WO2000044874A1 - Cationic particle and a process for making thereof - Google Patents

Cationic particle and a process for making thereof Download PDF

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Publication number
WO2000044874A1
WO2000044874A1 PCT/US1999/002082 US9902082W WO0044874A1 WO 2000044874 A1 WO2000044874 A1 WO 2000044874A1 US 9902082 W US9902082 W US 9902082W WO 0044874 A1 WO0044874 A1 WO 0044874A1
Authority
WO
WIPO (PCT)
Prior art keywords
cationic
particle
absorbing material
high absorbing
cationic particle
Prior art date
Application number
PCT/US1999/002082
Other languages
English (en)
French (fr)
Inventor
Manivannan Kandasamy
Kenji Naemura
Daniel James Dufton
Eric San Jose Robles
Aram Armand Dedeyan
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP2000596119A priority Critical patent/JP2002535480A/ja
Priority to CN99815982.4A priority patent/CN1334865A/zh
Priority to PCT/US1999/002082 priority patent/WO2000044874A1/en
Priority to CA002359319A priority patent/CA2359319C/en
Priority to US09/890,513 priority patent/US6627596B1/en
Priority to ES99905576T priority patent/ES2241261T3/es
Priority to EP99905576A priority patent/EP1149155B1/en
Priority to AT99905576T priority patent/ATE294228T1/de
Priority to BR9917013-2A priority patent/BR9917013A/pt
Priority to AU25708/99A priority patent/AU2570899A/en
Priority to DE69925037T priority patent/DE69925037T2/de
Publication of WO2000044874A1 publication Critical patent/WO2000044874A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • 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
    • C11D17/0034—Fixed on a solid conventional detergent ingredient
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds

Definitions

  • the present invention relates to a cationic surfactant particle, particulate detergent compositions containing such cationic particle, and a process for making thereof.
  • Cationic surfactants are a common surfactant as well as co-surfactant for use in detergent compositions and is commonly available in a liquid form.
  • detergent compositions will contain one or more types of surfactants which are designed to loosen and remove different types of soils and stains.
  • the present invention relates to a cationic particle containing an aqueous cationic surfactant solution adsorbed to a water-insoluble high absorbing material.
  • a process for making the cationic particle is also described herein.
  • the present invention relates to a cationic particle containing an aqueous cationic surfactant solution adsorbed to a water-insoluble high absorbing material. It is beneficial to have the cationic surfactant in a particulate form for various reasons, since cationic surfactants are commonly available in liquid solution form. For example, in processing particulate detergent compositions in non-tower processes, the liquid cationic surfactant may make the mixture during agglomeration sticky due to the excess moisture.
  • the cationic particle can be made a higher active particle, as compared to its liquid form, which provides formula space when formulating a particulate detergent composition.
  • the cationic particle of the present invention has good dispersion and solubility when used in the wash water.
  • the present invention also meets the aforementioned needs in the art by providing a cationic particle which can be used to produce a particulate detergent composition for flexibility in the ultimate density of the final composition.
  • the cationic particle of the present invention contains an aqueous cationic surfactant solution.
  • the cationic surfactant solution has at least about 70% water, preferably from about 40% to about 60%, more preferably from about 50% to about 60%, by weight of the surfactant solution.
  • the amount of cationic active in the aqueous cationic surfactant solution is at least about 30%, preferably from about 40% to 60%, more preferably from about 40% to 50%.
  • the cationic surfactant is selected from the group consisting of cationic ester surfactants, cationic mono-alkoxylated amine surfactants, cationic bis-alkoxylated amine surfactants and mixtures thereof.
  • Preferred quaternary ammonium surfactants are selected from mono C1-C30, preferably C6-C16 N- alkyl or alkenyl ammonium surfactants wherein remaining N positions are substituted by methyl, hydroxyethyl or hydroxypropyl groups.
  • Useful cationic surfactants include water-soluble quaternary ammonium compounds of the form R 4 R 5 R 6 R 7 N + X " , wherein R 4 is alkyl having from 10 to 20, preferably from 12-18 carbon atoms, and R 5 , R 6 , and R 7 are each C 1 to C 7 alkyl preferably methyl; X " is an anion, e.g. chloride. Examples of such trimethyl ammonium compounds include C 12 . 14 alkyl trimethyl ammonium chloride and cocoalkyl trimethyl ammonium methosulfate.
  • Cationic surfactants also useful is a cationic choline ester-type quat surfactant which are preferably water dispersible compounds having surfactant properties and comprise at least one ester (i.e. -COO-) linkage and at least one cationically charged group.
  • Suitable cationic ester surfactants including choline ester surfactants, have for example been disclosed in U.S. Patents Nos. 4,228,042, 4,239,660 and 4,260,529.
  • Preferred cationic ester surfactants are those having the formula:
  • is a C5-C31 linear or branched alkyl, alkenyl or alkaryl chain or M- .N + (RgR7R8)(CH2) s ; and Y, independently, are selected from the group consisting of COO, OCO, O, CO, OCOO, CONH, NHCO, OCONH and NHCOO wherein at least one of X or Y is a COO, OCO, OCOO, OCONH or NHCOO group; R2, R3, R4, R ⁇ > R7 and R ⁇ are independently selected from the group consisting of alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl and alkaryl groups having from 1 to 4 carbon atoms; and R5 is independently H or a C1-C3 alkyl group; wherein the values of m, n, s and t independently lie in the range of from 0 to 8, the value of b lies in the range from 0 to 20, and the values of a, u
  • R2 is independently selected from CH3 and -
  • M is selected from the group consisting of halide, methyl sulfate, sulfate, and nitrate, more preferably methyl sulfate, chloride, bromide or iodide.
  • Preferred water dispersible cationic ester surfactants are the choline esters having the formula:
  • R- j is a C-11-C19 linear or branched alkyl chain.
  • Particularly preferred choline esters of this type include the stearoyl choline ester quaternary methylammonium halides alkyl), palmitoyl choline ester quaternary methylammonium halides lkyl), myristoyl choline ester quaternary methylammonium halides alkyl), lauroyl choline ester quaternary methylammonium halides ⁇ alkyl), cocoyl choline ester quaternary methylammonium halides ⁇
  • the particularly preferred choline esters may be prepared by the direct esterification of a fatty acid of the desired chain length with dimethylaminoethanol, in the presence of an acid catalyst.
  • the reaction product is then quaternized with a methyl halide, preferably in the presence of a solvent such as ethanol, propylene glycol or preferably a fatty alcohol ethoxylate such as C- ⁇ o-C-18 fatty alcohol ethoxylate having a degree of ethoxylation of from 3 to 50 ethoxy groups per mole forming the desired cationic material.
  • a solvent such as ethanol, propylene glycol or preferably a fatty alcohol ethoxylate such as C- ⁇ o-C-18 fatty alcohol ethoxylate having a degree of ethoxylation of from 3 to 50 ethoxy groups per mole forming the desired cationic material.
  • They may also be prepared by the direct esterification of a long chain fatty acid of the desired chain length together with 2-haloethanol
  • Suitable cationic ester surfactants have the structural formulas below, wherein d may be from 0 to 20.
  • cationic ester surfactant are hydrolysable under the conditions of a laundry wash method.
  • Cationic surfactants useful herein also include alkoxylated quaternary ammonium (AQA) surfactant compounds (referred to hereinafter as "AQA compounds") having the formula:
  • R ⁇ is a linear or branched alkyl or alkenyl moiety containing from about
  • R2 is an alkyl group containing from one to three carbon atoms, preferably methyl;
  • R 3 and R 4 can vary independently and are selected from hydrogen (preferred), methyl and ethyl;
  • X" is an anion such as chloride, bromide, methylsulfate, sulfate, or the like, sufficient to provide electrical neutrality.
  • a and A' can vary independently and are each selected from C-1-C4 alkoxy, especially ethoxy (i.e., -CH2CH2O-), propoxy, butoxy and mixed ethoxy/propoxy; p is from 0 to about 30, preferably 1 to about 4 and q is from 0 to about 30, preferably 1 to about 4, and most preferably to about 4; preferably both p and q are 1.
  • EP 2,084, published May 30, 1979, by The Procter & Gamble Company which describes cationic surfactants of this type which are also useful herein..
  • AQA compounds wherein the hydrocarbyl substituent R ⁇ is C8-C ⁇
  • the levels of the AQA surfactants used to prepare finished laundry detergent compositions can range from about 0.1% to about 5%, typically from about 0.45% to about 2.5%, by weight.
  • AQA surfactants used herein. It is to be understood that the degree of alkoxylation noted herein for the AQA surfactants is reported as an average, following common practice for conventional ethoxylated nonionic surfactants. This is because the ethoxylation reactions typically yield mixtures of materials with differing degrees of ethoxylation. Thus, it is not uncommon to report total EO values other than as whole numbers, e.g., "EO2.5", “EO3.5”, and the like. Desi ⁇ nation R R2 ApR 3 AqR 4 AQA-1 C-12-C14 CH3 EO EO
  • Coco Methyl EO2 AQA-2 C-12-C16 CH3 (EO) 2 EO
  • the preferred bis-ethoxylated cationic surfactants herein are available under the trade name ETHOQUAD from Akzo Nobel Chemicals Company.
  • R ⁇ is C10-C18 hydrocarbyl and mixtures thereof, preferably C10. C12. C14 alkyl and mixtures thereof, and X is any convenient anion to provide charge balance, preferably chloride.
  • R ⁇ is derived from coconut (C-12-C14 alkyl) fraction fatty acids
  • R 2 is methyl and ApR 3 and A'qR 4 are each monoethoxy
  • this preferred type of compound is referred to herein as "CocoMeE02" or "AQA-1" in the above list.
  • Other preferred AQA compounds herein include compounds of the formula:
  • R1 is C10-C18 hydrocarbyl, preferably C10-C14 alkyl, independently p is 1 to about 3 and q is 1 to about 3
  • R2 is C1-C3 alkyl, preferably methyl
  • X is an anion, especially chloride.
  • cationic surfactants are described, for example, in the "Surfactant Science Series, Volume 4, Cationic Surfactants” or in the “Industrial Surfactants Handbook".
  • Classes of useful cationic surfactants described in these references include amide quats (i.e., Lexquat AMG & Schercoquat CAS), glycidyl ether quats (i.e., Cyostat 609), hydroxyalkyl quats (i.e., Dehyquart E), alkoxypropyl quats (i.e., Tomah Q-17-2), polypropoxy quats (Emcol CC-9), cyclic alkylammonium compounds (i.e., pyridinium or imidazolinium quats), and/or benzalkonium quats.
  • amide quats i.e., Lexquat AMG & Schercoquat CAS
  • glycidyl ether quats i.e.,
  • the cationic particle of the present invention also contains a water- insoluble high absorbing material.
  • the water-insoluble high absorbing material is a material having an oil absorption (using di-butyl phthalate) of preferably from about 140 mUIOOg to about 400 mL/100g, even more preferably from about 200 mL/100g to about 300 mUIOOg.
  • the high absorbing material is selected from the group consisting of aluminosilicate, precipitated silica, amorphous silica, talc, and mixtures thereof.
  • sodium aluminosilicates and amorphous precipitated silica are sodium aluminosilicates and amorphous precipitated silica.
  • An example of an amorphous precipitated silica is a porous hydrophyllic silica (trademark SIPERNAT 22S) available by DeGussa.
  • Another example of a precipitated silica is a white carbon, such as calcium silicate synthetic amorphous silica, (trademark Carplex) available by Shionogi and Company Ltd.
  • the ratio of the high absorbing material to the cationic surfactant active when forming the particle is from about 1 :3 to about 1 :1 , even more preferably from about 1 :2 to about 1 :1.
  • Absorption here means that the high absorbing material is coated with the cationic surfactant solution, and/or that the high absorbing material is impregnated with the cationic surfactant solution.
  • the finished cationic particle preferably has a mean particle size of greater than about 100 microns, and more preferably from about 100 microns to about 1000 microns, even more preferably from about 150 microns to about 650 microns.
  • a preferred finished cationic particle has the following composition, by weight percent of the cationic particle: cationic surfactant active from about 30% to about 65%; moisture content of from about 3% to about 15%; and the balance, the high absorbing material.
  • cationic surfactant active from about 30% to about 65%; moisture content of from about 3% to about 15%; and the balance, the high absorbing material.
  • filler and anionic surfactant may be included.
  • One embodiment for the cationic particle contain in addition, some anionic surfactant. If included, the ratio of anionic surfactant active to cationic surfactant active is from about 1 :10 to about 1 :30, preferably from about 1 :15 to about 1 :25.
  • the content of anionic surfactant is preferably from about 1% to about 5%.
  • anionic surfactant may in addition be included as an additional cleaning component for the final detergent composition.
  • the addition of small quantities of anionic surfactant in the cationic particle provides free flow characteristics to the cationic particle and provides a less sticky surface on the cationic particle.
  • the cationic particle optionally also contains a filler, such as soda ash, other silicate, and/or sulfate.
  • the cationic particle may be formulated in detergent compositions.
  • Such detergent compositions herein may optionally comprise other known detergent cleaning components including alkoxylated polycarboxylates, bleaching compounds, brighteners, chelating agents, clay soil removal / anti-redeposition agents, dye transfer inhibiting agents, enzymes, enzyme stabilizing systems, fabric softeners, polymeric soil release agents, polymeric dispersing agents, suds suppressors.
  • the detergent composition may also comprise other ingredients including carriers, hydrotropes, processing aids, dyes or pigments.
  • the preferred detergent compositions have a wide range of density, e.g., from about 300 g/l to about 1000 g/l, especially for high dense detergent agglomerates e.g., from about 600 g/l to about 850 g/l.
  • the cationic particle can be used to formulate detergent compositions.
  • the amount of cationic particle, by weight of the final detergent composition is preferably from about 0.5% to about 30%, more preferably from about 0.5% to about 10%.
  • Process Preferred examples of the process of making the cationic particle of the present invention is described below.
  • the cationic surfactant solution, high absorbing material, and optionally anionic surfactant and a filler are mixed and agitated to form a substantially homogenous mixture.
  • the mixture is then sprayed into a tower, wherein cationic particles are formed.
  • the cationic surfactant solution is added to the high absorbing material and agitated in a mixer to form a moist granular powder, or agglomerate.
  • the powder is then dried, such as in a fluid bed dryer, to form the finished cationic particle.
  • cationic surfactant solution (30-70% active), amorphous precipitated silica, optionally sodium carbonate, optionally sodium linear alkyl benzene sulfonate and water, are mixed in a crutcher tank mix. The mixture is then fed into the spray tower and cationic particles having about 150 microns are formed. The spray tower's drying temperature is about 160°C to 170°C.
  • 100 kg/hr of amorphous precipitated silica is fed into a mixer, such as a Loedige KM mixer, and 250 kg/hr of cationic surfactant solution is added to the mixer at one or more points while mixing takes place.
  • the calculated mean residence time in the mixer of the silica is about 1-10 minutes.
  • the moist granules from the mixer are then fed to a fluid bed dryer, where the moisture is removed by warm air at about 100°C to 150°C, preferably about 115°C to 130°C.
  • the resultant cationic particles have a mean particle size of about 100 to 1000 microns, preferably 350 to 650 microns.
  • the finished agglomerate particle is free-flowing without the need for additional ingredients.
  • the following examples show cationic particle compositions of the present invention :
  • Cationic surfactant A C12-14 Dimethyl Hydroxyethyl Ammonium
  • Chloride Solution Cationic surfactant B C8-10 Dimethyl Hydroxyethyl Ammonium

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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)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Peptides Or Proteins (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/US1999/002082 1999-02-01 1999-02-01 Cationic particle and a process for making thereof WO2000044874A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
JP2000596119A JP2002535480A (ja) 1999-02-01 1999-02-01 カチオン粒子およびその製造方法
CN99815982.4A CN1334865A (zh) 1999-02-01 1999-02-01 阳离子颗粒及其制取方法
PCT/US1999/002082 WO2000044874A1 (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof
CA002359319A CA2359319C (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof
US09/890,513 US6627596B1 (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof
ES99905576T ES2241261T3 (es) 1999-02-01 1999-02-01 Particula cationica y un procemineto para fabricar la misma.
EP99905576A EP1149155B1 (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof
AT99905576T ATE294228T1 (de) 1999-02-01 1999-02-01 Kationisches teilchen und verfahren zu seiner herstellung
BR9917013-2A BR9917013A (pt) 1999-02-01 1999-02-01 Partìcula catiÈnica e um processo para sua produção
AU25708/99A AU2570899A (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof
DE69925037T DE69925037T2 (de) 1999-02-01 1999-02-01 Kationisches teilchen und verfahren zu seiner herstellung

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1999/002082 WO2000044874A1 (en) 1999-02-01 1999-02-01 Cationic particle and a process for making thereof

Publications (1)

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WO2000044874A1 true WO2000044874A1 (en) 2000-08-03

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EP (1) EP1149155B1 (pt)
JP (1) JP2002535480A (pt)
CN (1) CN1334865A (pt)
AT (1) ATE294228T1 (pt)
AU (1) AU2570899A (pt)
BR (1) BR9917013A (pt)
CA (1) CA2359319C (pt)
DE (1) DE69925037T2 (pt)
ES (1) ES2241261T3 (pt)
WO (1) WO2000044874A1 (pt)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001081528A1 (en) * 2000-04-20 2001-11-01 Unilever Plc Granular detergent component and process for its preparation
US6573229B2 (en) 2000-04-12 2003-06-03 Unilever Home & Personal Care Usa Division Of Conopco Inc. Laundry wash compositions
US7018972B2 (en) 2001-10-25 2006-03-28 Unilever Home and Personal Care USA a division of Conopco, Inc. Process for the production of detergent granules
US7018971B2 (en) 2001-10-25 2006-03-28 Unilever Home And Personal Care Usa Division Of Conopco, Inc. Process for the production of detergent granules

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004018751A1 (de) * 2004-04-17 2005-11-03 Clariant Gmbh Verfahren zur Herstellung von quaternären Hydroxyalkylammonium Granulaten

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998013453A1 (en) * 1996-09-24 1998-04-02 The Procter & Gamble Company Detergent particle

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998013453A1 (en) * 1996-09-24 1998-04-02 The Procter & Gamble Company Detergent particle

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6573229B2 (en) 2000-04-12 2003-06-03 Unilever Home & Personal Care Usa Division Of Conopco Inc. Laundry wash compositions
WO2001081528A1 (en) * 2000-04-20 2001-11-01 Unilever Plc Granular detergent component and process for its preparation
US6596684B2 (en) 2000-04-20 2003-07-22 Unilever Home & Personal Care Usa Divison Of Conopco, Inc. Granular detergent component and process for its preparation
US7018972B2 (en) 2001-10-25 2006-03-28 Unilever Home and Personal Care USA a division of Conopco, Inc. Process for the production of detergent granules
US7018971B2 (en) 2001-10-25 2006-03-28 Unilever Home And Personal Care Usa Division Of Conopco, Inc. Process for the production of detergent granules

Also Published As

Publication number Publication date
ATE294228T1 (de) 2005-05-15
CA2359319A1 (en) 2000-08-03
DE69925037D1 (de) 2005-06-02
JP2002535480A (ja) 2002-10-22
ES2241261T3 (es) 2005-10-16
CN1334865A (zh) 2002-02-06
BR9917013A (pt) 2002-01-15
EP1149155B1 (en) 2005-04-27
CA2359319C (en) 2005-06-14
EP1149155A1 (en) 2001-10-31
DE69925037T2 (de) 2006-03-09
AU2570899A (en) 2000-08-18

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