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WO1994012601A1 - Preparations tensioactives visqueuses aqueuses - Google Patents

Preparations tensioactives visqueuses aqueuses Download PDF

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Publication number
WO1994012601A1
WO1994012601A1 PCT/EP1993/002963 EP9302963W WO9412601A1 WO 1994012601 A1 WO1994012601 A1 WO 1994012601A1 EP 9302963 W EP9302963 W EP 9302963W WO 9412601 A1 WO9412601 A1 WO 9412601A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight
formula
alkyl
ether sulfate
water
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1993/002963
Other languages
German (de)
English (en)
Inventor
Rainer Hofmann
Thomas Förster
Dieter Nickel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to EP93924051A priority Critical patent/EP0670877B1/fr
Priority to DE59304705T priority patent/DE59304705D1/de
Publication of WO1994012601A1 publication Critical patent/WO1994012601A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to low-concentration and highly viscous aqueous surfactant preparations which contain alkyl glycosides and certain alkyl or alkenyl ether sulfates, a process for their preparation and the use of such preparations as detergents or cleaners.
  • alkyl glycosides with long-chain alkyl groups belong to the nonionic surfactants.
  • the person skilled in the art also knows, for example in A.M. Schwartz, J.W. Perry, Surface Active Agents, Vol. I, Interscience Publishers, 1949, page 372 described that surfactant mixtures generally have synergistic effects and often have better cleaning properties than would result from the sum of the values of the individual components.
  • Detergents which contain alkyl glycosides in combination with at least one conventional anionic surfactant in a ratio of 1:10 to 10: 1 are described in European patent application EP 070074.
  • Detergents which contain alkyl glycosides and anionic surfactants are also known from European patent application EP 092 877.
  • liquid detergents are known from European patent application EP 105556, which contain alkyl glycosides, certain other nonionic surfactants and anionic surfactants.
  • From the international patent application WO 86/02943 alkylglycoside-containing liquid detergents are known which contain conventional anionic surfactants.
  • a process for the production of alkyl glycosides using catalytic amounts of an anionic surfactant in its acid form is known from European patent application EP 132043.
  • European patent application EP 132046 proposes to modify such a production process by adding certain bases after the actual reaction to neutralize the catalyst.
  • the preparatory detergents or cleaning agents mentioned in these documents are relatively highly concentrated aqueous solutions or pastes, since the components intended for the mixture to give finished compositions should have the highest possible active substance content. At the same time, they must be easy to handle, which means that they should have the lowest possible viscosity, flow and be easy to pump.
  • aqueous liquid products used by the consumer which include, in particular, liquid detergents, dishwashing detergents and universal cleaners, but also cosmetic products, for example hair shampoos or body-cleaning lotions, although the active substance content of such products is generally relative is low.
  • Such products therefore normally contain thickeners, which generally have the disadvantage that they themselves do not contribute to the cleaning performance of the surfactant component contained in the agents.
  • Typical thickeners are inorganic water-soluble salts, in particular sodium chloride, and salts of non-surface-active aromatic sulfonic acids, for example sodium cumene sulfonate.
  • Organic thickeners are usually fatty acid alkanolamides, such as coconut fatty acid onoethanolamide, lauric acid monoethanolamide, oleic acid diethanolamide and coconut fatty acid diethanolamide, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • fatty acid alkanolamides such as coconut fatty acid onoethanolamide, lauric acid monoethanolamide, oleic acid diethanolamide and coconut fatty acid diethanolamide, polyethylene glycol difatty acid esters and a number of water-soluble polymers.
  • agents which contain 15% by weight alkyl glycoside have a viscosity of less than 350 mPa.s at a content of approx. 0.5% by weight alkyl ether sulfate and the viscosity of such Agent goes through a minimum with the addition of increasing amounts of alkyl ether sulfate.
  • agents are generally both too highly concentrated and not viscous enough to be regarded as easy to handle.
  • the surfactant preparations according to the invention are accordingly gel-like aqueous
  • R 2 is an alkyl or alkenyl radical having 8 to 22 carbon atoms and up to 3 CC double bonds
  • p is the number 2 or 3
  • q is a number from 1 to 10, preferably from 1 to 5
  • X is an alkali metal ion, is an ammonium or alkyl- or hydroxyalkyl-substituted ammonium ion, the weight ratio of alkyl glycoside according to formula I to ether sulfate according to formula II being 35: 1 to 3: 1, preferably 15: 1 to 8: 1, and to 100 % By weight of water or a mixture of water with a water-miscible organic solvent.
  • gel-like preparations are understood to mean structured, isotropic, viscoelastic solutions with a viscoelastic network structure composed of rods. They preferably have a viscosity, measured at a temperature in the range from 20 ° C. to 25 ° C. at a shear rate of 10 s ⁇ *, from 400 mPa-s to 10,000 mPa-s, in particular from 500 mPa-s to 8000 mPa-s.
  • alkyl glycoside preparations according to the invention preferably contain
  • Some of the water, in particular not more than 5% by weight, based on the preparation according to the invention, can be mixed with a water-miscible organic solvent, preferably from the group comprising alcohols containing 1 to
  • Another object of the invention is a process for the preparation of storage-stable, gel-like surfactant preparations on an aqueous basis which have a viscosity in the range of 400 mPa at a temperature in the range from 20 ° C. to 25 ° C. at a shear rate of 10 s -1 . s to 10,000 mPa.s by mixing an aqueous solution containing an alkyl glycoside of the formula I,
  • R 1 is an alkyl radical having 8 to 22 carbon atoms
  • G is a glycose unit and n is a number between 1 and 10, with an ether sulfate of the formula II,
  • R 2 is an alkyl or alkenyl radical having 8 to 22 carbon atoms and up to 3 CC double bonds
  • p is the number 2 or 3
  • q is a number from 1 to 10, preferably from 1 to 10
  • X is an alkali metal ion, is an ammonium or alkyl- or hydroxyalkyl-substituted ammonium ion, in the weight ratio of alkyl glycoside according to formula I to ether sulfate according to formula II from 35: 1 to 3: 1, and with as much water or a mixture of water with a water-miscible one organic solvents that the total surfactant content in the preparation is 2.2% by weight to 12% by weight.
  • the procedure is preferably such that an aqueous paste which contains alkyl glycoside of the formula I in a concentration of 30% by weight to 60% by weight is mixed in such an amount with the ether sulfate or with an aqueous solution of the ether sulfate, that the sum of the surfactants in the resulting aqueous preparation is 2.5% by weight to 10% by weight and the resulting gel contains 90% by weight to 97.5% by weight of water.
  • the water can be mixed in at any point in the preparation of the agents according to the invention if the starting materials used do not already contain sufficient such solvent.
  • the Components heated to temperatures of 60 ° C to 80 ° C and mixed with conventional mixers, which are preferably heatable and are kept during the entire mixing process, in particular at temperatures in the range mentioned.
  • alkylglycosides suitable for the surfactant preparations according to the invention and their preparation are described, for example, in European patent applications EP 92355, EP 301 298, EP 357 969 and EP 362671 or the US Pat. No. 3,547,828.
  • the glycoside components ((G) n in formula I) of such alkyl glycosides are oligomers or polymers from naturally occurring aldose or ketose monomers, which include, in particular, glucose, mannose, fructose, galactose, talose, gulose, Altrose, Allose, Idose, Ribose, Arabinose, Xylose and Lyxose belong.
  • the oligomers consisting of such glycosidically linked monomers are characterized not only by the type of sugar they contain, but also by their number, the so-called degree of oligomerization.
  • the degree of oligomerization (n in formula I) can also take non-integer numerical values as the quantity to be determined analytically; it is generally between 1 and 10, for the alkyl glycosides which are preferably used below 1.5, in particular between 1.2 and 1.4.
  • the preferred monomer building block is glucose because of its good availability.
  • the alkyl portion (R1 in formula I) of the alkyl glycosides contained in the surfactant preparations according to the invention preferably also originates from easily accessible derivatives of renewable raw materials, in particular from fatty alcohols, although their branched chain isomers, in particular so-called oxo alcohols, are also used to prepare usable alkyl glycosides can be. Accordingly, the primary alcohols with linear octyl, decyl, dodecyl, tetradecyl, hexadecyl or octa-decyl radicals and mixtures thereof are particularly useful.
  • the alkyl glycosides can contain small amounts, for example 1 to 2%, of unreacted free fatty alcohol, which generally does not have a disadvantageous effect on the properties of the preparations produced therewith.
  • ether sulfates which can be used in the context of the invention are anionic surfactants which, as a rule, are obtained by the known reaction of aliphatic primary alcohols with preferably 1 to 10, in particular 1 to 5, molar equivalents of alkylene oxide, in particular ethylene oxide, and subsequent reaction with a sulfating reagent, for example, sulfur trioxide or chlorosulfonic acid, and subsequent neutralization and hydrolysis of the reaction products formed, preferably with alkali, ammonium or alkyl or hydroxyalkyl-substituted ammonium bases.
  • anionic surfactants which, as a rule, are obtained by the known reaction of aliphatic primary alcohols with preferably 1 to 10, in particular 1 to 5, molar equivalents of alkylene oxide, in particular ethylene oxide, and subsequent reaction with a sulfating reagent, for example, sulfur trioxide or chlorosulfonic acid, and subsequent neutralization and hydrolysis of the reaction products formed, preferably with alkali,
  • Ether sulfates to which the process according to the invention extends are preferably derived from alkoxylated, in particular ethoxylated, fatty alcohols having 12 to 22 carbon atoms, in particular 12 to 18 carbon atoms.
  • the degree of alkoxylation (q in formula II) is preferably 1 to 3.
  • the degree of alkoxylation as a quantity to be determined analytically can also assume non-integer numerical values.
  • Typical examples of starting materials for the ether sulfates which can be used according to the invention are lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol or behenyl alcohol and the corresponding unsaturated alcohols which can be obtained by reducing the carboxyl group from oleic acid, lauroleic acid, myristoleic acid, gadoleic acid, erucic acid, linoleic acid and linolenic acid.
  • the ether sulfates can also be derived from technical alcohol mixtures, such as are obtained, for example, from the hydrogenation of technical fatty acid ester mixtures of natural origin or from aldehydes from Roelen's oxosynthesis.
  • the ether sulfates produced in this way preferably contain as little as possible, in particular not more than 5% by weight, based on ether sulfate, of inorganic salt.
  • ether sulfate include the alkali metal chlorides and in particular the alkali metal sulfates. If salt contents in such low amounts do not already occur in the production of the ether sulfates described above, The ether sulfate can be brought to contents not exceeding 5% by weight, in particular from 0.1% to 1.5% by weight, based in each case on ether sulfate, of inorganic salt by known methods, for example by recrystallization become.
  • surfactant preparations according to the invention which contain such low-salt ether sulfate show a more pronounced, advantageous viscosity behavior in comparison with higher-salt ether sulfate, although the addition of inorganic salts, in particular sodium chloride, is usually considered to be thickening.
  • Ether sulfates have long been known to be good anionic surfactants. However, it was surprising that the viscosity of dilute aqueous alkyl glycoside solutions can be increased significantly by adding very small amounts of such anionic surfactants. In contrast, the addition of alkylbenzenesulfonate as an example of another anionic surfactant, which is also known to have high cleaning performance, reduces the viscosity of dilute aqueous alkylglycoside solutions.
  • the surfactant preparations according to the invention have excellent cleaning properties and high solubility in cold water. They are therefore preferably used as washing, rinsing or cleaning agents and in hair and body care or serve as storage-stable, easy-to-use premixes for the production of such agents.
  • builder substances such as zeolites and phyllosilicates, corrosion inhibitors, bleaching agents, bleach activators, optical brighteners, enzymes, graying inhibitors, antimicrobial agents, abrasives, foam stabilizers, preservatives, pH regulators, opacifiers and pearlescent agents, colorants and fragrances and additional surfactants are possible among the preparations according to the invention. Examples
  • Alkylglycoside to ether sulfate had the viscosities listed below (25 ° C, measured with a shear stress controlled rotation rheometer Carri-Med ( R ) CS 100 at a shear rate of 10 s ⁇ *), whereby for comparison also the values for equally concentrated ether sulfate free aqueous solutions are listed.
  • Table 1 Properties of 5% by weight preparations (25 ° C)
  • preparations not according to the invention which contained Ci2 / 14-alkyl glucoside and Na-Cn / 13-alkylbenzenesulfonate (Maranil ( R ), manufacturer Hüls). These had a viscosity of 270 mPa-s in 5% by weight solution (weight ratio 4.9: 0.1) and a viscosity of 360 mPa * s in 10% by weight solution (weight ratio 9: 1).
  • the preparations according to the invention have significantly higher viscosities.

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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)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

Avec des formulations aqueuses faiblement concentrées contenant 2 à 10 % en poids d'un alkylglucoside de formule R1-0(G)n, dans laquelle R1 désigne un reste alkyle avec 8 à 22 atomes de C, G une unité glucose et n un nombre de 1 à 10, on se propose d'améliorer la facilité de manipulation dans certaines conditions d'utilisation et on s'est fixé comme objectif que la formulation contienne des quantités aussi faibles que possible d'une substance active ne comportant pas d'alkylglucoside. Cet objectif a été atteint essentiellement par l'addition, en vue d'accroître la viscosité, de 0,05 à 2 % en poids d'un sulfate d'éther de formule R2-O-(CpH2p0)qSO3X, dans laquelle R2 désigne un reste alkyle ou alcényle ayant 8 à 22 atomes de C et jusqu'à trois liaisons doubles C-C, p représente le nombre 2 ou 3, q représente un nombre de 1 à 10 et X représente un ion de métal alcalin, un ion ammonium ou un ion ammonium substitué par un alkyle ou un hydroxyalkyle, le rapport en poids de l'alkylglucoside au sulfate d'éther étant compris entre 35:1 et 3:1.
PCT/EP1993/002963 1992-11-26 1993-10-26 Preparations tensioactives visqueuses aqueuses Ceased WO1994012601A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP93924051A EP0670877B1 (fr) 1992-11-26 1993-10-26 Preparations tensioactives visqueuses aqueuses
DE59304705T DE59304705D1 (de) 1992-11-26 1993-10-26 Viskose wässrige tensidzubereitungen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4239679.4 1992-11-26
DE4239679A DE4239679A1 (de) 1992-11-26 1992-11-26 Viskose wäßrige Tensidzubereitungen

Publications (1)

Publication Number Publication Date
WO1994012601A1 true WO1994012601A1 (fr) 1994-06-09

Family

ID=6473649

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/002963 Ceased WO1994012601A1 (fr) 1992-11-26 1993-10-26 Preparations tensioactives visqueuses aqueuses

Country Status (3)

Country Link
EP (1) EP0670877B1 (fr)
DE (2) DE4239679A1 (fr)
WO (1) WO1994012601A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007092351A3 (fr) * 2006-02-03 2008-04-24 Bayer Cropscience Lp Compositions herbicides concentrées stables

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5534500A (en) * 1993-09-13 1996-07-09 Henkel Corporation Process for preparing surfactant mixtures having high solids content
DE19723733A1 (de) * 1997-06-06 1998-12-10 Beiersdorf Ag Kosmetische und dermatologische Emulsionen, enthaltend Alkylglucoside und erhöhte Elektrolytkonzentrationen

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483787A (en) * 1983-12-28 1984-11-20 The Procter & Gamble Company Concentrated aqueous detergent compositions
EP0216301A2 (fr) * 1985-09-25 1987-04-01 Henkel Kommanditgesellschaft auf Aktien Agent de nettoyage liquide
JPH0356596A (ja) * 1989-07-26 1991-03-12 Kao Corp 洗浄剤組成物
JPH03166298A (ja) * 1989-11-25 1991-07-18 Mitsubishi Petrochem Co Ltd 液体洗浄剤組成物
EP0486784A2 (fr) * 1990-11-17 1992-05-27 Hüls Aktiengesellschaft Détergent liquide moussant à viscosité augmentée
WO1992021742A1 (fr) * 1991-05-29 1992-12-10 Henkel Kommanditgesellschaft Auf Aktien Preparation tensioactive liquide apte a l'ecoulement et au pompage

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4483787A (en) * 1983-12-28 1984-11-20 The Procter & Gamble Company Concentrated aqueous detergent compositions
EP0216301A2 (fr) * 1985-09-25 1987-04-01 Henkel Kommanditgesellschaft auf Aktien Agent de nettoyage liquide
JPH0356596A (ja) * 1989-07-26 1991-03-12 Kao Corp 洗浄剤組成物
JPH03166298A (ja) * 1989-11-25 1991-07-18 Mitsubishi Petrochem Co Ltd 液体洗浄剤組成物
EP0486784A2 (fr) * 1990-11-17 1992-05-27 Hüls Aktiengesellschaft Détergent liquide moussant à viscosité augmentée
WO1992021742A1 (fr) * 1991-05-29 1992-12-10 Henkel Kommanditgesellschaft Auf Aktien Preparation tensioactive liquide apte a l'ecoulement et au pompage

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 15, no. 202 (C - 0834) 23 May 1991 (1991-05-23) *
PATENT ABSTRACTS OF JAPAN vol. 15, no. 403 (C - 0875) 15 October 1991 (1991-10-15) *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007092351A3 (fr) * 2006-02-03 2008-04-24 Bayer Cropscience Lp Compositions herbicides concentrées stables
JP2009525345A (ja) * 2006-02-03 2009-07-09 バイエル クロップサイエンス エルピー 安定した濃縮除草剤組成物
US7842647B2 (en) 2006-02-03 2010-11-30 Bayer Cropscience Lp Stable, concentrated herbicidal compositions
US8445406B2 (en) 2006-02-03 2013-05-21 Bayer Cropscience Lp Stable, concentrated herbicidal compositions
EA018916B1 (ru) * 2006-02-03 2013-11-29 БАЙЕР КРОПСАЙЕНС ЛПи Жидкая гербицидная композиция
US9078432B2 (en) 2006-02-03 2015-07-14 Bayer Cropscience Lp Stable, concentrated herbicidal compositions
US9675063B2 (en) 2006-02-03 2017-06-13 Bayer Cropscience Lp Stable, concentrated herbicidal compositions
US10091990B2 (en) 2006-02-03 2018-10-09 Bayer Intellectual Property Gmbh Stable, concentrated herbicidal compositions
US10716304B2 (en) 2006-02-03 2020-07-21 Basf Se Stable, concentrated herbicidal compositions
US11375713B2 (en) 2006-02-03 2022-07-05 Basf Se Stable, concentrated herbicidal compositions
US11856949B2 (en) 2006-02-03 2024-01-02 Basf Se Stable, concentrated herbicidal compositions

Also Published As

Publication number Publication date
DE4239679A1 (de) 1994-06-01
DE59304705D1 (de) 1997-01-16
EP0670877B1 (fr) 1996-12-04
EP0670877A1 (fr) 1995-09-13

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