Synthetic Biodegradable and Biobased Polymers: Industrial Aspects and Technical Products (Advances in Polymer Science, 293)

Preface
	References
Contents
Biotechnological and Chemical Production of Monomers from Renewable Raw Materials
	1 The Chemical Value Chains
	2 Demand for Chemicals Produced with Renewable Energy and Renewable Raw Materials
	3 Renewable Raw Materials
	4 Introducing RRM into Established Chemical Value Chains
	5 The ``Efficiency Trap´´ for RRM Utilization
	6 Substitution of Fossil Naphtha by RRM in Existing Chemical Value Chains: The Biomass Balance (BMB) Approach
	7 Direct Chemical or Biotechnological Conversion of Specified First Gen RRM toward Dedicated Chemicals
		7.1 Direct Conversion of RRM to Chemical Products by Fermentation
		7.2 Conversion of RRM to Chemical Products Using Chemical Synthesis
		7.3 Examples for the Direct Conversion of RRM to Chemical Products by Biotechnology or Chemical Synthesis
			7.3.1 C2: Ethylene from Bioethanol
			7.3.2 C3: Lactic Acid (LA)
			7.3.3 C3: 3-Hydroxypropionate (3-HP)
			7.3.4 C3: 1,3-Propanediol (1,3-PDO)
			7.3.5 C4: 1,4-Butanediol (BDO)
			7.3.6 C4: Succinic Acid (SA)
			7.3.7 C5: 1,5-Diaminopentane (DAP) or Pentamethylenediamine (PMDA)
			7.3.8 C6: Isosorbide
			7.3.9 C6: Adipic Acid (ADA)
			7.3.10 C6: Caprolactam (CPL) and Hexamethylenediamin (HMD)
	8 Concluding Remarks
	References
The Terpenes Limonene, Pinene(s), and Related Compounds: Advances in Their Utilization for Sustainable Polymers and Materials
	1 Introduction
	2 Polymerization of Acyclic Terpenes
	3 Polymerization of Cyclic Terpenes
		3.1 Cycloolefin (Hydrocarbon) Polymers
		3.2 Polycarbonates and Polyesters from Terpenes
		3.3 Polyamides, Polyurethanes, and Others from Terpenes
	4 General Remarks
	5 Conclusion
	References
Polymer Biodegradability 2.0: A Holistic View on Polymer Biodegradation in Natural and Engineered Environments
	1 Introduction
	2 Definition of Polymer Biodegradability and Biodegradation
	3 Process Elucidation of Polymer Biodegradation
		3.1 Steps in Polymer Biodegradation
		3.2 Factors Controlling Polymer Biodegradation
			3.2.1 Polymer-Dependent Factors that Control Polymer Biodegradation
			3.2.2 Environment-Dependent Factors that Control Polymer Biodegradation
		3.3 Variation in Polymer Biodegradation Between Receiving Environments
	4 Setups and Analytical Methods to Study Biodegradation and to Test Biodegradability of Polymers
		4.1 Laboratory Incubations
		4.2 Mesocosm and Field Studies
		4.3 Recent Analytical Advancements in the Assessment of Polymer Biodegradation
			4.3.1 Stable-Carbon Isotope Labelling of Polymers
			4.3.2 Quantification of Residual Polymer
	5 Standard Tests and Certifications for Polymer Biodegradability and Biodegradation
		5.1 Motivation for Testing
		5.2 Levels of Testing
		5.3 Status of Standard Test Methods and Specifications
		5.4 Certifications
	6 Research Needs
		6.1 Variations in Polymer Biodegradation in and Across Different Receiving Environments
		6.2 Assessing Uncertainties Associated with the Transferability of Results of Polymer Biodegradability from Laboratory Tests t...
		6.3 Identification of Key Degrading Enzymes and Microbial Degraders
		6.4 Microbial Metabolic Utilization of Plastic and Polymer Carbon
		6.5 Slowly Biodegrading Polymers
	References
ecoflex and ecovio: Biodegradable, Performance-Enabling Plastics
	1 Introduction
	2 Biodegradability and Toxicology
		2.1 Mechanism of the Biodegradation of Polymers
		2.2 Biodegradation of ecoflex and ecovio
			2.2.1 Compostability of ecoflex and ecovio
			2.2.2 Biodegradation and Environmental Fate of ecovio M2351: Biodegradability Research Beyond Certification
			2.2.3 Biodegradation in the Marine Environment of ecovio
		2.3 Toxicological Assessment of Biodegradable Polymers
			2.3.1 Water-Soluble Intermediates: Daphnia Test
			2.3.2 Plant Growth Test
			2.3.3 Earthworm Acute Toxicity Test
			2.3.4 Assessment of Skin and Eye Irritation
			2.3.5 Assessment of Sensitization
			2.3.6 Acute Oral Toxicity
			2.3.7 Assessment of Mutagenicity
	3 Certified Compostable and Soil-Biodegradable Plastics: Their Role in a Circular Economy and Greenhouse Gas Emission Reductio...
		3.1 Compostable Plastics as an Enabler for Organics Recycling of Bio-waste
	4 ecoflex and ecovio
		4.1 ecoflex: A Completely Biodegradable Aliphatic-Aromatic Polyester
			4.1.1 Relevant Characteristics of ecoflex F
				Primary and Secondary Molecular Structure of ecoflex F
				Thermal Properties of ecoflex F
				Rheology of ecoflex F Melts
		4.2 ecovio: Blends of ecoflex and Other Biopolymers
			4.2.1 ecoflex/Starch Blends
				Starch as Raw Material for Plastics
				ecoflex/Starch Blends
			4.2.2 ecoflex/PLA Blends: ecovio
				Poly(Lactic Acid) (PLA), a Compostable, Renewable Polymer, and a Raw Material for Compostable Polymer Blends
				ecoflex/PLA Blends
	5 ecoflex and ecovio: Processing
		5.1 Extrusion
			5.1.1 Film Extrusion
				Blown Film Extrusion
				Cast Film Extrusion
			5.1.2 Extrusion Foaming
				Foam Sheet Extrusion
				Particle Foam
			5.1.3 Extrusion Coating
			5.1.4 Lamination
				Extrusion Lamination
				Adhesive Lamination
		5.2 Injection Molding
			5.2.1 Properties of ecovio Injection Molding Grades
			5.2.2 Processing of ecovio by Injection Molding
		5.3 Thermoforming
			5.3.1 Properties and Processing of ecovio by Thermoforming
		5.4 Additives and Post Treatment
			5.4.1 Additives
			5.4.2 Post Treatment
	6 Applications
		6.1 Bag Applications
			6.1.1 Organic Waste Bags
			6.1.2 Shopping (Carrier) Bags
			6.1.3 Fruit and Vegetable Bags
		6.2 Agricultural and Horticultural Applications
			6.2.1 Mulch Film
			6.2.2 ecovio for Horticulture
		6.3 Packaging
			6.3.1 Flexible Food Packaging
			6.3.2 Rigid Food Packaging
	7 Market Overview and Growth Drivers
	8 Outlook
	References
Biobased Synthesis and Biodegradability of CO2-Based Polycarbonates
	1 Introduction
	2 Monomer Synthesis
		2.1 Propylene Oxide
		2.2 Cyclohexene Oxide
		2.3 Limonene Oxide
		2.4 Vegetable Oil-Based Epoxides
	3 Polymerization
		3.1 Catalysts
		3.2 Mechanism
	4 Thermal and Mechanical Properties
	5 Degradation
	6 Conclusions
	References
Progress in Catalytic Ring-Opening Polymerization of Biobased Lactones
	1 Introduction
	2 Catalytic Processes for ROP of Lactones
		2.1 Coordination Ring-Opening Polymerization
			2.1.1 Tin Octanoate
			2.1.2 Aluminum-Based Catalysts
			2.1.3 Zinc-Based Systems
			2.1.4 Lanthanide Complexes
		2.2 Ring-Opening Polymerization Using Organocatalysts
			2.2.1 Tertiary Amines and Phosphines
			2.2.2 N-Heterocyclic Carbenes
			2.2.3 Guanidine/Amidine/Thiourea Cocatalysts
			2.2.4 Phosphazene Bases
			2.2.5 Organic Acids
		2.3 Enzymatic Ring-Opening Polymerization
	3 Lactones from Renewable Resources
		3.1 Terpene-Derived Monomers
			3.1.1 Limonene-Based Monomers
			3.1.2 Pinene-Based Monomers
		3.2 Sugar-Derived Monomers
			3.2.1 γ-Butyrolactone
			3.2.2 α-Methylene-γ-Butyrolactone
			3.2.3 γ-Methyl-α-Methylene-γ-Butyrolactone and α-Angelica Lactone
			3.2.4 Substituted Valerolactones
			3.2.5 β-Malolactonates
			3.2.6 D-Glucono-1,5-Lactone
		3.3 Amino Acid-Derived β-Lactones
		3.4 Fatty Acid-Derived Monomers
		3.5 Naturally Occurring Macrolactones
	4 Conclusion
	References
BioPBS (Polybutylene Succinate)
	1 Introduction
		1.1 History of Biodegradable Polymer
		1.2 Why PBS among Aliphatic Polyesters?
		1.3 Environmental Policy in Japan
	2 BioPBS and FORZEAS
		2.1 Development of Bio-Based PBS by MCC
		2.2 Comparison of Biodegradable Polymers
		2.3 Biomass Conversion of Raw Material
		2.4 Development of Biodegradable Polymer Compound FORZEAS
	3 Characteristic Feature of BioPBS
		3.1 BioPBS (Outline of Bio-Based PBS)
		3.2 Manufacturing Technology
		3.3 Basic Characteristics of PBS
		3.4 Biodegradability and Certification in Various Regions
		3.5 Certification of Bio-Content
		3.6 Food Contact Certification
		3.7 Molding Processability
		3.8 Storage Stability
		3.9 Examples of Applications
			3.9.1 Food Contact Application
			3.9.2 Agricultural Mulching Film
			3.9.3 Forest Protection Sheet
		3.10 Related Technological Developments and Topics
			3.10.1 PBS-Starch Compound
			3.10.2 Enzyme Degradation of PBS
	4 Future Outlook
	References
Chemical Synthesis of Polyhydroxyalkanoates via Metal-Catalyzed Ring-Opening Polymerization of Cyclic Esters
	1 Introduction
	2 Stereoselective ROP of β-Butyrolactone (β-BL)
		2.1 Isotactic P3HB from Enantiopure (R)-β-BL or (S)-β-BL
		2.2 Isotactic P3HB from rac-β-BL
		2.3 Syndiotactic P3HB from rac-β-BL
	3 ROP of Eight-Membered Cyclic Diolides
		3.1 Isotactic PHAs from rac-8DLR
		3.2 Syndiotactic PHAs from meso-8DLR
		3.3 Stereosequenced PHAs from Diastereomeric Monomer Mixtures 8DLR
	4 Summary and Outlook
	References
Biobased Polyamides: Academic and Industrial Aspects for Their Development and Applications
	1 Introduction: Structure of Polyamides and Their Possible Raw Material Resources
		1.1 Polyamides: General Considerations (Why Polyamides?) and Basic Facts
		1.2 Why Biogenic Resources? Aspects of Sustainability and Structure Elements
		1.3 Biogenic Raw Material Sources for Polyamides
		1.4 Examples from Nature (Polyamides Based on α-Amino Acids)
		1.5 Definitions of ``Bio´´-Terms
	2 Bio-Based Building Blocks for the Synthesis of Polyamides
		2.1 Structure Elements that are Accessible from Natural Compounds
		2.2 Sources of Raw Materials
			2.2.1 Fats and Oils
			2.2.2 Carbohydrates
				Furfural
				Hexoses
				Aldaric Acids (Oxidized Sugars)
			2.2.3 Lignin
			2.2.4 Terpenes
		2.3 Target Compounds: General Remarks
		2.4 General Remarks on Reaction Parameters for the Polyamide Synthesis
	3 Procedures
	4 Structure, Properties, and Applications: General Remarks
	5 Stage of Development
		5.1 Biopolyamides via Polycondensation Reactions
		5.2 Biopolyamides via Ring-Opening Polymerization
	6 Challenges for the Production and the Application of New Biobased Polyamides
	7 Conclusion and Outlook
	References
Correction to: The Terpenes Limonene, Pinene(s), and Related Compounds: Advances in Their Utilization for Sustainable Polymers...
	Correction to: Chapter ``The Terpenes Limonene, Pinene(s), and Related Compounds: Advances in Their Utilization for Sustainabl...