Aromatic Amines An Assessment of the Biological and Environmental Effects (1981) / Chapter Skim
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2,4-Diaminotoluene
2,4-Diaminotoluene
Pages 198-227
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From page 198... ...
their estimated annual capacities (Chemical Economics Handbook, 1977-1978; Stanford Research Institute International 1979; United States International Trade Commission, 1979~.
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NIP 57a 30 Not 36 25 47 36 11 NOR 36 NIP 15 Estimates of production capacities are based on an assumed 2,4diaminotoluene capacity of O .8 mete ic tons for each aetr ic ton of eoluene diisocyanate capacity, except for Air Products and Cbemicals, Inc., which does not produce toluene diisocyanate. b Not repor ted .
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companies produced 284, 072 . 4 metr ic tons of the 80/20 toluene di isocyanate mixture in 1978 (International Trade Commission, 1978~.
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Table 8-2 Annual Production of 2, 4-DTa .
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Total Percent of Total 83% 6 3 8 100% a Data from Chemical Economics Handbook, 1977-1978.
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2,4-DT is used as a developer for direct dyes, particularly to obtain black, dark blue, and brown shades, and to obtain navy blue and black colors on leather. It is also used to dye furs and was an ingredient in hair dye formulations until banned in 1971 (International Agency for Research on Cancer, 19781.
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Because the vapor pressure of 2,4-DT is 11 mm Hg at 150°C and it is soluble in hot water, the separated water is undoubtedly highly contaminated. This wastewater is probably treated before it is discharged.
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From page 205... ...
Only partial resolution of the components was obtained. The other HPLC system, which consisted of a column of Chromosorb Si 100 loaded with a 21% octadecyl phase subjected to a 17-minute linear gradient from 5% to 40% acetonitrile in water (containing 1.2 and 2.4 g/1 of sodium biphosphate and sodium hypophosphate, respectively} was more successful: all nine components of the mixture were separated with essentially baseline resolution.
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Although the TLC system resolved for the six dye components, it was not suitable for the other compounds since sulfanilic acid was not resolved from one of the dye components. The two aromatic amines (2,6- and 2,4-DT)
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Examples of such systems are AG 1-X4 (CH3co2-) developed with 0.1 mol acetate buffer in a 4:1 water-methanol mixture; BD-cellulose developed with 0.5 mol acetate buffer solution; Dowex 50-X4 (H+)
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From page 208... ...
discussions in the literature (details unavailable) involve in situ TLC determinations of toluenediamine and methylenedianiline isomers in the products of hydrolytic degradation of polyurethanes (Lesiak and Orl ikowska, 1978 ~ and an ultrasonic method to assay amine !
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The liver cytosol f rom hamsters had the most enzymat ic activity followed by guinea-pig, rabbit, mouse and rat. Human liver cytosol formed only trace amounts of acetyl derivatives while dog liver cytosol had no 209
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No information is available on the mechanism of metabolic activation of 2,4-DT. Acute Toxicity National Institute of Occupational Safety and Health (1979 } reported that the oral LDLo (lowest published lethal dose)
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Hey observed carcinoma of the liver in male Wistar rats fed diets containing 600 or 1,000 ppm 2,4-DT for 33 to 34 weeks e Tumor incidences at 36 weeks were 9/9 (1001) after a dosage of 1,000 ppm 2,4-DT and 7/11 (64%)
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From page 212... ...
These included lung tumors, squamous cell carcinoma of the skin and preputial gland, pancreatic acinar cell adenomas, subcutaneous f ibromas and f ibrosarcomas, and mesotheliomas. In parallel studies, groups of 50 B6C3F1 mice of each sex rece ived 2, 4-DT in feed at two dose levels, either 100 ppm or 200 ppm, for 101 weeks.
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and in the micronucleus test in the rat tHossack and Richardson, 1977~. Potentially genotoxic effects (chromatic and chromosomal gaps and breaks in peripheral lymphocytes)
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aelanogaster, Oregon X, Berlin K pOnc Fahmy and Fahmy, 1977 Blijleven, 1977 Chromosome Damage Micronucleus test in rat Chromosome damage humans a Mutagenic in the presence of S-9 (metabolic activation) b Tested without metabolic activation.
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(1977) reported a correlation between the 2,4-DT-induced morphologic transformation in an In vitro carcinogenesis system (using secondary culture target cells prepared from cryopreserved, primary Syrian hamster embryo cells)
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Mossack and Richardson t1977) obtained negative results in micronucleus tests of 2,4-DT and 11 other hair dye constituents.
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whose hair was not dyed. Possible confounding factors in these findings are that most tinters wear gloves when applying hair dyes and, even without gloves, percutaneous absorption of ha ir dye constituents may be effectively impeded by the horny surface of the bands and by the lack of sebaceous glands in the palms ; ha ir dye constituents are readily absorbed through the scalp, which contains numerous sebaceous glands; and the lower frequency of chromosomal aberrations in young men with dyed hair (compared with the frequency in slightly older men without dyed hair)
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It also induces cell transformation in an _ vitro mammalian carcinogenesis test system. However, there are no data, such as case reports or epidemiologic studies, on the carcinogenicity of 2,4-DT in humans.
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Recommendations for future research with 2,4-DT include studies of the mechanism by which the chemical is activated in rats, mice and humans, testing for carcinogenicity in additional species to obtain more data on the relationship between metabolism and carcinogenicity, and examination of the in vitro metabolism of 2,4-DT in human tissues to supplement the preliminary observations of Glinsukon et al.
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1980. Stanford Research Institute International, Menlo Park, Calif .
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UPS. International Trade Commission.
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1968. Determination of isomeric diaminotoluenes by direct gas-liquid chromatography.
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1968. Direct gas chromatographic analysis of i~omeric diaminotoluenes.
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1976. Dermal carcinogenicity study by mouse-skin painting with 2,4-toluenediamine alone or in representative hair dye formulations.
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1977. Examination of the potential mutagenicity of hair dye constituents using the micronucleus test.
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1978. Chromosomal damage and hair dyes.
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1955. Production of rat sarcoma by injections of propylene glycol solution of m-toloylenediamine.
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