Phthalic anhydride polyester resin

Resins used were two types of epoxy resins cured with anhydride and amine and iso-phthalic type polyester resin. 

Polyesters [2] find use in fibers [poly(ethylene terephthalate), poly(ethylene oxybenzoate), poly(ester ethers), poly(ester amides), etc.] [1], coatings (especially unsaturated polyesters) [4], plasticizers, adhesives, polyurethane base resins, films, etc. Cross-linked polyesters prepared from glycerol and phthalic anhydride (alkyd resins) have been reviewed [20], High-melting poly aryl esters have been investigated for high-temperature applications. 

Dicyclopentadiene-based polyester resins have several advantages over the conventional polyester resins based on phthahc anhydride. Besides the lower cost of the DCPD, low cost glycols like ethylene glycol can be used instead of the more expensive propylene glycol. Since the DCPD-based resins require less styrene than the phthalic anhydride based resin, there is less styrene emission in the production and processing of the DCPD-based resins. 

Most naphthalene produced is utilized in the manufacture of phthalic anhydride, for plasticizers, alkyd resins and polyesters. It is also used in the manufacture of 2-naphlhol and insecticides. Naphthalene derivatives are of importance, particularly as dyestufT intermediates. 

Used as fibres, particularly in textiles and film. Many other polyester polymers are of importance, e.g. unsaturated polyester resins from phthalic anhydride, propylene glycol and maleic anhydride used with reinforcement in boats, cars, etc. (alkyd resins). U.S. production 1983 1-7 megatonnes. 

Tetrachlorphthalic Anhydride and Tetrachlorphthalic Acid. Tetrachlorphthalic anhydride [117-08-8] (TCPA) is manufactured by the ferric chloride catalyzed chlorination of phthalic anhydride. The relatively low chlorine content and the lower flame retardant efficiency of the aromatic chlorides limit use to unsaturated polyester resin formulations that do not requite a high degree of flame retardancy. 

Chlorendic Acid. Chlorendic acid [115-28-6] and its anhydride [115-27-5] are widely used flame retardants. Chlorendic acid is synthesized by a Diels-Alder reaction of maleic anhydride and hexachlorocyclopentadiene (see CyclopentadlENE and dicyclopentadiente) in toluene followed by hydrolysis of the anhydride using aqueous base (60). The anhydride can be isolated directly from the reaction mixture or can be prepared in a very pure form by dehydration of the acid. The principal use of chlorendic anhydride and chlorendic acid has been in the manufacture of unsaturated polyester resins. Because the esterification rate of chlorendic anhydride is similar to that of phthalic anhydride, it can be used in place of phthalic anhydride in commercial polyester... 

The main uses of toluene are as a solvent in paints, rubber, and plastic cements and as a feedstock in the manufacture of organic chemicals, explosives, detergents, and polyurethane foams. Xylenes (which exist as three isomers) are used in the manufacture of DMT, alkyd resins, and plasticizers. Naphthalene is mainly used in the manufacture of dyes, pharmaceuticals, insect repellents, and phthalic anhydride (used in the manufacture of alkyd resins, plasticizers, and polyester). 

The largest user of phenol in the form of thermosetting resins is the plastics industry. Phenol is also used as a solvent and in the manufacture of intermediates for pesticides, pharmaceuticals, and dyestuffs. Styrene is used in the manufacture of synthetic rubber and polystyrene resins. Phthalic anhydride is used in the manufacture of DMT, alkyd resins, and plasticizers such as phthalates. Maleic anhydride is used in the manufacture of polyesters and, to some extent, for alkyd resins. Minor uses include the manufacture of malathion and soil conditioners. Nitrobenzene is used in the manufacture of aniline, benzidine, and dyestuffs and as a solvent in polishes. Aniline is used in the manufacture of dyes, including azo dyes, and rubber chemicals such as vulcanization accelerators and antioxidants. 

High purity orthoxylene is used almost solely in the manufacture of phthalic anhydride. The anhydride is an intermediate for the manufacture of plasticizers, alkyd resins, polyester resins and other derivatives, such as phenolphthalein. 

Phthalic anhydride is also used to make polyester and alkyd resins. It is a precursor for phthalonitrile by an ammoxidation route used to produce phthalamide and phathilimide. The reaction scheme for producing phthalonitrile, phthalamide, and phathilimide is shown in Figure 10-17. ... 

Phthalic anhydride, a polyol, and an unsaturated fatty acid are usually copolymerized to unsaturated polyesters for coating purposes. Many other combinations in variable ratios are possible for preparing these resins. The 1998 U.S. production of polyesters was approximately 1.7 billion pounds. 

Alkyd resin synthesis. This synthesis consists of two steps. In the first step, a triglyceride oil is reacted at ca. 250°C with polyols, such as glycerol or pentaery-thritol, in tire presence of a basic catalyst to form a monoglyceride. In the second step, phthalic anhydride, with or without another dibasic acid such as maleic anhydride, is added to the reaction medium and reacted at high temperature. The resulting product is a branched polyester (Scheme 2.56). 

Chemoenzymatic synthesis of alkyds (oil-based polyester resins) was demonstrated. PPL-catalyzed transesterification of triglycerides with an excess of 1,4-cyclohexanedimethanol mainly produced 2-monoglycerides, followed by thermal polymerization with phthalic anhydride to give the alkyd resins with molecular weight of several thousands. The reaction of the enzymatically obtained alcoholysis product with toluene diisocyanate produced the alkyd-urethane. 

Smith condensed phthalic anhydride with glycerol in 1901 to prepare a glassy brittle material. Kienle in 1924 started investigating these resins and called them alkyds, He modified the polyesters with drying oils. By this modification they become soluble, on exposure to oxygen rapid cross-linking occurs and... 

Mixed xylenes are used as an octane improver in gasoline and for commercial solvents, particularly in industrial cleaning operations. By far, most of the commercial activity is with the individual isomers. Para-xylene, the most important, is principally used in the manufacture of terephthalic acid and dimethyl terephthalate en route to polyester plastics and fibers (Dacron, films such as Mylar, and fabricated products such as PET plastic bottles). Ortho-xylene is used to make phthalic anhydride, which in turn is used to make polyester, alkyd resins, and PVC plasticizers. Meta-xylene is used to a limited extent to make isophthahc acid, a monomer used in making thermally stable polyimide, polyester, and alkyd resins. 

Applications. Phthalic anhydride is used largely to make plasticizer for polyvinyl chloride. It is also a feed for alkyd resins and. for unsaturated polyesters that are widely used in construction, rharine, and synthetic marble applications. Other minor applications are dyes, esters, drying oil modifiers and pharmaceutical intermediates. 

The phthalic acids are made by oxidation of the corresponding xylene isomer. They are used to make plasticizers and alkyd and polyester resins and fibers. Ortho-phthalic acid usually is not isolated because it loses a molecule of water so easily, forming phthalic anhydride, the commercially traded form of this strain of phthalic acid. 

Resins used were two types of epoxy resins (EP) and an unsaturated polyester resin (UP) as shown in Figure 1. EP is the bis-phenol-A type resin cured with methyl-tetrahydrophthalic anhydride (MTHPA) or 1,8-p-menthandiamine (MDA). UP is the iso-phthalic type resin which has ester bonds in the main chain and is crosslinked by styrene (10). 

The uses of phthalic anhydride include plasticizers (53%), unsaturated polyester resins (22%), and alkyd resins (15%). 

An unsaturated polyester resin consists of a linear polyester whose chain contains double bonds and an unsaturated monomer such as styrene that copolymerizes with the polyester to provide a cross-linked product. The most common unsaturated polyester is made by step growth polymerization of propylene glycol with phthalic and maleic anhydrides. Subsequent treatment with styrene and a peroxide catalyst leads to a solid, infusible thermoset. 

This is a very broad class of compounds commonly used in coatings. Over 400-500 different alkyd resins are commercially available. They are polyesters containing unsaturation that can be cross-linked in the presence of an initiator known traditionally as a drier. A common example is the alkyd formed from phthalic anhydride and a glyceride of linolenic acid obtained from various plants. Cross-linking of the multiple bonds in the long unsaturated chain R produces the thermoset polymer by linking R groups of separate molecules with each other. 

Unsaturated polyesters have been produced from reaction of ethylene glycol with phthalic anhydride, or maleic anhydride (structure 4.46). These polyesters may be dissolved in organic solvents and used as cross-linking resins for the production of fibrous glass-reinforced composites ... 

Maleic anhydride (2,5-furandione) is obtained as a by-product in the production of phthalic anhydride and by the vapor phase oxidation of butylene or crotonaldehyde. It is also obtained by the dehydration of maleic acid and by the oxidation of benzene. Maleic anhydride is used for the production of unsaturated polyester resin. This reactant, like most reactants, is fairly toxic and should be treated as such. 

The use of triols or tricarboxylic acids leads to cross-linked or network polyesters. For example, an alkyd resin is formed by the reaction of glycerol with phthalic anhydride [19]. 

The major uses of mixed xylene are in aviation gasoline and protective coatings, and as a solvent for alkyd resins, lacquers, enamels and rubber cements. wetrr-Xylene is used as a solvent, as an intermediate for dyes and organic synthesis, especially isophthalic acid and insecticides, and in aviation fuel or// o-xylene is used in manufacture of phthalic anhydride, vitamin and pharmaceutical synthesis, dyes, insecticides, motor fuels para-xylene is used in synthesis of terephthalic acid for polyester resins and fibres, vitamin and pharmaceutical syntheses, and insecticides (Lewis, 1993). 

Polyester resins can also be rapidly formed by the reaction of propylene oxide (5) with phthalic and maleic anhydride. The reaction is initiated with a small fraction of glycol initiator containing a basic catalyst such as lithium carbonate. Molecular weight development is controlled by the concentration of initiator, and the highly exothermic reaction proceeds without the evolution of any condensate water. Although this technique provides many process benefits, the low extent of maleate isomerization achieved during the rapid formation of the polymer limits the reactivity and ultimate performance of these resins. 

Dicylopentadiene Resins. Dicyclopentadiene (DCPD) can be used as a reactive component in polyester resins in two distinct reactions with maleic anhydride (7). The addition reaction of maleic anhydride in the presence of an equivalent of water produces a dicyclopentadiene acid maleate that can condense with ethylene or diethylene glycol to form low molecular weight, highly reactive resins. These resins, introduced commercially in 1980, have largely displaced 0 0-phthalic resins in marine applications because of beneficial shrinkage properties that reduce surface profile. The inherent low viscosity of these polymers also allows for the use of high levels of fillers, such as alumina trihydrate, to extend the resin-enhancing, flame-retardant properties for application in bathtub products (Table 4). 

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