WO2002083829A1 - Compositions activatrices de blanchiement melangees et procedes de blanchiement - Google Patents

Compositions activatrices de blanchiement melangees et procedes de blanchiement Download PDF

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Publication number
WO2002083829A1
WO2002083829A1 PCT/GB2002/001641 GB0201641W WO02083829A1 WO 2002083829 A1 WO2002083829 A1 WO 2002083829A1 GB 0201641 W GB0201641 W GB 0201641W WO 02083829 A1 WO02083829 A1 WO 02083829A1
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WO
WIPO (PCT)
Prior art keywords
bleaching
composition according
group
sodium
alkyl
Prior art date
Application number
PCT/GB2002/001641
Other languages
English (en)
Inventor
Ekram Haque
Carol A. Sheane
Original Assignee
Warwick International Group Limited
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 Warwick International Group Limited filed Critical Warwick International Group Limited
Publication of WO2002083829A1 publication Critical patent/WO2002083829A1/fr

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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
    • C11D3/3915—Sulfur-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
    • C11D3/3917—Nitrogen-containing compounds

Definitions

  • This invention relates to improved bleach activator and bleaching compositions.
  • the invention relates to novel bleaching and detergent compositions which provide an effective overall bleaching performance on textiles and fabrics over a wide variety of stains.
  • Detergent bleach compositions for washing at higher temperatures are well known in the art.
  • bleaching agents they normally contain a peroxide compound which liberates hydrogen peroxide in aqueous solution, such as the peroxyhydrates, including alkali metal perborates, percarbonates, perphosphates and persilicates, urea peroxide and the like.
  • these bleaching agents are only effective at higher temperatures of the bleaching solution, i.e. from 80°C up to the boil.
  • peroxide bleach compounds can be improved so as to become effective at lower wash temperatures, e.g. 40- 60°C, by the use of peroxyacid precursors, often also referred to as bleach activators.
  • GB patent 855,735 which discloses the broad class of "acyl organoamides", to which the currently most widely used N,N,N'N'-tetraacetyl ethylene diamine (TAED) belongs.
  • the substances that have been proposed and utilised as bleach activators are organic compounds which react with the perhydroxide anion (OOH " ) of the hydrogen peroxide yielded by the peroxide bleach in the bleaching solution, to form a peroxyacid which is more reactive than the peroxide bleach alone, to effect bleaching at bleach solution temperatures of below 60°C.
  • a particular type of stain which is effectively removed by one specific peroxyacid precursor-hydrogen peroxide combination may not be as effectively removed by another peroxyacid precursor/H 2 0 2 system. Since many classes of soiling are encountered in household and industrial practice, there is not one single bleach activator which is effective on all sorts of bleachable soiling and stains. Domestic soils contain hydrophilic and hydrophobic components.
  • EP-A-0257700 discloses the use of a bleach system comprising a percompound and a mixture of TAED and sodium nonanoyloxy benzene sulphonate.
  • EP-A-0202698 discloses a novel p-sulphophenyl alkyl carbonate, having an alkyl group containing 6 to 10 carbon atoms. Detergent compositions containing this type of activator are disclosed.
  • the present invention provides a bleaching composition
  • a bleaching composition comprising a carbonate bleach activator compound of the general structural formula (I)
  • R is selected from the group consisting of C 6 . 24 alkyl, C 6 . 24 alkenyl, C 6 . 2 alkynyl and C 7 . 24 aralkyl; R 1 is a 2 alkyl group, n is an integer of 0 to 4, M is a cation and m is 1 or 2; and a hydrophilic acyl organoamide bleach activator.
  • the present invention additionally provides a detergent composition and a method of bleaching a substrate utilising the above mentioned mixture of bleach activators.
  • group R is preferably a C 6 . 12 , more preferably C 6 . 10 , most preferably C 8 alkyl group.
  • R may be branched or linear, preferably linear. Where R is branched, R is preferably 2-ethylhexyl.
  • the aryl part may be substitute, for instance by C.,_ 18 alkyl, preferably
  • R 1 is preferably a C,. 6 alkyl group, most preferably a methyl or ethyl group.
  • n is preferably an integer of 0 or 1 , most preferably 0.
  • M is selected from the group consisting of alkali metals, alkaline earth metals and ammonium groups, more preferably alkali metals, most preferably sodium.
  • Preferred compounds of formula (I) are sodium or potassium p-(sulphophenyl n-octyl) carbonate, sodium or potassium p-(sulphophenyl n- nonyl) carbonate, and sodium or potassium p-(sulphophenyl n-decyl) carbonate.
  • compound (I) is sodium p- (sulphophenyl /7-octyl) carbonate.
  • the hydrophilic acyl organoamide is an amide derived from an organic carboxylic acid and an organic group substituted amine compound containing at least one acyl group attached to the nitrogen atom.
  • hydrophilic acyl organoamide is meant that it is the peracid of the acyl group which is hydrophilic.
  • peroxyacid precursor compounds falling under this group are:
  • N-acylhydantoins such as N,N'-diacetyl-5,5-dimethylhydantoin
  • Polyacylated alkylene diamines such as N,N,N',N'-tetraacetyl ethylene diamine (TAED) and N,N,N',N'-tetraacetyl methylene diamine (TAMD) as disclosed in British Patent No. 907,356;
  • alpha-Acyloxy-(N,N')-polyacyl malonamides such as alpha-acetoxy-(N,N')diacetyl malonamide as disclosed in U.S. Patent No. 3,183,266.
  • the acyl organoamide generally has the structural formula R 2 CONR 3 R 4 , in which R 2 is selected from Q, 2 alkyl, C 2 . 12 alkenyl and C 2 . 12 alkynyl groups, R 3 is a second acyl radical and R 4 is selected from C ⁇ alkyl, C 2 . 12 alkenyl and C 2 . 12 alkynyl groups, any of which may be substituted with one or more mono-or di- acyl amino groups.
  • the acyl organoamide comprises two amide groups linked through an alkanediyl group.
  • the acyl organoamide has the structural formula (II)
  • R 5 is a C, ⁇ alkanediyl group, preferably an ethanediyl group, and each R 6 is individually selected from a C,_ 6 alkyl group, preferably methyl, ethyl or propyl. Preferably all R 6 are the same.
  • the acyl organoamide is N,N,N',N'-tetracetylethylene diamine (TAED).
  • the above mentioned compounds are advantageously incorporated into a detergent composition which, in addition to the bleach activators, contains a bleaching agent, which under alkaline conditions generates hydrogen peroxide.
  • bleaching agents examples include alkali metal percarbonate, perborate, persilicate, perphosphate, persulphate and perpyrophosphate, herein after "percompounds".
  • a preferred bleaching agent is sodium percarbonate.
  • the bleaching agent can be present in the detergent composition in amounts of from 5-99% by weight.
  • the detergent composition of the invention may consist solely of a percompound and the bleach activator mixture when used as a pure bleach product or as a bleach additive to detergent compositions. In that case the composition will comprise from 50-99% percompound and from 50-1 % of the bleach activators, and optional diluents.
  • compound (I) is present in a detergent composition in an amount of 0.1 to 50% by weight, preferably 0.5 to 10% by weight, most preferably 1 to 2% by weight.
  • the organoamide is present in a detergent composition in an amount of 0.1 to 50% by weight, preferably 0.5 to 10% by weight, most preferably 3 to 5% by weight.
  • the detergent composition will contain at least one surface-active agent selected from the group consisting of soaps, synthetic anionic, nonionic, cationic, amphoteric and zwitterionic surfactants and mixtures thereof, in an amount of from about 2 to 40% by weight of the composition.
  • mixtures of the above surface-active agents are used; mixtures of synthetic anionic, synthetic nonionic surfactants and soap are commonly used.
  • Suitable anionic surfactants are alkali metal soaps of fatty acids, fatty acid-protein condensation products, primary or secondary alkyl sulphates, fatty-acid alkanolamide sulphates, sulphated alkyl- or alkylphenol-polyglycolethers, fatty acid isethionates, fatty acid taurides, alkylbenzene sulphonates, alkane sulphonates, olefin sulphonates, salts of alpha-sulpho fatty acids and esters thereof, and other known surface-active compounds of the sulphate and sulphonate type.
  • nonionic surfactants are alkyl and acyl polyglycolethers, alkylphenol polyglycolether, fatty acid alkanolamides and their ethoxylated products, ethoxylated polypropylene glycolethers, amine oxides and fatty acid sugar esters.
  • the bleach activators according to the present invention commonly are presented in a detergent matrix.
  • the bleach activators according to the invention may be used perse in a detergent composition.
  • the total amount of detergency matrix in a detergent composition of the invention will be from about 5% to about 70% by weight of the detergent composition.
  • detergent matrices are based on sodium tripolyphosphate, sodium orthophosphate, sodium pyrophosphate, sodium trimetaphosphate, sodium ethane-1-hydroxy-1 ,1-diphosphonate, sodium carbonate, sodium silicate, sodium citrate, sodium oxydiacetate, sodium nitrilotriacetate, sodium ethylenediaminetetraacetate, sodium salts of long-chain dicarboxylic acids, for instance straight-chain (C 10 to C 20 ) succinic acids and malonic acids, sodium salts of alpha-sulphonated long-chain monocarboxylic acids, sodium salts of polycarboxylic acids, i.e.
  • acids derived from the polymerization or copolymerization of unsaturated carboxylic acids and unsaturated carboxy acid anhydrides such as maleic acid, acrylic acid, itaconic acid, methacrylic acid, crotonic acid and aconitic acid, and the anhydrides of these acids, and also from the copolymerization of the above acids and anhydrides with minor amounts of other monomers, such as vinyl chloride, vinyl acetate, methyl methacrylate, methyl acrylate and styrene, polyacetal carboxylates, and, modified starches such as starches oxidized, for example, using sodium hypochlorite, in which some anhydroglucose units have been opened to give dicarboxyl units.
  • unsaturated carboxylic acids and unsaturated carboxy acid anhydrides such as maleic acid, acrylic acid, itaconic acid, methacrylic acid, crotonic acid and aconitic acid, and the anhydrides of these acids, and also from the copo
  • Preferred materials of this type have the formula: (Na 2 0) o / ⁇ ⁇ 2 0 3 (S ⁇ 0 2 ) ⁇ 3 . 3 . 3 and may be amorphous or crystalline, with some bound water usually in an amount of about 10-30% depending on the drying conditions used.
  • Such water-insoluble aluminosilicate cation-exchange materials are available as very finely divided powder, commercially known under various grades of zeolites, e.g. Zeolite A and Zeolite B.
  • any other non-interfering ingredients normally used in detergent compositions in minor amounts, which serve to improve the bleaching and laundering characteristics of the composition or which add aesthetic appeal to the composition, may also be incorporated.
  • a peroxide stabilising agent usually a heavy metal sequestrant such as ethylene diamine tetra(methylene phosphonic acid) or its alkali metal salts as disclosed in GB Patent No. 1 ,392,284, and other selected types of compounds as disclosed in GB Patent No. 2,033,937.
  • a heavy metal sequestrant such as ethylene diamine tetra(methylene phosphonic acid) or its alkali metal salts as disclosed in GB Patent No. 1 ,392,284, and other selected types of compounds as disclosed in GB Patent No. 2,033,937.
  • Other minor ingredients can include washing alkalis and buffering agents, sequestering agents such as EDTA, polymeric co-builders, suds-controlling agents, soil-suspending agents and anti-redeposition agents, enzymes, particularly proteolytic enzymes, corrosion inhibitors, optical brighteners, colouring agents, heavy metal catalysts, perfumes, bacteriostats and filler materials.
  • Such minor components comprise no more than about 20% by weight of the bleach composition.
  • the detergent composition according to the invention may be in a form-varying from-powdered to granular and may be prepared by methods known in the art, such as crystallisation or spray drying of an aqueous slurry or mechanical mixing of the substances.
  • the invention is not confined to solid detergent compositions but also comprises liquid detergent compositions containing the present bleaching activators.
  • the present bleaching activators may also be added separately, in the form of a detergent additive containing the bleach activators, to aqueous wash liquor containing at least a surfactant and a hydrogen peroxide generating bleaching agent.
  • the bleach activators may be applied in the form of powder, granule preferably provided in a matrix, such as described above or in the form of a solution or dispersion.
  • the bleaching activator may also be used in the form or a coated particle. Examples of suitable coating materials are ethoxylated fatty acids and poly(ethylene oxide).
  • the present invention also includes methods of bleaching fabrics and textiles in which the bleach composition and a bleaching agent are dissolved into the water to form a detergent liquor, which is then contacted with the fabric or textiles.
  • the present invention has particular utility in the fields of laundry and textile bleaching and cleaning.
  • the invention has been shown to be particularly effective in the bleaching and cleaning of laundry and textiles comprising both hydrophilic and hydrophobic stains. This is due to the hydrophobic nature of the carbonate bleach activator and the hydrophilic nature of the acyl organoamide.
  • the present invention will now be described with reference to the examples.
  • AS12 - an overall performance monitor for all temperatures. Has a low concentration of milkpowder and therefore also has a small (proteolytic) enzyme response. AS12 also responds to builder/water hardness, oxidising bleaches (slightly), wash time and product concentration.
  • E116 - blood / milk / carbon black stains Fixing of this stain can, in some circumstances, be used as a measure of bleach performance.
  • Action plan 4 Washes - Stain Removal as % Z Brightness
  • the 4% TAED/1% SC905 mixed system did not show any overall complimentary effects, although there was a slight improvement in stain removal when compared to TAED alone. This was the ratio of SC905 and TAED which showed benefits under European conditions (Example 1 ).
  • the mixed activator system consisting of 2.5% SC905 plus 2.5% TAED showed improved stain removal under Asia Pacific conditions compared with the sum of the individual activators.

Abstract

La présente invention concerne une composition de blanchiement comprenant un composé activateur de blanchiement de carbonate représenté par la formule structurelle générale (I) dans laquelle R est sélectionné dans le groupe comprenant C6-24 alkyle, C6-24 alcényle, C6-24 alcynyle et C7-24 aralkyle, R1 est un groupe C¿1-12? alkyle, n est un entier de 0 à 4, M est un cation et m est 1 ou 2; et un activateur de blanchiement d'organoamide acyle hydrophilique. La présente invention concerne également une composition détergente et un procédé de blanchiement d'un substrat utilisant le mélange d'activateurs de blanchiement mentionné ci-dessus.
PCT/GB2002/001641 2001-04-11 2002-04-08 Compositions activatrices de blanchiement melangees et procedes de blanchiement WO2002083829A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0109137A GB0109137D0 (en) 2001-04-11 2001-04-11 Mixed bleach activator compositions and methods of bleaching
GB0109137.0 2001-04-11

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WO2002083829A1 true WO2002083829A1 (fr) 2002-10-24

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2395488A (en) * 2002-11-22 2004-05-26 Reckitt Benckiser Nv Stain removal
EP1433839A1 (fr) * 2002-12-24 2004-06-30 Dalli-Werke GmbH & Co. KG Compositions de lavage et nettoyage optimisées pour un effet amélioré de blanchiment à basse température
WO2005073360A1 (fr) * 2004-01-16 2005-08-11 The Procter & Gamble Company Systeme de catalyseur organique
WO2006027179A1 (fr) * 2004-09-08 2006-03-16 Clariant Produkte (Deutschland) Gmbh Melanges d'agents de blanchiment
US7541324B2 (en) 2004-09-08 2009-06-02 Clariant Produkte (Deutschland) Gmbh Bleach activator mixtures
WO2009048611A3 (fr) * 2007-10-11 2009-06-18 Promega Corp Tensio-actifs clivables
WO2014090568A1 (fr) * 2012-12-12 2014-06-19 Unilever N.V. Composition de détergent

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0202698A1 (fr) * 1985-05-07 1986-11-26 Akzo Nobel N.V. P-sulphophénylalkylcarbonates et leur utilisation comme activeurs de blanchiment
US4686061A (en) * 1985-07-03 1987-08-11 Akzo Nv P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds
EP0333248A2 (fr) * 1988-03-17 1989-09-20 Unilever N.V. Précurseurs de blanchiment et leur utilisation dans des compositions de blonchiment et/ou de détergents
EP0402339A1 (fr) * 1989-06-05 1990-12-12 Monsanto Company Procédé pour la préparation d'esters de l'acide carbonique
US5175333A (en) * 1990-09-14 1992-12-29 Lever Brothers Company, Division Of Conopco, Inc. Transesterification route to quaternary ammonium substituted carbonate esters
US5705091A (en) * 1995-09-11 1998-01-06 The Clorox Company Alkoxylated peracid activators

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0202698A1 (fr) * 1985-05-07 1986-11-26 Akzo Nobel N.V. P-sulphophénylalkylcarbonates et leur utilisation comme activeurs de blanchiment
US4686061A (en) * 1985-07-03 1987-08-11 Akzo Nv P-sulphophenyl carbonates and detergent compositions and detergent additives containing these compounds
EP0333248A2 (fr) * 1988-03-17 1989-09-20 Unilever N.V. Précurseurs de blanchiment et leur utilisation dans des compositions de blonchiment et/ou de détergents
EP0402339A1 (fr) * 1989-06-05 1990-12-12 Monsanto Company Procédé pour la préparation d'esters de l'acide carbonique
US5175333A (en) * 1990-09-14 1992-12-29 Lever Brothers Company, Division Of Conopco, Inc. Transesterification route to quaternary ammonium substituted carbonate esters
US5705091A (en) * 1995-09-11 1998-01-06 The Clorox Company Alkoxylated peracid activators

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2395488A (en) * 2002-11-22 2004-05-26 Reckitt Benckiser Nv Stain removal
WO2004048507A1 (fr) * 2002-11-22 2004-06-10 Reckitt Benckiser N.V. Procede pour eliminer des taches
US7255112B2 (en) 2002-11-22 2007-08-14 Reckitt Benckiser N.V. Process of removing stains
EP1433839A1 (fr) * 2002-12-24 2004-06-30 Dalli-Werke GmbH & Co. KG Compositions de lavage et nettoyage optimisées pour un effet amélioré de blanchiment à basse température
WO2005073360A1 (fr) * 2004-01-16 2005-08-11 The Procter & Gamble Company Systeme de catalyseur organique
WO2006027179A1 (fr) * 2004-09-08 2006-03-16 Clariant Produkte (Deutschland) Gmbh Melanges d'agents de blanchiment
US7504372B2 (en) 2004-09-08 2009-03-17 Clariant Produkte (Deutschland) Gmbh Mixtures of bleaching agents
US7541324B2 (en) 2004-09-08 2009-06-02 Clariant Produkte (Deutschland) Gmbh Bleach activator mixtures
WO2009048611A3 (fr) * 2007-10-11 2009-06-18 Promega Corp Tensio-actifs clivables
JP2011501748A (ja) * 2007-10-11 2011-01-13 プロメガ コーポレイション 切断可能な界面活性剤
EP2584027A3 (fr) * 2007-10-11 2013-07-17 Promega Corporation Tensioactifs clivables
US9816054B2 (en) 2007-10-11 2017-11-14 Promega Corporation Cleavable surfactants
US10626349B2 (en) 2007-10-11 2020-04-21 Promega Corporation Cleavable surfactants
US11624041B2 (en) 2007-10-11 2023-04-11 Promega Corporation Cleavable surfactants
WO2014090568A1 (fr) * 2012-12-12 2014-06-19 Unilever N.V. Composition de détergent
AU2013357704B2 (en) * 2012-12-12 2016-07-07 Unilever Plc Detergent composition

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