CN102015035B - Composition and process for the destruction of organophosphorus and/or organosulphur pollutants - Google Patents
Composition and process for the destruction of organophosphorus and/or organosulphur pollutants Download PDFInfo
- Publication number
- CN102015035B CN102015035B CN200980115146.8A CN200980115146A CN102015035B CN 102015035 B CN102015035 B CN 102015035B CN 200980115146 A CN200980115146 A CN 200980115146A CN 102015035 B CN102015035 B CN 102015035B
- Authority
- CN
- China
- Prior art keywords
- composition
- acid
- hydroxy ethylene
- ethylene diphosphonic
- surfactant
- 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.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/38—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by oxidation; by combustion
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/02—Chemical warfare substances, e.g. cholinesterase inhibitors
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/04—Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/26—Organic substances containing nitrogen or phosphorus
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
Abstract
The invention relates to a decontaminating composition comprising: (i) perpropionic acid, (ii) dipicolinic acid, (iii) a salt of hydroxyethyldiethylphosphonic acid, (iv) a surface-active agent, and (v) an alkalinizing agent. The decontaminating compositions that are the subject of the invention have a high stability and high effectiveness, enabling a rapid destruction of the toxic organophosphorus or organosulphur agents.
Description
The present invention relates to the decontamination of organophosphor or organic sulfur pollutant and/or toxic agents, especially in chemical warfare reagent field or at agriculture field, for example be used for the decontamination of pesticide.It relates to the novel cleansing composition that comprises two kinds of specified stabilisers especially, and the method that is used for destroying these organophosphors and/or organic sulfur pollutant.
In chemical warfare reagent field, there are at present many organic phosphides that obtained by phosphoric acid and phosphonic acids, such as tabun, sarin or Suo Man.These compounds are owing to they have high neurotoxicity for the phosphorylation ability of cholinesterase, because acetylcholine gathering in organism, its inhibitory action causes death.
And, also there is poisonous organic sulfur product, such as industrial sulfide or war toxic agent, for example mustard gas of vesicant class.
In agriculture field, there is the organophosphor toxic compounds, such as the organophosphorus ester as pesticide and pesticide, the acylamino-phosphate, organic acylamino-phosphate, thiophosphate, Thiophosphonate and acylamino-Thiophosphonate, and the organosulfur compound of R-S-R ' type, R and R ' represent especially based on the group of hydrocarbon or based on the group of halogenated hydrocarbons.
In the organic phosphorus compound of knowing most, such as O, O-diethyl-O-p-nitrobenzophenone phosphate (Paraoxon), O, O-diethyl-O-p-nitrobenzophenone Thiophosphonate (Parathion) and O, the compound of O-diethyl-O-(2-isopropyl-4-methyl-6-pyrimidine radicals) thiophosphate (Diazinon) plays an important role as pesticide or as agricultural chemicals in agricultural.
And poisonous organosulfur compound is such as two chloro-2,2 '-diethyl thioether or 2-phenyl-2-chloro diethyl thioether, also be very corrosive chemical reagent, its stability can make them remaining in contaminated district for many years, and does not know to reduce how significantly toxicity.
It is a problem that the mass storage of product listed above exists.Removing of they means that especially the use cleansing composition is to be applied on product itself or contaminated material or the individual.Cleansing composition can be in the replacement mode or to use with the physical method combination of displacement toxic agents.
Therefore importantly, can have, especially in the situation that have a mind to or unexpected this compound, the toxicity of can the degrading product itself and the composition that makes fast and effectively the material decontamination of being polluted by toxic agents of using.
Now available compositions useful is in the presence of amine or calcium hypochlorite, and NaOH is in aqueous medium or the solution in Propylene Glycol (1,2-PD); Yet this solution is for fragile material, particularly light-metal alloy is corrosive.
What know is that the protophilic compound is effective product for the toxic agents of removing organophosphor and organic sulfur series.Therefore these toxic agents that can neutralize of the hydroxyl anion in strongly basic medium.Yet the validity of acquisition is attended by the severe corrosive for the material for the treatment of decontamination.
Other method is at more not alkaline medium, even close to using snperoxiaized compound in the medium of neutrality, such as hydrogen peroxide, tert-butyl hydroperoxide, perborate and peracid, this is because the performance of its while protophilic and oxidation.Use in the solution that various snperoxiaized compounds are the most common surfactants comprising the quaternary ammonium type, surfactant improves in the contact between peroxidization agent and toxic agents during the decontamination.
At present, make by all kinds of toxic agents (especially
) peroxide that proposes in the material decontamination of polluting, be the straight chain aqueous peracid solutions form that comprises long carbochain that pH is 6-8 with sulfur-containing compound, perhaps cross caproic acid aqueous solution form based on industrial peracid such as magnesium monoperoxyphthalate or phthalimido, these peracid in the two situation with surfactant, especially quaternary ammonium salt type surfactant combination.
Yet, the first peracid is that it( ) seldom can be commercial on industrial level that obtain and have middle equistability and a moderate solubility, the second peracid, although they can commercially obtain, but be solid form at ambient temperature, and at high temperature have middle equistability, and when using, be not easy to process.
Based on C
2-C
4Percarboxylic acids and be described in the International Application No. WO 01/30452 as detergent based on the Aquo-composition of pyridinedicarboxylic acid.Yet this compositions display goes out stability problem and uses the anhydrous percarboxylic acids that obtains by expensive Azotropic distillation method.
Comprising can be that the Aquo-composition of peroxidating reagent of peracid is described among the patent application EP 0894512 as detergent.Yet this based composition has relatively weak decontamination.
Therefore exist to having than those above-mentioned larger stability and the reality needs with novel cleansing composition of large validity, this novel cleansing composition can rapid damage organophosphor or organic sulfur toxic agents.
The applicant has developed the composition that can address the above problem, and has developed especially the composition with excellent stability and excellent validity, and it causes the rapid damage of toxic agents.
Therefore theme of the present invention at first is cleansing composition, and it comprises:
(i) Perpropionic Acid
(ii) pyridinedicarboxylic acid
(iii) hydroxy ethylene diphosphonic acid (HEDP or its salt),
(iv) surfactant, and
(v) basifier
Surprisingly, have been noted that such as top defined composition be sufficiently stable decontamination effectiveness to obtain to prolong.
Surprisingly, have been noted that the theme composition of the present invention that comprises Perpropionic Acid has the decontamination larger than the composition that comprises peracetic acid (embodiment 2 and 3) and renders a service.
Preferably, the salt of hydroxy ethylene diphosphonic acid is hydroxy ethylene diphosphonic acid sodium (HEDP).
For purposes of the invention, term " cleansing composition " is to represent can be used for making by the material decontamination of organophosphor and/or organosulfur compound pollution or for the composition that makes toxicity product degraded itself.
Advantageously, the Perpropionic Acid of use is aqueous solution form, and it is as in the presence of catalyst (such as sulfuric acid or boric acid) especially, those that the aqueous solution by hydrogen peroxide and the reaction of propionic acid obtain.This preparation method for example is described among the french patent application FR2462425.Different from the anhydrous solution of the Perpropionic Acid of in french patent application No.FR2464947 and FR2519634, describing, this aqueous solution is obtained by straightforward procedure, its unreal step of granting poisonous or inflammable organic solvent (such as 1,2-dichloroethanes or cyclohexane) azeotropic distillation.
Thus, the Perpropionic Acid of use is aqueous solution form, and it comprises: as the Perpropionic Acid of product, and as the propionic acid of responseless reactant, as the hydrogen peroxide of responseless reactant, and as sulfuric acid or the boric acid of catalyst.
Therefore cleansing composition defined above can also comprise, except compound (i)-(v):
-propionic acid
-hydrogen peroxide, and
-sulfuric acid and/or boric acid.
This composition is water-soluble liquid, and it is so that the cleansing composition of theme of the present invention is easy to use.
In a kind of specific embodiment of the present invention, composition defined above is aqueous solution form.Therefore, theme of the present invention still comprises the aqueous solution such as top defined cleansing composition.
The composition of theme of the present invention comprises basifier.Preferably basifier is selected from NaOH, potassium hydroxide, ammonium hydroxide, sodium carbonate or sodium acid carbonate, potash or saleratus, sodium phosphate, potassium phosphate, ammonium phosphate, sodium metasilicate, potassium silicate, ammonium silicate, Boratex, potassium borate, ammonium borate, and their mixture.Described one or more basifiers can be regulated the pH of theme composition of the present invention.Advantageously, theme composition of the present invention has and is higher than 7, preferably 8-12, the especially pH of 8.5-9.5.
Can be buffered in the pH of 7-10 according to composition of the present invention.When being alkaline compositions for the composition of theme of the present invention, pyridinedicarboxylic acid, Perpropionic Acid and HEDP can be the form of their corresponding salt.
The composition of theme of the present invention can also comprise alkaline buffer.For purposes of the invention, term " alkaline buffer " be used for representing single type alkaline buffer and alkaline buffer mixture the two.Composition according to the present invention comprises alkaline buffer, such as basic carbonate or alkaline silicate, and especially potash or sodium carbonate.
For purposes of the invention, term " surfactant " is used for representing anion, cationic, non-ionic or amphoteric surfactant, it is with 0 % by weight-25 % by weight with respect to the gross weight of said composition, and preferably the ratio of 5 % by weight-20 % by weight is used.
As cationic surfactant, can mention those of quaternary ammonium type, for example:
-softex kw
-hexadecyltrimethylammonium chloride
-hexadecyldimethyl benzyl ammonium 2-hydroxyethyl ammonium bromide,
Two (2-hydroxyethyl) ammonium bromides of-cetyl methyl,
-benzyltrimethylammonium bromide, and
-cetyl diaza-Isosorbide-5-Nitrae-dicyclo [2.2.2] octyl group ammonium bromide.
These surfactants are known, and the great majority in them can commercially obtain.They can be by by C.A.Bunton etc., J.Am.Chem.Soc., and 95,2912 (1973) and by L.Horner etc., Phosphorus and Sulfur, 11,339 (1981) methods of describing are prepared.
As operable non-ionic surface active agent randomly, can mention, for example:
The alkoxy fatty alcohols of-following formula: R-[(CH
2)
2O]
m-[CH
2CH (CH
3) O]
n-H
Wherein R comprises 8-22 carbon atom, the preferably alkyl of 12-14 carbon atom or alkenyl; N and m represent the integer of 0-50 independently, its summation n+m＞1;
The alkyl poly glucoside of-following formula: R " '-[glucose]
n-, R wherein " ' be C
8-C
16Alkyl and n are the integers of 1-3;
The ester of-reduced sugar, the ester of polyalcohol and their ethoxylated derivative, as, for example monostearate sorbitan ester, glycerin monostearate or glycol stearate perhaps comprise the monostearate sorbitan ester of the ethoxylation of 20 oxirane;
The alkylamide of the ethoxylation of-following formula:
Wherein R such as the definition of top institute and r and s are the integers of 0-15, its summation r+s＞1;
-alkyl pyrrolidone, its alkyl is C
6-C
20Alkyl; With their mixture.
Preferably, this Perpropionic Acid exists with the described aqueous solution form of for example 0.05-4.5mol/l concentration.
In a preferred embodiment, theme composition of the present invention comprises (representing with the weight with respect to the gross weight of said composition):
-4%-16% Perpropionic Acid,
-0.1%-2% pyridinedicarboxylic acid
-0.5%-5% ethoxy diethyl Alendronate
-5%-20% surfactant
-2%-20% basifier, and
The alkaline buffer of-5%-15% weight.
For the solution of theme of the present invention can also comprise at least a component that is selected from hydrotropic agent (such as urea or cumene sodium sulfonate), tackifier (such as xanthans), modified corn starch, hydroxyethylcellulose or defoamer.
Said composition can be powder, liquid, gel or form of suspension.
Preferably use with the aqueous solution with respect to the concentration of the 0.5 % by weight-40 % by weight Perpropionic Acid of the gross weight of this solution according to composition of the present invention.They can also with organic, not with the miscible solvent of water in emulsion or micro emulsion form after disperseing use, this solvent as, the aliphatic series that for example randomly is chlorinated or aromatic hydrocarbon, for example toluene, dimethylbenzene, carrene and tetrachloro-ethylene.
They can by spray, smear, spray, soak, dipping or any operation that other can make described composition and contaminated materials or individual contact come manually or mechanically to use.
Theme of the present invention still makes the method for toxic agents organophosphor or organic sulfur and/or pollutant decontamination, it comprise make described toxic agents and/or pollutant with as top defined composition contact.
Toxic agents described organophosphor or organic sulfur and/or pollutant can be for example in military field; war toxic agent organophosphor or organic sulfur, perhaps in agriculture field, plant protection reagent organophosphor or organic sulfur; especially pesticide, perhaps industrial pollutants.
Theme of the present invention still is used for making by the method for compound polluted material decontamination organophosphor and/or organic sulfur, comprise by spray, spraying or simple washing, perhaps described contaminated material is immersed in and comprises as in the container of top defined composition and will be applied on the contaminated material such as top defined composition.
Because the pH of theme composition of the present invention, when making this contaminated materials decontamination, described material can be selected from the sclerosis carrier that applies with polyurethane paint, non-sclerosis carrier (glycerine phthalic acid lacquer simultaneously, has highly porous surface, have elastomer) and smart devices (carrier inside, radio, electronic equipment).
Because their low-corrosiveness, these compounds can also be by being used for making individual decontamination with skin contact.
Perpropionic Acid is generally 5-10 with respect to the mol ratio of pollutant for organophosphor pollutant (being hydrolyzed into phosphate), perhaps is generally 3-5 for organic sulfur pollutant (being oxidizing to sulfone).
Theme of the present invention still is used for acquisition according to the method for cleansing composition of the present invention.This method comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid, pyridinedicarboxylic acid and hydroxy ethylene diphosphonic acid,
B) will comprise that in the Aquo-composition of surfactant, this surfactant is comprised of amine oxide and basifier in the composition dissolves that step obtains in a).
In another embodiment of the invention, the method that is used for the acquisition cleansing composition comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid and pyridinedicarboxylic acid
The composition dissolves that b) will obtain in a) in step is in Aquo-composition, and this Aquo-composition comprises surfactant, basifier and hydroxy ethylene diphosphonic acid and salt, preferably hydroxy ethylene diphosphonic acid sodium.
For instance, the hydroxy ethylene diphosphonic acid of theme composition of the present invention can be by Solutia company with trade (brand) name Dequest
Product sold forms, and hydroxy ethylene diphosphonic acid sodium can be by Solutia company with trade (brand) name Dequest
Product sold forms.Following examples illustrate the present invention and do not limit the scope of the invention.In these embodiments, percentage is by weight, except as otherwise noted.
Embodiment 1
The solution of Perpropionic Acid is prepared by mixing following material: 1000g propionic acid, 500g 70% hydrogen peroxide, 25g sulfuric acid, 7.5g pyridinedicarboxylic acid and 15g hydroxy ethylene diphosphonic acid (Dequest
).Stir at ambient temperature this mixture 12 hours to obtain equilibrium concentration.So the solution of preparation comprises:
| % by weight | |
| Perpropionic Acid | 38.2** |
| Hydrogen peroxide | 8.3* |
| Propionic acid | 33.8 |
| Water | 17.2 |
| Sulfuric acid | 1.0 |
| Pyridinedicarboxylic acid | 0.5 |
| Hydroxy ethylene diphosphonic acid | 1.0 |
* hydrogen peroxide uses cerous sulfate (IV) to carry out quantitative assay.
* gross activity oxygen carries out quantitative assay by iodometry.Perpropionic Acid is measured by the difference between gross activity oxygen and the hydrogen peroxide.
The solution of the previous preparation of 370g is mixed with following:
-70g Barquat MS 100 (from Lonza)
-100g
-90g potassium hydroxide
-190g potash, and
-900g water
Being used for decontamination uses.
Embodiment 2
The time dependent reactivity of the preparaton of preparation exists in embodiment 1
On decontamination in test.
In the glass reactor that stirs, the preparaton that 1.8g is prepared in embodiment 1 joins 50mg
In.Therefore initial detergent/toxic agents mol ratio is 5.8.Add after T minute sampling and stop this reaction by adding excessive sodium thiosulfate.Then 8ml is added in the sample with the saturated water of NaCl, 10ml 50/50 ethyl acetate/hexane and 0.1% dibutyl sebacate (interior mark).Take out organic phase and drying and remaining on sodium sulphate
Carry out quantitative assay by gas chromatography.
In embodiment 1, after the different ageing times of the preparaton of preparation, repeat this process.
The results are shown in the following table:
Embodiment 3 (not according to the present invention)
The preparaton based on Perpropionic Acid of describing in embodiment 1 is compared with the similar preparaton based on peracetic acid.The process that 39% peracetic acid solution basis and embodiment 1 are consistent is replaced propionic acid with acetic acid, and other component that then adds same amount is prepared.
Use according to the process of in embodiment 2, describing
The preparaton that test so obtains.Initial detergent/toxic agents mol ratio is 6.8.The results are shown in the following table:
Therefore these embodiment demonstrate with respect to the preparaton based on peracetic acid, based on the preparaton of Perpropionic Acid for the advantage that makes the decontamination of organophosphor toxic agents.
Claims (11)
1. cleansing composition, this cleansing composition are can be used for making the material decontamination of being polluted by organophosphor and/or organosulfur compound or be used for composition that toxicity product itself is degraded, and it comprises:
(i) Perpropionic Acid
(ii) pyridinedicarboxylic acid
(iii) hydroxy ethylene diphosphonic acid or its salt is a kind of,
(iv) surfactant, and
(v) basifier;
Be characterised in that Perpropionic Acid exists with 0.05-4.5mol/l concentration.
2. according to claim 1 composition, the salt that is characterised in that hydroxy ethylene diphosphonic acid is hydroxy ethylene diphosphonic acid sodium.
3. each composition according to claim 1 and 2 is characterised in that basifier is selected from NaOH, potassium hydroxide, ammonium hydroxide, sodium metasilicate, potassium silicate, ammonium silicate, Boratex, potassium borate, ammonium borate, and their mixture.
4. each composition according to claim 1 and 2 is characterised in that it also comprises alkaline buffer.
5. according to claim 4 composition is characterised in that this alkaline buffer is selected from basic carbonate or alkaline silicate.
6. each composition according to claim 1 and 2 is characterised in that it is buffered in the pH of 7-10.
7. according to claim 4 composition is characterised in that it comprises, and represents with the weight with respect to the gross weight of said composition:
-4%-16% Perpropionic Acid,
-0.1%-2% pyridinedicarboxylic acid
-0.5%-5% ethoxy diethyl Alendronate
-5%-20% surfactant
-2%-20% basifier, and
-5%-15% alkaline buffer.
8. make the method for toxic agents organophosphor or organic sulfur and/or pollutant decontamination, it comprises makes described toxic agents and/or pollutant and contacts such as each defined composition of front claim.
9. the preparation method of each cleansing composition according to claim 1-7 is characterised in that it comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid, pyridinedicarboxylic acid and hydroxy ethylene diphosphonic acid,
B) will comprise that in the Aquo-composition of surfactant and basifier, this surfactant is comprised of amine oxide in the composition dissolves that step obtains in a).
10. the preparation method of each cleansing composition according to claim 1-7 is characterised in that it comprises following consecutive steps:
A) acquisition comprises the composition of Perpropionic Acid and pyridinedicarboxylic acid
The composition dissolves that b) will obtain in a) in step is in Aquo-composition, and this Aquo-composition comprises surfactant, basifier and hydroxy ethylene diphosphonic acid salt.
11. the preparation method of cleansing composition according to claim 10 is characterised in that described hydroxy ethylene diphosphonic acid salt is hydroxy ethylene diphosphonic acid sodium.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0852911 | 2008-04-30 | ||
| FR0852911A FR2930732B1 (en) | 2008-04-30 | 2008-04-30 | COMPOSITION AND METHOD FOR THE DESTRUCTION OF ORGANOPHOSPHORUS AND / OR ORGANOSOUFRES POLLUTANTS |
| PCT/FR2009/050779 WO2009141548A2 (en) | 2008-04-30 | 2009-04-28 | Composition and process for the destruction of organophosphorus and/or organosulphur pollutants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102015035A CN102015035A (en) | 2011-04-13 |
| CN102015035B true CN102015035B (en) | 2013-02-13 |
Family
ID=40288819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980115146.8A Expired - Fee Related CN102015035B (en) | 2008-04-30 | 2009-04-28 | Composition and process for the destruction of organophosphorus and/or organosulphur pollutants |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP2271410B1 (en) |
| JP (1) | JP5437363B2 (en) |
| CN (1) | CN102015035B (en) |
| AT (1) | ATE528050T1 (en) |
| ES (1) | ES2374703T3 (en) |
| FR (1) | FR2930732B1 (en) |
| IL (1) | IL208609A (en) |
| WO (1) | WO2009141548A2 (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8871807B2 (en) | 2008-03-28 | 2014-10-28 | Ecolab Usa Inc. | Detergents capable of cleaning, bleaching, sanitizing and/or disinfecting textiles including sulfoperoxycarboxylic acids |
| MX2010010236A (en) | 2008-03-28 | 2010-10-20 | Ecolab Inc | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents. |
| US8809392B2 (en) | 2008-03-28 | 2014-08-19 | Ecolab Usa Inc. | Sulfoperoxycarboxylic acids, their preparation and methods of use as bleaching and antimicrobial agents |
| US8809245B2 (en) * | 2010-12-14 | 2014-08-19 | Robert E. Hill | Remedial composition and treatment method |
| US9321664B2 (en) | 2011-12-20 | 2016-04-26 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
| CA2867565C (en) | 2012-03-30 | 2021-01-19 | Victor KEASLER | Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water |
| US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
| US20140256811A1 (en) | 2013-03-05 | 2014-09-11 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
| US8822719B1 (en) | 2013-03-05 | 2014-09-02 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
| RU2669850C1 (en) * | 2017-08-28 | 2018-10-16 | Федеральное Государственное бюджетное учреждение "27 Научный центр" Министерства обороны Российской Федерации | Foam chloroactive agent and method for its preparation based on fluoro-organic foaming agent and n, n-dichloroarylsulfamides |
| FR3072390B1 (en) * | 2017-10-18 | 2019-12-20 | Quadrimex Chemical Sas | EXTEMPORANEOUS COMPOSITION COMPRISING A MIXTURE OF TWO PRODUCTS FOR THE DESTRUCTION OF ORGANOPHOSPHORUS AND / OR ORGANOSULFUR POLLUTANTS |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0894512A1 (en) * | 1997-07-31 | 1999-02-03 | Irdec S.A. | Use of stabilised decontaminating compositions for the decontamination of toxic agents and/or pollutants |
| EP0864532B1 (en) * | 1997-03-13 | 2001-08-01 | Mitsubishi Rayon Co., Ltd. | Process for producing of prussic acid and catalyst |
| CN1513569A (en) * | 2003-07-28 | 2004-07-21 | 华南农业大学 | Method of eliminating organic sulfur and ethyl carbamate pesticide residue |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9004080D0 (en) * | 1990-02-23 | 1990-04-18 | Interox Chemicals Ltd | Solutions of peracids |
| FR2761080B1 (en) * | 1997-03-21 | 2002-07-19 | Quadrimex | COMPOSITION BASED ON PERACIDS FOR THE CLEANING, DISINFECTION AND DECONTAMINATION OF SURFACES STAINED BY TOXIC AGENTS |
| FR2766724B1 (en) * | 1997-07-31 | 1999-10-22 | Irdec Sa | NON-AGGRESSIVE DECONTAMINANT COMPOSITIONS |
| FR2800291B1 (en) * | 1999-10-29 | 2004-07-09 | Atofina | COMPOSITION AND PROCESS FOR THE DESTRUCTION OF ORGANOPHOSPHORUS AND / OR ORGANOSULFUR POLLUTANTS |
| DE19960994A1 (en) * | 1999-12-17 | 2001-06-21 | Degussa | Process for the preparation of peroxycarboxylic acid solutions, in particular equilibrium peracetic acid and perpropionic acid |
-
2008
- 2008-04-30 FR FR0852911A patent/FR2930732B1/en not_active Expired - Fee Related
-
2009
- 2009-04-28 AT AT09750029T patent/ATE528050T1/en not_active IP Right Cessation
- 2009-04-28 CN CN200980115146.8A patent/CN102015035B/en not_active Expired - Fee Related
- 2009-04-28 EP EP09750029A patent/EP2271410B1/en not_active Not-in-force
- 2009-04-28 JP JP2011506755A patent/JP5437363B2/en not_active Expired - Fee Related
- 2009-04-28 WO PCT/FR2009/050779 patent/WO2009141548A2/en active Application Filing
- 2009-04-28 ES ES09750029T patent/ES2374703T3/en active Active
-
2010
- 2010-10-11 IL IL208609A patent/IL208609A/en not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0864532B1 (en) * | 1997-03-13 | 2001-08-01 | Mitsubishi Rayon Co., Ltd. | Process for producing of prussic acid and catalyst |
| EP0894512A1 (en) * | 1997-07-31 | 1999-02-03 | Irdec S.A. | Use of stabilised decontaminating compositions for the decontamination of toxic agents and/or pollutants |
| CN1513569A (en) * | 2003-07-28 | 2004-07-21 | 华南农业大学 | Method of eliminating organic sulfur and ethyl carbamate pesticide residue |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2271410A2 (en) | 2011-01-12 |
| JP5437363B2 (en) | 2014-03-12 |
| WO2009141548A2 (en) | 2009-11-26 |
| ATE528050T1 (en) | 2011-10-15 |
| JP2011522066A (en) | 2011-07-28 |
| CN102015035A (en) | 2011-04-13 |
| FR2930732B1 (en) | 2010-05-14 |
| FR2930732A1 (en) | 2009-11-06 |
| IL208609A (en) | 2013-12-31 |
| EP2271410B1 (en) | 2011-10-12 |
| ES2374703T3 (en) | 2012-02-21 |
| IL208609A0 (en) | 2010-12-30 |
| WO2009141548A3 (en) | 2010-03-25 |
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