Allergic contact dermatitis from unsaturated polyester resin consisting of maleic anhydride, phthalic anhydride, ethylene glycol and dicyclopentadiene.
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Allergens↗
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In vitro demonstration of specific IgE in phthalic anhydride hypersensitivity.
Clinical sensitization to phthalic anhydride occurred in a worker who developed symptoms of rhinorrhea, lacrimination, and wheezing after exposure to this chemical. Positive skin tests, provocative bronchial challenges, and a high serum titer of specific IgE (by the radioallergosorbent test) to phthalic anhydride corroborated his clinical hypersensitivity. Bronchial provocation studies using alcoholic-saline solutions of phthalic anhydride and phthalic anhydride dust resulted in immediate airway obstruction. The successful identification of specific IgE by the radioallergosorbent test demonstrates that this can be a useful in vitro technique for corroborating sensitization to this chemical.
Adult↗
The characteristics of specific IgG to phthalic anhydride (PA)-albumin conjugate.
Phthalic anhydride (PA), used in the chemical industry, binds to proteins and causes allergic reactions. It is important to study the characteristics of antibody to PA-protein. We produced specific IgG against PA-rabbit serum albumin (RSA) by administering subcutaneous injections of PA-RSA conjugate to two rabbits. Both rabbits' sera had high titers of IgG not only to PA-RSA but also to PA-human serum albumin (HSA) and HSA. In enzyme-linked immunosorbent assay (ELISA) and ELISA HSA inhibition, specific IgG to PA-HSA revealed cross-reactivity to three other phthalyl anhydride conjugates, hexahydrophthalic anhydride (HHPA)-HSA, methylhexahydrophthalic anhydride (MHHPA)-HSA, and methyltetrahydrophthalic anhydride (MTHPA)-HSA, in both sera. Titers of IgG to HHPA-HSA, MHHPA-HSA, and MTHPA-HSA were not significantly different. On affinity chromatography, highly specific IgG to PA hapten alone was purified. In the serum not binding to PA column, specific IgG to PA-HSA was significantly less than in original serum, but levels of specific IgG to other phthalyl anhydride-HSA were unchanged. Rabbits immunized with PA-RSA produced at least two types of IgG: one is to PA hapten alone and the other may be against new antigenic determinants (NADs) on HSA.
Animals↗
[Determination of malein anhydride in the presence of phthalic anhydride, alpha-naphthochinon and benzoic acid in the air].
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Air Pollution↗
Kinetic study of the hydrolysis of phthalic anhydride and aryl hydrogen phthalates.
The kinetics of the hydrolysis of phthalic anhydride and X-phenyl hydrogen phthalate (X = H, p-Me, m-Cl, and p-Cl) were studied. Several bases accelerate the reaction of phthalic anhydride: acetate, phosphate, N-methyl imidazole, 1,4-diazabicyclo[2,2,2]octane (DABCO), and carbonate. Phosphate, DABCO, and N-methyl imidazole react as nucleophiles, whereas the data do not allow the determination of whether the other bases react in the same way or as general bases catalyzing the water reaction. The rate constants for all of them including water and HO- define a Brönsted plot with beta = 0.46. The kinetics of the hydrolysis of the esters were studied below pH 6.20, and the mechanism involves the formation of phthalic anhydride, which then is hydrolyzed to the phthalic acid. Phenoxide ion has a very high rate constant for the reaction with phthalic anhydride, so above pH 6.20 it competes significantly with the hydrolysis of the anhydride. The reactions of the esters as a function of pH allow the determination of the kinetic pK(a) which are 3.06, 3.02, 2.95, and 2.93 for X = H, p-Me, m-Cl, and p-Cl, respectively. The data also show that the catalysis by the neighboring carboxy group takes place only when it is ionized (i.e., as carboxylate).
Hydrolysis↗
Serum IgE and lung function in workers exposed to phthalic anhydride.
A total of 23 phthalic anhydride (PA)-exposed workers (air levels up to 17 mg/m3) showed significantly (P less than 0.01) more workrelated symptoms in their eyes (48% vs 6%) and nose (39% vs 0) than did 18 unexposed control subjects. Two of the exposed workers had PA-associated asthma. Surprisingly, the control group exhibited significantly (P less than 0.05) more symptoms of nonspecific bronchial hyperreactivity (44% vs 13%). The exposed workers showed significantly higher levels of total serum IgE (medians, 32 vs 15 kIU/l, P less than 0.05), although values for specific IgE against PA did not differ. This may indicate that such exposure can facilitate the entry of common allergens. There was a significant difference in PA-specific IgG [enzyme-linked immunosorbent assay (ELISA) ratios 0.21 vs 0.12; P less than 0.01]. There were no differences in lung function with regard to vital capacity (VC) and forced expiratory volume (FEV1), closing volume expressed as a percentage of VC (CV%), volume of trapped gas (VTG) before and after inhalation of metacholine, or carbon monoxide transfer factor (TLCO), whereas exposed workers displayed significantly higher late expiratory flow rates (MEF50 and MEF25). In a [99mTc]-diethylenetriamine penta-acetate (DTPA) clearance test, there was no difference between exposed subjects and controls. In summary, exposure to PA did not cause subclinical effects of the lungs. Subjects with lower-airway symptoms showed lower FEV1, MEF50, and MEF25 values and higher VTG (after metacholine) than did those without symptoms.(ABSTRACT TRUNCATED AT 250 WORDS)
Adult↗
Induction of type I hypersensitivity in guinea pigs after inhalation of phthalic anhydride.
Guinea pigs were exposed through inhalation to phthalic anhydride (PA) dust at 0.5, 1.0, and 5.0 mg/m3, 3 hours/day for 5 consecutive days. Inhalation challenge with aerosolized phthalic anhydride-guinea pig serum albumin (PA-GPSA) conjugate elicited immediate-onset respiratory reactions in animals exposed to all three levels of dust. Inhalation challenge of a subgroup of animals with phthalic anhydride dust did not elicit an immediate response, as measured by changes in respiratory frequency and plethysmograph pressure. Serologic studies showed that these animals had allergic IgG1a antibody to PA-GPSA. There was a dose-dependent increase in specific IgG antibody activity, as measured by ELISA. Animals exposed to and challenged with 5.0 mg/m3 PA dust had significant numbers of hemorrhagic lung foci. Those animals with the greatest number of foci had high IgG antibody activity to PA, as measured by ELISA. This study showed that exposure to levels of PA dust as low as 0.5 mg/m3, below the current threshold limit value of 6.0 mg/m3, can sensitize animals to produce allergic antibody.
Administration, Inhalation↗
Phthalic acid excretion as an indicator of exposure to phthalic anhydride in the work atmosphere.
The concentration of phthalic acid was determined in the urine of nine subjects occupationally exposed to phthalic anhydride. For the determination, the urine samples were acidified, extracted with dimethyl ether, esterified with boron trifluoride/methanol and measured by electron capture gas chromatography. Environmental air samples were collected in Tenax tubes, eluted with methyl-t-butyl ether and assayed by electron capture gas chromatography. Significant correlations were found between the concentration in urine samples (range: 0.3-14.0 mumol/mmol creatinine), collected at different times of the day, and the time-weighed average atmospheric concentrations (range: 0.03-10.5 mg/m3). No conjugation of phthalic acid in the urine was observed. The detection limit for urine samples (10 ml) was 0.05 mumol/l) and that for air samples 0.4 microgram/m3. The method has potential for biological monitoring of workers exposed to phthalic anhydride. It was found that at atmospheric anhydride concentrations of about 30% of the hygienic reference value (6 mg/m3), which is applied in many market economies, a body-burden was caused which was not eliminated overnight.
Body Burden↗
Bioassay of phthalic anhydride for possible carcinogenicity.
A bioassay of phthalic anhydride for possible carcinogenicity was conducted by administering the test chemical in feed to F344 rats and B6C3F1 mice. Groups of 50 rats of each sex were administered the test chemical at one of two doses, initially either 25,000 or 50,000 ppm, for 32 weeks. Because of excessive depressions in the amount of body weight gained in the dosed groups, the doses for the males were then reduced to 12,500 and 25,000 ppm, respectively, and the doses for the females were reduced to 6,250 and 12,500 ppm. Administration of the test chemical at the lowered doses was continued for 72 weeks. The time-weighted average doses for the males were either 16,346 or 32,692 ppm, and those for the females were either 12,019 or 24,038 ppm. Matched controls consisted of 20 untreated mice of each sex. All surviving mice were killed at the end of the period of administration of the test chemical. Mean body weights of the high-dose male rats and of the low- and high-dose mice of each sex were lower than those of the corresponding controls; mean body weights of the low-dose male rats and of both the low- and high-dose female rats were essentially unaffected by administration of the test chemical. Depressions in the amount of body weight gained in the male and female mice were dose related throughout the bioassay. Survivals of the rats and mice were not affected by administration of the test chemical. No tumors occurred in the rats or mice of either sex at incidences that could be clearly related to the administration of the test chemical. It is concluded that under the conditions of this bioassay, phthalic anhydride was not carcinogenic for F344 rats or B6C3F1 mice of either sex.
Journal Article↗
[Specific serum IgG antibodies against phthalic anhydride in occupationally exposed workers].
Specific IgG antibodies against phthalic anhydride (PA) was determined in fifty heavily exposed workers, thirty non-exposed subjects and twelve patients with asthma as control groups. ELISA method was used by phthalic anhydride conjugated to human serum albumin antigen. The data demonstrated that specific IgG level was significantly increased only in heavily exposed workers. The average OD value was 0.6 +/- 0.47 (positive rate 78%), but 0.04 +/- 0.03 and 0.05 +/- 0.03 respectively in the two control groups. There was no association between the antibody level and clinical symptoms or the duration of exposure. The meaning of such increase requires further study. We believe, however, that in vitro specific IgG assay can be used as an indication of exposure to PA, or for etiological diagnosis of asthmatic patient and as a means to differential diagnosis.
Adult↗
Phthalic anhydride asthma.
A patient with occupational asthma caused by phthalic anhydride is described. Inhalation challenges under laboratory control produced immediate and delayed asthmatic responses. Repeat exposure to phthalic anhydride after treatment with cromolyn sodium showed inhibition of the late but not early bronchoconstrictive, asthmatic response.
Adult↗
Detection of specific IgE in isocyanate and phthalic anhydride exposed workers: comparison of RAST RIA, Immuno CAP System FEIA, and Magic Lite SQ.
Sera from 94 workers occupationally exposed to isocyanate were tested by RAST RIA, Immuno CAP FEIA, and Magic Lite SQ (ML) against the allergens HDI, MDI, TDI, and phthalic anhydride. Twenty sera showed increased levels of diisocyanate-specific IgE antibodies, and five sera were phthalic anhydride positive. High total IgE titer was not correlated with positive specific IgE titer (r = 0.47), showing that nonspecific IgE binding was low. The results of ML and CAP correlated well (r = 0.91), but tended to be slightly higher than the results obtained with the RAST isotope test. CAP and RAST data also correlated significantly (r = 0.90), but the correlation between ML and RAST data was lower (r = 0.82). The results of the new in vitro tests, CAP and ML, showed good reproducibility (5% CV for CAP and 8% CV for ML). In summary, the CAP and ML methods were found to be appropriate for routine diagnosis of specific IgE antibodies against the allergens HDI, MDI, TDI, and phthalic anhydride.
Adult↗
Mortality from lung cancer in an acetylene and phthalic anhydride plant. A case-referent study.
Mortality from lung cancer in an acetylene and phthalic anhydride plant: A case-referent study. Scand j work environ health 9 (1983) 455-462. The study tested the hypothesis that an excess of lung cancer observed in a small town of the Milano Province in Italy was attributable to occupational exposures in a chemical plant (SISAS) producing mainly acetylene, phthalic anhydride, and their derivatives. Exposures included a large number of chemicals, some of which are known or suspected carcinogens such as soot and phthalates. The local register of deaths was the source of the cases and referents. The cases (N = 43) were the male residents in the town who had died from lung cancer from 1976 to 1979. The referents were a sample of residents from the same town who had died during the same four-year period from causes other than respiratory cancer. Causes of death were validated through clinical data and relatives' reports. Information for a complete occupational history and on smoking habits was collected in interviews of the next of kin of each study subject. After control for age and smoking, the risk of dying from lung cancer for the subjects previously employed at the SISAS plant relative to those never occupationally exposed was 5.6 (95% confidence limits 1.9-16.2). The risk for exposure to lung carcinogens in work environments other than SISAS was 1.7 (95% confidence limits 0.9-3.5). On the whole, occupational exposure to chemical carcinogens accounted for about one-third of the total number of lung cancer deaths that occurred in the area during the study period. The results call for further investigation of specific chemicals, mainly soot and phthalates, in the etiology of lung cancer.
Acetylene↗
Effects of phthalic anhydride modification on horseradish peroxidase stability and activity.
Phthalic anhydride (PA) modification stabilizes horseradish peroxidase (HRP) by reversal of the positive charge on two of HRP's six lysine residues. Native and PA-HRP had half-inactivation temperatures of 51 and 65 degrees C and half-lives at 65 degrees C of 4 and 17 min, respectively. PA-HRP was more resistant to dimethylformamide at room temperature and tetrahydrofuran at 60 degrees C and to unfolding by heat, guanidine chloride, EDTA, and the reducing agent tris(2-carboxyethyl)phosphine hydrochloride. Binding of the hydrophobic probe Nile Red to the native enzyme and to PA-HRP was similar. The kinetics of both HRPs with the substrates ABTS, ferrocyanide, ferulic acid, and indole-3-propionic acid were measured, as was binding of the inhibitor benzhydroxamic acid. Small improvements in the catalytic properties were detected.
Binding Sites↗
Divergent immune responses to respiratory and contact chemical allergens: antibody elicited by phthalic anhydride and oxazolone.
In previous studies we observed that exposure of mice to the contact allergen 2,4-dinitrochlorobenzene (DNCB) and the respiratory allergen trimellitic anhydride (TMA) resulted in qualitatively different immune responses characteristic of selective Th1- and Th2-type T helper cell activation respectively. The purpose of the present investigation was to determine whether the effects recorded with DNCB and TMA are characteristic of immune responses to contact and respiratory chemical allergens in general. Experiments have been performed with phthalic anhydride, a known human respiratory sensitizer, and with oxazolone, a potent contact allergen. Under conditions of exposure where both chemicals elicited an IgG anti-hapten antibody response, only phthalic anhydride caused an increase in the serum concentration of IgE. Furthermore, like TMA, phthalic anhydride preferentially induced IgG2b rather than IgG2a antibody. In contrast, oxazolone, like DNCB, induced a markedly stronger IgG2a than IgG2b antibody response. These data provide confirmatory evidence that chemical respiratory allergens and chemical contact allergens elicit qualitatively different immune responses which reflect their clinical effects in man.
Allergens↗
[Formaldehyde and phthalic anhydride asthma. Demonstration of specific IgE antibodies with RAST].
Two patients with positive formaldehyde RAST and 3 with positive phthalic anhydride RAST are described, of whom 3 presented with a typical history of occupational asthma and one had only work-related rhinitis. The fifth case with specific IgE antibodies to formaldehyde had only a domestic exposure-effect relationship; asthmatic symptoms had first started some weeks after renovation of the patient's apartment. Thus far, failing proof of specific IgE antibodies, a true allergic reaction to formaldehyde in particular has been doubted. Presenting respiratory symptoms were considered to be probably due to irritant effects. The reported cases indicate that formaldehyde and phthalic anhydride may also exert their effect through immunologic mechanisms.
Adult↗
Solid-solid reaction between sulfacetamide and phthalic anhydride.
Thermal and kinetic data for the solid-state addition reaction of sulfacetamide and phthalic anhydride are presented. A compaction method was used so that the influence of some pharmaceutical parameters (compressional pressure, particle size, concentration, and temperature) on the reaction kinetics could be observed.
Chemical Phenomena↗
Establishing clinical and immunologic criteria for diagnosis of occupational immunologic lung disease with phthalic anhydride and tetrachlorophthalic anhydride exposures as a model.
Using a questionnaire and serum antibody studies, we evaluated 13 workers exposed to phthalic anhydride (PA) and tetrachlorophthalic anhydride (TCPA). The questionnaire was designed to identify symptoms compatible with anhydride-induced immunologic or irritant syndromes. Specific IgG and IgE for both PA-human serum albumin (PA-HSA) and TCPA-HSA were determined by enzyme-linked immunosorbent assay in two different laboratories. In addition, 11 workers had cutaneous testing with PA-HSA and TCPA-HSA, and nine workers were interviewed. One worker was found to have PA-associated asthma and rhinitis. We conclude that a questionnaire and serologic assays for specific IgG and IgE are helpful to identify workers who have or are at risk for developing occupational immunologic lung disease such as those induced by anhydrides. However, additional evaluation may be necessary in those workers with such diseases as intrinsic asthma that may be difficult to differentiate from occupational immunologic lung disease.
Air Pollutants, Occupational↗