US3928422A - Sulfosuccinates of polyhydroxy tertiary amines - Google Patents

Sulfosuccinates of polyhydroxy tertiary amines Download PDF

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Publication number
US3928422A
US3928422A US205395A US20539571A US3928422A US 3928422 A US3928422 A US 3928422A US 205395 A US205395 A US 205395A US 20539571 A US20539571 A US 20539571A US 3928422 A US3928422 A US 3928422A
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US
United States
Prior art keywords
sulfosuccinate
carbon atoms
esters
hydroxy
sulfosuccinates
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
US205395A
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English (en)
Inventor
Bjorn Sundby
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
Original Assignee
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 US205395A priority patent/US3928422A/en
Priority to US205290A priority patent/US3893930A/en
Priority to US00205396A priority patent/US3803036A/en
Priority to CA 157600 priority patent/CA1005455A/en
Priority to ES409051A priority patent/ES409051A1/es
Priority to DE19722258564 priority patent/DE2258564A1/de
Priority to SE7215669A priority patent/SE400308B/xx
Priority to IT54427/72A priority patent/IT973850B/it
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
Priority to SE7514180A priority patent/SE7514180L/xx
Priority to SE7514179A priority patent/SE7514179L/xx
Application granted granted Critical
Publication of US3928422A publication Critical patent/US3928422A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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

  • This invention relates to novel sulfosuccinates of Z-hydroxy alkyl tertiary 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.
  • the sulfonated esters of instant invention possess detergency, wetting, foaming, and emulsifying properties in both hard and soft waters and at both elevated and lower temperatures.
  • these compounds exhibit substantivity to materials such as cotton, hair, etc. and are excellent in textile softening activity. This high degree of substantivity is unexpected in a surface active material which itself functions to release adsorbed and absorbed substances from materials being washed. Consequently, instant surface active agents simultaneously clean and soften textiles.
  • R is a monovalent hydrocarbon radical of eight to 24 and preferably to carbon atoms
  • R is an alkyl or alkylol radical of one to six carbon atoms
  • R is a divalent hydrocarbon radical of one to six carbon atoms
  • 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,
  • X is a radical, it is preferred that such be ammonium, alkylamine or alkanolamine, eithe'r mono-, di-, or tri-alkylamine or mono-, dior tri-alkanolamine, in which the alkyl and alkanol groups of the salt-forming amines are of one to four 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 unsaturated dicarboxylic 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 eight to 24 and preferably 10 to 20 carbon atoms
  • R is an alkyl or hydroxyalkyl radical containing one to six carbon atoms
  • R is a hydroxy alkyl radical containing one to six carbon atoms.
  • radicals of this class are:
  • R R 2 R CHCH N-R OH+ C on R OH R 0 I 2 3 lg RI H2- 4 R5 OOH, R CHCH NR 0 --R COOX SO;,X
  • the sulfonation step propanolamine, N-propyl-N-ethanol-amine, N-propyll5 adds the sulfonate group to the unsaturated acid radical N-isopropanolamine, N-methyl-N-hydroxyethoxyethylat the point of unsaturation as illustrated by the followamine, N-butyl-N-hydroxy-ethoxyethylamine, N- ing equations when utilizing maleic anhydride:
  • R1CHCH2N-R4OCCH CHCOOH CHCH -NR.,oC (pH CH C00Na SO Na cyclohexyl-N-hydroxyethoxyethylamine, N-butyl-N-
  • the alcoholamine has at least two hydroxyl groups, one ethanolamine, di(hydroxyethoxyethyl)amine, mono(- in the long chain resulting from the epoxide ring open- 3O hydroxyethoxyethyl)amme, N-hydroxyethoxy-ethoxmg and one or more from the original alcoholamine.
  • yethyl- N-hydroxyethyl-N-hydr0xy-is0pr pylamine When utilizing equimolar amounts of reactants, the N-benzyl-N-hydroxyethylamine, or N-cyclo-hexyl-N-Z- primary hydroxyl is preferentially esterified into the hydroxy-Z-phenylethylamine. mono-ester, since it is the least stearically hindered and therefore the most reactive group.
  • the number example of an amine/epoxide reaction is the preparaof hydroxyl groups in the alcoholamine is determination of Z-hydroxyalkyl-diethanolamine. 4O tive of the formation of the mono-, di-, or tri-esters.
  • the unsaturated dicarboxylic acid anhydride may be The sulfonated esters formed in accordance with maleic anhydride or a substituted maleic anhydride. instant invention have one free carboxyl group and one Q sulfonate group for every esterified carboxyl radical as' E R shown by the following structural formulae:
  • 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 anh'ydride e.g., maleic anhydride
  • 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 50-90C 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.
  • 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.
  • 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 and prevents the production of a polymeric linear ester.
  • the esterification 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 monodiand 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, anti-static, 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 upon the sulfonated esters of instant invention as the sole detergent and fabric softener.
  • 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 containing 1.5 g. of detergent/liter water (0.15% product concentration) said detergent comprising 15% of the compound to be tested, 35% sodium tripolyphosphate and 50% sodium sulfate (based on dry ingredients), in soft and hard water, at both 70F and 120 F.
  • Three Spangler soil swatches were washed 10 minutes in a Tergotometer at 100 rpm, rinsed 5 minutes, and dried. The ingredients were dry-blended by conventional methods and added to the aqueous system in the Tergotometer.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US205395A 1971-12-06 1971-12-06 Sulfosuccinates of polyhydroxy tertiary amines Expired - Lifetime US3928422A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
BE792362D BE792362A (fr) 1971-12-06 Composition detergente et adoucissante
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
US00205396A US3803036A (en) 1971-12-06 1971-12-06 Detergent-softener compositions containing sulfosuccinates of 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 (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 (de) 1971-12-06 1972-12-04
CH1766072A CH576944A5 (de) 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
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
US409027A US3927073A (en) 1971-12-06 1973-10-24 Esters of dicarboxylic acids and polyhydroxy tertiary amines as new detergent softener compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/424,250 Continuation-In-Part US4056558A (en) 1971-12-06 1973-12-12 Sulfosuccinates of polyhydroxy tertiary amines as new detergent-softener compounds

Publications (1)

Publication Number Publication Date
US3928422A true US3928422A (en) 1975-12-23

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ID=27539516

Family Applications (4)

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

Country Status (6)

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US (4) US3928422A (de)
AU (1) AU4956372A (de)
CH (1) CH576944A5 (de)
DE (1) DE2258564A1 (de)
FR (1) FR2166982A5 (de)
GB (1) GB1420209A (de)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167420A (en) * 1977-08-26 1979-09-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Process for dispersing pigments and fillers using aminoalkanols and salt, alkoxylation and quaternization derivatives thereof
US4167421A (en) * 1977-08-26 1979-09-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Process for dispersing pigments and fillers using aminoalkanols and salt, alkoxylation and quaternization derivatives thereof
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
US4250050A (en) * 1977-01-03 1981-02-10 Henkel Kommanditgesellschaft Auf Aktien Sulfosuccinate emulsifiers
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4310683A (en) * 1975-05-07 1982-01-12 Witco Chemical Corporation Sulfosuccinate diesters
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2539349C2 (de) * 1975-09-04 1985-04-11 Hoechst Ag, 6230 Frankfurt Wäschenachbehandlungsmittel
NL7714317A (nl) * 1976-12-31 1978-07-04 Hoechst Ag Avivagemiddel en werkwijze voor het aviveren van textielmateriaal.
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 (de) * 1991-04-12 1992-10-15 Henkel Kgaa Verwendung von estern als textilweichmachender wirkstoff
DE4301197A1 (de) * 1993-01-19 1994-07-21 Rewo Chemische Werke Gmbh Poly(oxyalkylen)alkanolaminfettsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung
US6369146B1 (en) * 1999-10-26 2002-04-09 Air Products And Chemicals, Inc. Malic acid diester surfactants
WO2022140518A1 (en) 2020-12-23 2022-06-30 Ecolab Usa Inc. Non-cationic softeners and methods of use

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2176423A (en) * 1936-01-13 1939-10-17 American Cyanamid & Chem Corp Esters of sulphodicarboxylic acids
US2844608A (en) * 1953-01-26 1958-07-22 Bayer Ag Sulfodicarboxylic acid compounds
US3002995A (en) * 1958-09-02 1961-10-03 American Cyanamid Co Purification of salts of dialkyl esters of sulfosuccinic acid
US3349122A (en) * 1964-04-06 1967-10-24 Atlas Refinery Inc Process for the production of alkane sulfonates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR854314A (fr) * 1938-05-13 1940-04-10 Ig Farbenindustrie Ag Procédé pour traiter des matières fibreuses
FR1487622A (fr) * 1965-07-26 1967-07-07 Archer Daniels Midland Co Préparation de dérivés acylés d'amino-alcanols secondaires et de nu-oxydes de ces dérivés
US3454494A (en) * 1965-08-03 1969-07-08 Standard Chem Products Inc Textile softener compositions
US3649569A (en) * 1967-06-05 1972-03-14 Procter & Gamble Textile treating compounds compositions and processes for treating textiles
DK133307A (de) * 1968-06-12 Colgate Palmolive Co

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2176423A (en) * 1936-01-13 1939-10-17 American Cyanamid & Chem Corp Esters of sulphodicarboxylic acids
US2844608A (en) * 1953-01-26 1958-07-22 Bayer Ag Sulfodicarboxylic acid compounds
US3002995A (en) * 1958-09-02 1961-10-03 American Cyanamid Co Purification of salts of dialkyl esters of sulfosuccinic acid
US3349122A (en) * 1964-04-06 1967-10-24 Atlas Refinery Inc Process for the production of alkane sulfonates

Cited By (7)

* 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
US4250050A (en) * 1977-01-03 1981-02-10 Henkel Kommanditgesellschaft Auf Aktien Sulfosuccinate emulsifiers
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
US4167420A (en) * 1977-08-26 1979-09-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Process for dispersing pigments and fillers using aminoalkanols and salt, alkoxylation and quaternization derivatives thereof
US4167421A (en) * 1977-08-26 1979-09-11 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Process for dispersing pigments and fillers using aminoalkanols and salt, alkoxylation and quaternization derivatives thereof
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

Also Published As

Publication number Publication date
US3893930A (en) 1975-07-08
CH576944A5 (de) 1976-06-30
FR2166982A5 (de) 1973-08-17
US3803036A (en) 1974-04-09
DE2258564A1 (de) 1973-06-14
US3927073A (en) 1975-12-16
AU4956372A (en) 1974-06-06
GB1420209A (en) 1976-01-07

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