Benzisothiazolin-3-one
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Benzisothiazolinone (BIT) is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with the formula C6H4SN(H)CO. A white solid, it is structurally related to
isothiazole An isothiazole, or 1,2-thiazole, is a type of organic compound containing a five-membered aromatic ring that consists of three carbon atoms, one nitrogen atom, and one sulfur atom.''Heterocyclic Chemistry'', 3rd Edition, J.A. Joule, K. Mills, and ...
, 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 or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
.


Usage

Benzisothiazolinone has a
microbicide An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ...
and a fungicide 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 by ...
, for example in: * emulsion paints,
caulk Caulk or, less frequently, caulking is a material used to seal joints or seams against leakage in various structures and piping. The oldest form of caulk consisted of fibrous materials driven into the wedge-shaped seams between boards on ...
s, varnishes, adhesives, 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 any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...
, it is commonly used alone or as a mixture with
methylisothiazolinone Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications ...
. 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,
sealant Sealant is a substance used to block the passage of fluids through openings in materials, a type of mechanical seal. In building construction ''sealant'' is sometimes synonymous with '' caulking'' and also serve the purposes of blocking dust, so ...
s, 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 preservatives 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,
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 o ...
,
dish soap Dishwashing liquid (or washing-up liquid in British English), also known as dishwashing soap, dish detergent, and dish soap is a detergent used to assist in dishwashing. It is usually a highly-foaming mixture of surfactants with low skin irr ...
, and spray cleaner; by way of calculation they derived BIT NESILs of 0.0075%, 0.035%, 0.035%, 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 category-inline, Benzoisothiazolinones Preservatives