Handbook of Thermoset Plastics

Handbook of Thermoset Plastics
Third Edition
Edited by
Hanna Dodiuk , Sidney H. Goodman
Table of contents

1. Introduction
   History
   Definitions
   Cross-Linking and Curing
   Influence of Time, Temperature, and Mass
   Shelf Life and Pot Life
   Curing
   Staging
   Stoichiometric Considerations
   Prepolymerization and Adducting
   References
   Further Reading
2. Phenol–Formaldehydes
   Introduction
   Raw Materials
   Phenol
   Resinification (Production) of Phenol–Formaldehyde Resins
   Phenolic Resins in Friction Materials
   References
   Further Reading
3. Polybenzoxazine–new generation phenolics
   Introduction
   Synthesis of Benzoxazine Monomers (BZ)
   Ring-Opening Polymerization of Benzoxazines
   Regioselectivity and Cross-Linked Structure
   Inter/Intramolecular H-Bonding
   Kinetics of Thermal Cure
   Structure-Property Relationships
   Blends/Composites of Polybenzoxazines
   Green Chemistry Approaches in PBZ
   Click Chemistry in PBZ
   Stability and Degradation
   Outlook
   Acknowledgments
   References
4. Aminos
   Introduction
   Raw Materials
   Chemistry of UF Resins: Urea–Formaldehyde Condensation
   Chemistry of MF Resins: Melamine–Formaldehyde Condensation
   General Principles of Manufacture and Application
   Applications of Amino Resins
   References
5. Furans
   Introduction
   Resins from Furfuryl Alcohol and Furfural
   Photocross-Linkable Furan Polyesters
   Furan Polyurethane Foams
   Photoresists from Pending Furan Chromophores
   Ion-Exchange Resins Based on 2-Vinylfuran
   Networks Based on Diels-Alder Polycondensations
   References
6. Unsaturated Polyesters and Vinyl Esters
   Unsaturated Polyesters
   Vinyl Ester Resins
   Compounding of Unsaturated Polyester and Vinyl Ester Resins
   Property Modification of Unsaturated Polyesters
   Applicable Manufacturing Processes
   References
7. Allyls
   Introduction
   Polydiallyldiglycolcarbonate (CR-39)
   Polydiallyl Phthalates
   References
8. Epoxies
   Introduction
   Detailed Chemistry
   Characterization of Epoxies
   Applications
   References
   Further Reading
9. Polyurethanes
   Introduction
   General Characteristics of Polyurethanes
   Raw Materials Used in the Synthesis of Cross-Linked Polyurethanes
   Synthesis and Cross-Linking Reactions of Polyurethanes
   Morphology of Linear/Branched vs. Cross-Linked Polyurethanes
   Manufacturing Methods and Technical and Functional Properties of Thermosetting Polyurethanes
   References
10. High-Performance Polyimides and High Temperature Resistant Polymers
    Historical Perspective
    Polyimides from Condensation Reactions
    Thermoplastic Polyimides
    Addition-Curable Polyimides and Other Polymers
    Nadimide-Terminated Thermosetting Polyimides
    Maleimide-Terminated Thermosetting Polyimides
    Cyanate-Terminated Thermosetting Polymers
    High-Temperature Thermosetting Resins Based on Phthalonitrile
    Acetylene-Terminated Thermosetting Polymers
    Propargyl-Terminated Oligomers
    Phenylethynyl-Terminated Thermosetting Polymers
    Applicability of Thermoset Isoimides/Imides to Resin Transfer Molding Processing
    Galvanic Corrosion Resistance of Polyimide Composites
    High-Performance Polymers for Lightning Strike Protection
    Ultrahigh Temperature Resistant Polymers
    Chemical Structures Suitable for Ultrahigh Temperature Use
    Novel Cross–Linking Mechanisms for Stability at Ultrahigh Temperatures
    Thermosets as Dielectric Interlayers in Integrated Circuit (IC) Fabrication
    Polymer-Ceramic Materials
    Acknowledgments
    References
    Further Reading
11. Cyanate Esters
    Introduction
    Chemistry
    Characterization and Reaction Monitoring
    Processing of Cyanate Ester Resins
    Properties of Cyanate Esters
    Properties of Cyanate Ester Blends with Epoxy and BMI
    Recent Developments
    Applications
    Trade Names
    References
12. Maleimide-Based Alder-Enes
    Introduction to Bismaleimides
    Maleimide-Based Alder-Ene Polymers
    Alder-Ene Polymers from Various Allyl-Maleimide Compounds
    Alder-Ene Polymer Blends
    Nano-Modified Alder-Ene Polymers
    Shape Memory Alder-Ene Polymers
    Kinetics of Alder-Ene Polymerization
    Outlook
    Acknowledgments
    References
13. Syntactic Foams
    Introduction
    Syntactic Foams Based on Thermosets
    Recent Advances in Syntactic Foams
    Applications of Syntactic Foams
    Outlook
    Acknowledgments
    References
14. Silicones
    Introduction
    Silicone Elastomers
    Silicone Laminates
    Silicones in the Medical Device Industry
    Special Silicones
    Silicone Fluids
    Other Fluid Types/Copolymers
    References
15. Biobased Thermosets
    Polymers from Renewable Sources
    Determination of Bio-Based Content in Polymers
    Raw Materials for Renewable Sources Polymers
    Thermoset from Renewable Sources
    ReferencesBiobased Thermosets
    Polymers from Renewable Sources
    Determination of Bio-Based Content in Polymers
    Raw Materials for Renewable Sources Polymers
    Thermoset from Renewable Sources
    References
16. Nanotechnology Based Thermosets
    Introduction
    Nanoclays
    POSS
    Nano Silica
    Carbon Nanotubes (CNT)
    Graphene and Expanded Graphite
    Tungsten Disulfide
    References
17. Crosslinked Thermoplastics
    Introduction
    Radiation Cross-Linking of Thermoplastics
    Effects of Radiation Cross-Linking on Thermoplastic Polymers
    Chemical Cross-Linking with Organic Peroxides
    Effects of Peroxide Cross-Linking on Thermoplastic Polymers
    Cross-Linking of Thermoplastics Using Silane Grafting Reagents
    Effects of Silane Cross-Linking on Thermoplastic Polymers
    Comparison of Cross-Linking Methods
    Applications of Cross-Linked Thermoplastics
    References
18. Processing
    Introduction
    Processing of Monomers: Online Monitoring of Resin Synthesis
    Processing of Pre-Polymers: Online Monitoring of Resin Flow and Resin Cure During Composite Manufacture
    References
    Appendix. Polybenzoxazines – Commercial Information
    Commercial Benzoxazine Marketed by Huntsman
    Products by Henkel
    Index
    Note: Page numbers followed by “f” and “t” indicate figures and tables, respectively.
    A
    Abietic-type acids, 597
    598, 598f
    Acenaphthylene, 401
    Acetoxy cure, for silicones, 558
    560, 559t
    Acidic Ion Exchange Resin (AIER), 581
    Acrylation, of epoxidized triglycerides,
    582
    583, 583f
    Addition cure, RTV silicones, 561, 562t
    vs. condensation cure systems, 563t
    Adhesives
    phenolic bio-based, 41
    PRF, 39
    40
    reduced resorcinol content, 40
    41
    resorcinol, 37
    Aerospace industry, syntactic foams in, 546
    Albumin, 593
    Alder-ene polymer
    allyl compounds, 463
    486
    blends, 486
    495
    high-performance blends, 486
    491
    nano-modified, 495
    497
    overview, 462
    463
    polymerization
    kinetics, 499
    504
    reaction sequence, 462
    463, 463f
    shape memory, 497
    498
    thermoplastic-toughened, 491
    495
    Alkoxy cure, for silicones, 558
    559, 559t
    Alkyd resins, bio-based, 610
    611
    Allyls
    overview, 173
    174
    polydiallyldiglycolcarbonate
    (PDADGC), 174
    180
    applications, 178
    180
    formulation, 176
    polymerization, 176
    properties, 176
    177
    trade names, 180
    polydiallyl phthalates, 180
    187
    applications, 185
    187
    chemistry, 181
    formulation, 183
    general aspects, 180
    181
    polymerization, 181
    183
    properties, 183
    185
    trade names, 187
    Aluminium phosphate, 411
    412
    Amide cure, for silicones, 558
    Amino resins
    adhesive and bonding, 82
    83, 88
    composite wood materials, 88
    medium density fiberboard
    (MDF), 88
    particle board, 88
    coatings, 83
    84
    application, 88
    paper treatment, 88
    protective, 88
    textile treatment, 88
    laminating, 84
    application, 88
    89
    manufacturing, 80
    87
    mixed melamine resins, 79
    80
    molding, 84
    87
    application, 89
    90
    overview, 88
    89
    Anhydride, for curing epoxy syntactic
    foams, 523, 523f
    Animal proteins, 592
    593
    Applications, 142
    144
    cross-linked thermoplastics, 716
    734
    acrylates, 730
    733, 731t
    fluoride-containing polymers,
    733
    734
    heat-shrinkable tubing, 723
    730, 725t
    polyolefin foams, 716
    719
    rotational molding, 719
    723
    cyanate ester resins, 448
    450
    phenolic resins
    coating applications, 35
    laminating applications, 31
    32
    molding applications, 32
    34
    syntactic foams, 545
    548
    aerospace industry, 546
    buoyancy, 545
    546
    furniture, 547
    military, 547
    miscellaneous, 547
    548
    plug-assist materials, 547
    radomes, 546
    shielding electronic components, 548
    sports industry, 546
    547
    synthetic marble, 547
    thermal insulation materials, 546
    Art objects, 161
    ASTM D6866-11, 578
    B
    Baekeland, Leo, 2
    Beetle grades, 83
    84
    Benzocyclobutene, 399
    400
    Benzoxazines, 514, 514f
    curable moieties, 51
    56
    curing, 47, 47f
    ortho positions, 48, 48f
    regioselectivity, 47
    49
    ring-opening polymerization, 47, 47f
    4,40-biamaleimido diphenyl methane
    (BMPM), 459
    Bio-based content
    defined, 578
    in polymers, 578
    579
    Bio-based phenolic resins, 611
    615
    Biopolymers, 2
    4,40-bis(4-cyanatobenzyl) biphenyl
    (BBPCy), 442, 443f
    2,20-bis(4-cyanatophenyl)isopropylidene
    (DCBA), 433
    435
    Bismaleimide (BMI), 514
    515
    blends with epoxy resins, cyanate ester
    resins, 435
    437
    description, 459
    462
    drawbacks, 461
    flammability, 461
    glass transition temperatures, 514
    modification approaches, 462
    reaction mechanism, 459, 460f
    structure, 532f
    synthesis, 459
    462, 460f, 515f
    thermo-mechanical properties,
    compared to other high-performing
    resin, 461t
    761BMI. See Bismaleimide (BMI)
    Bulk molding compounds (BMC),
    155
    156
    Buoyancy applications, syntactic foams
    in, 545
    546
    C
    Carbohydrates, 588
    589
    polyols from, 607
    Carbon-carbon syntactic foams, 535
    applications, 548
    Carbon dioxide (CO2), 578
    Carbon fiber-reinforced polymer
    (CFRP), 546
    Carbon nanotubes (CNT)
    epoxy resin, 656
    659
    overview, 654
    665
    phenolic resin, 659
    665
    polyimides, 659
    665
    polyurethanes, 659
    665
    Cardanol, 592
    structure, 592f
    Cardanol-formaldehyde resins, 613
    Casted giftware, 161
    Celluloid, 577
    CEN/TS 16137, 578
    579
    CFRP. See Carbon fiber-reinforced
    polymer (CFRP)
    Chemometrics, 742
    744
    Chemosets, 3
    Clay-polymer nanocomposites, 413
    Coating applications, phenolic
    resins in, 35
    Co-condensation, between phenol and
    urea, 36
    Coefficient of thermal expansion (CTE)
    of epoxy syntactic foams, 525
    Cold box process, phenolic resin, 31
    Collagen, 593
    Composite wood products, phenolic
    resins, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    Compression, syntactic foams, 519
    520,
    519f
    Condensation cure RTV silicones,
    560
    561, 562t
    DBT, 560
    STO, 561
    vs. addition cure systems, 563t
    Core sandwich composites, syntactic
    foams, 542
    543
    closed-pore structure, 543
    low moisture absorption, 543
    one-step compression molding, 543
    Cornerstone Research Group (CRG),
    544
    545
    Cow milk, 592
    593
    CRG. See Cornerstone Research Group
    (CRG)
    Cross-linked acrylates, 730
    733, 731t
    Cross-linking, 3
    4
    applications, 716
    734
    acrylates, 730
    733, 731t
    fluoride-containing polymers,
    733
    734
    heat-shrinkable tubing, 723
    730, 725t
    polyolefin foams, 716
    719
    rotational molding, 719
    723
    comparison methods, 715
    716
    defined, 3
    dimensional behavior upon, cyanate
    ester, 433
    molecular functionality, 4
    silane grafting reagents, 712
    715
    effects, 715
    wih peroxides, 708
    polyethylene, 708
    711, 709f
    polypropylene, 711
    712
    wih radiation. See Radiation crossLinking
    Cultured marble and onyx, 161
    162
    Cumene process, for phenol, 15
    Cure schedule, 7, 8f
    Curing, 7
    8
    defined, 5
    Curing agent
    defined, 5
    6
    Cyanate ester resins
    applications, 448
    450
    blends with epoxy and BMI,
    435
    437, 436t
    curing, 427
    429
    cyclo-trimerization, 430
    dimensional behavior upon crosslinking, 433
    distinctive features, 426t
    epoxy resins, 435
    436
    gelation, 433
    glass transition temperature
    and tensile elongation-at-break,
    431, 432f
    heterocyclic aromatic structure, 427
    hydrolysis behavior, 433
    435
    industrial demand, 426, 426f
    metal catalyst, 430, 431t
    monomers, 427, 428t
    bio-based raw materials, 442
    445
    conferring flame retardance,
    440
    442
    modifying flexibility, 437
    440
    novel, 437
    445
    optical spectroscopy, 429
    overview, 437
    445
    processing, 430
    431
    catalyst composition, 430
    frontal polymerization, 445
    446
    microwave-assisted polymerization,
    446
    447
    nanoconfinement, 448
    plasma polymerization, 448
    properties, 425, 431
    435
    electrical, 431
    433
    mechanical, 431
    physical, 434t
    thermal, 431, 432f
    Raman spectroscopy, 429
    reaction scheme illustrating
    formation, 426f
    structural unit, 427, 427f
    thermal analysis, 429
    430
    trade names, 451, 451t
    viscosity, 427
    Cyanate esters syntactic foams, 514,
    530
    531
    Cymel grades, 84
    D
    DBT. See Dibutyl tin dilaurate (DBT)
    Denaturation, proteins, 592
    593
    Diallyl Bisphenol A (DABA), 532f
    Diamines, 459
    460
    Dianhydrohexytols, 588
    589
    Diazine, 401
    402
    Dibutyl tin dilaurate (DBT), 560
    Dielectric analysis sensors, 746
    748, 747f
    Differential scanning calorimetry
    (DSC), 750
    751
    Diglycidyl ether of bisphenol A
    (DGEBA), 512, 512f
    9,10-Dihydro-9-oxa-10-
    phosphaphenanthrene-10-oxide
    (DOPO), 442, 443f
    Dimethylsilicone fluids, 571, 571t
    Dow process, for phenol, 15
    Drying oils, 581
    DSC. See Differential scanning
    calorimetry (DSC)
    E
    EAS. See Epoxidized allyl soyate (EAS)
    Eco-Core, 525
    526
    Elastomeric syntactic foams, 535
    as stress relief coatings, 535, 548
    Elmet GmbH, 567
    568
    Engel Austria GmbH, 567
    568
    Engineering thermosets, 2
    Enone-containing triglycerides, 585, 586f
    EPB syntactic foam, 531, 532f
    modulus, 532, 533f
    strength, 532, 533f
    Epon resin, 595
    596
    Epoxidation
    of catechin using epichlorohydrin,
    596
    597, 597f
    of triglycerides, 582, 582f
    Epoxidized allyl soyate (EAS), 595
    596
    762 INDEXEpoxidized linseed oil, 597, 597f
    Epoxidized oils, 595
    chemical modification, 595
    596
    Epoxidized soybean oil (EBSO), 595
    Epoxidized soybean oil (ESO),
    524
    525, 525f
    Epoxy/nanoclay compositions, 625
    628
    Epoxy resins, 8
    acid-curing agents, 206
    210
    cyclic anhydrides, 207
    209
    Lewis acids, 206
    mercaptans, 209
    210
    organic acids, 207
    phenols, 206
    207
    polysulfides, 209
    210
    alkaline curing agents, 201
    206
    aliphatic amines, 202
    203
    amine adducts, 203
    aromatic amines, 204
    205
    cyclic amines, 203
    204
    Lewis bases, 201
    202
    polyamides, 205
    206
    applications, 243
    247
    blends with BMI, cyanate ester, 435
    437
    carbon nanotubes (CNT), 656
    659
    characterization, 216
    243
    chemoviscosity, 239
    240
    colorants, 214
    216
    cross-link density, 232
    240
    cross-linking, 200
    curing, 199
    200
    curing agents, 200
    differential scanning calorimetry
    (DSC), 234
    temperature-modulated, 234
    236
    diglycidyl ether of bisphenol A
    (DGEBA), 192
    195
    diluents
    nonreactive, 212
    213
    reactive, 210
    211
    dyes, 214
    216
    Dynamic Mechanical Analysis, 237
    238
    α-epoxy (or 1,2-epoxy), 192
    ethylene oxide, 192f
    fillers, 213
    214
    formulation principles, 210
    216
    gass transition, 232
    240
    gelation, 240
    241
    glycidyl group, 192f
    graphene and expanded graphite,
    667
    671
    heat, 220
    232
    historical development, 299
    314
    hydantoin resins, 196
    molecular weight, 232
    240
    nanoclays compositions, 625
    628
    novolacs, 195
    overview, 297
    299
    peracid resins, 195
    196
    POSS nanocomposites, 638
    641
    resinous modifiers, 211
    212
    rheological additives, 216
    stoichiometry, 200
    201
    structure, 532f
    Thermally Stimulated Depolarization,
    238
    239
    thermomechanical analysis (TMA),
    236
    237
    vitrification, 241
    243
    Epoxy syntactic foams, 512, 520
    525
    bulk density, 520
    521, 521f
    coefficient of thermal expansion
    (CTE), 525
    compressive strength, 520
    521, 521f
    curing agents, 523, 523f
    fracture toughness, 523
    glass transition temperature,
    523
    524, 523f
    materials and process details, 524t
    neat resins, 523
    524, 524f
    tensile properties with microballoon
    volume fraction, 520, 521f
    ESO. See Epoxidized soybean oil (ESO)
    Expanded graphite
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    F
    Fatty acids, 579
    581, 580t
    Fevernova, 546
    547, 547f
    FGSF. See Functionally graded syntactic
    foams (FGSF)
    Fiber board, 27
    Fiber Bragg Gratings (FBGs), 749
    750,
    750f
    Fiber optics
    embedded, 748
    749
    measurement, 748
    750
    Fiber-reinforced syntactic foams,
    535
    538
    flexural strength, 536, 536f
    length of fiber, 537
    538, 538f
    short carbon fiber (SCF), 538, 539f
    storage modulus, 538, 539f
    tensile and flexural properties, 537,
    538f
    thermal stability, 538, 539f
    mechanical properties, 536, 537f
    silica fiber, 536, 537f
    tensile strength, 536, 536f
    Young’s modulus, 537
    Fillers, phenolic resins, 23
    24
    Fluoride-containing polymers, 733
    734
    trade names, 734t
    Formaldehyde, 15
    16
    Formalin, 15
    16
    impurities, 16
    Frontal polymerization, cyanate ester
    resins, 445
    446
    Functionalized vegetable oils (FVO),
    524
    525
    Functionally graded syntactic foams
    (FGSF), 542
    RR-type, 542, 543f
    VF-type, 542, 543f
    Furan resins
    chromophores, 101
    103
    Diels-Alder (DA) reaction,
    95, 95f
    polycondensations, 105
    107
    hydroxymethylfuraldehyde (HMF),
    94
    95, 95f
    overview, 93
    96
    photocross-linkable, 100
    polyurethane foams, 101
    2-vinylfuran (VF), 103
    105
    Furfural (F)
    condensation, derivatives with
    aldehydes and ketones, 94f
    furfuryl alcohol (FA), 93
    mechanism of formation, 94f
    monomers prepared from, 94f
    overview, 93
    resins from, 96
    100
    Furfuryl alcohol (FA), 93
    resins from, 96
    100
    Furniture, syntactic foams in, 547
    FVO. See Functionalized vegetable
    oils (FVO)
    G
    Gelation, cyanate ester resins, 433
    General purpose thermosets, 2
    Geniomer, 568
    569, 569f
    Gliadin, 593
    Global warming, 578
    Glycerol, 588
    Glycerolysis, 585
    587, 587f
    Graphene and expanded graphite
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    Graphite, expanded
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    Guaiacol, 614f
    H
    Hand layup, 150
    151
    HCR. See High consistency silicone
    rubber (HCR)
    Heat-shrinkable tubing, 723
    730, 725t
    INDEX 763HEXA. See Hexamethylene tetramine
    (HEXA)
    Hexamethylene tetramine (HEXA), 16
    Hexamine. See Hexamethylene tetramine
    (HEXA)
    High consistency silicone rubber
    (HCR), 561
    563
    High temperature vulcanization (HTV),
    561
    566
    silicones, 561
    566
    Hydroformylation, of triglycerides, 583, 584f
    Hydrolysis behavior, cyanate ester resins,
    433
    435
    Hydroxylated oils, maleinization, 585, 586f
    Hydroxylation, of triglycerides, 583
    584
    Hydroxymethylfuraldehyde (HMF),
    94
    95, 95f
    I
    Impranil, 546
    547
    International Confederation for Thermal
    Analysis and Calorimetry
    (ICTAC), 753
    Isocyanate, and phenolic resins, 36
    37
    Isoidide, 588
    589, 588f
    Isomannide, 588
    589, 588f
    Isosorbide, 588
    589, 588f
    K
    Kienle, R. H., 610
    L
    Laccain, 14. See also Phenolic resins
    Laminates, silicones, 566
    Laminating applications, phenolic resins
    in, 31
    32
    LCA. See Life cycle assessment (LCA)
    Life cycle assessment (LCA), 577
    578
    Lignin, 443, 444f, 612
    613, 613f
    as additives, 590
    in epoxy resin networks, 596
    generic structure, 591f
    grafting of, 590
    591
    hydrolysis, 590
    methylolation, 614
    615
    nonphenolic hydroxypropyl, 590
    phenolation or phenolysis, 614
    615
    Lignins, and phenolic resins, 36
    Linear polymer, 3, 4f
    Lipids, 579
    Liquid Silicone Rubbers (LSR), 565
    Litidionite, organically modified, 412
    413
    Low dielectric constants, syntactic
    foams, 520
    LSR. See Liquid Silicone Rubbers (LSR)
    M
    Maleates, 585
    587
    Maleinization
    acrylated epoxidized oils, 583, 584f
    hydroxylated oils, 585, 586f
    Mannich bridge (CH2-N-CH2), 48
    49
    Mat molding, for UPR and VER, 157
    MCR ALS. See Multivariate curve
    resolution calculated by alternating
    least squares (MCR ALS)
    Medical device industry, silicones in,
    566
    567
    Melamine, 76
    Melamine-formaldehyde (MF) resins
    as adhesives, 75
    76
    condensation, 78
    80
    overview, 75
    raw materials, 75
    Melamine-urea-formaldehyde (MUF)
    resins, 79
    80
    copolymerization, 79
    80
    phenol, 80
    UF and MF mixtures, 79
    80
    Methacrylation, monoglycerides, 587
    Methylphenylpolysiloxane fluids,
    571
    573, 572t
    Methylpolysiloxane fluids, 569, 570t
    Methyl-tetrahydrophthalic anhydride
    (MTHPA), 524
    525, 525f
    Microballoon, in syntactic foams,
    515
    517, 517f
    Microspheres syntactic foams, 515
    517
    Microwave-assisted polymerization,
    cyanate ester resins, 446
    447
    Military, syntactic foams in, 547
    Moisture absorption, syntactic foams, 520
    Molding applications, phenolic resins in,
    32
    34
    Monoglycerides, 585
    587
    methacrylation, 587
    Monolithic flooring, 162
    Monomers, cyanate ester resins, 427, 428t
    bio-based raw materials, 442
    445
    conferring flame retardance, 440
    442
    modifying flexibility, 437
    440
    novel, 437
    445
    MTHPA. See Methyl-tetrahydrophthalic
    anhydride (MTHPA)
    Multivariate curve resolution calculated
    by alternating least squares (MCR
    ALS), 744
    N
    Nanoclays
    compositions
    epoxy, 625
    628
    phenolic resins, 631
    633
    polyimide, 635
    637
    polyurethane, 633
    635
    unsaturated polyesters, 628
    631
    nanocomposites, 625
    overview, 623
    625
    Nanoconfinement, cyanate ester
    resins, 448
    Nano reinforcement, in syntactic foams,
    539
    540
    Nano silica. See Silica nanocomposites
    NASA Ames Research Center, 546
    Natural oils, 579
    587. See also
    Triglycerides
    direct polymerization, 581
    double bonds, chemical modification
    of, 581
    585
    Natural rubber, 2
    Network polymer, 3, 4f
    NMR spectroscopy, 750
    Novocardt, 598
    Novolak phenolic resins, 19
    20
    vs. resole, 20
    O
    One-component RTV silicones, 557
    560
    acetoxy cure, 558
    560, 559t
    alkoxy cure, 558
    559, 559t
    amide cure chemistry, 558
    oxime cure chemistry/by-product, 558
    primers, 560
    Si-O-Si bonds, 557
    558
    Online monitoring tools
    overview, 739
    resin flow/cure, 744
    753
    dielectric analysis sensor, 746
    748
    embedded fiber optics, 748
    749
    Fiber Bragg Gratings (FBG),
    749
    750
    other methods, 750
    SMARTweave sensor, 746
    thermal analysis, 750
    753
    ultrasonic sensors, 748
    resin synthesis, 740
    744
    chemometrics, 742
    744
    general aspects, 740
    optical spectroscopy, 740
    744
    Raman spectroscopy, 742
    Optical fibers. See Fiber optics
    Optical spectroscopy, 740
    744
    FTIR, 741
    742
    infrared (IR), 741
    742
    nuclear magnetic resonance (NMR),
    741
    742
    Optical spectroscopy, cyanate ester
    resins, 429
    Organically modified litidionite, 412
    413
    Organic peroxides, chemical cross-linking
    with, 708
    Oxime cure chemistry/by-product,
    silicones, 558
    Ozonolysis, triglycerides, 583, 585f
    P
    [2.2]Paracyclophane, 397
    398
    Partially stabilized zirconium oxide
    (PSZ), 412
    Particle board, 27
    764 INDEXPeroxide cross-linking, 708
    polyethylene, 708
    711, 709f
    polypropylene, 711
    712
    Peroxide curing agents, silicone, 564t, 565
    Phenol, 15
    16
    cumene process, 15
    Dow process, 15
    Raschig process, 15
    urea and, co-condensation between, 36
    Phenol-formaldehyde resins. See Phenolic
    resins
    Phenolic microballoons, in syntactic
    foams, 517
    Phenolic (P1) and PN resin (PNM),
    527, 527f
    Phenolic resins
    bio-based, 611
    615
    carbon nanotubes (CNT), 659
    665
    coating applications, 35
    co-condensation between phenol and
    urea, 36
    composite wood products, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    description, 14
    15
    differences between resole and
    novolac, 20
    fillers, 23
    24
    friction materials, 29
    41
    graphene and expanded graphite,
    671
    674
    hexamethylene tetramine (HEXA), 16
    as insulation materials, 29
    isocyanate, addition of, 36
    37
    laminating applications, 31
    32
    lignins, addition of, 36
    modification, 35
    37
    molding applications, 32
    34
    nanoclay compositions, 631
    633
    nanoclays compositions, 631
    633
    novolak, 19
    20
    plywood, 25
    27
    POSS nanocomposites, 641
    646
    PRF. See Phenol-resorcinolformaldehyde (PRF)
    processing methods, 24
    25
    properties, 20
    23
    raw materials for, 15
    resinification, 16
    29
    polymerization process, 16
    19
    reaction mechanism, 16
    resole, 19
    silica nanocomposites, 650
    654
    tannins, addition of, 36
    37
    urea, addition of, 35
    36
    Phenolic syntactic foams, 512
    514,
    525
    528
    aldehyde groups, 528, 528f
    hollow carbon microspheres, 528,
    528f, 529f
    mechanical properties, 526
    527, 526t
    microballoon-based, 528
    PN resin (PNM), 527, 527f
    tensile and flexural strength, 526
    527
    Phenol-resorcinol-formaldehyde (PRF), 37
    adhesives, 39
    40
    Plant oil, 579
    581
    fatty acids, 579
    581, 580t
    polymers, 581
    triglycerides, 579
    581, 579f
    Plasma polymerization, cyanate ester
    resins, 448
    Plasticization, proteins, 592
    593
    Plug-assist materials, syntactic
    foams as, 547
    Plywood, 25
    27
    Polybenzimidazole syntactic foams, 534
    Polybenzoxazines (PBz), 514
    bio-based products, 67
    68
    blends, 61
    67
    co-reactive, 61
    64
    non-reactive, 61
    64
    chemical bridge structures, 48, 48f
    click chemistry, 68
    69
    composites
    fiber, 65
    66
    micro, 65
    66
    cross-linked structure, 47
    49, 49f
    inter/intramolecular H-bonding, 49
    main chain, 60
    61
    nanocomposites, 66
    67
    stability and degradation, 69
    syntactic foams
    mechanical strength, 529, 529f
    thermal curing, 49
    51
    unfunctionalized, 56
    60
    Polyester syntactic foams, 534
    Polyethylene
    peroxide cross-linking, 708
    711
    radiation cross-linking, 703
    silane cross-linking, 712
    715
    Polyhedral oligomeric silsesquioxanes
    (POSS)
    epoxy, 638
    641
    isocyanate groups, 642
    643
    N-phenylaminomethyl, 643
    octa(aminophenyl)-POSS, 644
    OpePOSS, 642
    overview, 637
    646
    phenolic resin, 644
    polyimides (PI), 644
    645
    polyurethanes, 641
    643
    silanols, 646
    silsesquioxanes, 644
    unsaturated polyester, 643
    644
    Polyimides
    acetylene-terminated, 361
    374
    imide oligomers, 364
    367
    oligomers, cure mechanism,
    369
    374
    quinoxalines, 362
    364
    sulfones, 364
    addition-curable, 335
    336
    adhesive formulations, 388
    AFR700B resins, 344
    aromatic characteristics, 298f
    carbon nanotubes (CNT), 659
    665
    coatings
    high-temperature resistant, 388
    insulative, 386
    condensation reactions, 299
    314
    conductive paint, 388
    conductive polymer blends, 386
    corrosion
    galvanic, 385
    387
    mechanism, 385
    386
    cyanate esters
    polyimide-based, 355
    356
    semi-interpenetrating polymer
    network (SIPN), 355
    cyanate-terminated, 351
    356
    graphene and expanded graphite,
    671
    674
    historical perspective, 297
    299
    hydrogen-free, 393
    395
    imide structural analogs, 387
    isoimide modification, 367
    369
    low-viscosity SIPN imide blends,
    384
    385
    maleimide-terminated, 344
    350
    modified nadimide end-caps, 343
    344
    nanoclay compositions, 635
    637
    nanoclays compositions, 635
    637
    nonmetallic conductive materials, 388
    NR-150 (DuPont), 318
    phenylethynyl-terminated, 374
    382
    phthalonitrile, 356
    361
    polyamic acid converted to, 298f
    polycyanurates
    electronic industry, 356
    flame retardancy, 356
    POSS nanocomposites, 641
    646
    propargyl-terminated oligomers, 374
    resin transfer molding (RTM)
    aerospace resins, 383
    384
    isoimides/imides applicability,
    382
    385
    polyimides, relevance of, 384
    silica nanocomposites, 650
    654
    thermoplastic, 314
    334
    Torlon®, 325
    328
    Ultem®, 318
    324
    ultrahigh temperature resistant
    polymers, 388
    389
    XU 218 (XIV), 329
    332
    Polyimide syntactic foams, 531
    532
    Polymer-ceramic materials, 409
    413
    INDEX 765Polymer-clay nanocomposites, 625
    Polymer concretes, 162
    164
    Polymeric microballoons, in syntactic
    foams, 517
    Polymerization, cyanate ester resins
    frontal, 445
    446
    microwave-assisted, 446
    447
    plasma, 448
    Polymerization process, phenolic
    resins, 16
    19
    Polymers
    biphenylene, 396
    397
    bisazoles, 390
    393
    phthalocyanine, 393
    ultrahigh temperature resistant,
    388
    389
    Polyolefin foams, 716
    719
    Polyols
    from carbohydrates, 607
    from lignocellulosic materials, 606
    from natural polyphenols, 607
    Polyols, from carbohydrates, 607
    Polyphenols, 589
    592
    Polypropylene
    peroxide cross-linking, 711
    712
    radiation cross-linking, 703
    707
    Polyurethanes (PU), 633
    635
    adhesives, 286
    287
    auxiliary agents, 264
    266
    bio-based, 601
    610
    from vegetable oils, 602
    606
    blowing agents, 264
    carbon nanotubes (CNT), 659
    665
    catalysts, 263
    264
    chain extenders, 263
    characteristics, 254
    258
    coatings, 286
    287
    cross-linked, 276
    277
    medicine, 287
    289
    cross-linking, 266
    274
    radical reactions, 272
    274
    via allophanate or biuret bonds,
    269
    via cross-linkers, 267
    269
    via isocyanates dimerization or
    trimerization, 270
    272
    via polyols, 266
    267
    foams, 284
    286
    graphene and expanded graphite,
    671
    674
    isocyanates, 258
    261
    health hazard evaluation, 258
    261
    linear/branched, 275
    276
    manufacturing methods, 277
    289
    nanoclays compositions, 633
    635
    oligomerols, 261
    263
    derived from glycolysates, 262
    other types, 263
    from renewable raw materials, 262
    unsaturated, 262
    overview, 253
    254
    POSS nanocomposites, 641
    646
    raw materials, 258
    266
    silica nanocomposites, 650
    654
    vegetable oils, 602
    606
    Polyurethane syntactic foams, 533
    534
    Polyvinyl chloride (PVC), 707
    708
    Polyvinylidene chloride (PVDC)
    microspheres, 547
    ultra low-density, 547
    Polyvinylidene fluoride (PVDF), 733
    734
    Pot life, 7
    Preform molding, for UPR and VER, 157
    Premix molding, for UPR and VER, 157
    Pre-preg process, 153
    Pressure-bag process, 153
    154
    PRF. See Phenol-resorcinol-formaldehyde
    (PRF)
    Primasetr PT-30, 439
    440, 441f
    Prolamine proteins, 593
    Propargyl ether novolac (PN)
    mechanical properties, 526t
    synthesis, 513, 513f
    Proteins, 592
    594
    albumin, 593
    animal and vegetable, 592
    593
    collagen, 593
    cow milk, 592
    593
    denaturation, 592
    593
    gliadin, 593
    gluten, 593
    plasticization, 592
    593
    prolamine, 593
    soy, 593
    594
    whey, 593
    zein, 593
    Prototype molding, for UPR and VER,
    156
    157
    Pultrusion, UPR and VER in, 158
    R
    Radiation cross-linking, 698
    703
    oxidation, 701
    702
    polyethylene, 703, 706t
    polymers, 702t
    polypropylene, 703
    707, 706t
    polyvinyl chloride (PVC), 707
    708
    Radomes, syntactic foams in, 546
    Raman spectroscopy, 742
    Raman spectroscopy, cyanate ester
    resins, 429
    Rapid Thermal Processing, 613
    Raschig process, for phenol, 15
    Renewable sources polymers
    bio-based polymers, 577
    578
    crbon content, 578
    579
    bio-based polyurethanes, 601
    610
    bio-based unsaturated polyester,
    598
    601
    epoxy, 594
    615
    natural oils, 579
    587. See also
    Triglycerides
    direct polymerization, 581
    double bonds, chemical modification,
    581
    585
    raw materials for, 579
    594
    Resin, defined, 5
    6
    Resin cure modeling, 750
    753
    Resin flow/cure analysis, online
    monitoring tools for, 744
    753
    dielectric analysis sensor, 746
    748
    embedded fiber optics, 748
    749
    Fiber Bragg Gratings (FBG), 749
    750
    other methods, 750
    SMARTweave sensor, 746
    thermal analysis, 750
    753
    ultrasonic sensors, 748
    Resin infusion process, 153
    154
    Resin synthesis, online monitoring tools,
    740
    744
    chemometrics, 742
    744
    general aspects, 740
    optical spectroscopy, 740
    744
    Raman spectroscopy, 742
    Resin transfer molding (RTM), 154
    155
    Resole phenolic resins, 19
    vs. novolak, 20
    Resorcinol adhesives, 37
    Resorcinol-formaldehyde (RF) resins, 37
    chemistry, 37
    39
    Room-temperature-vulcanizing (RTV)
    silicones, 557
    561
    addition cure, 561, 562t
    condensation cure, 560
    561, 562t
    DBT, 560
    STO, 561
    one-component, 557
    560
    acetoxy cure, 558
    560, 559t
    alkoxy cure, 558
    559, 559t
    amide cure chemistry, 558
    oxime cure chemistry/by-product, 558
    primers, 560
    Si-O-Si bonds, 557
    558
    two-component, 560
    vs. one-component, 560
    Rosin, 597
    598
    Rotational molding, 719
    723
    RR-type FGSF, 542, 543f
    RTV. See Room-temperature-vulcanizing
    (RTV) silicones
    Rubberized syntactic foams, 540
    542,
    542f
    S
    Saccharides, 588
    589
    Saran microballoons, 517, 547
    Sensors
    dielectric analysis, 746
    748, 747f
    SMARTweave, 746, 746f
    ultrasonic, 748, 748f
    766 INDEXSFRSF. See Short fiber-reinforced
    syntactic foams (SFRSF)
    Shape memory, UPR with, 164
    Shape memory polymer (SMP)-based
    syntactic foams, 543
    545
    compressed and expanded forms, 545f
    DMA studies, 543
    544, 544f
    durability, 544
    glass transition temperature, 543
    544
    thermomechanical properties, 544, 545f
    ultraviolet radiation, 544
    Sheet molding compounds (SMC), 155
    156
    Shelf life, 7
    Shell molding process, phenolic resin in, 31
    Shielding electronic components, syntactic
    foams in, 548
    Shirasu microballoons, 517
    Shock absorbers, syntactic foams as, 547
    Short carbon fiber (SCF), 538, 539f
    Short fiber-reinforced syntactic foams
    (SFRSF), 538, 539f
    Silane cross-linking, 712
    715
    effects, 715
    Silica nanocomposites
    epoxy resin, 646
    650
    overview, 646
    phenolic resin, 650
    654
    polyimides, 650
    654
    polyurethanes, 650
    654
    unsaturated polyesters, 650
    654
    Silicon alkoxide-derived polymer ceramic
    materials, 410
    411
    Silicone fluids, 569
    573
    copolymers, 573
    dimethylsilicone, 571, 571t
    methylphenylpolysiloxane, 571
    573,
    572t
    methylpolysiloxane, 569, 570t
    temperature on viscosity, effects on,
    569, 571t
    Silicone/glass microbubble foam, 535
    Silicones
    compounding, 564
    curing, 565
    566
    elastomers, 557
    thermoplastic, 568
    569
    fluids. See Silicone fluids
    high temperature vulcanization (HTV),
    561
    566
    laminates, 566
    medical device industry, 566
    567
    overview, 555
    557
    room-temperature-vulcanizing (RTV),
    557
    561
    addition cure, 561
    condensation cure, 560
    561
    one-component, 557
    560
    two-component, 560
    trade names, 573, 573t
    UV-activated, 567
    568
    Silicone syntactic foams, 534
    535
    SMARTweave sensors, 746, 746f
    Soccer balls, 546
    547
    Soft sensors, 744
    Solgel-derived polyimide-silica
    nanocomposites, 413
    Soy proteins, 593
    594
    Specialty thermosets, 2
    Sports industry, syntactic foams in,
    546
    547
    Spray layup, 151
    153
    Staging, 8
    10, 8f
    Stannous tin octoate (STO), 561
    STO. See Stannous tin octoate (STO)
    Strand board, 27
    Structural reaction injection molding
    (S-RIM), 155
    Styrene monomer, 111
    112
    Sugar, 588
    589
    Sugar-based epoxy systems, 596
    Sulfonalion process, 15
    Syntactic foams
    applications, 545
    548
    aerospace industry, 546
    buoyancy, 545
    546
    furniture, 547
    military, 547
    miscellaneous, 547
    548
    plug-assist materials, 547
    radomes, 546
    shielding electronic components, 548
    sports industry, 546
    547
    synthetic marble, 547
    thermal insulation materials, 546
    bismaleimides, 514
    515
    carbon-carbon, 535
    core sandwich composites, 542
    543
    cyanate esters, 514, 530
    531
    elastomeric, 535
    epoxy, 512, 520
    525
    features, 519
    520
    fiber-reinforced, 535
    538
    functionally graded, 542
    matrices used, 511
    515
    microspheres, 515
    517
    nano reinforcement, 539
    540
    overview, 511
    520
    phenolic, 512
    514, 525
    528
    polybenzimidazole, 534
    polybenzoxazines, 529
    polyester, 534
    polyimide, 531
    532
    polyurethane, 533
    534
    preparation, 518
    519
    coating method, 519
    impregnation techniques, 518
    properties, 519
    compression, 519
    520, 519f
    low dielectric constants, 520
    mechanical, 519
    moisture absorption, 520
    thermal, 520
    rubberized, 540
    542
    silicone, 534
    535
    SMP-based, 543
    545
    stress-strain curve for compression
    testing, 519
    520, 519f
    structure, 517
    518
    three-phase, 518, 518f
    two-phase, 517
    518, 518f
    Synthetic marble, syntactic foams in, 547
    Syringol, 614f
    T
    Tannins, 589, 613
    614
    condensed, 590f
    hydrolyzable, 589
    Tannins, and phenolic resins, 36
    37
    Tectosil, 561, 563f, 569
    Terpene-derived acid anhydride
    (TPAn), 597
    Thermal insulation materials, syntactic
    foams as, 546
    Thermal properties, syntactic foams, 520
    Thermosets
    categories of, 2, 3t
    defined, 1
    engineering, 2
    general purpose, 2
    historical milestones of, 3t
    relationship in chemistry, 2f
    specialty, 2
    Three-phase syntactic foams, 518, 518f
    Trans-anethol, and cyanate ester
    monomers, 443
    445, 445f
    Trelleborg Emerson & Cuming, Inc., 547
    2,2,4-tri(4-cyanatophenoxy)-
    4,6,6-tris-phenoxy-2?5,4?5,6?5-
    [1,3,5,2,4,6]-triazatriphosphine,
    442, 442f
    Triglycerides, 579
    581, 579f
    acrylation of epoxidized, 582
    583,
    583f
    conversion into mono/diglycerides/
    simple fatty acids, 585
    587
    double bonds, 581
    enone-containing, 585, 586f
    epoxidation, 582, 582f
    hydroformylation, 583, 584f
    hydroxylation, 583
    584
    maleinization
    acrylated epoxidized oils, 583, 584f
    hydroxylated oils, 585, 586f
    oxypolymerization, 581f
    ozonolysis, 583, 585f
    1,2,3-tris(4-cyanatophenyl) propane,
    439
    440, 441f
    Tungsten disulfide
    epoxy resin, 675
    overview, 674
    675
    INDEX 767Two-component RTV silicones, 560
    addition cure, 561, 562t
    vs. condensation cure systems, 563t
    condensation cure, 560
    561, 562t
    DBT, 560
    STO, 561
    vs. addition cure systems, 563t
    curing, 565
    566
    vs. one-component, 560
    U
    Ultrasonic sensors, 748, 748f
    Unsaturated polyesters
    applicable manufacturing processes
    overview, 148
    149
    work place safety, 149
    bio-based and recycled raw materials,
    120
    122
    carbonanotubes, 137
    139
    carbon nanofibers, 137
    139
    cross-linking by copolymerization with
    co-monomers, 116
    118
    cured, 123
    125
    chemical resistance, 124
    125
    flexible, 123
    124
    hydrolytical stability, 124
    125
    rigid general purpose (GP), 123
    embedding matrix for magnetostrictive
    materials, 166
    fiber-reinforced, 150
    160
    flame retardance, 139
    144
    inorganic filler materials, 139
    140
    structural modification, 140
    142
    foamed, 166
    general aspects, chemistry, 112
    in luminescent solar concentrators,
    165
    166
    manufacturing, 112
    116
    market situation, 112, 113f
    nanoclays as fillers, 137
    nanoclays compositions, 628
    631
    nanocomposites, 136
    139
    nanofibrous fillers, 137
    139
    nanoparticles, 139
    neat, 122
    overview, 111
    112
    polymeric capacitators in printed circuit
    boards, 166
    POSS nanocomposites, 641
    646
    processing equipment and
    manufacturing, 118
    119
    process intensification, 120
    property modification, 136
    148
    raw materials, 114t
    shrinkage, 144
    148
    anti-shrink additives, 148
    anti-shrink units, 148
    silica nanocomposites, 650
    654
    styrenated, 122
    123
    trade names & manufacturers, 167t
    ultrafine, 166
    vinyl ester resins, compounding with,
    129
    136
    aromatic tertiary amine/benzoyl
    peroxide-based catalysts, 131
    commercial pre-promoted resins,
    131
    132
    curing systems, 130
    132
    fiber reinforcements, 136
    fillers, 134
    136
    handling catalysts and promoters, 132
    heat curing systems, 132
    inhibitors, 132
    ketone peroxide-based catalysts,
    130
    131
    metal soaps, 130
    131
    overview, 129
    130
    room temperature (RT) curing,
    130
    132
    thickening agents, 136
    thixotropic/flow control agents,
    132
    134
    ultraviolet absorbers, 132
    vs. saturated polyesters, 112
    Unsaturated polyesters, bio-based,
    598
    601
    Unsaturated polyesters (UP), 628
    631
    Urea, 76
    phenol and, co-condensation between, 36
    phenolic resin and, 35
    36
    Urea-formaldehyde (UF) resins
    condensation, 76
    78
    overview, 75
    raw materials, 76
    Urethane elastomer/glass microbubble
    foam, 535
    V
    Vacuum-bag process, 153
    Vegetable oils, 579
    copolymerization, 581
    polyurethanes from, 602
    606
    Vegetable proteins, 592
    593
    Veriflex SMP, 543
    Verilyte®, 544
    545
    VF-type FGSF, 542, 543f
    Vinyl ester resins, 125
    129
    overview, 125
    126
    special qualities, 127
    129
    trade names & manufacturers, 167t
    with unsaturated polyster,
    compounding, 129
    136
    aromatic tertiary amine/benzoyl
    peroxide-based catalysts, 131
    commercial pre-promoted resins,
    131
    132
    curing systems, 130
    132
    fiber reinforcements, 136
    fillers, 134
    136
    handling catalysts and
    promoters, 132
    heat curing systems, 132
    inhibitors, 132
    ketone peroxide-based catalysts,
    130
    131
    metal soaps, 130
    131
    overview, 129
    130
    room temperature (RT) curing,
    130
    132
    thickening agents, 136
    thixotropic/flow control agents,
    132
    134
    ultraviolet absorbers, 132
    Vulcanization, 2
    W
    Wacker Chemie AG, 568
    Water board, 27
    Water extended polyester (WEP), 161
    WEP. See Water extended polyester
    (WEP)
    Whey proteins, 593
    Wood products, composite, phenolic
    resins, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    Working life. See Pot life
    Z
    Zein proteins, 593

Handbook of Thermoset Plastics
Third Edition
Edited by
Hanna Dodiuk , Sidney H. Goodman
Table of contents

1. Introduction
   History
   Definitions
   Cross-Linking and Curing
   Influence of Time, Temperature, and Mass
   Shelf Life and Pot Life
   Curing
   Staging
   Stoichiometric Considerations
   Prepolymerization and Adducting
   References
   Further Reading
2. Phenol–Formaldehydes
   Introduction
   Raw Materials
   Phenol
   Resinification (Production) of Phenol–Formaldehyde Resins
   Phenolic Resins in Friction Materials
   References
   Further Reading
3. Polybenzoxazine–new generation phenolics
   Introduction
   Synthesis of Benzoxazine Monomers (BZ)
   Ring-Opening Polymerization of Benzoxazines
   Regioselectivity and Cross-Linked Structure
   Inter/Intramolecular H-Bonding
   Kinetics of Thermal Cure
   Structure-Property Relationships
   Blends/Composites of Polybenzoxazines
   Green Chemistry Approaches in PBZ
   Click Chemistry in PBZ
   Stability and Degradation
   Outlook
   Acknowledgments
   References
4. Aminos
   Introduction
   Raw Materials
   Chemistry of UF Resins: Urea–Formaldehyde Condensation
   Chemistry of MF Resins: Melamine–Formaldehyde Condensation
   General Principles of Manufacture and Application
   Applications of Amino Resins
   References
5. Furans
   Introduction
   Resins from Furfuryl Alcohol and Furfural
   Photocross-Linkable Furan Polyesters
   Furan Polyurethane Foams
   Photoresists from Pending Furan Chromophores
   Ion-Exchange Resins Based on 2-Vinylfuran
   Networks Based on Diels-Alder Polycondensations
   References
6. Unsaturated Polyesters and Vinyl Esters
   Unsaturated Polyesters
   Vinyl Ester Resins
   Compounding of Unsaturated Polyester and Vinyl Ester Resins
   Property Modification of Unsaturated Polyesters
   Applicable Manufacturing Processes
   References
7. Allyls
   Introduction
   Polydiallyldiglycolcarbonate (CR-39)
   Polydiallyl Phthalates
   References
8. Epoxies
   Introduction
   Detailed Chemistry
   Characterization of Epoxies
   Applications
   References
   Further Reading
9. Polyurethanes
   Introduction
   General Characteristics of Polyurethanes
   Raw Materials Used in the Synthesis of Cross-Linked Polyurethanes
   Synthesis and Cross-Linking Reactions of Polyurethanes
   Morphology of Linear/Branched vs. Cross-Linked Polyurethanes
   Manufacturing Methods and Technical and Functional Properties of Thermosetting Polyurethanes
   References
10. High-Performance Polyimides and High Temperature Resistant Polymers
    Historical Perspective
    Polyimides from Condensation Reactions
    Thermoplastic Polyimides
    Addition-Curable Polyimides and Other Polymers
    Nadimide-Terminated Thermosetting Polyimides
    Maleimide-Terminated Thermosetting Polyimides
    Cyanate-Terminated Thermosetting Polymers
    High-Temperature Thermosetting Resins Based on Phthalonitrile
    Acetylene-Terminated Thermosetting Polymers
    Propargyl-Terminated Oligomers
    Phenylethynyl-Terminated Thermosetting Polymers
    Applicability of Thermoset Isoimides/Imides to Resin Transfer Molding Processing
    Galvanic Corrosion Resistance of Polyimide Composites
    High-Performance Polymers for Lightning Strike Protection
    Ultrahigh Temperature Resistant Polymers
    Chemical Structures Suitable for Ultrahigh Temperature Use
    Novel Cross–Linking Mechanisms for Stability at Ultrahigh Temperatures
    Thermosets as Dielectric Interlayers in Integrated Circuit (IC) Fabrication
    Polymer-Ceramic Materials
    Acknowledgments
    References
    Further Reading
11. Cyanate Esters
    Introduction
    Chemistry
    Characterization and Reaction Monitoring
    Processing of Cyanate Ester Resins
    Properties of Cyanate Esters
    Properties of Cyanate Ester Blends with Epoxy and BMI
    Recent Developments
    Applications
    Trade Names
    References
12. Maleimide-Based Alder-Enes
    Introduction to Bismaleimides
    Maleimide-Based Alder-Ene Polymers
    Alder-Ene Polymers from Various Allyl-Maleimide Compounds
    Alder-Ene Polymer Blends
    Nano-Modified Alder-Ene Polymers
    Shape Memory Alder-Ene Polymers
    Kinetics of Alder-Ene Polymerization
    Outlook
    Acknowledgments
    References
13. Syntactic Foams
    Introduction
    Syntactic Foams Based on Thermosets
    Recent Advances in Syntactic Foams
    Applications of Syntactic Foams
    Outlook
    Acknowledgments
    References
14. Silicones
    Introduction
    Silicone Elastomers
    Silicone Laminates
    Silicones in the Medical Device Industry
    Special Silicones
    Silicone Fluids
    Other Fluid Types/Copolymers
    References
15. Biobased Thermosets
    Polymers from Renewable Sources
    Determination of Bio-Based Content in Polymers
    Raw Materials for Renewable Sources Polymers
    Thermoset from Renewable Sources
    References
16. Nanotechnology Based Thermosets
    Introduction
    Nanoclays
    POSS
    Nano Silica
    Carbon Nanotubes (CNT)
    Graphene and Expanded Graphite
    Tungsten Disulfide
    References
17. Crosslinked Thermoplastics
    Introduction
    Radiation Cross-Linking of Thermoplastics
    Effects of Radiation Cross-Linking on Thermoplastic Polymers
    Chemical Cross-Linking with Organic Peroxides
    Effects of Peroxide Cross-Linking on Thermoplastic Polymers
    Cross-Linking of Thermoplastics Using Silane Grafting Reagents
    Effects of Silane Cross-Linking on Thermoplastic Polymers
    Comparison of Cross-Linking Methods
    Applications of Cross-Linked Thermoplastics
    References
18. Processing
    Introduction
    Processing of Monomers: Online Monitoring of Resin Synthesis
    Processing of Pre-Polymers: Online Monitoring of Resin Flow and Resin Cure During Composite Manufacture
    References
    Appendix. Polybenzoxazines – Commercial Information
    Commercial Benzoxazine Marketed by Huntsman
    Products by Henkel
    Index
    Note: Page numbers followed by “f” and “t” indicate figures and tables, respectively.
    A
    Abietic-type acids, 597
    598, 598f
    Acenaphthylene, 401
    Acetoxy cure, for silicones, 558
    560, 559t
    Acidic Ion Exchange Resin (AIER), 581
    Acrylation, of epoxidized triglycerides,
    582
    583, 583f
    Addition cure, RTV silicones, 561, 562t
    vs. condensation cure systems, 563t
    Adhesives
    phenolic bio-based, 41
    PRF, 39
    40
    reduced resorcinol content, 40
    41
    resorcinol, 37
    Aerospace industry, syntactic foams in, 546
    Albumin, 593
    Alder-ene polymer
    allyl compounds, 463
    486
    blends, 486
    495
    high-performance blends, 486
    491
    nano-modified, 495
    497
    overview, 462
    463
    polymerization
    kinetics, 499
    504
    reaction sequence, 462
    463, 463f
    shape memory, 497
    498
    thermoplastic-toughened, 491
    495
    Alkoxy cure, for silicones, 558
    559, 559t
    Alkyd resins, bio-based, 610
    611
    Allyls
    overview, 173
    174
    polydiallyldiglycolcarbonate
    (PDADGC), 174
    180
    applications, 178
    180
    formulation, 176
    polymerization, 176
    properties, 176
    177
    trade names, 180
    polydiallyl phthalates, 180
    187
    applications, 185
    187
    chemistry, 181
    formulation, 183
    general aspects, 180
    181
    polymerization, 181
    183
    properties, 183
    185
    trade names, 187
    Aluminium phosphate, 411
    412
    Amide cure, for silicones, 558
    Amino resins
    adhesive and bonding, 82
    83, 88
    composite wood materials, 88
    medium density fiberboard
    (MDF), 88
    particle board, 88
    coatings, 83
    84
    application, 88
    paper treatment, 88
    protective, 88
    textile treatment, 88
    laminating, 84
    application, 88
    89
    manufacturing, 80
    87
    mixed melamine resins, 79
    80
    molding, 84
    87
    application, 89
    90
    overview, 88
    89
    Anhydride, for curing epoxy syntactic
    foams, 523, 523f
    Animal proteins, 592
    593
    Applications, 142
    144
    cross-linked thermoplastics, 716
    734
    acrylates, 730
    733, 731t
    fluoride-containing polymers,
    733
    734
    heat-shrinkable tubing, 723
    730, 725t
    polyolefin foams, 716
    719
    rotational molding, 719
    723
    cyanate ester resins, 448
    450
    phenolic resins
    coating applications, 35
    laminating applications, 31
    32
    molding applications, 32
    34
    syntactic foams, 545
    548
    aerospace industry, 546
    buoyancy, 545
    546
    furniture, 547
    military, 547
    miscellaneous, 547
    548
    plug-assist materials, 547
    radomes, 546
    shielding electronic components, 548
    sports industry, 546
    547
    synthetic marble, 547
    thermal insulation materials, 546
    Art objects, 161
    ASTM D6866-11, 578
    B
    Baekeland, Leo, 2
    Beetle grades, 83
    84
    Benzocyclobutene, 399
    400
    Benzoxazines, 514, 514f
    curable moieties, 51
    56
    curing, 47, 47f
    ortho positions, 48, 48f
    regioselectivity, 47
    49
    ring-opening polymerization, 47, 47f
    4,40-biamaleimido diphenyl methane
    (BMPM), 459
    Bio-based content
    defined, 578
    in polymers, 578
    579
    Bio-based phenolic resins, 611
    615
    Biopolymers, 2
    4,40-bis(4-cyanatobenzyl) biphenyl
    (BBPCy), 442, 443f
    2,20-bis(4-cyanatophenyl)isopropylidene
    (DCBA), 433
    435
    Bismaleimide (BMI), 514
    515
    blends with epoxy resins, cyanate ester
    resins, 435
    437
    description, 459
    462
    drawbacks, 461
    flammability, 461
    glass transition temperatures, 514
    modification approaches, 462
    reaction mechanism, 459, 460f
    structure, 532f
    synthesis, 459
    462, 460f, 515f
    thermo-mechanical properties,
    compared to other high-performing
    resin, 461t
    761BMI. See Bismaleimide (BMI)
    Bulk molding compounds (BMC),
    155
    156
    Buoyancy applications, syntactic foams
    in, 545
    546
    C
    Carbohydrates, 588
    589
    polyols from, 607
    Carbon-carbon syntactic foams, 535
    applications, 548
    Carbon dioxide (CO2), 578
    Carbon fiber-reinforced polymer
    (CFRP), 546
    Carbon nanotubes (CNT)
    epoxy resin, 656
    659
    overview, 654
    665
    phenolic resin, 659
    665
    polyimides, 659
    665
    polyurethanes, 659
    665
    Cardanol, 592
    structure, 592f
    Cardanol-formaldehyde resins, 613
    Casted giftware, 161
    Celluloid, 577
    CEN/TS 16137, 578
    579
    CFRP. See Carbon fiber-reinforced
    polymer (CFRP)
    Chemometrics, 742
    744
    Chemosets, 3
    Clay-polymer nanocomposites, 413
    Coating applications, phenolic
    resins in, 35
    Co-condensation, between phenol and
    urea, 36
    Coefficient of thermal expansion (CTE)
    of epoxy syntactic foams, 525
    Cold box process, phenolic resin, 31
    Collagen, 593
    Composite wood products, phenolic
    resins, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    Compression, syntactic foams, 519
    520,
    519f
    Condensation cure RTV silicones,
    560
    561, 562t
    DBT, 560
    STO, 561
    vs. addition cure systems, 563t
    Core sandwich composites, syntactic
    foams, 542
    543
    closed-pore structure, 543
    low moisture absorption, 543
    one-step compression molding, 543
    Cornerstone Research Group (CRG),
    544
    545
    Cow milk, 592
    593
    CRG. See Cornerstone Research Group
    (CRG)
    Cross-linked acrylates, 730
    733, 731t
    Cross-linking, 3
    4
    applications, 716
    734
    acrylates, 730
    733, 731t
    fluoride-containing polymers,
    733
    734
    heat-shrinkable tubing, 723
    730, 725t
    polyolefin foams, 716
    719
    rotational molding, 719
    723
    comparison methods, 715
    716
    defined, 3
    dimensional behavior upon, cyanate
    ester, 433
    molecular functionality, 4
    silane grafting reagents, 712
    715
    effects, 715
    wih peroxides, 708
    polyethylene, 708
    711, 709f
    polypropylene, 711
    712
    wih radiation. See Radiation crossLinking
    Cultured marble and onyx, 161
    162
    Cumene process, for phenol, 15
    Cure schedule, 7, 8f
    Curing, 7
    8
    defined, 5
    Curing agent
    defined, 5
    6
    Cyanate ester resins
    applications, 448
    450
    blends with epoxy and BMI,
    435
    437, 436t
    curing, 427
    429
    cyclo-trimerization, 430
    dimensional behavior upon crosslinking, 433
    distinctive features, 426t
    epoxy resins, 435
    436
    gelation, 433
    glass transition temperature
    and tensile elongation-at-break,
    431, 432f
    heterocyclic aromatic structure, 427
    hydrolysis behavior, 433
    435
    industrial demand, 426, 426f
    metal catalyst, 430, 431t
    monomers, 427, 428t
    bio-based raw materials, 442
    445
    conferring flame retardance,
    440
    442
    modifying flexibility, 437
    440
    novel, 437
    445
    optical spectroscopy, 429
    overview, 437
    445
    processing, 430
    431
    catalyst composition, 430
    frontal polymerization, 445
    446
    microwave-assisted polymerization,
    446
    447
    nanoconfinement, 448
    plasma polymerization, 448
    properties, 425, 431
    435
    electrical, 431
    433
    mechanical, 431
    physical, 434t
    thermal, 431, 432f
    Raman spectroscopy, 429
    reaction scheme illustrating
    formation, 426f
    structural unit, 427, 427f
    thermal analysis, 429
    430
    trade names, 451, 451t
    viscosity, 427
    Cyanate esters syntactic foams, 514,
    530
    531
    Cymel grades, 84
    D
    DBT. See Dibutyl tin dilaurate (DBT)
    Denaturation, proteins, 592
    593
    Diallyl Bisphenol A (DABA), 532f
    Diamines, 459
    460
    Dianhydrohexytols, 588
    589
    Diazine, 401
    402
    Dibutyl tin dilaurate (DBT), 560
    Dielectric analysis sensors, 746
    748, 747f
    Differential scanning calorimetry
    (DSC), 750
    751
    Diglycidyl ether of bisphenol A
    (DGEBA), 512, 512f
    9,10-Dihydro-9-oxa-10-
    phosphaphenanthrene-10-oxide
    (DOPO), 442, 443f
    Dimethylsilicone fluids, 571, 571t
    Dow process, for phenol, 15
    Drying oils, 581
    DSC. See Differential scanning
    calorimetry (DSC)
    E
    EAS. See Epoxidized allyl soyate (EAS)
    Eco-Core, 525
    526
    Elastomeric syntactic foams, 535
    as stress relief coatings, 535, 548
    Elmet GmbH, 567
    568
    Engel Austria GmbH, 567
    568
    Engineering thermosets, 2
    Enone-containing triglycerides, 585, 586f
    EPB syntactic foam, 531, 532f
    modulus, 532, 533f
    strength, 532, 533f
    Epon resin, 595
    596
    Epoxidation
    of catechin using epichlorohydrin,
    596
    597, 597f
    of triglycerides, 582, 582f
    Epoxidized allyl soyate (EAS), 595
    596
    762 INDEXEpoxidized linseed oil, 597, 597f
    Epoxidized oils, 595
    chemical modification, 595
    596
    Epoxidized soybean oil (EBSO), 595
    Epoxidized soybean oil (ESO),
    524
    525, 525f
    Epoxy/nanoclay compositions, 625
    628
    Epoxy resins, 8
    acid-curing agents, 206
    210
    cyclic anhydrides, 207
    209
    Lewis acids, 206
    mercaptans, 209
    210
    organic acids, 207
    phenols, 206
    207
    polysulfides, 209
    210
    alkaline curing agents, 201
    206
    aliphatic amines, 202
    203
    amine adducts, 203
    aromatic amines, 204
    205
    cyclic amines, 203
    204
    Lewis bases, 201
    202
    polyamides, 205
    206
    applications, 243
    247
    blends with BMI, cyanate ester, 435
    437
    carbon nanotubes (CNT), 656
    659
    characterization, 216
    243
    chemoviscosity, 239
    240
    colorants, 214
    216
    cross-link density, 232
    240
    cross-linking, 200
    curing, 199
    200
    curing agents, 200
    differential scanning calorimetry
    (DSC), 234
    temperature-modulated, 234
    236
    diglycidyl ether of bisphenol A
    (DGEBA), 192
    195
    diluents
    nonreactive, 212
    213
    reactive, 210
    211
    dyes, 214
    216
    Dynamic Mechanical Analysis, 237
    238
    α-epoxy (or 1,2-epoxy), 192
    ethylene oxide, 192f
    fillers, 213
    214
    formulation principles, 210
    216
    gass transition, 232
    240
    gelation, 240
    241
    glycidyl group, 192f
    graphene and expanded graphite,
    667
    671
    heat, 220
    232
    historical development, 299
    314
    hydantoin resins, 196
    molecular weight, 232
    240
    nanoclays compositions, 625
    628
    novolacs, 195
    overview, 297
    299
    peracid resins, 195
    196
    POSS nanocomposites, 638
    641
    resinous modifiers, 211
    212
    rheological additives, 216
    stoichiometry, 200
    201
    structure, 532f
    Thermally Stimulated Depolarization,
    238
    239
    thermomechanical analysis (TMA),
    236
    237
    vitrification, 241
    243
    Epoxy syntactic foams, 512, 520
    525
    bulk density, 520
    521, 521f
    coefficient of thermal expansion
    (CTE), 525
    compressive strength, 520
    521, 521f
    curing agents, 523, 523f
    fracture toughness, 523
    glass transition temperature,
    523
    524, 523f
    materials and process details, 524t
    neat resins, 523
    524, 524f
    tensile properties with microballoon
    volume fraction, 520, 521f
    ESO. See Epoxidized soybean oil (ESO)
    Expanded graphite
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    F
    Fatty acids, 579
    581, 580t
    Fevernova, 546
    547, 547f
    FGSF. See Functionally graded syntactic
    foams (FGSF)
    Fiber board, 27
    Fiber Bragg Gratings (FBGs), 749
    750,
    750f
    Fiber optics
    embedded, 748
    749
    measurement, 748
    750
    Fiber-reinforced syntactic foams,
    535
    538
    flexural strength, 536, 536f
    length of fiber, 537
    538, 538f
    short carbon fiber (SCF), 538, 539f
    storage modulus, 538, 539f
    tensile and flexural properties, 537,
    538f
    thermal stability, 538, 539f
    mechanical properties, 536, 537f
    silica fiber, 536, 537f
    tensile strength, 536, 536f
    Young’s modulus, 537
    Fillers, phenolic resins, 23
    24
    Fluoride-containing polymers, 733
    734
    trade names, 734t
    Formaldehyde, 15
    16
    Formalin, 15
    16
    impurities, 16
    Frontal polymerization, cyanate ester
    resins, 445
    446
    Functionalized vegetable oils (FVO),
    524
    525
    Functionally graded syntactic foams
    (FGSF), 542
    RR-type, 542, 543f
    VF-type, 542, 543f
    Furan resins
    chromophores, 101
    103
    Diels-Alder (DA) reaction,
    95, 95f
    polycondensations, 105
    107
    hydroxymethylfuraldehyde (HMF),
    94
    95, 95f
    overview, 93
    96
    photocross-linkable, 100
    polyurethane foams, 101
    2-vinylfuran (VF), 103
    105
    Furfural (F)
    condensation, derivatives with
    aldehydes and ketones, 94f
    furfuryl alcohol (FA), 93
    mechanism of formation, 94f
    monomers prepared from, 94f
    overview, 93
    resins from, 96
    100
    Furfuryl alcohol (FA), 93
    resins from, 96
    100
    Furniture, syntactic foams in, 547
    FVO. See Functionalized vegetable
    oils (FVO)
    G
    Gelation, cyanate ester resins, 433
    General purpose thermosets, 2
    Geniomer, 568
    569, 569f
    Gliadin, 593
    Global warming, 578
    Glycerol, 588
    Glycerolysis, 585
    587, 587f
    Graphene and expanded graphite
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    Graphite, expanded
    epoxy resin, 667
    671
    overview, 665
    674
    phenolic resin, 671
    674
    polyimides, 671
    674
    polyurethanes, 671
    674
    Guaiacol, 614f
    H
    Hand layup, 150
    151
    HCR. See High consistency silicone
    rubber (HCR)
    Heat-shrinkable tubing, 723
    730, 725t
    INDEX 763HEXA. See Hexamethylene tetramine
    (HEXA)
    Hexamethylene tetramine (HEXA), 16
    Hexamine. See Hexamethylene tetramine
    (HEXA)
    High consistency silicone rubber
    (HCR), 561
    563
    High temperature vulcanization (HTV),
    561
    566
    silicones, 561
    566
    Hydroformylation, of triglycerides, 583, 584f
    Hydrolysis behavior, cyanate ester resins,
    433
    435
    Hydroxylated oils, maleinization, 585, 586f
    Hydroxylation, of triglycerides, 583
    584
    Hydroxymethylfuraldehyde (HMF),
    94
    95, 95f
    I
    Impranil, 546
    547
    International Confederation for Thermal
    Analysis and Calorimetry
    (ICTAC), 753
    Isocyanate, and phenolic resins, 36
    37
    Isoidide, 588
    589, 588f
    Isomannide, 588
    589, 588f
    Isosorbide, 588
    589, 588f
    K
    Kienle, R. H., 610
    L
    Laccain, 14. See also Phenolic resins
    Laminates, silicones, 566
    Laminating applications, phenolic resins
    in, 31
    32
    LCA. See Life cycle assessment (LCA)
    Life cycle assessment (LCA), 577
    578
    Lignin, 443, 444f, 612
    613, 613f
    as additives, 590
    in epoxy resin networks, 596
    generic structure, 591f
    grafting of, 590
    591
    hydrolysis, 590
    methylolation, 614
    615
    nonphenolic hydroxypropyl, 590
    phenolation or phenolysis, 614
    615
    Lignins, and phenolic resins, 36
    Linear polymer, 3, 4f
    Lipids, 579
    Liquid Silicone Rubbers (LSR), 565
    Litidionite, organically modified, 412
    413
    Low dielectric constants, syntactic
    foams, 520
    LSR. See Liquid Silicone Rubbers (LSR)
    M
    Maleates, 585
    587
    Maleinization
    acrylated epoxidized oils, 583, 584f
    hydroxylated oils, 585, 586f
    Mannich bridge (CH2-N-CH2), 48
    49
    Mat molding, for UPR and VER, 157
    MCR ALS. See Multivariate curve
    resolution calculated by alternating
    least squares (MCR ALS)
    Medical device industry, silicones in,
    566
    567
    Melamine, 76
    Melamine-formaldehyde (MF) resins
    as adhesives, 75
    76
    condensation, 78
    80
    overview, 75
    raw materials, 75
    Melamine-urea-formaldehyde (MUF)
    resins, 79
    80
    copolymerization, 79
    80
    phenol, 80
    UF and MF mixtures, 79
    80
    Methacrylation, monoglycerides, 587
    Methylphenylpolysiloxane fluids,
    571
    573, 572t
    Methylpolysiloxane fluids, 569, 570t
    Methyl-tetrahydrophthalic anhydride
    (MTHPA), 524
    525, 525f
    Microballoon, in syntactic foams,
    515
    517, 517f
    Microspheres syntactic foams, 515
    517
    Microwave-assisted polymerization,
    cyanate ester resins, 446
    447
    Military, syntactic foams in, 547
    Moisture absorption, syntactic foams, 520
    Molding applications, phenolic resins in,
    32
    34
    Monoglycerides, 585
    587
    methacrylation, 587
    Monolithic flooring, 162
    Monomers, cyanate ester resins, 427, 428t
    bio-based raw materials, 442
    445
    conferring flame retardance, 440
    442
    modifying flexibility, 437
    440
    novel, 437
    445
    MTHPA. See Methyl-tetrahydrophthalic
    anhydride (MTHPA)
    Multivariate curve resolution calculated
    by alternating least squares (MCR
    ALS), 744
    N
    Nanoclays
    compositions
    epoxy, 625
    628
    phenolic resins, 631
    633
    polyimide, 635
    637
    polyurethane, 633
    635
    unsaturated polyesters, 628
    631
    nanocomposites, 625
    overview, 623
    625
    Nanoconfinement, cyanate ester
    resins, 448
    Nano reinforcement, in syntactic foams,
    539
    540
    Nano silica. See Silica nanocomposites
    NASA Ames Research Center, 546
    Natural oils, 579
    587. See also
    Triglycerides
    direct polymerization, 581
    double bonds, chemical modification
    of, 581
    585
    Natural rubber, 2
    Network polymer, 3, 4f
    NMR spectroscopy, 750
    Novocardt, 598
    Novolak phenolic resins, 19
    20
    vs. resole, 20
    O
    One-component RTV silicones, 557
    560
    acetoxy cure, 558
    560, 559t
    alkoxy cure, 558
    559, 559t
    amide cure chemistry, 558
    oxime cure chemistry/by-product, 558
    primers, 560
    Si-O-Si bonds, 557
    558
    Online monitoring tools
    overview, 739
    resin flow/cure, 744
    753
    dielectric analysis sensor, 746
    748
    embedded fiber optics, 748
    749
    Fiber Bragg Gratings (FBG),
    749
    750
    other methods, 750
    SMARTweave sensor, 746
    thermal analysis, 750
    753
    ultrasonic sensors, 748
    resin synthesis, 740
    744
    chemometrics, 742
    744
    general aspects, 740
    optical spectroscopy, 740
    744
    Raman spectroscopy, 742
    Optical fibers. See Fiber optics
    Optical spectroscopy, 740
    744
    FTIR, 741
    742
    infrared (IR), 741
    742
    nuclear magnetic resonance (NMR),
    741
    742
    Optical spectroscopy, cyanate ester
    resins, 429
    Organically modified litidionite, 412
    413
    Organic peroxides, chemical cross-linking
    with, 708
    Oxime cure chemistry/by-product,
    silicones, 558
    Ozonolysis, triglycerides, 583, 585f
    P
    [2.2]Paracyclophane, 397
    398
    Partially stabilized zirconium oxide
    (PSZ), 412
    Particle board, 27
    764 INDEXPeroxide cross-linking, 708
    polyethylene, 708
    711, 709f
    polypropylene, 711
    712
    Peroxide curing agents, silicone, 564t, 565
    Phenol, 15
    16
    cumene process, 15
    Dow process, 15
    Raschig process, 15
    urea and, co-condensation between, 36
    Phenol-formaldehyde resins. See Phenolic
    resins
    Phenolic microballoons, in syntactic
    foams, 517
    Phenolic (P1) and PN resin (PNM),
    527, 527f
    Phenolic resins
    bio-based, 611
    615
    carbon nanotubes (CNT), 659
    665
    coating applications, 35
    co-condensation between phenol and
    urea, 36
    composite wood products, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    description, 14
    15
    differences between resole and
    novolac, 20
    fillers, 23
    24
    friction materials, 29
    41
    graphene and expanded graphite,
    671
    674
    hexamethylene tetramine (HEXA), 16
    as insulation materials, 29
    isocyanate, addition of, 36
    37
    laminating applications, 31
    32
    lignins, addition of, 36
    modification, 35
    37
    molding applications, 32
    34
    nanoclay compositions, 631
    633
    nanoclays compositions, 631
    633
    novolak, 19
    20
    plywood, 25
    27
    POSS nanocomposites, 641
    646
    PRF. See Phenol-resorcinolformaldehyde (PRF)
    processing methods, 24
    25
    properties, 20
    23
    raw materials for, 15
    resinification, 16
    29
    polymerization process, 16
    19
    reaction mechanism, 16
    resole, 19
    silica nanocomposites, 650
    654
    tannins, addition of, 36
    37
    urea, addition of, 35
    36
    Phenolic syntactic foams, 512
    514,
    525
    528
    aldehyde groups, 528, 528f
    hollow carbon microspheres, 528,
    528f, 529f
    mechanical properties, 526
    527, 526t
    microballoon-based, 528
    PN resin (PNM), 527, 527f
    tensile and flexural strength, 526
    527
    Phenol-resorcinol-formaldehyde (PRF), 37
    adhesives, 39
    40
    Plant oil, 579
    581
    fatty acids, 579
    581, 580t
    polymers, 581
    triglycerides, 579
    581, 579f
    Plasma polymerization, cyanate ester
    resins, 448
    Plasticization, proteins, 592
    593
    Plug-assist materials, syntactic
    foams as, 547
    Plywood, 25
    27
    Polybenzimidazole syntactic foams, 534
    Polybenzoxazines (PBz), 514
    bio-based products, 67
    68
    blends, 61
    67
    co-reactive, 61
    64
    non-reactive, 61
    64
    chemical bridge structures, 48, 48f
    click chemistry, 68
    69
    composites
    fiber, 65
    66
    micro, 65
    66
    cross-linked structure, 47
    49, 49f
    inter/intramolecular H-bonding, 49
    main chain, 60
    61
    nanocomposites, 66
    67
    stability and degradation, 69
    syntactic foams
    mechanical strength, 529, 529f
    thermal curing, 49
    51
    unfunctionalized, 56
    60
    Polyester syntactic foams, 534
    Polyethylene
    peroxide cross-linking, 708
    711
    radiation cross-linking, 703
    silane cross-linking, 712
    715
    Polyhedral oligomeric silsesquioxanes
    (POSS)
    epoxy, 638
    641
    isocyanate groups, 642
    643
    N-phenylaminomethyl, 643
    octa(aminophenyl)-POSS, 644
    OpePOSS, 642
    overview, 637
    646
    phenolic resin, 644
    polyimides (PI), 644
    645
    polyurethanes, 641
    643
    silanols, 646
    silsesquioxanes, 644
    unsaturated polyester, 643
    644
    Polyimides
    acetylene-terminated, 361
    374
    imide oligomers, 364
    367
    oligomers, cure mechanism,
    369
    374
    quinoxalines, 362
    364
    sulfones, 364
    addition-curable, 335
    336
    adhesive formulations, 388
    AFR700B resins, 344
    aromatic characteristics, 298f
    carbon nanotubes (CNT), 659
    665
    coatings
    high-temperature resistant, 388
    insulative, 386
    condensation reactions, 299
    314
    conductive paint, 388
    conductive polymer blends, 386
    corrosion
    galvanic, 385
    387
    mechanism, 385
    386
    cyanate esters
    polyimide-based, 355
    356
    semi-interpenetrating polymer
    network (SIPN), 355
    cyanate-terminated, 351
    356
    graphene and expanded graphite,
    671
    674
    historical perspective, 297
    299
    hydrogen-free, 393
    395
    imide structural analogs, 387
    isoimide modification, 367
    369
    low-viscosity SIPN imide blends,
    384
    385
    maleimide-terminated, 344
    350
    modified nadimide end-caps, 343
    344
    nanoclay compositions, 635
    637
    nanoclays compositions, 635
    637
    nonmetallic conductive materials, 388
    NR-150 (DuPont), 318
    phenylethynyl-terminated, 374
    382
    phthalonitrile, 356
    361
    polyamic acid converted to, 298f
    polycyanurates
    electronic industry, 356
    flame retardancy, 356
    POSS nanocomposites, 641
    646
    propargyl-terminated oligomers, 374
    resin transfer molding (RTM)
    aerospace resins, 383
    384
    isoimides/imides applicability,
    382
    385
    polyimides, relevance of, 384
    silica nanocomposites, 650
    654
    thermoplastic, 314
    334
    Torlon®, 325
    328
    Ultem®, 318
    324
    ultrahigh temperature resistant
    polymers, 388
    389
    XU 218 (XIV), 329
    332
    Polyimide syntactic foams, 531
    532
    Polymer-ceramic materials, 409
    413
    INDEX 765Polymer-clay nanocomposites, 625
    Polymer concretes, 162
    164
    Polymeric microballoons, in syntactic
    foams, 517
    Polymerization, cyanate ester resins
    frontal, 445
    446
    microwave-assisted, 446
    447
    plasma, 448
    Polymerization process, phenolic
    resins, 16
    19
    Polymers
    biphenylene, 396
    397
    bisazoles, 390
    393
    phthalocyanine, 393
    ultrahigh temperature resistant,
    388
    389
    Polyolefin foams, 716
    719
    Polyols
    from carbohydrates, 607
    from lignocellulosic materials, 606
    from natural polyphenols, 607
    Polyols, from carbohydrates, 607
    Polyphenols, 589
    592
    Polypropylene
    peroxide cross-linking, 711
    712
    radiation cross-linking, 703
    707
    Polyurethanes (PU), 633
    635
    adhesives, 286
    287
    auxiliary agents, 264
    266
    bio-based, 601
    610
    from vegetable oils, 602
    606
    blowing agents, 264
    carbon nanotubes (CNT), 659
    665
    catalysts, 263
    264
    chain extenders, 263
    characteristics, 254
    258
    coatings, 286
    287
    cross-linked, 276
    277
    medicine, 287
    289
    cross-linking, 266
    274
    radical reactions, 272
    274
    via allophanate or biuret bonds,
    269
    via cross-linkers, 267
    269
    via isocyanates dimerization or
    trimerization, 270
    272
    via polyols, 266
    267
    foams, 284
    286
    graphene and expanded graphite,
    671
    674
    isocyanates, 258
    261
    health hazard evaluation, 258
    261
    linear/branched, 275
    276
    manufacturing methods, 277
    289
    nanoclays compositions, 633
    635
    oligomerols, 261
    263
    derived from glycolysates, 262
    other types, 263
    from renewable raw materials, 262
    unsaturated, 262
    overview, 253
    254
    POSS nanocomposites, 641
    646
    raw materials, 258
    266
    silica nanocomposites, 650
    654
    vegetable oils, 602
    606
    Polyurethane syntactic foams, 533
    534
    Polyvinyl chloride (PVC), 707
    708
    Polyvinylidene chloride (PVDC)
    microspheres, 547
    ultra low-density, 547
    Polyvinylidene fluoride (PVDF), 733
    734
    Pot life, 7
    Preform molding, for UPR and VER, 157
    Premix molding, for UPR and VER, 157
    Pre-preg process, 153
    Pressure-bag process, 153
    154
    PRF. See Phenol-resorcinol-formaldehyde
    (PRF)
    Primasetr PT-30, 439
    440, 441f
    Prolamine proteins, 593
    Propargyl ether novolac (PN)
    mechanical properties, 526t
    synthesis, 513, 513f
    Proteins, 592
    594
    albumin, 593
    animal and vegetable, 592
    593
    collagen, 593
    cow milk, 592
    593
    denaturation, 592
    593
    gliadin, 593
    gluten, 593
    plasticization, 592
    593
    prolamine, 593
    soy, 593
    594
    whey, 593
    zein, 593
    Prototype molding, for UPR and VER,
    156
    157
    Pultrusion, UPR and VER in, 158
    R
    Radiation cross-linking, 698
    703
    oxidation, 701
    702
    polyethylene, 703, 706t
    polymers, 702t
    polypropylene, 703
    707, 706t
    polyvinyl chloride (PVC), 707
    708
    Radomes, syntactic foams in, 546
    Raman spectroscopy, 742
    Raman spectroscopy, cyanate ester
    resins, 429
    Rapid Thermal Processing, 613
    Raschig process, for phenol, 15
    Renewable sources polymers
    bio-based polymers, 577
    578
    crbon content, 578
    579
    bio-based polyurethanes, 601
    610
    bio-based unsaturated polyester,
    598
    601
    epoxy, 594
    615
    natural oils, 579
    587. See also
    Triglycerides
    direct polymerization, 581
    double bonds, chemical modification,
    581
    585
    raw materials for, 579
    594
    Resin, defined, 5
    6
    Resin cure modeling, 750
    753
    Resin flow/cure analysis, online
    monitoring tools for, 744
    753
    dielectric analysis sensor, 746
    748
    embedded fiber optics, 748
    749
    Fiber Bragg Gratings (FBG), 749
    750
    other methods, 750
    SMARTweave sensor, 746
    thermal analysis, 750
    753
    ultrasonic sensors, 748
    Resin infusion process, 153
    154
    Resin synthesis, online monitoring tools,
    740
    744
    chemometrics, 742
    744
    general aspects, 740
    optical spectroscopy, 740
    744
    Raman spectroscopy, 742
    Resin transfer molding (RTM), 154
    155
    Resole phenolic resins, 19
    vs. novolak, 20
    Resorcinol adhesives, 37
    Resorcinol-formaldehyde (RF) resins, 37
    chemistry, 37
    39
    Room-temperature-vulcanizing (RTV)
    silicones, 557
    561
    addition cure, 561, 562t
    condensation cure, 560
    561, 562t
    DBT, 560
    STO, 561
    one-component, 557
    560
    acetoxy cure, 558
    560, 559t
    alkoxy cure, 558
    559, 559t
    amide cure chemistry, 558
    oxime cure chemistry/by-product, 558
    primers, 560
    Si-O-Si bonds, 557
    558
    two-component, 560
    vs. one-component, 560
    Rosin, 597
    598
    Rotational molding, 719
    723
    RR-type FGSF, 542, 543f
    RTV. See Room-temperature-vulcanizing
    (RTV) silicones
    Rubberized syntactic foams, 540
    542,
    542f
    S
    Saccharides, 588
    589
    Saran microballoons, 517, 547
    Sensors
    dielectric analysis, 746
    748, 747f
    SMARTweave, 746, 746f
    ultrasonic, 748, 748f
    766 INDEXSFRSF. See Short fiber-reinforced
    syntactic foams (SFRSF)
    Shape memory, UPR with, 164
    Shape memory polymer (SMP)-based
    syntactic foams, 543
    545
    compressed and expanded forms, 545f
    DMA studies, 543
    544, 544f
    durability, 544
    glass transition temperature, 543
    544
    thermomechanical properties, 544, 545f
    ultraviolet radiation, 544
    Sheet molding compounds (SMC), 155
    156
    Shelf life, 7
    Shell molding process, phenolic resin in, 31
    Shielding electronic components, syntactic
    foams in, 548
    Shirasu microballoons, 517
    Shock absorbers, syntactic foams as, 547
    Short carbon fiber (SCF), 538, 539f
    Short fiber-reinforced syntactic foams
    (SFRSF), 538, 539f
    Silane cross-linking, 712
    715
    effects, 715
    Silica nanocomposites
    epoxy resin, 646
    650
    overview, 646
    phenolic resin, 650
    654
    polyimides, 650
    654
    polyurethanes, 650
    654
    unsaturated polyesters, 650
    654
    Silicon alkoxide-derived polymer ceramic
    materials, 410
    411
    Silicone fluids, 569
    573
    copolymers, 573
    dimethylsilicone, 571, 571t
    methylphenylpolysiloxane, 571
    573,
    572t
    methylpolysiloxane, 569, 570t
    temperature on viscosity, effects on,
    569, 571t
    Silicone/glass microbubble foam, 535
    Silicones
    compounding, 564
    curing, 565
    566
    elastomers, 557
    thermoplastic, 568
    569
    fluids. See Silicone fluids
    high temperature vulcanization (HTV),
    561
    566
    laminates, 566
    medical device industry, 566
    567
    overview, 555
    557
    room-temperature-vulcanizing (RTV),
    557
    561
    addition cure, 561
    condensation cure, 560
    561
    one-component, 557
    560
    two-component, 560
    trade names, 573, 573t
    UV-activated, 567
    568
    Silicone syntactic foams, 534
    535
    SMARTweave sensors, 746, 746f
    Soccer balls, 546
    547
    Soft sensors, 744
    Solgel-derived polyimide-silica
    nanocomposites, 413
    Soy proteins, 593
    594
    Specialty thermosets, 2
    Sports industry, syntactic foams in,
    546
    547
    Spray layup, 151
    153
    Staging, 8
    10, 8f
    Stannous tin octoate (STO), 561
    STO. See Stannous tin octoate (STO)
    Strand board, 27
    Structural reaction injection molding
    (S-RIM), 155
    Styrene monomer, 111
    112
    Sugar, 588
    589
    Sugar-based epoxy systems, 596
    Sulfonalion process, 15
    Syntactic foams
    applications, 545
    548
    aerospace industry, 546
    buoyancy, 545
    546
    furniture, 547
    military, 547
    miscellaneous, 547
    548
    plug-assist materials, 547
    radomes, 546
    shielding electronic components, 548
    sports industry, 546
    547
    synthetic marble, 547
    thermal insulation materials, 546
    bismaleimides, 514
    515
    carbon-carbon, 535
    core sandwich composites, 542
    543
    cyanate esters, 514, 530
    531
    elastomeric, 535
    epoxy, 512, 520
    525
    features, 519
    520
    fiber-reinforced, 535
    538
    functionally graded, 542
    matrices used, 511
    515
    microspheres, 515
    517
    nano reinforcement, 539
    540
    overview, 511
    520
    phenolic, 512
    514, 525
    528
    polybenzimidazole, 534
    polybenzoxazines, 529
    polyester, 534
    polyimide, 531
    532
    polyurethane, 533
    534
    preparation, 518
    519
    coating method, 519
    impregnation techniques, 518
    properties, 519
    compression, 519
    520, 519f
    low dielectric constants, 520
    mechanical, 519
    moisture absorption, 520
    thermal, 520
    rubberized, 540
    542
    silicone, 534
    535
    SMP-based, 543
    545
    stress-strain curve for compression
    testing, 519
    520, 519f
    structure, 517
    518
    three-phase, 518, 518f
    two-phase, 517
    518, 518f
    Synthetic marble, syntactic foams in, 547
    Syringol, 614f
    T
    Tannins, 589, 613
    614
    condensed, 590f
    hydrolyzable, 589
    Tannins, and phenolic resins, 36
    37
    Tectosil, 561, 563f, 569
    Terpene-derived acid anhydride
    (TPAn), 597
    Thermal insulation materials, syntactic
    foams as, 546
    Thermal properties, syntactic foams, 520
    Thermosets
    categories of, 2, 3t
    defined, 1
    engineering, 2
    general purpose, 2
    historical milestones of, 3t
    relationship in chemistry, 2f
    specialty, 2
    Three-phase syntactic foams, 518, 518f
    Trans-anethol, and cyanate ester
    monomers, 443
    445, 445f
    Trelleborg Emerson & Cuming, Inc., 547
    2,2,4-tri(4-cyanatophenoxy)-
    4,6,6-tris-phenoxy-2?5,4?5,6?5-
    [1,3,5,2,4,6]-triazatriphosphine,
    442, 442f
    Triglycerides, 579
    581, 579f
    acrylation of epoxidized, 582
    583,
    583f
    conversion into mono/diglycerides/
    simple fatty acids, 585
    587
    double bonds, 581
    enone-containing, 585, 586f
    epoxidation, 582, 582f
    hydroformylation, 583, 584f
    hydroxylation, 583
    584
    maleinization
    acrylated epoxidized oils, 583, 584f
    hydroxylated oils, 585, 586f
    oxypolymerization, 581f
    ozonolysis, 583, 585f
    1,2,3-tris(4-cyanatophenyl) propane,
    439
    440, 441f
    Tungsten disulfide
    epoxy resin, 675
    overview, 674
    675
    INDEX 767Two-component RTV silicones, 560
    addition cure, 561, 562t
    vs. condensation cure systems, 563t
    condensation cure, 560
    561, 562t
    DBT, 560
    STO, 561
    vs. addition cure systems, 563t
    curing, 565
    566
    vs. one-component, 560
    U
    Ultrasonic sensors, 748, 748f
    Unsaturated polyesters
    applicable manufacturing processes
    overview, 148
    149
    work place safety, 149
    bio-based and recycled raw materials,
    120
    122
    carbonanotubes, 137
    139
    carbon nanofibers, 137
    139
    cross-linking by copolymerization with
    co-monomers, 116
    118
    cured, 123
    125
    chemical resistance, 124
    125
    flexible, 123
    124
    hydrolytical stability, 124
    125
    rigid general purpose (GP), 123
    embedding matrix for magnetostrictive
    materials, 166
    fiber-reinforced, 150
    160
    flame retardance, 139
    144
    inorganic filler materials, 139
    140
    structural modification, 140
    142
    foamed, 166
    general aspects, chemistry, 112
    in luminescent solar concentrators,
    165
    166
    manufacturing, 112
    116
    market situation, 112, 113f
    nanoclays as fillers, 137
    nanoclays compositions, 628
    631
    nanocomposites, 136
    139
    nanofibrous fillers, 137
    139
    nanoparticles, 139
    neat, 122
    overview, 111
    112
    polymeric capacitators in printed circuit
    boards, 166
    POSS nanocomposites, 641
    646
    processing equipment and
    manufacturing, 118
    119
    process intensification, 120
    property modification, 136
    148
    raw materials, 114t
    shrinkage, 144
    148
    anti-shrink additives, 148
    anti-shrink units, 148
    silica nanocomposites, 650
    654
    styrenated, 122
    123
    trade names & manufacturers, 167t
    ultrafine, 166
    vinyl ester resins, compounding with,
    129
    136
    aromatic tertiary amine/benzoyl
    peroxide-based catalysts, 131
    commercial pre-promoted resins,
    131
    132
    curing systems, 130
    132
    fiber reinforcements, 136
    fillers, 134
    136
    handling catalysts and promoters, 132
    heat curing systems, 132
    inhibitors, 132
    ketone peroxide-based catalysts,
    130
    131
    metal soaps, 130
    131
    overview, 129
    130
    room temperature (RT) curing,
    130
    132
    thickening agents, 136
    thixotropic/flow control agents,
    132
    134
    ultraviolet absorbers, 132
    vs. saturated polyesters, 112
    Unsaturated polyesters, bio-based,
    598
    601
    Unsaturated polyesters (UP), 628
    631
    Urea, 76
    phenol and, co-condensation between, 36
    phenolic resin and, 35
    36
    Urea-formaldehyde (UF) resins
    condensation, 76
    78
    overview, 75
    raw materials, 76
    Urethane elastomer/glass microbubble
    foam, 535
    V
    Vacuum-bag process, 153
    Vegetable oils, 579
    copolymerization, 581
    polyurethanes from, 602
    606
    Vegetable proteins, 592
    593
    Veriflex SMP, 543
    Verilyte®, 544
    545
    VF-type FGSF, 542, 543f
    Vinyl ester resins, 125
    129
    overview, 125
    126
    special qualities, 127
    129
    trade names & manufacturers, 167t
    with unsaturated polyster,
    compounding, 129
    136
    aromatic tertiary amine/benzoyl
    peroxide-based catalysts, 131
    commercial pre-promoted resins,
    131
    132
    curing systems, 130
    132
    fiber reinforcements, 136
    fillers, 134
    136
    handling catalysts and
    promoters, 132
    heat curing systems, 132
    inhibitors, 132
    ketone peroxide-based catalysts,
    130
    131
    metal soaps, 130
    131
    overview, 129
    130
    room temperature (RT) curing,
    130
    132
    thickening agents, 136
    thixotropic/flow control agents,
    132
    134
    ultraviolet absorbers, 132
    Vulcanization, 2
    W
    Wacker Chemie AG, 568
    Water board, 27
    Water extended polyester (WEP), 161
    WEP. See Water extended polyester
    (WEP)
    Whey proteins, 593
    Wood products, composite, phenolic
    resins, 27
    fiber board, 27
    particle board, 27
    plywood, 25
    27
    strand board, 27
    water board, 27
    Working life. See Pot life
    Z
    Zein proteins, 593

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