Sensitizers in PTBP-formaldehyde resins.
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Dermatitis, Contact↗
Biomedical subjects
M Bruze
Publications and source records attributed to M Bruze.
Demonstration of contact sensitizers in resins and products based on phenol-formaldehyde.
12 phenol-formaldehyde resins were investigated with regard to the presence of 14 contact sensitizers by using high-pressure liquid chromatography. The allergens consisted of simple methylol phenols, dihydroxydiphenyl methanes, 4,4(1)-dihydroxy-(hydroxymethyl)-diphenyl methanes and 2,4(1)-dihydroxy-(hydroxymethyl)-diphenyl methanes. Four substances, 2,4-dimethylol phenol, 2,6-dimethylol phenol, 4,4(1)-dihydroxydiphenyl methane and 2,4(1)-dihydroxydiphenyl methane, were isolated from a resol resin and identified by mass-spectrometry and nuclear magnetic resonance spectrometry. The highest concentrations (up to 15% w/w) of allergens were noted for methylol phenols in resol resins based on phenol and formaldehyde. The corresponding novolak resins showed a high content of dihydroxydiphenyl methanes. There was great variation in concentration of the sensitizers between the resins. None of these sensitizers were demonstrated in the resin based on paratertiary-butyl phenol. Products based on phenol-formaldehyde resins were also investigated for the presence of allergens. Uncured impregnated paper for laminate production and uncured mineral wool contained the same concentrations of the sensitizers as some of the resins studied. The curing process decreased the content of all the allergens investigated in all products, but the sensitizers did not disappear, and they may thus be present in finished products.
Allergens↗
Seasonal influence on routine patch test results.
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Humans↗
Sensitizing capacity of dihydroxydiphenyl methane (bisphenol F) in the guinea pig.
The sensitizing capacity of 2,2(1)-dihydroxydiphenyl methane (2,2(1)-HPM), 4,4(1)-dihydroxydiphenyl methane (4,4(1)-HPM) and 2,4(1)-dihydroxydiphenyl methane (2,4(1)-HPM) was investigated with the guinea pig maximization test. These compounds are known contact sensitizers in phenol-formaldehyde resins. The study was performed to assess and compare their sensitizing capacities. A weak sensitizing capacity of 2,2(1)-HPM was demonstrated when the results for 2 separate series were added, while no sensitizing capacity was demonstrated for 4,4(1)-HPM or 2,4(1)-HPM. The compounds tested were chromatographically pure.
Animals↗
Demonstration of Kathon CG in some commercial products.
The preservative Kathon CG has become one of the most common sensitizers. It has, however, been difficult to explain the sensitization and to assess the clinical relevance of the contact allergy, partly due to lack of specification of the preservative in products. A high-performance liquid chromatography method was used to demonstrate Kathon CG in 123 commercial products of both "leave on" and "rinse off" types. 38 of these contained Kathon CG in the range of 1-15 ppm of active ingredients. There were no differences between "leave on" and "rinse off" products concerning the relative number of products containing Kathon CG and the concentrations of the preservative.
Allergens↗
Patch testing with colophony at 60% concentration.
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Female↗
Sensitizing capacity of 4,4(1)-dihydroxy-(hydroxymethyl)-diphenyl methanes in the guinea pig.
The sensitizing capacity of 4,4(1)-dihydroxy-3-(hydroxymethyl)-diphenyl methane (4,4(1)-H-3-HPM), 4,4(1)-dihydroxy-3,3(1)-di-(hydroxymethyl)-diphenyl methane 4,4(1)-H-3,3(1)--HPM) and 4,4(1)-dihydroxy-3,5-di-(hydroxymethyl)-diphenyl methane (4,4(1)-H-3,5-HPM) was investigated using the guinea pig maximization text. These compounds are known contact sensitizers in phenol-formaldehyde resins (P-F-R). The study was performed in order to assess and compare the degrees of the sensitizing capacities of these chemically related substances. The animals were also rechallenged with the sensitizer and 5 related compounds, all known to be present in P-F-R, in order to study the cross-reaction patterns. 4,4(1)-H-3,3(1)-HPM was demonstrated to be a strong sensitizer and 4,4(1)-H-3-HPM and 4,4(1)-H-3,5-HPM to be moderate sensitizers. With 4,4(1)-H-3,3(1)-HPM as the sensitizer, 4,4(1)-H-3-HPM and 4,4(1)-H-3,5-HPM were cross-reacting substances and simple methylol phenols were possible cross-reacting compounds. Possible cross-reactivity were indicated between the three 4,4(1)-H-HPM when 4,4(1)-H-3-HPM and 4,4(1)-H-3,5-HPM respectively were the sensitizers. The chemical investigation by high pressure liquid chromatography indicated that the compounds tested were pure and separable.
Animals↗
Contact allergy to phenol-formaldehyde resins.
Adverse reactions to phenol-formaldehyde resins include depigmentation, irritant dermatitis, chemical burns and allergic contact dermatitis. Allergic contact dermatitis from phenol-formaldehyde resin has mainly been ascribed to resins based on paratertiary-butyl phenol and formaldehyde, and such a resin is included in the ICDRG standard patch test series. When 1220 patients were patch tested with this resin as well as with 2 other phenol-formaldehyde resins, based on phenol and formaldehyde, 26 patients were positive to at least 1 resin. The figures for positive reactions to paratertiary-butyl phenol-formaldehyde resin and the 2 other resins were 0.8%, 1.0% and 3.0% (440 tested subjects), respectively. Therefore, a battery of phenol-formaldehyde resins should be used for screening purposes, since patch testing with the paratertiary-butyl phenol-formaldehyde resin is not sufficient to identify patients with contact allergy to phenol-formaldehyde resins. Several of the 26 patients were patch tested with the basic substances phenol, formaldehyde and paratertiary-butyl phenol, but only 1 positive reaction to formaldehyde was noted. The sensitizing capacity of 2-methylol phenol, 4-methylol phenol and 2,4,6-trimethylol phenol, all 3 compounds being possible ingredients of resins based on phenol and formaldehyde, was demonstrated; 5 of 14 resin positive patients reacted to at least 1 of these methylol phenols.
Chemical Phenomena↗
Contact allergy to 3-methylol phenol, 2,4-dimethylol phenol and 2,6-dimethylol phenol.
Thirteen patients with contact allergy to phenol-formaldehyde resins (P-F-R) were patch tested with 3-methylol phenol, 2,4-dimethylol phenol and 2,6-dimethylol phenol. Nine patients reacted to at least 1 compound, all giving positive test responses to 2,4-dimethylol phenol. Seven patients reacted simultaneously to 2,6-dimethylol phenol while only 1 patient reacted to 3-methylol phenol. Negative test responses were noted in 20 controls. Chemical investigation by high pressure liquid chromatography indicated that the compounds tested were pure and separable. The 3 reported sensitizers may, theoretically, be generated during the manufacture of P-F-R. 2,4-Dimethylol phenol and 2,6-dimethylol phenol have been demonstrated and there has been chromatographic evidence of 3-methylol phenol in the P-F-R used in the routine test series at the department.
Benzyl Alcohols↗
Antinuclear antibodies in mice induced by long wave ultraviolet radiation (UVA).
PUVA therapy has been reported to induce antinuclear antibodies (ANA). The generation of ANA following ultraviolet irradiation was studied experimentally in albino mice. When treated with long wave ultraviolet radiation (UVA) from blacklight fluorescent tubes a significant number of animals developed positive ANA titres, whereas no change was noted in groups, treated with PUVA, 8-methoxypsoralen only or medium wave ultraviolet irradiation (UVB) respectively. The tendency for UVA-irradiated mice to develop ANA was stronger when higher ANA titres were compared. UVA induces ANA in mice, and PUVA-induced ANA may be due to the UVA component of this therapy.
Animals↗
Antinuclear antibodies appearing during PUVA therapy.
Antinuclear antibodies (ANA) were studied in patients receiving PUVA therapy. Ten patients out of 124, (8%), considered for PUVA had ANA prior to therapy. During PUVA treatment ANA appeared in 34 out of 100 patients. Eight patients with ANA initially were treated and in 4 of them a significant increase in ANA titre was noted. A statistically significant difference was noted, when the first and last ANA tests for each patient were compared. No such difference was seen in a control group consisting of 33 patients. All PUVA patients generating ANA were evaluated clinically and with a laboratory screening. This evaluation was negative in all patients except one who developed ANA of the nucleolar staining pattern together with symptoms consistent with a collagen vascular disease. The ANA titres were generally low and the staining pattern was of the homogeneous type in all patients but one.
Adolescent↗
Contact sensitizers in resins based on phenol and formaldehyde.
A paratertiary-butyl phenol-formaldehyde resin is present in the routine patch test series of the International Contact Dermatitis Research Group. This resin was not sufficient to trace patients with contact allergy to resins based on phenol and formaldehyde (P-F-R). A particular resol resin (P-F-R-2) was demonstrated to be a good tracer of patients with P-F-R hypersensitivity. 2-methylol phenol (2-MP), 4-methylol phenol (4-MP) and 2,4,6-trimethylol phenol (2,4,6-MP) were, besides formaldehyde, known sensitizers in P-F-R. The sensitizing potentials were confirmed both in humans and in guinea pigs. Eleven new contact sensitizers in P-F-R were established. A consistently performed patch testing, including testing with serial dilutions of each sensitizer, facilitated comparisons and conclusions concerning (a) assessment of irritancy/allergenicity, (b) determination of highest acceptable contaminations, (c) evaluation of clinical relevance and (d) choice of substances for cross-reactivity testing. Six theoretically possible substances in P-F-R, 3-methylol phenol, 2,4-dimethylol phenol, 2,6-dimethylol phenol, 2,21-dihydroxydiphenyl methane (2,21-HPM), 4,41-dihydroxydiphenyl methane (4,41-HPM) and 2,41-dihydroxydiphenyl methane (2,41-HPM), were established as contact sensitizers and also demonstrated and identified in P-F-R-2. Five sensitizers were isolated from P-F-R-2 and identified to be 4,4-dihydroxy-3-(hydroxymethyl)-diphenyl methane (4,41-H-3-HPM), 4,41-dihydroxy-3,31-di-(hydroxymethyl)-diphenyl methane (4,41-H-3,31-HPM), 4,4-dihydroxy-3,5-di-(hydroxymethyl)-diphenyl methane (4,41-H-3,5-HPM), 2,41-dihydroxy-3,31-di-(hydroxymethyl)-diphenyl methane and 2,4-dihydroxy-31,51-di-(hydroxymethyl)-diphenyl methane. Nine sensitizers, 2-MP, 4-MP, 2,4,6-MP, 2,21-HPM, 4,41-HPM, 2,41-HPM, 4,41-H-3-HPM, 4,41-H-3,31-HPM and 4,41-H-3,5-HPM, were investigated using guinea pigs for sensitizations. The guinea pig maximization test was modified to increase standardization, enable a blind evaluation and also statistical comparisons between test animals and appropriate control animals. All 9 substances, except 4,41-HPM and 2,41-HPM, were established as contact sensitizers in guinea pigs. The 4,41-H-HPM were the most potent allergens. Phenol-formaldehyde resins and products based on P-F-R were investigated for the presence of 14 contact sensitizers. The concentrations varied and the highest concentrations were demonstrated for simple methylol phenols in P-F-R of the resol type.(ABSTRACT TRUNCATED AT 400 WORDS)
Allergens↗
Contact allergy to dihydroxydiphenyl methanes (bisphenol F).
16 patients with contact allergy to phenol-formaldehyde resins (P-F-R) were patch tested with 3 dihydroxydiphenyl methanes (bisphenol F). The chemical investigation by high pressure liquid chromatography indicated that the dihydroxydiphenyl methanes (HPM) were pure and separable. 9 patients reacted to at least one HPM and all these gave positive test responses to 2,4(1)-HPM. 3 patients reacted simultaneously to 2,4(1)-HPM and 4,4(1)-HPM and one of these 3 patients reacted simultaneously to all 3 HPM. No positive test responses were noted in 100 controls. 8 of the 9 patients were also patch tested with 8 compounds with similar chemical structures to the HPM. Possible cross-reactions were observed in 2 patients for 4-hydroxydiphenyl methane, 4,4(1)-dihydroxydiphenyl-2-propane (bisphenol A) and diethylstilbestrol. The 3 reported sensitizers may, theoretically, be generated during the manufacture of P-F-R. 2,4(1)-HPM and 4,4(1)-HPM have been demonstrated and there have been indications of 2,2(1)-HPM in the P-F-R used in the routine test series at the department.
Benzhydryl Compounds↗
Effect of ultraviolet irradiation of photopatch test substances in vitro.
The mechanisms behind allergic photocontact reactions are not clear. For certain photoactive substances the generation of photoproducts may be one step in the sequence of events inducing photoallergy. 26 photoactive substances were studied by thin layer chromatography (TLC) before and after long-wave or medium-wave ultraviolet irradiation for 1, 3 and 5 h (10.8, 32.4, 54 J/cm2 and 1.1, 3.2, 5.4 J/cm2). The formation of photoproducts was demonstrated for 13 substances. For 8 of these, photoproducts were formed regardless of type of ultraviolet exposure while for 5 compounds photoproducts were demonstrated only after long-wave ultraviolet irradiation. All photoactive compounds forming photoproducts did so after UVA irradiation which is in accordance with the finding of action spectra for photoallergic reactions in human skin within this region. No photoproducts were demonstrated for 13 of the tested substances.
Allergens↗
Thin layer chromatography and high pressure liquid chromatography of musk ambrette and other nitromusk compounds including photopatch studies.
For qualitative and quantitative analysis of musk ambrette and 4 other nitromusk compounds (musk ketone, moskene, musk tibetine, musk xylene) thin layer chromatography (TLC) and high pressure liquid chromatography (HPLC) techniques were developed. By TLC a reasonable separation was obtained and the limit of detection was 2-5 x 10(-7) g. By HPLC the separation was even better and the limit of detection for musk ambrette was 2 x 10(-9) g. The correlation between the amount of musk ambrette/ketone and the HPLC peak was linear. The TLC and HPLC techniques were used to demonstrate the presence of nitromusks in several commercial products, mainly aftershave lotions and eau-de-toilettes preparations. By ultraviolet spectrophotometry, absorption spectra were studied for the nitromusk compounds. The absorption maximum for musk ambrette was at 264 nm, that for moskene at 253 nm. Photopatch testing was carried out in 13 patients photoallergic to musk ambrette. Only 3 patients also reacted to other nitromusks. Photoallergey to musk ketone and musk tibetine is reported for the first time.
Chromatography, High Pressure Liquid↗
Contact allergy to photoproducts of musk ambrette.
A patient with photocontact allergy to musk ambrette was investigated with patch and photopatch testing with dilutions of musk ambrette and 4 other nitro-musk compounds (musk ketone, moskene, musk tibetine, musk xylene) as well as with in vitro ultraviolet-irradiated solutions of musk ambrette. Besides a strong photoallergy to musk ambrette, a plain contact allergy to photoproducts of musk ambrette was demonstrated. An attempt to isolate the photoproducts causing the plain contact allergy was performed by using a preparative thin layer chromatography technique. These isolated photoproducts were not, however, responsible for the contact allergy to the photodecomposed musk ambrette.
Adult↗
Use of buffer solutions for patch testing.
Acid and alkaline products must usually be diluted before patch testing in order to be non-irritant. The use of ordinary solvents for the dilution often means low-concentration products to be tested. By using buffer solutions, the possible test concentrations can be increased at least many hundred fold.
Buffers↗
Simultaneous patch test sensitization to 4 chemically unrelated compounds in a standard test series.
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Adult↗