 Index

WA, 313 hard composites, 275 Amine, tertiary, 476 helmets, 276 Ammonia, 465 HJ1 armor system, 275, 276 2 and 4-hydroxymethylphenol (HMP), Kevlar, 275, 276 170, 171, 173, 174 para-aramid fiber, 275 Appendage polyethylene fibers, 275 allyl, 42 requirements, 276 ethynyl, 42 S-2 glass, 275, 276 Applications spectra, 275 cement, 508 Bamboo, 169 glass melting furnaces, 508 Bench life, 470 incinerators, 508 Benzene, 9, 11, 12, 14, 22 linings for steel Benzoxazine (BZ), 71, 72, 75, 87, 267, basic oxygen furnace, 509 273, 526 blast furnace, 509 co-reactions, 4, 527 continuous casting equipment, 509 electronics, 4, 527 electric furnace, 509 excellent dimensional stability, 42 secondary refining equipment, 509 fiber reinforced composites, 4 torpedo car, 509 Gurit, 42, 72 Asbestos-free, 345, 360 Henkel, 42, 72 AsWood, 162 intermediates, 83 Atomic Absorption spectroscopy (AA), low dielectric properties, 42 118–119 low water absorption, 42 Atomic force microscopy (AFM), 62, novolaks, 83 126, 130 ring opening, 42 Attenuated total reflectance (ATR), 109 Bicarbonates, 173 Autoclave, 271, 279–282 Binder component Automated bonding evaluation system epoxy resin, 337 (ABES), 126 hide glue, 337 Automotive applications, 384, 387, phenolic resin, 337 408–419 urea resin, 337 urethane resin, 337 B Binders Bac2, 81 bonded abrasive, 322 Backing material chemical, 455 cotton cloth, 318 cold-box, 487 kraft paper, 318 components, 221 nonwoven nylon, 318 core, 451 polyester, 318 core/mold, 455 vulcanized fiber, 318 foundry, 451 Baekeland, 45 furfuryl alcohol-containing, 470 Bakelite, 1 hot-box, 469 heat and pressure patent, 1 inorganic, 454, 498 legacy, 1 alumina cement, 508 Ballistics, 275–277 bittern, 508 composite armor, 275 sodium phosphate, 508 dyneema, 275 lignite, 499 Index 531

low emission, 498 Butyl rubber bladders, 446 metal bond, 310 BZ. See Benzoxazine mold/core, 460 organic, 454, 455 furan resin, 508 C molasses, 508 California Air Resources Board (CARB), phenolic resin, 508 162 pitch, 508 formaldehyde emissions, 2, 525 polyvinyl alcohol, 508 Phase I, 525 phenolic-based, 497 Phase I, 2 phenolic resin, 474 Phase II, 2, 525 polysaccharide-based, 499 Caprolactame, 19 protein-based, 498 CARB. See California Air Resources Board resin-based, 497 Carbohydrates, 175 resinoid, 322 Carbolic oil, 19 resinoid bond, 310 Carbon, 267, 269, 271, 277–279, rubber, 322 282, 296, 302 synthetic, 460 glassy carbon, 513 vitrified bond, 310 graphitizable carbon, 513 vitrified, metal, 322 Carbonates, 172, 174, 179 warm-box, 469 Carbon fiber reinforced phenolic molding Biodiesel, 487 compounds, 425–428 Bipolar plates, 81 Carbon-phenolic composites, 277 Bismaleimide (BMI), 69, 84, 85, 87 Cargo liners Bisphenol, 9–11, 13, 19, 22, 71 impact resistance, 274 Bisphenol-A, 54, 55, 66 requirements, 274 Bisphenol F, 41, 53–55, 58, 60, 66, Casting 79, 87, 527 aluminum, 461 epoxy diluent, 528 blocks, 456 PAPS, 528 boxless, 486 polycarbonate resin, 528 die, 456 Blowing agents, 190, 195, 196, 198, differential, 456 200, 202, 203 engine, 468 BMC. See Bulk molding compound ferrous, 451 BMI. See Bismaleimide flaskless, 486 Bond, 320 heads, 456 Bonded abrasive structure iron, 457, 466 bond, 307 nonferrous, 451 grain, 307 steel, 475 pore, 307 suspension, 456 voids, 307 Catalysts, 273, 283, 287, 292, 293, BPO, 87 296, 298, 299, 301, 302 B-stage, 277, 278, 281 oxalic acid, 149 BT resin, 69 patented delayed action catalysts, 267 Bubble columns, 15, 16 sulfuric acid, 149 Bulk molding compound (BMC), 275, Caustic soda (NaOH), 16, 18–22 293–295 CBN grinding wheels, 336 532 Index

CE. See Cyanate esters Continuous-ﬂow stirred-tank reactor CERP, 465 (CSTR), 48, 86 Challenges methylolated phenols, 527 cross-link density, 266, 267 Continuous press, 163 shrinkage, 266, 267, 273, 287, 292 ContiTherm1, 163 volatiles, 265, 266, 273, 279–281, 287, Cores 292, 296, 299 boiler, 468 Charged aerosol detector, 105 CO2-hardened, 482 Chemistry, 170 cold-box, 456 Chemometrics/PLS algorithms, 112 hollow, 463 China, 160, 161 hot-box, 456 Chloroprene, 440–441 rotor, 468 Chopped strands, 271, 296, 299 solid, 463 Cleavage, 16–18, 20–22 water jacket, 468 CNE. See o-cresol formaldehyde Cresols, 9, 10, 19–21 novolak epoxy Cresylic acids, 20 Coal, 19 Cross-link, 181 Coal tar, 9–11, 19, 20 CSTR. See Continuous-ﬂow stirred-tank Coast Guard, 290, 292 reactor Coated abrasives CTBN, 75 backing, 337 CTE, 71 backing material, 308 Cumene, 9, 11, 13–19, 22 binder, 337 Cumene hydroperoxide (CHP), 9, 13, cloth, 308 15–18 grain, 308, 337 Cumene-to phenol process, 9, 11, 13–15, non-woven, 308 19, 21 paper, 308 Cumylphenols, 17 vulcanized paper, 308 Curelastomer Coatings, 490 curing behavior, 76 Cold-setting, 176, 177 special rheometer, 76 Combustion Cure rate, 163 energy recovery, 518 Curie-point pyrolyzer, 104 thermal recycling, 518 Curing Commercial, 263 cold, 460 aircraft gas, 460 Airbus, 3 hot, 460 Boeing, 3 warm, 460 FST, 4 Curing process Commutator applications, 406–408 oven, 326 Composite, 155 program patterns, 326 Composites market, 263–266 Cut-off wheels, glass cloth insert, Compression molding, 266, 271, 276, 332 280, 293–295 Cutting tools Computer simulation, 48 bits, 308 Condensation, 170, 171 work material, 308 Confocal laser scanning microscopy, Cyanate esters (CE), 68, 70–72, 87, 129 273 Consumption, 157 bisphenols, 68 Index 533

phenolic novolaks, 68 DOPO, ﬂame retardant, 42 trimerization, 68 Double vacuum bag (DVB) process, 281 Cyclohexanone, 13, 19 Downturn, 158 DPM. See Dihydroxy diphenyl methylene Dry blending, 165 D DSC. See Differential Scanning Calorimetry DEA. See Dielectric analysis DVB. See Double vacuum bag process Decorative laminates, 244, 247–259 Dynamic mechanical analysis (DMA), 62, Degussa, Evonik, 82 63, 123–125 Depressed center grinding wheels, 333 Developing regions, 158 E 2,4-DHMP. See 2,4-Dihdroxymethyl ECN. See Epoxy o-cresol novolak phenol Electrical applications, 404–406 Diacetone alcohol, 17 Electrical laminates, 69 Diamond grinding wheels, 336 Emissions, 457 Diazo naphtho quinone (DNQ), 364–365 Emulsiﬁers, 190, 200–202, 204 Dicumyl peroxide (DCP), 17, 18 Emulsion, 180 Dielectric analysis (DEA), 126 Emulsion polymer isocyanate (EPI), 168 Dielectric constant, 69 End of cure, 124 Differential scanning calorimetry (DSC), Energy, 159, 180 49, 50, 63, 79, 121–123, 179 Environmental impact, 156 2,4-Dihdroxymethyl phenol (2,4-DHMP), formaldehyde, 511 45, 46, 170 hexamethylenetetramine, 511 9,10-Dihydro-9-oxa-10- phenol, 511 phosphaphenanthrene (DOPO) Enzyme DOPO-HB, 67 formaldehyde free, 65 DOPO-PN, 67 HRP, 65 ODOPB, 67 SBP, 65 Dihydroxy diphenyl methylene (DPM) EPA method 8315A, 97 o,p’, 46 EPI. See Emulsion polymer isocyanate p,p’, 46 Epoxide resins, 11, 22 Dimethylbenzyl alcohol, 16 Epoxies, 69, 71, 84 Dimethylol, 52 Epoxy o-cresol novolak (ECN), 67 Dimethylol phenol, 45 Esters 2,6-Dimethylol phenol (2,6-DMP), 53 dibasic, 483 Dinitrophenylhydrazine, 97 methyl, 487 Dioctyl adipate, 483 Ether, benzylic, 477 Diphenyl methylene diisocyanate (MDI), Evaporative light scattering detector, 105 160, 178, 179, 182 Exterior, 166 polymeric, 476 Extraction, 18, 19 Direct oxidation, 9, 11, 12 Extruder, 165 Dissipation factor, 69 Distillation, 9, 14, 16–19, 21, 22 DMA. See Dynamic mechanical analysis F 2,6-DMP. See 2,6-Dimethylol phenol F****, 162 3D network, 80 Fabrication processes, 269–303 DOPO. See 9,10-Dihydro-9-oxa-10- Factory Mutual Research protocol, 286 phosphaphenanthrene Fast cure systems 534 Index

resorcinol, 3 Fire, smoke and toxicity (FST), 265–268, tannins, 3 271, 274, 276, 282, 287, 288, 290, 294 Faster curing, 272, 273 characteristics, 63 Fatigue, 403–404, 417, 418, 421, 435–437 properties, 275 Features of phenolic resins Fire testing, 205 fixed carbon, 510 Flexibility, 356–358 green body strength, 510 Floral foam, 192–193 hazardous properties, 510 Fluorescence microscopy, 129 size stability, 510 f-MWNT. See Functionalized multi-wall Ferriox, 58 carbon nanotubes Fiberglass, 269, 275, 289, 293, 296 Foam, 165 manufacturers, 268 resins, 201–203 phenolic compatible, 268 structure, 190–192 S-2 glass, 276 testing, 204–207 surface chemistry, 268 Foaming processes Fiber glass insulation batch, 197–198 formaldehyde free, 2 continuous, 198–200 Fiber reinforced plastics (FRP), 85 semi-continuous, 200 Fibers, 348, 351–354 Focused ion beam (FIB) microscopy, 129 aramid, 269 Formaldehyde, 13, 21, 22 boron, 269 adducts, 27 nylon, 270 Cannizzaro, 28 polyester, 270 consumption, 26, 32–35 quartz, 269 disproportionation reaction, 28 rayon, 270 metal oxide, 25, 29–31 single filament rovings, 270 methanol conversion, 31 unidirectional tapes made up of multiple silver catalyst, 29, 30 single filament yarns, 270 Formaldehyde analysis, 97–99 woven biaxial fabrics, 270 Formaldehyde emissions, 161, 162 Filament winding, 69, 283–289, 296, 298 Formic acid, 16 markets, 286, 287 Fourier transform infrared spectroscopy products, 286 (FTIR), 50, 53, 62 tow, 271, 285, 286 Freeze-drying, 122 Filament wound, 286, 289 Friction materials Fillers, 204, 386–389 brake lining, 345–347, 349, 351, alkaline metal oxide, 317 353, 359 calcium carbonate, 317 clutch, 345, 346, 349–350, 352–354, calcium chloride, 317 356, 359 calcium sulfate, 317 disk pad, 345–348, 350–353, 356, cryolite, 317 357, 360 glass chip, 317 FRP. See Fiber reinforced plastics iron, 317 FST. See Fire, smoke and toxicity mechanical recycling, 518 FTIR. See Fourier transform infrared sulfide, 317 spectroscopy wollastonite, 317 Fuel cells, 87 zinc sulfide, 317 Functional groups Finite element, 428–431 cyanate, 66 Fire, 263 epoxy, 66 Index 535

oxazine ring, 66 H Functionalized multi-wall carbon Hand lay-up, 266, 269, 280, 296, 299, nanotubes (f-MWNT), 69, 72 301–303 Furfuryl alcohol, 470 applications, 299, 301, 302 gel coat, 299, 301 surface paste, 299, 301, 303 G Hardboard, 168 Gas chromatography, 102–104 Hazardous air pollutant (HAP), 465 Gas chromatography-mass spectrometry HDF. See High density fiberboard (GC-MS), 102–104 Headspace gas chromatography (HS-GC), Gasification, 19 103 GCxGC. See Two dimensional gas Headspace gas chromatography mass chromatography spectrometry (HS-GC-MS), 103 Gel permeation chromatography (GPC), 58, Health and Safety 59, 61, 99–102 classification, 36, 37 number average Mw, 100 Heating polydispersity, 100 backing, 340 relative Mw, 101 jumbo roll, 340 weight average Mw, 100 oven, 340 z-average Mw, 100 Heavy-duty grinding wheel, 334–336 Gel point, 96 Hemiformal, 48, 50 Gel point/gel time, 125 Henkel, 42, 72 Generator, 485 Hexamine, 458 GIC, 71, 75 High carbon yield, 279 Glass cloth High char yield, 279 novolac, 318 High density fiberboard (HDF), 168 resole, 318 High ortho, 56, 77 Glass insulation, 52 transition metal salt, 43 Global consumption, 156 High ortho resins, divalent metal salts, 57 Glulam, 166, 176, 177 High pressure liquid chromatography GPC. See Gel permeation chromatography (HPLC), 50, 52, 104–106 Grain High pressure liquid chromatography mass alumina, 313 spectrometry (HPLC-MS), 104–106 dulled grain, 320 HILIC. See Hydrophobic interaction liquid self-renewing, 320 chromatography silicon carbide, 313 HMMT, 62 Grain size 2-HMP. See 2-Hydroxymethyl phenol fine size grain, 316 4-HMP. See 4-Hydroxymethyl phenol large size grain, 316 HN, 79 Greenhouse gases, 104 Honeycomb, 271, 273, 282, 283, 526 Green products, 161 require, 282 Grinding wheel requirements, 282 center-less grinding wheels, 334 Honeycomb core, 282 coolant water, 334 Honeymoon, 176 cylindrical grinding wheels, 334 Housing market, 158 roll grinding wheels, 334 HPLC. See High pressure liquid Gurit, 42, 72 chromatography 536 Index

HPLC-MS. See High pressure liquid L chromatography mass spectrometry Labor costs, 159 Huggins constant, 77 Lambda value, 203, 205–206 Hybrid, 178 Laminated veneer lumber (LVL), 157, 160, Hydrogenation, 18 164, 167, 180 Hydrogen peroxide (H2O2), 11, 12 Laminate properties, 256–259 Hydrolysis, 521 compact boards, 257 feedstock recycling, 520 fire-retardant laminates, 258–259 Hydroperoxide, cumene, 496 post formable laminates, 257 Hydrophobic interaction liquid standard HPL laminates, 256 chromatography (HILIC), 105 Laser light scattering, 101 Hydroxyacetone, 17, 18 Latent curing agents Hydroxymethyl, 174 amines, 81 2- and 4-Hydroxymethyl phenol (HMP), 45, hydroxylamine, 81 46, 52, 53 organic acids, 81 stable salt, 81 Latex dips, 449, 450 I LC-MS, 105 IARC. See International Agency for Lederer-Manasse reaction, 45 Research on Cancer Lexan, 66 Impact resistance, 287, 289 Lignin, 176, 499 Impact strength, 288 Linkages, 172 Impregnation process, 246, 249–250 Liquid, 165 Infrared (IR) Liquid crystal display (LCD) aromatic substitution bands, 110 size of the glass plate, 380 array detectors, 110 spin & slit, 380 band assignments, 109 Liquid resin microscopes, 109 base catalyst, 330 spectroscopy, 106–111 molecular weight, 330 Infusion molding, 266, 273, 296–303 viscosity, 330 Inhibitors, 484 LOI, 67 Insulation foam, 191–195, 202–207 Long fiber reinforced materials, 422–425 Insulation resin, peak identification table, Loss modulus, 123, 125 107–108 Low temperature curing systems, 287 Interference microscopy, 129 Lumber, 167 International Agency for Research on LVL. See Laminated veneer lumber Cancer (IARC), 36, 37, 162 IR. See Infrared Isocyanate, 179 M ISO methods, 99 Make coat table, 100 blistering, 339 spreading roll, 339 static electrical application, 339 J MALDI-TOF-MS, 102 Japan, 160 MALLS. See Multi angle laser light scattering K Manufacturing process, 143–145 KIC, 71, 75 for coated abrasives Kinetics, 169, 172 make coat, 337 Kraft, 176 size coat, 338 Index 537

heating/firing, 507–508 ortho, 45 mixing, 507 para, 45 molding, 507 a-Methylstyrene (AMS), 13, 16–18 for a resinoid grinding wheel MHS. See Mark-Houwink-Sakarada coated grain, 322 Microscopy mix, 322 glass-resin composites, 128 oven, 322 sample preparation, 127 press, 322 Microwave preheater, 164 Market factors, 159 MIL-R-9299C, 276, 280, 283 Market trends Mineral wool, 52 China, 312 application and properties, 218–220 Germany, 312 consolidated companies, 210 India, 312 emissions, 210, 211, 222–226, 228, Japan, 312 230, 231, 233, 238, 239 Thailand, 312 energy saving, 210, 211 USA, 311 glass wool, 211, 214–220, 238 Mark-Houwink-Sakarada (MHS), 42, 77 global aspects, 210–211 Mass spectrometry (MS) growth, 211, 220 ion trap/quadrupole, 105 insulation binder, 209–240 Materials, 87 insulation terms, 210–213 2-MBF. See 2-Methylbenzofurane market trends, 211 MDF. See Medium density fiberboard slag wool, 214, 218 MDI. See Diphenyl methylene diisocyanate spinner, 214, 215 Mechanical strength testing (of foam), stone wool, 211, 218–220 206–207 Mineral wool binders, 87 Medium density fiberboard (MDF), Mineral wool insulation 168, 182 ammonium sulfate, 3 Melamine formaldehyde, 526 reduced crystalline dimer, 3 Melamine formaldehyde (MF), oriented Mining foam, 191, 192, 195, 203, 205 strand board, 525 Mixing equipment Melamine–urea–formaldehyde (MUF), 182 high pressure, 198–200 wood panels, 2 low pressure, 198–200 Mesityloxide (MOX), 17, 18 Mixing process Meta–para cresol novolaks grain, 322 ADR, 366 liquid resin, 322 average molecular weight (Mw), 366 powdered filler, 324 Methanol, 16 powdered resin, 324 methanol process, 32 solvent, 322 Methods of classification, chemical Modifications, 273 composition, 504 impact modifiers, 267 2-Methylbenzofurane, 17, 18 phenolic backbone, 267 Methylene Diphenyl Isocyanate (MDI), 526 Modified novolaks oriented strand board, 525 alkyl halides, 65 Methylene glycol, 54 dialcohols, 65 Methyl formate, 493–494 diethers, 65 Methyl hydroperoxide (MHP), 16 olefin, 65 Methylol, 52 phenols, 65 Methylol phenol, 47, 181 rosin, 65 basic conditions, 45 Modulus of elasticity (MOE), 126 538 Index

MOE. See Modulus of elasticity chemical toolbox, 527 Moisture, 164, 166 multifunctional, 62 Molar ratio, 140, 141, 146 multifunctionality, 527 Molding compounds, 267, 271, 294, 295 nanoparticles, 62 carbon fiber, 4 novolak, 62 long glass fiber, 4 resole, 62 Molding materials scratch resistant, 3 carbon fiber, 526 thermooxidative stability, 3 long glass fiber, 526 NaOH, 171 Molding procedure Natural products cold press molding, 324 cashew, 75 hot press molding, 324 co-reactant, 42 semi-hot press molding, 324 furfural, 75 Molding process, 271, 294, 384, 392–398 furfuryl alcohol, 75 Molds lignin, 75 disposable (nonpermanent), 453 linseed oil, 75 metal, 468 soy, 75 resin-bonded, 454 starch, 75 reusable (permanent), 453 tannin, 75 sand, 468 tung oil, 75 Molecular weight distribution (MWD), Natural products 41, 57–59, 77, 87 phenol replacement, 42 Molecular weights of glycolated novolak, solvent, 42 120 Near infrared (NIR), 112–114 Monomers, 519, 521 band assignments, 113 chemical recycling, 518 glass/phenolic prepreg, 113 feedstock recycling, 518 in-line monitoring, 114 MPN, 85, 86 resin/wax adhesive, 113 MS. See Mass spectrometry Network MUF. See Melamine–urea–formaldehyde cure, 528 Multi angle laser light scattering (MALLS), linear novolak, 88, 528 102 novolak cure, 87 Multi-opening press, 271 New areas, carbon foam, 4 Multiwall carbon nanotubes (MWNT), 70 Nitrile, 440, 441 MUpF, 182 Nitrous oxide (N2O), 11 MWD. See Molecular weight distribution NMR. See Nuclear magnetic resonance MWNT. See Multiwall carbon nanotubes No-bake, alkyd oil, 481 Noise, 348, 349, 355–357, 359 Nomex1, 271, 282 N Nomex honeycomb, 272 Nanoclay, 64, 70 Non-Newtonian liquid, 125 Nanofabricated thermal probes, 129 Non-woven fabric Nanoindentation mapping, 129 heavy duty industrial application, 342 Nanoparticles, 499 household use, 342 Nanotechnology, 87 nylon, 342 ablation, 3 polyester, 342 BZ, 62 Normal phase liquid chromatography–GC, CE, 62 103 Index 539

North America, 157 Open/closed cell content (of foam), 190, Novolak curing agents 195, 207 bisoxazolines, 82 Optical ﬂuorescence microscopy, 126 BZ, 82 Optical microscopy, 128 hexa, 82 Oregon State University (OSU), 69 oxazolidines, 82 Organosolv, 177 solid resole, 82 Oriented strandboard (OSB), 157, 167, Novolak process, 41 178, 181, 182 PAPS, 4, 58 Oriented strand lumber (OSL), 167 phosphoric acid, 58 Ortho position, 52 Novolaks OSB. See Oriented strandboard acidic conditions, 43 OSL. See Oriented strand lumber BZ, 76 OSU. See Oregon State University mechanism of cure, 76 Other formaldehyde materials network, 76 cyclic Formals, 38 organophosphonic acid, 57 HMTA, 38 PAPS, 527 other aldehydes, 39 phenolic, 458 trioxane, 38 two-phase process, 57 Oven to B-stage, 282 Nuclear magnetic resonance (NMR), 48–50, Oxazolidine, 267 52–56, 79, 171 aminoalcohols, 42, 83 APT (attached proton test), 116 biocides, 84 computerized spectral assignments, 116 curing agent, 84 DEPT, 116, 117 PRF resins, 42 DQF COSY/TOCSY, 117 pultrusion, 42 formaldehyde, 97 release formaldehyde, 84 formaldehyde peak assignments, 98 Oxidation, 11, 16, 18 INEPT, 117 Oxygen, 9, 11–13, 15, 16 phenolic band assignments, 115 quantitation, 116 spectroscopy, 114, 117–118 P Palmarole, Adeka, 82 PAPS. See Phosphoric acid phase separation O Paraformaldehyde, 28, 37, 38, 55 o-cresol, 486 Parallel strand lumber (PSL), 167 o-cresol formaldehyde novolak epoxy Paramagnetic reagents, 117 (CNE), 67 Para position, 52 Off-shore, 286, 290, 292 Parquet, 169 Oil, 159, 178 Particle board (PB), 168 Oligomers, 521, 522 PB. See Particle board chemical recycling, 518 PBO. See Phenylene bisoxazoline dimeric, 45 PEI. See Polyether imide feedstock recycling, 518, 522 Peroxide, methyl ethyl ketone, 496 recycled material, 522 PES. See Plasma emission spectroscopy; trimeric, 45 Polyethersulfone virgin material, 522 Phenol, 9–22, 465 o-methylolphenol, 55, 57 Phenol formaldehyde co-reaction Onset of cure, 124 melamine, 4 540 Index

olefin, 4 Phenol monomers ring formation, 4 m-cresol, 370 urea, 4 meta–para cresol ratio, 370 Phenolic, 155, 383–437 p-cresol, 371 alkaline, 474 trimethylphenol, 370 Phenolic can coating GCxGC, 103 xylenol, 370 Phenolic foam, fiber reinforced, 4 Phenol removal, 18 Phenolic hydroxyl Phenol resorcinol formaldehyde (PRF), 168 allyl, 85 Phenol resorcinol formaldehyde (PRF) ethynyl groups, 85 resins, 84 Phenolic resin for coated abrasive Phenol-urea-formaldehyde (PUF), 180, 181 anti-blister agent, 341 Phenylene bisoxazoline (PBO), 526 base catalyst, 341 co-reactions, 527 high-boiling-point solvent, 341 high strength, 42 liquid resole, 341 high Tg, 42 viscosity, 341 hot wet strength, 4 Phenolic resin for insulating mineral wool improved toughness, 4 ammonium hydroxide, 231–234 novolak, 4 ammonium sulfate, 224, 235–239 polyaryl ether amide, 42 curing process, 236 toughness, 42, 83 de-dusting oil, 234 Phosphoric acid phase separation (PAPS), emulsifier, 234 59–61, 87 extenders, 225, 239–240 PI. See Polyimide general chemistry, 221–225 Plasma emission spectroscopy (PES), inorganic catalyzed resins, 224, 225 118–119 organic catalyzed resins, 224–225 Plasticisers, 203 PFU resin, 224 Plastics industry, cornerstone, 1 properties of insulation resins, 229–231 Plywood, 157, 160 silanes, 234–235 Plywood glue line, 127 urea, 223, 225–229 p-methylolphenol, 55 water, 221–223, 225, 240 PMUF, wood panels, 2 Phenolic resin for refractories PN, 85, 86 novolak Polycarbonates, 22 liquid novolak, 514 Polyether imide (PEI), 69 powdered novolak, 514 Polyethersulfone (PES), 69 resole Polyimide (PI), 69, 71 liquid resole, 514 Polyisocyanates, 470 powdered resole, 514 Polymer Phenolic resin, meta–para cresol novolaks, epoxies, 310 363 phenolic resin, 310 Phenolic resins, 9–11, 13, 19–22 polyimide, 310 Airbus, 526 thermoplastic polymer, 310 Boeing, 526 thermoset resins, 310 fiber reinforced composites, 526 urethanes, 310 high heat resistance, 527 Polyols 5 million tons/year, 2 aromatic, 480 plywood, 525 polyether, 479 pultrusion, 526 Polyphenylene oxide (PPO), 66, 69 Index 541

Polysiloxane, 289 shell, 462 Polysulfone, 69 shell molding, 462 Polyurethane (PUR), 71, 168 SO2-cured, 461 Pores, 320 solidification, 459 Powder resin vacuum distillation, 150 flow, 331 Process control instruments, 112–114 hexamine content, 331 Processing molecular weight, 331 belt, 340 particle size, 331 bonding, 341 PPO. See Polyphenylene oxide cutting, 341 Pre-preg/molding compound, 278 flap wheel, 340 Pre-pregs, 4, 271–273, 277, 279–281, jumbo roll, 340 285, 286, 293 roll, 340 epoxy, 273 shaping, 341 molding processes, 271 sheet, 340 novolac, 273 slitting, 341 rubber-modified, 273 Production line treater, 270 agitator, 149 Pressing process, 250–254 condenser, 148 CPL production, 254–255 discharger, 148 double band press, 254–255 distillation water tank, 148 HPL production, 251–254 jacket, 149 multi opening presses, 250–253 mass flow meter, 149 short cycle presses, 253–254 pastillator, 151 Pressure sensitive adhesives, 440–442 reactor, 148 PRF. See Phenol resorcinol formaldehyde steel belt conveyer, 151 Process tank, 148 acetal, 495 vacuum, 150 batch process, 151 Propylene carbonate, accelerator, 46 charge, 149 Protein, 181, 182 cold-box, 459 PSF. See Polysulfone continuous production process, 147 PSL. See Parallel strand lumber core, 457 PT-15, 69 coremaking, 451 PT resins, 68 dehydration, 150 PUF. See Phenol-urea-formaldehyde discharge, 150, 151 Pultruded FRPs, 291 gas curing, 460 Pultruded grating, 291 heat curing, 461 Pultrusion, 289–293, 296 high-pressure reaction, 151 glue-laminated timber beams, 291 hot-box, 459 markets, 289, 291 mold, 457 US suppliers, 292 molding, 455 PUR. See Polyurethane no-bake, 459 Purity phenolic urethane cold-box, 456 metal contamination, 377 precipitation, 459 particle, 377 production, 457 PVB, 277 reaction, 150 Pyrolysis, feedstock recycling, 519, 520 reflux, 150 Pyrolysis gas chromatography, 104 542 Index

Q furan, 460 Quality control methods, 99 furfuryl alcohol, 495 Quickstep process, 281, 282 hot-box, 466 Quinone methide, 53 nonmodiﬁed, 469 novolak, 461 organic, 451 R part 1, 477 Radio frequency, 164 part 2, 479 Railway market, test standards, 274 phenolic, 451 Raman spectroscopy, 62, 111–112 polyols, 480 carbon–carbon composites, 112 potassium-based, 475 curing/pyrolysis, 111 reactive, 459 reaction monitoring, 112 resin coated, 461 Raw materials, 144 resole, 468 analysis, 96–99 resorcinol, 458 catalyst, 140, 141, 146 sodium-based, 475 formaldehyde, 148 synthetic, 460 formalin, 141, 142, 146, 148 urea, 462 phenol, 140–142, 146, 148 Resin transfer molding (RTM), 69, 71, 72, Reaction monitoring, 110 86, 296, 299, 300 Reactivity, 170, 172 market, 297 Reclamation Resole curing systems mechanical, 475 acid, 80 thermal, 475 amides, 80 Regions, 160 anhydrides, 80 Renewable raw materials base, 80 cashew, 3, 528 carbonates, 80 furfural, 3 carboxylic acid esters, 80 lignin, 3, 528 thermal conditions, 80 linseed oil, 3 Resoles soy, 3 addition, 41, 47 tannins, 3, 528 base catalyst, 43 tung oil, 3 condensation, 47 Renewable raw materials molding, insulation resins, 41 87 methylol phenols, 46 Replacement, 175 mineral wool, 41 Resin infusion, 282 ortho-condensed, 470 Resins, 155 phenolic, 459 acrylate, 459 Resorcinol, 9, 10, 21–22, 177 acrylic, 496 Rheometry, 125 alkyd, 481 RN, 77, 79 amino, 500 RN-H, 77 A-stage, 95–96 RN-L, 77 base, 478 RTM. See Resin transfer molding benzylic ether, 477 RTM /VARTM, 263 B-stage, 95–96 Rubber reinforcing, 442, 448–449 C-stage, 95–96 Rubber tackiﬁers, 443–445 epoxy, 461 Runaway, 17 Index 543

S Semiconductor Sands ArF, 378 acid curing, 476 g, i-line, 378 acid demand value (ADV), 466 KrF, 378 alkali-free, 470 Shape alkaline, 494 shaped refractories, 504 blowing, 486 unshaped refractories, 504 chromite, 454 Sheet molding compound (SMC), 275, coated, 462 293–295 core, 457 SiC, 69 coremaking, 466 Silicate, sodium, 482 dry, 464 Silicon carbide free-ﬂowing, 464 C, 313 graphite, 454 GC, 313 green, 455 Single vacuum bag (SVB) process, 281 heated, 486 Size coat, 339–340 lake, 466 Size exclusion chromatography, mineral, 454 99–102 mixed, 484, 486 SMC. See Sheet molding compound moist, 468 Sodium phenate (NaPh), 13, 18 mold, 457 Solid fuel molding, 466, 470 energy recovery, 523 new, 475 life cycle assessment olivine, 454 (LCA), 524 precision, 456 Solid State NMR, 114 quartz, 454 Solvents reclaimed, 473, 474 furan-group, 330 resin coated, 459 furfural, 330 shakeout, 475 furfuryl alcohol, 330 shooting, 486 nonpolar, 483 silica, 454 polar, 483 spent, 475, 482 Solvolysis thermally regenerated, 475 feedstock recycling, 520 wet, 466 supercritical ﬂuid, 520 zircon, 454 Soyad, 182, 526 Sandwich, 263, 271–274, 282, 293 SpaceShipOne, 282 Sandwich panels, 282 Stabilizer Saturation testing (of foam), 207 guanamines, 31 Scanning electron microscopy (SEM), polyvinylalcohol, 32 62, 75, 126 Steam-air preheater, 163 Scrimber, 169 Storage modulus, 123, 125 SCRIMP, 298–299 Strength, 387–389, 394, 396, 398, 401, 404, market, 299 406–408, 410, 411, 414, 417, 418, 420, requirements, 299 422, 423, 427, 429, 431, 435, 437 Scrubber, 485 Structure, 166, 167, 173 Self-Accelerating-Decomposition- Substitution (Sn)/Unsubstitution (Un) Temperature (SADT), 16 indices, 117 SEM. See Scanning electron microscopy Sugar, 175 544 Index

Sulphonate, 176 Tolerance, 166 Super grain Toluene, 11, 20, 21 cubic boron nitride, 315 Toughened, 273 diamond, 315 Toughening agents Surface markets, 246–248 co-reactants, 74 System flexibility, 74 no-bake, 461 Toughness, 273, 274, 292, 301 phenolic, 461 Transmission electron microscopy (TEM), urethane, 461 62 Trends cost of energy, 86 T Triacetin, 174 Tan delta, 123, 125 Triethylamine (TEA), 52, 53 Tannins, 175, 176, 469 2,4,6-Trihydroxymethyl phenol (2,4, Tar, 18, 19 6-THMP), 46, 170, 171 Tar acids, 19, 20 Trihydroxymethyl phenol (THMP), 46 TEA. See Triethylamine Trimerization, 480 TEC. See Thermal expansion Trimethylol, 52 coefficient Trimethylol phenol, 45, 48 TEM. See Transmission electron Two dimensional gas chromatography microscopy (GCxGC), 103 Temperature, 473 Tetraethyl o-silicate (TEOS), 491 Tg, 71, 72, 78, 80, 82, 83, 86 TGA. See Thermal gravimetric analysis U TGA/IR, 121 Ultra high pressure liquid chromatography, Thermal decomposition, 104 105 Thermal expansion coefficient (TEC), 67 UL 94 V0, 67 Thermal gravimetric analysis (TGA), 61, Urea, 177 63, 69, 120–121 Urea formaldehyde (UF), 526 Thermal mechanical analysis (TMA), oriented strand board, 525 63, 126 Urea–resorcinol–formaldehyde (URF), Thermoplastic vulcanizates, 446 177 Thermoset resin market Urethane, 476 epoxies, 264 URF. See Urea–resorcinol–formaldehyde phenolic, 264 US suppliers, 292 polyesters, 264, 290, 291 vinyl esters, 264, 290, 291 Thixotropic agents, 204 V THMP. See Trihydroxymethyl phenol Vacuum assist resin transfer molding 2,4,6-THMP. See 2,4,6-Trihydroxymethyl (VARTM), 297, 298 phenol Vacuum bag, 263, 271, 272, 280, 281, 297 THMP condensation, 173 VARTM, 297, 298 Time of flight mass spectroscopy Viscometric detection, 101 (TOF-MS), 118 VOC. See Volatile organic compounds TMA. See Thermal mechanical analysis Volatile organic compounds (VOC), 120, TOF-MS. See Time of flight mass 161, 180, 488 spectroscopy Volume, 155 TOF-MS of glycolated novolac, 119 Vulcanization, 443, 445, 446, 448, 450 Index 545

W X WAXD. See Wide-angle X-ray XN, 77, 79 diffraction XN-L, 77 Wear, 348, 355–357 X-ray mapping, 127 Wet chemical methods, 97 Xylenols, 9, 10, 19–21 Wide-angle X-ray diffraction (WAXD), Xylok, 79 62 Xylok resins, 77 Wideline NMR, 117 Wood, 155 adhesives, 158 Z composite, 156 Zeolite, 54 Work time, 470 Zinc acetate, 57