WO2000078908A1 - Detergent particles and processes for making them - Google Patents
Detergent particles and processes for making them Download PDFInfo
- Publication number
- WO2000078908A1 WO2000078908A1 PCT/US2000/016916 US0016916W WO0078908A1 WO 2000078908 A1 WO2000078908 A1 WO 2000078908A1 US 0016916 W US0016916 W US 0016916W WO 0078908 A1 WO0078908 A1 WO 0078908A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- detergent
- mixer
- acid
- mean particle
- base particles
- Prior art date
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- 239000003599 detergent Substances 0.000 title claims abstract description 261
- 239000002245 particle Substances 0.000 title claims abstract description 161
- 238000000034 method Methods 0.000 title claims abstract description 51
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- 238000002156 mixing Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 130
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- 230000000694 effects Effects 0.000 claims description 3
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- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000014366 other mixer Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- BTRXYXNWHKNMAB-UHFFFAOYSA-N phosphoric acid;dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.OP(O)(O)=O BTRXYXNWHKNMAB-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- IFIDXBCRSWOUSB-UHFFFAOYSA-N potassium;1,3-dichloro-1,3,5-triazinane-2,4,6-trione Chemical compound [K+].ClN1C(=O)NC(=O)N(Cl)C1=O IFIDXBCRSWOUSB-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- NJKRDXUWFBJCDI-UHFFFAOYSA-N propane-1,1,2,3-tetracarboxylic acid Chemical class OC(=O)CC(C(O)=O)C(C(O)=O)C(O)=O NJKRDXUWFBJCDI-UHFFFAOYSA-N 0.000 description 1
- NJEVMKZODGWUQT-UHFFFAOYSA-N propane-1,1,3,3-tetracarboxylic acid Chemical class OC(=O)C(C(O)=O)CC(C(O)=O)C(O)=O NJEVMKZODGWUQT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BZYSAMJFNABQQM-UHFFFAOYSA-M sodium boric acid hydrogen carbonate 2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound C([O-])(O)=O.B(O)(O)O.[Na+].B(O)(O)O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O BZYSAMJFNABQQM-UHFFFAOYSA-M 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
- MSFGZHUJTJBYFA-UHFFFAOYSA-M sodium dichloroisocyanurate Chemical compound [Na+].ClN1C(=O)[N-]C(=O)N(Cl)C1=O MSFGZHUJTJBYFA-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- QSKQNALVHFTOQX-UHFFFAOYSA-M sodium nonanoyloxybenzenesulfonate Chemical compound [Na+].CCCCCCCCC(=O)OC1=CC=CC=C1S([O-])(=O)=O QSKQNALVHFTOQX-UHFFFAOYSA-M 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- PYILKOIEIHHYGD-UHFFFAOYSA-M sodium;1,5-dichloro-4,6-dioxo-1,3,5-triazin-2-olate;dihydrate Chemical compound O.O.[Na+].[O-]C1=NC(=O)N(Cl)C(=O)N1Cl PYILKOIEIHHYGD-UHFFFAOYSA-M 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- RPQSWSMNPBZEHT-UHFFFAOYSA-M sodium;2-acetyloxybenzenesulfonate Chemical compound [Na+].CC(=O)OC1=CC=CC=C1S([O-])(=O)=O RPQSWSMNPBZEHT-UHFFFAOYSA-M 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- KQHKITXZJDOIOD-UHFFFAOYSA-M sodium;3-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=CC(C([O-])=O)=C1 KQHKITXZJDOIOD-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000004173 sunset yellow FCF Substances 0.000 description 1
- 235000012751 sunset yellow FCF Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004026 tertiary sulfonium compounds Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
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
- C11D3/50—Perfumes
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
-
- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
- C11D17/065—High-density particulate detergent compositions
-
- 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
- C11D3/0063—Photo- activating compounds
Definitions
- the present invention relates to particulate detergent compositions and an improved process for making such compositions
- the detergent compositions of the invention are suitable for any cleaning process, such as laundry and dishwashing detergent compositions
- Such particulate compositions may be used directly m their particulate form or may first be formed into detergent tablets by any standard tablettmg process such as compaction
- detergent compositions In order to meet the needs of the consumer, in addition to providing good cleaning, detergent compositions must meet many additional requirements including good aesthetics, good flow properties, good solubility and good dispensing performance into wash water In order to meet all of these requirements, the complexity of detergent compositions and range of products offered has grown Formulation flexibility for producing such complex compositions is therefore extremely important and many methods for formulating detergent compositions are already known
- the present invention therefore reduces these problems by providing a process in which such low dosage/high impact ingredients can be dispersed uniformly throughout a detergent formulation Segregation is minimised without the need to incorporate high levels of fillers to form such low dosage/high impact ingredients into larger particles
- a method for making a detergent particles comprising selecting detergent base particles having a geomet ⁇ c mean particle diameter from 500 - 2000 microns, in a moderate to low shear mixer adhe ⁇ ng detergent active particulates to the detergent base particles, wherein the detergent active particulates have a geomet ⁇ c mean particle diameter no greater than 40% of the geometric mean particle diameter of the detergent base particles and comprise a detergent active selected from perfumes, enzymes, photobleaches. catalysts, soil release polymers, suds suppressors, bleaching compounds, whitening agents and layered silicates.
- the present invention also provides detergent particles produced by such a process, and detergent compositions incorporating these particles
- a detergent active particulate is bound to the detergent base particulate, the two components subsequently appearing in a detergent composition as an individual detergent particle.
- the detergent active particulates preferably have a geometric mean particle diameter which is below 200 ⁇ m, preferably below 150 ⁇ m and even below 100 ⁇ m.
- the geomet ⁇ c mean particle diameter of the detergent active particulates is generally above lO ⁇ m preferably above 20 ⁇ m and may even be above 40 ⁇ m or above 60 ⁇ m
- the phrase "geomet ⁇ c mean particle diameter" means the geometric mass median diameter of a set of discrete particles as measured by any standard mass- based particle size measurement technique, preferably by dry sieving
- a suitable sieving method is in accordance with ISO 31 18 (1976).
- a suitable device is the Ro-Tap testing sieve shaker Model B using 8 inch sieves of selected sizes.
- the phrase "geomet ⁇ c standard deviation" or “span” of a particle size distribution means the geomet ⁇ c breadth of the best-fitted log-normal function to the above-mentioned particle size data which can be accomplished by the ratio of the diameter of the 84.13 percentile divided by the diameter of the 50 th percentile of the cumulative distribution (D 84 , 3 /D 5 o); See Gotoh et al, Powder Technology Handbook, pp. 6-1 1 , Marcel Dekker 1997.
- the detergent base particles have a geometric mean particle diameter from 500 to
- the geomet ⁇ c mean particle diameter of the detergent base particles is generally greater than 550 ⁇ m or even greater than 600 ⁇ m or 650 ⁇ m. Preferably, the geomet ⁇ c mean particle diameter of the detergent base particles is below 1500 ⁇ m.
- the detergent particles produced preferably have a geomet ⁇ c standard deviation of from 1 to about 2, preferably from 1.0 to 1.7. more preferably from about 1.0 to about 1 4.
- Preferred fully formulated detergents comprising the detergent particles also have such a geomet ⁇ c standard deviation.
- the geometric mean particle diameter of the detergent active particulates is no greater than 20% of the geomet ⁇ c mean particle diameter of the detergent base particles more preferably no greater than 10% and may even be below 5% of the geometric mean particle diameter of the detergent base particles Generally m the detergent particles, no more than 25wt% is derived from the detergent active particulates, preferably no greater than 10 wt%. The invention may even be useful where the proportion of the detergent particles derived from the detergent active particulates is no greater than 5 or even no greater than 2 wt%.
- bulk density refers to the uncompressed, untapped powder bulk density, as measured by pouring an excess of particulate sample through a funnel into a smooth metal vessel (e.g. a 500ml volume cylinder) scraping off the excess off the heap above the nm of the vessel, measuring the remaining mass of powder and dividing the mass by the volume of the vessel.
- a smooth metal vessel e.g. a 500ml volume cylinder
- the bulk density of the detergent particles produced and also of the detergent base particles is generally above 200 g/1 and may be as high as 1500 g/1. It is particularly preferred that the bulk density a finished detergent composition compnsing the detergent particles produced according to the present invention is greater than 550 g/1, preferably greater than 600 g/1 or even above 650 g/1.
- the bulk density of the detergent particles produced is therefore generally from 400g/l to 1 100 g/1, generally above 500g/l or even above 550 or 650g/l, generally less than l OOOg/l or below 900g/l.
- the invention may be particularly useful for forming detergent particles having a low bulk density such as below 550 or even below 500 or 450 g 1.
- the detergent base particles for use m the method of the present mvention may compnse a single detergent ingredient m particulate form or may be a pre-mix of detergent ingredients. Where the detergent base particles comprise a pre-mix, the separate detergent ingredients may simply be mixed together or may comprise a pre-formed particulate compnsing any combination of two or more detergent ingredients, or mixtures thereof, optionally with single detergent ingredients. Suitable pre-formed particulates for the base particles may have been formed by spray-drymg, agglomeration, marume ⁇ sation. extrusion or compaction, all of which methods for combining detergent ingredients are well-known m the art.
- Particularly preferred pre-formed particulates are powders obtained from spray-drymg processes, agglomerates and extrudates. Spray-d ⁇ ed powders are particularly useful. Pre-formed particulates made according to at least one low shear mixing step, for example in a fluidised bed. for example by fluid bed agglomeration are particularly preferred. Particularly preferred particles are as described m our co-pending application filed today under reference number CM2158F.
- Suitable spray-drymg processes for forming such pre-formed particulates are desc ⁇ bed for example in EP-A-763594 or EP-A-437888.
- Suitable processes for forming pre-formed particulates which are agglomerates are described for example W093/25378, EP-A-367339, EP-A-420317 or EP-A-506184 and suitable processes for forming pre-formed particulates by extrusion are described for example in W091/02047.
- Such pre-formed particulates may be added to the mixer in their wet or dry state. They are preferably added to the mixer in their dry state as addition in their wet state may have an adverse effect on flow into the mixer. Alternatively it may be preferred that the pre-formed particulates are formed in a first stage of a moderate to low shear mixer and the detergent active particulates are added in a second stage so that the pre-formed particulates may be m a wet state when they are contacted with the detergent active particulates.
- the pre-formed particulate may be for example an agglomerate, blown powder or extrudate which has not yet undergone a final drying stage.
- a solvent used as a binding agent for the processing is present in higher amounts than are desirably present m a finished particulate detergent.
- the solvent is water and wet particulates will have a free water content for example of froml5 to 30 wt % of the pre-formed particulate.
- the pre-formed particulate will already have undergone a drying step prior to addition to the mixer so that the water content will be below 15 wt %, preferably below 10 wt %.
- the free water content of the detergent base particles on entry into the mixer will be below 15 wt %, preferably below 10 wt %.
- the detergent base particles comprise a surfactant or mixture of surfactants. Suitable surfactants are described below.
- the surfactant content of the detergent base particles or a pre-formed particulate component forming all or part of the detergent base particles is preferably from 5 to 80 % by weight of the particulate component. Amounts of surfactants above 10 or even above 30% may be preferred. Amounts of surfactant below 70% or even below 50% may be preferred.
- the detergent base pre-formed particulate component comprises surfactant, generally it will in addition comprise a builder or alkalinity agent such as sodium carbonate, zeolite, or phosphate.
- each of these components individually, or m mixtures may be present m amounts above 5%, preferably above 10% or even above 20% by weight of the content of the pre-formed particulate component.
- Particularly preferred builder components are sodium carbonate and/or zeolite. Zeolite A and zeolite MAP are both suitable.
- the detergent base particles preferably also comprises an organic builder such as a poly carboxylic acid and/or salt such as citric acid, tarta ⁇ c acid, malic acid, succimc acid and their salts or a polymeric polycarboxylate such as polymers based on acrylic acids or maleic acids or co-polymers thereof.
- Such components are generally present in the particle at levels below 15 wt % of the paniculate component, preferably below 10 wt % of the particulate component
- chelants such as phosphonate chelants NTA, DTPA and succi c acid derivative chelants. as desc ⁇ bed below
- these components are preferably present in the detergent base particles m amounts below 5 wt % or even below 2 wt %
- Suds supressors and/or soil release polymers and/or bleach activators are also preferred ingredients m pre-formed particulates
- Suitable detergent ingredients for incorporation either into the detergent particles themselves, or for post-addition to formulate a fully formulated detergent composition are discussed below.
- the detergent active particulates are selected from perfumes, enzymes, photobleaches, catalysts, soil release polymers, suds suppressors, bleaching compounds, whitening agents and layered silicates.
- Preferred detergent active particulates comprise perfume. Any perfume or perfume composition can be used. However, it must be solid or m combination with other components so that it has a solid form. For example it may be loaded onto a particulate earner such as zeolite, or any other known solid carrier, for example as described in WO94/16046, ES93000006, EP-A- 535942, and EP-A-294206. More preferably it is present m encapsulated form. Suitable encapsulates are described for example m W094/12613. EP-A-539025, EP-A-478326, EP-A-
- EP-A-382464 EP-A-346034, EP-A-70719.
- Particularly preferred encapsulates compnse starch.
- Preferred perfumes contain at least one component with a low molecular weight volatile component, e.g. having a molecular weight of from 150 to 450 or preferably 350.
- the perfume component comprises an oxygen-contammg functional group.
- Preferred functional groups are aldehyde, ketone. alcohol or ether functional groups or mixtures thereof.
- the detergent active particulates may comprise one or more enzymes.
- Suitable enzymes include the commercially available lipases. cutmases. amvlases. neutral and alkaline proteases, cellulases. endolases, esterases, pectmases, lactases and peroxidases conventionally incorporated into detergent compositions. Suitable enzymes are discussed in US Patents 3,519,570 and 3,533,139.
- Preferred commercially available protease enzymes include those sold under the tradenames Alcalase, Savmase, P ⁇ mase, Durazym. and Esperase by Novo Industries A/S
- Protease enzyme may be incorporated into the compositions in accordance with the invention at a level of from 0.0001% to 4% active enzyme by weight of the composition.
- Preferred amylases include, for example, ⁇ -amylases, described m more detail m GB- 1,269,839 (Novo).
- Preferred commercially available amylases include for example, those sold under the tradename Rapidase by Gist-Brocades, and those sold under the tradename Termamyl, Duramyl and BAN by Novo Industries A/S.
- Preferred amylase enzymes may be those described in PCT/ US 9703635, and in W095/26397 and W096/23873.
- Amylase enzyme may be incorporated into the composition accordance with the invention at a level of from 0.0001% to 2% active enzyme by weight.
- Lipolytic enzyme may be present at levels of active hpolytic enzyme of from 0.0001% to 2% by weight, preferably 0.001% to 1% by weight, most preferably from 0.001% to 0.5% by weight based on the content in the final detergent composition.
- the lipase may be fungal or bacterial in origin being obtained, for example, from a lipase producing strain of Humicola sp., Thermomyces sp. or Pseudomonas sp. including Pseudomonas pseudoalcah genes or Pseudomas fluorescens. Lipase from chemically or genetically modified mutants of these strains are also useful herein.
- a preferred lipase is derived from Pseudomonas pseudoalcaligenes, which is described in EP-B-0218272.
- Another preferred lipase is obtained by cloning the gene from Humicola lanuginosa and expressing the gene in Aspergillus oryza. as host, as described m European Patent Application, EP-A-0258 068, which is commercially available from Novo Industri A/S, Bagsvaerd, Denmark, under the trade name Lipolase.
- This lipase is also described in U.S. Patent 4,810,414. Huge-Jensen et al, issued March 7, 1989.
- Photobleaches Preferred detergent active particulates comprise photobleach particles
- Preferred photo- bleaches herein comprise a compounds having a porphin or porphyrin structure Porphm and porphyrin. in the literature, are used as synonyms, but conventional] ⁇ porphin stands for the simplest porphyrin w ithout any substituents.
- m porphyrin is a sub-class of porphin
- the references to porphin m this application will include porphynn
- the porphin structures preferably comprise a metal element or cation, preferably Ca, Mg, P. Ti, Cr, Zr, In. Sn or Hf, more preferably Ge, Si or Ga. or more preferably Al . most preferably Zn.
- the photo-bleach or component is substituted with substituents selected from alkyl groups such as methyl, ethyl, propyl, t-butyl group and aromatic ring systems such as pyridyl, pyndyl-N-oxide, phenyl, naphthyl and anthracyl moieties.
- alkyl groups such as methyl, ethyl, propyl, t-butyl group and aromatic ring systems such as pyridyl, pyndyl-N-oxide, phenyl, naphthyl and anthracyl moieties.
- One preferred group of photobleaches comprise a polymeric component and a photobleaching component integrated with one another, whereby the weight ratio of polyme ⁇ c component to photobleaching component is from 1.1 to 1000.1, preferably 20:1 to 100:1
- Particularly preferred polymenc compounds are formed from monome ⁇ c units selected from N- vmylpyrolidone, N-vmylacetamide, N-vmyl lmidazole, N-vmyl oxazohdone, N-v yltnazole, 4- vmylpyridme and 4-v ⁇ nylpy ⁇ l ⁇ dme-N-ox ⁇ de.
- Preferred photo-bleachmg compounds are metals, preferably zmc, phthalocyammes or aluminium Such photo-bleaches are described in GB 2329397A.
- esters may be made using additional monomers capable of being incorporated into the ester structure through one. two. three, four or more positions, without, of course, forming a densely crosshnked overall structure.
- Suitable SRPs include a sulfonated product of a substantially linear ester ohgomer comprised of an ohgome ⁇ c ester backbone of terephthaloyl and oxyalkyleneoxy repeat units and allyl-de ⁇ ved sulfonated terminal moieties covalently attached to the backbone, for example as described in U.S. 4,968,451, November 6, 1990 to J.J. Scheibel and E P Gosselmk.
- SRA's include: the partly- and fully- anio c-end-capped oligome ⁇ c esters of U.S. 4,721,580, January 26, 1988 to Gosselmk, such as ohgomers from ethylene glycol ("EG"), PG, DMT and Na-3,6-d ⁇ oxa-8-hydroxyoctanesulfonate; the nonio c-capped block polyester o gomenc compounds of U.S. 4,702,857.
- SRPs also include: simple copolyme ⁇ c blocks of ethylene terephthalate or propylene terephthalate with polyethylene oxide or polypropylene oxide terephthalate, see U.S. 3,959,230 to Hays, May 25, 1976 and U.S.
- cellulosic derivatives such as the hydroxyether cellulosic polymers available as METHOCEL from Dow; the C ] -C alkyl celluloses and C_ ⁇ hydroxyalkvl celluloses, see U.S. 4,000,093, December 28, 1976 to Nicol, et al.; and the methyl cellulose ethers having an average degree of substitution (methyl) per anhydroglucose unit from about 1.6 to about 2.3 and a solution viscosity of from about 80 to about 120 centipoise measured at 20°C as a 2% aqueous solution.
- Such materials are available as METOLOSE SMI 00TM and METOLOSE SM200TM. which are methyl cellulose ethers manufactured by Shin-etsu Kagaku Kogyo KK.
- a highly preferred particulate suds suppressing system is described in EP-A-0210731 and compnses a sihcone antifoam compound and an organic earner material having a melting point m -l i ⁇
- R ] is anilmo.
- R2 is morphihno and M is a cation such as sodium
- the brightener is 4.4'-b ⁇ s[(4-an ⁇ l ⁇ no-6-morph ⁇ l ⁇ no-s-t ⁇ az ⁇ ne-2-yl)ammo]2,2'- stilbenedisulfo c acid, sodium salt.
- This particular brightener species are sold by Ciba Geigy Corporation as Tinopal-DMS-XTM and Tinopal AMS-GXTM.
- Lavered Silicates Suitable cry stalline layered silicates are described for example in US 4.664,839 Crystalline layered silicates rich in delta-phase are preferred such as those described in W097/19156 Catalysts
- the detergent active particulates may also comprise catalyst particulates Suitable catalysts include transition metal-containmg bleach catalyst
- One suitable type of bleach catalyst is a catalyst system comprising a heavy metal cation of defined bleach catalytic activity, such as copper, iron or manganese cations, an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminium cations, and a sequestrant/chelant havmg defined stability constants for the catalytic and auxiliary metal cations, particularly ethyl enediamine tetraacetic acid, ethylenediamme tetra(methvlenephosphon ⁇ c acid) and water-soluble salts thereof
- a heavy metal cation of defined bleach catalytic activity such as copper, iron or manganese cations
- an auxiliary metal cation having little or no bleach catalytic activity such as zinc or aluminium cations
- a sequestrant/chelant havmg defined stability constants for the catalytic and
- bleach catalysts include the manganese-based complexes disclosed US 5,246,621 and US 5.244,594 Preferred examples of these catalysts include MnTV2(u-0)3( 1,4,7- tnmethyl-l,4,7-triazacyclononane)2-(PF6)2, MnIII2(u-0)l(u-Oac)2(l J 4.7-t ⁇ methul- 1,4,7- tnazacyclononane)2-(C104)2, MnIV4(u-0)6( 1 ,4,7-t ⁇ axacyclononane)4-(C104)2, Mn ⁇ TMnrV4(u-0)l(u-Oac)2-(l ,4,7-t ⁇ methyl-l ,4,7-tr ⁇ azacyclononane)2-(C104)3, and mixtures thereof Others are described in EP-A-549272 Other suitable ligands include 1,5,9-tnmethyl- 1,5,9-triazacyclodo
- the preferred proportion of detergent active particulates to detergent base powder will vary dependent upon the relative particle sizes of these two components.
- the weight percentage of any one of the detergent active particulates will be no greater than 10wt%, preferably below 5 wt% or even below 2 or 1 wt% of the detergent base particles
- the geometric mean particle size of the detergent active particulates is no greater than 20%, preferably no greater than 10 % or even below 5 or even 2 or 1% of the geometric mean particle size of the detergent base particles.
- detergent base particles of the present invention are passed into a fluid bed optionally having multiple internal "stages" or “zones"
- a stage or zone is any discrete area within the fluid bed. and these terms are used interchangeably herein
- the process conditions within a stage may be different or similar to the other stages the fluid bed/dryer It is understood that two adjacent fluid beds are equivalent to a single fluid bed having multiple stages.
- the various feed streams of detergent base particles and detergent active particulates can be added either at the same or at the different stages, depending on. for example, the particle size and moisture level of the feed stream Feeding different streams to different stages can minimize the heat load on the fluid bed. and optimize the particle size and increase uniformity of the shape of the detergent particles produced
- any anionic surfactants useful for detersive purposes can be comprised in the detergent composition. These can include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of the anionic sulfate. sulfonate, carboxylate and sarcosinate surfactants. Anionic sulfate and sulfonate surfactants are preferred.
- the anionic surfactants may be present m the detergent particle in amounts below 25 WT % or even below 20 wt % but in a final detergent composition comprising the particle, is preferably present at a level of from 0.1 % to 60%. more preferably from 1 to 40%. most preferably from 5% to 30% by weight.
- anionic surfactants include the anionic carboxylate surfactants such as alkyl ethoxy carboxylates, alkyl polyethoxy polycarboxylates and soaps ("alkyl carboxyls") such as water- soluble members selected from the group consisting of the water-soluble salts of 2-methyl-l - undecanoic acid, 2-ethyl-l -decano ⁇ c acid, 2-propyl-l -nonano ⁇ c acid. 2-butyl-l-octano ⁇ c acid and 2-pentyl-l -heptano ⁇ c acid. Certain soaps may also be included as suds suppressors.
- suitable anionic surfactants are the alkali metal sarcos ates of formula R-CON (R ⁇ ) CH2
- Preferred surfactant combinations are mixtures of the preferred alkyl sulfate and/ or sulfonate and alkyl ethoxysulfate surfactants optionally with catiomc surfactant. Such mixtures have been disclosed PCT Patent Application No WO 93/18124
- Anionic sulfonate surfactants suitable for use herein include the salts of C5-C20 linear alkylbenzene sulfonates, alkyl ester sulfonates, Cg-C22 primary or secondary alkane sulfonates.
- Polyhydroxy fatty acid amides suitable for use herein are those having the structural formula R 2 CONR 1 Z wherein : RI is H, C1-C4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl, ethoxy, propoxy, or a mixture thereof, preferable C j -C4 alkyl: and R2 is a C5-C31 hydrocarbyl; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof.
- Z preferably will be derived from a reducing sugar m a reductive animation reaction; more preferably Z is a glycityl.
- Suitable alkylpolysaccha ⁇ des for use herein are disclosed in U.S. Patent 4,565,647,
- alkylpolyglycosides have the formula:
- R2 ⁇ (C n H 2n O)t(glycosyl) x wherem R*- is selected from the group consisting of alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl. and mixtures thereof in which the alkyl groups contain from 10 to 18 carbon atoms; n is 2 or 3; t is from 0 to 10. and x is from 1.3 to 8.
- the glycosyl is preferably derived from glucose.
- Suitable amphote ⁇ c surfactants for use herein include the amine oxide surfactants and the alkyl amphocarboxyhc acids.
- Suitable amine oxides include those compounds having the formula R ⁇ (OR 4 ) ⁇ N ⁇ (R ⁇ )2 wherem R ⁇ is selected from an alkyl, hydroxyalkyl, acylamidopropoyl and alkyl phenyl group, or mixtures thereof, containing from 8 to 26 carbon atoms; R 4 is an alkylene or hydroxyalkylene group containing from 2 to 3 carbon atoms, or mixtures thereof; x is from 0 to 5, preferably from 0 to 3; and each R ⁇ is an alkyl or hydroxyalkyl group containing from 1 to 3, or a polyethylene oxide group containing from 1 to 3 ethylene oxide groups.
- Prefe ⁇ ed are C ] j -C ⁇ g alkyl dimethylamine oxide, and C ⁇ _,. ⁇ acylamido alkyl dimethylamine oxide.
- Zwitterionic surfactants can also be incorporated into the detergent compositions in accord with the invention. These surfactants can be broadly described as denvatives of secondary and tertiary ammes, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds. Betaines such as Ci 2- ] dimethyl-ammonio hexanoate and the Cj Q -i g acylamidopropane (or ethane) dimethyl (or diethyl) betaines and sultame surfactants are exemplary zwittenonic surfactants for use herein.
- Suitable cationic surfactants to be used herein include the quaternary ammonium surfactants.
- the quaternary ammonium surfactant is a mono C ⁇ -Cj ⁇ , preferably Cg-
- N-alkyl or alkenyl ammonium surfactants wherein the remaining N positions are substituted by methyl, hydroxyethyl or hydroxypropyl groups.
- Preferred are also the mono-alkoxylated and bis-alkoxylated amine surfactants.
- Cationic ester surfactants such as cho ne ester surfactants, have for example been disclosed in US Patents No.s 4228042, 4239660 and 4260529 are also suitable as are cationic mono-alkoxylated amme surfactants preferably of the general formula I: R' ⁇ ((CH 2 ) 2 . 4 O),. 5 H
- R * is Cj -Cj g hydrocarbyl and mixtures thereof, especially C ⁇ Q-C _ alkyl, preferably
- CJ Q and Ci 2 alkyl. and X is any convenient anion to provide charge balance, preferably chlonde or bromide
- the levels of the cationic mono-alkoxylated amine surfactants in the detergent compositions of the invention are generally from 0 1% to 20%, preferably from 0.2% to 7%, most preferably from 0.3% to 3.0% by weight
- Cationic bis-alkoxylated amine surfactant such as
- R 1 is C j Q -C j hydrocarbyl and mixtures thereof, preferably C J O, C ⁇ 2, C]4 alkyl and mixtures thereof.
- X is any convenient anion to provide charge balance, preferably chloride.
- the detergent particles or detergent compositions containing them preferably compnse a bleach activator, preferably comprising an organic peroxyacid bleach precursor. It may be preferred that the composition comprises at least two peroxy acid bleach precursors, preferably at least one hydrophobic peroxyacid bleach precursor and at least one hydrophihc peroxy acid bleach precursor, as defined herein.
- the production of the organic peroxyacid occurs then by an in situ reaction of the precursor with a source of hydrogen peroxide.
- the bleach activator may alternatively, or addition comprise a preformed peroxy acid bleach
- bleach activator is present in the detergent particle. It may be preferred that the bleach activator is present as a separate, admixed particle.
- Preferred hydrophobic peroxy acid bleach precursor preferably comprise a compound having an oxy- benzene sulphonate group, preferably NOBS, DOBS, LOBS and or NACA-OBS
- Preferred hydrophihc peroxy acid bleach precursors preferably compnses TAED
- Peroxyacid bleach precursors are compounds which react with hydrogen peroxide in a perhydrolysis reaction to produce a peroxyacid.
- peroxyacid bleach precursors may be represented as
- hydrophobic peroxyacid bleach precursors produce a peroxy acid of the formula above wherem X is a group comprising at least 6 carbon atoms and a hydrophihc peroxyacid bleach precursor produces a peroxyacid bleach of the formula above wherem X is a group comprising 1 to 5 carbon atoms.
- L group The leaving group, hereinafter L group, must be sufficiently reactive for the perhydrolysis reaction to occur within the optimum time frame (e.g., a wash cycle). However, if L is too reactive, this activator will be difficult to stabilize for use m a bleaching composition.
- Preferred L groups are selected from the group consisting of:
- R is an alkyl. aryl, or alkaryl group containing from 1 to 14
- R is an alkyl chain containing from 1 to 8 carbon atoms.
- R is H or R
- Y is
- R , R and R may be substituted by essentially any functional group including, for example alkyl, hydroxy, alkoxy, halogen, amine, mtrosyl, amide and ammonium or alkyl ammmonium groups
- the preferred solubilizing groups are -SO- ' M , -CO- ' M , -SO " M , -N (R ) 4 X " and
- M is an alkyl chain containing from 1 to 4 carbon atoms
- M is a cation which provides solubility to the bleach activator
- X is an anion which provides solubility to the bleach activator.
- M is an alkali metal, ammonium or substituted ammonium cation, with sodium and potassium being most preferred
- X is a halide, hydroxide, methylsulfate or acetate anion.
- Peroxyacid bleach precursor compounds are preferably present m final detergent compositions at a level of from 0.5% to 30% by weight, more preferably from 1% to 15% by weight, most preferably from 1.5% to 10% by weight
- the ratio of hydrophihc to hydrophobic bleach precursors, when present, is preferably from 10: 1 to 1 10. more preferably from 5; 1 to 1 :5 or even from 3:1 to 1.3.
- Suitable peroxyacid bleach precursor compounds typically contain one or more N- or O-acyl groups, which precursors can be selected from a wide range of classes. Suitable classes include anhyd ⁇ des, esters, lmides, lactams and acylated denvatives of lmidazoles and oximes.
- Alkyl percarboxyhc acid bleach precursors form percarboxyhc acids on perhydrolysis Preferred precursors of this type provide peracetic acid on perhydrolysis Preferred alkyl percarboxyhc precursor compounds of the imide type include the N-,N,N ⁇ N' tetra acetylated alkylene diam es wherem the alkylene group contains from 1 to 6 carbon atoms, particularly those compounds in which the alkylene group contains 1.
- Tetraacetyl ethylene diamme is particularly preferred as hydrophihc peroxy acid bleach precursor
- Other prefe ⁇ ed alkyl percarboxyhc acid precursors include sodium 3, 5.5 -tn -methyl hexanoyloxybenzene sulfonate (iso-NOBS).
- NOBS nonanoyloxybenzene sulfonate
- ABS acetoxybenzene sulfonate
- pentaacetyl glucose Amide substituted alkyl peroxyacid precursor compounds are suitable herein, including those of the following general formulae-
- R' is an aryl or alkaryl group with from about 1 to about 14 carbon atoms
- R 2 is an alkylene, arylene, and alkarylene group containing from about 1 to 14 carbon atoms
- R ⁇ is H or an alkyl, aryl, or alkaryl group containing 1 to 10 carbon atoms and L can be essentially any leaving group.
- R 1 preferably contains from about 6 to 12 carbon atoms
- R 2 preferably contains from about 4 to 8 carbon atoms.
- R ⁇ may be straight chain or branched alkyl, substituted aryl or alkylaryl containing branching, substitution, or both and may be sourced from either synthetic sources or natural sources including for example, tallow fat. Analogous structural vanations are permissible for R ⁇ .
- R2 can include alkyl, aryl, wherem said R 2 may also contain halogen, nitrogen, sulphur and other typical substituent groups or organic compounds.
- R ⁇ is preferably H or methyl.
- R* and R ⁇ should not contain more than 18 carbon atoms total Amide substituted bleach activator compounds of this type are described in EP-A-0170386. It can be preferred that
- R and R-> forms together with the nitrogen and carbon atom a ring structure
- bleach precursors of this type include amide substituted peroxyacid precursor compounds selected from (6-octanam ⁇ do-caproyl)oxybenzenesulfonate, (6- decanamido-caproyl) oxybenzene- sulfonate, and the highly preferred (6-nonanam ⁇ docaproyl)oxy benzene sulfonate, and mixtures thereof as descnbed m EP-A-0170386
- Perbenzoic acid precursor compounds which provide perbenzoic acid on perhydrolysis benzoxazm organic peroxyacid precursors, as disclosed for example in EP-A-332294 and EP-A- 482807 and cationic peroxyacid precursor compounds which produce cationic peroxyacids on perhydrolysis are also suitable Cationic peroxyacid precursors are described in U.S.
- Suitable cationic peroxyacid precursors include any of the ammonium or alkyl ammonium substituted alkyl or benzoyl oxybenzene sulfonates, N-acylated caprolactams, and monobenzoyltetraacetyl glucose benzoyl peroxides
- Preferred cationic peroxyacid precursors of the N-acylated caprolactam class include the t ⁇ alkyl ammonium methylene benzoyl caprolactams and the t ⁇ alkyl ammonium methylene alkyl caprolactams.
- the particles or compositions of the present invention may contain, in addition to, or as an alternative to an organic peroxyacid bleach precursor compound, a preformed organic peroxyacid , typically at a level of from 0.1% to 15% by weight, more preferably from 1% to 10% by weight.
- a preferred class of organic peroxyacid compounds are the amide substituted compounds as described m EP-A-0170386.
- Other organic peroxyacids include diacyl and tetraacylperoxides, especially diperoxydodecanedioc acid, diperoxytetradecanedioc acid and diperoxyhexadecanedioc acid.
- Mono- and diperazelaic acid, mono- and diperbrassyhc acid and N-phthaloylammoperoxicaproic acid are also suitable herein
- Inorganic persalts are a preferred source of peroxide. Preferably these salts are present at a level of from 0.01% to 50% by weight, more preferably of from 0.5% to 30% by weight of the particle or composition of the invention.
- inorganic perhydrate salts include perborate, percarbonate, perphosphate, persulfate and persi cate salts.
- the inorganic perh y drate salts are normally the alkali metal salts.
- the inorganic perhydrate salt may be included as the crystalline solid without additional protection. For certain perhydrate salts however, the preferred executions of such granular compositions utilize a coated form of the matenal which provides better storage stability for the perhydrate salt m the granular product.
- Suitable coatings compnse inorganic salts such as alkali metal silicate, carbonate or borate salts or mixtures thereof, or organic matenals such as waxes, oils, or fatty soaps.
- Sodium perborate is a preferred perhydrate salt and can be in the form of the monohydrate of nominal formula NaB ⁇ 2H2 ⁇ 2 or the tetrahydrate NaB ⁇ 2H2 ⁇ 2-3H2 ⁇ .
- Alkali metal percarbonates, particularly sodium percarbonate are preferred perhydrates herein
- Sodium percarbonate is an addition compound having a formula corresponding to 2Na2C ⁇ 3.3H2 ⁇ 2, and is available commercially as a crystalline solid.
- Potassium peroxymonopersulfate is another inorganic perhydrate salt suitable for use herein.
- chelants refers to detergent ingredients which act to sequester (chelate) heavy metal ions These components may also have calcium and magnesium chelation capacity. but preferably selectively bind heavy metal ions such as iron, manganese and copper.
- Chelants are generally present the detergent particle or final detergent composition at a level of from 0.005% to 10%, preferably from 0.1 % to 5%, more preferably from 0.25% to 7.5% and most preferably from 0.3% to 2% by weight of the compositions or component
- Suitable chelants include organic phosphonates, such as the ammo alkylene poly (alkylene phosphonates), alkali metal ethane 1 -hydroxy disphosphonates and nitrilo trimethylene phosphonates, preferably, diethylene t ⁇ amme penta (methylene phosphonate), ethylene diamine tn (methylene phosphonate) hexamethylene diamine tetra (methylene phosphonate) and hydroxy- ethylene 1 ,1 diphosphonate, 1 ,1 hydroxyethane diphosphonic acid and 1,1 hydroxyethane dimethylene phosphonic acid.
- organic phosphonates such as the ammo alkylene poly (alkylene phosphonates), alkali metal ethane 1 -hydroxy disphosphonates and nitrilo trimethylene phosphonates, preferably, diethylene t ⁇ amme penta (methylene phosphonate), ethylene diamine tn (methylene phosphonate) hex
- Suitable chelants for use herein include nitrilotnacetic acid and polyammocarboxyhc acids such as ethylenediammotetracetic acid, ethylenediamine disuccimc acid, ethylenediamine digluta ⁇ c acid, 2-hydroxypropylened ⁇ amme disuccimc acid or any salts thereof, and lmmodiacetic acid denvatives such as 2-hydroxyethyl diacetic acid or glyceryl immo diacetic acid, described in EP-A-317,542 and EP-A-399,133.
- nitrilotnacetic acid and polyammocarboxyhc acids such as ethylenediammotetracetic acid, ethylenediamine disuccimc acid, ethylenediamine digluta ⁇ c acid, 2-hydroxypropylened ⁇ amme disuccimc acid or any salts thereof
- lmmodiacetic acid denvatives such as 2-hydroxyethyl diacetic acid or glyceryl immo diacetic acid
- EP-A-516.102 The lmmodiacetic ac ⁇ d-N-2- hydroxypropyl sulfonic acid and aspartic acid N-carboxymethyl N-2-hydroxypropyl-3-sulfon ⁇ c acid sequestrants described in EP-A-516.102 are also suitable herein.
- the ⁇ -alanme-N,N'-d ⁇ acet ⁇ c acid, aspartic ac ⁇ d-N,N'-d ⁇ acet ⁇ c acid, aspartic acid-N-monoacetic acid and immodisuccmic acid sequestrants descnbed m EP-A-509,382 are also suitable.
- EP-A-476.257 descnbes suitable amino based sequestrants.
- EP-A-510,331 describes suitable sequestrants derived from collagen. keratin or casem.
- EP-A-528,859 descnbes a suitable alkyl lmmodiacetic acid sequestrant
- Dipico nic acid and 2-phosphonobutane-l ,2,4-t ⁇ carboxyl ⁇ c acid are alos suitable.
- Glycmamide- N,N'-d ⁇ succm ⁇ c acid Glycmamide- N,N'-d ⁇ succm ⁇ c acid (GADS).
- EDDG ethylenediamme-N-N'-digluta ⁇ c acid
- HPDDS 2- hydroxypropylenediamine-N-N'-disuccimc acid
- chelating agents comprising a ammo or am e group can be bleach-sensitive and are suitable m the compositions of the invention Water-Soluble Builder Compound
- the component or compositions herein preferably contain a water-soluble builder compound, typically present in detergent compositions at a level of from 1 % to 80% by weight preferably from 10% to 60% by weight, most preferably from 15% to 40% by weight
- the detergent compositions of the invention may comprise phosphate-contam g builder material Preferably present at a level of from 0 5% to 60%. more preferably from 5% to 50%, more preferably from 8% to 40%
- the phosphate-containing builder matenal preferably comprises tetrasodium pyrophosphate or even more preferably anhydrous sodium t ⁇ polyphosphate
- Suitable water-soluble builder compounds include the water soluble monomenc polycarboxylates, or their acid forms, homo or copolyme ⁇ c polycarboxylic acids or their salts which the polycarboxylic acid comprises at least two carboxylic radicals separated from each other by not more that two carbon atoms, borates, and mixtures of any of the foregoing
- the carboxylate or polycarboxylate builder can be momomenc or o gomenc in type although monomenc polycarboxylates are generally preferred for reasons of cost and performance
- Suitable carboxylates containing one carboxy group include the water soluble salts of lactic acid, glycohc acid and ether de ⁇ vatives thereof
- Polycarboxylates containing two carboxy groups include the water-soluble salts of succimc acid, malonic acid, (ethylenedioxy) diacetic acid, maleic acid, diglycohc acid, tarta ⁇ c acid, tartronic acid and fuma ⁇ c acid, as well as the ether carboxylates and the sulfinyl carboxylates
- Polycarboxylates or their acids containing three carboxy groups include, in particular, water-soluble citrates, aconitrates and citraconates as well as succmate derivatives such as the carboxymethyloxysuccmates descnbed B ⁇ tish Patent No.
- the most preferred polycarboxylic acid containing three carboxy groups is citnc acid, preferably present at a level of from 0.1% to 15%, more preferably from 0 5% to 8% by weight
- Polycarboxylates containing four carboxy groups include oxydisuccmates disclosed in Bntish Patent No 1 ,261 ,829, 1 , 1 ,2,2-ethane tetracarboxylates, 1 , 1 ,3,3-propane tetracarboxylates and 1 ,1, 2, 3 -propane tetracarboxylates
- Polycarboxylates containing sulfo substituents include the sulfosuccinate de ⁇ vatives disclosed in British Patent Nos 1.398,421 and 1.398,422 and in U.S Patent No 3.936.448. and the sulfonated pyrolysed citrates desc ⁇ bed in British Patent No 1,439.000.
- Preferred polycarboxylates are hydroxy carboxylates containing up to three carboxy groups per molecule, more particularly citrates.
- the parent acids of the monomenc or oligome ⁇ c polycarboxylate chelatmg agents or mixtures thereof with their salts, e g citric acid or citrate/citric acid mixtures are also contemplated as useful builder components
- Water-soluble builders are the alkali metal tnpolyphosphates. sodium, potassium and ammonium pyrophosphate. sodium and potassium and ammonium pyrophosphate. sodium and potassium orthophosphate. sodium polymeta/phosphate in which the degree of polymerization ranges from about 6 to 21 , and salts of phytic acid
- organic polymeric compounds include the water soluble organic homo- or co-polymeric polycarboxylic acids or their salts in which the polycarboxylic acid compnses at least two carboxyl radicals separated from each other by not more than two carbon atoms Polymers of the latter type are disclosed m GB-A- 1 ,596,756.
- salts are polyacrylates of MWt 1000-5000 and their copolymers with maleic anhydnde, such copolymers having a molecular weight of from 2000 to 100,000, especially 40,000 to 80,000.
- the polyammo compounds are useful herein including those de ⁇ ved from aspartic acid such as those disclosed m EP-A-305282, EP-A-305283 and EP-A-351629
- the particles or detergent compositions of the present invention may contain a partially soluble or insoluble builder compound, typically present detergent compositions at a level of from 0.5% to 60% by weight, preferably from 5% to 50% by weight, most preferably from 8% to 40% weight.
- a partially soluble or insoluble builder compound typically present detergent compositions at a level of from 0.5% to 60% by weight, preferably from 5% to 50% by weight, most preferably from 8% to 40% weight.
- largely water insoluble builders include the sodium alummosihcates As mentioned above, it may be preferred in one embodiment of the invention, that only small amounts of alummo silicate builder are present.
- Suitable aluminosilicate zeolites have the unit cell formula a z [(Al ⁇ 2) z (S ⁇ 2)v]- XH2O where z and y are at least 6; the molar ratio of z to y is from 1.0 to 0.5 and x is at least 5, preferably from 7.5 to 276, more preferably from 10 to 264
- the aluminosilicate matenal are hydrated form and are preferably crystalline, containing from 10% to 28%, more preferably from 18% to 22% water m bound form
- the aluminosilicate zeolites can be naturally occurnng matenals. but are preferably synthetically denved. Synthetic crystalline aluminosilicate ion exchange materials are available under the designations Zeolite A. Zeolite B, Zeolite P. Zeolite X, Zeolite HS and mixtures thereof. Zeolite A has the formula
- zeolite MAP builder The zeolite MAP can be present at a level of from 1 % to 80%, more preferably from 15% to 40% by weight Zeolite MAP is described m EP 384070A (Unilever). It is defined as an alkali metal alumino-sihcate of the zeolite P type having a silicon to aluminium ratio not greater than 1.33, preferably within the range from 0.9 to 1.33 and more preferably within the range of from 0.9 to 1.2 Of particular interest is zeolite MAP having a silicon to aluminium ratio not greater than 1.15 and. more particularly, not greater than 1.07
- the zeolite MAP detergent builder has a particle size, expressed as a median particle size d5 Q value of from 1.0 to 10.0 micrometres, more preferably from 2.0 to 7.0 micrometres, most preferably from 2.5 to 5 0 micrometres.
- the d5Q value indicates that 50% by weight of the particles have a diameter smaller than that figure.
- the particle size may, m particular be determined by conventional analytical techniques such as microscopic determination using a scanning electron microscope or by means of a laser granulometer, described herein Other methods of establishing d5 ⁇ values are disclosed in EP 384070A.
- compositions herein are dyes and dyed particles or speckles, which can be bleach-sensitive.
- the dye as used herein can be a dye stuff or an aqueous or nonaqueous solution of a dye stuff. It may be preferred that the dye is an aqueous solution comprising a dyestuff, at any level to obtain suitable dyeing of the detergent particles or speckles, preferably such that levels of dye solution are obtained up to 2% by weight of the dyed particle.
- the dye may also be mixed with a non-aqueous carrier material, such as non-aquous liquid matenals including nonionic surfactants
- a non-aqueous carrier material such as non-aquous liquid matenals including nonionic surfactants
- the dye also comprising other ingredients such as organic binder matenals, which may also be a non-aqueous liquid
- the dyestuff can be any suitable dyestuff.
- suitable dyestuffs include E104 - food yellow 13 (quinolme yellow), El 10 - food yellow 3 (sunset yellow FCF), E131 - food blue 5 (patent blue V), Ultra Ma ⁇ ne blue (trade name). El 33 - food blue 2 (bnlhant blue FCF). El 40 - natural green 3 (chlorophyll and chlorphyll s). El 41 and Pigment green 7 (chlorinated Cu phthalocyanme) Prefe ⁇ ed dyestuffs may be Monastral Blue BV paste (trade name) and or Pig asol Green (trade name)
- Preferred enzymes are discussed above with respect to the detergent active particulates
- the same enzymes are preferred as components of the detergent base powder or as additional detergent ingredients added to the detergent particles of the invention to form a fully formulated detergent
- the detergent particles or compositions herein also preferably contain from about
- photo-bleachmg agents are preferred ingredients of the compositions and are preferably present in the form of the detergent active particulates as discussed above However, they may optionally be present m the detergent base particles or as additional detergent ingredients for addition to the detergent particles of the invention for forming the fully formulated detergnet compositions of the invention
- Organic Polymeric Ingredients are preferred additional herein and are preferably present as components of any particulate components where they may act such as to bind the paniculate component together
- organic polymeric compound it is meant herein essentially any polymeric organic compound commonly used as dispersants.
- Polymeric soil release agents which are described above are also preferably present as detergent active particulates. However they may be present alternatively or in addition, in the detergent base particles or as additional detergent ingredients for addition to the detergent particles of the invention for formulating a finished detergent composition.
- Those bleaching agents which yield a hypochlo ⁇ te species m aqueous solution include alkali metal and alkaline earth metal hypochlo ⁇ tes, hypochlonte addition products, chloramines. chlonmmes, chloramides, and chlo ⁇ mides. Specific examples include sodium hypochlo ⁇ te, potassium hypochlonte. monobasic calcium hypochlonte. dibasic magnesium hypochlonte. chlo ⁇ nated t ⁇ sodium phosphate dodecahydrate, potassium dichloroisocyanurate.
- a preferred bleaching agent for use in the compositions of the instant invention is sodium hypochlonte. potassium hypochlonte. or a mixture thereof.
- a preferred chlonne-based bleach can be Tnclosan (trade name)
- hypochlo ⁇ te-yielding bleaching agents are available in solid or concentrated form and are dissolved in water during preparation of the compositions of the instant invention Some of the above materials are available as aqueous solutions.
- Lipase (1) Lipolytic enzyme, having 2.0% by weight of active enzyme, sold by
- Endolase Endoglucanase enzyme having 1.5% by weight of active enzyme, sold by NOVO Industnes A/S PB4 Sodium perborate tetrahydrate of nominal formula NaB02.3H2 O.H202-
- NAC-OBS (6-nonam ⁇ docaproyl) oxybenzene sulfonate
- TAED Tetraacetylethylenediamme
- Bnghtener 1 Disodium 4,4'-b ⁇ s(2-sulphostyryl)b ⁇ phenyl Brightener 2 : Disodium 4,4'-b ⁇ s(4-an ⁇ lmo-6-morpholmo-l .3.5-t ⁇ az ⁇ n-2-yl)ammo) st ⁇ lbene-2.2'-d ⁇ sulfonate
- PVPV1 Copolymer of polyvinylpyrohdone and vmyhmidazole with an average molecular weight of 20,000
- SRP 1 Anionically end capped poly esters SRP 2 Diethoxylated poly (1, 2 propylene terephtalate) short block polymer PEI Polyethyleneimine with an average molecular weight of 1800 and an average ethoxylation degree of 7 ethyleneoxy residues per nitrogen Sihcone antifoam Polydimethylsiloxane foam controller with siloxane-oxyalkylene copolymer as dispersing agent with a ratio of said foam controller to said dispersing agent of 10: 1 to 100: 1
- Opacifier Water based monostyrene latex mixture, sold by BASF
- This Example illustrates a process according to this invention which produces uniform free flowing, good dispensing and dissolving detergent particles with uniformity of colour and particle shape
- Multiple detergent starting ingredients are dry mixed an orbital vertical screw mixer of 200kg batch size, and several batches prepared This bulk premix is added into a honzontal rotating drum type mixer with internal baffles - a laboratory scale example having batch size 40kg A proportion of premix is sampled and added to the mixer The smaller particles which pose a segregation nsk are dry mixed into the mixer
- Binding agent C45AE7, is sprayed into the mixer using an air atomised nozzle
- the product is left to mix for 2 minutes and anti-cakmg agent (zeolite A) is added into the mixer and mixed for a further 1 minute
- anti-cakmg agent zeolite A
- the product is run into a storage box
- Other detergent additives such as enzymes, percarbonate and dyed carbonate speckles are post-added m a mixing step with other liquid additives such as perfume, to form the final detergent
- Example II This Example also illustrates the process of the invention and incorporates the parameters of Example I
- a premix of dry detergent materials is prepared as in example 1 , of composition as listed below.
- a proportion of premix is sampled and added to the mixer.
- C45AE7 mixed with PEG 4000 is sprayed into the mixer using an air atomised nozzle
- the premix of increased cohesivity is left to mix for 1 mmute
- the smaller particles which pose a segregation risk are dry mixed into the mixer.
- the product is left to mix for 2 minutes and anti- cakmg agent (zeolite A) is added into the mixer and mixed for a further 1 mmute.
- the product is run into a storage box.
- Other detergent additives such as enzymes, percarbonate and dyed carbonate speckles are post-added m a mixing step with other liquid additives such as perfume, to form the final detergent
- Example 2 also illustrates the process of the invention and incorporates the parameters of Example I
- a premix of dry detergent materials is prepared as example 1. of composition as listed below
- a proportion of premix is sampled and added to the mixer.
- Binding agent, C45AE5 is sprayed into the mixer using an air atomised nozzle
- the premix of increased cohesivity is left to mix for 1 mmute.
- the smaller particles which pose a segregation risk are dry mixed into the mixer
- the product is left to mix for 2 minutes and anti-cakmg agent (zeolite A) is added into the mixer and mixed for a further 15 seconds
- anti-cakmg agent zeolite A
- Other detergent additives such as enzymes, percarbonate and dyed carbonate speckles are post- added m a mixing step with other liquid additives such as perfume, to form the final detergent Component % Weight of Total Feed
- Example 2 also illustrates the process of the invention and incorporates the parameters of Example I.
- a premix of dry detergent matenals is prepared as m example 1, of composition as listed below. A proportion of premix is sampled and added to the mixer. Bonding agent, C45AE7, is sprayed into the mixer using an air atomised nozzle. The premix of increased cohesivity is left to mix for 1 minute. The smaller particles which pose a segregation nsk are dry mixed into the mixer. A further spray-on of bonding agent is applied to fix the small particles firmly to the surface of the larger host particles. The product is left to mix for 2 minutes and anti- cakmg agent (zeolite A) is added into the mixer and mixed for a further 1 mmute. The product is run into a storage box Other detergent additives such as enzymes, percarbonate and dyed carbonate speckles are post-added in a mixing step with other liquid additives such as perfume, to form the final detergent
- Example 2 also illustrates the process of the invention and incorporates the parameters of Example I.
- a premix of dry detergent materials is prepared as in example 1, of composition as listed below.
- a proportion of premix is sampled and added to the mixer.
- the fine segregatable particles are dispersed into a earner fluid such as C45AE7 in a tank, using low shear agitation, mixed for 10 minutes.
- the suspension of fine particles in fluid is pumped to a spray nozzle and atomised onto the premix particles m the mixer
- the product is left to mix for 2 minutes and anti-cakmg agent (zeolite A) is added into the mixer and mixed for a further 1 mmute.
- the product is run into a storage box.
- Other detergent additives such as enzymes, percarbonate and dyed carbonate speckles are post-added a mixing step with other liquid additives such as perfume, to form the final detergent.
- compositions In the following examples all levels are quoted as % by weight of the full finished detergent composition:
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002375408A CA2375408A1 (en) | 1999-06-21 | 2000-06-20 | Detergent particles and processes for making them |
MXPA02000060A MXPA02000060A (en) | 1999-06-21 | 2000-06-20 | Detergent particles and processes for making them. |
AU56257/00A AU5625700A (en) | 1999-06-21 | 2000-06-20 | Detergent particles and processes for making them |
JP2001505653A JP2003503545A (en) | 1999-06-21 | 2000-06-20 | Detergent particles and methods for producing them |
BRPI0011836-2A BR0011836B1 (en) | 1999-06-21 | 2000-06-20 | A process for producing a particle, detergent particle and detergent composition. |
EP00941565A EP1187900A1 (en) | 1999-06-21 | 2000-06-20 | Detergent particles and processes for making them |
US09/979,529 US6833346B1 (en) | 1999-06-21 | 2000-06-20 | Process for making detergent particulates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14009499P | 1999-06-21 | 1999-06-21 | |
US60/140,094 | 1999-06-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000078908A1 true WO2000078908A1 (en) | 2000-12-28 |
Family
ID=22489731
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/016916 WO2000078908A1 (en) | 1999-06-21 | 2000-06-20 | Detergent particles and processes for making them |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1187900A1 (en) |
JP (1) | JP2003503545A (en) |
CN (1) | CN1181175C (en) |
AR (1) | AR024429A1 (en) |
AU (1) | AU5625700A (en) |
BR (1) | BR0011836B1 (en) |
CA (1) | CA2375408A1 (en) |
MX (1) | MXPA02000060A (en) |
WO (1) | WO2000078908A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005080542A1 (en) * | 2004-02-13 | 2005-09-01 | The Procter & Gamble Company | Active containing delivery particle |
DE102005036346A1 (en) * | 2005-07-29 | 2007-02-01 | Henkel Kgaa | Granulates/agglomerate for detergents or cleaning agents comprises dust portion content from the elutriation method, surfactant content, and nuclear particle |
EP1881059A1 (en) * | 2006-07-18 | 2008-01-23 | The Procter and Gamble Company | Active containing delivery particle |
EP2007867A2 (en) * | 2006-04-20 | 2008-12-31 | The Procter and Gamble Company | Flowable particulates |
EP3256239B1 (en) * | 2015-02-10 | 2021-08-18 | Novozymes A/S | Method for mixing of particles |
WO2022104631A1 (en) * | 2020-11-19 | 2022-05-27 | The Procter & Gamble Company | Method of making detergent compositions comprising perfume |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1918362A1 (en) * | 2006-10-16 | 2008-05-07 | The Procter & Gamble Company | Low builder, highly water-soluble, low-density solid laundry detergent composition |
CN105886137A (en) * | 2014-12-15 | 2016-08-24 | 上海和黄白猫有限公司 | High-density low temperature quickly dissolved washing powder and preparation method thereof |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3714051A (en) * | 1969-09-24 | 1973-01-30 | Colgate Palmolive Co | Process for making enzyme-containing granules |
FR2285453A1 (en) * | 1974-09-23 | 1976-04-16 | Colgate Palmolive Co | Low foaming detergent compsns - prepd. by mixing polyorgano siloxane with anionic and non ionic detergents and auxiliary detergent salt |
GB2120695A (en) * | 1982-04-15 | 1983-12-07 | Colgate Palmolive Co | Fabric softening detergent |
GB2190921A (en) * | 1986-05-27 | 1987-12-02 | Unilever Plc | Granular detergent composition |
DE4243704A1 (en) * | 1992-12-23 | 1994-06-30 | Henkel Kgaa | Granular detergents and / or cleaning agents |
WO2000018875A1 (en) * | 1998-09-25 | 2000-04-06 | The Procter & Gamble Company | Granular detergent composition having improved appearance and solubility |
-
2000
- 2000-06-20 WO PCT/US2000/016916 patent/WO2000078908A1/en not_active Application Discontinuation
- 2000-06-20 CA CA002375408A patent/CA2375408A1/en not_active Abandoned
- 2000-06-20 CN CNB008118728A patent/CN1181175C/en not_active Expired - Fee Related
- 2000-06-20 MX MXPA02000060A patent/MXPA02000060A/en active IP Right Grant
- 2000-06-20 BR BRPI0011836-2A patent/BR0011836B1/en not_active IP Right Cessation
- 2000-06-20 JP JP2001505653A patent/JP2003503545A/en not_active Withdrawn
- 2000-06-20 AU AU56257/00A patent/AU5625700A/en not_active Abandoned
- 2000-06-20 EP EP00941565A patent/EP1187900A1/en not_active Withdrawn
- 2000-06-21 AR ARP000103096 patent/AR024429A1/en not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3714051A (en) * | 1969-09-24 | 1973-01-30 | Colgate Palmolive Co | Process for making enzyme-containing granules |
FR2285453A1 (en) * | 1974-09-23 | 1976-04-16 | Colgate Palmolive Co | Low foaming detergent compsns - prepd. by mixing polyorgano siloxane with anionic and non ionic detergents and auxiliary detergent salt |
GB2120695A (en) * | 1982-04-15 | 1983-12-07 | Colgate Palmolive Co | Fabric softening detergent |
GB2190921A (en) * | 1986-05-27 | 1987-12-02 | Unilever Plc | Granular detergent composition |
DE4243704A1 (en) * | 1992-12-23 | 1994-06-30 | Henkel Kgaa | Granular detergents and / or cleaning agents |
WO2000018875A1 (en) * | 1998-09-25 | 2000-04-06 | The Procter & Gamble Company | Granular detergent composition having improved appearance and solubility |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005080542A1 (en) * | 2004-02-13 | 2005-09-01 | The Procter & Gamble Company | Active containing delivery particle |
US7671005B2 (en) * | 2004-02-13 | 2010-03-02 | The Procter & Gamble Company | Active containing delivery particle |
DE102005036346A1 (en) * | 2005-07-29 | 2007-02-01 | Henkel Kgaa | Granulates/agglomerate for detergents or cleaning agents comprises dust portion content from the elutriation method, surfactant content, and nuclear particle |
EP2007867A2 (en) * | 2006-04-20 | 2008-12-31 | The Procter and Gamble Company | Flowable particulates |
EP1881059A1 (en) * | 2006-07-18 | 2008-01-23 | The Procter and Gamble Company | Active containing delivery particle |
EP3256239B1 (en) * | 2015-02-10 | 2021-08-18 | Novozymes A/S | Method for mixing of particles |
WO2022104631A1 (en) * | 2020-11-19 | 2022-05-27 | The Procter & Gamble Company | Method of making detergent compositions comprising perfume |
Also Published As
Publication number | Publication date |
---|---|
AU5625700A (en) | 2001-01-09 |
AR024429A1 (en) | 2002-10-02 |
BR0011836B1 (en) | 2012-06-12 |
CA2375408A1 (en) | 2000-12-28 |
MXPA02000060A (en) | 2002-07-02 |
BR0011836A (en) | 2002-03-05 |
CN1181175C (en) | 2004-12-22 |
CN1375001A (en) | 2002-10-16 |
JP2003503545A (en) | 2003-01-28 |
EP1187900A1 (en) | 2002-03-20 |
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