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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United States
Prior art keywords
detergent
accordance
maleate
composition
ester
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Expired - Lifetime
Application number
US205290A
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English (en)
Inventor
Bjorn Sundby
Harold Eugene Wixon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Colgate Palmolive Co
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Colgate Palmolive Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE792362D priority Critical patent/BE792362A/xx
Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US00205396A priority patent/US3803036A/en
Priority to US205290A priority patent/US3893930A/en
Priority to US205395A priority patent/US3928422A/en
Priority to ZA727938A priority patent/ZA727938B/xx
Priority to CA 157600 priority patent/CA1005455A/en
Priority to ES409051A priority patent/ES409051A1/es
Priority to DE19722258564 priority patent/DE2258564A1/de
Priority to IT54427/72A priority patent/IT973850B/it
Priority to SE7215669A priority patent/SE400308B/xx
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 US3893930A publication Critical patent/US3893930A/en
Priority to SE7514180A priority patent/SE7514180L/xx
Priority to SE7514179A priority patent/SE7514179L/xx
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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US205290A 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines Expired - Lifetime US3893930A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
BE792362D BE792362A (fr) 1971-12-06 Composition detergente et adoucissante
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
US205395A US3928422A (en) 1971-12-06 1971-12-06 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 (es) 1971-12-06 1972-11-28 Un metodo para preparar esteres de acidos dicarboxilicos y poli (hidroxiaminas terciarias).
DE19722258564 DE2258564A1 (de) 1971-12-06 1972-11-30 Verbindungen mit tensid- und weichspueleigenschaften und deren verwendung
IT54427/72A IT973850B (it) 1971-12-06 1972-12-01 Composto detergente ed ammorbidente e detersivo che lo contiene
SE7215669A SE400308B (sv) 1971-12-06 1972-12-01 Detergentkomposition med ingaende mjukgoringsegenskaper
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 (cg-RX-API-DMAC10.html) 1971-12-06 1972-12-04
CH1766072A CH576944A5 (cg-RX-API-DMAC10.html) 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 (sv) 1971-12-06 1975-12-16 Sett att samtidigt rengora och mjukgora textilier
SE7514179A SE7514179L (sv) 1971-12-06 1975-12-16 Detergentmjukgoringskomposition

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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US3893930A true US3893930A (en) 1975-07-08

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Application Number Title Priority Date Filing Date
US205290A Expired - Lifetime US3893930A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
US205395A Expired - Lifetime US3928422A (en) 1971-12-06 1971-12-06 Sulfosuccinates of polyhydroxy tertiary amines
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

Family Applications After (3)

Application Number Title Priority Date Filing Date
US205395A Expired - Lifetime US3928422A (en) 1971-12-06 1971-12-06 Sulfosuccinates of polyhydroxy tertiary amines
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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US (4) US3893930A (cg-RX-API-DMAC10.html)
AU (1) AU4956372A (cg-RX-API-DMAC10.html)
CH (1) CH576944A5 (cg-RX-API-DMAC10.html)
DE (1) DE2258564A1 (cg-RX-API-DMAC10.html)
FR (1) FR2166982A5 (cg-RX-API-DMAC10.html)
GB (1) GB1420209A (cg-RX-API-DMAC10.html)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
US4430236A (en) 1981-06-22 1984-02-07 Texize, Division Of Mortonthiokol Liquid detergent composition containing bleach

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4310683A (en) * 1975-05-07 1982-01-12 Witco Chemical Corporation Sulfosuccinate diesters
NL7714317A (nl) * 1976-12-31 1978-07-04 Hoechst Ag Avivagemiddel en werkwijze voor het aviveren van textielmateriaal.
DE2700072A1 (de) * 1977-01-03 1978-07-13 Henkel Kgaa Emulgatoren fuer die emulsionspolymerisation
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
DE2738538A1 (de) * 1977-08-26 1979-03-01 Henkel Kgaa Dispergieren von pigmenten
DE2738539A1 (de) * 1977-08-26 1979-03-01 Henkel Kgaa Dispergieren von pigmenten
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Also Published As

Publication number Publication date
GB1420209A (en) 1976-01-07
US3928422A (en) 1975-12-23
FR2166982A5 (cg-RX-API-DMAC10.html) 1973-08-17
US3803036A (en) 1974-04-09
AU4956372A (en) 1974-06-06
US3927073A (en) 1975-12-16
DE2258564A1 (de) 1973-06-14
CH576944A5 (cg-RX-API-DMAC10.html) 1976-06-30

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