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US3803036A - Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines - Google Patents

Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines Download PDF

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Publication number
US3803036A
US3803036A US00205396A US20539671A US3803036A US 3803036 A US3803036 A US 3803036A US 00205396 A US00205396 A US 00205396A US 20539671 A US20539671 A US 20539671A US 3803036 A US3803036 A US 3803036A
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Prior art keywords
detergent
sulfosuccinate
composition
carbon atoms
salts
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US00205396A
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B Sundby
H Wixon
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Colgate Palmolive Co
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Colgate Palmolive Co
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Priority to BE792362D priority Critical patent/BE792362A/en
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US205395A priority patent/US3928422A/en
Priority to US00205396A priority patent/US3803036A/en
Priority to US205290A priority patent/US3893930A/en
Priority to CA 157600 priority patent/CA1005455A/en
Priority to ES409051A priority patent/ES409051A1/en
Priority to DE19722258564 priority patent/DE2258564A1/en
Priority to SE7215669A priority patent/SE400308B/en
Priority to IT54427/72A priority patent/IT973850B/en
Priority to AU49563/72A priority patent/AU4956372A/en
Priority to FR7243002A priority patent/FR2166982A5/fr
Priority to CH1766072A priority patent/CH576944A5/xx
Priority to GB5624572A priority patent/GB1420209A/en
Priority to US409027A priority patent/US3927073A/en
Priority to US05/424,250 priority patent/US4056558A/en
Application granted granted Critical
Publication of US3803036A publication Critical patent/US3803036A/en
Priority to SE7514180A priority patent/SE7514180L/en
Priority to SE7514179A priority patent/SE7514179L/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • 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
    • Y10S516/04—Protein or carboxylic compound containing

Definitions

  • ABSTRACT A detergent composition having inherent softening properties consisting essentially of a builder salt and a detergent selected from the group consisting of watersoluble sulfosuccinates of polyhydroxy tertiary amines having the structural formula:
  • R is a monovalent hydrocarbon radical of 8 to 24, preferably 10 to 20 carbon atoms; R is an alkyl or alkylol radical containing 1 to 6 carbon atoms, and R is an alkylol radical containing 1. to '6 carbon atoms, and salts thereof.
  • the reaction mixture consists of sulfonated mono-, di-, and/or tri-esters, depending on the number of reactive hydroxyl groups in the alcoholamine and the amount of dicarboxylic acid utilized. Since the aforedefined sulfonated esters and salts thereof uniquely possess both detergency and softening properties, they may constitute the sole detergent ingredient in the composition, although the presence of other detergents is not precluded.
  • detergent compositions comprising certain sulfosuccinates of 2-hydroxyalkyl tertiary alcoholamines and salts 'thereof in conjunction with water-soluble detergency builder salts possess all detergent composition or can be conveniently prepared in the form of bars, flakes, granular or tableted granular compositions.
  • a principal object of the present invention is to provide novel detergent compositions wherein the detergent component thereof possesses, in addition to detergency characteristics, fabric-softening characteristics, and is completely compatible with conventional water-soluble detergency builder salts.
  • sulfosuccinates of polyhydroxy tertiary amines and salts thereof possess the unusual characteristics of excellent detergency and fabric soft ening ability in addition to complete compatibility with water-soluble detergency builder salts conventionally employed in detergent compositions. Accordingly, the present invention is directed to such detergent compositions based upon aforesaid sulfosuccinates of 2- hydroxy alkyl tertiary alcoholamine and water-soluble detergency builder salts.
  • the sulfosuccinates of 2-hydroxyalkyl tertiary alcohol amines employed in the novel detergent compositions of the present invention possess both detergency and fabric softening ability and consist predominantly of the mono-ester having the formula:
  • R is a monovalent hydrocarbon radical of 8 to 24 and preferably 10 to 20 carbon atoms
  • R is an alkyl or alkylol radical of 1 to 6 carbon atoms
  • R is a divalent hydrocarbon radical (residue of the sulfonated dicarboxylic acid)
  • X is hydrogen or a salt-forming element or radical. If X is an element, it is preferred that it should be an alkali metal such as potassium, sodium and lithium or other suitable saltforming metal.
  • X is a radical, it is preferred that such be ammonium, alkylamine or alkanolamine, either mono-', di-or tri-alkylamine or mono-, di-, or trialkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of 2 to 4 carbon atoms, preferably 2 to 3 carbon atoms.
  • the novel sulfonated esters of the present invention can be prepared by a two step synthesis comprising the esterification of the polyhydroxy tertiary amine with an unsaturateddicarboxylic acid and subsequently sulfonating the ester with an alkali metal sulfite salt or by other suitable sulfonating means. More specifically, the ester may be formed by reacting the unsaturated dicarboxylic acid or preferably the anhydride thereof with a polyhydroxy tertiary amine having the structure:
  • R is a monovalent hydrocarbon radical of 8 to 24 and preferably 10 to 20 carbon atoms
  • R is an alkyl or hydroxyalkyl radical containing 1 to 6 carbon atoms
  • R is a hydroxy alkyl radical containing 1 to 6 carbon atoms.
  • g radicals of this class are:
  • radicals of di(isopropanol)amine N-methyl-N- isopropanol-amine, N-ethyl-N-ethanolamine, N-ethyl- N-isopropanolamine, N-propyl-N-ethanolamine, N-propyl-N-isopropanolamine, N-methyl-N-hydroxyethoxyethylamine, N-butyl-N-hydroxyethoxyethylamine, N-cyclohexyl-N-hydroxyethoxyethylamine, N-butyl-N-ethanolamine, di(hydroxyethoxyethyl)amine, mono( hydroxyethooxyethoxyethyl)amine, N-hydroxyethoxy-ethoxyethyl-N-methylamine, N-hydroxyethyl
  • the polyhydroxy tertiary amines are known compounds which may be prepared by condensing secondary alcoholamines with long chain epoxides.
  • a typical example of an amine/epoxide reaction is the preparation of 2-hydroxyalkyl-diethanolamine.
  • the unsaturated dicarboxylic acid anhydride may be maleic anhydride or a substituted maleic anhydride:
  • the alcoholamine has at least two hydroxyl groups, one in the long chain resulting from the'epoxide ring opening and one or more from the original alcohola-. mine.
  • the primary hydroxyl is preferentially. esterified into the mono-ester, since it is the least stearically hindered and therefore most reactive group.
  • the other hydroxyl radicals react to form the di-ester, triester, etc. and mixtures thereof.
  • the number of hydroxyl group's in the alcoholamine is determinative of the formation of the mono-, di-, or tri-esters.
  • esterification of the 2-hydroxyalkylalcoholamines with the unsaturated dicarboxylic acid anhydride is an exothermic reaction which can be carried out in aprotic solvent, ether, chloroform or acetone, but it can also be carried out neat.
  • the latter method is preferable as an industrial process, since no solvent is involved, thereby not giving any by-products.
  • the powdered acid anhydride (e.g., maleic anhydride) is added gradually to the liquid alcoholamine which is held at a temperature of about 100 C.
  • the product is cooled and subsequently sulfonated by the addition of the ester to an aqueous solution of a sulfite salt.
  • the mixture is heated to about 5090 C with agitation for a period of about 30-60 minutes.
  • a clear, viscous solution is obtained.
  • the final product may be freeze dried and is obtained in the form, of a solid, which is insoluble in acetone, ether, etc., but very soluble in water.
  • esterification is controlled so that only one mole of water is removed per mole of alcohol. Termination of esterification at this point ensures the formation of mono-, di-, and/or tri-esters as defined in copending application Ser. No. 205,395, filed Dec. 6, 1971 in the name of Bjorn Sundby and prevents the production of a polymeric linear ester.
  • the esterification reaction may be controlled by conventional methods of cooling or by other suitable means.
  • the products obtained are usually clear, viscous solutions of sulfonated mono-, di-, tri-esters and mixtures thereof, readily soluble in water.
  • the sulfonated monodi-, and tri-esters can be readily separated and purified by chromatographic techniques in the usual manner. However, separation is not necessary.
  • The'mixture of mono-, di-, and/or tri-esters can be used as the effective detergent, due to their combined property of detergency and fabric conditioning (softening, antistatic, etc.).
  • the high viscosity solutions that some members of this series form render them particularly useful in shampoos.
  • sulfonated esters examples include:
  • novel sulfonated esters of the present invention in addition to possessing excellent detergency and fabric softening properties, have been found to be compatible with the various detergent builders and other additives conventionally employed in detergent compositions. Accordingly, it is possible to formulate a detergent composition based on the sulfonated ester of instant invention as the detergent and fabric softener.
  • novel detergent compositions of the present invention may contain one or more watersoluble detergency builder salts either of the organic or the inorganic type.
  • water-soluble inorganic detergency builder salts are alkali metal carbonates, bicarbonates, phosphates, polyphosphates, sulfates, borates and silicates, etc.
  • Specific examples of such salts are sodium, potassium and lithium tripolyphosphates, carbonates, pyrophosphates, orthophosphates and hexamethaphosphates; sodium, potassium and lithium sulfates; sodium, potassium and lithium silicates; sodium carbonate, bicarbonate, sequicarbonate; sodium tetraborate and mixtures thereof.
  • organic alkaline detergency builder salts examples include (l) alkali metal amino polycarboxylates (e.g., sodium and potassium ethylenediamine-tetraacetates, N-(2-hydroxyethyl)- ethylenediaminetriacetates, nitrilo triacetates, and
  • N-(2-hydroxyethyl)-nitrilo diacetates (2) alkali metal salts of phytic acid (e.g., sodium and potassium phytates See U.S. Pat. No. 2,739,942); (3) watersoluble salts of ethane-l-hydroxy-l, l-diphosphonate (e.g., the trisodium and tripotassium salts See U.S. Pat. No. 3,159,581 (4) water-soluble salts of methylene diphosphonic acid (e.g., trisodium and tripotassium methylene diphosphonate and the other salts described in U.S. Pat. No.
  • phytic acid e.g., sodium and potassium phytates See U.S. Pat. No. 2,739,942
  • watersoluble salts of ethane-l-hydroxy-l, l-diphosphonate e.g., the trisodium and tripotassium salts See U.
  • water-soluble salts of substituted methylene diphosphonic acids e.g., trisodium and tripotassium ethylidene, isopropyl- ,idene, benzylmethylidene, and halomethylidene diphosphonates
  • water-soluble salts of polycarboxylate polymers and copolymers e.g., polymers of itaconic acid, aconitic acid, maleic acid; mesaconic acid; fumaric acid; methylene malonic acid; and citronic acid and copolymers with themselves and other compatible monomers such as ethylene
  • mixtures of organic and inorganic builder salts is also contemplated by instant invention.
  • the sulfonated ester or salt thereof is generally employed in an amount of from about 5 to 30% by weight of the total composition. While the watersoluble detergency builder salts comprise from about to about 95% by weight of the total composition.
  • the sulfonated dicarboxylic acidpolyhydroxy tertiary amine ester comprises about 10 25% by weight while the detergent builders comprise from about of the total composition.
  • the detergent compositions of this invention can contain any of the usual adjuvants, diluents and additives; for example, anionic, nonionic, ampholytic, cationic or zwitterionic detergents, perfumes, antitarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, suds builders, suds depressors, enzymes and the like, without detracting from the advantageous properties of the composition.
  • anionic detergents are sodium xylene sulfonate, sodium toluene sulfonate, sodium coconut soap, sodium dodecyl benzene sulfonate and potassium tallow alkyl sulfate.
  • nonionic detergents are dodecyl-dimethylamine oxide and the condensation product of coconut fatty alcohol with .5 moles of ethylene oxide.
  • An example of a zwitterionic detergent is 3-(N-N-dimethyl-N-hexadecylammonio )-2- hydroxypropane-l-sulfonate.
  • An example of an ampholytic detergent is sodium 3-dodoecylaminopropionate.
  • a cationic detergent is cetyltrimethylammonium bromide.
  • the detergent compositions of the present invention are excellent compositions for all types of cleaning operations, the compositions of the present invention are extremely effective for the cleaning of textiles as in a conventional laundry or washing machine.
  • the detergent compositions of the present invention can be effectively used for laundering fabrics in water having a temperature of from about 60 F to about 212 F, the detergent composition of the present invention exhibiting unusually effective detergency and fabric softening characteristics in both cold and hot water.
  • the step of washing the fabrics with the detergent composition of the present invention is followed by rinsing and drying of the fabric.
  • the detergent composition concentration in the wash solution should range from about 0.05% to about 0.5% by total weight, and the detergent composition should be added so as to provide an effective detergent and fabric softening amount of the sulfonated esters of 2-hydroxyalkyla1coho1amine of at least 0.005%.
  • the addition of the fabrics and the detergent composition can be conducted in any suitable conventional manner.
  • the fabrics can be added to the container or washer either before or after the washing solution is added.
  • the fabrics are then agitated in the detergent solution for varied periods of time, a wash cycle of from 8 to 15 minutes being generally used in the washing cycle of an automatic agitator type washer.
  • the detergent composition is drained off of the fabrics and the fabrics are rinsed in substantially pure water.
  • the fabrics can be rinsed as many times as desired. After rinsing of the fabrics, the fabrics are dried first by spinning and then by contact with the air as in conventional hanging of the fabrics on a clothesline or in an automatic dryer type system.
  • the organic detergent and water softening component as well as the builders and any minor ingredients are incorporated into the composition prior to its conversion into the final product form, e.g., detergent granules, flakes, bar, etc.
  • the individual components of, the novel detergent composition of the presentinvention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
  • EXAMPLE I The instant novel sulfonated esters and salts thereof were tested for their detergency properties as well as their efficacy as fabric softeners.
  • the Spangler soil detergency tests were run using an aqueous solution con- 7' TABLE 1 ARd (Soil Removal) Compound 1.
  • Control-Linear tridecyl benzene sulfonate 3.
  • Disodium sulfosuccinate of N-(Z-OHC J diethanolamine 4.
  • Disodium sulfosuccinate of NB-TAP 300 PPM NB-TAP 300 PPM diisopropanolamine i EXAMPLEH Similarly, the test for softening effect on cotton materials is run by washing one terry cloth towel in 17 gallons of NB tap water at 120 F and air drying. The softness is rated on a scale of 1 to 10, with 1 indicating no softness and 10 representing maximum softness.
  • EXAMPLE VI The sulfosuccinate of Example V was acidified with lactic acid. Fabric was washed with an aqueous solution thereof, rinsed and dried, in accordance with the procedure in Example 1, resulting in a softness rating of 10.
  • Example VIII The composition of Example VII was acidified with lactic acid, thereby forming a clear, viscous liquid. Fabric treated therewith exhibited excellent softness.
  • EXAMPLE IX 15 g of an 8% solution of disodium sulfosuccinate of N-(2-hydroxyoctadecyl) diethanolamine 15 g of an 8% solution of N-( 2-hydroxy C sarcosine.
  • the two ingredients were acidified with lactic acid, forming a translucent, viscous liquid. Fabric treated herewith exhibited excellent softness and whiteness.
  • this composition was a clear, l-phase, moderately viscous liquid which may be used in the wash cycle with known commercial laundry detergents as both a softener and detergency booster.
  • a detergent composition having inherent softening properties comprising about 530% by weight of water soluble sulfosuccinate estersof polyhydroxy tertiary amines, said amines having the structural formula:
  • R is an alkyl radical of 8 to 24 carbon atoms
  • R is an alkyl or alkylol radical of l to 6 carbon atoms
  • R is an alkylol radical of l to 6 carbon atoms or the alkali metal, ammonium, alkyl amine and alkanol amine salts thereof, the alkyl and alkanol groups of said amines containing from 2 to 4 carbon atoms, and about -95% water soluble builder salts
  • said water soluble sulfosuccinate esters being selected from the group consisting of mono, di and trisulfosuccinates containing respectively 1, 2 and 3 carboxyl groups and respectively I, 2 and 3 sulfo groups, and mixtures thereof.
  • R and R are as defined above, R is an alkylene radical of l to 6 carbon atoms, R,, is an ethylene radical and X is hydrogen or salt-forming element or radical selected from the group consisting of alkali metal, ammonium, alkyl amine and alkanol amine, the alkyl and alkanol groups of said amines containing from 2 to 4 carbon atoms.
  • composition in accordance with claim 1 which contains disodium sulfosuccinate of N-(2-hydroxy hexadecyl)-diethanolamine.
  • Acomposition in accordance with claim l,whic,h contains sulfosuccinate of N-(Z-hydroxyoctadecyl) methylethanolamine.

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Abstract

A detergent composition having inherent softening properties consisting essentially of a builder salt and a detergent selected from the group consisting of water-soluble sulfosuccinates of polyhydroxy tertiary amines having the structural formula:

WHEREIN R1 is a monovalent hydrocarbon radical of 8 to 24, preferably 10 to 20 carbon atoms; R2 is an alkyl or alkylol radical containing 1 to 6 carbon atoms, and R3 is an alkylol radical containing 1 to 6 carbon atoms, and salts thereof. The reaction mixture consists of sulfonated mono-, di-, and/or triesters, depending on the number of reactive hydroxyl groups in the alcoholamine and the amount of dicarboxylic acid utilized. Since the aforedefined sulfonated esters and salts thereof uniquely possess both detergency and softening properties, they may constitute the sole detergent ingredient in the composition, although the presence of other detergents is not precluded.

Description

United States Patent 1 Sundby et al.
[451 Apr. 9, 1974 DETERGENT-SOFTENER COMPOSITIONS CONTAINING SULFOSUCCINATES OF POLYHYDROXY TERTIARY AMINES [75] Inventors: Bjorn Sundby, Piscataway; Harold Eugene Wixon, New Brunswick,
21 Appl. No.: 205,396
[52] US. Cl... 252/8.75, 117/1395 C, 117/1395 Q, 252/526, 252/545, 260/481 R Primary ExaminerHerbert B. Guynn Attorney, Agent, or FirmHerbert S. Sylvester; Murray M. Grill; Norman Blumenkopf 57] ABSTRACT A detergent composition having inherent softening properties consisting essentially of a builder salt and a detergent selected from the group consisting of watersoluble sulfosuccinates of polyhydroxy tertiary amines having the structural formula:
wherein R is a monovalent hydrocarbon radical of 8 to 24, preferably 10 to 20 carbon atoms; R is an alkyl or alkylol radical containing 1 to 6 carbon atoms, and R is an alkylol radical containing 1. to '6 carbon atoms, and salts thereof. The reaction mixture consists of sulfonated mono-, di-, and/or tri-esters, depending on the number of reactive hydroxyl groups in the alcoholamine and the amount of dicarboxylic acid utilized. Since the aforedefined sulfonated esters and salts thereof uniquely possess both detergency and softening properties, they may constitute the sole detergent ingredient in the composition, although the presence of other detergents is not precluded.
' 7 Claims, N0 Drawings DETERGENT-SOFTENER COMPOSITIONS CONTAINING SULFOSUCCINATES OF POLYHYDROXY TERTIARY AMINES This invention relates to novel detergent compositions containing sulfosuccinates of 2-hydroxy alkyltertiary alcohol amines and salts thereof. It has been discovered that said compounds are useful surface active agents and are substantive to a variety of fibrous materials. Thus, they may be used as emulsifiers, solubilizing agents for lipophilic materials, wetting agents, detergents and softeners for textiles and hair.
Since the introduction of commercial synthetic organic detergents and emulsifiers to replace the conventional water-soluble higher fatty acid soaps, much research work has been performed in an effort to improve such compounds and compositions including them, with the object of obtaining better and more convenient laundering of textiles. As a result, a wide variety of types of surface active agents and detergents have been produced and many such compositions have been manufactured commercially and have been introduced to the market place. As better products were made, the goals set for researchers on detergency were increased and the properties of the desired products were such as to have been thought impossible of attainment only a few years before. Although the cleaning function of surface active materials is still very important and products which clean better than competitive compounds are always in demand, additional attributes of cleaning compounds were desired. For example, with the increasing importance of cold water washing, detergent compositions were desired which would be capable of successfully cleaning and whitening textiles and laundry in cold water, as well as in hot water. Such washing capability is of importance in making a product acceptable for the washing of wool and other shrink-sensitive materials. In addition, softening agents have been found to be a desirable, and in some instances, a necessary ingredient in the washing of textiles. However, because of the incompatibility of softeners and detergents, it has been necessary to utilize the textile softener in the final rinse as a separate step in a washing cycle. The objections to this procedure are obvious; one must be present during the washing cycle and few washing machines include devices for the addition of softeners in the final rinse.
Accordingly, it has long been the desire of the detergent industry to develop a detergent composition possessing detergency and fabric softening characteristics and compatibility with conventional water-soluble detergency builder salts.
It has now been discovered in accordance with the present invention that detergent compositions comprising certain sulfosuccinates of 2-hydroxyalkyl tertiary alcoholamines and salts 'thereof in conjunction with water-soluble detergency builder salts possess all detergent composition or can be conveniently prepared in the form of bars, flakes, granular or tableted granular compositions.
Accordingly, a principal object of the present invention is to provide novel detergent compositions wherein the detergent component thereof possesses, in addition to detergency characteristics, fabric-softening characteristics, and is completely compatible with conventional water-soluble detergency builder salts.
Still further objects and advantages of the novel detergent composition of the present invention will become more apparent from the following more detailed description thereof.
In accordance with the present invention, it has now been discovered that sulfosuccinates of polyhydroxy tertiary amines and salts thereof possess the unusual characteristics of excellent detergency and fabric soft ening ability in addition to complete compatibility with water-soluble detergency builder salts conventionally employed in detergent compositions. Accordingly, the present invention is directed to such detergent compositions based upon aforesaid sulfosuccinates of 2- hydroxy alkyl tertiary alcoholamine and water-soluble detergency builder salts.
The sulfosuccinates of 2-hydroxyalkyl tertiary alcohol amines employed in the novel detergent compositions of the present invention, possess both detergency and fabric softening ability and consist predominantly of the mono-ester having the formula:
wherein R is a monovalent hydrocarbon radical of 8 to 24 and preferably 10 to 20 carbon atoms, R is an alkyl or alkylol radical of 1 to 6 carbon atoms, R, is a divalent hydrocarbon radical of l to 6 carbon atoms (R,- OH=R R is a divalent hydrocarbon radical (residue of the sulfonated dicarboxylic acid), X is hydrogen or a salt-forming element or radical. If X is an element, it is preferred that it should be an alkali metal such as potassium, sodium and lithium or other suitable saltforming metal. If X is a radical, it is preferred that such be ammonium, alkylamine or alkanolamine, either mono-', di-or tri-alkylamine or mono-, di-, or trialkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of 2 to 4 carbon atoms, preferably 2 to 3 carbon atoms.
The novel sulfonated esters of the present invention can be prepared by a two step synthesis comprising the esterification of the polyhydroxy tertiary amine with an unsaturateddicarboxylic acid and subsequently sulfonating the ester with an alkali metal sulfite salt or by other suitable sulfonating means. More specifically, the ester may be formed by reacting the unsaturated dicarboxylic acid or preferably the anhydride thereof with a polyhydroxy tertiary amine having the structure:
wherein R is a monovalent hydrocarbon radical of 8 to 24 and preferably 10 to 20 carbon atoms, R is an alkyl or hydroxyalkyl radical containing 1 to 6 carbon atoms, R is a hydroxy alkyl radical containing 1 to 6 carbon atoms. Examples of g radicals of this class are:
' CfiiCHiOH CHaCIhOH CHzCHzOH and related compounds in which the radicals contain more carbon atoms than in the formula shown above, e.g., radicals of di(isopropanol)amine, N-methyl-N- isopropanol-amine, N-ethyl-N-ethanolamine, N-ethyl- N-isopropanolamine, N-propyl-N-ethanolamine, N-propyl-N-isopropanolamine, N-methyl-N-hydroxyethoxyethylamine, N-butyl-N-hydroxyethoxyethylamine, N-cyclohexyl-N-hydroxyethoxyethylamine, N-butyl-N-ethanolamine, di(hydroxyethoxyethyl)amine, mono( hydroxyethooxyethoxyethyl)amine, N-hydroxyethoxy-ethoxyethyl-N-methylamine, N-hydroxyethyl-N-hydroxy-isopropylamine, N-benzyl-N-hydroxyethylamine, or N-cyclehexyl-N-2- hydroxy-Z-phenylethylamine.
The polyhydroxy tertiary amines are known compounds which may be prepared by condensing secondary alcoholamines with long chain epoxides. A typical example of an amine/epoxide reaction is the preparation of 2-hydroxyalkyl-diethanolamine.
The unsaturated dicarboxylic acid anhydride may be maleic anhydride or a substituted maleic anhydride:
a R JK a The reaction is predominantly in accordance with the following equations:
i I B H-CHg-N-Qh-O J3 RA-COOX The alcoholamine has at least two hydroxyl groups, one in the long chain resulting from the'epoxide ring opening and one or more from the original alcohola-. mine. When utilizing equimolar amounts of reactants, the primary hydroxyl is preferentially. esterified into the mono-ester, since it is the least stearically hindered and therefore most reactive group. However, when more than one mole of the acid anhydride is used, the other hydroxyl radicals react to form the di-ester, triester, etc. and mixtures thereof. Similarly, the number of hydroxyl group's in the alcoholamine is determinative of the formation of the mono-, di-, or tri-esters.
CODE
COOH
mono-, dl-, an tri-esters CHICHzOH COOH COOH Ric 11-42mm (ll-esters CHa OH alkyl C O OH R141 H-C Hr-N-CHaC H2O CHQO HzOH R4 C O O H many and til-esters The esterification of the 2-hydroxyalkylalcoholamines with the unsaturated dicarboxylic acid anhydride is an exothermic reaction which can be carried out in aprotic solvent, ether, chloroform or acetone, but it can also be carried out neat. The latter method is preferable as an industrial process, since no solvent is involved, thereby not giving any by-products. The powdered acid anhydride (e.g., maleic anhydride) is added gradually to the liquid alcoholamine which is held at a temperature of about 100 C. When the reaction is over, the product is cooled and subsequently sulfonated by the addition of the ester to an aqueous solution of a sulfite salt. The mixture is heated to about 5090 C with agitation for a period of about 30-60 minutes. A clear, viscous solution is obtained. The final product may be freeze dried and is obtained in the form, of a solid, which is insoluble in acetone, ether, etc., but very soluble in water. When utilizing a solvent during the esterification step, the. reactants are first dissolved therein and the solution refluxed until the reaction is complete. Evaporation of the solvent yields a resin-like, waxy product, insoluble in water, which is subsequently sulfonated as above. When utilizing the unsaturated dicarboxylic acid in lieu of the anhydride,
esterification is controlled so that only one mole of water is removed per mole of alcohol. Termination of esterification at this point ensures the formation of mono-, di-, and/or tri-esters as defined in copending application Ser. No. 205,395, filed Dec. 6, 1971 in the name of Bjorn Sundby and prevents the production of a polymeric linear ester. The esterification reaction may be controlled by conventional methods of cooling or by other suitable means.
The products obtained are usually clear, viscous solutions of sulfonated mono-, di-, tri-esters and mixtures thereof, readily soluble in water. The sulfonated monodi-, and tri-esters can be readily separated and purified by chromatographic techniques in the usual manner. However, separation is not necessary. The'mixture of mono-, di-, and/or tri-esters can be used as the effective detergent, due to their combined property of detergency and fabric conditioning (softening, antistatic, etc.). The high viscosity solutions that some members of this series form render them particularly useful in shampoos.
Examples of sulfonated esters in accordance with the present invention include:
sulfosuccinate of N-(2-hydroxy hexadecyl) diethanolamine sulfosuccinate of N-(2-hydroxy octadecyl) diethanolamine sulfosuccinate of N-(Z-hydroxy octadecyl) diisopropanolamine sulfosuccinate of N-(Z-hydroxy octadecyl) diglycolamine sulfosuccinate of N-(2-hydroxy octadecyl) methylethanolamine sulfosuccinate of N-(2-hydroxy dodecyl) diethanolamine sulfosuccinate of N-(2-hydroxy dodecylYdiisopropE nolamine sulfosuccinate of N-(2-hydroxy dodecyl) diglycolamine sulfosuccinate of N-(Z-hydroxy dodecyl) methylethanolamine sulfosuccinate of N-(2-hydroxy tetradecyl) diethanolamine Further examples of sulfonated esters of 2- hydroxylalkyl tertiary alcoholamine and processes for producing the same can be found in co-pending application Ser. No. 205,395, filed Dec. 6, 1971 in the name of Bjorn Sundby.
The novel sulfonated esters of the present invention, in addition to possessing excellent detergency and fabric softening properties, have been found to be compatible with the various detergent builders and other additives conventionally employed in detergent compositions. Accordingly, it is possible to formulate a detergent composition based on the sulfonated ester of instant invention as the detergent and fabric softener.
In addition to the aforedefined sulfonated esters or salts thereof, the novel detergent compositions of the present invention may contain one or more watersoluble detergency builder salts either of the organic or the inorganic type.
Examples of water-soluble inorganic detergency builder salts are alkali metal carbonates, bicarbonates, phosphates, polyphosphates, sulfates, borates and silicates, etc. Specific examples of such salts are sodium, potassium and lithium tripolyphosphates, carbonates, pyrophosphates, orthophosphates and hexamethaphosphates; sodium, potassium and lithium sulfates; sodium, potassium and lithium silicates; sodium carbonate, bicarbonate, sequicarbonate; sodium tetraborate and mixtures thereof. Examples of organic alkaline detergency builder salts are (l) alkali metal amino polycarboxylates (e.g., sodium and potassium ethylenediamine-tetraacetates, N-(2-hydroxyethyl)- ethylenediaminetriacetates, nitrilo triacetates, and
N-(2-hydroxyethyl)-nitrilo diacetates); (2) alkali metal salts of phytic acid (e.g., sodium and potassium phytates See U.S. Pat. No. 2,739,942); (3) watersoluble salts of ethane-l-hydroxy-l, l-diphosphonate (e.g., the trisodium and tripotassium salts See U.S. Pat. No. 3,159,581 (4) water-soluble salts of methylene diphosphonic acid (e.g., trisodium and tripotassium methylene diphosphonate and the other salts described in U.S. Pat. No. 3,213,030;) (5) water-soluble salts of substituted methylene diphosphonic acids (e.g., trisodium and tripotassium ethylidene, isopropyl- ,idene, benzylmethylidene, and halomethylidene diphosphonates;) (6) water-soluble salts of polycarboxylate polymers and copolymers (e.g., polymers of itaconic acid, aconitic acid, maleic acid; mesaconic acid; fumaric acid; methylene malonic acid; and citronic acid and copolymers with themselves and other compatible monomers such as ethylene); and mixtures thereof. Similarly, mixtures of organic and inorganic builder salts is also contemplated by instant invention.
In the detergent composition of the present invention, the sulfonated ester or salt thereof is generally employed in an amount of from about 5 to 30% by weight of the total composition. While the watersoluble detergency builder salts comprise from about to about 95% by weight of the total composition. Preferably, the sulfonated dicarboxylic acidpolyhydroxy tertiary amine ester comprises about 10 25% by weight while the detergent builders comprise from about of the total composition.
The detergent compositions of this invention can contain any of the usual adjuvants, diluents and additives; for example, anionic, nonionic, ampholytic, cationic or zwitterionic detergents, perfumes, antitarnishing agents, anti-redeposition agents, bacteriostatic agents, dyes, fluorescers, suds builders, suds depressors, enzymes and the like, without detracting from the advantageous properties of the composition. Examples of anionic detergents are sodium xylene sulfonate, sodium toluene sulfonate, sodium coconut soap, sodium dodecyl benzene sulfonate and potassium tallow alkyl sulfate. Examples of nonionic detergents are dodecyl-dimethylamine oxide and the condensation product of coconut fatty alcohol with .5 moles of ethylene oxide. An example of a zwitterionic detergent is 3-(N-N-dimethyl-N-hexadecylammonio )-2- hydroxypropane-l-sulfonate. An example of an ampholytic detergent is sodium 3-dodoecylaminopropionate. An example of a cationic detergent is cetyltrimethylammonium bromide.
While the detergent compositions of the present invention are excellent compositions for all types of cleaning operations, the compositions of the present invention are extremely effective for the cleaning of textiles as in a conventional laundry or washing machine. Thus, the detergent compositions of the present invention can be effectively used for laundering fabrics in water having a temperature of from about 60 F to about 212 F, the detergent composition of the present invention exhibiting unusually effective detergency and fabric softening characteristics in both cold and hot water. Preferably, the step of washing the fabrics with the detergent composition of the present invention is followed by rinsing and drying of the fabric. The detergent composition concentration in the wash solution should range from about 0.05% to about 0.5% by total weight, and the detergent composition should be added so as to provide an effective detergent and fabric softening amount of the sulfonated esters of 2-hydroxyalkyla1coho1amine of at least 0.005%.
In washing fabrics, the addition of the fabrics and the detergent composition can be conducted in any suitable conventional manner. Thus, for example, the fabrics can be added to the container or washer either before or after the washing solution is added. The fabrics are then agitated in the detergent solution for varied periods of time, a wash cycle of from 8 to 15 minutes being generally used in the washing cycle of an automatic agitator type washer. As stated above, following the washing of the fabrics, the detergent composition is drained off of the fabrics and the fabrics are rinsed in substantially pure water. Here again, as a matter of choice, the fabrics can be rinsed as many times as desired. After rinsing of the fabrics, the fabrics are dried first by spinning and then by contact with the air as in conventional hanging of the fabrics on a clothesline or in an automatic dryer type system. I In the preparation ofthe novel detergent compositions of the present invention, generally, the organic detergent and water softening component as well as the builders and any minor ingredients are incorporated into the composition prior to its conversion into the final product form, e.g., detergent granules, flakes, bar, etc. However, the individual components of, the novel detergent composition of the presentinvention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
Various embodiments hr" the present invention will now be illustrated by reference to the following specific examples. It is to be understood, however, that such examples are presented for purposes of illustration only, and the present invention is in no way to be deemed as limited thereby.
EXAMPLE I The instant novel sulfonated esters and salts thereof were tested for their detergency properties as well as their efficacy as fabric softeners. The Spangler soil detergency tests were run using an aqueous solution con- 7' TABLE 1 ARd (Soil Removal) Compound 1. Disodium sulfosuccinate of N-(2- hydroxyhexadecyl) diethanolamine 2. Control-Linear tridecyl benzene sulfonate 3. Disodium sulfosuccinate of N-(Z-OHC J diethanolamine 4. Disodium sulfosuccinate of N-(Z-OHC methyl ethanolamine 5. Disodium sulfosuccinate of NB-TAP 300 PPM NB-TAP 300 PPM diisopropanolamine i EXAMPLEH Similarly, the test for softening effect on cotton materials is run by washing one terry cloth towel in 17 gallons of NB tap water at 120 F and air drying. The softness is rated on a scale of 1 to 10, with 1 indicating no softness and 10 representing maximum softness.
TABLE 2 Softness Ratings 1. 10g Al sulfosuecinate of N-(Z-hydroxy 7 hexadecyl) diethanolarnine, 40g Pentasodium Tripolyphosphate (NaTPP) 2. 10% sulfosuccinate of N-(Z-hydroxy l0 octadecyl) methylethanolamine 40% NaTPP 3. 10% sulfosuccinate of N-(Z-hydroxy 10 octadecyl) diisopropanol amine, 40% NaTPP 4. 5g Al sodium sulfosuccinate in (l). 10g Al 5 linear dodecyl benzene sulfonate, 40g NaTPP 5. 30g sulfosuccinate of N-( Z-hydroxyoctadecyl) l0 diethanolamine 6. Linear tridecyl benzene sulfonate 1 The results shown above indicate an unexpectedly excellent detergency in hard and soft water, both cold and hot, as compared to commercial detergent linear tridecyl benzene sulfonate. In addition to possessing excellent detersive properties, instant sulfonated esters exhibit excellent fabric softening characteristics, not possessed by the control. Similar results are obtained with other sulfonated esters of Z-hydroxy alkyl. tertiary alcohol amines of instant invention and salts thereof.
EXAMPLE [I1 Other typical detergent-softening compositions include:
80% sodium tripolyphosphate, and
20% a. sulfosuccinate of N-(Z-OI-I dodecyl) methylethanolamine b. sulfosuccinate of N-(2-OH octadecyl) methylethanolamine c. sulfosuccinate of N-(2-OI-I dodecyl) diisopropanolamine d. sulfosuccinate of N-(2-OH octadecyl) diisopropanolamine e. sulfosuccinate of N-(Z-OH dodecyl) diethanolamine f. sulfosuccinate of N-(2-OH octadecyl) diethanolamine g. sulfosuccinate of N-(2-Ol-I dodecyl) diglycolamine h. sulfosuccinate of N-(Z-OI-I octadecyl) digly'colamine EXAMPLE IV 40 g sodium tripolyphosphate 5 g disodium sulfosuccinate of 2-hydroxy hexadecyl diethanolamine 8 10 g linear tridecyl benzene sulfonate.
Fabric treated with an aqueous solution of the above ingredients in accordance with the method in Example I, gave a softness rating of 5.
EXAMPLE V Repeat Example IV, but omit the linear tridecyl benzene sulfonate and increase the sulfosuccinate content to 10 g. i
The elimination of the sulfonate and an increase in the sulfosuccinate yielded a superior softness rating, namely 7.
EXAMPLE VI The sulfosuccinate of Example V was acidified with lactic acid. Fabric was washed with an aqueous solution thereof, rinsed and dried, in accordance with the procedure in Example 1, resulting in a softness rating of 10.
EXAMPLE VII g of an'8% solution of disodium sulfosuccinate of N-( 2-hydroxyoctadecyl) diethanolamine.
10 g of an 8% solution of 2-heptadecyl-l-methyl-l- [(2-stearoylamido)ethyl] imidazolinium methyl sulfate.
The two ingredients were blended and isopropanol added to form a clear solution. Fabric treated with this solution exhibited a softness rating of 10.
EXAMPLE VIII The composition of Example VII was acidified with lactic acid, thereby forming a clear, viscous liquid. Fabric treated therewith exhibited excellent softness.
EXAMPLE IX 15 g of an 8% solution of disodium sulfosuccinate of N-(2-hydroxyoctadecyl) diethanolamine 15 g of an 8% solution of N-( 2-hydroxy C sarcosine.
The two ingredients were acidified with lactic acid, forming a translucent, viscous liquid. Fabric treated herewith exhibited excellent softness and whiteness.
EXAMPLE X Other typical detergent-softening compositions. include: I
40% sodium tripolyphosphate 45% sodium sulfate 15% disodium sulfosuccinate of N-(2 hydroxyoctadecyl) diisopropanolamine.
EXAMPLE XI 40% sodium tripolyphosphate 45% sodium sulfate 15% disodium sulfosuccinate hydroxyoctadecyl) methyl ethanolamine.
EXAMPLE XII 30 g of an 8% aqueous solution of disodium sulfosuccinate of N-(Z-hydroxyoctadecyl) diethanolamine tested in accordance with the procedure of Example 2 gave a softness rating of 10.
At room temperature, this composition was a clear, l-phase, moderately viscous liquid which may be used in the wash cycle with known commercial laundry detergents as both a softener and detergency booster.
The present invention has been described in conjunction with various illustrations and embodiments thereof set forth in the specification. However, it is evident that equivalents may be substituted for the present compounds and procedural steps, without departing from the principles of this invention or the spirit thereof. Those of skill in the art will recognize what equivalents and substitutes are also within the scope of the present disclosure.
What is claimed:
1. A detergent composition having inherent softening properties comprising about 530% by weight of water soluble sulfosuccinate estersof polyhydroxy tertiary amines, said amines having the structural formula:
wherein R, is an alkyl radical of 8 to 24 carbon atoms, R is an alkyl or alkylol radical of l to 6 carbon atoms, and R is an alkylol radical of l to 6 carbon atoms or the alkali metal, ammonium, alkyl amine and alkanol amine salts thereof, the alkyl and alkanol groups of said amines containing from 2 to 4 carbon atoms, and about -95% water soluble builder salts, said water soluble sulfosuccinate esters being selected from the group consisting of mono, di and trisulfosuccinates containing respectively 1, 2 and 3 carboxyl groups and respectively I, 2 and 3 sulfo groups, and mixtures thereof. a 1 I 2. A detergent composition in accordance with claim 1, wherein the sulfonated mono-ester has the formula:
wherein R and R are as defined above, R is an alkylene radical of l to 6 carbon atoms, R,, is an ethylene radical and X is hydrogen or salt-forming element or radical selected from the group consisting of alkali metal, ammonium, alkyl amine and alkanol amine, the alkyl and alkanol groups of said amines containing from 2 to 4 carbon atoms.
3. A composition in accordance with claim 1, which contains disodium sulfosuccinate of N-(2-hydroxy hexadecyl)-diethanolamine. f
4. Acomposition in accordance with claim l,whic,h contains sulfosuccinate of N-(Z-hydroxyoctadecyl) methylethanolamine.
5. A composition-in accordance with claim 1, which contains sulfosuccinate of N-( 2-hydroxyoctadecyl) di- 7. A method in accordance with claim 6, wherein the isopropanolamine. detergent composition constitutes about ODS-0.5% by 6. A method of simultaneously cleaning and softenweight of the aqueous bath. ing textiles which comprises laundering said textiles in an aqueous bath containing the composition of claim 1. 5

Claims (6)

  1. 2. A detergent composition in accordance with claim 1, wherein the sulfonated mono-ester has the formula:
  2. 3. A composition in accordance with claim 1, which contains disodium sulfosuccinate of N-(2-hydroxy hexadecyl)-diethanolamine.
  3. 4. A composition in accordance with claim 1, which contains sulfosuccinate of N-(2-hydroxyoctadecyl) methylethanolamine.
  4. 5. A composition in accordance with claim 1, which contains sulfosuccinate of N-(2-hydroxyoctadecyl) diisopropanolamine.
  5. 6. A method of simultaneously cleaning and softening textiles which comprises laundering said textiles in an aqueous bath containing the composition of claim 1.
  6. 7. A method in accordance with claim 6, wherein the detergent composition constitutes about 0.05- 0.5% by weight of the aqueous bath.
US00205396A 1971-12-06 1971-12-06 Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines Expired - Lifetime US3803036A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
BE792362D BE792362A (en) 1971-12-06 DETERGENT AND SOFTENING COMPOSITION
US205395A US3928422A (en) 1971-12-06 1971-12-06 Sulfosuccinates of polyhydroxy tertiary amines
US00205396A US3803036A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines
US205290A US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
CA 157600 CA1005455A (en) 1971-12-06 1972-11-27 Esters of dicarboxylic acids and sulphonated dicarboxylic acids with n-hydroxyalkyl-ethanolamines
ES409051A ES409051A1 (en) 1971-12-06 1972-11-28 A method for preparing steres of dicarboxilic acids and poly (tertiary hydroxyamines). (Machine-translation by Google Translate, not legally binding)
DE19722258564 DE2258564A1 (en) 1971-12-06 1972-11-30 COMPOUNDS WITH SURFACTANT AND SOFTENING PROPERTIES AND THEIR USE
IT54427/72A IT973850B (en) 1971-12-06 1972-12-01 COMPOUND CLEANSING AND SOFTENING AND DETERGENT THAT CONTAINS IT
SE7215669A SE400308B (en) 1971-12-06 1972-12-01 DETERGENT COMPOSITION WITH NON-SOFTENING PROPERTIES
AU49563/72A AU4956372A (en) 1971-12-06 1972-12-01 Esters and sulphonated esters of dicarboxylic acids and 2-hydroxy alkyl alcohol-amimes
FR7243002A FR2166982A5 (en) 1971-12-06 1972-12-04
CH1766072A CH576944A5 (en) 1971-12-06 1972-12-05
GB5624572A GB1420209A (en) 1971-12-06 1972-12-06 Surface active esters of dicarboxylic acids and polyhydroxy tertiary maines
US409027A US3927073A (en) 1971-12-06 1973-10-24 Esters of dicarboxylic acids and polyhydroxy tertiary amines as new detergent softener compounds
US05/424,250 US4056558A (en) 1971-12-06 1973-12-12 Sulfosuccinates of polyhydroxy tertiary amines as new detergent-softener compounds
SE7514180A SE7514180L (en) 1971-12-06 1975-12-16 WAY TO CLEAN AND SOFT TEXTILES AT THE SAME TIME
SE7514179A SE7514179L (en) 1971-12-06 1975-12-16 DETERGENT SOFTENING COMPOSITION

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US20540871A 1971-12-06 1971-12-06
US00205396A US3803036A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines
US205395A US3928422A (en) 1971-12-06 1971-12-06 Sulfosuccinates of polyhydroxy tertiary amines
US205290A US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
US409027A US3927073A (en) 1971-12-06 1973-10-24 Esters of dicarboxylic acids and polyhydroxy tertiary amines as new detergent softener compounds

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US00205396A Expired - Lifetime US3803036A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing sulfosuccinates of polyhydroxy tertiary amines
US409027A Expired - Lifetime US3927073A (en) 1971-12-06 1973-10-24 Esters of dicarboxylic acids and polyhydroxy tertiary amines as new detergent softener compounds

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DE2700072A1 (en) * 1977-01-03 1978-07-13 Henkel Kgaa EMULSIONS FOR EMULSION POLYMERIZATION
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
DE2738539A1 (en) * 1977-08-26 1979-03-01 Henkel Kgaa DISPERSING PIGMENTS
DE2738538A1 (en) * 1977-08-26 1979-03-01 Henkel Kgaa DISPERSING PIGMENTS
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition
US4430236A (en) 1981-06-22 1984-02-07 Texize, Division Of Mortonthiokol Liquid detergent composition containing bleach
US4681903A (en) * 1985-08-24 1987-07-21 Bayer Aktiengesellschaft Polyester polyols, a process for their production and their use in the isocyanate polyaddition process
DE4111966A1 (en) * 1991-04-12 1992-10-15 Henkel Kgaa USE OF ESTERS AS A TEXTILE WEIGHTING AGENT
DE4301197A1 (en) * 1993-01-19 1994-07-21 Rewo Chemische Werke Gmbh Poly (oxyalkylene) alkanolamine fatty acid esters, process for their preparation and their use
US6369146B1 (en) * 1999-10-26 2002-04-09 Air Products And Chemicals, Inc. Malic acid diester surfactants

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US3349122A (en) * 1964-04-06 1967-10-24 Atlas Refinery Inc Process for the production of alkane sulfonates
FR1487622A (en) * 1965-07-26 1967-07-07 Archer Daniels Midland Co Preparation of acylated derivatives of secondary amino alkanols and of nu-oxides of these derivatives
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