isothiazolinone

Isothiazolinone is a heterocyclic compound used as a biocide

. Here is an introduction to it:

Basic Information

  • Formula and Structure: The general formula is , and its molecular weight is 264.75226
  • . It exists in the form of white solid, structurally related to isothiazole.
  • Production Method: It can be prepared on an industrial scale by the ring - closure of 3 - mercapto propanamides, which are produced from acrylic acid via 3 - mercaptopropionic acid. The ring - closure of the thiol - amide is typically effected by chlorination or oxidation of the 3 - sulfanyl propanamide to the corresponding disulfide.

Main Derivatives

  • Methylisothiazolinone (MIT): It is one of the commonly used derivatives, often used in combination with other substances.
  • Chloromethylisothiazolinone (CMIT): Usually used in a mixture with MIT, such as a 3:1 mixture of CMIT:MIT sold as Kathon.
  • Benzisothiazolinone (BIT): It has good antibacterial properties and is widely used in industrial fields.
  • Octylisothiazolinone (OIT): It is often used in antifouling agents and some coatings.
  • Dichloro - octyl - isothiazolinone (DCOI): Especially used as an antifouling agent, such as paint for ship hulls.

Properties and Applications

  • Antimicrobial Properties: It can inhibit life - sustaining enzymes, especially those with thiols at their active sites, thus having strong antimicrobial activity against bacteria, fungi, and algae. It is widely used in cooling water systems, fuel storage tanks, pulp and paper mill water systems, oil extraction systems, and wood preservation to control microbial growth.
  • Use in Personal Care Products
  • : It is frequently used in shampoos and other hair care products as a preservative to prevent microbial contamination.
  • Isothiazolinone Use in Coatings
    • : It can be added to certain paint formulations to improve the antibacterial and antifungal properties of the paint and extend its service life.

    Safety Issues

    • Aquatic Toxicity: Isothiazolinones have high aquatic toxicity and pose a threat to various marine invertebrates and fish.
    • Allergic Reactions: Some derivatives, such as CMIT, can cause hypersensitivity by direct contact or via the air. MIT is often used in combination with CMIT, and sensitization to this family of preservatives has been observed since the late 1980s. In 2013, the substance was declared the contact allergen of the year by the American Contact Dermatitis Society.

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