US3272750A - Process and composition containing an oxygen releasing compound and an organic carbonate - Google Patents

Process and composition containing an oxygen releasing compound and an organic carbonate Download PDF

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Publication number
US3272750A
US3272750A US277721A US27772163A US3272750A US 3272750 A US3272750 A US 3272750A US 277721 A US277721 A US 277721A US 27772163 A US27772163 A US 27772163A US 3272750 A US3272750 A US 3272750A
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United States
Prior art keywords
ester
carbonate
per
sodium
carboxyphenyl
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Expired - Lifetime
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US277721A
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English (en)
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Chase Basil Hugh
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Lever Brothers Co
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Lever Brothers Co
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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
    • C11D3/3907—Organic compounds
    • C11D3/391—Oxygen-containing 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3915—Sulfur-containing compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Definitions

  • This invention relates to processes of bleaching and to bleaching compositions; in particular it relates to processes and to compositions suitable for removing stains from textile materials.
  • compositions contain an inorganic persalt such as sodium perborate or percarbonate to provide bleaching properties.
  • per-salts provide a satisfactory bleach when the detergent is used at the boil, but at lower temperatures their action is rather slow. This disadvantage is becoming important with the growing use of washing machines Which operate at a temperatom of, for example, 50-60 C. It is an object of the present invention to provide a more effective bleach in the normal washing period at this temperature than is obtained with the per-salt alone.
  • Processes and compositions according to the invention also find application in the textile industry and in commercial laundering.
  • Esters which may be used in bleaching compositions and processes of the invention are those which give a titre of 1.0 millilitres or more in this test after one minute or after five minutes, or both.
  • a bleaching process in which is used an aqueous solution of hydrogen peroxide and an ester of carbonic acid or pyrocarbonic acid which gives a titre of not less than 1.0 millilitres of 0.1 N sodium thiosulphate in the test defined above.
  • the present invention further provides a bleaching composition which contains an inorganic per-salt together with an ester of carbonic acid or pyrocarbonic acid which gives a titre of not less than 1.0 ml. of 0.1 N sodium thiosulphate in the test defined above.
  • Esters which give a titre of not less than 1.0 ml. of 0.1 N sodium th'iosulphate in the test defined above and hence may be used according to the invention include compounds Within the class R O.CO.OR in which R exerts an electron attracting effect and R is an alkyl, aryl, or alicyclic radical or a substituted alkyl, aryl or alicyclic radical.
  • esters should not yield easily oxidisable hydrolysis products such as polyhydric phenols.
  • esters within the scope of the invention that is those which give a titre of at least 1.0 ml. of 0.1 N sodium thiosulphate in the test defined above, are:
  • inorganic per-salt is meant a salt which will give rise to hydrogen peroxide in aqueous solution.
  • Suitable compounds are alkali metal perborates, percarbonates, perpyrophosphates and persilicates. These are believed not to be true per-salts in the strict chemical sense but to contain hydrogen peroxide of crystallisation, which is liberated in aqueous solution.
  • the invention can be applied to bleaching baths such as are used for treating textiles, to wash liquors, such are used in commercial laundering and to solid bleaching compositions.
  • Solid bleaching compositions may contain, in addition to a per-salt and an ester according to the invention, inert salts, alkaline agents and a small proportion of detergent.
  • the invention may further be applied to detergent compositions, which contain an organic detergent, which may be soap or an organic soapless detergent. Suitable organic soap'less detergents are the alkylaryl sulphonates, alkyl sulphates and the salts of esters or ethers of isethionic acid.
  • compositions according to the invention should preferably contain one or more alkaline substances in amounts such that similar compositions not containing esters would give a pH value within the range 9-11 when dissolved at the desired bleaching concentration.
  • Most common detergent compositions contain alkaline material sufiicient for this purpose. Suitable alkaline materials are, for instance, soap, alkali-metal carbonates, phosphates (including orthophosphates and water-soluble condensed phosphates, such as tripolyphospirates and pyrophosphates) and silicates.
  • alkali sufficient to give an initial pH of 9-11 is preferably present in the bleaching or Wash liquor before addition of the ester.
  • compositions according to the invention may contain any of the conventional adjuncts present in detergent compositions. There may be mentioned, supplementary builders, inert and organic materials such as alkali metal sulphates, chlorides, carboxyrnethylcellulose and fluorescent agents.
  • compositions according to the invention must not contain water in an amount sufiicient to permit appreciable chemical reaction between the components prior to use.
  • per-salt and ester which may be present in compositions according to the invention will depend on the time and temperature of bleaching, the degree of bleaching required, the concentration of the bleaching solution and the individual ester and per-salt used. Under most conditions, these proportions should be such as to give a per-salt concentration in solution equivalent to 0.001 to 0.1% available oxygen.
  • compositions according to the invention containing widely varying ratios of per-salt to ester. It is convenient to measure the activity of the per-salt in terms of available oxygen. Generally ratios of from A to 2 and particularly from /2 to 1 /2. molecules of ester per 1 atom of available oxygen are preferred. (In converting such ratios to ratios by weight, account must be taken of the molecular weight of the ester and the avialable oxygen content of the per-salt used.) In particular, it is preferred to use approximately chemically equivalent amounts of ester and per-salt.
  • the preferred weight ratio is from 2 to 15 parts of ester to 1 part of hydrogen peroxide (100%) depending on the molecular Weight of the ester used.
  • compositions according to the invention are to be used primarily as a bleach, for instance, for addition to alkaline textile bleaching baths or wash liquors, such compositions may contain any proportion of ester and per-salt, these components being preferably present in the ratio of M1. to 2 molecules of ester per 1 atom of available oxygen, preferably /2 to 1 /2 molecules per 1 atom of available oxygen.
  • compositions of the invention When an organic detergent is present in compositions of the invention, improvements in bleaching can be obtained at normal washing concentrations. Thus, for example, using a detergent composition of the invention at a concentration of 1% in aqueous solution improvements may be obtained if amounts of as little as 1% of persalt and 2% of ester by weight of the composition are present. In such compositions, the amount of per-salt taken should provide at least 0.1% available oxygen based on the composition.
  • detergent compositions will contain from about to about 50% by Weight of organic detergent.
  • the mixed ester/per-salt content may be as high as 70% by weight provided that these components are taken in ratios of A to 2, preferably /2 to 1 /2 molecules of ester per 1 atom of available oxygen.
  • Etfective proportions of ester and per-salt in detergent compositions will lie in general within the range of 2% to 30% of ester and 1% to 75% of per-salt by weight of the composition.
  • Example Bleaching solutions were prepared containing:
  • a length of cotton cloth was stained by immersion in boiling tea extract for one hour. It was then thoroughly rinsed, dried and cut into pieces whose percent refiectances were measured in a Hunter reflectometer using the blue filter. The percent reflectance of the test pieces was measured again after bleaching. The bleach obtained 'was expressed as the difference in the two percent readings on each test-piece.
  • esters other than p-carboxyphenyl phenyl carbonate and diethyl pyrocarbonate can be prepared by reacting an alkyl chloroformate and a pehnol.
  • a process for bleaching textile materials comprising the step of placing the article to be bleached in an aqueous solution of hydrogen peroxide and an ester selected from the class consisting of (a) esters of carbonic acid having the formula R O-COOR wherein each of R and R is an organic radical, R exerting an electron attracting effect, and (b) diethyl pyrocarbonate, said esters having a titer in the per-acid formation test of not less than 1.0 ml. of 0.1 N Na S O the hydrogen peroxide and ester being present in amounts suflicient to provide from about A to about 2 molecules of ester per atom of available oxygen.
  • an ester selected from the class consisting of (a) esters of carbonic acid having the formula R O-COOR wherein each of R and R is an organic radical, R exerting an electron attracting effect, and (b) diethyl pyrocarbonate, said esters having a titer in the per-acid formation test of not less than 1.0
  • a process for bleaching soiled textile material comprising the steps of placing the article to be bleached in an aqueous solution of hydrogen peroxide and an ester selected from the class consisting of (a) esters of carbonic acid having the formula R OCOOR wherein each of R and R is an organic radical, R exerting an electron attracting effect, and (b) diethyl pyrocarbonate, said esters having a titer in the per-acid formation test of not less than 1.0 ml.
  • a composition for use in bleaching textile material consisting essentially of an inorganic per-salt selected from the group consisting of the alkali metal perborates, percarbonates, perpyrophosphates, and persilicates, and an ester selected from the class consisting of (a) esters of carbonic acid having the formula R -O-COOR wherein each of R and R is an organic radical, R exerting an electron-attracting effect, and (b) diethyl pyrocarbonate, said esters having a titer in the per-acid formation test of not less than 1.0 ml. of 0.1 N Na S O the hydrogen peroxide and ester being present in amounts sufiicient to provide from about A to about 2 molecules of ester per atom of available oxygen.
  • composition according to claim which exhibits a pH between about 9 and about 11 when placed in an aqueous solution.
  • a composition for bleaching textile material which is an aqueous solution of hydrogen peroxide and an ester selected from the group consisting of (a) esters of carbonic acid having the formula R O-CO-O-R wherein each of R and R is an organic radical, R exerting an electron-attracting effect, and (b) diethyl pyrocarbonate, said esters having a titer in the per-acid formation test of not less than 1.0 ml. of 0.1 N Na S O the hydrogen peroxide and ester being present in amounts sufficient to provide from about A to about 2 molecules of ester per atom of available oxygen.
  • a process for bleaching textile materials comprising the steps of placing the article to be bleached in an aqueous solution of hydrogen peroxide and an ester selected from the class consisting of sodium p-sulfophenyl ethel carbonate, sodium p-sulfophenyl methyl carbonate, sodium p-sulfophenyl phenyl carbonate, diethyl pyrocarbonate, p-carboxyphenyl ethyl carbonate, p-carboxyphenyl methyl carbonate, p-carboxyphenyl phenyl carbonate, o-carboxyphenyl ethyl carbonate, o-carboxyphenyl methyl carbonate, p-carboxyphenyl n-propyl carbonate, p-carboxyphenyl n-butyl carbonate, benzyl pcarboxyphenyl carbonate, sodium p-sulfophenyl n-propyl carbonate,
  • a process according to claim 8 including the additional steps of allowing said article to remain in said solution at a temperature substantially below the boiling point thereof for a normal washing period, and thereafter rinsing said article.
  • a composition for use in bleaching textile materials consisting essentially of an inorganic per-salt selected from the group consisting of the alkali metal perborates, percarbonates, perpyrophosphates, and persilicates, and an ester selected from the class consisting of sodium p-sulfophenyl ethyl carbonate, sodium p-sulfophenyl methyl carbonate, sodium p-sulfophenyl phenyl carbonate, diethyl pyrocarbonate, p-carboxyphenyl ethyl carbonate, p-carboxyphenyl methyl carbonate, p-carboxyphenyl phenyl carbonate, o-carboxyphenyl ethyl carbonate, o-carboxyphenyl methyl carbonate, p-carboxyphenyl n-propyl carbonate, p-carboxyphenyl n-butyl carbonate, benzyl p-carboxy
  • a composition for bleaching textile materials which is an aqueous solution of hydrogen peroxide and an ester selected from the group consisting of sodium p-sulfophenyl ethyl carbonate, sodium p-sulfophenyl methyl carbonate, sodium p-sulfophenyl phenyl carbonate, diethyl pyrocarbonate, p-carboxyphenyl ethyl carbonate, pcarboxyphenyl methyl carbonate, p-carboxyphenyl phenyl carbonate, o-carboxyphenyl ethyl carbonate, o-carboxyphenyl methyl carbonate, p-carboxyphenyl n-propyl carbonate, p-carboxyphenyl n-butyl carbonate, benzyl p-carboxyphenyl carbonate, sodium p-sulfophenyl n-propyl carbonate, sodium p-sulfophenyl

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
US277721A 1962-05-07 1963-05-03 Process and composition containing an oxygen releasing compound and an organic carbonate Expired - Lifetime US3272750A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17379/62A GB970950A (en) 1962-05-07 1962-05-07 Bleaching and detergent compositions

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AT (1) AT250889B (en))
BE (1) BE631982A (en))
CH (2) CH414525A (en))
DE (1) DE1444024A1 (en))
DK (1) DK116791B (en))
ES (1) ES287714A1 (en))
FI (1) FI42851B (en))
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Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3349035A (en) * 1964-05-12 1967-10-24 Degussa Activated bleaching composition
WO1982002896A1 (en) * 1981-02-25 1982-09-02 Gen Electric Composition,compound and process
US4681592A (en) * 1984-06-21 1987-07-21 The Procter & Gamble Company Peracid and bleach activator compounds and use thereof in cleaning compositions
US4686061A (en) * 1985-07-03 1987-08-11 Akzo Nv P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds
US4751015A (en) * 1987-03-17 1988-06-14 Lever Brothers Company Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions
US4818426A (en) * 1987-03-17 1989-04-04 Lever Brothers Company Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions
JPH024765A (ja) * 1988-03-17 1990-01-09 Unilever Nv 漂白剤の前駆物質並びにその漂白剤及び／又は洗剤組成物への使用
US4904406A (en) * 1988-03-01 1990-02-27 Lever Brothers Company Quaternary ammonium compounds for use in bleaching systems
US4933103A (en) * 1987-03-23 1990-06-12 Kao Corporation Bleaching composition
US5043089A (en) * 1985-05-07 1991-08-27 Akzo N.V. P-sulphophenyl alkyl carbonates and detergent compositions and detergent additives containing these compounds
US5055217A (en) * 1990-11-20 1991-10-08 Lever Brothers Company, Division Of Conopco, Inc. Polymer protected bleach precursors
US5124480A (en) * 1989-10-10 1992-06-23 Monsanto Company Peroxygen bleach activators and bleaching compositions
US5130045A (en) * 1987-10-30 1992-07-14 The Clorox Company Delayed onset active oxygen bleach composition
US5143641A (en) * 1990-09-14 1992-09-01 Lever Brothers Company, Division Of Conopco, Inc. Ester perhydrolysis by preconcentration of ingredients
US5183584A (en) * 1989-10-10 1993-02-02 Monsanto Company Peroxygen bleach activators and bleaching compositions
US5183918A (en) * 1989-08-25 1993-02-02 Monsanto Company Process for the production of carbonate esters
US5234616A (en) * 1987-10-30 1993-08-10 The Clorox Company Method of laundering clothes using a delayed onset active oxygen bleach composition
US5252770A (en) * 1989-06-05 1993-10-12 Monsanto Company Process for the production of carbonate esters
EP0427224B1 (en) * 1989-11-08 1995-02-01 Kao Corporation Novel polycationic compound and bleach composition containing the same
US5705091A (en) * 1995-09-11 1998-01-06 The Clorox Company Alkoxylated peracid activators
GB2395488A (en) * 2002-11-22 2004-05-26 Reckitt Benckiser Nv Stain removal
US8729296B2 (en) 2010-12-29 2014-05-20 Ecolab Usa Inc. Generation of peroxycarboxylic acids at alkaline pH, and their use as textile bleaching and antimicrobial agents
US8846107B2 (en) 2010-12-29 2014-09-30 Ecolab Usa Inc. In situ generation of peroxycarboxylic acids at alkaline pH, and methods of use thereof
US8889900B2 (en) 2010-12-29 2014-11-18 Ecolab Usa Inc. Sugar ester peracid on site generator and formulator
US9321664B2 (en) 2011-12-20 2016-04-26 Ecolab Usa Inc. Stable percarboxylic acid compositions and uses thereof
US9518013B2 (en) 2014-12-18 2016-12-13 Ecolab Usa Inc. Generation of peroxyformic acid through polyhydric alcohol formate
US9845290B2 (en) 2014-12-18 2017-12-19 Ecolab Usa Inc. Methods for forming peroxyformic acid and uses thereof
US9926214B2 (en) 2012-03-30 2018-03-27 Ecolab Usa Inc. Use of peracetic acid/hydrogen peroxide and peroxide-reducing agents for treatment of drilling fluids, frac fluids, flowback water and disposal water
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
US11040902B2 (en) 2014-12-18 2021-06-22 Ecolab Usa Inc. Use of percarboxylic acids for scale prevention in treatment systems
US11260040B2 (en) 2018-06-15 2022-03-01 Ecolab Usa Inc. On site generated performic acid compositions for teat treatment
US12058999B2 (en) 2018-08-22 2024-08-13 Ecolab Usa Inc. Hydrogen peroxide and peracid stabilization with molecules based on a pyridine carboxylic acid
US12096768B2 (en) 2019-08-07 2024-09-24 Ecolab Usa Inc. Polymeric and solid-supported chelators for stabilization of peracid-containing compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2911208A1 (de) * 1979-03-22 1980-10-02 Bayer Ag Mikrobizides mittel und seine verwendung
GB8619152D0 (en) * 1986-08-06 1986-09-17 Unilever Plc Conditioning fabrics
GB8619153D0 (en) * 1986-08-06 1986-09-17 Unilever Plc Fabric conditioning composition

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2770639A (en) * 1955-01-17 1956-11-13 Monsanto Chemicals Method of producing aliphatic and alicyclic carbonates
US2837555A (en) * 1956-09-20 1958-06-03 Dow Chemical Co Preparation of carbonate esters
US2843567A (en) * 1954-12-20 1958-07-15 Eastman Kodak Co Alkaline earth metal titanium alkoxide catalysts for preparing aromatic polycarbonates
US2916345A (en) * 1959-12-08 Process for dyeing articles of polyeth-
GB836988A (en) * 1955-07-27 1960-06-09 Unilever Ltd Improvements in or relating to bleaching and detergent compositions
US3017424A (en) * 1957-04-08 1962-01-16 Bayer Ag Process for the production of diarylcarbonates
US3078294A (en) * 1961-03-17 1963-02-19 Dow Chemical Co Process for making pyrocarbonate esters

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2916345A (en) * 1959-12-08 Process for dyeing articles of polyeth-
US2843567A (en) * 1954-12-20 1958-07-15 Eastman Kodak Co Alkaline earth metal titanium alkoxide catalysts for preparing aromatic polycarbonates
US2770639A (en) * 1955-01-17 1956-11-13 Monsanto Chemicals Method of producing aliphatic and alicyclic carbonates
GB836988A (en) * 1955-07-27 1960-06-09 Unilever Ltd Improvements in or relating to bleaching and detergent compositions
US2837555A (en) * 1956-09-20 1958-06-03 Dow Chemical Co Preparation of carbonate esters
US3017424A (en) * 1957-04-08 1962-01-16 Bayer Ag Process for the production of diarylcarbonates
US3078294A (en) * 1961-03-17 1963-02-19 Dow Chemical Co Process for making pyrocarbonate esters

Cited By (76)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3349035A (en) * 1964-05-12 1967-10-24 Degussa Activated bleaching composition
WO1982002896A1 (en) * 1981-02-25 1982-09-02 Gen Electric Composition,compound and process
JPS58500368A (ja) * 1981-02-25 1983-03-10 ゼネラル・エレクトリック・カンパニイ 組成物、化合物および製法
US4535108A (en) * 1981-02-25 1985-08-13 General Electric Company Flame retardant polycarbonate
US4681592A (en) * 1984-06-21 1987-07-21 The Procter & Gamble Company Peracid and bleach activator compounds and use thereof in cleaning compositions
EP0484324A3 (en) * 1984-06-21 1992-08-26 The Procter & Gamble Company Cleaning compositions containing bleach activator compounds
US5043089A (en) * 1985-05-07 1991-08-27 Akzo N.V. P-sulphophenyl alkyl carbonates and detergent compositions and detergent additives containing these compounds
US4686061A (en) * 1985-07-03 1987-08-11 Akzo Nv P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds
US4751015A (en) * 1987-03-17 1988-06-14 Lever Brothers Company Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions
US4818426A (en) * 1987-03-17 1989-04-04 Lever Brothers Company Quaternary ammonium or phosphonium substituted peroxy carbonic acid precursors and their use in detergent bleach compositions
US4933103A (en) * 1987-03-23 1990-06-12 Kao Corporation Bleaching composition
US5130045A (en) * 1987-10-30 1992-07-14 The Clorox Company Delayed onset active oxygen bleach composition
US5234616A (en) * 1987-10-30 1993-08-10 The Clorox Company Method of laundering clothes using a delayed onset active oxygen bleach composition
US4904406A (en) * 1988-03-01 1990-02-27 Lever Brothers Company Quaternary ammonium compounds for use in bleaching systems
JPH024765A (ja) * 1988-03-17 1990-01-09 Unilever Nv 漂白剤の前駆物質並びにその漂白剤及び／又は洗剤組成物への使用
US5252770A (en) * 1989-06-05 1993-10-12 Monsanto Company Process for the production of carbonate esters
US5183918A (en) * 1989-08-25 1993-02-02 Monsanto Company Process for the production of carbonate esters
US5183584A (en) * 1989-10-10 1993-02-02 Monsanto Company Peroxygen bleach activators and bleaching compositions
US5124480A (en) * 1989-10-10 1992-06-23 Monsanto Company Peroxygen bleach activators and bleaching compositions
EP0427224B1 (en) * 1989-11-08 1995-02-01 Kao Corporation Novel polycationic compound and bleach composition containing the same
US5143641A (en) * 1990-09-14 1992-09-01 Lever Brothers Company, Division Of Conopco, Inc. Ester perhydrolysis by preconcentration of ingredients
US5055217A (en) * 1990-11-20 1991-10-08 Lever Brothers Company, Division Of Conopco, Inc. Polymer protected bleach precursors
US5705091A (en) * 1995-09-11 1998-01-06 The Clorox Company Alkoxylated peracid activators
GB2395488A (en) * 2002-11-22 2004-05-26 Reckitt Benckiser Nv Stain removal
US20060042662A1 (en) * 2002-11-22 2006-03-02 Laurence Geret Process of removing stains
US7255112B2 (en) 2002-11-22 2007-08-14 Reckitt Benckiser N.V. Process of removing stains
US9861101B2 (en) 2010-12-29 2018-01-09 Ecolab Usa Inc. Continuous on-line adjustable disinfectant/sanitizer/bleach generator
US10010075B2 (en) 2010-12-29 2018-07-03 Ecolab Usa Inc. Water temperature as a means of controlling kinetics of onsite generated peracids
US8858895B2 (en) 2010-12-29 2014-10-14 Ecolab Usa Inc. Continuous on-line adjustable disinfectant/sanitizer/bleach generator
US8877254B2 (en) 2010-12-29 2014-11-04 Ecolab Usa Inc. In situ generation of peroxycarboxylic acids at alkaline pH, and methods of use thereof
US8889900B2 (en) 2010-12-29 2014-11-18 Ecolab Usa Inc. Sugar ester peracid on site generator and formulator
US8933263B2 (en) 2010-12-29 2015-01-13 Ecolab Usa Inc. Water temperature as a means of controlling kinetics of onsite generated peracids
US9192909B2 (en) 2010-12-29 2015-11-24 Ecolab USA, Inc. Sugar ester peracid on site generator and formulator
US11311011B2 (en) 2010-12-29 2022-04-26 Ecolab Usa Inc. Continuous on-line adjustable disinfectant/sanitizer/bleach generator
US9365509B2 (en) 2010-12-29 2016-06-14 Ecolab Usa Inc. Continuous on-line adjustable disinfectant/sanitizer/bleach generator
US9505715B2 (en) 2010-12-29 2016-11-29 Ecolab Usa Inc. Sugar ester peracid on site generator and formulator
US12274263B2 (en) 2010-12-29 2025-04-15 Ecolab Usa Inc. Continuous on-line adjustable disinfectant/sanitizer/bleach generator
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US10433547B2 (en) 2014-12-18 2019-10-08 Ecolab Usa Inc. Generation of peroxyformic acid through polyhydric alcohol formate
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US11772998B2 (en) 2014-12-18 2023-10-03 Ecolab Usa Inc. Use of percarboxylic acids for scale prevention in treatment systems
US9845290B2 (en) 2014-12-18 2017-12-19 Ecolab Usa Inc. Methods for forming peroxyformic acid and uses thereof
US10233149B2 (en) 2014-12-18 2019-03-19 Ecolab Usa Inc. Methods for forming peroxyformic acid and uses thereof
US11771673B2 (en) 2018-06-15 2023-10-03 Ecolab Usa Inc. On site generated performic acid compositions for teat treatment
US11260040B2 (en) 2018-06-15 2022-03-01 Ecolab Usa Inc. On site generated performic acid compositions for teat treatment
US12058999B2 (en) 2018-08-22 2024-08-13 Ecolab Usa Inc. Hydrogen peroxide and peracid stabilization with molecules based on a pyridine carboxylic acid
US12096768B2 (en) 2019-08-07 2024-09-24 Ecolab Usa Inc. Polymeric and solid-supported chelators for stabilization of peracid-containing compositions

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FI42851B (en)) 1970-08-03
GB970950A (en) 1964-09-23
DE1444024A1 (de) 1969-12-11
CH573663A4 (en)) 1965-12-15
NL292430A (en))
ES287714A1 (es) 1963-07-16
CH414525A (de) 1966-12-30
CH405573A (de) 1966-01-15
DK116791B (da) 1970-02-16
AT250889B (de) 1966-12-12
BE631982A (en))

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