US3359208A

US3359208A - Detergent composition

Info

Publication number: US3359208A
Application number: US559706A
Authority: US
Inventors: Cahn Arno; Thaddeus J Kaniecki
Original assignee: Lever Brothers Co
Current assignee: Lever Brothers Co
Priority date: 1962-02-15
Filing date: 1966-06-23
Publication date: 1967-12-19
Anticipated expiration: 1984-12-19

Description

United States Patent 3,359,208 DETERGENT COMPOSITION Arno Calm, Pearl River, and Thaddeus J. Kaniecki, Brooklyn, N.Y., assignors to Lever Brothers Company, New York, N.Y., a corporation of Maine No Drawing. Original application Feb. 11, 1965, Ser. No. 431,982, now Patent No. 3,267,135, dated Aug. 16, 1966. Divided and this application June 23, 1966, Ser. No. 559,706

8 Claims. (Cl. 252-137) ABSTRACT OF THE DISCLOSURE A group of N-(Z-hydroxyalkyl)-N-rnethyltaurine-N- oxides is disclosed which have particular value as the active detergent component in heavy duty detergent formulations. Synthesis procedure for preparing the compounds is also disclosed.

This is a division of our copending application Ser. No. 431,982 filed Feb. 11, 1965, now Patent No. 3,267,- 135, which in turn was a continuation-in-part of our copending application, Ser. No. 173,377, now Patent No. 3,171,787.

This invention relates to detergent compositions containing N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides or alkali metal salts thereof as active ingredients.

The compounds,

where R is an alkyl group having from 8 to 18 carbon atoms, and M is selected from the group consisting of hydrogen and alkali metals, have been discovered.

The novel N-(2-hydroxyalkyl)-N-methyltaurine-N-oxides are excellent surface-active agents and show detergency characteristics both alone and in the presence of conventional builder salts, such as alkali metal sulfates, carbonates, silicates, phosphates, borates, and mixtures thereof. The presence of conventional detergent builders generally improves the detergency of the compositions. Additional components, such as carboxymethylcellulose which improves the dirt suspending properties of the Washing solution, may be used. Also, other synthetic detergents, soaps, perfumes, abrasives, foam stabilizers, germicidal agents, coloring agents and the like, may be included in the detergent compositions of this invention. Accordingly, they are useful in dish washing detergents, non-soap bars, soap bars, bars containing mixtures of soaps and non-soaps, shampoos, and to other applications known to those skilled in the art where surface active properties are desired.

As will be noted below, another significant advantage of the compounds of this invention is that the compounds within the series having the best detergent characteristics are those where R has a chain length of 13 to 18 carbon atoms, and can thus be obtained from less expensive raw materials.

The N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides of this invention are prepared by the oxidation of the corresponding N-(Z-hydroxyalkyl)-N-methyltaurine, according to the following equation:

OH CH3 1 I ROHCHaIlICHzCHzSOaM 1120 R and M having the same meaning as given above. While hydrogen peroxide is the preferred oxidizing agent, others, such as ozone, which have been described in the literature for the conversion of amines to amine oxide may be used.

The N-(2hydroxyalkyl)-N-methyltaurine may be prepared with ease from starting materials which are relatively inexpensive and commercially available. A desirable method of preparing these compounds is by the simple addition of N-methyltaurine to a long chain 1,2-epoxyalkane. This simple addition technique produces the desired N-(Z-hydroxyalkyl)-N-methyltaurine, and the reaction product is free from inorganic salts which are difficult to remove. The preparation of the epoxide starting material may be by conventional methods such as oxidation of the compounds derived from petroleum sources.

The following examples describe the preparation and characteristics of the compounds of this invention, and

Example 1 A series of the novel compounds of this invention was prepared according to the following general procedure.

60 ml. of 30% hydrogen peroxide (0.536 mole) were slowly added to a warm alcoholic solution of sodium N-(Z-hydroxyalkyl)-N-methyltaurine, prepared by dissolving 0.134 mole of sodium N-(Z-hydroxyalkyD-N- methyltaurine in 350 ml. of 95% ethyl alcohol. The resultant solution was maintained at -50 C. for 24 hours. The excess hydrogen peroxide was then decomposed by placing a 1" x 2" piece of platinum foil into the solution and allowing it to remain there for 2 to 4 days. When gas bubbles no longer formed on the surface of the platinum, it was removed from the reaction solution and the solvent was evaporated off. The last traces of solvent were removed by drying the residue at reduced pressure. The residue was finely powdered and suspended in 200 ml. of acetone. The suspension was warmed to 40 C., filtered and the product air dried. Final drying was for 6 hours in a vacuum oven at 30 mm. and 50 C. Table I lists the compounds prepared with this procedure.

Example 2 A series of N (Z-hydroxyalkyl)-N-methyltaurine-N- oxides was prepared by the method of Example 1 and tested for detergency by the Terg-O-Tometer Detergency Test. This test gives an empirical measurement of the amount of soil removed from the fabric under simulated washing conditions. Sample swatches of cloth soiled in a standard manner with a standard soil are placed in a miniature washing machine, the Terg-O-Tometer apparatus, and laundered in the presence of a measured amount of detergent and water of a standard hardness. A Terg-O- Tometer apparatus is described in the Journal of the American Oil Chemists Society, vol. 27, May 1950, pp.

153-159. After rinsing and drying, the reflectance of the cloths is measured and compared with the reflectance of the soiled cloths before washing.

In the detergency test referred to herein, the Terg-O- Tometer apparatus was maintained in a water bath adjusted to maintain the temperature of the washing solution at 120 F. '2 F. The paddle oscillation was brought to ninety complete cycles per minute and the paddle oscillated through a 320 arc.

With the agitators in position on the machine, the detergent was added in the desired amount to the washpot of the machine. 1250 ml. of water having a hardness of 180 ppm. CaCO (60 parts magnesium and 120 parts calcium calculated as calcium carbonate) were added. The machine was started and the solution agitated until the detergent was dissolved.

Cloth swatches approximately 4% inches by 6 inches were then added and were washed for twenty minutes, after which the test swatches were removed from the solution and hand squeezed. The washpot was refilled with clear rinse water of the same hardness used for washing at a temperature of 120 F. ;2 F., and, with the agitators running, the cloths were rinsed for minutes. The cloths were then removed, hand squeezed and ironed dry. The reflectance of the cleaned cloths was measured with the Hunter Reflectometer using the green filter.

The Terg-O-Tometer test was carried out in duplicate. The reflectance values in the table below represent the average of the actual reflectance readings taken from eight cloth swatches. Each of the N-(2-hydroxyalkyl)-N- methyltaurine-N-oxides was evaluated alone and in the presence of tetrapotassium pyrophosphate, a conventional builder. Table II summarizes the results obtained.

TABLE II Terg-O-Tometer-Homologous series of sodium N-(2- hydroxyalkyl)-N-methyltaurine-N-oxides of formula:

Sodium N-(Z-hydroxyalkyl)-N-methyltaurine-N-0xides were prepared from sodium N-(Z-hydroxyalkyl)-N-methyltaurines, which were in turn prepared by reacting N- methyltaurine with a 1,2-epoxyalkane mixture in which the alkane portion had, in one case, carbon chain lengths ranging from C to C and in the other case, from C to C The method of preparation described in Example 1 was employed. These compounds were evaluated by the Terg-O-Tometer Test, both alone and in the presence of tetrapotassium pyrophosphate. The mixed alkyl products showed slight detergency alone and gave a good-toexcellent response to building. Table III below gives the results of these evaluations.

4 TABLE 111 Terg-O-Torneter Tests of sodium N-(Z-hydroxyalkyD- N-methyltaurine-N-oxides of formula:

'Tetrapotasslum pyrophosphate.

Example 4 Three compounds of this invention were evaluated according to the RAP Mildness Evaluation Test for Detergents. In this test, a 2% aqueous solution of the compound was tested on rabbit skin and the results rated according to the following scale.

Mildness rating:

0No epidermal erosion (very mild) l-Foci or small patches of erosion (fair mildness) 225% to 50% destruction of epidermis (irritating) 3-Greater than 50% epidermal erosion (very irritating) Table IV below gives the compounds tested and the results of the test.

TABLE IV Compound Mildness Remarks Rating Sodium N(2-hydroxydodecyl)-l l- 0 Epidermis methyltaurine-N-oxide. normal. Sodium N-(2-hydroxytetradoeyD- 0 Do.

N-niethyltaurine-N-oxide. Sodium N-(2-hydroxyoctadecyl)- 0 Do.

N-methyltaurine-N-oxide.

The compounds of the present invention are also of exceptional utility in the preparation of heavy-duty detergent formulations. Because such formulations are commonly used in combination with hypochlorite bleaches, it is important that they exhibit good sudsing and suds stability in the presence of such bleaches.

Example 5 Using the above described formulation, test solutions Were made by diluting the powdered detergent in water at a concentration of 3.59 ozs./ 16 gals.

Test Cond tions Foam Volume, ml.

Vacuum N Bleach With Bleach 1 Water Foam Gleaner Hardness Booster Dirt RF. 2 ES. 3 RF. F.S

0 Yes 90 40 100 40 sufficient sodium hypochlorite bleach was used to provide 200 p.p.m. of available chlorine.

2 Foam formation, mins.

3 Foam stability, 5 mins.

4 The foam formation and stability was tested in the presence of 0.05% vacuum cleaner dirt.

5 Laurie isopropauolamide was added at a concentration correspondng to 2.9% by weight of the basic test formulation.

The following are typical heavy-duty detergent formulations which may be used. These formulations, if tested as described in Example 5, Will yield similar improvements in foam formation and foam stability in the presence of a hypochlorite bleach.

Percent N (2-hydroxyoctadecyl)-N-methyltaurine-N-oxide 10 The nonylphenol-ethylene oxide adduct contains an average of 6 moles of ethylene oxide.

N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxide 2 10 Sodium tripolyphosphate 15 Tetrasodium pyrophosphate 35 Laurie isopropanolamide 3 Carboxymethylcellulose 0.3 Water 10 Sodium sulfate 26.7

The alkyl group is a mixture of Clg-CQO alkyl groups.

N-(Z-hydroxydodecyl)-N-methyltaurine-N-oxide 5 Linearalkylbenzenesulfonate (Na) 3 10 Coconut fatty acid monoethanolamide 3 Tetrasodium pyrophosphate 35 Sodium tripolyphosphate 15 Water 8 Sodium sulfate 24 3 The alkyl portion of the linear alkylbenzenesulfonate has an average of 12 carbon atoms.

Sodium C C alcohol-3-ethylene oxide sulfate 5 N (2 hydroxytetradecyl)-N-methyltaurine-N- oxide 5 Tetrapotassium pyrophosphate 40 Coconut fatty acid monoethanolamide 4 Laurie isopropanolamide 4 Sodium xylenesulfonate 3 Carboxymethylcellulose 0.3 Water 10 Sodium sulfate 28.7

N (2 hydroxyoctadecyl) N-methyltaurine-N- Oxide 3 C -C alcohol-7.5-ethylene oxide 7 Coconut fatty acid monoethanolamide 5 Carboxyrnethylcellulose 0.3 Sodium toluenesulfonate 8 Tetrapotassium pyrophosphate 50 Water 26 Sodium sulfate 16.7

We claim: 1. A detergent composition consisting essentially of a compound of the formula wherein R is an alkyl group having from 8 to 18 carbon atoms and M is selected from the group consisting of hydrogen and the alkali metals in an amount suflicient to impart detergency to said composition and an inorganic builder salt in an amount effective to improve the detergency of said compound.

2. The detergent composition of claim 1, wherein the compound is a N-(Z-hydroxyhexadecyl) -N-methyltaurine- N-oxide.

3. The detergent composition of claim 1, wherein the compound is a N-(Z-hydroxyoctadecyl)-N-methyltaurine- N-oxide.

4. The detergent composition of claim 1, wherein the compound is the sodium salt of N-(2-hydroxyhexadecyl)- N-methyltaurine-N-oxide.

5. The detergent composition of claim 1, wherein the compound is the sodium salt of N-(Z-hydroxyoctadecyD- N-methyltaurine-N-oxide.

6. The detergent composition of claim 1, wherein R in the compound is a mixture of alkyl groups, the carbon chains of which vary from C to C 7. The composition according to claim 1 wherein said builder is at least one member of the group consisting of alkali metal sulfates, carbonates, silicates, phosphates, and borates and wherein said compound is present in an amount of at least about 3% by Weight of said composition and wherein said builder is present in an amount of at least about 20% by weight of said composition.

8. A composition according to claim 7 wherein said builder is at least one member of the group consisting of alkali metal tripolyphosphates and alkali metal pyrophosphates.

References Cited UNITED STATES PATENTS 1,944,300 1/1934 Ott et al 260-513 2,658,072 11/1953 Kosmin 260-513 2,929,788 3/1960 Freese et al. 252137 3,042,623 7/1962 Greene 252137 3,113,026 12/1963 Sprung 26050'1 LEON D. ROSDOL, Primary Examiner. S. E. DARDEN, Assistant Examiner.

Claims

1. A DETERGENT COMPOSITION CONSISTING ESSENTIALLY OF A COMPOUND OF THE FORMULA