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US3893930A - Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines - Google Patents

Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines Download PDF

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Publication number
US3893930A
US3893930A US205290A US20529071A US3893930A US 3893930 A US3893930 A US 3893930A US 205290 A US205290 A US 205290A US 20529071 A US20529071 A US 20529071A US 3893930 A US3893930 A US 3893930A
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Prior art keywords
detergent
accordance
maleate
composition
ester
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US205290A
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Bjorn Sundby
Harold Eugene 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 US205290A priority patent/US3893930A/en
Priority to US205395A priority patent/US3928422A/en
Priority to US00205396A priority patent/US3803036A/en
Priority to ZA727938A priority patent/ZA727938B/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 IT54427/72A priority patent/IT973850B/en
Priority to AU49563/72A priority patent/AU4956372A/en
Priority to SE7215669A priority patent/SE400308B/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 US3893930A publication Critical patent/US3893930A/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 water soluble esters of dicarboxylic acids and 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 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 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.
  • This invention relates to novel detergent-composithey may be used as emulsifiers, solubilizing agents for lipophilic materials, wetting agents, detergent and softeners for textiles and hair.
  • detergent compositions comprising certain esters of dicarboxylic acids and 2- hydroxyalkyl tertiary alcohol amines and salts thereof in conjunction with water soluble detergency builder salts possess all of the characteristics desired.
  • the aforedefined esters possess not only exceptional detergency characteristics, but possess fabric softening characteristics and are completely compatible with conventional water soluble detergency builder salts.
  • the combination of the present invention comprising the esters of dicarboxylic acidss and 2-hydroxy alkyl alcoholamines and the conventional water soluble detergency builder salts can be produced both as a homogeneous single phase liquid detergent composition or can be conveniently prepared in the form of bars, flakes, granular or tableted granular compositions.
  • esters of dicarboxylic acid and polyhydroxy tertiary amines and salts thereof possess the unusual characteristics of excellent detergency and fabric softening 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 esters of dicarboxylic acids and Z-hydroxy alkyl tertiary alcoholamine and water soluble detergency builder salts.
  • esters of dicarboxylic acids and Z-hydroxyalkyl tertiary alcohol amines employed in the novel detergent compositionsof 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 l to 6 carbon atoms
  • R is a divalent hydrocarbon radical of l to 6 carbon atoms
  • R OH R R is a saturated, unsaturated, aliphatic or aromatic divalent hydrocarbon radical (residue of the 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 salt-forming metal, capable ofmaking the compounds water soluble.
  • X is a radical it is preferred that such be ammonium, alkylamine or alkanolamine, either mono-, di-, or tiralkylamine or m'ono-, di or trialkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of l to 4 carbon atoms, preferably 2 to 3 carbon atoms.
  • novel esters of the present invention are prepared by reacting the dicarboxylic acid or preferably the anhydride thereof with a polyhydroxy tertiary amine having the structure: i
  • R is a monovalent hydrocarbon radical of 8 to 2'4 and preferably 10 to 20 carbon atoms
  • R is an alkyl atomsExa'mple's of radicalsof this class are:
  • the dicarboxylic acid may be saturated, unsaturated, substituted or unsubstituted aliphatic or aromatic and include phthalic, succinic, maleic, glutaric, tartaric, malic, adipic, diphenic, naphthalic, etc.
  • R radicals are as aforedefined, and equimolar amounts of reactants are used.
  • 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 alcoholamine.
  • the primary hydroxyl is preferentially esterified into the mono-ester, since it is the least stearically hindered and therefor the most reactive group.
  • the other hydroxyl radicals react to form the di-ester, tri-ester, etc. and mixtures thereof.
  • the number of hydroxyl groups in the alcoholamine is determinative of the formation of the mono-, di-, or triesters.
  • CHCH2" N CH2OCH2CH2OH R4 COOH monoand di-esters The esters formed in accordance with instant invention have one free carboxyl group for every esterified carboxyl radical as shown by the following structural formulae:
  • the esterification of the 2-hydroxyalkylalcohola mines .with the dicarboxylic acid anhydride is ,an exethermic reaction which can be carried out in aprotic solvent, ether, chloroform or acetone, but it can alsobe carried out neat.
  • the latter method is preferable as an industrial process, since no solvent is involved.
  • the powdered acid anhydride e.g. maleic anhydride
  • the product is obtained as a high viscosity melt, that rapidly solidifies upon Cooling.
  • the ester. e.g. maleate
  • the alkali metal salt e.g.
  • reaction by neutralizing with a dilute aqueous solution of alkali metal hydroxide such as a NaOl-l.
  • alkali metal hydroxide such as a NaOl-l.
  • the reactants are first dissolved therein and the solution refluxed until the esterification is complete. Evaporation of the solvent yields a resin-like waxy product, insoluble in water, but readily soluble in a dilute aqueous sodium hydroxide solution.
  • the reaction is controlled so that only one mole of water is removed per mole of alcohol. Termination of the reaction at this point ensures the formation of the esters of instant invention and prevents the production of a polymeric lin ear ester.
  • the reaction may be controlled by conventional methods of cooling or by other suitable means.
  • the products obtained are usually yellow or light yellow viscous mono-, di-, tri-esters and mixtures thereof, resin-like in appearance, insoluble in water, but readily soluble in alcohol, acetone, chloroform and in dilute aqueous sodium hydroxide wherein the sodium salt of the ester is formed.
  • the mono-, diand tri-esters can be readily separated and purified by chromatographic techniques in the usual manner.
  • the sodium salts of instant novel'esters are homogeneous andvery watersolublefConsequently, instant esters and salts thereof have been found to be particularly useful as detergents, due to their combined property of detergency and fabri'cconditioning (softening, anti-static, etc.
  • esters in accordance with the present invention includez' 1 N(Z-hydroxydodecyl)-methylethanolamine maleate N-(2-hydroxyoctadecyl)-methylethanolamine maleate N-(Z-hydroxydodecyl)-diisopropanolamine maleate N-(Z-hyroxyoctadecyl)-diisopropanolamine maleate N-(Z-hydroxydodecyl)-diethanolamine maleate N-(2 -hydroxyoctadecyl)-diethanolamine maleate N-(2 -hydroxydodecyl)-diglycolamine maleate N-(2-hydroxyoctadecyl)-diglycolamine maleate N-(2-hydroxypentadecyl)-diethanolamine phthalate N-(Z-hydroxyoctadecyl)-diethanolamine phthalate Further examples of esters of dicarboxylic acid and Z-hydroxyalky
  • novel esters of the present invention in addition to possessing excellent detergency and Water 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 tertiary alcohol amine-dicarboxylic acid ester as the detergent and,water softener. Because of the unusual compatibility of the esters of the present invention with the various detergent builders it is possible to prepare both solid phase detergent compositions and liquid detergent compositions.
  • novel detergent compositions of the present invention may contain one or more water soluble 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 are (1 alkali metal amino polycarboxylates (e.g.
  • sodium and potassium ethylenediaminetetraacetates sodium and potassium ethylenediaminetetraacetates, N-(2-hydroxyethyl)- ethylenediaminetriacetates, nitrilo triacetates, and N-(Z-hydroxyethyl)-nitrilo diacetates);
  • alkali metal salts of phytic acid e.g., sodium and potassium phytates See US. Pat. No. 2,739,942
  • water soluble salts of ethane-l-hydroxy-l, l-diphosphonate e.g. the trisodium and tripotassium salts See U.S. Pat. No. 3,159,581)
  • water soluble salts of methylene diphosphonic acid e.g.
  • mixtures of organic and inorganic builder salts is alsocontemplated by instant invention.
  • the active ester or salt thereof is generally employed in an amount of from about 5 to 30 percent by weight of the total composition. While the water soluble detergency builder salts comprise from about to about95 percent by weight of the total composition.
  • the dicarboxylic acid-polyhydroxy tertiary amine ester comprises about 10 25 percent by weight while the detergent builders comprise from about percent 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.
  • Examples or nonionic detergents are dodecyldimethylamine oxide and the condensation product of coconut fatty alcohol with 5.5 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-dodecylaminopropionate.
  • An example of 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 60F to about 212F, 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 percent to about 0.5 percent by total weight, and the detergent composition should be added so as to provide an effective detergent and water softening amount of the 2-hydroxyalkylalcoholaminedicarboxylic acid ester component of at least 0.005 percent.
  • 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 minutes being generally used in the washing cycle of an automatic agitator type washer.
  • the detergent composition is drained off of thefabrics and the fabrics are rinsed in substantially pure water.
  • the fabrics can be rinsed as many times as desired.
  • 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 preparation of the 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 from e.g. detergent granules. flakes. bar, etc.
  • the individual components of the novel detergent composition of the present invention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
  • EXAMPLE 1 The instant novel 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 containing 1.5 g. of detergent/liter water (0.15 percent product concentration), said detergent comprising 15 percent of the compound to be tested, 35 percent sodium tripolyphosphate and 50 percent sodium sulfate (based on dry in- 8 gredients), in soft and hard water at both F and 120F.
  • Three Spangler soil swatches were washed 10 minutes in a Tergotometer with the rotor at 100 rpm, rinsed and dried. The ingredients were dry-blended by conventional methods and added to the aqueous system in the Tergotometer.
  • the test for softening effect on cotton materials is run using a terry cloth towel in three gallons of 100 p.p.m. hardness water. After washing in a miniature washing machine, the towel is rinsed in the normal manner and dried. The softness is rated on a scale of 1 to 10, with 1 indicating no softness and 10 representing maximum softness.
  • N-(Z-OH dodecyl) methylethanolaminemaleate b. N-(2-OH)octadecyl) methylethanolamine maleate c. N-(Z-OH) dodecyl) diisopropanolamine maleate d. N-(2-OH)octadecyl) diisopropanolamine maleate e. N-(2-OH) dodecyl) diethanolamine maleate f. N-(Z-OH) octadecyl) diethanolamine maleate g. N-(Z-OH) dodecyl) diglycolamine maleate h.
  • EXAMPLE VII 7r Ingredient 13.2 Ester of Z-Hydroxy hexadecyl diethanolamine and maleic anhydride 86.8 Water At room temperature, this composition is a clear, 1- phase, moderately viscous liquid which may be used in the wash cycle with known commercial laundry detergents as both a softener and detergency booster. Softness rating is 10.
  • a detergent composition having inherent softening properties containing as essential ingredients about -530 percent weight of a dual detergent and softening compound selected from the group consisting of esters of dicarboxylic acids of the group consisting of phthalic, succinic, maleic, glutaric, tartaric, malic, adipic, diphenic and naphthalic acids and polyhydroxy tertiary mono functional amines, said amine having the structural formula:
  • R is an alkyl radical of 8 to 24 carbon atoms
  • R is an alkyl or alkylol radical containing 1 to 6 carbon atoms
  • R is an alkylol radical containing 1 to 6 carbon atoms and the alkali metal, ammomium, mono-, diand trialkyl, or mono-, diand trialkanol amines salts of said ester in which the alkyl and alkanol groups of the amine contain from 1 to 4 carbon atoms salts thereof and about -95 percent by weight of watersoluble builder salt.
  • a detergent composition having inherent softening properties containing as essential ingredients about 5-30% by weight of a dual detergent and softening compound selected from the group consisting of esters of dicarboxylic acid selected from the group consisting of maleic acid, phthalic acid and anhydrides thereof and polyhydroxy tertiary monofunctional amines, said amine having the structural formula:
  • R is an alkyl radical of 8 to 24 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 the alkali metal, ammonium, mono-, diand trialkyl, or mono-, diand trialkanol amines salts of said ester in which the alkyl and alkanol groups of the amine contain from I to 4 carbon atoms, salts thereof and about 7095 percent by weight of watersoluble builder salt.
  • R and R are as defined above, R is an alkylene radical of 1 to 6 carbon atoms, R is ethylene and X is hydrogen or salt-forming element or radical.
  • composition in accordance with claim 1, wherein the salt of the ester is sodium phthalate of N- (2-hydroxyhexadecyl)-diethanolamine.
  • a detergent composition in accordance with claim 1 wherein said builder is sodium tripolyphosphate.
  • a detergent composition in accordance with claim further containing detergent selected from the g cup-consisting of anionic, nonionic, ampholytic, cationic and zwitterionic detergent.
  • a detergent composition in accordance with claim 1 wherein said ester is selected from the group consisting of:
  • N-(Z-OH) octadecyl) diglycolamine maleate N-(Z-OH) octadecyl) diglycolamine maleate.

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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 esters of dicarboxylic acids and 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 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 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 [191 Sundby et al.
[ 1 July 8,1975
[ DETERGENT-SOFTEN'ER COMPOSITIONS CONTAINING ESTERS OF DICARBOXYLIC ACIDS AND POLYHYDROXY TERTIARY AMINES [75] Inventors: Bjorn Sundby, Piscataway; Harold Eugene Wixon, New Brunswick,
21 Appl. No.: 205,290
[52] U.S. Cl 252/8.8; 1l7/l39.5 CQ; 252/529; 252/546; 252/548 Primary ExaminerTh0mas J. Herbert, Jr. Assistant Examiner--Bruce H. Hess Attorney, Agent, or Firm-Steven J. Baron; Norman Blumenkopf; Herbert S. Sylvester [57] 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 esters of dicarboxylic acids and 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 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 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.
15 Claims, N0 Drawings DETERGENT-SOFTENER"COMPOSITIONS CONTAINING ESTERSOF DICARBOXYLIC ACIDS AND POLYHYDROXY TERTIARY AMINES I This invention relates to novel detergent-composithey may be used as emulsifiers, solubilizing agents for lipophilic materials, wetting agents, detergent and softeners for textiles and hair.
Since the introduction of commercial synthetic organic detergents and emulsifiers to replace the conventional watersoluble 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.
It has now been discovered in accordance with the present invention that detergent compositions comprising certain esters of dicarboxylic acids and 2- hydroxyalkyl tertiary alcohol amines and salts thereof in conjunction with water soluble detergency builder salts possess all of the characteristics desired. Thus, in this respect it has been discovered that the aforedefined esters possess not only exceptional detergency characteristics, but possess fabric softening characteristics and are completely compatible with conventional water soluble detergency builder salts. Thus, the combination of the present invention comprising the esters of dicarboxylic acidss and 2-hydroxy alkyl alcoholamines and the conventional water soluble detergency builder salts can be produced both as a homogeneous single phase liquid detergent composition or can be conveniently prepared in the form of bars, flakes, granular or tableted granular compositions.
Accordingly, it is an object of the present invention to provide novel detergency 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 certain esters of dicarboxylic acid and polyhydroxy tertiary amines and salts thereof possess the unusual characteristics of excellent detergency and fabric softening 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 esters of dicarboxylic acids and Z-hydroxy alkyl tertiary alcoholamine and water soluble detergency builder salts.
The esters of dicarboxylic acids and Z-hydroxyalkyl tertiary alcohol amines employed in the novel detergent compositionsof 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 l to 6 carbon atoms, R, is a divalent hydrocarbon radical of l to 6 carbon atoms (R OH R R is a saturated, unsaturated, aliphatic or aromatic divalent hydrocarbon radical (residue of the 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 salt-forming metal, capable ofmaking the compounds water soluble. If X is a radical it is preferred that such be ammonium, alkylamine or alkanolamine, either mono-, di-, or tiralkylamine or m'ono-, di or trialkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of l to 4 carbon atoms, preferably 2 to 3 carbon atoms.
The novel esters of the present invention are prepared by reacting the dicarboxylic acid or preferably the anhydride thereof with a polyhydroxy tertiary amine having the structure: i
OH R.-
\vvherein R is a monovalent hydrocarbon radical of 8 to 2'4 and preferably 10 to 20 carbon atoms, R is an alkyl atomsExa'mple's of radicalsof this class are:
, CH2CH2OH CH CH OH ,ca ca on c H-JCH-JOH CHgCHgOH CHZCHQOH CHgCHgOH The dicarboxylic acid may be saturated, unsaturated, substituted or unsubstituted aliphatic or aromatic and include phthalic, succinic, maleic, glutaric, tartaric, malic, adipic, diphenic, naphthalic, etc.
The reaction is predominently in accordance with the following equation:
I ll
R CH CH-,N-R ,OC-R,-,-COOH.
wherein the R radicals are as aforedefined, and equimolar amounts of reactants are used. 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 alcoholamine. When utilizing equimolar amounts of reactants, the primary hydroxyl is preferentially esterified into the mono-ester, since it is the least stearically hindered and therefor the 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, tri-ester, etc. and mixtures thereof. Similarly, the number of hydroxyl groups in the alcoholamine is determinative of the formation of the mono-, di-, or triesters.
C "2C H- OH COOH R W mono-, d1,-
x and tri-esters COOH COOH
+ R mono-. di-
esters COOH OH alkyl COOH 5. R|CHCH2" N CH2OCH2CH2OH R4 COOH monoand di-esters The esters formed in accordance with instant invention have one free carboxyl group for every esterified carboxyl radical as shown by the following structural formulae:
mono-ester;
The esterification of the 2-hydroxyalkylalcohola mines .with the dicarboxylic acid anhydride is ,an exethermic reaction which can be carried out in aprotic solvent, ether, chloroform or acetone, but it can alsobe carried out neat. The latter method is preferable as an industrial process, since no solvent is involved. The powdered acid anhydride (e.g. maleic anhydride) is added gradually to the liquid alcoholamine which is held at a temperature of about 100C. The product is obtained as a high viscosity melt, that rapidly solidifies upon Cooling. The ester. (e.g. maleate) may be converted to the alkali metal salt (e.g. sodium) by neutralizing with a dilute aqueous solution of alkali metal hydroxide such as a NaOl-l. When utilizing a solvent, the reactants are first dissolved therein and the solution refluxed until the esterification is complete. Evaporation of the solvent yields a resin-like waxy product, insoluble in water, but readily soluble in a dilute aqueous sodium hydroxide solution. When utilizing the dicarboxylic acid in lieu of the anhydride, the reaction is controlled so that only one mole of water is removed per mole of alcohol. Termination of the reaction at this point ensures the formation of the esters of instant invention and prevents the production of a polymeric lin ear ester. The reaction may be controlled by conventional methods of cooling or by other suitable means.
The products obtained are usually yellow or light yellow viscous mono-, di-, tri-esters and mixtures thereof, resin-like in appearance, insoluble in water, but readily soluble in alcohol, acetone, chloroform and in dilute aqueous sodium hydroxide wherein the sodium salt of the ester is formed. The mono-, diand tri-esters can be readily separated and purified by chromatographic techniques in the usual manner. The sodium salts of instant novel'esters are homogeneous andvery watersolublefConsequently, instant esters and salts thereof have been found to be particularly useful as detergents, due to their combined property of detergency and fabri'cconditioning (softening, anti-static, etc.
Examples of esters in accordance with the present invention includez' 1 N(Z-hydroxydodecyl)-methylethanolamine maleate N-(2-hydroxyoctadecyl)-methylethanolamine maleate N-(Z-hydroxydodecyl)-diisopropanolamine maleate N-(Z-hyroxyoctadecyl)-diisopropanolamine maleate N-(Z-hydroxydodecyl)-diethanolamine maleate N-(2 -hydroxyoctadecyl)-diethanolamine maleate N-(2 -hydroxydodecyl)-diglycolamine maleate N-(2-hydroxyoctadecyl)-diglycolamine maleate N-(2-hydroxypentadecyl)-diethanolamine phthalate N-(Z-hydroxyoctadecyl)-diethanolamine phthalate Further examples of esters of dicarboxylic acid and Z-hydroxyalkyl tertiary alcoholamine and processes for producing the same can be found in copending applica tion Ser. No. IR2338 Ser. No. 205,408, filed in the name of Bjorn Sundby on Dec. 6, 1971.
The novel esters of the present invention, in addition to possessing excellent detergency and Water 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 tertiary alcohol amine-dicarboxylic acid ester as the detergent and,water softener. Because of the unusual compatibility of the esters of the present invention with the various detergent builders it is possible to prepare both solid phase detergent compositions and liquid detergent compositions.
In addition to the aforedefined esters or salts thereof, the novel detergent compositions of the present invention may contain one or more water soluble 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 (1 alkali metal amino polycarboxylates (e.g. sodium and potassium ethylenediaminetetraacetates, N-(2-hydroxyethyl)- ethylenediaminetriacetates, nitrilo triacetates, and N-(Z-hydroxyethyl)-nitrilo diacetates); (2) alkali metal salts of phytic acid (e.g., sodium and potassium phytates See US. Pat. No. 2,739,942; (3) water soluble 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 andtripotassium methylene diphosphonate and the other salts described in US. Pat. No. 3,213,030; (5) water soluble salts of substitutedmethylene diphosphonic acids (e.g., trisodium and tripotassium ethylidene, isopropylidene, 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 citraconic acid and copolymers with themselves and other compatible monomers such as ethylene); and mixtures thereof. Similarly, mixtures of organic and inorganic builder salts is alsocontemplated by instant invention.
In the detergent composition ofthe present invention the active ester or salt thereof is generally employed in an amount of from about 5 to 30 percent by weight of the total composition. While the water soluble detergency builder salts comprise from about to about95 percent by weight of the total composition. Preferably, the dicarboxylic acid-polyhydroxy tertiary amine ester comprises about 10 25 percent by weight while the detergent builders comprise from about percent of the total composition. is
The detergent compositions of this invention can containany 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 or nonionic detergents are dodecyldimethylamine oxide and the condensation product of coconut fatty alcohol with 5.5 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-dodecylaminopropionate. 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 60F to about 212F, 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 percent to about 0.5 percent by total weight, and the detergent composition should be added so as to provide an effective detergent and water softening amount of the 2-hydroxyalkylalcoholaminedicarboxylic acid ester component of at least 0.005 percent.
ln 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 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 thefabrics 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.
'l n the preparation of the 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 from e.g. detergent granules. flakes. bar, etc. However, the individual components of the novel detergent composition of the present invention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
Various embodiments of 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 1 The instant novel 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 containing 1.5 g. of detergent/liter water (0.15 percent product concentration), said detergent comprising 15 percent of the compound to be tested, 35 percent sodium tripolyphosphate and 50 percent sodium sulfate (based on dry in- 8 gredients), in soft and hard water at both F and 120F. Three Spangler soil swatches were washed 10 minutes in a Tergotometer with the rotor at 100 rpm, rinsed and dried. The ingredients were dry-blended by conventional methods and added to the aqueous system in the Tergotometer.
Similarly the test for softening effect on cotton materials is run using a terry cloth towel in three gallons of 100 p.p.m. hardness water. After washing in a miniature washing machine, the towel is rinsed in the normal manner and dried. The softness is rated on a scale of 1 to 10, with 1 indicating no softness and 10 representing maximum softness.
The results shown above indicate an unexpectedly excellent detergency in hard and soft water, both cold and hot, as compared to commercial detergentlinear tridecyl benzene sulfonate. In addition to possessing excellent detersive properties, instant esters exhibit excellent fabric softening characteristics, not possessed by the control. Similar results are obtained with other 2- hydroxy alkyl tertiary alcohol aminedicarboxylic esters and salts thereof.
EXAMPLE 11 Other typical detergent-softening compositions include:
% sodium tripolyphosphate, and
20% (a) N-(Z-OH dodecyl) methylethanolaminemaleate b. N-(2-OH)octadecyl) methylethanolamine maleate c. N-(Z-OH) dodecyl) diisopropanolamine maleate d. N-(2-OH)octadecyl) diisopropanolamine maleate e. N-(2-OH) dodecyl) diethanolamine maleate f. N-(Z-OH) octadecyl) diethanolamine maleate g. N-(Z-OH) dodecyl) diglycolamine maleate h. N(2-OH) octadecyl) diglycolamine maleate EXAMPLE in 71 Ingredients 80 7 Sodium tripolyphosphate 20 Sodium salt of the ester of Z-hydroxy hexadecyl diethanolamine and maleic anhydride.
This composition tested in accordance with the procedure in Example I gave a softness value of 8.-When the ester content is increased to 23 percent, the softness value is increased to 10."
EXAMPLE IV The following composition tested in accordance with the method of Examplel yielded a softness value of 10.
Weight in grams' Ingredients 40 g. Sodium tripolyphosphate g. Sodium salt of the maleate of 2- hydroxy hexadecyl diethanolamine. g. Linear tridecyl benzene sulfonate EXAMPLE V Weight in grams Ingredient 40 g. Sodium tripolyphosphate 5 g. Sodium phthalate of Z-hydroxy hexadecyl diethanolamine 10 g. Linear tridecyl benzene sulfonate This composition tested in accordance with the method in Example I gave a softness rating of 8.
EXAMPLE VI Ingredients 23 Sodium phthalate of Z-hydroxyhexadecyl diethanolamine 77 Sodium tripolyphosphate Fabric washed with this composition in accordance with the procedure in Example 1 exhibited a softness rating of 10.
EXAMPLE VII 7r Ingredient 13.2 Ester of Z-Hydroxy hexadecyl diethanolamine and maleic anhydride 86.8 Water At room temperature, this composition is a clear, 1- phase, moderately viscous liquid which may be used in the wash cycle with known commercial laundry detergents as both a softener and detergency booster. Softness rating is 10.
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.
' l. A detergent composition having inherent softening properties containing as essential ingredients about -530 percent weight of a dual detergent and softening compound selected from the group consisting of esters of dicarboxylic acids of the group consisting of phthalic, succinic, maleic, glutaric, tartaric, malic, adipic, diphenic and naphthalic acids and polyhydroxy tertiary mono functional amines, said amine having the structural formula:
i" l R, CHCH2 NR;,
wherein R is an alkyl radical of 8 to 24 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 the alkali metal, ammomium, mono-, diand trialkyl, or mono-, diand trialkanol amines salts of said ester in which the alkyl and alkanol groups of the amine contain from 1 to 4 carbon atoms salts thereof and about -95 percent by weight of watersoluble builder salt.
2. A detergent composition having inherent softening properties containing as essential ingredients about 5-30% by weight of a dual detergent and softening compound selected from the group consisting of esters of dicarboxylic acid selected from the group consisting of maleic acid, phthalic acid and anhydrides thereof and polyhydroxy tertiary monofunctional amines, said amine having the structural formula:
OH R
wherein R is an alkyl radical of 8 to 24 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 the alkali metal, ammonium, mono-, diand trialkyl, or mono-, diand trialkanol amines salts of said ester in which the alkyl and alkanol groups of the amine contain from I to 4 carbon atoms, salts thereof and about 7095 percent by weight of watersoluble builder salt.
3. A detergent composition in accordance with claim 1, wherein said ester consists of mono-, di-, and triesters and/or mixtures thereof.
4. A detergent composition in accordance with claim 1 wherein the ester has the formula:
wherein R and R are as defined above, R is an alkylene radical of 1 to 6 carbon atoms, R is ethylene and X is hydrogen or salt-forming element or radical.
5. A composition in accordance with claim 1, wherein the ester is N-(2-hydroxy hexadecyl)- diethanol-amine maleate.
6. A composition in accordance with claim 1, wherein the salt of the ester is sodium phthalate of N- (2-hydroxyhexadecyl)-diethanolamine.
7. A composition in accordance with claim 1, wherein the ester is N-(2-hydroxyhexadecyl) diethanolamine phthalate.
an aqueous bath containing the composition of claim 1.
9. A method in accordance with claim 8, wherein the detergent composition constitutes about ODS-0.5% by weight of the aqueous bath.
10. A method in accordance with claim 9, wherein the ester constitutes about .005% by weight of the aqueous bath.
11. A detergent composition in accordance with claim 1 wherein said builder is sodium tripolyphosphate.
12. A composition in accordance with claim 4 wherein X is selected from the group consisting of alkali metal, ammonium, mono-, diand trialkylamine and mono-, diand trialkanolamine wherein the alkyl and alkanol groups of said amine contain from 1 to 4 carbon atoms.
13. A detergent composition in accordance with claim further containing detergent selected from the g cup-consisting of anionic, nonionic, ampholytic, cationic and zwitterionic detergent.
14. A detergent composition in accordance with claim 13 wherein said detergent is linear tridecyl benzene sulfonate.
15. A detergent composition in accordance with claim 1 wherein said ester is selected from the group consisting of:
N-( 2-OH) dodecyl) methylethanolamine maleate;
N-(Z-Ol-l) octadecyl) methylethanolamine maleate;
N-(2-Ol-l) dodecyl) diisopropanolamine maleate;
N-( 20H) octadecyl) diisopropanolamine maleate;
N-(ZOl-l) dodecyl) diethanolamine maleate;
N-(Z-OH) octadecyl) diethanolamine maleate;
N-( 2-Ol-l) dodecyl) diglycolamine maleate;
N-(Z-OH) octadecyl) diglycolamine maleate.

Claims (15)

1. A DETERGENT COMPOSITION HAVING INHERENT SOFTENING PROPERTIES CONTAINING AS ESSENTIAL INGREDINTS ABOUT 5-30 PERCENT WEIGHT OF A DUAL DETERGENT AND SOFTENING COMPOUND SELECTED FROM THE GROUP CONSISTING OF PHTHALIC, SUCCINIC, MALEIC, GLUTARIC GROUP CONSISTING OF PHTHALIC, SUCCINIC, MALEIC, GLUTARIC, TARTARIC, MALIC, ADIPIC, DIPHENIC AND NAPHTHALIC ACIDS AND POLYHYDROXY TERTIARY MONO FUNCTIONAL AMINS, SAID AMINE HAVING THE STRUCTURAL FORMULA: R1-CH(-OH)-CH2-N(-R2)-R3 WHEREIN R1 IS AN ALKYL RADICAL OF 8 TO 24 CARBON ATOMS, R2 IS AN ALKYL OR ALKYLOL RADICAL CONTAINING 1 TO 6 CARBON ATOMS, AND R3 IS AN ALKYL RADICAL CONTAINING 1 TO 6 CARBON ATOMS AND THE ALKALI METAL, AMMOMIUM, MONO- DI-AND TRIALKYL, OR MOMO-, DI-AND TRIALKANOL AMINES SALTS OF SAID ESTER IN WHICH THE ALKYL AND ALKANOL GROUPS OF THE AMINE CONTAIN FROM 1 TO 4 CARBON ATOMS SALTS THEREOF AND ABOUT 70-95 PERCENT BY WEIGHT OF WATER-SOLUBLE BUILDER SALT.
2. A detergent composition having inherent softening properties containing as essential ingredients about 5-30% by weight of a dual detergent and softening compound selected from the group consisting of esters of dicarboxylic acid selected from the group consisting of maleic acid, phthalic acid and anhydrides thereof and polyhydroxy tertiary monofunctional amines, said amine having the structural formula:
3. A detergent composition in accordance with claim 1, wherein said ester consists of mono-, di-, and tri-esters and/or mixtures thereof.
4. A detergent composition in accordance with claim 1 wherein the ester has the formula:
5. A composition in accordance with claim 1, wherein the ester is N-(2-hydroxy hexadecyl)-diethanol-amine maleate.
6. A composition in accordance with claim 1, wherein the salt of the ester is sodium phthalate of N-(2-hydroxyhexadecyl)-diethanolamine.
7. A composition in accordance with claim 1, wherein the ester is N-(2-hydroxyhexadecyl) diethanolamine phthalate.
8. A method of simultaneously cleaning and sOftening textiles which comprises laundering said textiles in an aqueous bath containing the composition of claim 1.
9. A method in accordance with claim 8, wherein the detergent composition constitutes about 0.05-0.5% by weight of the aqueous bath.
10. A method in accordance with claim 9, wherein the ester constitutes about .005% by weight of the aqueous bath.
11. A detergent composition in accordance with claim 1 wherein said builder is sodium tripolyphosphate.
12. A composition in accordance with claim 4 wherein X is selected from the group consisting of alkali metal, ammonium, mono-, di- and trialkylamine and mono-, di- and trialkanolamine wherein the alkyl and alkanol groups of said amine contain from 1 to 4 carbon atoms.
13. A detergent composition in accordance with claim 1 further containing detergent selected from the group consisting of anionic, nonionic, ampholytic, cationic and zwitterionic detergent.
14. A detergent composition in accordance with claim 13 wherein said detergent is linear tridecyl benzene sulfonate.
15. A detergent composition in accordance with claim 1 wherein said ester is selected from the group consisting of: N-(2-OH) dodecyl) methylethanolamine maleate; N-(2-OH) octadecyl) methylethanolamine maleate; N-(2-OH) dodecyl) diisopropanolamine maleate; N-(2OH) octadecyl) diisopropanolamine maleate; N-(2OH) dodecyl) diethanolamine maleate; N-(2-OH) octadecyl) diethanolamine maleate; N-(2-OH) dodecyl) diglycolamine maleate; N-(2-OH) octadecyl) diglycolamine maleate.
US205290A 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines Expired - Lifetime US3893930A (en)

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BE792362D BE792362A (en) 1971-12-06 DETERGENT AND SOFTENING COMPOSITION
US205290A US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
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
ZA727938A ZA727938B (en) 1971-12-06 1972-11-09 Detergent softener compositions
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
AU49563/72A AU4956372A (en) 1971-12-06 1972-12-01 Esters and sulphonated esters of dicarboxylic acids and 2-hydroxy alkyl alcohol-amimes
SE7215669A SE400308B (en) 1971-12-06 1972-12-01 DETERGENT COMPOSITION WITH NON-SOFTENING PROPERTIES
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

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US20540871A 1971-12-06 1971-12-06
US205290A US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
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
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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US205290A Expired - Lifetime US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
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CH576944A5 (en) 1976-06-30
US3803036A (en) 1974-04-09
AU4956372A (en) 1974-06-06
US3927073A (en) 1975-12-16
US3928422A (en) 1975-12-23
GB1420209A (en) 1976-01-07
DE2258564A1 (en) 1973-06-14
FR2166982A5 (en) 1973-08-17

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