Polymer Degradation and Synthesis Quiz
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Questions and Answers

What is a characteristic of surface erosion in the context of hydrolytic degradation?

  • Degradation and mass loss occur uniformly throughout the bulk of the biomaterial.
  • The rate of polymer degradation and mass loss is greater at the surface than water diffusion into the bulk. (correct)
  • Water diffusion into the biomaterial is faster than degradation at the surface.
  • The degradation rate at the water-biomaterial interface is slower than water diffusion into the bulk.

    • In bulk erosion, how does the rate of water diffusion compare to the degradation rate?

  • Water diffusion and degradation occur at a similar rate.
  • Water diffusion is much faster than the degradation rate at the surface. (correct)
  • Water diffusion is the same as the rate of mass loss.
  • Water diffusion is significantly slower than the degradation rate.

    • Which of the following best describes how mass loss occurs in surface erosion?

  • Mass loss is uniform throughout the material.
  • Mass loss occurs predominantly at the water-biomaterial interface. (correct)
  • Mass loss is negligible on the surface compared to the bulk.
  • Mass loss only occurs after significant water diffusion into the bulk material.

    • According to the content, can degradation mechanisms be considered independent?

    <p>No, the content states both mechanisms are <em>not necessarily independent</em> of each other. (D)</p> Signup and view all the answers

    What is the primary factor that distinguishes bulk erosion from surface erosion?

    <p>The relative rates of water diffusion and polymer degradation. (A)</p> Signup and view all the answers

    Which method is NOT described as a way to synthesize aliphatic polyesters?

    <p>Electrochemical polymerization (C)</p> Signup and view all the answers

    In ring-opening polymerization (ROP) of lactones, how is the molecular weight of the polymer primarily determined in a living/controlled polymerization?

    <p>By the monomer-to-initiator molar ratio (B)</p> Signup and view all the answers

    What is a key characteristic of ring-opening polymerization (ROP) of lactones with a living/controlled mechanism?

    <p>It results in polymers with a narrow molecular weight distribution (B)</p> Signup and view all the answers

    In coordination-insertion ring-opening polymerization, what is the role of the organometallic compound such as Sn(Oct)2?

    <p>It acts as an initiator or a catalyst depending on the conditions (C)</p> Signup and view all the answers

    What is the primary mechanism of monomer insertion into the metal alkoxide bond in coordination-insertion ring opening polymerization?

    <p>Acyl-oxygen bond cleavage followed by insertion (B)</p> Signup and view all the answers

    What chemical process is primarily responsible for the breakdown of resorbable polymers like PLGA?

    <p>Hydrolytic degradation by water molecules (B)</p> Signup and view all the answers

    Which of the following factors does NOT directly influence the degradation rate of a resorbable biomedical polymer?

    <p>The cost of manufacturing the polymer. (B)</p> Signup and view all the answers

    What does the term 'assimilation' refer to, in the context of resorbable biomaterials?

    <p>The clearance of degradation products by the body. (C)</p> Signup and view all the answers

    Which type of chemical bond is most likely to be broken during hydrolytic degradation of a polymer?

    <p>Ester, amide and glycosidic bonds. (A)</p> Signup and view all the answers

    What is the immediate consequence of degradation on the molecular weight of a polymer?

    <p>The molecular weight decreases. (C)</p> Signup and view all the answers

    Besides material parameters, what other group of factors influences the degradation rate of a resorbable biomedical device?

    <p>The device size, geometry, and external environmental conditions. (C)</p> Signup and view all the answers

    What does degradation involve?

    <p>The breakdown of the structure and subsequent assimilation by the body. (A)</p> Signup and view all the answers

    What is the primary difference between hydrolytic and enzymatic degradation?

    <p>Hydrolytic uses water and enzymatic uses enzymes in the breakdown. (D)</p> Signup and view all the answers

    Which of the following polymers are significantly used as biomaterials?

    <p>PLLA and PDLLA (B)</p> Signup and view all the answers

    Compared to PGA, what effect does the methyl group in PLA have on its properties?

    <p>It makes it more hydrophobic and more stable against hydrolysis (C)</p> Signup and view all the answers

    Approximately how long does it take for high molecular weight PLLA to be completely resorbed in vivo?

    <p>More than 4 years (A)</p> Signup and view all the answers

    What is the primary reason for the faster degradation rate of PLGA compared to pure PGA and PLLA?

    <p>Decreased crystallinity due to copolymerization (D)</p> Signup and view all the answers

    According to the information provided, which of the following PLGA compositions degrades the fastest?

    <p>PLGA 50:50 (A)</p> Signup and view all the answers

    Based on the provided table, which product has the longest resorption time?

    <p>Resorb x® and Resorb xG Plates (C)</p> Signup and view all the answers

    What is the main reason for the U-shape trend observed in the degradation time of PLGAs?

    <p>Decrease in crystallinity with increasing comonomer content (A)</p> Signup and view all the answers

    Which of the following is NOT a characteristic of high performance polymers, as described in the text?

    <p>High cost (D)</p> Signup and view all the answers

    What method was used to assess the fiber morphology of the PCL scaffolds?

    <p>Scanning electron microscopy (SEM) (D)</p> Signup and view all the answers

    How many measurements were taken to determine the average fiber diameters of the PCL scaffolds using SEM images?

    <p>20 (A)</p> Signup and view all the answers

    Which of the following statements best describes the degradation of PCL?

    <p>PCL degradation is mainly affected by enzymatic degradation. (C)</p> Signup and view all the answers

    What is the general trend in fiber diameter of PCL during degradation?

    <p>Moderate to severe diameter reduction (B)</p> Signup and view all the answers

    What was used to assess how the fiber diameters decreased in size?

    <p>Analysis of SEM images (D)</p> Signup and view all the answers

    How many SEM images were used per sample to calculate the average fiber diameter?

    <p>4 (D)</p> Signup and view all the answers

    What feature of the PCL scaffolds was directly quantified using the SEM images?

    <p>Average fiber diameters (C)</p> Signup and view all the answers

    The degree of diameter reduction in PCL fibers varies depending on which factor?

    <p>Enzyme nature (C)</p> Signup and view all the answers

    What change in mechanical properties is observed in supramolecular PCL after oxidation?

    <p>Increased Young's modulus and decreased strain at break. (C)</p> Signup and view all the answers

    What does a tensile test measure in the context of material properties?

    <p>The mechanical behavior of a material under applied force. (D)</p> Signup and view all the answers

    Which of the following best describes plastic deformation?

    <p>An irreversible change in material shape where energy is dissipated. (D)</p> Signup and view all the answers

    What does the term 'ultimate elongation' ($\epsilon_f$) refer to in material testing?

    <p>The total amount of stretch a material can undergo before fracture. (A)</p> Signup and view all the answers

    What is Young's modulus (E) indicative of in a tensile test?

    <p>The materials stiffness or resistance to deformation. (B)</p> Signup and view all the answers

    What is a possible cause for observing a change towards a more brittle behaviour in PCL after oxidation?

    <p>Annealing of the material at 37°C, resulting in increased crystallinity. (C)</p> Signup and view all the answers

    What does the yield strength ($\sigma_y$) represent?

    <p>The force at which the material deforms plastically. (D)</p> Signup and view all the answers

    How is strain measured during a typical tensile test?

    <p>Via optical, mechanical or electrical methods of dimension change. (A)</p> Signup and view all the answers

    Flashcards

    Hydrolytic Degradation

    Hydrolytic degradation is the breakdown of synthetic materials by water molecules.

    Bulk Degradation

    In bulk degradation, water diffuses throughout the material, causing it to break down from the inside out.

    Surface Erosion

    In surface erosion, water only affects the surface of the material, causing it to erode away.

    Water Diffusion Rate

    The rate at which water diffuses into the material determines whether it undergoes bulk degradation or surface erosion.

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    Interdependence of Degradation Mechanisms

    Both bulk degradation and surface erosion are not always distinct processes, they can sometimes occur together.

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    Resorption

    The process of breaking down a material and incorporating its components into the surrounding environment.

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    Degradation

    The breakdown of a material, usually through chemical processes like hydrolysis, enzymatic reactions, or oxidation.

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    Enzymatic Degradation

    Degradation involving enzymes, biological catalysts that speed up chemical reactions in living organisms.

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    Oxidative Degradation

    Degradation where oxygen reacts with the material, causing it to deteriorate.

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    Material Parameters

    The strength of the bonds in a polymer's backbone, its molecular weight, and the material's interaction with water, among other factors.

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    Device and External Conditions

    The size, shape, and surrounding environment of a biomedical device, including pH, temperature, and tissue type.

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    Degradation Kinetics

    The process of breaking down a material with chemical reactions on a molecular level, even if diffusion may affect the overall speed.

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    Ring-Opening Polymerization (ROP) of Lactones

    A process where a cyclic monomer, a lactone, opens its ring and forms a long chain polymer.

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    Lactones in ROP

    Monomers used in ROP are cyclic esters with different ring sizes and potential substituents.

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    High Molecular Weight Polymers in ROP

    ROP can produce polymers with high molecular weights due to the chain-growth mechanism.

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    Living/Controlled ROP

    A type of ROP where the polymerization is controlled, leading to polymers with a narrow range of molecular weights and predictable lengths.

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    Organometallic Initiators/Catalysts in ROP

    Organometallic compounds, like tin(II) octoate, are often used as initiators/catalysts to start the ROP process.

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    Strain at Break

    Refers to the ability of a material to stretch or deform before breaking.

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    Young's Modulus

    A measure of a material's stiffness, representing the resistance to deformation under stress.

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    Annealing

    A process where a material's internal structure changes, often leading to increased strength and rigidity.

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    Crystallinity

    A state of a material where its molecules are arranged in a highly ordered, repeating pattern, enhancing its strength and rigidity.

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    Elastic Deformation

    A type of deformation where a material returns to its original shape after the stress is removed.

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    Plastic Deformation

    A type of deformation where a material does not fully recover to its original shape after the stress is removed.

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    Yield Strength

    The point at which a material begins to deform permanently.

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    Ultimate Strength

    The maximum stress a material can withstand before breaking.

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    SEM Image Quantification

    The process of assessing and measuring the size and shape of fibers in a material using a scanning electron microscope (SEM).

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    Average Fiber Diameter

    The diameter of the fibers in a scaffold, determined by taking multiple measurements on SEM images.

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    Scaffold Fiber Morphology

    The process of determining how the size and shape of scaffold fibers change over time.

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    Fiber Diameter Reduction

    The process of quantifying and measuring the changes in fiber diameter in a scaffold due to degradation.

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    PCL Degradation Variability

    PCL is mainly degraded by enzymes, but the rate and severity of degradation depends on which specific enzyme is involved.

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    Morphological Analysis

    The process of using SEM images to analyze and quantify changes in scaffold morphology over time.

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    Differentiating Degradation Mechanisms

    The ability to distinguish and differentiate between the effects of enzymatic and non-enzymatic degradation on scaffold fibers.

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    Biomaterial Polymers

    PLLA and PDLLA are the most commonly used biocompatible polymers in biomaterials.

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    High-Performance Polymer

    A polymer material that exhibits high mechanical strength, stiffness, versatility in processing, and is relatively inexpensive.

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    PLA's Hydrophobicity

    PLA's methyl group makes it more resistant to water breakdown (hydrolysis) than PGA.

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    PLLA Resorption Time

    High molecular weight PLLA, a type of biocompatible polymer, takes over 4 years to be fully absorbed by the body.

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    Poly(L-lactide-co-glycolide) (PLGA)

    A copolymer formed by randomly combining PLLA and PGA. It degrades faster than pure PLLA or PGA, with the fastest degradation occurring at a 50:50 ratio.

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    PLGA Degradation Rate

    PLGA's degradation rate is faster than its individual components due to decreased crystallinity. The less crystalline a material is, the easier it is for water to penetrate and break it down.

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    Bioresorbable Implants

    Implants made from PLA and PLGA are designed to break down and be absorbed by the body over time, making them suitable for temporary support.

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    Implant Degradation Time

    The degradation time of an implant varies depending on its composition and the type of polymers used. For example, 85:15 PLGA implants typically resorb in 12 months.

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    Study Notes

    Lecture Plan

    • Dates: 15.10.2024 - 18.02.2025
    • Topics: Fundamentals of Biomedical Materials, Physicochemical properties of polymer materials, Synthetic biomedical polymers (resorbable and non-resorbable), Biomedical hydrogels, Additive Manufacturing of biomedical polymers, Protein adsorption, Immune response, Smart textiles, wearable devices, biosensors, Case studies on medical devices, and student presentations.
    • Lecturers: del Campo, Müller, Asensio, Steudter, Sankaran, Trujillo

    Lecture 3: Synthetic, Resorbable Biomedical Polymers

    • Topic: Synthetic, resorbable biomedical polymers
    • Lecturer: Aránzazu del Campo

    Outline

    • Degradation & Clearance mechanisms: Degradation and clearance mechanisms of biomedical polymers.
    • Resorbable aliphatic polyesters: Resorbable aliphatic polyesters.
    • Other resorbable polymers: Other resorbable polymers (to be covered in a later lecture)

    Classification of Polymeric Biomaterials

    • Resorbable: Poly(lactic-co-glycolic acid) (PLGA)
      • Vicryl sutures, 6–0, V-18 needle, 70 cm purple filament.
      • Tensile strength:
        • 2 weeks: 75%
        • 3 weeks: 50%
        • 4 weeks: 25%
      • Complete absorption within 56–70 days
    • Durable: Nylon
      • Ethilon sutures, 2–0, FS needle, 45 cm blue filament.
      • Non-absorbable, sterile monofilament suture of long-chain aliphatic polymers (Nylon 6 and Nylon 6,6).

    Example Resorbable Biomedical Polymer

    • Polymer: Poly(D,L-lactide-co-glycolide) (PLGA) (Resomer®)
    • Applications: Dental membrane, bone & tissue regeneration, tracheal implant, cardiovascular stents, breast implants, shoulder balloon, tissue scaffold, and more.
    • Other examples of applications: Craniomaxillofacial implants, suture anchors, Spinal fusion, fixation plates, and more.

    Resorbable Material

    • Definition: Breakdown of a structure and subsequent assimilation of resulting components into the environment.
    • Breakdown mechanisms: Hydrolytic, enzymatic, oxidative degradation and Dissolution
    • Assimilation: Clearance by the body through metabolic processing or excretion.

    Degradation

    • Hydrolytic Degradation: Cleavage of water-labile bonds (glycosides, carbonates, esters, or amides) in the polymer backbone by water molecules.
    • Enzymatic Degradation: Breakdown of polymers by enzymes
    • Oxidative Degradation: Deterioration of polymers through oxidation by atmospheric oxygen or other oxidants in the biological environment.

    Factors Influencing Degradation Rate

    • Material Parameters: Polymer backbone chemistry, molar mass, hydrophobicity/hydrophilicity, crystallinity, water adsorption, diffusion, degradation products solubility and diffusion.
    • Device and External Conditions: Device size and geometry, pH, temperature, tissue type, pathology, and environmental conditions.

    Factors Influencing Degradation of Bioresorbable Devices

    • Processing: Sterilization, annealing, machining, additive manufacturing, compression molding, injection molding, and extrusion.
    • Material Properties: Chemical composition (monomer ratio, crystalline/amorphous, molecular weight, stereoisomerism), secondary ingredients, geometry, additive, interfacial reaction, and dispersion/orientation.

    Degradation Mechanisms

    • Surface Erosion: Polymer degradation and mass loss primarily at the water-biomaterial interface. Water diffusion rate is slower than the degradation rate.
    • Bulk Erosion: Water diffusion into the biomaterial is faster than degradation at the surface, leading to degradation throughout the bulk material.

    Hydrolytically Degradable Polymers

    • Polymers: Polymers possessing water-labile bonds in their backbone for breakdown in an aqueous environment (the body).
    • Hydrolytic Degradation: Scission of water-labile bonds (glycosides, carbonates, esters, amides) in the polymer backbone.

    Hydrolytic Degradation Rates of Biomedical Polymers

    • Polymers': Polycarbonates, polyesters, polyamides, polyphosphoesters, polyurethanes, polyacetals, poly(ortho esters), polyanhydrides, and polyphosphazenes.
    • Degradation rates: Rates for each category of polymers are listed according to degradation time in 1 cm thickness.

    Degradation Rates of Biomedical Polymers

    • Classifications: Polymers are categorized by the rates and conditions causing the breakdown and degradation
    • Characteristics: Tables list degradation rates, compositions, structures, and applications for different polymer groups, including polyphosphazenes, polyanhydrides, polyacetals, poly(ortho esters), and polyphosphoesters.

    Clearance of Biomedical Polymers by the Body

    • Biodegradable polymers: Cleave bonds in the backbone, producing small molecules absorbed in the body's biochemical pathways. Examples include Poly(L-glutamic acid) and poly(aspartic acid), producing monomeric amino acids.
    • Semi-degradable polymer backbones: Composed of non-degradable blocks with degradable linkers.
    • Renal elimination: Rate inversely correlates with the molecular weight (MW).

    Aliphatic Polyesters

    • Wide Use: Widely used in degradable biomedical polymers.
    • Primary Processes:
      • Hydrolysis of ester bonds (autocatalytic process): water diffuses into amorphous regions & cleaves ester bonds.
      • Degradation proceeds at the surface and/or in the bulk of the polymer
      • Degradation is influenced by various factors such as chemical composition, stereochemistry, monomer sequence, molecular weight, etc.

    Synthesis of Aliphatic Polyesters

    • Polycondensation: Hydroxyacids or diols with diacids/diesters yield aliphatic polyesters.
    • Ring-opening Polymerization (ROP) of lactones: Synthesis method for aliphatic polyesters.
    • Bacterial Synthesis: A synthesis method for aliphatic polyesters.

    Ring Opening Polymerization of Lactones

    • Lactones: Monomers of ring sizes exhibiting substituents.
    • High Molecular Weight Polymer: Obtainable from living/controlled polymerization.
    • Ratio-dependent Molecular Weight: Molecular weight determined by the initiator to monomer ratio.

    Coordination-insertion ROP

    • Organometallics: Typical initiators, such as Sn(Oct)2.
    • Mechanism: Initiator coordinates to the carbonyl group, followed by acyl-oxygen bond cleavage and monomer insertion into the metal-alkoxide bond.
    • Catalyst: In the presence of nucleophiles, the organometallic acts as a catalyst.

    Polyglycolide (PGA)

    • Monomer: Glycolide, derived from glycolic acid (from sugar fermentation).
    • Molar Mass: > 100 kDa
    • Tg (°C): 36 °C
    • Tm (°C): 223 °C
    • Crystallinity (%): 45–55%
    • Degradation: 1–6 months
    • Modulus: 7–8.4 GPa
    • Strength: ~900 MPa in oriented fibers
    • Elongation at Break (%): 30%
    • Polymer Type: Thermoplastic

    PGA Biomedical Devices

    • Examples: Degradable sutures (DEXON®), internal bone pins (Biofix®)
    • Limitations: Rapid degradation leads to loss of mechanical strength and significant local glycolic acid production, potentially resulting in adverse inflammatory responses.

    Polylactide (PLA)

    • Monomer: L-lactide (from bacterial fermentation of starch/sugar; biobased) or L-lactide + D-lactide
    • Molar Mass: > 100 kDa
    • Tg (°C): 50–65 °C
    • Tm (°C): 170–190 °C (amorphous)
    • Crystallinity (%): 37%
    • Degradation: >4 years
    • Modulus: 3.5 GPa
    • Strength: 80 MPa
    • Elongation at Break (%): 30–40%

    Poly(L-lactide-co-glycolide (PLGA)

    • Random copolymer of PLLA and PGA: Degradation rates faster than pure PGA and PLLA, with the fastest rate at a 50/50 ratio.
    • Semi-crystalline structure: Crystallinity decreases as the copolymerization ratio moves away from pure homopolymer structures.

    Applications of Bioresorbable Implants (PLA and PLGA based)

    • Orthopedic Applications: Various uses in orthopedic applications such as implants, and more.

    PLGA Biomedical Products

    • Sutures: Vicryl®, Vicryl Rapide®, Vicryl Plus Antibacterial®
    • Other products: Polysorb®, Purasorb®

    Biological & Physiological Pathways

    • PLA Degradation: Lactic acid, Krebs cycle, carbon dioxide, water
    • PGA Degradation: Glycolic acid, glyoxylic acid, glycine, serine, pyruvate, kidney.
    • PLGA Degradation: similar processes to those above with additional products from both the PLA and PGA portions of the polymer.

    Polyhydroxyalkanoates (PHA)

    • Bioplastic origins: Synthesized by microorganisms.
    • Structures: Homopolymers, random, or block copolymers.
    • Bacterial species variability: PHA production can depend on the bacterial species and growth conditions.

    Poly(3-hydroxybutyrate) (PHB)

    • Synthesis: Fermentation methods: batch, fed-batch, or continuous cultures.
    • Carbon sources: Inexpensive carbon sources such as beet and cane molasses, corn starch, alcohols, and vegetable oils.
    • Polymer properties: Semi-crystalline, isotactic, processability with ranges for melting and glass transition points.
    • Degradation: Hydrolytic degradation results in the formation of D(-)-3-hydroxybutyric acid, a normal blood constituent. Degradation product is less acidic than PGLA.

    Poly(4-hydroxybutyrate) (P4HB)

    • GalaFLEX™ Scaffold: Plastic and reconstructive surgery application.
    • Soft Tissue Reinforcement: Intended for soft tissue reinforcement during healing after surgery.

    Poly(hydroxyvalerate-co-3-hydroxybutyrate) (PHBV)

    • Copolymerization: 3-hydroxyvalerate with PHB to create PHBV.
    • Crystallinity and properties: Less crystalline than PHB with melting and glass transition temperatures that vary according to 3HV content.
    • Applications: Bone, cartilage, tendon, skin, and nerve tissue engineering.

    Polycaprolactone (PCL)

    • Properties: Semicrystalline polyester with great organic solvent solubility, low tensile strength but high elongation at breakage.
    • Tg (Glass/Transition Temperature): 55-60 °C
    • Tm (Melting Temperature): -54 °C
    • Degradation: Degradation rates depend on molecular weight and crystallinity. Can be enzymatically degraded or copolymerized/blended with other polymers.
    • Applications: Tissue engineering, scaffolds for bone, ligament, cartilage, skin, nerve, and vascular tissues.

    Study of Enzymatic & Oxidative Degradation of PCL

    • Materials: Semicrystalline PCL, PCL-BU (bis-urea), PCL-UPy (ureidopyrimidinone).
    • Degradation phases: Materials contain separated soft blocks (semicrystalline PCL) and hard blocks (interacting H-bonding units).
    • Oxidative Degradation: hydrogen peroxide and cobalt (II) chloride generate hydroxyl radicals.

    Degradation of PCL in Vitro

    • Mass Loss and Molecular Weight: Methods and data for testing the mass loss and molecular weight reduction during enzymatic and/or oxidative degradation for a variety of PCL variants.
    • SEM Images: Microscopy analysis of the degradation of PCL fibrous structures post-treatment with various solvents, enzymes, and more.
    • Quantification of Fiber Diameter: The method and resulting data are provided in graphs for the quantification of fiber diameter reduction post-treatment.

    Mechanical Properties of PCL in Vitro

    • Tensile test principles: Stress/strain, displacement, deformation rates, and measurement principles.
    • Mechanical properties evaluation: Young’s modulus, yield strength, yield elongation, ultimate strength, and ultimate elongation are tested in this category of PCL, post-treatment with lipase or oxidative compounds..

    Study of Enzymatic and Oxidative Degradation of PCL Materials

    • Summary of Results: The susceptibility of each material to degradation is presented by a color scale.
    • Enzymatic Degradation: PCL scaffolds are rapidly degraded, resulting in mass loss, change in fiber morphology, and weakening.
    • Oxidative Degradation: Supramolecular PCLs (UPy- and BU-containing) are less prone to enzymatic hydrolysis and show either less or no mass change.

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    WS2024 Lecture 3: Degradable Biomedical Polymers Handout PDF

    Description

    This quiz covers key concepts related to hydrolytic degradation, including surface and bulk erosion mechanisms, as well as synthesis methods for aliphatic polyesters. Participants will test their understanding of ring-opening polymerization and its characteristics. Dive in to assess your knowledge on these important polymer science topics!

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