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Octhilinone is a member of the class of 1,2-thiazole that is 1,2-thiazol-3-one substituted on the nitrogen (position 2) by an octyl group. A fungicide and antibacterial agent, it is used for treatment of canker and other fungal and bacterial diseases in fruit trees.
CAS No: 26530-20-1
2-Octyl-3(2H)-isothiazolone; 2-Octyl-4-isothiazolin-3-one; 2-n-Octyl-4-isothiazolin-3-one; Kathon 4200; Kathon 893; Kathon 893F; Kathon LM; Kathon LP preservative; Kathon SP 70; Micro-chek 11; Micro-chek 11D; Micro-chek skane; Microbicide M-8; Octhilinone; Pancil; Pancil-T; RH 893; Skane 8; Skane M-8; Skane M8; Vinylzene IT 3000DIDP; 2-Octyl-2H-isothiazol-3-one; 2-Octyl-3-isothiazolone; 3(2H)-Isothiazolone, 2-octyl-; 4-Isothiazolin-3-one, 2-octyl; Octhilinone; 2-n-Octyl-4-isothiazolin-3-one; 2-Octyl-4-isothiazolin-3-one; 2-octylisothiazol-3(2H)-one; 2-Octyl-3-isothiazolone; Pancil; 2-Octyl-2H-isothiazol-3-one; 3(2H)-Isothiazolone, 2-octyl-; 2-Octyl-3(2H)-isothiazolone; Skane 8; Skane M-8; Kathon 893F; Micro-chek skane; Kathon LM; Microbicide M-8; 2-octyl-1,2-thiazol-3-one; Micro-chek 11; Micro-chek 11D; Kathon SP 70;Kathon LP preservative; Kathon 4200; 4-Isothiazolin-3-one, 2-octyl-; UNII-4LFS24GD0V; Octyl-3(2H)-isothiazolone; 2-Octyl-3-isothioazolone; 2-Octyl-3-isothiazolinone; Octyl-4-isothiazol-3-one; 2-n-Octyl-3-isothiazolone; Skane M8; Caswell No. 613C; Kathon; Vinylzene IT 3000DIDP; RH 893; 2-octyl-1,2-thiazol-3(2H)-one; Skane M 8; 2-Octyl-4-Isothiazolin-3-Ketone; ZINC2012904; Tox21_201459; Tox21_300566; ANW-26014; MFCD00072473; RH-893; Octhilinone 10 microg/mL in Acetonitrile; 2-Octyl-3(2H)-isothiazolone, Octhilinone; 2-Octyl-4-isothiazolin-3-one, PESTANAL(R), analytical standard; Octhilinone ; 2-Octyl-3(2H)-isothiazolone; 2-Octyl-2H-isothiazol-3-one; Octyl-3(2H)-isothiazolone;
Assay: 45% ；98%
Appearance: Yellowish transparent thick liquid
Capacity: 5000MT per year
Packaging: 1000 kg per IBC drum, 200 kg per drum
2-Octyl-4-isothiazolin-3-one Details:
Chemical name: 2-Octyl-4-isothiazolin-3-one
Molecular formula: C11H19NOS
Molecular weight: 213.34
Applying Wood Preservatives
Railroad ties, marine pilings, fence posts, and telephone poles may be pressure treated with creosote, pentachlorophenol, and ammoniacal copper arsenate (ACA) or chromated copper arsenate (CCA).
Pentachlorophenol, creosote, and chromated copper arsenate were banned for sale in the United States to consumers as wood preservatives. CCA is still used commercially as a wood preservative
Leather Tanning and Processing
Tanners may be exposed to chromium, sulfuric acid, leather dust, and H2S. Tanning uses either vegetable or chromium (III) solutions. Other potential exposures include: nitrosamines, chromate pigments, benzidine-based dyes, formaldehyde, and aromatic organic solvents. Calcium oxide is a dehairing agent. Hydrogen sulfide can evolve if acid reacts with sodium sulfide, also used for dehairing. Ammonia is generated from ammonium buffering salts and protein putrefaction. Various biocides are used. Leather tanning and processing is not classifiable as to carcinogenicity to humans. Leather production includes hide preparation, tanning, and finishing. Preparation chemicals include DDT, zinc chloride, formaldehyde, mineral oils, arsenious anhydride, and phenols.
Tanning chemicals include calcium hydroxide, sodium sulfide, sulfuric acid, formic acid, hydrogen sulfide, aniline-based dyes, and solvents (dichloromethane, benzene, ethanol, tetrachloroethane, trichloroethylene). Finishing chemicals include formaldehyde, aniline, nitrocellulose, and resins. [PMID 16586406] The three Swedish plants studied opened in 1860, 1897, and 1906 and closed in the late 1980s to early 1990s. Potential carcinogens were used: chromium, chlorophenols, aniline dyes, formaldehyde, methyl mercury, arsenic, benzene, and chlorinated solvents. Arsenic sulfides were used until 1950, methyl mercury (fungicide) until 1960, chlorophenols (fungicide) until 1980, and benzidine dyes until 1980.
The three steps in leather processing are: 1. "Preparation of hides (curing, soaking and hair removal liming) and pre-tanning stage (bating and pickling) in a special shed (called beam house)." 2. "Tanning stage (tanning, sammying and shaving)." 3. "Post-tanning or finishing stage (drying, fat liquoring and finishing)." See the agent "Leather dust."
Metal Machining
In conventional machining, metal exposure from the cutting tool is insignificant. Stainless steel machining may expose the operator to chromium, nickel, and cobalt. Besides the conventional method, other types of metal machining include electrochemical, electrical discharge, hard metal, laser, and waterjet cutting. [Burgess, p. 146] Ethanolamines are used in metalworking fluids to stabilize pH and prevent corrosion. Biocides are used to inhibit bacterial and fungal growth in metalworking fluid reservoirs. Nitrosamines have been found in metalworking fluids. Hypersensitivity pneumonitis (HP) may develop in workers exposed to microbially contaminated, water-based metalworking fluids.] See the agent "Oil mist, mineral."
Painting (Pigments, Binders, and Biocides)
Spray painters who use isocyanates in polyurethane coatings or aliphatic amines in epoxy paint systems have a high risk for occupational asthma. Biocides are commonly added to paints. ingredients in paints can be classified into pigments, solvents, and vehicles. Vehicles are the binders that hold the paint together and include the following types: epoxy, alkyd, urethane, vinyl, and phenolic. In the shipyard industry, copper is common in anti-fouling paints and zinc is used in "preconstruction primers." [ILO Encyclo: Ship and Boat Construction and Repair] Powdered paints, used increasingly in the transportation equipment industry, contain epoxy formulations. Manual spray painting is still necessary in the production of commercial trucks, buses, construction equipment, and farm machinery.
Lead and chromate-based paints are still used in this segment of the transportation equipment industry. [ILO Encyclo, 3:91.1-91.8] In the aerospace industry, zinc chromate is used in primer paints. [ILO Encyclo, 3:90.1-90.13] See "Painting (Solvents)."
Using Disinfectants or Biocides
Disinfectants are chemicals used to inhibit or kill microorganisms. Disinfectants are also called antiseptics or biocides. Disinfectants are generally used in physical media (solutions or on surfaces) while antiseptics are applied to skin or other living tissue. Some of these agents are also used as preservatives for food, drugs, and other domestic and industrial products. Many of these chemicals are skin and respiratory sensitizers. The following can cause occupational asthma: glutaraldehyde, formaldehyde, sodium bisulfite, chloramine T, hexachlorophene, chlorohexidine, benzalkonium chloride, isononanoyl oxybenzene sulfonate, lauryl dimethyl benzyl ammonium chloride, and isothiazolinones. A study of 175 workers exposed to chloramines, aldehydes, and quaternary ammonium disinfectants in the food industry showed increased acute irritation symptoms but not chronic respiratory symptoms
Working with Glues and Adhesives
In the past, benzene was commonly used as a glue solvent in the shoe industry. N-hexane is another toxic solvent that has been used as a glue solvent. Urea-formaldehyde and phenol-formaldehyde glues are used in plywood and particleboard manufacturing. Epoxy resins, isocyanates, acrylates, and curing agents are also used to make synthetic glues and adhesives
Application field
OIT, Mainly used in the synthetic leather, genuine leather, polymer, and paints industries to protect against mildews
Performance characteristics
1. Serve as a broad-spectrum, long-lasting biocide to kill bacteria and fungi of all kinds.
2. Can be uniformly dispersed in the slurries of acrylic resin and polyurethane resin.
3. Excellent resistance to high temperature.
4. Applicable in the medium of the pH value in the range of 3 to 9.
5. Low toxicity; completely in line with the strictest EU standards.
Cautions
For use in the synthetic leather, genuine leather, and polymer industries, the concentration of using is recommended to be 0.3-1.0% (w/w); instructions for the concentration of using in the paint industry will be offered by the company’s technology division depending actual applications.
Performance characteristics
1. Demonstrate an excellent bactericidal effect; with broad-spectrum, long-lasting features.
2. Low toxicity; easy to operate; can be added at any production step.
3. Applicable in the medium of the pH value in a range of 5 to 9.
4. Good uniformity of dispersion; contain no VOC; with thermal stability.
5. Not combustible and easy to transport and use.
6. Stable in the intense ultraviolet or acid rain environment.
Octylisothiazolinone is recommended for a wide range of applications including paints, adhesives and sealants where protection is required in the dry state. Description; 2-Octylisothiazolinone is a clear glycolic solution, dry film fungicide, free from Carbendazim and diuron.
Octylisothiazolinone is a biocide that has been reported as a moderate, but rare contact allergen. Octylisothiazolinone has been used for targeted testing only. All octylisothiazolinone-patch test results registered in the Allergen Bank between January 1992 and February 2012 were analyzed. A total of 20 out of 648 patients patch tested with octylisothiazolinone had positive reactions. The majority of the patients (90%) with relevant sensitizations to octylisothiazolinone had been exposed in occupational settings and most patients were painters. Octylisothiazolinone is a relevant sensitizer.
Usage and Cautions
1. It is recommended to use the concentration of using in the range of 0.1 to 0.5%, depending on the actual applications. This product is also widely used for sterilization of interior and exterior latex paints to protect against mildews; suitable for use in the production of eco-friendly latex paints; it is recommended to adopt the adding concentration of 0.1 – 0.3% depending on the performance and service environment of paints.
2. This product should be used in the medium of pH≤9.5.
3. Wear protective clothes, rubber gloves, goggles and masks.
2-Octyl-4-isothiazolin-3-one Storage
Keep container tightly closed
Store in a cool dry well-ventilated place
About this substance
This substance is used in formulation or re-packing.
Biocidal Uses
This substance is approved for use as a biocide in the EEA and/or Switzerland, for: wood preservation.
This substance is being reviewed for use as a biocide in the EEA and/or Switzerland, for: product preservation, preservation films, preservation of fibres, leather, rubber, or polymers, preservation for construction materials, preservation for liquid systems, preservation for working / cutting fluids.
Formulation or re-packing
This substance is used in the following products: biocides (e.g. disinfectants, pest control products).
Manufacture
An aqueous dispersion of octylisothiazolinone (“OIT”) has been found to be a superior vehicle for delivering OIT to wood for protecting the wood from discoloration by mold or fungi. The OIT dispersion can be applied to the wood by spraying, dipping or pressure treating, among other methods.
Field of the Invention
The present invention relates to dispersions of octylisothiazolinone and to products and processes for increasing the resistance of wood against attack by surface mold and sapstain fungi.
Descriptionon of the related art
Protecting wood from discoloration by spraying it with or immersing it in liquid solutions of octylisothiazolinone (hereinafter referred to as “OIT”) is well known. OIT solutions are publicly used to combat molds that have pigmented spores, such as Stachybotrys chartarum and Penicillium sp., and sapstain fungi that have pigmented hyphae, such as Aureobasidium pullulans.
Wood contains four main types of material: cellulose, hemi-cellulose, lignin, and actives. Cellulose and hemi-cellulose make up the fibril structure of wood cell walls. Lignin acts as a poly-phenolic glue that holds the cellulosic fibrils together. Extractives are the sugars, starches, oils, etc. that generally reside within the wood cell voids along with water.
Fibrils are groups of cellulosic molecules in bundles of about 12 nm or less diameter, typically about 2 to 4 nm diameter. Cellulose is the primary fibril component. Hemicellulose, which is considered a chemical precursor to cellulose, is also present in the fibrils.
Fibrils bundle together to form the wood fiber within a cell wall. Each cell wall is comprised of four layers: a primary cell wall layer, an S1 layer, an S2 layer, and an inner cell wall layer. The fibrils are oriented in different directions, depending upon which layer of the cell wall the fibril was formed in.
The primary cell wall is a relatively thin, outermost layer of the cell wall. Fibrils in the primary cell wall layer can be oriented in various directions, fibril direction in the primary cell wall layer is amorphous.
Due to the structure of cellulose, fibrils, and cell walls; water has interesting effects on wood. First, water can fill the cellular voids and water can also adsorb onto the cellulose (not to be confused with absorption into the cellulose). A hydrogen-bonding interaction occurs between the cellulose and the adsorbed water. Consequently, when wood is dried, the first water that is driven off is water located within the cellular voids (also known as “free water”). The last bit of water to be driven off is the water adsorbed onto the fibrils of the cell wall (also known as “bound water”).
Wood shrinks and swells with the addition or removal of bound water. Additional energy is required to remove bound water due to hydrogen bonding. Aqueous solutions, being solutions of water, are typically adsorbed into the wood fiber.
For the present purposes, “fungal attack” means infestation by wood destroying fungi (typically Basidiomycetes fungi), which attack and digest the cell wall constituents: cellulose, hemi-cellulose, and lignin. By digesting the cell wall, wood-destroying fungi undermine the strength and integrity of the wood. Preservative treatments for wood have historically focused on protecting the cell wall structural integrity, and thereby the durability of the wood.
For example, pressure treating with preservatives is a method of forcing preservatives into the structure of the cell wall. In the method, one or more preservatives are forced from the sawn surfaces of a board into the center of the board and wood destroying fungi are killed when they come into contact with the biocide. Most pressure treating processes utilize biocide dissolved in a liquid solution, and attempt to force the biocidal solution between the fibrils of the cell wall.
Previous researchers have also described special solvents for dissolving OIT, and emulsions which facilitate dilution of concentrated OIT-containing formulations to produce OIT solutions.
Other known pressure processes employ preservatives in the form of aqueous dispersions. The dispersions contain tiny biocidal particles that are forced by pressure into the cell wall fibers. The aqueous solutions swell the fibrils and the tiny particles are forced among the fibrils. Because wood-destroying fungi grow among and eat the fibrils, this is an effective way to bring the biocidal particles into contact with wood destroying fungi. However, the treatments used to combat wood-destroying fungi are inadequate against wood-discoloring molds and fungi.
Wood-discoloring molds and fungi are presently a major of concern in the lumber industry. The simple fact is that consumers do not like to buy discolored, moldy-looking wood. Consumers are not satisfied with strong lumber that is looks unhealthy. Wood-discoloring molds and fungi do not negatively impact the structural integrity of the wood, because they do not digest the cell wall. The hyphae of wood-discoloring fungi grow within the cell voids, not within the cell walls. Consequently, the traditional approach of forcing biocidal solutions or biocidal dispersion into fibrils of the cells walls is inefficient and largely ineffective against wood-discoloring molds and fungi.
Despite the impressive achievements of previous researchers, the wood industry still has a need for improved preservative products that can efficiently increase the resistance of wood and wood products to discoloration by mold and fungi.
Octylisothiazolinone (OIT) is a contact allergen ofmoderate potency (1). It is a biocide and preservative,marketed for use in a range of industrial products suchas polishes, paints, cleaners and metalworking fluids forsome 30 years (2). Accordingly, most cases of reportedallergic contact dermatitis from OIT are of occupationalorigin (1–5). However, a Swedish investigation reportedthat 3% of detergents on the Swedish market containedOIT (6). OIT is also registered as an antimicrobial agentin the European Commission database (CosIng) withinformation on cosmetic substances and ingredients withthe INCI-name octylisothiazolinone.
Octylisothiazolinone preservatives and industrial biocides:
OIT has been identified as an ingredient in timber coatings and primers, inks, and sealing agents. According to industry information, OIT has domestic use in architectural paints and in decking oils.
OIT is used as biocides and preservatives in recirculating water cooling systems .They are nonoxidising biocides that are used to control microbial contaminated systems and prevent recontamination.
OIT is also used as preservatives in polymer emulsions, paper-coating materials, wood treatment solutions and in hydraulic fluids. OIT is used to preserve textiles made from fibres, leather and rubber. It is also used as a preservative in household cleaning products and laundry mildewcides. OIT has reported cosmetic uses as an antibacterial agent in shampoo and other cosmetics and has also been reported to be present in tattoo inks.
2-octyl-isothiazol-3(2 H)-one (OIT) is used as film preservative in water-based polymer resin paints and renders to prevent the growth of moulds and bacteria. It is known that biocides leach from facades with rainwater and end up in the environment via stormwater runoff
OIT is an active substance proposed for use as a wood preservative (use classes 1 and 2) in
Product Type 8 of the Biocidal Products Regulation. It is for the control of bluestain fungi through application by dipping/immersion and vacuum impregnation.
The assessment of the biocidal activity of the active substance demonstrates that it has a sufficient level of efficacy against the target organism(s) and the evaluation of the summary data provided in support of the efficacy of the accompanying product, establishes that the product may be expected to be efficacious.
Data have been provided to support application by dipping/immersion. However vacuum pressure impregnation is not currently supported by efficacy data. This mode of application could be applied for at product authorisation stage.
OIT and its derivatives applications
in different fields since they present useful biological properties, such as antimicrobial, antibacterial, antifungal, antiviral, anticancer, and anti-inflammatory activities [1]. Furthermore, isothiazoles have
been described to act as inhibitors of proteases for the treatment of anxiety and depression, as inhibitors of aldose reductase, and as 5-hydroxytryptamine receptor antagonists
1). Chemically, isothiazole
(1,2-thiazole) is a five-membered heteroaromatic that is considered to be derived from thiophene, in which the second position is occupied by a nitrogen atom (Figure 1) [2].
The noticeable biological effects observed for isothiazole-containing compounds have generated an enormous interest on this scaffold for drug discovery and development programs, which resulted in a steady increase in the number of related patent applications as well as in the successful introduction
of isothiazole-based derivatives to the market. Among them, the most extensively used for industrial applications and reactive intermediates, for the synthesis of various organic substances including pharmaceuticals and agrochemicals, are those based on isothiazolin-3-one (isothiazolinone).
Octylisothiazolione (OIT), is only used in industrial products and non-cosmetic consumer products such as paints and leather products and also pose a problem in special occupations. We have Octylisothiazolinone (OIT) for the care chemicals industry.
Summary of the invention
It has now been discovered that an aqueous dispersion of OIT in water is surprisingly more effective for increasing the resistance of pressure treated wood to discoloration by mold and fungi, as compared to aqueous and non-aqueous solutions of OIT.
In one aspect, the invention is a two-phase composition for inhibiting wood discoloration by mold having pigmented spores or by sapstain fungi. The composition includes a disperse phase in the form of solid or liquid particles of measurable size, which disperse phase includes octylisothiazolinone and a surfactant. The surfactant may be nonionic, preferably a polyalkoxylated ether or polyalkoxylated alcohol.
The composition also includes a continuous liquid phase containing water and, optionally, a rheology modifier. The size of the particles is in the range of about 0.1 to about 10 microns.
In another aspect, the invention is a process for increasing the resistance of wood to attack by surface mold and sapstain fungi. The process includes suffusing a two-phase composition over or through wood to place the composition within the voids of wood cells, immediately adjacent wood cell walls. The composition is composed of a disperse phase in the form of solid or liquid particles of measurable size, which includes octylisothiazolinone and a surfactant; and a continuous liquid phase, which includes water and, optionally, a rheology modifier.
Detailed desciption of a preferred embodiment
In a preferred embodiment, the invention is a two-phase composition for inhibiting wood discoloration by mold having pigmented spores or sapstain fungi.
Now to, a disperse phase of the composition is in the form of solid or liquid particles 1. The particles 1 contain at least octylisothiazolinone and a surfactant. The particles 1 are physically stable at OIT concentrations in the range of about 50 to about 500 ppm, based on the total weight of the dispersion. Preferably, the amount of OIT present in the composition is in the range of about 50 ppm to about 60 percent by weight. More preferably, the OIT present in the composition is 2-n-octyl-4-isothiazolin-3-one.
The particles of the inventive dispersion are small enough to move inside the cell voids and travel from one wood cell to another via intercellular pits , but are too large to be adsorbed or absorbed within the cell wall. The particles of the inventive dispersion are effective at inhibiting discoloring mold having pigmented spores or sapstain fungi, because the particles become concentrated in cell voids where the hyphae of mold having pigmented spores or sapstain fungi grow.
The particles are of a size that permits them to travel within individual wood cells without necessarily being adsorbed or absorbed by the wood fiber. Preferably, the particles 1 have a mean average size in the range of about 0.1 to about 50 microns; more preferably, about 0.5 to about 10 microns.
For the present purposes, “mean average” and “arithmetic mean” are synonyms which are both defined as the value obtained by dividing the sum of a set of quantities by the number of quantities in the set.
Depicts a previously known OIT solution 2 absorbed or adsorbed within cell walls 6. While concentrating OIT solution 2 within cell walls 6 may be satisfactory for inhibiting wood-destroying fungi that act by entering cell walls , it is has now been discovered that OIT dispersion particles 2 concentrated within or immediately adjacent to cell voids 3 are more effective for inhibiting wood discoloration by mold having pigmented spores or sapstain fungi.
A continuous phase of the dispersion is liquid and includes water. A thixotropic rheology modifier is often useful for physically stabilizing the dispersion. When present, the amount of thixotropic rheology modifier should be in the range of about 0.01 ppm to about 0.1 percent by weight.
For the present purposes, “rheology” means the deformation and flow of matter, especially non-Newtonian flow of liquids and plastic flow of solids. For the present purposes, “thixotropic” means having a viscosity that decreases when a stress is applied, as when stirred.
The composition is conveniently transported in concentrated form and diluted with water at or near the point of use. Preferably, the concentrated form of the composition contains about 5 percent to about 50 percent OIT by weight. Preferably, the diluted form of the composition contains about 100 ppm to about 2 percent OIT by weight.
The surfactant is preferably a non-ionic surfactant. For the present purposes, “non-ionic surfactant” means a surfactant without a charged moiety. Polyalkoxylated ethers or polyalkoxylated alcohols are especially preferred for the surfactant. For example, the surfactant may be a polymer of ethylene oxide and propylene oxide. The surfactant may be present in the composition in an amount in the range of about 0.1 ppm to about 10 percent by weight; preferably, about 1 ppm to about 0.5 percent by weight; more preferably about 2 ppm to about 2 percent by weight.
The following examples and procedures are presented to communicate the invention, and are not meant to limit the invention in any way. Examples described in the present tense are hypothetical examples. Unless otherwise indicated, all references to parts, percentages or proportions are based on weight.
IUPAC Names:
2-N-Octyl-4-isothiazolin-3-on
2-n-Octyl-4-isothiazolin-3-one
2-n-Octyl-4-isothiazolinone-3-one
2-octil-2H-isotiazol-3-ona
2-octyl-1,2-thiazol-3-one
2-octyl-2,3-dihydro-1,2-thiazol-3-one
2-octyl-2,3-dihydro-1,2-thiazol-3-one
2-Octyl-2H-isothiazol-3-one
2-octyl-2H-isothiazol-3-one
2-octyl-2h-isothiazol-3-one
2-octylisothiazol-3(2H)-one
octhilinone (ISO)
Octylisothiazolinone
Regulatory Names:
2-octyl-2H-isothiazol-3-one
2-octyl-2H-isothiazol-3-one
2-octyl-2H-isothiazol-3-one (OIT)
Octhilinone
octhilinone (ISO)
octhilinone (ISO); 2-octyl-2H-isothiazol-3-one
octhilinone (ISO); 2-octyl-2H-isothiazol-3-one; [OIT]
octhilinone (ISO);2-octyl-2H-isothiazol-3-one
octhilinone (ISO);2-octyl-2H-isothiazol-3-one; [OIT]
