Epoxidation epoxy resins

The commercial interest in epoxide (epoxy) resins was first made apparent by the publication of German Patent 676117 by I G Farben in 1939 which described liquid polyepoxides. In 1943 P. Castan filed US Patent 2 324483, covering the curing of the resins with dibasic acids. This important process was subsequently exploited by the Ciba Company. A later patent of Castan covered the hardening of epoxide resins with alkaline catalysts used in the range 0.1-5% This patent, however, became of somewhat restricted value as the important amine hardeners are usually used in quantities higher than 5%. 

Epoxides. Epoxy resins are more expensive than other equivalent theimosets (e.g. polyesters) but they an generally out-perform these materials due to better... 

In the system epoxide (epoxy resin) — anhydride, we can thus expect the presence of anhydride, epoxy- and proton donor groups. In their study of the reaction mechanism, Fisch and Hofmann 20 22-24) proposed a sequence of reactions leading to the crosslinking of epoxy resins or to the formation of linear polyesters. The first step is the reaction of the anhydride with hydroxyl groups giving a monoester (Eq.(l))... 

Trimethylolpropane epoxidation, epoxy resin precursors Peracetic acid... 

The main industrial uses of petoxycatboxyhc acids ate in the manufacture of epoxides, synthetic glycerol (qv), and epoxy resins (qv) (165,167,168). They also have been used as disinfectants (177), fungicides, and bleaching agents and for shrink-proofing wool (34). 

The majority of 2-methylphenol is used in the production of novolak phenoHc resins. High purity novolaks based on 2-methylphenol are used in photoresist appHcations (37). Novolaks based on 2-methylphenol are also epoxidized with epichlorohydrin, yielding epoxy resins after dehydrohalogenation, which are used as encapsulating resins in the electronics industry. Other uses of 2-methylphenol include its conversion to a dinitro compound, 4,6-dinitro-2-methylphenol [534-52-1] (DNOC), which is used as a herbicide (38). DNOC is also used to a limited extent as a polymerization inhibitor in the production of styrene, but this use is expected to decline because of concerns about the toxicity of the dinitro derivative. 

Epoxy Resins. Epoxy resins (qv) or polyether resins are thermosets used as the binder for terrazzo dooring. The epoxy resin often is made from epichlorohydrin and bisphenol A. An excess of epichlorohydrin is used to assure that the intermediate product contains terminal epoxide groups. 

The addition—reaction product of bisphenol A [80-05-07] and glycidyl methacrylate [106-91-2] is a compromise between epoxy and methacrylate resins (245). This BSI—GMA resin polymerizes through a free-radical induced covalent bonding of methacrylate rather than the epoxide reaction of epoxy resins (246). Mineral fillers coated with a silane coupling agent, which bond the powdered inorganic fillers chemically to the resin matrix, are incorporated into BSI—GMA monomer diluted with other methacrylate monomers to make it less viscous (245). A second monomer commonly used to make composites is urethane dimethacrylate [69766-88-7]. 

Specialty Epoxy Resins. In addition to bisphenol, other polyols such as aUphatic glycols and novolaks are used to produce specialty resins. Epoxy resins may also include compounds based on aUphatic, cycloaUphatic, aromatic, and heterocycHc backbones. Glycidylation of active hydrogen-containing stmctures with epichlorohydrin and epoxidation of olefins with peracetic acid remain the important commercial procedures for introducing the oxirane group into various precursors of epoxy resins. 

Cycloaliphatic Epoxy Resins. This family of aUphatic, low viscosity epoxy resins consists of two principal varieties, cycloolefins epoxidized with peracetic acid and diglycidyl esters of cycHc dicarboxyhc acids. 

The reactions of carboxyUc acids and anhydrides with epoxy resins have been extensively studied in a variety of investigations, particularly References 27—31. The general reaction of epoxide resins and anhydrides is... 

The epoxide resins (also widely known as epoxy resins and, occasionally, as ethoxyline resins) are characterised by the possession of more than one 1,2-epoxy group (I) per molecule. This group may lie within the body of the molecule but is usually terminal. 

The linear polymer formed is cured hy cross-linking either with an acid anhydride, which reacts with the -OH groups, or hy an amine, which opens the terminal epoxide rings. Cresols and other hisphenols are also used for producing epoxy resins. 

Epoxy resins have a wide range of molecular weights (=1,000-10,000). Those with higher molecular weights, termed phenoxy, are hydrolyzed to transparent resins that do not have the epoxide groups. These could he used in molding purposes, or crosslinked hy diisocyanates or hy cyclic anhydrides. 

For this use, the preferred powders are based on acrylic, epoxy or polyester and epoxy resins. For best colour, epoxy resins are crosslinked with anhydrides of dicarboxylic acids in the straight epoxy coatings, or with saturated polyesters of high acid content in the epoxy-polyester type. Acrylics contain epoxide rings via, for example, glycidyl methacrylate (CH2=C(CH3) —CO—O—CHj—CH —CH2), and these groups crosslink... 

Few non.chemists know exactly what an epoxide is. but practically everyone has used an "epoxy glue for household repairs or an epoxy resin for a protective coating. Epoxy resins and adhesives generally consist of two components that are mixed just prior to use. One component is a liquid "prepolymer/ and the second is a "curing agent" that reacts with the prepolymer and causes it to solidify. 

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