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Nylon 66
Nylon 66
Nylon 66
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Nylon 66
Names
IUPAC name
Poly[imino(1,6-dioxohexamethylene) iminohexamethylene]
Systematic IUPAC name
Poly(azanediyladipoylazanediylhexane-1,6-diyl)
Other names
Poly(hexamethylene adipamide),Poly(N,N'-hexamethyleneadipinediamide), Maranyl, Ultramid, Zytel, Akromid, Durethan, Frianyl, Vydyne
Identifiers
ChemSpider
  • None
ECHA InfoCard 100.130.739 Edit this at Wikidata
Properties
(C12H22N2O2)n
Density 1.140 g/ml (Zytel)
Melting point 264 °C (507 °F)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Non-hazardous
GHS labelling:
GHS07: Exclamation mark
Warning
Flash point 305.5 °C (581.9 °F; 578.6 K)
485.1 °C (905.2 °F; 758.2 K)
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nylon 66 (loosely written nylon 6-6, nylon 6/6, nylon 6,6, or nylon 6:6) is a type of polyamide or nylon. It, and nylon 6, are the two most common for textile and plastic industries. Nylon 66 is made of two monomers each containing six carbon atoms, hexamethylenediamine and adipic acid, which give nylon 66 its name.[1] Aside from its superior physical characteristics, nylon 66 is attractive because its precursors are inexpensive.

Synthesis and manufacturing

[edit]
Hexamethylenediamine (top) and adipic acid (bottom), monomers used for polycondensation of Nylon 66.

Nylon 66 is synthesized by polycondensation of hexamethylenediamine and adipic acid. Equivalent amounts of hexamethylenediamine and adipic acid are combined in water. In the original implementation, the resulting ammonium/carboxylate salt was isolated and then heated either in batches or continuously to induce polycondensation.[2]

n(HOOC−(CH2)4−COOH) + n(H2N−(CH2)6−NH2) → [−OC−(CH2)4−CO−NH−(CH2)6−NH−]n + (2n-1) H2O

Removing water drives the reaction toward polymerization through the formation of amide bonds from the acid and amine functions. Alternatively, the polymerization is conducted on a concentrated aqueous mixture formed of hexamethylenediamine and adipic acid.[3]

It can either be extruded and granulated at this point or directly spun into fibers by extrusion through a spinneret (a small metal plate with fine holes) and cooling to form filaments.

Applications

[edit]

In 2011 worldwide production was two million tons. At that time, fibers consumed just over half of production and engineering resins the rest. It is not used in film applications as it cannot be biaxially oriented.[4] Fiber markets represented 55% of the 2010 demand with engineering thermoplastics being the remainder.[5]

Nylon 66 is frequently used when high mechanical strength, rigidity, good stability under heat and/or chemical resistance are required.[6] It is used in fibers for textiles and carpets and molded parts. For textiles, fibers are sold under various brands, for example Nilit brands or the Cordura brand for luggage, but it is also used in airbags, apparel, and for carpet fibres under the Ultron brand. Nylon 66 lends itself well to make 3D structural objects, mostly by injection molding. It has broad use in automotive applications; these include "under the hood" parts such as radiator end tanks, rocker covers, air intake manifolds, and oil pans,[7] as well as numerous other structural parts such as hinges,[8] and ball bearing cages. Other applications include electro-insulating elements, pipes, profiles, various machine parts, zip ties, conveyor belts, hoses, polymer-framed weapons, and the outer layer of turnout blankets.[9] Nylon 66 is also a popular guitar nut material.[10]

Nylon 66, especially glass fiber reinforced grades, can be effectively fire retardant with halogen-free products. Phosphorus-based flame retardant systems are used in these fire-safe polymers and are based on aluminium diethyl phosphinate and synergists. They are designed to meet UL 94 flammability tests as well as Glow Wire Ignition Tests (GWIT), Glow Wire Flammability Test (GWFI) and Comparative Tracking Index (CTI). Its main applications are in the electrical and electronics (E&E) industry.

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Nylon 66

View on Grokipedia
from Grokipedia
Nylon 66 is a synthetic polymer, chemically known as poly(hexamethylene adipamide), formed through the of and , two monomers each containing six carbon atoms—hence the designation "66". The repeating unit of its structure is [–NH–(CH₂)₆–NH–CO–(CH₂)₄–CO–], resulting in a linear chain that exhibits strong hydrogen bonding between groups, contributing to its characteristic crystallinity and mechanical performance. Developed at E.I. du Pont de Nemours and Company (), Nylon 66 was first synthesized on February 28, 1935, by Wallace H. Carothers and his team as part of a broader research effort into polyesters and polyamides. The team achieved high-molecular-weight polymers by using a molecular still to remove water during polymerization, followed by cold drawing to orient the polymer chains and enhance fiber properties. DuPont patented the material in 1938 and began commercial production in 1939 at a dedicated plant in , initially targeting applications that mimicked . Nylon 66 possesses notable mechanical properties, including high tensile strength (80-100 MPa for fibers), excellent elasticity, abrasion resistance, and toughness, with a around 255°C and of 1.14-1.15 g/cm³. It demonstrates good chemical resistance to alkalis and many solvents but is susceptible to degradation by strong acids, which can hydrolyze the bonds back to the monomers. These attributes make it versatile for diverse applications, such as fibers for and apparel, cords, ropes, conveyor belts, automotive components like parts and , and industrial uses including nets and .

History

Invention and Early Development

The invention of Nylon 66 stemmed from the pioneering work of Wallace H. Carothers, an American chemist recruited by in 1928 to lead fundamental research in and polymer science at the company's Experimental Station in . Carothers' team systematically explored condensation polymerization, focusing on high-molecular-weight compounds formed from bifunctional monomers, with polyamides emerging as a key area of investigation starting in 1934. This research built on earlier successes like synthetic rubber and aimed to create novel materials with fiber-forming potential, diverging from natural polymers like and . In early 1935, Carothers and his colleagues, including Julian Hill and Donald Coffman, conducted experiments reacting various diamines with dicarboxylic acids to produce polyamides, evaluating their ability to form strong, elastic fibers. On February 28, 1935, they successfully synthesized the first sample of what would become Nylon 66 by polymerizing hexamethylenediamine with adipic acid, selected for their commercial availability from benzene derivatives and the resulting polymer's superior melt viscosity and fiber properties compared to alternatives like polyamide 5,10. This combination yielded a linear polyamide with the repeating unit denoted as "66" due to the six-carbon chains in each monomer, marking a breakthrough in achieving polymers with molecular weights around 12,000 through water removal using a molecular still. Carothers died by suicide on April 29, 1937, before seeing the commercial success of his work. The initial synthesis was patented on September 27, 1938, as U.S. Patent 2,130,523, titled "Linear Polyamides and Their Production," with Carothers listed as the inventor and DuPont as assignee; the application had been filed on December 30, 1936. By 1938, lab-scale fiber production was achieved through melt spinning under high pressure (around 4,000 psi) to address the polymer's high melting point near its decomposition temperature, enabling the drawing of continuous filaments. Early challenges included precisely controlling molecular weight to ensure sufficient chain length for mechanical strength and inducing crystallinity via cold-drawing techniques, which enhanced elasticity but required iterative refinement to avoid brittleness. These hurdles were overcome through collaborative efforts involving over 230 scientists, laying the groundwork for Nylon 66's transition from laboratory curiosity to viable material.

Commercialization and Milestones

initiated commercial production of Nylon 66 at its plant on December 15, 1939, marking the first large-scale manufacturing of a . The company launched its initial consumer product, nylon stockings branded simply as "nylon," on May 15, 1940, in , before a national rollout that generated immediate demand, with four million pairs selling out in four days. This debut positioned Nylon 66 as the pioneering synthetic alternative to , revolutionizing women's with its durability and sheer appearance. With the ' entry into , redirected nearly all Nylon 66 production to military applications following , with the shift largely complete by early 1942, replacing imported in parachutes, tire cords for and vehicles, ropes, tents, and flak jackets. This shift boosted output dramatically; by 1945, monthly production reached approximately 4,000 tons to support the war effort, with 90% of the material allocated to defense needs. The material's strength and elasticity proved critical for these uses, contributing to Allied logistics and advancements. Post-war, civilian production resumed in , fueling a surge in consumer textiles during the as demand for durable fabrics in , , and exploded amid economic recovery and suburban growth. In the , Nylon 66 expanded into plastics, leveraging its mechanical properties for molded components in automotive and electrical applications. During the early , DuPont licensed Nylon technology to companies including in (1951) to expand global production and diversify applications.

Chemistry

Monomers and Structure

Nylon 66 is synthesized from two monomers: , with the chemical formula H₂N-(CH₂)₆-NH₂, and , with the formula HOOC-(CH₂)₄-COOH. Each of these monomers contains six carbon atoms, which is the origin of the "66" designation in the 's name. The systematic IUPAC name for Nylon 66 is poly[imino(1,6-dioxo-1,6-hexanediyl)imino-1,6-hexanediyl], and it is also known as poly(hexamethylene adipamide). The repeating unit of the polymer chain is represented as [-NH-(CH₂)₆-NH-CO-(CH₂)₄-CO-], with a molecular formula of (C₁₂H₂₂N₂O₂)ₙ per unit. The amide linkages (-NH-CO-) in the repeating unit enable the formation of strong intermolecular hydrogen bonds between adjacent polymer chains, which contributes to the material's crystallinity and structural integrity. Commercial grades of Nylon 66 typically exhibit a weight-average molecular weight in the range of 15,000 to 30,000 g/mol, corresponding to a of approximately 70 to 130 units.

Polymerization Mechanism

Nylon 66 is synthesized via a step-growth reaction, in which the groups of react with the groups of to form linkages, releasing as a . This process proceeds through the formation of an intermediate nylon salt (hexamethylenediammonium adipate), which is then heated to drive the . The reaction is catalyzed by the acidic itself, and no additional catalysts are typically required. The balanced equation for the polymerization is: n\ceHOOC−(CH2)4−COOH+n\ceH2N−(CH2)6−NH2→\ce[−NH−(CH2)6−NH−CO−(CH2)4−CO−]n+(2n−1)\ceH2On \ce{HOOC-(CH2)4-COOH} + n \ce{H2N-(CH2)6-NH2} \to \ce{[-NH-(CH2)6-NH-CO-(CH2)4-CO-]_n} + (2n-1) \ce{H2O} This equilibrium reaction favors the reactants unless water is continuously removed to shift the equilibrium toward polymer formation, commonly achieved through vacuum distillation or azeotropic distillation techniques. High temperatures (around 250–280°C) are applied under pressure initially, followed by reduced pressure to facilitate water evaporation. To attain high molecular weight, a precise 1:1 stoichiometric ratio of the monomers is maintained, often ensured by the controlled formation of the nylon salt. Deviations can limit chain growth due to end-group imbalance. Side reactions, such as the cyclization of end groups to form small cyclic oligomers, compete with chain extension, particularly at elevated temperatures, and are minimized by optimizing reaction conditions and .

Properties

Physical and Mechanical Properties

Nylon 66 is a semi-crystalline characterized by a of 1.14 g/cm³ in its unfilled form, which contributes to its lightweight yet robust nature suitable for various structural applications. This value is typical for unreinforced grades, such as DuPont's Zytel 101, and remains relatively consistent across processing conditions. The 's semi-crystalline structure features crystalline regions comprising 40–50% of the material, with the degree of crystallinity influencing its overall toughness and resistance to deformation. Higher crystallinity levels enhance stiffness and strength but can reduce flexibility, as the ordered molecular chains in crystalline domains provide greater intermolecular forces compared to amorphous regions. In terms of mechanical properties, Nylon 66 demonstrates notable tensile strength, ranging from 80–100 MPa for drawn fibers to 50–80 MPa for molded resins, depending on processing and conditioning. For instance, high-tenacity fibers achieve the upper end of this range due to orientation during , while unreinforced resins exhibit values around 65 MPa on average under standard testing. Elongation at break for fibers typically falls between 20–60%, allowing for significant before failure, which is attributed to the polymer's ability to undergo plastic deformation in both crystalline and amorphous phases. These properties make Nylon 66 resilient under load, with the semi-crystalline morphology balancing rigidity and energy absorption. Moisture absorption is a key physical characteristic of Nylon 66, with equilibrium uptake of 2.5–4.5% at 65% relative humidity, which can lead to dimensional changes of up to 0.5–1% in linear expansion. This hygroscopic arises from between molecules and the groups in the chain, affecting mechanical performance by plasticizing the material and reducing modulus by 30–50%. Compared to , Nylon 66's more symmetric molecular structure results in slightly lower moisture sensitivity and enhanced overall mechanical integrity.

Thermal and Chemical Properties

Nylon 66, a semicrystalline , has a temperature ranging from 50 °C to 60 °C in its dry state, marking the onset of segmental mobility in the amorphous regions. Its lies between 255 °C and 265 °C, allowing processing via melt techniques while maintaining structural integrity below this threshold. These thermal transitions enable applications requiring dimensional stability at moderate temperatures but limit use in high-heat environments without reinforcement. The exhibits stability up to approximately 300 °C, above which begins, releasing volatile products such as , , and hydrocarbons. under load varies significantly with formulation: unreinforced Nylon 66 deflects around 80–90 °C at 1.8 MPa, whereas glass-filled variants can withstand 150–200 °C or higher, enhancing suitability for components exposed to elevated temperatures. Chemically, Nylon 66 demonstrates strong resistance to nonpolar substances, including oils, greases, fuels, ethers, esters, ketones, and most hydrocarbons, due to its nonreactive backbone. However, it shows poor resistance to strong acids and oxidizing agents, which protonate or cleave the bonds, leading to rapid degradation. Prolonged exposure to hot or induces , breaking peptide-like linkages and reducing molecular weight over time. Unstabilized Nylon 66 is sensitive to ultraviolet radiation, undergoing photo-oxidation that results in yellowing, chain scission, and embrittlement upon extended exposure. Its flammability is characterized by a limiting oxygen index of 20–24%, yielding a UL 94 V-2 rating in standard grades; flame-retardant variants, incorporating phosphorus or halogen-free additives, achieve V-0 self-extinguishing behavior.

Manufacturing

Industrial Synthesis Processes

The industrial synthesis of Nylon 66 commences with the formation of hexamethylenediammonium adipate salt through the neutralization of adipic acid with hexamethylenediamine in an aqueous medium, typically using equimolar amounts to ensure stoichiometric balance. The reactants are mixed in a reactor, often with water to form a 60-70% solution, followed by purification to remove impurities such as iron or color bodies that could affect polymer quality; the salt is then concentrated, sometimes to 80 wt% solids, and stored for subsequent processing. This step is critical for controlling the polymerization reaction, as deviations in salt purity or composition can lead to inconsistent molecular weights. The core occurs in an via a batch process, where the concentrated salt solution, often stabilized with 0.5% acetic , is charged and heated to 250–280°C under of approximately 1.5–2 MPa (18 ) to prevent premature and promote initial . As temperature rises, is maintained until reaching the target, after which it is gradually reduced to atmospheric levels while venting to remove and drive the polycondensation forward; the reaction is held at 270–280°C for 30–45 minutes under (10–50 mmHg) to extend chain length and achieve the desired . The nitrogen-purged environment minimizes oxidation, ensuring the molten reaches a relative suitable for end-use. Post-polymerization, the viscous melt is extruded through a die into a bath for and solidification, then cut into uniform pellets or chips using an underwater pelletizer; for production, the melt is directly fed to a for . Additives such as antioxidants, delustrants, or nucleating agents are incorporated during melt to enhance stability and performance. Pellets are dried in a fluid bed dryer at 80–100°C to remove residual moisture below 0.2%, preventing during storage or remelting. Process variations include traditional batch autoclave methods, which offer flexibility for small-scale or specialty runs, versus modern continuous processes employing tubular reactors followed by continuous stirred-tank reactors (CSTRs) at 250–300°C and 1–10 atm for higher throughput and consistent quality. For high-viscosity grades used in resins, post-condensation solid-state is applied, where dried pellets are heated under at 200–250°C to further increase molecular weight without melting.

Production Scale and Market Overview

Global production of Nylon 66 reached approximately 2.3 million metric tons in 2024, reflecting steady demand in key sectors. This volume positions Nylon 66 as a major segment within the broader market, accounting for roughly 60% of total polyamide output when combined with as the dominant types. Capacity for Nylon 66 production stood at approximately 3.4 million metric tons globally in 2024, with utilization rates influenced by availability and end-market recovery. Leading producers include Ascend Performance Materials , which operates integrated facilities for vertical control; Shenma Industrial Group , responsible for about 15% of global output; and DuPont de Nemours, alongside and , which maintain significant manufacturing footprints. dominates production, holding over 50% of the global share, driven by 's expansive industrial base and proximity to sources. As of late 2025, 's Nylon 66 capacity has reached 1.27 million tons (37% of global), with emerging technologies, such as a breakthrough method developed by the , enhancing sustainability prospects. The Nylon 66 market was valued at approximately USD 9.9 billion in 2024 and is projected to grow at a (CAGR) of 4.7% through 2035. This expansion is primarily fueled by rising automotive demand for lightweight, high-strength components such as engine parts and airbags. Nylon 66 production relies heavily on , derived from the oxidation of , which forms a critical link in the alongside . The have seen disruptions from crises and global strains, including post-COVID recovery challenges and volatility in raw material pricing due to geopolitical tensions, leading to periodic shortages and cost increases.

Applications

Fibers and Textiles

Nylon 66 fibers are manufactured through a melt-spinning process, in which chips are heated to a molten state and extruded through a to produce continuous filaments, typically ranging from 5 to 20 denier for uses. These undrawn filaments are then stretched or drawn to approximately three to four times their original length in a controlled environment, aligning the polymer chains to enhance tensile strength, elasticity, and dimensional stability. For applications requiring bulk and loft, such as in blended yarns or nonwovens, the filaments undergo crimping to introduce waves or curls before being cut into staple lengths of 1 to 6 inches. In textile applications, Nylon 66 constitutes a major portion of production, serving diverse products including apparel like and , durable upholstery fabrics such as , high-strength ropes, and resilient carpets. Its versatility stems from processing into fine-denier monofilaments for sheer or heavier multifilament yarns for industrial cordage and floor coverings. The material's prominence in these areas highlights its role in both consumer and , where it provides longevity under repeated use. Key advantages of Nylon 66 fibers in textiles include exceptional abrasion resistance, which outperforms many synthetic alternatives and suits high-wear items like carpets and outerwear, and excellent elastic recovery (nearly 100% after 3-6% elongation), enabling shape retention in garments. Additionally, the fibers accept acid dyes effectively, allowing for deep penetration and vibrant, fast colors through ionic bonding with the polymer's amine end groups. These properties make Nylon 66 ideal for demanding textile environments. Historically, Nylon 66 gained widespread adoption in the for women's , offering a sheer, durable alternative to that transformed and sparked consumer demand during its commercial debut in 1940. Today, it is frequently blended with natural fibers like for improved breathability or with elastomers such as to boost stretch and recovery in activewear and form-fitting apparel.

Engineering and Industrial Uses

Nylon 66 is widely utilized in and industrial applications due to its versatility as a , enabling the production of durable, high-performance parts through processes like injection molding and . In these forms, it serves as a base material for structural components that require strength, , and resistance to , often enhanced by reinforcements such as glass fibers. One of the primary engineering applications of Nylon 66 is in the , where it is used for components like end tanks, manifolds, and gears, benefiting from its ability to withstand high temperatures and mechanical stresses under engine conditions. Glass fiber-reinforced Nylon 66, typically containing up to 40% reinforcement, provides enhanced stiffness and dimensional stability, making it suitable for under-the-hood parts that must endure vibrations and thermal cycling. For instance, in systems, these reinforced grades reduce weight compared to metal alternatives while maintaining load-bearing capacity. In the electrical and electronics sector, Nylon 66 resins are employed in connectors, housings, and cable ties, leveraging their excellent electrical insulation properties and flame retardancy in specialized grades. Fire-retardant variants, certified to UL94 V-0 standards, are particularly valued for circuit board components and , where they prevent ignition and self-extinguish rapidly upon flame exposure. These materials also exhibit low moisture absorption relative to other polyamides, ensuring consistent performance in humid environments. Consumer and industrial goods further demonstrate Nylon 66's adaptability, appearing in items such as power tools, fasteners, and appliance housings, where its impact resistance and processability allow for complex moldings. High-impact grades, often blended with elastomers, enhance flexibility for applications like bearings and bushings, reducing friction and extending in mechanical assemblies. Nylon 66 also plays a role in advanced manufacturing techniques, including filaments for prototyping engineering parts, where its thermal stability supports layer adhesion and post-processing. Composites incorporating Nylon 66 matrices with fillers like are emerging for lightweight structural elements in and machinery, offering a balance of rigidity and toughness. As of , recent developments include chemically recycled Nylon 66 for reduced carbon emissions and applications in medical devices and renewable energy components. These blends with elastomers further tailor properties for flexible yet durable components, such as seals and gaskets in industrial equipment.

Environmental Impact

Lifecycle and Emissions

The production of Nylon 66 generates significant , estimated at approximately 8-10 kg CO₂ equivalent per kg of , primarily stemming from the synthesis of its monomers, (HMDA) and . The production process, involving the oxidation of cyclohexane-derived intermediates with , is a major contributor, releasing (N₂O) as a byproduct at rates of up to 300 kg per tonne of before abatement. This N₂O, with a 298 times that of CO₂ over 100 years, accounts for a substantial portion of the emissions, though modern abatement technologies achieve 90-99% reduction efficiency. Lifecycle assessments of Nylon 66 reveal high in the stage, requiring around 139 MJ per kg (or 139 GJ per tonne), dominated by and as primary fuels. consumption is also notable, at approximately 663 m³ per tonne, encompassing process and cooling needs across the . Upstream sourcing, including derivation for both monomers, contributes over 70% of total lifecycle GHG emissions due to energy-intensive cracking and oxidation steps. Efforts to mitigate upstream impacts include shifts toward bio-based monomers in the , with pilot-scale production of renewable from wood tar achieving up to 96% CO₂ emission reductions compared to routes. Companies like OzoneBio have demonstrated scaled synthesis of 100% biobased Nylon 66 pellets in 2025, verified for industrial applications, signaling potential for broader adoption in reducing fossil dependencies. At end-of-life, of Nylon 66 releases oxides () due to the polymer's content, with emissions arising from the thermal conversion of groups during . Landfilling, a common disposal method, leads to microplastic leaching into as the polymer degrades slowly under anaerobic conditions, contributing to environmental in landfill sites.

Degradation and Recycling

Nylon 66 exhibits high chemical stability due to its linkages, but it undergoes degradation through several mechanisms under specific environmental conditions. Hydrolytic degradation occurs via acid- or base-catalyzed of the amide bonds, breaking the chains into monomers like and , particularly in moist or aqueous environments. Thermal degradation predominates above 250°C, involving scission and volatilization of cyclic oligomers such as , leading to reduced molecular weight and mechanical properties. , induced by UV radiation, causes scission and oxidation, forming carbonyl groups and lowering tensile strength, especially in exposed applications like textiles. The persistence of Nylon 66 in the environment is notable due to its slow rate, often taking years to decades in under natural conditions, as microbial enzymes struggle to hydrolyze the strong bonds. This durability contributes to its accumulation as , with textile-derived Nylon fibers accounting for a significant portion of marine microplastic through laundering and abrasion, persisting in oceans and entering food chains. Recycling strategies for Nylon 66 address its end-of-life management, with mechanical recycling involving melt reprocessing of collected waste into pellets for , though limited to about 20 reprocessing loops before significant degradation reduces performance due to chain shortening and loss of . Chemical recycling offers higher value recovery through to monomers; methods, such as alkaline or acidic processes, achieve yields up to 90% of and , enabling repolymerization into virgin-quality Nylon 66. Recent advances in Nylon 66 emphasize , with the low-carbon recycled Nylon market valued at USD 2.8 billion in 2024 and projected to reach USD 7.2 billion by 2034, driven by demand for eco-friendly materials in automotive and textiles. Enzymatic pilots, leveraging nylon hydrolases from like Brevibacillus , have demonstrated up to 22% weight loss in over 35 days in lab settings, with industrial-scale trials emerging by 2025 to complement traditional methods. Challenges in Nylon 66 recycling include contamination from mixed waste streams, such as dyes and other polymers, which complicates sorting and reduces recycling efficiency. Emerging alternatives like bio-based nylons, derived from renewable monomers, are gaining traction to mitigate these issues and enhance biodegradability without compromising performance.

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