EP0058751B1 - Use of n-oxyalkylated derivatives of aniline as polymer dissolving components in floor cleaning compositions - Google Patents

Use of n-oxyalkylated derivatives of aniline as polymer dissolving components in floor cleaning compositions Download PDF

Info

Publication number
EP0058751B1
EP0058751B1 EP81108390A EP81108390A EP0058751B1 EP 0058751 B1 EP0058751 B1 EP 0058751B1 EP 81108390 A EP81108390 A EP 81108390A EP 81108390 A EP81108390 A EP 81108390A EP 0058751 B1 EP0058751 B1 EP 0058751B1
Authority
EP
European Patent Office
Prior art keywords
aniline
floor cleaning
cleaning compositions
dissolving components
polymer dissolving
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.)
Expired
Application number
EP81108390A
Other languages
German (de)
French (fr)
Other versions
EP0058751A1 (en
Inventor
Rudolf Beck
Sigrid Dr. Scholz-Weigl
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.)
Huels AG
Original Assignee
Chemische Werke Huels AG
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 Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of EP0058751A1 publication Critical patent/EP0058751A1/en
Application granted granted Critical
Publication of EP0058751B1 publication Critical patent/EP0058751B1/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/30Amines; Substituted amines ; Quaternized amines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/43Solvents

Definitions

  • N-phenyldiethanolamine is mainly used to dissolve the polymers in floor cleaning agents (self-wax wax removal) (prepared by adding 2 moles of ethylene oxide to aniline without adding any contact) (WE Draper, LP Johnson, Soap & Chemical Specialties January 1971, Page 38 to 44, 74 and 75).
  • floor cleaning agents self-wax wax removal
  • This blue color is unpleasant because it makes the original color bluish. Due to the cleaning, this blue coloring is not uniform, but leads to more or less intense coloring. Splashes of drops that are not removed result in deep blue color dots. These blue discolorations can only be removed very poorly or not at all.
  • n assumes a value from 1 to 5, in particular from 1 to 3.
  • N-oxalkylated derivatives of aniline can thus be used according to the invention as a polymer-dissolving component in floor cleaning agents: reaction products of o-toluidine, p-toluidine, p-phenylenediamine, N-methylaniline with the corresponding number of moles of ethylene oxide and / or propylene oxide, preferably reaction products of Aniline with the corresponding mole number of ethylene oxide and / or propylene oxide.
  • the N-oxalkylated aniline derivatives in question can be prepared by adding the corresponding number of moles of ethylene oxide and / or propylene oxide to aniline and substituted aromatic amines in the presence of alkaline catalysts.
  • alkaline catalysts Na methylate, Na ethylate, Na n-propylate, sodium hydroxide, potassium hydroxide, potassium methylate and sodium phenolate.
  • aniline derivatives can be used as starting materials for the addition of ethylene oxide and / or propylene oxide: o-toluidine, p-toluidine, p-phenylenediamine, N-methylaniline.
  • the most important effect of the products to be used according to the invention is that they do not show the disturbing blue color of the agent of the prior art. Furthermore, some of them have a significantly improved dissolving effect on the polymers used in self-waxing floors.
  • PVC sheets that had been pretreated with commercially available floor care products were used for cleaning.
  • the care products were colored with a dark color (R 28032 ex. Conc. BASF) for better evaluation of the cleaning tests.
  • the Gardner scrubber was used for cleaning.
  • the cleaning effect was determined with the filter color measuring device RFC 3 from Zeiss.
  • Figure 1 shows the cleaning effect of various N-oxyalkylated aniline derivatives compared to N-phenyldiethanolamine.
  • the floor cleaning agents in which the agent to be used according to the invention is used, consist i. a. from an anionic and / or nonionic surfactant and optionally an inorganic basic compound.

Description

Für die Lösung der Polymeren in Fußbodenreinigungsmitteln (Fußbodenselbstglanzwachsentfernung) wird hauptsächlich N-Phenyldiethanolamin

Figure imgb0001
(hergestellt durch Anlagerung von 2 Molen Ethylenoxid an Anilin ohne Kontaktzugabe) eingesetzt (W. E. Draper, L. P. Johnson, Soap & Chemical Specialties Januar 1971, Page 38 bis 44, 74 und 75). Dieses Produkt hat den Nachteil, daß es sich selbst und auch die zu reinigenden Oberflächen, wie Stein, Holz, Kunststoffe und lackierte Oberflächen, nach einer gewissen Zeit blau verfärbt. Diese Blaufärbung ist unangenehm, weil dadurch die ursprüngliche Farbe blaustichig wird. Bedingt durch die Reinigung ist diese Blaufärbung nicht einheitlich, sondern führt zu mehr oder weniger starken Einfärbungen. Spritztropfen, die nicht entfernt werden, ergeben tiefblaue Farbpunkte. Diese Blauverfärbungen lassen sich nur sehr schlecht oder gar nicht mehr entfernen.N-phenyldiethanolamine is mainly used to dissolve the polymers in floor cleaning agents (self-wax wax removal)
Figure imgb0001
(prepared by adding 2 moles of ethylene oxide to aniline without adding any contact) (WE Draper, LP Johnson, Soap & Chemical Specialties January 1971, Page 38 to 44, 74 and 75). The disadvantage of this product is that it turns itself and the surfaces to be cleaned, such as stone, wood, plastics and painted surfaces, blue after a certain time. This blue color is unpleasant because it makes the original color bluish. Due to the cleaning, this blue coloring is not uniform, but leads to more or less intense coloring. Splashes of drops that are not removed result in deep blue color dots. These blue discolorations can only be removed very poorly or not at all.

Es wurde nun gefunden, daß diese störenden Blaufärbungen nicht auftreten bei Verwendung von N-oxalkylierten Derivaten des Anilins der allgemeinen Formel

Figure imgb0002
in der R1 und R2 Wasserstoff oder die NH2-Gruppe oder niedere Alkylgruppen mit 1 bis 4 C-Atomen bedeuten, jedoch nicht gleich sein müssen, R3 für Wasserstoff oder eine niedere Alkylgruppe mit 1 bis 4 C-Atomen, R4 für Wasserstoff oder die Methylgruppe und n für Werte von 1,0 bis 5,0 steht, als polymerlösende Komponente in Fußbodenreinigungsmitteln.It has now been found that these disturbing blue stains do not occur when using N-oxyalkylated derivatives of the aniline of the general formula
Figure imgb0002
in which R 1 and R 2 denote hydrogen or the NH 2 group or lower alkyl groups with 1 to 4 C atoms, but need not be the same, R 3 for hydrogen or a lower alkyl group with 1 to 4 C atoms, R 4 represents hydrogen or the methyl group and n stands for values from 1.0 to 5.0, as a polymer-dissolving component in floor cleaning agents.

Bevorzugt eingesetzt werden Verbindungen der allgemeinen Formel

Figure imgb0003
in der n einen Wert von 1 bis 5, insbesondere von 1 bis 3, annimmt.Compounds of the general formula are preferably used
Figure imgb0003
in which n assumes a value from 1 to 5, in particular from 1 to 3.

Es lassen sich erfindungsgemäß somit beispielsweise folgende N-oxalkylierte Derivate des Anilins als polymerlösende Komponente in Fußbodenreinigungsmitteln einsetzen : Umsetzungsprodukte von o-Toluidin, p-Toluidin, p-Phenylendiamin, N-Methylanilin mit der entsprechenden Molzahl Ethylenoxid und/oder Propylenoxid, vorzugsweise Umsetzungsprodukte von Anilin mit der entsprechenden Molzahl Ethylenoxid und/oder Propylenoxid.The following N-oxalkylated derivatives of aniline can thus be used according to the invention as a polymer-dissolving component in floor cleaning agents: reaction products of o-toluidine, p-toluidine, p-phenylenediamine, N-methylaniline with the corresponding number of moles of ethylene oxide and / or propylene oxide, preferably reaction products of Aniline with the corresponding mole number of ethylene oxide and / or propylene oxide.

Die betreffenden N-oxalkylierten Anilinderivate lassen sich herstellen durch Anlagerung der entsprechenden Molzahl Ethylenoxid und/oder Propylenoxid an Anilin sowie substituierte aromatische Amine in Gegenwart von alkalischen Katalysatoren. Als alkalische Katalysatoren lassen sich verwenden : Na-methylat, Na-ethylat, Na-n-propylat, Natriumhydroxid, Kaliumhydroxid, Kaliummethylat und Natriumphenolat.The N-oxalkylated aniline derivatives in question can be prepared by adding the corresponding number of moles of ethylene oxide and / or propylene oxide to aniline and substituted aromatic amines in the presence of alkaline catalysts. The following can be used as alkaline catalysts: Na methylate, Na ethylate, Na n-propylate, sodium hydroxide, potassium hydroxide, potassium methylate and sodium phenolate.

Herstellung von N-(ß-hydroxi-oxethyl-) anilinProduction of N- (ß-hydroxy-oxethyl-) aniline

Unter Stickstoffatmosphäre wurden an 465 g (5 Mole) Anilin im Autoklaven bei ca. 140 °C und 3 bar in Gegenwart von 2,3 g Na-Methylat 440 g (10 Mole) Ethylenoxid angelagert. Nach beendeter Reaktion wurde eine halbe Stunde mit Stickstoff gespült und das angefallene Reaktionsprodukt ohne weitere Aufarbeitung eingesetzt.Under a nitrogen atmosphere, 440 g (10 moles) of ethylene oxide were added to 465 g (5 moles) of aniline in an autoclave at approx. 140 ° C. and 3 bar in the presence of 2.3 g of Na methylate. After the reaction had ended, the mixture was flushed with nitrogen for half an hour and the reaction product obtained was used without further workup.

Als Ausgangsstoffe für die Anlagerung von Ethylenoxid und/oder Propylenoxid können folgende Anilin-Derivate herangezogen werden : o-Toluidin, p-Toluidin, p-Phenylendiamin, N-Methylanilin.The following aniline derivatives can be used as starting materials for the addition of ethylene oxide and / or propylene oxide: o-toluidine, p-toluidine, p-phenylenediamine, N-methylaniline.

Der wichtigste Effekt der erfindungsgemäß zu verwendenden Produkte besteht darin, daß sie die störende Blaufärbung des Mittels des Standes der Technik nicht zeigen. Ferner haben sie zum Teil eine deutlich verbesserte lösende Wirkung auf die in Fußbodenselbstglanzwachsen eingezetzten Polymeren.The most important effect of the products to be used according to the invention is that they do not show the disturbing blue color of the agent of the prior art. Furthermore, some of them have a significantly improved dissolving effect on the polymers used in self-waxing floors.

Einige der erfindungsgemäßen Produkte wurden in nachfolgender Rezeptur eines Fußbodenreinigungsmittels eingearbeitet und für Reinigungsversuche verwendet :

  • 2,5 % n-Dodecylbenzolsulfonat-Na-Salz
  • 3,0 % Fettsäuretriethanolaminsalz
  • 2,0 % Fettsäureamidpolyglykolether
  • 2,0 % Butyldiglykol
  • 3,Q % Triethanolamin
  • 3,0 % Ethylendiamintetraacetat
  • 5,0% N-oxethyliertes Anilin

Rest zu 100% TrinkwasserSome of the products according to the invention were incorporated into the following formulation of a floor cleaning agent and used for cleaning tests:
  • 2.5% n-dodecylbenzenesulfonate Na salt
  • 3.0% fatty acid triethanolamine salt
  • 2.0% fatty acid amide polyglycol ether
  • 2.0% butyl diglycol
  • 3, Q% triethanolamine
  • 3.0% ethylenediaminetetraacetate
  • 5.0% N-oxyethylated aniline

Rest 100% drinking water

Zur Reinigung wurden PVC-Platten, die mit handelsüblichen Fußbodenpflegemitteln (Glänzer, emsal, eingetragene Warenzeichen) vorbehandelt waren, verwendet. Die Pflegemittel wurden zur besseren Auswertung der Reinigungsversuche mit einem dunklen Farbton (R 28032 ex. conc. Fa. BASF) eingefärbt.PVC sheets that had been pretreated with commercially available floor care products (gloss, emsal, registered trademarks) were used for cleaning. The care products were colored with a dark color (R 28032 ex. Conc. BASF) for better evaluation of the cleaning tests.

Zur Reinigung wurde das Scheuergerät nach Gardner benutzt. Die Reinigungswirkung wurde mit dem Filterfarbmeßgerät RFC 3 der Fa. Zeiss festgestellt.The Gardner scrubber was used for cleaning. The cleaning effect was determined with the filter color measuring device RFC 3 from Zeiss.

Ergebnisse:

  • Reinigungswirkung in Prozent Aufhellung
    Figure imgb0004
Results:
  • Cleaning effect in percent brightening
    Figure imgb0004

In der Abbildung 1 wird die Reinigungswirkung verschiedener N-oxalkylierter Anilin-Derivate im Vergleich zum N-Phenyldiethanolamin dargestellt.Figure 1 shows the cleaning effect of various N-oxyalkylated aniline derivatives compared to N-phenyldiethanolamine.

Dabei zeigt sich, daß die erfindungsgemäß einzusetzenden Produkte mit 1 bis 2 Mol EO deutlich bessere Reinigungsergebnisse ergeben als der Stand der Technik. Höher oxethylierte Produkte sind weniger gut.It shows that the products to be used according to the invention with 1 to 2 mol EO give significantly better cleaning results than the prior art. Products with higher levels of ethoxylation are less good.

Es muß jedoch darauf hingewiesen werden, daß unter praxisnahen Gebrauchsbedingungen auch nach mehreren Wochen keine unerwünschte Blaufärbung festgestellt wurde.However, it must be pointed out that, under practical conditions of use, no undesirable blue color was found even after several weeks.

Rezepturbeispiele für FußbodenreinigungsmittelRecipe examples for floor cleaning agents

Figure imgb0005
Figure imgb0005

Die Fußbodenreinigungsmittel, in welchen das erfindungsgemäß zu verwendende Mittel eingesetzt wird, bestehen i. a. aus einem anionischen und/oder nichtionischen Tensid und gegebenenfalls einer anorganischen basischen Verbindung.The floor cleaning agents, in which the agent to be used according to the invention is used, consist i. a. from an anionic and / or nonionic surfactant and optionally an inorganic basic compound.

Claims (3)

1. The use of an N-oxyalkylated derivative of an aniline as a polymer solvent component in a floor cleaning composition, characterised in that a derivative of the general formula
Figure imgb0009
where R1 and R2 are hydrogen, NH2 or lower alkyl of 1 to 4 carbon atoms but are not identical with one another, R3 is hydrogen or lower alkyl of 1 to 4 carbon atoms, R4 is hydrogen or methyl and n is from 1.0 to 5.0, is used.
2. A use according to claim 1, characterised in that an aniline derivative of the general formula
Figure imgb0010
where n is from 1 to 5, is used.
3. A use according to claim 1 or 2, characterised in that an aniline derivative of the general formula
Figure imgb0011
where n is from 1 to 3, is used.
EP81108390A 1981-02-21 1981-10-16 Use of n-oxyalkylated derivatives of aniline as polymer dissolving components in floor cleaning compositions Expired EP0058751B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3106491 1981-02-21
DE3106491A DE3106491C2 (en) 1981-02-21 1981-02-21 Use of N-oxalkylated derivatives of aniline as polymer-dissolving components in floor cleaning agents

Publications (2)

Publication Number Publication Date
EP0058751A1 EP0058751A1 (en) 1982-09-01
EP0058751B1 true EP0058751B1 (en) 1984-04-11

Family

ID=6125420

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81108390A Expired EP0058751B1 (en) 1981-02-21 1981-10-16 Use of n-oxyalkylated derivatives of aniline as polymer dissolving components in floor cleaning compositions

Country Status (3)

Country Link
US (1) US4425266A (en)
EP (1) EP0058751B1 (en)
DE (2) DE3106491C2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891160A (en) * 1982-12-23 1990-01-02 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4857114A (en) * 1987-04-13 1989-08-15 Amway Corporation Floor polish remover
DE19718065A1 (en) * 1997-04-29 1998-11-05 Henkel Kgaa Detergent for post-curing polyurethane hotmelts

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA714018A (en) 1961-05-26 1965-07-20 Colgate-Palmolive Company Hard surface cleaning compositions
US3954648A (en) 1969-12-22 1976-05-04 Pennwalt Corporation Coatings removal composition containing an alkali metal hydroxide, an oxygenated organic solvent, and an amine
US3766076A (en) 1970-11-05 1973-10-16 Oxy Metal Finishing Corp Stripping composition and process
US3723148A (en) 1971-03-15 1973-03-27 Oxy Metal Finishing Corp Process for recovering coating materials
GB1438948A (en) 1972-08-11 1976-06-09 Unilever Ltd Solvent type cleaners
US4077896A (en) 1975-01-15 1978-03-07 Minnesota Mining And Manufacturing Company Wax-stripping cleaning composition

Also Published As

Publication number Publication date
DE3163102D1 (en) 1984-05-17
EP0058751A1 (en) 1982-09-01
US4425266A (en) 1984-01-10
DE3106491C2 (en) 1982-12-09
DE3106491A1 (en) 1982-09-02

Similar Documents

Publication Publication Date Title
DE3417912C1 (en) Siloxanes containing betaine groups, their production and use in cosmetic preparations
EP2778170B1 (en) Phosphoric acid esters, their preparation and use
DE2203141C3 (en) Colored particles and their use in all-purpose cleaning agents
EP2363422A1 (en) Silicon-organic graft copolymers containing nitrogen
DE102004053384A1 (en) Liquid, viscous agent based on an organofunctional silane system for the production of weather-resistant protective coatings to prevent contamination of surfaces
DE1291749B (en) Process for the preparation of amine oxides
DE10147650A1 (en) Hydrophilic emulsifiers based on polyisobutylene
DE2155004C3 (en) Carpet and upholstery cleaning agents
DE1771548A1 (en) Metalworking and anti-corrosion agents
WO2002083626A2 (en) Alkyl and/or alkenyl glycerol carbamates
EP0058751B1 (en) Use of n-oxyalkylated derivatives of aniline as polymer dissolving components in floor cleaning compositions
DE1020144B (en) Detergents and cleaning agents
DE602004006552T2 (en) Gemini glycidyl ether adducts of polyhydroxyalkylalkylenediamines
EP1354905A2 (en) Method for producing ether-carboxylic acids having low pour point
DE1172791B (en) Detergent made from synthetic detergent substances
DE3541813C2 (en) Thickener for preparations containing surfactants based on polyether derivatives
DE2711000A1 (en) PROCESS FOR THE PRODUCTION OF Aqueous Coating Agents or PAINT
DE102004010505A1 (en) Process for the solvent-free production of low residual salt ether carboxylic acids
WO2003040073A1 (en) Alkyl(en)ylglycerinether carboxylic acids
DE102014216380A1 (en) Emulsions of aminosiloxanes and silicates
DE1053139B (en) Textile oil based on mineral oil
DE69915747T2 (en) Process for the treatment of fruits and vegetables after harvest, with the purification of phytosanitary products contaminated with primary aromatic amines
WO1996009763A1 (en) Use of surfactants to boost the anti-microbial properties of a carboxylic acid amide
EP0670299A1 (en) Dedusting agent
DE1959652A1 (en) Acid detergents

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): DE FR GB IT NL

17P Request for examination filed

Effective date: 19820805

ITF It: translation for a ep patent filed

Owner name: SOCIETA' ITALIANA BREVETTI S.P.A.

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): DE FR GB IT NL

REF Corresponds to:

Ref document number: 3163102

Country of ref document: DE

Date of ref document: 19840517

ET Fr: translation filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19841001

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19841031

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19841106

Year of fee payment: 4

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19860501

GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19860630

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19860701

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881121