US2619467A - Detergent mixtures containing - Google Patents

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US2619467A
US2619467A US2619467DA US2619467A US 2619467 A US2619467 A US 2619467A US 2619467D A US2619467D A US 2619467DA US 2619467 A US2619467 A US 2619467A
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beta
amino
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foam
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    • 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • 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
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • C11D1/90—Betaines
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/33—Amino carboxylic acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/05—Organic amine, amide, or n-base containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

  • the present invention relates to novel detergent compositions which possess unusual properties which render them of extreme value.
  • the detregent compositions of the present in vention are composed of a plurality of ingredients, one of which has the following formula:
  • R is an aliphatic hydrocarbon group containing from twelve to eighteen carbon atoms, and X is a cation which renders the compound water soluble.
  • Another essential ingredient of the composition is a detergent having greater hydrophilic properties than the above compounds.
  • Typical cations in the compounds of the above formula include the alkali metal ions, ammonium ions, and organic base ions. These compounds in and of themselves possess certain detergent and surface-active properties. Some of them, particularly those in which R is a C12 group, are excellent surface-active agents and detergents by themselves. Others within this group, particularly those in which the B group contains from C14 to C18, and especially those in which R contains from C16 to 018, are less effective as foaming agents, although they do possess certain detergent surface-active properties.
  • They may be isolated pure amines, or may be composed of mixtures of amines, for example the mixture of amines obtained from the mixed acids of a fat or oil. They may be made from any selected saturated or unsaturated fractions of such oil acids. In general the compounds having the above formula possess similar properties but differ in the extent of their surface active and detergent properties.
  • the hydrophilic surface-active agents which may be used with the beta-amino propionates are of a wide variety. They include the betaamino propionates having the above formula in which R has less than twelve carbon atoms, preferably from 6 to 10 carbon atoms. Typical of these compounds are the ones in which R is a normal heptyl or octyl group. They also include alkyl aryl sulfonates, particularly where the alkyl group is a short chain group containing 1 to 6 carbon atoms. Typical compounds include toluene sulfonate, xylene sulfonate. These sulfonates are preferably used in the form of a soluble salt.
  • ionic hydrophilic surface-active agents also include soluble salts of sulfates of a large variety of hydroxy compounds, including the fatty alcohols of intermediate molecular weight, polyalkylene oxide derivatives of compounds having lipophilic groups, such as alkylated phenols, fatty acid amides, and fatty acids, particularly ethylene oxide derivatives of such compounds.
  • the hydrophilic surface-active agents useful in the present invention also include non-ionic materials such as alkylene oxide condensation products of alkylated phenol, polyalkylene glycol esters of higher fatty acids, and alkylene oxide derivatives of higher fatty acid amides, particularly ethylene oxide derivatives of such compounds.
  • the alkyl-substituted beta-amino propionic acid salts may also be mixed with a variety of other materials. For example, they may be mixed either by themselves or in admixture with the hydrophilic wetting agents, with such builders as various phosphate salts. sulfate salts, carbonates, silicates, borates, particularly the alkali metal salts of these various acids. Other-soil removing agents such as carboxymethyl cellulose; and-related materials may also be compounded with these products. beta-amino propionic acid salts maybe mixed with beta-amino propionic acid salts derived from rosin amines. These are found to result intre mendous increases in the foaming properties of the alkyl-substituted beta-amino propionic acidsalts.
  • Example 1 A comparison was made between the foamin ability of a 0.1% solution of the sodium salt of beta-amino propionicacid prepared from the amines derived fromsoybean oil acids, with a 0.1% solution of a mixture of the same beta.-
  • Example 2 A comparison was made between the foaming abilityof a 0.1% solution of the sodium salt of beta-amino propionic acid prepared from the amines derived from soybean oil acids. with a 0.1% solution of a mixture of the same betaamino 'propionic acid salt with the sodium salt of beta-amino propionic acid derived from n-heptyl amine, with the following results:
  • Example 4 Acomparison was made between a 0.1% solution of the sodium beta-amino propionates derived from the soybean oil acid amines with a 0.1% solution of amixture composed of parts of'the soybean oil acid amine derivative and 15 parts-of the sodium salt of beta-amino propionic acid derived from rosin acid amines. The comparison was made in accordance with the Ross Miles foaming test referred to in Example 1. The results. show that the sample composed solely of the-soybean oil acid amine derivative produced 31 mm. of foam, whereas the mixture produced 143 mm; Therosin acid derivative by itself produced a foam of 113mm.
  • The-beta-amino propionate salts havingthe formula herein described are also compatible with soaps in general, and the soaps may be used as extenders for these beta-amino propionates.
  • a detergent composition comprising n a mixture of a beta-amino propionate compound having the formula RNHCHzCHzCOOX RNHCHzCI-IzCOOX in which R is an aliphatic. hydrocarbon group containing from 12 to 18 carbon atoms and X is a cation which renders the compound watersoluble, and a water-soluble salt of an alkylaryl sulfonate in which. the allryl group. contains from car on a oms.
  • a detergent composition comprising a mixture of a beta-amino propionate compound having the formula RNHCI-IzCHzCOOX in which R is an aliphatic hydrocarbon group containing from 12 to 18 carbon atoms and X is a cation which renders the compound water-soluble, and an ethylene oxide derivative of an alkyl phenol.
  • a detergent composition comprising a mixture of beta-amino propionat compounds having the following formula RNI-ICI-IgCI-IzCOOX in which X is an alkali metal and in which R is th mixed aliphatic hydrocarbon groups of the amines derived from a fatty oil, said composition also containing a, compound having the above formula in which X is an alkali metal and in which R. is an aliphatic hydrocarbon group containing from 6 to 10 carbon atoms.

Description

PatentedNov. 25, 1952 UNEE TENT
DETERGENT MIXTURES CONTAINING BETA AMINO PROPIONATES No Drawing. Application April 16, 1949, Serial No. 88,049
5 Claims.
The present invention relates to novel detergent compositions which possess unusual properties which render them of extreme value.
The detregent compositions of the present in vention are composed ofa plurality of ingredients, one of which has the following formula:
RNHCHzCHzCOOX in which R is an aliphatic hydrocarbon group containing from twelve to eighteen carbon atoms, and X is a cation which renders the compound water soluble. Another essential ingredient of the composition is a detergent having greater hydrophilic properties than the above compounds. Typical cations in the compounds of the above formula include the alkali metal ions, ammonium ions, and organic base ions. These compounds in and of themselves possess certain detergent and surface-active properties. Some of them, particularly those in which R is a C12 group, are excellent surface-active agents and detergents by themselves. Others within this group, particularly those in which the B group contains from C14 to C18, and especially those in which R contains from C16 to 018, are less effective as foaming agents, although they do possess certain detergent surface-active properties.
These compounds may be prepared by the re action of the corresponding amine with an ester of acrylic acid in accordance with my copending application, Serial No. 609,329, filed August 6, 1945, now Patent No. 2,468,012 issued April 19, 1949, entitled Beta Amino Propionates. This reaction results in the simple addition of the amine to the acrylic ester. The ester thus obtained may readily be hydrolyzed and converted to any suitable cationic derivative. The amines which may be employed for this condensation include the fatty amines containing from to 18 carbon atoms, either saturated or unsaturated, and either straight or branched chain. They may be isolated pure amines, or may be composed of mixtures of amines, for example the mixture of amines obtained from the mixed acids of a fat or oil. They may be made from any selected saturated or unsaturated fractions of such oil acids. In general the compounds having the above formula possess similar properties but differ in the extent of their surface active and detergent properties.
It has been found that the surface-active properties and detergent properties of these compounds can be improved by mixing them with other surface-active agents which have a more predominantly hydrophilic character.
The hydrophilic surface-active agents which may be used with the beta-amino propionates are of a wide variety. They include the betaamino propionates having the above formula in which R has less than twelve carbon atoms, preferably from 6 to 10 carbon atoms. Typical of these compounds are the ones in which R is a normal heptyl or octyl group. They also include alkyl aryl sulfonates, particularly where the alkyl group is a short chain group containing 1 to 6 carbon atoms. Typical compounds include toluene sulfonate, xylene sulfonate. These sulfonates are preferably used in the form of a soluble salt. These ionic hydrophilic surface-active agents also include soluble salts of sulfates of a large variety of hydroxy compounds, including the fatty alcohols of intermediate molecular weight, polyalkylene oxide derivatives of compounds having lipophilic groups, such as alkylated phenols, fatty acid amides, and fatty acids, particularly ethylene oxide derivatives of such compounds. The hydrophilic surface-active agents useful in the present invention also include non-ionic materials such as alkylene oxide condensation products of alkylated phenol, polyalkylene glycol esters of higher fatty acids, and alkylene oxide derivatives of higher fatty acid amides, particularly ethylene oxide derivatives of such compounds.
All of the above compounds appear to alter the physical characteristics of the high molecular weight substituted beta-amino propionates. The effect of these added agents, however, is not uniform in all cases. Some of them appear to make foaming compositions out of the beta-amino propionates which in and of themselves are incapable of efiecting any great degree of foam formation. For example, the beta-amino propionate in which R, is predominantly the C18 hydrocarbon radical, is found not to produce any great amount of foam upon being agitated in water. The addition of a sodium salt of the beta-amino propionic acid in which the amino group is substituted with a normal heptyl or octyl group, produces copious quantities of foam with the C18 beta-amino propionate. Likewise, .the addition of certain ethylene oxide derivatives of alkyl phenols to the C18 beta-amino propionates, results in the production of large quantities of foam. In other instances the effect of the added agent may be upon the character of the foam. For example, sodium beta-dodecylaminopropionate by itself produces copious quantities of foam. The addition of a small quantity of the sodium salt of the sulfate of lauryl alcohol produces a mixture that gives foam of higher quality than that which results from either of the ingredients alone. A similar result is obtained by the addition of sodium salt of xylene sulfonic acid to the sodium beta-dodecylaminopropionate.
The alkyl-substituted beta-amino propionic acid salts may also be mixed with a variety of other materials. For example, they may be mixed either by themselves or in admixture with the hydrophilic wetting agents, with such builders as various phosphate salts. sulfate salts, carbonates, silicates, borates, particularly the alkali metal salts of these various acids. Other-soil removing agents such as carboxymethyl cellulose; and-related materials may also be compounded with these products. beta-amino propionic acid salts maybe mixed with beta-amino propionic acid salts derived from rosin amines. These are found to result intre mendous increases in the foaming properties of the alkyl-substituted beta-amino propionic acidsalts.
The following examples will serve to illustrate the invention:
Example 1 A comparison was made between the foamin ability of a 0.1% solution of the sodium salt of beta-amino propionicacid prepared from the amines derived fromsoybean oil acids, with a 0.1% solution of a mixture of the same beta.-
amino propionate with an ethylene oxide derivative of an alkyl phenol in which the mixture was composed of 95 parts of the beta-amino propionate and parts of the alkyl phenol ethylene oxidewderivative. The-comparison was made in ihestandard Ross Miles foaming test. The results show that the beta-amino propionate QQmpOund by itself gave 31 mm. of foam, whereas the mixture gave 115 mm. The ethylene oxide derivative of the alkyl phenol at 0.1 gave 94 mm.
of; foam byitself under similar conditions.
Example 2 A. comparison was made between the foaming abilityof a 0.1% solution of the sodium salt of beta-amino propionic acid prepared from the amines derived from soybean oil acids. with a 0.1% solution of a mixture of the same betaamino 'propionic acid salt with the sodium salt of beta-amino propionic acid derived from n-heptyl amine, with the following results:
De r e t aggi None. 39 mm. 44 mm. 45 mm. m -v H b l A spigrtiii.
Hep yl )+S r (B) 52.2% ret l o te Soy (B) ultanate ov (B) Similarly, the alkyl-substituted This example demonstrates how a very inexpensive material such as sodium xylene sulfonate can be used in high concentration with the more expensive beta-amino propionate salt, and at the same time materially improve its foaming characteristics'.- Thus a substantial increase-in foaming properties is obtained along with a very substantial reduction in the cost of the composition.
Example 4 Acomparison was made between a 0.1% solution of the sodium beta-amino propionates derived from the soybean oil acid amines with a 0.1% solution of amixture composed of parts of'the soybean oil acid amine derivative and 15 parts-of the sodium salt of beta-amino propionic acid derived from rosin acid amines. The comparison was made in accordance with the Ross Miles foaming test referred to in Example 1. The results. show that the sample composed solely of the-soybean oil acid amine derivative produced 31 mm. of foam, whereas the mixture produced 143 mm; Therosin acid derivative by itself produced a foam of 113mm.
The-beta-amino propionate salts havingthe formula herein described are also compatible with soaps in general, and the soaps may be used as extenders for these beta-amino propionates.--
The above examples are intended tobe illustrative only and not as limiting the invention. It will be apparent from theexamples that considerable variation is possible in the relative pro portions of ingredients. The example s showthat various characteristic properties may be developed by varying relative proportions; It is also apparent that the specificexamples show the effect of typical compounds within the group which they represent. It will bgapparent-that other compounds within the samegroup may be used'in the examples withthe sameor similar effect.
While various modifications of'the invention have been described, it will be apparent that other modifications are possible without departing from the spirit of the invention.
I claim as my invention:
1. A detergent composition compris n a mixture of a beta-amino propionate compound having the formula RNHCHzCHzCOOX RNHCHzCI-IzCOOX in which R is an aliphatic. hydrocarbon group containing from 12 to 18 carbon atoms and X is a cation which renders the compound watersoluble, and a water-soluble salt of an alkylaryl sulfonate in which. the allryl group. contains from car on a oms.
3. A detergent compositioncomprising a mixture of a beta-amino propionate compound having the formula RNHCI-IzCHzCOOX in which R is an aliphatic hydrocarbon group containing from 12 to 18 carbon atoms and X is a cation which renders the compound water-soluble, and an ethylene oxide derivative of an alkyl phenol.
4. A detergent composition comprising a mixture of beta-amino propionat compounds having the following formula RNI-ICI-IgCI-IzCOOX in which X is an alkali metal and in which R is th mixed aliphatic hydrocarbon groups of the amines derived from a fatty oil, said composition also containing a, compound having the above formula in which X is an alkali metal and in which R. is an aliphatic hydrocarbon group containing from 6 to 10 carbon atoms.
ARTHUR F. ISBELL.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,968,793 Bertsch July 31, 1934 1,970,578 Schoeller Aug. 21, 1934 2,097,864 Platz Nov. 2, 1937 2,164,781 Platz July 4, 1939 2,195,974 Reppe Apr. 2, 1940 2,413,968 Hallowell Jan. 7, 1947

Claims (1)

1. A DETERGENT COMPOSITION COMPRISING A MIXTURE OF A BETA-AMINO PROPIONATE COMPOUND HAVING THE FORMULA
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Cited By (30)

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US2731421A (en) * 1956-01-17 Tottuwrpmt
US2781379A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781377A (en) * 1956-03-09 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781381A (en) * 1956-05-24 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781380A (en) * 1956-05-24 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781349A (en) * 1956-04-02 1957-02-12 Hans S Mannheimer Certain salts of 2-hydrocarbon imidazolinium di-alkanoic acid salts of detergent sulfonic acids or sulfate acids
US2781374A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781375A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2833722A (en) * 1955-03-01 1958-05-06 Du Pont Detergent compositions
US2870093A (en) * 1956-01-09 1959-01-20 Lever Brothers Ltd Polyphosphate compositions containing coco-beta-alanine and 2-mercaptothiazoline
US2877187A (en) * 1955-08-10 1959-03-10 Lever Brothers Ltd Detergent containing beta, beta'-decylaminobisethanolpropionamide
US2880178A (en) * 1954-10-07 1959-03-31 Lever Brothers Ltd Detergent composition
US2929788A (en) * 1955-03-07 1960-03-22 Gen Mills Inc Detergent compositions composed of alkylaryl sulfonates and n-alkyl beta-aminopropionates
US2950255A (en) * 1956-07-03 1960-08-23 Gillette Co Detergent composition
US2953526A (en) * 1955-12-20 1960-09-20 Gen Aniline & Film Corp Ampholytic compositions in wet treatments
US2962448A (en) * 1955-07-15 1960-11-29 Diversey Corp Detergent composition
US2980624A (en) * 1957-01-04 1961-04-18 Gen Aniline & Film Corp Dry cleaning compositions
US2999069A (en) * 1957-11-18 1961-09-05 Johnson & Johnson Detergent composition
US3018251A (en) * 1957-01-11 1962-01-23 Gen Aniline & Film Corp Dry cleaning compositions
US3031408A (en) * 1959-08-07 1962-04-24 B T Babbitt Inc Aerosol oven cleanser
US3055836A (en) * 1957-12-24 1962-09-25 Johnson & Johnson Detergent composition
US3093591A (en) * 1957-05-03 1963-06-11 Gen Mills Inc Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
US3102859A (en) * 1960-09-19 1963-09-03 Gen Mills Inc Method for control of paraffin deposition
US3156656A (en) * 1958-01-06 1964-11-10 Gillette Co Aqueous shampoo composition
US3174929A (en) * 1960-08-17 1965-03-23 Gen Mills Inc Method of rejuvenating oil and gas wells
US3235457A (en) * 1962-12-07 1966-02-15 Gillette Co Humectant
US3442812A (en) * 1965-11-26 1969-05-06 Colgate Palmolive Co Detergent bars
US4107096A (en) * 1977-10-11 1978-08-15 Texaco Development Corp. Low foaming beta-amino propionic acid surface active agents
WO1980001142A1 (en) * 1978-12-08 1980-06-12 Fmc Corp Compositions for making stable emulsions and dispersions
US5922909A (en) * 1998-03-31 1999-07-13 Akzo Nobel Nv Process for the selective control of Zwitterionic amphoteric compositions

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US2097864A (en) * 1934-07-31 1937-11-02 Gen Aniline Works Inc Process of preparing amino-carboxylic acids and products obtainable thereby
US2195974A (en) * 1936-05-19 1940-04-02 Ig Farbenindustrie Ag Process of producing new amino-carboxylic acids
US2413968A (en) * 1944-10-30 1947-01-07 Du Pont Process for manufacture of nu-alkyl glycines

Cited By (30)

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US2731421A (en) * 1956-01-17 Tottuwrpmt
US2880178A (en) * 1954-10-07 1959-03-31 Lever Brothers Ltd Detergent composition
US2833722A (en) * 1955-03-01 1958-05-06 Du Pont Detergent compositions
US2929788A (en) * 1955-03-07 1960-03-22 Gen Mills Inc Detergent compositions composed of alkylaryl sulfonates and n-alkyl beta-aminopropionates
US2962448A (en) * 1955-07-15 1960-11-29 Diversey Corp Detergent composition
US2877187A (en) * 1955-08-10 1959-03-10 Lever Brothers Ltd Detergent containing beta, beta'-decylaminobisethanolpropionamide
US2953526A (en) * 1955-12-20 1960-09-20 Gen Aniline & Film Corp Ampholytic compositions in wet treatments
US2870093A (en) * 1956-01-09 1959-01-20 Lever Brothers Ltd Polyphosphate compositions containing coco-beta-alanine and 2-mercaptothiazoline
US2781377A (en) * 1956-03-09 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781349A (en) * 1956-04-02 1957-02-12 Hans S Mannheimer Certain salts of 2-hydrocarbon imidazolinium di-alkanoic acid salts of detergent sulfonic acids or sulfate acids
US2781381A (en) * 1956-05-24 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781380A (en) * 1956-05-24 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781375A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781374A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2781379A (en) * 1956-07-02 1957-02-12 Hans S Mannheimer Detergent sulphonic acid and sulphate salts of certain amphoteric detergents
US2950255A (en) * 1956-07-03 1960-08-23 Gillette Co Detergent composition
US2980624A (en) * 1957-01-04 1961-04-18 Gen Aniline & Film Corp Dry cleaning compositions
US3018251A (en) * 1957-01-11 1962-01-23 Gen Aniline & Film Corp Dry cleaning compositions
US3093591A (en) * 1957-05-03 1963-06-11 Gen Mills Inc Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
US2999069A (en) * 1957-11-18 1961-09-05 Johnson & Johnson Detergent composition
US3055836A (en) * 1957-12-24 1962-09-25 Johnson & Johnson Detergent composition
US3156656A (en) * 1958-01-06 1964-11-10 Gillette Co Aqueous shampoo composition
US3031408A (en) * 1959-08-07 1962-04-24 B T Babbitt Inc Aerosol oven cleanser
US3174929A (en) * 1960-08-17 1965-03-23 Gen Mills Inc Method of rejuvenating oil and gas wells
US3102859A (en) * 1960-09-19 1963-09-03 Gen Mills Inc Method for control of paraffin deposition
US3235457A (en) * 1962-12-07 1966-02-15 Gillette Co Humectant
US3442812A (en) * 1965-11-26 1969-05-06 Colgate Palmolive Co Detergent bars
US4107096A (en) * 1977-10-11 1978-08-15 Texaco Development Corp. Low foaming beta-amino propionic acid surface active agents
WO1980001142A1 (en) * 1978-12-08 1980-06-12 Fmc Corp Compositions for making stable emulsions and dispersions
US5922909A (en) * 1998-03-31 1999-07-13 Akzo Nobel Nv Process for the selective control of Zwitterionic amphoteric compositions

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