EP0189085B1 - Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage - Google Patents

Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage Download PDF

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Publication number
EP0189085B1
EP0189085B1 EP86100364A EP86100364A EP0189085B1 EP 0189085 B1 EP0189085 B1 EP 0189085B1 EP 86100364 A EP86100364 A EP 86100364A EP 86100364 A EP86100364 A EP 86100364A EP 0189085 B1 EP0189085 B1 EP 0189085B1
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Prior art keywords
cationic surfactants
carbon atoms
quaternary ammonium
ammonium compounds
acid
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EP86100364A
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German (de)
English (en)
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EP0189085A2 (fr
EP0189085A3 (en
Inventor
Jürgen Dr. Geke
Horst Dr. Rutzen
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to AT86100364T priority Critical patent/ATE56698T1/de
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Publication of EP0189085A3 publication Critical patent/EP0189085A3/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
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the invention relates to new, improved cationic surfactants based on quaternary ammonium compounds and the use of such cationic surfactants in industrial cleaning solutions.
  • aqueous solutions which contain surfactants in addition to other auxiliaries, such as builder substances, complexing agents, organic or inorganic corrosion protection agents and optionally other substances.
  • surfactants in addition to other auxiliaries, such as builder substances, complexing agents, organic or inorganic corrosion protection agents and optionally other substances.
  • DE-A-27 12 900 and DE-A-32 47 431 propose processes in which, in addition to other detergent components, quaternary ammonium compounds are used as cationic surfactants in the alkaline pH range, in which organic ammonium nitrogen atoms are used Residues, especially alkyl residues of different chain lengths, are bound.
  • Counterions of the ammonium cations used are, for example, anions such as chloride, sulfate or methyl sulfate, which are known as anions which cause corrosion.
  • the necessary content of such anions undesirably promotes corrosion on system parts and treated metal surfaces. This is an extremely disadvantage, in particular when treating metal surfaces with aqueous products, in particular when higher application concentrations of cationic surfactants are desired. Corrosion occurs not only in the long term during the intermediate storage of treated parts, but also directly when treating corresponding surfaces with the aqueous application solutions.
  • DE-A-30 48 642 also discloses surfactant mixtures for cleaning bottles and other objects with hard surfaces (porcelain, plastic, metal) which contain cationic surfactants based on ammonium compounds.
  • cationic surfactants based on ammonium compounds.
  • a disadvantage of these surfactants is that they contain chloride, bromide or methyl sulfate as anions. In this case, too, the anions counteract the desired corrosion protection on system parts (e.g. dishwashers) and treated surfaces as a result of the treatment with such surfactant mixtures.
  • quaternary ammonium compounds which contain at least one long-chain hydroxyalkyl radical by reacting the salt of a tertiary amine and an inorganic or organic acid in water with an epoxy compound which has at least one terminal epoxy group and at least 6 C atoms, at atmospheric pressure and temperatures between 40 and 100 ° C and a pH of at least 7 are known from DE-A-33 21 608.
  • Suitable acids are: boric acid, carbonic acid, phosphoric acid, phenol, capric acid and acidic salts of carbonic acid, phosphoric acid and sulfuric acid.
  • the compounds prepared in this way are used as textile softeners or antistatic agents or as antimicrobials.
  • the resulting quaternary ammonium compounds were also unable to meet the high demands in terms of user-friendliness and corrosion protection that are placed on commercially available cationic surfactants.
  • the anions of numerous organic acids are not suitable for the formation of cationic surfactants because the resulting quaternary ammonium compounds are poorly water-soluble. They are produced in paste-like form and, due to their poor water solubility, cannot be assembled in industrial cleaners.
  • ammonium cations which contain numerous hydroxyalkyl groups, cause troublesome precipitates in water which is not completely demineralized, which likewise makes the use of such cationic surfactants impossible.
  • cationic surfactants are often expected to have a demulsifying and / or defoaming effect on emulsions and / or anionic surfactants or emulsifiers.
  • the quaternary ammonium compounds disclosed in the said application had no demulsifying effect on emulsions and / or anionic emulsifiers.
  • DE-A-26 31 733 also describes a process for promoting condensation and / or polymerization reactions of organic isocyanates, in which a catalytic amount of a quaternary hydroxyalkylammonium compound of the general formula used.
  • the radical R 4 can mean an alkyl group with 1 to 15 C atoms and the radicals R i , R 2 and R 3 independently of one another alkyl groups or hydroxyalkyl groups with 1 to 20 C atoms or a benzyl group.
  • the anion is preferably derived from the following acids: formic acid, acetic acid, hexanoic acid and the straight-chain or branched heptanoic acids, octanoic acids, decanoic acids and hexadecanoic acids; Neoacids such as 3,3-dimethylbutanoic acid, unsaturated aliphatic acids such as oleic acid, acrylic acid, methacrylic acid, undecenoic acid and aromatic acids such as benzoic acid, phenylacetic acid and salicylic acid.
  • other di- (hydroxyalkyl) compounds of the general formula have already been recommended as emulsifiers, wetting agents and the like.
  • the object of the present invention was to provide new, improved cationic surfactants based on quaternary ammonium compounds which do not have the disadvantages of the prior art.
  • cationic surfactants should be made available for industrially usable cleaning agents, the components of which inhibit the corrosion process, ensure a sufficient demulsifying effect with regard to anionic contamination and can be readily packaged in aqueous industrial cleaners, i.e. are easily water-soluble, do not cause troublesome precipitates and are compatible with other components commonly used in industrial cleaners.
  • the object is achieved by cationic surfactants based on quaternary ammonium compounds, the ammonium nitrogen atom of which contains at least two alkyl radicals, a 2-hydroxyalkyl radical originating from the reaction with a terminal epoxide carrying 10 to 24 carbon atoms and optionally an arylalkyl group and the anion of which carries the anion is an organic carboxylic acid with 5 to 16 carbon atoms.
  • cationic surfactants not only have good demulsifying properties with regard to anionic surfactants or emulsifiers, but also make the treated surfaces hydrophobic in corresponding industrial cleaners, and help prevent corrosion by ensuring that the application liquids run off the treated surfaces well and without running and even an antistatic effect can be achieved on plastic surfaces.
  • linear or branched alkyl radicals which R 1 and R 2 can represent are methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl and hexadecyl.
  • Quaternary ammonium compounds in which R 2 is hydrogen and R 1 is a linear or branched alkyl radical having 8 to 22 carbon atoms for example n-octyl, n-decyl, n-dodecyl, n-tetradecyl or n-hexadecyl, are preferred.
  • the total number of carbon atoms in both substituents R 1 and R 2 must be in the range from 8 to 22 carbon atoms.
  • the R 5 radical bonded to the ammonium nitrogen atom represents alkyl radicals such as, for example, n-butyl, i-butyl, tert-butyl, n-pentyl, tert-butylmethyl or n-hexyl or phenalkyl radicals such as benzyl, phenylethyl or phenylpropyl.
  • the counter anion in the cationic surfactants according to the invention is the anion of an organic carboxylic acid having 5 to 16 carbon atoms
  • the radical R 6 in the general formula 1 represents alkyl radicals such as, for example, n-butyl, i-butyl, tert-butyl, pentyl, Hexyl, octyl, 2-ethyl-hexyl, n-nonyl, i-nonyl, decyl, dodecyl or pentadecyl.
  • the isononanoate anion is particularly preferred.
  • Benzyldimethyl-2-hydroxydodecylammonium isononanoate (BDHAI), the benzyldimethyl-2-hydroxydodecylammonium salt of 9/13 versatic acid R , benzyldimethyl-2-hydroxydodecylammonium isopalmitate, butyldimethyl-2-hydroxydodecylammonylononononanoanoidonanoononanoatonate.
  • benzyldimethyl 2-hydroxydodecylammonium isonanoanoate is particularly preferred.
  • the compounds of the general formula I according to the invention can be prepared by methods known per se by adding the salt of a tertiary amine of the general formula
  • reaction mixture before the start Implementation has a pH of at least 7.
  • the epoxides of the general formula IV used to prepare the quaternary ammonium compounds according to the invention can thus be epoxides having 10 to 24 carbon atoms in which the oxirane ring is located at any point in the molecule.
  • the amines used to prepare the quaternary ammonium compounds of the general formula I are preferably tertiary alkyl, hydroxyalkyl or alkylarylamines, with dimethylbutylamine and dimethylbenzylamine being particularly preferred.
  • the carboxylic acids used to prepare the quaternary ammonium compounds according to the invention are preferably monocarboxylic acids having 5 to 8 carbon atoms in the alkyl radical. Isononanoic acid is particularly preferably used.
  • the quaternary ammonium compounds according to the invention are used as cationic surfactants in industrial cleaning solutions. They have the advantage over other cationic surfactants as well as quaternary ammonium compounds already known from the prior art that they do not contain any corrosive counterions or lead to undesirable precipitations.
  • acids are even able to inhibit the corrosion process on cleaned metal surfaces.
  • the lack of accumulation of corrosive anions in the baths and the inhibitory effect of the carboxylic acid anions thus improve the corrosion protection properties in aqueous media. This applies equally to parts that have to be temporarily stored before the further processing process, as well as to parts that are to be processed immediately.
  • the improved corrosion protection is particularly noticeable in the case of parts which have been treated with industrial cleaners containing quaternary ammonium compounds and which, due to their geometry, have a creative effect.
  • the risk of corrosion on such parts was particularly high, since if the solvent, usually water, evaporated, there was a risk that the ingredients and thus the corrosive components would be heavily concentrated. This is prevented when using industrial cleaning solutions containing the quaternary ammonium compounds according to the invention as cationic surfactants.
  • the cationic surfactants according to the invention offer a further advantage in that an advantageous hydrophobization of the cleaned surfaces, in particular the cleaned metal surfaces, is observed. Furthermore, corrosion of the treated parts is avoided by a very good drainage behavior of the application liquid.
  • aqueous industrial cleaning solutions which contain the quaternary ammonium compounds according to the invention as cationic surfactants can also be used for cleaning plastics, since they have an antistatic effect. It is precisely this that will open up such products to a wide range of applications in the future, since plastic surfaces, similar to metal surfaces, are being cleaned with an increasing tendency in spray processes.
  • the quaternary ammonium compounds according to the invention are suitable for use in all cleaning agents which are important for industrial cleaning. They can be used in sprayable cleaners, e.g. neutral to weakly alkaline cleaners or acid cleaners may be present, especially in cleaning solutions that are sprayed onto the parts to be cleaned under high pressure. Equally, however, they can also be used with advantage in immersion cleaners based on nonionic surfactants.
  • Quaternary ammonium compounds according to the invention are also used as cationic surfactants which act as demulsifiers or antifoams in industrial cleaning solutions for spraying or dipping.
  • the new improved cationic surfactants based on quaternary ammonium compounds are made up with other components, which are conventional for industrial cleaning solutions, by processes known per se.
  • these solutions may also contain other additives, for example alkanolamines, phosphates, borates or contain nitrites.
  • inhibitors in particular for non-ferrous metals, or biocides such as, for example, hexahydrotriazine derivatives and / or phenols and / or chlorophenols can be added to the solutions to prevent bacterial and / or fungal attack in the spraying or immersion systems.
  • Detergent solutions with application concentrations in the range from 0.5 to 5% were produced, which were intended for detergents to be applied in spraying.
  • the solutions had the following compositions (data in% by weight):
  • the cleaning agents formulated as described above could easily be applied by spraying. They showed little or no tendency to foam. The cleaning baths were stable for a long time and their cleaning power did not deteriorate over this time. Due to the use of the quaternary ammonium compounds according to the invention, the metal surfaces treated with the cleaners in the spray did not corrode, but instead had increased corrosion protection in comparison with treatment with conventional cleaners.
  • the cleaning agents formulated as described above had a high cleaning power on treated metal surfaces over a long period of time and their baths were very stable. Metal surfaces that had been treated with the above-described cleaners in immersion had improved corrosion protection compared to metal surfaces treated with conventional cleaners.
  • the emulsion cleavage was carried out according to the following test:
  • the cleaning compositions composed as described above showed good cleaning action and a uniform, run-free drainage behavior on the treated parts.
  • BDHAI shows a significantly better corrosion protection behavior.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Claims (12)

1. Nouveaux tensioactifs cationiques à base de composés d'ammonium quaternaire, caractérisés en ce qu'ils présentent la formule générale
Figure imgb0009
dans laquelle
R1 représente un résidu alkyle linéaire ou ramifié comportant 1 à 22 atomes de C,
R2 correspond à de l'hydrogène ou à un résidu alkyl linéaire ou ramifié comportant 1 à 21 atomes de C, le nombre total des atomes de C4 des substituants R1 et R2 étant compris entre 8 et 22, et
R3 et R4 sont un méthyle, un éthyle, un 2-hydroxyéthyle ou un 2-hydroxypropyle,
R5 représente des résidus alkyle comportant 4 à 6 atomes C ou des résidus phénalkyle dont le résidu alkyle comporte 1 à 3 atomes de C et
R6 correspond à des résidus alkyle linéaire ou ramifiés comportant 4 à 15 atomes de C.
2. Tensioactifs cationiques selon la revendication 1, caractérisés en ce que dans la formule générale I, R1 est un résidu alkyle comportant 8 à 22 atomes de C et R2 est un atome d'hydrogène.
3. Tensioactifs cationiques selon la revendication 2, caractérisés en ce que dans la formule générale I, R' est un résidu décyle ou tétradécyle.
4. Tensioactifs cationiques selon la revendication 1, caractérisés en ce que R3 et R4 représentent des groupements méthyle.
5. Tensioactifs cationiques selon la revendication 1, caractérisés en ce que dans la formule générale I, R5 représente un résidu benzyle ou n-butyle.
6. Tensioactifs cationiques selon la revendication 1, caractérisés en ce que dans la formule générale I, R6 représente un résidu isooctyle.
7. Isononanoate de benzyldiméthyl-2-hydroxydodécylammonium.
8. Sel de benzyldiméthyl-2-hydroxydodécylammonium de l'acide 9/13 versatique.
9. Isopalmitate de benzyldiméthyl-2-hydroxydodécylammonium.
10. Isononanoate de butyldiméthyl-2-hydroxydodécylammonium.
11. Isononanoate de benzyldiméthyl-2-hydoxyhexadécylammonium.
12. Utilisation des tensioactifs cationiques à base de composés d'ammonium quaternaire selon les revendications 1 à 11, dans des nettoyants à projeter, dans des nettoyants en bains, et dans des additifs désémulsifiants à des solutions de nettoyants industriels ou d'autres nettoyants.
EP86100364A 1985-01-21 1986-01-13 Agents tensio-actifs cationiques à base de composés d'ammonium quaternaire et leur utilisation dans les compositions pour nettoyage Expired - Lifetime EP0189085B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86100364T ATE56698T1 (de) 1985-01-21 1986-01-13 Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853501775 DE3501775A1 (de) 1985-01-21 1985-01-21 Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln
DE3501775 1985-01-21

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EP0189085A2 EP0189085A2 (fr) 1986-07-30
EP0189085A3 EP0189085A3 (en) 1987-02-25
EP0189085B1 true EP0189085B1 (fr) 1990-09-19

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US (1) US4678605A (fr)
EP (1) EP0189085B1 (fr)
JP (1) JPS61192330A (fr)
AT (1) ATE56698T1 (fr)
AU (1) AU579443B2 (fr)
BR (1) BR8600200A (fr)
CA (1) CA1259011A (fr)
DE (2) DE3501775A1 (fr)
ZA (1) ZA86412B (fr)

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DE3620011A1 (de) * 1986-06-13 1987-12-17 Henkel Kgaa Neue kationtenside auf der basis von quartaeren ammoniumverbindungen und ihre verwendung in reinigungsmitteln
DE3811247A1 (de) * 1988-04-02 1989-10-12 Henkel Kgaa Quartaere ammoniumverbindungen
DE3816328A1 (de) * 1988-05-13 1989-11-23 Hoechst Ag Verfahren zur herstellung von quaternaeren ammoniumsalzen langkettiger aliphatischer carbonsaeuren und verwendung dieser ammoniumsalze
DE4001595A1 (de) * 1990-01-20 1991-07-25 Henkel Kgaa Demulgierende, pulverfoermige oder fluessige reinigungsmittel und deren verwendung
US5202049A (en) * 1990-11-06 1993-04-13 Elf Atochem North America, Inc. Sealer finish remover compositions
US5096610A (en) * 1990-11-06 1992-03-17 Atochem North America, Inc. Floor finish remover compositions
DE4334368C2 (de) * 1993-10-08 1995-12-14 Henkel Kgaa Schwach schäumende polymerfreie Reinigungsmittel
US6251847B1 (en) * 1996-12-06 2001-06-26 Henkel Corporation Composition and method for cleaning/degreasing metal surfaces, especially composites of copper and aluminum
US5824163A (en) * 1997-02-28 1998-10-20 Henkel Corporation Metal cleaning process that does not damage plastic
DE10141707B4 (de) * 2001-08-25 2008-07-24 Chemetall Gmbh Verfahren zur antistatischen Beschichtung von Kunststoff-Formteil-Oberflächen, von mit Kunststoff oder/und Lack beschichteten Formteilen und Verwendung der nach den Verfahren behandelten Kunststoff- oder/und Lackoberflächen
WO2007063691A1 (fr) * 2005-11-29 2007-06-07 Sanyo Chemical Industries, Ltd. Agent bacteriolytique
CA2632231C (fr) * 2005-12-02 2012-06-26 Baker Hughes Incorporated Inhibition de solides a base de naphtenate et d'emulsions dans le petrole brut
DE112008003374B4 (de) * 2007-12-14 2017-05-11 Aisin Aw Co., Ltd. Oberflächenaktiver Stoff
CN102177218A (zh) * 2008-08-11 2011-09-07 M-I澳大利亚股份有限公司 一种抑制烃中乳液形成的组合物和方法
EP2604674A1 (fr) * 2011-12-12 2013-06-19 Basf Se Utilisation d'alkylamine quaternisé comme additif dans des carburants et des lubrifiants
US20180110220A1 (en) * 2016-10-21 2018-04-26 Ecolab Usa Inc. Reduced inhalation hazard of quaternary ammonium compounds-ph driven physiological response

Citations (2)

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US2759975A (en) * 1952-05-28 1956-08-21 Gen Aniline & Film Corp Mixed alkyl-benzyl-alkylol quaternary ammonium salts
US4040992A (en) * 1975-07-29 1977-08-09 Air Products And Chemicals, Inc. Catalysis of organic isocyanate reactions

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US3636114A (en) * 1968-07-16 1972-01-18 Union Carbide Corp Novel quaternary ammonium compounds and method for preparation thereof
BE793339A (fr) * 1970-10-20 1973-06-27 Henkel & Cie Gmbh Agent de traitement complementaire du linge et son procede de preparation
DE2712900C2 (de) * 1977-03-24 1986-04-10 Henkel KGaA, 4000 Düsseldorf Verfahren zur Reinigung von Metallen im Spritzverfahren
DE2849065A1 (de) * 1978-11-11 1980-05-22 Basf Ag Verwendung von quartaeren ammoniumsalzen als leitsalze
DE3048642A1 (de) * 1980-12-23 1982-07-15 Hoechst Ag, 6000 Frankfurt "tensidgemisch zur reinigung harter oberlaechen"
DE3246124A1 (de) * 1982-12-13 1984-06-14 Henkel KGaA, 4000 Düsseldorf Reinigungsverfahren
DE3247431A1 (de) * 1982-12-22 1984-06-28 Henkel KGaA, 4000 Düsseldorf Verfahren zur regenerierung bzw. zum recycling von waessrigen entfettungs- und reinigungsloesungen
DE3321608A1 (de) * 1983-06-15 1984-12-20 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung von quartaeren ammoniumverbindungen
US4595526A (en) * 1984-09-28 1986-06-17 Colgate-Palmolive Company High foaming nonionic surfacant based liquid detergent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2759975A (en) * 1952-05-28 1956-08-21 Gen Aniline & Film Corp Mixed alkyl-benzyl-alkylol quaternary ammonium salts
US4040992A (en) * 1975-07-29 1977-08-09 Air Products And Chemicals, Inc. Catalysis of organic isocyanate reactions

Also Published As

Publication number Publication date
JPS61192330A (ja) 1986-08-26
DE3674216D1 (de) 1990-10-25
AU579443B2 (en) 1988-11-24
AU5247386A (en) 1986-07-24
BR8600200A (pt) 1986-09-30
CA1259011A (fr) 1989-09-05
EP0189085A2 (fr) 1986-07-30
DE3501775A1 (de) 1986-07-24
ATE56698T1 (de) 1990-10-15
US4678605A (en) 1987-07-07
EP0189085A3 (en) 1987-02-25
ZA86412B (en) 1986-09-24

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