Sensitizing capacity and cross‐reaction pattern of the isomers of diglycidyl ether of bisphenol F in the guinea pig

Pontén, Ann; Zimerson, Erik; Sörensen, Östen; Bruze, M.

doi:10.1034/j.1600-0536.2002.470507.x

Cited by 30 publications

(38 citation statements)

References 10 publications

(11 reference statements)

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“…Allergic reactions to DGEBA‐R and DGEBF‐R were observed most frequently, with a high degree of cross‐reactivity, almost exactly to the same extent as recently described by Pontén et al in their investigation of occupational contact allergies in a wind turbine rotor blade factory (9). The same authors have recently proven immunological cross‐reactivity between DGEBA and 2 isomers of DGEBF, namely p , p ′‐DGEBF and o , p ′‐DGEBF (8, 21, 22). Our patch test preparation was made from Epicote 862 ® , which, according to a chemical analysis performed at the Department of Dermatology in Malmö, contained 38% of p , p ′‐DGEBF, 36% of o , p ′‐DGEBF, 13% of o , o ′‐DGEBF and approximately 1% of DGEBA.…”

Section: Discussionmentioning

confidence: 93%

An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002

Geier

Lessmann

Hillen³

et al. 2004

Contact Dermatitis

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Epoxy resin systems (ERSs) are a frequent cause of occupational allergic contact dermatitis. Sensitization occurs not only to the resins, but also to hardeners and reactive diluents. However, only a fraction of the ERS components currently in use are available for patch testing. With the multicentre study EPOX 2002, we attempted to improve diagnostics in this field by patch testing with components currently used in ERSs. During the first study period (October 2002 to July 2003), in addition to commercially available ERS patch test substances, 16 study substances (1 resin, 9 hardeners and 6 reactive diluents) were patch tested in 70 patients with suspected contact allergy due to ERSs and 22 patients with a prior positive patch test reaction to epoxy resin (ER) in the standard series. Most frequently, allergic reactions to ER based on diglycidyl ether of bisphenol A and F were observed (55.2% and 43.7%, respectively). Agreement between positive reactions to both resins, which can be explained by immunological cross-sensitization and/or coexposure, was substantial [Cohen's kappa 0.65 (95% CI: 0.49-0.80)]. Among the reactive diluents, 1,6-hexanediol diglycidyl ether (1,6-HDDGE) and 1,4-butanediol diglycidyl ether (1,4-BDDGE) were the most frequent allergens, with 19.5% and 18.4% positive reactions, respectively. Although agreement between positive reactions to 1,6-HDDGE and 1,4-BDDGE was even better than with the 2 resins, the sample size is considered too small to decide reliably whether 1,6-HDDGE alone could serve as a marker allergen for both. Allergic reactions to p-tert-butylphenyl glycidyl ether and to phenyl glycidyl ether (PGE) occurred in 11.5% of the patients tested, with only moderate agreement. All patients positive to cresyl glycidyl ether (6.8%) also reacted to PGE. Of the hardeners tested, m-xylylene diamine was the most frequent allergen (13.8%), followed by isophorone diamine (5.7%). No reactions were observed to several substances, the test concentration of which may have been too low and will be increased in the future.

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Section: Discussionmentioning

confidence: 93%

An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002

Geier

Lessmann

Hillen³

et al. 2004

Contact Dermatitis

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“…10 Allergic contact dermatitis from various epoxy resin system components 6, 11-4 18 including DGEBA and DGEBF 5,19 has been reported. The skin sensitization potential has been investigated experimentally in vivo in mice and guinea pigs for DGEBA, 20,21 DGEBF, 21,22 PGE 23,24 and others. 25 DGEBA, DGEBF and PGE are strong sensitizers in both species according to regulatory classifications.…”

Section: Introductionmentioning

confidence: 99%

Analogues of the Epoxy Resin Monomer Diglycidyl Ether of Bisphenol F: Effects on Contact Allergenic Potency and Cytotoxicity

O’Boyle

Delaine

Luthman

et al. 2012

Chem. Res. Toxicol.

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Diglycidyl ethers of bisphenol A (DGEBA) and bisphenol F (DGEBF) are widely used as components in epoxy resin thermosetting products. They are known to cause occupational and non-occupational allergic contact dermatitis. The aim of this study is to investigate analogues of DGEBF with regard to contact allergy and cytotoxicity. A comprehensive knowledge of the structural features that contribute to the allergenic and cytotoxic effects of DGEBF will guide the development of future novel epoxy resin systems with reduced health hazards for those coming into contact with them. It was found that the allergenic effects of DGEBF were dependent on its terminal epoxide groups. In contrast, it was found that the cytotoxicity in monolayer cell culture was not only dependent on the presence of epoxide groups, but also on other structural features.

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“…24,25 Epoxy chemicals are also implicated in non-occupational contact allergy. 17,26 Skin sensitization potential has been investigated experimentally in vivo in mice and guinea pigs for DGEBA, 27,28 DGEBF 28,29 and others. 30,31 DGEBA and DGEBF are classified as strong sensitizers in both species according to regulatory guidelines.…”

Section: Introductionmentioning

confidence: 99%

Epoxy Resin Monomers with Reduced Skin Sensitizing Potency

O’Boyle

Niklasson

Tehrani‐Bagha

et al. 2014

Chem. Res. Toxicol.

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Epoxy resin monomers, including diglycidyl ethers of bisphenol A and F (DGEBA and DGEBF), are extensively used as building blocks for thermosetting polymers. However, they are known to cause widespread contact allergy. This research describes a number of alternative epoxy resin monomers, designed with the aim of reducing the skin sensitizing potency whilst maintaining the ability to form thermosetting polymers. The compounds were designed, synthesized, assessed for skin sensitizing potency using the in vivo murine local lymph node assay, and tested for technical applicability using thermogravimetric analysis and differential scanning calorimetry. All the novel epoxy resin monomers had decreased skin sensitization potencies compared to DGEBA and DGEBF. With respect to EC3 values, which is the estimated concentration of a substance required to induce a 3-fold increase in sensitization compared to a control, the best of the new monomers had a value approximately 2.5 times higher than those of DGEBA and DGEBF. The diepoxides were reacted with triethylenetetramine and four out of the six novel monomers gave polymers with a thermal stability comparable to that obtained with DGEBA and DGEBF. The new epoxy resin monomers have the potential to replace DGEBA and DGEBF, leading to a decreased incidence of contact allergy due to epoxy resins, decreased healthcare costs, and an increased quality of life for those handling thermosetting materials.

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Sensitizing capacity and cross‐reaction pattern of the isomers of diglycidyl ether of bisphenol F in the guinea pig

Cited by 30 publications

References 10 publications

An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002

An attempt to improve diagnostics of contact allergy due to epoxy resin systems. First results of the multicentre study EPOX 2002

Analogues of the Epoxy Resin Monomer Diglycidyl Ether of Bisphenol F: Effects on Contact Allergenic Potency and Cytotoxicity

Epoxy Resin Monomers with Reduced Skin Sensitizing Potency

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