EP2714877B1 - Systèmes activateurs pour composés peroxygénés - Google Patents
Systèmes activateurs pour composés peroxygénés Download PDFInfo
- Publication number
- EP2714877B1 EP2714877B1 EP12722337.8A EP12722337A EP2714877B1 EP 2714877 B1 EP2714877 B1 EP 2714877B1 EP 12722337 A EP12722337 A EP 12722337A EP 2714877 B1 EP2714877 B1 EP 2714877B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- iii
- acid
- salts
- mixtures
- lewis acid
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims description 51
- 239000012190 activator Substances 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims description 47
- 239000002841 Lewis acid Substances 0.000 claims description 25
- 150000007517 lewis acids Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 18
- 238000004061 bleaching Methods 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 14
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 13
- 238000004140 cleaning Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- JDIBGQFKXXXXPN-UHFFFAOYSA-N bismuth(3+) Chemical class [Bi+3] JDIBGQFKXXXXPN-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000004753 textile Substances 0.000 claims description 11
- RJMMFJHMVBOLGY-UHFFFAOYSA-N indium(3+) Chemical class [In+3] RJMMFJHMVBOLGY-UHFFFAOYSA-N 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- DOSGOCSVHPUUIA-UHFFFAOYSA-N samarium(3+) Chemical class [Sm+3] DOSGOCSVHPUUIA-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
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- 229910000337 indium(III) sulfate Inorganic materials 0.000 claims description 4
- XGCKLPDYTQRDTR-UHFFFAOYSA-H indium(iii) sulfate Chemical compound [In+3].[In+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGCKLPDYTQRDTR-UHFFFAOYSA-H 0.000 claims description 4
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- YZDZYSPAJSPJQJ-UHFFFAOYSA-N samarium(3+);trinitrate Chemical compound [Sm+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O YZDZYSPAJSPJQJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
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- 239000003446 ligand Substances 0.000 description 17
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- PATMLLNMTPIUSY-UHFFFAOYSA-N phenoxysulfonyl 7-methyloctanoate Chemical compound CC(C)CCCCCC(=O)OS(=O)(=O)OC1=CC=CC=C1 PATMLLNMTPIUSY-UHFFFAOYSA-N 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QSKQNALVHFTOQX-UHFFFAOYSA-M sodium nonanoyloxybenzenesulfonate Chemical compound [Na+].CCCCCCCCC(=O)OC1=CC=CC=C1S([O-])(=O)=O QSKQNALVHFTOQX-UHFFFAOYSA-M 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- CVYDEWKUJFCYJO-UHFFFAOYSA-M sodium;docosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCC([O-])=O CVYDEWKUJFCYJO-UHFFFAOYSA-M 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3932—Inorganic compounds or complexes
Definitions
- the present invention relates to the use of systems of Lewis acid and Peroxocarbonklare redesignnder under perhydrolysis conditions for the activation of peroxygen compounds, in particular for bleaching of Farbanschmutzungen in the washing of textiles, and detergents, cleaners and disinfectants containing such systems.
- Inorganic peroxygen compounds particularly hydrogen peroxide and solid peroxygen compounds which dissolve in water to release hydrogen peroxide, such as sodium perborate and sodium carbonate perhydrate, have long been used as oxidizing agents for disinfecting and bleaching purposes.
- the oxidation effect of these substances in dilute solutions depends strongly on the temperature; Thus, for example, with H 2 O 2 or alkali perborate in alkaline bleaching liquors only at temperatures above about 80 ° C, a sufficiently fast bleaching of soiled textiles.
- the oxidation effect of the inorganic peroxygen compounds can be improved by addition of so-called bleach activators which are able to provide peroxycarboxylic under the abovementioned perhydrolysis and for the numerous proposals, especially from the classes of N- or O-acyl compounds, for example several times acylated alkylenediamines, in particular tetraacetylethylenediamine, acylated glycolurils, in particular tetraacetylglycoluril, N-acylated hydantoins, hydrazides, triazoles, hydrotriazines, urazoles, diketopiperazines, sulphurylamides and cyanurates, and also carboxylic anhydrides, in particular phthalic anhydride and alkylsuccinic anhydrides, carboxylic esters, in particular sodium nonanoyloxybenzenesulphonate, sodium isononanoyloxy Benzenesulfonate,
- the present invention aims to improve the oxidation and bleaching performance of inorganic peroxygen compounds by accelerating the formation of peroxycarboxylic acid from peroxycarboxylic acid-providing bleach activator and peroxygen bleach, especially at low temperatures in the range of about 15 ° C to 45 ° C.
- the invention relates to the use of a system of Lewis acid and peroxocarbonklare redesignnder under perhydrolysis substance as activator for in particular inorganic peroxygen compounds in oxidation, washing, cleaning or disinfecting solutions, wherein the Lewis acid among the bismuth (III) salts, the Indium (III) salts and the samarium (III) salts and mixtures thereof.
- Another object of the invention is the use of Lewis acid to accelerate the formation of peroxycarboxylic in particular inorganic peroxygen compound and Peroxocarbonklare redesignnder under perhydrolysis conditions, especially when washing textiles or when cleaning hard surfaces, and in particular in aqueous systems, wherein the Lewis acid under bismuth (III) salts, indium (III) salts and samarium (III) salts and mixtures thereof.
- a further subject matter is a process for the preparation of peroxycarboxylic acid, in particular in aqueous solution, from in particular inorganic peroxygen compound and peroxocarbonsaurellefernder under perhydrolysis conditions, which is characterized in that Lewis acid is used, wherein the Lewis acid under the bismuth (III) - Salts, the indium (III) salts and the samarium (III) salts and mixtures thereof is selected.
- the mole ratio of peroxycarboxylic acid to the compound to Lewis acid is preferably 100: 1 to 1:50, more preferably 10: 1 to 1: 5, and most preferably 2: 1 to 1: 4.
- the Lewis acid system and the peroxycarboxylic acid-providing compound under perhydrolysis conditions is preferably used for bleaching paint stains when washing textiles, especially in aqueous surfactant-containing liquors.
- bleaching of color stains is to be understood in its broadest sense and includes both the bleaching of dirt present on the textile, the bleaching of debris located in the wash liquor, and the deoxidation of the wash liquor in the wash liquor Textile dyes that detach under the washing conditions of textiles before they can be applied to different colored textiles.
- Another preferred embodiment of the invention is the use of the Lewis acid system and under perhydrolysis conditions of peroxycarboxylic acid-providing compound in hard surface cleaning solutions, especially for dishes, for bleaching stained soils, for example tea.
- bleaching is understood as meaning both the bleaching of dirt on the hard surface, in particular tea, and the bleaching of dirt removed from the hard surface in the dishwashing liquor, and the Lewis acid becomes below the bismuth (III) salts, the indium (III) salts and the samarium (III) salts and mixtures thereof.
- detergents, cleaners and disinfectants which contain the abovementioned system of Lewis acid and peroxycarboxylic acid-yielding compound under perhydrolysis conditions.
- the system of Lewis acid and Peroxocarbonklander under perhydrolysis conditions in the sense of an activator can be used wherever it depends on a particular increase in the oxidation effect of the peroxygen compounds at low temperatures, for example in bleaching of textiles or hair, in the oxidation of organic or inorganic intermediates and in disinfection.
- Lewis acids are electrophilic electron pair acceptors, so they can attach electron pairs. They have at least one unoccupied orbital in their valence electron shell.
- Lewis acids are selected from bismuth (III) salts, indium (III) salts, and samarium (III) salts and mixtures thereof, including bismuth (III) oxinitrate, indium (III) sulfate, and Samarium (III) nitrate and mixtures of these are particularly preferred.
- Compounds which give peroxocarboxylic acid under perhydrolysis conditions can in particular be compounds which give perbenzoic acid which is optionally substituted under perhydrolysis conditions and / or aliphatic peroxycarboxylic acids having 1 to 12C atoms, in particular 2 to 4 carbon atoms, alone or in mixtures.
- Suitable are the bleach activators cited at the outset which carry O- and / or N-acyl groups, in particular of the stated C atom number and / or optionally substituted benzyl groups.
- polyacylated alkylenediamines in particular tetraacetylethylenediamine (TAED), acylated glycolurils, in particular tetraacetylglycoluril (TAGU), acylated triazine derivatives, in particular 1,5-diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT), N- Acylimides, in particular N-nonanoylsuccinimide (NOSI), acylated phenolsulfonates or carboxylates or the sulfonic or carboxylic acids of these, especially nonanoyl or Isononanoyl- or Lauroyloxybenzolsulfonat (NOBS or iso-NOBS or LOBS) or Decanoyloxybenzoat
- acylated polyhydric alcohols in particular triacetin, ethylene glycol diacetate and 2,5-diacetoxy-2,5-dihydrofuran and acetylated sorbitol and mannitol or mixtures thereof (SORMAN), acylated sugar derivatives, in particular pentaacetylglucose (PAG), pentaacetylfruktose, tetraacetylxylose and octaacetyllactose , acetylated, optionally N-alkylated glucamine and gluconolactone, and / or N-acylated lactams, for example N-benzoyl-caprolactam.
- PAG pentaacetylglucose
- PAG pentaacetylfruktose
- tetraacetylxylose tetraacetylxylose
- the use of the present invention is to provide conditions under which the peroxygen compound and the Lewis acid bleach-enhancing system and peroxycarboxylic acid-providing compound can react with each other under perhydrolysis conditions, with the aim of obtaining more strongly oxidizing secondary products.
- Such conditions are especially present when the reactants meet in aqueous solution.
- This can be done by separately adding the peroxygen compound and the bleach-enhancing system to an optionally detergent or cleaner-containing solution.
- the process according to the invention is particularly advantageously carried out using a washing, cleaning or disinfecting agent which contains the said bleaching-intensifying system and optionally a peroxidic oxidizing agent.
- the peroxygen compound may also be added to the solution separately, in bulk or as a preferably aqueous solution or suspension, when a peroxygen-free agent is used.
- the conditions can be varied widely.
- the amounts of peroxygen compounds are generally chosen so that in the solutions between 10 ppm and 10% active oxygen, preferably between 50 and 5000 ppm of active oxygen are present.
- An inventive washing, cleaning or disinfecting agent preferably contains 0.01% by weight to 10% by weight, in particular 1% by weight to 3% by weight, of peroxycarboxylic acid-yielding compound under perhydrolysis conditions in addition to conventional ingredients compatible with the peroxygen compound and the system used according to the invention.
- the system or its individual components used in accordance with the invention may or may, as well as the peroxygen compound, if desired, be adsorbed to carriers in a manner known in principle and / or embedded in enveloping substances.
- the detergents, cleaners and disinfectants according to the invention which may be present as particularly pulverulent solids, in densified particle form, as homogeneous solutions or as suspensions or dispersions, may contain, in principle, all known ingredients customary in such agents besides the bleach-enhancing system used according to the invention.
- the detergents and cleaners according to the invention may in particular be builders, surface-active surfactants, organic and / or inorganic peroxygen compounds, water-miscible organic solvents, enzymes, sequestering agents, electrolytes, pH regulators and other auxiliaries, such as optical brighteners, grayness inhibitors, dye transfer inhibitors, foam regulators, additional peroxygen Activators and dyes and fragrances included.
- a disinfectant according to the invention may contain conventional antimicrobial active ingredients in addition to the previously mentioned ingredients to enhance the disinfecting action against special germs.
- antimicrobial additives are preferably not more than 10% by weight, particularly preferably from 0.1% by weight to 5% by weight, in the disinfectants according to the invention.
- Suitable peroxygen compounds especially organic peracids or peracid salts of organic acids such as phthalimidopercaproic, perbenzoic acid or salts of diperdodecanedioic acid, hydrogen peroxide and under the cleaning conditions hydrogen peroxide releasing inorganic salts such as perborate, percarbonate and / or persilicate and hydrogen peroxide inclusion compounds, such as H 2 O 2 -urea adducts, into consideration.
- Hydrogen peroxide can also be produced by means of an enzymatic system, ie an oxidase and its substrate.
- solid peroxygen compounds are to be used, they can be used in the form of powders or granules, which can also be enveloped in a manner known in principle.
- the peroxygen compounds can be added to the washing or cleaning liquor as such or in the form of these containing agents, which may in principle contain all conventional detergents, cleaners or disinfectant ingredients.
- Particular preference is given to using alkali metal percarbonate, alkali metal perborate monohydrate or hydrogen peroxide in the form of aqueous solutions which contain from 3% by weight to 10% by weight of hydrogen peroxide.
- a washing or cleaning agent according to the invention contains peroxygen compounds, these are present in amounts of preferably up to 25% by weight, in particular from 1% by weight to 20% by weight and more preferably from 7% by weight to 15% by weight. % present, while in disinfectants according to the invention preferably from 0.5 wt .-% to 40 wt .-%, in particular from 5 wt .-% to 20 wt .-%, of peroxygen compounds are included.
- compositions of the invention may contain one or more surfactants, in particular anionic surfactants, nonionic surfactants and mixtures thereof come into question.
- Suitable nonionic surfactants are in particular alkyl glycosides and ethoxylation and / or propoxylation of alkyl glycosides or linear or branched alcohols each having 12 to 18 carbon atoms in the alkyl moiety and 3 to 20, preferably 4 to 10 alkyl ether groups.
- N-alkyl-amines vicinal diols, fatty acid esters and fatty acid amides, which correspond to said long-chain alcohol derivatives with respect to the alkyl part, and of alkylphenols having 5 to 12 carbon atoms in the alkyl radical.
- Suitable anionic surfactants are in particular soaps and those which contain sulfate or sulfonate groups with preferably alkali ions as cations.
- Usable soaps are preferably the alkali salts of the saturated or unsaturated fatty acids having 12 to 18 carbon atoms. Such fatty acids can also be used in incompletely neutralized form.
- Useful surfactants of the sulfate type include the salts of the sulfuric acid half-esters of fatty alcohols having 12 to 18 carbon atoms and the sulfation products of said nonionic surfactants having a low degree of ethoxylation.
- Suitable surfactants of the sulfonate type include linear alkylbenzenesulfonates having 9 to 14 carbon atoms in the alkyl moiety, alkane sulfonates having 12 to 18 carbon atoms, and olefin sulfonates having 12 to 18 carbon atoms, which are formed in the reaction of corresponding monoolefins with sulfur trioxide, and alpha-sulfofatty acid esters resulting from the sulfonation of fatty acid methyl or ethyl esters.
- Such surfactants are in the cleaning or washing agents according to the invention in proportions of preferably 5 wt .-% to 50 wt .-%, in particular from 8 wt .-% to 30 wt .-%, while the inventive disinfectants as well as inventive compositions for cleaning dishes preferably 0.1 wt .-% to 20 wt .-%, in particular 0.2 wt .-% to 5 wt .-% surfactants containing.
- An agent according to the invention preferably contains at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
- the water-soluble organic builder substances include polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycinediacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid and polyaspartic acid, polyphosphonic acids, in particular aminotris (methylenephosphonic acid), ethylenediaminetetrakis (methylenephosphonic acid) and 1-hydroxyethane-1,1-diphosphonic acid, polymeric hydroxy compounds such as dextrin and polymeric (poly) carboxylic acids, in particular by oxidation of polysaccharides accessible polycarboxylates, polymeric acrylic acids, methacrylic acids, maleic acids and copolymers thereof, which also small amounts of polymerizable May contain copolymerized substances without carboxylic
- the relative average molecular weight (here and below: weight average) of the homopolymers of unsaturated carboxylic acids is generally between 5,000 and 200,000, of the copolymers between 2,000 and 200,000, preferably 50,000 to 120,000, each based on free acid.
- a particularly preferred acrylic acid-maleic acid copolymer has a relative average molecular weight of 50,000 to 100,000.
- Suitable, although less preferred, compounds of this class are copolymers of acrylic or methacrylic acid with vinyl ethers, such as vinylmethyl ethers, vinyl esters, ethylene, propylene and styrene, in which the acid content is at least 50% by weight.
- the first acidic monomer or its salt is derived from a monoethylenically unsaturated C 3 -C 8 -carboxylic acid and preferably from a C 3 -C 4 -monocarboxylic acid, in particular from (meth) -acrylic acid.
- the second acidic monomer or its salt can be a derivative of a C 4 -C 8 -dicarboxylic acid, with maleic acid being particularly preferred.
- the third monomeric unit is formed in this case of vinyl alcohol and / or preferably an esterified vinyl alcohol.
- vinyl alcohol derivatives which are an ester of short-chain carboxylic acids, for example C 1 -C 4 carboxylic acids, with vinyl alcohol.
- Preferred polymers contain from 60% by weight to 95% by weight, in particular from 70% by weight to 90% by weight, of (meth) acrylic acid or (meth) acrylate, particularly preferably acrylic acid or acrylate, and maleic acid or Maleinate and 5 wt .-% to 40 wt .-%, preferably 10 wt .-% to 30 wt .-% of vinyl alcohol and / or vinyl acetate.
- the second acidic monomer or its salt may also be a derivative of an allylsulfonic acid which is in the 2-position with an alkyl radical, preferably with a C 1 -C 4 -alkyl radical, or an aromatic radical which is preferably derived from benzene or benzene derivatives , is substituted.
- Preferred terpolymers contain from 40% by weight to 60% by weight, in particular from 45 to 55% by weight, of (meth) acrylic acid or (meth) acrylate, particularly preferably acrylic acid or acrylate, from 10% by weight to 30% by weight. %, preferably 15 wt .-% to 25 wt .-% methallylsulfonic acid or Methallylsulfonat and as the third monomer 15 wt .-% to 40 wt .-%, preferably 20 wt .-% to 40 wt .-% of a carbohydrate.
- This carbohydrate may be, for example, a mono-, di-, oligo- or polysaccharide, mono-, di- or oligosaccharides being preferred. Particularly preferred is sucrose.
- the use of the third monomer presumably incorporates predetermined breaking points into the polymer which are responsible for the good biodegradability of the polymer.
- These terpolymers generally have a relative average molecular weight between 1,000 and 200,000, preferably between 200 and 50,000 and in particular between 3,000 and 10,000.
- Further preferred copolymers are those which have as monomers acrolein and acrylic acid / acrylic acid salts or vinyl acetate.
- the organic builder substances can be used, in particular for the preparation of liquid agents, in the form of aqueous solutions, preferably in the form of 30 to 50 percent by weight aqueous solutions. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali metal salts.
- organic builder substances may be present in amounts of up to 40% by weight, in particular up to 25% by weight and preferably from 1% by weight to 8% by weight. Quantities close to the stated upper limit are preferably used in paste-form or liquid, in particular water-containing, agents according to the invention.
- Suitable water-soluble inorganic builder materials are, in particular, polyphosphates, preferably sodium triphosphate.
- water-insoluble inorganic builder materials are in particular crystalline or amorphous, water-dispersible alkali metal aluminosilicates, in amounts not exceeding 25 wt .-%, preferably from 3 wt .-% to 20 wt .-% and in particular in amounts of 5 wt .-% to 15 wt. -% used.
- the detergent-grade crystalline sodium aluminosilicates particularly zeolite A, zeolite P, and zeolite MAP, and optionally zeolite X, are preferred.
- Amounts near the above upper limit are preferably used in solid, particulate agents.
- suitable aluminosilicates have no particles with a particle size greater than 30 .mu.m and preferably consist of at least 80% by weight of particles having a size of less than 10 .mu.m.
- Their calcium binding capacity is generally in the range of 100 to 200 mg CaO per gram.
- water-soluble inorganic builder materials may be included.
- polyphosphates such as sodium triphosphate
- these include in particular the water-soluble crystalline and / or amorphous alkali metal silicate builders.
- Such water-soluble inorganic builder materials are preferably present in agents according to the invention in amounts of from 1% by weight to 20% by weight, in particular from 5% by weight to 15% by weight.
- the alkali silicates useful as builder materials preferably have a molar ratio of alkali oxide to SiO 2 below 0.95, in particular from 1: 1.1 to 1:12, and may be amorphous or crystalline.
- Preferred alkali metal silicates are the sodium silicates, in particular the amorphous sodium silicates, with a molar ratio of Na 2 O: SiO 2 of 1: 2 to 1: 2.8.
- the crystalline silicates which may be present alone or in admixture with amorphous silicates, are crystalline layer silicates with the general formula of Na 2 Si x O used 2x + 1 ⁇ y H 2 O in which x, known as the modulus, an integer of 1, 9 to 4 and y is a number from 0 to 20 and preferred values for x are 2, 3 or 4.
- Preferred crystalline Phyllosilicates are those in which x in the abovementioned general formula assumes the values 2 or 3.
- both ⁇ - and ⁇ -sodium disilicates are preferred.
- amorphous alkali silicates practically anhydrous crystalline alkali silicates of the abovementioned general formula in which x is a number from 1.9 to 2.1, can be used in inventive compositions.
- a crystalline sodium layer silicate with a modulus of 2 to 3 is used, as can be prepared from sand and soda.
- Sodium silicates with a modulus in the range of 1.9 to 3.5 are used in a further embodiment of inventive agents.
- a granular compound of alkali silicate and alkali carbonate is used, as is commercially available, for example, under the name Nabion® 15.
- Machine dishwashing detergents according to the invention are preferably of low alkalinity and contain the customary alkali carriers, for example alkali metal silicates, alkali metal carbonates and / or alkali hydrogen carbonates.
- Alkali silicates may be used in amounts of up to 30% by weight. %, based on the total mean.
- the use of the highly alkaline metasilicates as alkali carriers is preferably completely dispensed with.
- the alkali carrier system preferably used in the inventive compositions is a mixture of carbonate and bicarbonate, preferably sodium carbonate and bicarbonate, which is present in an amount of up to 60 wt .-%, preferably 10 wt .-% to 40 wt .-% , Depending on which pH is ultimately desired, the ratio of carbonate used and bicarbonate used varies, but usually an excess of sodium bicarbonate is used, so that the weight ratio of bicarbonate to carbonate is generally from 1: 1 to 15: 1.
- dishwashing compositions according to the invention, 20 wt.% To 40 wt.% Of water-soluble organic builders, in particular alkali citrate, 5 wt.% To 15 wt.% Alkali carbonate and 20 wt 40 wt .-% Alkalidisilikat included.
- bleach-activating compounds such as nitriles, from which perimic acids are formed may be present.
- nitriles include in particular aminoacetonitrile derivatives with quaternized nitrogen atom according to the formula in the R 1 is -H, -CH 3 , a C 2-24 -alkyl or alkenyl radical, a substituted C 1-24 -alkyl or C 2-24 -alkenyl radical having at least one substituent from the group -Cl, -Br, -OH, -NH 2 , -CN and -N (+) -CH 2 -CN, an alkyl or alkenylaryl radical having a C 1-24 -alkyl group, or a substituted alkyl- or alkenylaryl radical having at least one, preferably two, optionally substituted C 1-24 alkyl group (s) and optionally further substituents on the aromatic ring, R 2 and R 3 are
- Oxygen-carrying sulfonimines and / or acylhydrazones can also be used.
- the presence of bleach-catalyzing transition metal complexes is also possible. These are preferably selected from the cobalt, iron, copper, titanium, vanadium, manganese and ruthenium complexes.
- Suitable ligands in the transition metal complexes are both inorganic and organic compounds, in addition to carboxylates in particular compounds having primary, secondary and / or tertiary amine and / or alcohol functions, such as pyridine, pyridazine, pyrimidine, pyrazine, imidazole, pyrazole , Triazole, 2,2'-bispyridylamine, tris (2-pyridylmethyl) amine, 1,4,7-triazacyclononane, 1,4,7-trimethyl-1,4,7-triazacyclononane, 1,5,9-trimethyl -1,5,9-triazacyclododecane, (bis ((1-methylimidazol-2-yl) methyl)) - (2-pyridylmethyl) amine, N, N '- (bis (1-methylimidazole-2-yl) yl) -methyl) -ethylenediamine, N-bis (2-benzimidazolylmethyl
- the complex contains further, preferably anionic and among these in particular mono- or bidentate ligands.
- these include in particular the halides such as fluoride, chloride, bromide and iodide, and the (NO 2 ) - group, that is, a nitro ligand or a nitrito ligand.
- the (NO 2 ) - group may also be chelated to a transition metal, or it may bridge two transition metal atoms asymmetrically or ⁇ 1 -O-bridge.
- the transition metal complexes to be used in the activator system according to the invention may also contain further, generally simpler ligands, in particular mono- or polyvalent anion ligands.
- ligands for example, nitrate, actetate, trifluoroacetate, formate, carbonate, citrate, perchlorate and complex anions such as hexafluorophosphate.
- the anion ligands should provide charge balance between the transition metal central atom and the ligand system.
- the presence of oxo ligands, peroxo ligands and imino ligands is also possible.
- such ligands can also act bridging, so that polynuclear complexes arise.
- both metal atoms in the complex need not be the same.
- binuclear complexes in which the two transition metal central atoms have different oxidation numbers is also possible.
- anionic counterions which neutralize the cationic transition metal complex are present in the transition metal complex compounds to be used according to the invention.
- anionic counterions include in particular nitrate, hydroxide, hexafluorophosphate, sulfate, chlorate, perchlorate, the halides such as chloride or the anions of carboxylic acids such as formate, acetate, benzoate or citrate.
- transition metal complex compounds are Mn (IV) 2 ( ⁇ -O) 3 (1,4,7-trimethyl-1,4,7-triazacyclononane) di-hexafluorophosphate, [N, N'-bis [(2 hydroxy-5-vinylphenyl) methylene] -1,2-diaminocyclohexane] manganese (III) chloride, [N, N'-bis [(2-hydroxy-5-nitrophenyl) methylene] -1,2- diaminocyclohexane] manganese (III) acetate, [N, N'-bis [(2-hydroxyphenyl) methylene] -1,2-phenylenediamine] -manganese (III) acetate, [N, N'-bis [(2-Hydroxyphenyl) methylene] -1,2-diaminocyclohexane] manganese (III) chloride, [N, N'-bis [(2-hydroxyphenyl) m
- Suitable enzymes in the compositions according to the invention are, in particular, those from the class of proteases, lipases, cutinases, amylases, pullulanases, xylanases, hemicellulases, cellulases, peroxidases and oxidases or mixtures thereof, the use of protease, amylase, lipase and / or cellulase particularly preferred is.
- the proportion is preferably 0.2 wt .-% to 1.5 wt .-%, in particular 0.5 wt .-% to 1 wt .-%.
- the enzymes can be adsorbed in a customary manner on carriers and / or embedded in coating substances or incorporated as concentrated, as anhydrous liquid formulations.
- Suitable gravel inhibitors or soil release agents are cellulose ethers, such as carboxymethylcellulose, methylcellulose, hydroxyalkylcelluloses and cellulose mixed ethers, such as methylhydroxyethylcellulose, methylhydroxypropylcellulose and methylcarboxymethylcellulose.
- cellulose ethers such as carboxymethylcellulose, methylcellulose, hydroxyalkylcelluloses and cellulose mixed ethers, such as methylhydroxyethylcellulose, methylhydroxypropylcellulose and methylcarboxymethylcellulose.
- sodium carboxymethylcellulose and mixtures thereof with methylcellulose are used.
- Commonly used soil release agents include copolyesters containing dicarboxylic acid units, alkylene glycol units and polyalkylene glycol units.
- the proportion of grayness inhibitors and / or soil-release active ingredients in compositions according to the invention is generally not more than 2% by weight and is preferably from 0.5% by weight to 1.5% by weight.
- derivatives of diaminostilbene disulfonic acid or their alkali metal salts may be included.
- salts of 4,4'-bis (2-anilino-4-morpholino-1,3,5-triazin-6-yl-amino) -stilbene-2,2'-disulphonic acid or similarly constructed compounds which are suitable instead of the morpholino group carry a diethanolamino group, a methylamino group or a 2-methoxyethylamino group.
- brighteners of the substituted 4,4'-distyryl-diphenyl type may be present, for example, 4,4'-bis (4-chloro-3-sulfostyryl) -diphenyl.
- mixtures of brighteners can be used.
- brighteners of the 1,3-diaryl-2-pyrazolines type for example 1- (p-sulfamoylphenyl) -3- (p-chlorophenyl) -2-pyrazoline, and compounds of similar construction are particularly suitable.
- the content of the composition in optical brighteners or brightener mixtures is generally not more than 1 wt .-%, preferably 0.05 wt .-% to 0.5 wt .-%. In a preferred embodiment of the invention, the agent is free of such agents.
- the usual foam regulators which can be used in the compositions according to the invention include, for example, polysiloxane-silica mixtures, the finely divided silica contained therein preferably being silanated or otherwise rendered hydrophobic.
- the polysiloxanes can consist of both linear compounds as well as crosslinked polysiloxane resins and mixtures thereof.
- Further antifoams are paraffin hydrocarbons, in particular microparaffins and paraffin waxes whose melting point is above 40 ° C., saturated fatty acids or soaps having in particular 20 to 22 carbon atoms, for example sodium behenate, and alkali metal salts of phosphoric mono- and / or dialkyl esters in which the alkyl chains each having 12 to 22 carbon atoms.
- the proportion of foam regulators can preferably 0.2 wt .-% to 2 wt .-% amount.
- organic solvents which can be used in the compositions according to the invention, especially if they are in liquid or pasty form, are alcohols having 1 to 4 C atoms, in particular methanol, ethanol, isopropanol and tert-butanol, diols having 2 to 4 C atoms , in particular ethylene glycol and propylene glycol, and mixtures thereof and the derivable from said classes of compound ethers.
- Such water-miscible solvents are present in compositions according to the invention in amounts of preferably not more than 20% by weight, in particular from 1% by weight to 15% by weight.
- the compositions according to the invention can contain system- and environmentally compatible acids, in particular citric acid, acetic acid, tartaric acid, malic acid, lactic acid, glycolic acid, succinic acid, glutaric acid and / or adipic acid. but also mineral acids, in particular sulfuric acid or alkali hydrogen sulfates, or bases, in particular ammonium or alkali metal hydroxides.
- Such pH regulators are preferably not more than 10 wt .-%, in particular from 0.5 wt .-% to 6 wt .-%, contained in the inventive compositions.
- compositions according to the invention presents no difficulties and can be carried out in a manner known in the art, for example by spray-drying or granulation, wherein peroxygen compound and bleach catalyst are optionally added separately later.
- compositions according to the invention in the form of solutions containing aqueous or other conventional solvents are produced particularly advantageously by simply mixing the ingredients, which can be added in bulk or as a solution in an automatic mixer.
- compositions according to the invention are preferably in the form of pulverulent, granular or tablet-like preparations which are prepared in a manner known per se, for example by mixing, granulating, roll compacting and / or spray-drying the thermally stable components and admixing the more sensitive components, in particular enzymes, bleaches and the bleach-activating system can be expected to be prepared.
- inventive compositions having an increased bulk density in particular in the range from 650 g / l to 950 g / l, a process comprising an extrusion step is preferred.
- the procedure is preferably such that all ingredients are mixed together in a mixer and the mixture by means of conventional tablet presses, such as eccentric or rotary presses with pressing pressures in the range of 200 ⁇ 10 5 Pa to 1 500 ⁇ 10 5 Pa pressed. you thus obtains without difficulty fracture-resistant, yet sufficiently rapidly soluble under application conditions tablets with flexural strength of usually over 150 N.
- a tablet produced in a weight of 15 g to 40 g, in particular from 20 g to 30 g, with a diameter of 35 mm up to 40 mm.
- compositions according to the invention in the form of non-dusting, storage-stable free-flowing powders and / or granules with high bulk densities in the range from 800 to 1000 g / l can also be effected by using the builder components with at least a proportion of liquid mixture components in a first process substep while increasing the bulk density of this premix and subsequently - if desired after intermediate drying - the other constituents of the agent, including the bleach-activating system, combined with the thus obtained premix.
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Claims (8)
- Utilisation d'un système d'acide de Lewis et d'une substance précurseur de peracide dans des conditions de perhydrolyse comme activateur de composés peroxydes dans des solutions d'oxydation, de lavage, de nettoyage ou de désinfection, l'acide de Lewis étant choisi parmi les sels de bismuth (III), les sels d'indium (III), les sels de samarium (III) et leurs mélanges.
- Utilisation d'acide de Lewis pour accélérer la formation d'acide peroxocarboxylique à partir d'un composé peroxyde et d'une substance précurseur de peracide dans des conditions de perhydrolyse, où l'acide de Lewis est choisi parmi les sels de bismuth (III), les sels d'indium (III), les sels de samarium (III) et leurs mélanges.
- Utilisation d'un système d'acide de Lewis et d'une substance produit un peracide dans des conditions de perhydrolyse pour blanchir des encrassements colorés au cours du lavage de textiles, en particulier dans un bain aqueux contenant des tensioactifs ou dans des solutions de nettoyage pour surfaces dures, en particulier pour la vaisselle, pour le blanchiment de taches colorées, en particulier de thé, l'acide de Lewis étant choisi parmi les sels de bismuth (III), les sels d'indium (III), les sels de samarium (III) et leurs mélanges.
- Procédé de fabrication de peracide à partir de peroxyde et d'une substance produisant un peracide dans des conditions de perhydrolyse, caractérisé en ce qu'on utilise un acide de Lewis choisi parmi les sels de bismuth (III), les sels d'indium (III), les sels de samarium (III) et leurs mélanges.
- Utilisation selon une des revendications 1 à 3 ou procédé selon la revendication 4, caractérisée en ce qu'il s'agit d'un peroxyde minéral.
- Utilisation ou procédé selon une des revendications précédentes, caractérisé en ce que le rapport molaire du composé libérant un peracide à l'acide de Lewis se situe entre 100:1 et 1:50, en particulier entre 10:1 et 1:5.
- Utilisation ou procédé selon une des revendications précédentes, caractérisé en ce que l'acide de Lewis est choisi parmi l'oxynitrate de bismuth (III), le sulfate d'indium (III) et le nitrate de samarium (III), ainsi que leurs mélanges.
- Utilisation ou procédé selon une des revendications précédentes, caractérisé en ce qu'on choisit le composé précurseur de peracide en conditions de perhydrolyse parmi les composés qui donnent, dans des conditions de perhydrolyse, de l'acide perbenzoïque éventuellement substitué et/ou des peracides aliphatiques avec 1 à 12 atomes de carbone, en particulier de 2 à 4 atomes de carbone, seuls ou en mélange.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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PL12722337T PL2714877T3 (pl) | 2011-05-24 | 2012-05-16 | Układy aktywatorów dla związków nadtlenowych |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102011076417A DE102011076417A1 (de) | 2011-05-24 | 2011-05-24 | Aktivatorsysteme für Persauerstoffverbindungen |
PCT/EP2012/059085 WO2012159944A1 (fr) | 2011-05-24 | 2012-05-16 | Systèmes activateurs pour composés peroxygénés |
Publications (2)
Publication Number | Publication Date |
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EP2714877A1 EP2714877A1 (fr) | 2014-04-09 |
EP2714877B1 true EP2714877B1 (fr) | 2017-07-05 |
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EP12722337.8A Active EP2714877B1 (fr) | 2011-05-24 | 2012-05-16 | Systèmes activateurs pour composés peroxygénés |
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EP (1) | EP2714877B1 (fr) |
DE (1) | DE102011076417A1 (fr) |
PL (1) | PL2714877T3 (fr) |
WO (1) | WO2012159944A1 (fr) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10031081B2 (en) | 2013-03-05 | 2018-07-24 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
US10172351B2 (en) | 2015-09-04 | 2019-01-08 | Ecolab Usa Inc. | Performic acid on-site generator and formulator |
US10233149B2 (en) | 2014-12-18 | 2019-03-19 | Ecolab Usa Inc. | Methods for forming peroxyformic acid and uses thereof |
US10285401B2 (en) | 2015-09-10 | 2019-05-14 | Ecolab Usa Inc. | Self indicating antimicrobial chemistry |
US10542751B2 (en) | 2014-12-18 | 2020-01-28 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US10893674B2 (en) | 2013-03-05 | 2021-01-19 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US11260040B2 (en) | 2018-06-15 | 2022-03-01 | Ecolab Usa Inc. | On site generated performic acid compositions for teat treatment |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9321664B2 (en) | 2011-12-20 | 2016-04-26 | Ecolab Usa Inc. | Stable percarboxylic acid compositions and uses thereof |
US9752105B2 (en) | 2012-09-13 | 2017-09-05 | Ecolab Usa Inc. | Two step method of cleaning, sanitizing, and rinsing a surface |
DE102014209241A1 (de) * | 2014-05-15 | 2015-11-19 | Henkel Ag & Co. Kgaa | Wasch- und Reinigungsmittel mit erhöhter Bleichleistung |
WO2019113926A1 (fr) | 2017-12-15 | 2019-06-20 | Rhodia Operations | Composition contenant un complexe métallique de lanthanide |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2297096A (en) * | 1995-01-20 | 1996-07-24 | Procter & Gamble | Bleaching composition. |
US6416687B1 (en) * | 1996-08-21 | 2002-07-09 | The Procter & Gamble Company | Bleaching compositions |
FR2792500B1 (fr) * | 1999-04-23 | 2004-05-21 | Internat Redox Dev | Composition aqueuse, notamment sous forme de gel, a base de ho2f , acides et ions metalliques, procede de preparation notamment quand lesdits ions sont ag2+ et utilisation dans le domaine de la desinfection et/ou du traitement de surface |
GB2402132B (en) * | 2003-05-28 | 2005-10-19 | Reckitt Benckiser Nv | Dishwasher anti-corrosion composition |
DE102009017724A1 (de) * | 2009-04-11 | 2010-10-14 | Clariant International Limited | Bleichmittelgranulate |
-
2011
- 2011-05-24 DE DE102011076417A patent/DE102011076417A1/de not_active Withdrawn
-
2012
- 2012-05-16 EP EP12722337.8A patent/EP2714877B1/fr active Active
- 2012-05-16 WO PCT/EP2012/059085 patent/WO2012159944A1/fr active Application Filing
- 2012-05-16 PL PL12722337T patent/PL2714877T3/pl unknown
Non-Patent Citations (1)
Title |
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None * |
Cited By (20)
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US10031081B2 (en) | 2013-03-05 | 2018-07-24 | Ecolab Usa Inc. | Peroxycarboxylic acid compositions suitable for inline optical or conductivity monitoring |
US10165774B2 (en) | 2013-03-05 | 2019-01-01 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
US11206826B2 (en) | 2013-03-05 | 2021-12-28 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
US11026421B2 (en) | 2013-03-05 | 2021-06-08 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US10893674B2 (en) | 2013-03-05 | 2021-01-19 | Ecolab Usa Inc. | Efficient stabilizer in controlling self accelerated decomposition temperature of peroxycarboxylic acid compositions with mineral acids |
US10542751B2 (en) | 2014-12-18 | 2020-01-28 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US10233149B2 (en) | 2014-12-18 | 2019-03-19 | Ecolab Usa Inc. | Methods for forming peroxyformic acid and uses thereof |
US10709131B2 (en) | 2014-12-18 | 2020-07-14 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US11684067B2 (en) | 2014-12-18 | 2023-06-27 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US10834924B2 (en) | 2014-12-18 | 2020-11-17 | Ecolab Usa Inc. | Generation of peroxyformic acid through polyhydric alcohol formate |
US11325887B2 (en) | 2014-12-18 | 2022-05-10 | Ecolab Usa Inc. | Methods for forming peroxyformic acid and uses thereof |
US10899707B2 (en) | 2014-12-18 | 2021-01-26 | Ecolab Usa Inc. | Methods for forming peroxyformic acid and uses thereof |
US10172351B2 (en) | 2015-09-04 | 2019-01-08 | Ecolab Usa Inc. | Performic acid on-site generator and formulator |
US10729131B2 (en) | 2015-09-04 | 2020-08-04 | Ecolab Usa Inc. | Performic acid on-site generator and formulator |
US11737460B2 (en) | 2015-09-04 | 2023-08-29 | Ecolab Usa Inc. | Performic acid on-site generator and formulator |
US10555523B2 (en) | 2015-09-10 | 2020-02-11 | Ecolab Usa Inc. | Self indicating antimicrobial chemistry |
US10285401B2 (en) | 2015-09-10 | 2019-05-14 | Ecolab Usa Inc. | Self indicating antimicrobial chemistry |
US11576378B2 (en) | 2015-09-10 | 2023-02-14 | Ecolab Usa Inc. | Self indicating antimicrobial chemistry |
US11260040B2 (en) | 2018-06-15 | 2022-03-01 | Ecolab Usa Inc. | On site generated performic acid compositions for teat treatment |
US11771673B2 (en) | 2018-06-15 | 2023-10-03 | Ecolab Usa Inc. | On site generated performic acid compositions for teat treatment |
Also Published As
Publication number | Publication date |
---|---|
DE102011076417A1 (de) | 2012-11-29 |
PL2714877T3 (pl) | 2017-12-29 |
EP2714877A1 (fr) | 2014-04-09 |
WO2012159944A1 (fr) | 2012-11-29 |
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