WO1991009100A1 - Oxydes amines de composes amphoteres, leur preparation et leur emploi - Google Patents

Oxydes amines de composes amphoteres, leur preparation et leur emploi Download PDF

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Publication number
WO1991009100A1
WO1991009100A1 PCT/SE1990/000813 SE9000813W WO9109100A1 WO 1991009100 A1 WO1991009100 A1 WO 1991009100A1 SE 9000813 W SE9000813 W SE 9000813W WO 9109100 A1 WO9109100 A1 WO 9109100A1
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WO
WIPO (PCT)
Prior art keywords
amine oxides
compounds
carbon atoms
hydrogen
amine
Prior art date
Application number
PCT/SE1990/000813
Other languages
English (en)
Inventor
Jadwiga Palicka
Hans Olof Lagnemo
Original Assignee
Berol Nobel Ab
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 Berol Nobel Ab filed Critical Berol Nobel Ab
Publication of WO1991009100A1 publication Critical patent/WO1991009100A1/fr

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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds

Definitions

  • Amine oxides of amphoteric compounds their preparation and their use
  • the present invention relates to new compounds which are amine oxides of certain amphoteric compounds.
  • the invention also relates to the preparation of such compounds and to the use of the compounds as surface active compounds in detergent and shampoo compositions and further also to the particular use of the compounds as surface active agents and stabilizers in detergent compositions containing perborates.
  • R - [N - (CHR 1 ) x ] y - N - Q B B wherein R is a higher hydrocarbon group, R ⁇ _ is hydrogen or a lower alkyl group, x is 2 or 3, y is 0 to 4, Q is a group -R2COOM wherein R2 is an alkylene group and M is hydrogen or another cation and B is hydrogen or a group Q are per se known.
  • R is a higher hydrocarbon group
  • R ⁇ _ is hydrogen or a lower alkyl group
  • x is 2 or 3
  • Q is a group -R2COOM wherein R2 is an alkylene group and M is hydrogen or another cation and B is hydrogen or a group Q are per se known.
  • Compounds of this type are disclosed for example in the European patent applications 160507, 162600, 214868 and 314648.
  • the present invention relates to amine oxides of amphoteric compounds of this type and more particularly to amine oxides of amphoteric compounds having the general formula (I)
  • R is a hydrocarbon group having 7 to 22 carbon atoms
  • R ] _ is hydrogen or alkyl with 1 to 6 carbon atoms
  • x is 2 or 3
  • y is 0 or an integer of 1 to 4
  • Q is (R2-COOM) where R2 is alkylene with 1 to 6 carbon atoms
  • M is H, an alkali metal, an alkaline earth metal, an ammonium or a substituted ammonium ion
  • B is hydrogen or is defined according to Q.
  • the hydrocarbon group R can be straight or branched, saturated or unsaturated, and may contain substituents such as hydroxyl groups, ethoxy groups or carbonyl groups.
  • R is preferably an alkyl or alkenyl group, but can also be a cycloalkyl-alkyl group, an aralkyl or aralkenyl group where the alkyl or alkenyl group contains at least 6 carbon atoms.
  • R suitably contains 12 to 22 carbon atoms, preferably 12 to 20 carbon atoms.
  • R is a hydrocarbon group originating from natural fatty acids and particularly from tallow or coco fatty acid.
  • R ⁇ _ is hydrogen or a lower alkyl group, suitably with 1 to 6 carbon atoms and preferably hydrogen or a methyl group, x is 2 or 3 and y is suitably 1, 2, 3 or 4 and preferably 1, 2 or 3.
  • the group R 2 is suitably a methylene or ethylene group, preferably "a methylene group.
  • M is hydrogen or an ion from the groups alkali metals, alkaline earth metals, ammonium or sub ⁇ stituted ammonium such as for example mono-, di- or trihyd- roxyethy ⁇ ammonium. M is preferably alkali metal, especially sodium. It is particularly preferred that all groups B in the compounds of the above given general formulae are groups Q.
  • At least one of the amine groups in the amphoteric compounds is oxidized.
  • Useful compounds can be defined by the general formula (II)
  • M and B have the above given definitions.
  • the te " rm amine oxide is used to include also compounds wherein only some of the amine groups have been oxidized.
  • Especially preferred amine oxides are those of compounds according to formula (I) included in formula (III)
  • amine oxides of mixtures of amphoteric compounds with above given formulae with differ ⁇ ent values for y particularly mixtures of compounds wherein y is 1, 2 and 3.
  • the amine oxides can be prepared by reacting the amphoteric compound or the mixture of these with a per-com- pound such as a peracid or hydrogen peroxide under acid conditions. It is especially preferred to oxidize the amphoteric compounds with hydrogen peroxide and hereby the amount of hydrogen peroxide is suitably within the range of from 2 to 10 moles per mole amphoteric compound, preferably within the range of from 2 to 4 moles.
  • the temperature at the reaction is suitably within the range from ambient temperature to 60°C and preferably from around 20 to about 40°C.
  • an aqueous solution of the amphoteric compound with a concentration of from about 25 to about 40 per cent by weight and to oxidize this with an aqueous hydrogen peroxide solution having a concentration of from 35 to 75 per cent by weight.
  • the reaction is suitably carried out for a time of between 3 and 24 hours.
  • the obtained product is an aqueous solution of the amine oxides of the amphoteric compounds and can be used as such without isolation of the compounds. Residual hydrogen peroxide in the solutions can be removed by per se known methods.
  • the amine oxides of the present invention can be used for the same purposes as the amphoteric compounds them ⁇ selves are used and especially as surface active agents in detergent compositions and shampoo compositions, particu ⁇ larly in detergent compositions. They can hereby be used in combination with per se known conventional components in such compositions.
  • the invention also relates to detergent compositions containing the amine oxides.
  • the amine oxides are suitably used in amounts of from 0.3 per cent by weight, based- on the total detergent composition, and amounts up to 40 per cent by weight can be used.
  • the ' amine oxide are used particularly as surface active agents amounts of at least 2 per cent by weight are preferably used and especially amounts within the range of from 2 to 10 per cent by weight.
  • anionic and/or nonionic tensides and/or soaps are used.
  • Anionic tensides are suitably present in amounts of from 2 to 20 per cent by weight, whereby the amounts"- depend on the amount of amine oxide and lower amounts of anionic tensides are used with higher amounts of amine oxides.
  • the anionic tensides can for example be linear alkylbenzene sulfonate, secondary alkane sulfonate, al- cohol-ethoxy sulfate or alpha-olefin sulfonate.
  • the non ⁇ ionic tensides are suitably present in an amount of from 2 to 10 per cent by weight and can for example comprise alkoxylated compounds, such as fatty alcohols, alkyl phenols and alkyl amines.
  • the soaps are suitably present in amounts of from 2 to 4 per cent by weight and can for example comprise sodium- or potassium salts of tallow.
  • compositions can moreover comprise per se known components such as water glass, enzymes, builders such as phosphates, zeolites, NTA and carbonates, fillers such as sodium sulfate, carbonates and bicarbonates, bleach activators such as TAED (tetraacetylethylene diamine) or TAGU (tetra- acetylglucoluril) , diperoxy acids, foam regulators, per- fumes and colorants.
  • TAED tetraacetylethylene diamine
  • TAGU tetra- acetylglucoluril
  • the amine oxides can of course also be used together with the amphoteric compounds from which they are prepared and of course with other amphoteric compounds.
  • the detergent compositions are suitably in powder form and can be prepared in a conventional manner, such as by dry blending, agglomeration or . spray drying a slurry of the components.
  • the amine oxides are used in deter- gent compositions containing perborates or in liquid structured bleach compositions containing perborates for stabilization.
  • the bleaching at washing with such composi ⁇ tions is thereby enhanced.
  • Commercial detergent composi- tions usually contain perborates which in alkaline aqueous solutions release hydrogen peroxide. This is decomposed into H + and H ⁇ 2 ⁇ , which has a bleaching effect at washing.
  • the hydrogen peroxide is to a high degree decom ⁇ posed into ' free radicals, which do not have a bleaching effect, in the presence of metal ions which are commonly present in the wash water such as copper,, iron and man ⁇ ganese.
  • a common method for preventing the decomposition into free radicals is the addition of complexing agents, such as phosphonates and EDTA, to the detergent composi- tion.
  • complexing agents such as phosphonates and EDTA
  • part of the hydrogen peroxide is anyhow decomposed to free radicals at the washing.
  • complexing agents are also doubtful with regard to environment.
  • the amine oxides of the amphoteric compounds enhance the bleaching effect at washing in the presence of perborates. They can inhibit the decomposition of .hydrogen peroxide to free radicals at washing, which probably depends on their complexing abili- ty.
  • bleach activators are compounds which react further with the hydrogen peroxide, or the hydrogen peroxide sources, during the wash-process and form peroxicarboxylic acids which give the bleaching at lower temperatures.
  • One example of such a bleach activator is the commercial product TAED, tetraacetylethylene di- amine, which gives good bleaching effect at 40 to 60°C.
  • the present amine oxides also show good effect in stabiliz ⁇ ing perborates when a detergent containing perborate and TAED is used for washing.
  • the perborate in the detergent compositions can be present as mono- or tetrahydrate with an alkali metal, such as for example sodium, as positive counter ion.
  • Perborates are usually used in detergent compositions in amounts of from 6 to 30 per cent by weight, based on total composi ⁇ tion.
  • the amine oxides of the amphoteric compounds are for stabilization suitably used in a weight ratio to the . perborate of at least 1:20 and up to 1:3. When the amine .
  • the amounts in the detergent com ⁇ positions are suitably from 0.3 to 2 per cent by weight based on the detergent composition.
  • the upper limit is not critical since excess of the amine oxides will have other positive effects in the compositions.
  • This product is " commercially available under the trade name Ampholak 7T ⁇ ( R ' .
  • the concentration of the amphoteric compounds in aqueous solution was 30 per cent by weight.
  • hydrogen peroxide was added as a 35% aqueous solution.
  • the hydrogen peroxide was used in varying amounts calculated as moles of H2O2 per mole of amphoteric com ⁇ pound.
  • the oxidation was carried out both at a temperature of 20°C and 40°C.
  • Residual amount 70 60 57 45 20°C

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Oxydes aminés de composés amphotères ayant la formule générale (I), dans laquelle R est un groupe hydrocarbone ayant 7 à 22 atomes de carbone, R1 est hydrogène ou alkyle avec 1 à 6 atomes de carbone, x vaut 2 ou 3, y vaut 0 ou un entier de 1 à 4 et Q est (R2-COOM) où R2 est alkylène avec 1 à 6 atomes de carbone, M est H, un métal alcalin, un métal alcalino-terreux, un ammonium ou un ion ammonium substitué, et B est hydrogène ou est défini selon Q, au moins un des groupes aminés des composés étant oxydé. Les oxydes aminés peuvent être préparés par réaction du composé amphotère avec un percomposé, notamment avec du peroxyde d'hydrogène. Les oxydes aminés sont utiles dans des compositions de détergent et de shampooing et notamment dans des compositions détergentes renfermant des perborates.
PCT/SE1990/000813 1989-12-11 1990-07-12 Oxydes amines de composes amphoteres, leur preparation et leur emploi WO1991009100A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8904177A SE8904177D0 (sv) 1989-12-11 1989-12-11 Tvaettmedelskomposition
SE8904177-6 1989-12-11

Publications (1)

Publication Number Publication Date
WO1991009100A1 true WO1991009100A1 (fr) 1991-06-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1990/000813 WO1991009100A1 (fr) 1989-12-11 1990-07-12 Oxydes amines de composes amphoteres, leur preparation et leur emploi

Country Status (6)

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EP (2) EP0505427A1 (fr)
AT (1) ATE135037T1 (fr)
DE (1) DE69025728T2 (fr)
DK (1) DK0433257T3 (fr)
SE (1) SE8904177D0 (fr)
WO (1) WO1991009100A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8361946B2 (en) 2004-04-08 2013-01-29 Akzo Nobel N.V. Detergent composition

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0856577B1 (fr) * 1997-02-03 2004-05-06 The Procter & Gamble Company Compositions de nettoyage aqueuses liquides
DE102016201293A1 (de) * 2016-01-28 2017-08-03 Henkel Ag & Co. Kgaa Amphiphile, carboxyalkylierte Polyamine als Antiknitterwirkstoff
DE202016101250U1 (de) 2016-03-08 2016-04-27 Klaus Lokietz Transportbox

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3712918A (en) * 1972-05-31 1973-01-23 Millmaster Onyx Corp Amphoteric surface-active agents
EP0160507A2 (fr) * 1984-04-25 1985-11-06 Eric Graham Fishlock-Lomax Composition pour shampooing
EP0162600A1 (fr) * 1984-04-25 1985-11-27 Eric Graham Fishlock-Lomax Compositions de nettoyage
EP0214868A2 (fr) * 1985-09-10 1987-03-18 Berol Nobel Ab Agents tensioactifs à utilisation dans des compositions de nettoyage
EP0314648A2 (fr) * 1987-10-26 1989-05-03 Berol Nobel Ab Compositions détergentes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047168A (en) * 1988-01-21 1991-09-10 Colgate-Palmolive Co. Sugar ethers as bleach stable detergency boosters

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3712918A (en) * 1972-05-31 1973-01-23 Millmaster Onyx Corp Amphoteric surface-active agents
EP0160507A2 (fr) * 1984-04-25 1985-11-06 Eric Graham Fishlock-Lomax Composition pour shampooing
EP0162600A1 (fr) * 1984-04-25 1985-11-27 Eric Graham Fishlock-Lomax Compositions de nettoyage
EP0214868A2 (fr) * 1985-09-10 1987-03-18 Berol Nobel Ab Agents tensioactifs à utilisation dans des compositions de nettoyage
EP0314648A2 (fr) * 1987-10-26 1989-05-03 Berol Nobel Ab Compositions détergentes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8361946B2 (en) 2004-04-08 2013-01-29 Akzo Nobel N.V. Detergent composition

Also Published As

Publication number Publication date
DK0433257T3 (da) 1996-06-17
SE8904177D0 (sv) 1989-12-11
DE69025728D1 (de) 1996-04-11
DE69025728T2 (de) 1996-07-25
EP0505427A1 (fr) 1992-09-30
EP0433257A1 (fr) 1991-06-19
EP0433257B1 (fr) 1996-03-06
ATE135037T1 (de) 1996-03-15

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