US3597361A - Method of preparing agglomerated detergent composition - Google Patents

Method of preparing agglomerated detergent composition Download PDF

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Publication number
US3597361A
US3597361A US826341A US3597361DA US3597361A US 3597361 A US3597361 A US 3597361A US 826341 A US826341 A US 826341A US 3597361D A US3597361D A US 3597361DA US 3597361 A US3597361 A US 3597361A
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ingredients
sulfonic acid
sodium
caustic soda
alkyl aryl
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US826341A
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Clark A Sumner
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Lever Brothers Co
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Stauffer Chemical Co
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Assigned to LEVER BROTHERS COMPANY, INCORPORATED, 390 PARK AVENUE, NEW YORK, NEW YORK 10022, A MAINE CORP. reassignment LEVER BROTHERS COMPANY, INCORPORATED, 390 PARK AVENUE, NEW YORK, NEW YORK 10022, A MAINE CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: STAUFFER CHEMICAL COMPANY, A DE CORP
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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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2/00—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic
    • B01J2/12—Processes or devices for granulating materials, e.g. fertilisers in general; Rendering particulate materials free flowing in general, e.g. making them hydrophobic in rotating drums
    • 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
    • C11D11/0088—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 the liquefied ingredients being sprayed or adsorbed onto solid particles

Definitions

  • This invention relates to a method of producing a detergent composition. More particularly, it relates to a process utilizing known detergent composition ingredients such as, e.g., laundry detergent ingredients for producing agglomerates of these ingredients, such process having several advantages over prior art process.
  • One such advantage is that it is more economical than prior art processes.
  • Another advantage is that laundry detergents having characteristics similar to those obtained by well-known spray-dried processes can be obtained without several of the disadvantages of such processes.
  • spray-driers are available, both of the jet and of the disc type, and also using both counter-current and con-current airflow patterns.
  • spray-driers for detergent powders are of the countercurrent airflow, jet-spray type, which produce a large bead with a minimum of dust and a medium bulk density.
  • spray-drying processes for preparing laundry detergents have the disadvantage, among others, that the spray-drier needed in the process involves a large capital outlay.
  • the other principal process for preparing laundry detergent powders involves the absorption of a surfactant onto inorganic salts in conventional beaded powder mixers such as ribbon mixers, plough mixers, incorporators, or screw mixers.
  • This method of producing powders is to charge the mixer with the dry ingredients, start the mixing, and to pump (or pour) a liquid surfactant through a jet into the powder slowly while mixing.
  • the rate of addition of the liquid surfactant must be adjusted so that the liquid is absorbed as it reaches the surface of the powder; if not, hard crystalline lumps will be formed.
  • This process permits only a limited amount of active matter to be incorporated into the powder, and it yields materials with only limited application for household use.
  • the laundry detergent composition prepared by the process of this invention is free-flowing, non-caking and non-friable. Laundry detergents having characteristics similar to those obtained with the spray-dried process, are obtained without the expense of the spray-drier. Several of the limitations of processes involving absorption are overcome.
  • a principal object of the present invention is to provide a process for the preparation of detergent composition.
  • An object of the present invention is to prepare by a unique process involving agglomeration the well-known spray-dried detergents.
  • Still another object of this invention is to prepare a homogeneous, non-segregating substantially dustfree agglomerate of laundry detergent ingredients in either a batch or continuous operation.
  • a further object is to provide a process for preparing laundry detergent compositions wherein it is possible in one operation to mix dry particulate ingredients, and then add a sodium salt of alkyl aryl sulfonic acid, as hereinafter defined, prepared in situ by merging sprays of liquid caustic soda, as hereinafter defined, and an alkyl aryl sulfonic acid and run on a batch or continuous basis to produce a laundry detergent composition.
  • dry laundry detergent composition ingredients in particulate form such as in powder or fine crystalline form, are charged into a bed of material being agglomerated in a suitable agglomeration zone.
  • a preferred agglomeration zone comprises an elongated cylindrical confined zone which is rotated about its longitudinal axis and which is adapted with suitable means for maintaining a continuously falling curtain of the detergent ingredients communicating between an upper portion of the confined zone and a bed of the material maintained in the bottom portion thereof.
  • a sodium salt of alkyl aryl sulfonic acid is brought into contact with the particulate ingredients in the falling curtain, preferably of a constant density, thereby wetting the particles to form agglomerates, preferably without the sodium salt of alkyl aryl sulfonic acid, contacting any part of the apparatus being used.
  • the agglomerated particles fall into the bed of material maintained in the bottom portion of the agglomeration zone where they are subjected to shear which breaks the few large oversize agglomerates that happen to form into desirable uniform-sized particles.
  • the rotating and tumbling action of the bed produces agglomerated particles of the laundry detergent composition of the desired size.
  • Particle size of the agglomerates can be varied by controlling the rate of rotation of the drum, the length of time of rotation, and the amount of the sodium salt of alkyl aryl sulfonic acid applied.
  • the discrete droplets of the sodium salt of alkyl aryl sulfonic acid are prepared in situ in the said agglomeration zone by merging sprays of liquid caustic soda, hereinafter defined, and alkyl aryl sulfonic acid, hereinafter defined, both materials having been sprayed as discrete droplets through suitable spray nozzles at the proper angle.
  • the apparatus may generally comprise a frame 10 having an angularly adjustable bed 12, two-way acting power means 14 to selectively positioned bed 12 at any desired angle relative to the horizontal a cylindrical drum 16, means 18 and 20 to rotatably support the drum on bed 12, and variable speed drive means 22, 24 and 26 to rotate the drum.
  • Drum 16 comprises: an outer cylindrical shell or wall 28; an annular end plate 32 defining a feed opening 34 through which the particulate ingredients 36 are loaded; an annular end plate 38 defining a discharge opening 40 through which the agglomerated detergent composition 44 is discharged through hopper 42; a spiral conveyor vane 5-2 to move the particulate ingredients and/or partially agglomerated particle 36 through the drum toward the feed opening 34; and a spiral conveyor vane 46 to move the particulate ingredients 36 and/or agglomerated particle 44 toward the discharge opening 40; a feed line 56 provided with a plurality of spaced spray nozzles 58 (FIGS.
  • a second feed line 57 provided with a plurality of spaced spray nozzles 57 and a cylindrical bundle of parallel-spaced cylindrical rods 60 which develop the continuously falling curtain and are carried between conveyor vanes 46 and 52 and positioned between drum end plates 32 and'38. It will be appreciated that, except for feed line 56 and 57, the components of drum 16 rotate together as an integrated unit. Nozzles 58 and 59 should be positioned so that the material sprayed from them, as hereinafter specified, intersect each other between nozzles 58 and 59 and said falling curtain.
  • the angle of the intersection of said sprays from nozzles 58 and 59 is not critical but it should be as small as possible to allow maximum intimate contact of the two sprays, thus giving maximum reaction time, and should not be so great as to prevent the reaction product of the two particular materials being sprayed from being carried onto said falling curtains.
  • the ingredients for the detergent composition, especially laundry detergent composition include the following: (a) alkaline condensed phosphate, (b) sodium or potassium silicates, (c) neutral soluble salts, (d) sodium salt of alkyl aryl sulfonic acid, and optionally, (e) alkalies, and (f) such materials as insoluble inorganic builders and special purpose additives.
  • the alkaline condensed phosphates preferably are those having an Na O or K to P 0 ratio of about 1:1 to 2: 1. More preferably, they are the pyrophosphates and polyphosphates, the more desirable are those that rapidly hydrate.
  • the most preferred alkaline condensed phosphate is sodium tripolyphosphate. About to 70 parts by weight of the alkaline condensed phosphate per 100 parts is useful in the composition, preferably the amount is about to 60 parts by weight.
  • the alkaline condensed 4 phosphates can be used in anhydrous form or in a hydrated or partly hydrated form, preferably the anhydrous form.
  • the sodium or potassium silicates preferably are those having an Na O or K 0 to SiO ratio of about 123.75 to 2:1. More preferred, are the sodium silicates having an Na O to SiO ratio of about 1:3.22 to 1:25. Preferably, about 5 to 20 partsby weight silicate (on an anhydrous basis) per parts detergent should be used. A more preferred ratio is about 1 to 10.
  • the silicate can be used in its anhydrous form or in its hydrated form or as a water solution of these forms or a combination thereof.
  • Water solutions of silicates are known as liquid silicates and normally are the sodium silicates having an Na O:SiO ratios ranging from about 121.60 to about 113.75.
  • Liquid caustic soda is (1) a solution of caustic soda (NaOH) in a suitable solvent, preferably water, which solution is maintained in a liquid state at ambient tem peratures by heating if necessary or (2) 100% caustic soda maintained in a liquid state by heating it to above its melting point.
  • a suitable solvent preferably water
  • the caustic soda should be about a 40% or greater aqueous solution or 100% c austic soda, more preferably, the caustic soda should be about a 73% or greater aqueous solution or 100% caustic soda. Most preferably, it should be about a 73% aqueous solution.
  • the concentration of caustic soda which can be employed in the practice of the present invention, includes the readily available concentrations of about 50 and 73% NaOH in aqueous solution.
  • aqueous solution of caustic soda is in a solid state at ambient temperature, it will be necessary to heat in order to liquify it before spraying it as previously described. Such is also true of 100% caustic soda; however, here it must be melted to a molten state.
  • the sodium salts of the so-called alkyl aryl sulfonic acid that are useful in the practice of this invention are well-known by those skilled in the art.
  • This material is the reaction product of liquid caustic soda and alkyl aryl sulfonic acid, both hereinafter defined.
  • About 8 to 30 parts by weight of said sodium salt per 100 parts detergent is useful in the practice of this invention. It is preferred to use 15 to 25 parts by weight per 100 parts detergent.
  • the salt is prepared in situ in the agglomeration zone useful in the practice of this invention by simultaneously spraying liquid caustic soda, heretofore defined, and alkyl aryl sulfonic acid, heretofore described, in the manner heretofore described.
  • alkyl aryl sulfonic acids that are useful are a recognized group of chemical compounds and are wellknown by those skilled in the art. Most of these compounds are the sulfonation product of an alkylated aromatic nucleus, which product can be neutralized with caustic soda to prepare the class of anionic surface-active agents known as alkylarenesulfonates, or commonly, alkyl aryl sulfonates. These alkyl aryl sulfonic acids are described in numerous literature articles, for example, Kirk- Othmer Encyclopedia of Chemical Technology, vol. 13, Sulfonation and Sulfation, pages 317-337, and Surface- Active Agents, pages 513-523.
  • the preferred alkyl aryl sulfonic acids are those in which the alkyl group is straight or branched (most preferably straight) and contain 10 through 18 carbon atoms and the aryl group is benzene.
  • the straight chained ones being the biodegradable type.
  • Another preferred alkyl aryl sulfonic acid is the so-called alpha olefin sulfonic acid, particularly those taught in US. 3,332,874 through 3,332,880 incorporated herein by reference.
  • the most preferred alkyl aryl sulfonic acid is dodecylbenzene sulfonic acid, wherein in the manufacture thereof, the petroleum fraction used to form the side chain is so chosen as to have an average molecular weight corresponding to twelve carbon atoms, but is, of course, a mixture.
  • alkalies includes sodium hydroxide, sodium carbonate, sodium bicarbonate, sodium sesquicarbonate, sodium borate (borax) or the potassium analogs thereof.
  • neutral soluble salts include sodium sulfate and sodium chloride. About 1 to 60 parts by weight of the neutral soluble salts per 100 parts detergent is useful. It is preferred to use 3 to parts by weight of the neutral soluble salts per 100 parts of the detergent.
  • the detergent products of the process of this invention contain an alkaline condensed phosphate, sodium or potassium silicates, neutral soluble salts, the surfactant and one or more optional ingredients, including alkalies.
  • These materials include insoluble inorganic builders, such as clays; various organic builders and special purpose additives, such as sodium carboxymethyl cellulose; heavy metal sequestering agents; foam builders and stabilizers; solubilizing additives; optical bleach or brightening agents; corrosion inhibitors; tarnish inhibitors, and others, ineluding enzymes.
  • active chlorine containing compounds are active chlorine containing compounds. These compounds are defined in US. application Ser. No. 764,634, filed Oct. 11, 1968, and are defined therein as follows:
  • the active chlorine-containing compound imparts germicidal, bleaching, water sheeting, and protein removing action to the detergent compositions.
  • They include chlorinated trisodium phosphate, trichlorocyanuric acid, the sodium salt of dichlorocyanuric acid, the potassium salt of dichlorocyanuric acid, sodium hypochlorite and 1,3-dichloro-5,5-dimethyl-hydantoin.
  • the ingredients of the detergent composition are combined as follows: According to one method, all the particulate ingredients are mixed to form a homogeneous mixture, if they are not already so mixed.
  • Such particulate ingredients are the alkaline condensed phosphate, and, if desired, sodium or potassium silicates, alkalies, neutral soluble salts, and optional particulate ingredients.
  • liquid caustic soda and the alkyl aryl sulfonic acids are simultaneously sprayed each from a separate system of nozzles in such a manner that the two sprays intersect each other, preferably at an acute angle, and the resulting spray mixture reaction product continues and is sprayed as discrete droplets into a falling curtain of the particulate ingredients.
  • Water can be sprayed either before, during, or after the spraying of the sodium salt of alkyl aryl sulfonic acid to hydrate hydratable ingredients.
  • the sodium salt of alkyl aryl sulfonic acid is added onto the particulate ingredients that are not fully hydrated.
  • the size of the agglomerates that can be produced in the practice of this invention is between about 10 and about 60 US. mesh size, preferably a mesh size between 12 and about 40 is produced.
  • the particle size of the powdered dry ingredient used in preparing the agglomerates is about 100 US. mesh size.
  • the liquid sodium silicate is sprayed at a temperature of about 180 F. at a pressure of about 80 psi. for about 10 minutes.
  • the rotation is continued for about 2030 minutes to cool the resulting agglomerates.
  • a method of producing agglomerates of detergent ingredients which comprises (1) charging dry particulate detergent ingredients consisting essentially of (A) about 20 to 80 parts by weight of an alkaline condensed phosphate having a Na O or K 0 to P 0 ratio of about 1:1 to 2:1, (B) about 5 to 20 parts by weight sodium or potassium silicate (on an anhydrous basis) having an Na O or K 0 to SiO ratio of about 1:3.75 to 2:1, (C) about 1 to 60 parts by weight of a neutral soluble salt, all per 100 parts detergent into an agglomeration zone, (2) maintaining a continuously falling curtain of said ingredients in said zone (3) contacting said ingredients in said falling curtain with about 8 to 30 parts by weight per 100 parts detergent a sodium salt of alkyl benzene sulfonic acid to agglomerate said particulate material, said sodium salt of alkyl benzene sulfonic acid, said alkyl group having 10 to 18 carbon atoms, being prepared in situ in said agglomeration zone by merg
  • alkyl benzene sulfonic acid is an alkyl benzene sulfonic acid in which said alkyl group is linear and has from 10 to 18 carbon atoms.
  • said dry particulate detergent ingredients consist essentially of (A) about 30 to 60 parts by Weight sodium tripolyphosphate (B) to 20 parts by weight sodium silicate (on an anhydrous basis) having an Na O to SiO ratio of about 1:3.22 to 1:2.5 (C) about 3 to parts by weight of a neutral soluble salt, all per 100 parts detergent and to parts by weight per parts detergent of said sodium salt of alkyl benzene sulfonic acid is used to contact said dry particulate ingredients.
  • detergent ingredients also include materials selected from the group consisting of alkalies, insoluble inorganic builders and special purpose additives.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
US826341A 1969-05-21 1969-05-21 Method of preparing agglomerated detergent composition Expired - Lifetime US3597361A (en)

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AU (1) AU1480270A (xx)
BE (1) BE750645A (xx)
BR (1) BR7019192D0 (xx)
CA (1) CA919052A (xx)
DE (1) DE2024476A1 (xx)
ES (1) ES379752A1 (xx)
FR (1) FR2048577A5 (xx)
IL (1) IL34560A0 (xx)
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3886098A (en) * 1971-03-15 1975-05-27 Colgate Palmolive Co Manufacture of free flowing particulate detergent composition containing nonionic detergent
US4040988A (en) * 1974-09-27 1977-08-09 The Procter & Gamble Company Builder system and detergent product
US4427417A (en) 1982-01-20 1984-01-24 The Korex Company Process for preparing detergent compositions containing hydrated inorganic salts
US4501499A (en) * 1983-09-15 1985-02-26 Purex Corporation Agglomerator
US4761248A (en) * 1986-11-06 1988-08-02 Kerr-Mcgee Chemical Corporation Process for preparing particulate detergent products
EP0345090A2 (en) * 1988-06-03 1989-12-06 Colgate-Palmolive Company Process for manufacturing particulate detergent composition directly from in situ produced anionic detergent salt
US5024782A (en) * 1989-06-16 1991-06-18 The Clorox Company Zeolite agglomeration process and product
US5066425A (en) * 1990-07-16 1991-11-19 The Procter & Gamble Company Formation of high active detergent particles
US5205958A (en) * 1989-06-16 1993-04-27 The Clorox Company Zeolite agglomeration process and product
US5573697A (en) * 1995-05-31 1996-11-12 Riddick; Eric F. Process for making high active, high density detergent granules
US5714451A (en) * 1996-03-15 1998-02-03 Amway Corporation Powder detergent composition and method of making
US5714450A (en) * 1996-03-15 1998-02-03 Amway Corporation Detergent composition containing discrete whitening agent particles
US5990068A (en) * 1996-03-15 1999-11-23 Amway Corporation Powder detergent composition having improved solubility
US5998351A (en) * 1996-03-15 1999-12-07 Amway Corporation Discrete whitening agent particles method of making, and powder detergent containing same
US6174851B1 (en) * 1998-12-19 2001-01-16 Henkel Kommanditgesellschaft Auf Aktien Process for the production of detersive granules
US6177397B1 (en) 1997-03-10 2001-01-23 Amway Corporation Free-flowing agglomerated nonionic surfactant detergent composition and process for making same
US20090286710A1 (en) * 2008-05-14 2009-11-19 Nigel Patrick Somerville Roberts Solid Laundry Detergent Composition Comprising Light Density Silicate Salt

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3886098A (en) * 1971-03-15 1975-05-27 Colgate Palmolive Co Manufacture of free flowing particulate detergent composition containing nonionic detergent
US4040988A (en) * 1974-09-27 1977-08-09 The Procter & Gamble Company Builder system and detergent product
US4427417A (en) 1982-01-20 1984-01-24 The Korex Company Process for preparing detergent compositions containing hydrated inorganic salts
US4501499A (en) * 1983-09-15 1985-02-26 Purex Corporation Agglomerator
US4761248A (en) * 1986-11-06 1988-08-02 Kerr-Mcgee Chemical Corporation Process for preparing particulate detergent products
EP0345090A2 (en) * 1988-06-03 1989-12-06 Colgate-Palmolive Company Process for manufacturing particulate detergent composition directly from in situ produced anionic detergent salt
US4919847A (en) * 1988-06-03 1990-04-24 Colgate Palmolive Co. Process for manufacturing particulate detergent composition directly from in situ produced anionic detergent salt
EP0345090A3 (en) * 1988-06-03 1991-07-31 Colgate-Palmolive Company Process for manufacturing particulate detergent composition directly from in situ produced anionic detergent salt
US5024782A (en) * 1989-06-16 1991-06-18 The Clorox Company Zeolite agglomeration process and product
US5205958A (en) * 1989-06-16 1993-04-27 The Clorox Company Zeolite agglomeration process and product
US5066425A (en) * 1990-07-16 1991-11-19 The Procter & Gamble Company Formation of high active detergent particles
US5573697A (en) * 1995-05-31 1996-11-12 Riddick; Eric F. Process for making high active, high density detergent granules
US5714451A (en) * 1996-03-15 1998-02-03 Amway Corporation Powder detergent composition and method of making
US5714450A (en) * 1996-03-15 1998-02-03 Amway Corporation Detergent composition containing discrete whitening agent particles
US5990068A (en) * 1996-03-15 1999-11-23 Amway Corporation Powder detergent composition having improved solubility
US5998351A (en) * 1996-03-15 1999-12-07 Amway Corporation Discrete whitening agent particles method of making, and powder detergent containing same
US6008174A (en) * 1996-03-15 1999-12-28 Amway Corporation Powder detergent composition having improved solubility
US6080711A (en) * 1996-03-15 2000-06-27 Amway Corporation Powder detergent composition and method of making
US6177397B1 (en) 1997-03-10 2001-01-23 Amway Corporation Free-flowing agglomerated nonionic surfactant detergent composition and process for making same
US6174851B1 (en) * 1998-12-19 2001-01-16 Henkel Kommanditgesellschaft Auf Aktien Process for the production of detersive granules
US20090286710A1 (en) * 2008-05-14 2009-11-19 Nigel Patrick Somerville Roberts Solid Laundry Detergent Composition Comprising Light Density Silicate Salt
US20090286711A1 (en) * 2008-05-14 2009-11-19 Nigel Patrick Somerville Roberts Solid Laundry Detergent Composition Comprising Light Density Silicate Salt
EP2123742A1 (en) 2008-05-14 2009-11-25 The Procter and Gamble Company A solid laundry detergent composition comprising light density silicate salt
EP2123743A1 (en) 2008-05-14 2009-11-25 The Procter and Gamble Company A solid laundry detergent composition comprising light density silicate salt
EP2128235A1 (en) 2008-05-14 2009-12-02 The Procter and Gamble Company A solid laundry detergent composition comprising light density silicate salt
US7727947B2 (en) 2008-05-14 2010-06-01 The Procter & Gamble Company Process for the preparation of a solid laundry detergent composition comprising light density silicate salt
US7732394B2 (en) 2008-05-14 2010-06-08 The Procter & Gamble Company Solid laundry detergent composition comprising light density silicate salt

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ZA703417B (en) 1971-01-27
BR7019192D0 (pt) 1973-01-18
DE2024476A1 (xx) 1970-12-23
IL34560A0 (en) 1970-07-19
AU1480270A (en) 1971-11-18
CA919052A (en) 1973-01-16
FR2048577A5 (xx) 1971-03-19
BE750645A (fr) 1970-11-20
ES379752A1 (es) 1972-08-01
NL7007346A (xx) 1970-11-24

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