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Contact Allergy to Epoxy Resins of the Bisphenol F-type

Pontén, Ann LU (2003)
Abstract
Epoxy resins based on bisphenol A are well-known contact allergens and often cause occupational contact allergy. The most important allergen is the monomer diglycidyl ether of bisphenol A (DGEBA). Epoxy resins of the bisphenol F-type contain 3 isomers of the diglycidyl ether of bisphenol F; p,p'-DGEBF, o,p'-DGEBF, and o,o'-DGEBF, whereas epoxy resin(s) based on bisphenol A (DGEBA-R) contain virtually only 1 isomer of DGEBA. The allergenicity of DGEBA has been investigated earlier, but the DGEBF isomers have not previously been investigated as contact allergens. When an epoxy resin based on bisphenol F was inserted in the standard patch test series of our department, it was found that contact allergy to this type of epoxy resin was at least... (More)
Epoxy resins based on bisphenol A are well-known contact allergens and often cause occupational contact allergy. The most important allergen is the monomer diglycidyl ether of bisphenol A (DGEBA). Epoxy resins of the bisphenol F-type contain 3 isomers of the diglycidyl ether of bisphenol F; p,p'-DGEBF, o,p'-DGEBF, and o,o'-DGEBF, whereas epoxy resin(s) based on bisphenol A (DGEBA-R) contain virtually only 1 isomer of DGEBA. The allergenicity of DGEBA has been investigated earlier, but the DGEBF isomers have not previously been investigated as contact allergens. When an epoxy resin based on bisphenol F was inserted in the standard patch test series of our department, it was found that contact allergy to this type of epoxy resin was at least as common as contact allergy to DGEBA-R. A majority of the patients reacted to both types of epoxy resins. Both p,p'-DGEBF and o,p'-DGEBF were shown to be sensitizers in humans, while o,o'-DGEBF elicited surprisingly few reactions. p,p'-DGEBF was found to be a sensitizer and at least as strong as DGEBA. All 3 DGEBF isomers were found to be strong sensitizers in animal studies. It was also found that DGEBA, p,p'-DGEBF and o,p'-DGEBF cross-reacted with one another to a high degree, while o,o'-DGEBF did not. o,o'-DGEBF was assumed to be a sensitizer mainly in the absence of the other 3 substances. Humans are then generally not sensitized to o,o'-DGEBF, since it does not occur alone in the epoxy resins of the bisphenol F-type. For the individuals with contact allergy both to DGEBA-R and epoxy resins of the bisphenol F-type, concomitant sensitization as well as cross-sensitization might be the case. When contact allergy to epoxy resins of the bisphenol F-type is suspected, this type of epoxy resin should be patch tested, especially if the DGEBA-R patch test is negative. Depending on the clinical situation, the patch-test concentration recommended is 0.25-0.5%. Consecutive patch testing with epoxy resins of the bisphenol F-type at a concentration of 1.0% is not recommended due to the possibility of patch-test sensitization. It was found that the sensitivity of the thin-layer chromatography method was around 200 times more sensitive for DGEBA than for DGEBF isomers. In patients with contact allergy to DGEBA-R, the cause of allergic contact dermatitis might be an epoxy resin of the bisphenol F-type. The latter resins are most probably not detected by the TLC method developed for DGEBA-R. If the product is analyzed only with the TLC method, the relevance of the contact allergy to DGEBA-R might therefore remain unrecognized. In an industrial investigation among 603 workers exposed to epoxy resins 20.3% of the 325 patch-tested workers had occupational ACD. Approximately 15% of the workers with occupational ACD had contact allergy to DGEBA-R and 36% had contact allergy both to epoxy resins of the bisphenol F-type and DGEBA-R. Around 40% of the patch-tested workers were estimated to have skin disease either caused or aggravated by work. Although a well-known occupational contact allergen, a high frequency of contact allergy to DGEBA-R among exposed workers was found. Thorough instruction concerning protection, most importantly for new employees, as well as the development of production methods that minimize exposure, especially to DGEBA-R, are necessary measures for preventing occupational dermatoses among workers exposed to ERS in the manufacture of rotor blades for wind turbines. (Less)
Abstract (Swedish)
Popular Abstract in Swedish

Kontaktallergi är en vanlig orsak till eksem i arbetslivet. Ett av de viktigaste arbetsrelaterade allergenen är epoxiharts. Det allergiframkallande ämnet i det vanligaste epoxihartset visades på 1970-talet vara det ämne, diglycidyleter av bisfenol A (DGEBA), som hartset är uppbyggt av. Dessa epoxihartser är sedan decennier med i den standardserie med allergiframkallande ämnen som patienter med misstänkt kontakteksem undersöks med. En del epoxihartser innehåller diglycidyleter av bisfenol F (DGEBF) istället för DGEBA. Till skillnad från DGEBA förekommer DGEBF i 3 olika varianter (isomerer). Hitintills har DGEBF isomererna inte varit undersökta med tanke på sin allergiframkallande förmåga. När en... (More)
Popular Abstract in Swedish

Kontaktallergi är en vanlig orsak till eksem i arbetslivet. Ett av de viktigaste arbetsrelaterade allergenen är epoxiharts. Det allergiframkallande ämnet i det vanligaste epoxihartset visades på 1970-talet vara det ämne, diglycidyleter av bisfenol A (DGEBA), som hartset är uppbyggt av. Dessa epoxihartser är sedan decennier med i den standardserie med allergiframkallande ämnen som patienter med misstänkt kontakteksem undersöks med. En del epoxihartser innehåller diglycidyleter av bisfenol F (DGEBF) istället för DGEBA. Till skillnad från DGEBA förekommer DGEBF i 3 olika varianter (isomerer). Hitintills har DGEBF isomererna inte varit undersökta med tanke på sin allergiframkallande förmåga. När en bisfenol F-epoxiharts sattes in i vår avdelnings standardserie i samma koncentration som bisfenol A-epoxiharts (1.0%) konstaterades att allergi mot bisfenol F-epoxiharts var minst lika vanlig som allergi mot bisfenol A-epoxiharts. En majoritet av patienterna reagerade mot båda typerna av epoxiharts, men det fanns också flera patienter som enbart reagerade mot bisfenol F-epoxiharts. De 3 DGEBF isomererna separerades, renades och identifierades. När var och en av dem testades på patienter med kontaktallergi mot bisfenol F-epoxiharts visade det sig att 2 av dem framkallade allergiska reaktioner, men att den tredje gjorde det ytterst sällan. Den allergiframkallande förmågan hos alla 3 DGEBF isomererna jämfört med DGEBA undersöktes i djurförsök. Alla 4 ämnena visade sig vara starka allergen i djurförsöket. DGEBA och de 2 DGEBF isomerer som framkallade allergiska reaktioner hos människor korsreagerade med varandra, det vill säga om djuret redan var allergiskt mot ett av ämnena reagerade det för ett eller flera av de andra också. Om resultaten från djurförsöket appliceras på människor betyder det att människor som blivit allergiska mot bisfenol F-epoxihartser ofta reagerar om de kommer i kontakt med bisfenol A-epoxiharts och vice versa. Den DGEBF isomer som de epoxiallergiska patienterna inte reagerade mot korsreagerade inte i någon större utsträckning med de andra ämnena. Resultaten kan tolkas så att den isomer som inte gav några reaktioner huvudsakligen kan åstadkomma allergi i frånvaro av de 2 övriga DGEBF isomererna eller DGEBA. Tunnskiktskromatografi kan användas för att upptäcka DGEBA i produkter misstänkta att orsaka allergiskt kontakteksem. Vår underökning visade att det behövdes 200 gånger mer av DGEBF isomererna för att upptäcka dem med tunnskiktskromatografi jämfört med DGEBA. Betydelsen av en konstaterad kontaktallergi mot bisfenol A- och F-epoxihartser riskerar därför att inte kunna fastställas om den misstänkta produkten undersöks enbart med tunnskiktskromatografi. I en studie av 603 arbetare anställda inom epoxibaserad tillverkning av vindkraftverk kontaktallergitestades 325 arbetare, eftersom de hade misstänkt arbetsorsakat eksem. Cirka 40% av de testade hade ett eksem som antingen orsakades eller förvärrades av arbetet. Av de testade arbetarna hade 10.5% kontaktallergi mot bisfenol A-epoxiharts, och sammanlagt 20.3% hade arbetsorsakad kontaktallergi. Cirka 15% av dem med arbetsorsakad kontakallergi reagerade mot bisfenol A-epoxiharts och 36% reagerade mot både bisfenol F-epoxiharts och bisfenol A-epoxiharts. Arbetsorsakad kontaktallergi diagnostiserades primärt inom ramen för vår studie hos 55 arbetare. Av dem hade 23 tidigare sökt läkare på grund av sina hudbesvär. Av dessa 23 hade 12 (52%) kontaktallergi mot epoxiharts i standardserien, när de testades i vår studie, vilket visar vikten av lapptestning när det gäller undersökning av eksem som kan vara arbetsrelaterat. (Less)
Please use this url to cite or link to this publication:
author
supervisor
opponent
  • Professor Anderson, Chris, Linköping University Hospital
organization
publishing date
type
Thesis
publication status
published
subject
keywords
thin-layer chromatography, occupational dermatitis, isomers, bisphenol F, bisphenol A, DGEBF, DGEBA, epoxy resin of the bisphenol F-type, Epoxy resin, contact allergy, Dermatology, venereology, Dermatologi, venereologi, Occupational health, industrial medicine, Yrkesmedicin, arbetsmiljömedicin
pages
154 pages
publisher
Ann Pontén, Department of Occupational and Environmental Dermatology, Malmö University Hospital, SE-205 02 Malmö,
defense location
Hudklinikens föreläsningssal, Universitetssjukhuset MAS, Malmö
defense date
2003-05-30 10:15:00
external identifiers
  • other:ISRN: LUMEDW/MEHM-1014-SE
ISBN
91-628-5669-3
language
English
LU publication?
yes
additional info
Article: I. Chemical analysis of monomers in epoxy resins based on bisphenol F and A. Pontén A, Zimerson E, Sörensen Ö, Bruze M.(In manuscript) Article: II. Contact allergy to the isomers of diglycidyl ether of bisphenol F.Pontén A, Zimerson A, Bruze M.(Accepted for publication in Acta Dermato-Venereologica) Article: III. Sensitizing capacity and cross-reaction pattern of the isomers of diglycidyl ether of bisphenol F in the guinea pig.Pontén A, Zimerson E, Sörensen Ö, Bruze M.Contact Dermatitis 2002:47:293-298. (Reprinted with the permission of the publisher.) Article: IV. Epoxy-based production of wind turbine rotor blades: occupational contact allergies.Pontén A, Carstensen O, Rasmussen K, Gruvberger B, Isaksson M, Bruze M. (Submitted to Contact Dermatitis) Article: V. Epoxy-based production of wind turbine rotor blades: occupational dermatoses.Pontén A, Carstensen O, Rasmussen K, Gruvberger B, Isaksson M, Bruze M. (Submitted to Contact Dermatitis)
id
05bebdc5-3268-4e32-b7ba-0e793e4af704 (old id 465862)
date added to LUP
2016-04-04 11:30:34
date last changed
2018-11-22 14:34:09
@phdthesis{05bebdc5-3268-4e32-b7ba-0e793e4af704,
  abstract     = {{Epoxy resins based on bisphenol A are well-known contact allergens and often cause occupational contact allergy. The most important allergen is the monomer diglycidyl ether of bisphenol A (DGEBA). Epoxy resins of the bisphenol F-type contain 3 isomers of the diglycidyl ether of bisphenol F; p,p'-DGEBF, o,p'-DGEBF, and o,o'-DGEBF, whereas epoxy resin(s) based on bisphenol A (DGEBA-R) contain virtually only 1 isomer of DGEBA. The allergenicity of DGEBA has been investigated earlier, but the DGEBF isomers have not previously been investigated as contact allergens. When an epoxy resin based on bisphenol F was inserted in the standard patch test series of our department, it was found that contact allergy to this type of epoxy resin was at least as common as contact allergy to DGEBA-R. A majority of the patients reacted to both types of epoxy resins. Both p,p'-DGEBF and o,p'-DGEBF were shown to be sensitizers in humans, while o,o'-DGEBF elicited surprisingly few reactions. p,p'-DGEBF was found to be a sensitizer and at least as strong as DGEBA. All 3 DGEBF isomers were found to be strong sensitizers in animal studies. It was also found that DGEBA, p,p'-DGEBF and o,p'-DGEBF cross-reacted with one another to a high degree, while o,o'-DGEBF did not. o,o'-DGEBF was assumed to be a sensitizer mainly in the absence of the other 3 substances. Humans are then generally not sensitized to o,o'-DGEBF, since it does not occur alone in the epoxy resins of the bisphenol F-type. For the individuals with contact allergy both to DGEBA-R and epoxy resins of the bisphenol F-type, concomitant sensitization as well as cross-sensitization might be the case. When contact allergy to epoxy resins of the bisphenol F-type is suspected, this type of epoxy resin should be patch tested, especially if the DGEBA-R patch test is negative. Depending on the clinical situation, the patch-test concentration recommended is 0.25-0.5%. Consecutive patch testing with epoxy resins of the bisphenol F-type at a concentration of 1.0% is not recommended due to the possibility of patch-test sensitization. It was found that the sensitivity of the thin-layer chromatography method was around 200 times more sensitive for DGEBA than for DGEBF isomers. In patients with contact allergy to DGEBA-R, the cause of allergic contact dermatitis might be an epoxy resin of the bisphenol F-type. The latter resins are most probably not detected by the TLC method developed for DGEBA-R. If the product is analyzed only with the TLC method, the relevance of the contact allergy to DGEBA-R might therefore remain unrecognized. In an industrial investigation among 603 workers exposed to epoxy resins 20.3% of the 325 patch-tested workers had occupational ACD. Approximately 15% of the workers with occupational ACD had contact allergy to DGEBA-R and 36% had contact allergy both to epoxy resins of the bisphenol F-type and DGEBA-R. Around 40% of the patch-tested workers were estimated to have skin disease either caused or aggravated by work. Although a well-known occupational contact allergen, a high frequency of contact allergy to DGEBA-R among exposed workers was found. Thorough instruction concerning protection, most importantly for new employees, as well as the development of production methods that minimize exposure, especially to DGEBA-R, are necessary measures for preventing occupational dermatoses among workers exposed to ERS in the manufacture of rotor blades for wind turbines.}},
  author       = {{Pontén, Ann}},
  isbn         = {{91-628-5669-3}},
  keywords     = {{thin-layer chromatography; occupational dermatitis; isomers; bisphenol F; bisphenol A; DGEBF; DGEBA; epoxy resin of the bisphenol F-type; Epoxy resin; contact allergy; Dermatology; venereology; Dermatologi; venereologi; Occupational health; industrial medicine; Yrkesmedicin; arbetsmiljömedicin}},
  language     = {{eng}},
  publisher    = {{Ann Pontén, Department of Occupational and Environmental Dermatology, Malmö University Hospital, SE-205 02 Malmö,}},
  school       = {{Lund University}},
  title        = {{Contact Allergy to Epoxy Resins of the Bisphenol F-type}},
  year         = {{2003}},
}