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Polycaprolactone
Polycaprolactone
Polycaprolactone
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Polycaprolactone
Names
IUPAC name
(1,7)-Polyoxepan-2-one
Systematic IUPAC name
Poly(hexano-6-lactone)
Other names
2-Oxepanone homopolymer
6-Caprolactone polymer
Identifiers
Abbreviations PCL
ChemSpider
  • none
Properties
(C6H10O2)n
Density 1.145 g/cm3
Melting point 60 °C (140 °F)
Thermal conductivity 0.05 W/(m K) @25°C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
PCL beads, as sold for industrial or hobbyist use.

Polycaprolactone (PCL) is a synthetic, semi-crystalline, biodegradable polyester with a melting point of about 60 °C and a glass transition temperature of about −60 °C.[2][3] The most common use of polycaprolactone is in the production of speciality polyurethanes. Polycaprolactones impart good resistance to water, oil, solvent and chlorine to the polyurethane produced.

This polymer is often used as an additive for resins to improve their processing characteristics and their end use properties (e.g., impact resistance). Being compatible with a range of other materials, PCL can be mixed with starch to lower its cost and increase biodegradability or it can be added as a polymeric plasticizer to polyvinyl chloride (PVC).

Polycaprolactone is also used for splinting, modeling, and as a feedstock for prototyping systems such as fused filament fabrication 3D printers.

Synthesis

[edit]

PCL is prepared by ring opening polymerization of ε-caprolactone using a catalyst such as stannous octoate. A wide range of catalysts can be used for the ring opening polymerization of caprolactone.[4] Low molecular weight alcohols are commonly added to regulate the molecular weight of the polymer.

Biomedical applications

[edit]

PCL is degraded by hydrolysis of its ester linkages in physiological conditions (such as in the human body) and has therefore received a great deal of attention for use as an implantable biomaterial. In particular it is especially interesting for the preparation of long term implantable devices, owing to its degradation which is even slower than that of polylactide.

PCL has been widely used in long-term implants and controlled drug release applications. However, when it comes to tissue engineering, PCL suffers from some shortcomings such as slow degradation rate, poor mechanical properties, and low cell adhesion. The incorporation of calcium phosphate-based ceramics and bioactive glasses into PCL has yielded a class of hybrid biomaterials with remarkably improved mechanical properties, controllable degradation rates, and enhanced bioactivity that are suitable for bone tissue engineering.[5] PCL–Hydroxyapatite composite scaffolds for bone tissue engineering can mimic the composition and morphology of the bone mineral phase and can be 3D printed into intricate designs. [6]

PCL has been approved by the Food and Drug Administration (FDA) in specific applications used in the human body as (for example) a drug delivery device, suture, or adhesion barrier.[7] PCL is used in the rapidly growing field of human esthetics following the recent introduction of a PCL-based microsphere dermal filler belonging to the collagen stimulator class (Ellansé).[8]

Through the stimulation of collagen production, PCL-based products are able to reduce facial ageing signs such as volume loss and contour laxity, providing an immediate and long-lasting natural effect.[8][9] It is being investigated as a scaffold for tissue repair by tissue engineering, GBR membrane. It has been used as the hydrophobic block of amphiphilic synthetic block copolymers used to form the vesicle membrane of polymersomes.

A variety of drugs have been encapsulated within PCL beads for controlled release and targeted drug delivery.[10]

In dentistry (as the composite named Resilon), it is used as a component of "night guards" (dental splints) and in root canal filling. It performs like gutta-percha, has similar handling properties, and for re-treatment purposes may be softened with heat, or dissolved with solvents like chloroform. Similar to gutta-percha, there are master cones in all ISO sizes and accessory cones in different sizes and taper available. The major difference between the polycaprolactone-based root canal filling material (Resilon and Real Seal) and gutta-percha is that the PCL-based material is biodegradable,[11] whereas gutta-percha is not. There is a lack of consensus in the expert dental community as to whether a biodegradable root canal filling material, such as Resilon or Real Seal is desirable.

Hobbyist and prototyping

[edit]
Homemade bicycle light mount made from PCL

PCL also has many applications in the hobbyist market where it is known as Re-Form, Polydoh, Plastimake, NiftyFix, Protoplastic, InstaMorph, Polymorph, Shapelock, ReMoldables, Plastdude, TechTack, or Friendly Plastic. It has physical properties of a very tough, nylon-like plastic that softens to a putty-like consistency at only 60 °C, easily achieved by immersing in hot water.[12] PCL's specific heat and conductivity are low enough that it is not hard to handle by hand at this temperature. This makes it ideal for small-scale modeling, part fabrication, repair of plastic objects, and rapid prototyping where heat resistance is not needed. Though softened PCL readily sticks to many other plastics when at higher temperature, if the surface is cooled, the stickiness can be minimized while still leaving the mass pliable.

Biodegradation

[edit]

Bacillota and Pseudomonadota can degrade PCL.[13] Penicillium sp. strain 26-1 can degrade high density PCL; though not as quickly as thermotolerant Aspergillus sp. strain ST-01. Species of Clostridium can degrade PCL under anaerobic conditions.

See also

[edit]

References

[edit]

Further reading

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Polycaprolactone

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from Grokipedia
Polycaprolactone (PCL) is a synthetic, biodegradable, and biocompatible produced through the of ε-caprolactone, characterized by its semicrystalline structure, hydrophobicity, and slow degradation rate via , making it suitable for long-term biomedical applications. PCL exhibits a low temperature of approximately -60°C and a ranging from 59°C to 64°C, which contribute to its flexibility, , and ease of into various forms such as films, fibers, and scaffolds. Its mechanical properties, including adjustable strength and elasticity, can be tailored by varying molecular weight and blending with other materials, enhancing its utility in load-bearing applications. Biocompatibility is well-established, with PCL meeting standards for interaction with human tissues and fluids, as its degradation products—primarily and water—are non-toxic and fully eliminated from the body. The polymer's degradation occurs in two phases: initial hydrolysis of ester bonds followed by enzymatic breakdown, with the rate depending on factors like molecular weight (typically 1-4 years for biomedical uses) and environmental conditions, allowing controlled release in systems. PCL finds extensive use in for creating 3D scaffolds that support cell growth in , , and regeneration, as well as in sutures like Monocryl™ and drug-eluting implants like Capronor™ for contraception. In esthetic medicine, PCL-based fillers such as Ellansé® stimulate production for facial and hand rejuvenation, leveraging its and gradual resorption. Emerging applications include dressings and artificial vessels, driven by ongoing into nanocomposites for improved mechanical and biological .

Overview and Properties

Chemical Structure

Polycaprolactone (PCL) is a biodegradable aliphatic synthesized via of the cyclic ε-caprolactone, which has the molecular formula C₆H₁₀O₂. The resulting features a repeating unit of –[O–(CH₂)₅–CO]–, forming a linear chain with linkages that connect the oxygen and carbonyl groups, giving the overall (C₆H₁₀O₂)ₙ, where n represents the . This structure consists of five methylene (–CH₂–) groups flanked by an (–COO–) linkage, contributing to the polymer's flexibility and hydrophobicity at the molecular level. Commercial grades of PCL typically exhibit number-average molecular weights (Mₙ) ranging from 3,000 to g/mol, with the degree of polymerization influencing chain length and structural regularity. Higher molecular weights generally promote greater chain entanglement and semi-crystalline ordering due to the ability of the linear aliphatic chains to fold and pack into crystalline domains, while lower weights result in more amorphous characteristics. PCL can be incorporated into copolymers, such as multiblock or graft structures with poly() (PLA), where PCL segments are covalently linked to PLA chains to form hybrid repeating units that maintain the core ester-based backbone. These structural integrations allow for tailored chain architectures without altering the fundamental PCL repeating motif. The ε-caprolactone lacks chiral centers, resulting in PCL chains with uniform structural regularity along the backbone, facilitating linear extension and contributing to the polymer's semi-crystalline nature through van der Waals interactions between methylene sequences. This uniformity ensures consistent chain conformation in standard syntheses, unlike stereoregular polymers with chiral units.

Physical and Mechanical Properties

Polycaprolactone (PCL) is a characterized by distinct thermal properties that influence its processability and performance. Its typically ranges from 58°C to 60°C, allowing for low-temperature processing, while the temperature is approximately -60°C, resulting in a rubbery state at . The degree of crystallinity is around 56%, which is influenced by the linear aliphatic structure of the polymer chains that enables ordered packing but limits complete . PCL exhibits a density of approximately 1.14 g/cm³, contributing to its nature in bulk applications. It demonstrates good in organic solvents such as and , facilitating solution-based processing, but remains insoluble in due to its hydrophobic backbone. In terms of mechanical properties, PCL displays moderate tensile strength of 10.5–16.1 MPa and a of about 0.35 GPa for solid forms, indicating flexibility rather than rigidity. Its elongation at break can reach up to 800%, highlighting exceptional that arises from the soft, semicrystalline matrix. Rheologically, PCL melt exhibits low due to its low , making it suitable for and molding processes; it also shows shear-thinning behavior with a Newtonian plateau at low shear rates, enhancing flow under processing conditions. Electrically, PCL is an insulator with a constant of approximately 3.2 across frequencies and low inherent conductivity, suitable for non-conductive applications. In certain formulations, PCL demonstrates shape memory effects, where temporary shapes are fixed below the or temperature and recover to the original form upon heating to around 60°C, with recovery rates exceeding 90% in optimized systems.
PropertyValueNotes
58–60°CEnables low-temperature melt processing
-60°CContributes to rubbery behavior at ambient conditions
Crystallinity~56%Semicrystalline nature affects mechanical
1.14 g/cm³Typical for bulk PCL
Tensile Strength10.5–16.1 MPaFor solid PCL
0.35 GPaIndicates flexible response
Elongation at BreakUp to 800%High
Constant~3.2At 0.5–3.5 GHz

Synthesis and Production

Polymerization Methods

The primary method for synthesizing polycaprolactone (PCL) is the (ROP) of ε-caprolactone (ε-CL), which proceeds via anionic, cationic, or coordination-insertion mechanisms to yield high-molecular-weight polymers with controlled structures. In anionic ROP, nucleophilic initiators such as alkoxides attack the carbonyl carbon of ε-CL, forming chain ends that propagate the reaction, though sensitivity to impurities and intramolecular often limit molecular weights. Cationic ROP involves or alkylation of the by acids or Lewis acids, leading to activated susceptible to nucleophilic attack, but it typically produces lower molecular weights and is less controllable due to side reactions. The coordination-insertion mechanism, widely adopted for its efficiency, employs metal catalysts like stannous octoate (Sn(Oct)2) that coordinate with the , facilitating acyl-oxygen bond cleavage and insertion into the growing chain, often initiated by alcohols or water to achieve narrow polydispersity indices (e.g., Đ ≈ 1.3–1.5) and molecular weights up to 100,000 g/mol. The ROP reaction is represented as: n ϵ-CL→[−(CH2)5COO−]nn \ \epsilon\text{-CL} \rightarrow \left[ -(\text{CH}_2)_5 \text{COO}- \right]_n Typically conducted under bulk (solvent-free) conditions at 100–180°C for 24–72 hours, molecular weight is precisely controlled by the monomer-to-initiator ratio, with Sn(Oct)2 at loadings of 0.01–0.1 mol% enabling near-quantitative conversions. Alternative routes include polycondensation of 6-hydroxyhexanoic acid, which involves stepwise esterification and water elimination at high temperatures (>200°C) over extended periods, but yields lower molecular weights (typically <10,000 g/mol) and broad polydispersity due to equilibrium limitations and side products. Enzymatic polymerization, using lipases such as Novozym 435 (Candida antarctica lipase B), catalyzes ROP at milder conditions (60–80°C in toluene) via a serine hydrolase mechanism that activates the monomer's lactone ring, though it generally results in moderate molecular weights (up to 84,000 g/mol) and requires optimization to mitigate enzyme deactivation. For tailored properties, PCL is often synthesized as copolymers with lactide or glycolide through ROP, either sequentially (to form block structures, e.g., using Sn(Oct)2 at 150°C for 30 hours with 1:1 monomer feeds) or randomly (statistical incorporation via simultaneous feeding), enabling adjustable degradation rates but prone to composition drift from differing monomer reactivities. Challenges in these methods include side reactions like (), which degrade chain length and introduce cyclics, necessitating conditions and post-purification steps such as or catalyst removal to ensure .

Commercial Production

Polycaprolactone (PCL) was first synthesized in the mid-1930s by researchers at , including , through the of ε-caprolactone, marking an early milestone in synthetic development. Commercial production began in the 1970s when introduced PCL under the trade name Tone polymer, initially targeting applications in adhesives and coatings due to its favorable mechanical properties and biodegradability. This commercialization leveraged advances in techniques, enabling scalable manufacturing that positioned PCL as a versatile industrial material by the late . In 2019, Perstorp sold its Capa™ caprolactone business to Ingevity, which continues production under the Capa™ brand. Major global producers of PCL include Ingevity, , and , with Ingevity holding the largest market share through its Capa™ product line, often used in ecoflex blends for biodegradable packaging. As of 2025, worldwide production capacity is estimated at around 55,000 tons per year, driven by growing demand in biomedical and sustainable plastics sectors, though concentrated among these key players in and . Industrial manufacturing primarily employs bulk (ROP) of ε-caprolactone using catalysts such as stannous octoate in continuous or semi-continuous reactors at temperatures up to 175°C under inert atmosphere to achieve high molecular weights (typically 40,000-80,000 g/mol). Post-polymerization, purification occurs via in solvents like or acetone to remove unreacted and impurities, ensuring product consistency for downstream uses. PCL is available in various grades tailored to end-use requirements, including high-purity medical-grade variants for implants and systems, which undergo stringent sterilization and low-residual testing, and industrial-grade options for general plastics and adhesives with broader impurity tolerances. Cost factors for industrial-grade PCL range from approximately $5-10 per kg, influenced by prices for ε-caprolactone and production scale, making it economically competitive with other polyesters despite its biodegradability premium. Recent advances since 2020 focus on bio-based ε-caprolactone derived from renewable sources like or via chemoenzymatic routes, such as to followed by cyclization, supporting initiatives by Ingevity and others to reduce dependency. Regulatory aspects include U.S. (FDA) approval for PCL in biomedical applications since the 1970s for uses like devices and sutures, with expanded clearances in the for resorbable implants due to its demonstrated and slow degradation profile. This approval underscores PCL's safety in human applications, provided medical-grade specifications are met, facilitating its integration into clinical products worldwide.

Applications

Biomedical Applications

Polycaprolactone (PCL) is widely utilized in biomedical applications due to its excellent , biodegradability, and tunable mechanical properties, making it suitable for use without eliciting significant adverse reactions. Studies demonstrate low in PCL-based materials, with cell viability exceeding 90% in and cultures, and minimal inflammatory responses observed, such as reduced formation rates below 5% after implantation. Its slow degradation profile, typically spanning 2–4 years, supports temporary structures that gradually transfer load to regenerating tissues while producing non-toxic byproducts like and . In , PCL serves as a primary material for scaffolds promoting and regeneration, often fabricated via or to create porous structures with interconnected pores of 100–500 μm, ideal for cell infiltration and nutrient diffusion. For instance, electrospun PCL fibers blended with enhance osteoblast adhesion and proliferation, leading to improved formation in rat calvarial defect models. These scaffolds integrate well with cells like osteoblasts, supporting osteogenic differentiation without foreign body reactions. PCL excels in systems, particularly for controlled release of hydrophobic therapeutics through microspheres and nanoparticles that leverage its degradation kinetics for sustained elution over weeks to months. Microspheres encapsulating , a hydrophobic anticancer agent, achieve release profiles extending 60 days, minimizing burst effects and enabling targeted with reduced systemic toxicity. This degradation-controlled mechanism ensures predictable kinetics, influenced by factors like molecular weight and environmental esterases. For , PCL is incorporated into sutures, films, and membranes that provide mechanical support while promoting tissue repair. The FDA-approved Monocryl sutures, a of glycolide and ε-caprolactone, offer high tensile strength (approximately 25 MPa) and complete absorption within 90–120 days, reducing risks and scarring compared to non-absorbable alternatives. PCL films applied as dressings facilitate epithelialization by maintaining a moist environment and exhibiting properties when loaded with agents like silver nanoparticles. In implants and prosthetics, PCL enables long-term degradable devices such as orthopedic fixation pins and vascular stents, where its flexibility and strength (tensile modulus 300–500 MPa) support load-bearing while degrading to avoid secondary surgeries. Biodegradable PCL stents coated on metallic frameworks show potential for integration in animal models. These applications benefit from PCL's ability to form composites that mimic native tissue . Recent developments from 2020–2025 have advanced PCL in , where hydrogels combined with PCL provide shear-thinning bioinks for precise deposition of cell-laden constructs, achieving resolutions below 200 μm for complex tissue mimics like . Antimicrobial PCL composites, incorporating silver nanoparticles or magnesium, exhibit over 99% bacterial reduction against while maintaining , addressing infection control in implants and scaffolds. As of 2025, emerging trends include AI-optimized production for sustainable and stimuli-responsive PCL systems for , supporting market growth at a projected CAGR of 9.5% from 2025 to 2034. These innovations, often via fused deposition modeling, enhance customization for .

Industrial and Consumer Applications

Polycaprolactone (PCL) is widely utilized as a filament material in fused deposition modeling (FDM) for and prototyping due to its low of approximately 55–60°C, which enables compatibility with standard desktop printers and facilitates easy post-processing, such as reshaping in hot water. This property makes PCL suitable for hobbyist applications, including custom prototyping of non-structural parts and educational models, where its biodegradability adds an environmental advantage over traditional filaments like (ABS). Its mechanical flexibility, derived from a temperature of -60°C, further supports printability in low-temperature environments without requiring specialized equipment. In packaging, PCL serves as a base for biodegradable films that provide barrier properties against oxygen and moisture, often blended with to enhance flexibility and reduce brittleness for applications like wraps and agricultural covers. These -PCL blends exhibit improved tensile strength and elongation, making them viable for short-term solutions that degrade under composting conditions. For adhesives, PCL is incorporated into hot-melt formulations, leveraging its nature to create flexible, solvent-resistant bonds suitable for and products, with adhesion strength enhanced by additives like isolate. PCL reinforces composites and blends, particularly with (PLA) or (PBAT), to produce durable plastics with balanced stiffness and toughness for industrial uses. In automotive parts, PCL-PLA blends contribute to lightweight components such as interior panels, where PCL addition improves impact resistance while maintaining biodegradability. For , PCL-based mulches, often combined with PBAT, offer weed suppression and retention, degrading fully within 6–12 months to minimize needs. Among consumer products, PCL enables time-release fertilizers by encapsulating nutrients like , controlling release over 30–60 days to optimize for plants such as mung beans while reducing leaching. It is also explored in biodegradable fishing nets, where PCL monofilaments degrade in marine environments to mitigate ghost fishing impacts. In textiles, PCL-based shape-memory polymers allow fabrics to recover from deformation upon heating, applied in adaptive for enhanced comfort and durability. The PCL market has seen expansion in sustainable packaging following post-2020 regulations, such as the European Union's Single-Use Plastics Directive, driving adoption in eco-friendly films and reducing reliance on petroleum-based alternatives. This growth is projected at a (CAGR) of 5.5% from 2024 to 2032, reaching USD 1.85 billion, fueled by demand for biodegradable options in consumer goods. Examples include PCL in eco-friendly toys, where its non-toxicity and moldability support sustainable designs like flexible action figures that biodegrade safely. Despite these advantages, PCL's higher production cost limits broader adoption in cost-sensitive sectors, though this is addressed through copolymers like PET-PCL blends that incorporate recycled PET to lower expenses while preserving biodegradability.

Biodegradation and Environmental Impact

Degradation Mechanisms

Polycaprolactone (PCL) primarily degrades through hydrolytic mechanisms involving the cleavage of bonds in its backbone by water molecules, leading to chain scission and formation of hydroxyl and end groups. This process is autocatalytic, particularly at neutral pH, where the generated s lower the local pH and accelerate further . The rate of hydrolytic degradation is significantly influenced by the 's crystallinity, with amorphous regions degrading faster than crystalline domains, resulting in an initial preferential breakdown of less ordered segments. Enzymatic degradation of PCL is mediated by lipases that adsorb onto the polymer surface and catalyze ester bond hydrolysis, often achieving substantial weight loss under controlled conditions. Lipases from Candida antarctica can cause up to 87% weight loss in PCL films within 72 hours, while those from Pseudomonas species result in 70-75% weight loss over 3-8 days. Typical kinetics show 10-20% weight loss in the first few months, depending on enzyme concentration and PCL molecular weight, with surface erosion dominating the process. Microbial degradation involves bacteria and fungi that colonize PCL surfaces, forming biofilms and producing enzymes that facilitate breakdown, ultimately leading to CO₂ evolution in aerobic environments. Bacteria such as Amycolatopsis species and Pseudomonas spp. exhibit strong degradative activity, with some strains achieving over 80% degradation in 10 days at 37°C. Fungi like Fusarium spp. and Chaetomium globosum contribute through cutinase and lipase secretion, enabling complete degradation of thin PCL films in 28 days under optimal conditions. Several factors modulate the overall degradation rate of PCL, including molecular weight, , and surface area. Lower molecular weight PCL degrades more rapidly due to increased mobility, while above 37°C enhance enzymatic and hydrolytic rates, with optimal activity often around 50°C for thermophilic microbes. Higher surface area, as in porous or nanofibrous forms, accelerates degradation by providing more sites for microbial attachment and water penetration; in , PCL exhibits a of 2-4 years under ambient conditions. The primary degradation product is 6-hydroxyhexanoic acid, which further metabolizes into smaller oligomers and ultimately mineralizes to CO₂ and water via β-oxidation pathways in microbial systems. Analytical techniques for monitoring PCL degradation include (GPC) to quantify chain scission through reductions in molecular weight and polydispersity, and (DSC) to track changes in crystallinity, such as increases from 39% to 95% as amorphous regions are preferentially eroded.

Environmental Considerations

Polycaprolactone (PCL) exhibits a relatively low environmental footprint in lifecycle assessments, particularly when compared to conventional plastics like (PET), benefiting from its biodegradability which offsets emissions through end-of-life decomposition. This lower carbon profile is attributed to efficient synthesis routes that minimize energy inputs and enable biological breakdown, reducing long-term atmospheric contributions. Certain PCL-based materials demonstrate compostability under industrial conditions and can meet standards such as ASTM D6400, which requires at least 90% within 180 days at 58°C and no ecotoxic residues. However, concerns arise regarding microplastic formation in marine environments, where incomplete degradation of PCL fragments can release sub-micron particles that persist and potentially harm aquatic ecosystems, as observed in hydrolytic studies showing toxicity to primary producers. Efforts to mitigate this include enhanced microbial degradation strategies to accelerate breakdown in . The shift toward bio-based PCL variants addresses dependency, with developments using renewable monomers like soybean-derived polyols via , enabling partial bio-content (up to ~30-50% depending on ratios). As of 2025, commercial production of such alternatives remains limited, with ongoing research into renewable feedstocks. supports this transition; PCL is listed under EU REACH for safe use, with biodegradable claims verified through certifications like EN 13432, influencing adoption amid bans on non-degradable plastics in and . As of 2025, the EU's revised Packaging and Packaging Waste Regulation emphasizes verifiable biodegradability claims for plastics like PCL. Future challenges include PCL's slower degradation in landfills under anaerobic conditions, which can occur within months to years depending on specifics (e.g., ~0.2 years for thin films), limiting its circularity compared to aerobic environments. Recycling is further complicated by blends with other polymers, such as PLA or PBAT, due to immiscibility leading to property deterioration during mechanical reprocessing and contamination risks. Despite these hurdles, PCL offers positive impacts by reducing ; in , biodegradable mulching films prevent accumulation of persistent residues, while in , it replaces non-degradable films, minimizing marine litter through controlled composting.

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