EP0231886B1 - Utilisation d'amines grasses éthoxylées comme solubiliseurs - Google Patents

Utilisation d'amines grasses éthoxylées comme solubiliseurs Download PDF

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Publication number
EP0231886B1
EP0231886B1 EP87101229A EP87101229A EP0231886B1 EP 0231886 B1 EP0231886 B1 EP 0231886B1 EP 87101229 A EP87101229 A EP 87101229A EP 87101229 A EP87101229 A EP 87101229A EP 0231886 B1 EP0231886 B1 EP 0231886B1
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EP
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Prior art keywords
mol
cleaning
fatty amines
ethoxylated fatty
cleaner
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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
EP87101229A
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German (de)
English (en)
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EP0231886B2 (fr
EP0231886A3 (en
EP0231886A2 (fr
Inventor
Thomas Wershofen
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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
Priority to AT87101229T priority Critical patent/ATE68518T1/de
Publication of EP0231886A2 publication Critical patent/EP0231886A2/fr
Publication of EP0231886A3 publication Critical patent/EP0231886A3/de
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines

Definitions

  • the invention relates to the use of ethoxylated fatty amines as solubilizers or solubilizers in active ingredient or cleaner concentrates for cleaning agent solutions, in particular in cleaner concentrates for automatic bottle cleaning.
  • solubilizers or solubilizers In general, substances that are sparingly soluble or insoluble in water can be brought into solution by adding so-called solubilizers or solubilizers to the aqueous solutions.
  • the solution-mediating effect of such additives is based in many cases on the fact that the molecules of the substance added as a solubilizer have a surfactant-like structure, that is to say they have a hydrophilic and a hydrophobic part of the molecule.
  • the solubilizer molecules form micelles in which the hydrophilic ends of the molecules are directed outwards towards the water and the hydrophobic ends of the molecules are directed towards the inside of the micelles.
  • Substances that are insoluble in the aqueous phase are incorporated into the interior of the micelles during solubilization and thus appear to be dissolved in the aqueous phase.
  • the amount of solubilizer required to obtain a clear solution depends not only on the amount of substance to be dissolved, but also on the solubilizing ability of the solubilizer.
  • any dirt that is stuck inside the bottle is removed to enable the bottle to be refilled hygienically.
  • the shelf life of the bottled beverage depends, among other things, on the completeness of the removal of mechanical, biological or microbiological contamination.
  • bottles are usually re-labeled when refilled. It is therefore necessary to completely remove not only external soiling but also labels and glue residues, thus creating the prerequisites for labeling (now mandatory under food law).
  • alkaline cleaning agent solutions with a large number of components which, in addition to larger amounts of alkali metal hydroxides, for example 1 to 2%, in particular sodium hydroxide, also contain other components, their quality and quantity is tailored to the specific cleaning problem.
  • the cleaning agent solutions are produced in the corresponding cleaning systems by adding a cleaning concentrate, which contains all the necessary additives for problem-free cleaning, to the process water and then adding sodium hydroxide.
  • detergent concentrates In addition to readily water-soluble additives, such as inorganic salts and inorganic and organic acids, most detergent concentrates also contain poorly water-soluble components that separate from the liquid detergent concentrates over long periods of storage under unfavorable storage conditions, thereby preventing the detergent from being fully effective in the application solutions.
  • Such components are, in particular, the wetting agents and anti-foaming agents contained in the cleaner concentrates, the absence of which in the cleaning solution leads to improper functioning of the cleaning system and thus to unacceptable failures. Such failures are e.g. caused by a foaming of the system or by unreleased labels.
  • cleaner concentrates containing sodium cumene sulfonate become significantly more expensive due to the high price of the solubilizer for large amounts of use, - in some cases, cleaner concentrates contain up to 25% of this substance - so that, for economic reasons alone, there is a need for a cheaper compound which acts as a solubilizer.
  • sodium cumene sulfonate as a detergent component has no further favorable effects on the cleaning ability of the cleaning or application solutions. Its only function is therefore to keep other poorly soluble components contained in the cleaner concentrate stably dissolved in the aqueous solution.
  • solubilizers Lower, mostly branched alcohols, for example isopropanol, are also known from the prior art as solubilizers.
  • solubilizers are also known from the prior art as solubilizers.
  • the disadvantage of this is that its handling requires special protective measures, since isopropanol is not only easily flammable, but also has a low flash point.
  • solubilizer is significantly worse than that of sodium cumene sulfonate.
  • solubilizers or solubilizers which stably bring even poorly soluble components of the cleaner concentrate into solution and thus ensure unlimited storage stability of cleaner concentrates which comprise components which contain highly hydrophobic groups. Because the stability of such solutions even at higher Temperature, as it sometimes occurs in storage rooms, was necessary to stabilize the cleaner concentrate both for temperatures below freezing and for temperatures up to 50 C for an unlimited time.
  • the solubilizers provided should be inexpensively accessible and, in addition to having a stabilizing effect on the cleaner concentrates, should also take on other tasks in the cleaning process.
  • the primary aim was to accelerate the detachment of bottle labels, faster and better removal of contaminating residues, and also better emulsification of the detached dirt residues in the cleaning solution after use.
  • ethoxylated fatty amines of the general formula (I) can be used, in which R 1 is a straight-chain or branched alkyl radical having 8 to 24 C atoms and R 2 is a group stands.
  • Ethoxylated fatty amines of the type mentioned with saturated alkyl radicals R 1 are just as suitable as those with unsaturated alkyl radicals R 1.
  • the preferred range of chain length for the alkyl radical R 1 is 12 to 18 carbon atoms.
  • Fatty amines of this type can be produced from native sources by methods known per se. They can be used either individually or in the naturally occurring mixtures with alkyl radicals of different chain lengths for the ethoxylation and can be used according to the invention as ethoxylated products.
  • the ethoxylation reaction is also known as such and is carried out on the fatty amines, which are preferably obtainable from native sources, in a manner known per se. In practice, this also produces mixtures with a different number (n + m) of ethoxy radicals. According to the invention, preference is given to compounds in which the average degree of ethoxylation (n + m) is in the range from 2 to 15. Ethoxylated fatty amines with an average degree of ethoxylation (n + m) in the range from 10 to 15 are particularly preferred.
  • active substance concentrates for cleaners can also use ethoxylated diamines of the general formula (I) in which R 2 is for a group where R 3 is an alkylene radical having 2 to 6 carbon atoms and x or y are each an integer from 0 to 30.
  • R 2 is for a group where R 3 is an alkylene radical having 2 to 6 carbon atoms and x or y are each an integer from 0 to 30.
  • Alkylene radical here means alkyl radicals which each have free valences at the terminal C atoms (also called “polymethylene radicals”).
  • Such diamines preferably have a degree of ethoxylation in the range from 2 to 15, particularly preferably in the range from 10 to 15, in which case the total number of ethoxy groups is meant. This means that in the general formula (I) the sum (n + x + y) is in the range from 2 to 15 or preferably from 10 to 15.
  • preferred fatty amines are accessible from natural sources, for example from natural fats and oils, and can be used for the ethoxylation either directly from the native sources or after chemical processing, for example hydrogenation of unsaturated side chains.
  • natural sources for example from natural fats and oils
  • preferred fatty amines are accessible from natural sources, for example from natural fats and oils, and can be used for the ethoxylation either directly from the native sources or after chemical processing, for example hydrogenation of unsaturated side chains.
  • coconut amine tallow fatty amine, oleyl amine, octadecyl amine, tallow fatty oleyl amine, stearyl amine and, as diamine, tallow fat propylene diamine.
  • the average degree of ethoxylation is preferably in the range between 2 and 15.
  • the amount of the ethoxylated fatty amines of the general formula (I) used according to the invention is in the range from 1 to 15% by weight of one or more fatty amines, based on the total weight of the cleaner concentrate, with several fatty amines together not exceeding the concentration value of 15%.
  • the solubilizing effect of the ethoxylated fatty amines mentioned is noticeable in that the cleaner concentrates containing a large number of cleaner components are stable for an unlimited time at high (50 ° C.) and low (-18 ° C.) temperatures.
  • the ethoxylated fatty amines are used as solubilizers according to the invention, a clear product is obtained after freezing the cleaner concentrates and thawing them, in which the organic components such as wetting agents and anti-foaming agents also remain clearly dissolved.
  • the cleaner concentrates which also contain further cleaner components are prepared by methods known per se, the individual components being mixed together in any order.
  • the aqueous solution of the ethoxylated fatty amine of the general formula (I), which is effective as a solubilizer, is advantageously introduced, and the further cleaner components are then added.
  • the pH of the cleaner concentrates is reduced to one Range from 1 to 7 set.
  • the aqueous cleaner compositions prepared as concentrates are added to the process water of the bottle cleaning machine in concentrations which depend on the degree of soiling of the bottles to be cleaned and the water hardness and, if appropriate, other parameters.
  • the cleaning agent concentration in the process solutions is in the range of 0.1 to 0.5% by weight.
  • concentrations are also conceivable, in particular if the hardness of the process water or the high degree of contamination of the bottles make a higher concentration of one of the detergent components necessary.
  • concentrations are also conceivable which are below 0.1% by weight or above 0.5% by weight, based on the application solution.
  • Alkali metal hydroxides preferably sodium hydroxide
  • Alkali metal hydroxides are then generally metered in separately to the process or cleaning solutions.
  • the sodium hydroxide concentrations in the process solutions are usually in the range of 1 to 3%.
  • Cleaner concentrates of the composition given in Examples 1 to 4 and in the comparative examples were prepared by methods known per se. In each case, the water and the ethoxylated fatty amine, or the corresponding comparative compound, acting as solubilizer, were introduced and the remaining detergent components were added successively.
  • the labels may be used during the test period, i.e. until completely detached from the bottle surface, do not fray and after removal from the cleaning solution no signs of being drawn up, i.e. have adsorbed surfactants.
  • Example 1 In addition, laboratory tests were carried out on bottles, the aluminum foils on the bottle neck below the opening. The peeling times are given in Example 1, Table 2.
  • the foaming behavior was assessed in accordance with DIN draft 53902.
  • the cleaning liquors containing a fatty amine ethoxylate were examined in the Götte foam whipping apparatus (DIN 53902, Part 1).
  • Increasing amounts of a test foam (P3 R optenite) were added to the bases and the foam amounts were measured after 5 times 100 beats. The values determined here are shown in Table 4 in Example 6.
  • Label detachment tests were carried out on different beverage bottles, all of which were provided with ChromaluxR labels.
  • cleaning solutions were applied to the various bottles, which had a NaOH content of 1.5% by weight and a cleaning agent concentrate content of 0.2% by weight.
  • a cleaning solution was prepared from this in accordance with the procedure described in Example 1, in which the amount of active compound was 0.2% and which additionally contained 1.5% by weight of NaOH.
  • the peel-off times in the label peel test are shown in Table 1 above.
  • Example 1 The cleaning concentrates given in Example 1 and in Comparative Examples 1 and 2 were used to prepare cleaning solutions (0.2% cleaning concentrate and 1.5% sodium hydroxide) and the duration of the dissolution of aluminum bottle neck foils was determined (test conditions: water 0 ° d, temperature 75 ° C).
  • the cleaner concentrates were clear immediately after their production and showed no separation of individual components.
  • the solutions remained clear even after prolonged storage (3 months to 1 year) at 5 ° C and at 50 C and did not change optically after they had been frozen and thawed.

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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)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Mise en oeuvre d'une ou de plusieurs amines grasses éthoxylées de la formule générale (I)
Figure imgb0016
dans laquelle
n représente un nombre entier de 2 à 30,
R1 correspond à un radical alkyle saturé ou insaturé, à chaîne droite ou ramifiée, comportant 8 à 24 atomes de C, et
R2 est un groupement
Figure imgb0017
ou un groupement
Figure imgb0018
dans lequel
R3 représente un radical alkylène comportant 2 à 6 atomes de C,
m, x et y correspondent chacun à un nombre entier de 0 à 30,
comme solubiliseurs dans des concentrés de produits nettoyants pour des solutions nettoyantes
2. Mise en oeuvre d'une ou de plusieurs amines grasses éthoxylées de la formule générale (I) selon la revendication 1, dans laquelle les sommes (n + m) ou (n + x + y) sont comprises dans l'intervalle de 10 à 15.
3. Mise en oeuvre d'une ou de plusieurs amines grasses éthoxylées de la formule générale (I) selon les revendications 1 et 2 dans des concentrés de produits nettoyants pour le lavage des bouteilles.
4. Mise en oeuvre d'une ou de plusieurs amines grasses éthoxylées de la formule générale (I) selon les revendications 1 à 3, à raison de 1 à 15% en poids rapporté à la composition totale du concentré.
EP87101229A 1986-02-06 1987-01-29 Utilisation d'amines grasses éthoxylées comme solubiliseurs Expired - Lifetime EP0231886B2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87101229T ATE68518T1 (de) 1986-02-06 1987-01-29 Verwendung ethoxylierter fettamine als loesungsvermittler.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863603579 DE3603579A1 (de) 1986-02-06 1986-02-06 Verwendung ethoxylierter fettamine als loesungsvermittler
DE3603579 1986-02-06

Publications (4)

Publication Number Publication Date
EP0231886A2 EP0231886A2 (fr) 1987-08-12
EP0231886A3 EP0231886A3 (en) 1989-08-30
EP0231886B1 true EP0231886B1 (fr) 1991-10-16
EP0231886B2 EP0231886B2 (fr) 1994-08-03

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ID=6293459

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EP87101229A Expired - Lifetime EP0231886B2 (fr) 1986-02-06 1987-01-29 Utilisation d'amines grasses éthoxylées comme solubiliseurs

Country Status (7)

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US (1) US4803012A (fr)
EP (1) EP0231886B2 (fr)
AT (1) ATE68518T1 (fr)
CA (1) CA1323283C (fr)
DE (2) DE3603579A1 (fr)
DK (1) DK166590B1 (fr)
ES (1) ES2026466T5 (fr)

Cited By (1)

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DE102022207153A1 (de) 2022-07-13 2024-01-18 Henkel Ag & Co. Kgaa Waschaktive Verbindungen auf Basis einer Kombination von Anionen und Kationentensid

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US5145608A (en) * 1986-02-06 1992-09-08 Ecolab Inc. Ethoxylated amines as solution promoters
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US5881728A (en) * 1996-07-26 1999-03-16 Wisconsin Alumni Research Foundation Digital subtraction magnetic resonance angiography with image artifact suppression
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US8404899B2 (en) * 2007-09-27 2013-03-26 Sanyo Chemical Industries, Ltd. Aliphatic amine alkylene oxide adduct
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US8993502B2 (en) 2008-02-21 2015-03-31 S. C. Johnson & Son, Inc. Cleaning composition having high self-adhesion to a vertical hard surface and providing residual benefits
JP2011513510A (ja) * 2008-02-21 2011-04-28 エス．シー． ジョンソン アンド サン、インコーポレイテッド 高い自己接着性を有し残留による利益を提供する洗浄組成物
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US8143206B2 (en) * 2008-02-21 2012-03-27 S.C. Johnson & Son, Inc. Cleaning composition having high self-adhesion and providing residual benefits
US8980813B2 (en) 2008-02-21 2015-03-17 S. C. Johnson & Son, Inc. Cleaning composition having high self-adhesion on a vertical hard surface and providing residual benefits
US9410111B2 (en) 2008-02-21 2016-08-09 S.C. Johnson & Son, Inc. Cleaning composition that provides residual benefits
PL3540033T3 (pl) 2010-11-11 2023-12-04 Ecolab Usa Inc. Proces czyszczenia i usuwania etykiet z butelek
US9487735B2 (en) 2012-05-14 2016-11-08 Ecolab Usa Inc. Label removal solution for low temperature and low alkaline conditions
WO2013172925A1 (fr) 2012-05-14 2013-11-21 Ecolab Usa Inc. Solution de retrait d'étiquette pour des bouteilles de boisson consignées
US9637677B2 (en) * 2014-09-04 2017-05-02 Ideal Energy Solutions IP Control, LLC Aqueous cleaning composition and method

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Publication number Priority date Publication date Assignee Title
DE102022207153A1 (de) 2022-07-13 2024-01-18 Henkel Ag & Co. Kgaa Waschaktive Verbindungen auf Basis einer Kombination von Anionen und Kationentensid
WO2024012732A1 (fr) 2022-07-13 2024-01-18 Henkel Ag & Co. Kgaa Composés actifs au lavage basés sur une combinaison d'anions et de détergent cationique

Also Published As

Publication number Publication date
DK166590B1 (da) 1993-06-14
EP0231886B2 (fr) 1994-08-03
ATE68518T1 (de) 1991-11-15
EP0231886A3 (en) 1989-08-30
US4803012A (en) 1989-02-07
DE3603579A1 (de) 1987-08-13
DK53187D0 (da) 1987-02-02
DE3773688D1 (de) 1991-11-21
ES2026466T3 (es) 1992-05-01
DK53187A (da) 1987-08-07
ES2026466T5 (es) 1995-08-16
CA1323283C (fr) 1993-10-19
EP0231886A2 (fr) 1987-08-12

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