Allergenic degradation products of para‐tertiary butylphenolformaldehyde plastic

Malten, K. E.; Seutter, E.

doi:10.1111/j.1600-0536.1985.tb01113.x

Cited by 29 publications

(6 citation statements)

References 3 publications

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“…This might indicate the involvement of degradation products in the sensitization process. Degradation products were suggested as important sensitizers in PTBP‐F‐R allergy by Malten & Seutter in 1985 (15). Dimethylene ether bridges, the connecting bonds between the p‐ tert butylphenol units in the linear trimer XIII, can be broken by the addition of water under certain conditions.…”

Section: Discussionmentioning

confidence: 99%

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

Zimerson

Bruze

2002

Contact Dermatitis

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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.

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Section: Discussionmentioning

confidence: 99%

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

Zimerson

Bruze

2002

Contact Dermatitis

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“…Neoantigens can induce autoimmunity by activating immune reactivity to both the modified and unadulterated autoantigens, resulting in CD8 + cytotoxic T‐cell migration to the skin and progressive destruction of drug‐exposed and unexposed melanocytes . Melanocytes are absent from depigmented lesions exposed to 4‐TBP , as 4‐TBP induces melanocyte apoptosis . 4‐TBP is preferentially cytotoxic to melanocytes .…”

Section: Mechanism Of Action Of Topical Depigmenting Agentsmentioning

confidence: 99%

Enhanced bleaching treatment: opportunities for immune‐assisted melanocyte suicide in vitiligo

Webb

Eby

Hariharan

et al. 2014

Experimental Dermatology

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Depigmentation in vitiligo occurs by progressive loss of melanocytes from the basal layer of the skin, and can be psychologically devastating to patients. T cell-mediated autoimmunity explains the progressive nature of this disease. Rather than being confronted with periods of rapid depigmentation and bouts of repigmentation, patients with long-standing, treatment-resistant vitiligo can undergo depigmentation treatment. The objective is to remove residual pigmentation in order to achieve a cosmetically acceptable result- that of skin with a uniform appearance. In the USA, only the use of mono-benzyl ether of hydroquinone (MBEH) is approved for this purpose. However, satisfactory results can take time to appear, and there is a risk of repigmentation. MBEH induces necrotic melanocyte death followed by a cytotoxic T cell response to remaining, distant melanocytes. As cytotoxic T cell responses are instrumental to depigmentation, we propose that combining MBEH with immune adjuvant therapies will accelerate immune-mediated melanocyte destruction to achieve faster, more definitive depigmentation than with MBEH alone. Since Toll-like Receptor (TLR) agonists-imiquimod, CpG, and Heat Shock Protein 70 (HSP 70)-all support powerful Th1 responses, we propose that using MBEH in combination with these agents can achieve superior depigmentation results for vitiligo patients.

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“…Allergic contact dermatitis has been reported from contact with, among other things, glues, shoes, watchstraps, athletic tape, a hearing aid, and ink of a marking pen. The following substances have been reported as allergens in the resin: formaldehyde, p-tert-butylphenol (PTBP), 2-methylol p-tert-butylphenol (2-MPTBP), 2,6-dimethylol p-tert-butylphenol (2,6-MPTBP), some degradation products, and a few larger phenolic compounds (4)(5)(6)(7)(8)(9). Simultaneous patch test reactions to balsam of Peru, hydroabietyl alcohol, a resin based on phenol and formaldehyde (P-F-R) and PTBP-F-R have been reported (10).…”

mentioning

confidence: 99%

Contact allergy to the monomers of p‐tert‐butylphenol‐formaldehyde resin in the guinea pig

Zimerson

Bruze

1998

Contact Dermatitis

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In patients hypersensitive to p-tert-butylphenol-formaldehyde resin (PTBP-F-R), and butylphenol derivatives therein, it is for diagnostic, therapeutic and preventive reasons necessary to know the identity of the primary sensitizing substances, their sensitizing capacities as well as their cross-reaction patterns. The monomers in PTBP-F-R, 2-methylol p-tert-butylphenol (2-MPTBP) and 2,6-dimethylol p-tert-butylphenol (2,6-MPTBP), have been shown to be contact sensitizers in man. The aim of this study was to investigate the sensitizing capacities of the monomers and establish cross-reacting patterns in the guinea pig with the guinea pig maximization test. 2,6-MPTBP was shown to be a strong sensitizer while it was indicated that 2-MPTBP was a sensitizer. Animals sensitized to 2,6-MPTBP showed cross-reactions to 2-MPTBP and p-tert-butylcatechol. No cross-reactions were shown to p-tert-butylphenol, tert-butyl 4-hydroxyanisole (BHA) and 3,5-di-tert-butyl 4-hydroxytoluene (BHT).

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Allergenic degradation products of para‐tertiary butylphenolformaldehyde plastic

Cited by 29 publications

References 3 publications

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

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

Enhanced bleaching treatment: opportunities for immune‐assisted melanocyte suicide in vitiligo

Contact allergy to the monomers of p‐tert‐butylphenol‐formaldehyde resin in the guinea pig

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