Polyester
3508478
226071661
2008-07-16T18:26:01Z
ChemGardener
423122
polyester doesn't have to be Terylene. Removed the aka which redirected to polyethylene terephthalate.
{{Cleanup|date=March 2008}}
{{For|the 1981 motion picture|Polyester (film)}}
[[Image:SEMexample.jpg|thumb|[[Scanning electron microscope|SEM]] picture of a bend in a high-surface area polyester [[fiber]] with a seven-lobed cross section]]
'''Polyester''' is a category of [[polymer]]s which contain the [[ester]] [[functional group]] in their main chain. Although there are many polyesters, the term "polyester" as a specific material most commonly refers to [[polyethylene terephthalate]] (PET). Polyesters include naturally-occurring chemicals, such as in the [[cutin]] of [[plant cuticle]]s, as well as [[synthetic]]s such as [[polycarbonate]] and [[polybutyrate]].
Polyesters may be produced in numerous forms such as fibers, sheets and three-dimensional shapes. Polyesters as [[thermoplastic]]s may change shape after the application of heat. While combustible at high temperatures, polyesters tend to shrink away from flames and self-extinguish upon ignition. Polyester fibers have high tenacity and E-modulus as well as low water absorption and minimal shrinkage in comparison with other industrial fibers.
==Applications==
Polyesters are the most widely used man-made fiber in the world. Woven polyester fabrics are used in consumer apparel and home furnishings such as bed sheets, bedspreads, curtains and draperies. Similarly, industrial polyesters are used in tyre reinforcements, ropes, fabrics for conveyor belts, safety belts, coated fabrics and plastic reinforcements with high [[energy absorption]]. Polyester fiberfills are also used to stuff pillows, comforters and cushion padding.
Polyester fabrics are claimed to have a "less natural" feel when compared to similarly-woven fabrics made from natural fibers (i.e. [[cotton]] in textile uses). However, polyester fabrics may exhibit other advantages over natural fabrics, such as improved wrinkle resistance. As a result, polyester fibers are sometimes spun together with natural fibers to produce a cloth with blended properties.
[[Image:Polyester Shirt, close-up.jpg|thumb|Close-up of a polyester shirt]]
Polyesters are also used to make bottles, films, [[tarpaulin]], canoes, [[liquid crystal display]]s, [[hologram]]s, [[filter (chemistry)|filter]]s, [[dielectric]] film for [[capacitor]]s, [[Electrical insulation|film insulation]] for [[wire]] and insulating tapes.
Liquid crystalline polyesters are among the first industrially-used liquid crystalline polymers. They are used for their mechanical properties and heat-resistance. These traits also important in their application as an abradable seal in jet engines.
[[Thermoset]]ting polyester are used as [[casting]] materials, [[fiberglass]] laminating resins, and non-metallic auto-body fillers. Fiberglass-reinforced, unsaturated polyesters find wide application in bodies of yachts and as body parts of cars.
Polyesters are also widely used as a finish on high-quality wood products such as [[guitar]]s, [[piano]]s and vehicle / yacht interiors. [[Burns London|Burns Guitars]], [[Rolls-Royce car|Rolls Royce]] and [[Sunseeker]] are a few companies that use polyesters to finish their products. [[Thixotropic]] properties of spray-applicable polyesters make them ideal for use on open-grain timbers, as they can quickly fill wood grain, with a high-build film thickness per coat. Cured polyesters can be sanded and polished to a high-gloss, durable finish.
==Polyester fiber properties==
===Mechanical properties===
'''Energy absorption of chemical fiber reinforced plastics''' (impact, bending and tensile tests)
Investigation of the practical requirements for measuring the energy absorption of composite materials, and development of a suitable method for carrying out such measurements. A number of dynamic testing methods for measuring the energy absorption of laminates are reviewed, including animpact bending test, repeated-impact tests, an impact tensile test, and a ram bending test. Also discussed are impact tests on plate laminates. Particular emphasis is placed in these studies on composites with a chemical fiber reinforcement. It is established that a relation exists between the quasi-static energy absorption of the fibers and the dynamic energy absorption of the composite. Composites with commercial polyester and polyamide fibers lead to the highest energy absorptions, in which case the testing apparatus has a significant effect.
===Chemical properties===
==The polyester industry==
===Some basics===
To get an idea about coverage, importance and complexity of the polyester industry, some basic information about polyester or [[polyethylene terephthalate]] (PET) at first:
What is polyester?
Polyester is a synthetic polymer made of purified [[terephthalic acid]] (PTA) or its dimethyl ester [[dimethyl terephthalate]] (DMT) and mono[[ethylene glycol]] (MEG). It ranges after polyethylene and polypropylene at the third place in terms of market size.
The main raw materials are described as follows:
*'''Purified Terephthalic Acid – PTA – CAS-No.: 100-21-0'''
:Synonym: 1,4 Dibenzenedicarboxylic acid,
:Sum formula; C6H4(COOH)2 , mol weight: 166,13
*'''Dimethylterephthalate – DMT- CAS-No: 120-61-6'''
:Synonym: 1,4 Dibenzenedicarboxylic acid dimethyl ester
:Sum formula C6H4(COOCH3)2 , mol weight: 194,19
*'''Mono Ethylene Glycol – MEG – CAS No.: 107-21-1'''
:Synonym: 1,2 Ethanediol
:Sum formula: C2H6O2 , mol weight: 62,07
More information about polyester raw materials one can find for PTA <ref>[http://www.inchem.org/documents/sids/sids/100-21-0.pdf PTA<!-- Bot generated title -->]</ref>,DMT <ref>[http://www.inchem.org/documents/sids/sids/120616.pdf DMT<!-- Bot generated title -->]</ref> and MEG <ref> http://www.inchem.org/documents/pims/chemical/pim227.htm MEG<!-- Bot generated title -->]</ref>, at the webpage INCHEM "Chemical Safety Information from Intergovernmental Organizations".
To make finally a polymer of high molecular weight one needs a catalyst. The most common catalyst
is [[antimony trioxide]] (or antimony tri acetate)
'''Antimony trioxide – ATO – CAS-No.: 1309-64-4'''
Synonym: non, mol weight: 291,51
Sum formula: Sb2O3
In 2008 about 10 000 t Sb2O3 are used to produce around 49 Mio t polyethylene terephthalate.
Polyester is described as follows:
'''Polyethylene Terephthalate CAS-No.: 25038-59-9'''
Synonym / abbreviations: polyester, PET, PES
Sum Formula: H-[C10H8O4]-n=60-120 OH, mol unit weight: 192,17
What are the success factors of the unbroken capacity growth of polyethylene terephthalate?
*The relatively easy accessible raw materials PTA or DMT and MEG
*The very well understood and described simple chemical process of polyester synthesis
*The low toxicity level of all raw materials and side products during production and processing
*The possibility to produce PET in a closed loop at low emissions to the environment
*The outstanding mechanical and chemical properties of polyester
*The recycle ability
*The wide variety of intermediate and final products made of polyester
All these facts are making this polymer one of the key elements of our daily life.
In table 1 we see the estimated world polyester production for [[textile]] polyester, bottle polyester resin, film polyester mainly for [[packaging]] and specialty polyesters for engineering plastics, which are the main fields of application. According to this table, the world's total polyester production might exceed 50 million tons per annum before the year 2010.
Table 1: World polyester production
{| class="wikitable"
|
! Market size per year
|-
| '''Product Type'''
| 2002 [Mio t/a]
| 2008 [Mio t/a]
|-
| Textile-PET
| 20
| 39
|-
| Resin, Bottle/A-PET
| 9
| 16
|-
| Film-PET
| 1.2
| 1.5
|-
| Special Polyester
| 1
| 2.5
|-
| '''TOTAL'''
| 31.2
| 49
|}
With its production volume and product diversity, polyester ranges after [[polyethylene]] (33.5%), [[polypropylene]] (19,5%) with a market share of about 18% in third position among all plastic materials produced worldwide.
The polyester production chain, and the relative polyester industry chain, will now be explained in greater detail and step by step.
===Raw material producer===
The raw materials PTA, DMT and MEG are mainly produced by large chemical companies which are sometimes integrated down to the crude oil refinery where p-xylene is the base material to produce PTA and [[liquefied petroleum gas]] (LPG) is the base material to produce MEG.
Large PTA producers are for instance BP, Reliance, Sinopec, SK-Chemicals, Mitsui and Eastman Chemicals. MEG production is in the hand of about 10 global players which are headed by MEGlobal a JV of DOW and PIC Kuweit followed by Sabic.
Let us assume the average production capacity of a single polyester plant is about 200 t/day: we are talking about nearly 500 polyester plants around the globe. Adding to this figure the continuously-growing polyester recycling industry, which is estimated to have processed about 3 million t polyester waste in 2007 alone (5 million T/a in 2010 estimated) and where each plant produces on average about 10 000 t/a, we have another 500 plants. This is 1000 polyester production plants, all needing specific and polyester-dedicated engineering and equipment, machinery, process technology and know-how, producing, processing and recycling polyester.
Among the world's largest polyester producers are the following companies:
Artenius, Advansa, DAK, DuPont, Eastman/Voridian, Hyosung, Huvis, Indorama, Invista, Jiangsu Sanfangxian, M&G Group, Mitsui, Mitsubishi, NanYa Plastics,Reichhold, Reliance, Rongsheng, Sabic, Teijin, Toray, Tonkun, Tuntex, Wellman, Yizheng Sinopec and Sanfanxiang.
One should notice that China's capacity to produce and process polyester in more than 500 plants is nearly half that of the world's polyester capacity meanwhile. More information about polyester in China can be found under the web site of China Chemical Fiber Economic Information Network <ref>[http://www.ccfei.net China Chemical Fiber Economic Information Network<!-- Bot generated title -->]</ref>.
===Polyester processing===
After the first stage of polymer production in the melt phase, the product stream divides into two different application areas which are mainly textile applications and packaging applications. In figure 2 the main applications of textile and packaging polyester are listed.
Table 2: Textile and packaging polyester application list
{| class="wikitable"
|-
! POLYESTER-BASED POLYMER (MELT or PELLETS)
|-
| '''[[Textile]]'''
| '''[[Packaging]]'''
|-
| Staple fiber (PSF)
| Bottles for CSD, Water, Beer, Juice, Detergents
|-
| Filaments POY, DTY, FDY
| A-PET Film
|-
| Technical yarn and tire cord
| Thermoforming
|-
| Non-woven and spunbond
| BO-PET Biaxial oriented Film
|-
| Mono-filament
| Strapping
|}
Abbreviations:
PSF = Polyester Staple Fiber;
POY = Partially Oriented Yarn;
DTY = Draw Textured Yarn;
FDY = Fully Drawn Yarn;
CSD = Carbonated Soft Drink;
A-PET = Amorphous Polyester Film;
BO-PET = Biaxial Oriented Polyester Film;
A comparable small market segment (<< 1 million t/a) of polyester is used to produce engineering plastics and masterbatch.
In order to produce the polyester melt with a high efficiency, high-output processing steps like staple fiber (50–300 t/d per spinning line) or POY /FDY (up to 600 t/d split into about 10 spinning machines) are meanwhile more and more horizontal, integrated, direct processes. This means the polymer melt is directly converted into the textile fibers or filaments without the common step of pelletizing. We are talking about full horizontal integration when polyester is produced at one site starting from crude oil or distillation products in the chain oil -> benzene -> PX -> PTA -> PET melt -> fiber / filament or bottle-grade resin. Such integrated processes are meanwhile established in more or less interrupted processes at one production site. Eastman Chemicals introduced at first the idea to close the chain from PX to PET resin with their so-called INTEGREX® process. The capacity of such horizontal, integrated productions sites is >1000 t/d and can easily reach 2500 t/d.
Besides the above mentioned large processing units to produce staple fiber or yarns, there are ten thousands of small and very small processing plants, so that one can estimate that polyester is processed and recycled in more than 10 000 plants around the globe. This is without counting all the companies involved in the supply industry, beginning with engineering and processing machines and ending with special additives, stabilizers and colors. This is a gigantic industry complex and it is still growing by 4–8% per annum, depending on the world region. Useful information about the polyester industry can be found under <ref>[http://www.ce-pip.com Chemical Engineering – Polyester Information Platform<!-- Bot generated title -->]</ref> where a “Who is Producing What in the Polyester Industry” is gradually being developed.
==Synthesis==
Synthesis of polyesters is generally achieved by a polycondensation reaction. See "[[condensation reaction]]s in polymer chemistry".
The General equation for the reaction of a diol with a diacid is :
(n+1) R(OH)<sub>2</sub> + n R´(COOH)<sub>2</sub> ---> HO[ROOCR´COO]<sub>n</sub>ROH + 2n H<sub>2</sub>O
===Azeotrope esterification===
In this classical method, an [[alcohol]] and a [[carboxylic acid]] react to form a carboxylic ester.
To assemble a polymer, the water formed by the reaction must be continually removed by [[azeotrope]] distillation.
===Alcoholic transesterification===
''See main article on [[transesterification]].''
{|
|- style="vertical-align:center;"
|
O
\\
C - O<font color="#ff0000">CH<sub>3</sub></font> + <font color="#00c000">OH</font>[Oligomer2]
/
[Oligomer1]
| <math>\leftrightarrow</math>
|
O
\\
C - O[Oligomer2] + <font color="#ff0000">CH<sub>3</sub></font><font color="#00c000">OH</font>
/
[Oligomer1]
|- style="text-align:center;"
| (ester-terminated oligomer + alcohol-terminated oligomer)
|
| (larger oligomer + methanol)
|}
===Acylation (HCl method)===
The acid begins as an acid chloride, and thus the polycondensation proceeds with emission of [[hydrochloric acid]] (HCl) instead of water. This method can be carried out in solution or as an [[vitreous enamel|enamel]].
:'''Silyl method'''
:In this variant of the HCl method, the carboxylic acid chloride is converted with the trimethyl silyl ether of the alcohol component and production of trimethyl silyl chloride is obtained
===Acetate method (esterification)===
:'''Silyl acetate method '''
===Ring-opening polymerization===
[[Aliphatic]] polyesters can be assembled from [[lactone]]s under very mild conditions, catalyzed [[anionic]]ally, [[cationic]]ally or [[metallorganic]]ally.
===Thermosetting===
Thermosetting [[resin]]s are generally copolymers of unsaturated polyesters with [[styrene]]. Polyester saturation is governed through the use of [[maleic acid]] or [[fumaric acid]]. In [[vinyl ester]]s, saturation (or lack thereof) is found in the alcohol group of the polyester. The double bond of unsaturated polyester reacts with styrene resulting in a 3-D cross-linked structure. This structure acts as a thermoset. The [[cross-link]]ing is initiated through an [[exothermic]] reaction involving an [[organic peroxide]], such as [[methyl ethyl ketone peroxide]] or [[benzoyl peroxide]].
==References==
*''Textiles'', by Sara Kadolph and Anna Langford. 8th Edition, 1998.
{{reference list}}
{{Plastics}}
{{fibers}}
==External links==
*[http://www.ce-pip.com/search.php Chemical Engineering - Polyester Information Platform]
[[Category:Carboxylate esters]]
[[Category:Packaging materials]]
[[Category:Plastics]]
[[Category:Polyesters| ]]
[[Category:Synthetic resins]]
[[Category:Synthetic fibers]]
[[Category:Thermoplastics]]
[[Category:Dielectrics]]
[[Category:Airship technology]]
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