WO2013075827A1 - Utilisation de polymères obtenus par polymérisation radicalaire en émulsion en tant qu'épaississants pour des produits de nettoyage - Google Patents

Utilisation de polymères obtenus par polymérisation radicalaire en émulsion en tant qu'épaississants pour des produits de nettoyage Download PDF

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Publication number
WO2013075827A1
WO2013075827A1 PCT/EP2012/004831 EP2012004831W WO2013075827A1 WO 2013075827 A1 WO2013075827 A1 WO 2013075827A1 EP 2012004831 W EP2012004831 W EP 2012004831W WO 2013075827 A1 WO2013075827 A1 WO 2013075827A1
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Prior art keywords
cleaner
use according
mol
monomer
group
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PCT/EP2012/004831
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German (de)
English (en)
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WO2013075827A4 (fr
Inventor
Aleksandrovic-Bondzic Vesna
Mertens Sascha
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Centrum Für Angewandte Nanotechnologie (Can) Gmbh
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Publication of WO2013075827A1 publication Critical patent/WO2013075827A1/fr
Publication of WO2013075827A4 publication Critical patent/WO2013075827A4/fr

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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
    • 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
    • C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C11D3/3765—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes

Definitions

  • the invention relates to the use of a novel polymer with thickening properties as thickener for inanimate surface cleaners.
  • the invention does not relate to the use of a novel polymer having thickening properties as thickener in cosmetic or dermatological preparations such as shampoos or shower preparations.
  • Thickening polymers are able to interact in hydrophilic, especially in aqueous preparations, both with itself and with other substances in such a way that they influence viscosity and flow behavior.
  • EP 1 465 932 B1 describes alkali-swellable and alkali-soluble associative polymers prepared from a monomer mixture of (a) at least one acidic vinyl monomer or a salt thereof, (b) at least one nonionic vinyl monomer, (c) a first associative monomer having a first hydrophobic end group, (d) a second associative monomer having a second hydrophobic end group or a semihydrophobic monomer or a combination thereof and optionally (e) a crosslinking monomer or chain transfer agent or a combination thereof.
  • WO 2009/019225 A2 describes an aqueous dispersion of a copolymer having polymerized units a) at least one ethylenically unsaturated carboxylic acid, b) at least one nonionically unsaturated surfactant monomer, c) at least one C 1 - to C 2 -alkyl acrylate, wherein the number of alkyl groups the alkyl acrylate average alkyl chain length 2.1 to 4, is. After neutralization with alkali, the dispersion serves as an associative thickener, in particular for liquid washing and cleaning agent formulations.
  • the preparation of a thickener with satisfactory properties requires the addition of associative monomers.
  • the object of the present invention is therefore to find as transparent as possible thickeners, with which it is possible to thicken storage-stable surfactant-containing detergent preparations without any turbidity, but at the same time have the best possible thickening properties, ie shear thinning in the thickened preparation, ie a very high viscosity at rest and have a low viscosity under the action of high shear forces, and, moreover, have low tan ⁇ values, but in the preparation do not necessarily require the addition or only a small addition of associative monomers.
  • sociative monomers monomers of the type "A-P-H", where A is an ethylenically unsaturated group, such as a
  • Methacrylic, acrylic, allyl or vinyl group, P contains a spacer of one
  • the object is achieved by the use of a polymer as a thickener for cleaning products for inanimate surfaces, in particular for household cleaning products, cleaning products for cleaning hard surfaces, automotive cleaning products and detergents, characterized in that the polymer by free-radical emulsion polymerization of (A) at least one acidic Vinyl monomer or its salt, (B) at least one nonionic vinyl monomer, (C) at least one monomer containing an unsaturated end group and a polyoxyalkylene part, (D) at least one crosslinking monomer, the polymerization being controlled so as to be at least temporarily the gel effect occurs, achieved by that
  • the metering time is 30-40 minutes, based on a reaction vessel without internal cooling, when the monomers are added together; at a reaction volume of 100 ml to 15 I, the metering time up to 90 minutes, preferably 60 minutes, based on a reaction vessel without internal cooling, when the monomer (D) is added delayed by up to 10 minutes;
  • the metering time is at least 40 minutes, preferably 60-120, particularly preferably 120-180 minutes, based on a reaction vessel without internal cooling.
  • the thickeners used according to the invention are capable of stabilizing various pigments and other additives and air bubbles in a preparation.
  • the thickeners used according to the invention show a higher transparency than other thickeners at the same pH.
  • a protective colloid is, for example, allyl-modified hydroxymethylcellulose.
  • the monomers in the preparation of the polymer used are preferably in contents of from 10 to 75 wt .-%, preferably 30 to 50 wt .-% of monomers (A), particularly preferably 35 to 49 wt .-%, monomers (B) of From 10 to 90% by weight, preferably from 30 to 80% by weight, particularly preferably from 47 to 60% by weight, of monomers (C) in amounts of from 0.5 to 40% by weight, preferably from 1 to 10% by weight, particularly preferably from 2 to 6% by weight, and monomers (D) in contents of up to 1% by weight, preferably 0 , 05 to 0.5 wt .-%, particularly preferably 0, 1 to 0.35 wt .-% used.
  • the acidic vinyl monomer (A) used is preferably one from the group of vinyl monomers having carboxyl groups, more preferably from the group of acrylic acid or methacrylic acid or the alkali metal, alkaline earth metal, ammonium or alkylammonium salts of methacrylic acid, most preferably from the group the methacrylic acid or the alkali, alkaline earth, ammonium or alkylammonium salts of methacrylic acid.
  • the nonionic vinyl monomer (B) is preferably a hydrophobic nonionic vinyl monomer and / or selected from the group of Cr to C22 alkyl acrylates or C 1 to C 2 alkyl methacrylates or mixtures thereof.
  • the mass ratio of the monomers (A) to (B) is preferably 1: 2.2 to 2: 1.
  • the monomer (C) is preferably selected from the group of vinylpolyalkylene glycols or polymerizable surfactants or mixtures thereof, preferably from the group of allyl alcohol alkoxylate, allyl polyalkylene glycol ethers (EO 30 mol),
  • Allyl polyalkylene glycol ether (EO 20 mol), allyl polyalkylene glycol ether (EO 20 mol, PO 20 mol), 1,4-butanediol vinyl ether (EO / PO 30 mol), polyalkylene glycol allyl butyl ether (EO 25 mol, PO 8 mol), vinyl polyalkylene glycol ether (EO 40 mol),
  • the crosslinking monomer (D) is preferably selected from the group of polyol acrylates or polyol methacrylates having at least two acrylate groups or
  • Preferred uses according to the invention for such polymers are the use in all-purpose cleaners, in floor cleaners, in window cleaners, in dishwashing detergents, in bathroom cleaners, in toilet cleaners, in drain cleaners, in tile cleaners. in carpet cleaners, in glass cleaners, in hygiene cleaners, in oven cleaners, in furniture cleaners or in gel detergents.
  • Preferred uses of the invention are also in the field of cleaning products for engines, car shampoos, car window cleaner, paint cleaner, brake cleaner, insect remover, convertible top cleaner, upholstery cleaner or rim cleaner.
  • Hard surfaces according to the invention for example, floors, tiles, tiles, plastics and other hard surfaces in the home, in toilets, in public sanitary facilities, in swimming pools, saunas, sports facilities or in doctor or massage practices understood.
  • the detergents and cleaners may contain customary ingredients for this product group, such as builder substances, special polymers, for example those with co-builder properties, foam inhibitors, dyes and possibly additional fragrances (perfumes), pH adjusters, thickeners, polyethylene glycols, bleaches, such as peroxo Bleaches and chlorine bleaches, bleach activators, bleach stabilizers, bleach catalysts, enzymes, in particular proteases, amylases or cellulases, enzyme stabilizers, dye transfer inhibitors and scorch inhibitors, without the ingredients being restricted to these substance groups.
  • customary ingredients for this product group such as builder substances, special polymers, for example those with co-builder properties, foam inhibitors, dyes and possibly additional fragrances (perfumes), pH adjusters, thickeners, polyethylene glycols, bleaches, such as peroxo Bleaches and chlorine bleaches, bleach activators, bleach stabilizers, bleach catalysts, enzymes, in particular proteases, amylases or cellulases, enzyme stabilize
  • nanoparticles for example a combination of zinc oxide and copper or magnesium, prepared according to WO 201 1/033040 A2. These nanoparticles have antibacterial properties.
  • important ingredients of the detergent compositions are also washing aids, for example, and not limiting optical brighteners, UV-protective substances and Soll Repellents, especially substances that counteract the re-soiling of fibers are mentioned.
  • Suitable optical brighteners are derived, for example, from the substance classes of 4,4'-diamino-2,2'-stilbenedisulfonic acids (flavone acids), 4,4'-distyrylbiphenyls, methylumbelliferones, coumarins, dihydroquinolinones, etc., which are described in [0090] of document DE 10 2007 036 910 A1 are called.
  • Suitable UV protective substances are the UV absorbers mentioned in [0101] of the document DE 10 2007 036 910 A1 or those mentioned in [0185] of the document DE 10 2007 058 342 A1.
  • Non-ionic cellulose ethers such as methylcellulose and. Serve as polymers with dirt-repellent and / or soil-dissolving properties
  • Substances which counteract the re-soiling of fibers are, for example, alcohol ethoxylate propoxylates, which are described in the document DE 10 2005 018 501 A1.
  • binding and disintegration aids may also be present.
  • binder synthetic organic polymers having a suitable melting temperature, in particular, e.g. Polyethylene glycol, such as polyethylene glycol having an average molecular weight of 500 g / mol (PEG 1500).
  • suitable binders are polyvinylpyrrolidone (PVP),
  • Disintegration aids are, for example, carbonate / citric acid systems, it also being possible to use other organic acids, and also synthetic polymers such as polyvinylpyrrolidone or natural polymers or modified natural substances such as cellulose and starch and their derivatives, alginates or casein derivatives.
  • Other disintegration aids based on cellulose are described in the document WO 1999/029826 A1.
  • the cleaning agents can each be solid or liquid. Likewise, they may also be in a form comprising solid and liquid components or subsets of the components side by side.
  • the thickeners used in the invention require in their preparation no addition of associative monomers or only an addition of these monomers in low concentrations of at most 1 wt .-%. In the production of the thickeners, however, associative thickeners can generally also be used in amounts of more than 1% by weight.
  • Surfactants for the cleaning products in use with the thickeners are, in particular, fatty alcohol ethoxylates, linear alkylbenzenesulfonates,
  • the surfactant is usually used in amounts of up to 50 wt .-%.
  • thickening preparations for detergent products preferably up to 20% by weight of the thickening polymer is used. In this concentration range added suspended matter does not settle. Suspending substances may be, for example, pearls, pigments or air bubbles.
  • the cleaning agents are, so far as they are gelatinized preparations with yield point, adjusted so that they have a yield value of 0.5 to 20 Pa, preferably 1 to 6 Pa.
  • a yield point the critical shear stress of the Flow curve viewed.
  • the flow limit is determined, for example, as follows: The flow curve is measured on a shear stress controlled rheometer (Malvern Gemini HR nano) at 25 ° C ⁇ 1 ° C with 20 mm plate / plate geometry at a gap between 0.8 mm and 1, 2 mm. It is filled in a gentle way. A suitable constant shear stress ramp is specified. Before the test, a corresponding structure recovery time is maintained and the critical shear stress is specified at the maximum of the flow curve.
  • the cleaning agents preferably have a tan ⁇ value of 0.05 to 0.6, preferably 0, 1 to 0.5.
  • the "tan ⁇ value" in the sense of the present invention is equal to the quotient of the loss modulus and the storage modulus, measured in each case at 40 ° C.
  • the tan ⁇ value is determined as follows: The loss and storage modulus are determined by a dynamic frequency test run with a shear stress controlled rheometer (Malvern Gemini HR nano) at 40 ° C ⁇ 1 ° C with 20 mm plate / plate geometry measured at a gap between 0.8 mm and 1, 2 mm, whereby a structure-gentle filling takes place following parameters:
  • the frequency test is carried out with a corresponding structure recovery time before the test and the tan ⁇ value in the frequency range between 0.05 rad / s and 3.0 rad / s specified, preferably between 0.08 rad / s and 1, 0 rad / s ,
  • Preferred formulations with the thickener used according to the invention have a turbidity value of NTU (Nephelometry Turbidity Unit) ⁇ 20 at pH ⁇ 6.2.
  • NTU Nephelometry Turbidity Unit
  • preparations with a haze value> 20 can also be used as cleaning agents, where the use of transparent preparations does not matter.
  • the detergents in which the thickener is used may have an acidic, basic or neutral pH.
  • the cleaning product may be an aqueous cleaning product, preferably with a water content of 15 to 99% by weight.
  • the thickeners are used in alcoholic cleaning products according to the invention, in which the alcohol content is preferably 0.1 to 85 wt .-%.
  • the information on the ratios of the monomers is percent by weight. In each case about 1 kg of polymer was produced. Here is:
  • R1 100 polyglycol
  • R1 100 (Clariant)
  • Polymer A was distributed in water. Texapon N 70 and Ufasan 50 were added. The solution was homogenized. The pH was adjusted to 6.2 with sodium hydroxide. Subsequently, Tego® Betain F 50 was added. With the homogenization, the finished mixture was obtained. Worlee beads Jojoba were carefully distributed in the resulting mixture.
  • the hand dishwashing detergent is transparent and colorless.
  • the Worlee beads are prevented from sinking by the A polymer. Tan ⁇ was measured. This was 0.13, which confirms the stabilization of the beads and air bubbles over a longer period of time.
  • Polymer A was dispersed in water and mixed with the two surfactants Tergitol 15-S-7 and Ufasan 50. The mixture was homogenized. After adjusting the pH to 6.2 with sodium hydroxide, the alcohol was added. The mixture was carefully homogenized.
  • the polymer A causes a slower course of the glass cleaner than the same composition without the thickener on a vertical surface and thus improved contact time and dirt removal.
  • the glass cleaner is thin and sprayable.
  • Example 3 The procedure was as in Example 3, but with the difference that the pH was adjusted to a value of 8.0 with sodium hydroxide.
  • the all-purpose cleaner can be easily dosed by the thickening.
  • the air bubbles stabilized in the formulation are intended to arouse increased consumer interest in the consumer.
  • the long-term stabilization of air bubbles was confirmed by measuring a tan ⁇ of 0.28.
  • Zinc oxide / copper nanoparticles size: about 30 nm long and 5-7 nm diameter, rod-shaped, about 10 wt .-% copper
  • the CANdot ® s of series D are prevented from sinking by the polymer C, so that the gel no longer needs to be homogenized before further processing.

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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)
  • Dispersion Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Utilisation de nouveaux polymères en tant qu'épaississants pour des produits de nettoyage contenant des tensioactifs, qui, outre divers produits de nettoyage, comprennent aussi des détergents. Ces épaississants sont obtenus par polymérisation radicalaire en émulsion d'au moins un monomère vinylique acide ou de son sel, d'un monomère vinylique non ionique, d'un monomère présentant un groupe terminal insaturé et une fraction polyoxyalkylène ainsi que d'un monomère à réticulation transversale. Grâce à ces nouveaux polymères, il est possible d'épaissir des produits de nettoyage tout en leur conservant une transparence élevée.
PCT/EP2012/004831 2011-11-25 2012-11-22 Utilisation de polymères obtenus par polymérisation radicalaire en émulsion en tant qu'épaississants pour des produits de nettoyage WO2013075827A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011119332.8 2011-11-25
DE102011119332A DE102011119332A1 (de) 2011-11-25 2011-11-25 Verwendung von über radikalische Emulsionspolymerisation erhältlichen Polymeren als Verdicker für Reinigungsmittel

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WO2013075827A1 true WO2013075827A1 (fr) 2013-05-30
WO2013075827A4 WO2013075827A4 (fr) 2013-08-29

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0711828A2 (fr) 1994-11-14 1996-05-15 Unilever Plc Compositions détergentes
WO1999029826A1 (fr) 1997-12-08 1999-06-17 Henkel Kommanditgesellschaft Auf Aktien Corps moules de detergent a desintegration amelioree
WO2003062288A1 (fr) * 2002-01-18 2003-07-31 Noveon Ip Holdings Corp. Polymeres associatifs gonflant aux alcalis, procedes et composition
DE102005018501A1 (de) 2005-04-21 2006-10-26 Clariant Produkte (Deutschland) Gmbh Wasch- und Reinigungsmittel enthaltend Alkohol-Ethoxylat-Propoxylate
WO2009019225A2 (fr) 2007-08-03 2009-02-12 Basf Se Dispersion d'épaississant associatif
DE102007036910A1 (de) 2007-08-06 2009-02-12 Henkel Ag & Co. Kgaa Verdicktes, flüssiges Wasch- oder Reinigungsmittel
DE102007058342A1 (de) 2007-12-03 2009-06-04 Henkel Ag & Co. Kgaa Verminderung der Biofilmbildung durch multifunktionelle Copolymere
WO2011033040A2 (fr) 2009-09-16 2011-03-24 Centrum Für Angewandte Nanotechnologie (Can) Gmbh Particules antibactériennes et leur synthèse
DE102010022063A1 (de) 2010-05-31 2011-12-01 Beiersdorf Ag Neues verdickendes Polymer

Family Cites Families (7)

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PL351567A1 (en) * 1999-04-20 2003-05-05 Basf Ag Hydrogel-forming polymer mixture
DE10059830A1 (de) * 2000-12-01 2002-06-13 Clariant Gmbh Kationisch modifizierte Kammpolymere auf Basis von Acryloyldimethyltaurinsäure
AU785016B2 (en) * 2001-06-14 2006-08-24 Rohm And Haas Company Semi-continuous bimodal emulsion polymerization
DE10344527A1 (de) * 2003-09-25 2005-04-21 Beiersdorf Ag Schäumende Zubereitungen mit Fließgrenze
DE102004020544A1 (de) * 2004-04-27 2005-11-24 Basf Ag Copolymere mit N-heterocyclischen Gruppen und deren Verwendung als Additiv in Waschmitteln
ES2371698T3 (es) * 2007-10-12 2012-01-09 Basf Se Formulaciones de detergentes para lavado de platos que contienen una mezcla de policarboxilatos con modificación hidrófuga y policarboxilatos con modificación hidrófila.
DE102011078087A1 (de) 2011-06-27 2012-12-27 Beiersdorf Ag Neues verdickendes Polymer II

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0711828A2 (fr) 1994-11-14 1996-05-15 Unilever Plc Compositions détergentes
WO1999029826A1 (fr) 1997-12-08 1999-06-17 Henkel Kommanditgesellschaft Auf Aktien Corps moules de detergent a desintegration amelioree
WO2003062288A1 (fr) * 2002-01-18 2003-07-31 Noveon Ip Holdings Corp. Polymeres associatifs gonflant aux alcalis, procedes et composition
EP1465932B1 (fr) 2002-01-18 2008-07-09 Lubrizol Advanced Materials, Inc. Polymeres associatifs gonflant aux alcalis, procedes et composition
DE102005018501A1 (de) 2005-04-21 2006-10-26 Clariant Produkte (Deutschland) Gmbh Wasch- und Reinigungsmittel enthaltend Alkohol-Ethoxylat-Propoxylate
WO2009019225A2 (fr) 2007-08-03 2009-02-12 Basf Se Dispersion d'épaississant associatif
DE102007036910A1 (de) 2007-08-06 2009-02-12 Henkel Ag & Co. Kgaa Verdicktes, flüssiges Wasch- oder Reinigungsmittel
DE102007058342A1 (de) 2007-12-03 2009-06-04 Henkel Ag & Co. Kgaa Verminderung der Biofilmbildung durch multifunktionelle Copolymere
WO2011033040A2 (fr) 2009-09-16 2011-03-24 Centrum Für Angewandte Nanotechnologie (Can) Gmbh Particules antibactériennes et leur synthèse
DE102010022063A1 (de) 2010-05-31 2011-12-01 Beiersdorf Ag Neues verdickendes Polymer

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WO2013075827A4 (fr) 2013-08-29
DE102011119332A1 (de) 2013-05-29

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