WO1996009276A1 - Compositions detergentes - Google Patents

Compositions detergentes Download PDF

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Publication number
WO1996009276A1
WO1996009276A1 PCT/US1995/011797 US9511797W WO9609276A1 WO 1996009276 A1 WO1996009276 A1 WO 1996009276A1 US 9511797 W US9511797 W US 9511797W WO 9609276 A1 WO9609276 A1 WO 9609276A1
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Prior art keywords
independently
hydrocarbyl
compound according
detergent
detergent composition
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PCT/US1995/011797
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English (en)
Inventor
Frederick Edward Hardy
Barry Thomas Ingram
Alison Lesley Main
Christian Leo Marie Vermote
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The Procter & Gamble Company
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Priority to EP95933835A priority Critical patent/EP0782561A4/fr
Publication of WO1996009276A1 publication Critical patent/WO1996009276A1/fr

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    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/16—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by an inorganic acid or a derivative thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/65—Mixtures of anionic with cationic compounds

Definitions

  • the present invention relates to detergent compositions comprising a surfactant which provides suds supressing benefits.
  • the sudsing profile of a detergent composition is also an important factor to be considered by the detergent manufacturer. It is generally considered that high sudsing is not a desirable feature of a laundry detergent composition for laundering conducted in automatic washing machines. However, high levels of surfactant in a detergent composition usually results in an increase in the sudsing of the detergent composition. This problem is particularly acute if the surfactant system comprises high levels of anionic surfactant. Thus, in order to control the suds profile, such compositions require the addition of a suds suppressor. However, the suds suppressors currently available are generally expensive and also provide no other performance benefit to the composition other than suds suppression. Therefore, it is desirable that their presence is minimised.
  • the cationic compounds of the present invention readily hydrolyse in the wash liquor and these hydrolysis products then act as suds suppressors.
  • the hydrolysis products can thus act to suppress the sudsing produced by other surfactants which may be preferred components of the detergent composition.
  • the hydrolysis products tend to be formed in the latter stages of the washing process, when sudsing is at its greatest and suds suppression is most required.
  • another advantage of the presence of the suds suppressing hydrolysis products is that the amount of additional suds suppressor required in the formulation is reduced.
  • the cationic compounds of the present invention have a dual function as a component of a surfactant system providing improved cleaning and as precursors of suds suppression agents in detergent compositions.
  • a further advantage of the cationic compounds of the present invention is that they are also low sudsing compounds per se.
  • Cationic surfactants have been described in the art in detergent compositions to provide fabric care benefits and enhanced cleaning. See for example US 4 239 660, US 4 259 217, US 4 260 529, US 4 228 042, EP 021 491 and EP 000 234. Branched cationic species for softening have been disclosed in DE 3402 146.
  • Ri and R2 are independently a C4 to Cj2 hydrocarbyl, and wherein c is 1 or 0, provided that where c is 1 , X and Y are independently selected from
  • X is O C O f
  • R ⁇ and R4 are independently Ci to C4 hydrocarbyl or a benzyl group, a and b are independently from 0 to 4,
  • R5 is a C ⁇ to C9 hydrocarbyl or Ci to C9 polyalkylene oxide having an average degree of polymerization of from 1 to 9, d is 0 to 2,
  • Q is a cationic group, e is 1 or 2
  • M is an anion providing electrical neutrality and mixtures of any of the foregoing compounds.
  • a detergent composition comprising an anionic surfactant and a compound according to the formula: R
  • the present invention also relates to a method of washing fabrics comprising contacting said fabrics with an aqueous solution comprising at least 0.005% compound hereinbefore defined according to the present invention or at least 0.1 % of a detergent composition according to the present invention.
  • the sum of the carbon chain lengths of Ri and R2 is from 10 to 18, more preferably from 12 to 18 and the difference in said carbon chain lengths of Ri and R2 is 4 or less, preferably 3 or less, most preferably 2 or less.
  • Ri and R2 are independently C to Cio linear alkyl groups and most preferably have the same number of carbon atoms.
  • c is 1 or 0, provided that where c is 1 , X and Y are independently selected from
  • R3 and R4 are independently Cj to C4, preferably linear C ⁇ to C2 hydrocarbyl or a benzyl group.
  • R3 or R4 comprises a benzyl group
  • a and b are independently from 0 to 4, preferably from 1 to 2.
  • R5 is a Ci to Ci8, preferably a Ci to C9 group selected from alkyls, alkenyls, alkylaryls, and polyalkylene oxide, preferably ethylene or propylene having an average degree of polymerization of from 1 to 9.
  • d is 0 to 2.
  • Q is any cationic group and e is 1 or 2.
  • Suitable cationic groups for use herein may be selected from:
  • e is equal to two, cationic components containing two cationic charge centres are formed.
  • a preferred type of cationic group for use herein are the alkoxylated alkyl quaternaries. Examples of such groups are given below:
  • each p is from 1 to 12, preferably from 1 to 10 (with the total ethylene oxide groups in a molecule not exceeding about 13). It is preferred that these compounds contain no more than a total of about 10, preferably no more than about 7, ethylene oxide groups in order to obtain the best removal of greasy and oily soils.
  • the compositions of the present invention are preferably substantially free of cationic compounds containing about 13 or more ethylene oxide groups. These compounds tend to be relatively non-biodegradable, do not enhance the cleaning or fabric conditioning benefits provided by the compositions and may, in some circumstances, decrease the overall laundering performance provided by them. It is to be noted that polyethoxylated cationic surfactants having relatively low levels of ethoxylation, such as those described above, exhibit better biodegradability characteristics and may be advantageously included in the compositions of the present invention.
  • M is a counter ion and may be any anion which results in the compound becoming water dispersible.
  • the counterions are present in an appropriate number to give electrical neutrality.
  • Suitable anions may be selected from halides, sulphates and nitrates and are preferably chloride, bromide, iodide and methyl sulphate and mixtures thereof.
  • Another aspect of the present invention relates to a detergent composition
  • a detergent composition comprising an anionic surfactant and a compound according to the formula: R
  • R3 and R4 are independently Ci to C4 hydrocarbyl or a benzyl group a and b are independently from 0 to 4, R5 is a C ⁇ to C9 hydrocarbyl or Ci to C9 polyalkylene oxide having an average degree of polymerization of from 1 to 9, d is 0 to 2, Q is an cationic group, e is 1 or 2, M is an anion providing electrical neutrality and mixtures thereof.
  • R and R2 are Ctj to Ci2, selected from alkyl, alkenyl and alkylaryl groups and which may be branched or linear.
  • Ri and R2 are independently alkyl groups.
  • the sum of the carbon chain lengths of Rj and R2 is from 10 to 18, more preferably from 12 to 18 and the difference in said carbon chain lengths of Ri and R2 is 4 or less, preferably 3 or less, most preferably 2 or less.
  • Ri and R2 have the same number of carbon atoms.
  • R3 and R4 are preferably linear Ci to C2 hydrocarbyl or a benzyl group. More preferably only R3 or R4 comprises a benzyl group, a and b are preferably from 1 to 2.
  • R5 is preferably a Ci to C9 group selected from alkyls, alkenyls, alkylaryls, and polyalkylene oxide, preferably propylene or ethylene having an average degree of polymerization of from 1 to 9.
  • Q is preferably selected from one of the cationic groups I to VI, preferably I, III and IV, most preferably I and III.
  • cationic compounds for use in anionic detergent compositions of this aspect of the present invention are betaine ester derivatives having the formula: O CH, ⁇ +
  • Surfactants suitable for use herein include the conventional C ⁇ j-Ci8 alkyl benzene sulphonates ("LAS") and primary, branched-chain and random C10-C20 alkyl sulphates ("AS"), the C10-C18 secondary (2,3) alkyl sulphates of the formula CH3(CH2) x (CHOS ⁇ 3 ' M + ) CH3 and CH3 (CH2) y (CHOS ⁇ 3 ' M + ) CH2CH3 where x and (y + 1) are integers of at least about 7, preferably at least about 9, and M is a water-solubilizing cation, especially sodium, unsaturated sulphates such as oleyl sulphate, the C10-C18 alkyl alkoxy sulphates ("AE X S"; especially EO 1-7 ethoxy sulphates), Cifj-Cis alkyl alkoxy carboxylates (especially the EO 1-5 ethoxycarboxylates), the C ⁇ r
  • sugar- derived surfactants include the N-alkoxy polyhydroxy fatty acid amides, such as C10-C18 N-(3-methoxypropyl) glucamide.
  • the N-propyl through N-hexyl C12-C18 glucamides can be used for low sudsing.
  • C10-C20 conventional soaps may also be used. If high sudsing is desired, the branched-chain soaps may be used. Mixtures of anionic and nonionic surfactants are especially useful.
  • Other conventional useful surfactants such as linear cationic surfactants are listed in standard texts.
  • the detergent compositions preferably comprise from 1 % to 80%, preferably from 1 % to 60%, most preferably from 5% to 40% of surfactant.
  • Preferred surfactants for use herein are linear alkyl benzene sulphonate, alkyl sulphates, alkyl alkoxylated nonionic surfactants or mixtures thereof.
  • Detergent builders can optionally be included in the compositions herein to assist in controlling mineral hardness. Inorganic as well as organic builders can be used. Builders are typically used in fabric laundering compositions to assist in the removal of paniculate soils.
  • the level of builder can vary widely depending upon the end use of the composition and its desired physical form. When present, the compositions will typically comprise at least 1 % builder. Liquid formulations typically comprise from 5% to 50%, more typically about 5% to about 30%, by weight, of detergent builder. Granular formulations typically comprise from 10% to 80%, more typically from 15% to 50% by weight, of the detergent builder. Lower or higher levels of builder, however, are not meant to be excluded. 12
  • Inorganic or P-containing detergent builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates (exemplified by the tripolyphosphates, pyrophosphates, orthophosphates and glassy polymeric meta-phosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulphates, and aluminosilicates (see, for example, U.S. Patents 3,159,581; 3,213,030; 3,422,021; 3,400,148 and 3,422,137).
  • silicate builders are the alkali metal silicates, particularly those having a Si ⁇ 2:Na2 ⁇ ratio in the range 1.6:1 to 3.2:1 and layered silicates, such as the layered sodium silicates described in U.S. Patent 4,664,839, issued May 12, 1987 to H. P. Rieck.
  • NaSKS-6 is the trademark for a crystalline layered silicate marketed by Hoechst (commonly abbreviated herein as "SKS-6").
  • Hoechst commonly abbreviated herein as "SKS-6”
  • the Na SKS-6 silicate builder does not contain aluminum.
  • NaSKS-6 has the delta-Na2S.2 ⁇ 5 morphology form of layered silicate.
  • SKS-6 is a highly preferred layered silicate for use herein, but other such layered silicates, such as those having the general formula NaMSi x ⁇ 2 ⁇ + l*yH2 ⁇ wherein M is sodium or hydrogen, x is a number from 1.9 to 4, preferably 2, and y is a number from 0 to 20, preferably 0 can be used herein.
  • Various other layered silicates from Hoechst include NaSKS-5, NaSKS-7 and NaSKS-11, as the alpha, beta and gamma forms.
  • delta-Na2Si2 ⁇ 5 (NaSKS-6 form) is most preferred for use herein.
  • Other silicates may also be useful such as for example magnesium silicate, which can serve as a crispening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
  • magnesium silicate which can serve as a crispening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
  • Examples of carbonate builders are the alkaline earth and alkali metal carbonates as disclosed in German Patent Application No. 2,321,001 published on November 15, 1973.
  • Aluminosilicate builders are useful in the present invention. Aluminosilicate builders are of great importance in most currently marketed heavy duty granular detergent compositions, and can also be a significant builder ingredient in liquid detergent formulations. Aluminosilicate builders include those having the empirical formula:
  • aluminosilicate ion exchange materials are commercially available. These aluminosilicates can be crystalline or amorphous in structure and can be naturally-occurring aluminosilicates or synthetically derived. A method for producing aluminosilicate ion exchange materials is disclosed in U.S. Patent 3,985,669, Krummel, et al, issued October 12, 1976. Preferred synthetic crystalline aluminosilicate ion exchange materials useful herein are available under the designations Zeolite A, Zeolite P (B), Zeolite MAP and Zeolite X. In an especially preferred embodiment, the crystalline aluminosilicate ion exchange material has the formula:
  • This material is known as Zeolite A.
  • the aluminosilicate has a particle size of about 0.1-10 microns in diameter.
  • polycarboxylate builders include a variety of categories of useful materials.
  • One important category of polycarboxylate builders encompasses the ether polycarboxylates, including oxydisuccinate, as disclosed in Berg, U.S. Patent 3,128,287, issued April 7, 1964, and Lamberti et al, U.S. Patent 3,635,830, issued January 18, 1972. See also "TMS/TDS" builders of U.S. Patent 4,663,071, issued to Bush et al, on May 5, 1987.
  • Suitable ether polycarboxylates also include cyclic compounds, particularly alicyclic compounds, such as those described in U.S. Patents 3,923,679; 3,835,163; 4,158,635; 4,120,874 and 4,102,903.
  • ether hydroxypolycarboxylates copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1, 3, 5-trihydroxy benzene-2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid
  • various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid
  • polycarboxylates such as mellitic acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.
  • Citrate builders e.g., citric acid and soluble salts thereof (particularly sodium salt), are polycarboxylate builders of particular importance for heavy duty liquid detergent formulations due to their availability from renewable resources and their biodegradability. Citrates can also be used in granular compositions, especially in combination with zeolite and/or layered silicate builders. Oxydisuccinates are also especially useful in such compositions and combinations.
  • succinic acid builders include the C5-C20 alkyl and alkenyl succinic acids and salts thereof.
  • a particularly preferred compound of this type is dodecenylsuccinic acid.
  • succinate builders include: laurylsuccinate, myristylsuccinate, palmitylsuccinate, 2- dodecenylsuccinate (preferred), 2-pentadecenylsuccinate, and the like. Laurylsuccinates are the preferred builders of this group, and are described in European Patent Application 86200690.5/0,200,263, published November 5, 1986.
  • Fatty acids e.g., Ci2-Cj8 monocarboxylic acids
  • Ci2-Cj8 monocarboxylic acids can also be incorporated into the compositions alone, or in combination with the aforesaid builders, especially citrate and/or the succinate builders, to provide additional builder activity.
  • Such use of fatty acids will generally result in a diminution of sudsing, which should be taken into account by the formulator.
  • the detergent compositions herein may also optionally contain one or more iron and/or manganese chelating agents.
  • chelating agents can be selected from the group consisting of amino carboxylates, amino phosphonates, poly functionally-substituted aromatic chelating agents and mixtures therein, all as hereinafter defined. Without intending to be bound by theory, it is believed that the benefit of these materials is due in part to their exceptional ability to remove iron and manganese ions from washing solutions by formation of soluble chelates.
  • Amino carboxylates useful as optional chelating agents include ethylenediaminetetracetates, N-hydroxyethylethylenediaminetriacetates, nitrilotriacetates, ethylenediamine tetraproprionates, triethylenetetraamine hexacetates, diethylenetriaminepentaacetates, and ethanoldiglycines, alkali metal, ammonium, and substituted ammonium salts therein and mixtures therein.
  • Amino phosphonates are also suitable for use as chelating agents in the compositions of the invention when at lease low levels of total phosphorus are permitted in detergent compositions, and include ethylenediaminetetrakis (methylenephosphonates) as DEQUEST. Preferred, these amino phosphonates to not contain alkyl or alkenyl groups with more than about 6 carbon atoms.
  • Polyfunctionally-substituted aromatic chelating agents are also useful in the compositions herein. See U.S. Patent 3,812,044, issued May 21, 1974, to Connor et al.
  • Preferred compounds of. this type in acid form are dihydroxydisulfobenzenes such as l,2-dihydroxy-3,5-disulfobenzene.
  • these chelating agents will generally comprise from 0.1 % to 10% by weight of the detergent compositions herein, more preferably, from 0.1 % to 3.0% by weight of such compositions.
  • the detergent compositions herein may optionally contain bleaching agents or bleaching compositions containing a bleaching agent and one or more bleach activators.
  • bleaching agents will typically be at levels of from 1 % to 30%, more typically from 5% to 20%, of the detergent composition, especially for fabric laundering.
  • the amount of bleach activators will typically be from 0.1 % to 60%, more typically from 0.5% to 40% of the bleaching composition comprising the bleaching agent-plus-bleach activator.
  • the bleaching agents used herein can be any of the bleaching agents useful for detergent compositions in textile cleaning, hard surface cleaning, or other cleaning purposes that are now known or become known. These include oxygen bleaches as well as other bleaching agents. Peroxygen bleaching agents can also be used. Suitable peroxygen bleaching compounds include sodium carbonate peroxyhydrate and equivalent "percarbonate" bleaches, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, and sodium peroxide. Persulfate bleach (e.g., OXONE, manufactured commercially by DuPont) can also be used.
  • a preferred percarbonate bleach comprises dry particles having an average particle size in the range from about 500 micrometers to about 1,000 micrometers, not more than about 10% by weight of said particles being smaller than about 200 micrometers and not more than about 10% by weight of said particles being larger than about 1,250 micrometers.
  • the percarbonate can be coated with silicate, borate or water- soluble surfactants.
  • Percarbonate is available from various commercial sources such as FMC, Solvay and Tokai Denka.
  • bleaching agent that can be used without restriction encompasses percarboxylic acid bleaching agents and salts thereof. Suitable examples of this class of agents include magnesium monoperoxyphthalate hexahydrate, the magnesium salt of metachloro perbenzoic acid, 4-nonylamino-4-oxoperoxybutyric acid and diperoxydodecanedioic acid.
  • Such bleaching agents are disclosed in U.S. Patent 4,483,781, Hartman, issued November 20, 1984, U.S. Patent Application 740,446, Burns et al, filed June 3, 1985, European Patent Application 0,133,354, Banks et al, published February 20, 1985, and U.S. Patent 4,412,934, Chung et al, issued November 1, 1983.
  • Highly preferred bleaching agents also include 6-nonylamino-6-oxoperoxycaproic acid as described in U.S. Patent 4,634,551, issued January 6, 1987 to Burns et al.
  • bleaching agents can also be used.
  • Peroxygen bleaching agents, the perborates, e.g., sodium perborate (e.g., mono- or tetra-hydrate) , the percarbonates, etc. are preferably combined with bleach activators, which lead to the in situ production in aqueous solution (i.e., during the washing process) of the peroxy acid corresponding to the bleach activator.
  • bleach activators e.g., sodium perborate (e.g., mono- or tetra-hydrate)
  • bleach activators e.g., sodium perborate (e.g., mono- or tetra-hydrate)
  • bleach activators e.g., sodium perborate (e.g., mono- or tetra-hydrate)
  • bleach activators e.g., mono- or tetra-hydrate
  • RlN(R5)C(0)R2C(0)L or R1C(0)N(R*5)R2C(0)L wherein R is an alkyl group containing from about 6 to about 12 carbon atoms, R2 is an alkylene containing from 1 to about 6 carbon atoms, R5 is H or alkyl, aryl, or alkaryl containing from about 1 to about 10 carbon atoms, and L is any suitable leaving group.
  • a leaving group is any group that is displaced from the bleach activator as a consequence of the nucleophilic attack on the bleach activator by the perhydrolysis anion.
  • a preferred leaving group is phenyl sulfonate.
  • bleach activators of the above formulae include (6-octanamido-caproyl)oxybenzenesulfonate, (6- nonanamidocaproyl)- oxybenzenesulfonate, (6-decanamido- caproyl)oxybenzenesulfonate, and mixtures thereof as described in U.S. Patent 4,634,551 , incorporated herein by reference.
  • lactam activators include benzoyl caprolactam, octanoyl caprolactam, 3,5,5- trimethylhexanoyl caprolactam, nonanoyl caprolactam, decanoyl caprolactam, undecenoyl caprolactam, benzoyl valerolactam, octanoyl valerolactam, decanoyl valerolactam, undecenoyl valerolactam, nonanoyl valerolactam, 3,5,5-trimethylhexanoyl valerolactam and mixtures thereof. See also U.S. Patent 4,545,784, issued to Sanderson, October 8, 1985, incorporated herein by reference, which discloses acyl caprolactams, including benzoyl caprolactam, adsorbed into sodium perbor
  • Bleaching agents other than oxygen bleaching agents are also known in the art and can be utilized herein.
  • One type of non-oxygen bleaching agent of particular interest includes photoactivated bleaching agents such as the sulfonated zinc and/or aluminum phthalocyanines. See U.S. Patent 4,033,718, issued July 5, 1977 to Holcombe et al. If used, detergent compositions will typically contain from 0.025% to 1.25%, by weight, of such bleaches, especially sulfonate zinc phthalocyanine.
  • the bleaching compounds can be catalyzed by means of a manganese compound.
  • a manganese compound Such compounds are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. Pat. 5,246,621, U.S. Pat. 5,244,594; U.S. Pat. 5,194,416; U.S. Pat. 5,114,606; and European Pat. App. Pub. Nos.
  • Preferred examples of these catalysts include Mn ⁇ 2( u "0 3 l ,4,7-trimethyl-l ,4,7-triazacyclononane)2(PF6)2, Mnm2(u-0) ⁇ (u-OAc)2(l,4,7-trimethyl-l,4,7-triazacyclononane)2- (Cl ⁇ 4)2, Mn IV 4(u-0)6(l,4,7-triazacyclononane)4(Cl ⁇ 4)4, Mn ⁇ lMn ⁇ (u-0) ⁇ (u-OAc)2-(l,4,7-trimethyl-l,4,7-triazacyclononane)2(Cl ⁇ 4)3, Mn IV (l,4,7-trimethyl-l,4,7-triazacyclononane)- (OCH3)3(PF6), and mixtures thereof.
  • metal-based bleach catalysts include those disclosed in U.S. Pat. 4,430,243 and U.S. Pat. 5,114,611.
  • the use of manganese with various complex ligands to enhance bleaching is also reported in the following United States Patents: 4,728,455; 5,284,944; 5,246,612; 5,256,779; 5,280,117; 5,274,147; 5,153,161; 5,227,084;
  • the detergent composition may comprise any other ingredients commonly employed in conventional detergent compositions such as soaps, polymeric soil release agents, anti- redeposition agents, polymeric dispersing agents, suds suppressors, dye transfer inhibitors, perfumes, softeners, brighteners, enzymes and enzyme stabilisers.
  • the detergent compositions of the present invention may be in granular, liquid or gel form or bar form. Preferably the compositions are granular.
  • the detergent compositions may be prepared by combining the ingredients in the required amounts in any suitable order by conventional means. When formulated as free following particles i.e in powdered or granulated form any conventional technique employed in the manufacture of detergent compositions may be used. To prevent premature hydrolysis of the compounds of the present invention in the formulation prior to washing, the maintenance of elevated temperatures under alkaline aqueous conditions should be avoided. Consequently, dry-mixing, agglomeration, granulation and extrusion techniques are preferable means of producing free flowing particle compositions.
  • the cationic compounds can be synthesised by methods known in the art.
  • reaction mixture was left to stir for 16 hours at room temperature after which the white precipitate of pyridinium chloride was filtered off and the reaction mixture was washed with distilled water (3x150 ml), dried over MgS04 and the solvent removed under reduced pressure, yielding l-[(4-chloromethyl)benzoyloxy](2-butyl)-octanyl as a colourless oil which was subsequently dried under vacuum.
  • N,N-dimethylethanolamine (0.12 mol, 13.3 ml) was mixed with a solution of l-[4-chloromethylbenzoyloxy]2-butyl-octanyl (0.12 mol, 40.7 g) in chloroform (150 ml), and the reaction mixture was left to stir for 48 hours at room temperature. After removal of the solvent, the oil recovered was added dropwise to some petroleum spirit (40-60°C) on contact with which a white precipitate forms.
  • Thionyl chloride (50g, 0.42 mole) was placed in a 250ml round bottomed flask fitted with a magnetic stirrer, dropping funnel and reflux water condenser and equipped with calcium chloride drying tubes to prevent ingress of moisture. With stirring, at 20°C, 2-n-hexyldecanoic acid (50g, 0.195 mole) was added over 30 minutes via the dropping funnel. The resulting reaction mixture was heated to 40°C, by means of an oil bath, and stirred at that temperature for 3 hours, completeness of reaction being confirmed by infra-red spectroscopy. Excess thionyl chloride and residual, by-product gases were removed by means of a rotary vacuum evaporator to yield 53g of liquid product.
  • N,N-dimethylethanolamine (34.4g, 0.386 mole) and 100ml of diethyl ether were placed in a 500ml round bottomed flask fitted with a magnetic stirrer, dropping funnel and reflux condenser and equipped with calcium chloride tubes to prevent ingress of moisture.
  • 2-n-hexyldecanoyl chloride 53g, 0.193 mole
  • the resulting suspension was heated to reflux, by means of an oil bath, and stirred at that temperature for 2 hours.
  • by-product hydrochloride was removed by filtration and then the ether was removed by means of a rotary vacuum evaporator to yield 63g of liquid product.
  • reaction mixture was stirred at 0°C for 3 hours and then, with continued stirring, a further 18g (0.19 mole) of precooled (0°C) methyl bromide was quickly added via the dropping funnel.
  • the condenser and dropping funnel were removed from the flask which was then stoppered and allowed to stand, at 20°C, for 72 hours.
  • the flask was cooled to 0°C by means of an ice bath and, with stirring, 150mls of a 20% w/v solution of phosgene in toluene (0.30 mole of phosgene) was added over 30 minutes. The resulting reaction mixture was allowed to warm to 20°C and stirred at that temperature for 2 hours.
  • the dropping funnel was removed from the flask which was then stoppered and allowed to stand, at 20 °C, for 18 hours.
  • the toluene and residual phosgene and hydrogen chloride were removed by means of a rotary vacuum evaporator to yield 63g of liquid product.
  • the product was characterised by infra-red spectroscopy (chloroformate carbonyl, singlet 1780 cm-1).
  • granular detergent compositions are prepared by combining the listed ingredients in the amounts indicated below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention concerne des composés cationiques et leur utilisation dans des compositions détergentes. Ces composés présentent le double avantage d'être tensioactifs et de supprimer l'effet moussant.
PCT/US1995/011797 1994-09-22 1995-09-18 Compositions detergentes WO1996009276A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP95933835A EP0782561A4 (fr) 1994-09-22 1995-09-18 Compositions detergentes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9419099A GB9419099D0 (en) 1994-09-22 1994-09-22 Detergent composition
GB9419099.8 1994-09-22

Publications (1)

Publication Number Publication Date
WO1996009276A1 true WO1996009276A1 (fr) 1996-03-28

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PCT/US1995/011797 WO1996009276A1 (fr) 1994-09-22 1995-09-18 Compositions detergentes

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EP (1) EP0782561A4 (fr)
GB (1) GB9419099D0 (fr)
WO (1) WO1996009276A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0842246A1 (fr) * 1995-07-08 1998-05-20 The Procter & Gamble Company Composition detergente comprenant un tensioactif cationique du type ester et une protease
EP0912703A1 (fr) * 1996-05-31 1999-05-06 The Procter & Gamble Company Compositions detergentes
US10570452B2 (en) 2009-04-06 2020-02-25 Vanda Pharmaceuticals, Inc. Method of predicting a predisposition to QT prolongation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228042A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group
US5021197A (en) * 1988-06-16 1991-06-04 Mitsubishi Gas Chemical Company, Inc. Process for production of sulfonium compounds
US5047577A (en) * 1985-10-01 1991-09-10 Ethyl Corporation Quaternary ammonium compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2148097A1 (fr) * 1992-11-30 1994-06-09 Jean-Pol Boutique Nettoyage a l'aide de surfactifs mixtes non ioniques/anioniques, a base d'amide d'acide gras polyhydroxyle, produisant peu de mousse

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228042A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group
US5047577A (en) * 1985-10-01 1991-09-10 Ethyl Corporation Quaternary ammonium compounds
US5021197A (en) * 1988-06-16 1991-06-04 Mitsubishi Gas Chemical Company, Inc. Process for production of sulfonium compounds

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0782561A4 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0842246A1 (fr) * 1995-07-08 1998-05-20 The Procter & Gamble Company Composition detergente comprenant un tensioactif cationique du type ester et une protease
EP0842246A4 (fr) * 1995-07-08 2000-01-12 Procter & Gamble Composition detergente comprenant un tensioactif cationique du type ester et une protease
EP0912703A1 (fr) * 1996-05-31 1999-05-06 The Procter & Gamble Company Compositions detergentes
EP0912703A4 (fr) * 1996-05-31 1999-12-01 Procter & Gamble Compositions detergentes
US10570452B2 (en) 2009-04-06 2020-02-25 Vanda Pharmaceuticals, Inc. Method of predicting a predisposition to QT prolongation

Also Published As

Publication number Publication date
GB9419099D0 (en) 1994-11-09
EP0782561A1 (fr) 1997-07-09
EP0782561A4 (fr) 1998-01-28

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