WO2007013324A1 - 有機過酸ポリマー組成物およびその製造方法 - Google Patents
有機過酸ポリマー組成物およびその製造方法 Download PDFInfo
- Publication number
- WO2007013324A1 WO2007013324A1 PCT/JP2006/314169 JP2006314169W WO2007013324A1 WO 2007013324 A1 WO2007013324 A1 WO 2007013324A1 JP 2006314169 W JP2006314169 W JP 2006314169W WO 2007013324 A1 WO2007013324 A1 WO 2007013324A1
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- WO
- WIPO (PCT)
- Prior art keywords
- acid
- polymer
- organic
- organic peracid
- composition
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 199
- 150000004967 organic peroxy acids Chemical class 0.000 title claims abstract description 131
- 239000000203 mixture Substances 0.000 title claims abstract description 121
- 238000000034 method Methods 0.000 title claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 106
- 150000007524 organic acids Chemical class 0.000 claims abstract description 66
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 50
- 238000002156 mixing Methods 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000004061 bleaching Methods 0.000 claims description 55
- 238000004519 manufacturing process Methods 0.000 claims description 42
- 238000004140 cleaning Methods 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000003381 stabilizer Substances 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 12
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 11
- 229920002125 Sokalan® Polymers 0.000 claims description 7
- 238000007865 diluting Methods 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000004584 polyacrylic acid Substances 0.000 claims description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 6
- 239000012895 dilution Substances 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- 229940005740 hexametaphosphate Drugs 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 235000011007 phosphoric acid Nutrition 0.000 claims description 6
- 229940048084 pyrophosphate Drugs 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 230000000249 desinfective effect Effects 0.000 claims description 5
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 3
- 229920001444 polymaleic acid Polymers 0.000 claims description 3
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 5
- 239000007844 bleaching agent Substances 0.000 abstract description 5
- 239000012459 cleaning agent Substances 0.000 abstract description 4
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 230000009965 odorless effect Effects 0.000 abstract 1
- 230000001954 sterilising effect Effects 0.000 description 45
- 238000004659 sterilization and disinfection Methods 0.000 description 27
- 230000000694 effects Effects 0.000 description 26
- 238000005406 washing Methods 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 150000004965 peroxy acids Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 239000004744 fabric Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 4
- -1 bleaches Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000004453 electron probe microanalysis Methods 0.000 description 3
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 238000004378 air conditioning Methods 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000010842 industrial wastewater Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940097156 peroxyl Drugs 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ADKBGLXGTKOWIU-UHFFFAOYSA-N butanediperoxoic acid Chemical compound OOC(=O)CCC(=O)OO ADKBGLXGTKOWIU-UHFFFAOYSA-N 0.000 description 1
- LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/06—Oxidation
-
- 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
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
-
- 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
- C11D3/3945—Organic per-compounds
-
- 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
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
Definitions
- the present invention relates to a composition comprising an organic peracid polymer having excellent sterilizing, bleaching and cleaning effects.
- organic peracids include formic acid, peracetic acid, perpropionic acid, perbutyric acid, permalonic acid, persuccinic acid, perdaltalic acid, peradipic acid, pertartaric acid, perquenic acid, perbenzoic acid, perbenzoic acid. Phthalic acid and the like are known. These peracids are useful in applications such as disinfectants, bleaches, cleaning agents, and epoxidizing agents. However, these organic peracids are not necessarily satisfying in terms of stability, odor, water solubility, etc.! /.
- Patent Document 1 discloses a fungicide composition containing a peracid and an organic polymer.
- the peracid used here is sufficient for sterilization and bleaching. It has the disadvantage of not having cleaning performance.
- Patent Document 1 Japanese Patent Laid-Open No. 61-158907
- An object of the present invention is to obtain an organic peracid polymer-containing composition having excellent sterilization and bleaching ability, good stability and little odor, and sufficient water solubility.
- the carbon in the organic acid polymer can be used. It was found that the conversion of a boxyl group into a peroxycarboxyl group by peroxyhydrogen can be carried out efficiently.
- the present invention relates to a sterilizing “bleaching” cleaning composition and a method for producing the same as shown in the following (1) to (21).
- Sterilization / bleaching / washing characterized by containing as an active ingredient an organic peracid polymer in which at least one part of the carboxyl group in the constituent unit of the organic acid polymer is converted to a peroxyl lpoxyl group Composition.
- composition according to claim 1 wherein a conversion ratio of a carboxyl group to a peroxycarboxyl group in the organic peracid polymer is 5% or more.
- composition according to claim 1 or 2 wherein the organic peracid polymer has a molecular weight of 500 to 100,000.
- the organic peracid polymer is selected from the group consisting of perpolyacrylic acid, perpolymethacrylic acid, perpolymaleic acid, peracrylic acid copolymer, permethacrylic acid copolymer and permaleic acid copolymer, and salts thereof 1
- composition according to claim 6, wherein the inorganic acid is one or more selected from the group power of sulfuric acid, orthophosphoric acid and pyrophosphoric acid.
- composition according to any one of claims 1 to 7, further comprising a stabilizer (8) The composition according to any one of claims 1 to 7, further comprising a stabilizer.
- the stabilizer is one or more selected from orthophosphate, 1-hydroxyethane-1,1-bis (phosphonic acid) or a salt thereof, pyrophosphate, hexametaphosphate and dipicolinic acid.
- a method for producing a composition containing an organic peracid polymer in which at least a part of the carboxyl groups in the structural unit of the organic acid polymer is converted to a peroxy carboxyl group A method for producing an organic peracid polymer-containing composition comprising a mixing step of mixing at least the following components (i) to (iv):
- the organic acid polymer strength polyacrylic acid, polymethacrylic acid, polymaleic acid, allylic acid copolymer, methacrylic acid copolymer and maleic acid copolymer, and their salt strength is also one or more selected The production method according to any one of claims 10 to 13.
- the mixing ratio of components (i) to (iv) in the mixing step is organic acid polymer; 3 to 60% by weight, hydrogen peroxide; 2 to 60% by weight, inorganic acid; 0.1 to 10% by weight
- the stabilizer is further mixed in the mixing step.
- the stabilizer is orthophosphate, 1-hydroxyethane-1,1-bis (phosphonic acid) or a salt thereof, pyrophosphate, hexametaphosphate and dipicolinic acid.
- the method further comprises a dilution step of adding a diluent after the mixing step.
- the production method according to any one of claims 10 to 18.
- organic peracid polymer-containing composition produced by the production method according to any one of claims 10 to 19, wherein the organic peracid polymer is 2 to 50% by weight, hydrogen peroxide 2 to 50
- organic peracid polymer-containing composition characterized by containing 0.1% by weight and 10% by weight of an inorganic acid.
- Patent Document 1 discloses a fungicide composition containing a peracid and an organic polymer, but does not describe an organic peracid polymer. Further, in Patent Document 1, even when a peroxyhydrogen is used as the peracid compound and an organic acid polymer is used as the organic polymer, the organic peracid polymer in the case of containing no inorganic acid as the acid catalyst is used. The production is slight and the performance as an organic peracid polymer cannot be exhibited.
- the composition of the present invention containing an organic peracid polymer as an active ingredient is a composition containing a peracid product such as an organic peracid that has been used for conventional sterilization 'bleaching' washing, or simply Compared to a mixture of organic acid polymer and hydrogen peroxide, etc., it has excellent sterilization 'bleaching' cleaning ability and high sterilization / bleaching / cleaning effect even when compared with the same effective oxygen concentration. Furthermore, the composition of the present invention is stable because the organic peracid polymer is decomposed, so that the sterilization / bleaching / washing effect does not deteriorate even after long-term storage. In addition, the organic peracid polymer used in the present invention has little odor and has sufficient water solubility, so it is easy to use even when diluted. Therefore, it is highly practical and can be used comfortably not only for industrial use but also for general household use.
- the peroxy-reaction (equilibrium reaction) of the carboxyl group in the organic acid polymer by peroxy-hydrogen is the peroxycarboxyl. It proceeds rapidly in the direction of group formation and reaches an equilibrium state where the percentage of peroxycarboxyl groups is high. Therefore, a high concentration organic peracid polymer can be produced using an aqueous solution containing a high concentration of organic acid polymer. Therefore, a composition containing a sufficient amount of the organic peracid polymer can be obtained.
- the equilibrium reaction is difficult to proceed when the organic acid polymer is in a low concentration state. Although it is not easy to efficiently obtain a low-concentration organic peracid polymer composition having a relatively high water content, the above-described equilibrium reaction can be efficiently advanced at a high concentration by using the method of the present invention. Since an organic peracid polymer composition can be produced, an organic peracid polymer composition of any concentration can be efficiently obtained by diluting the organic peracid polymer composition thus obtained. Can do.
- the sterilizing and bleaching / cleaning composition of the present invention contains an organic peracid polymer as an active ingredient.
- the organic peracid polymer in the present invention has a structure in which at least a part of the carboxyl groups are replaced (converted) with a peroxycarboxyl group in the organic acid polymer having a carboxyl group in the structural unit. Let's go.
- the organic peracid polymer of the present invention is one or more selected from these powerful group forces, and may be used alone or in combination of two or more.
- the lower limit of the conversion ratio of the carboxyl group to the peroxycarboxyl group is preferably 5%, more preferably 7%, still more preferably 10%, and the upper limit is preferably 90%, more preferably 70%. %, More preferably 50%. If the conversion rate is too low, the sterilization 'bleaching' washing effect as an organic peracid is not sufficiently exhibited, and if the conversion rate is too high, it may be difficult to produce.
- the molecular weight of the organic peracid polymer is preferably 500 to 100,000, more preferably 2000 to 20,000. If the molecular weight of the organic peracid polymer is too low, the sterilization 'floating' cleaning effect as an organic peracid will not be fully exerted, and if the molecular weight is too high, it may be difficult to produce
- the concentration of the organic peracid polymer in the disinfecting and bleaching 'cleaning composition of the present invention is preferably Is 2 to 50% by weight, more preferably 2 to 15% by weight. That is, the sterilizing “floating” cleaning composition of the present invention can contain an organic peracid polymer at a relatively high concentration. A product having an organic peracid polymer concentration that is too high is difficult to produce. If the concentration of the organic peracid polymer is too low, the sterilizing / bleaching / cleaning effect as an organic peracid may not be sufficiently exerted.
- the sterilizing / bleaching / cleaning composition of the present invention has excellent sterilizing / bleaching / cleaning ability of organic peracid polymer, so that even when diluted, it exhibits its excellent sterilizing / bleaching / cleaning effect. Can be made. Therefore, the organic peracid polymer concentration is not particularly limited.
- the concentration of the organic peracid polymer of the present invention can be determined by the following mathematical formula (1).
- the conversion ratio (%) of the carboxyl group to the percarboxyl group can be obtained from the formula (1) (see the formula (2)).
- P is the concentration of the organic peracid polymer (wt%)
- Q is the concentration of the organic acid polymer (percentage wt) before being peroxylated
- R is the conversion of the carboxyl group to a percarboxyl group. Conversion ratio (%)
- C represents the molecular weight per carboxyl group of the organic acid polymer, respectively.
- the composition of the present invention may contain hydrogen peroxide in addition to the organic peracid polymer.
- a peroxyhydrogen used to peroxylate the carboxyl group in the structural unit of the organic acid polymer to convert it to a peroxycarboxyl group during the production of the composition.
- Hydrogen peroxide itself has a disinfecting, bleaching and cleaning ability, so that sufficient amount of organic peracid polymer can be obtained by an equilibrium reaction with organic acid polymer that not only contributes to the disinfection and bleaching 'cleaning effect of the whole composition. This contributes to the formation and maintenance of (stability in aqueous solution). Therefore, the combination of an organic peracid polymer and peroxyhydrogen is used to further enhance the sterilization / bleaching 'cleaning effect of the composition of the present invention. Can be increased.
- the concentration of hydrogen peroxide in the composition of the present invention is preferably 2 to 50 wt%, more preferably 5 to 30 wt%. If the concentration of hydrogen peroxide is too low, the amount of the organic peracid polymer produced by the equilibrium reaction with the organic acid polymer may be insufficient, and the sterilization / bleaching / washing effect of the present invention may not be sufficiently exerted. On the other hand, even if the concentration of hydrogen peroxide is too high, the above effect is not enhanced, and there may be a problem in safety.
- the inorganic acid makes the effect of increasing the concentration of the organic peracid polymer in the composition of the present invention remarkable.
- the reason for this is thought to be that the percarboxyl group of the carboxyl group is promoted by suppressing the dissociation of the carboxyl group in the organic acid polymer due to the influence of the inorganic acid. That is, in the absence of an inorganic acid, it is difficult to obtain a high concentration organic peracid polymer composition as in the present invention.
- the inorganic acid is preferably selected from the group consisting of sulfuric acid, orthophosphoric acid, and pyrophosphoric acid. These may be used alone or in combination of two or more.
- the concentration of the inorganic acid is 0.1 to 10% by weight, preferably 0.3 to 5% by weight. If the concentration of the inorganic acid is too low, sufficient effects cannot be obtained, and if the concentration is too high, the effects are not high.
- the composition of the present invention preferably contains a stabilizer.
- a stabilizer By adding a stabilizer, the stability of the organic peracid polymer and peroxyhydrogen is improved.
- any peracid stabilizer can be used, especially orthophosphate, 1-hydroxyethane 1,1 bis (phosphonic acid) or its salt, pyrophosphate, hexametaphosphate, and Dipicolinic acid power is preferably selected.
- the salt include a sodium salt and a potassium salt, and a sodium salt is more preferable. These may be used alone or in combination of two or more.
- the concentration of the stabilizer is preferably 0.01 to 5% by weight, more preferably 0.02 to 3% by weight.
- Stabilizers may be used as necessary. However, if the stabilizer concentration is too low, a sufficient peracid stabilizing effect may not be obtained. On the other hand, even if the stabilizer concentration is too high, the stabilizing effect does not increase. [0032] ⁇ Other ingredients>
- the sterilizing / bleaching / cleaning composition of the present invention if necessary, additives such as general sterilizing and whitening / cleaning agents, such as surfactants, thickeners, and fragrances are used. Further, a coloring agent or the like may be appropriately blended.
- the remainder other than the organic peracid polymer, hydrogen peroxide, inorganic acid, and stabilizers and other additives added as needed is mainly water.
- the pH of the sterilizing / bleaching / cleaning composition of the present invention is 3 or less, preferably pH 1 or less. If the pH exceeds 3, a composition having a high organic peracid polymer concentration may not be obtained. If the composition of the present invention contains an inorganic acid, it is usually at most PH3.
- the sterilizing / bleaching / cleaning composition of the present invention can be used by diluting to any organic peracid polymer concentration.
- the diluent include water and an aqueous alcohol solution.
- the dilution factor is not particularly limited, but is preferably 1.1 to: LOOOO times, more preferably 1.1 to 1000 times.
- the production method of the present invention is a method for producing a composition containing an organic peracid polymer in which at least a part of carboxyl groups in the structural unit of an organic acid polymer is converted to a peroxycarboxyl group, It includes a mixing step of mixing the following components (i) to (iv).
- the organic acid polymer, hydrogen peroxide, inorganic acid, and water are mixed and dissolved, and the resulting mixture is preferably held for 1 hour to 1 month (more preferably 4 hours to 20 days).
- the mixing dissolution temperature in a mixing process is not specifically limited, Preferably it is 10-80 degreeC, More preferably, it is 20-70 degreeC.
- the carboxyl group in the organic acid polymer reacts with hydrogen peroxide and is gradually replaced with a peroxycarboxyl group.
- the reaction between the organic acid polymer and peroxyhydrogen proceeds as an equilibrium reaction of the organic peracid polymer, hydrogen peroxide, and organic acid polymer, and reaches the maximum substitution rate after approximately 1 hour to 1 month. After that, the substitution ratio becomes almost constant. Increasing the concentration of hydrogen peroxide increases the substitution rate. That is, the higher the concentration of the organic acid polymer and hydrogen peroxide, the higher the concentration of organic peracid polymer formed.
- the organic acid polymer used in the production method of the present invention is not particularly limited as long as it is a polymer having a carboxyl group in its constituent unit, and specifically, polyacrylic acid, polymethacrylic acid, polymaleic acid, acrylic acid copolymer. , Methacrylic acid copolymers and maleic acid copolymers, and the group power of their salt strength, which may be selected alone or in combination of two or more.
- the molecular weight of the organic acid polymer is preferably 500 to 100,000, more preferably 2000 to 20,000. If the molecular weight of the organic acid polymer is too low, an organic peracid polymer having a sufficiently high sterilization / bleaching / washing effect may not be obtained. If the molecular weight is too high, it may be difficult to produce the organic peracid polymer-containing composition.
- the charged amount (used amount or mixing ratio) of the organic acid polymer is preferably 3 to 60% by weight, more preferably 5 to 40% by weight, based on the entire charged raw material (mixed raw material). If the amount of the organic acid polymer used is too small, the concentration of the organic peracid polymer in the resulting organic peracid polymer-containing composition will be low, and the organic peracid polymer-containing composition will have a sufficient sterilization 'bleaching-washing effect'. May not be demonstrated. On the other hand, even if the amount of the organic acid polymer used is too large, the concentration of the organic peracid polymer does not necessarily increase according to the amount used.
- the peroxyhydrogen used in the production method of the present invention the same peroxyhydrogen as contained in the above-mentioned disinfecting “bleaching” cleaning composition of the present invention can be used.
- the purification method include a method of contacting with ion exchange resin or chelate resin. It is done.
- peroxyhydrogen itself has a sterilizing 'bleaching' cleaning ability, it can be used only to contribute to the sterilization and bleaching 'cleaning effect of the entire organic peracid polymer-containing composition.
- the equilibrium reaction with the acid polymer contributes to the production and maintenance of a sufficient amount of organic peracid polymer. Therefore, a composition containing a high concentration organic peracid polymer can be obtained by combining and mixing the organic acid polymer and peroxyhydrogen.
- the amount of hydrogen peroxide charged is preferably 2 to 60 wt%, more preferably 5 to 40 wt%. If the amount of peroxyhydrogen used is too small, the amount of the organic peracid polymer produced by the equilibrium reaction with the organic acid polymer will be insufficient, and the sterilization / bleaching 'cleaning effect of the present invention may not be sufficiently exhibited. is there. On the other hand, even if the concentration of peroxyhydrogen is too high, the concentration of organic peracid polymer does not necessarily increase according to the amount used.
- An inorganic acid makes the effect which raises the density
- the reason is considered to be that the dissociation of the carboxyl group in the organic acid polymer is suppressed by the influence of the inorganic acid, thereby promoting the percarboxyl group of the carboxyl group. That is, in the absence of an inorganic acid, it may be difficult to obtain a high-concentration organic peracid polymer-containing composition.
- the inorganic acid used in the production method of the present invention is the same as the inorganic acid contained in the sterilizing 'bleaching' cleaning composition of the present invention, that is, as the inorganic acid, sulfuric acid, orthophosphoric acid, and pyrroline.
- a group force that also has acid power can be selected. These may be used alone or in combination of two or more.
- the amount of the inorganic acid charged is preferably 0.1 to LO weight%, more preferably 0.3 to 5 weight%. If the amount of inorganic acid used is too small, a sufficient concentration of organic peracid polymer may not be formed. On the other hand, even if the amount of inorganic acid used is too large, the concentration of the organic peracid polymer is not necessarily increased.
- a stabilizer may be used as necessary. Add stabilizer As a result, the stability of the produced organic peracid polymer and peroxyhydrogen is improved. Any stabilizer can be used as long as it is a peracid stabilizer.
- Orthophosphate, 1-hydroxyethane-1, which is the same as that used in the above-mentioned bactericidal 'bleaching' cleaning composition of the present invention. , 1 Bis (phosphonic acid) or a salt thereof, pyrophosphate, hexametaphosphate, and dipicolinic acid are preferably selected. Examples of the salt include sodium salt and potassium salt, and sodium salt is more preferable. These may be used alone or in combination of two or more.
- the stabilizer when added, it may be added to the composition containing the organic peracid polymer, the peroxyhydrogen and the inorganic acid after the organic peracid polymer is formed in the mixing step, but the organic acid polymer, It is preferable to add hydrogen peroxide and an inorganic acid simultaneously when mixing.
- the remainder other than the organic acid polymer, hydrogen peroxide, inorganic acid, and stabilizer added as needed is mainly water.
- the amount of water charged is preferably 20 to 90% by weight, more preferably 30 to 70% by weight.
- general additives used in addition to sterilizing / bleaching / cleaning agents for example, surfactants, thickeners, fragrances, coloring agents, and the like are appropriately added. Is possible.
- an organic peracid polymer is produced by an equilibrium reaction between the organic acid polymer and hydrogen peroxide.
- the amount of the inorganic acid that functions as an acid catalyst is preferably 0.5 to 30% of the amount of the organic acid polymer charged.
- the lower limit of the conversion ratio of the carboxyl group of the organic acid polymer to the peroxycarboxyl group is preferably 5%, more preferably 7%, still more preferably 10%, and the upper limit. Preferably it is 90%, more preferably 70%, still more preferably 50%.
- a high concentration organic peracid polymer can be produced by using an inorganic acid as a catalyst for the equilibrium reaction between the organic acid polymer and hydrogen peroxide. If the conversion ratio is too low, the organic peracid polymer-containing composition is sterilized. • If the bleaching 'cleaning effect is not fully demonstrated and the conversion rate is too high, it may be difficult to manufacture.
- a dilution step in which a diluent is further added can be included.
- the diluent include water and an aqueous alcohol solution.
- the dilution factor is not particularly limited, but is preferably 1.1 to: LOOOO times, more preferably 1.1 to 1000 times.
- a mixed solution containing a high concentration organic acid polymer and peroxyhydrogen is prepared, and a high concentration organic peracid is obtained by an equilibrium reaction between the organic acid polymer and peracid hydrogen.
- a composition containing an organic peracid polymer having an arbitrary concentration can be efficiently produced.
- the equilibrium reaction between the organic acid polymer and hydrogen peroxide does not proceed rapidly, and an arbitrary concentration of It may be difficult to efficiently produce a composition containing an organic acid polymer.
- an organic peracid polymer-containing composition containing an organic peracid polymer in a high concentration can be obtained by the above production method.
- This organic peracid polymer-containing composition is an aqueous solution and contains at least an organic peracid polymer, hydrogen peroxide and an inorganic acid.
- the concentration of the organic peracid polymer in the composition is 2 to 50% by weight, preferably 2 to 15% by weight, and the concentration of hydrogen peroxide is 2 to 50% by weight, preferably 5 to 30% by weight,
- the concentration of the inorganic acid is 0.1 to 10% by weight, preferably 0.3 to 5% by weight.
- the concentration of the organic peracid polymer is too low, the effects of sterilization / bleaching / washing as an organic peracid are not sufficiently exhibited, and if the concentration is too high, it is difficult to produce. If the concentration of hydrogen peroxide is too low, a sufficient sterilization 'bleaching' cleaning effect cannot be obtained, and if it is too high, the effect will not increase. If the concentration of the inorganic acid is too low, sufficient sterilization / bleaching / cleaning effect cannot be obtained, and if the concentration is too high, the effect is not high.
- the organic peracid polymer-containing composition may contain other optional components including a stabilizer.
- the organic peracid polymer-containing composition of the present invention comprises a composition containing the organic peracid polymer, hydrogen peroxide and inorganic acid at the above concentrations, and further diluted to contain these components at any concentration.
- the organic peracid polymer-containing diluted composition can be appropriately prepared.
- the diluent examples include water and an aqueous alcohol solution.
- the dilution ratio is not particularly limited, and is preferably S S, preferably ⁇ or 1.1 to: LOOOO times, more preferably or 1.1 to LOOO times.
- the sterilizing / bleaching / washing composition or organic peracid polymer-containing composition of the present invention can be used for sterilization, bleaching, and washing without being diluted or diluted 1 to 10,000 times.
- the sterilizing / bleaching / washing composition or organic peracid polymer-containing composition of the present invention can be used for sterilization, bleaching, and washing without being diluted or diluted 1 to 10,000 times.
- Medical equipment beverage food containers, industrial wastewater, cooling water for air conditioning equipment, clothing, cooking utensils, dishes, bathrooms, kitchens, washing tubs, bath tubs, furniture, pet sterilization, bleaching, washing, etc. it can.
- P is the concentration of the organic peracid polymer (% by weight)
- M is the peroxycarbon box obtained by the above titration.
- W is (molecular weight per carboxyl group of polymer + 1
- % means “% by weight”.
- the raw materials used are as follows.
- the diluent is water.
- Example 7 The composition after 7 days was diluted, and 0.01 ⁇ : LN—NaOH was used to adjust the pH to 7.
- the "effective oxygen concentration” means the concentration of oxygen that is theoretically released when the peroxyhydrogen or organic peracid polymer is decomposed to become water or organic acid polymer with respect to the entire composition. This means the total of the component derived from hydrogen peroxide and the component derived from the organic peroxide polymer.
- the content derived from hydrogen peroxide is calculated as hydrogen peroxide concentration X 16Z34
- the content derived from organic peracid polymer is calculated as organic peracid polymer concentration X 16 / (molecular weight per carboxyl group of organic acid polymer + 16).
- Example 7 In the composition 7 days after the preparation of Example 7, the effective oxygen concentration derived from hydrogen peroxide was 11.1% at 23.5 X 16Z34, and the effective oxygen concentration derived from the organic peracid polymer was 7.2 X 16Z ( 72 + 16) is 1.3%, and the total effective oxygen concentration is 12.4%.
- R 0 is the reflectance of a clean white cloth
- R 1 is the reflectance of the contaminated fabric before bleaching
- Example 7 Seven days after the effective oxygen concentration of the composition diluted 9.9 times 1.8% organic peracid polymer-containing solution, and 17.7 times the effective oxygen concentration of 0.7% The following bactericidal tests were carried out using the organic peroxide polymer-containing solutions as test solutions. The results are shown in Table 6.
- SCDLP medium Soybean 'casein' digest 'broth medium with lecithin' polysorbate 80 '; manufactured by Nippon Pharmaceutical
- GPLP medium glucose' peptone with lecithin polysorbate 80
- Example 13 10. The same bactericidal test as in Example 13 was performed using 5% hydrogen peroxide solution (effective oxygen concentration: 4.9%) and 2.1% hydrogen peroxide solution (effective oxygen concentration: 1.0%). . The results are shown in Table 6.
- composition containing the organic peracid polymer of the present invention exhibits a much superior bleaching ability and sterilizing ability as compared with the case where hydrogen peroxide containing the same effective oxygen concentration is used.
- composition of the present invention contains a sufficient amount of an organic peracid polymer compared to a mixture of an organic acid polymer and hydrogen peroxide, and thus has excellent sterilization, bleaching, and cleaning capabilities. It has sufficient strength and stability, and has sufficient water solubility with little odor. Therefore, it is highly practical and industrial Not only can it be used comfortably for general households.
- the composition of the present invention can be used for sterilization, bleaching, and washing without diluting or diluting 1 to 1 to L0000 times.
- it can be used for medical equipment, beverage food containers, industrial wastewater, cooling water for air conditioning equipment, clothing, cooking utensils, tableware, bathroom, kitchen, washing tub, bath tub, furniture, pet sterilization, bleaching, washing, etc. it can.
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Abstract
Description
Claims
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US11/989,429 US8110603B2 (en) | 2005-07-27 | 2006-07-18 | Organic peracid polymer composition and process for producing the same |
JP2006524137A JP5369376B2 (ja) | 2005-07-27 | 2006-07-18 | 有機過酸ポリマー組成物およびその製造方法 |
CN2006800304072A CN101243133B (zh) | 2005-07-27 | 2006-07-18 | 有机过酸聚合物组合物及其制造方法 |
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EP3138401B1 (de) * | 2015-09-04 | 2019-01-02 | WCP Weidner Chemie-Produktions-GmbH | Zusammensetzung zur desinfektion |
US10285401B2 (en) | 2015-09-10 | 2019-05-14 | Ecolab Usa Inc. | Self indicating antimicrobial chemistry |
BR112018069405B1 (pt) * | 2016-03-22 | 2022-08-16 | Stepan Company | Composição compreendendo peroxiácidos não-alfa substituídos |
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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 |
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 |
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 |
US11206826B2 (en) | 2013-03-05 | 2021-12-28 | Ecolab Usa Inc. | Defoamer useful in a peracid composition with anionic surfactants |
Also Published As
Publication number | Publication date |
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US20100143491A1 (en) | 2010-06-10 |
CN101243133A (zh) | 2008-08-13 |
KR20080039385A (ko) | 2008-05-07 |
TWI396735B (zh) | 2013-05-21 |
CN101243133B (zh) | 2011-08-31 |
JPWO2007013324A1 (ja) | 2009-02-05 |
TW200712200A (en) | 2007-04-01 |
US8110603B2 (en) | 2012-02-07 |
KR101290547B1 (ko) | 2013-07-31 |
JP5369376B2 (ja) | 2013-12-18 |
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