The Chemistry of Bio-based Polymers Scrivener Publishing 100 Cummings Center, Suite 541J Beverly, MA 01915-6106 Publishers at Scrivener Martin Scrivener (martin@scrivenerpublishing.com) Phillip Carmical (pcarmical@scrivenerpublishing.com) The Chemistry of Bio-based Polymers Johannes Karl Fink Montanuniversität Leoben, Austria Copyright © 2014 by Scrivener Publishing LLC All rights reserved Co-published by John Wiley & Sons, Inc Hoboken, New Jersey, and Scrivener Publishing LLC, Salem, Massachusetts Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood 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commercial damages, including but not limited to special, incidental, consequential, or other damages For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002 Wiley also publishes its books in a variety of electronic formats Some content that appears in print may not be available in electronic formats For more information about Wiley products, visit our web site at www.wiley.com For more information about Scrivener products please visit www.scrivenerpublishing.com Cover design by Russell Richardson Library of Congress Cataloging-in-Publication Data: ISBN 978-1-118-83725-2 Printed in the United States of America 10 Contents Preface xiii An Overview of Methods and Standards 1.1 History of Biodegradable Plastics 1.2 Green Chemistry 1.2.1 Genetic Engineering 1.3 Commercial Situation 1.4 Environmental Situation 1.4.1 Problems with Biobased Composites 1.4.2 Biodegradation 1.5 Properties of Biodegradable Polymers 1.6 Special Methods of Synthesis 1.6.1 Conventional Methods 1.6.2 Click Chemistry 1.6.3 Enzymatic Polymerization 1.6.4 Chemoenzymatic Polymerization 1.6.5 Vine-twining Polymerization 1.6.6 Bacterial Synthesis 1.7 Biodegradability Standards 1.7.1 Guidelines for the Development of Standards 1.7.2 Specifications for Compostable Plastics 1.7.3 Ultimate Anaerobic Biodegradability 1.7.4 Aerobic Biodegradability 1.7.5 Biodegradability of Plastics in Sea water 1.8 Test of the Biological Origin References v 1 10 12 14 14 15 16 17 19 20 20 21 21 21 24 26 29 35 vi Contents Part I Bio-based Polymers Degradation and Chemistry 43 Vinyl Based Polymers 2.1 Polyolefins 2.1.1 Degradability 2.1.2 Degradation Mechanism 2.1.3 Pro-degradants 2.2 Poly(styrene) Elastomers 2.3 Poly(vinyl alcohol) 2.3.1 Plasticized Compositions 2.3.2 Hydrogels 2.4 Poly(vinyl butyral) 2.4.1 Blends with Poly(3-hydroxybutyrate) 2.4.2 Blends with Poly(lactic acid) 2.4.3 Paper coatings 2.4.4 Fibers 2.4.5 Membranes 2.4.6 Solar Cells 2.4.7 Adhesive for Safety Glass References 45 45 46 46 47 48 48 49 50 51 52 53 53 54 55 56 57 60 Acid and Lactone Polymers 3.1 Poly(lactic acid) 3.1.1 Production Processes for Poly(lactic acid) 3.1.2 Surface Modification of Fibers 3.1.3 Influence of Fabrication Methods and Kenaf Fiber Length 3.1.4 Kenaf fibers for Reinforcement of PP 3.1.5 Reinforced Composites 3.1.6 Laminated Composites from Kenaf Fiber 3.1.7 Copolyesters 3.1.8 Transparent Crystalline Poly(lactic acid) 3.1.9 Laminated Biocomposites 3.2 Poly(glycolic acid)s 3.2.1 Glycolic acid 3.2.2 Polymers, Copolymers, and Blends 3.2.3 Condensation Polymer of Glycerol 63 63 63 69 69 70 71 71 72 73 73 74 74 76 76 Contents 3.3 Butyrolactone-based Vinyl Monomers 3.3.1 Tulipalin A 3.3.2 a-Methylene-g-valerolactone 3.4 Poly(caprolactone) References vii 77 77 78 81 83 Ester and Amide Polymers 4.1 Poly(ester)s 4.1.1 Methyl-10-undecenoate 4.1.2 Poly(butylene adipate) Copolyesters 4.1.3 Poly(hydroxyalkanoate)s 4.1.4 Poly(hydroxybutyrate) 4.1.5 Poly(hydroxyvalerate) 4.1.6 Poly(3-hydroxyhexanoic acid) 4.1.7 Poly(b-hydroxyoctanoate) 4.1.8 Poly(g-glutamic acid) 4.1.9 Poly(butylene succinate) 4.1.10 Dianhydrohexitols based Polymers 4.1.11 Aliphatic-Aromatic Copolyesters 4.1.12 Succinate Based Polyesters 4.1.13 Sebacate Based Polyesters 4.1.14 Unsaturated Polyesters 4.1.15 Sulfonated Polyesters 4.2 Plant oil-based Biopolymers 4.2.1 Plant Oils with Acrylic Moities 4.2.2 Plant Oils with Phosphorus Moities 4.2.3 Vanillin Based Monomers 4.2.4 Vegetable oil Thermosets 4.3 Poly(amide)s 4.3.1 Soy Based Bio-plastic and Chopped Industrial Hemp 4.3.2 Soy bean based Composites References 87 87 87 87 88 89 91 93 94 95 95 98 102 108 108 112 113 117 118 120 121 123 124 Carbohydrate Related Polymers 5.1 Starch 5.1.1 Starch Modification 5.1.2 Starch Granules 137 137 138 140 124 124 131 viii Contents 5.1.3 5.1.4 5.1.5 5.1.6 5.1.7 5.1.8 5.1.9 5.1.10 Baked Foams High Starch Polymer Destructurization of Natural Starch Melt Processable Starch Wet-spinning Processes for Starch Pre-gelled Starch Suspensions Processing of Natural Starch Granular Starch as Additive to Conventional Polymers 5.2 Cellulose 5.2.1 Liquid Crystalline Derivatives 5.2.2 Cellulose Fibers 5.2.3 Modified Cellulose Fibers 5.3 Cellulose ethers 5.4 Cellulose esters 5.5 Cellulose ether esters 5.6 Lignin 5.7 Biodegradable Nanocomposites 5.7.1 Oxidation of Spruce and Pulps 5.7.2 Modified Cellulose Nanofibers 5.7.3 Biobased Epoxy Nanocomposites 5.8 Chitin References 140 140 142 143 145 145 146 146 149 150 151 154 158 158 158 160 162 162 164 164 164 167 Other Polymer Types 6.1 Terpenes 6.1.1 Grafted Terpene 6.1.2 Thiol-Ene Additions 6.1.3 Pinenes 6.2 Poly(urethane)s 6.2.1 Poly(ester urethane)s 6.3 Cationic Lipopolymers 6.4 Plastics from Bacteria 6.4.1 Biodegradability of Poly(hydroxyalkanoate) 6.5 Biobased Epoxy Resins 6.5.1 Poloxamers 6.6 Phosphate Containing Polymers 6.7 Polyketals 171 171 171 172 172 176 177 178 179 180 180 181 181 187 328 The Chemistry of Bio-based Polymers Calcium hydroxyapatite, 247 Carboplatin, 188 Carboxymethyl cellulose, 273 Carrageenan, 228 Cellobiose, 306 Chitosan, 81, 216, 224, 231, 280 Chloramphenicol, 251 Chlorcyclizine, 251 2-Chloro-1,3,2-dioxaphospholane, 184 1-Chloro-3-ethoxy-1,1,3,3-tetrabutyldistannoxane, 90 2-Chloro-2-oxo-1,3,2-dioxaphospholane, 184 Chlorpheneramine, 251 Citric acid, 115, 138, 148, 239, 269 Coniferyl alcohol, 160 p-Coumaryl alcohol, 160 Crotonic acid, 229 α-Cyclodextrin, 18 β-Cyclodextrin, 18 γ-Cyclodextrin, 18 1,3-Cyclohexanedicarboxylic acid, 103 1,4-Cyclohexane-dicarboxylic acid, 103 1,3-Cyclohexanedimethanol, 104 1,4-Cyclohexanedimethanol, 104 Cyclohexanone, 81 Cyclohexylammonium benzoate, 205 1,3-Cyclopentanedicarboxylic acid, 103 Decanoic acid, 229 Di-N-acetylchito-biosehexacetate, 165 2,2 -Diamino-1,1 -binaphthalene, 65 1,2-Diaminocyclohexane, 65 4,6-Diamino-1,2-dihydro-2,2-dimethyl-1-(2,6-xylyl)-1,3,5-triazine, 13 2,4-Diamino-6-(2-(dodecasylamino)ethyl)-1,3,5-triazine, 13 2,4-Diamino-6-(2-methoxyethyl)-1,3,5-triazine, 13 2,4-Diamino-6-(o-methoxyphenyl)-1,3,5-triazine, 13 2,4-Diamino-6-methyl-1,3,5-triazine, 13 2,4-Diamino-6-phenyl-1,3,5-triazine, 13 Di-tert-butylcarbodiimide, 12 2-(3,5-Di-tert-butyl-2-hydroxyphenyl)-5-chlorobenzotriazole, 13 Dibutyl peroxide, 214 1,2-Dichloroethane, 90, 184 1,3-Dichloro-1,1,3,3-tetrabutyldistannoxane, 95 Dicumyl peroxide, 281 Dicyclohexylammonium nitrate, 205 N,N -Dicyclohexylcarbodiimide, 12, 292 Index 4,4 -Dicyclohexylmethane diisocyanate, 12, 69 Diethyl aluminum dichloride, 173 Diethylamine, 78 N,N-Diethyl cyclohexylamine, 57 Diethylene glycol, 104 Diethylene glycol monomethyl ether, 68 Diethylenetriaminepentacetic acid, 57 Diethyl phthalate, 105 Diethylzinc, 255 Dihydrocarvone, 254, 254 5-(N-2,3-Dihydroxypropylacetamido)-2,4,6-triiodo-N,N -bis(2,3-dihydroxypropyl) isophthalamide, 242 Diisobutylcarbodiimide, 12 N,N -Diisopropylcarbodiimide, 12 Dimethyl adipate, 115 2-(Dimethylamino) pyridine, 57 4-(Dimethylamino) pyridine, 57 Dimethylcarbodiimide, 12 2,5-Dimethyl-2,5-di(tert-butyl peroxy) hexane, 287 Dimethyl formamide, 184 Dimethyl glutarate, 116 2,2-Dimethyl glutaric acid, 103 2,2-Dimethyl-1,3-propylene glycol, 104 Dimethyl succinate, 96, 219 Dimethyl terephthalate, 102, 115, 219 Di-β-naphthylcarbodiimide, 12 3,4 -Diphenyl ether dicarboxylic acid, 114 4,4 -Diphenyl ether dicarboxylic acid, 114 3,4 -Diphenyl sulfide dicarboxylic acid, 114 4,4 -Diphenyl sulfide dicarboxylic acid, 114 3,4 -Diphenyl sulfone dicarboxylic acid, 114 4,4 -Diphenyl sulfone dicarboxylic acid, 114 2-(4,6-Diphenyl-1,3,5-triazine-2-yl)-5-[(hexyl)oxy]phenol, 13 Distearylthiodipropionate, 277 1,2-Di-10-Undecenoylglycerol, 122 1,3-Di-10-undecenoylglycerol, 122 Docosanedioic acid, 114 1,2-Epoxybutane, 161 9,10-Epoxy-18-hydroxyoctadecanoic acid, 123 Erucamide, 58 Erucic acid, 111 Erucyl stearamide, 58 Ethyl acrylate, 125 Ethyl butyrate, 30 329 330 The Chemistry of Bio-based Polymers Ethyl cellulose, 233 Ethylene bis-12-hydroxystearic acid amide, 68 Ethylene carbonate, 98 Ethylene diamine, 57 Ethylene diamine monoacetic acid, 57 Ethylene glycol, 104, 178, 184, 202, 219 Ethylene glycol dimethacrylate, 214 Ethylene glycol monobutyrate, 49 Ethylene vinyl acetate, 275 5-Fluorouracil, 183, 183 Formic acid, 304 Fructose, 187 Glucose, 306 α-D-Glucose-1-phosphate, 19, 20 Glutaraldehyde, 52, 54 Glutaric acid, 114 Glycidyl acrylate, 105 Glycidyl methacrylate, 105 Glycolic acid, 66 Hexadecanedioic acid, 114 2,4-Hexadienoic acid, 229 1,1,1,3,3,3-Hexamethyldisilazane, 183, 184 Hexamethylene bis-12-hydroxystearic acid amide, 68 1,6-Hexamethylene diisocyanate, 67, 178 1,6-Hexanediol, 17, 104 Hexanoic acid, 229 2-Hexenoic acid, 229 Hexyl acrylate, 125 2-Hexyldecanoic acid, 229 Hyaluronic acid, 225, 232, 232 Hydrocinnamic acid, 229 trans-β-Hydromuconic acid, 229 Hydroxyapatite, 54 2-(2 -Hydroxy-3 -tert-butyl-5 -methylphenyl)-5-chlorobenzotriazole, 13 2-(2 -Hydroxy-5 -tert-butylphenyl)benzotriazole, 13 3-Hydroxybutyric acid, 66 γ-Hydroxybutyric-β-cyclodextrin, 19 3-Hydroxybutyrolactone, 6-Hydroxycaproic acid, 66 2,4-Hydroxydodecanoic acid, 229 Hydroxyethyl cellulose, 216 2-Hydroxyethyl-2-(2-hydroxyethylimino)propanoate, 270, 271 2-(2-Hydroxyethylimino)propane-1-ol, 270, 271 Hydroxyethyl methacrylate, 50 Index 3-Hydroxyhexanoic acid, 90 Hydroxymethylfurfural, 80, 304 2-(Hydroxymethyl)-1,3-propanediol, 115 Hydroxypivalic acid, 103 3-Hydroxypropionic acid, Hydroxypropyl methyl cellulose, 216, 230 γ-Hydroxyvaleric acid, 66 Iodoaminopurine, 184 Iododeoxyuridine, 251 Isophorone diisocyanate, 12, 176 Isophthalic acid, 114 4-Isopropylbenzoic acid, 229 Itaconic acid, 2, Lactic acid, 66 Lauric acid, 93, 228 Lichenan, 310 Lignocellulose, 308 Limonene, 172, 174 Maleic acid, 215 Malonic acid, 114 2-Mercaptoethanol, 178 Meso-lactide, 64 2-(Methacryoyloxy)ethyl succinate, 50 2-Methoxy-2-oxo-1,3,2-dioxaphospholane, 185 Methyl acrylate, 174 4,4 -Methylene bis(benzoic acid), 114 4,4 -Methylene-bis-(2,6-di-tert-butylphenol), 13 α-Methylene-γ-butyrolactone, 77, 78 3-Methylenecyclopentene, 175 Methylene diphenyl-4,4 -diisocyanate, 178 α-Methylene-γ-valerolactone, 78–80 Methyl methacrylate, 77, 125 N-Methylmorpholine oxide, 160 3-Methyl-1-phenyl-2-phospholene-1-oxide, 12 N-Methyl-2-pyrrolidone, 54 Methyl ricinoleate, 72 Methyl-10-undecenoate, 87 Methylvaleric acid, 229 Miconazole, 251 β-Myrcene, 172, 175 1,4-Naphthalene dicarboxylic acid, 114 2,7-Naphthalenedicarboxylic acid, 114 1,5-Naphthalic acid, 103 2,6-Napthalene dicarboxylic acid, 114 331 332 The Chemistry of Bio-based Polymers Nitrocellulose, 291 2,5-Norbornanedicarboxylic acid, 103 Octadecanamide, 58 Octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 13 1,8-Octanediol, 17 Octanoic acid, 229 Oleyl alcohol, 117 N-Oleyl palmitamide, 58 Oxalic acid, 114 2-Oxo-4-thiazolidinecarboxylic acid, 284 Paracetamol, 233 Pectin, 234 Penicillin, 238 15-Pentadecanolactone, 17 Pentaerythritol, 104 Pentaerythritol tetrakis 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 218 i-Pentane, 214 1,5-Pentanediol, 104 4-Pentenoic acid, 229 Phenylalanine, 289 Phenylbutazone, 251 N,N -(1,4-Phenylenedimethylidene)bis(2-(2-aminoethoxy)ethanol), 270, 271 N,N -(1,4-Phenylenedimethylidene) bis(ethanolamine), 270, 271 Phosphenol-pyruvate carboxylase, 30 Phosphotungstic acid, 75 Picolinic acid, 289 Pimelic acid, 114 α-Pinene, 172 β-Pinene, 172 Poly(ether imide), 178 Poly(D,L-lactide-co-ethylene methyl phosphate), 185 Poly(phosphate), 182 Poly(phosphite), 182 Poly(phosphonate), 182 Potassium thioacetate, 118 1,3-Propanediol, 30, 72, 180 γ-Propiolactone, 285 1,2-Propylene glycol, 218 Propylene oxide, 158, 181 Pyromellitic acid, 114 Rapeseed oil, 178 R,R-lactide, 64 Index Sebacic acid, 112, 114 S,S-lactide, 64 Sodium montmorillonite, 140 Sorbitol, 49, 141 Spiro-bis-dimethylenecarbonate, 281 Stearyl erucamide, 58 Suberic acid, 114 Succinic acid, 114 Terephthalic acid, 114 Tetra-n-butylammonium chloride, 173 Tetra-n-butyl-titanate, 96 Tetracosanedioic acid, 114 2,2,4,4-Tetramethyl-1,3-cyclobutanediol, 104 2,2,6,6-Tetramethylpiperidine-1-oxyl, 162 Tetramethylxylylene diisocyanate, 12 γ-Thiobutyrolactone, 284 2-Thioxo-4-thiazolidinecarboxylic acid, 284 Tin octoate, 66 Triethylene glycol, 202 Triisobutyl aluminum, 175 Triisopropyl aluminium, 111 Trimellitic acid, 114 3-(Trimethoxysilyl)propyl methacrylate, 273 Trimethylhexane-1,6-diisocyanate, 254 2,2,4-Trimethyl-1,6-hexanediol, 104 Trimethylolpropane, 64, 249 Tris(2-aminoethyl)amine, 57 Tris(2-hydroxyethyl)trimellitate, 116 Trisodium 1-phosphono-2-phosphino ethane, 286 Tris(pentafluorophenyl)gallium, 45 Trityl tetrakis(pentafluorophenyl)borate, 80 Undecanedioic acid, 114 δ-Valerolactone, 285 4-Vinylpyridine, 190 Wollastonite, 276 D-Xylulose, 307 Zeolite, 75 General Index Abiotic oxidation, 47 Abrasive materials, 279 Abiotic sterile control, 27 Acetalization, 51 333 334 The Chemistry of Bio-based Polymers Activation energy, 16 Adverse immunological reaction, 248 Anti-thrombogenic drugs, 258 Antioxidants, 12, 47, 212, 277 Antisense oligonucleotides, 188 Aquatic animals, 208 Arterial rupture, 255 Aseptic cartons, 204 Atherosclerotic plaque, 262 Bacteria, 179, 227, 300, 301, 304, 311 Bacterial fructans, 187 Batch mixer, 105 Bioceramics, 259 Biodegradability, 9, 20, 46, 88, 91, 147, 198, 300 Biodegradability standards, 20 Biodiesel, 299, 303, 313, 314 Bioethanol, 299, 302, 307, 309, 314 Biotically mediated oxidation, 48 Blow molding, 81, 144 Carbon dioxide sequestration, 124 Cellobiohydrolase, 306 Cellulose whiskers, 94 Chain extenders, 67, 102 Chemotherapeutic compounds, 188 Chewing gum, 218 Claisen reaction, Corrosion inhibitor, 204 Cotton linter, 71, 159 Crosslinking agent, 54, 214, 243, 254, 281 Cycloaddition, 15 Decorative surface coverings, 278 Degradative oxidation, 148 Dehydration acid-catalyzed, 98 polycondensation, 64 Delignification, 305, 308 Dendrimers, 16 Depolymerization, 65 Depressurization time, 55 Desiccation, 2, 55 Detergents, 16 Detoxification, 305 Diapers, 188, 212 Diblock copolymer, 284 Diels-Alder reaction, Diffusion, 231, 291 Digestion anaerobic, 23, 24 bacterial, 138 Dimensional stability, 276 Disposable absorbent articles, 210, 272 Disposable packaging, 197 Double screw kneader, 214 Drug delivery, 63, 95, 223, 231 implantable systems, 258 Dual carbon-isotopic fingerprinting, 29 Dual pore scaffolds, 239 Edmundson method, 184 Effervescent mixture, 239 Elastic modulus, 14, 102, 180 Elasticity enhancer, 141 Elastomers, 2, 48, 160, 175, 179 Electrodeposition, 238 Electrospinning, 54, 234, 259 Elmendorf tear strength, 104 Embolization, 242 Emulsifier, 227 Encapsulant, 56 Endcapper, 286 Endothelial cell growth factor, 250 Enzymatic biodegradation, 11 Enzymatic catalysis, 16, 308 Enzymatic degradation, 303, 308 Enzymatic erosion, 93 Enzymatic hydrolysis, 138, 308, 311 Enzymatic polymerization, 14, 16 Enzyme nomenclature, 305 Epidermal growth factor, 250 Epidermal tissues, 232 Esterification, 75, 95, 313 Index Ethenolysis, 117 Etherification, 158 Exfoliated clay nanoplatelets, 164 Fermentation inhibitors, 304, 312 Fermentor, 93 Fiber reinforced composites, 10, 72, 74, 124 Fibrillation, 163 Fibroblasts, 248, 259 Fickian diffusion, 231 Filaments, 108 Filler dispersion, 10 Fillers, 275 high aspect ratio, 276 Fire resistance, 277 Flame retardancy, 121, 214 Flammability, 277 Flexographic printing, 290 Flexural strength, 71, 124 Flooring materials, 275 Flory-Fox equation, 100 Fluorescence, 289 Foams, 213, 215, 239, 278 gelled, 216 Fogging, 200 Follicle stimulating hormon, 251 Fossil fuel, 29, 161, 303 Fountain-flowing, 293 Fragrance, Free radical polymerization, 77 Freeze-drying, 243 Functional polymers, 19 Fungal degradation, 300, 301 Gel casting, 243 Gelling agent, 217, 228, 231 Genetic engineering, 4, 307 Germs, 112 Glucose isomerase, 16, 307 Grafting, 92, 146, 178, 233 Granular starch, 146 Grignard reaction, Grubbs reaction, 117 Hatch-Slack photosynthetic cycle, 30 335 Heat deflection temperature, 70, 124, 162, 276 Heat-reactivation temperature, 217 Heterolytic fission, 118 Heteropolyacids, 75 Hill equation, 301 Hollow fiber membranes, 55 Homogeneous nucleation, 79 Homopolymerization, 255 Hormones, 188, 225 Hospital disposables, 46 Hue, 68 Humidification, 55 Humidity sensor, 55 Hunting activity, 208 Hyaluronic acid, 225 Hydrocolloids foamed, 215 marine, 224 Hydrogel macromers, 225 Hydrogels, 50, 95, 225, 241 Hydrogenation, 78, 79, 311 Hydrolase, 109 Hydrolyzable ester bonds, 254 Hydrophobicity, 172, 188 Hygiene articles, 218 Immunomodulators, 188 Implantable medical devices, 227, 256 In situ gelation, 258 Incineration, Incubation, 47 Injectable matrices, 258 Injection molding, 71, 124, 227, 242, 287 Inoculated soil, 301 Intercalation, 162 Interfacial adhesion, 10, 124 Interfacial interaction, 143 Interfacial polycondensation, 183 Intracoronary stent, 255 Isoelectric point, 55 Isotopic fractionation, 29 Izod impact strength, 70, 180 336 The Chemistry of Bio-based Polymers Jellyfish, 208 Juice, 9, 204 Ketene dimers, 154 Laccase, 308 Lactobacillus, 305 Landfills, 7, 207 Laser scanning microscopy, 152 Latex, 94, 290 Latex stabilization, 94 Letterpress presses, 290 Lewis acid catalyst, 183 Light-transmitting laminates, 57 Lightweight compostable packaging, 198 Lipase, 17 Lipopolymers, 178 Liposomes, 226 Liquid crystalline polymer, 150 Litter, 198 Loud speakers, 292 Lubricants, 282 Maize, 303 Malignant melanoma, 238 Mango, 234 Mangrove, 180 Masterbatch, 105, 204 Mediterranean region, 47 Melt transurethane method, 177 Michael reaction, 178 Microalgae, 314 Microbes, 213 Microcapsules, 225 Microcrystalline cellulose, 105 Microdenier fibers, 116 Microdroplets, 226 Microemulsions, 226 Microfibers, 259 Microneedles, 226 Microorganisms, 10, 25, 67, 111, 150, 208, 270, 289, 300 Micropellets, 281 Microspheres, 225, 290 Mineral nutrients, 27 Miniemulsion polymerization, 79 Molasses, 176, 303, 311 Molecular beam mass spectrometry, 313 Mucoadhesion, 234 Multifunctional monomer, 254 Multigene transformation, Multiple regression analysis, 230 Murein sacculus, 94 Mutagenesis, 307 Mutants, 307 Nanoclay, 140, 276 Nanocomposites, 10, 151, 162 Nanocrystals, 149 Nanofillers, 158 Nanoparticles, 54, 287 Nerve growth factor, 237 Neurotoxin implants, 252 Nonwoven fabrics, 270 Nucleophilic substitution reaction, 46 Oilfield applications, 188, 286 Olefin isomerization, 295 Olefin metathesis, 117, 121, 295 Olive oil, 90 Organoclay, 126, 164 Orodispersible tablet, 233 Osteoblasts, 248 Oxidative chain scission, 138 Oxidative dehydration, Ozone layer, Ozonolysis reaction, 111 Packaging materials, 8, 197 Paperboard containers, 54, 203 Periodontal disease, 248 Periodontal ligament cells, 248 Pharmacokinetic modifiers, 188 Photoperoxidation, 121 Photosynthetic carbon metabolism, 30 Pollutants, 7, 208, 314 Poloxamers, 181 Polydispersity, 79 Polyenes, 121, 295 Polymerizable hydrogels, 242 Index ζ-Potential, 55 Prepolymers, 50 Pro-degradant, 47 Prosthetic devices, Proteinaceous network, 189 Pumice, 279 Radiocarbon dating, 29 Radiopacity, 241 Rate-controlling polymers, 225 Reactive distillation, 313 Recombinant DNA techniques, 91 Recycled paper pulp, 145 Reppe reaction, 310 Respirometer, 24 Reverse osmosis, 109 Ring-opening polyaddition, 164 Rosin-Rammler function model, 294 Rotary embossing, 205 Salt leaching, 240 Sawdust, 216 Scaffolds, 189, 239, 335 Scale inhibitor, 188, 286 Schiff base, 14, 65 Schotten-Baumann reaction, 249 Scouring pads, 279 Sea water, 26, 108 Semiconducting wafer, 280 Semicrystalline polymer, 52 Septage sediments, 95 Shape memory polymers, 252 Slip agents, 57, 212 Sloppy gel, 272 Softwood, 162 Solid waste, 24, 203, 280 Spark-ignition, 312 Sprayable resin, 210 Starch-debranching enzymes, 139 Steam reforming, 313 Stenosis, 255 Stents, 188, 255, 257, 258 Stereoelective polymerization, 14 Stiles’ reagent, 78 Strawberries, 310 337 Subcutaneous implantation, 93 Superabsorbent materials, 272 Supramolecular bola-amphiphiles, 19 Surface acoustic wave resonator, 55 Sutures, 63, 179, 252 Tablet disintegrant, 231 Tackifier, 218, 269 Tearing resistance, 104, 142 Telechelic prepolymers, 65 Therapeutic radionuclides, 188 Thermochemical pretreatment, 303 Thermogelling Materials, 258 Thermosets, 123 Thermosetting prepolymers, 249 Thermotolerant yeast, 309, 310 Thiol-ene polyaddition, 121 Thrombosis, 262 Tissue engineering, 109, 223, 238, 239, 258, 284 Tissue growth promoters, 250 Tissue inflammation, 246 Topoisomerase inhibitor, 188 Toughening agent, 69 Transesterification, 49, 87, 96, 215, 295 Transgenic plants, Transplantation, 238 Tropical grasses, 30 Twin screw extruder, 74, 105, 258 Ultraviolet absorbers, 12, 56 Ultraviolet irradiation, 281 Unfolding process, 18 Vine-twining polymerization, 14, 19 Viscoelastic fluid, 232 Wastewater treatment, 92 Waxes, 218 Wells-Dawson 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