WO1995017091A1 - Formulations a liberation lente repoussant les insectes et leurs utilisations - Google Patents

Formulations a liberation lente repoussant les insectes et leurs utilisations Download PDF

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Publication number
WO1995017091A1
WO1995017091A1 PCT/US1994/014745 US9414745W WO9517091A1 WO 1995017091 A1 WO1995017091 A1 WO 1995017091A1 US 9414745 W US9414745 W US 9414745W WO 9517091 A1 WO9517091 A1 WO 9517091A1
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WO
WIPO (PCT)
Prior art keywords
formulation
repellent
insect repellent
insect
owf
Prior art date
Application number
PCT/US1994/014745
Other languages
English (en)
Inventor
Raymond J. Tucci
Nathan M. Dry
Original Assignee
Tucci Associates, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tucci Associates, Inc. filed Critical Tucci Associates, Inc.
Priority to CA002179743A priority Critical patent/CA2179743A1/fr
Priority to JP7517583A priority patent/JPH09510184A/ja
Priority to AU15165/95A priority patent/AU703959B2/en
Priority to EP95906680A priority patent/EP0735817A4/fr
Priority to BR9408411A priority patent/BR9408411A/pt
Publication of WO1995017091A1 publication Critical patent/WO1995017091A1/fr
Priority to NO962652A priority patent/NO962652L/no

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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/06—After-treatment with organic compounds containing nitrogen
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/18—Vapour or smoke emitting compositions with delayed or sustained release
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A01N25/28—Microcapsules or nanocapsules
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/06—Nitrogen directly attached to an aromatic ring system
    • 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
    • A01N37/18—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 containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/415—Amides of aromatic carboxylic acids; Acylated aromatic amines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/11—Starch or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/08—Processes in which the treating agent is applied in powder or granular form
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/12—Processes in which the treating agent is incorporated in microcapsules
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
    • D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
    • D06N3/0056—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the compounding ingredients of the macro-molecular coating
    • D06N3/0059—Organic ingredients with special effects, e.g. oil- or water-repellent, antimicrobial, flame-resistant, magnetic, bactericidal, odour-influencing agents; perfumes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/46—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
    • D06P1/48—Derivatives of carbohydrates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5292—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds containing Si-atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/001—Special chemical aspects of printing textile materials
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • D06P5/004—Transfer printing using subliming dyes

Definitions

  • the present invention relates to slow-release microcapsular insecticidal formulations comprising the insect repellent N,N' -diethyl-m-toluamide.
  • the invention also relates to woven, non-woven, and knit substrates that are treated with the formulations of the invention.
  • insect repellents are effective when applied to the skin as a spray or lotion, their effectiveness is known to decline with time. Furthermore, in order for an insect repellent to be effective, the insect repellent must be applied in a concentrated amount to a small area of the face, neck, and hands or on selected areas of a wearer's garment.
  • the invention provides for a microcapsular insecticidal composition comprising a pyrethroid and a biological synergist capable of controlling insects for up to four (4) days.
  • the invention provides for a tent fabric coated on the inside with a composition which renders it water repellent, flame retardant and insect repellent using permethrin as the insect repellent. Permethrin is protected against oxygen with a plasticizer. The outside of the tent is coated with a composition which renders it water repellent and flame retardant exclusive of the insect repellent.
  • the insect- repellent composition has an effective life of more than six (6) months.
  • the invention relates to compositions, devices and methods for controlling insect activity wherein an insect control agent is self-adhered to a rough-surfaced fiber and provides extended control of insect activity.
  • the microencapsulated insect control agents disclosed in Barber are named as the preferred insecticide for use in Ronning' s invention.
  • Ronning teaches that smooth-surfaced fibers do not act as good sites for adhesion of microencapsulated insect control agents.
  • the invention relates to elongated flexible insect-repellent strips secured to or retained in cavities in various ar ⁇ ticles of apparel to repel insects from the person wearing such apparel.
  • the invention relates to a coated fabric that is flame resistant and water repellent and includes a polyfunctional isocyanate as an adhesion promoter and binder to adhere the coating to the substrate in a flake proof manner.
  • BDUs Uniforms used by the U.S. Military with amylopectin fabric wrinkle inhibitor and permethrin insect/arthropod repellent in combination.
  • the invention relates to textiles impregnated with insect- repellent compositions including piperonyl butoxide and pyrethrin, wetting agent, thickener and an agent for preventing migration of the pyrethrin and piperonyl butoxide repellent into foods stored in contact with the textiles and for otherwise retaining the repellent in the textiles.
  • This invention provides for fabric substrates treated with formulations which comprise an insect repellent such as for example N,N' -diethyl-m-toluamide (DEET) which is known to effectively control a variety of insects.
  • DEET N,N' -diethyl-m-toluamide
  • DEET is environmentally safe and leaves no harmful residues.
  • DEET has been found to be stable at both reduced and elevated temperatures and under storage conditions.
  • DEET is effective on biting flies, chiggers, deerflies, fleas, leeches, mosquitoes, and ticks.
  • Several factors influence the efficacy of DEET as an insect repellent, such as, for example, extreme environmental conditions, the extent of absorption and elimination, the type of repellent formulation, and the avidity of the test species.
  • the efficacy of DEET is reduced by increased perspiration rate and the duration of repellent activity is influenced by wash-off, abrasion from the treated surface and absorption. Water, from either rainfall or perspi
  • the insect repellent is comprised in microcapsules with a diameter of from about 0.005 mm to about 1.800 mm.
  • the insect repellent N,N' -diethyl-m-toluamide (DEET) can be together formulated and spray-dried to form mi- crocapsules in powder form.
  • the formulation has novel properties in that the microencapsulated DEET can be time- released and the rate of release of the DEET can be con ⁇ trolled by varying the amounts of heavy alcohol or plas- ticizers used in the process.
  • the DEET can time-release over a period of time spanning of from about 24 hours to about several months and is affected by the method of storage of the powder and exposure to light and air.
  • time-release of DEET can be attributed to the entrapment of the DEET in the resulting structure of the capsule-forming compounds and the entrapping effect of the silicone elastomers.
  • the time-release property of the DEET and the overall stability of the powder can be affected by further coating the microcapsule with for example a wax compound (bee wax, gelatin or polyethylene glycol and derivatives) for an intermediate coating or with for example a ceramic compound (clay, slip, china or ivory) for a harder coating or a protective layer.
  • microcapsules and the powder include solubility in water and water-based compounds (such as for example lotions, cremes, latex paints, acrylic-based paints and sealers) as well as its solubility in oil, hydrocarbon solvents and the like. It is to be noted that before formulation, all compounds entering into the formulation including DEET were insoluble in water.
  • insect-repellent formulations of the invention can be applied to a wide range of fabric substrates without being limited by the coarseness or smoothness of the fabric substrate.
  • volatility is one of the functional attributes associated with insect repellency, and a high volatility lowers the long term effectiveness of the insect repellent
  • this invention provides for an insect-repellent formulation which lowers the volatility of the insect repellent thus prolonging its effectiveness.
  • insect-repellent formulations of the invention can be combined with a wide range of fabric treatment formulations.
  • the resulting formulations can be applied to any suitable fabric substrate depending on the intended use of the fabric and the fabric treatment process such as, for example, cottons, knits, polyesters or blends, fiberglass, wovens or non-wovens and heat-sensitive substrates such as acetates and mode-acrylates and nylon.
  • the formulations can be applied such that multiple layers of super thin laminates are produced and the insect repellent is thus slowly released at each laminate interface as it ruptures.
  • the slow-release insect-repellent formulation of the invention can be prepared by first formulating the insect repellent N,N' -diethyl-m-toluamide with an oleophilic chemical such as a silicone compound such as for example elastomeric or monomeric silicone, and then by mechanical/ and or chemical entrapment of the resulting compound in a carbohydrate matrix, such as for example a starch compound including but not limited to corn starch, potato starch, technical starch, rice starch and any of the synthetic starches. Silicone, which is immiscible with water, is dissolved with the DEET which is also immiscible with water. The DEET-silicone solution is mixed into a starch solution with the resulting solution being miscible in water.
  • an oleophilic chemical such as a silicone compound such as for example elastomeric or monomeric silicone
  • the DEET molecule is entrapped in the lattice-like structure of the starch molecule which has the effect of lowering the vapor pressure of the insect repellent thus reducing its volatility.
  • the DEET is slowly released from the lattice ⁇ like structure of the starch molecule with the net effect of the formation of a slow-release insect-repellent formulation.
  • the slow-release insect-repellent formulation consists of from about 40% to about 75% starch, and of from about 10% to about 35% N,N'- diethyl-m-toluamide, and of from about 15% to about 25% silicone, preferably about 65% starch, about 15% N,N'- diethyl-m-toluamide and about 20% silicone on a dry weight basis.
  • the slow-release insect- repellent microcapsules have a particle size of from about 0.005 mm to about 1.800 mm.
  • the slow-release insect-repellent formulation of the invention is prepared by first dissolving starch in water at its boiling point.
  • the starch solution is cooled to room temperature by further addition of water and the insecticide N,N' -diethyl-m-toluamide and silicone are slurried into the starch solution.
  • the formulation is spray dried using conventional spray drying equipment such that the slurry produces a fine white powder comprising DEET of from about 8% to about 11% and with a moisture of from about 3% to about 8%, total solids of from about 10% to about 15% and little or no odor.
  • the resultant slow-release insect-repellent formulations of the invention are a non-irritant to the skin or mucous membranes and are nontoxic.
  • the slow-release insect-repellent formulation of the invention can be formulated for application on fabric substrate in high yields without affecting the functionality, esthetic appearance, hand or feel of the treated substrate and without leaving any residual odor.
  • the slow-release insect-repellent formulation can be combined with a cationic softener and applied as a finishing rinse to a fabric substrate that has been already dyed.
  • the slow-release insect-repellent formulation can be combined into a formulation comprising of from about 2% to about 10% on the weight of the fabric (owf) of the slow-release insect- repellent formulation and of from about 2% to about 6% (owf) cationic softener.
  • This formulation can be exhausted onto the fabric substrate under mildly acidic conditions, for example using acetic acid such that the pH is of from about 5.50 to about 6.60 with the slow-release insect-repellent formulation adhering to the cationic sites in dyeing and the cationic softener adhering to the fabric substrate.
  • the slow-release insect-repellent formulation composition can be combined in a formulation comprising of from about 90% to about 98%
  • the slow-release insect-repellent formulation can be combined in a formulation comprising of from about 90% to about 98% (owf) of a pigment printing paste formulation and of from about 2% to about 10% (owf) of the slow-release insect-repellent formulation.
  • the slow-release insect-repellent formulation cross-links with the pigment binder during pigment dyeing and printing to link on to the cellulose groups of the fabric substrate.
  • the slow-release insect-repellent formulation can be combined in a formulation comprising of from about 90% to about 98% (owf) of water repellent formulation and of from about 2% to about 10% (owf) of the slow-release insect-repellent formulation.
  • the slow-release insect-repellent formulation can be used in a final rinse formulation.
  • Fabric substrates after dyeing, pigment padding and printing, with the appropriate formulation which comprises the slow-release insect-repellent formulation of the invention, can be given a resin finish for hand, appearance and dimensional stability.
  • the resin finish acts as a super thin laminate and provides the treated fabric with an insect-repellent finish and more particularly when the resin used is urea- formaldehyde by the cross-linking of the molecular structure of the cotton fiber to the cellulose fiber during resin curing conditions.
  • the slow-release insect-repellent formulation is trapped during the reaction of the urea- formaldehyde with the cellulose molecule in the cotton fabric.
  • substrate fabrics of 100% cotton and a 50/50 polyester/cotton blend can be treated with a resin finish comprising of from about 2% to about 5% (owf) of the slow-release insect-repellent formulation of the invention and of about 95% to about 98% (owf) of a resin finish formulation.
  • the slow-release insect-repellent formulation can be used in heat transfer printing using a wide range of substrate fabrics.
  • of from about 2% to about 10% weight/ weight (w/w) of the slow-release insect-repellent formulation can be combined with of from about 2% to about
  • (w/w) extender The fabric was processed by heat transfer printing, i.e., by vaporization of the dye from the paper to the fabric at the sublimation temperature of the dye.
  • the ink dispersion can omitted and 100% (w/w) extender can be used. In both cases, the adhesion of the heat transfer paper to the fabric prevents the insect repellent from volatilizing and escaping resulting in greater durability.
  • Example I From about 2% to about 10% (w/w) of the slow- release insect-repellent formulation of Example I can be combined with about 100% extender.
  • the fabric was processed by heat transfer printing, i.e., by vaporization of the dye from the paper to the fabric at the sublimation temperature of the dye.
  • an insect-repellent formulation can be prepared by mixing into a starch slurry a mixture of silicone about 4% (w/w) and the insect-repellent N,N'- diethyl-m-toluamide about 8% (w/w) .
  • the starch slurry is formed by dissolving about 8% (w/w) starch into about 80% (w/w) water at its boiling point.
  • the mixture of insect repellent and silicone is added to the starch mixture after cooling the slurry to room temperature.
  • the resultant slurry is spray dried in a spray drying chamber at an inlet temperature of about 230°F using an atomizing force of from about 2400 to about 3200 psig from a cocurrant atomizer.
  • the slurry produces a fine white powder comprising of from about 0.1% to about 25% DEET and with about 5% moisture and about 15% total solids.
  • From about 2% to about 10% (owf) of the slow- release insect-repellent formulation of Example I can be combined with about 2% (owf) cationic softener (for example, Alpha Soft GMR from Alpha Chemical) and exhausted on a fabric substrate that has been dyed on a jigg, beck or jet at about 120°F, for about fifteen (15) minutes and at a pH of from about 5.50 to about 6.60, adjusted with acetic acid.
  • 2% (owf) cationic softener for example, Alpha Soft GMR from Alpha Chemical
  • From about 2% to about 10% (owf) of the slow- release insect-repellent formulation of Example I can be combined with a pigment padding formulation of about 0.06% (owf) aqueous ammonia, about 4.78% (owf) padding emulsion (for example, padding emulsion #8908 from BASF) , about 2.39% (owf) antimigrant (for example, antimigrant #09-99515 from BASF) , about 0.48% (owf) ammonium sulphate, water, and a variable weight percent of a pigment dye depending on the shade.
  • the resulting formulation is padded on to the fabric at from about 85% to about 90% wet pick up, dried at about 275°F and cured at about 340°F for about thirty (30) seconds.
  • From about 2% to about 10% (owf) of the slow- release insect-repellent formulation of Example I can be combined with a resin finishing composition suitable for treating 100% cotton and comprising about 3.6% (owf) cationic softener, about 1.2% (owf) silicone softener, and about 9.6% (owf) glyoxal reactant.
  • From about 2% to about 10% (owf) of the slow- release insect-repellent formulation of Example I can also be combined with a resin finishing composition suitable for treating 50/50 polyester/cotton and 'comprising about 3.6% cationic softener, about 1.2% (owf) silicone softener, and about 2.4% (owf) glyoxal reactant.
  • the resin finishing formulation can be applied to a fabric substrate that has been dyed, pigment padded, and/or printed as in the above Examples.
  • the resin finish acts as a super thin laminate and provides an additional insect-repellent coating.
  • the chemical mixture is padded on at from about 85% to about 90% wet pickup, dried at about 275°F and cured at about 340° for twenty (20) seconds.
  • Example VIII From about 2% to about 10% (w/w) of the slow- release insect-repellent formulation of Example I can be combined with about 2% ink dispersion and about 85% ex ⁇ tender.
  • the fabric was processed by heat transfer printing, i.e., by vaporization of the dye from the paper to the fabric at the sublimation temperature of the dye.
  • Example I From about 2% to about 10% (w/w) of the slow- release insect-repellent formulation of Example I can be combined with about 100% extender.
  • the fabric was processed by heat transfer printing, i.e., by vaporization of the dye from the paper to the fabric at the sublimation temperature of the dye.
  • the slow-release insect-repellent formulations of the invention were found to afford the wearer complete protection under all types of weather and infestation conditions. Furthermore, the insect-repellency effectiveness of the fabric substrate treatment was found to span up to a period of about several hours to about twelve (12) months.
  • a production trial was initiated on four (4) fabric substrates, knit and woven cotton, poly/cotton and poly/nylon.
  • the fabrics were dyed with the slow-release insect-repellent formulation applied during dyeing or resin finishing as one type of group of fabrics.
  • Another group of knitted and woven fabrics were pad dyed, printed and resin finished with the slow-release insect-repellent formulation applied at the dyeing, printing and resin finishing steps.
  • Garments such as shirts, hats, and the like were produced from the treated fabric substrates.
  • the garments were tested under conditions encountered during outdoor activities.
  • the garments were found to repel insects under outdoor conditions during activities such as hiking, hunting, and fishing in coastal, pasmont and mountain conditions during day and night wear.
  • the treated garments were compared to untreated counterparts under the same conditions.
  • garments were tested on mosquitoes. The mosquitoes would land on exposed skin and promptly bite. By contrast, when the mosquitoes landed on the treated fabric at any location on the garment, they would only remain for about four (4) to about six (6) seconds before taking off .
  • the slow-release insect-repellent formulation of the invention can incorporate different insect control agents such as, for example, permethrin and more generally alkylamides and alkylneodecamides.
  • the slow-release insect-repellent formulation can be applied on a wide range of fabric substrates in ⁇ cluding but not limited to textile blends, woven and non- woven, knits, fibers, leather and synthetic adaptations of leather, flocked fabrics, wood and wood derivatives, plastic and laminates, cable, sheeting, film fiberglass and plexiglass.
  • the slow-release insect-repellent formulation can be also be comprised in moth proofing formulation, packaging material, and paint formulations.
  • a longer-term repellency can e obtained when such capsules are used in the manufacture of commercial finishes such as caulking formulations, paint sealers, wall and floor coverings and the like.
  • the formulations of the invention can have a wide applicability in situations requiring a lower concentration of DEET.
  • the slow-release insect-repellent formulation can be incorporated with a scent or a fragrance or pheromones or with any other formulations that could be conducive to applications in sporting, farming, or hunting situations.
  • higher concentrations of up to from about 20% to about 25% solids of the repellent can be used in caulking compounds.

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  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Toxicology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Formulations à libération lente à base de l'insectifuge N,N'-diéthyl-m-toluamide. L'invention décrit également des substrats en tissus qui sont traités avec les formulations de l'invention. Des procédés de préparation de ces formulations insectifuges et de traitement de substrats en tissu sont également décrits.
PCT/US1994/014745 1993-12-23 1994-12-22 Formulations a liberation lente repoussant les insectes et leurs utilisations WO1995017091A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002179743A CA2179743A1 (fr) 1993-12-23 1994-12-22 Formulations a liberation lente repoussant les insectes et leurs utilisations
JP7517583A JPH09510184A (ja) 1993-12-23 1994-12-22 徐放性昆虫忌避製剤及びその利用
AU15165/95A AU703959B2 (en) 1993-12-23 1994-12-22 Slow release insect repellent formulations and uses
EP95906680A EP0735817A4 (fr) 1993-12-23 1994-12-22 Formulations a liberation lente repoussant les insectes et leurs utilisations
BR9408411A BR9408411A (pt) 1993-12-23 1994-12-22 Formulações repelentes de insetos de liberação lenta e usos
NO962652A NO962652L (no) 1993-12-23 1996-06-21 Langtidsvirkende insektmidler samt anvendelse derav

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17341693A 1993-12-23 1993-12-23
US08/173,416 1993-12-23

Publications (1)

Publication Number Publication Date
WO1995017091A1 true WO1995017091A1 (fr) 1995-06-29

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EP (1) EP0735817A4 (fr)
JP (1) JPH09510184A (fr)
AU (1) AU703959B2 (fr)
BR (1) BR9408411A (fr)
CA (1) CA2179743A1 (fr)
NO (1) NO962652L (fr)
WO (1) WO1995017091A1 (fr)
ZA (1) ZA9410235B (fr)

Cited By (18)

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WO1997016195A1 (fr) * 1995-11-02 1997-05-09 Eli Lilly & Company (Nz) Limited Compositions en poudre mouillable d'antibiotiques ionophores
WO1998018998A1 (fr) * 1996-10-29 1998-05-07 Senecal Rene E Insecticide hydrofuge pour toile de tente
WO1998023149A1 (fr) * 1996-11-26 1998-06-04 Stephen Baker Bande insectifuge
GB2335143A (en) * 1996-11-26 1999-09-15 Stephen Baker Mosquito-repellent band
WO2001050859A1 (fr) * 2000-01-10 2001-07-19 Tucci & Associates, Inc. Compositions insectifuges a liberation lente et leurs utilisations
US6365174B1 (en) 1995-11-02 2002-04-02 Eli Lilly And Company Wettable powder compositions of ionophore antibiotics
EP1243689A1 (fr) * 2001-03-22 2002-09-25 Cognis Iberia, S.L. Procédé d'apprêt antimicrobien de fibres ou non-tissés
FR2840329A1 (fr) * 2002-05-30 2003-12-05 Protex Nouveau procede d'application de microcapsules par epuisement sur des supports textiles et fixation de ces microcapsules et articles textiles obtenus
GB2434592A (en) * 2006-01-27 2007-08-01 Intelligent Fabric Technologie Fabrics comprising insect repellent containing microcapsules
EP1880641A1 (fr) * 2005-04-29 2008-01-23 Chen-Chang Technology Co., Ltd. Filet en fils anti-insectes et procede de fabrication du filet
EP1944408A2 (fr) 2006-12-20 2008-07-16 Utexbel NV Procédé de formation d'un tissu doté de propriétés répulsives contre les insectes, l'eau et l'huile
WO2008083017A3 (fr) * 2006-12-29 2009-07-09 Southern Mills Inc Tissus insectifuges et leurs procédés de fabrication
US7811952B2 (en) 2006-04-20 2010-10-12 Southern Mills, Inc. Ultraviolet-resistant fabrics and methods for making them
EP2632257A2 (fr) * 2010-10-25 2013-09-04 Vanderbilt University Compositions pour inhiber la capacité d'insectes à détecter des hôtes
EP2839070A4 (fr) * 2012-04-24 2015-08-12 Argaman Technologies Ltd Procédé pour l'application en surface de composés chimiques sur des fibres aussi bien synthétiques que naturelles et système correspondant
WO2016124306A1 (fr) * 2015-02-02 2016-08-11 Merck Patent Gmbh Formulation en poudre contenant des insectifuges
US9578881B2 (en) 2011-05-06 2017-02-28 Vanderbilt University Compositions for inhibition of insect sensing
US10791739B2 (en) 2015-03-25 2020-10-06 Vanderbilt University Binary compositions as disruptors of orco-mediated odorant sensing

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DE102006016907A1 (de) * 2006-04-11 2007-10-25 Cognis Ip Management Gmbh Zur Insektenabwehr ausgerüstete Fasern und textile Flächengebilde
JP6026113B2 (ja) * 2012-02-22 2016-11-16 槌屋ティスコ株式会社 シール材
JP2019001768A (ja) * 2017-06-09 2019-01-10 大和化学工業株式会社 害虫忌避マイクロカプセル組成物及び該マイクロカプセルによって処理された繊維・不織布構造物。

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US3859121A (en) * 1971-01-07 1975-01-07 Us Agriculture Formulations for preparing long lasting insect repellent finishes for textile fabrics
US4765982A (en) * 1982-04-30 1988-08-23 Minnesota Mining And Manufacturing Company Insect control device
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Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6326015B1 (en) * 1993-12-23 2001-12-04 Tucci Associates, Inc. Slow-release insect-repellent fabric composition and related methods
WO1997016195A1 (fr) * 1995-11-02 1997-05-09 Eli Lilly & Company (Nz) Limited Compositions en poudre mouillable d'antibiotiques ionophores
US6365174B1 (en) 1995-11-02 2002-04-02 Eli Lilly And Company Wettable powder compositions of ionophore antibiotics
US6458377B1 (en) 1995-11-02 2002-10-01 Eli Lilly And Company Wettable powder compositions of ionophore antibiotics
WO1998018998A1 (fr) * 1996-10-29 1998-05-07 Senecal Rene E Insecticide hydrofuge pour toile de tente
WO1998023149A1 (fr) * 1996-11-26 1998-06-04 Stephen Baker Bande insectifuge
GB2335143A (en) * 1996-11-26 1999-09-15 Stephen Baker Mosquito-repellent band
GB2335143B (en) * 1996-11-26 2001-04-18 Stephen Baker Insect repellent apparel
WO2001050859A1 (fr) * 2000-01-10 2001-07-19 Tucci & Associates, Inc. Compositions insectifuges a liberation lente et leurs utilisations
EP1243689A1 (fr) * 2001-03-22 2002-09-25 Cognis Iberia, S.L. Procédé d'apprêt antimicrobien de fibres ou non-tissés
WO2002077359A1 (fr) * 2001-03-22 2002-10-03 Cognis Iberia S. L. Procede d'appretage antimicrobien de fibres ou de non tisses
FR2840329A1 (fr) * 2002-05-30 2003-12-05 Protex Nouveau procede d'application de microcapsules par epuisement sur des supports textiles et fixation de ces microcapsules et articles textiles obtenus
EP1880641A4 (fr) * 2005-04-29 2010-04-28 Chen Chang Technology Co Ltd Filet en fils anti-insectes et procede de fabrication du filet
EP1880641A1 (fr) * 2005-04-29 2008-01-23 Chen-Chang Technology Co., Ltd. Filet en fils anti-insectes et procede de fabrication du filet
GB2434592B (en) * 2006-01-27 2009-06-24 Intelligent Fabric Technologies Plc Fabrics and Materials Comprising Insect Repellent-Containing Microcapsules
GB2434592A (en) * 2006-01-27 2007-08-01 Intelligent Fabric Technologie Fabrics comprising insect repellent containing microcapsules
US7887826B2 (en) 2006-01-27 2011-02-15 Intelligent Fabic Technologies PLC Insect repellent fabric
US7811952B2 (en) 2006-04-20 2010-10-12 Southern Mills, Inc. Ultraviolet-resistant fabrics and methods for making them
US7862865B2 (en) 2006-04-20 2011-01-04 Southern Mills, Inc. Ultraviolet-resistant fabrics and methods for making them
EP1944408A2 (fr) 2006-12-20 2008-07-16 Utexbel NV Procédé de formation d'un tissu doté de propriétés répulsives contre les insectes, l'eau et l'huile
BE1017425A3 (nl) * 2006-12-20 2008-09-02 Utexbel Nv Insectenwerende water en olieafstotende behandeling van textiel.
WO2008083017A3 (fr) * 2006-12-29 2009-07-09 Southern Mills Inc Tissus insectifuges et leurs procédés de fabrication
US9332757B2 (en) 2010-10-25 2016-05-10 Vanderbilt University Composition for inhibition of insect host sensing
EP2632257A2 (fr) * 2010-10-25 2013-09-04 Vanderbilt University Compositions pour inhiber la capacité d'insectes à détecter des hôtes
EP2632257A4 (fr) * 2010-10-25 2014-06-25 Univ Vanderbilt Compositions pour inhiber la capacité d'insectes à détecter des hôtes
US10091997B2 (en) 2010-10-25 2018-10-09 Vanderbilt University Composition for inhibition of insect host sensing
US10701938B2 (en) 2010-10-25 2020-07-07 Vanderbilt University Composition for inhibition of insect host sensing
US10813355B2 (en) 2011-05-06 2020-10-27 Vanderbilt University Compositions for inhibition of insect sensing
US9578881B2 (en) 2011-05-06 2017-02-28 Vanderbilt University Compositions for inhibition of insect sensing
US10188105B2 (en) 2011-05-06 2019-01-29 Vanderbilt University Compositions for inhibition of insect sensing
US11484032B2 (en) 2011-05-06 2022-11-01 Vanderbilt University Compositions for inhibition of insect sensing
EP2839070A4 (fr) * 2012-04-24 2015-08-12 Argaman Technologies Ltd Procédé pour l'application en surface de composés chimiques sur des fibres aussi bien synthétiques que naturelles et système correspondant
US9995002B2 (en) 2012-04-24 2018-06-12 Argaman Technologies Ltd. Method for the surface application of chemical compounds to both synthetic and natural fibers and a system for same
WO2016124306A1 (fr) * 2015-02-02 2016-08-11 Merck Patent Gmbh Formulation en poudre contenant des insectifuges
US10893675B2 (en) 2015-02-02 2021-01-19 Merck Patent Gmbh Powder formulation containing insect repellent
US10791739B2 (en) 2015-03-25 2020-10-06 Vanderbilt University Binary compositions as disruptors of orco-mediated odorant sensing
US11856955B2 (en) 2015-03-25 2024-01-02 Vanderbilt University Binary compositions as disruptors of Orco-mediated odorant sensing

Also Published As

Publication number Publication date
BR9408411A (pt) 1997-08-05
EP0735817A4 (fr) 1998-09-09
AU1516595A (en) 1995-07-10
NO962652L (no) 1996-08-21
JPH09510184A (ja) 1997-10-14
AU703959B2 (en) 1999-04-01
ZA9410235B (en) 1995-09-12
CA2179743A1 (fr) 1995-06-29
EP0735817A1 (fr) 1996-10-09
NO962652D0 (no) 1996-06-21

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