General Description

2,2'-Dithiobis(benzothiazole) is a versatile compound with various properties and applications. It has excellent solubility in rubber polymers, ensuring uniform distribution and enhancing performance. It offers heat resistance and aging stability, maintaining rubber properties over time. Additionally, it is non-staining and non-discoloring, making it suitable for light-colored rubber products. DBTH is widely used as a rubber accelerator in tire manufacturing, conveyor belts, and shoe soles. It also serves as a corrosion inhibitor in metalworking fluids and lubricants. Moreover, it is a chemical intermediate in the production of dyes, pharmaceuticals, and agrochemicals. However, toxicity studies indicate potential harmful effects and the need for further investigation. Overall, 2,2'-Dithiobis(benzothiazole) is a valuable compound in the rubber industry and other sectors.

Figure 1. 2,2'-Dithiobis(benzothiazole)

Properties

2,2'-Dithiobis(benzothiazole) possesses several notable properties that contribute to its effectiveness in rubber applications. Firstly, it has excellent solubility in various rubber polymers, enabling easy incorporation into rubber compounds. This property ensures uniform distribution throughout the material, enhancing its overall performance. Secondly, MBTS exhibits moderate reactivity, allowing it to promote the vulcanization process at a controlled rate. Its ability to facilitate the cross-linking of polymer chains enhances the mechanical strength, elasticity, and durability of rubber products. Additionally, MBTS offers good heat resistance and aging stability to rubber compounds. This property ensures that the vulcanized rubber maintains its properties over an extended period, even under high-temperature conditions or exposure to environmental factors. Furthermore, it is worth mentioning that MBTS is non-staining and non-discoloring, making it suitable for light-colored or white rubber products where visual aesthetics are important. In summary, 2,2'-Dithiobis(benzothiazole) possesses desirable properties such as good solubility, controlled reactivity, heat resistance, and non-staining characteristics, making it a valuable accelerator in the rubber industry. ¹

Applications

2,2'-Dithiobis(benzothiazole) (DBTH) finds various applications in different industries. One of its primary uses is as a rubber accelerator in the production of vulcanized rubber products. DBTH enhances the curing process by promoting crosslinking between rubber molecules, resulting in improved strength, elasticity, and durability of rubber materials. It is commonly employed in the manufacturing of automotive tires, conveyor belts, shoe soles, and other rubber goods. In addition to its role in rubber production, DBTH is utilized as a corrosion inhibitor in metalworking fluids and lubricants. It provides protection against corrosion by forming a protective film on metal surfaces, preventing oxidation and degradation. This application is particularly important in industries such as automotive, aerospace, and machinery, where metal components are exposed to harsh environments or corrosive substances. Moreover, DBTH is employed as a chemical intermediate in the synthesis of various organic compounds. It serves as a building block for the production of dyes, pharmaceuticals, and agrochemicals, contributing to the development of these industries. Overall, 2,2'-Dithiobis(benzothiazole) plays a critical role in the rubber industry, acts as a corrosion inhibitor, and serves as a versatile chemical intermediate in different sectors, supporting advancements in technology, infrastructure, and various other applications. ²

Toxicity

2,2'-Dithiobis(benzothiazole) is one of the twelve benzothiazole compounds that were evaluated for their toxic potential in a study. The research focused on two rainbow trout epithelial cell lines, RTgill-W1 and RTL-W1, to assess the toxicological effects of these BTHs. Results showed that most of the tested BTHs, including DBTH, exhibited cytotoxicity and caused a temporary increase in reactive oxygen species (ROS) levels, except for N,N-dicyclohexyl-2-benzothiazolsulfene amide (NNA), DBTH, and 2-(p-aminophenyl)-6-methylbenzothiazole-7-sulfonic acid (MBTHS).Interestingly, neither N-acetyl cysteine (NAC) nor IM-54 was able to inhibit the cytotoxicity caused by these BTHs, suggesting that the imbalance of ROS did not contribute to cell death. Furthermore, exposure to 2-aminobenzothiazole (2ABTH) and 2-hydroxy-benzothiazole (OHBTH) led to DNA strand breaks after 1 day of exposure, while benzothiazole (BTH) caused DNA strand breaks after 12 days of exposure. This suggests that these BTHs have the potential to alter xenobiotic metabolism and activate the aryl hydrocarbon receptor. Overall, the study highlights the toxic actions of certain BTHs in vitro, including 2,2'-Dithiobis(benzothiazole), and emphasizes the need for further investigation of these BTHs in vivo. ³

Reference

1. Jung JH, McLaughlin JL, Stannard J, Guin JD. Isolation, via activity-directed fractionation, of mercaptobenzothiazole and dibenzothiazyl disulfide as 2 allergens responsible for tennis shoe dermatitis. Contact Dermatitis, 1988, 19(4):54–259.

2. Chipinda I, Hettick JM, Simoyi RH, Siegel PD. Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Chem Res Toxicol. 2007 Aug;20(8):1084-1092.

3. Zeng F, Sherry JP, Bols NC. Evaluating the toxic potential of benzothiazoles with the rainbow trout cell lines, RTgill-W1 and RTL-W1. Chemosphere. 2016 Jul;155:308-318.