Department of Chemistry Polymer Science Freie Universität Berlin Biodegradable polymers Environment friendly materials Cristiane Henschel Advanced Topics in Polymer Synthesis Polymer Science Master Program Freie Universität Berlin November 13 th , 2013
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Biodegradable Polymers - Advanced Topic in Polymers Synthesis
Presentation on "Biodegradable Polymers", done for the course "Advanced Topic in Polymers Synthesis" on the "Polymer Science Master Program" by "Cristiane Henschel"
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Department of Chemistry Polymer Science Freie Universität Berlin
functionalization and biomedical application. Progress in polymer science 2012, 37 (2), 237-280.
11. Hottle, T. A.; Bilec, M. M.; Landis, A. E., Sustainability assessments of bio-based polymers. Polymer Degradation
and Stability 2013, 98 (9), 1898-1907.
12. Yates, M. R.; Barlow, C. Y., Life cycle assessments of biodegradable, commercial biopolymers—A critical review.
Resources, Conservation and Recycling 2013, 78, 54-66.
Department of Chemistry Polymer Science Freie Universität Berlin
Questions?
Bioegradable Polymers Evironment Friendly Materials Cristiane Henschel Advanced Topics in Polymer Synthesis Polymer Science Master Program Freie Universität Berlin November 13th, 2013
Thank you for your attention!
Department of Chemistry Polymer Science Freie Universität Berlin
Extras
Bioegradable Polymers
Evironment Friendly Materials
Cristiane Henschel
Advanced Topics in Polymer Synthesis
Polymer Science Master Program
Freie Universität Berlin
November 13th, 2013
Department of Chemistry Polymer Science Freie Universität Berlin
Biodegradable Polymers
• Synthetic
– Poly(ε-caprolactone) - PCL
– Poly(glycolic acid) – PGA
– Poly(lactic acid) - PLA
– Polyhydroxyalkanoates – PHA’s
– Thermoplastic Starch – TPS
– Poly(ethylene glycol) – PEG
– Poly(dioxanone) – PDO
• Natural
– Polysaccharides • Starch
• Chitin and Chitosan
• Pectin
– Proteins • Gelatin
• Casein
PGA
PCL
PDO
PEG
Department of Chemistry Polymer Science Freie Universität Berlin
Biodegradable Groups
R1 C X
O
R2
OH2
R1 C OH
O
+ HX R2Where X= O, N, S
R1 C O
O
R2
Ester
R1 C NH
O
R2
Amide
R1 C S
O
R2
Thioester
X C X'
O
R2R1
OH2
+ HX' R2X C OH
O
R1
Where
X and X’=
O, N, S O C O
O
R2R1 NH C O
O
R2R1 NH C NH
O
R2R1
Carbonate Urethane Urea
Department of Chemistry Polymer Science Freie Universität Berlin
Biodegradable Groups
R1 C X
O
C
O
R2
OH2
+R1 C OH
O
HX C
O
R2
R1 C NH
O
C
O
R2 R1 C O
O
C
O
R2
Imide Anhydride
Where X and X’= O, N, S
R C O C R'
H H
H H
OH2
R C OH
H
H
R' C OH
H
H
+
RO P OR'
O
OR''
OH P OH
O
OR''
OH2
+ +R OH OH R'
Department of Chemistry Polymer Science Freie Universität Berlin
Factors Influence the
Degradation Behavior
Chemical Structure and Chemical Composition
Distribution of Repeat Units in Multimers
Molecular Weight
Polydispersity
Presence of Low Mw Compounds (monomer, oligomers, solvents, plasticizers, etc)
Presence of Ionic Groups
Presence of Chain Defects
Presence of Unexpected Units
Configurational Structure
Morphology (crystallinity, presence of microstructure, orientation and residue stress)
Processing methods & Conditions
Method of Sterilization
Annealing
Storage History
Site of Implantation
Absorbed Compounds
Physiochemical Factors (shape, size)
Mechanism of Hydrolysis (enzymes vs water)
Department of Chemistry Polymer Science Freie Universität Berlin
Poly(vinyl alcohol) - PVA
“Among the vinyl polymers produced industrially, PVA
is the only one known to be mineralized by
microorganism. PVA ia water soluble and biodegradable
and hence, used to make water soluble and
biodegradable carriers, which may be useful in the
manufacture of delivery systems for chemicals such as
fertilizers, pesticides and herbicides.
PVA is completely degraded and utilized by bacterial
strain, Pseudomonas O-3, as a sole source of carbon and
energy.”
Premraj, R.; Mukesh, D.; Biodegradation of Polymers.
Indian Journal of Biotechnology, 2005, 4(2), 186-193.
Department of Chemistry Polymer Science Freie Universität Berlin
Polyamides
“Polyamides contain the same amide bound as in
polypeptides. Nevertheless polyamides have a high
crystallinity and strong chains interactions so that the rate of
biodegradation is lower than that of polypeptides. Enzymes
and microorganisms can degrade low molecular weight
oligomers. Biodegradation could be increased by the
introduction of various side groups as benzyl, hydroxyl and
methyl groups, through copolymerization for instance.”