US3882035A - Iminodiacetonitrile derivatives as peroxygen bleach activators - Google Patents

Iminodiacetonitrile derivatives as peroxygen bleach activators Download PDF

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Publication number
US3882035A
US3882035A US343314A US34331473A US3882035A US 3882035 A US3882035 A US 3882035A US 343314 A US343314 A US 343314A US 34331473 A US34331473 A US 34331473A US 3882035 A US3882035 A US 3882035A
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United States
Prior art keywords
iminodiacetonitrile
compound
composition according
formula
bleaching
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Expired - Lifetime
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US343314A
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English (en)
Inventor
Frank Fred Loffelman
Thomas Eugene Brady
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LEAD'S METAL PRODUCTS Inc
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US343314A priority Critical patent/US3882035A/en
Priority to AR252458A priority patent/AR206602A1/es
Priority to CA191,756A priority patent/CA1021109A/en
Priority to GB599174A priority patent/GB1417356A/en
Priority to PH15510A priority patent/PH11578A/en
Priority to DE19742407906 priority patent/DE2407906A1/de
Priority to DD176842A priority patent/DD111425A5/xx
Priority to IT49064/74A priority patent/IT1008372B/it
Priority to NL7403306A priority patent/NL7403306A/xx
Priority to JP49030659A priority patent/JPS49127882A/ja
Priority to FR7409571A priority patent/FR2222427B1/fr
Priority to BE142217A priority patent/BE812563A/xx
Priority to BR2203/74A priority patent/BR7402203D0/pt
Application granted granted Critical
Publication of US3882035A publication Critical patent/US3882035A/en
Assigned to LEAD'S METAL PRODUCTS, INC. reassignment LEAD'S METAL PRODUCTS, INC. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KOPERNAK, RUDY
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/3925—Nitriles; Isocyanates or quarternary ammonium nitriles
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/72—Treatment of water, waste water, or sewage by oxidation
    • C02F1/722—Oxidation by peroxides
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/30—Nature of the water, waste water, sewage or sludge to be treated from the textile industry
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/42—Nature of the water, waste water, sewage or sludge to be treated from bathing facilities, e.g. swimming pools

Definitions

  • AN(CH CN) wherein A represents an acyl group selected from aroyl, substituted aroyl, lower alkanoyl and the residue of a heterocyclic acid chloride, or a 4,6-substituted-striazinyl group in which the 4 and 6 positions can contain an N(CH CN) group, are bleach activators of high strength and good storage stability in peroxygen bleaching compositions.
  • This invention relates to bleaching compositions, and more particularly to improved bleaching compositions containing hydrogen peroxide releasing compounds and activators for such compounds as defined below, and to compositions of the activators and hydrogen peroxide releasing compounds with detergents.
  • the invention provides improved bleaching compositions comprising hydrogen peroxide or a hydrogen peroxide releasing compound and an effective amount of an. activator.
  • the activators are derivatives of iminodiacetonitrile represented by Formula l:
  • A is an acyl group selected from aroyl, substituted aroyl, lower (C -C alkanoyl and the residue of a heterocyclic carboxylic acid chloride; or a 4,6-disubstituted-s-triazinyl group in which the substituent groups are selected from amino, diethylamino and N(CH CN) groups,
  • U.S. Pat. No. 2,927,840 discloses bleaching compositions comprising a peroxygen compound and an organic nitrile, including iminodiacetonitrile.
  • the use of various N-acyl compounds as bleach activators has previously been disclosed.
  • French Pat. No. 1,583,330 discloses the use of N-acyl derivatives of heterocycles such as imidazole, pyrazole and triazole
  • British Pat. No. 1,046,251 discloses the use of N-acyl derivatives of pyridazine, triazole and pyrazole as peroxygen salt activators in bleaching compositions for textile materials.
  • 1,489,926 discloses the use of the acyl-containing non-heterocycles N- acetyl-N-methyl-p-toluenesulfonamide and N- propionyl-N-methyl-p-toluenesulfonamide.
  • a perborate bleaching composition containing an activator such as any of these can be shown to remove a greater percentage of tea stain from a textile material than the same bleaching composition in which activator is omitted.
  • peroxygen bleaching compositions containing such activators have not proved satisfactory for one or more reasons, such as inadequate bleaching or instability at 50 to 70C., the typical working temperature range of modern laundry washing machines; or because of unsatisfactory compatibility with detergents or other materials with which associated; or because of objectionable odor; or because the activators tend to deteriorate during storage of the bleaching composition under a variety of conditions of tempera ture and humidity.
  • a bleach activator must, in particular, maintain its high activity in a formulation over a long period of time as such or in the presence of a peroxide releasing agent or in the presence of a detergent composition.
  • Commercial products are often subject to storage for considerable periods of time in hot, humid warehouses or on the supermarket shelf before consumer use, and to be satisfactory the activity must be maintained without appreciable loss during such periods.
  • a preferred species of activator within the definition of Formula I is benzoyliminodiacetonitrile (Formula ll):
  • a perborate bleaching composition containing (ll) as the activator removes more than twice as much tea stain from the textile as the same bleaching composition without the activatorv Furthermore, (II) has excellent storage stability as illustrated herein.
  • compositions of the invention are the provision of dry oxygen bleaching compositions which not only exhibit good bleaching activity at relatively low-water temperatures, but also are safer and easier to handle than liquid bleach products. They are relatively safe for all fabrics as well as for dyes thereon, for human and animal hair bleaching compositions, and exhibit germicidal activity. In addition, the compositions are useful for bleaching ground wood pulp.
  • the novel bleach activators of this invention can be prepared by well known methods.
  • Ben zoyliniinodiacetonitrile for example. can be prepared by reaction of benzoyl chloride with iminodiacetoni trile according to the following equation.
  • aroyl. substituted aroyl. alkanoyl and heterocynch acyl derivatives can be prepared similarly from the appropriate carbosylic acid halides (or anhydrides in some instances).
  • Typical carboxylic acid halides lor anhydridesi that can be chosen for reaction with the iminodiacetonitrile to give the products of this invention include those such p-chlorobenzoyl chloride salicyloyl chloride o nitrobenzoyl chloride p-nitrobenzoyl chloride o-hromobenzoyl chloride terephthaloyl chloride p-fluorohenzoyl chloride m-methoxybenzoyl chloride I.4-dimethylhenzoyl bromide pltrifluoroniethyllbcnzoyl chloride o methylbenzoyl bromide p ethylhenroyl bromide l-naphthoyl chloride 3-hydrosyCataphthoyl chloride acetic anhydride propionic anhydride propionyl chloride butyryl chloride hutyric anhydride eaproie anhydride caproy'l chloride furoy
  • the preferred species of the invention are those derived from aromatic carboxvlic acid halides. cyanuric chlorides, and lower aliphatic carboxvlic acid halides.
  • the bleaching compositions of the invention contain the activating compound and the hydrogen peroxide releasing; compound in a molar ratio ranging from aiiout l:l to about l.lll. respectively, with a preferred range of about ill to 5;].
  • the actual ratio of activator to bleach can. of course. be varied widely for varying applications.
  • the oxygen bleaches useful in these bleaching com positions are hydro ien peroxide and organic peroxides and inorganic pero: salts that liberate hydrogen peroxide in Water.
  • nnples of peroxide bleaching compounds are urea peroxide.
  • bcnzoyl peroxide methyl ethyl kctonc peroxide. and the like.
  • l isamples of inorganic pero' en hie-aching compounds are alkali metal pcri'iorates. percarbonates. perphosphates per sulfates. rnoiiopcrsulfates. and the like. Mixtures oftivo or more bleaching compounds can, of course. be used if desired.
  • peroxide releasing compounds as mentioned above may be used in the compositions of the invention preferred peroxide releasing; compounds are sodium perborate l for economic conside ationsi and sodium pcrearbonate [for ecoli'igieal con sidcrationsl.
  • the activated bleach compositions of the invention are useful for bleach klflpllcliilllllfi for various substrates including fabrics. particularly when incorporated with detergent compositions for household or commercial launderin purposes
  • a most iniprotant property of such detergent compositions is the ability to remove stains inchiding food stains such as those of coffee. tea. wine and the like as well as to maintain purity of white in uncolo ed textile
  • soiling in general may be removed such as grass stains. urine and the like.
  • peroxygen releasing compound and eroxvgen bleach. activator. such detergent compositions may contain other optional additives such as germicides gieides. enzymes. optical bright eners. Colorants. perfun' 2. thickeners. emulsion or suspension stabilizers. and the like, including builders. such as sodium p'nospluitc. salts. carbonates. silicates. and the like as usually encountered in the art.
  • the detergent component of such activated bleach compositions may be any of the conventional types such kit anionic. cationic. nonionic or arnphoteric.
  • Bleaching compositions may generally be used also for their germicidal properties in various applications
  • Two of the stained cotton swatches are placed in a stainless steel Terg-O Tometer manufactured by US. Testing Company.
  • One liter of distilled water at 120F. is introduced and 40 grams of unstained cotton fabric for control of microbial growth.
  • Applications may be 5 are added so as to provide a typical household washing made to any surface or substrate where such control is hi lmh r ti f ab ut 20 to 1. Then 2,0 desired.
  • compositions also may be both sides.
  • the formulation was such as to protiveness of this composition determined by the followvide 20 grams of Tide detergent 033 gram of sodium mg test Procedure: perborate and the indicated amount (grams) of activa- Five'gfflm Swatches of deslzed, X 80 cottongfabnc tor per liter of solution.
  • the molar ratio of activator to are stained with tea in the following manner. Five tea Sodium perborate in each instance was 1.11
  • the test bags are placed in one liter of water and boiled for five procedure was the Same as described in Example 2. minutes.
  • the swatches are then immersed in the tea Suits f the testing i Examples 3-9 as we as Examp
  • wt of Activator (Grarrcl 76 Stain Removed Examples l0-l2.
  • the formulation was such as to provide 2.0 grams of Tide detergent, 0.33 gram of sodium perborate and the indicated amount (grams) of activator per liter of solution.
  • the mole ratio of activator to sodium perborate in each instance was l:l.1.
  • the test procedure was the same as described in Example 2. Results of the testing in Examples 10-12 are summarized in Table II.
  • EXAMPLE 14 Storage Stability of Benzoyliminodiacetonitrile
  • the storage stability of benzoyliminodiacetonitrile in a dry bleaching composition was determined by testing the bleaching effectiveness of such a composition after three months storage (a) at room temperature in a closed container, and (b) at 80F. and 80% relative hurnidity in an open container with the bleaching effectiveness of a freshly prepared composition.
  • the bleach composition and the test procedure were the same as that described in Example 2, except that the dry composition in each case was prepared by mixing the dry ingredients (detergent, perborate and benzoyliminodiacetonitrile) and, after storage, adding the mixture to the bleach bath water.
  • the freshly prepared composition was made as described in Example 2 (by adding the dry ingredients, separately, to the bleach bath water).
  • EXAMPLE 16 Preparation of 2,4,6-Tris( biscyanomethylamino )-s-triazine
  • EXAMPLE 1 Preparation of 2,6-Diethylamino-4-bis( cyanomethyl)amino-s-triazine 2,6-Dichlor0-4-bis( cyanomethyl )amino-s-triazine (2.0 g, 0.008 mole) was added to 10 ml diethylamine in 20 ml dimethylacetamide at steam bath temperature. After about 5-10 minutes, a solid precipitated and the reaction mixture was drowned in water. The solid was filtered and recrystallized from methanol, mp 94-96C.
  • a bleaching composition comprising hydrogen peroxide or a hydrogen peroxide releasing compound of the group of organic peroxides and inorganic peroxygen salts and an activating amount of an iminodiacetonitrile compound represented by the formula:
  • A is an acyl group selected from aroyl. substituted aroyl, lower alkanoyl and the residue of a heterocyclic carboxylic acid halide; or a 4,6-disubstituted-s triazinyl group in which the substituent groups are se lected from amino. diethylamino and bis(cyanomethyl- )amino groups.
  • a composition according to claim 1 wherein A in the iminodiacetonitrile compound represents an unsubstituted benzoyl or naphthoyl radical or a substituted benzoyl or naphthoyl radical having a substituent se lected from halo, nitro, hydroxy, carboxy, C C alkyl. C -C alkoxy and halosubstituted C C alkyl groups.
  • composition according to claim 2 wherein the iminodiacetonitrile compound has the formula:
  • composition according to claim 2 wherein the iminodiacetonitrile compound has the formula:
  • composition according to claim 2 wherein the iminodiacetonitrile compound has the formula:
  • composition according to claim 2 wherein the iminodiacetonitrile compound has the formula:
  • a composition according to claim 1 wherein A in the iminodiacetonitrile compound is the residue of a heterocyclic carboxylic acid halide selected from furoyl, thenoyl and picolinoyl groups.
  • composition according to claim 9 wherein the iminodiacetonitrile compound has the formula:
  • a composition according to claim 1 containing a detergent containing a detergent.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
US343314A 1973-03-21 1973-03-21 Iminodiacetonitrile derivatives as peroxygen bleach activators Expired - Lifetime US3882035A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US343314A US3882035A (en) 1973-03-21 1973-03-21 Iminodiacetonitrile derivatives as peroxygen bleach activators
AR252458A AR206602A1 (es) 1973-03-21 1974-01-01 Composicion de blanqueo activada con un derivado de iminodiacetonitrilo
CA191,756A CA1021109A (en) 1973-03-21 1974-02-05 Iminodiacetonitrile derivatives as peroxygen bleach activators
GB599174A GB1417356A (en) 1973-03-21 1974-02-08 Iminodiacetonitrile derivatives as peroxygen bleach activators
PH15510A PH11578A (en) 1973-03-21 1974-02-14 Iminodiacetonitrile derivatives as peroxygen bleach activators
DE19742407906 DE2407906A1 (de) 1973-03-21 1974-02-19 Iminodiacetonitril-derivate und ihre verwendung als persauerstoff-bleichaktivatoren
DD176842A DD111425A5 (enrdf_load_stackoverflow) 1973-03-21 1974-02-27
IT49064/74A IT1008372B (it) 1973-03-21 1974-03-07 Composizione candeggiante
NL7403306A NL7403306A (enrdf_load_stackoverflow) 1973-03-21 1974-03-12
JP49030659A JPS49127882A (enrdf_load_stackoverflow) 1973-03-21 1974-03-19
FR7409571A FR2222427B1 (enrdf_load_stackoverflow) 1973-03-21 1974-03-20
BE142217A BE812563A (fr) 1973-03-21 1974-03-20 Compositions de blanchiment contenant un peroxyde et un activateur du type iminodiacetonitrile
BR2203/74A BR7402203D0 (pt) 1973-03-21 1974-03-21 Composicao alvejante aperfeicoada

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US (1) US3882035A (enrdf_load_stackoverflow)
JP (1) JPS49127882A (enrdf_load_stackoverflow)
AR (1) AR206602A1 (enrdf_load_stackoverflow)
BE (1) BE812563A (enrdf_load_stackoverflow)
BR (1) BR7402203D0 (enrdf_load_stackoverflow)
CA (1) CA1021109A (enrdf_load_stackoverflow)
DD (1) DD111425A5 (enrdf_load_stackoverflow)
DE (1) DE2407906A1 (enrdf_load_stackoverflow)
FR (1) FR2222427B1 (enrdf_load_stackoverflow)
GB (1) GB1417356A (enrdf_load_stackoverflow)
IT (1) IT1008372B (enrdf_load_stackoverflow)
NL (1) NL7403306A (enrdf_load_stackoverflow)
PH (1) PH11578A (enrdf_load_stackoverflow)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986974A (en) * 1975-11-25 1976-10-19 American Cyanamid Company Aroyl-n-hydroxyformimidoyl halides as bleach activators
US3986973A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Cyanoformates and cyanoformamides as bleach activators
US3986972A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Acyl nitrile compounds as peroxygen bleach activators
US4199466A (en) * 1978-08-21 1980-04-22 Shell Oil Company Activated bleaching process and compositions therefor
US4915863A (en) * 1987-08-14 1990-04-10 Kao Corporation Bleaching composition
US5281361A (en) * 1990-05-30 1994-01-25 Lever Brothers Company, Division Of Conopco, Inc. Bleaching composition
US5741437A (en) * 1995-06-07 1998-04-21 The Clorox Company N-alkyl ammonium acetonitrile bleach activators
US5792218A (en) * 1995-06-07 1998-08-11 The Clorox Company N-alkyl ammonium acetonitrile activators in dense gas cleaning and method
US5814242A (en) * 1995-06-07 1998-09-29 The Clorox Company Mixed peroxygen activator compositions
US5888419A (en) * 1995-06-07 1999-03-30 The Clorox Company Granular N-alkyl ammonium acetontrile compositions
US5929013A (en) * 1995-03-09 1999-07-27 Johnson Company Ltd. Bleach product
US6010994A (en) * 1995-06-07 2000-01-04 The Clorox Company Liquid compositions containing N-alkyl ammonium acetonitrile salts
US6159391A (en) * 1996-08-20 2000-12-12 S. C. Johnson & Son, Inc. Bleaching agent compositions
US6183665B1 (en) 1995-06-07 2001-02-06 The Clorox Company Granular N-alkyl ammonium acetonitrile compositions
US6235218B1 (en) 1995-06-07 2001-05-22 The Clorox Company Process for preparing N-alkyl ammonium acetonitrile compounds
US6764613B2 (en) 1995-06-07 2004-07-20 Mid-America Commercialization Corporation N-alkyl ammonium acetonitrile salts, methods therefor and compositions therewith
US20070071537A1 (en) * 2005-09-29 2007-03-29 Reddy Kiran K Wiper with encapsulated agent

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS587497A (ja) * 1981-07-06 1983-01-17 ダスキンフランチヤイズ株式会社 蛋白質乃至ペプチド系の汚染用漂白剤組成物
EP0136973A1 (de) * 1983-08-09 1985-04-10 Benedikt Strausak Zusammensetzung zur Aufbereitung und Entkeimung von Gebrauchswasser und ihre Verwendung

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927840A (en) * 1955-07-08 1960-03-08 Degussa Process for the treatment of fibrous materials
US3172869A (en) * 1965-03-09 Acryloniteils resins plasticized with a cyangethylated amide

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3172869A (en) * 1965-03-09 Acryloniteils resins plasticized with a cyangethylated amide
US2927840A (en) * 1955-07-08 1960-03-08 Degussa Process for the treatment of fibrous materials

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986973A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Cyanoformates and cyanoformamides as bleach activators
US3986972A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Acyl nitrile compounds as peroxygen bleach activators
US3986974A (en) * 1975-11-25 1976-10-19 American Cyanamid Company Aroyl-n-hydroxyformimidoyl halides as bleach activators
US4199466A (en) * 1978-08-21 1980-04-22 Shell Oil Company Activated bleaching process and compositions therefor
US4915863A (en) * 1987-08-14 1990-04-10 Kao Corporation Bleaching composition
US4978770A (en) * 1987-08-14 1990-12-18 Kao Corporation Quaternary ammonium salts of dicyano substituted teriary alkylene diamines as bleach activators
US5281361A (en) * 1990-05-30 1994-01-25 Lever Brothers Company, Division Of Conopco, Inc. Bleaching composition
US5929013A (en) * 1995-03-09 1999-07-27 Johnson Company Ltd. Bleach product
US6017464A (en) * 1995-06-07 2000-01-25 The Clorox Company Dimeric N-alkyl ammonium acetonitrile bleach activators
US6046150A (en) * 1995-06-07 2000-04-04 The Clorox Company Liquid compositions containing N-alkyl ammonium acetonitrile salts
US5877315A (en) * 1995-06-07 1999-03-02 The Clorox Company Dimeric N-Alkyl ammonium acetonitrile bleach activators
US5888419A (en) * 1995-06-07 1999-03-30 The Clorox Company Granular N-alkyl ammonium acetontrile compositions
US5741437A (en) * 1995-06-07 1998-04-21 The Clorox Company N-alkyl ammonium acetonitrile bleach activators
US5959104A (en) * 1995-06-07 1999-09-28 The Clorox Company N-alkyl ammonium acetonitrile bleach activators
US5814242A (en) * 1995-06-07 1998-09-29 The Clorox Company Mixed peroxygen activator compositions
US5958289A (en) * 1995-06-07 1999-09-28 The Clorox Company N-alkyl ammonium acetonitrile bleach activators
US5792218A (en) * 1995-06-07 1998-08-11 The Clorox Company N-alkyl ammonium acetonitrile activators in dense gas cleaning and method
US6010994A (en) * 1995-06-07 2000-01-04 The Clorox Company Liquid compositions containing N-alkyl ammonium acetonitrile salts
US6764613B2 (en) 1995-06-07 2004-07-20 Mid-America Commercialization Corporation N-alkyl ammonium acetonitrile salts, methods therefor and compositions therewith
US6183665B1 (en) 1995-06-07 2001-02-06 The Clorox Company Granular N-alkyl ammonium acetonitrile compositions
US6235218B1 (en) 1995-06-07 2001-05-22 The Clorox Company Process for preparing N-alkyl ammonium acetonitrile compounds
US6159391A (en) * 1996-08-20 2000-12-12 S. C. Johnson & Son, Inc. Bleaching agent compositions
US20070071537A1 (en) * 2005-09-29 2007-03-29 Reddy Kiran K Wiper with encapsulated agent
US7614812B2 (en) 2005-09-29 2009-11-10 Kimberly-Clark Worldwide, Inc. Wiper with encapsulated agent

Also Published As

Publication number Publication date
NL7403306A (enrdf_load_stackoverflow) 1974-09-24
FR2222427B1 (enrdf_load_stackoverflow) 1977-10-07
PH11578A (en) 1978-03-31
GB1417356A (en) 1975-12-10
CA1021109A (en) 1977-11-22
AR206602A1 (es) 1976-08-06
DD111425A5 (enrdf_load_stackoverflow) 1975-02-12
IT1008372B (it) 1976-11-10
DE2407906A1 (de) 1974-09-26
BR7402203D0 (pt) 1974-11-05
JPS49127882A (enrdf_load_stackoverflow) 1974-12-06
BE812563A (fr) 1974-09-20
FR2222427A1 (enrdf_load_stackoverflow) 1974-10-18

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