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WO1989011524A1 - Ethers d'alkyle polyglycol antimousse pour detergents (ii) - Google Patents

Ethers d'alkyle polyglycol antimousse pour detergents (ii) Download PDF

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Publication number
WO1989011524A1
WO1989011524A1 PCT/EP1989/000543 EP8900543W WO8911524A1 WO 1989011524 A1 WO1989011524 A1 WO 1989011524A1 EP 8900543 W EP8900543 W EP 8900543W WO 8911524 A1 WO8911524 A1 WO 8911524A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
foam
atoms
polyglycol ethers
froth
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/EP1989/000543
Other languages
German (de)
English (en)
Inventor
Karl-Heinz Schmid
Gilbert Schenker
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 WO1989011524A1 publication Critical patent/WO1989011524A1/fr
Anticipated expiration legal-status Critical
Ceased 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
    • 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
    • C11D1/8255—Mixtures of compounds all of which are non-ionic containing a combination of compounds differently alcoxylised or with differently alkylated chains
    • 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
    • C11D1/721—End blocked 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0026—Low foaming or foam regulating compositions

Definitions

  • the invention relates to the use of selected end group capped polyethylene glycol ethers as foam-suppressing additives in low-foam cleaning agents.
  • the new auxiliaries of the invention should also be suitable in particular for cleaning processes which generate a lot of foam, for example in automatic dishwashing for household and commercial use, or e.g. to suppress unwanted foam formation during machine cleaning of bottles in the beverage industry.
  • Cleaning agents intended for use in trade and industry in particular those for cleaning metal, glass and ceramic surfaces, generally contain substances which are able to counteract undesirable foam development.
  • foam press additives is in most cases due to the fact that the contaminants detached from the substrates and accumulating in the cleaning baths act as foaming agents, such as in the dishwashing of the foam produced from food or in the bottle washing that caused by the detachment and the decomposition of labels by foam formed by caustic soda.
  • anti-foam mittein also be necessary due to the fact that the cleaning agents themselves contain components that give rise to undesirable foam formation under the given working conditions.
  • anionic surfactants widely used in cleaning agents.
  • Addition products of alkylene oxides with organic compounds with reactive hydrogen atoms in the molecule have long been used as foam-suppressing additives.
  • addition products of propylene oxide with aliphatic polyalcohols - see, for example, DE-PS 12 80 455 and DE-PS 16 21 592 - and with aliphatic polyamines - cf. for example DE-PS 12 89 597 and DE-PS 16 21 593 - and addition products of ethylene oxide and propylene oxide with aliphatic polyamines, especially ethylenediamine - cf. DE-PS 19 44 569 - proven in practice.
  • these alkylene oxide addition products also have the alkali stability which is usually required for use in commercial and industrial cleaning agents.
  • the compounds in this class are not sufficiently biodegradable to meet the applicable legal requirements.
  • R 1 is a straight-chain or branched alkyl radical or alkene radical having 8 to 18 carbon atoms
  • R 2 is an alkyl radical with 4 to 8 carbon atoms
  • n is a number from 7 to 12.
  • R 1 is a fatty alcohol radical having 12 to 18 carbon atoms and R 2 is the n-butyl radical, where n is the number 10, has proven particularly useful in practice.
  • the teaching of the present invention is based on the surprising finding that even more effective auxiliaries of the type concerned here can be obtained by slightly varying the structure of the last-mentioned end group-sealed fatty alcohol polyethylene glycol ethers.
  • foam-suppressing additives are often distinguished by the fact that they are very effective in combating foam in the temperature range of approximately 50 ° C. and above, but their use at temperatures of approximately 20 ° C. leads to comparatively weaker foam damping.
  • the additives according to the invention described below have a particular effectiveness precisely at low temperatures and also exhibit this property when they are blended with structure-like, known components.
  • the invention accordingly relates to the use of polyethylene glycol ethers of the general formula (I)
  • R 1 is a straight-chain or branched alkyl or alkenyl radical having 8 to 14 carbon atoms
  • R 2 is an alkyl radical having 8 to 10 carbon atoms
  • n is a number from 2 to 8, as foam-suppressing additives for low-foam cleaning agents.
  • R 2 C 8 -alkyl radical, the numerical value from 2 to 6 applies to n.
  • the preferred compounds of the general formula (I) contain a radical R 1 of the type indicated with 8 to 10 carbon atoms.
  • the preferred radical R 2 in the compounds according to the invention is the decyl radical, in particular the n-decyl radical.
  • the preferred values for n in the general formula (I) are 2 to 6 and in particular 4 to 6.
  • the decisive modification of the polyethylene glycol ethers according to the invention of the general formula (I) compared to the structure-like compounds of the aforementioned DE-OS 33 15 951 lies in the variation of the R 2 residue.
  • the carbon number of this resres compared to that above-described residues and is at least 8 carbon atoms.
  • the end group-capped fatty alcohol polyglycol ethers of the formula (I) are prepared in accordance with the details of DE-OS 33 15 951.
  • the fatty alcohols of higher carbon atom described above are advantageously reacted with ethylene oxide in a molar ratio of 1: 2 to 1: 8 and then etherified the hydroxyl groups present in the reaction product obtained.
  • the reaction with ethylene oxide takes place under the known alkoxylation conditions, preferably in the presence of suitable alkaline catalysts.
  • the etherification of the free hydroxyl groups is preferably carried out under the known conditions of Williamson's ether synthesis using straight-chain or branched C 8 to C 10 alkyl halides.
  • n-decyl radical for the radical R 2 from the general formula (I) is of particular importance in the course of the inventive action.
  • examples of such a final etherification are accordingly n-decyl halides, such as n-decyl iodide.
  • the invention is not restricted to this; further examples are n-octyl chloride, 2-ethylhexyl chloride, n-nonyl chloride, i-nonyl chloride and n-decyl chloride.
  • alkyl halide and alkali in a stoichiometric excess, for example from 10 to 50%, over the hydroxyl groups to be etherified.
  • polyglycol ethers of the formula (I) are used in which n denotes a number from 4 to 6.
  • the end group-sealed polyglycol ethers of the formula (I) to be used according to the invention are in an important Aus imple mentation in admixture with structurally identical polyethylene glycol ethers, but in which the radical R 1 is a straight-chain or branched alkyl or alkenyl radical having 8 to 18 carbon atoms and n is a number from 7 to 12, and preferably from 8 to 10.
  • the invention thus provides to blend the polyglycol ethers described here with the foam-suppressing additives from DE-OS 33 15 951.
  • Mixing ratios of the two types in the range from 10 to 90 to 90 to 10% by weight are suitable for this embodiment, in particular in weight ratios from 60 to 40 to 40 to 60% by weight.
  • One area of application for such mixtures is, for example, machine bottle cleaners or cleaning agents for the dairy industry.
  • end group-capped polyglycol ethers of the formula (I) which are now to be used according to the invention are also notable for high alkali and acid stability. Their foam-preventing effect in alkaline and neutral cleaning liquors is strengthened in the specified sense, moreover they also meet the legal requirements for biodegradability.
  • a further area of application for the end group-sealed polyglot containers of the formula (I) are, for example, liquid or powder detergents for automatic dishwashing for household and commercial use.
  • the use of these substances in powder cleaners has the additional effect that these substances act as an anti-caking agent ("anti-caking agent") in such a way that on the one hand they prevent the powder grains from sticking together when the powder products are stored and thus maintain good powder ripeness and on the other hand can bind the dust that forms as abrasion when moving the powder.
  • the end group-capped polyglycol ethers of the formula (I) are sprayed in a controlled manner onto the dry, agitated and therefore well-mixed solid granulate constituents which consist of framework substances, alkali metal carbonates and silicates.
  • Lödige and Eirich mixers can be used as granulators.
  • the cleaning agents in which the end group-capped polyglycol ethers of the invention are used can contain the constituents customary in such agents, such as wetting agents, builders and complexing agents, alkalis or acids, corrosion inhibitors and optionally also organic solvents.
  • Suitable wetting agents are nonionic surface-active compounds such as polyglycol ethers, which are obtained by adding ethylene oxide to alcohols, especially fatty alcohols, alkylphenols, fatty amines and carboxamides, and anionic wetting agents such as alkali metal, amine and alkylolamine salts of fatty acids, alkylsulfuric acids, alkylsulfonic acids and alkylbenzenesulfonic acids.
  • the builders can include alkali metal orthophosphates, polymer phosphates, silicates, borates, carbonates, polyacrylates and gluconates, as well as citric acid, nitrilotriacetic acid, ethylenediaminetetraacetic acid, 2-hydroxyalkane-1,1-diphosphonic acid and ethylenediaminophenamic acid and ethylenediamine and complexing agents. Contain phosphonoalkane polycarboxylic acids such as phosphonobutane tricarboxylic acid and alkali metal salts of these acids.
  • Highly alkaline cleaning agents in particular those for bottle cleaning, contain considerable quantities of caustic alkali in the form of sodium and / or potassium hydroxide. If special cleaning effects are desired, the cleaning agents can be organic solvents, for example alcohols, gasoline fractions and chlorinated hydrocarbons and free alkylolamines.
  • cleaning agents are once understood to mean the aqueous solutions intended for direct application to the substrate to be cleaned, but the term cleaning agents also includes the concentrates and solid mixtures intended for the preparation of the application solutions.
  • the ready-to-use solutions can be acidic to strongly alkaline; they are generally used at temperatures of around 20 to 90 ° C.
  • test foamer a 1% strength aqueous solution of the triethernolamine salt of tetrapropylene benzene sulfonate
  • test foamer 1 ml of a 1% strength aqueous solution of the triethernolamine salt of tetrapropylene benzene sulfonate
  • the end group-sealed polyglycol ethers to be used according to the invention give effective effects even in low concentrations. They are preferably added to the cleaning agents in amounts such that their concentration in the ready-to-use solutions is approximately in the range from 50 to 500 ppm.
  • a cleaning solution of one liter was prepared, which was 4 g of whisked whole egg (egg white + egg yolk), 3 g of a dishwasher cleaner of the following recipe

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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

Des éthers de polyéthylène-glycol de formule générale R1O-(CH2CH2O)n-R2, où R1 est un résidu alkyle ou alkényle à chaîne droite ou ramifié avec 8 à 14 atomes de C, R2 est un résidu alkyle avec 8 à 10 atomes de C, et n est un nombre compris entre 2 et 8, à condition que dans le mode de réalisation dans lequel R2 est un résidu alkyle C8, n soit un nombre compris entre 2 et 6, sont utilisés comme additifs antimousse pour des détergents faiblement moussants.
PCT/EP1989/000543 1988-05-27 1989-05-18 Ethers d'alkyle polyglycol antimousse pour detergents (ii) Ceased WO1989011524A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3818014A DE3818014A1 (de) 1988-05-27 1988-05-27 Schaumdrueckende alkylpolyglykolether fuer reinigungsmittel (ii)
DEP3818014.6 1988-05-27

Publications (1)

Publication Number Publication Date
WO1989011524A1 true WO1989011524A1 (fr) 1989-11-30

Family

ID=6355234

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1989/000543 Ceased WO1989011524A1 (fr) 1988-05-27 1989-05-18 Ethers d'alkyle polyglycol antimousse pour detergents (ii)

Country Status (5)

Country Link
EP (2) EP0415970A1 (fr)
JP (1) JPH03504612A (fr)
DE (1) DE3818014A1 (fr)
WO (1) WO1989011524A1 (fr)
ZA (1) ZA894026B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5205959A (en) * 1989-08-30 1993-04-27 Henkel Kommanditgesellschaft Auf Aktien Alkali-stable foam inhibitors
US9181393B2 (en) 2011-08-17 2015-11-10 Dow Global Technologies, Llc Biorenewable biodegradable surfactants

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3942727A1 (de) * 1989-12-22 1991-06-27 Henkel Kgaa Verwendung einer kombination nichtionischer tenside
DE60027549T2 (de) * 1999-02-22 2007-04-26 The Procter & Gamble Company, Cincinnati Maschinengeschirrspülmittel enthaltend ausgewählte nichtionische tenside
US7012052B1 (en) 1999-02-22 2006-03-14 The Procter & Gamble Company Automatic dishwashing compositions comprising selected nonionic surfactants

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1012821A (en) * 1962-02-06 1965-12-08 Rohm & Haas Polyethenoxy ethers
US3684723A (en) * 1964-04-21 1972-08-15 Lever Brothers Ltd Detergent composition
GB1445716A (en) * 1973-04-24 1976-08-11 Diversey Ltd Cleaning compositions
EP0124815A2 (fr) * 1983-05-02 1984-11-14 Henkel Kommanditgesellschaft auf Aktien Utilisation d'éthers de polyglycol comme additifs supprimant la mousse dans des agents de nettoyage peu écumants

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1012821A (en) * 1962-02-06 1965-12-08 Rohm & Haas Polyethenoxy ethers
US3684723A (en) * 1964-04-21 1972-08-15 Lever Brothers Ltd Detergent composition
GB1445716A (en) * 1973-04-24 1976-08-11 Diversey Ltd Cleaning compositions
EP0124815A2 (fr) * 1983-05-02 1984-11-14 Henkel Kommanditgesellschaft auf Aktien Utilisation d'éthers de polyglycol comme additifs supprimant la mousse dans des agents de nettoyage peu écumants

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5205959A (en) * 1989-08-30 1993-04-27 Henkel Kommanditgesellschaft Auf Aktien Alkali-stable foam inhibitors
US9181393B2 (en) 2011-08-17 2015-11-10 Dow Global Technologies, Llc Biorenewable biodegradable surfactants

Also Published As

Publication number Publication date
EP0343504A1 (fr) 1989-11-29
EP0415970A1 (fr) 1991-03-13
ZA894026B (en) 1990-01-31
DE3818014A1 (de) 1989-11-30
JPH03504612A (ja) 1991-10-09

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