WO1993020167A1 - Acidic activated bleaching compositon - Google Patents

Acidic activated bleaching compositon Download PDF

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Publication number
WO1993020167A1
WO1993020167A1 PCT/US1993/002944 US9302944W WO9320167A1 WO 1993020167 A1 WO1993020167 A1 WO 1993020167A1 US 9302944 W US9302944 W US 9302944W WO 9320167 A1 WO9320167 A1 WO 9320167A1
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WO
WIPO (PCT)
Prior art keywords
composition according
hydrogen peroxide
compositions
organic peracid
peracid precursor
Prior art date
Application number
PCT/US1993/002944
Other languages
French (fr)
Inventor
Frederick Edward Hardy
Raffaele Scoccianti
Stefano Scialla
Barbara Manfredi
Original Assignee
The Procter & Gamble Company
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 The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU39399/93A priority Critical patent/AU668936B2/en
Priority to JP5517617A priority patent/JPH07505437A/en
Priority to BR9306183A priority patent/BR9306183A/en
Publication of WO1993020167A1 publication Critical patent/WO1993020167A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3947Liquid compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3902Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905Bleach activators or bleach catalysts
    • C11D3/3907Organic compounds
    • C11D3/391Oxygen-containing compounds

Definitions

  • the present invention relates to bleaching compositions, mainly for use in laundry applications.
  • the compositions according to the present invention which comprise hydrogen peroxide as well as peracid precursors, are stable upon storage.
  • hydrogen peroxide bleach activators have been developed and have been extensively described in the art. These activators are mainly transition metals or peracid precursors. Peracid precursors react with hydrogen peroxide to yield peracids. Peracids are the "activated" bleaching compounds which are efficient at low temperatures.
  • a bleaching composition comprising hydrogen peroxide, an organic peracid precursor selected from a specific class, e.g. glycol and glycerin esters, and by formulating said composition in a narrow, acidic pH range.
  • the mildly acidic pH range allows for adequate chemical stability of both the hydrogen peroxide and the organic peracid precursor.
  • the activation of hydrogen peroxide trough the formation of a peracid is enhanced by the pH raise which occurs upon dilution in the wash water, especially when a detergent composition bringing further alkalinity is also present in the wash water.
  • Glycol esters have been often described as solvents in detergent and bleaching compositions. Such compositions are described for instance in US 3 956 159. These compositions have a pH of 6.5 and above.
  • J 62252500 discloses bleaching compositions which comprise a bleach activator, including triacetin. These compositions are formulated at neutral or weakly basic pH.
  • Bleaching compositions for various applications comprising triacetin are also disclosed in J62001792, J62001794 J 62001796, and J61Q42600 (abstracts).
  • compositions according to the present invention are clear aqueous bleaching compositions comprising hydrogen peroxide as well as an organic peracid precursor, characterized in that the compositions have a pH in the range of from about 3.5 to about 6, and that the organic peracid precursor is a compound according to the formula:
  • R 1# R 2 , R 3 are independently selected from -H, -OH, -C-0-R 4 or -0-C-R 4 where R ⁇ is
  • compositions according to the present invention are clear aqueous liquid compositions which comprise hydrogen peroxide.
  • the compositions according to the present invention comprise from about 0.5 % to about 20 % by weight of the total composition of hydrogen peroxide, more preferably from about 2 % to about 15 %, most preferably from about 4 % to about 9%.
  • compositions according to the present invention further comprise a specific organic peracid precursor according to the formula:
  • R ⁇ , R , R 3 are independently selected from -H, -OH, -C-0-R 4 or -0-C-R 4 where R 4 is
  • Preferred such peracid precursors for use in the compositions according to the present invention are selected from ethylene glycol diesters, triacetin and diacetin, or mixtures thereof. Particularly preferred compounds are triacetin and ethylene glycol diacetate. Tributyrin also displays excellent stability in the compositions according to the present invention but is less preferred because it is less soluble in the compositions according to the present invention.
  • compositions according to the present invention typically comprise from about 1 % to about 15 % by weight of the total composition of such an organic peracid precursor, or mixtures thereof.
  • the desired amount of organic peracid precursor can also be defined in relation to the amount of hydrogen peroxide in the composition. Accordingly, the compositions according to the present invention preferably comprise from about 0.1 to about 2 moles of organic peracid precursor per mole of hydrogen peroxide.
  • compositions according to the present invention have a pH in the range of from about 3.5 to about 6, most preferably from about 3.5 to about 5, most preferably about 4.
  • the pH of the composition can be adjusted and buffered with such chemicals as organic and inorganic acids which are stable to oxidation, citric acid, sulphuric acid, sodium hydroxide, ammonia and amines.
  • Preferred buffer for use in the compositions according to the present invention is citric acid. It is essential that the pH of the composition remains within the above range as said range is critical to ensure adequate chemical stability of the hydrogen peroxide and of the specific organic peracid precursors used in the compositions according to the present invention.
  • compositions according to the present invention may comprise surfactants.
  • Preferred surfactants for use herein are well known anionic surfactants such as alkyl benzene sulphonates and alkyl sulfates, and/or nonionic surfactants such as ethoxylated a ⁇ d/or propoxylated alcohols. All surfactants for use herein must be resistant to oxidation by peracids and hydrogen peroxide, and are preferably water-soluble.
  • the compositions according to the present invention can comprise from 0% to about 30% by weight of the total composition of surfactants, preferably from about 0.5 % to about 15 %, most preferably from about 2 % to 8 %.
  • compositions according to the present invention may further comprise peroxide stabilizers such as stannates, 8-hydroxyquinoline, pyrophosphates and phosphonates.
  • Chelating agents may also be useful in the context of the present invention; suitable chelants include EDTA, NTA and DETPA, picolinic and dipicolinic acids and amino polyphosphonates, although some of these are poorly environmentally compatible.
  • Radical scavengers can also be used herein, such as butylated hydroxy toluene and other hindered hydroxy benzenes, or sodium benzoate. Butylated hydroxy toluene is a highly preferred ingredient as it has been observed that it stabilizes the peracid precursors according to the present invention, as well as hydrogen peroxide.
  • compositions according to the present invention can also comprise such optional ingredients as whitening agents, dyes, builders, thickeners, hydrotropes, perfumes, all of which need to be compatible with the mildly acidic pH and the oxidizing environment of the compositions according to the present invention.
  • compositions according to the present invention are further illustrated in the following examples.
  • compositions are made by mixing together the listed ingredients in the listed proportions.

Abstract

Aqueous bleaching compositions are disclosed which comprise hydrogen peroxide as well as an organic peracid precursor selected from a specific class of glycol and glycerin esters. The compositions have a pH in the range of from about 3.5 to about 6. The disclosed compositions are both physically and chemically stable.

Description

Acidic activated bleaching composition
Technical field
The present invention relates to bleaching compositions, mainly for use in laundry applications. The compositions according to the present invention, which comprise hydrogen peroxide as well as peracid precursors, are stable upon storage.
Background
Bleaching compositions using hydrogen peroxide have been extensively described in the art. Such hydrogen peroxide bleaches have an advantage over chlorine bleaches in that they are environmentally more compatible. Another advantage is that they are "milder" bleaches. This latter advantage is especially significant in laundry applications as hydrogen peroxide bleaches are safer to fabrics.
A major drawback of hydrogen peroxide bleaches is that they are less active than chlorine bleaches at low temperatures which are often encountered in modern laundering applications. Thus, hydrogen peroxide bleach activators have been developed and have been extensively described in the art. These activators are mainly transition metals or peracid precursors. Peracid precursors react with hydrogen peroxide to yield peracids. Peracids are the "activated" bleaching compounds which are efficient at low temperatures.
A problem which occurs in the formulation of such "activated" hydrogen peroxide bleaching compositions is the difficulty to obtain a composition which is both chemically and physically stable. Indeed, such compositions of the prior art are either turbid suspensions of insoluble activators with good chemical stability, or clear compositions with poor chemical stability which causes significant and undesired oxygen release.
It has now been found that this problem could be addressed by formulating a bleaching composition comprising hydrogen peroxide, an organic peracid precursor selected from a specific class, e.g. glycol and glycerin esters, and by formulating said composition in a narrow, acidic pH range. The mildly acidic pH range allows for adequate chemical stability of both the hydrogen peroxide and the organic peracid precursor. The activation of hydrogen peroxide trough the formation of a peracid is enhanced by the pH raise which occurs upon dilution in the wash water, especially when a detergent composition bringing further alkalinity is also present in the wash water.
Glycol esters have been often described as solvents in detergent and bleaching compositions. Such compositions are described for instance in US 3 956 159. These compositions have a pH of 6.5 and above.
J 62252500 (abstract) discloses bleaching compositions which comprise a bleach activator, including triacetin. These compositions are formulated at neutral or weakly basic pH.
Bleaching compositions for various applications, comprising triacetin are also disclosed in J62001792, J62001794 J 62001796, and J61Q42600 (abstracts).
Summary of the invention
The compositions according to the present invention are clear aqueous bleaching compositions comprising hydrogen peroxide as well as an organic peracid precursor, characterized in that the compositions have a pH in the range of from about 3.5 to about 6, and that the organic peracid precursor is a compound according to the formula:
Figure imgf000005_0001
wherein x is 0 or 1, R1# R2, R3 are independently selected from -H, -OH, -C-0-R4 or -0-C-R4 where RΛ is
II II *
0 O c l~ 4 alkyl, with the proviso that at least two of R^, R2 or R3 are -0-C-R4; or mixtures thereof.
O
Detailed description of the invention
The compositions according to the present invention are clear aqueous liquid compositions which comprise hydrogen peroxide. Preferably, the compositions according to the present invention comprise from about 0.5 % to about 20 % by weight of the total composition of hydrogen peroxide, more preferably from about 2 % to about 15 %, most preferably from about 4 % to about 9%.
The compositions according to the present invention further comprise a specific organic peracid precursor according to the formula:
Figure imgf000006_0001
wherein x is 0 or 1, R^, R , R3 are independently selected from -H, -OH, -C-0-R4 or -0-C-R4 where R4 is
11 11 o o
C1-C alkyl, with the proviso that at least two of R^, R2 or R3 are -0-C-R4; or mixtures thereof. All these
0 compounds are well known chemicals which are commercially available or can be synthesized according to the chemical literature.
Preferred such peracid precursors for use in the compositions according to the present invention are selected from ethylene glycol diesters, triacetin and diacetin, or mixtures thereof. Particularly preferred compounds are triacetin and ethylene glycol diacetate. Tributyrin also displays excellent stability in the compositions according to the present invention but is less preferred because it is less soluble in the compositions according to the present invention.
The compositions according to the present invention typically comprise from about 1 % to about 15 % by weight of the total composition of such an organic peracid precursor, or mixtures thereof. The desired amount of organic peracid precursor can also be defined in relation to the amount of hydrogen peroxide in the composition. Accordingly, the compositions according to the present invention preferably comprise from about 0.1 to about 2 moles of organic peracid precursor per mole of hydrogen peroxide.
The compositions according to the present invention have a pH in the range of from about 3.5 to about 6, most preferably from about 3.5 to about 5, most preferably about 4. The pH of the composition can be adjusted and buffered with such chemicals as organic and inorganic acids which are stable to oxidation, citric acid, sulphuric acid, sodium hydroxide, ammonia and amines. Preferred buffer for use in the compositions according to the present invention is citric acid. It is essential that the pH of the composition remains within the above range as said range is critical to ensure adequate chemical stability of the hydrogen peroxide and of the specific organic peracid precursors used in the compositions according to the present invention.
The compositions according to the present invention may comprise surfactants. Preferred surfactants for use herein are well known anionic surfactants such as alkyl benzene sulphonates and alkyl sulfates, and/or nonionic surfactants such as ethoxylated aήd/or propoxylated alcohols. All surfactants for use herein must be resistant to oxidation by peracids and hydrogen peroxide, and are preferably water-soluble. The compositions according to the present invention can comprise from 0% to about 30% by weight of the total composition of surfactants, preferably from about 0.5 % to about 15 %, most preferably from about 2 % to 8 %.
The compositions according to the present invention may further comprise peroxide stabilizers such as stannates, 8-hydroxyquinoline, pyrophosphates and phosphonates. Chelating agents may also be useful in the context of the present invention; suitable chelants include EDTA, NTA and DETPA, picolinic and dipicolinic acids and amino polyphosphonates, although some of these are poorly environmentally compatible. Radical scavengers can also be used herein, such as butylated hydroxy toluene and other hindered hydroxy benzenes, or sodium benzoate. Butylated hydroxy toluene is a highly preferred ingredient as it has been observed that it stabilizes the peracid precursors according to the present invention, as well as hydrogen peroxide.
The compositions according to the present invention can also comprise such optional ingredients as whitening agents, dyes, builders, thickeners, hydrotropes, perfumes, all of which need to be compatible with the mildly acidic pH and the oxidizing environment of the compositions according to the present invention.
The compositions according to the present invention are further illustrated in the following examples.
Examples
The following compositions are made by mixing together the listed ingredients in the listed proportions.
pH 4
Figure imgf000009_0001
Ingredients: % by weight:
V VI VII VIII
Hydrogen peroxide 6.0 8.0 3.5 5.0 Na alkyl sulphate 2.8 2.0 4.0 3.5 Triacetin 3.0 5.0 Ethylene glycol diacetate 4.0 5.0 Citric acid 1.0 1.0 1.0 1.0 Na stannate 0.0015 0.0015 0.0010 0.0015 Na hydroxide pH 4 pH 4 pH 4 pH 4 Water & minors up to 100 %

Claims

hat is claimed is:
1. An aqueous bleaching composition comprising hydrogen peroxide and an organic peracid precursor, characterized in that the compositions have a pH in the range of from about 3.5 to about 6, and that the organic peracid precursor is a compound according to the formula:
Figure imgf000011_0001
wherein x is 0 or 1, Rlf R2, R3 are independently selected from -H, -OH, -C-0-R4 or -0-C-R4 where R4
II 4 l( 4 4 0 O is C1-C4 alkyl, with the proviso that at least two of Rl' R2 or R3 are -0-C-R4; or mixtures thereof.
2. A composition according to claim 1 which has a pH in the range of from about 3.5 to about 5.
3. A composition according to claim 2 which has a pH of about 4.
A composition according to any of the preceding claims wherein the organic peracid precursor is selected from ethylene glycol diesters, triacetin, diacetin, or mixtures thereof.
5. A composition according to claim 4 wherein the organic peracid precursor is selected from triacetin and ethylene glycol diacetate.
6. A composition according to any of the preceding claims which comprises from about 0.5 % to about 20 % by weight of the total composition of hydrogen peroxide.
7. A composition according to any of the preceding claims which comprises from about 1 % to about 15 % by weight of the total composition of said organic peracid precursor.
8. A composition according to claim 6 which comprises from about 0.1 to about 2 moles of said organic peracid precursor per mole of hydrogen peroxide.
9. A composition according to any of the preceding claims which comprises from about 0.5 % to about 15 % by weight of the total composition of a surfactant.
10.A composition according to any of the preceding claims which comprises citric acid.
11.A composition according to any of the preceding claims which comprises butylated hydroxy toluene.
PCT/US1993/002944 1992-04-03 1993-03-29 Acidic activated bleaching compositon WO1993020167A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU39399/93A AU668936B2 (en) 1992-04-03 1993-03-29 Acidic activated bleaching compositon
JP5517617A JPH07505437A (en) 1992-04-03 1993-03-29 Acid activated bleaching composition
BR9306183A BR9306183A (en) 1992-04-03 1993-03-29 Acid-activated bleach composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19920200961 EP0563460B1 (en) 1992-04-03 1992-04-03 Acidic activated bleaching composition
EP92200961.8 1992-04-03

Publications (1)

Publication Number Publication Date
WO1993020167A1 true WO1993020167A1 (en) 1993-10-14

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EP (1) EP0563460B1 (en)
JP (1) JPH07505437A (en)
CN (1) CN1078254A (en)
AU (1) AU668936B2 (en)
BR (1) BR9306183A (en)
DE (1) DE69226072T2 (en)
ES (1) ES2118105T3 (en)
IE (1) IE930263A1 (en)
TW (1) TW299351B (en)
WO (1) WO1993020167A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5753138A (en) * 1993-06-24 1998-05-19 The Procter & Gamble Company Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations
US5879409A (en) * 1996-02-23 1999-03-09 The Procter & Gamble Company Bleach additive and bleaching compositions having glycine anhydride activators
US6221341B1 (en) * 1997-11-19 2001-04-24 Oraceutical Llc Tooth whitening compositions

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU688356B2 (en) * 1993-08-03 1998-03-12 Procter & Gamble Company, The A process of cleaning carpets using active oxygen compounds in an acidic aqueous medium
GB9600159D0 (en) * 1996-01-05 1996-03-06 Warwick Int Group Process for bleaching or disinfecting a substrate
US7919122B2 (en) 2003-04-02 2011-04-05 Kao Corporation Composition for production of a sterilizer and a process for producing organic peracid
DE60320778D1 (en) * 2003-07-08 2008-06-19 Procter & Gamble Liquid bleach activator composition
JP2012502173A (en) * 2008-09-10 2012-01-26 ダニスコ・ユーエス・インク Enzymatic textile bleaching composition and method of use
US8546449B2 (en) 2011-03-24 2013-10-01 Enviro Tech Chemical Services, Inc. Methods and compositions for the generation of peracetic acid on site at the point-of-use

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956159A (en) * 1974-11-25 1976-05-11 The Procter & Gamble Company Stable concentrated liquid peroxygen bleach composition
JPS6142600A (en) * 1984-08-06 1986-03-01 花王株式会社 Fungicidal composition
JPS621796A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS621794A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS621792A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS62252500A (en) * 1986-04-25 1987-11-04 花王株式会社 Bleaching composition
US4800038A (en) * 1988-01-21 1989-01-24 Colgate-Palmolive Company Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners
US5047168A (en) * 1988-01-21 1991-09-10 Colgate-Palmolive Co. Sugar ethers as bleach stable detergency boosters
US5151212A (en) * 1990-03-21 1992-09-29 The Belzak Corporation Peroxygen compound activation

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0125781B1 (en) * 1983-04-14 1987-08-12 Interox Chemicals Limited Peroxygen compounds

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956159A (en) * 1974-11-25 1976-05-11 The Procter & Gamble Company Stable concentrated liquid peroxygen bleach composition
JPS6142600A (en) * 1984-08-06 1986-03-01 花王株式会社 Fungicidal composition
JPS621796A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS621794A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS621792A (en) * 1985-06-28 1987-01-07 花王株式会社 Bleaching composition
JPS62252500A (en) * 1986-04-25 1987-11-04 花王株式会社 Bleaching composition
US4800038A (en) * 1988-01-21 1989-01-24 Colgate-Palmolive Company Acetylated sugar ethers as bleach activators detergency boosters and fabric softeners
US5047168A (en) * 1988-01-21 1991-09-10 Colgate-Palmolive Co. Sugar ethers as bleach stable detergency boosters
US5151212A (en) * 1990-03-21 1992-09-29 The Belzak Corporation Peroxygen compound activation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5753138A (en) * 1993-06-24 1998-05-19 The Procter & Gamble Company Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations
US5879409A (en) * 1996-02-23 1999-03-09 The Procter & Gamble Company Bleach additive and bleaching compositions having glycine anhydride activators
US6221341B1 (en) * 1997-11-19 2001-04-24 Oraceutical Llc Tooth whitening compositions

Also Published As

Publication number Publication date
BR9306183A (en) 1998-06-23
TW299351B (en) 1997-03-01
DE69226072T2 (en) 1999-02-25
AU668936B2 (en) 1996-05-23
DE69226072D1 (en) 1998-08-06
EP0563460B1 (en) 1998-07-01
EP0563460A1 (en) 1993-10-06
AU3939993A (en) 1993-11-08
JPH07505437A (en) 1995-06-15
CN1078254A (en) 1993-11-10
ES2118105T3 (en) 1998-09-16
IE930263A1 (en) 1993-10-06

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