US3171787A - Dentifrice compositions containing surface-active n-(2-hydroxyalkyl)-n-methyltaurine-n-oxide - Google Patents

Dentifrice compositions containing surface-active n-(2-hydroxyalkyl)-n-methyltaurine-n-oxide Download PDF

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US3171787A
US3171787A US173377A US17337762A US3171787A US 3171787 A US3171787 A US 3171787A US 173377 A US173377 A US 173377A US 17337762 A US17337762 A US 17337762A US 3171787 A US3171787 A US 3171787A
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methyltaurine
hydroxyalkyl
oxide
compounds
sodium
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US173377A
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Cahn Arno
Thaddeus J Kaniecki
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Lever Brothers Co
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Lever Brothers Co
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Priority to NL135294D priority Critical patent/NL135294C/xx
Priority to NL288984D priority patent/NL288984A/xx
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Priority to US173377A priority patent/US3171787A/en
Priority to GB5660/63A priority patent/GB1009190A/en
Priority to FR924685A priority patent/FR1357681A/en
Priority to DEU9580A priority patent/DE1277859B/en
Priority to US431982A priority patent/US3267135A/en
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Publication of US3171787A publication Critical patent/US3171787A/en
Priority to US559706A priority patent/US3359208A/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • 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
    • C11D10/00—Compositions of detergents, not provided for by one single preceding group
    • C11D10/04—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap
    • C11D10/045—Compositions of detergents, not provided for by one single preceding group based on mixtures of surface-active non-soap compounds and soap based on non-ionic surface-active compounds and soap
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds

Definitions

  • This invention relates to N-(2-hydroxyalkyl)-N-methyltaurine-N-oxides, alkali metal salts thereof, and methods of preparation.
  • the invention additionally relates to detergent and dentifrice compositions containing N-(Z- hydroxyalkyl)-N-methyltaurine-N-oxides and alkali metal salts thereof as active ingredients.
  • R is an alkyl group having from 8 to 18 carbon atoms
  • M is selected from the group consisting of hydrogen and alkali metals
  • novel compounds of this invention are excellent surface active agents, and are useful in detergent and dentifrice formulations.
  • the N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides 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.
  • 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.
  • detergents may be included in the detergent com positions 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.
  • N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides of this invention are particularly useful in dentifrice compositions, such as toothpaste. These compounds produce a large amount of foam, and do not lose their foaming power during the normal storage period while the compound is in contact with the other toothpaste ingredients. By comparison, the parent compounds, before conversion to the N-oxide, rapidly lose all ability to form a foam during storage.
  • N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides are prepared by the oxidation of the corresponding N-(Z-hydroxyalkyl)-N-methyltaurine, according to the following equation:
  • the N-(2-hydroxyalkyl)-N-methyltaurine may be prepared with ease from starting materials which are relatively inexpensive and commercially available, as described in our co-pending application Serial No. 116,706, filed June 15, 1961.
  • 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. Inorganic salts are highly objectionable, particularly when the compounds are to be used in detergent formulations.
  • the preparation of the epoxide starting material may be by conventional methods such as oxidation of the compounds derived from petroleum sources.
  • EXAMPLE II A series of N-(Z-hydroxyalkyl)-N-methyltaurine-N- oxides was prepared by the method of Example I 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.
  • Cloth swatches approximately 4 /2 inches by 6 inches were then added and the washing was continued 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 R12 R, and, with the agitators running, the cloths were rinsed for 5 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.
  • EXAMPLE III Sodium N- (2-hydroxyalkyl) -N-methyltaurine-N-oxides were prepared from sodium N (2-hydroxyalkyl) -N-' methyltaurines, which were in turn prepared by reacting N-methyltaurine witha 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 I 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 goodto-excellent response to building. Table III below gives the results of these evaluations.
  • Table III TERG-O-TOMETER TESTS OF SODIUM N-(2-HYDROXY- ALKYL)-N-METHYLTAURINE N OXIDES OF FOR- MULA u R-C H-C HgIl]-CH3C Hg-S QQNB.
  • EXAMPLE IV 7 Three compounds of this invention were evaluated ac- I cording 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.
  • the toothpaste was thoroughly dispersed by gentle stirring, and the dispersion then transferred to a ml. graduated cylinder.
  • the beaker was washed with 15 m1. of distilled water and the washings also transferred to the cylinder.
  • the cylinder was then inverted 25 times and allowed to rest for 5 minutes before reading the foam volume.
  • a toothpaste containing 2% of N-(Z-hydroxytetradecyl)-N-methyltaurine-N-oxide produced a 70 ml. foam volume in this test as compared with a foam volume of 40 ml. obtained with a toothpaste containing a conventional detergent, sodium lauryl sulfate, at a level of 1.16%. No change in the foaming power of the N-oxide toothpaste was noted over a one month aging period, while a similar toothpaste containing N-(2-hydroxytetradecyl)- N-methyltaurine as the detergent, failed to exhibit any foam whatsoever after the same period of storage.
  • EXAMPLE VI Another important property of toothpaste is freedom from irritation of mucous membranes.
  • a mucous membrane study was made comparing the irritation potential of a toothpaste containing N (2 hydroxytetradecyl)-N- methyltaurine-N-oxide at a 2% concentration level and a similar toothpaste containing 1.14% of sodium lauryl sulfate.
  • each toothpaste was applied to the vaginal tissue of each of six young adult female rabbits. These were divided into two groups, one for each formulation, placing three animals in each group. The paste was applied for three consecutive days and observations made over seven days for signs of irritation to the mucous membrane. No inflammatory reaction was noticed in either group of rabbits. The experimental paste was determined to be without primary irritation.
  • a dentifrice composition comprising an abrasive and 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.

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  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
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  • General Health & Medical Sciences (AREA)
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Description

United States Patent M This invention relates to N-(2-hydroxyalkyl)-N-methyltaurine-N-oxides, alkali metal salts thereof, and methods of preparation. The invention additionally relates to detergent and dentifrice compositions containing N-(Z- hydroxyalkyl)-N-methyltaurine-N-oxides and 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 compounds of this invention are excellent surface active agents, and are useful in detergent and dentifrice formulations. The N-(Z-hydroxyalkyl)-N-methyltaurine-N-oxides 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 com positions 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 particularly useful in dentifrice compositions, such as toothpaste. These compounds produce a large amount of foam, and do not lose their foaming power during the normal storage period while the compound is in contact with the other toothpaste ingredients. By comparison, the parent compounds, before conversion to the N-oxide, rapidly lose all ability to form a foam during storage.
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:
R and M having the same meaning as given above. While hydrogen peroxide is the preferred oxidizing agent, others 3,l7l,787 Patented Mar. 2, 1965 such as ozone, which have been described in the literature for the conversion of amines to amine oxide may be used.
The N-(2-hydroxyalkyl)-N-methyltaurine may be prepared with ease from starting materials which are relatively inexpensive and commercially available, as described in our co-pending application Serial No. 116,706, filed June 15, 1961. 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. Inorganic salts are highly objectionable, particularly when the compounds are to be used in detergent formulations. 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 also illustrate their usefulness as active ingredients in detergent and dentifrice formulations.
EXAMPLE I 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) was slowly added to a warm alcoholic solution of sodium N-(Z-hydroxyalkyl) -N-methyltaurine, prepared by dissolving 0.134 mole of sodium N-(Z-hydroxyalkyl)-N-methyltaurine in 350 ml. of ethyl alcohol. The resultant solution was maintained at 4050 C. for 24 hours. The excess hydrogen peroxide was then decomposed by placing a 1" x 2" pieces 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.
Table l GENERIC FORIVIULA.
t RCHCHg-N-CHg-CH1SO3NL Where R: Yield (isolated), percent C H 97.5
n -v 14 29 98 o n 97.5 C9H19-C13H27 (mixture) c13H27-C13H37 L.
EXAMPLE II A series of N-(Z-hydroxyalkyl)-N-methyltaurine-N- oxides was prepared by the method of Example I 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.
tergent was added in the desired amount to the washpot of the machine. 1250 ml. of water having a hardness of 180 p.p.m. CaCO (60 parts magnesium and 120 parts calcium calculated as calcium carbonate) was added. The machine was started and the solution agitated until the detergent was dissolved.
Cloth swatches approximately 4 /2 inches by 6 inches were then added and the washing was continued 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 R12 R, and, with the agitators running, the cloths were rinsed for 5 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 11 TERG-OTOMETERHOMOLOGOUS SERIES OF SODIUM N (Z-HYDROXYALKYL) -N-METHYLTAUBINE-N-OXIDES OF FORMULA 1 Tetrapotassium pyrophosphate.
EXAMPLE III Sodium N- (2-hydroxyalkyl) -N-methyltaurine-N-oxides were prepared from sodium N (2-hydroxyalkyl) -N-' methyltaurines, which were in turn prepared by reacting N-methyltaurine witha 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 I 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 goodto-excellent response to building. Table III below gives the results of these evaluations.
. Table III TERG-O-TOMETER TESTS OF SODIUM N-(2-HYDROXY- ALKYL)-N-METHYLTAURINE N OXIDES OF FOR- MULA u R-C H-C HgIl]-CH3C Hg-S QQNB.
Reflectance Readings, Hunter Refleetometer with Green Filter Compound 0.025% by Level, weight of 0.05% by compoundweight plus 0.05% by weight of 'IKPP 1 R=CgH!9-C13Hz7 mix; 42. 9 48.2 R=C13H27'-'ClBI'I37 mix 42. 6 51. 0 (Sodium) Dodecylbenzenesulfonate. 42. 9 46. 9 TKPP 1 43. 8 Water 4]. 2 Soil Cloth-Initial Average 39. 0
1 Tetrapotassium pyrophosphate.
EXAMPLE IV 7 Three compounds of this invention were evaluated ac- I cording 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.
Table IV below gives the compounds tested and the results of the test.
Table IV Compound Mildness Remarks Rating Sodium N-(2-hydroxydodecyl)-N-Methyltaurine- 0 Epidermis N-Oxlde. normal. Sodium N-(2-hydroxytetradeeyl)-N-Methyltau- 0 Do.
rine-N-Oxide. Sodium N-(2-hydroxyoetadecyl)-N-Methyltau- 0 Do.
rine-N-Oxide.
EXAMPLE v Ingredient: Percent by weight Dicalcium phosphate dihydrate 50.00
Other powdered abrasives 5.50 Gum binder .50 Humectant, flavor, and misc. ingredients 36.15 Glycerine 5.85
N (Z-hydroxytetradecyl) -N-methyltaurine-N- oxide 1 2.00
. 1 Where sodium lauryl sulfate was used, it was added at a level of 1.16%, and the glycerine level adjusted to 6.69%.
The toothpaste was thoroughly dispersed by gentle stirring, and the dispersion then transferred to a ml. graduated cylinder. The beaker was washed with 15 m1. of distilled water and the washings also transferred to the cylinder. The cylinder was then inverted 25 times and allowed to rest for 5 minutes before reading the foam volume.
A toothpaste containing 2% of N-(Z-hydroxytetradecyl)-N-methyltaurine-N-oxide produced a 70 ml. foam volume in this test as compared with a foam volume of 40 ml. obtained with a toothpaste containing a conventional detergent, sodium lauryl sulfate, at a level of 1.16%. No change in the foaming power of the N-oxide toothpaste was noted over a one month aging period, while a similar toothpaste containing N-(2-hydroxytetradecyl)- N-methyltaurine as the detergent, failed to exhibit any foam whatsoever after the same period of storage.
EXAMPLE VI Another important property of toothpaste is freedom from irritation of mucous membranes. A mucous membrane study was made comparing the irritation potential of a toothpaste containing N (2 hydroxytetradecyl)-N- methyltaurine-N-oxide at a 2% concentration level and a similar toothpaste containing 1.14% of sodium lauryl sulfate.
A small amount of each toothpaste was applied to the vaginal tissue of each of six young adult female rabbits. These were divided into two groups, one for each formulation, placing three animals in each group. The paste was applied for three consecutive days and observations made over seven days for signs of irritation to the mucous membrane. No inflammatory reaction was noticed in either group of rabbits. The experimental paste was determined to be without primary irritation.
EXAMPLE VII 6 We claim: 1. A dentifrice composition comprising an abrasive and 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.
2. The dentifrice composition of claim 1, wherein the compound is N-(Z-hydroxydodecyl)-N-methy1taurine-N- oxide.
3. The dentifrice composition of claim 1, wherein the compound is N-(Z-hydroxytetradecyl)-N-methyltaurine- N-oxide.
4. The dentifrice composition of claim 1, wherein the compound is the sodium salt of N-(2-hydroxydodecyl)- N-methyltaurine-N-oxide.
5. The dentifrice composition of claim 1, wherein the compound is the sodium salt of N-(2-hydroxytetradecyl)- N-methyltaurine-N-oxide.
6. The dentifrice composition of claim 1, wherein the compound is one where R is a mixture of C to- C alkyl groups.
7. The dentifrice composition of claim 1, wherein the compound is the sodium salt of N-(2-hydroxyhexadecyl)- N-methyltaurine-N-oxide.
8. In a method of cleaning teeth, the step of applying to the surface of the teeth, a compound of the formula wherein R is an alkyl group having from 8 to 18 carbon atoms and M is a member of the group consisting of hydrogen and the alkali metals.
References (Zited in the file of this patent UNITED STATES PATENTS 2,191,199 Hall Feb. 20, 1940 2,465,737 Martin Mar. 29, 1949 2,618,607 Sanders Nov. 18, 1952 2,618,608 Schaeifer Nov. 18, 1952 2,694,727 Cross at al Nov. 16, 1954 2,697,116 Stayner Dec. 14, 1954 2,812,284 Sanders Nov. 5, 1957 2,830,082 Sexton et a1. Apr. 8, 1958

Claims (1)

1. A DENTIFRICE COMPOSITION COMPRISING AN ABRASIVE AND A COMPOUND OF THE FORMULA
US173377A 1962-02-15 1962-02-15 Dentifrice compositions containing surface-active n-(2-hydroxyalkyl)-n-methyltaurine-n-oxide Expired - Lifetime US3171787A (en)

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Application Number Priority Date Filing Date Title
NL135294D NL135294C (en) 1962-02-15
NL288984D NL288984A (en) 1962-02-15
US173377A US3171787A (en) 1962-02-15 1962-02-15 Dentifrice compositions containing surface-active n-(2-hydroxyalkyl)-n-methyltaurine-n-oxide
GB5660/63A GB1009190A (en) 1962-02-15 1963-02-12 N-hydroxyalkyl-n-methyltaurine-n-oxides
FR924685A FR1357681A (en) 1962-02-15 1963-02-13 Process for the preparation of organic compounds, in particular of n- (2-hydroxyalkyl) -n-methyl-taurine-n-oxides
DEU9580A DE1277859B (en) 1962-02-15 1963-02-14 Process for the preparation of N- (2-hydroxyalkyl) -N-methyltaurine-N-oxides
US431982A US3267135A (en) 1962-02-15 1965-02-11 Nu-(2-hydroxyalkyl)-nu-methyltaurine-nu-oxides
US559706A US3359208A (en) 1962-02-15 1966-06-23 Detergent composition

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Cited By (1)

* Cited by examiner, † Cited by third party
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US4582651A (en) * 1979-12-27 1986-04-15 Nippon Paint Co., Ltd. Process for preparing hydroxyalkylaminosulfonic acids

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US2191199A (en) * 1937-09-17 1940-02-20 Hall Lab Inc Abrasive detergent composition
US2465737A (en) * 1946-04-29 1949-03-29 Nat Drug Co Gamma-hydroxy-n-butyryl taurine and salts thereof
US2618608A (en) * 1952-09-12 1952-11-18 Procter & Gamble Detergent compositions containing metal discoloration inhibitors
US2618607A (en) * 1952-11-18 Liquid
US2694727A (en) * 1951-09-07 1954-11-16 Gen Aniline & Film Corp N-alkylbenzenesulfonyl-n-alkyl taurates
US2697116A (en) * 1951-09-25 1954-12-14 California Research Corp Quaternary taurine type compounds as surface-active agents
US2812284A (en) * 1953-04-15 1957-11-05 Procter & Gamble Oral detergent composition and dentifrice comprising same
US2830092A (en) * 1952-09-30 1958-04-08 Carl J Claus Method for the conversion of ortho esters to acetals

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US2618607A (en) * 1952-11-18 Liquid
US2191199A (en) * 1937-09-17 1940-02-20 Hall Lab Inc Abrasive detergent composition
US2465737A (en) * 1946-04-29 1949-03-29 Nat Drug Co Gamma-hydroxy-n-butyryl taurine and salts thereof
US2694727A (en) * 1951-09-07 1954-11-16 Gen Aniline & Film Corp N-alkylbenzenesulfonyl-n-alkyl taurates
US2697116A (en) * 1951-09-25 1954-12-14 California Research Corp Quaternary taurine type compounds as surface-active agents
US2618608A (en) * 1952-09-12 1952-11-18 Procter & Gamble Detergent compositions containing metal discoloration inhibitors
US2830092A (en) * 1952-09-30 1958-04-08 Carl J Claus Method for the conversion of ortho esters to acetals
US2812284A (en) * 1953-04-15 1957-11-05 Procter & Gamble Oral detergent composition and dentifrice comprising same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4582651A (en) * 1979-12-27 1986-04-15 Nippon Paint Co., Ltd. Process for preparing hydroxyalkylaminosulfonic acids

Also Published As

Publication number Publication date
DE1277859B (en) 1968-09-19
NL135294C (en)
NL288984A (en)
GB1009190A (en) 1965-11-10

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