Benzisothiazolin-3-one
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Benzisothiazolinone (BIT) is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula C6H4SN(H)CO. A white solid, it is structurally related to isothiazole, and is part of a class of molecules called isothiazolinones. BIT is widely used as a preservative and
antimicrobial An antimicrobial is an agent that kills microorganisms (microbicide) or stops their growth (bacteriostatic agent). Antimicrobial medicines can be grouped according to the microorganisms they are used to treat. For example, antibiotics are used aga ...
.


Usage

Benzisothiazolinone has a microbicide and a
fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...
mode of action. It is widely used as a
preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or ...
, for example in: * emulsion paints,
caulk Caulk (also known as caulking and calking) is a material used to Seal (mechanical), seal Joint (building), joints or seams against leakage in various structures and piping. The oldest form of caulk consisted of fibrous materials driven into ...
s,
varnish Varnish is a clear Transparency (optics), transparent hard protective coating or film. It is not to be confused with wood stain. It usually has a yellowish shade due to the manufacturing process and materials used, but it may also be pigmente ...
es,
adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...
s, inks, and photographic processing solutions * home cleaning and car care products; laundry detergents, stain removers and fabric softeners; * industrial settings, for example in textile spin-finish solutions, leather processing solutions, preservation of fresh animal hides and skins * agriculture in pesticide formulations * gas and oil drilling in muds and packer fluids preservation. In
paints Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...
, it is commonly used alone or as a mixture with methylisothiazolinone. Typical concentrations in products are 200–400  ppm depending on the application area and the combination with other biocides. According to a study in Switzerland, 19% of the paints, varnishes and coatings contained BIT in 2000. The fraction in adhesives, sealants, plasters and fillers was shown at that time as 25%. A later study in 2014 shows a dramatic rise in usage, to 95.8% of house paints. Home cleaning and other care products that are high in water are easily contaminated by microorganisms, so isothiazolinones are often used as a preservative in these products because they are good at combatting a broad array of bacteria, fungi, and yeasts. A Swiss investigation found that BIT is used in concentrations between 50 and 500 ppm in tattooing ink. According to regulations in the EU and Switzerland, BIT cannot be used in cosmetics. However, it is allowed in the United States and Canada.


Health hazards

Given sufficient dose and duration, dermal exposure can produce skin sensitization and allergic contact dermatitis, and is classified as an irritant for skin and eyes. BIT's low molar mass allows for it to penetrate the epidermis and then react with the skin macromolecules, which causes the irritation. Benzisothiazolinone has also been linked with Systemic Contact Dermatitis via airborne contact. In 2012, the Scientific Committee on Consumer Safety in Europe found BIT's "sensitising potential is of concern...Sensitisation from related isothiazolinones is an important problem in consumers. This has occurred because there has been consumer exposure before safe levels of exposure relevant to sensitisation have been established. Benzisothiazolinone is a skin sensitiser in animal models with potency similar to methylisothiazolinone. Methylisothiazolinone, at 100 ppm (0.01%) in cosmetic products is causing contact allergy and allergic contact dermatitis in the consumer. Benzisothiazolinone is known to be a sensitiser in man and has induced sensitisation at circa 20 ppm in gloves." The opinion further states: "There is no information on what may be safe levels of exposure to benzisothiazolinone in cosmetic products from the point of view of sensitisation. Until safe levels of exposure have been established, the use of benzisothiazolinone in cosmetic products as a preservative or for other functions cannot be considered safe in relation to sensitisation." Later, in 2013, researchers published a study that set out to derive the highest concentration of BIT in certain consumer products that would result in exposures below the No Expected Sensitization Induction Level (NESIL); that is, where normal use would yield a dose below the level at which skin sensitization might occur. The products under consideration were
sunscreen Sunscreen, also known as sunblock, sun lotion or sun cream, is a photoprotection, photoprotective topical product for the Human skin, skin that helps protect against sunburn and prevent skin cancer. Sunscreens come as lotions, sprays, gels, fo ...
,
laundry detergent Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form. While powdered and liquid detergents hold roughly equal share of ...
, dish soap, and spray cleaner; by way of calculation they derived BIT NESILs of 0.0075%, 0.035%, 0.035%, and 0.021%, respectively. They then performed a pilot examination via bulk sample analysis of one representative product from each category labelled as containing BIT. Their findings showed all BIT concentrations well below the derived NESIL, with 0.0009% and 0.0027% for sunscreen and dish soap, respectively, and no detection in the laundry detergent and spray cleaner products, meaning the concentration was at or below the limit of detection of 0.0006%.


References


Literature

* Wilfried Paulus: ''Directory of Microbicides for the Protection of Materials and Processes''. Springer Netherland, Berlin 2006, .


External links

*{{Commons-inline Preservatives