Polymers from Plant Oils

Alessandro Gandini is a physical chemist who has taught and conducted research for the last fifty years at academic and other institutions in Switzerland, UK, Canada, USA, Cuba, France, Brazil and Portugal, after his first degree in Italy. His main scientific interests are polymer synthesis and characterization, with a special emphasis on polymers from renewable resources, photochemistry, and the physical chemistry of surfaces and interfaces. He has published more than 400 scientific contributions and is an Honorary Doctor of the Saint Petersburg Forestry Academy and of Havana University, and was invested with the Ermine decoration of Grenoble National Polytechnic Institute, France. Talita M. Lacerda received her PhD degree in chemistry in 2012 from the São Carlos Institute of Chemistry, University of São Paulo, Brazil. After holding a post-doc position in Professor Alessandro Gandini's research group (2012-2016) and in Professor Michael Meier's research group (2013-2014), she moved in 2016 to the Biotechnology Department of Lorena School of Engineering, University of São Paulo. Her main research interests include the synthesis and chemical modification of polymers and the development of biocomposites based on renewable resources.

• Preface to First Edition viiPreface to the Second Edition ix1 Introduction 11.1 Setting the Stage 1References 72 Basic Chemical Notions 92.1 Drying Mechanism 92.2 Reactive Sites 112.2.1 Reactions of the Ester Group 122.2.2 Reactions of Unsaturated Bonds 13References 193 Polymerisation of Pristine Oils and their Fatty Acids 233.1 Polymerisation of Unsaturated Oils and Fatty Acids 233.2 Specific Case of Castor Oil 26References 314 Monomers and Polymers from Chemically Modified Plant Oils and their Fatty Acids 334.1 Epoxidised Structures 334.1.1 Direct Polymerisation 334.1.2 Reactions with Amines and Anhydrides 364.1.3 Acrylation Reactions 394.2 Polyol Structures for Polyurethanes 434.3 Polyisocyanates for Polyurethanes 474.4 Polyether and Polyester Diols for Thermoplastic Polyurethanes 494.5 Diols and Diacids for Linear Polyesters 514.6 Monomers for Linear Polyamides and Polycarbonates 574.7 Vinyl, Acrylic and Other Monomers for Linear Chain-growth Polymerisation 594.8 Monomers for Other, Less Common Linear Polymers 644.9 Special Cases of Castor Oil and Ricinoleic Acid 644.10 Special Case of Glycerol 69References 735 Metathesis Reactions Applied to Plant Oils and Polymers Derived from the Ensuing Products 835.1 General Considerations 835.2 Metathesis Reactions as Tools for the Synthesis of Monomers and Polymers Derived from Vegetable Oils 875.2.1 Metathesis Reactions for Monomer Synthesis 875.2.2 Olefin Metathesis Applied to Polymer Synthesis 925.2.2.1 Acyclic Diene Metathesis Polymerisation 925.2.2.2 Acyclic Triene Metathesis Polymerisation 975.2.2.3 Ring-opening Metathesis Polymerisation 985.2.2.4 Special Cases of Acetal Metathesis Polymerisation and Alternating Diene Metathesis Polymerisation 101References 1046 Thiol-ene and Thiol-yne Reactions for the Transformation of Oleochemicals into Monomers and Polymers 1096.1 General Considerations 1096.2 Thiol-ene Reaction as a Tool for the Synthesis of Monomers and Polymers Derived from Vegetable Oils 1126.2.1 Thiol-ene Reactions for Monomer Synthesis 1126.2.2 Thiol-ene Reactions Applied to Polymer Synthesis 1206.2.3 Thiol-ene Reactions for Chemical Modifications after Polymerisation 1256.3 Thiol-yne Reaction as a Tool for the Synthesis of Monomers and Polymers Derived from Vegetable Oils 1276.4 Final Considerations 130References 1307 Diels–Alder Reactions and Polycondensations Applied to Vegetable Oils and their Derivatives 135References 142