Exploratory investigation of the effect of nylon grain size on ablation of phenolic nylon
Exploratory investigation of nylon grain size effect on ablation of phenolic nylon
NYLON↗
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Factors modulating the hydrolysis of Nylon-6,6 by a nylon hydrolase enzyme
The enzymatic hydrolysis of polyamides offers a promising approach to reduce the environmental impact of chemical recycling by enabling lower reaction temperatures, eliminating toxic organic solvents, and enhancing product selectivity. Achieving this goal will require increasing the low overall yield of enzymatic hydrolysis. In this work, we studied the mechanism of hydrolysis of commercial Nylon-6,6 polymer with a thermostable Nylon hydrolyzing enzyme and identified the substrate characteristics that influence the efficiency and deconstruction product yield. These results will guide the development of effective substrate pre-treatment methods to improve the yield of valuable oligoamide building blocks via enzymatic hydrolysis.
Bocharova, Vera [Oak Ridge National Laboratory (OR↗
Absorption of water and lubricating oils into porous nylon
Oil and water absorption from air into sintered porous nylon can be described by infiltration into the pores of the material. This process can be modeled by a diffusion-like mechanism. For water absorption, we find a formal diffusion coefficient of 1.5 x 10(exp -4)sq cm/min when the nylon is initially dry. The diffusion coefficient is 4 x 10(exp -6)sq cm/min when the nylon is oil-impregnated prior to air exposure. In a 52% RH atmosphere, dry nylon absorbs 3% w/w water, and oil-impregnated nylon absorbs 0.6% w/w water. For oil absorption there are three steps: (1) surface absorption and infiltration into (2) larger and (3) smaller pores. Surface absorption is too fast to be measured in these experiments. The diffusion coefficient for the second step is 6 x 10(exp -4)sq cm/min for SRG-60 oil into dry nylon and 4 x 10(exp -4)sq cm/min for air-equilibrated nylon. The diffusion coefficient for the third step is about 1 x 10(exp -6)sq cm/min for both cases. The total amount of oil absorbed is 31% w/w. The interaction between water and nylon is not as strong as that between water and cotton-phenolic: oil can replace water, and only a small amount of water can enter previously oil-impregnated nylon.
Bertrand, P. A.↗
A Circular and Tacticity‐Independent Crystalline Mono‐Substituted Nylon‐6 Platform: Unexpected Large Positional Effects on Crystallizability and Performance
Seeking recyclable, more sustainable alternatives to nylon 6 has drawn much attention, but achieving its variants with both crystallinity and enhanced recyclability still remains a challenge. Here, by utilizing bio-derivable mono-substituted racemic lactam monomers, we reveal surprisingly large effects of methyl substitution positions on the nylon-6 backbone on crystallizability, thermomechanical performance, and recyclability of the resulting atactic nylon-6 variants. While γ-methyl substitution gives an amorphous nylon, all other four methyl-substitution positions (α, β, δ, and ε) afford, unexpectedly, crystalline nylons with melting temperatures ranging from 145°C to 200°C and tunable mechanical performance from being stiff and strong (α, ε) to ductile (β, δ). Investigations reveal that the crystallinity of atactic nylons arises independently of stereoregularity, which is driven by the amide backbone with robust hydrogen-bonding interactions and countered by the chain flexibility regulated by the substitution position. These nylons can be chemically recycled back to their parent monomers with high isolated yields up to 92%, enabling a circular, tacticity-independent crystalline nylon platform.
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
Alcoholysis of nylon 6 waste to ε-caprolactam promoted by phosphoric acid
Nylon 6 is widely used in high-performance materials. However, the inherent structural rigidity of nylon 6 inhibits catalytic depolymerization to its monomer, ε-caprolactam. Here, in this study, we demonstrate an acid-catalyzed alcoholysis process that depolymerizes nylon 6 to ε-caprolactam, achieving yields up to 74% using n-propanol as solvent and phosphoric acid as catalyst at 220°C for 2 h. We further applied the process to commercial nylon-containing products, demonstrating ε-caprolactam yields of 67% to 76%. Process modeling and techno-economic analysis estimated a minimum selling price of recycled nylon 6 at $\$$1.79/kg, 30% lower than the 5-year average market price of virgin nylon 6. These estimates depend on assumed costs and process performance and may vary with future conditions. Life cycle assessment indicated that nylon 6 produced via alcoholysis can reduce greenhouse gas emissions by up to 63% compared with primary production. Overall, this study demonstrates a facile, cost-effective, and environmentally beneficial process for nylon 6 chemical recycling.
09 BIOMASS FUELS↗
Improved nylon polymerization using amide diads
Nylons, a major class of synthetic polyamides, are widely used due to their excellent mechanical strength, thermal stability, and chemical resistance. Conventional nylon production relies on the polymerization of lactams or stoichiometric nylon salts. However, applying these approaches to unconventional precursors such as bio-derived glutaric acid produces polymers with low molecular weight and limited applications. To address these challenges, we demonstrated that chemically-synthesized nylon diads enable the production of higher-molecular-weight polyamides compared with traditional salts. We then identified a biosynthetic approach using amide synthetases to convert unprotected bifunctional substrates into nylon-relevant diads. Using a cofactor regeneration system, enzymatic diad synthesis was scaled to produce sufficient material for laboratory-scale characterization and solid-state polymerization. Amide synthetases demonstrated broad substrate scope, catalyzing the regioselective assembly of diverse nylon-relevant diacids, diamines, and ω-amino acids. This strategy offers a novel route to synthesize challenging nylon monomers and advances production of bioderived nylons.
Qian, Liangyu [Oak Ridge National Laboratory (ORNL↗
Chemical Recycling of Carbon Fiber-Reinforced Nylon Composites
Nylon-based fiber-reinforced composites are widely used in various sectors due to their strength, durability, and lightweight properties. Despite their widespread use, recycling these composites is difficult due to the inability to separate fibers and thermal instability of nylon at high temperatures. Consequently, most nylon composites are landfilled, leading to significant economic loss. Current fiber recovery methods (i.e., pyrolysis) are energetically inefficient and preclude recovery of the matrix. Dissolution methods, such as using hexafluoroisopropanol (HFIP), allow recovery of polymer and fiber but are economically taxing and require extensive safety infrastructure. Herein we report tailored glycolysis of nylon-6 composites, resulting in separated constituent fibers and nylon-6 oligomers. Deconstruction kinetics reveal nylon’s molecular weight reductions from 32,600 to 2000 g/mol, while SEM and tensile testing confirm recovered fiber integrity. In conclusion, this approach offers a pathway to reclaim high-value materials from nylon composites, providing a strategy for the chemical recycling of fiber-reinforced composites.
Zheng, Jackie [Univ. of Tennessee, Knoxville, TN (↗
Identification and characterization of substrate- and product-selective nylon hydrolases
Enzymes can rapidly and selectively hydrolyze diverse natural and anthropogenic polymers, but few have been shown to hydrolyze synthetic polyamides. Here, in this work, we synthesized and characterized a panel of 95 enzymes from the N-terminal nucleophile hydrolase superfamily with 30%–50% pairwise amino acid identity. We found that nearly 40% of the enzymes had substantial nylon hydrolase activity, but there was no relationship between phylogeny and activity, nor any evidence of prior evolutionary selection for nylon hydrolysis. Several newly identified hydrolases showed substrate selectivity, generating up to 20-fold higher product titers with nylon-6,6 versus nylon-6. However, the yield was still less than 1%, necessitating further optimization before potential applications. Finally, we determined the crystal structure and oligomerization state of a nylon-6,6-selective hydrolase to elucidate structural factors that could affect activity and selectivity. These new enzymes provide insights into nylon hydrolase evolution and opportunities for analysis and engineering of improved hydrolases.
nylon↗
Tailored glycolysis of Nylon 6 to enable upcycling into high-strength adhesives
Nylon is a high-strength polyamide widely used in automotive, textiles, packaging, etc. However, its durability makes nylon waste difficult to manage, with recycling limited to mechanical grinding to make fillers. Here, we report a catalytic glycolysis approach to deconstruct Nylon 6 into controlled-length oligomers, enabling upcycling into value-added materials. A low-molecular-weight oligomer (M n = 1.8 kg/mol) was repolymerized with diepoxy-terminated poly(bisphenol A-co-epichlorohydrin) via mechanochemistry to create a high-performance adhesive. This copolymer achieves lap shear strengths over 22 MPa on steel and bonds steel to carbon fiber composites, nearly tripling the performance of commercial adhesives even at 90°C. Thermomechanical analyses show that the adhesive retains thermal stability similar to nylon 6 but melts at lower temperatures, allowing easier processing. The material can be reprocessed and reused without significant performance loss. This study demonstrates a strategy to convert nylon 6 waste into valuable materials, offering a sustainable path for difficult-to-recycle plastics.
Nylon waste↗
Nylon separators
A nylon separator was placed in a flooded condition in K0H solution and heated at various high temperatures ranging from 60 C to 110 C. The weight decrease was measured and the molecular weight and decomposition product were analyzed to determine: (1) the effect of K0H concentration on the hydrolysis rate; (2) the effect of K0H concentration on nylon degradation; (3) the activation energy at different K0H concentrations; and (4) the effect of oxygen on nylon degradation. The nylon hydrolysis rate is shown to increase as K0H concentration is decreased 34%, giving a maximum rate at about 16%. Separator hydrolysis is confirmed by molecular weight decrease in age of the batteries, and the reaction of nylon with molecular oxygen is probably negligible, compared to hydrolysis. The extrapolated rate value from the high temperature experiment correlates well with experimental values at 35 degrees.
Lim, H. S.↗
Nylon and teflon scribe effect on NBR to Chemlok 233 and NBR to NBR bond interfaces
A study was requested by Manufacturing Engineering to determine what effects marking with nylon (6/6) and Teflon scribes may have on subsequent bonding. Witness panel bond specimens were fabricated by the development lab to test both acrylonitrile butadiene rubber (NBR) to Chemlok and NBR to NBR after controlled exposure. The nylon rod used as a scribe tool demonstrates virtually no bond deterioration when used to scribe lines on either the Chemlok to NBR surfaces or the NBR to NBR interface. Lab test results indicate that the nylon rod-exposed samples produce tensile and peel values very similar to the control samples and the Teflon exposed samples produce tensile and peel values much lower than the control samples. Visual observation of the failure surfaces of the tested samples shows that Teflon scribing produces an obvious contamination to the surface and the nylon produces no effect. Photographs of test samples are provided. It is concluded that Teflon stock used as a scribe tool on a Chemlok 233 to NBR surface or an NBR to NBR surface has a detrimental effect on the bond integrity on either of these bond interfaces. Therefore, it is recommended that the nylon rod continue to be used where a scribe line is required in the redesigned solid rocket motor segment insulation layup operations. The use of Teflon scribes should not be considered.
Jensen, S. K.↗
Challenges and Opportunities in the Enzymatic Recycling of Nylons
Enzymatic depolymerization has the potential to contribute to nylon waste recycling. However, the implementation of a viable industrial process still lags far behind progress in enzymatic polyester recycling. Here we review the current biocatalytic nylon recycling landscape, highlighting biochemical, structural, and materials science barriers that currently limit depolymerization extents. We detail efforts to identify, engineer, and characterize new nylon depolymerases, where currently even the best biocatalysts rarely exceed ~1 wt% conversion of solid polymer to products. Based on our analyses, we suggest that limited substrate accessibility due to substrate crystallinity and hydrogen bonding, rather than intrinsic enzyme inefficiency or instability, is the primary bottleneck to enhanced depolymerization. Guided by successes in polyester enzymatic recycling, we outline a research roadmap combining nylonase engineering with polymer pretreatment, chemo-enzymatic cascades, and process analyses to accelerate development of viable enzymatic nylon recycling processes.
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
Novel insight into the kinetics of amide bond glycolysis for nylon-6 depolymerization
Chemical recycling of nylon-6 to short-chain oligomers and monomer ε-caprolactam via catalytic glycolysis is a potential solution for plastic waste remediation. Here, in this work, the kinetics of amide bond glycolysis (with ethylene glycol) in nylon-6 and the model compound N-phenethyl-3-phenylpropanamide (M1) were evaluated at 473 K in the presence of the cyclic amidine catalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene. Rates of polymer glycolysis were determined by the time-dependent shift in molecular weight distribution, whereas rates of M1 glycolysis were determined using liquid chromatography. The similarity of the first-order rate constants for glycolysis of nylon-6 and M1 at 473 K with 0.03 M amidine catalyst (5 mol% relative to amide bonds), 1.22 × 10 −5 s −1 and 2.18 × 10 −5 s −1 , respectively, confirmed the suitability of M1 as a model compound for nylon-6 glycolysis. Similar rates of glycolysis in the presence of other cyclic amidine catalysts as well as sodium methoxide revealed little influence of base strength. Glycolysis rates were unexpectedly non-linear in catalyst loading and deactivation occurred with long reaction times, presumably by non-selective decomposition of products as detected by liquid chromatography.
Depolymerization rate and rate constant↗
Enzymatic Nylon Deconstruction: Enzyme Discovery, Engineering, and Opportunities
Nylons are widely used synthetic polyamides valued for their strength, versatility, and durability across diverse applications. However, their petrochemical origin and energy-intensive production underscore the need for efficient, circular solutions. Conventional recycling methods remain limited by incomplete recovery, material degradation, and costly sorting requirements. Enzymatic depolymerization offers a selective, low-energy alternative capable of processing mixed waste streams under mild conditions. While significant progress has been achieved for polyesters, enzymatic degradation of polyamides is still at an early stage. The discovery of nylon hydrolases demonstrated the potential of biological systems to evolve catalysts for synthetic polyamides, yet reported depolymerization yields remain low. These limitations reflect both the structural complexity of nylons and the need for improved enzyme discovery and engineering. In conclusion, this review highlights recent advances, key challenges, and future directions for enzymatic nylon recycling, outlining its potential role enabling mixed polymer waste to be used as a green feedstock for remanufacturing.
Amides↗
Moisture dependence of positron annihilation spectra in nylon-6
Positron annihilation time spectra have been measured in nylon-6 samples as a function of their moisture content. The measured average long life component lifetime values are: 1722 + or - 47 ps (dry), 1676 + or - 40 ps (14.6 percent saturation value), 1719 + or - 26 ps (29.3 percent saturation value), 1720 + or - 35 ps (50 percent of saturation value), 1857 + or - 35 ps (78.1 percent saturation value), and 1936 + or - 57 ps (saturated). It appears that nylon-6 has a special affinity for water at low concentration levels where H2O molecules enter between the (C = O - H-N) chemical bonds between nylon molecular chains. As the water concentration increases beyond a critical level, nylon-6 specimens start trapping H2O molecules in other bond sites or potential wells. The trapped water increases the free volume in the test specimens and reduces Ps atom formation as well as its subsequent decay rate.
Singh, J. J.↗
Novel use of positively charged nylon transfer membranes for trapping indoleacetic acid or other small anions during efflux from plant tissues
Positively charged nylon blotting membranes were used as an anion binding medium to trap [14C]indoleactic acid (IAA) as it exited cells at the basal ends of Coleus blumei L. stem and Zea mays L. coleoptile segments. Autoradiography was used to visualize where the [14C] that moved out of the cut ends was localized on the nylon membrane. Diffusion of [14C]IAA from the initial point of contact with the nylon membrane was minimal. Comparison of the autoradiograms with anatomical tissue prints of the cut ends of the segments was used to determine what tissues participate in IAA movement. The results of these initial studies were consistent with other reports suggesting that [14C]IAA movement was primarily associated with vascular tissues in both C. blumei stems and corn coleoptiles, but the resolution was not sufficient to identify which vascular tissues were involved in IAA transport. With further refinements, this technique could also be used for studying the movement of other small charged molecules through plant tissues.
NASA Discipline Plant Biology↗
Reaction Optimization for Enzymatic Deconstruction of Industrially Relevant Nylon Composites
Plastics such as polyamides (PAs) possess unique physicochemical properties that make them indispensable in modern society. However, their energy‐intensive production and challenging end‐of‐life management highlight the urgent need for efficient recycling or remanufacturing solutions. Enzymatic depolymerization offers a promising route toward circular recycling, yet remains constrained by limited enzyme characterization, lack of validation under industrially relevant conditions and substrates, and overall performance. Here, we optimized the reaction conditions for three recently discovered nylon‐degrading enzymes. One of them, Nyl12, achieved product titers with PA6 and PA66 that exceed previously reported values, without enzyme engineering or substrate pretreatment. We further demonstrated the scalability of the process and its application to complex PA‐based materials used in microelectronic components. Analysis of substrate features, including surface area and particle size, revealed key parameters governing enzymatic activity and provided a framework for future pretreatment and process optimization efforts. In combination, these efforts provide a new benchmark for enzymatic nylon recycling.
nylon↗
Measuring tropospheric HNO3 - Problems and prospects for Nylon filter and mist chamber techniques
A series of laboratory and field measurements was performed to evaluate the mist chamber technique for determining tropospheric HNO3 concentrations. Both the mist chamber and standard Nylon filter techniques exhibit high collection efficiency and excellent agreement measuring HNO3 vapors from a permeation source. When simultaneously sampling ambient air in eastern Virginia, the Nylon filter measured an average of 70 percent higher HNO3 concentration than the mist chamber technique. The results indicate that O3 causes a low-level positive artifact interference in HNO3 measurements performed with the filter technique. This O3-induced error is small, however, compared to the large difference between atmospheric HNO3 concentrations determined with the two techniques. It is hypothesized that unidentified (organic?) nitrogen species in the atmosphere react for form NO3(-) on the filter and this phenomenon may interfere with Nylon filter measurements of HNO3 vapor. These potential interferences did not appear to affect measurements of HNO3 with the mist chamber method.
Talbot, R. W.↗