Dyestuff Intermediates Research Articles

Sulfonamide based antimicrobial reactive dyes: A study of their synthesis, fastness and antimicrobial activity

The cellulosic fiber dyeing, and antimicrobial finishing are two energy extensive processes. In the present study, an attempt has been made to combine these two processes, which would in turn save time, energy, and cost. In this regard, a new series of reactive dyes (SM1-SM6) has been synthesized using antimicrobial sulfonamide components as dyestuff intermediates. The resultant dyes were characterized through different spectroscopic techniques, and evaluated for build-up profile and different color fastness properties. Pharmacological activities of synthesized dyes against S. aureus, E. coli, and C. albicans were investigated and showed moderate to good antibacterial and antifungal activity. The dyes SM5 and SM3 exhibited maximum inhibition against S. aureus and E. coli respectively (around 76.66%). Samples dyed with SM4 displayed the most effective zone of inhibition i.e., 30.03 ± 0.31 mm against E. coli while SM5 showed highest zone of inhibition against C. albicans measured as 28.00 ± 0.28 mm.

Biotreatment of sulfonated dyestuffs with energy recovery in microbial fuel cell: Influencing parameters, kinetics, degradation pathways, mechanisms, and phytotoxicity assessment

Removal of recalcitrant sulfonated dyestuff intermediates from wastewater has been an urgent challenge for environmental technologies. In this regard, the biodegradations of monoazo Methyl Orange (MO) and diazo dyes Reactive Black 5 (RB5) towards wastewater treatment and bioelectricity generation in microbial fuel cell were investigated and compared through the studies on azo dye concentration, aeration, sampling points arrays, and electrode spacings. The degradation of diazo RB5 yielded higher chemical oxygen demand removal, decolourization efficiencies, and power generation over monoazo MO. The decolourization efficiency of RB5 (97.62%) increased with an increase of RB5 concentration (50 mg/L), suggesting that the system has the capability of removing higher RB5 concentration. However, contrary results were obtained with MO due to its toxicity. This study also demonstrated that the decolourization rate of diazo RB5 (0.1533 h−1) was ≈ 53% higher than monoazo MO (0.0727 h−1). The findings revealed that the degradation kinetic was remarkably influenced by the chemical structure of dye, where dye with more electron-withdrawing groups at para position are more susceptible to be reduced. Higher output voltage (568.59 mV) and power generation (108.87 mW/m2) were attained with RB5 due to electron donor availability and electron-shuttling characteristics of RB5 decolourized intermediates. Furthermore, detailed degradation pathways of MO and RB5 were presented based on the UV–vis and GC-MS results. The phytotoxicity assessment via Sorghum bicolor seeds had further verified the reduction in toxicity after the treatment of azo dyes.

Preliminary Investigation of Kaduna-Grown Cashew Nutshell Liquid as a Natural Precursor for Dyestuffs, Pigments and Binders for Leather Finishing

The ever-increasing cost of petroleum based products and the increasing environmental concerns and legislation worldwide are forcing industries to look for inexpensive, renewable, locally available and environmentally friendly raw materials. Cashew (Anacardium occidentale) nutshell liquid (CNSL) is one such material that can be polymerized compared to simple phenols from petrochemicals, which have restrictions. CNSL was extracted from cashew nuts purchased from local farmers in Kaduna, Kaduna state (North of Nigeria) using n-Hexane. The crude extract was analyzed for Iodine Value (88mgI 2 /100g), Acid value (141mgKOH/g), Saponification Value (53mgKOH/g), Refractive Index (1.689 @ 25 0 C) and pH (3). The results show that CNSL from the Kaduna-grown cashew nuts is a semi-drying oil and suitable for the synthesis of resins and dyestuff intermediates. It, therefore, has a great potential as a natural precursor for dyestuff, pigments and binders for leather finishing.

Structural analysis of sulfonated monoazo dyestuff intermediates by electrospray tandem mass spectrometry and matrix-assisted laser desorption/ionization post-source decay mass spectrometry

Sulfonated azo molecules containing hydroxy groups ortho- or para- to the azo linkage exhibit azo/hydrazone tautomerism, which affects their coloristic properties and also the fragmentation pathways observed in tandem mass spectrometry. Electrospray tandem MS and matrix-assisted laser desorption/ionization post-source decay are used in this work to study the fragmentation mechanisms of such molecules. The two techniques show closely matching product ion distributions, the predominant fragmentation pathways depending on the extent of tautomerism in each molecule. Evidence of tautomerism is afforded by comparing the product ions of the hydroxyazo molecules with their methoxyazo analogues where tautomerism is not possible. Keto-tautomers show cleavage of the single N–N bond whereas the azo forms dissociate via the azo C–N bonds, followed in both cases by neutral losses of SO2. In addition, the simple introduction of a nitro group on a naphthyl group in an azo dye is shown to have a marked influence on its observed fragmentation. © 1998 John Wiley & Sons, Ltd.

FACTORS AFFECTING THE OCCURRENCE OF UROTHELIAL TUMORS IN DYE WORKERS EXPOSED TO AROMATIC MINES

Past studies have analyzed individual jobs in dyestuff factories, materials manufactured and handled, age at exposure, and the duration of exposure in factories as factors related to the occurrence of urothelial tumors. None of these studies was based on long-term observation, and the factors involved in the occurrence of urothelial tumors remain controversial. In this study, various factors that may affect the occurrence of urothelial tumors in dye workers were assessed by multivariate analysis. Three hundred and sixty-three workers in nine member factories of the Dyestuff Industrial Cooperative Association were included the study. Factory A is a large dyestuff chemical factory in Wakayama City with 218 dye workers. The other eight smaller factories employ a total of 145 dye workers. Correlations of tumor occurrence with a variety of factors, such as dyestuff intermediates manufactured and handled, types of job in the factory, age at the beginning of occupational exposure, and the duration of exposure were examined by multivariate analysis using multiple logistic models. Urothelial tumors were found in 58 (16.0%) of the 363 dye workers in the nine member factories of the Cooperative Association examined in the present study. The incidence in workers in Factory A, 5.5% (12 patients), was significantly (P < 0.01) lower than the overall incidence, while that in the eight small factories, 31.7% (46 patients), was significantly (P < 0.01) higher than the overall incidence. The risk factors significantly related to tumor occurrence in the 363 dye workers were benzidine (odds ratio, 8.302) as a dyestuff intermediate, manufacturing work (odds ratio, 4.631), and a long period of exposure (odds ratio, 1.018). Correlations of the tumor occurrence with the various factors were examined by multivariate analysis using multiple logistic models. In the total of 363 workers, benzidine as an intermediate (P < 0.05), manufacturing work (P < 0.01) and the duration of exposure (P < 0.01) were found to have contributed to the urothelial tumor occurrence. In Factory A, benzidine as an intermediate (P < 0.01) and duration of exposure (P < 0.05) contributed significantly to tumor occurrence. 1) The manufacturing and handling of benzidine and duration of exposure contribute significantly to the occurrence of occupational urothelial tumor, the former more strongly than the latter; 2) the contribution of different job types to tumor occurrence may be dependent upon the industrial health and safety practices in each factory.

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. Part I. The role of aniline, benzidine, alpha-naphthylamine, and beta-naphthylamine. 1954.

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. Part I. The role of aniline, benzidine, alpha-naphthylamine, and beta-naphthylamine. 1954.

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry

A fast‐atom bombardment tandem mass spectrometry screening procedure for the presence of involatile sulphonated dyestuff intermediates

AbstractThe introduction of more rigorous regulations aimed at controlling the use of sulphonated dyestuffs and dyestuff intermediates has pointed to the need for screening methods for the presence of these involatile compounds. Although much work has been caried out recently on the mass spectrometric behaviour of these compounds, it has been concerned principally with the production of molecular weight information using novel ionization methods rather than with any attempt to obtain structurally diagnostic fragment ions. In this mass spectrometric investigation of a range of naphthalene sulphonic acid salts, positive‐ion and negative‐ion fast‐atom bombardment (FAB) mass spectra have been obtained and FAB‐tandem mass spectrometry (MS/MS) has been used to acquire spectra (daugher‐ion, parent‐ion and neutral‐loss) in an attempt to develop a useful screening method. On known compounds, best results were found when using a negative‐ion neutral‐loss scan to detect the loss of 64 mass units (corresponding to loss of SO2). This was confirmed by successful use of this scan to screen a sample of sulphonate residues.

OSHA takes new route to exposure limits

The Occupational Safety & Health Administration's first formal attempt at mediated rulemaking has resulted in publication of a proposed rule limiting workers' exposure to 4,4'- methylenedianiline (MDA), a hepatotoxin and potential human carcinogen, to 10 ppb averaged over eight hours. The current limit is 100 ppb. OSHA estimates that about 4000 workers are exposed to MDA. The agency expects the proposed standard to prevent from two to 23 cancer deaths per year, as well as reduce liver damage. Six U.S. companies produce about 605 million lb of MDA annually, according to OSHA, with 98% being used directly in the manufacture of methylenediphenyl diisocyanate, a component of urethane resins. The remaining 2% is used as a precursor in the manufacture of plastic fibers, antioxidants, dyestuff intermediates, and composite materials. OSHA says it will cost industry about $8.2 million per year to comply with the proposed standard. The proposed rule is based on the consensus recommendations of ...

Proton magnetic resonance spectra of some naphthalene derivatives

Abstract The chemical shifts of the ring protons of some monosubstituted naphthalenes were assigned from 250 MHz spectra, and the assignments were used to assist in the interpretation of the spectra of a number of naphthalene sulfonic acids which are commonly used as dyestuff intermediates. A table of parameters is presented which would assist in the identification of complex azo dyes that are derived from these naphthalene derivatives.

ROLE OF N-ACETYLTRANSFERASE PHENOTYPES IN BLADDER CARCINOGENESIS: A PHARMACOGENETIC EPIDEMIOLOGICAL APPROACH TO BLADDER CANCER

A large excess of patients with bladder cancer who have previously been exposed to N-substituted aryl compounds as a result of the production of dyestuff intermediates have the slow phenotype of the enzyme N-acetyltransferase. Among bladder-cancer patients in general, those presenting with T3 or T4 disease or carcinoma-in-situ also show an excess of the slower subtypes. Either N-substituted aryl compounds more frequently produce tumours with this invasive potential if linked with slow acetylation or slow acetylators are more susceptible to tumour production when exposed to some N-substituted aryl compounds. It is suggested that acetylator status could be used to identify susceptible individuals in potentially hazardous occupations.

Carcinogenicity of dyestuff intermediates: Murthy, A. S. K., Russfield, A. B., Hagopian, M., Monson, R., Snell, J. & Weisburger, E. K. (1979). Carcinogenicity and nephrotoxicity of 2-amino-1-amino-2-methyl-, and 2-methyl-1-nitro-anthraquinone. Toxicology Lett.4, 71

Carcinogenicity of dyestuff intermediates: Murthy, A. S. K., Russfield, A. B., Hagopian, M., Monson, R., Snell, J. & Weisburger, E. K. (1979). Carcinogenicity and nephrotoxicity of 2-amino-1-amino-2-methyl-, and 2-methyl-1-nitro-anthraquinone. Toxicology Lett.4, 71

膀胱がん発生機作

Since the discovery of industrial bladder cancer by Rehn in 1895, many incidences of the occupational bladder cancer have been reported with the progress of dyestuff industry. On the other hand, various industrial bladder carcinogens have been found in aromatic amines of dyestuff intermediates experimentally and epidemiologically. The biochemical mechanisms that the metabolites of the parent aromatic amines have more potent carcinogenic action than the parent chemicals have been found. From these findings, some chemicals being slightly changed in their chemical structure were produced and it was found that these chemicals were usefull for dyestuff intermediates as well as quite safe for cancer induction. It is very necessary for the prevention that new aromatic amines should be checked in order to know whether they are carcinogenic or not. From this point of view, 5-aminoacenaphtene and 5-nitroacenaphthene, the intermediates of fluorescent whitening agents, were examined by the author, and it was proved experimentally that these new aromaiic amines have carcinogenic action to mice.

環境中の芳香族アミン類の検出法について

There are some aromatic amines of which carcinogenesity was proved experimentally. These were recognized as such also from the fact that the industrial cancer was associated with the manufacture of some aromatic amines used as dyestuff intermediates. The most hazardous aromatic amines as the intermediates are such as α-naphthylamine, β-naphthylamine and benzidine. The environmental hygienic conditions are necessary for the prevention of industrial cancer in dyestuff factories. Therefore, it is of importance to know how much the environment of the factory is polluted by these amines. In Great Britain, at the same time when the Association of British Chemical Manufacturers sponsored a major research project on the industrial bladder tumour in the chemical industry in 1947, analytical methods for the determination of the most carcinogenic amines, namely benzidine and β-naphthylamine, were required. Considerable research was done and led to the development of sensitive methods for the determination of the amines in plant atmospheres, plant deposits, and on worker's clothings. In the laboratory of our department, these analytical methods were modified and new methods by collumn and thin layer chromatography were added to them for the determination of these amines. These methods can be used in dyestuff, pigment and rubber factories.

Industrial Poisoning by Dyestuff Intermediates

Industrial Poisoning by Dyestuff Intermediates

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. II. Further consideration of the role of aniline and of the manufacture of auramine and magenta (fuchsine) as possible causative agents.

In a previous communication (Part I) on occupa tional bladder tumours (Case, Hosker, McDonald, and Pearson, 1954), the primary object was to consider the statistical evidence which had been collected about the manufacture and use of the dyestuff intermediates aniline, benzidine, a naphthylamine, and ?-naphthylamine, and their relation to occupational tumours of the urinary bladder. It was concluded that aniline manufacture and use were probably not a cause of the disease, but that certain aniline workers who were employed in the manufacture of magenta (fuchsine) might be in some danger of developing occupational bladder tumours. At the same time it was suggested that the manufacture of auramine might also be a source of danger, and arrangements were made for a more detailed investigation of the occurrence of bladder tumours in workmen exposed to the manufacture of magenta, in which process aniline is necessarily used, and the manufacture of auramine, where aniline is not used. This investigation, being part of the A.B.C.M. Papilloma Research Scheme (Association of British Chemical Manufacturers, 1953), was of necessity confined to the same firms as had hitherto been investigated and the data relate only to the manu facture of magenta and auramine. These substances differ from the other substances so far studied

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. I. The role of aniline, benzidine, alpha-naphthylamine, and beta-naphthylamine.

Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. I. The role of aniline, benzidine, alpha-naphthylamine, and beta-naphthylamine.

Infrared Spectra of Dyestuff Intermediates

Infrared Spectra of Dyestuff Intermediates

The Chemical Age Year Book, Diary and Directory, 1927

IN addition to a very convenient diary, this book contains information of special interest to the chemist. Short notices are given of such subjects as research organisations, chemical and allied societies, patenting of invention, use of industrial chemicals, trade name of dye-stuff intermediates, certain stock-exchange prices, etc. Various tables of constants and chemical data are included. A chemical directory and a number of trade advertisements form a large part of the volume. At the present time there are so many excellent collections of physical and chemical constants available that the advisability of including such information, especially in an abridged form as in this diary, may be doubted. On the whole, however, the material selected for inclusion takes up only a small portion of the book, and the data may have definite value in special circumstances. The binding and general appearance of the book are excellent. This may partly justify the price, which is rather high compared with that of diaries generally. The Chemical Age Year Book, Diary and Directory, 1927. Pp. 155 + Diary. (London: Benn Bros., Ltd., 1927.) 10s. 6d. net.