Synthesis of Modified Polycaprolactams Obtained from Renewable Resources

Oelmann, Stefan; Meier, Michael A. R.

doi:10.1002/macp.201500257

Cited by 13 publications

(11 citation statements)

References 45 publications

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“…Gel permeation chromatography/size exclusion chromatography (SEC) measurements were performed in hexafluoroisopropanole and show polymer mass values ( M n / M w ) from 1400/3300 to 1900/5600 (Figure A; line shows calibration curve with circles as limits, Table ; Table S1, Supporting Information). This is in similar range to some structurally different biobased polyamides synthesized via different procedures, and better than the previously described menthone‐based polyamides …”

Section: Introductionsupporting

confidence: 79%

“…They can be synthesized via polycondensation of dicarboxylic acids and diamines or via ring‐opening polymerization (ROP) of lactams . Within the past years, several interesting biobased polyamides have been described, for instance based on sebacic acid (or other platform chemicals from castor oil), succinic acid, brassylic acid, abietic acid, limonene, fatty acids (or their methyl esters), and furan‐2,5‐dicarboxylic acid . Furthermore, terpenoid ketones are very promising feedstocks for polyamide synthesis, as they can be converted into lactams, which are then polymerized via ROP to result in polyamides, in analogy to the “old” Nylon‐6 (polyamide‐6) synthesis from cyclohexanone via ε‐caprolactam (Scheme , box).…”

Section: Introductionmentioning

confidence: 99%

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Sustainable Chiral Polyamides with High Melting Temperature via Enhanced Anionic Polymerization of a Menthone-Derived Lactam

Winnacker

Neumeier

Zhang³

et al. 2016

Macromol. Rapid Commun.

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Polyamides are very important polymers that find applications from commodities up to the automotive and biomedical sectors, and their impact is continuously growing. The synthesis of structurally significant, chiral, and sustainable polyamides is described via a new, convenient, and solvent-free anionic polymerization of a biobased ε-lactam, which is obtained from the renewable terpenoid ketone l-menthone in a one-step synthesis. These polyamides are shown to have outstanding structural and thermal properties, which are thus introduced via the structure and chirality of the natural lactam monomer and which are discussed and compared with those of petroleum-based, established, and commercial polyamide Nylon-6. X-ray data reveal a remarkable degree of crystallinity in these green polymers and emphasize the impact of their structural features on the resulting properties.

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Section: Introductionsupporting

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Sustainable Chiral Polyamides with High Melting Temperature via Enhanced Anionic Polymerization of a Menthone-Derived Lactam

Winnacker

Neumeier

Zhang³

et al. 2016

Macromol. Rapid Commun.

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“…For instance, starting from 2‐cyclohex‐1‐enone (obtained from cyclohexene derived from polyunsaturated fatty acid methyl esters, FAME), a thia Michael addition can be applied for the preparation of SR‐modified cyclohexanones ( 13, Scheme ). After oxidation to 14 and oxime formation ( 15 ), suchlike monomeric lactam precursors ( CL‐SO 2 R 1–3 ) were obtained with high regioselectivity via Beckmann rearrangement of the corresponding oximes . Polycaprolactams ( PCL‐SO 2 R 1–3 ) can then be obtained by means of Sn(Oct) 2 as catalyst (Scheme ).…”

Section: Biobased Polyamides Via Ring‐opening Polymerization Of Lactamentioning

confidence: 99%

Biobased Polyamides: Recent Advances in Basic and Applied Research

Winnacker

Rieger

2016

Macromol. Rapid Commun.

228

161

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Polyamides represent a very important class of polymers for a wide range of applications. After establishing in the 1930s with Nylon and Perlon, their impact on many branches has been continuously growing. In the context of developing sustainable polymers from renewable resources, many polyamides have meanwhile been described, which are based on natural building blocks. In addition to their sustainability, these biobased starting materials can provide special structural features to the resulting polymers and their properties, e.g., side groups, functionalities, or stereoinformation. While some biopolyamides are known for decades and well established (e.g., PA-11, Rilsan), many other promising candidates have been described in fundamental research studies, which have high potential but whose capability-especially for large scale and/or high-performance materials-will have to be proved in the future. Other candidates are very interesting from a scientific point of view, but with less potential for a market establishment due to price and/or feasibility reasons. This article aims at collating the recent developments in the field of biopolyamides and elucidating their properties and potential for different applications.

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“…Only one example of fatty acid-based PA produced via ROP has been reported in the literature. 460 Indeed, the multi-step synthesis involved to obtain a polymerizable lactam is not viable at the industrial scale. Contrarily, terpenes and glucose were mentioned in a recent review 429 to be good candidates for the preparation of sustainable lactams.…”

Section: Figure 79mentioning

confidence: 99%

Bio-Sourced Polymers: Recent Advances

Cramail

Bizet

Lamarzelle

et al. 2020

Series on Chemistry, Energy and the Environment

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Synthetic polymers are of major interest in the chemical industry, with a world production superior to 350Mt in 2016. They find applications in all the branches of industry, from packaging films to the stateof-the-art materials for sports and leisure activities, construction and aerospace industry or medical applications. Half of the amount of molecules produced by the petrochemical industry thus finds itself incorporated in the elaboration of polymer materials. With a production of 160Mt / year, ethylene can be considered as the major example of petroleum-based monomers. Green Chemistry introduced in 1998 by Anastase et al. (refer to Chapter 1 of this book), aims at providing solutions to reduce environmental impacts of our society. More precisely, this pursue of a more sustainable chemistry consists in using a source of renewable carbon to both reduce the dependence on fossil resources and thus stabilize greenhouse gas emissions (in particular CO 2 ) at the end of life. The use of renewable resources is of major interest in the elaboration of bio-sourced polymers. By using them, it is possible to mimick the fossil-based polymers -drop-in structures such as biopolyethylene-or to design new chemical structures, such as poly(lactic acid), PLA. Nowadays, the vegetal-based chemistry (renewable resources) mobilizes less than 0.5 % of arable land in the world. Some reminders of the definitions of the terms biomass, biopolymer, biodegradable polymer, bio-sourced polymer, bioplastic, biorefinery may be necessary: Biomass: material of biological origin (elaborated by alive bodies) with the exception of the materials of geological or fossil formation.Biopolymer: polymer developed by alive bodies, extracted from the biomass. Examples: polysaccharides, proteins, bacterial polymers.Biodegradable polymer: polymer the main degradation mechanism of which can be biotic, by enzymatic way. Under the action of micro-organisms and in the presence of oxygen (aerobic conditions), the organic compound decomposes totally within few months into carbon dioxide, water and mineral salts, with the appearance of a new biomass; in the absence of oxygen (anaerobic conditions), the organic compound decomposes totally within few months into carbon dioxide, methane, mineral salts and creation of a new biomass.Bio-sourced (or bio-based) polymer: synthetic polymer partially (generally > 20 %) or totally obtained from by-products stemming from the biomass. The bio-sourced character of a polymer can be determined in particular from its content in C14, according to the standard ASTM D6866. For the materials of totally fossil origin, the content in C14 is null.Bioplastic: term of popularization which indicates a 'biobased plastic' (restricted definition) and/or biodegradable (wider definition).Biorefinery: by analogy with a classic refinery, which works from fossil resources, a bio-refinery handles biomasses to produce, according to the cases, energy, fuels, materials, chemical and polymer products and/or animal and human feed. Today, two biopolymers ac...

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Synthesis of Modified Polycaprolactams Obtained from Renewable Resources

Cited by 13 publications

References 45 publications

Sustainable Chiral Polyamides with High Melting Temperature via Enhanced Anionic Polymerization of a Menthone-Derived Lactam

Sustainable Chiral Polyamides with High Melting Temperature via Enhanced Anionic Polymerization of a Menthone-Derived Lactam

Biobased Polyamides: Recent Advances in Basic and Applied Research

Bio-Sourced Polymers: Recent Advances

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