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EP0876459B1 - Agents de rin age contenant des polymeres cationiques - Google Patents

Agents de rin age contenant des polymeres cationiques Download PDF

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Publication number
EP0876459B1
EP0876459B1 EP19960929315 EP96929315A EP0876459B1 EP 0876459 B1 EP0876459 B1 EP 0876459B1 EP 19960929315 EP19960929315 EP 19960929315 EP 96929315 A EP96929315 A EP 96929315A EP 0876459 B1 EP0876459 B1 EP 0876459B1
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Prior art keywords
alkyl
carbon atoms
formula
weight
group
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EP19960929315
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German (de)
English (en)
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EP0876459B9 (fr
EP0876459A1 (fr
Inventor
Christian Nitsch
Willi Buchmeier
Peter Jeschke
Ludwig Schieferstein
Herbert Fischer
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Henkel AG and Co KGaA
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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/fr
Publication of EP0876459B1 publication Critical patent/EP0876459B1/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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular 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
    • 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
    • C11D3/2075—Carboxylic acids-salts 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
    • 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
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • 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
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3776—Heterocyclic 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 the cleaning process, the dirt is easier let peel off.
  • the object of the present invention is to provide a rinse aid by which Use heavily adhering soiling in subsequent cleaning processes like oatmeal 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 the 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 e.g. 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 stands for 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 known end-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 stands for an industrial, C 12/14 cocoalkyl radical, a for 0, b for 5 to 10 and R11 for a butyl group (Dehypon® LS-54 or LS- 104, Henkel KGaA).
  • the use of mixed ethers which are closed 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 according to the relevant Preparative organic chemistry processes can be obtained.
  • Representative of the extensive literature here is the documents 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.

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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)
  • Detergent Compositions (AREA)
  • Polyamides (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyethers (AREA)
  • Epoxy Compounds (AREA)

Claims (6)

  1. Utilisation comme composés soil-release dans des agents de rinçage pour lave-vaisselle, d'homo- ou de copolymères cationiques, qui renferment des motifs monomères de la formule I
    Figure 00170001
    dans laquelle
    R1 représente l'hydrogène ou un groupe méthyle et
    R2, R3 et R4 peuvent être identiques ou différents et correspondre à l'hydrogène ou à un groupe alkyle(alcényle) en C1-8, R8 est un groupe alkylène à chaíne droite, cyclique ou ramifiée comportant 2 à 8 atomes de C et
    X représente un anion monovalent ou la partie 1/m d'un anion m-valent.
  2. Utilisation selon la revendication 1, caractérisée en ce que les polymères cationiques renferment les monomères de la formule I dans une proportion de 40 à 100 mol %.
  3. Utilisation selon une des revendications 1 à 2 comme polymère soil-release pour le nettoyage des salissures renfermant de l'amidon.
  4. Agent de rinçage renfermant
    a) 0,1 à 30 % en poids de polymères cationiques, selon la revendication 1,
    b) 0,5 à 30 % en poids d'acides carboxyliques organiques, en particulier l'acide citrique
    c) 0,5 à 30 % en poids de tensioactifs non ioniques sélectionnés parmi le groupe des polypropylèneglycol/polyéthylèneglycoléthers d'alcools gras fermés au niveau des groupes terminaux et comportant des groupes OH terminaux, des alkylpolyglycosides, des N-alkylpolyhydroxyalkylamides d'acides gras en C6-C22, des alcanolamides d'acides gras en C6-C22, des aminoxydes d'alkyle gras et des mélanges quelconques des composés qui précèdent et
    d) 10 à 98,1 % en poids d'eau.
  5. Agent de rinçage selon la revendication 4, caractérisé en ce que l'on met en oeuvre comme acide carboxylique organique, de l'acide citrique.
  6. Agent de rinçage selon la revendication 4 ou 5, caractérisé en ce que l'on met en oeuvre comme tensioactifs non ioniques, des éthers mixtes de la formule III,
    Figure 00180001
    dans laquelle R10 représente un radical alkyle et/ou alcényle aliphatique, linéaire ou ramifié comportant 8 à 14 atomes de carbone, R11 correspond à un radical alkyle linéaire ou ramifié présentant 1 à 4 atomes de carbone ou un radical benzyle, a est égal à 0 ou à un nombre de 1 à 2 et b représente un nombre de 5 à 15,
    des polypropylèneglycol/polyéthylèneglycoléthers d'alcools gras de la formule IV,
    Figure 00190001
    dans laquelle R12 représente un radical alkyle et/ou alcényle aliphatique, linéaire ou ramifié comportant 8 à 16 atomes de carbone, c est égal à 0 ou à un nombre de 1 à 3 et d représente un nombre de 1 à 5, ou
    des alkylpolyglycosides de la formule V, R13O-[G]p dans laquelle R13 représente un radical alkyle comportant 8 à 22 atomes de carbone, G correspond à un radical de sucre présentant 5 ou 6 atomes de carbone, de préférence un radical de glucose, et p est égal à un nombre de 1 à 10.
EP19960929315 1995-09-04 1996-08-23 Agents de rin age contenant des polymeres cationiques Expired - Lifetime EP0876459B9 (fr)

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 (fr) 1995-09-04 1996-08-23 Agents de rinçage contenant des polymeres cationiques

Publications (3)

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

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ID=7771176

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EP19960929315 Expired - Lifetime EP0876459B9 (fr) 1995-09-04 1996-08-23 Agents de rin age contenant des polymeres cationiques

Country Status (6)

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

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EP1063281A3 (fr) * 1999-06-25 2004-01-21 JohnsonDiversey, Inc. Agent de rinçage et procédé d'utilisation dudit agent de rinçage
GB0009029D0 (en) 2000-04-12 2000-05-31 Unilever Plc Laundry wash compositions
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DE102005060431A1 (de) * 2005-12-15 2007-06-21 Henkel Kgaa Maschinelles Geschirrspülmittel
US8450378B2 (en) * 2006-02-09 2013-05-28 Gojo Industries, Inc. Antiviral method
US9629361B2 (en) 2006-02-09 2017-04-25 Gojo Industries, Inc. Composition and method for pre-surgical skin disinfection
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KR101723248B1 (ko) 2008-12-02 2017-04-04 디버세이, 인크 양이온성 전분을 포함하는 식기 세척 시스템
UA109772C2 (uk) * 2009-07-02 2015-10-12 Агент для підвищення гідрофільності ґрунту і способи його застосування
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Also Published As

Publication number Publication date
DE19532542B4 (de) 2008-12-18
DE59607240D1 (de) 2001-08-09
US6025314A (en) 2000-02-15
WO1997009408A1 (fr) 1997-03-13
EP0876459B9 (fr) 2004-07-28
ES2160253T3 (es) 2001-11-01
DE19532542A1 (de) 1997-03-06
EP0876459A1 (fr) 1998-11-11
ATE202797T1 (de) 2001-07-15

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