EP0876459B9 - Klarspülmittel mit kationischen polymeren - Google Patents

Klarspülmittel mit kationischen polymeren Download PDF

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Publication number
EP0876459B9
EP0876459B9 EP19960929315 EP96929315A EP0876459B9 EP 0876459 B9 EP0876459 B9 EP 0876459B9 EP 19960929315 EP19960929315 EP 19960929315 EP 96929315 A EP96929315 A EP 96929315A EP 0876459 B9 EP0876459 B9 EP 0876459B9
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EP
European Patent Office
Prior art keywords
alkyl
carbon atoms
formula
weight
group
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
EP19960929315
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German (de)
English (en)
French (fr)
Other versions
EP0876459B1 (de
EP0876459A1 (de
Inventor
Christian Nitsch
Willi Buchmeier
Peter Jeschke
Ludwig Schieferstein
Herbert Fischer
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
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0876459A1 publication Critical patent/EP0876459A1/de
Publication of EP0876459B1 publication Critical patent/EP0876459B1/de
Application granted granted Critical
Publication of EP0876459B9 publication Critical patent/EP0876459B9/de
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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2075Carboxylic acids-salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/22Carbohydrates or derivatives thereof
    • C11D3/222Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3776Heterocyclic compounds, e.g. lactam

Definitions

  • the invention relates to the use of cationic polymers as soil release compounds in rinse aid for dishwashers.
  • rinse aids for dishwashers are mixtures of low-foaming fatty alcohol polyethylene / polypropylene glycol ether, solubilizers (for example cumene sulfonate), organic acids (for example citric acid) and solvents (for example ethanol).
  • solubilizers for example cumene sulfonate
  • organic acids for example citric acid
  • solvents for example ethanol
  • EP-A-0 167 382 describes liquid detergent compositions which can contain cationic polymers as thickeners.
  • cationic polymers become hydroxypropyltrimethylammonium guar; copolymers of aminoethyl methacrylate and acrylamide and copolymers of dimethyldiallylammonium chloride and acrylamide.
  • EP-A-0 342 997 describes all-purpose cleaners, the cationic polymers may contain, in particular polymers with imino groups are used.
  • DE-OS-26 16 404 describes cleaning agents for glass, the cationic Contain cellulose derivatives.
  • the addition of the cationic cellulose derivatives in the agents better drainage of the water to get streak-free cleaned glass.
  • Cleaning agents for hard surfaces contain cationic homo- and / or copolymers as so-called soil-release polymers. These polymers have quaternized ammonium alkyl methacrylate groups as monomer units. These compounds are used to make the surfaces like this equip that the next time cleaning the dirt is easier let peel off.
  • the object of the present invention is to provide a rinse aid by means of which Use heavily adhering soiling in subsequent cleaning processes such as oat flakes and other starch deposits can be easily removed from the dishes.
  • Suitable anions in formula I are, for example, halide ions, such as chloride or bromide, SO 4 2- or CH 3 SO 4 - .
  • the preferred polymers can be the monomer units with the formula I in one Contain from 40 mol% to 100 mol%.
  • the proportion of monomer units with of the formula I should preferably not fall below 40 mol%, since otherwise the polymers do not have sufficient water solubility.
  • Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, Crotonic acid and the like, olefins such as ethylene, propylene and butene, alkyl esters of unsaturated carboxylic acids such as methyl acrylate, ethyl acrylate, methyl methacrylate, their Hydroxy derivatives such as 2-hydroxy-ethyl methacrylate, unsaturated aromatic compounds such as styrene, methyl styrene, vinyl styrene and heterocyclic compounds such as Vinyl pyrrolidone can be used.
  • Preferred comonomers are acrylic acid, Methacrylic acid and vinyl pyrrolidone used.
  • the cationic polymers described above can be used in amounts from 0.1% by weight to 30% % By weight, based on the rinse aid, are used.
  • Water-soluble homopolymers or copolymers are preferably used as cationic polymers Monomer units with the above formula I used.
  • organic carboxylic acids are aliphatic hydroxy di and tricarboxylic acids such as malic acid (monohydroxysuccinic acid), tartaric acid (dihydroxysuccinic acid); saturated aliphatic dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, glutaric acid, Adipic acid, gluconic acid (hexane-pentahydroxy-1-carboxylic acid), but preferably anhydrous citric acid.
  • the carboxylic acids are preferably used in amounts from about 1 to 20% by weight.
  • the surfactant base of the rinse aid is preferably formed by nonionic surfactants, which can preferably be contained in an amount of 2 to 20% by weight.
  • the nonionic surfactants are preferably selected from the group of mixed ethers of the formula III, wherein R 10 for a linear or branched, aliphatic alkyl and / or alkenyl radical with 8 to 14 carbon atoms, R 11 for a linear or branched alkyl radical with 1 to 4 carbon atoms or a benzyl radical, a for 0 or numbers from 1 to 2 and b represents numbers from 5 to 15, the fatty alcohol polypropylene glycol / polyethylene glycol ether of the formula IV, wherein R 12 is a linear or branched, aliphatic alkyl and / or alkenyl radical having 8 to 16 carbon atoms, c is 0 or numbers from 1 to 3 and d is numbers from 1 to 5, and the alkyl polyglycosides of the formula V, R 13 O- [
  • Mixed ethers of the formula II are to be understood as meaning known end group-capped fatty alcohol polyglycol ethers which can be obtained by the relevant methods of preparative organic chemistry.
  • Fatty alcohol polyglycol ethers are preferably reacted in the presence of bases with alkyl halides, in particular butyl or benzyl chloride.
  • Typical examples are mixed ethers of the formula (I) in which R 10 represents an industrial, C 12/14 cocoalkyl radical, a represents 0, b represents 5 to 10 and R11 represents a butyl group (Dehypon® LS-54 or LS- 104, Henkel KGaA).
  • the use of mixed ethers capped with butyl or benzyl groups is particularly preferred for technical reasons.
  • the fatty alcohol polypropylene / polyethylene glycol ether with the formula III are known nonionic surfactants which are obtained by adding initially propylene oxide and then ethylene oxide or exclusively ethylene oxide to fatty alcohols.
  • Typical examples are polyglycol ethers of the formula IV in which R 12 represents an alkyl radical having 12 to 18 carbon atoms, c represents 0 or 1 and d represents numbers from 2 to 5. (Dehydol® LS-2, LS-4, LS-5, from Henkel KGaA, Düsseldorf / FRG).
  • the fatty alcohols are preferably only ethoxylated, ie c is zero.
  • Alkyl polyglycosides with the formula IV are known substances that according to the relevant Preparative organic chemistry processes can be obtained. Representative of the extensive literature on EP-A-0 301 298 and WO 90/3977.
  • the alkyl polyglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl polyglycosides are thus alkyl polyglucosides.
  • Alkyl polyglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferably used. From an application point of view, those alkyl polyglycosides are preferred whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.6.
  • Solubilizers e.g. Cumene sulfonate, as well as color and Fragrances in question, being in the agents according to the invention in a preferred embodiment solution brokers are dispensed with.
  • the mixture was heated to 70 ° C. and left at this temperature for 30 minutes. Subsequently was allowed to react for a further hour at 80 ° C.
  • the cleaning performance was then rated on a scale from 0 to 10, 0 means no cleaning and 10 means complete cleaning.

Landscapes

  • 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)
  • Detergent Compositions (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyethers (AREA)
  • Epoxy Compounds (AREA)
  • Polyamides (AREA)
EP19960929315 1995-09-04 1996-08-23 Klarspülmittel mit kationischen polymeren Expired - Lifetime EP0876459B9 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19532542 1995-09-04
DE19532542A DE19532542B4 (de) 1995-09-04 1995-09-04 Klarspülmittel mit kationischen Polymeren
PCT/EP1996/003724 WO1997009408A1 (de) 1995-09-04 1996-08-23 Klarspülmittel mit kationischen polymeren

Publications (3)

Publication Number Publication Date
EP0876459A1 EP0876459A1 (de) 1998-11-11
EP0876459B1 EP0876459B1 (de) 2001-07-04
EP0876459B9 true EP0876459B9 (de) 2004-07-28

Family

ID=7771176

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19960929315 Expired - Lifetime EP0876459B9 (de) 1995-09-04 1996-08-23 Klarspülmittel mit kationischen polymeren

Country Status (6)

Country Link
US (1) US6025314A (es)
EP (1) EP0876459B9 (es)
AT (1) ATE202797T1 (es)
DE (2) DE19532542B4 (es)
ES (1) ES2160253T3 (es)
WO (1) WO1997009408A1 (es)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999005248A1 (en) * 1997-07-23 1999-02-04 Unilever Plc Automatic dishwashing compositions containing water soluble cationic or amphoteric polymers
US5981456A (en) * 1997-07-23 1999-11-09 Lever Brothers Company Automatic dishwashing compositions containing water soluble cationic or amphoteric polymers
EP1078032A1 (en) * 1998-05-11 2001-02-28 Unilever Plc Machine dishwashing compositions and rinse aid compositions
EP1063281A3 (en) * 1999-06-25 2004-01-21 JohnsonDiversey, Inc. Rinse aid composition and method for using the same
GB0009029D0 (en) 2000-04-12 2000-05-31 Unilever Plc Laundry wash compositions
GB0009877D0 (en) * 2000-04-20 2000-06-07 Unilever Plc Granular detergent component and process for its preparation
DE10032611A1 (de) 2000-07-07 2002-01-24 Henkel Kgaa Maschinengeschirrspülmittel mit Zusatznutzen
US6326343B1 (en) * 2000-09-08 2001-12-04 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Three-in-one composition for dishwashing machines
WO2002031095A1 (en) * 2000-10-10 2002-04-18 Johnsondiversey, Inc. A detergent composition and method for warewashing
US6786223B2 (en) * 2001-10-11 2004-09-07 S. C. Johnson & Son, Inc. Hard surface cleaners which provide improved fragrance retention properties to hard surfaces
US6701940B2 (en) * 2001-10-11 2004-03-09 S. C. Johnson & Son, Inc. Hard surface cleaners containing ethylene oxide/propylene oxide block copolymer surfactants
DE10342631B4 (de) * 2003-09-15 2006-04-13 Henkel Kgaa Maschinelle Geschirrspülmittel mit spezieller Polymermischung
DE10342632A1 (de) * 2003-09-15 2005-04-07 Henkel Kgaa Maschinelle Geschirrspülmittel mit speziellen Polymeren
US7580523B2 (en) * 2004-01-16 2009-08-25 The Directv Group, Inc. Distribution of video content using client to host pairing of integrated receivers/decoders
DE102004015401A1 (de) * 2004-03-26 2005-10-20 Henkel Kgaa Maschinelles Geschirrspülmittel
DE102005025041A1 (de) * 2005-05-30 2006-12-07 Bell Flavors & Fragrances Duft Und Aroma Gmbh Mittel zur Anwendung in Spülmaschinen sowie Vorrichtung für dessen dosierte Einbringung während der Spül- und Trocknungsphasen
GT200600375A (es) 2005-08-17 2007-03-14 Composición limpiadora ácida que contiene un polímero de hidrofilización
DE102005060431A1 (de) * 2005-12-15 2007-06-21 Henkel Kgaa Maschinelles Geschirrspülmittel
US9629361B2 (en) 2006-02-09 2017-04-25 Gojo Industries, Inc. Composition and method for pre-surgical skin disinfection
US8119115B2 (en) * 2006-02-09 2012-02-21 Gojo Industries, Inc. Antiviral method
US8450378B2 (en) * 2006-02-09 2013-05-28 Gojo Industries, Inc. Antiviral method
US20070185216A1 (en) * 2006-02-09 2007-08-09 Marcia Snyder Antiviral method
EP2014757A1 (en) * 2007-07-05 2009-01-14 JohnsonDiversey, Inc. Rinse aid
JP2012510342A (ja) 2008-12-02 2012-05-10 ディバーシー・インコーポレーテッド カチオン性澱粉を含有する器物洗浄システム
AU2009322572B2 (en) 2008-12-02 2014-07-17 Diversey, Inc. Cleaning of a cooking device or appliance with a composition comprising a built-in rinse aid
UA109772C2 (uk) * 2009-07-02 2015-10-12 Агент для підвищення гідрофільності ґрунту і способи його застосування
JP2013542279A (ja) * 2010-10-01 2013-11-21 ロディア オペレーションズ 硬質表面用洗浄組成物

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Publication number Priority date Publication date Assignee Title
GB1553201A (en) * 1975-04-18 1979-09-26 Colgate Palmolive Co Method of cleaning glass or glazed articles
FI823446L (fi) * 1981-10-16 1983-04-17 Unilever Nv Foerbaettrad komposition foer maskinell diskning och skoeljning
US4454060A (en) * 1983-06-09 1984-06-12 Colgate-Palmolive Company Liquid detergent composition with a cationic foam stabilizing copolymer containing pendant quaternary nitrogen groups and pendant hydrophobic groups
GB8416884D0 (en) * 1984-07-03 1984-08-08 Procter & Gamble Liquid cleansing composition
DE3723826A1 (de) * 1987-07-18 1989-01-26 Henkel Kgaa Verfahren zur herstellung von alkylglykosiden
GB8811953D0 (en) * 1988-05-20 1988-06-22 Unilever Plc General-purpose cleaning compositions
DE3833780A1 (de) * 1988-10-05 1990-04-12 Henkel Kgaa Verfahren zur direkten herstellung von alkylglykosiden
US5576425A (en) * 1988-10-05 1996-11-19 Henkel Kommanditgesellschaft Auf Aktien Process for the direct production of alkyl glycosides
EP0467472A3 (en) * 1990-07-16 1993-06-02 Colgate-Palmolive Company Hard surface liquid cleaning composition with anti-soiling polymer
DE4131898A1 (de) * 1991-09-25 1993-04-01 Henkel Kgaa Zubereitungen zur haarbehandlung
DE69320082T2 (de) * 1992-03-10 1999-05-06 Rohm & Haas Verwendung von wasserlöslichen Polymeren in Reinigungsmittelzusammensetzungen und für solche Anwendungen geeignete wasserlösliche Polymere
DE4301459A1 (de) * 1993-01-20 1994-07-21 Huels Chemische Werke Ag Wäßriges Weichspülmittel für die Behandlung von Textilien
JPH06288871A (ja) * 1993-03-31 1994-10-18 Hino Motors Ltd 同期撮影装置
DE4318171A1 (de) * 1993-06-01 1994-12-08 Henkel Kgaa Wäßrige tensidische Zubereitungen

Also Published As

Publication number Publication date
DE19532542B4 (de) 2008-12-18
DE59607240D1 (de) 2001-08-09
ES2160253T3 (es) 2001-11-01
US6025314A (en) 2000-02-15
EP0876459B1 (de) 2001-07-04
WO1997009408A1 (de) 1997-03-13
EP0876459A1 (de) 1998-11-11
ATE202797T1 (de) 2001-07-15
DE19532542A1 (de) 1997-03-06

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