Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/34—Nitriles

Definitions

• This invention relates to a dispersion of an antimicrobial agent for use in water-based and solvent-based protective coatings such as paints.
• Antimicrobial agents such as 2,4,5,6-tetrachloroisophthalonitrile are used in water-based and solvent-based protective coatings such as paints. These agents are almost insoluble in water and are sparingly soluble in organic solvents.
• 2,4,5,6-tetrachloroisophthalonitrile is soluble to the extent of about 0.6 ppm in water at 25°C and is soluble at 25°C in xylene 8% (wt/wt), cyclohexane 3%, acetone 2% and kerosene at less than 1%.
• a tetrachloroisophthalonitrile dispersion is prepared by dispersing finely divided tetrachloroisophthalonitrile powder in a vehicle which is a mixture of calcium alkyl aryl sulfonate, nonionic surfactant, ester, coupling agent and optionally lecithin.
• the vehicle provides a water and organic solvent compatib le dispersion having pourable and pumpable viscosities as well as settling resistance.
• the resulting dispersion is an antimicrobial agent for use in both water-based a nd solvent-based protective coating such as paints.
• Useful tetrachloroisophthalonitrile dispersions may contain the rang es of indicated and preferred ingredients shown below:
• the tetrachloroisophthalonitrile is 2,4,5,6-tetrachloroisophthalonitrile, also known as 2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile or 1, 3- dicyano-2,4,5,6-tetrachIorobenzene. It is available under the registered trade names of Nopcocide ® N-96, Daconil ® 2787, Termil ® and Forturf ® . It has the structural formula:
• This tetrachloroisophthalonitrile is a broad spectrum foliage and fruit protectant fungicide as well as an industrial antimicrobial agent. It may be prepared by the process described in U.S. Patent 3,290,353 - Battershell and Bluestone, December 6, 1966, wherein halogenated aromatic nitriles are prepared from the corresponding ring-chlorinated acid chlorides. The acid chloride is converted to the corresponding amide by dissolving the acid chloride in a suitable organic solvent and introducing ammonia to form the amide. Either anhydrous or aqueous ammonia is employed.
• the ring-chlorinated aromatic amide is dried and then reacted with a dehydrating agent such as phosphorus pentoxide or phosphorus oxychloride to obtain the nitrile.
• a dehydrating agent such as phosphorus pentoxide or phosphorus oxychloride
• the calcium alkyl aryl suifonate used in the vehicle may be Witco Chemical Corp. Emcol ® D-24-25 (25% ethanol) or Witconate ® 605-T (25% xylene type solvent), calcium dodecyl benzene sulfonate, alkaline earth petroleum sulfonates and lead alkyl aryl sulfonates.
• the alkyl aryl sulfonates may have from 6 to 18 carbon atom alkyl groups.
• nonionic surfactants for the vehicle include nonylphenol ethoxylated with 4 moles ethylene oxide, castor oil ethoxylated with 43 moles ethylene oxide, octylphenol plus 15 moles ethylene oxide, ethoxylated alcohols, e.g., tridecyl alcohol with 10 moles ethylene oxide, dinonylphenol with 1.5 moles ethylene oxide and ethoxylated blown oil. It is to be understood that ethoxylates containing from about 1 to about 150 moles of ethylene oxide based on the above may be used.
• Esters which may be used include isodecyl oleate, methyl oleate, butyl oleate, propyl stearate, 2-ethylhexyl tallate, isopropyl myristate, phosphate esters (triethyl phosphate, tributoxyethyl phosphate, tricresyl phosphate) and plasticizers (dioctyl phthalate, butylbenzyl phthlate, glyceryl trioleate, sebacic acid esters, diisodecyl adipate, epoxidized soya oils, tributyl citrate, octylene glycol dibenzoate and polyesters).
• phosphate esters triethyl phosphate, tributoxyethyl phosphate, tricresyl phosphate
• plasticizers dioctyl phthalate, butylbenzyl phthlate,
• the coupling agents in the vehicle may be butyl Carbitol, butyl Cellosolve ® (2-butoxyethanol), Carbitol (diethylene glycol monoethyl ether), Cellosolve ® , hexyl Cellosolve ® , butoxytriglycol, butyl Carbitol (diethylene glycol monobutyl ether), 1-butoxy-ethoxy-2-propanol, phenyl glycol ether, polyglycols, dibutyl Carbitol, butyl Cellosolve ® acetate, Carbitol acetate, hexylene glycol diacetate and Tergitol ® XD (polyalkylene glycol ether).
• lecithin products for the vehicle include soya lecithin, alkoxylated lecithin, fractionated lecithin, hydrolyzed lecithin, hydroxylated lecithin, halogenated lecithin, sulfonated lecithin, coacervated lecithin and bleached lecithin.
• the vehicle may be prepared by blending the above ingredients in th e desired proportions at room temperature, heating if necessary, to obtain a homogeneous mixture and then cooling to room temperature.
• the tetrachloroisophthalonitrile is then added to the vehicle and mixed until a uniform dispersion is obtained.
• the antimicrobial agent is usually added slowly and dispersed by mixing from about 15 to about 60 minutes.
• the consistency or viscosity of the dispersion after mixing is about 15000 to about 30000 cps. If a lower viscosity is desired, higher shear dispersing equipment must be utilized, e.g., homogenizer or 3-roll mill. This equipment will reduce the viscosity to about 7000 to about 10000 cps. The viscosity will also vary depending on the concentration of tetrachloroisophthalonitrile present.
• the tetrachloroisophthalonitrile dispersion may be added to either water-based or solvent-based protective coating formulations. From about 2 to about 100 lbs of the dispersion per 100 gallons of formulation is required. The dispersion may be added to the finished protective coating formulation or may be incorporated as one of the components during manufacture of the protective coating formulation.
• the dispersion is useful in water-based protective coatings such as acrylic, polyvinyl-acetate and vinyl-acrylic emulsions for the trade-sales coatings industry.
• the dispersion may be used in solvent-based protective coatings such as long oil alkyds, medium oil alkyds, short oil alkyds and linsee d oil based systems for the trade-sales coatings industry. Additional details on both types of coatings are given on pages 500 and 501 of Volume 13 of the Encyclopedia of Polymer Science and Technology (Interscience Publishers, New York, N.Y. 1970).
• the products of this invention may be varied to increase water and/or solvent, e.g. , polypropylene, mineral spirits, xylene dispersibility of Nopcocide N-96.
• solvent e.g. , polypropylene, mineral spirits, xylene dispersibility of Nopcocide N-96.
• increasing the ethoxylated castor oil content will increase the dispersibility of Nopcocide N-96 in water but will decrease the mineral spirits dispersibility.
• Propoxylated or low (1-5 moles) ethoxylated alcohols will improve mineral spirits dispersibility, whereas ethoxylated alcohols with 15-60 moles ethylene oxide will improve water dispersibility.
• Nopcocide N-96 dispersions The stability of Nopcocide N-96 dispersions was determined by placing 4 ounce samples in capped glass jars in a circulating air oven at 120° to
• Emcol D-24-25 (calcium alkylbenzene sulfonate. 75% active in ethanol). 19 nonionic surfactant (nonylphenol plus 5 moles ethylene oxide). 30 fatty acid ester (Isodecyl oleate).
• Nopcocide N-96 A 50%, by weight, dispersion of Nopcocide N-96 was prepared using 50 parts, by weight, of the vehicle and 50 parts of Nopcocide N-96 by adding the biocide into the vehicle slowly and disperse for 30 minutes using a laboratory stirrer. Dispersion consistency at this stage was 17000 cps. After homogenizing in a laboratory hand homogenizer, the viscosity decreased to 8150 cps (Brookfield LVF model).
• Nopcocide N-96 dispersions were prepared using the quantities of ingredients shown in Table I and I (continued). These dispersions were prepared following the procedure in Example I and are designated as A 5 through Q in the table.
• Nopcocide N— 96 dispersion designated as Q in Table I was evaluated in a water-based protective coating formulation, an acrylic (50% solids) resin emulsion system at a level of 2.0% based on total weight of paint. Physical and optical characteristics of the formulation were not affected by the presence of the Nopcocide N-96 dispersion in the system. .Results of the evaluation are given below.
• EXAMPLE IV The 50% Nopcocide N-96 dispersion designated as Q in Table I was evaluated in a water-based protective coating, a polyvinyl acetate (55% solids) paint system at a level of 2.0% based on total weight of paint. The physical and optical characteristics of the formulation were not affected by the presence of the Nopcocide N-96 dispersion in the system. Results of this evaluation are shown in Table II. The Hegman Grind in all of the dispersions including the control after four weeks storage at 120 F showed no change and was still 5.0. If the biocide fails photosensitivity test at indicated level, all further screening is discontinued.
• Nopcocide N-96 dispersion designated as Q in Table I was evaluated in a water-based protective coating formulation, a vinyl-acrylic (55% solids) system at a level of 2.0% (total weight of paint). No problems incorporating the dispersion in the formulation were encountered and no changes in film appearance of the dried coating were observed.
• Nopcocide N-96 dispersion designated as Q in Table I was evaluated in a linseed-oil house paint system at a level of 2.0% (total weight of paint). No problems incorporating the dispersion in the formulation were encountered and no changes in film appearance of the dried coating were observed.
• Nopcocide N-96 dispersion designated as Q in Table I was evaluated in a solvent-based protective coating formulation, a linseed-oil primer paint system at a level of 2.0% (total weight of paint). No problems incorporating the dispersion in the formulation were encountered and no changes in the appearance of the dried film were noted.
• EXAMPLE VIII The 50% Nopcocide N-96 dispersion designated as Q in Table I was evaluated in a solvent-based protective coating formulation, an alkyd house paint system at a level of 2.0% (total weight of paint). No problems incorporating the dispersion in the formulation were noted and no changes in film appearance of the dried coating were observed. While the invention has been described with reference to certain specific embodiments thereof, it is understood that it is not to be so limited since alterations and changes may be made therein which are within the full and intended scope of the appended claims.

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• Life Sciences & Earth Sciences (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Pest Control & Pesticides (AREA)
• Zoology (AREA)
• Agronomy & Crop Science (AREA)
• Materials Engineering (AREA)
• Health & Medical Sciences (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Environmental Sciences (AREA)
• Paints Or Removers (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Colloid Chemistry (AREA)

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  • 1979-02-20 ES ES477912A patent/ES477912A1/es not_active Expired
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  • 1979-02-21 WO PCT/US1979/000095 patent/WO1979000654A1/en unknown
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