Furan Polymers and their Reactions (eBook)

Alessandro Gandini, PhD, is a retired professor from the National Polytechnic Institute, Grenoble, France and subsequently worked as an invited teacher and researcher at the Universities of São Paulo, Brazil, Aveiro, Portugal and Bologna, Italy. He is a pioneering researcher in the field of polymers from renewable resources. Talita Martins Lacerda, PhD, is an Assistant Professor at the Lorena School of Engineering, University of São Paulo, Brazil. She has researched and published extensively in the field of polymer synthesis from biomass resources.

Foreword vii

Preface viii

1 A Brief History 1

2 The Peculiar Chemical Features of the Furan Heterocycle and the Synthesis of Furfural and Hydroxymethylfurfural 3

2.1 Free Radical Reactions 3

2.2 Electrophilic Reactions 5

2.3 Photochemistry 5

2.4 Hydrolysis Reactions 9

2.5 The Diels-Alder Reaction 10

2.6 Furfural and Hydroxymethylfurfural as Industrial Commodities and as Building Blocks for Furan Monomers 11

3 Polymers from Furfural and Furfuryl Alcohol 18

3.1 Furfural Resins 18

3.2 Furfuryl Alcohol Resins 21

4 Polymers from Chain Polyaddition Reactions 37

4.1 Free Radical Systems 37

4.2 Cationic Systems 42

4.3 Anionic Systems 51

4.4 Stereospecific Systems 57

5 Polymers from Polycondensation (Step) Reactions 61

5.1 Polyesters 61

5.2 Polyamides 90

5.3 Polyurethanes 103

5.4 Polyureas, Polyparabanic Acids, Polybenzoxazines, polySchiff Bases, and Polyhydrazides 114

5.5 Conjugated Furan Oligomers and Polymers 124

5.6 Epoxy Resins 134

6 The Furan/Maleimide Diels-Alder Reaction Applied to Polymer Synthesis and Modification 147

6.1 Polycondensations (Step-growth Polymerizations) 148

6.2 Polymer Modification and Cross-linking 156

6.3 Miscellaneous Systems 180

6.4 A New Paradigm: Aromatics from Furans 186

7 Chemical and Biological Degradation 192

8 General Conclusions 200

Index 202