Glycidyl amines

Aromatic and Heterocyclic Glycidyl Amine Resins. Among the specialty epoxy resins containing an aromatic amine backbone, the following are commercially significant. 

Resinous adducts, 10 394 Resinous odor, 3 229t Resins. See also Epoxy resins Lacquer resins Novolac resins Phenolic resins Resole resins Thermoplastic resins acidic cation-exchange, 12 191 advanced materials, 1 693 antilipemic agents, 5 141 aromatic glycidyl amine, 10 372—373 chromatographic, 14 383-384 for coatings, 7 95-107 derived from furfuryl alcohol, 12 271— 272... 

Glycidyl amine epoxy resins are reaction products of aromatic amines and epichlorohy-drin. They have high modulus and high glass transition temperature. These resins find use in aerospace composites and high-temperature adhesive formulations. 

The work described herein relates primarily to lamination and bonding processes. However, the techniques are generic to most forms of thermoset resin processing. In the discussion which follows many of the resin systems contain glycidyl amines. The bulk of the epoxy formulations used in the aerospace industry today are based on tetraglycidylmethylenedianiline, I (TGMDA) and with diaminodi phenylsulfone, II (DOS). Systems based on... 

More recently, trifunctional and tetrafunctional resins (Tactix 742, namely the triglycidyl ether of tn 5(hydroxyphenyl) methane, and Shell 1153, namely a diaryl-methylene-bridged DGEBA) have been trialled, but the alternative approach of curing glycidyl amine resins with aromatic amines has proven to be more widely employed to achieve high Tg. These resins were shown earlier in Scheme 1.4. 

High conversion of cycloahphatic epoxy groups in the triepoxide ACECs on curing with aromatic amines is noticeable. This phenomenon can be attributed to the catalytic effect of secondary hydroxyl groups being formed as a result of the glycidyl-amine addition as well as - to a lesser extent - the increase in reactivity as discussed above. All this secures an increased mechanical strength and heat resistance of cured ACECs (Table 9). 

Figure 6.17 Diglycidyl ether of bisphenol A (formula 1), an epoxidised novolak formula 2), TGMDA (formula 3) and new generation (aromatic and glycidyl ) amine resins (formulae 4 and 5)...

Another commercially important aromatic glycidyl amine resin is trigly-cidyl isocyanurate (TGIC), which is discussed in the Weatherable Epoxy Resins section. 

By reacting epichlorohydrin with aromatic diamines, it is possible to manufacture epoxy resins with higher functionality than DGEBA or DGEiBF resins. As shown in Fig. 5.9, the structure of tetraglycidyl methylene dianiline epoxy, the most important glycidyl amine, is characterized by four epoxy... 

Glycidyl amine resins are prepared hy reaction of epichlorhydrin with either primary diamines, monoamines or aminophenols. Each primary amine gives rise to two epoxide substituents. The reaction again involves two steps reaction of the epichlorhydrin with an active hydrogen to form the chlorohydrin, followed by ring closure with sodium hydroxide to generate the new epoxide. The common glycidyl amines are the reaction products of epichlorhydrin with diamino diphenyl methane and with p-aminophenol. 

Glycidyl amines have been prepared by the reaction of epichlorohydrin with aliphatic or aromatic amines followed by dehydrohalogenation [32], The aromatic glycidyl amines are much more stable on storage than the aliphatic types and can be cured with acid or anhydride curing agents to give resins. 

There are two main categories of epoxy resins glycidyl epoxy, and non-glycidyl epoxy. The former are further classified as glycidyl-ether, glycidyl-ester and glycidyl-amine. 

Multifunctional epoxy resins such as aromatic glycidyl ether resins and aromatic glycidyl amine resins are commercially available. Commercially important epoxy phenol Novolac resins and epoxy cresol Novolac resins are prepared from excess epichlohydrin and phenol-formaldehyde or o-cresol-formaldehyde resins. The high functionality of these Novolac resins increases crosslink density and improves thermal stability and chemical resistance ... 

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 ... 

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