DE1228365B - Detergent composition containing tertiary phosphine oxides - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

ClId

German class: 23 e - 2

Number: 1228 365

File number: P 28961IV a / 23 e

Filing date: March 10, 1962

Opening day: November 10, 1966

The invention relates to detergent substances, namely new tertiary phosphine oxides, and detergents, which contain these tertiary phosphine oxides.

As organic detergents continue to improve, it has been found that certain Properties are very desirable. These include resistance to hardness builders and high detergency and solvency for hard water soaps such as lime soap. True, there are a number of organic ones Detergents with these properties, however, find detergent substances that also have more have desirable properties, a wider field of application.

Thermal stability is a very desirable property that many detergents lack. These Stability is particularly advantageous when detergents are used during use or processing, E.g. when spray drying granular detergents that are exposed to heat.

As further desirable properties of organisehen Detergents are among the bacteriostatic effectiveness as well as resistance to hydrolysis common conditions of use.

Another advantageous property of organic detergents is their low hygroscopicity. Hygroscopic detergent substances in bar soap or granular detergents impair the Use value of these products. Bar soap becomes soft and greasy, and granular detergents tend to care caking lose their flowability and no longer dissolve quickly.

The invention relates to a detergent composition containing tertiary phosphine oxides of the general formula RR'R "P -> O, in which R is an alkyl, alkenyl or monohydroxyalkyl radical with 10 to 18 carbon atoms and R 'and R " Denote alkyl or monohydroxyalkyl radicals having 1 to 3 carbon atoms.

The phosphine oxides used in the present invention are likely to be resonance hybrids as follows Border structures:

R '

The detergents according to the invention have excellent detergency and dissolving power for Alkaline earth soaps as well as resistance to hydrolysis and do not form with calcium and magnesium

Containing tertiary phosphine oxides
Detergent composition

Applicant:

The Procter & Gamble Company,

Cincinnati, Ohio (V. St. A.)

Representative:

Dipl.-Chem. Dr. H. G. Eggert, patent attorney,

Cologne-Lindenthal, Peter-Kintgen-Str. 2

Named as inventor:

Robert Gene Laughlin, Cincinnati, Ohio;

John Thomas Yoke, Tucson, Ariz. (V. St. A.)

Claimed priority:

V. St. ν. America March 17, 1961 (96 383)

water-insoluble soaps. They are bacteriostatically effective and also have thermal stability, low hygroscopicity and high detergency in cold water. The latter property is special Desirable in areas where hot water is not readily available, and when washing Fabrics such as wool and wrinkle-resistant fabrics which are adversely affected by hot water.

Examples of the compounds used according to the invention are dodecyldimethylphosphine oxide, Tetradecyldimethylphosphine oxide, tetradecylmethylethylphosphine oxide, Cetyldimethylphosphine oxide, stearyldimethylphosphine oxide, cetylethylpropylphosphine oxide, Dodecyl diethylphosphine oxide, tetradecyl diethylphosphine oxide, dodecyldipropylphosphine oxide, Dodecyldi- (hydroxymethyl) phosphine oxide, dodecyldi- (2-hydroxyethyl) phosphine oxide, tetradecylmethyl-2-hydroxypropylphosphine oxide, Oleyldimethylphosphine oxide and 2-hydroxydodecyldimethylphosphine oxide.

Tertiary phosphine oxides as a general class of compounds are known. However, it was surprising found that the special trialkylphosphine oxides described above are extremely effective organic due to their properties Represent detergents.

609 710/286

Only certain tertiary phosphine oxides have the properties listed above. With these particular ones Phosphine oxides R, R 'and R "must have the meanings given above. If R is more contains more than 18 or less than 10 carbon atoms, the desired detergency, foam properties and the solvency for hard water soaps is not achieved. Likewise, the products do not have these properties and no bacteriostatic activity if R 'and R "contain more than 3 carbon atoms.

Of the tertiary phosphine oxides, the C ₁₀ - to C ₁₈ -alkyldimethylphosphine oxides, in particular the C ₁₂ - to C ^ -alkyldimethylphosphine oxides, are preferably used. The C ₁₀ - to Cjg-Alkyldimethylphosphinoxde have very good bacteriostatic effectiveness against Gram-positive bacteria. (The results of some experiments also show effectiveness against gram-negative microorganisms.) These phosphine oxides are also hygroscopic to the desired low degree. Their solubility in water is higher than that of the C ₁₀ to C ₁₈ alkyl diethyl and dipropylphosphine oxides. The last-mentioned phosphine oxides, however, have a higher solubility in oils (e.g. higher fatty triglycerides) than the dimethyl compounds. Despite the lower solubility of the diethyl compounds, their washing properties are just as good as those of the dimethyl compounds.

The alkenyldimethylphosphine oxides are not hygroscopic to the desired minor extent as are the corresponding alkyldimethylphosphine oxides. However, the alkenyl compounds have a certain thermal stability. The tertiary phosphine oxides in which R, R 'or R "is an α-monohydroxyalkyl group do not have the high heat resistance as the compounds in which R, R' or R" is an alkyl group. When the hydroxyl substituent in the monohydroxyalkyl radical is not in the α-position, e.g. B. in the ß- or / position, a certain thermal stability can be achieved. The monohydroxyalkyldimethylphosphine oxides are not hygroscopic to the extent desired.

The tertiary phosphine oxides, for their production within the scope of the present invention no patent protection is claimed can be prepared by methods similar to the known tertiary Phosphine oxides. These methods are from K. Darrell Berlin and George B. Butler in Chemical Reviews ", Vol. 60, June 1960, pp. 243-259. In general, according to the Invention eligible tertiary phosphine oxides by oxidation of the corresponding tertiary Phosphines, for example with hydrogen peroxide, are produced.

In the tertiary phosphine oxides according to the invention, R can be derived from natural fats and oils or from synthetic products. Mixtures of phosphine oxides in which the chain length of the radicals R _{varies in the range from C 10} to C ₁₈ , as is the case, for example, with the alkyl radicals from coconut fatty alcohol (or distilled coconut fatty alcohol), are very suitable.

The compounds according to the invention are useful as such as detergents and surface-active compounds usable. Appropriately, they are used with other substances to detergents, in particular to solid products such as bar soap, flakes or granular detergents. These detergents can be about 5 to 80% of the tertiary phosphine oxides according to the invention and about 20 to 95% anion-active organic detergents, nonionic organic detergents, water-soluble inorganic ones Contain alkali salts as builders, organic complexing agents or mixtures thereof.

Granular or flaky detergents preferably contain about 5 to 50% of those according to the invention Phosphine oxides. Bar soap contains around 5 to 50% of these phosphine oxides when used with anionic active ingredients Detergents, e.g. B. soap, and optionally with alkaline or organic builders or inert fillers are used. Bar products contain about 40 to 80% of phosphine oxides optionally contained according to the invention as the only detergent substance, while the rest consists of inert fillers or builders.

Both soap and synthetic detergents are suitable as anionic organic detergents used alone or in a mixture. Suitable soaps are, for example, the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C ₁₀ to C ₂₀ ). The sodium and potassium salts of the fatty acid mixtures obtained from coconut oil and tallow, ie sodium or potassium tallow and coconut soap, are particularly advantageous. Examples of anion-active organic synthetic detergents are: alkyl glyceryl ether sulfonates, alkyl sulfates,. Alkyl monoglyceride sulfates or sulfonates, alkyl polyglycol ether sulfates, acyl sarcosinates, acyl esters of isethionates, acyl-N-methyl taurides, alkylbenzenesulfonates, alkylphenol polyglycol ether sulfonates. In these compounds, the alkyl radicals and the acyl radicals each contain 10 to 20 carbon atoms. They are in the form of the water-soluble salts, e.g. B. the sodium, potassium, ammonium and alkylolammonium salts are used. Specific examples are sodium lauryl sulfate, potassium N-methyl lauroyl tauride and triethanolamine dodecylbenzenesulfonate.

Examples of non-ionic organic detergents are: Polyethylene oxide condensates of alkylphenols in which the alkyl radical contains 6 to 12 carbon atoms (e.g. tert-octylphenol) and the amount of ethylene oxide is equal to a molar ratio of ethylene oxide to alkylphenol Range from 10: 1 to 25: 1; the condensation products of ethylene oxide with the product of the reaction of propylene oxide and ethylene diamine with a molecular weight of the condensation products of 5,000 to 11,000; the coridation products of about 5 to 30 moles of ethylene oxide with 1 mole of a straight-chain or branched aliphatic alcohol with 8 to 18 carbon atoms (e.g. lauryl alcohol) and C ₁₀ - to C ₁₈ -A ^ yWi- (C ₁ -C ₂ -alkyl) -amine oxides (e.g. dodecyldimethylamine oxide).

As water-soluble inorganic alkali salts, which are used as builders alone or in a mixture, Alkali carbonates, borates, phosphates, polyphosphates, bicarbonates and silicates are suitable. Specific examples of such salts are sodium tripolyphosphate, sodium carbonate, sodium tetraborate, sodium pyrophosphate, Sodium bicarbonate, potassium tripolyphosphate, sodium hexametaphosphate, sodium sesquicarbonate, Sodium mono- and di-orthophosphate and potassium bicarbonate. These inorganic salts increase the detergency of the invention used phosphine oxides.

5 6

As organic complexing agents, alone or in fen. The ether layer was twice with 200 cm ³

Mixtures are used, for example, a 20% Na ₂ SO ₄ solution washed. the

wise alkali aminopolycarboxylates, e.g. B. Sodium ether layer was dried _{over CaSO 4.} Of the

and potassium ethylenediamine tetraacetate, sodium and residue was then with a micro-Claisen-

Potassium N- (2-hydroxyethyl) ethylenediamine triacetate, 5 apparatus distilled. The weight of the received

Sodium and potassium nitrilotriacetate and sodium dodecyldimethylphosphine was 26.7 g (yield

and potassium N- (2-hydroxyethyl) nitrile diacetate. Also 43%).

mixed salts of these polycarboxylates can add 24.2 g of this dedecyldimethylphosphine (0.105

be turned. The alkali salts of phytic acid, mol) were at room temperature with 500 cm ^{3 of} water

z. B. sodium phytate, are also suitable as organic io ser and 135 cm ^{3 of} 3% H ₂ O ₂ (0.119 mol) stirred.

Sche complexing agent (see U.S. Patent 2739942). The temperature rose to 44 ° C. The reaction pro-

The preferred detergents contain about 10 bis dukt has then been subjected to freeze drying.

30% of the tertiary phosphine oxides according to the invention were obtained 23.5 g of dodecyldimethylphosphine

manure and at least the same amount of sodium trioxide (yield 91%).

polyphosphate. Expediently, in these 15 The elemental analysis of the product obtained

Added detergents containing C ₁₂ to C ₁₄ alkyldimethyl had the following result:

phosphine oxides used. Calculated C 68.5%, H 12.6%, P 12.6%;

Dodecyldimethylphosphine oxide, the good foam found .... C 68.1%, H 12.5%, P 12.6%. has properties.

The detergents or cleaning agents according to the invention described in Example 1 above can be used as desired and can essentially be summarized in the following equations: auxiliaries, diluents and additives:
hold, e.g. B. ampholytic detergents, cationic detergents, perfumes, means of connection- ^RBr + ^M S -> RMgBr (1)
fogging and preventive measures 25 2 RMgBr + CdCl

the repositioning of the dirt, bacteriostati- _ ^ m \ qj + ² MeCl + MeBr (2)

see agents, dyes, fluorescers, foaming agents, ² 22

Antifoam agents and the like (R ^ Cd + 2 PCl ₃

-► 2 RPCl ₂ + CdCl ₂ (3)

B is ρ ie 1 1 3o _RFC ^ _{+ R} , _{MgI + R} " _MgI

274 g dodecyl bromide (1.1 mol) in 1100 cm ³ ether "* ^RR ' ^R " ^P + ^M S ^C1 2 + W ₈ ( ⁴ )

(Diethyl ether) were added to 24.3 g of magnesium turnings RR'R "P + H ₂ O ₂ ^ RR'R" P- ^ O + H ₂ O (5) (1.0 mol) in 1100 cm ^{3 of} ether. The addition

took place over a period of 70 minutes. The 35 where R, R 'and R "have the meanings already mentioned

obtained dodecyl magnesium bromide (Grignard's gene have.

Reagent) in ether was chilled in ice. To this (These reactions are not quantitative, however;

The reagent was 100.8 g of cadmium chloride (0.55 mol), some side reactions take place.)

given. The mixture obtained was then subjected to 2 hours in the reactions represented by the equations im

vigorously stirred. 40 Example 1 were shown for this mixture, as well as in the reactions

171.8 g of PCl ₃ (1.25 mol) were added to 1000 cm ^{3 of} ether. those represented by the equations in Example 2

During this addition, over a period of time, the desired alkyl radicals in RR'R "P

60 minutes took place, the mixture was vigorously -> 0 by choosing the appropriate reaction

stirs. The temperature was kept at -50 ° C. products are received. For example, if a dodec

The resulting mixture was desired for an additional 60 minutes 45 cylmethylpropylphosphine oxide is

stirred at this temperature and stand for 16 hours - the reaction represented by equation (4) each

calmly. It was then filtered and the lower 1 mole of methyl magnesium iodide and propyl magnesium

hit washed with 800 cm ^{3 of} ether. The lower iodide is used. However, in such a re-

blow was discarded. The ether became from the filtrate action a coarse mixture of phosphine oxides, the

distilled off. The residue was distilled twice, containing this compound, to be obtained

lates. The water solubility of Dodecyldimethylphos-

The boiling fraction contained predominantly dichlorododephine oxide at room temperature was 5%. The ther-

cylphosphine. the stability of this connection is excellent

73.8 g of dichlorododecyl phosphine distillate (0.272 mol) net. After heating for 2 hours at 175 ° C. in stickin 300 cm ^{3 of} ether, it was practically unchanged with a material made from 84.0 g. The compound methyl iodide and 14.6 g magnesium metal in 1200 cm ³ resists hydrolysis to a high degree and the Grignard reagent produced in ether is degraded only by the action of force, e.g. B. enforces. ^{The reaction was carried out at 5 °} C. in a bath consisting of ice and salt, alkali melt or acidification at high temperature. The fact that dodecyldimethylphosphine oxide, a crystalline Nard's reagent was added to the mixture of dichloro solid, is only very slightly hygroscopic, dodecylphosphine and ether can be seen drop by drop over a period of 60 minutes after standing in the moist for several days. The reaction room air did not lose its crystal form. Much mixture was stirred for 1 hour after the addition. Other crystalline organic detergents were then carefully mixed with 140 g of NH ₄ Cl in 500 cm ^{3 of} syrupy masses when they were subjected to the same test under water. Then 110 g of Na ₂ SO _{4 were} thrown into 65. ^{He added 600 cm 3 of} water to further quantitative tests in order to give the desired result that the amount of water which this compound produced was salted out to form the ethereal layer. The layers at 21 ° C and a relative humidity of 80% were separated, the water layer was absorbed, is very low (0.2% of the sample weight).

The bacteriostatic effectiveness of dodecyldimethylphosphine oxide was determined. In a aqueous matrix was already with a concentration of 17.5 to 19 ppm of this compound bacteriostatic point for aureus muscle (gram-positive) reached. The bacteriostatic point is concentration the connection in which germ growth and reproduction are prevented. This high bacteriostatic effectiveness is remarkable.

Example 2

34.5 g of sodium (1.50 mol) were reacted with 291 g of dibutyl phosphite (0.50 mol) for 2 hours at 100 ° C. with stirring. To this reaction mixture, 414 g (1.50 mol) of tetradecyl bromide was added over a period of 45 minutes at the same temperature. The mixture was then stirred for 6 hours. After cooling, the mixture was ^{washed with 1500 cm 3 of} water and 250 cm ^{3 of} 2% strength aqueous acetic acid and then twice more with 2% strength aqueous acetic acid. The heptane was distilled off and then the mixture was distilled.

362 g of the ^{dibutyl tetradecanephosphonate obtained were hydrolyzed with 1550 cm 3 of} hydrobromic acid to give tetradecanephosphonic acid. The butyl bromide formed was removed by distillation.

192 g of the tetradecanephosphonic acid (0.69 mol) were reacted _{slowly with 316 g of PCl 5} (1.52 mol) on a steam bath and under a stream of _{N 2.} The reaction mixture was heated with steam for 30 minutes. Then SO _{2 was} bubbled through the mixture for 90 minutes. Volatile impurities were removed with a vacuum pump.

62.3 g of the tetradecanephosphonyl dichloride obtained (0.2 mol) in 150 cm ^{3 of} ether were reacted with 0.6 mol of methyl magnesium chloride (Grignard's reagent) at -73 ° C. The reaction mixture was stirred at room temperature for 6 hours and left to stand for 16 hours. Then 498 cm ^{3 of} a semisaturated NH ₄ Cl solution were added. Two layers formed. The ether layer was removed and the aqueous layer was extracted with ether. The ether layer and the ether extract from the aqueous layer were mixed and then dried.

34 g of tetradecyldimethylphosphine oxide were obtained (yield 62%). The product was distilled (Boiling point 138 to 140 ° C at 1 mm Hg) and recrystallized once from hexane. Analysis of the product resulted in the following values:

This procedure is summarized below:

Il

NaP (OC ₄ H ₉ ), + RBr
O

RP (OC ₄ H ₉ ) ₂ + NaBr

RP (OC ₄ H ₉ ), + 2 HBr
O

RP (OH) ₂ + 2C ₄ H ₉ Br

RP (OH) ₂ + 2 PCl ₅
O

RPCl ₀

RPCL + 2POCL + 2HCl

+ R'MgCl + R "MgCl
RR'R'T- ^ O + 2 MgCl ₂

Calculated .. C 70.00%, H 12.75%, P 11.30%; found ... C69.8%, H 12.7%, P 11.0%.

Tetradecyl diethylphosphine oxide was prepared in a similar manner, except that ethyl magnesium chloride was used used in place of methyl magnesium chloride in an equivalent molar amount.

Dodecyl diethylphosphine oxide was prepared by the same procedure except that instead of tetradecyl bromide, dodecyl bromide was used in an equivalent molar amount.

Using a method similar to that described in Example 2, dodecyldimethylphosphine oxide, Octadecyldimethylphosphinoxyd and Octadecyldiäthylphosphinoxyd produced. The essential equi- (The However, reactions are not quantitative; some side reactions take place.)

To determine the washing properties of the phosphine oxides used according to the invention, the Ability of these compounds to remove lipid soiling from fabrics was measured. To this end test strips with a certain amount of artificial lipid soil (a mixture of Olive oil, stearic acid, oleic acid and tallow fatty alcohol). These soiled test strips were washed in a tergotometer using water having a temperature of 60 ° C and contained 0.10 percent by weight of the product to be tested. (The test with the tergotometer is described in "Detergency Evaluation and 'Testing" by J. C. Harris, Interscience Publishers, Inc. [1954], p. 60.) The test strips are weighed dry before and after washing. The washing effect The lower the amount of residual lipid soiling expressed as a percentage, the better is.

When using soft water with 0.10% dodecyldimethylphosphine oxide, 34.9% remained Dirt back. In the same test, sodium dodecylbenzenesulfonate, a widely used one Active detergent for heavy duty detergents, the remaining amount of dirt 52.4%. Dodecyldimethylphosphine oxide is therefore superior to dodecylbenzenesulfonate in terms of detergency. It achieves the washing effect of sodium tallow alkyl sulphate, which is one of the best detergent substances available on the market coarse and mild detergents are used.

When used under the same conditions in the tergotometer test described above with Water of 12 ° d.H. were with dodecyldimethylphosphine oxide (as an organic detergent) in one

Detergents containing builders (20% organic detergent, 50% sodium tripolyphosphate and 30% sodium sulfate) obtained results that were better than those obtained with dodecylbenzenesulfonate and matched the results obtained with talc alkyl sulfate.

Detergents containing builders that contained 30% sodium sulfate, 50% sodium tripolyphosphate and 20% dodecyldimethylphosphine oxide, dodecyl diethyl phosphine oxide, tetradecyl dimethyl phosphine oxide or tetradecyl diethyl phosphine oxide, but those which contained the same detergents containing detergent sulfone oxide (which, of course, contained detergent stains) of the same composition when removing lipid soiling (of course) , was superior and achieved the detergent effect of the same detergents containing tallow alkyl sulfate. The same basic mixture, which, however, contains octadecyldimethylphosphine oxide or octadecyl diethylphosphine oxide, has satisfactory washing properties, but they are not as good as the detergents containing the C ₁₂ and C ₁₄ homologues.

The phosphine oxides described above all had good solvency for lime soap as well a thermal stability similar to that described above for dodecyldimethylphosphine oxide was comparable.

Granular detergents of the following composition were produced:

17.5% dodecyldimethylphosphine oxide,

23.0% sodium sulfate,

50.0% sodium tripolyphosphate,

6.0% sodium silicate,

3.5% water.

A 0.436% aqueous solution of this detergent was used to clean dirty dishes second hand. The water had a temperature of 46 ° C and a hardness of 12 ° d.H. By mechanical stirring for 40 seconds formed a stable foam of more than 2.5 cm in height.

The phosphine oxides according to the invention can be used in cleaning agents with the following composition will:

Granular detergent

10% dodecyl diethylphosphine oxide,

10% sodium dodecylbenzenesulfonate (with tetrapropylene-derived dodecyl residue),

50% sodium tripolyphosphate,
30% sodium sulfate.

Piled toilet bar soap

Granular detergent

10% tetradecyldimethylphosphine oxide,

10% condensation product of 1 mole of nonylphenol

and 9 moles of ethylene oxide,
50% sodium pyrophosphate,

3% sodium carbonate,

3% trisodium phosphate,
24% sodium sulfate.

Piled toilet bar soap

10% dodecyldimethylphosphine oxide,
15% soda soap from coconut oil,
60% soda soap made from tallow,
15% water.

55

60 50% dodecylmethylethylphosphine oxide,
25% sebum fatty acid,
15% water,

5% corn starch,

5% triethanolamine ethylenediamine tetraacetate.

Abrasives

85% silica powder,

15% detergent, consisting of 85% trisodium phosphate and 15% dodecylmethyl-2-hydroxyethylphosphine oxide.

If the washing-active phosphine oxides according to the invention, in particular the C ₁₀ - to C ₁₈ -alkyldimethylphosphine oxides, are combined with the water-soluble inorganic alkali salts or organic complexing agents of the above-mentioned type serving as builders, heavy duty detergents of excellent effectiveness are obtained in both cold and hot water . "Cold" is to be understood as meaning water temperatures of 10 to 38 ° C., in particular 16 to 32 ° C., while "hot" refers to the temperatures used in conventional laundry, ie of 38 ° C. and above. It is completely surprising that the phosphine oxides according to the invention, when used in heavy duty detergents, have an excellent washing effect in cold water. They are much more effective in this regard than soap, such as coconut oil soap, and also more effective than the detergent actives commonly used in heavy duty detergents, such as alkylbenzene sulfonates and alkyl sulfates.

It was found that, in addition to the above-described, phosphine oxides as detergent substances containing detergents and cleaning agents extremely effective coarse detergents in homogeneous liquid form with the preferred phosphine oxides. These liquid Detergents can contain: about 4 to 15% preferred phosphine oxides according to the invention, 0 to about 12% anionic and / or nonionic detergent substances of the type described above, about 5 to 15% of a solubilizer, e.g. B. a low molecular weight aryl sulfonate (e.g. sodium or Potassium toluene or xylene sulfonate) and about 8 to 30% of a water-soluble inorganic Alkali salt as a builder or an organic complexing agent of the type described above, remainder Water. Up to about 5% sodium silicate can advantageously be used as a corrosion inhibitor in these detergents be admitted. The following recipe is an example of a homogeneous, liquid heavy duty detergent, the excellent foam properties and excellent washing performance both in cold and cold also in warm water has:

6% sodium dodecylbenzenesulfonate (with tetrapropylene-derived dodecyl residue),

6% alkyldimethylphosphine oxide (where the alkyl group is a mixture of lauryl and myristyl radicals),
20% potassium pyrophosphate,

8 «/ ο toluenesulfonate,

3.8% sodium silicate solids,

0.3% carboxymethyl hydroxyethyl cellulose,

0.3% perfume,

Rest water.

609 710/286

Claims (3)

Patent claims: 1. detergent composition, characterized by a content of tertiary phosphine oxides of the general formula RR'R "P -> ■ 0, in which R is an alkyl, alkenyl or monohydroxyalkyl radical having 10 to 18 carbon atoms and R 'and R "are alkyl or monohydroxyalkyl radicals with Mean 1 to 3 carbon atoms. 2. Detergent composition according to claim 1, characterized by a content of the tertiary Phosphine oxides from 5 to. 80%, 3. Detergent composition according to claim 1, characterized by a content of alkyldimethylphosphine oxides with alkyl radicals with a chain length of 12 to 14 carbon atoms. Considered publications: German Patent No. 1038 692; Belgian Patent No. 450,966; U.S. Patent Nos. 2,656,372, 2693 482, 724 718.2 765 279.2 774 786.2 784 208.2 913 498; Chemical Reports, 94, pp. 392 to 397 (1961); Chemisches Zentralblatt, p. 5177 (1953); Proceedings of the Chemical Society, 10, p. 351 (I960); Kosolapoff, Organophosphorus Compounds, 1950, pp. 42, 61, 98, 99,123,124,139.