The nitrosation of nylon

Porter, M. R.

doi:10.1002/pol.1958.1203312641

Cited by 17 publications

(5 citation statements)

References 10 publications

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“…One such example is the conversion of a polyamide to a polyester via thermal decomposition of a poly(nitroso-amide), which represents a combination of nitrogen deletion and oxygen insertion edits (Figure 8A). 4 In the reported transformation, nylon 6,6 yarn was nitrosated using a mixture of nitrogen tetroxide, acetic acid, and sodium acetate, and then heated to induce the backbone transformation (Figure 8A). At temperatures <100 °C, >95% conversion to the poly(ester) was determined by IR and elemental analysis of the products; however the polymer molecular weight was estimated to drop precipitously due to chain-scission: from 10,000-12,000 g/mol to 300-500 g/mol.…”

Section: Combinations Of Different Elementary Editsmentioning

confidence: 99%

“…At temperatures <100 °C, >95% conversion to the poly(ester) was determined by IR and elemental analysis of the products; however the polymer molecular weight was estimated to drop precipitously due to chain-scission: from 10,000-12,000 g/mol to 300-500 g/mol. 4 The resulting poly(ester) yarns had several differences in properties compared to their poly(amide) counterparts. As the percent of ester incorporation increases, the moisture retention decreases, which we speculate is due to the increased hydrophobicity of the poly(ester) compared to the poly(amide).…”

Section: Combinations Of Different Elementary Editsmentioning

confidence: 99%

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Editing of Polymer Backbones

Zhukhovitskiy

Ditzler

King

et al. 2022

Preprint

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Polymers are at the epicenter of modern technological progress and ensuing environmental pollution. Considerations of both polymer functionality and lifecycle are crucial in these contexts, and the polymer backbone—the core of a polymer—is at the root of these issues. Just as the meaning of a sentence can be altered through editing the words, so too could the function and sustainability of a polymer be transformed through chemical modification of its backbone. Yet, polymer modification has primarily been focused on the polymer periphery. In this Review, we attempt to bring a greater focus to transformations of the polymer backbone by defining some concepts fundamental to this topic (e.g., “polymer backbone” and “backbone editing”), collecting and categorizing examples of backbone editing scattered throughout a century’s-worth of chemistry literature, and outlining critical directions for further research. In so doing, we lay the foundation for the field of polymer backbone editing and hope to accelerate its development.

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Section: Combinations Of Different Elementary Editsmentioning

confidence: 99%

Section: Combinations Of Different Elementary Editsmentioning

confidence: 99%

Editing of Polymer Backbones

Zhukhovitskiy

Ditzler

King

et al. 2022

Preprint

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“…Our aim herein differs from our previous reports: in this work, we seek to modify polymer architecture while maintaining the class to which the polymer belongs, e.g., a polyester remains a polyester, and use catalytic reagents instead of stoichiometric ones. Critically, most reported polymer backbone edits are highly backbone-specific, which in turn limits their implementation, ,− and we sought to address this challenge within the context of architectural editing to ensure broad utility. We identified the transition-metal-catalyzed formal [3,3]-sigmatropic oxo-rearrangement (SOR) of allylic esters and carbamates (Figure ) as a potential candidate transformation for this purpose.…”

Section: Introductionmentioning

confidence: 99%

Architectural Editing of Polyesters and Polyurethanes via Palladium(II)-Catalyzed [3,3]-Sigmatropic Oxo-Rearrangements

Ditzler,

Rapagnani,

Berney

et al. 2024

J. Am. Chem. Soc.

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Architecture underlies the thermomechanical properties of polymers. Yet, few strategies are available to tune a polymer’s architecture after it is prepared without altering its chemical composition. The ability to edit the architecture of a polymer would dramatically expand the accessible architecture-property space of polymeric materials. Herein, we disclose a backbone rearrangement approach to tune the short-chain branching of polymers. Specifically, we demonstrate that palladium(II)-catalyzed [3,3]-sigmatropic oxo-rearrangements can transform branched polyesters and polyurethanes to their linear counterparts. While the effects on materials properties are generally subtle in the case of polyesters, more dramatic changes are observed in the case of polyurethanes: two polyurethanes undergo a soluble-to-insoluble transition, and one exhibits a dramatic increase in both strain at break and toughness after rearrangement. Additionally, the incorporation of alkenes in the polymer backbone through the rearrangement enables facile deconstruction via ethenolysis. In all, we disclose a powerful and broad-scope strategy to edit the architecture of polymer backbones and thereby tune their physical and chemical properties.

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“…The blends of PET and PC have been widely studied in recent years. [4][5][6][7][8][9][10] Researchers often improve mechanical properties and compatibility of different components by reactive blending, which is a low-cost method to produce a compatible blend, because of the copolymer formed during the process. V. N. Ignatov et al 4,11 used acetyl acetonate as the catalyzer to accelerate transesteritication.…”

Section: Introductionmentioning

confidence: 99%

Properties and morphology of recycled poly(ethylene terephthalate)/bisphenol a polycarbonate/poly(styrene‐b‐(ethylene‐co‐butylene)‐b‐styrene) blends by low‐temperature solid‐state extrusion

Guo

Zhang

Yin

et al. 2007

Polymers for Advanced Techs

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Among the various methods available for recycling plastics waste, blending technology is a straightforward and relatively simple method for recycling. In this paper, a new blending technology, low-temperature solid-state extrusion, was discussed. Several recycled poly(terephthalate ethylene)/ bisphenol a polycarbonate/poly(styrene-b-(ethylene-co-butylene)-b-styrene) blends (R-PET/PC/ SEBS blends) have been prepared by this technology. The results show that thermal and hydrolytic degradation of R-PET is improved when extruding temperature was between the glass transition temperature (T g ) and cold crystallization temperature (T cc ). Elongation at break and notched impact strength were increased evidently, from 15.9% to 103.6, and from 8.6 kJ/m 2 to 20.4 kJ/m 2 , respectively. The appropriate rotating speed of screws was between 100 and 150 rpm. At the same time, the appropriate rotating speed of the screws brings a suitable shear viscosity ratio of R-PET and PC, which is of advantage to blending of R-PET and PC together with SEBS. Dispersion of minor phase, PC and SEBS, became finer and smaller, to about 1 mm. Chain extender, Methylenediphenyl diisocyanate (MDI) can react with the end-carboxyl group and end-hydroxyl group of R-PET. FT-IR spectra testified that the reactions have been happened in the extruding process. A chain extending reaction not only increased the molecular weight of PET and PC, but also can synthesize PET-g-PC copolymer to act as a reactive compatilizer. An SEM micrograph shows that a micro-fiber structure of PET was formed in the blend sample.

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The nitrosation of nylon

Cited by 17 publications

References 10 publications

Editing of Polymer Backbones

Editing of Polymer Backbones

Architectural Editing of Polyesters and Polyurethanes via Palladium(II)-Catalyzed [3,3]-Sigmatropic Oxo-Rearrangements

Properties and morphology of recycled poly(ethylene terephthalate)/bisphenol a polycarbonate/poly(styrene‐b‐(ethylene‐co‐butylene)‐b‐styrene) blends by low‐temperature solid‐state extrusion

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