Polyethylene terephthalate monomer

Condensation polymerization differs from addition polymerization in that the polymer is formed by reaction of monomers, each step in the process resulting in the elimination of some easily removed molecule (often water). E.g. the polyester polyethylene terephthalate (Terylene) is formed by the condensation polymerization (polycondensation) of ethylene glycol with terephthalic acid ... 

Those polymers which are the condensation product of two different monomers are named by applying the preceding rules to the repeat unit. For example, the polyester formed by the condensation of ethylene glycol and terephthalic acid is called poly(oxyethylene oxyterphthaloyl) according to the lUPAC system, as well as poly (ethylene terephthalate) or polyethylene terephthalate. 

Here the polymer grows by successive esterification with elimination of water and no termination step. Polymers formed by linking monomers with carboxylic acid groups and those that have alcohol groups are known as polyesters. Polymers of this type are widely used for the manufacture of artificial fibers. For example, the esterification of terephthalic acid with ethylene glycol produces polyethylene terephthalate. 

Polyethylene terephthalate also has the tendency, because it is produced by a condensation polymerization process, to depolymerize under high pressure and temperatures in the presence of water. Although this is usually a negative attribute, it can be utilized to regenerate pure monomers which can be repolymerized to make fresh polymer. This avoids the issues experienced by reprocessing resins, as the new resin has not experienced a previous heat history. A major drawback to this process is the requirement that the monomers used in polymerization processes must be highly pure, Unfortunately, this process is extremely costly and not performed on a commercial scale. 

Example PET. Let us consider polyethylene terephthalate) (PET, C oHK(h n, Ppet=1-35 g/cm3) of tpET =2 mm thickness and an X-radiation wavelength X= 0.15418 nm (CuKa). We set up a table with one row for each chemical element and sum both the masses and the mass absorption coefficients multiplied by the masses. After normalization to the molecular mass of the PET monomer, 192.17 amu, we find (p/p)pet = 1291.97/192.17 cm2/g a value 6.72 cm2/g. Considering the density ppet we find for the linear absorption coefficient Ppet =... 

Poly(trimethylene terephthalate) (PTT) is a newly commercialized aromatic polyester. Although available in commercial quantities only as recently as 1998 [1], it was one of the three high-melting-point aromatic polyesters first synthesized by Whinfield and Dickson [2] nearly 60 years ago. Two of these polyesters, polyethylene terephthalate) (PET) and poly(butylene terephthalate) (PBT), have become well-established high-volume polymers. PTT has remained an obscure polymer until recent times because one of its monomers, 1,3-propanediol (PDO), was not readily available. PDO was sold as a small-volume fine chemical at more than 10/lb., and was therefore not suitable as a raw material for commercial polymers. 

Claims of perpetual motion create moments of mirth and consternation for those knowledgeable in the laws of thermodynamics. Yet, is it only hyperbole when a responsible journal such as the European Plastics News [1] proclaims that depolymerization of polyethylene terephthalate (PET) can be repeated indefinitely The second law of thermodynamics brings us back to reality. The depolymerization of PET does not operate at 100% yields, but does offer the opportunity for near-stoichiometric recovery of the monomers used to make the polyester. With high yields of potentially valuable monomers, the commercial potential for polyester depolymerization to regain feedstocks must be considered. 

Monomers commonly used in the manufacture of polyethylene terephthalate (PET) and copolyesters for food packaging. 

For most step polymerizations, for example, in the synthesis of polyl hexamethylene adipa-mide) or polyethylene terephthalate), two reactants or monomers are used in the process, and the polymer obtained contains two different kinds of structures in the chain. This is not the case for chain polymerizations, where only one monomer need be used to produce a polymer. However, chain polymerizations can be carried out with mixtures of two monomers to form polymeric products wiht two different structures in the polymer chain. This type of chain polymerization process in which two monomers are simultaneously polymerized is termed a copolymerization, and the product is a copolymer. It is important to stress that the copolymer is not an alloy of two homopolymers hut contains units of both monomers incorporated into each copolymer molecule. The process can be depicted as... 

Polymerization of esters to produce polyesters is an important commercial process. Polyethylene terephthalate or PET is one of the most common plastics used in food containers (Table 15.4). This ester is formed by the reaction of ethylene glycol and terephthalic acid (Figure 15.17). PET and other polyesters consist of esters linked together. Notice that both terephthalic acid and ethylene glycol have two carboxyls and two hydroxyls, respectively. When a polyester such as PET is formed, a monomer con-... 

Table 7. Polymerization of vinyl monomers by vibromilling polyethylene terephthalate). Composition change with milling time (33)...

The same technique was applied to a mixture of polyethylene terephthalate and acrylic acid (34). The polymerizations were followed by looking at the acid number of the product the parameters studied were time, temperature, and monomer content see Fig.9a,b,c. The hydrophilicity, the solubility of the copolymer in benzyl alcohol, aniline, and a mixture of phenol and CHQ3 were increased by graft copolymerization. 

Fig. 9a-c. Polymerization of acrylic acid by vibromilling polyethylene terephthalate a) effect of milling time at 18° C on acid number of interpolymers b) effect of temperature after 3 h milling on interpolymer acid number c) monomer effect on interpolymer add number... 

Condensation monomers having the benzimidazolin-2-one ring system have found utility as modifiers in polyester synthesis. In particular, halogenated diols (73) and dicarboxylic acids (74) may be incorporated (78MI11100) into polyethylene terephthalate) or poly(butyl-ene terephthalate) at fairly low levels to impart flame retardancy. This can be accomplished without adverse effects upon other polymer properties. 

High speed stirring has be claimed by Nozaki for giving block copolymers from polymer-monomer mixtures (775). Among the polymers which have been subjected to such a degradation are addition polymers (polyvinyl chloride, polystyrene, polyacrylamide) as well as cellulose derivatives, phenol-formaldehyde linear condensation products and polyethylene terephthalate. 

Similarly the ozonization of several polyamides, mixed polyamides and polyethylene terephthalate followed by grafting of vinyl monomers has been successfully attempted (134, 135). 

Terephthalic acid (benzene 1,4-dicarboxylate, TPA) and isophthalic acid (benzene 1,3-dicarboxylate, IPA) are reactive bi-functional acids used as monomers to make plastics and coatings. TPA is a starting material for polyethylene terephthalate (PET). TPA and IPA are used to make polyester lacquers and coatings including the internal coatings of food cans. 

Condensation fibers such as nylon and polyethylene terephthalate are formed when two or more different monomers react, releasing small molecules such as water, and forming amide or ester bonds between the monomers. Nylon, first produced by DuPont in 1938, became a mainstay of the hosiery industry and is now the most widely used fiber in carpet manufacture. Polyethylene terephthalate, produced by formation of an ester bond between terephthalic acid and ethylene glycol, is by far the most widely used synthetic fiber. 

DuPont offers a family of biodegradable polymers based on polyethylene terephthalate (PET) technology known commercially as Biomax. Proprietary monomers are incorporated into the polymer, creating sites that are susceptible to hydrolysis. At elevated temperatures, the large polymer molecules are cleaved by moisture into smaller molecules, which are then consumed by naturally occurring microbes and converted to carbon dioxide, water and biomass. Biomax can be recycled, incinerated or landfilled, but is designed specifically for disposal by composting. 

Polyvinyl chloride and polyethylene terephthalate were re-cycled by Guffey [7] by heating to between 285°C and 360°C for 15 to 60 minutes to re-generate the corresponding monomers. 

In 2001 it was estimated that the world merchant market for catalysts was worth ca. US 25 billion, divided roughly equally between refining, petrochemicals, polymers, environmental (20-25% each) and with about 11% being used in fine chemicals. Refining is about the production of fuels (Chapter 3, Box 2), petrochemicals cover many of the basic commodity chemicals and the monomers required for the polymer industries fine chemicals include pharmaceuticals and agrochemicals, as well as flavours and fragrances and environmental is about exhaust gas and waste product clean-up. Vehicle catalytic converters use catalysts, as does the production of the main tonnage polymers polyethylene, polypropylene, polystyrene, polyvinyl chloride and polyethylene terephthalate. 

Acetic acid is used in the manufacture of a wide variety of products including adhesives, polyester fibres, plastics, paints, resins and solvents. About 40% of the acetic acid made industrially is used in the manufacture of vinyl acetate monomer for the plastics industry other large uses are to make cellulose acetate, a variety of acetate esters that are used as solvents, as well as monochloracetic acid, a pesticide. Acetic acid is also used as a solvent for the oxidation of p-xylene to terephthalic acid, a precursor to the important polyester, polyethylene terephthalate (PET). A minor, but important use is as non-brewed condiment, a vinegar substitute widely used in British fish and chip shops this is made using food-grade industrial acetic acid and is less expensive than fermentation vinegar. 

Polyethylene terephthalate (PET). At temperatnres above 300°C PET pyrolysis proceeds via a random-chain scission of the ester links to yield a mixture of terephthalic acid monomer and vinyl ester oligomers [47], The presence in the monomer of oxygen and a benzene ring imphes that the decomposition prodncts contain aromatic and oxygenated carbon componnds, like CO2, ketones and aldehydes [27],... 

A special case in terms of application of rotary kiln technology is the pyrolysis of mono fractions such as styrene, PMMA, polycarbonate, or polyethylene terephthalate. Polymethylmethacrylate is an example illustrate the advantages in using fluidized beds or rotary kilns. The feed material does not have a heteroatom problem and the pyrolysis product can easily be handled as a monomer source instead of feedstock. Therefore the... 

A monomer needed to synthesize polyethylene terephthalate (PET), a polymer used to make plastic sheeting and soft drink bottles (Section 22.16), shows a strong absorption in its IR spectrum at 1692 cm" and two singlets in its h NMR spectrum at 8.2 and 10.0 ppm. What is the structure of this monomer (molecular formula CsHeO ) ... 

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