WO1998020964A2 - Sulfates d'alcool gras et sulfates d'ether alcoylique avec des ions antagonistes de trialkylammonium ainsi que leur production et utilisation - Google Patents

Sulfates d'alcool gras et sulfates d'ether alcoylique avec des ions antagonistes de trialkylammonium ainsi que leur production et utilisation Download PDF

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Publication number
WO1998020964A2
WO1998020964A2 PCT/EP1997/006098 EP9706098W WO9820964A2 WO 1998020964 A2 WO1998020964 A2 WO 1998020964A2 EP 9706098 W EP9706098 W EP 9706098W WO 9820964 A2 WO9820964 A2 WO 9820964A2
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WO
WIPO (PCT)
Prior art keywords
formula
alkyl radical
compounds
och
sulfur trioxide
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.)
Ceased
Application number
PCT/EP1997/006098
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German (de)
English (en)
Other versions
WO1998020964A3 (fr
Inventor
Bernd Papenfuhs
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
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
Application filed by Clariant GmbH filed Critical Clariant GmbH
Priority to AU53171/98A priority Critical patent/AU5317198A/en
Publication of WO1998020964A2 publication Critical patent/WO1998020964A2/fr
Publication of WO1998020964A3 publication Critical patent/WO1998020964A3/fr
Anticipated expiration legal-status Critical
Ceased 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/08—Monoamines containing alkyl groups having a different number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/06—Hydrogenosulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
    • 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
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-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
    • 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
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • the invention relates to new surfactants with high surface activity, which consist of a fatty alcohol sulfate or alkyl ether sulfate and a trialkyl-substituted ammonium ion.
  • the invention also includes the production of these surfactants and their use, which also means the use in compositions.
  • the invention relates to compounds of the formulas I and II below
  • R 1 is an alkyl group with 6 to 22 carbon atoms
  • R 2 is an alkyl group with 1 to 4 carbon atoms
  • R 3 is an alkyl group with 6 to 22 carbon atoms, which can be largely fluorinated, and n is a number from 0 to 10,
  • R 4 is an alkyl group with 6 to 22 carbon atoms
  • R 5 is an alkyl group with 1 to 4 carbon atoms
  • R 6 is an alkyl group with 6 to 22 carbon atoms, which may be largely fluorinated
  • n is a number from 0 to 10.
  • Organic sulfates that contain long hydrophobic alkyl groups such as fatty alcohol sulfates or sulfated fatty alcohol alkoxylates, are effective and versatile anionic surfactants. They are usually prepared from the corresponding alcohols with typical sulfating agents such as oleum, gaseous sulfur trioxide, S0 3 / pyridine Complex or chlorosulfonic acid.
  • the compounds of the formulas I and Ii according to the invention can be obtained from mixtures of the corresponding tertiary amines and alcohols in very good quality by the sulfation reaction in a falling film reactor with an S0 3 / air (1 to 10 Vol .-% S0 3 ) or S0 3 / inert gas mixture (for example nitrogen) is carried out as a so-called "one-pot process.
  • an S0 3 / air (1 to 10 Vol .-% S0 3 ) or S0 3 / inert gas mixture for example nitrogen
  • the sulfur trioxide is formed by complexing with the tertiary amines used activated so that the sulfation reaction proceeds smoothly and with a particularly good yield.
  • the pH can optionally be adjusted by adding acid or base.
  • the products of the formulas I and II according to the invention can be combined as desired with other surfactants, for example with alkali or alkaline earth ether sulfates based on glycol monoalkyl ethers or corresponding alkyl sulfates or alkyl sulfonates.
  • the surfactants according to the invention dissolve in water, lower alcohols, lower glycols or a mixture of these solvents. The same applies to compositions of the active compounds according to formulas I and II with suitable cosurfactants.
  • Fluorine-containing surfactants according to formulas I and II in which the radicals R 3 and R 6 are fluoroalkyl groups, reduce the surface tension particularly strongly. In 0.1% concentration at pH 7, they give very good values in the Ross-Miles foam height test and in the whipped foam volume test. Since no toxicological data are yet available for fluorine-containing compounds according to formulas I and II, their use should still be limited to technical applications in closed systems.
  • a homogeneous mixture consisting of 196.6 g (1, 0 mol) of a C 12/16 fatty alcohol and 228.8 g (1, 0 mol) of a C 12/1 -Alkyldimethylamins is in a falling film reactor (reactor temperature 50 ° C) with a 2.2 vol .-% S0 3 containing S0 3 / air mixture in a molar ratio of 0.98 (S0 3 to amine) reacted.
  • the colorless product paste which flows off at 45 ° C. and has a pH of 5.7 (measurement in 1% strength aqueous solution) contains 93.5% of the complex compound according to the invention (determined by potentiometric surfactant titration).
  • Example 2 Analogously to Example 1, an equimolar mixture of the components (in each case one mol corresponds to 160.0 g of dimethyloctylamine and 365.0 g of LZ96 oxyethylate) is reacted with sulfur trioxide in a falling film reactor.
  • the product which is thin at 45 ° C. and contains 87.9% of the complex according to the invention (potentiometric surfactant titration), is still readily stirrable (pH 6.3).
  • R 1 C 12/14 H 25/29
  • R 2 CH 3
  • R 3 nC 6 F 13 (CH 2) 2
  • ⁇ 0th
  • Example 2 Analogously to Example 1, an equimolar mixture of the components each corresponds to one mole of 228.8 g of amine and 426.3 g of the perfluorohexylethanol (®Fluowet EA 600) in a falling film reactor reacted with sulfur trioxide.
  • the flowing light brown product paste contains 85.2% of the complex compound according to the invention (determined by potentiometric surfactant titration).
  • R C 12/14 H 25/29>
  • R CH 3>
  • Example 2 Analogously to Example 1, an equimolar mixture of the components (each corresponding to one mole of 228.8 g of amine and 660.0 g of ®Fluowet OTN oxyethylate), which in this case must be stirred in the metering vessel, since otherwise it is separated into two phases, reacted with sulfur trioxide in a falling film reactor.
  • the emerging brown sulfation product contains 88.6% of the complex compound according to the invention (determined by potentiometric surfactant titration).
  • Example 2 Analogously to Example 1, an equimolar mixture of the components, each corresponding to one mole (300.3 g of amidamine and 196.6 g of fatty alcohol), is reacted with sulfur trioxide in a falling film reactor. A highly viscous light brown product paste is obtained which contains 92.4% of the target compound (potentiometric surfactant titration); the pH is 5.8.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des complexes tensioactifs fortement moussant produits par sulfitage de mélanges alcool/trialkylamine dans un procédé en récipient unique utilisant, de préférence, de l'anhydride sulfurique gazeux dilué. L'invention concerne également des compositions contenant non seulement les complexes tensioactifs mais aussi des tensioactifs connus et des solvants appropriés. Les complexes tensioactifs conviennent à une pluralité d'utilisations, par exemple, pour les détergents et formulations cosmétiques. Sous une forme partiellement fluorée, ils sont particulièrement adaptés comme émulsifiants pour les formulations techniques.
PCT/EP1997/006098 1996-11-12 1997-11-05 Sulfates d'alcool gras et sulfates d'ether alcoylique avec des ions antagonistes de trialkylammonium ainsi que leur production et utilisation Ceased WO1998020964A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU53171/98A AU5317198A (en) 1996-11-12 1997-11-05 Fatty alcohol sulfates and alkylethersulfates with trialkylammonium counter-ions and well as their production and use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19646587.7 1996-11-12
DE19646587A DE19646587A1 (de) 1996-11-12 1996-11-12 Neue Fettalkoholsulfate und Alkylethersulfate mit Trialkylammonium-Gegenionen sowie ihre Herstellung und Verwendung

Publications (2)

Publication Number Publication Date
WO1998020964A2 true WO1998020964A2 (fr) 1998-05-22
WO1998020964A3 WO1998020964A3 (fr) 1998-10-29

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PCT/EP1997/006098 Ceased WO1998020964A2 (fr) 1996-11-12 1997-11-05 Sulfates d'alcool gras et sulfates d'ether alcoylique avec des ions antagonistes de trialkylammonium ainsi que leur production et utilisation

Country Status (3)

Country Link
AU (1) AU5317198A (fr)
DE (1) DE19646587A1 (fr)
WO (1) WO1998020964A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1354872A1 (fr) * 2002-04-17 2003-10-22 Kao Corporation Sels d'amines d'esters d'acide sulfurique, sels d'amines d'acides sulfuriques, leur préparation et compositions adoucissantes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011015046A1 (de) * 2011-03-24 2012-09-27 Sasol Germany Gmbh Hochkonzentrierte fließfähige Salze von Alkylpolyalkoxysulfaten
ITTO20130186A1 (it) * 2013-03-08 2014-09-09 Zschimmer & Schwarz Italiana S P A Procedimento per la preparazione di composizioni anidre di alchil(etossi)solfati

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891143A (en) * 1984-01-06 1990-01-02 Woodward Fred E Water insoluble antistatic compositions
GB2254325B (en) * 1991-04-03 1995-03-15 Kao Corp Ammonium salts and hair treating agent containing the same
JP2625068B2 (ja) * 1992-10-06 1997-06-25 花王株式会社 新規アンモニウム塩、その製法及び中間体アミドアミン、並びに毛髪処理剤
US5387372A (en) * 1993-03-05 1995-02-07 Colgate-Palmolive Company Composition for cleansing body with high foaming action
EP0785978A1 (fr) * 1994-10-13 1997-07-30 The Procter & Gamble Company Composition detergente contenant des amines et des tensioactifs anioniques

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1354872A1 (fr) * 2002-04-17 2003-10-22 Kao Corporation Sels d'amines d'esters d'acide sulfurique, sels d'amines d'acides sulfuriques, leur préparation et compositions adoucissantes
US7179783B2 (en) 2002-04-17 2007-02-20 Kao Corporation Sulfuric acid amine salt, sulfonic acid amine salt, production thereof and softener composition

Also Published As

Publication number Publication date
DE19646587A1 (de) 1998-05-14
AU5317198A (en) 1998-06-03
WO1998020964A3 (fr) 1998-10-29

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