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WO1996018610A1 - Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters - Google Patents

Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters Download PDF

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Publication number
WO1996018610A1
WO1996018610A1 PCT/EP1995/003583 EP9503583W WO9618610A1 WO 1996018610 A1 WO1996018610 A1 WO 1996018610A1 EP 9503583 W EP9503583 W EP 9503583W WO 9618610 A1 WO9618610 A1 WO 9618610A1
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WO
WIPO (PCT)
Prior art keywords
formula
amphiphilic compounds
compounds according
spacer
independently
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/EP1995/003583
Other languages
German (de)
English (en)
Inventor
Klaus Kwetkat
Wulf Ruback
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.)
Huels AG
Original Assignee
Huels AG
Chemische Werke Huels AG
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 Huels AG, Chemische Werke Huels AG filed Critical Huels AG
Priority to AU35661/95A priority Critical patent/AU3566195A/en
Publication of WO1996018610A1 publication Critical patent/WO1996018610A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
    • 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
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/17—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing carboxyl groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides

Definitions

  • the invention relates to amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on esters.
  • amphiphilic substances A wide variety of anionic, cationic, nonionic and zwitterionic compounds are known as amphiphilic substances. The vast majority of these substances consist of a hydrophilic head group and at least one hydrophobic part.
  • amphiphilic substances there are ecological reasons, e.g. B. bezüg ⁇ Lich the reduction in packaging and transportation, the need to achieve ever greater effect per mass of substance used. Since optimization by mixing amphiphilic substances only continues to a very limited extent, new amphiphilic substances with a higher degree of efficiency are required. In particular, substances with lower critical micelle formation concentrations and / or lower surface and interfacial tensions have to be found in order to be able to significantly reduce the amount of active substance used.
  • cationic surface-active compounds can be obtained by adding long-chain alkyl halides to permethylated alkylenediamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, (1991) 1072; R. Zana, Y. Talmon, Nature, 362 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 9 (1993) 1465].
  • Anionic surface-active compounds with at least two hydrophilic and at least two hydrophobic groups have hitherto been produced only on the basis of diglycidyl ethers (US Pat. No. 5,160,450, JP 01,304,033, JP 4,124,165).
  • diglycidyl ethers are considered toxicologically unsafe and are quite expensive.
  • epichlorohydrin is used for their production, which leads to large amounts of residues, so that these compounds are no longer appropriate from an ecotoxicological as well as an economical point of view.
  • amphiphilic compounds which have at least two hydrophilic and at least two hydrophobic groups, the amphiphilic compounds having a very high degree of effectiveness, based on the amount used, and which are also made from readily available raw materials which are not technically large Accidental by-products can be produced.
  • amphiphilic di- or oligoesters the base of which can be prepared from di-, oligo- or polyols and fatty acids or fatty acid methyl esters.
  • the corresponding di- or oligoesters can be sulfonated.
  • sulfonated fatty acid methyl esters can also be transesterified with di-, oligo- or polyols and then neutralized.
  • amphiphilic compounds according to the invention are compounds of the general formula I.
  • R, R, R, M and M 'in formula I have the meanings described below:
  • R and R independently of one another represent an unbranched or branched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 6 to 18 carbon atoms.
  • R and R are in particular the radicals methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n -
  • R means a spacer consisting of an unbranched or branched
  • the spacer R means in particular
  • the spacer can additionally contain 1 to 4 carbonyl, carboxyl, amino or acylamino groups at any point in the chain;
  • the spacer R further contains 0 to 20, preferably 1 to 12, oxygen and / or nitrogen atoms, 0 to 4 sulfur and 0 to 3 phosphorus atoms, at least one of the heteroatoms occurring at least once.
  • amphiphilic compounds according to the invention are usually characterized by extremely low critical micelle formation concentrations (CMC) and very low surface and interfacial tensions (e.g. against paraffin), which is due to their special structure - at least two hydrophilic groups and at least two hydrophobic groups - must be returned.
  • CMC critical micelle formation concentrations
  • hydrophilic suspending capacity is about halfway between that of conventional surfactants and that of pentasodium tripolyphosphate.
  • amphiphilic compounds according to this invention are particularly suitable as emulsifiers, demulsifiers, detergents, dispersants and hydrotropes in industry and in the home, for example in the fields of metalworking, ore extraction, surface finishing, washing and cleaning, cosmetics, medicine and food processing and preparation.
  • nonionic surface-active substances which can be used for a combination include fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, polyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene-dericinoleedirate, or urethane oil derivatives, or polyoxyethylene-dericin derivative or di-urethane oil derivatives , Polyoxyethylene fatty acid amides, polyoxyethylene alkylamines, alkanolamines, alkyl amine oxides, derivatives of protein hydrolyzates, hydroxy mixed ethers, alkyl polyglycosides and alkyl glucamides.
  • anionic surface-active substances that can be used for combinations are soaps, ether carboxylic acids and their salts, alkyl sulfonates, o-olefin sulfonates, sulfonates of higher fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hydroxymixed ether sulfates, salts of phosphate esters, taurides, isethionates , linear alkylbenzenesulfonates, cumene sulfonates, alkylarylsulfonates, sulfates of polyoxyethylene fatty acid ide and salts of acylamino acids.
  • cationic common surface-active substances examples include aikyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylam onium salts, alkylpyridine salts, alkylisoquinolinium salts, benzethonium chlorides and cationic acylamino acid derivatives.
  • ampholytic surface-active substances examples include amino acids, betaines, sulfobetaines, imidazoline derivatives, soybean lipids and lecithin.
  • amphiphilic compounds according to the invention can also be combined with one another.
  • additives can also be added to the amphiphilic compounds according to the invention.
  • Such additives are specially selected for a formulation and usually include inorganic salts such as sodium chloride and sulfate, as well as builders, hydrotropics, UV absorbers, plasticizers, chelating agents, viscosity modifiers and fragrances.
  • the abovementioned compounds can be prepared from di-, oligo- or polyols and at least twice the equivalent of sulfonated fatty acid methyl esters or by at least double sulfonation of the di-, oligo- or polyester and with aqueous alkali or alkaline earth metal hydroxides or aqueous ammonia or neutralize alkanols. If necessary, the products are bleached in aqueous solution with hydrogen peroxide (0.1 to 2.0%, based on solids).

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

Abstract

L'invention concerne des composés amphiphiles de formule générale (I), comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes à base d'esters. Ces composés amphiphiles sont généralement tensioactifs et sont utilisés en particulier sous forme d'émulsifiants, désémulsifiants, détergents, agents dispersants et hydrotropes, à usage industriel et domestique, par exemple dans les domaines de l'usinage des métaux, de l'extraction de minerais, du traitement de surface, du lavage et du nettoyage, des cosmétiques, de la médecine, du traitement et de la préparation des aliments.
PCT/EP1995/003583 1994-12-17 1995-09-12 Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters Ceased WO1996018610A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU35661/95A AU3566195A (en) 1994-12-17 1995-09-12 Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4445133A DE4445133A1 (de) 1994-12-17 1994-12-17 Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Estern
DEP4445133.4 1994-12-17

Publications (1)

Publication Number Publication Date
WO1996018610A1 true WO1996018610A1 (fr) 1996-06-20

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ID=6536160

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003583 Ceased WO1996018610A1 (fr) 1994-12-17 1995-09-12 Composes amphiphiles comportant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes a base d'esters

Country Status (4)

Country Link
AU (1) AU3566195A (fr)
DE (1) DE4445133A1 (fr)
WO (1) WO1996018610A1 (fr)
ZA (1) ZA9510680B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997009304A1 (fr) * 1995-09-01 1997-03-13 HÜLS Aktiengesellschaft Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2166142A (en) * 1937-01-21 1939-07-18 Benjamin R Harris Sulphocarboxylic acid esters
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
CH273548A (de) * 1949-02-04 1951-02-15 Hoffmann La Roche Verfahren zur Darstellung eines wasserlöslichen Stilböstrolderivates.
US3173940A (en) * 1962-04-16 1965-03-16 Eastman Kodak Co Polyoxyloweralkylene glycol di alpha-sulpho monocarboxylates and salts thereof
US3268563A (en) * 1962-05-03 1966-08-23 Petrolite Corp Esters of an alpha-sulfo carboxylic acid and a glycol
WO1993025646A1 (fr) * 1992-06-17 1993-12-23 Lion Corporation Composition detergente peu agressive pour la peau
DE4300935A1 (de) * 1993-01-15 1994-07-21 Henkel Kgaa Sulfonierte Diester

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2166142A (en) * 1937-01-21 1939-07-18 Benjamin R Harris Sulphocarboxylic acid esters
US2460968A (en) * 1943-09-28 1949-02-08 Innovations Chimiques Sinnova Method for the obtainment of aliphatic sulfonic acids and esters thereof
CH273548A (de) * 1949-02-04 1951-02-15 Hoffmann La Roche Verfahren zur Darstellung eines wasserlöslichen Stilböstrolderivates.
US3173940A (en) * 1962-04-16 1965-03-16 Eastman Kodak Co Polyoxyloweralkylene glycol di alpha-sulpho monocarboxylates and salts thereof
US3268563A (en) * 1962-05-03 1966-08-23 Petrolite Corp Esters of an alpha-sulfo carboxylic acid and a glycol
WO1993025646A1 (fr) * 1992-06-17 1993-12-23 Lion Corporation Composition detergente peu agressive pour la peau
DE4300935A1 (de) * 1993-01-15 1994-07-21 Henkel Kgaa Sulfonierte Diester

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997009304A1 (fr) * 1995-09-01 1997-03-13 HÜLS Aktiengesellschaft Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Also Published As

Publication number Publication date
AU3566195A (en) 1996-07-03
DE4445133A1 (de) 1996-06-20
ZA9510680B (en) 1996-07-13

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