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| Names | |
|---|---|
| Other names Poly(ethylene 2,6-naphthalate) PEN | |
| Identifiers | |
| ChemSpider |
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| Properties | |
| (C14H10O4)n | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Polyethylene naphthalate (poly(ethylene 2,6-naphthalate) or PEN) is a polyester derived from naphthalene-2,6-dicarboxylic acid and ethylene glycol. As such it is related to poly(ethylene terephthalate), but with superior barrier properties.
Two major manufacturing routes exist for polyethylene naphthalate (PEN), i.e. an ester or an acid process, named according to whether the starting monomer is a diester or a diacid derivative, respectively. In both cases for PEN, the glycol monomer is ethylene glycol. Solid-state polymerization (SSP) of the melt-produced resin pellets is the preferred process to increase the average molecular weight of PEN. [1]
Because it provides a very good oxygen barrier, it is well-suited for bottling beverages that are susceptible to oxidation, such as beer. It is also used in making high performance sailcloth.
Significant commercial markets have been developed for its application in textile and industrial fibers, films, and foamed articles, containers for carbonated beverages, water and other liquids, and thermoformed applications. It is also an emerging material for modern electronic devices.
It also has been found to show excellent scintillation properties and is expected to replace classic plastic scintillators. [2]
The two condensed aromatic rings of PEN confer on it improvements in strength and modulus, chemical and hydrolytic resistance, gaseous barrier, thermal and thermo-oxidative resistance and ultraviolet (UV) light barrier resistance compared to polyethylene terephthalate (PET). PEN is intended as a PET replacement, especially when used as a substrate [3] for flexible integrated circuits.
A monomer is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization.
Petrochemicals are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sources such as maize, palm fruit or sugar cane.
Polyethylene or polythene (abbreviated PE; IUPAC name polyethene or poly(methylene)) is the most commonly produced plastic. It is a polymer, primarily used for packaging (plastic bags, plastic films, geomembranes and containers including bottles, etc.). As of 2017, over 100 million tonnes of polyethylene resins are being produced annually, accounting for 34% of the total plastics market.
A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling.
Polyethylene terephthalate (or poly(ethylene terephthalate), PET, PETE, or the obsolete PETP or PET-P), is the most common thermoplastic polymer resin of the polyester family and is used in fibres for clothing, containers for liquids and foods, and thermoforming for manufacturing, and in combination with glass fibre for engineering resins.
Although PET is used in several applications, as of 2022 only bottles are collected at a substantial scale. The main motivations have been either cost reduction or recycle content of retail goods. An increasing amount is recycled back into bottles, the rest goes into fibres, film, thermoformed packaging and strapping. After sorting, cleaning and grinding, 'bottle flake' is obtained, which is then processed by either:
Polyglycolide or poly(glycolic acid) (PGA), also spelled as polyglycolic acid, is a biodegradable, thermoplastic polymer and the simplest linear, aliphatic polyester. It can be prepared starting from glycolic acid by means of polycondensation or ring-opening polymerization. PGA has been known since 1954 as a tough fiber-forming polymer. Owing to its hydrolytic instability, however, its use has initially been limited. Currently polyglycolide and its copolymers (poly(lactic-co-glycolic acid) with lactic acid, poly(glycolide-co-caprolactone) with ε-caprolactone and poly (glycolide-co-trimethylene carbonate) with trimethylene carbonate) are widely used as a material for the synthesis of absorbable sutures and are being evaluated in the biomedical field.
Low-density polyethylene (LDPE) is a thermoplastic made from the monomer ethylene. It was the first grade of polyethylene, produced in 1933 by Dr John C. Swallow and M.W Perrin who were working for Imperial Chemical Industries (ICI) using a high pressure process via free radical polymerization. Its manufacture employs the same method today. The EPA estimates 5.7% of LDPE is recycled in the United States. Despite competition from more modern polymers, LDPE continues to be an important plastic grade. In 2013 the worldwide LDPE market reached a volume of about US$33 billion.
Polyester is a category of polymers that contain one or two ester linkages in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.
Polytrimethylene terephthalate (PTT), is a polyester synthesized and patented in 1941. It is produced by a method called condensation polymerization or transesterification. The two monomer units used in producing this polymer are: 1,3-propanediol and terephthalic acid or dimethyl terephthalate. Similar to polyethylene terephthalate, the PTT is used to make carpet fibers.
In polymer chemistry photo-oxidation is the degradation of a polymer surface due to the combined action of light and oxygen. It is the most significant factor in the weathering of plastics. Photo-oxidation causes the polymer chains to break, resulting in the material becoming increasingly brittle. This leads to mechanical failure and, at an advanced stage, the formation of microplastics. In textiles the process is called phototendering.
Cyclohexanedimethanol (CHDM) is a mixture of isomeric organic compounds with formula C6H10(CH2OH)2. It is a colorless low-melting solid used in the production of polyester resins. Commercial samples consist of a mixture of cis and trans isomers. It is a di-substituted derivative of cyclohexane and is classified as a diol, meaning that it has two OH functional groups. Commercial CHDM typically has a cis/trans ratio of 30:70.
2,6-Dimethylnaphthalene (2,6-DMN) is a polycyclic aromatic hydrocarbon. It is one of the ten dimethylnaphthalene isomers, which are derived from naphthalene by the addition of two methyl groups.
2,6-Naphthalenedicarboxylic acid is an organic compound with the formula C10H6(CO2H)2. This colorless solid is one of several isomers of naphthalenedicarboxylic acid. It is a precursor to the high performance polyester polyethylene naphthalate (PEN, poly(ethylene-2,6-naphthalene dicarboxylate)). It is also used in the synthesis of some metal-organic frameworks.
Ideonella sakaiensis is a bacterium from the genus Ideonella and family Comamonadaceae capable of breaking down and consuming the plastic polyethylene terephthalate (PET) using it as both a carbon and energy source. The bacterium was originally isolated from a sediment sample taken outside of a plastic bottle recycling facility in Sakai City, Japan.
Polyethylene furan-2,5-dicarboxylate, also named poly(ethylene furan-2,5-dicarboxylate), polyethylene furanoate and poly(ethylene furanoate) and generally abbreviated as PEF, is a polymer that can be produced by polycondensation or ring-opening polymerization of 2,5-furandicarboxylic acid (FDCA) and ethylene glycol. As an aromatic polyester from ethylene glycol it is a chemical analogue of polyethylene terephthalate (PET) and polyethylene naphthalate (PEN). PEF has been described in (patent) literature since 1951, but has gained renewed attention since the US department of energy proclaimed its building block, FDCA, as a potential bio-based replacement for purified terephthalic acid (PTA) in 2004.
PETases are an esterase class of enzymes that catalyze the breakdown (via hydrolysis) of polyethylene terephthalate (PET) plastic to monomeric mono-2-hydroxyethyl terephthalate (MHET). The idealized chemical reaction is:
The enzyme MHETase is a hydrolase, which was discovered in 2016. It cleaves 2-hydroxyethyl terephthalic acid, the PET degradation product by PETase, to ethylene glycol and terephthalic acid. This pair of enzymes, PETase and MHETase, enable the bacterium Ideonella sakaiensis to live on the plastic PET as sole carbon source.
The methods for sequence analysis of synthetic polymers differ from the sequence analysis of biopolymers. Synthetic polymers are produced by chain-growth or step-growth polymerization and show thereby polydispersity, whereas biopolymers are synthesized by complex template-based mechanisms and are sequence-defined and monodisperse. Synthetic polymers are a mixture of macromolecules of different length and sequence and are analysed via statistical measures.
Plastic degradation in marine bacteria describes when certain pelagic bacteria break down polymers and use them as a primary source of carbon for energy. Polymers such as polyethylene (PE), polypropylene (PP), and polyethylene terephthalate (PET) are incredibly useful for their durability and relatively low cost of production, however it is their persistence and difficulty to be properly disposed of that is leading to pollution of the environment and disruption of natural processes. It is estimated that each year there are 9-14 million metric tons of plastic that are entering the ocean due to inefficient solutions for their disposal. The biochemical pathways that allow for certain microbes to break down these polymers into less harmful byproducts has been a topic of study to develop a suitable anti-pollutant.