EP2336280A1 - Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage - Google Patents

Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage Download PDF

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Publication number
EP2336280A1
EP2336280A1 EP09015094A EP09015094A EP2336280A1 EP 2336280 A1 EP2336280 A1 EP 2336280A1 EP 09015094 A EP09015094 A EP 09015094A EP 09015094 A EP09015094 A EP 09015094A EP 2336280 A1 EP2336280 A1 EP 2336280A1
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EP
European Patent Office
Prior art keywords
oligo
alkyl
glycosides
foam
glucoside
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.)
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Application number
EP09015094A
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German (de)
English (en)
Inventor
Rainer Eskuchen
Sabine Both
Arnold Benert
Ditmar Kischkel
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Cognis IP Management GmbH
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Cognis IP Management GmbH
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Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP09015094A priority Critical patent/EP2336280A1/fr
Priority to EP10782205A priority patent/EP2507354A1/fr
Priority to PCT/EP2010/007177 priority patent/WO2011066925A1/fr
Priority to US13/513,762 priority patent/US20120245070A1/en
Publication of EP2336280A1 publication Critical patent/EP2336280A1/fr
Withdrawn legal-status Critical Current

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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
    • 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 present invention relates to the use of certain branched alkyl (oligo) glycosides in detergents.
  • Alkyl (oligo) glycosides have long been known nonionic surfactants, which are used both in cosmetics but also in detergents and cleaners.
  • the advantages of these surfactant classes are in particular their good biodegradability, but also the fact that these surfactants can be obtained from renewable raw materials.
  • Alkyl and alkenyl oligoglycosides follow the formula R'O- [G] p in the R 'for an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G for a sugar radical having 5 or 6 carbon atoms and p for numbers from 1 to 10 stands. They can be obtained by the relevant methods of preparative organic chemistry. Representative of the extensive literature is here on the review of Biermann et al.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses having 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the index number p in the general formula (I) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
  • alkyl (oligo) glycosides based on unbranched fatty alcohols
  • such compounds which contain branched radicals R '.
  • R ' branched radicals
  • the alcohol moiety may be branched in 2-position, and as branching, for example, an ethyl or propyl radical is disclosed.
  • the document also discloses the suitability of such illustrated Alkyl (oligo) glycosides for detergents and cleaners.
  • the agents contain branched alkyl (oligo) glycosides.
  • Guerbet alcohols and in particular 2-ethylhexyl alcohol and 2-propylheptyl alcohol, are mentioned as branched alcohols.
  • EP 1 292 660 A1 describe single-phase microemulsions containing branched alkyl (oligo) glycosides.
  • a first subject of the present application therefore relates to the use of alkyl (oligo) glycosides according to the general formula (I) RO- [G] x (I) where G is a glycoside radical, x is a number from 1 to 3 and R is a branched radical in which R 1 is a linear alkyl radical having 1 to 6 C atoms, and R 2 is a methyl or ethyl radical and n can assume numbers from 1 to 10 as hydrotop for aqueous systems.
  • hydrotropy refers to the phenomenon that a sparingly soluble substance becomes water-soluble in the presence of a second component, which itself is not a solvent.
  • hydrotropes or hydrotropes are termed hydrotropes or hydrotropes. They act as solubilizers with different mechanisms of action: substances that tend to form association colloids, such.
  • surfactants z. By formation of micelles.
  • B. allow the solubility of long-chain, otherwise water-insoluble alcohols.
  • the z. B. used in the formulation of liquid detergents are xylene or cumene sulfonate.
  • Other substances eg.
  • urea or N-methylacetamide increase the solubility by a structure-breaking effect, in which the water structure is degraded in the vicinity of the hydrophobic group of a poorly soluble substance.
  • a solubility increase can also be brought about by the formation of mixed crystals with the hydrotropic substance in the bottom body of the component to be dissolved.
  • Solutions of hydrotrope are used instead of organic solvents for extraction purposes.
  • the solutions are non-volatile, non-flammable and non-toxic, can be easily regenerated and generally have higher HLB values.
  • Particularly preferred is currently the cumene sulfonate, which, however, is not biodegradable.
  • alkyl (oligo) glycosides of the formula (I) are preferably selected in which R is a 2-Propyhlheptylrest.
  • alkyl (oligo) glycosides of the formula (I) is preferably carried out in amounts of 0.5 to 10 wt .-%, preferably 1 to 5 wt .-% and in particular in amounts of 2 to 4 wt .-%, based on the watery system.
  • aqueous systems are both detergents and cleaners, but also cosmetic preparations in question.
  • Aqueous systems within the meaning of the present technical teaching contain at least 50 wt .-% water and preferably 50 to 99 wt .-%, or in particular 65 to 95 wt .-% water.
  • the alkyl (oligo) glycosides according to the formula (I) are preferably used as hydrotropes in cleaners and here preferably in aqueous all-purpose cleaners, dishwashing detergents and bath cleaners.
  • dishwashing agents are particularly preferred since the alkyl (oligo) glycosides of the formula (I) have good compatibility with plastics and, in particular, the tendency for so-called crack corrosion is lower than for other nonionic surfactants.
  • branched alkyl (oligo) glycosides of the present invention used in the present invention have comparable properties as the cumene sulfonate, however, they are better biodegradable and based on natural, renewable resources.
  • the propylheptylglucoside was diluted with water to a paste having a solids concentration of 65-75%.
  • This aqueous solution was bleached at 90 ° C with the addition of hydrogen peroxide (35%) and sodium hydroxide solution (20%) to a Hazen color number ⁇ 50.
  • the Hazen color number was determined using the colorimeter Lico 300 from Dr. Ing. Long measured.
  • the glucoside solution is diluted to 10% active substance and filtered through a 0.45 ⁇ filter into an 11 mm round cuvette.
  • the following 3 products according to the invention were prepared according to the general procedure, and a 2-ethylhexyl glycoside for comparison:
  • the foam device enables a dynamic "Ross-Miles" test.
  • the surfactant liquid is continuously pumped in the circulation and pumped to the liquid level.
  • the intrinsic foam behavior of active substances or formulations is tested as a function of the temperature.
  • For solid samples always prepare a preliminary solution, unless the dissolution behavior is investigated. 500mL dist. Water is poured into the double-walled 2 liter graduated cylinder of the free-fall circuit apparatus. In the thermostat, the desired temperature profile (8 ° C to 80 ° C in 45 minutes) is opened and tempered to the corresponding start temperature ⁇ 1 ° C in the measuring cylinder.
  • the temperature profile and the peristaltic pump are started.
  • 0.2 ml of the test substance or formulation with 0.2 ml of active substance is pipetted into the water pumped in the circulation.
  • the stopwatch is to start.
  • the resulting total volume (foam and liquid) is recorded with the associated temperatures and times. The recording of the measured values in areas with rapid foam height change takes place at short intervals in order to reproduce the course more accurately.
  • the result of the temperature-dependent foam height is for 4 alkyl polyglucosides in illustration 1 been presented.
  • a C8 / 10 fatty alcohol glucoside Glucopon 225 DK
  • a C12 / 14 fatty alcohol glucoside Glucopon 600 UP
  • a 2-ethylhexyl glucoside Berol AG 6202, Akzo Nobel
  • the branched 2-ethylhexyl APG shows a low foam height over the entire temperature range.
  • the APG based on propylheptanol from Example 1 shows a similar foaming behavior over the entire temperature range.
  • the low foaming capacity is comparable to 2-ethylhexyl APG.
  • Texapon NSO, Dehyton PK 45 and the substance to be tested are weighed in succession, to 100 g with dist. Water filled and mixed. Optionally, the pH is adjusted with citric acid. From this formulation, a 2.5% solution is prepared using hard water (15 ° dH). This is then whipped in a 800ml beaker with a mizer disk for 10s at 2000 revolutions. For this purpose, the stirrer is operated for 10 s at 2000 revolutions. The foam is spooned onto a Ceran plate and photographed using a spatula spoon. For foam evaluation, the height of the foam in the beaker is measured and the foam quality is rated 1-6 grades based on the benchmarks listed below, where 1 stands for the best and 6 for the worst foam quality.
  • Table 3 shows the foam heights for 4 different APGs: ⁇ u> Table 3 ⁇ / u> 9% * Texapon NSO + 3% Dehyton PK45 foam height foam quality + --- 6.5 cm 4-5 + 2% * propylheptylxyloside (Ex. 2) 10.0 cm 1 - 2 + 2% * propylheptyl glucoside (Ex. 3) 9.5 cm 1 - 2 + 2% * ethylhexyl glucoside (Ex. 4) 6.0 cm 2 - 3 + 2% * Plantacare 1200 UP 5.5 cm 3 - 4 * based on active substance (AS)
  • AS active substance
  • the foam height or the foam structure of surfactant-containing formulations is greatly improved by the addition of propylheptyl glycosides.
  • the comparative examples with the ethyhexyl glucoside and the Plantacare 1200 UP show that other alkylpolyglycosides show these properties to a much lesser extent.
  • the cleaning performance of the investigated APGs was carried out using a modified and automated Gardner test.
  • the main features of the test method were published as an IPP quality standard in S ⁇ FW 112. 10/1986 (Gardner test).
  • the method is based on wiping a test soil treated white soil carrier under defined conditions with a sponge soaked in the test material.
  • the cleaning effect is measured by means of digital image evaluation against the untreated dirt carrier. For better comparability, all the glucosides were neutralized so that the test measured only the cleaning performance of the surfactant and not in the presence of alkali.
  • Table 4 shows the cleaning performance of the investigated 4 APGs: Component to 1% by weight (AS) Measured cleaning performance in% Linear C8 / 10 fatty alcohol glucoside, neutralized 68 Linear C12 / 14 fatty alcohol glucoside, neutralized 61 2-ethylhexyl glucoside, neutralized 55 Glucoside from Example 1, Propylheptylglucosid neutralized 90
  • alkyl polyglucosides are used as solubilizers in order to formulate foam-controlling surfactants into cleaning formulations, ie to obtain a homogeneous cleaning solution.
  • foam-controlling surfactants are generally difficult to formulate into aqueous systems because of their hydrophobicity.
  • the propylheptyl glucoside shows significantly better solubilizing properties than the linear fatty alcohol glucoside and the 2-ethylhexyl glucoside
  • Table 6 shows the results: ⁇ u> Table 6 ⁇ / u> PMMA PC SECTION Plexiglass 8 N Makrolon 3103 Terez 3010 7d 14d 7d 14d 7d 14d Propylheptylglucosid 1 1 1 1.5 1 1 C8 / 10 fatty alcohol glucoside, linear 1 1 1 1 1 1 1 1 Fettalkoholethoxylat 3 4 3 3 3 3 2-ethylhexyl glucoside 1 1.5 2 2.75 2 2 2
  • linear and the propylheptylglucoside have the best material compatibility and are therefore suitable for use on these surfaces.
  • the fatty alcohol ethoxylate and the 2-ethylhexyl glucoside show no good material compatibility.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Saccharide Compounds (AREA)
EP09015094A 2009-12-05 2009-12-05 Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage Withdrawn EP2336280A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP09015094A EP2336280A1 (fr) 2009-12-05 2009-12-05 Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage
EP10782205A EP2507354A1 (fr) 2009-12-05 2010-11-26 Utilisation d'alkyl(oligo)glycosides ramifiés dans des produits de nettoyage
PCT/EP2010/007177 WO2011066925A1 (fr) 2009-12-05 2010-11-26 Utilisation d'alkyl(oligo)glycosides ramifiés dans des produits de nettoyage
US13/513,762 US20120245070A1 (en) 2009-12-05 2010-11-26 Use Of Branched Alkyl(Oligo)Glycosides In Cleaning Agents

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Application Number Priority Date Filing Date Title
EP09015094A EP2336280A1 (fr) 2009-12-05 2009-12-05 Utilisation d'alkyl (oligo)glycosides ramifiés dans des produits de nettoyage

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EP10782205A Withdrawn EP2507354A1 (fr) 2009-12-05 2010-11-26 Utilisation d'alkyl(oligo)glycosides ramifiés dans des produits de nettoyage

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014146958A1 (fr) * 2013-03-22 2014-09-25 Basf Se Mélanges d'alkylpolyglycosides, leur préparation et leurs utilisations
WO2015000792A1 (fr) * 2013-07-03 2015-01-08 Basf Se Mélanges de composés, leur préparation, et utilisations
EP2998311A1 (fr) * 2014-09-17 2016-03-23 Basf Se Mélange d'alkylglycoside, sa fabrication et son utilisation

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2968003B1 (fr) * 2010-11-25 2013-06-07 Seppic Sa Nouvel agent hydrotrope, son utilisation pour solubiliser des tensioactifs no-ioniques, compositions les comprenant.
EP3266859A1 (fr) * 2016-07-05 2018-01-10 Basf Se Composition appropriée comme agent d'élimination de dégraissage et/ou de dépôts de type huile grasse

Citations (5)

* 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
WO1997030140A1 (fr) * 1996-02-14 1997-08-21 Stepan Company Produit de nettoyage pour surfaces dures, contenant un hydrotrope et laissant peu de residus
JPH09315932A (ja) * 1996-03-27 1997-12-09 Shiseido Co Ltd 可溶化剤及びそれを含有する化粧料
US5744441A (en) * 1994-06-01 1998-04-28 Henkel Corporation Enhanced performance of amphoteric surfactants
WO1999021948A1 (fr) * 1997-10-29 1999-05-06 Akzo Nobel N.V. Compositions fortement alcalines contenant un glycoside d'hexyle en qualite d'hydrotrope

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
SE9300955L (sv) 1993-03-23 1994-09-24 Berol Nobel Ab Alkylglykosid och dess användning
SE523226C2 (sv) * 2000-05-25 2004-04-06 Akzo Nobel Nv En mikroemulsion innehållande en grenad alkylglykosid
DE10046250A1 (de) * 2000-09-19 2002-03-28 Cognis Deutschland Gmbh Verfahren zur Herstellung von hellfarbigen Alkyl-und/oder Alkenyloligoglycosid-Mischungen und deren Verwendung in Wasch-, Spül-und Reinigungsmittel
DE10153768A1 (de) * 2001-11-02 2003-05-15 Cognis Deutschland Gmbh Hydroxymischether mit Polymeren

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5744441A (en) * 1994-06-01 1998-04-28 Henkel Corporation Enhanced performance of amphoteric surfactants
DE4439091A1 (de) * 1994-11-02 1996-05-09 Henkel Kgaa Oberflächenaktive Mittel
WO1997030140A1 (fr) * 1996-02-14 1997-08-21 Stepan Company Produit de nettoyage pour surfaces dures, contenant un hydrotrope et laissant peu de residus
JPH09315932A (ja) * 1996-03-27 1997-12-09 Shiseido Co Ltd 可溶化剤及びそれを含有する化粧料
WO1999021948A1 (fr) * 1997-10-29 1999-05-06 Akzo Nobel N.V. Compositions fortement alcalines contenant un glycoside d'hexyle en qualite d'hydrotrope

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9845446B2 (en) 2013-03-22 2017-12-19 Basf Se Mixtures, their preparation, and uses
WO2014146958A1 (fr) * 2013-03-22 2014-09-25 Basf Se Mélanges d'alkylpolyglycosides, leur préparation et leurs utilisations
CN105073968A (zh) * 2013-03-22 2015-11-18 巴斯夫欧洲公司 烷基聚糖苷的混合物，其制备及应用
RU2660416C2 (ru) * 2013-07-03 2018-07-06 Басф Се Смеси соединений, их получение и применение
US9738858B2 (en) 2013-07-03 2017-08-22 Basf Se Mixtures of compounds, their preparation, and uses
CN105339378A (zh) * 2013-07-03 2016-02-17 巴斯夫欧洲公司 化合物的混合物、其制备和用途
WO2015000792A1 (fr) * 2013-07-03 2015-01-08 Basf Se Mélanges de composés, leur préparation, et utilisations
CN105339378B (zh) * 2013-07-03 2018-09-14 巴斯夫欧洲公司 化合物的混合物、其制备和用途
EP2998311A1 (fr) * 2014-09-17 2016-03-23 Basf Se Mélange d'alkylglycoside, sa fabrication et son utilisation
WO2016041698A1 (fr) * 2014-09-17 2016-03-24 Basf Se Mélange d'alkylglucosides et d'alkylxylosides, leur préparation et leur utilisation
CN107074901A (zh) * 2014-09-17 2017-08-18 巴斯夫欧洲公司 烷基葡糖苷和烷基木糖苷的混合物、其制备和用途
US10184094B2 (en) 2014-09-17 2019-01-22 Basf Se Mixture, their manufacture and use
CN107074901B (zh) * 2014-09-17 2022-09-27 巴斯夫欧洲公司 烷基葡糖苷和烷基木糖苷的混合物、其制备和用途

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EP2507354A1 (fr) 2012-10-10
WO2011066925A1 (fr) 2011-06-09
US20120245070A1 (en) 2012-09-27

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