EP0652932B1 - Procede de fabrication d'agents tensioactifs non ioniques stables au stockage - Google Patents

Procede de fabrication d'agents tensioactifs non ioniques stables au stockage Download PDF

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Publication number
EP0652932B1
EP0652932B1 EP93915972A EP93915972A EP0652932B1 EP 0652932 B1 EP0652932 B1 EP 0652932B1 EP 93915972 A EP93915972 A EP 93915972A EP 93915972 A EP93915972 A EP 93915972A EP 0652932 B1 EP0652932 B1 EP 0652932B1
Authority
EP
European Patent Office
Prior art keywords
alkyl
oligoglycosides
carbon atoms
alkenyl
crystallization
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.)
Expired - Lifetime
Application number
EP93915972A
Other languages
German (de)
English (en)
Other versions
EP0652932A1 (fr
Inventor
Manfred Weuthen
Thomas Engels
Hermann Hensen
Holger Tesmann
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
Publication of EP0652932A1 publication Critical patent/EP0652932A1/fr
Application granted granted Critical
Publication of EP0652932B1 publication Critical patent/EP0652932B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3707—Polyethers, e.g. polyalkyleneoxides
    • 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
    • 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
    • C11D1/825—Mixtures of compounds all of which are non-ionic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives thereof
    • 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
    • C11D1/72—Ethers of polyoxyalkylene glycols
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/02—Organic and inorganic agents containing, except water

Definitions

  • the invention relates to a process for the preparation of storage-stable nonionic surfactants with improved crystallization resistance, in which alk (en) yl oligoglycosides are added to selected crystallization moderators.
  • Alk (en) yl oligoglycosides are important non-ionic surfactants which, due to their good detergent properties and high environmental compatibility, are being used increasingly in detergents, dishwashing detergents and cleaning agents.
  • alk (en) yl oligoglycosides available for a certain period of time, for example as aqueous solutions or pastes, until they are finished.
  • aqueous alk (en) yl oligoglycosides show a strong tendency to crystallize, the homogeneity of such preparations decreases over time when they are stored under ambient conditions and form them agglomerates containing water of crystallization, which greatly reduce the pumpability of the products.
  • alk (en) yl oligoglycosides are therefore not stored at room temperature, but at temperatures of at least 40 ° C. In this way, crystallization of the preparations can be largely prevented, but storage at elevated temperature is associated with additional effort and can also severely impair the color quality of the products.
  • EP-A 0 388 810 aqueous compositions which contain alkyl glucosides and short-chain primary alcohols.
  • EP-A 0 487 262 relates to a process for the preparation of storage-stable alkyl glucosides in which fatty alcohol polyglycol ethers are added to the aqueous pastes as stabilizers. Mixtures of alkyl glucosides and ethoxylated fatty alcohols are also mentioned in the documents EP-A 0 377 807 and EP-A 0 405 967 .
  • EP-A 0 408 965 discloses aqueous compositions of alkyl glucosides and polyethylene glycols.
  • mixtures of alkyl glucosides based on linear and branched fatty alcohols are suitable for the production of liquid cleaning agents.
  • the object of the invention was therefore to develop a process by means of which alk (en) yl oligoglucosides can be stored at temperatures below 40 ° C. without impairing the pumpability of the products through the formation of crystalline agglomerates.
  • Alkyl and alkenyl oligoglycosides are known substances that can be obtained by the relevant methods of preparative organic chemistry. Representative of the extensive literature, reference is made here to the documents EP-A1-0 301 298 and WO 90/3977 .
  • the alkyl and / or alkenyl oligoglycosides can differ from aldoses or ketoses with 5 or 6 carbon atoms, preferably derive the glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened C 12/14 coconut alcohol with a DP of 1 to 3 are preferred.
  • the crystallization moderators can be added to the alkyl and / or alkenyl oligoglycosides in amounts of 0.01 to 7, preferably 1 to 3% by weight, based on the alkyl and / or alkenyl oligoglycosides. It has proven advantageous here to use iron (III) ions in amounts of 0.01 to 0.5% by weight in order to reliably prevent discoloration of the products catalyzed by Fe ions.
  • the process according to the invention is used to stabilize aqueous preparations which contain alkyl and / or alkenyl oligoglycosides.
  • the solids content of these preparations can be 1 to 70% by weight, preferably 30 to 60% by weight, the problem of reduced storage stability due to crystallization only becoming more important with products of higher concentration.
  • the aqueous preparations can also contain other ingredients customary for washing, rinsing and cleaning agents, such as: anionic, nonionic, amphoteric or zwitterionic surfactants, oil bodies, builders, hydrotropes, adjusting agents, optical brighteners, graying inhibitors , Defoamers and perfumes.
  • aqueous preparations which can be obtained by the process according to the invention and contain alkyl and / or alkenyl oligoglycosides are color-stable at storage temperatures of about 30 ° C. and show practically no tendency towards crystallization; at the same time the solubility limit is lowered. They are therefore suitable for the production of detergents, dishwashing detergents and cleaning products and products for hair and body care, in which they can be present in amounts of 1 to 50, preferably 10 to 30,% by weight, based on the composition.
  • SET melting end points
  • Tab. 1 shows the melting end points for the hydrates with the highest SET. The results are to be evaluated in such a way that when the coconut alkyl oligoglucoside is stored there is no crystallization above the stated SET and only a greatly delayed crystallization below the SET.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)
  • Detergent Compositions (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

On obtient des agents tensioactifs non ioniques stables au stockage offrant une meilleure résistance à la cristallisation, en ajoutant, à des préparations aqueuses renfermant des alkyl- et/ou alcényloligoglucosides de formule (I): R1O-[G]p dans laquelle R1 désigne un reste alkyle et/ou alcényle linéaire ayant 6 à 22 atomes de carbone, G désigne un reste glucidique ayant 5 ou 6 atomes de carbone et p est un nombre compris entre 1 et 10, des modérateurs de cristallisation choisis dans le groupe comprenant a) des alkyloligoglucosides à base d'alcools primaires à chaînes courtes, b) des alkyloligoglucosides à base d'alcools de Guerbet, c) des alkyloligoglucosides à base de polyols, d) des alcools primaires à chaînes courtes, e) des polyglycoléthers d'alcools gras, f) des polyéthylèneglycols, g) le glucose, et h) des ions fer(III).

Claims (4)

  1. Procédé de fabrication de tensioactifs non ioniques stables au stockage, dans lequel on ajoute des modérateurs de cristallisation aux préparations aqueuses contenant des alkyl- et/ou alcényloligoglycosides de formule (I),

            R1O-[G]p     (I)

    dans laquelle R1 représente un radical alkyle et/ou alcényle avec 6 à 22 atomes de carbone, G représente un radical sucre avec 5 ou 6 atomes de carbone et p des nombres de 1 à 10,
    caractérisé en ce que
    les modérateurs sont choisis dans le groupe formé de :
    a) alkyloligoglycosides à base d'alcools primaires à chaîne courte avec 1 à 4 atomes de carbone,
    b) alkyloligoglycosides à base de polyols,
    c) glucose et,
    d) ions ferriques- (III)
  2. Procédé selon la revendication 1,
    caractérisé en ce qu'
    on met en oeuvre comme composant (a) des butylglucosides.
  3. Procédé selon les revendications 1 et 2,
    caractérisé en ce qu'
    on met en oeuvre comme composant (b) des alkyloligoglycosides à base de polyols, qui suivent la formule (II),

            HO-(CH2CH2O)n-[G]p

    dans laquelle n représente des nombres de 1 à 10 et G et p ont les significations indiquées ci-dessus.
  4. Procédé selon les revendications 1 à 3,
    caractérisé en ce qu'
    on met en oeuvre les modérateurs de cristallisation en quantités de 0,01 à 7 % en poids, par rapport aux alkyl et/ou alcényloligoglycosides.
EP93915972A 1992-07-30 1993-07-21 Procede de fabrication d'agents tensioactifs non ioniques stables au stockage Expired - Lifetime EP0652932B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4225224A DE4225224A1 (de) 1992-07-30 1992-07-30 Verfahren zur Herstellung von lagerstabilen nichtionischen Tensiden
DE4225224 1992-07-30
PCT/EP1993/001939 WO1994003569A1 (fr) 1992-07-30 1993-07-21 Procede de fabrication d'agents tensioactifs non ioniques stables au stockage

Publications (2)

Publication Number Publication Date
EP0652932A1 EP0652932A1 (fr) 1995-05-17
EP0652932B1 true EP0652932B1 (fr) 1997-05-14

Family

ID=6464481

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93915972A Expired - Lifetime EP0652932B1 (fr) 1992-07-30 1993-07-21 Procede de fabrication d'agents tensioactifs non ioniques stables au stockage

Country Status (6)

Country Link
US (1) US5556573A (fr)
EP (1) EP0652932B1 (fr)
JP (1) JPH07509515A (fr)
DE (2) DE4225224A1 (fr)
ES (1) ES2102044T3 (fr)
WO (1) WO1994003569A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19737604C1 (de) * 1997-08-28 1999-04-22 Kao Corp Verwendung einer Zusammensetzung als Haarwaschmittel

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4439091A1 (de) * 1994-11-02 1996-05-09 Henkel Kgaa Oberflächenaktive Mittel
DE19506207A1 (de) 1995-02-23 1996-08-29 Goldschmidt Ag Th Lagerstabile, konzentrierte Tensidzusammensetzung auf der Basis von Alkylglucosiden
FR2733246B1 (fr) * 1995-04-21 1997-05-23 Seppic Sa Composition anti-mousse comprenant un tensioactif non ionique et un alkylpolyglycoside
FR2734496B1 (fr) * 1995-05-24 1997-07-04 Seppic Sa Composition emulsionnante a base d'alkylpolyglycosides, et ses utilisations
JPH093498A (ja) * 1995-06-20 1997-01-07 Th Goldschmidt Ag 貯蔵安定性の濃縮水性界面活性剤組成物
US6117934A (en) * 1997-02-03 2000-09-12 Henkel Corporation Alkylpolyglycoside containing surfactant blends for emulsion polymerization
US6149774A (en) * 1998-06-10 2000-11-21 Delsys Pharmaceutical Corporation AC waveforms biasing for bead manipulating chucks
DE19901062A1 (de) * 1999-01-14 2000-07-20 Cognis Deutschland Gmbh Verfahren zur Kristallisationsinhibierung von Tensidkonzentraten
DE10129484A1 (de) * 2001-06-21 2003-03-20 Cognis Deutschland Gmbh Alkyl- und/oder Alkenyloligoglycosid-Zubereitungen mit verminderten Magnesiumsalzkonzentrationen
CN111304017B (zh) * 2020-03-24 2022-09-20 万华化学集团股份有限公司 温和低泡洗衣凝珠及其制备方法

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US2888489A (en) * 1957-01-24 1959-05-26 Dow Chemical Co Polyglycol ether surface-active agents
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US3547828A (en) * 1968-09-03 1970-12-15 Rohm & Haas Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
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DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
JP2587262B2 (ja) * 1988-01-06 1997-03-05 株式会社資生堂 洗浄剤組成物
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JPH0692600B2 (ja) * 1988-11-25 1994-11-16 日本コーンスターチ株式会社 高級アルキルグリコシド組成物
EP0377807B1 (fr) * 1988-12-07 1994-02-09 Henkel Kommanditgesellschaft auf Aktien Détergent liquide hautement alcalin et sans phosphate
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19737604C1 (de) * 1997-08-28 1999-04-22 Kao Corp Verwendung einer Zusammensetzung als Haarwaschmittel
DE19737604C5 (de) * 1997-08-28 2008-02-07 Kao Corp. Verwendung einer Zusammensetzung als Haarwaschmittel

Also Published As

Publication number Publication date
US5556573A (en) 1996-09-17
ES2102044T3 (es) 1997-07-16
JPH07509515A (ja) 1995-10-19
WO1994003569A1 (fr) 1994-02-17
EP0652932A1 (fr) 1995-05-17
DE59306461D1 (de) 1997-06-19
DE4225224A1 (de) 1994-02-03

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