Sensitizing capacity of some trimers in p‐tert‐butylphenol‐formaldehyde resin

Abstract

Contact allergy to p-tert-butylphenol formaldehyde resin (PTBP-F-R) is not rare. This resin consists of a large number of substances, most of which are still unknown. For diagnostic and preventive reasons the chemical identity of the sensitizers should be known, as well as their sensitizing capacities, cross-reaction patterns and presence in the environment. The aims of this study were to investigate the sensitizing capacities and potential cross-reacting patterns for 4-tert-butyl- 2,6-bis-(5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzyloxymethyl)-phenol (XIII), 4-tert-butyl-2- (5 - tert - butyl - 2 - hydroxy-benzyloxymethyl) - 6 - (5 - tert - butyl - 2 - hydroxy - 3 - hydroxymethyl-benzyloxy methyl)-phenol (XIVa) and 7,15,23-tri-tert-butyl-25,26,27-trihydroxy-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix(3)arene (XVIII) by the guinea pig maximization test. 4-tert-Butyl-2,6-bis-hydroxymethyl-phenol, 4-tert-butylbenzene-1,2-diol, 4-tert-butyl-2-hydroxymethyl-phenol, 4-tert-butyl-phenol, 4-tert-butyl-2-(5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzyloxymethyl)-6-hydroxymethyl-phenol, 4-tert-butyl-2-[5-tert-butyl-3-(5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzyloxymethyl) - 2 -hydroxy-benzyloxymethyl] - 6 - (5 - tert-butyl- 2 -hydroxy- 3 -hydroxymethyl-benzyloxymethyl)- phenol and were used as potential cross-reacting substances. In this study it is strongly indicated that the linear trimer XIII has a sensitizing capacity in the guinea pig which was significant when compared to the controls (p = 0.024). No cross-reactions were detected in animals induced with the linear trimer XIII. The linear trimer XIVa and the cyclic trimer XVIII failed to induce sensitization.

Contact Allergy to Trimers in <i>p-tert</i>-Butylphenol-Formaldehyde Resin

“…In a previous study we have shown that the sensitizing capacities of the trimers XIII, XIVa and XVIII are considerably lower than those of the dimers IX and X [17]. Animal studies and the present study suggest a possibility of lowering the elicitation and sensitization qualities of PTBP-F-R.…”

Concentration variability of potent allergens of p-tert-butylphenol-formaldehyde resin (PTBP-FR) in patch test preparations and commercially available PTBP-FR

“…Two main allergens in the resin with high sensitizing capacity in guinea pigs have been isolated and described. [35][36][37][38][39][40] Elicitation studies in sensitized patients have demonstrated that these allergens play a vital role in contact allergy to PTBP-FR in humans. [41][42][43][44] The allergens are the dimers, 4-tert-butyl-2-(5-tert-butyl-2-hydroxy-3-hydroxymethyl-benzyloxymethyl)-6-hydroxymethylphenol and 4-tert-butyl-2-(5-tert-butyl-2-hydroxy-benzyloxymethyl)-6hydroxymethylphenol.…”

“…PTBP‐FR contains hundreds of compounds, which have not been comprehensively identified chemically. Two main allergens in the resin with high sensitizing capacity in guinea pigs have been isolated and described 35–40 . Elicitation studies in sensitized patients have demonstrated that these allergens play a vital role in contact allergy to PTBP‐FR in humans 41–44 .…”

Experimental and Theoretical Investigations of the Autoxidation of Geranial: A Dioxolane Hydroperoxide Identified as a Skin Sensitizer

“…In investigations of p-tert-butylphenol-formaldehyde resins, a number of trimers have been identified. As weak sensitizers, 37 these show that oligomer oxidation products could be of importance in oxidation mixtures of compounds that are prone to polymerization. The present study shows that also potent sensitizers can be formed in polymerization reactions.…”