Extraction of haptens from solid products and their delivery to the skin, exemplified by dithiocarbamates from rubber gloves

Bergendorff, Ola; Persson, Christina; Hansson, Christer

doi:10.1111/j.0105-1873.2005.00616.x

Cited by 5 publications

(8 citation statements)

References 14 publications

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“…However, there has been a lack of suitable methods for analyses of dithiocarbamates. A newly published work, which has been optimized in our laboratory, has opened the field of dithiocarbamate analyses concomitant to thiuram and MBT analyses (4, 5). The present work shows that, among rubber‐sensitive patients, there are probably several missed contact allergies to allergens formed during vulcanization.…”

Section: Discussionmentioning

confidence: 67%

“…A chemical analysis of the diving mask was performed by extracting 0.5 g of the diving mask with 5 ml acetone (4). The extract was analysed by high‐performance liquid chromatography using a non‐metal column, all according to a procedure presented earlier (4, 5). In the extract, we found MBT but also BT‐DEC, an unusual accelerator with the trade names Nocceler 64 or Ethylac.…”

Section: Case Reportmentioning

confidence: 99%

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Contact dermatitis to a rubber allergen with both dithiocarbamate and benzothiazole structure

Bergendorff

Hansson

2007

Contact Dermatitis

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Contact dermatitis to rubber products are often caused by additives used during manufacture, and diagnosed from patch test with established rubber allergen series. In these series the compounds are divided into separate groups such as thiurams, dithiocarbamates and mercaptobenzothiazoles. The objectives were to investigate the substances with allergenic structures present in a diving mask giving rise to facial dermatitis, also those substances including structures from different groups of rubber chemicals. The rubber material was analysed by high-performance liquid chromatography and diode-array detector. The patient was tested by epicutaneous tests using pure substances, extracts and authentic rubber material. 2-Benzothiazolyl-N,N-diethylthiocarbamylsulfide, was found in the diving mask and the patient showed positive reaction to the pure compound and to extracts of the diving mask. This compound has structures of both mercaptobenzothiazole and thiuram/dithiocarbamate in its formulae. Besides the established groups of rubber accelerators, uncommon allergens with structures from more than one group can be formed or added at vulcanization. Chemical analysis of the product is needed to find these allergens.

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Section: Discussionmentioning

confidence: 67%

Section: Case Reportmentioning

confidence: 99%

Contact dermatitis to a rubber allergen with both dithiocarbamate and benzothiazole structure

Bergendorff

Hansson

2007

Contact Dermatitis

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“…These data do not display effects from the rubber matrix. Although in another experiment that we have published (6), a recovery of about 77% was obtained. In that case, a glove that itself contained dithiocarbamates was extracted several times with new portions of solvent until the extract was almost devoid of dithiocarbamates.…”

Section: Resultsmentioning

confidence: 87%

“…1 sample (0.5 g) of each glove was cut into small pieces with a pair of scissors and placed in a 10‐ml test‐tube with a Teflon‐lined screw cap containing 5 ml acetone (ScherfChroma, Germany) (6). The test‐tube was placed on a shaker, and after 10‐min extraction at room temperature, the extract was pipetted into a round‐bottomed flask and evaporated under vacuum.…”

Section: Methodsmentioning

confidence: 99%

High‐performance liquid chromatography analysis of rubber allergens in protective gloves used in health care

2006

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A high-performance liquid chromatography (HPLC) method developed for analysis of zinc dithiocarbamates was validated and used to perform a survey of disposable medical gloves used in southern Sweden. The gloves were extracted with acetone at room temperature for 10 min by shaking. The extracts were injected into a polyether ether ketone lined HPLC column, and peaks were analysed by a diode-array detector. The survey shows that of 19 gloves analysed, 10 contained zinc diethyldithiocarbamate (0.070-3.5 mg/g), 3 contained zinc pentamethylenedithiocarbamate (1.0-4.3 mg/g), 4 contained zinc dibutyldithiocarbamate (0.9-1.1 mg/g), and 2 contained 2-mercaptobenzothiazole (0.005-0.008 mg/g). None of them contained thiurams.

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“…At the Department of Dermatology at Lund University Hospital, we have for many years worked on the analysis of rubber items (2–5) as well as studying the chemistry of various rubber additives (6, 7). As the question of chemical changes occurring during vulcanization often arose, it was natural to collaborate with a Swedish rubber factory (Trelleborg AB, Trelleborg, Sweden) to investigate the chemistry of allergenic rubber additives.…”

mentioning

confidence: 99%

Chemical changes in rubber allergens during vulcanization

et al. 2007

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Allergic contact dermatitis to rubber is caused by residues of chemicals used in manufacturing a rubber product. Several different additives are used to achieve a final product of the desired characteristics. Accelerators such as thiurams, dithiocarbamates, and mercaptobenzothiazoles are often among the additives responsible for allergic reactions recognized by dermatologists. The chemistry of the vulcanization process is complicated; as it occurs at an elevated temperature with a mixture of reactive chemicals, the compositions of the initial and final products differ. This paper investigates the changes in composition of common allergens during vulcanization, doing so by chemically analysing various rubber formulations at different stages of the process. Major changes were found in which added chemicals were consumed and new ones produced. An important observation is that thiuram disulfides rarely appear in the final rubber although they may have been used as additives. Instead, thiurams are often converted to dithiocarbamates or to products formed by addition to mercaptobenzothiazole structures, if these have been used together with thiurams as accelerators.

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Extraction of haptens from solid products and their delivery to the skin, exemplified by dithiocarbamates from rubber gloves

Cited by 5 publications

References 14 publications

Contact dermatitis to a rubber allergen with both dithiocarbamate and benzothiazole structure

Contact dermatitis to a rubber allergen with both dithiocarbamate and benzothiazole structure

High‐performance liquid chromatography analysis of rubber allergens in protective gloves used in health care

Chemical changes in rubber allergens during vulcanization

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