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WO1999066016A1 - Utilisation de 1,3-dioxolan-2-ones dans des produits de lavage et de nettoyage - Google Patents

Utilisation de 1,3-dioxolan-2-ones dans des produits de lavage et de nettoyage Download PDF

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Publication number
WO1999066016A1
WO1999066016A1 PCT/EP1999/003869 EP9903869W WO9966016A1 WO 1999066016 A1 WO1999066016 A1 WO 1999066016A1 EP 9903869 W EP9903869 W EP 9903869W WO 9966016 A1 WO9966016 A1 WO 9966016A1
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WO
WIPO (PCT)
Prior art keywords
dioxolan
weight
agents
detergent
detergents
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/EP1999/003869
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German (de)
English (en)
Inventor
Thorsten LÖHL
Ansgar Behler
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 WO1999066016A1 publication Critical patent/WO1999066016A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C07D317/38—Ethylene carbonate
    • 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
    • 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
    • C11D3/2096—Heterocyclic compounds
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3942—Inorganic per-compounds

Definitions

  • the present invention relates to improving the solubility of detergents and cleaning agents containing surfactants.
  • Detergents and cleaning agents exist in the market in a variety of configurations, both for washing textiles in household and industrial washing, and for cleaning soiled surfaces from objects such as dishes, furniture, carpets or rooms such as kitchens or sanitary rooms to complete Industrial plants.
  • the washing and cleaning performance of these agents is largely based on the use of surface-active substances, i.e. surfactants.
  • alkylene carbonates as nitrogen-free amphiphile in cleaning agents containing anionic surfactants and cleaning agents for hard surfaces which contain 0.5 to 5% by weight of C 6.14 alkylene carbonate (s) is described in international patent application WO98 / 00418 (Colgate). According to this document, the use of the alkylene carbonates together with the anionic surfactant leads to analphotrophic mixtures which can provide a higher surfactant concentration at the solid-liquid interface.
  • the present invention was based on the object of improving the solubility and the rate of dissolution of detergents and cleaning agents containing surfactants, in particular the solubility profile of detergents and cleaning agents which contain nonionic surfactants should be improved.
  • the invention therefore relates to the use of 1,3-dioxolan-2-ones in detergents and cleaning agents for improving the solubility of surfactants.
  • the 1,3-dioxolan-2-ones to be used according to the invention are usually used in washing and cleaning agents in amounts of 0.5 to 20% by weight, preferably 1.5 to 15% by weight and in particular 2 5 to 10 wt .-%, each based on the detergent and cleaning agent used.
  • the ratio of surfactant to 1,3-dioxolan-2-one is between 20: 1 and 1: 5, preferably between 10: 1 and 1: 2 and in particular between 5: 1 and 1: 1.
  • 1,3-dioxolan-2-ones to be used according to the invention are cyclic esters of carbonic acid and can be described by the following structure:
  • R represents a substituted or unsubstituted alkyl, alkenyl or alkylaryl radical.
  • R radicals are methyl, ethyl, n-propyl, iso-propyl and hydroxymethyl and hydroxyethyl radicals.
  • Ethylene carbonate is a colorless crystalline compound that melts at 39 ° C and boils at 238 ° C.
  • the ethylene carbonate which is readily soluble in water, alcohols and organic solvents, can be produced from ethylene oxide and liquid CO 2 using large-scale syntheses.
  • Propylene carbonate is a water-bright, easily movable liquid with a density of 1.2057 "3 , the melting point is -49 ° C, the boiling point is 242 ° C.
  • Propylene carbonate is also commercially available at 200 ° C due to the reaction of propylene oxide and CO 2 and 80 bar.
  • Glycerol carbonate is accessible by transesterification of ethylene carbonate or dimethyl carbonate with glycerol, with by-products of ethylene glycol or methanol.
  • Another synthetic route starts from glycidol (2,3-epoxy-1-propanol), which is under pressure is reacted in the presence of catalysts with CO 2 to glycerol.
  • glycerol is a clear, mobile liquid with a density of 1.398 like "3, boiling at 125-130 ° C (0.15 mbar).
  • glycerol carbonate for example in amounts of from 1.0 to 17.5% by weight, preferably from 2.0 to 12.5% by weight and in particular from 3.0 to 7, 5 wt .-%, each based on the detergent and cleaning agent, is used.
  • 1,3-dioxolane-2-one extends to detergents and cleaning agents containing surfactants.
  • the applicant assumes that the property of the cyclic carbonic acid esters to decompose in an alkaline medium into the diol (or polyol) and carbon dioxide in question has a positive effect on the dissolution and dissolution rate of surfactants.
  • Anionic and nonionic as well as cationic and amphoteric surfactants are usually used as surfactants in washing and cleaning agents.
  • Important non-surfactant components are, in particular, builders (bleaching agents), bleaching agents, bleach activators, bleaching catalysts, enzymes, pH regulators, fragrances, perfume carriers, fluorescent agents, dyes, foam inhibitors, silicone oils, anti-redeposition agents, optical brighteners, graying inhibitors. Color transfer inhibitors and corrosion inhibitors.
  • the 1,3-dioxolan-2-ones can be used in all detergents and cleaning agents containing surfactants, regardless of their physical state or their further composition.
  • Both liquid detergents such as hand dishwashing detergents, glass cleaners, floor detergents and industrial cleaners and liquid detergents for washing textiles can thus benefit from the teaching according to the invention. It does not matter whether these agents have been formulated on a water basis or are to be manufactured as anhydrous agents, for example non-aqueous liquid detergents.
  • Solid agents can be in powder or granule form or further compressed, for example extruded or tableted.
  • the use according to the invention is particularly advantageous in the case of the highly concentrated and more highly compressed products with high bulk densities.
  • solid washing and cleaning agents are hand washing agents, conventional washing powders for use in household washing machines, so-called compact washing agents, machine dishwashing detergents, scouring and cleaning powders or conventional washing and cleaning agents in the form of compact washing and cleaning agent bodies or tablets.
  • the 1,3-dioxolan-2-ones have a disintegration-promoting effect on the molded article itself. In molded articles, they therefore not only act as solubility improvers and accelerators for the surfactants, but also as disintegration aids for the molded article itself.
  • Another object of the invention is a process for the preparation of detergent-containing detergents and cleaning agents which improve solubility, in which 1,3-dioxolan-2-one is used in amounts of 0.5 to 20% by weight, preferably 1.5 to 15% % By weight and in particular from 2.5 to 10% by weight. each based on the detergent and cleaning agent, inko ⁇ oriert in the agent. by introducing the 1,3-dioxolan-2-one (s) into the compositions via a mixture with at least one surfactant.
  • detergents and cleaning agents which are improved and accelerated to dissolve.
  • solubility-improving detergents and cleaning agents are a further subject of the present invention and contain surfactant (s), builders and optionally further ingredients, and they additionally contain 1,3-dioxolan-2-one in amounts of 0.5 to 20% by weight. , preferably from 1.5 to 15% by weight, particularly preferably from 2.5 to 12.5% by weight and in particular from 5 to 10% by weight, in each case based on the detergent and cleaning agent.
  • washing and cleaning agents if they contain nonionic surfactant (s).
  • nonionic surfactant s
  • preferred washing and cleaning agents additionally contain one or more builders.
  • Agents are preferred here which contain zeolite (s) and / or amorphous or crystalline silicate (s) in amounts of 5 to 50% by weight, preferably 10 to 45% by weight and in particular 15 to 40% by weight. -%, each based on the detergent and cleaning agent.
  • Suitable crystalline, layered sodium silicates have the general formula NaMSi 0 2x + 1 H 2 O, where M is sodium or hydrogen, x is a number from 1.9 to 4 and y is a number from 0 to 20 and preferred values for x 2, 3 or 4.
  • M sodium or hydrogen
  • x is a number from 1.9 to 4
  • y is a number from 0 to 20 and preferred values for x 2, 3 or 4.
  • Such crystalline layered silicates are described, for example, in European patent application EP-A-0 164 514.
  • Preferred crystalline layered silicates of the formula given are those in which M represents sodium and x assumes the values 2 or 3.
  • both ⁇ - and ⁇ -sodium disilicate Na 2 Si 2 O 5 'yH 2 O are preferred, with ⁇ -sodium disilicate being able to be obtained, for example, by the method described in international patent application WO-A-91/08171.
  • Amorphous sodium silicates with a Na 2 O: SiO 2 modulus from 1: 2 to 1: 3.3, preferably from 1: 2 to 1: 2.8 and in particular from 1: 2 to 1: 2.6, which are delayed in dissolution, can also be used and have secondary washing properties.
  • the delay in dissolution compared to conventional amorphous sodium silicates can be caused in various ways, for example by surface treatment, compounding, compacting / compression or by overdrying.
  • the term “amo ⁇ h” is also understood to mean “roentgenamo ⁇ h”.
  • silicates in X-ray diffraction experiments do not provide sharp X-ray reflections, as are typical for crystalline substances, but at most one or more maxima of the scattered X-rays, which have a width of several degree units of the diffraction angle.
  • it can very well lead to particularly good builder properties if the silicate particles are used in electron diffraction experiments. provide nice or even sharp diffraction maxima. This is to be integrated in such a way that the products have microcrystalline areas of size 10 to a few hundred nm, values up to max. 50 nm and in particular up to max. 20 nm are preferred.
  • Such so-called X-ray silicates which also have a delay in dissolution compared to conventional water glasses, are described, for example, in German patent application DE-A-44 00 024. Particularly preferred are compressed / compacted amorphous silicates, compounded amorphous silicates and over-dried x-ray silicates.
  • the finely crystalline, synthetic and bound water-containing zeolite used is preferably zeolite A and / or P.
  • zeolite P zeolite MAP® (commercial product from Crosfield) is particularly preferred.
  • zeolite X and mixtures of A, X and / or P are also suitable.
  • Commercially available and can preferably be used in the context of the present invention for example a co-crystallizate of zeolite X and zeolite A (about 80% by weight of zeolite X) ), which is sold by CONDEA Augusta SpA under the brand name VEGOBOND AX ® and by the formula
  • the zeolite can be used both as a builder in a granular compound and can also be used for a kind of "powdering" of the entire mixture to be used, usually both ways of incohering the zeolite into the premix.
  • Suitable zeolites have an average particle size of less than 10 ⁇ m (volume distribution; measurement method: Coulter Counter) and preferably contain 18 to 22% by weight, in particular 20 to 22% by weight, of bound water.
  • phosphates As builder substances, it is also possible to use the generally known phosphates as builder substances, provided that such use is not avoided for ecological reasons. should be avoided.
  • the sodium salts of orthophosphates, pyrophosphates and in particular tripolyphosphates are particularly suitable.
  • Usable organic builders that can also be used in the washing and cleaning agents according to the invention are, for example, the polycarboxylic acids which can be used in the form of their sodium salts, such as citric acid, adipic acid, succinic acid, glutaric acid, tartaric acid, sugar acids, aminocarboxylic acids, nitrilotriacetic acid (NTA), provided that such use is not objectionable for ecological reasons, as well as mixtures of these.
  • Preferred salts are the salts of polycarboxylic acids such as citric acid, adipic acid, succinic acid, glutaric acid, tartaric acid, sugar acids and mixtures of these.
  • bleaching agents Another group of ingredients that can be used with advantage in detergents and cleaning agents according to the invention are the bleaching agents.
  • the bleaching agents include sodium perborate tetrahydrate and sodium perborate monohydrate are of particular importance.
  • Further bleaching agents that can be used are, for example, sodium percarbonate, peroxypyrophosphates, citrate perhydrates and H 2 O 2 -supplying peracidic salts or peracids, such as perbenzoates, peroxophthalates, diperazelaic acid, phthaloiminoperic acid or diperdodecanedioic acid. If cleaning agents according to the invention for machine dishwashing are produced, bleaching agents from the group of organic bleaching agents can also be used.
  • Typical organic bleaching agents are the diacyl peroxides, such as dibenzoyl peroxide.
  • Other typical organic bleaching agents are peroxy acids, examples of which include alkyl peroxy acids and aryl peroxy acids.
  • Preferred representatives are (a) peroxybenzoic acid and its ring-substituted derivatives, such as alkyl, but also peroxy- ⁇ -naphthoic acid and magnesium monope ⁇ hthalat, (b) the aliphatic or substituted aliphatic peroxy acids, such as peroxylauric acid, peroxystearic acid, ⁇ -phthalimidoperoxycaproic acid [Phthaloimi- noperoxyhexanklakla (PAP)], o-carboxybenzamidoperoxycaproic acid, N-nonenylamidoperadipic acid and N-nonenylamidopersuccinate, and (c) aliphatic and araliphatic peroxydicarboxylic acids, such as 1,12
  • Diperoxyazelaic acid, diperocysebacic acid, diperoxybrassylic acid, the diperoxyphthalic acids, 2-decyldiperoxybutane-l, 4-diacid, N, N-terephthaloyl-di (6-aminopercaproic acid) can be used.
  • Chlorine or bromine-releasing substances can also be used as bleaching agents in machine dishwashing agents according to the invention.
  • Suitable chlorine or bromine-releasing materials include, for example, heterocyclic N-bromo- and N-chloramides, for example trichloroisocyanuric acid, tribromoisocyanuric acid, dibromoisocyanuric acid and / or dichloroisocyanuric acid (DICA) and / or their salts with cations such as potassium and sodium.
  • DICA dichloroisocyanuric acid
  • Hydantoin compounds such as 1,3-dichloro-5,5-dimethylhydanthoin are also suitable.
  • detergents and cleaning agents are particularly preferred which contain one or more bleaching agents from the group sodium perborate monohydrate, sodium perborate tetrahydrate or sodium percarbonate.
  • bleach activators can be incorporated into the agents according to the invention.
  • Bleach activators which can be used are compounds which, under perhydrolysis conditions, aliphatic peroxocarboxylic acids preferably having 1 to 10 carbon atoms. in particular give 2 to 4 carbon atoms, and / or optionally substituted perbenzoic acid.
  • Suitable substances are those which carry O- and / or N-acyl groups of the number of carbon atoms mentioned and / or optionally substituted benzoyl groups.
  • TAED tetraacet
  • bleach catalysts can also be incorporated into the moldings.
  • These substances are bleach-enhancing transition metal salts or transition metal complexes such as, for example, Mn, Fe, Co, Ru or Mo salt complexes or carbonyl complexes.
  • Mn-, Fe-. Co, Ru, Mo, Ti, V and Cu complexes with N-containing tripod ligands as well as Co, Fe, Cu and Ru amine complexes can be used as bleaching catalysts.
  • the examples show that the dissolution time of the nonionic surfactant can be reduced by almost 90% or 30% by adding glycerol carbonate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Selon l'invention, la solubilité de produits de lavage et de nettoyage contenant des tensioactifs est améliorée si l'on utilise, dans ces produits, comme agent améliorant la solubilité, de la dioxolan-2-one non substituée ou substituée à la position 4 ou aux positions 4 et 5. L'invention concerne en outre un procédé de production de produits de lavage et de nettoyage à solubilité améliorée, ainsi que de tels produits de lavage et de nettoyage à solubilité améliorée.
PCT/EP1999/003869 1998-06-12 1999-06-04 Utilisation de 1,3-dioxolan-2-ones dans des produits de lavage et de nettoyage Ceased WO1999066016A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1998126327 DE19826327A1 (de) 1998-06-12 1998-06-12 Verwendung von 1,3-Dioxolan-2-onen in Wasch- und Reinigungsmitteln
DE19826327.9 1998-06-12

Publications (1)

Publication Number Publication Date
WO1999066016A1 true WO1999066016A1 (fr) 1999-12-23

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PCT/EP1999/003869 Ceased WO1999066016A1 (fr) 1998-06-12 1999-06-04 Utilisation de 1,3-dioxolan-2-ones dans des produits de lavage et de nettoyage

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DE (1) DE19826327A1 (fr)
WO (1) WO1999066016A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004031167A1 (fr) 2002-10-01 2004-04-15 Basf Aktiengesellschaft Carbonates d'alkylglycidol en tant que co-tensioactifs
CN105754737A (zh) * 2014-12-19 2016-07-13 北京绿伞化学股份有限公司 一种用于水溶性膜包装的浓缩洗衣液及其制备方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2896510B1 (fr) * 2006-01-24 2008-03-21 Alain Michel Delaite Nettoyant tapis, tissus, moquettes
DE102007016391A1 (de) * 2007-04-03 2008-10-09 Henkel Ag & Co. Kgaa Farbschützendes Wasch- oder Reinigungsmittel
DE102007023875A1 (de) * 2007-05-21 2008-11-27 Henkel Ag & Co. Kgaa Reinigungsmittel
DE102007016382A1 (de) * 2007-04-03 2008-10-09 Henkel Ag & Co. Kgaa Vergrauungsinhibierendes Waschmittel
DE102007016383A1 (de) * 2007-04-03 2008-10-09 Henkel Ag & Co. Kgaa Fixierung von Duftstoffen aus Wasch- und Reinigungsmitteln an harten und weichen Oberflächen
EP2380958A1 (fr) * 2010-04-19 2011-10-26 The Procter & Gamble Company Composition détergente solide comprenant du carbonate de glycérol

Citations (2)

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Publication number Priority date Publication date Assignee Title
US4594111A (en) * 1984-10-04 1986-06-10 Coonan Edmund C Liquid phase cleaner-solvent
US5098594A (en) * 1988-05-20 1992-03-24 The Boeing Company Carbonate/diester based solvent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4594111A (en) * 1984-10-04 1986-06-10 Coonan Edmund C Liquid phase cleaner-solvent
US5098594A (en) * 1988-05-20 1992-03-24 The Boeing Company Carbonate/diester based solvent

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Title
DATABASE WPI Derwent World Patents Index; XP002900653 *
DATABASE WPI Derwent World Patents Index; XP002900654 *
DATABASE WPI Derwent World Patents Index; XP002900655 *
DATABASE WPI Derwent World Patents Index; XP002900656 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004031167A1 (fr) 2002-10-01 2004-04-15 Basf Aktiengesellschaft Carbonates d'alkylglycidol en tant que co-tensioactifs
EP1549631B1 (fr) * 2002-10-01 2014-01-08 Basf Se Carbonates d'alkylglycidol en tant qu'agents co-tensioactifs
CN105754737A (zh) * 2014-12-19 2016-07-13 北京绿伞化学股份有限公司 一种用于水溶性膜包装的浓缩洗衣液及其制备方法
CN105754737B (zh) * 2014-12-19 2019-03-01 北京绿伞化学股份有限公司 一种用于水溶性膜包装的浓缩洗衣液及其制备方法

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Publication number Publication date
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