Bisphenol A Fumarate Polyesters

Polyester ICI Americas (Atlac 382-05 AC) PE Bisphenol A-Fumarate Polyester + 1% CoNap + DMA 50% Styrene MEKP 100 2 6-12 152-305... 

Standard bisphenol-A fumarate resins are derived from the propylene glycol or oxide diether of bisphenol-A and fumaric acid. The aromatic structure provided by the bisphenol-A provides several benefits. Thermal stability is improved, and the heat distortion point of the resin is mainly raised from the more rigid nature of the aromatic structure. The number of interior chain ester groups is reduced so the resistance to hydrolysis and saponification is increased. Bisphenol A fumarate polyesters have the best hydrolysis resistance of any commercial unsaturated polyester. 

Solvents such as benzene, carbon disulfide, ether, methyl ethyl ketone, toluene, xylene, trichloroethylene, and trichloroethane will attack the resin. Sulfuric acid above 70%, sodium hydroxide, and 30% chromic acid will also attack the resin. Refer to Table 3.8 for the compatibility of bisphenol-A fumarate polyester resin with selected corrodents. Table 3.9 lists the compatibility of hydrogenated bisphenol-A fumarate polyesters with selected corrodents. Reference [1] provides a more comprehensive listing. 

Compatibility of Bisphenol A-Fumarate Polyester with Selected Corrodents... 

Chem. Descrip. Bisphenol A fumarate polyester resin Uses Polyester for reinforced thermoset plastic equip, incl. filament wound and hand lay-up tanks, pipes, pumps, flooring, stacks, scrubber, equip, handling corrosives, and in fiberglass linings, coatings, and monolithic toppings... 

Polyesters, Although typically not as strong as the epoxies, polyesters offer good resistance to mineral acids, bleaching solutions, and salts. The most commonly used polyester resins for pipe are isophthalic polyesters and bisphenol A fumarate polyesters. Isophthalics have poorer resistance to caustics and oxidizers. Bisphenol A fumarates have improved resistance to these materials and are widely used in paper mills for bleach hues. 

Fig. 4.14 Penetration of sulfur from 25% H2SO4 into glass reinforced bisphenol-A fumarate polyester laminates, with and without surfacing mat. (Regester 1969)...

Isophthalic Bisphenol A fumarate Hydrogenated bisphenol A Halogenated polyester Terephthalate (PET)... 

Unsaturated polyesters are the most versatile class of thermosetting polymers. They are macromolecules made up of an unsaturated component, (i.e., maleic anhydride or its trans isomer, fumaric acid, which provides the sites for further reaction) and a saturated dibasic acid or anhydride with dihydric alcohols or oxides (typically phthalic anhydride which can be replaced by aliphatic acid, like adipic acid, for improved flexibility). If blends of phthalic anydride (or isophthalic acid) and maleic anhydride/fumaric acid are used, ortho (or iso) resins (Figure 6.18) are obtained. On the other hand, if propoxylated or ethoxylated bisphenol A is used with fumaric acid, bisphenol A fumarates are obtained, if a blend of chlorendic... 

A = bisphenol A epoxy—aliphatic amine hardener 1 -B = bisphenol A epoxy—aromatic amine hardener 1 -C = bisphenol F epoxy (epoxy novolac) 2-D = polyester resin—chlorendic acid type 2- E = polyester resin—bisphenol A fumarate type 3- F = vinyl ester resin 3-G = vinyl ester novolac resin ... 

The vinyl urethanes are normally derived from hydroxyl-terminated unsaturated polyester alkyds, e.g., propoxylated bisphenol A fumarate, which have been end-capped with a polyisocyanate and then subsequently end-capped with an hydroxy alkyl methacrylate. Thus, these resins have both terminal acrylic and in-chain maleate/fumarate unsaturation, the ratio depending on the oligomer molecular weight and the functionality of the polyisocyanate. High molecnlar weight results in a lower terminal in-chain unsaturation ratio, while a polyisocyanate fimctionality > 2 increases the ratio. A typical oligomer structure is shown in Structure 9.3 [13,14]. 

The chlorendic and bisphenol A fumarate resins offer improved chemical resistance over the isophthalics (see Table 10.1). The essentially neutral curing systems provide capability for application to concrete substrates. When properly formulated the polyester resins provide installation flexibility to a wide range of temperatures, humidity, and contaminants. 

Unsaturated polyester resins formulated with either carbon or silica fillers are used as polymer concretes. Bisphenol A fumarate resins and chlorendic acid resins are the two primarily used to formulate polyester concrete. Either resin can provide corrosion protection from normal atmospheric pollutants. Of the two, the chlorendic resins have a somewhat superior overall corrosion resistance (see Table 10.2). 

Vinyl Esters. These resins include chemical features of both epoxies aud polyesters. Vinyl ester resins offer better chemical resistance, somewhat higher temperature limits, aud better solvent resistance than ordinary polyesters but generally do not compare to epoxies in these properties. Vinyl ester resins are preferred over polyesters because they are more chemical-resistant than the isophthalics and less brittle than the bisphenol A fumarates. Typical services are in fertilizer plants (acid lines), chlorine plants (chlorine-saturated briue hues), and paper mills (caustic and black-hquor lines). 

HCR-197 is a chemical resistant polyester laminate produced by the match metal molding of fiberglass mat, inert fillers and ATLAC 382 resin. The ATLAC 382 system is bisphenol A fumarate resin. 

The most commonly used molecular ratios of unsaturated to saturated dicarbonic acid range from 1 1 to 3 1. An exception is the sole use of fumaric acid for the manufacturing of alkali resistant UP resins with bisphenol A. Hydrolyzed polyester as well as dicyclopentadienes are often used for cost reasons and require altered processing conditions due to their different reaction sequence. Both types of resin reach a level of hydrolysis resistance that is above that of UP standard resins. 

Other minor raw materials are used for specific needs. Fumaric acid [110-17-8], the geometric isomer of maleic acid, is selected to maximize thermal or corrosion performance and is the sole acid esterified with bisphenol A diol derivatives to obtain optimum polymer performance. Cycloaliphatics such as hydrogenated bisphenol A (HBPA) and cydohexanedimethanol (CHDM) are used in selective formulations for electrical applications. Tetrahydrophthalic anhydride [85-43-8] (THPA) can be used to improve resilience and impart useful air-drying properties to polyester resins intended for coating or lining applications. 

Bisphenol A Polyester A thermoset unsaturated polyester based on bisphenol A and fumaric acid. 

The uses of polyesters are many and varied and they have traditionally held a major part of the anticorrosion market in the broad sense. For corrosion-resistant chemical process equipment, more expensive and specialized polyesters are used. The acids are then generally isophthalic or fumaric acids, with the hydroxyl functionality being provided by neopentyl glycol or bisphenol A. 

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