Triglycidyl p-aminophenol

Figure 12.5 shows an example of the cured structure of a thermoset resin using two different epoxide monomers with two different amine hardeners. The epoxies are triglycidyl p-aminophenol (TGAP) and tetraglycidyl 4,4-diaminodiphenylmethane (TGDDM), which are tri- and tetra-fiinctional, respectively (n = 3 and n = 4, respectively) and the two hardeners are 4,4-diamino-diphenylsulphone (DDS) and dicyandiamide (DICY). 

Dow developed the phenol novolac epoxy resins, Shell introduced polyglycidyl ethers of tetrafunctional phenols, and Union Carbide developed a triglycidyl p-aminophenol resin. These products continue to find uses today in highly demanding applications such as semiconductor encapsulants and aerospace composites where their performance justifies their higher costs relative to bisphenol A based epoxies. 

Epoxy resins derived from multifunctional aromatic glycidyl amine resins such as triglycidyl-p-aminophenol and tetraglycidyl-4,4 -diaminodiphenylmethane have excellent properties at elevated temperatures ... 

An interesting anhydride-cured composition was reported, where 3,3, 4,4 -benzophenone tetracarboxylic dianhydride (BDTA) was found to form a liquid solution with triglycidyl p-aminophenol (TGpAP) that cured at room temperature to give a product with good high-temperature properties. 

Epichlorohydrin is reacted with a variety of hydroxy, carboxy, and amino compounds to form monomers with two or more epoxide groups, and these monomers are then used in the reaction with bisphenol A [Lohse, 1987]. Examples are the diglycidyl derivative of cyclohex-ane-l,2-dicarboxylic acid, the triglycidyl derivatives of p-aminophenol and cyanuric acid, and the polyglycidyl derivative of phenolic prepolymers. Epoxidized diolefins are also employed (Sec. 9-8). 

Triglycidyl Ether of p-Aminophenol. The triglycidyl derivative of p-aminophenol was originally developed by Union Carbide (58) and is currently marketed by Huntsman under the designation MY 0500 and 0510. Epoxidation of p-aminophenol is carried out with a large excess of epichlorohydrin under carefiilly controlled conditions, since the triglycidylated resin exhibits limited thermal stability and polymerizes vigorously under the influence of its tertiary amine moiety. 

The effect of chain scissions is thus an increasing function of Tg. Let us consider, for instance, an epoxy network based on the triglycidyl derivative of p-aminophenol (TGAP) cross-linked by diaminodiphenylmethane (DDM) in stoichiometric proportion. The characteristics are (Pascault etal., 2002) Tg = 494 K, F = 23 g.mol", Tgi = 293 K and j = 3 (trifunctional cross-links). Then, it follows that ... 

Union Carbide Corporation in the late 1950s (9) developed the triglycidyl derivative cf p-aminophenol and the technology was later sold to CIBA Products Ccmpany (now CIBA-GEIGY). 

Table 10.6 Comparison of some stoichiometric, fully cured epoxide-amine networks Tg, glass transition temperature [Ar], aromatic group concentration F, flex parameter (see text) n, crosslink density and [OH], hydroxyl concentration. Note DGEBD = diglycidyl ether of butane diol DGEBA = diglycidyl ether of bisphenol A (i = degree of polymerization) and TGAP = triglycidyl derivative of p-aminophenol ...

Triglycidylp-AminophenoI DerivedResins. Resins derived from triglycidyl -aminophenol [5026-74-7] originally developed by Union Carbide Corp. (7) are currendy marketed by CIBA-GEIGY. Synthesis is conducted by reaction of epichlorohydrin with the phenoHc and amino groups followed by dehydrohalogenation. The product is a viscous Hquid (1.5-5 Pa-s (15—50 P) at 25 C) which is considerably more reactive toward amines than standard bisphenol A-derived resins. The epoxy equivalent weight is 105—114. 

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