385:
Tere resins, known as PET UPR resins, which are produced by catalytically cracking PET resin in the reactor to yield a mixture of terephthalic acid and ethylene glycol. Additional acids and glycols are then added along with maleic anhydride and a new polymer is produced. The end product is functionally the same as a Tere resin, but can often be lower cost to manufacture as scrap PET can be sourced cheaply. If a glycol-modified PET (PET-G) is used, exceptional properties can be imparted to the resin due to some of the exotic materials used in PET-G production. Tere and PET-UPR resins are used in many applications including cured-in-place pipe.
373:. This type of resin is known as a Nadic resin and is referred to as a poor man's Ortho, due to sharing many similar properties of an Ortho resin along with the extremely low cost of DCPD raw material. In another process, maleic anhydride is first opened with water or another alcohol to form maleic acid and is then reacted with DCPD where an alcohol from the maleic acid reacts across one of the double bonds of the DCPD. This product is then used to end-cap the UPR resin which yields a product with unsaturation on the end-groups. This type of resin is referred to as a DCPD resin.
298:
306:
314:
363:
catalysts, such as N,N-dimethylacetoacetamide (DMAA), are often employed in the synthesis process which converts the maleates into fumarates; the isomerization can also be encouraged with increased reaction time and temperature. Within the UPR industry, the classification of the resins is generally
384:
Tere resins are often used when high modulus and strength are desired, but the low color properties of an Iso resin is not necessary. Terephthalic acid is generally lower cost than isophthalic acid, but both give similar strength characteristics to a UPR product. There exists a special sub-set of
380:
Iso resins are generally on the higher end of UPR products, both because of the relatively higher cost of the isophthalic acid as well as the superior properties they possess. Iso resins are the primary type of resin used in gel coat applications, which is similar to a paint, but is sprayed into a
358:
In unsaturated polyester (UPR) chemistry, unsaturation sites are present along the chain, usually by incorporation of maleic anhydride, but maleic acid and fumaric acid are also used. Maleic acid and fumaric acid are isomers where maleic is the cis-isomer and fumaric is the trans-isomer. The ester
188:
to other unsaturated bonds in adjacent molecules, linking them in the process. Unsaturation is generally in the form of maleate and fumarate species along the polymer chain. Maleate/fumarate generally does not self-polymerize via radical reactions, but readily reacts with styrene. Maleic anhydride
635:
381:
mold before the FRP is molded leaving a coating on the part. Gel coat resins must have lower color (almost clear) so as to not impart additional color to the part or so that they can be dyed properly. Gel coats must also have strong resistance to UV-weathering and water blistering.
364:
based on the primary saturated acid. For example, a resin containing primarily terephthalic acid is known as a Tere resin, a resin containing primarily phthalic anhydride is known as an Ortho resin, and a resin containing primarily isophthalic acid is known as an Iso resin.
193:, and are in fact the textbook case of this phenomenon. This is one reason that styrene has been so hard to displace in the market as the industry standard reactive diluent for unsaturated polyester resins, despite increasing efforts to displace the material such as
351:, in which a difunctional (or higher order) acid or acyl halide is reacted with a difunctional (or higher order) alcohol. Polyesters are produced commercially both as saturated and unsaturated resins. The most common and highest volume produced polyester is
229:
exothermically. The use of excessive initiator especially with a catalyst present can, therefore, cause charring or even ignition during the curing process. Excessive catalyst may also cause the product to fracture or form a rubbery material.
205:
is a more appropriate term. Transition metal salts are usually added as a catalyst for the chain-growth crosslinking reaction, and in the industry this type of additive is known as a promoter; the promoter is generally understood to lower the
368:
is also a common UPR raw material, and can be incorporated two different ways. In one process, the DCPD is cracked in situ to form cyclopentadiene which can then be reacted with maleate/fumarate groups along the polymer chain via a
175:
is the most common diluent and the industry standard. The diluent allows control over the viscosity of the resin, and is also a participant in the curing reaction. The initially liquid resin is converted to a solid by
376:
Ortho resins comprise the most common type of UPR, and many are known as general purpose resins. FRP composites utilizing ortho resins are found in such application as boat hulls, bath ware, and bowling ball cores.
77:
applications. Departments of
Transportation in the USA also specify them for use as overlays on roads and bridges. In this application they are known AS Polyester Concrete Overlays (PCO). These are usually based on
98:
applications also prefer styrene free. Most polyester resins are viscous, pale coloured liquids consisting of a solution of a polyester in a reactive diluent which is usually styrene, but can also include
633:, Miller, Gregory C.; Moore, William & Kinnin, Lucian A. et al., "Non-leaching styrene-free cured-in-place pipe system suitable for potable water applications", issued 2021-12-09
355:, which is an example of a saturated polyester and finds utilization in such applications as fibers for clothing and carpet, food and liquid containers (such as a water/soda bottles), as well as films.
359:
forms of these two molecules are maleate and fumarate, respectively. When curing a UPR, the fumarate form is known to react more rapidly with the styrene radical, so
266:
233:
Unsaturated polyesters (UPR) are utilized in many different industrially relevant markets, but in general are used as the matrix material for various types of
73:(FRP)—are typically used in restaurants, kitchens, restrooms and other areas that require washable low-maintenance walls. They are also used extensively in
278:
269:. Wind turbine blades also use them as well as many more processes. UPRs are also used in non-reinforced applications with common examples being
210:
of the radical initiator. Cobalt salts are the most common type of promoter used. Common radical initiators used are organic peroxides such as
537:
131:
with multiple alcohol or hydroxy functional groups, with unsaturated and in some cases saturated dibasic acids. Typical polyols used are
197:. The initial free radicals are induced by adding a compound that easily decomposes into free radicals. This compound is known as the
274:
695:
347:
are a category of polymers in which ester functionality repeats within the main chain. Polyesters are a classic example of
598:
Joanna Klein
Nagelvoort (2009). "Resin Composition Suitable for (Re)Lining of Tubes, Tanks, and Vessels". EP 2097369 B1.
658:
393:
Lichens have been shown to deteriorate polyester resins, as can be seen in archaeological sites in the Roman city of
237:. Glass fiber-reinforced composites comprise the largest segment into which UPRs are used and can be processed via
880:
717:
262:
511:
194:
171:. Unsaturated polyesters are generally sold to parts manufacturers as a solution of resin in reactive diluent;
70:
215:
168:
630:
885:
352:
348:
94:
free systems mainly due to odor issues, but also over concerns that styrene is a potential carcinogen.
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616:
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50:
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54:
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reactions, is continuously removed by distillation, driving the reaction to completion via
164:
116:
8:
870:
330:
258:
250:
124:
74:
824:
333:, with water formed as the condensate by-product. An ester can also be produced with an
841:
808:
745:
234:
226:
190:
34:
809:"Microorganisms Attack Synthetic Polymers in Items Representing Our Cultural Heritage"
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and cut with styrene at high levels—usually up to 50%. Polyesters are also used in
79:
42:
38:
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136:
23:
675:
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185:
100:
95:
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The finished cure is most likely weaker than an equal amount of an epoxy resin
864:
741:
394:
360:
181:
148:
90:
based materials are also used. Many companies have and continue to introduce
62:
30:
850:
27:
832:
676:"Catalysts, Accelerators and Inhibitors for Unsaturated Polyester Resins"
490:
334:
83:
554:
246:
177:
66:
763:
470:
344:
305:
301:
Mechanism for the DMAA catalyzed isomerization of maleate to fumarate
222:
46:
806:
198:
104:
792:
Johan
Bjorksten; Henry Tovey; Betty Harker; James Henning (1956).
475:
447:
More difficult to mix than other resins, such as a two-part epoxy
441:
270:
172:
132:
91:
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The toxic nature of its fumes, and especially of its catalyst,
120:
65:. Wall panels fabricated from polyester resins reinforced with
337:
and an alcohol, in which case the condensate by-product is a
322:
87:
58:
41:
is a commonly used raw material with diacid functionality in
716:
Brøndsted, Povl; Lilholt, Hans; Lystrup, Aage (2005-08-04).
526:
451:
629:
418:
Polyesters can withstand a temperature up to 80 °C.
313:
715:
597:
555:"2K Polymer Systems Ltd: Bonded Anchors: P - Polyester"
424:
Relatively low shrinkage at between 4–8% during curing.
409:
Adequate resistance to water and variety of chemicals.
776:
682:, Dordrecht: Springer Netherlands, pp. 204–239,
674:
Weatherhead, R. G. (1980), Weatherhead, R. G. (ed.),
454:, pose a safety risk if proper protection isn't used
427:
Linear thermal expansion ranges from 100–200 x 10 K.
718:"Composite Materials for Wind Power Turbine Blades"
436:Polyester resin has the following disadvantages:
405:Polyester resin offers the following advantages:
862:
648:
807:Francesca Cappitelli; Claudia Sorlini (2008).
680:FRP Technology: Fibre Reinforced Resin Systems
421:Polyesters have good wetting to glass fibres.
412:Adequate resistance to weathering and ageing.
651:Industrial Plastics: Theory and Applications
673:
457:Not appropriate for bonding many substrates
325:is formed as the condensation product of a
184:at unsaturated bonds, which propagate in a
512:"Functional Polyester Resins for Coatings"
840:
509:
312:
304:
296:
110:
734:10.1146/annurev.matsci.35.100303.110641
538:"8-5 Overlays on Existing Bridge Decks"
863:
813:Applied and Environmental Microbiology
163:. Water, a condensation by-product of
722:Annual Review of Materials Research
649:Erik Lokensgard (19 January 2016).
13:
14:
897:
794:Polyesters and Their Applications
388:
180:chains. This is done by creating
431:
353:Polyethylene terephthalate (PET)
287:engineered stone/cultured marble
800:
785:
770:
756:
253:(known as relining in Europe),
777:Fred W. Billmeyer Jr. (1962).
764:"Trusted Solutions | AOC"
709:
667:
642:
623:
591:
571:
547:
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189:and styrene are known to form
45:polyester resins. Unsaturated
1:
510:Lewarchik, Ron (2022-09-14).
496:
400:
71:fiberglass reinforced plastic
688:10.1007/978-94-009-8721-0_10
292:
267:resin transfer molding (RTM)
216:methyl ethyl ketone peroxide
7:
779:Textbook of Polymer Science
516:Prospector Knowledge Center
464:
225:and, as with other resins,
195:California's Proposition 65
115:Unsaturated polyesters are
10:
902:
119:formed by the reaction of
26:formed by the reaction of
321:In organic chemistry, an
201:within the industry, but
147:; typical acids used are
481:Thermoset polymer matrix
366:Dicyclopentadiene (DCPD)
208:bond dissociation energy
169:Le Chatelier's principle
309:Example of a DCPD resin
51:sheet moulding compound
16:Type of synthetic resin
881:Thermosetting plastics
611:Cite journal requires
318:
310:
302:
191:alternating copolymers
55:bulk moulding compound
486:Thermosetting polymer
316:
308:
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221:Polyester resins are
117:condensation polymers
111:Unsaturated polyester
833:10.1128/AEM.01768-07
371:Diels-alder reaction
825:2008ApEnM..74..564C
349:step-growth polymer
251:cured-in-place pipe
125:polyhydric alcohols
75:cured-in-place pipe
49:resins are used in
35:polyhydric alcohols
579:"Polyester Resins"
319:
317:Example of a Nadic
311:
303:
279:bowling ball cores
886:Polymer chemistry
697:978-94-009-8721-0
273:, shirt buttons,
157:terephthalic acid
145:diethylene glycol
129:organic compounds
86:adhesives though
893:
876:Synthetic resins
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283:polymer concrete
263:spray-up molding
255:filament winding
212:benzoyl peroxide
161:maleic anhydride
153:isophthalic acid
141:propylene glycol
80:isophthalic acid
39:Maleic anhydride
24:synthetic resins
20:Polyester resins
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339:hydrogen halide
327:carboxylic acid
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137:ethylene glycol
123:(also known as
113:
17:
12:
11:
5:
899:
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728:(1): 505–538.
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660:978-1305855687
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613:|journal=
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389:Biodegradation
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259:vacuum molding
186:chain reaction
165:esterification
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96:Drinking water
63:laser printers
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432:Disadvantages
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395:Baelo Claudia
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361:isomerization
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223:thermosetting
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183:
182:free radicals
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178:cross-linking
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150:
149:phthalic acid
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101:vinyl toluene
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93:
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31:organic acids
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25:
21:
819:(3): 564–9.
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793:
787:
778:
772:
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721:
711:
701:, retrieved
679:
669:
650:
644:
625:
604:cite journal
593:
582:. Retrieved
573:
562:. Retrieved
559:www.2kps.net
558:
549:
532:
519:. Retrieved
515:
505:
435:
404:
392:
383:
379:
375:
357:
343:
320:
232:
220:
114:
103:and various
19:
18:
491:Vinyl ester
335:acyl halide
84:anchor bolt
69:—so-called
43:unsaturated
871:Polyesters
865:Categories
703:2021-05-15
584:2019-08-19
564:2018-04-05
521:2022-09-21
497:References
401:Advantages
345:Polyesters
275:mine-bolts
247:pultrusion
235:composites
135:including
67:fiberglass
742:1531-7331
471:Polyester
415:Low cost.
293:Chemistry
271:gel coats
203:initiator
105:acrylates
47:polyester
851:18065627
750:15095678
465:See also
199:catalyst
57:and the
842:2227722
821:Bibcode
476:Styrene
442:styrene
440:Strong
397:Spain.
331:alcohol
329:and an
173:styrene
133:glycols
121:polyols
92:styrene
28:dibasic
849:
839:
748:
740:
694:
657:
637:
285:, and
159:, and
143:, and
746:S2CID
541:(PDF)
444:odour
323:ester
88:epoxy
59:toner
847:PMID
738:ISSN
692:ISBN
655:ISBN
617:help
452:MEKP
227:cure
33:and
22:are
837:PMC
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243:BMC
239:SMC
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