Bisphenol-A diglycidyl ether

Systematic name . 2,2 -[(1 -Methylethylidene)bis(4,1 -phcny Icncoxy methylene) bis-(oxirane) 

2 Structural and molecular formulae and relative molecular mass 

Pure ( analytical grade ) bisphenol A diglycidyl ether was tested in one experiment by skin application in CFl mice no epidermal, but a few dermal tumours were observed in males and there was a small increase in the incidence of lymphoreticular/haemato-poietic tumours in females (lARC, 1989). No subsequent studies were available to the Working Group. 

It was noted that glycidaldehyde, a metabolite of bisphenol A diglycidyl ether, is carcinogenic to experimental animals and classified as possibly carcinogenic to humans group 2B) (see this volume). 

Other Data Relevant to an Evaluation of Carcinogenicity and its Mechanisms 

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DGEBA. See Bisphenol A, diglycidyl ether. Bisphenol A, diglycidyl ether (DGEBA) [1675-54-3]... 

Bisphenol A diglycidyl ether [1675-54-3] reacts readily with methacrylic acid [71-49-4] in the presence of benzyl dimethyl amine catalyst to produce bisphenol epoxy dimethacrylate resins known commercially as vinyl esters. The resins display beneficial tensile properties that provide enhanced stmctural performance, especially in filament-wound glass-reinforced composites. The resins can be modified extensively to alter properties by extending the diepoxide with bisphenol A, phenol novolak, or carboxyl-terrninated mbbers. 

Comparable process techniques involving the reaction of bisphenol A diglycidyl ether with methacrylic acid produce the corresponding hydroxy... 

The term epoxy is familiar to nonchemists because of the widespread use of epoxy glues and resins. These are crosslinked polyether thermoplastics made from a liquid resin which is typically a mixture of bisphenol A diglycidyl ether (70) and a polymer (71 Scheme 86). The liquid resin is cured or hardened to the final resin by mixing with a crosslinking reagent, which can be an acid, a di- or poly-alcohol, or a di- or poly-amine (Scheme 86). 

Figure 14.4 Chemical structures of two common epoxy chain extenders for PET (a) a diepoxide, e.g. Shell Epon 828, based on bisphenol A diglycidyl ether (b) a tetraepoxide, e.g. Ciba MY721, based on tetraglycidyl diaminodiphenyl methane (TGDDM)...

Three groups of substances are regulated individually, i.e. vinyl chloride monomer in plastics (78/142/EEC), nitrosamines in rubber teats and soothers (93/11/EEC), and bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, and novolac glycidyl ethers in plastics and coatings (2002/16/EC). 

Figure 14.1 Structures of (a) bisphenol A, (b) bisphenol A diglycidyl ether, and (c) bisphenol F diglycidyl ether.

Hammarling, L., Gustavsson, H., Svensson, K. and Oskarsson, A. (2000). Migration of bisphenol-A diglycidyl ether (BADGE) and its reaction products in canned foods. Food Addit. Contam., 17, 11, 937 3. 

Bisphenol A diglycidyl ether (see also Glycidyl ethers) Bisulfites (see Sultiir dioxide and some sulfites, bisulfites and metabisulfites)... 

Preparation of a Cured Epoxy Resin by the Room Temperature Reaction of Bisphenol A Diglycidyl Ether with Polyamines... 

A luminescent unit was prepared by the Shinozaki et al. (1) by mixing iridium complexes, (I) and (II), with bisphenol A diglycidyl ether and 5-methylhexa-hydrophthalic anhydride. Additional luminescent derivatives, (III) and (IV), were prepared by Igarashi (2). 

BISPHENOL A DIGLYCIDYL ETHER Diglyddyl Ether, Blsphenol A-epIchlorohydrin Resin NL 1 1 2... 

As reported in numerous studies 61 -66), the reactivity of the glycidyl groups in Bisphenol A diglycidyl ether is virtually the same. At the same time, a small negative 54 61) or positive 51 substitution effect has been observed. However, in some other cases this effect can be substantial 20). 

Figure 1. Two possible routes of oxidative dealkylation of the glycidyl moiety of bisphenol A diglycidyl ether...

Bisphenol A diglycidyl ether is a contact allergen among people who have worked with low-molecular-weight epoxy resins (lARC, 1989). 

Bisphenol A diglycidyl ether has low oral and dermal lethal toxicity in rats and... 

Bisphenol A diglycidyl ether applied to the skin of pregnant rabbits had no effect upon fetal development (lARC, 1989). Daily oral administration by gavage during gestational days 6-15 of up to 640 mg/kg bw per day to rats and 1250 mg/kg bw per day to mice had no effect upon the incidence of malformations in either species. These maternally toxic doses produced fetal toxicity in mice, but not in rats (Morrissey et al., 1987). 

One study of workers exposed to bisphenol A diglycidyl ether showed no increase in chromosomal aberrations in peripheral blood lymphocytes (lARC, 1989). 

No epidemiological data relevant to the carcinogenicity of bisphenol A diglycidyl ether were available. 

Bisphenol A diglycidyl ether is not classifiable as to its carcinogenicity to humans... 

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