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WO1996013564A1 - Compositions non aqueuses comprenant des amides d'acides gras polyhydroxyles - Google Patents

Compositions non aqueuses comprenant des amides d'acides gras polyhydroxyles Download PDF

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Publication number
WO1996013564A1
WO1996013564A1 PCT/US1995/013562 US9513562W WO9613564A1 WO 1996013564 A1 WO1996013564 A1 WO 1996013564A1 US 9513562 W US9513562 W US 9513562W WO 9613564 A1 WO9613564 A1 WO 9613564A1
Authority
WO
WIPO (PCT)
Prior art keywords
fatty acid
liquid premix
weight
polyhydroxy fatty
chain
Prior art date
Application number
PCT/US1995/013562
Other languages
English (en)
Inventor
Paul Amaat Raymond Gerard France
Steven Rene Ongena
Carole Patricia Denise Wilkinson
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
Publication of WO1996013564A1 publication Critical patent/WO1996013564A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • This invention concerns liquid premixes comprising certain nonionic surfactants, including fatty acid amides, which are suitable for further processing into detergent
  • the polyhydroxy fatty acid amides are one class of nonionic surfactants which are currently being investigated for use in detergent compositions.
  • One problem with this class of surfactants is that concentrated aqueous solutions
  • WO 9206160 published April 16th, 1992, describes aqueous compositions comprising polyhydroxy fatty acid amides and ethoxylated nonionic surfactants. Ratios between 1:5 and 5:1 are claimed.
  • Non-aqueous premixes of polyhydroxy fatty acid amide.
  • Ethoxylated nonionic surfactants are suitable for this purpose if they are added at high levels, for example 2 parts ethoxylated nonionic to 1 part polyhydroxy fatty acid amide.
  • WO9000189 published January 11th, 1990, describes a process of spraying nonionic surfactant premix on to a base powder. It is claimed that solubility and dispersibility are improved if the nonionic premix comprises from 1% to 40% of hydrophobic substance containing polar groups (such as fatty acid, fatty acid ester, fatty acid amide, fatty amine, fatty alcohol or quaternary ammonium compound).
  • hydrophobic substance containing polar groups such as fatty acid, fatty acid ester, fatty acid amide, fatty amine, fatty alcohol or quaternary ammonium compound.
  • EP592754 published April 20th, 1994, describes a liquid premix comprising polyhydroxy fatty acid amide and a borate functional material.
  • the benefit claimed is that the premix does not solidify or gel at temperatures above about 20-30°C.
  • borate functional materials may be
  • the present invention addresses the problem of providing an alternative melting point depressant for use in non-aqueous liquid premixes comprising polyhydroxy fatty acid amide. It has been found that choline ester acts to reduce the melting point of a typical polyhydroxy fatty acid amide / ethoxylated nonionic premix. The presence of 10% by weight of choline ester reduces the melting point by about 12°C. The possibility of storage and handling at lower
  • temperatures has the further benefit of handling higher concentrations of polyhydroxy fatty acid amide than would be possible without the melting point depressant, and additionally reduces the rate of product decomposition.
  • the present invention provides storage-stable, pumpable fluid compositions which contain
  • the invention provides such fluid compositions using ingredients which are either innocuous in the finished detergent composition, or which can provide desirable benefits to said finished
  • compositions Accordingly, removal of such ingredients is not required.
  • the invention concerns a concententrated liquid premix comprising polyhydroxy fatty acid amide of the formula:
  • R is C5-C31 hydrocarbyl, preferably straight-chain
  • R1 is C1-C8, preferably C1-C4 hydrocarbyl.
  • Z is polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 2, preferably at least 3 hydroxyls directly connected to the chain, wherein the liquid premix further comprises from 1% to 30% , preferably from 5% to 10%, by weight of choline ester.
  • polyhydroxy fatty acid amide is C12-C18 linear alkyl N-methyl glucamine at a level of at least 25% by weight, even more preferably from 50% to 80% by weight, and most preferably from 60% to 75% by weight.
  • the molar ratio of the polyhydroxy fatty acid amide to the choline ester is from 20:1 to 2:1.
  • liquid premix is essentially anhydrous.
  • Preferred embodiments may, however comprise from 5% to 50% by weight of ethoxylated nonionic surfactant, and may also optionally comprise from 1% to 40% by weight of a solvent chosen from propylene glycol, ethanol, glycerine or mixtures thereof.
  • the present invention also concerns a process of treating the liquid premix mentioned above to form granules by spraying the premix onto a preformed adsorbent detergent power.
  • granules may be formed by agglomerating finely divided detergent powders in the presence of the premix, preferably in a high shear mixer.
  • concentrate liquid premix herein is meant percentages of the polyhydroxy fatty acid amide typically in the range of at least 25% by weight, preferably 35% to 80% by weight, and most preferably from 45% to 75% by weight.
  • pumpable herein is meant a viscosity below about 20 000 mPas, preferably below about 12 000 mPas.
  • Viscosity is measured by means of a Brookfield Viscometer Model DVII with a Thermosel System. The viscosity of the systems is measured at 80°C.
  • stable liquid premix herein is meant a homogeneous, fluid, nonbirefringent liquid. This can be estimated visually using polarised light, and can be confirmed using a microscope under polarised light. There should be no crystallisation or precipitation when a sample is examined by the naked eye.
  • Polyhydroxy fatty acid amides may be produced by reacting a fatty acid ester and an N-alkyl polyhydroxy amine.
  • the preferred amine for use in the present invention is N-(R1)-CH2(CH2OH)4-CH2-OH and the preferred ester is a C12-C20 fatty acid methyl ester. Most preferred is the reaction product of N-methyl glucamine with C12-C20 fatty acid methyl ester.
  • Nonionic surfactant systems and granular detergents made from such systems have been described in WO 92 6160, published on 16th April, 1992.
  • This application describes (example 15) a granular detergent composition prepared by fine dispersion mixing in an Eirich RV02 mixer which comprises N-methyl glucamide (10%), nonionic surfactant (10%).
  • the polyhydroxy fatty acid amide may be present in compositions of the present invention at a level of from 0% to 40% by weight of the detergent component or composition, preferably from 1% to 30% by weight, even more preferably from 1% to 20% by weight.
  • Preferred choline ester derivatives having the following formula :
  • R is a C5 to C30 straight chain or branched chain alkyl or alkenyl
  • X is an anion, which makes the compound at least water-dispersible, preferably selected from the group consisting of halide, methyl sulfate, sulfate, and nitrate, preferably methyl sulfate, chloride, bromide or iodide.
  • ester linkage in the above formula is replaced with a reverse ester, amide or reverse amide linkage.
  • p may be from 0 to 20.
  • the preferred choline-derivative cationic substances 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, forming the desired cationic material.
  • the choline-derived cationic materials may also be prepared by the direct esterification of a long chain fatty acid of the desired chain length together with 2- haloethanol, in the presence of an acid catalyst material. The reaction product is then used to quaternize.
  • Trimethylamine forming the desired cationic component.
  • Other suitable choline esters for use herein have the formula:
  • t is 0 or 1
  • y is from 1 to 20
  • R and X are as defined above.
  • the choline esters herein can be present at levels of from 0% to 50% by weight of the compositions, preferably from 1% to 30% by weight, even more preferably from 1% to 20% by weight.
  • non-aqueous premixes of the present invention may be incorporated into granular laundry detergent compositions by any of the techniques known in the art. Granulation by agglomeration is one particularly preferred process.
  • Spraying the premix onto a prepared base powder is an alternative preferred process.
  • Suitable agglomeration techniques are described in more detail in the Applicants co-pending European Application number 9401094.3, filed on 21st April 1994.
  • the liquid premix of the present invention is intimately mixed with finely divided detergent powders, such as sodium aluminosilicate or other builders, in a high shear mixer, such as a Loedige® CB unit.
  • Agglomerates may be finished in further mixing units, such as a Loedige® KM, or a fluidised bed.
  • Suitable techniques for spraying the premix onto prepared base powder as described in more detail in the Applicants co-pending Patent Application WO9405761, published on 17th March 1994.
  • N-methyl glucamide is CH 3 (CH2) n CO N CH 3 CH 2
  • the choline ester is handled in a propylene glycol solvent in a ratio of 7 parts choline ester to 3 parts propylene glycol (Examples 1 to 3) or 3 parts alkyl ethoxylate
  • Each of the liquid premix compositions of Examples 1 to 3 and A to F were prepared by mixing the raw materials in the appropriate ratios.
  • the compositions were maintained at a temperature above the indicated melting point during transportation and storage.
  • the lower storage temperatures of Examples 1 to 3, compared to Examples A to F, resulted in slower rates of degradation of the premix.
  • liquid premix compositions were then sprayed on to a detergent base powder that had been prepared by
  • agglomeration of surfactants, builders etc.
  • dry mixing of granular percarbonate bleach, citric acid, granular suds suppressor, granular bleach activator, granular carbonate and bicarbonate, enzymes and
  • the ratio was 1 part liquid premix to 9 parts detergent base powder.
  • the temperature of the premix was reduced immediately before the spraying step to between 10° and 20°C below the indicated melting point so that crystallisation of the premix was starting to occur, but not to the extent that it would cause blockage of the nozzles.
  • Example temperature was between 46°C and 50°C for Examples 1 to 3, and between 58°C and 62°C for Examples A to F (i.e a reduction of about 12°C in spraying on temperature).
  • Example C being worse than Example A and F being worse than example D.
  • Example 1 to 3 showed better stability of the heat sensitive components, such as enzymes, than Examples A to F.

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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

L'invention concerne un prémélange liquide concentré comprenant un amide d'acide gras polyhydroxyle de la formule (I) dans laquelle R représente hydrocarbyle C5-C31, de préférence alcényle ou alkyle C7-C19 à chaîne droite, R1 représente hydrocarbyle C1-C8, de préférence C1-C4, et Z représente un polyhydroxyhydrocarbyle présentant une chaîne hydrocarbyle linéaire avec au moins 2, et de préférence au moins 3 hydroxyles directement liés à la chaîne, où le prémélange comprend entre 1 et 30 %, de préférence entre 5 et 10 %, en poids d'ester de choline.
PCT/US1995/013562 1994-10-28 1995-10-12 Compositions non aqueuses comprenant des amides d'acides gras polyhydroxyles WO1996013564A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP94203141.0 1994-10-28
EP94203141A EP0709449A1 (fr) 1994-10-28 1994-10-28 Compositions non-aqueuses contenant des amides d'acide gras polyhydroxylé

Publications (1)

Publication Number Publication Date
WO1996013564A1 true WO1996013564A1 (fr) 1996-05-09

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EP (1) EP0709449A1 (fr)
WO (1) WO1996013564A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013234281A (ja) * 2012-05-10 2013-11-21 Lion Corp 粒状洗浄剤の製造方法

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9606913D0 (en) 1996-04-02 1996-06-05 Unilever Plc Surfactant blends processes for preparing them and particulate detergent compositions containing them
US8933131B2 (en) 2010-01-12 2015-01-13 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
JP2014506581A (ja) 2011-02-17 2014-03-17 ザ プロクター アンド ギャンブル カンパニー バイオベースの直鎖アルキルフェニルスルホネート
MX340089B (es) 2011-02-17 2016-06-23 Procter & Gamble Composiciones que comprenden mezclas de alquil fenil sulfonatos de c10-c13.
JP6729925B2 (ja) 2012-05-30 2020-07-29 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド Ｎ−メチル−ｎ−アシルグルカミン含有組成物
EP2858621B1 (fr) * 2012-05-30 2016-09-14 Clariant International Ltd Solutions tensioactives contenant des n-méthyl-n-c8-c10-acylglucamines et des n-méthyl-n-c12-c14-acylglucamines
US10813862B2 (en) 2012-05-30 2020-10-27 Clariant International Ltd. Use of N-methyl-N-acylglucamines as solubilizers
WO2013178668A2 (fr) * 2012-05-30 2013-12-05 Clariant International Ltd. Solutions tensioactives contenant des n-méthyl-n-oleylglucamines et des n-méthyl-n-c12-c14-acylglucamines
DE102012021647A1 (de) 2012-11-03 2014-05-08 Clariant International Ltd. Wässrige Adjuvant-Zusammensetzungen
DE102014005771A1 (de) 2014-04-23 2015-10-29 Clariant International Ltd. Verwendung von wässrigen driftreduzierenden Zusammensetzungen
DE102015219651A1 (de) 2015-10-09 2017-04-13 Clariant International Ltd. Zusammensetzungen enthaltend Zuckeramin und Fettsäure
DE202015008045U1 (de) 2015-10-09 2015-12-09 Clariant International Ltd. Universelle Pigmentdispersionen auf Basis von N-Alkylglukaminen
DE202016003070U1 (de) 2016-05-09 2016-06-07 Clariant International Ltd. Stabilisatoren für Silikatfarben
US20210071118A1 (en) * 2017-11-29 2021-03-11 Basf Se Compositions, their manufacture and use

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
WO1990000189A1 (fr) * 1988-07-02 1990-01-11 Henkel Kommanditgesellschaft Auf Aktien Additif d'agent de lavage a dispersibilite amelioree
WO1992006160A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Systemes tensioactifs non ioniques contenant des amides d'acides gras de polyhydroxy et un ou plusieurs tensioactifs non ioniques supplementaires
WO1994005761A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Procede de production de detergent en poudre de haute densite et compositions obtenues selon ce procede
EP0592754A1 (fr) * 1992-10-13 1994-04-20 The Procter & Gamble Company Compositions fluides contenant des amides d'acide gras polyhydroxylé

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5194639A (en) * 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
CA2131173C (fr) * 1992-03-16 1998-12-15 Brian J. Roselle Compositions de liquides contenant des amides d'acides gras polyhydroxyliques

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
WO1990000189A1 (fr) * 1988-07-02 1990-01-11 Henkel Kommanditgesellschaft Auf Aktien Additif d'agent de lavage a dispersibilite amelioree
WO1992006160A1 (fr) * 1990-09-28 1992-04-16 The Procter & Gamble Company Systemes tensioactifs non ioniques contenant des amides d'acides gras de polyhydroxy et un ou plusieurs tensioactifs non ioniques supplementaires
WO1994005761A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Procede de production de detergent en poudre de haute densite et compositions obtenues selon ce procede
EP0592754A1 (fr) * 1992-10-13 1994-04-20 The Procter & Gamble Company Compositions fluides contenant des amides d'acide gras polyhydroxylé

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013234281A (ja) * 2012-05-10 2013-11-21 Lion Corp 粒状洗浄剤の製造方法

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Publication number Publication date
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