EP0017052A1 - Use of stabilizers against decoloration in alkaline cleaning formulations containing non-ionic tensides - Google Patents

Use of stabilizers against decoloration in alkaline cleaning formulations containing non-ionic tensides Download PDF

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Publication number
EP0017052A1
EP0017052A1 EP80101343A EP80101343A EP0017052A1 EP 0017052 A1 EP0017052 A1 EP 0017052A1 EP 80101343 A EP80101343 A EP 80101343A EP 80101343 A EP80101343 A EP 80101343A EP 0017052 A1 EP0017052 A1 EP 0017052A1
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color
surfactants
alkaline cleaning
formulations containing
containing non
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EP80101343A
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German (de)
French (fr)
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EP0017052B1 (en
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Knut Dr. Oppenlaender
Rainer Dr. Strickler
Johannes Dr. Perner
Wolfgang Dr. Trieselt
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BASF SE
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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
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • 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

Definitions

  • the invention relates to nonionic surfactants based on polyalkylene oxides or alkoxylation products of hydrophobic compounds containing -OH or -NH groups, not by closing the end hydroxyl groups, but by a low content of heterocyclic compounds which, as a common structural feature, have a -CO Contain -0- or -CO-NH grouping, are stabilized against discoloration by decomposition, and such color-stabilized nonionic surfactant-containing alkaline cleaner formulations.
  • the surfactants used are often those which, despite their good cleaning action, produce little foam or even have a foam-suppressing effect, but special problems can also require highly foaming surfactants.
  • the invention was therefore based on the object of searching for nonionic low-foam surfactants which, with otherwise unchanged application behavior, are stable against the action of strong alkalis and oxidizing agents.
  • cyclic esters and amides such as lactones, lactams and cyclic carbonic acid esters with polyhydric alcohols, such as glycol, 1,2-propylene glycol or glycerol, all of which obey the formula defined in the claim.
  • the color stabilizers are dissolved in the liquid, nonionic surfactant by stirring, advantageously in the heat.
  • 0.1 to 5% by weight of stabilizer is added, based on the surfactant. Less than 0.1% by weight caused a decrease in stability and more than 5% by weight means no additional advantages. Preferably 0.5 to 3% by weight is chosen.
  • nonionic surfactant is not liquid at room temperature, it is melted and proceeded as described. After the color stabilizer has dissolved in it, let it solidify again.
  • the color-stabilized surfactants and cleaning agents according to the invention can therefore be in liquid or solid form.
  • the color-stabilized surfactants are mixed with the other components, in particular the alkaline builders mentioned at the outset and, if appropriate, other additives such as oxidizing agents, fragrances and colorants and disinfectants to prepare the cleaning formulations.
  • other additives such as oxidizing agents, fragrances and colorants and disinfectants to prepare the cleaning formulations.
  • the color stabilizers have been shown to be effective with almost all ethylene oxide and ethylene oxide / propylene oxide surfactants, i.e. no time-consuming tests are required to select special surfactants, for example.
  • Detergent formulations which contain the color-stabilized surfactants according to the invention are generally composed of 70 to 99, preferably 90 to 99% by weight of inorganic alkaline builder and 30 to 1, preferably 10 to 1% by weight, in each case on the entire formulation related, together to surfactant.
  • the alkylene oxide adducts were tested in such a way that they were stored at different temperatures for 24 days with and without addition of stabilizer.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

Farbstabilisierte nichtionische Tenside, die Polyalkylenoxidgruppen mit endständigen Hydroxylgruppen gebunden enthalten, gekennzeichnet durch einen Gehalt an 0,1 bis 5 Gew.%, bezogen auf das Tensid - an mindestens einer Verbindung der Formel <IMAGE> in der X für O, CH2, C2H4 oder C3H6, Y für O oder NH und Z für H, CH3 oder CH2OH stehen, als Farbstabilisator. Vertreter dieser Verbindungsgruppe sind z.B. Äthylencarbonat, Propylencarbonat, Glycerincarbonat, γ-Butyrolacton, ε-Valerolacton, δ-Caprolacton oder Pyrrolidon. Auch Gemische sind wirksam. Besonders wirksam sind sie in stark alkalischen Reinigerformulierungen.Color-stabilized nonionic surfactants containing polyalkylene oxide groups bonded with terminal hydroxyl groups, characterized by a content of 0.1 to 5% by weight, based on the surfactant, of at least one compound of the formula <IMAGE> in the X for O, CH2, C2H4 or C3H6, Y represent O or NH and Z represent H, CH3 or CH2OH, as a color stabilizer. Representatives of this connection group are e.g. Ethylene carbonate, propylene carbonate, glycerol carbonate, γ-butyrolactone, ε-valerolactone, δ-caprolactone or pyrrolidone. Mixtures are also effective. They are particularly effective in strongly alkaline cleaner formulations.

Description

Die Erfindung betrifft nichtionische Tenside auf der Basis von Polyalkylenoxiden oder von Alkoxylierungsprodukten hydrophober, -OH- oder -NH-Gruppen enthaltender Verbindungen, die nicht durch Verschluß der End-Hydroxylgruppen, sondern durch einen geringen Gehalt heterocyclischen Verbindungen, die als gemeinsames Strukturmerkmal eine -CO-0- oder -CO-NH-Gruppierung enthalten, gegen eine Verfärbung durch Zersetzung stabilisiert sind, und derartige farbstabilisierte nichtionische Tenside enthaltende alkalische Reinigerformulierungen.The invention relates to nonionic surfactants based on polyalkylene oxides or alkoxylation products of hydrophobic compounds containing -OH or -NH groups, not by closing the end hydroxyl groups, but by a low content of heterocyclic compounds which, as a common structural feature, have a -CO Contain -0- or -CO-NH grouping, are stabilized against discoloration by decomposition, and such color-stabilized nonionic surfactant-containing alkaline cleaner formulations.

Als Hauptbestandteile in Reinigerformulierungen für mechanisch intensive Reinigungsprozesse, z.B. bei der Plaschenwäsche oder bei Haushaltsgeschirrspülmaschinen, sind alkalisch reagierende Gerüstsubstanzen wie Phosphate, Silikate, Carbonate und zum anderen auch Ätzalkalien enthalten. Wesentlicher und notwendiger Bestandteil solcher Reinigerformulierungen sind neben eventuellen weiteren Zusätzen wie vor allem Oxidations- und Desinfektionsmitteln auch nichtionische Tenside der bekannten Tensidklassen, von denen als wichtigste zu nennen sind:

  • Alkylenoxidmisch- und Blockpolymerisate; alkoxylierte Äthylen- oder Propylenpolyamine oder Fettalkohole, wobei die Alkylenoxidkomponente entweder aus reinem Äthylenoxid oder reinem Propylenoxid oder beiden besteht, und wobei im letztgenannten Fall die Polyaddition mit dem Alkylenoxid--Gasgemisch oder nacheinander (in Blockform) durchgeführt werden kann.
The main constituents of cleaning formulations for mechanically intensive cleaning processes, e.g. for washing dishes or household dishwashers, contain alkaline-reacting framework substances such as phosphates, silicates, carbonates and, on the other hand, caustic alkalis. An essential and necessary component of such cleaner formulations are, in addition to any other additives such as, in particular, oxidizing and disinfecting agents, nonionic surfactants of the known classes of surfactants, the most important of which are:
  • Alkylene oxide copolymers and block polymers; alkoxylated ethylene or propylene polyamines or fatty alcohols, the alkylene oxide component consisting either of pure ethylene oxide or pure propylene oxide or both, and in the latter case the polyaddition can be carried out with the alkylene oxide gas mixture or in succession (in block form).

Als Tenside werden dabei häufig solche eingesetzt, die trotz guter reinigender Wirkung wenig Schaum entwickeln oder sogar schaumdämpfend wirken, jedoch können spezielle Probleme auch stark schäumende Tenside erforderlich machen.The surfactants used are often those which, despite their good cleaning action, produce little foam or even have a foam-suppressing effect, but special problems can also require highly foaming surfactants.

Mitunter kommt es in Abhängigkeit von der Zusammensetzung des Reinigers oder der auf den Reiniger einwirkenden Temperaturen zu Verfärbungen. Diese zumeist braunen Verfärbungen sind auf chemische Reaktion zwischen nichtionischem Tensid, Alkali und oxidierend wirkenden Substanzen wie Luftsauerstoff oder Chlorträgern im konfektionierten Reiniger selbst zurückzuführen. Die farblichen Veränderungen können zwar zum einen nur äußerlicher Natur sein, ohne eine Veränderung der anwendungstechnischen Eigenschaften zu bedingen. Bei Handelsprodukten, die vorzugsweise in den Haushalt gelangen, ist jedoch ein nicht ansprechendes Aussehen verkaufshindernd. Zum anderen kann die Wechselwirkung zwischen Tensid, Alkali und Oxidationsmittel auch soweit gehen, daß Veränderungen der anwendungstechnischen Eigenschaften festzustellen sind. Es hat sich gezeigt, daß die freien Hydroxylgruppen der nichtionischen Tenside der Angriffspunkt für Alkali und Oxidationsmittel sind. Aus diesem Grunde hat es nicht an Bestrebungen·gefehlt, die Hydroxylgruppe durch chemische Reaktion in alkalistabile Derivate zu überführen. Als wesentliche Beispiele sind die Verätherung mit z.B. Benzylchlorid oder die Acetalisierung zu erwähnen. Diese Operationen liefern dann auch nichtionische endgruppenverschlossene Tenside, die ausreichend stabil sind. Der Endgruppenverschluß bewirkt jedoch auch eine Veränderung der physikalisch-chemischen Eigenschaften. So werden z.B. Trübungspunkt und Löslichkeit in Wasser herabgesetzt. Aus ökonomischer Sicht ist zu erwähnen, daß die genannten chemischen Reaktionen, die zu endgruppenverschlossenen nichtionischen Tensiden führen, nicht einfach durchzuführen sind, und deshalb die Produkte nicht unerheblich verteuern. Es ist ferner zu erwähnen, daß durch den Endgruppenver- schluß die biologische Abbaubarkeit solcher Tenside ver- schlechtert wird. Dies kann sogar soweit gehen, daß gesetzlich vorgeschriebene Mindestabbauraten nicht mehr erfüllt werden.Depending on the composition of the cleaner or the temperatures acting on the cleaner, discolouration may occur. This mostly brown discoloration is due to the chemical reaction between non-ionic surfactant, alkali and oxidizing substances such as atmospheric oxygen or chlorine carriers in the ready-made cleaner itself. On the one hand, the color changes can only be of an external nature, without requiring a change in the application properties. In the case of commercial products, which preferably end up in the household, an unappealing appearance hinders sales. On the other hand, the interaction between surfactant, alkali and oxidizing agent can go so far that changes in the application properties can be determined. It has been shown that the free hydroxyl groups of the nonionic surfactants are the target for alkali and oxidizing agents. For this reason there has been no lack of efforts to convert the hydroxyl group into alkali-stable derivatives by chemical reaction. Etherification with, for example, benzyl chloride or acetalization should be mentioned as essential examples. These operations then also provide nonionic endgroup-sealed surfactants that are sufficiently stable. However, the end group closure also causes a change in the physico-chemical properties. For example, the cloud point and solubility in water are reduced. From an economic point of view it should be mentioned that the chemical reactions mentioned, which lead to end-capped nonionic surfactants, are not easy to carry out and therefore make the products more expensive. It should also be mentioned that the end group Finally, the biodegradability of such surfactants is deteriorated. This can even go so far that legally prescribed minimum degradation rates are no longer met.

Der Erfindung lag daher die Aufgabe zugrunde, nach nichtionischen schaumarmen Tensiden zu suchen, die bei sonst unverändertem anwendungstechnischem Verhalten gegen die Einwirkung von starken Alkalien und Oxidationsmitteln stabil sind.The invention was therefore based on the object of searching for nonionic low-foam surfactants which, with otherwise unchanged application behavior, are stable against the action of strong alkalis and oxidizing agents.

Es wurde nun gefunden, daß diese Aufgabe durch Zusätze von 0,1 bis 5, vorzugsweise 0,5 bis 3 Gew.%, bezogen auf nichtionische Tenside, an Verbindungen gelöst werden kann, wie sie gemäß dem Patentanspruch definiert wird.

Figure imgb0001
in der X für 0, CH2, C2H4 oder C3H6, Y für 0 oder NH und Z für H, CH3 oder CH30H stehen, als Farbstabilisator.It has now been found that this object can be achieved by adding 0.1 to 5, preferably 0.5 to 3,% by weight, based on nonionic surfactants, of compounds as defined in the patent claim.
Figure imgb0001
 in which X stands for 0, CH 2 , C 2 H 4 or C 3 H 6 , Y for 0 or NH and Z for H , CH3 or CH 3 0H, as a color stabilizer.

Beispiele für solche Verbindungen sind cyclische Ester und Amide, wie Lactone, Lactame und cyclische Kohlensäureester mit mehrwertigen Alkoholen, wie Glycol, 1,2-Propylenglycol oder Glycerin, die alle der im Patentanspruch definierten Formel gehorchen.Examples of such compounds are cyclic esters and amides, such as lactones, lactams and cyclic carbonic acid esters with polyhydric alcohols, such as glycol, 1,2-propylene glycol or glycerol, all of which obey the formula defined in the claim.

Einzelner Vertreter dieser Verbindungsgruppe, in der als gemeinsames Strukturmerkmal immer die -CO-O-(Ester)- oder -CO-NH-(Amid)-Struktur auftritt, sind beispielsweise Äthylencarbonat, Propylencarbonat, Glycerincarbonat, Äthylencarbamat, Propylencarbamat, γ-Butyrolacton, δ-Valerolacton, ε-Caprolactam oder Pyrrolidon. Erfindungsgemäß wirken auch Gemische dieser Verbindungen.Individual representatives of this connecting group, in which the -CO-O- (ester) - or -CO-NH- (amide) structure always occurs as a common structural feature, are, for example, ethylene carbonate, propylene carbonate, glycerol carbonate, ethylene carbamate, propylene carbamate, γ-butyrolactone, δ-valerolactone, ε-caprolactam or pyrrolidone. Mixtures of these compounds also act according to the invention.

Die Farbstabilisatoren werden in dem flüssigen, nichtionischen Tensid durch Rühren, zweckmäßigerweise in der Wärme, gelöst.The color stabilizers are dissolved in the liquid, nonionic surfactant by stirring, advantageously in the heat.

Man setzt erfindungsgemäß - bezogen auf das Tensid - 0,1 bis 5 Gew.% an Stabilisator zu. Weniger als 0,1 Gew.% bewirkten eine Abnahme der Stabilität und mehr als 5 Gew.% bedeuten keine zusätzlichen Vorteile. Vorzugsweise wählt man 0,5 bis 3 Gew.%.According to the invention, 0.1 to 5% by weight of stabilizer is added, based on the surfactant. Less than 0.1% by weight caused a decrease in stability and more than 5% by weight means no additional advantages. Preferably 0.5 to 3% by weight is chosen.

Sofern das nichtionische Tensid bei Raumtemperatur nicht flüssig ist, wird es aufgeschmolzen und wie geschildert verfahren. Nachdem sich der Farbstabilisator darin gelöst hat, läßt man es wieder erstarren. Die erfindungsgemäß farbstabilisierten Tenside und Reinigungsmittel können also in flüssiger oder fester Form vorliegen.If the nonionic surfactant is not liquid at room temperature, it is melted and proceeded as described. After the color stabilizer has dissolved in it, let it solidify again. The color-stabilized surfactants and cleaning agents according to the invention can therefore be in liquid or solid form.

Die farbstabilisierten Tenside werden genau wie bisher die nicht farbstabilisierten zur Herstellung der Reinigerformulierungen mit deren übrigen Komponenten, insbesondere den eingangs genannten alkalischen Gerüstsubstanzen und gegebenenfalls weiteren Zusätzen wie Oxidationsmitteln, Duft- und Farbstoffen und Desinfektionsmitteln abgemischt. Für diese Mischungen besteht - im Gegensatz zu den nicht farbstabilisierten Mischungen - praktisch keine Gefahr einer augenfälligen Verfärbung beim Lagern, auch nicht in der Wärme. Es hat sich gezeigt, daß die Farbstabilisatoren bei fast allen Äthylenoxid und nthylenoxid/Propylenoxid--Tensiden wirksam sind, d.h. es sind keine zeitraubenden Versuche notwendig, etwa spezielle Tenside auszuwählen.As before, the color-stabilized surfactants are mixed with the other components, in particular the alkaline builders mentioned at the outset and, if appropriate, other additives such as oxidizing agents, fragrances and colorants and disinfectants to prepare the cleaning formulations. In contrast to the non-color-stabilized mixtures, there is practically no risk of any discolouration during storage, even in the heat. The color stabilizers have been shown to be effective with almost all ethylene oxide and ethylene oxide / propylene oxide surfactants, i.e. no time-consuming tests are required to select special surfactants, for example.

Reinigerformulierungen, welche die erfindungsgemäß farb- stabilisierten Tenside enthalten., setzen sich im allgemeinen aus 70 bis 99, vorzugsweise 90 bis 99 Gew.% an anorganischer alkalischer Gerüstsubstanz und 30 bis 1, vorzugsweise 10 bis 1 Gew.%, jeweils auf die gesamte Formulierung bezogen, an Tensid zusammen.Detergent formulations which contain the color-stabilized surfactants according to the invention are generally composed of 70 to 99, preferably 90 to 99% by weight of inorganic alkaline builder and 30 to 1, preferably 10 to 1% by weight, in each case on the entire formulation related, together to surfactant.

Die nun folgenden Beispiele erläutern die Erfindung. Angegebene Prozent sind Gewichtsprozente.The following examples illustrate the invention. The percentages given are percentages by weight.

BeispieleExamples

Die Alkylenoxid-Addukte wurden in der Weise geprüft, daß sie 24 Tage mit und ohne Stabilisatorzusatz bei verschiedenen Temperaturen gelagert wurden.The alkylene oxide adducts were tested in such a way that they were stored at different temperatures for 24 days with and without addition of stabilizer.

Die Proben bei Raumtemperatur (RT) wurden ohne NaOH-Zusatz gelagert; bei 50 und 70°C gelagerte Proben enthielten festes Ätznatron. Nach dieser Zeit wurden Jodfarbzahl und Farbe des Ätznatrons bestimmt.The samples at room temperature (RT) were stored without the addition of NaOH; Samples stored at 50 and 70 ° C contained solid caustic soda. After this time, the iodine color number and the color of the caustic soda were determined.

In der folgenden Tabelle sind in den ersten 3 senkrechten Spalten die Jodfarbzahlen, in den letzten beiden Benotungen angegeben, die aufgrund der visuellen Betrachtung des festen Ätznatrons vorgenommen wurde.In the following table the iodine color numbers are given in the first 3 vertical columns, in the last two grades, which was made on the basis of the visual inspection of the solid caustic soda.

Es wurden Noten von a (sehr gut, kein brauner Belag) bis e (sehr schlecht, dicker brauner Belag) vergeben. Die Tabelle zeigt deutlich die wesentlich verbesserte Farbstabilität der Tenside mit den erfindungsgemäßen Zusätzen gegenüber den nichtstabilisierten. In der Tabelle bedeuten "EO" Äthylenoxid und "PO" Propylenoxid.

Figure imgb0002
Figure imgb0003
 Grades from a (very good, no brown coating) to e (very poor, thick brown coating) were awarded. The table clearly shows the significantly improved color stability of the surfactants with the additives according to the invention compared to the unstabilized ones. In the table, "EO" means ethylene oxide and "PO" propylene oxide.
Figure imgb0002
Figure imgb0003

Claims (2)

1. Farbstabilisierte nichtionische Tenside, die Polyalkylenoxidgruppen mit endständigen Hydroxylgruppen gebunden enthalten, gekennzeichnet durch einen Gehalt an 0,1 bis 5 Gew.%, bezogen auf das Tensid - an mindestens einer Verbindung der Formel
Figure imgb0004
in der X für 0, CH2, C2H4 oder C3H6, Y für 0 oder NH und Z für H, CH3 oder CH3OH stehen, als Farbstabilisator. 1st Color-stabilized nonionic surfactants containing polyalkylene oxide groups bonded with terminal hydroxyl groups, characterized by a content of 0.1 to 5% by weight, based on the surfactant, of at least one compound of the formula
Figure imgb0004
 in which X is 0 , CH 2 , C 2 H 4 or C 3 H 6 , Y is 0 or NH and Z is H, CH 3 or CH 3 OH, as a color stabilizer. 2. Verwendung von farbstabilisierten Tensiden gemäß Anspruch 1 als Wirksubstanz in stark alkalischen Reinigungsmitteln.2. Use of color-stabilized surfactants according to claim 1 as active substance in strongly alkaline cleaning agents.
EP80101343A 1979-03-16 1980-03-14 Use of stabilizers against decoloration in alkaline cleaning formulations containing non-ionic tensides Expired EP0017052B1 (en)

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DE19792910402 DE2910402A1 (en) 1979-03-16 1979-03-16 COLOR-STABILIZED, NON-ionic surfactants and alkaline detergent formulations that contain these surfactants
DE2910402 1979-03-16

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GB8803114D0 (en) * 1988-02-11 1988-03-09 Bp Chem Int Ltd Bleach activators in detergent compositions
GB8803113D0 (en) * 1988-02-11 1988-03-09 Bp Chem Int Ltd Anhydrides in detergent compositions
EP3107989A1 (en) * 2014-02-19 2016-12-28 The Procter & Gamble Company Composition comprising benefit agent and aprotic solvent
US9556406B2 (en) * 2014-02-19 2017-01-31 Milliken & Company Compositions comprising benefit agent and aprotic solvent

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GB1483186A (en) * 1973-09-21 1977-08-17 Ici Ltd Aqueous wetting compositions

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Publication number Priority date Publication date Assignee Title
EP2380958A1 (en) * 2010-04-19 2011-10-26 The Procter & Gamble Company Solid detergent composition comprising glycerol carbonate

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DE2910402A1 (en) 1980-09-25
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EP0017052B1 (en) 1982-05-26

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