EP0444262B2 - Détergent liquide moussant - Google Patents

Détergent liquide moussant Download PDF

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Publication number
EP0444262B2
EP0444262B2 EP90123844A EP90123844A EP0444262B2 EP 0444262 B2 EP0444262 B2 EP 0444262B2 EP 90123844 A EP90123844 A EP 90123844A EP 90123844 A EP90123844 A EP 90123844A EP 0444262 B2 EP0444262 B2 EP 0444262B2
Authority
EP
European Patent Office
Prior art keywords
weight
liquid
alkyl
cleaning formulation
cleaning
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
EP90123844A
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German (de)
English (en)
Other versions
EP0444262A3 (en
EP0444262A2 (fr
EP0444262B1 (fr
Inventor
Dieter Dr. Balzer
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.)
Sasol Germany GmbH
Original Assignee
Sasol Germany GmbH
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Filing date
Publication date
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Application filed by Sasol Germany GmbH filed Critical Sasol Germany GmbH
Publication of EP0444262A2 publication Critical patent/EP0444262A2/fr
Publication of EP0444262A3 publication Critical patent/EP0444262A3/de
Publication of EP0444262B1 publication Critical patent/EP0444262B1/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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • 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 an environmentally compatible, liquid cleaning agent.
  • Liquid, foaming cleaning agents aim at the manual cleaning of hard surfaces, especially in the Household, such as B. ceramics, porcelain, glass, metal and plastic.
  • the most important application area is manual Detergent for cleaning dishes.
  • Modern products consist of neutral aqueous formulations based on foaming surfactants.
  • the main components are sulfonates, such as. B. alkylbenzenesulfonates or sec-alkanesulfonates, both combined with Fatty alcohol ether sulfates or also fatty alcohol sulfates (EP-A-0 112 047).
  • Small amounts of fatty acid alkanolamides are used and less often added oxyethylates.
  • Other common ingredients are solubilizers, colors and fragrances, Preservatives etc.
  • the rinsing process usually takes place at a slightly elevated temperature (30 to 50 ° C) in dilute solutions. Of particular importance, because of the long skin contact of the user, the skin compatibility of the detergent.
  • the foaming power of the solution plays a role considerable role, for example in the sense that the longer the cleaning solution foams during the rinsing process, the greater is also their cleaning power.
  • Generally accepted test methods are a) the plate test, the end point of which is determined by the Foam decay is determined, and b) fat titration, as a measure of cleaning power, both of which are very similar Results (see G. Jakobi in H. Stache, Tensid Taschenbuch, 2nd edition, Kunststoff 1981, p. 252 ff.).
  • the object of the invention was therefore a very skin-friendly cleaning agent with an excellent cleaning effect with moderate foaming power, the cleaning surfactants of which are largely biologically available are degradable.
  • alkyl polyglycosides in detergents and cleaning agents is in combination with other surfactants known.
  • AT-PS 135 333 already describes the effect of lauryl glycoside combined with the sodium salt of Ricin oil sulfuric acid esters as a wool detergent.
  • alkyl polyglycosides are used in combination with Builder substances, such as nitrilotriacetic acid or sodium tripolyphosphate, are described as detergents.
  • the combination EP-A-0 105 556 claims alkyl polyglycosides with fatty alcohol oxyethylates as the liquid detergent.
  • US Pat. No. 171 describes the preparation and use of a mixture of branched C 7 -C 30 alkyl monoglycosides and branched and straight-chain alkyl polyglycosides with degrees of glycosidation of 2 and higher.
  • Such mixtures using, for example, 2-ethylhexyl glycosides have the advantage of 20 ° C to be liquid, even with high solids contents.
  • dishwashing detergents which are used exclusively as cleaning surfactants are alkyl polyglycosides contain, achieve excellent cleaning effects when these alkyl polyglycosides are sufficiently hydrophobic Have structure. This is achieved by using fatty alcohols with relatively long hydrocarbon chains in the synthesis, the proportions of fatty alcohol to monosaccharide units to be selected that the average degree of glycosidation (glycoside units per fatty alkyl radical) is not too high.
  • Alkyl polyglycosides used according to the invention satisfy the general formula RO-Zn, in which R represents a linear or branched, saturated or unsaturated aliphatic alkyl radical and Z n represents a polyglycosyl radical.
  • the alkyl polyglycosides used according to the invention can be based on renewable methods using known methods Raw materials are manufactured. For example, dextrose in the presence of an acid catalyst with n-butanol converted to butyl polyglycoside mixtures, which also with long-chain alcohols in the presence of an acid Catalyst to the desired alkyl polyglycoside mixtures are glycosidated.
  • the structure of the products can be varied within certain limits.
  • the alkyl radical R is selected by the choice of the long chain Alcohol.
  • the industrially accessible surfactant alcohols in particular native fatty alcohols from the hydrogenation of fatty acids or fatty acid derivatives.
  • the polyglycosyl radical Z n is determined, on the one hand, by the selection of the carbohydrate and, on the other hand, by the setting of the average degree of polymerization n. B. according to DE-OS 19 43 689.
  • polysaccharides e.g. B. starch, maltodextrins, dextrose, galactose, mannose, xylose, etc.
  • the industrially available carbohydrates starch, maltodextrins and especially dextrose are preferred.
  • alkyl polyglycosides are always mixtures of oligomers, which in turn represent mixtures of different isomeric forms. They exist side by side with ⁇ - and ⁇ -glycosidic bonds in pyranose and furanose form. The linkages between two saccharide residues are also different.
  • Alkyl polyglycosides used according to the invention can also be prepared by mixing alkyl polyglycosides with alkyl monoglycosides.
  • the latter can e.g. B. according to EP-A 0 092 355 using polar solvents, such as acetone, from alkyl polyglycosides.
  • polar solvents such as acetone
  • the degree of glycosidation is expediently determined by 1 H NMR certainly.
  • the cleaning agents according to the invention usually contain 3 to 50 percent by weight, preferably 5 to 30 Weight percent, total alkyl polyglycoside in aqueous solution.
  • the total polyglycoside consists of at least two components, a hydrophilic component I and one hydrophobic component II.
  • I has no or very little cleaning action and serves to increase the Solubility in water or to lower the clear point.
  • the hydrophobic component II is the actual cleaning agent. It is completely surprising with the mixture that the cleaning effect of component II is largely retained remains, although I itself has practically no cleaning effect.
  • the measure for adjusting the hydrophilicity is primarily the hydrophobic remainder of the alkyl polyglycoside.
  • hydrophobic alkyl radical is in the range ⁇ C 10 .
  • the adjustment of the hydrophobic component is a little more subtle.
  • the alkyl residue should be> C 10 , at the same time the degree of glycosidation should be reduced to such an extent that the cleaning effect is optimal.
  • the quantitative ratio of the two components I / II should be between 1: 1 and 1:10, preferably between 1: 2 and 1: 5.
  • the alkyl polyglycosides are considered to be extremely environmentally friendly.
  • the degree of biodegradation determined by means of sewage treatment plant simulation mode II / DOC analysis for the alkyl polyglycosides according to the invention at 96 ⁇ 3%. This number can be seen against the background that According to this test method (total degradation), a degree of degradation> 70% indicates that the substance is readily degradable.
  • Acute oral toxicity LD 50 (rat) as well as aquatic toxicity LC 50 (gold orfe) and EC 50 (daphnia) and values of> 10,000 mg / kg, 12 or 30 mg / l are 3 to 5 times cheaper than the corresponding values of the most important surfactants today. The same applies to the skin and mucous membrane compatibility, which is particularly important for detergents.
  • alkyl polyglycosides according to the invention fall due to the synthesis as about 50% aqueous amber solutions on.
  • solvents such as low molecular weight, mono- and polyhydric alcohols and glycol ethers
  • Particularly suitable solvents are ethanol, Isopropanol, propylene glycol-1.2, etc.
  • the ratio of alkyl polyglycoside / solvent can be 1: 1 to 4: 1.
  • solubility can be achieved especially at low temperatures increase significantly.
  • Alkali and alkaline earth metal halides have proven to be suitable electrolytes.
  • the relationship of solvent / electrolyte can be 1: 1 to 4: 1.
  • cleaning agents according to the invention in small amounts (0.1 to 3 percent by weight) are common dyes and perfume oils and alkanolamines or hydrotropics, such as non-surfactant alkylbenzenesulfonates with 1 to 3 carbon atoms in the alkyl radical - usually as sodium salts - and urea.
  • water-soluble polymers such as carboxymethyl cellulose, Hydroxyethyl cellulose, xanthans, polyethylene oxide, polyacrylate, etc. can be added.
  • Citric acid, EDTA, NTA and other complexing agents have proven to be further suitable additives.
  • Watch glasses loaded with grease are manually at elevated temperature with a brush in the surfactant solution cleaned.
  • the test conditions (preparations, geometries, amounts and concentrations of substances, temperatures, Temperature gradients, times) are precisely defined.
  • the test is carried out by several people and delivers well reproducible results.
  • Disappearing foam shows the number of cleaned plates (watch glasses). As soiling served lard, which was applied to the glasses at 50.0 ° C, which then defined a The cooling process is subject to 23 ° C (room temperature). The initial rinse temperature is also 50 ° C.
  • Table 1 compares the cleaning effect of individual surfactants, which increases strongly with alkyl polyglycosides Molecular hydrophobicity increases.
  • Table 2 demonstrates that even a strong increase in the surfactant concentration only has unsatisfactory cleaning effects results when the alkyl polyglycoside is too hydrophilic, as in the case of Triton CG 110.
  • Table 3a compares the cleaning action of the alkyl polyglycosides according to the invention with those of optimized branded products depending on the detergent concentration for a medium water hardness; Table 3b the analogous conditions for soft water.
  • Mini plate test concentration of detergent: 0.075 g / l, drinking water: 13 ° dH surfactant Number of cleaned plates a) C 10 -C 13 alkylbenzenesulfonate Na 10 b) C 12 C 14 -O (EO) 2 SO 4 Na 14 c) C 12 C 14 O (EO) 8 H 8th d) C 8 C 10 G 1.8 (Triton CG 110) 0 e) C 10 C 12 G 1.5 1 f) C 10 C 12 G 1.2 5 g) C 12 C 13 G 1.7 14 h) C 12 C 14 G 1.4 18 i) C 12 C 14 G 1.2 22
  • Examples e) to i) are according to the invention.
  • Mini plate test with Triton CG 110 (Rohm & Haas) depending on the water hardness and the surfactant concentration water hardness Wash-active substance g / l Number of cleaned plates a) 2 0,075 0 b) 2 0.15 1 c) 13 0.15 0 d) 13 0.3 1
  • Table 4 summarizes the physical data of some of the preparations according to the invention.
  • Your solubility behavior (Klarrios) on the one hand and their cleaning values (mini plate test) on the other hand demonstrate the high level Effectiveness of the new cleaning systems.

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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)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Detergent Compositions (AREA)

Claims (6)

  1. Produit nettoyant moussant liquide,
    caractérisé par le fait qu'il est constitué
       de 3 à 40 % en poids d'un alkylpolyglycoside I,
       de 3 à 40 % en poids d'un alkylpolyglycoside II,
       de 0 à 10 % en poids d'un tiers-solvant,
       de 0 à 10 % en poids d'un électrolyte,
       de 0 à 3 % d'additifs, et
       le complément à 100 % en poids étant constitué d'eau,
    où l'alkylpolyglycoside I correspond à la formule (I) R1-O-Zn1 dans laquelle R1 est un radical alkyle saturé ou insaturé, à chaíne droite ou ramifiée, ayant de 7 à 10 atomes de carbone, et Zn1 est un radical polyglycosyle dans lequel n1 = 1 à 3 motifs hexose ou pentose, ou leurs mélanges,
    et l'alkylpolyglycoside II correspond à la formule (II) R2-O-Zn2 dans laquelle R2 est un radical alkyle saturé ou insaturé, à chaíne droite ou ramifiée, ayant de 11 à 18 atomes de carbone, et Zn2 est un radical polyglycosyle dans lequel n2 = 1 à 3 motifs hexose ou pentose, ou leurs mélanges.
  2. Produit nettoyant moussant liquide selon la revendication 1,
    caractérisé par le fait que R2 est un radical alkyle gras ayant de 12 à 18 atomes de carbone, et Zn2 est un radical polyglycosyle dans lequel n2 = 1,1 à 2 motifs glycoside.
  3. Produit nettoyant moussant liquide selon l'une des revendications précédentes,
    caractérisé par le fait que le rapport pondéral de R1-O-Zn1 à R2-O-Zn2 est compris entre 1 : 1 et 1 : 10.
  4. Produit nettoyant moussant liquide selon l'une des revendications précédentes,
    caractérisé par le fait qu'on utilise comme tiers-solvant des monoalcools et polyalcools à faible masse moléculaire, des éthers de polyalcool, des alcanolamines et/ou des substances hydrotropes.
  5. Produit nettoyant moussant liquide selon l'une des revendications précédentes,
    caractérisé par le fait qu'on utilise comme électrolytes des halogénures de métaux alcalins ou des halogénures de métaux alcalino-terreux, ou encore leurs mélanges.
  6. Utilisation du produit nettoyant moussant liquide selon l'une des revendications précédentes, comme agent de rinçage à la main.
EP90123844A 1990-02-26 1990-12-11 Détergent liquide moussant Expired - Lifetime EP0444262B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4005958 1990-02-26
DE19904005958 DE4005958A1 (de) 1990-02-26 1990-02-26 Fluessiges, schaeumendes reinigungsmittel

Publications (4)

Publication Number Publication Date
EP0444262A2 EP0444262A2 (fr) 1991-09-04
EP0444262A3 EP0444262A3 (en) 1992-01-22
EP0444262B1 EP0444262B1 (fr) 1996-02-28
EP0444262B2 true EP0444262B2 (fr) 2004-10-06

Family

ID=6400955

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90123844A Expired - Lifetime EP0444262B2 (fr) 1990-02-26 1990-12-11 Détergent liquide moussant

Country Status (3)

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EP (1) EP0444262B2 (fr)
DE (2) DE4005958A1 (fr)
DK (1) DK0444262T3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4110506A1 (de) * 1991-03-30 1992-10-01 Huels Chemische Werke Ag Emulgatoren zur herstellung von in der kosmetik oder medizin verwendbaren oel-in-wasser-emulsionen etherischer oele
EP0607198B1 (fr) * 1991-10-10 2001-02-14 Cognis Corporation Preparation de melanges ameliores contenant des agents tensio-actifs alkylpolyglycosides
US5449763A (en) * 1991-10-10 1995-09-12 Henkel Corporation Preparation of alkylpolyglycosides
DE4225224A1 (de) * 1992-07-30 1994-02-03 Henkel Kgaa Verfahren zur Herstellung von lagerstabilen nichtionischen Tensiden
DE4319700A1 (de) * 1993-06-16 1994-12-22 Henkel Kgaa Ultramilde Tensidmischungen
DE4319699A1 (de) * 1993-06-16 1994-12-22 Henkel Kgaa Ultramilde Tensidmischungen
AU675833B2 (en) * 1994-03-23 1997-02-20 Amway Corporation Concentrated all-purpose light duty liquid cleaning composition and method of use
DE19933404A1 (de) * 1999-07-21 2001-01-25 Henkel Kgaa Reinigungsmittel für harte Oberflächen
DE19944543C2 (de) * 1999-09-17 2002-04-18 Cognis Deutschland Gmbh Tensidgemische
AU2010357689B2 (en) * 2010-07-19 2014-06-12 Colgate-Palmolive Company Cleansing composition with decyl and coco glucosides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4725489A (en) † 1986-12-04 1988-02-16 Airwick Industries, Inc. Disposable semi-moist wipes
EP0280143A1 (fr) † 1987-02-25 1988-08-31 Henkel Kommanditgesellschaft auf Aktien Agent de nettoyage liquide
US5449763A (en) † 1991-10-10 1995-09-12 Henkel Corporation Preparation of alkylpolyglycosides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547828A (en) * 1968-09-03 1970-12-15 Rohm & Haas Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
US4488981A (en) * 1983-09-06 1984-12-18 A. E. Staley Manufacturing Company Lower alkyl glycosides to reduce viscosity in aqueous liquid detergents
USH171H (en) * 1985-06-24 1986-12-02 A. E. Staley Manufacturing Company Branched chain glycosides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4725489A (en) † 1986-12-04 1988-02-16 Airwick Industries, Inc. Disposable semi-moist wipes
EP0280143A1 (fr) † 1987-02-25 1988-08-31 Henkel Kommanditgesellschaft auf Aktien Agent de nettoyage liquide
US5449763A (en) † 1991-10-10 1995-09-12 Henkel Corporation Preparation of alkylpolyglycosides

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C.F. Putnik et al, Soap Cosmet. Chem. Spec., 1986, 62, n°6, S. 34-37, 74 †
J. Falbe, Surfactants in consumer products Springer-Verlag, Heidelberg, 1987, S. 104-106 †

Also Published As

Publication number Publication date
EP0444262A3 (en) 1992-01-22
EP0444262A2 (fr) 1991-09-04
DK0444262T3 (da) 1996-07-01
DE4005958A1 (de) 1991-08-29
EP0444262B1 (fr) 1996-02-28
DE59010166D1 (de) 1996-04-04

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