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EP0847385A1 - Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene - Google Patents

Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Info

Publication number
EP0847385A1
EP0847385A1 EP96923979A EP96923979A EP0847385A1 EP 0847385 A1 EP0847385 A1 EP 0847385A1 EP 96923979 A EP96923979 A EP 96923979A EP 96923979 A EP96923979 A EP 96923979A EP 0847385 A1 EP0847385 A1 EP 0847385A1
Authority
EP
European Patent Office
Prior art keywords
amphiphilic compounds
compounds according
acetylene
acid
hydrophobic groups
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.)
Withdrawn
Application number
EP96923979A
Other languages
German (de)
English (en)
Inventor
Klaus Kwetkat
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
Publication of EP0847385A1 publication Critical patent/EP0847385A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • 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
    • A61K8/55—Phosphorus compounds
    • A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • 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
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/60—Unsaturated compounds containing ether groups, groups, groups, or groups the non-carboxylic part of the ether being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols

Definitions

  • the invention relates to anionic amphiphilic compounds with several hydrophilic and hydrophobic groups based on acetylene derivatives.
  • 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. with regard to the reduction of packaging and transport costs, the need to achieve ever greater effect per mass of substance used. Because an optimization by mixing amphiphilic substances requires higher efficiency. 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. In addition, they must be readily available, preferably from easily accessible starting substances.
  • cationic surface-active compounds can be obtained by adding long-chain alkyl halides to permethylated alkylenediamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, 7 (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 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 up-to-date from an ecotoxicological and economic point of view.
  • amphiphilic anionic compounds which have at least two hydrophilic and at least two hydrophobic groups, are readily water-soluble and have good surfactant properties and high efficiency, and are prepared from readily available technical raw materials without a large amount of undesired by-products can.
  • anionic acetylene derivatives which can be prepared by functionalizing acetylene diols.
  • the acetylenediols are either prepared by known processes by reacting acetylene with alkali metal hydroxides and then with methyl ketones either in an aqueous or non-aqueous medium (e.g. BSI Shergina et al., Izx, Akad. Nauk SSSR, Ser. Khim., 1977 , (6), 1447 (CA: 8_7_: - 101877); DE 37 11 282, JP 52046009.) or with aldehydes or obtained by coupling two terminal alkynols (e.g. DE 2520735, JP 50108204).
  • aqueous or non-aqueous medium e.g. BSI Shergina et al., Izx, Akad. Nauk SSSR, Ser. Khim., 1977 , (6), 1447 (CA: 8_7_:
  • Functionalization is the reaction of the alkynyl diols with SO / inert gas (or oleum or chlorosulfonic acid or amidosulfonic acid) and subsequent neutralization with a base (not when using amidosulfonic acid) or with polyphosphoric acid and subsequent neutralization, or with one Halogenacetic acid, a sulton and subsequent neutralization or with a taurine and subsequent neutralization.
  • SO / inert gas or oleum or chlorosulfonic acid or amidosulfonic acid
  • a base not when using amidosulfonic acid
  • polyphosphoric acid and subsequent neutralization or with one Halogenacetic acid, a sulton and subsequent neutralization or with a taurine and subsequent neutralization.
  • the compounds according to the invention are all compounds of the general formula (I):
  • R to R in the formula (I) have the meanings described below:
  • R to R. independently of one another represent hydrogen, an unbranched or branched, saturated or unsaturated hydrocarbon radical having 1 to 22, preferably 6 to 18, carbon atoms, it being possible for only R or R “and R— or R to stand for hydrogen at the same time.
  • r can assume the values 1 to 4, preferably 1 or 2, X and Y independently of one another represent the substituents
  • n 0 to 20, preferably 0 to 8
  • m 0 to 20, preferably 0 to 12
  • n + m 0 to 40, preferably 0 to 20,
  • alkoxylate units if present, can be included randomly or in blocks and the order is arbitrary and where M is an alkali, ammonium or alkanolammonium ion or stoichiometrically an alkaline earth metal ion.
  • 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 can be attributed to their special structure - at least two hydrophilic groups and at least two hydrophobic groups got to.
  • CMC critical micelle formation concentrations
  • hydrophilic suspending capacity is about halfway between the conventional ones Surfactants and that of the pentasodium tripolyphosphate is.
  • amphiphilic compounds according to this invention are particularly suitable as emulsifiers, demulsifiers, detergents, dispersants and hydro tropics and antistatic agents in industry and in the household, for example in the fields of metalworking, ore extraction, textile auxiliaries, surface finishing, washing and cleaning, cosmetics, Medicine and food processing and preparation.
  • nonionic surface-active substances which can be used for a combination are 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-ricinoleic acid ethylenediethoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenedioleoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediaminoxyethylene acid ethylenediamine ethylenedioleoxyethoxyethenoethoxyethylene acid ethylenediethoxyethylene acid ethylenedioleoxyethoxyethoxy acid ethylenedioleoxye
  • anionic surface-active substances which can be used for combinations include soaps, ether carboxylic acids and their salts, alkyl sulfonates, ⁇ -olefin sulfonates, ⁇ -sulfofatty acid derivatives, sulfonates of higher fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hydroxy mixed ether sulfates, salts of phosphate esters , Taurides, isethionates, linear alkylbenzenesulfonates, cumene sulfonates, alkylarylsulfonates, sulfates of polyoxyethylene fatty acid amides and salts of acylamino acids.
  • cationic common surface-active substances which can be used for combinations include alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, alkylpyridinium salts, alkylisoquinolinium salts, benzethonium chlorides and cationic acylamino acid derivatives.
  • ampholytic surface-active substances examples include amino acids, betaines, sulfobetaines, imidazoline derivatives, soybean oil 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.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Polyethers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des composés amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes à base de dérivés d'acétylène.
EP96923979A 1995-09-01 1996-07-09 Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene Withdrawn EP0847385A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19532293 1995-09-01
DE19532293A DE19532293A1 (de) 1995-09-01 1995-09-01 Anionische amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von Acetylenderivaten
PCT/EP1996/002994 WO1997009304A1 (fr) 1995-09-01 1996-07-09 Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Publications (1)

Publication Number Publication Date
EP0847385A1 true EP0847385A1 (fr) 1998-06-17

Family

ID=7771015

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96923979A Withdrawn EP0847385A1 (fr) 1995-09-01 1996-07-09 Composes amphiphiles anioniques comportant plusieurs groupes hydrophiles et hydrophobes a base de derives d'acetylene

Country Status (5)

Country Link
EP (1) EP0847385A1 (fr)
JP (1) JPH11513032A (fr)
AU (1) AU6418996A (fr)
DE (1) DE19532293A1 (fr)
WO (1) WO1997009304A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19717264A1 (de) 1997-04-24 1998-10-29 Huels Chemische Werke Ag Amphiphole Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Di, Oligo- oder Polyenen
ES2831379T3 (es) * 2003-10-09 2021-06-08 Ambrx Inc Derivados poliméricos para la modificación selectiva de proteínas

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3831822A1 (de) * 1988-09-19 1990-04-05 Henkel Kgaa Verfahren zur herstellung von sulfonaten gegebenenfalls ethoxylierter und/oder propoxylierter fettalkohole
DE3932492A1 (de) * 1989-09-28 1991-05-02 Henkel Kgaa Salze von sulfonierten estern von dicarbonsaeuren mit ungesaettigten fettalkoholen bzw. -alkoxylaten, verfahren zu ihrer herstellung und ihre verwendung als oberflaechenaktive mittel
DE4316214A1 (de) * 1993-05-14 1994-11-17 Henkel Kgaa Sulfonierte Diester
DE4441363A1 (de) * 1994-11-21 1996-05-23 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf Basis von Di-, Oligo- oder Polyolethern
DE4445133A1 (de) * 1994-12-17 1996-06-20 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Estern

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9709304A1 *

Also Published As

Publication number Publication date
AU6418996A (en) 1997-03-27
DE19532293A1 (de) 1997-03-06
WO1997009304A1 (fr) 1997-03-13
JPH11513032A (ja) 1999-11-09

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