US20090187060A1 - Method and Formulation for Neutralizing Toxic Chemicals and Materials - Google Patents

Method and Formulation for Neutralizing Toxic Chemicals and Materials Download PDF

Info

Publication number
US20090187060A1
US20090187060A1 US12/017,749 US1774908A US2009187060A1 US 20090187060 A1 US20090187060 A1 US 20090187060A1 US 1774908 A US1774908 A US 1774908A US 2009187060 A1 US2009187060 A1 US 2009187060A1
Authority
US
United States
Prior art keywords
method
active ingredient
acid
monoxime
oxime
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US12/017,749
Inventor
Timothy G. Henry
Barbara B. Price
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EMERGENT PROTECTIVE PRODUCTS CANADA ULC
Original Assignee
E-Z-Em 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 E-Z-Em Inc filed Critical E-Z-Em Inc
Priority to US12/017,749 priority Critical patent/US20090187060A1/en
Assigned to E-Z-EM, INC. reassignment E-Z-EM, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PRICE, BARBARA B., HENRY, TIMOTHY G.
Publication of US20090187060A1 publication Critical patent/US20090187060A1/en
Assigned to EMERGENT PROTECTIVE PRODUCTS CANADA ULC. reassignment EMERGENT PROTECTIVE PRODUCTS CANADA ULC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BRACCO DIAGNOSTICS INC., BRACCO USA INC., EZEM CANADA INC., E-Z-EM, INC.
Application status is Abandoned legal-status Critical

Links

Classifications

    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/36Detoxification by using acid or alkaline reagents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D3/00Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
    • A62D3/30Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
    • A62D3/33Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by chemical fixing the harmful substance, e.g. by chelation or complexation
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/02Chemical warfare substances, e.g. cholinesterase inhibitors
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/04Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/22Organic substances containing halogen
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/24Organic substances containing heavy metals
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/26Organic substances containing nitrogen or phosphorus
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/20Organic substances
    • A62D2101/28Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40Inorganic substances
    • A62D2101/43Inorganic substances containing heavy metals, in the bonded or free state
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40Inorganic substances
    • A62D2101/45Inorganic substances containing nitrogen or phosphorus
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40Inorganic substances
    • A62D2101/47Inorganic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
    • AHUMAN NECESSITIES
    • A62LIFE-SAVING; FIRE-FIGHTING
    • A62DCHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
    • A62D2101/00Harmful chemical substances made harmless, or less harmful, by effecting chemical change
    • A62D2101/40Inorganic substances
    • A62D2101/49Inorganic substances containing halogen

Abstract

The present invention is directed to a formulation and associated method for neutralizing one or more toxic chemical and/or materials including toxic industrial chemicals and toxic industrial materials, such as irritants, heavy metals, radioactive metals, acids and acid irritants, pesticides, and various agricultural chemicals, (collectively referred to as toxic chemical, materials, or simply toxins) as well as decontaminating surfaces that have come into contact with these agents. As a result, the formulation of the present invention can be used for neutralizing a broad spectrum of toxic chemicals and materials. In one embodiment, the active ingredient comprises 2, 3, butanedione monoxime (also known as diacetyl monoxime (DAM)), and alkali salts thereof such as potassium 2,3-butanedione monoxime (KBDO). The formulation also typically includes a carrier in which the active ingredient is dispersed. In one embodiment, the carrier comprises polyethylene glycol (PEG); monomethoxypolyethylene glycol(mPEG); and combinations and derivatives thereof.

Description

    FIELD OF THE INVENTION
  • The present invention relates generally to formulations and methods for neutralizing chemical agents, and more particularly, to formulations and methods for neutralizing a broad spectrum of chemical agents.
  • BACKGROUND OF THE INVENTION
  • The risk of exposure to various chemical and biological agents is an ever increasing concern for military personnel as well as civilians. This concern is particularly heightened in view of recent terrorist attacks. In particular, terrorist threats involving such agents are increasing in the United States as well as abroad. In response to this threat, various countermeasures have been developed that are capable of neutralizing certain chemical weapon agents. For example, so called nerve agents, such as sarin, soman, and tabun are examples of phosphorous containing compounds which can be altered chemically to remove their toxicity. Since many of these compounds share a common or similar chemical moiety, a single chemical countermeasure can be used to neutralize many of them.
  • In addition to chemical and biological agents, there also exists a wide variety of contaminants such as toxic industrial chemicals (TIC's) and toxic industrial materials (TIM's) that raise concerns over public safety. Such contaminants include industrial chemicals, pesticides, and herbicides and other materials that may be released in the environment during normal processing, disposal, waste handling, or accidental discharge. Generally, such contaminates comprise a broad spectrum of chemical compositions that are not readily neutralized or destroyed with a single chemical countermeasure. As a result, exposure to such contaminants requires that an appropriate countermeasure be selected in order to effectively neutralize the contaminant. Further, many countermeasures are only effective if they are applied prior to an exposure and are unable to effectively neutralize contaminants after a person has been exposed.
  • The problems with selecting an appropriate countermeasure are of particular concern in environments where a wide variety of toxic chemicals/materials are being used. For example, many modern factories use a wide variety of different chemicals and substances in their every day operation and processes. As a result, there exists a wide variety of different toxic chemical/materials to which personnel within the factory may be exposed. Since exposure to many of these chemicals/materials can result in severe injuries to the exposed workers, and in some cases death, there is a need to provide countermeasures that can be used to effectively treat individuals after exposure.
  • Unfortunately, this creates problems with respect to the feasibility of maintaining an adequate number of the appropriate countermeasures, as well as problems associated with educating personnel on selecting the appropriate countermeasure. Such problems can be heightened in emergency situations after an exposure has occurred. As a result, it may be difficult to find and apply the appropriate countermeasure in a timely fashion, which can result in prolonged exposure and an increase in the severity of the injury. Further, many chemical countermeasures, such as chemical disinfectants like hypochlorite solutions are useful but are corrosive to most metals and fabrics, and to human skin. Liquid-like foam disinfectants have also been used, and generally require water and pressurized gases for efficient application. As such, they are typically not practical under many circumstances.
  • In addition to factories, such problems can also be experienced in many households across the country. For example, the typical kitchen sink cabinet may include many different chemical/materials ranging from household cleaning products to pesticides. Similar to the chemicals/materials that may be found in a typical factory, exposure to household chemicals can also result in severe injury. However, most households today do not even include the most basic of countermeasures, and as a consequence, water is often the first choice in an attempt to cleanse exposed skin or surfaces. Since many chemical/materials do not react or are insoluble in water, the use of water can further exacerbate the exposure and severity of the injury by spreading the chemical/materials around and thereby increasing the area of contact with the toxic chemical/material.
  • In addition to chemical countermeasures, physical decontamination methods can also be used to neutralize many toxic chemical/materials. Physical decontamination usually involves dry heat for an extended period of time or steam or super-heated steam for about 20 minutes. In some cases, UV light can be used effectively, but it is generally difficult to implement in actual practice. Such physical decontamination methods cannot be used in the case of exposure to human skin, and are often impractical to use under many circumstances. Accordingly, there still exists a need for effective countermeasures that can be used to neutralize many of the toxic chemical/materials that may be encountered in factories, as well as in the home.
  • BRIEF SUMMARY OF THE INVENTION
  • In one alternative embodiment, the present invention is directed to a formulation and associated method for neutralizing toxic chemicals and materials, and a broad spectrum of toxic chemical and/or materials including, but not limited to, toxic industrial chemicals and toxic industrial materials, such as, for example, irritants, heavy metals, radioactive metals, acids and acid irritants, pesticides, and various agricultural chemicals, (collectively referred to as toxic chemical, materials, or simply toxins) as well as decontaminating surfaces that have come into contact with these agents. As a result, the formulation of the present invention can be used for neutralizing a wide variety of toxic chemicals and materials.
  • In particular, the present invention comprises a formulation having one or more active moieties that are capable of neutralizing one or more chemical agents including, but not limited to, acids, toxic industrial chemicals, toxic industrial materials, metal ions, and pesticides.
  • In one embodiment, the formulation may include an active ingredient having a nitrogen oxime moiety and a carbonyl moiety that is capable of neutralizing a variety of toxins via a nucleophilic or electrophilic attack. In one embodiment, the active ingredient comprises 2, 3, butanedione monoxime (also known as diacetyl monoxime (DAM)), and alkali salts thereof such as potassium 2,3-butanedione monoxime (KBDO). The formulation may also include a carrier in which the active ingredient is dispersed. In one embodiment, the carrier may comprise polyethylene glycol (PEG); monomethoxypolyethylene glycol(mPEG); and combinations and derivatives thereof.
  • In one embodiment, the formulation of the present invention can be used to neutralize a wide variety of toxic industrial chemical and materials. In one such embodiment, DAM and its salts, such as KBDO, include three potentially nucleophilic atoms that are capable of nucleophilic attack on reactive moieties on the targeted chemical. For example, the structure of DAM includes three nucleophilic atoms: the carbonyl oxygen, the oxime nitrogen and, to a lesser extent, the oxime oxygen. The nucleophilic atoms are capable of attacking and neutralizing a wide variety of toxic chemicals. In addition to neutralizing toxins that are susceptible to nucleophilic attack, DAM and KBDO can be used to neutralize acid toxins as well. In some embodiments, DAM and KBDO can also be used to chelate metal ions and thereby can be used to effectively remove and neutralize the metal ions. In yet a further embodiment, the DAM and KBDO may be present in a carrier, such as PEG or mPEG, that is capable of solublizing and neutralizing various TICs and TIMs.
  • In yet another embodiment, the present invention can be used to neutralize many acids and acid anhydrides that may be encountered in a manufacturing or production environment, such as, for example, sulfuric acid (H2SO4), hydrochloric acid (HCl), hydrofluoric acid (HF), perchloric acid (HClO4), hydrobromic acid (HBr), hydroiodic acid (HI), nitric acid (HNO3), nitrous acid (HNO2), acetic acid, arsine (AsH3), hydrogen selenide, hydrogen sulfide (H2S), acid byproducts of nitrogen dioxide (NO2), sulfur dioxide (SO2), maleic anhydride, acetic anhydride, mixed anhydrides, and any salt, ester or derivative thereof, or any combination thereof, and the like.
  • In addition to neutralizing acids, the formulation may also be used to neutralize a wide variety of irritants that are commonly used in many industrial circumstances. For example, may toxic industrial or toxic materials include one or more reactive moieties that are susceptible of nucleophilic attack by one or more of the nucleophilic atoms of DAM. Such toxins may include, without limitation, 1,1′-bi(ethylene oxide), acrylonitriles, allyl alcohols, allyl chlorides, methyl mercaptan, phosgene, hydrazine, and the like, and any salt, ester or derivative thereof or any combination thereof.
  • In one embodiment, the formulation of the present invention may be capable of neutralizing toxins that are soluble in glycols such as hydrazine, phosphine, and toluene diisocyanates (mixed isomers). The present invention may also be used to neutralize some oxidizing and corrosive toxins.
  • In one alternative embodiment, the present invention is directed to a method for neutralizing a broad spectrum of toxic industrial chemicals and materials in which a composition having an active ingredient is applied to a toxic industrial chemical or material to thereby neutralize the toxic industrial chemical or and material. In one embodiment, the active ingredient comprises 2,3, butanedione monoxime or an alkali salt thereof.
  • In one alternative embodiment, the formulation of the present invention can be used to neutralize various metals and radionuclides, such as heavy metals, lead, transition metals, radioactive metals, Pu, Th, U, Zr, Nb, Ru, actinides, lanthanides, rare earth elements and combinations thereof, for example, via a chelating or ring forming reaction. In this embodiment, the DAM acts as a chelating agent to form a chelate complex in which the metal is bound to two or more atoms of the chelating agent. In one embodiment, DAM is capable of chelating with metal ions to form a five to seven member ring.
  • In one alternative embodiment, the present invention provides a method for neutralizing or sequestering metal atoms in which a composition having at least one nucleophilic carbonyl moeity and at least one nucleophilic oxime nitrogen moiety is reacted with a metal. Reaction of the composition and the metal chelates the metal to form a ring structure in which the at least one nucleophilic carbonyl moiety and at least one nucleophilic oxime nitrogen moiety are bonded to the metal.
  • In one alternative embodiment, the formulation of the present invention may also be used to neutralize a wide variety of pesticides. In one embodiment, formulations of the present invention can be used to neutralize pesticides containing organophosphates (OPs), pyrethroids (SP), carboxy moieties, and carbamates, or any combination thereof. In one embodiment a first DAM molecule reacts with a pesticide containing OP to produce a phosphorylated oxime. In a subsequent reaction, a second DAM molecule then reacts with the phosphonylated oxime to produce a non-toxic substituted phosphonic acid. In one embodiment, OPs pesticides that can be neutralized with DAM include, but are not limited to, azinphos-methyl, chlorpyrifos, diazinon, disulfoton, ethoprop, fonofos, malathion, methyl parathion, parathion, phorate, and terbufos.
  • In a further embodiment, the formulation of the present invention may also be used to neutralize pesticides containing carbamates, such as 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime (Aldicarb); 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (carbofuran, furadan, or curator); 3-hydroxycarbofuran; ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate (fenoxycarb); 1-naphthyl methylcarbamate (carbaryl also known under the tradename Sevin); ethienocarb, examples: 3-hydroxycarbofuran, aldicarb sulfone, aldicarb sulfoxide, butylate, S-ethyl dipropylthiocarbamate (EPTC), methiocarb, methomyl, molinate, oxamyl, pebulate, propham, propoxur, thiobencarb, triallate and 2-(1-methylpropyl)phenyl N-methylcarbamate.
  • In one alternative embodiment, the present invention is directed to a method of neutralizing a broad spectrum of pesticides, such as organophosphates, carbamates, organochlorine, and pyrethroids, in which a composition containing 2,3, butanedione monoxime or an alkali salt thereof is reacted with a pesticide to thereby neutralize the pesticide.
  • In one embodiment, the composition containing the active ingredient is applied in an amount that ranges from about 1:1 to 20:1 to the amount of pesticide to which a person or surface has been exposed. In some embodiments, the amount may range from about 2:1 to 15:1, and in particular from about 5:1 to 10:1. Following treatment of the toxin with the active ingredient, water may be used to remove any residual of the toxin and formulation from a surface or skin of a person that has been treated.
  • In one embodiment, the formulation can be provided as a topical skin protectant (TSP), such as a lotion or cream, that can be applied to human skin prior to, or after exposure to toxic chemicals or materials. In some embodiments, the formulation can be provided in the form of a liquid, gel, powder, emulsion, foam, spray, and the like. In one embodiment, the formulation can be used to decontaminate surfaces that have been exposed to toxic chemicals or materials, including but not limited to metal surface, stone surfaces, and plastic surfaces.
  • DETAILED DESCRIPTION OF THE INVENTION
  • The present invention now will be described more fully hereinafter with reference to the accompanying drawings, in which some, but not all embodiments of the inventions are shown. Indeed, these inventions may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will satisfy applicable legal requirements. Like numbers refer to like elements throughout.
  • In one embodiment of the invention, the formulation provides one or more decontaminants that can be used to neutralize a broad spectrum of toxic chemicals and materials. In the context of the present invention, the term “neutralization’ includes the detoxification, decontamination, mitigation, or otherwise substantial destruction of toxins so that they reduce the acute adverse effects in humans or animals. Methods of neutralization include, but are not limited to, nucleophilic attack, electrophilic attack, chelating reactions, acid-base reactions, solubilization, sequestration, and combinations thereof.
  • In one embodiment, the formulation includes an active ingredient having a nitrogen oxime moiety and a carbonyl moiety that is capable of neutralizing a variety of toxins via a nucleophilic or electrophilic attack. In another embodiment the active ingredient includes a nitrogen oxime moiety and a carbonyl moiety. In yet another embodiment, the active ingredient comprises 2, 3, butanedione monoxime, also known as diacetyl monoxime (DAM), and salts thereof inducing, but not limited to, alkali salts such as potassium 2,3-butanedione monoxime (KBDO) and sodium 2,3-butanedione monoxime, and alkaline earth salts such as calcium 2,3-butanedione monoxime. The structure of DAM is illustrated by formula (I) below.
  • Figure US20090187060A1-20090723-C00001
  • In one alternative embodiment, additional oximes that may be used in the practice of the invention include derivatives of DAM in which the alkyl group of DAM includes four to six carbon atoms. For example, in one embodiment, the active ingredient may include one or more of 2,3 pentandione monoxime, 3,4 pentandione monoxime, 3,4 hexanone monoxime, 2,3 hexananone monoxime and 4,5 hexanone monoxime (alternate names may include 2,3-pentanedione 3-oxime (CAS 609-29-0) 2 oximo pentane-3-one, 3, oximo pentane-4-one, 2,3-Pentanedione, 3-oxime, 2,4-Pentanedione oxime, Pentane-2,3-dione 2-oxime, 2,3,4-Pentanetrione, 3-oxime, 2,4-Pentanedione, dioxime, 2,4-Pentanedione, 2,4-dioxime, and combinations thereof. Unless otherwise stated, the reference to DAM herein includes diacetyl monoxime, 2,3-butanedione monoxime, salts thereof, as well as derivatives thereof. When the formulation is applied to a susceptible toxin, one or more of the reactive moieties reacts with the targeted toxin to thereby neutralize the toxin. In one embodiment, the toxin is at least substantially decomposed into end products that can be removed with water or by other means.
  • In one embodiment, the formulations of the present invention can be delivered and applied to the toxins in a variety of manners and phases to provide the necessary detoxification and decontamination. For example, the formulation can be in the form of a topical skin protectant (TSP), such as a lotion or cream, a liquid solution or suspension, a foam, and the like. In one alternative embodiment, formulations of the present invention may be in the form of a gel or coating. Gels and coatings suitable for the present invention are generally known in the art.
  • As discussed in greater detail below, an alternative embodiment of the present invention may generally comprise an activated solution or product that can be applied to a surface or skin of an individual in need thereof, or dispersed into the air to neutralize or other wise detoxify one or more toxic chemicals/materials.
  • In one embodiment, the formulation may generally include one or more active ingredients that are capable of binding, absorbing, solubilizing, or otherwise neutralizing a targeted chemical compound. The formulation may also typically include a carrier in which the active ingredient is dispersed. In one embodiment, the carrier comprises polyethylene glycol (PEG); monomethoxypolyethylene glycol(mPEG); and combinations and derivatives thereof. In one embodiment, the active ingredient may be dispersed in a base comprising a macrocycle chosen from 1,4,7,10,13,16-hexaoxacyclooctadecane and 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane together with a carrier chosen from dioxolane, tetraglyme, dimethoxyethane, a polyethylene glycol, or a polyethylene glycol mono- or di-ether. In another embodiment, the formulation may also include water or other solvent in amounts sufficient to ensure dissolution of the active ingredient in the base.
  • In one alternative embodiment, the base contains substantially equal amounts of the macrocycle and of the active ingredient. The amount of water or solvent present in the formulation is generally dependent on the desired end use of the formulation. For example, in creams and similar applications, the amount of water included may be small, such as less than about 5% of the base. In other embodiments, it may be desirable that the amount of water present be kept to a minimum as otherwise unwanted side reactions between the active ingredient and the water or solvent may occur. In some embodiments, the formulation will contain no water or solvent at all.
  • As discussed above, the formulation may include a carrier, such as polyethylene glycol, monomethoxypolyethylene glycol, or polyethylene glycol ether. These compounds have the formula R—O—CH2CH2O)nCH2CH2OR in which either R may be hydrogen or an alkyl group, including but not limited to methyl or ethyl, and “n” indicates the chain length. In one alternative embodiment, “n” can have a range of values. Generally, as “n” increases, the compound becomes more viscous. For example, in cream applications it may be desirable for the formulation to be relatively thick and viscous, and therefore it may be desirable to include a thickening agent. Generally, at value of “n” that represents a molecular weight of 1500 no thickening agent may be needed for the formulation to be in the form of a cream. In one embodiment, at least one of the R groups, and most preferably both, are other than hydrogen, and are typically methyl or ethyl.
  • In one embodiment, the formulation may be in the form of oil in water or water in oil emulsions. Other components of such emulsions may include emulsifying agents and oils conventionally used in barrier creams or lotion type formulations such as mineral or silicone oils.
  • In some embodiments, the formulation may also include one or more additional additives, such as surfactants, moisturizers, fragrances, fillers, coloring agents, emulsifiers, thickening agents, and the like provided the additives are inert to the active ingredient. In one alternative embodiment, the formulation may include a pharmaceutically acceptable inert solid as a thickener, which is also inert toward the active ingredient. Typical usable solids may include silicas, titania, fuller's earth, clays, bentonite and the like.
  • Neutralization of Toxic Industrial Chemicals and Materials
  • In one embodiment, formulations of the present invention can be used to neutralize a wide variety of toxic industrial chemical and materials, commonly referred to as TICS and TIMS, respectively. Many TICS and TIMS may include acids and skin irritants that can cause burning and irritation to the skin. In one embodiment, the formulation of the present invention may be used to neutralize and/or mitigate the harmful effects of these various toxins and thereby help ameliorate burns and skin irritations that may result from exposure thereto. In some embodiments, the formulation of the present invention may also be formulated to be applied to surfaces that have been exposed to TICS and TIMS. TICS and TIMS may include chemical materials found in manufacturing, production, and maintenance facilities and do not necessarily include chemical warfare agents such as, for example, vesicants (e.g., mustard gas) and nerve gas.
  • DAM and its salts, such as KBDO, include three potentially nucleophilic atoms that are capable of nucleophilic attack on reactive moieties on the targeted chemical. For example, the structure of DAM includes three nucleophilic atoms: the carbonyl oxygen, the oxime nitrogen and, to a lesser extent, the oxime oxygen. The nucleophilic atoms are capable of attacking and neutralizing a wide variety of toxic chemicals. In addition to neutralizing toxins that are susceptible to nucleophilic attack, DAM and KBDO can be used to neutralize acid toxins as well. In some embodiments, DAM and KBDO can also be used to chelate metal ions and as a result can be used to effectively remove and neutralize various metal ions. In yet a further embodiment, the DAM and KBDO may be present in a carrier, such as PEG or mPEG, that is capable of solublizing and neutralizing various TICs and TIMs.
  • In some embodiments, formulations in accordance with the present invention can be used to neutralize many acids and acid anhydrides that may be encountered in the work place. Such acids may include, without limitation, sulfuric acid (H2SO4), hydrochloric acid (HCl), hydrofluoric acid (HF), perchloric acid (HClO4), hydrobromic acid (HBr), hydroiodic acid (HI), nitric acid (HNO3), nitrous acid (HNO2), acetic acid, arsine (AsH3), hydrogen selenide, hydrogen sulfide (H2S), acid byproducts of nitrogen dioxide (NO2), sulfur dioxide (SO2), fluoroacetic acid, chloroacetic acid, malonic acid, formic acid, phosphoric acids, acid anhyrides such as maleic anhydride, acetic anhydride, and the like. In this embodiment, the active ingredient (e.g., DAM) and its salt KBDO are basic and are capable of reacting with acids to thereby neutralize them. In some cases, workers exposed to an acid have attempted to remove the acid by applying water, which only exacerbates the situation. In the present invention, the formulation can be applied to the skin in order to quickly neutralize the acid component and thereby help prevent further injury to the worker.
  • In addition to neutralizing acids, the formulation may also be used to neutralize a wide variety of irritants that are commonly used in many industrial circumstances. For example, many toxic industrial chemicals or toxic industrial materials include one or more reactive moieties that are susceptible of nucleophilic attack by one or more of the nucleophilic atoms of DAM. Typical reactive moieties that are susceptible to nucleophilic attack may include, carbonyls, allyls, epoxides, amides, nitriles, acid anhydrides, and the like. Such toxins may include, without limitation, 1,1′-bi(ethylene oxide), acrylonitriles, allyl alcohols, allyl chlorides, methyl mercaptan, acetic anhydride, fluoroacetic acid, and the like. In one embodiment, the formulation of the present invention may also be used to neutralize phosgene via a nucleophilic attack by one or more of the nucleophilic atoms of DAM.
  • In one alternative embodiment, formulations of the present invention can also be used to neutralize toxins that are soluble in alcohols, such as glycols. In this embodiment, the active ingredient is typically present in a glycol based carrier such as PEG or mPEG. In this embodiment, the carrier is capable of solublizing and thereby neutralizing the toxin. In one embodiment, the formulation of the present invention may be capable of neutralizing toxins such as hydrazine, phosphine, and toluene diisocyanates (mixed isomers).
  • In the case of hydrazine, it is believed that the active ingredient of the formulation (e.g., DAM) reacts with the basic hydrazine to help neutralize hydrazine's basicity while the glycol based carrier concomitantly assists the active ingredient by at least substantially solubilizing hydrazine. As a result, the formulation of the present invention can be used to help safely neutralize hydrazine so that the hydrazine can be removed by washing the exposed skin or surface with water.
  • In some embodiments, the formulation may also be used to neutralize corrosive toxins, including but not limited to, ammonia, anhydrous ammonia, and oxidizing toxins, such as chlorine.
  • Generally, the amount of the formulation that is needed to neutralize the toxic industrial chemicals or materials will depend on the amount of the toxic industrial chemicals or materials to which the person or surface has been exposed. In one embodiment, the composition containing the active ingredient may be applied in an amount that ranges from about 1:1 to 20:1 to the amount of toxic industrial chemicals or materials to which a person or surface has been exposed. In some embodiments, the amount may range from about 2:1 to 15:1, and in particular from about 5:1 to 10:1. In one embodiment, after application of the formulation to the toxic industrial chemical or material, water can be used to remove any residual from the skin or surface that has been treated.
  • Neutralization of Heavy Metals and Radioactive Metals
  • In one alternative embodiment, the formulation of the present invention can be used to neutralize various metal and radionuclides, such as heavy metals, lead, transition metals: radioactive metals Pu, Th, U, Zr, Nb, Ru, actinides, lanthanides, rare earths and combination thereof, for example, via a chelating or ring forming reaction. In this embodiment, the DAM acts as a chelating agent to form a chelate complex in which the metal is bound to two or more atoms of the chelating agent.
  • The structure of DAM can form a stable 5 to 7 ring structure with transition metals, actinides, lanthanides and heavy metals. For example, 2,3-butanedione monoxime may form a 5 membered ring with various metals, and derivatives of DAM, such as 2, 4 hexanedione 2 oxime, may form 6 member ring structures. Generally, the resulting ring structure having between 5 and 7 sides provides a relatively stable reaction product in which the metal is effectively bound by the DAM. As shown in Formula (1) above, DAM includes a carbonyl oxygen and an oxime nitrogen moiety. These moieties can function as ligands that each form a bond or coordinate with the metal at more than one of the metals coordination sites. For example in the case of a lead atom, the ═N and ═O of DAM bind to a separate coordinate site of Pb to form a stable 5 membered ring.
  • Generally, metals having an empty or partially empty outer electron shell can coordinate with DAM to form a chelate complex. In one embodiment, DAM can coordinate with metals, such as transition metals, heavy metals, and actinide and transuranic metals to form a bi-dentate ligand. DAM has three nucleophilic atoms, the carbonyl oxygen, the oxime nitrogen and, to a lesser extent, the oxime oxygen. The potassium salt oximate (KBDO) has these same nucleophilic atoms and is generally believed to be more strongly nucleophilic than the neutral oxime. For example, in one embodiment DAM may chelate with Pb to form a square planar coordination complex. In yet another embodiment, a possible lead and DAM or KBDO complex is depicted below. The two dashed lines from the Pb to the oxime N and carbonyl O are the coordination bonds that form a five membered ring. In some embodiments, another molecule of DAM or KBDO can be accommodated by the Pb atom, using remaining sp3d2 orbitals to make a square planar complex as depicted below.
  • Figure US20090187060A1-20090723-C00002
  • In another embodiment, DAM and KBDO may be used to complex with actinide and transuranic metals to remove them from solutions and/or surfaces. It is believed that this is especially effective in decontaminating surfaces which have been exposed to radioactive materials from a radiological weapon or radiological dispersal device (RDD), or other form of spreading radioactive materials on surfaces/areas.
  • Generally, the amount of the formulation that is needed to neutralize the metals will depend on the amount of the metal to which the person or surface has been exposed. In one embodiment, the composition containing the active ingredient may be applied in an amount that ranges from about 1:1 to 20:1 to the amount of metal to which a person or surface has been exposed. In some embodiments, the amount may range from about 2:1 to 15:1, and in particular from about 5:1 to 10:1. In one embodiment, after application of the composition to the metal, water can be used to remove any residual from the skin or surface that has been treated.
  • Neutralization of Pesticides
  • In one alternative embodiment, the formulation of the present invention may also be used to neutralize a wide variety of pesticides. Pesticides used in the United States are generally categorized in several major classes: organophosphates, carbamates, organochlorine, and pyrethroids. In one embodiment, formulations of the present invention can be used to neutralize pesticides containing organophosphates (OPs), pyrethroids (SP), carboxy moieties, and carbamates. Pesticides generally include chemicals and materials commonly used in insecticides, and do not necessarily include chemical warfare agents such as vesicants and nerve gas.
  • It is believed that in the neutralization of OP pesticides, the nitrogen oxime of DAM react with active phosphorus center of the OP in a nucleophilic attack. The nucleophilic attack results in the OP compound decomposing into reaction byproducts. In this reaction, a first molecule of DAM reacts with the OP to produce a phosphorylated oxime. In a subsequent reaction, a second DAM molecule then reacts with the phosphonylated oxime to produce a non-toxic substituted phosphonic acid. In one embodiment, OPs pesticides that can be neutralized with DAM include, but are not limited to, azinphos-methyl, chlorpyrifos, diazinon, disulfoton, ethoprop, fonofos, malathion, methyl parathion, parathion, phorate, and terbufos.
  • Pesticides containing carbonyls, such as carbamates, can cause cholinesterase inhibition poisoning by reversibly inactivating the enzyme acetylcholinesterase. In a further embodiment, the formulation of the present invention may also be used to neutralize pesticides containing carbamates, such as 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime (Aldicarb); 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate (carbofuran, furadan, or curator); 3-hydroxycarbofuran; ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate (fenoxycarb); 1-naphthyl methylcarbamate (carbaryl also known under the tradename Sevin); ethienocarb, 3-hydroxycarbofuran; aldicarb sulfone; aldicarb sulfoxide; butylate; S-ethyl dipropylthiocarbamate (EPTC); methiocarb; methomyl; molinate; oxamyl; pebulate; propham; propoxur; thiobencarb; triallate; and 2-(1-methylpropyl)phenyl N-methylcarbamate. It is believed that the carbonyl at the center of the carbonate is electrophilic and therefore susceptible to nucleophilic attack by the oxime of DAM.
  • In some embodiments, the carrier may also provide an effective means for neutralizing carbamates by removing or sequestering the carabate. In one embodiment, the carrier may comprise a polyglycol, such as PEG or mPEG, that is capable of solubilizing carbamates to thereby remove and neutralize the carbamate.
  • Generally, the amount of the formulation that is needed to neutralize the pesticides will depend on the amount of the pesticide to which the person or surface has been exposed. In one embodiment, the composition containing the active ingredient may be applied in an amount that ranges from about 1:1 to 20:1 to the amount of pesticide to which a person or surface has been exposed. In some embodiments, the amount may range from about 2:1 to 15:1, and in particular from about 5:1 to 10:1. In one embodiment, after treatment of the pesticide with the formulation, water can be used to remove residual from the skin or surface that has been treated.
  • As discussed above, formulations in accordance with the invention can be formulated to be delivered and applied to toxins in a variety of manners and phases. For example, the formulation can be provided as a topical skin protectant (TSP), such as a lotion or cream, that can be applied to human skin prior to, or after exposure to toxic chemicals or materials. In some embodiments, the formulation can be provided in the form of a liquid, gel, powder, emulsion, foam, spray, and the like. In one embodiment, the formulation can be used to decontaminate surfaces that have been exposed to toxic chemicals or materials.
  • Generally, the amount of active ingredient in the formulations is from about 1 to 90; 1 to 50; or 1 to 25 weight percent, based on the total weight of the formulation. In one embodiment, the amount of active ingredient in the formulation is between about 2 and 20 weight percent, and in particular between about 4 and 18 weight percent, and more particularly between about 5 and 15 weight percent, based on the total weight of the formulation.
  • Tables 1 and 2 below describe exemplary, non-limiting embodiments of the present invention in which the formulation is in the form of a cream.
  • TABLE 1
    Cream Formulation
    Concentration
    Composition Ingredient (Wt. %)
    Carrier MPEG 550 60 to 95
    Active Ingredient KBDO/DAM 0.5 to 20 
    Water Water  5 to 15
  • TABLE 2
    Cream Formulation
    Ingredient Wt. %
    KBDO 14.7 ± 0.5 
    DAM 0.78 to 0.95
    MPEG 550 75.98
    Purified Water  8.44
  • As noted above, formulations of the present invention may be in the form of a aerosols, lotions, creams and gels. Generally, the desired viscosity of the formulations will depend on the intended use, which can be readily ascertained by one skilled in the art. For example, gels will generally have a viscosity that is greater than the viscosity of a lotion, cream, or aerosol. Table 3 below lists some exemplary viscosities for formulations that are in accordance with embodiments of the present invention.
  • TABLE 3
    Representative Viscosities
    Viscosity Range
    Form [cp]
    Aerosol   <100
    Lotion  100 to 5,000
    Cream 5,000 to 25,000
    Gel >25,000

    In one embodiment, formulations in accordance with the present invention may have a viscosity between 140 and 180 cp at +25° C.
  • In one alternative embodiment, formulations in accordance with the present invention may be produced by varying blends of MPEG. For example, in one embodiment, mPEGs of varying viscosity can be blended in proportions to increase or decrease the resulting viscosity of the end product.
  • In one embodiment, the formulation's viscosity may be increased by physico-mechanical process of emulsification. Tables 4 and 5 below illustrate non-limiting, exemplary formulations that are in accordance with embodiments of the present invention.
  • TABLE 4
    Lotion base, example of formula
    Ingredient Wt. %
    Mineral oil 25
    Dioctyldodecyl dodecanedioate 2
    Dimethicone 1
    Glyceryl stearate 6
    Cetyl esters 1
    Polysorbate 60 4
    Cetyl alcohol 1
    Glycerin 5
    Water 55
  • TABLE 5
    Cream base, example of formula
    Ingredient Wt. %
    Emulsifying wax 2
    Dioctyldodecyl dodecanedioate 5
    Cetearyl alcohol (and) ceteareth 20 2
    Glyceryl stearate (and) PEG 100 stearate 1
    C12-15 alcohol benzoate 2
    Glyceryl stearate 2
    Cetyl alcohol 2
    Montmorillonite 1
    Water 80
  • Many modifications and other embodiments of the inventions set forth herein will come to mind to one skilled in the art to which these inventions pertain having the benefit of the teachings presented in the foregoing descriptions and the associated drawings. Therefore, it is to be understood that the inventions are not to be limited to the specific embodiments disclosed and that modifications and other embodiments are intended to be included within the scope of the appended claims. Although specific terms are employed herein, they are used in a generic and descriptive sense only and not for purposes of limitation.

Claims (24)

1. A method for neutralizing a broad spectrum of toxic industrial chemicals and materials, the method comprising the steps of:
applying a composition having an active ingredient to a toxic industrial chemical or material to thereby neutralize said toxic industrial chemical or and material, wherein the active ingredient comprises one or more of 2,3, butanedione monoxime, an alkali or alkaline salt thereof, or a derivative thereof.
2. The method of claim 1, wherein the toxic industrial material is an acid or an agent including a moiety that is susceptible to nucleophilic attack by a nucleophilic carbonyl atom or a nucleophilic oxime nitrogen atom or an oxygen atom.
3. The method of claim 2, wherein the toxic industrial chemical or material is selected from the group consisting of 1,1′-bi(ethylene oxide), acrylonitriles, allyl alcohols, allyl chlorides, methyl mercaptan, and phosgene.
4. The method of claim 1, wherein the toxic chemical or material is an acid.
5. The method of claim 3, wherein the acid is selected from the group consisting of sulfuric acid (H2SO4), hydrochloric acid (HCl), hydrofluoric acid (HF), perchloric acid (HClO4), hydrobromic acid (HBr), hydroiodic acid (HI), nitric acid (HNO3), nitrous acid (HNO2), acetic acid, arsine (AsH3), hydrogen selenide, hydrogen sulfide (H2S), acid byproducts of nitrogen dioxide (NO2), sulfur dioxide (SO2), phosphoric acids, acetic anhydride, maleic anhydride, mixed anhydries, fluoroacetic aceid, and chloroacetic acid.
6. The method of claim 1, wherein the active ingredient is dispersed in a carrier that is selected from the group consisting of polyethylene glycol, monomethoxypolyethylene glycol, and polyethylene glycol ether.
7. The method of claim 6, wherein the toxic industrial chemical or material is selected from the group consisting of hydrazine, chlorine, and ammonia.
8. The method of claim 1, wherein the composition containing the active ingredient is applied in an amount ranging from about 1:1 to 20:1 based on the amount of toxic industrial chemical or material.
9. The method of claim 1, wherein the active ingredient is selected from the group consisting of 2,3 pentandione monoxime, 3,4 pentandione monoxime, 3,4 hexanone monoxime, 2,3 hexananone monoxime and 4,5 hexanone monoxime (alternate names may include 2,3-pentanedione 3-oxime (CAS 609-29-0) 2 oximo pentane-3-one, 3, oximo pentane-4-one, 2,3-Pentanedione, 3-oxime, 2,4-Pentanedione oxime, Pentane-2,3-dione 2-oxime, 2,3,4-Pentanetrione, 3-oxime, 2,4-Pentanedione, dioxime, 2,4-Pentanedione, 2,4-dioxime, and combinations thereof.
10. The method of claim 1, wherein the step of neutralizing said toxic industrial chemical or and material comprise sequestering said toxic industrial chemical or and material
11. A method for neutralizing metal atoms, the method comprising the steps of:
reacting a composition having an active ingredient having at least one nucleophilic carbonyl moeity and at least one nucleophilic oxime nitrogen moiety with a metal; and
chelating the metal to form a ring structure in which the at least one nucleophilic carbonyl moiety and at least one nucleophilic oxime nitrogen moiety are bonded to the metal.
12. The method of claim 11, wherein the active ingredient comprises 2,3, butanedione monoxime or an alkali or alkaline salt thereof.
13. The method of claim 11, wherein the active ingredient comprises potassium 2,3, butanedione monoxime.
14. The method of claim 11, wherein the metal is selected from the group consisting of heavy metals, lead, transition metals, radioactive metals, Pu, Th, U, Zr, Nb, Ru, actinides, lanthanides, rare earth metals, and combination thereof.
15. The method of claim 11, wherein the ring has 5 to 7 sides.
16. The method of claim 11, wherein the active ingredient is selected from the group consisting of 2,3 pentandione monoxime, 3,4 pentandione monoxime, 3,4 hexanone monoxime, 2,3 hexananone monoxime and 4,5 hexanone monoxime (alternate names may include 2,3-pentanedione 3-oxime (CAS 609-29-0) 2 oximo pentane-3-one, 3, oximo pentane-4-one, 2,3-Pentanedione, 3-oxime, 2,4-Pentanedione oxime, Pentane-2,3-dione 2-oxime, 2,3,4-Pentanetrione, 3-oxime, 2,4-Pentanedione, dioxime, and 2,4-Pentanedione, 2,4-dioxime, and combinations thereof.
17. The method of claim 11, wherein the composition containing the active ingredient is applied in an amount ranging from about 1:1 to 20:1 based on the amount of metal.
18. The method of claim 11, wherein the active ingredient comprises 2,3, butanedione monoxime, and further comprising the steps of:
reacting the metal with a first and second molecule of 2,3, butanedione monoxime to form a chelated metal having a square planar complex.
19. The method of claim 11, wherein the composition is applied to the skin of a person in need thereof.
20. A method of neutralizing a broad spectrum of pesticides, the method comprising: reacting a composition having an active ingredient with a pesticide to thereby neutralize said pesticide, wherein the active ingredient comprises 2,3, butanedione monoxime or an alkali salt thereof, and wherein the pesticide is selected from the group consisting of organophosphates, carbamates, organochlorine, and pyrethroids.
21. The method of claim 20, wherein the pesticide includes a carbamate selected from the group consisting of 2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate, 3-hydroxycarbofuran; ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate, 1-naphthyl methylcarbamate, ethienocarb, 3-hydroxycarbofuran, aldicarb sulfone, aldicarb sulfoxide, butylate, S-ethyl dipropylthiocarbamate, methiocarb, methomyl, molinate, oxamyl, pebulate, propham, propoxur, thiobencarb, triallate, and 2-(1-methylpropyl)phenyl N-methylcarbamate.
22. The method of claim 20, wherein the composition is applied to the skin of a person in need thereof.
23. The method of claim 20, wherein the composition is a cream, a gel, or a lotion.
24. The method of claim 20, wherein the active ingredient is dispersed in a carrier and wherein the method further comprises reacting the carrier with the pesticide to thereby sequester the pesticide.
US12/017,749 2008-01-22 2008-01-22 Method and Formulation for Neutralizing Toxic Chemicals and Materials Abandoned US20090187060A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/017,749 US20090187060A1 (en) 2008-01-22 2008-01-22 Method and Formulation for Neutralizing Toxic Chemicals and Materials

Applications Claiming Priority (29)

Application Number Priority Date Filing Date Title
US12/017,749 US20090187060A1 (en) 2008-01-22 2008-01-22 Method and Formulation for Neutralizing Toxic Chemicals and Materials
SG10201704671XA SG10201704671XA (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
CA2905681A CA2905681A1 (en) 2008-01-22 2008-12-30 Method and formulation for neutralzing toxic chemicals and materials
CA2712324A CA2712324C (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
CN201510617667.0A CN105344058A (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing pesticides
CN2008801281715A CN101977658B (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
EP08871506A EP2247348A2 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
BRPI0822225-8A BRPI0822225A2 (en) 2008-01-22 2008-12-30 Method and compositions for neuralização materials and toxic chemicals
CN201310126374.3A CN103212182B (en) 2008-01-22 2008-12-30 And the formulation and method of toxic chemicals and substances
KR1020107018020A KR20100103872A (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
JP2010544304A JP2011511656A (en) 2008-01-22 2008-12-30 Methods and formulations for neutralizing toxic chemicals and toxic materials
PCT/US2008/088547 WO2009094098A2 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
AU2008348284A AU2008348284C1 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
KR1020147025482A KR20140112582A (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
KR1020157011751A KR101657605B1 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
RU2010134593/05A RU2495697C2 (en) 2008-01-22 2008-12-30 Method and formulation for neutralising toxic chemicals and materials
KR1020137016374A KR20130080867A (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
EP17162076.8A EP3246071A1 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
SG2011089984A SG177188A1 (en) 2008-01-22 2008-12-30 Method and formulation for neutralizing toxic chemicals and materials
IL206925A IL206925A (en) 2008-01-22 2010-07-11 Method and formulation for neutralizing toxic chemicals and materials
US13/284,465 US20130144103A1 (en) 2008-01-22 2011-10-28 Method and Formulation for Neutralizing Toxic Chemicals and Materials
RU2013127598/05A RU2013127598A (en) 2008-01-22 2013-06-18 A method and formulation for neutralizing toxic chemicals and materials
US13/920,416 US9604085B2 (en) 2008-01-22 2013-06-18 Method and formulation for neutralizing toxic chemicals and materials
HK13113983.7A HK1186426A1 (en) 2008-01-22 2013-12-17 Method and formulation for neutralizing toxic chemicals and materials
JP2015126525A JP2015186618A (en) 2008-01-22 2015-06-24 Method and formulation for neutralizing toxic chemicals and toxic materials
IL240329A IL240329D0 (en) 2008-01-22 2015-08-03 Method and formulation for neutralizing toxic chemicals and materials
IL240332A IL240332D0 (en) 2008-01-22 2015-08-03 Method and formulation for neutralizing toxic chemicals and materials
HK16109999.4A HK1223322A1 (en) 2008-01-22 2016-08-22 Method and formulation for neutralizing pesticides
US15/272,208 US20170072239A1 (en) 2008-01-22 2016-09-21 Method and Formulation for Neutralizing Toxic Chemicals and Materials

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US84062510A Division 2010-07-21 2010-07-21

Publications (1)

Publication Number Publication Date
US20090187060A1 true US20090187060A1 (en) 2009-07-23

Family

ID=40512136

Family Applications (4)

Application Number Title Priority Date Filing Date
US12/017,749 Abandoned US20090187060A1 (en) 2008-01-22 2008-01-22 Method and Formulation for Neutralizing Toxic Chemicals and Materials
US13/284,465 Abandoned US20130144103A1 (en) 2008-01-22 2011-10-28 Method and Formulation for Neutralizing Toxic Chemicals and Materials
US13/920,416 Active US9604085B2 (en) 2008-01-22 2013-06-18 Method and formulation for neutralizing toxic chemicals and materials
US15/272,208 Abandoned US20170072239A1 (en) 2008-01-22 2016-09-21 Method and Formulation for Neutralizing Toxic Chemicals and Materials

Family Applications After (3)

Application Number Title Priority Date Filing Date
US13/284,465 Abandoned US20130144103A1 (en) 2008-01-22 2011-10-28 Method and Formulation for Neutralizing Toxic Chemicals and Materials
US13/920,416 Active US9604085B2 (en) 2008-01-22 2013-06-18 Method and formulation for neutralizing toxic chemicals and materials
US15/272,208 Abandoned US20170072239A1 (en) 2008-01-22 2016-09-21 Method and Formulation for Neutralizing Toxic Chemicals and Materials

Country Status (13)

Country Link
US (4) US20090187060A1 (en)
EP (2) EP3246071A1 (en)
JP (2) JP2011511656A (en)
KR (4) KR101657605B1 (en)
CN (3) CN103212182B (en)
AU (1) AU2008348284C1 (en)
BR (1) BRPI0822225A2 (en)
CA (2) CA2712324C (en)
HK (2) HK1186426A1 (en)
IL (3) IL206925A (en)
RU (2) RU2495697C2 (en)
SG (2) SG177188A1 (en)
WO (1) WO2009094098A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9714346B1 (en) 2016-09-16 2017-07-25 Tda Research, Inc. Triarylmethane dye-oximate compounds

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106857628A (en) * 2017-01-11 2017-06-20 北京长江脉医药科技有限责任公司 Disinfectant comprising disinfection and pesticide degradation active components
CN106883937A (en) * 2017-01-11 2017-06-23 北京长江脉医药科技有限责任公司 Disinfection cleaning agent capable of degrading pesticide residues

Citations (51)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2557973A (en) * 1946-03-12 1951-06-26 Wilbur F Kamm Ointments
US2934451A (en) * 1945-03-14 1960-04-26 William W Prichard Anti-vesicant coating composition
US4469744A (en) * 1980-07-11 1984-09-04 E. I. Du Pont De Nemours And Company Protective clothing of fabric containing a layer of highly fluorinated ion exchange polymer
US4513047A (en) * 1984-01-23 1985-04-23 Burlington Industries, Inc. Sorbent internally ribbed carbon-containing material and protective garment fabricated therefrom
US4518650A (en) * 1980-07-11 1985-05-21 E. I. Du Pont De Nemours And Company Protective clothing of fabric containing a layer of highly fluorinated ion exchange polymer
US4789736A (en) * 1985-03-11 1988-12-06 Amersham International Plc Complexes of technetium-99m with propylene amine oximes
US4869897A (en) * 1987-10-22 1989-09-26 The Procter & Gamble Company Photoprotection compositions comprising sorbohydroxamic acid
US5071877A (en) * 1986-10-24 1991-12-10 Bannard Robert A B Metal oximate/polyethylene glycols chemicals decontaminant system
US5075297A (en) * 1983-11-22 1991-12-24 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Broad spectrum chemical decontaminant system
US5077316A (en) * 1983-11-22 1991-12-31 Her Majesty Queen As Represented By Minister Of National Defence Canada Metal phenoxide/polyethylene glycols chemical decontaminant system
US5364617A (en) * 1990-04-26 1994-11-15 The Procter & Gamble Company Chelator compositions comprising oxime compounds
US5607979A (en) * 1995-05-30 1997-03-04 The United States Of America As Represented By The Secretary Of The Army Topical skin protectants
US5695775A (en) * 1994-08-13 1997-12-09 Hasso von Blucher Decontaminating of skin or materials contaminated by chemical warfare agents
US6017750A (en) * 1998-11-12 2000-01-25 The United States Of America As Represented By The Secretary Of The Army Hydrolysis and biodegradation of the chemical warfare vesicant agent HT
US6019941A (en) * 1996-01-30 2000-02-01 Porcello; Joseph A. Method for disinfecting dermal surfaces and inanimate surfaces, and particularly air ducts
US6121506A (en) * 1996-12-12 2000-09-19 Commodore Applied Technologies, Inc. Method for destroying energetic materials
US6224885B1 (en) * 1996-05-17 2001-05-01 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Barrier cream comprising hexamethylenetetramine or derivative thereof
US20020037268A1 (en) * 1999-05-19 2002-03-28 Kevin Stack Antimicrobial sanitizing lotion with skin protection properties
US6403653B1 (en) * 2000-06-02 2002-06-11 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using reactive nanoparticles
US6410604B1 (en) * 2000-06-02 2002-06-25 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing OPAA enzymes and clecs
US6410603B1 (en) * 2000-06-02 2002-06-25 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using combinations of reactive nanoparticles and polyoxometalates or metal salts
US6414039B1 (en) * 2000-06-02 2002-07-02 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing polyoxometalates and/or coinage metal complexes
US6417236B1 (en) * 2000-06-02 2002-07-09 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using hybrid organic polysilsesquioxane materials
US6420434B1 (en) * 2000-06-02 2002-07-16 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using polyoxometallates
US6437005B1 (en) * 2000-06-02 2002-08-20 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using polymer coated metal alloys
US6451293B1 (en) * 1997-03-05 2002-09-17 Pentapharm Ag Combination of erythrulose and a reducing sugar with self-tanning properties
US6472437B1 (en) * 2000-06-02 2002-10-29 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants
US6472438B1 (en) * 2000-06-02 2002-10-29 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing S-330
US6479723B1 (en) * 1999-03-15 2002-11-12 The Chief Controller, Research And Development, Defence Research And Development Organization Of Ministry Defence Process for chemical destruction of sulphur mustard
US6525237B1 (en) * 1999-02-19 2003-02-25 Her Majesty The Queen As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Broad spectrum decontamination formulation and method of use
US20030039619A1 (en) * 2000-01-28 2003-02-27 Joachim Bunger Galenic formulation
US20030049287A1 (en) * 1999-12-14 2003-03-13 Ley Jakob Peter Catechol oximes and their use in cosmetic and dermatological preparations
US20030055090A1 (en) * 2001-07-25 2003-03-20 Lin Ai J. Antivesicant compounds and methods of making and using thereof
US20030083321A1 (en) * 2001-09-25 2003-05-01 Lerner David S. Composition and method for minimizing or avoiding adverse effects of vesicants
US6566574B1 (en) * 1998-06-30 2003-05-20 Sandia Corporation Formulations for neutralization of chemical and biological toxants
US6569353B1 (en) * 1998-06-11 2003-05-27 Lynntech, Inc. Reactive decontamination formulation
US6586477B1 (en) * 2002-10-31 2003-07-01 Sporicidin Company Teat dip composition containing phenol and phenate
US20030157037A1 (en) * 2000-05-24 2003-08-21 Joachim Bunger Use of aryl oximes for the prophylaxis and/or treatment of erythema formation and/or inflammatory reaction of the skin
US20030176470A1 (en) * 2000-05-24 2003-09-18 Joachim Bunger Topical composition containing at least one aryl oxime, and method for the preparation thereof
US6653519B2 (en) * 1998-09-15 2003-11-25 Nanoscale Materials, Inc. Reactive nanoparticles as destructive adsorbents for biological and chemical contamination
US20040022867A1 (en) * 2002-07-19 2004-02-05 Tucker Mark D. Decontamination formulation with sorbent additive
US20040067205A1 (en) * 2002-05-06 2004-04-08 Braue Ernest H. Active topical skin protectants containing amines, polyalkenimines and /or derivatives
US6723891B1 (en) * 2002-08-07 2004-04-20 The United States Of America As Represented By The Secretary Of The Army Molybdate/peroxide microemulsions useful for decontamination of chemical warfare agents
US6723349B1 (en) * 1999-10-12 2004-04-20 Emory University Polyoxometalate materials, metal-containing materials, and methods of use thereof
US6723890B2 (en) * 1998-06-30 2004-04-20 Sandia Corporation Concentrated formulations and methods for neutralizing chemical and biological toxants
US20050032913A1 (en) * 2003-08-08 2005-02-10 Steris Inc. Decontamination of prion-contaminated surfaces with phenols
US20050059566A1 (en) * 2000-01-05 2005-03-17 Brown Jerry S. Chemical and biological warfare decontaminating solution using peracids and germinants in microemulsions, process and product thereof
US20050129914A1 (en) * 2003-11-20 2005-06-16 Rim Peter B. Protective fabrics
US20050159307A1 (en) * 2002-05-03 2005-07-21 Nelya Okun Materials for degrading contaminants
US20080230689A1 (en) * 2005-05-06 2008-09-25 Smiths Detection Inc. Chemical identification of peroxide-based explosives
US20080255431A1 (en) * 2004-08-06 2008-10-16 Ramot At Tel Aviv Univeristy Ltd. Early Detection and Warning of Harmful Agents

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US686221A (en) * 1901-01-21 1901-11-05 Charles Hart Die-stock.
GB686221A (en) * 1950-05-27 1953-01-21 Mond Nickel Co Ltd Improvements in the recovery of nickel from solutions
JPS595341B2 (en) * 1975-06-17 1984-02-03 Sumitomo Chemical Co
NL194030C (en) 1989-03-15 2001-05-03 Secr Defence Brit Cream or lotion.
DE69019992D1 (en) 1990-11-02 1995-07-13 Canada Minister Defence Metalloximat / polyethylene glycols chemical decontamination.
AU4341793A (en) 1992-06-05 1994-01-04 Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland, The Composite fabrics for protection against chemical agents
CN1175982A (en) * 1995-02-16 1998-03-11 亨凯尔公司 Modifiers for aldoxime extractant of metal values
US5902816A (en) * 1997-02-21 1999-05-11 Synapse Pharmaceuticals International, Inc. Method for treatment of heavy metal poisoning
FR2769234B1 (en) * 1997-10-02 1999-11-26 France Etat decontamination composition
FR2777193B1 (en) * 1998-04-14 2001-06-08 Coletica Particle hydroxamic chelating group of metal ions and their use in cosmetics or pharmacy
US7276468B1 (en) 1998-06-30 2007-10-02 Sandia Corporation Granulated decontamination formulations
US6821738B2 (en) 1999-01-20 2004-11-23 The Board Of Regents For Oklahoma State University Broad spectrum bio-detection of nerve agents, organophosphates, and other chemical warfare agents
AU7999600A (en) 1999-10-08 2001-04-23 University Of Akron, The Insoluble nanofibers of linear poly(ethylenimine) and uses therefor
DE10010373C1 (en) 2000-03-02 2002-02-21 Bundesrep Deutschland Skin decontaminant against chemical skin and nerve warfare agents, comprises a silicone-based emulsion of chloramine, alkaline oxime salt and emulsifiers, and a separate acid glycerol-based dispersion containing diacetyl monoxime
US20030054949A1 (en) * 2001-05-23 2003-03-20 Chang Eddie L. Immobilized metalchelate complexes for catalysis and decontamination of pesticides and chemical warfare nerve-agents
CN1264616C (en) 2001-09-07 2006-07-19 株式会社神户制钢所 Neutralization theatment method for solid residue in waste chemical weapon
US7279129B2 (en) 2002-05-14 2007-10-09 Nanoscale Corporation Method and apparatus for control of chemical or biological warfare agents
FR2841802B1 (en) * 2002-07-08 2005-03-04 Commissariat Energie Atomique Composition, foam and surface decontamination process
US6827766B2 (en) * 2002-10-08 2004-12-07 United States Air Force Decontaminating systems containing reactive nanoparticles and biocides
WO2004052918A2 (en) 2002-12-09 2004-06-24 The Trustees Of Columbia University In The City Of New York Peptides and methods for deactivation of organophosphorus-based nerve agents and insecticides
KR20040051958A (en) * 2002-12-13 2004-06-19 주식회사 두산 Sphingolipid derivatives modified by polyethylene glycol and composition containing the same
AU2003290393A1 (en) 2003-01-07 2004-07-29 Hadasit Medical Research Services & Development Ltd. Composition comprising a desferrioxamine-metal complex and its use for treating tissue damage following exposure to warfare agent
EP1589977A1 (en) 2003-01-14 2005-11-02 U.S. Army Medical Research and Material Command Dept. of the Army Topical ointment for vesicating chemical warfare agents
US7125497B1 (en) * 2003-05-22 2006-10-24 Sandia Corporation Reactive formulations for a neutralization of toxic industrial chemicals
EP1787101B1 (en) 2004-09-09 2014-11-12 Life Technologies Corporation Laser microdissection apparatus and method
DE102004044621A1 (en) 2004-09-13 2006-03-30 Owr Ag Improved detoxification solution
CA2989941A1 (en) 2004-09-23 2006-03-30 Arc Pharmaceuticals, Inc. Pharmaceutical compostions and methods relating to inhibiting fibrous adhesions or inflammatory disease using low sulphate fucans
US20070229834A1 (en) * 2004-10-22 2007-10-04 Patel C Kumar N System and method for high sensitivity optical detection of gases
CN100348575C (en) * 2005-04-04 2007-11-14 浙江新宇化工有限公司 Method for preparing aldoxime or ketoxime
US20100022010A1 (en) * 2005-05-24 2010-01-28 Chemmotif Inc. Chemical agent detection method and apparatus
US20070065587A1 (en) * 2005-08-26 2007-03-22 Hatle Loren L Method for removal of surface contaminants from substrates
US20090112042A1 (en) 2007-10-24 2009-04-30 Atomic Energy Council - Institute Of Nuclear Energy Research Decontamination method of metal surface contaminated by radioactive element
WO2009149227A1 (en) * 2008-06-06 2009-12-10 Lubrizol Advanced Materials, Inc. Ester compounds for use in personal care products

Patent Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2934451A (en) * 1945-03-14 1960-04-26 William W Prichard Anti-vesicant coating composition
US2557973A (en) * 1946-03-12 1951-06-26 Wilbur F Kamm Ointments
US4469744A (en) * 1980-07-11 1984-09-04 E. I. Du Pont De Nemours And Company Protective clothing of fabric containing a layer of highly fluorinated ion exchange polymer
US4518650A (en) * 1980-07-11 1985-05-21 E. I. Du Pont De Nemours And Company Protective clothing of fabric containing a layer of highly fluorinated ion exchange polymer
US5077316A (en) * 1983-11-22 1991-12-31 Her Majesty Queen As Represented By Minister Of National Defence Canada Metal phenoxide/polyethylene glycols chemical decontaminant system
US5075297A (en) * 1983-11-22 1991-12-24 Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Broad spectrum chemical decontaminant system
US4513047A (en) * 1984-01-23 1985-04-23 Burlington Industries, Inc. Sorbent internally ribbed carbon-containing material and protective garment fabricated therefrom
US4789736A (en) * 1985-03-11 1988-12-06 Amersham International Plc Complexes of technetium-99m with propylene amine oximes
US5071877A (en) * 1986-10-24 1991-12-10 Bannard Robert A B Metal oximate/polyethylene glycols chemicals decontaminant system
US4869897A (en) * 1987-10-22 1989-09-26 The Procter & Gamble Company Photoprotection compositions comprising sorbohydroxamic acid
US5364617A (en) * 1990-04-26 1994-11-15 The Procter & Gamble Company Chelator compositions comprising oxime compounds
US5695775A (en) * 1994-08-13 1997-12-09 Hasso von Blucher Decontaminating of skin or materials contaminated by chemical warfare agents
US5607979A (en) * 1995-05-30 1997-03-04 The United States Of America As Represented By The Secretary Of The Army Topical skin protectants
US6019941A (en) * 1996-01-30 2000-02-01 Porcello; Joseph A. Method for disinfecting dermal surfaces and inanimate surfaces, and particularly air ducts
US6224885B1 (en) * 1996-05-17 2001-05-01 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Barrier cream comprising hexamethylenetetramine or derivative thereof
US20010046995A1 (en) * 1996-05-17 2001-11-29 The Secretary Of State For Defence, Great Britain And Northern Ireland Barrier cream comprising hexamethylenetetramine or derivative thereof
US6375962B2 (en) * 1996-05-17 2002-04-23 The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland Barrier cream comprising hexamethylenetetramine or derivative thereof
US6121506A (en) * 1996-12-12 2000-09-19 Commodore Applied Technologies, Inc. Method for destroying energetic materials
US6451293B1 (en) * 1997-03-05 2002-09-17 Pentapharm Ag Combination of erythrulose and a reducing sugar with self-tanning properties
US6569353B1 (en) * 1998-06-11 2003-05-27 Lynntech, Inc. Reactive decontamination formulation
US20040009095A1 (en) * 1998-06-11 2004-01-15 Anthony Giletto Reactive decontamination formulation
US6723890B2 (en) * 1998-06-30 2004-04-20 Sandia Corporation Concentrated formulations and methods for neutralizing chemical and biological toxants
US6566574B1 (en) * 1998-06-30 2003-05-20 Sandia Corporation Formulations for neutralization of chemical and biological toxants
US6653519B2 (en) * 1998-09-15 2003-11-25 Nanoscale Materials, Inc. Reactive nanoparticles as destructive adsorbents for biological and chemical contamination
US6017750A (en) * 1998-11-12 2000-01-25 The United States Of America As Represented By The Secretary Of The Army Hydrolysis and biodegradation of the chemical warfare vesicant agent HT
US6525237B1 (en) * 1999-02-19 2003-02-25 Her Majesty The Queen As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government Broad spectrum decontamination formulation and method of use
US6479723B1 (en) * 1999-03-15 2002-11-12 The Chief Controller, Research And Development, Defence Research And Development Organization Of Ministry Defence Process for chemical destruction of sulphur mustard
US20020037268A1 (en) * 1999-05-19 2002-03-28 Kevin Stack Antimicrobial sanitizing lotion with skin protection properties
US6723349B1 (en) * 1999-10-12 2004-04-20 Emory University Polyoxometalate materials, metal-containing materials, and methods of use thereof
US20040185116A1 (en) * 1999-10-12 2004-09-23 Hill Craig L. Polyoxometalate materials, metal-containing materials, and methods of use thereof
US20030049287A1 (en) * 1999-12-14 2003-03-13 Ley Jakob Peter Catechol oximes and their use in cosmetic and dermatological preparations
US20050059566A1 (en) * 2000-01-05 2005-03-17 Brown Jerry S. Chemical and biological warfare decontaminating solution using peracids and germinants in microemulsions, process and product thereof
US20030039619A1 (en) * 2000-01-28 2003-02-27 Joachim Bunger Galenic formulation
US20030176470A1 (en) * 2000-05-24 2003-09-18 Joachim Bunger Topical composition containing at least one aryl oxime, and method for the preparation thereof
US20030157037A1 (en) * 2000-05-24 2003-08-21 Joachim Bunger Use of aryl oximes for the prophylaxis and/or treatment of erythema formation and/or inflammatory reaction of the skin
US6437005B1 (en) * 2000-06-02 2002-08-20 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using polymer coated metal alloys
US6403653B1 (en) * 2000-06-02 2002-06-11 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using reactive nanoparticles
US6420434B1 (en) * 2000-06-02 2002-07-16 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using polyoxometallates
US6410603B1 (en) * 2000-06-02 2002-06-25 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using combinations of reactive nanoparticles and polyoxometalates or metal salts
US6410604B1 (en) * 2000-06-02 2002-06-25 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing OPAA enzymes and clecs
US6472437B1 (en) * 2000-06-02 2002-10-29 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants
US6417236B1 (en) * 2000-06-02 2002-07-09 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants using hybrid organic polysilsesquioxane materials
US6414039B1 (en) * 2000-06-02 2002-07-02 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing polyoxometalates and/or coinage metal complexes
US6472438B1 (en) * 2000-06-02 2002-10-29 The United States Of America As Represented By The Secretary Of The Army Active topical skin protectants containing S-330
US20030055090A1 (en) * 2001-07-25 2003-03-20 Lin Ai J. Antivesicant compounds and methods of making and using thereof
US20030083321A1 (en) * 2001-09-25 2003-05-01 Lerner David S. Composition and method for minimizing or avoiding adverse effects of vesicants
US20050159307A1 (en) * 2002-05-03 2005-07-21 Nelya Okun Materials for degrading contaminants
US20040067205A1 (en) * 2002-05-06 2004-04-08 Braue Ernest H. Active topical skin protectants containing amines, polyalkenimines and /or derivatives
US20040022867A1 (en) * 2002-07-19 2004-02-05 Tucker Mark D. Decontamination formulation with sorbent additive
US6723891B1 (en) * 2002-08-07 2004-04-20 The United States Of America As Represented By The Secretary Of The Army Molybdate/peroxide microemulsions useful for decontamination of chemical warfare agents
US6586477B1 (en) * 2002-10-31 2003-07-01 Sporicidin Company Teat dip composition containing phenol and phenate
US20050032913A1 (en) * 2003-08-08 2005-02-10 Steris Inc. Decontamination of prion-contaminated surfaces with phenols
US20050129914A1 (en) * 2003-11-20 2005-06-16 Rim Peter B. Protective fabrics
US20080255431A1 (en) * 2004-08-06 2008-10-16 Ramot At Tel Aviv Univeristy Ltd. Early Detection and Warning of Harmful Agents
US20080230689A1 (en) * 2005-05-06 2008-09-25 Smiths Detection Inc. Chemical identification of peroxide-based explosives

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9714346B1 (en) 2016-09-16 2017-07-25 Tda Research, Inc. Triarylmethane dye-oximate compounds

Also Published As

Publication number Publication date
IL206925A (en) 2015-08-31
CA2712324A1 (en) 2009-07-30
KR20150055629A (en) 2015-05-21
CN101977658A (en) 2011-02-16
RU2495697C2 (en) 2013-10-20
RU2013127598A (en) 2014-12-27
IL206925D0 (en) 2010-12-30
EP3246071A1 (en) 2017-11-22
JP2015186618A (en) 2015-10-29
HK1186426A1 (en) 2017-06-09
IL240332D0 (en) 2015-09-24
CN101977658B (en) 2013-04-24
CA2712324C (en) 2016-02-09
KR20140112582A (en) 2014-09-23
BRPI0822225A2 (en) 2015-06-23
EP2247348A2 (en) 2010-11-10
IL240329D0 (en) 2015-09-24
AU2008348284B2 (en) 2012-08-02
AU2008348284A1 (en) 2009-07-30
CN103212182A (en) 2013-07-24
KR20100103872A (en) 2010-09-28
HK1223322A1 (en) 2017-07-28
US20170072239A1 (en) 2017-03-16
CN103212182B (en) 2016-03-16
RU2010134593A (en) 2012-02-27
WO2009094098A3 (en) 2010-04-08
CA2905681A1 (en) 2009-07-30
JP2011511656A (en) 2011-04-14
CN105344058A (en) 2016-02-24
US20130144103A1 (en) 2013-06-06
US9604085B2 (en) 2017-03-28
SG10201704671XA (en) 2017-07-28
AU2008348284C1 (en) 2012-11-29
KR101657605B1 (en) 2016-09-19
KR20130080867A (en) 2013-07-15
WO2009094098A2 (en) 2009-07-30
US20130281538A1 (en) 2013-10-24
SG177188A1 (en) 2012-01-30

Similar Documents

Publication Publication Date Title
US6210695B1 (en) Leave-on antimicrobial compositions
US20110201693A1 (en) Hydroalcoholic antimicrobial composition with skin health benefits
FI94208C (en) The biocidal composition
US4850729A (en) Decontaminating composition and delivery system therefor
US7271137B2 (en) Decontamination formulations for disinfection and sterilization
US5405602A (en) Nonaqueous cold sterilant
US6582683B2 (en) Dermal barrier composition
EP0145750B1 (en) Methods for decontaminating soil
US5620527A (en) Cleansing and disinfecting method
UA85264C2 (en) Liquid and aqueous pesticidal composition, using composition for protecting plants, method for controlling organisms harmful for plants and method for protecting farm crops from damage or infestation with harmful organisms
EP0598412A2 (en) Skinprotection composition
US4594239A (en) Method for neutralizing offensive chemicals
NZ534368A (en) Synergistic insecticidal mixtures comprising clothianidin
CO5200793A1 (en) antimicrobial multipurpose microemulsion containing a cationic surfactant
EP1998907B1 (en) Polymer composition and method for removing contaminates from a substrate
EP1219285A3 (en) Hair bleach composition and hair dye composition
WO2003053333A3 (en) Concentrated frormulations and methods for neutralizing chemical and biological toxants
US8143309B2 (en) Methods and composition for treating a material
US5961957A (en) Foam compositions
EP0882450A3 (en) Cholesterol-lowering composition comprising coenzyme Q
WO1998055092A1 (en) Mild, rinse-off antimicrobial liquid cleansing compositions
EP0576748A1 (en) Skin protection lotion
US6405626B1 (en) Decontaminating and dispersion suppressing foam formulation
CA2727385C (en) Compositions containing a solvated active agent suitable for dispensing as a compressed gas aerosol
JP2006501962A (en) Decontamination system comprising reactive nanoparticles and biocides

Legal Events

Date Code Title Description
AS Assignment

Owner name: E-Z-EM, INC., NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HENRY, TIMOTHY G.;PRICE, BARBARA B.;REEL/FRAME:021191/0095;SIGNING DATES FROM 20080512 TO 20080702

STCB Information on status: application discontinuation

Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION

AS Assignment

Owner name: EMERGENT PROTECTIVE PRODUCTS CANADA ULC., CANADA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BRACCO USA INC.;BRACCO DIAGNOSTICS INC.;E-Z-EM, INC.;AND OTHERS;REEL/FRAME:033358/0541

Effective date: 20130801