WO1997007089A1 - Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide aminosuccinique - Google Patents

Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide aminosuccinique Download PDF

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Publication number
WO1997007089A1
WO1997007089A1 PCT/EP1996/003114 EP9603114W WO9707089A1 WO 1997007089 A1 WO1997007089 A1 WO 1997007089A1 EP 9603114 W EP9603114 W EP 9603114W WO 9707089 A1 WO9707089 A1 WO 9707089A1
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WO
WIPO (PCT)
Prior art keywords
amphiphilic compounds
compounds according
amphiphilic
hydrophobic groups
acid derivatives
Prior art date
Application number
PCT/EP1996/003114
Other languages
German (de)
English (en)
Inventor
Klaus Kwetkat
Michael Brock
Herbert Koch
Original Assignee
HÜLS Aktiengesellschaft
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 HÜLS Aktiengesellschaft filed Critical HÜLS Aktiengesellschaft
Priority to AU66998/96A priority Critical patent/AU6699896A/en
Publication of WO1997007089A1 publication Critical patent/WO1997007089A1/fr

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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
    • C09K23/28—Aminocarboxylic acids
    • 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
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
    • 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
    • C11D1/04—Carboxylic acids or salts thereof
    • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325—Amines
    • D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines

Definitions

  • the invention relates to amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid 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. Since optimization by mixing amphiphilic substances only continues to a 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 amounts 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 alkyl diamines [R. Zana, M. Benrraou, R. Rueff, Langmuir, 2 (1991) 1072; R. Zana, Y. Talmon, Nature, M2 (1993) 228; E. Alami, G. Beinert, P. Marie, R. Zana, Langmuir, 2 (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 ether (US Pat. No. 5,160,450, JP 01304033, 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 Connections from an ecotoxicological as well as an economic point of view are no longer up to date.
  • the object was therefore to find amphiphilic compounds which have at least two hydrophilic and at least two hydrophobic groups, have good surfactant properties and high efficiency, and can be prepared from technically readily available raw materials without large amounts of undesired by-products.
  • amphiphilic N, N'-dialkyl-N, N'-disuccinic diesters which can be prepared by adding N.N'-dialkyldiamines to two equivalents of maleic acid and then esterifying with alcohols or alcohol ethoxylates.
  • 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.
  • the substituents 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-undecyl , n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, n-uneicosyl, n-docosyl and their various branched chain isomers
  • 2 R denotes an aliphatic or aromatic, cyclic or acyclic spacer having 2 to 16, preferably 2 to 12 carbon atoms and each having 0 to 6 oxygen and / or nitrogen atoms, which can also be branched.
  • M and M represent an alkali, ammonium, alkanolammonium or 1/2 alkaline earth ion.
  • R and R independently of one another represent an unbranched or branched, saturated or unsaturated hydrocarbon radical having 1 to 18, preferably 1 to 6, carbon atoms.
  • the substituents 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-undecyl , n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and their branched-chain isomers and the corresponding mono-, di- or tri-unsaturated radicals.
  • 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
  • paraffin very low surface and interfacial tensions
  • most of them have a very high hydrophilic suspending capacity, which 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 hydro tropics as well as antistatic agents in industry and household, for example in the fields of metalworking, ore extraction, surface finishing, plastics production, textile auxiliaries, washing and cleaning, especially of textiles or of hard surfaces, cosmetics, medicine and food processing and preparation.
  • nonionic surface-active substances that can be used for a combination are fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, ethoxylates of higher alcohols, poly- lyoxyethylene fatty acid glycerides, polyoxyethylene propylene glycol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene castor oil or hardened castor oil derivatives, polyoxyethylene lanolin derivatives, polyoxyethylene fatty acid amides, polyoxyethylene alkyl amines, alkanolamines, alkyl amine oxyoxides, derivatives of hydroxyl amide hydoxides, hydroxyl amide hydrolysers, derivatives of hydroxyl amide oxides, Examples of anionic surface-active substances which can be used for combinations are soaps, ether carboxylic acids and their salts, alkyl sulfate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium
  • Examples of common cationic surfactants that can be used for combinations include alkyl trimethyl ammonium salts, alkyl dimethyl ammonium salts, alkyl dimethyl benzyl ammonium salts, alkyl pyridinium 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, and also builders, hydrotropics, UV absorbers, plasticizers, chelating agents, viscosity modifiers and fragrances.
  • the above compounds can be prepared from N, N'-dialkylated diamines and two equivalents of maleic acid at temperatures from 80 to 180 ° C.
  • the esterification is carried out with two equivalents of alcohol or alcohol alkoxylate — the hydrophilicity of the products can be precisely coordinated with this — in the presence a catalyst, preferably a basic catalyst, at temperatures from 60 to 190 ° C.
  • the neutralization is carried out with aqueous alkali or alkaline earth metal hydroxides or aqueous ammonia or alkanolamines.

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

Abstract

L'invention a pour objet des composés amphiphiles de formule générale (I), ayant au moins deux groupes hydrophiles et au moins deux groupes hydrophobes à base de dérivés d'acide aminosuccinique. Les composés amphiphiles conformes à l'invention sont, pour la plupart, tensio-actifs et peuvent être utilisés comme émulsifiants, désémulsifiants, détergents, dispersants et hydrotropiques, à usage à la fois industriel et domestique, par exemple dans les domaines ci-après: usinage des métaux, extraction des minerais, amélioration des surfaces, lavage et nettoyage, cosmétique, médecine, traitement et préparation des produits alimentaires.
PCT/EP1996/003114 1995-08-12 1996-07-16 Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide aminosuccinique WO1997007089A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU66998/96A AU6699896A (en) 1995-08-12 1996-07-16 Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19529767A DE19529767A1 (de) 1995-08-12 1995-08-12 Amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von Aminobernsteinsäurederivaten
DE19529767.9 1995-08-12

Publications (1)

Publication Number Publication Date
WO1997007089A1 true WO1997007089A1 (fr) 1997-02-27

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PCT/EP1996/003114 WO1997007089A1 (fr) 1995-08-12 1996-07-16 Composes amphiphiles a plusieurs groupes hydrophiles et hydrophobes a base de derives d'acide aminosuccinique

Country Status (3)

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AU (1) AU6699896A (fr)
DE (1) DE19529767A1 (fr)
WO (1) WO1997007089A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6586365B2 (en) 2000-10-06 2003-07-01 Monsanto Technology, Llc Method for reducing pest damage to corn by treating transgenic corn seeds with clothianidin pesticide
US6593273B2 (en) 2000-10-06 2003-07-15 Monsanto Technology Llc Method for reducing pest damage to corn by treating transgenic corn seeds with pesticide
EP2020236A1 (fr) 1999-10-25 2009-02-04 Laboratoire Theramex Médicament contraceptif à base d'un progestatif et d'un estrogéne, son mode de préparation et son utilisation
CN106732168A (zh) * 2016-12-15 2017-05-31 钦州市钦南区科学技术情报研究所 一种表面活性剂组合物及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3077487A (en) * 1959-06-17 1963-02-12 Victor Chemical Works Lower alkylene and lower alkylenephenylene-lower alkylene polyamine bis n, n'-lower alkylene di and tri carboxylic acids, esters, salts, and chelates
DE2341045A1 (de) * 1972-08-21 1974-03-07 Ciba Geigy Ag Diester-amin-addukte, verfahren zu deren herstellung und deren verwendung als weichgriffmittel
EP0590879A1 (fr) * 1992-10-02 1994-04-06 Betz Europe, Inc. Méthode et composition pour l'inhibition du dépôt de silice et de silicate

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3077487A (en) * 1959-06-17 1963-02-12 Victor Chemical Works Lower alkylene and lower alkylenephenylene-lower alkylene polyamine bis n, n'-lower alkylene di and tri carboxylic acids, esters, salts, and chelates
DE2341045A1 (de) * 1972-08-21 1974-03-07 Ciba Geigy Ag Diester-amin-addukte, verfahren zu deren herstellung und deren verwendung als weichgriffmittel
EP0590879A1 (fr) * 1992-10-02 1994-04-06 Betz Europe, Inc. Méthode et composition pour l'inhibition du dépôt de silice et de silicate

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Title
CHEMICAL ABSTRACTS, vol. 103, no. 9, 2 September 1985, Columbus, Ohio, US; abstract no. 070920, MUKHOMETZYANOV A G ET AL: "Synthesis and complexing properties of complexing agents derived from dicarboxylic acids. IX. N,N'-Bis(2-hydroxyethyl)-N,N'-bis(1,2- dicarboxyethyl)ethylenediamine" XP002013680 *
CHEMICAL ABSTRACTS, vol. 112, no. 15, 9 April 1990, Columbus, Ohio, US; abstract no. 138185, LAPINA G P: "Effect of the chelator EDBODSA and of ferric ion-EDBODSA chelate on the composition and content of free amino acids in seedlings of fiber flax" XP002013681 *
CHEMICAL ABSTRACTS, vol. 116, no. 10, 9 March 1992, Columbus, Ohio, US; abstract no. 092508, GORELOV I P ET AL: "Ferric chelates ethylenediaminedisuccinic acid containing phenolic groups: investigation and application for treating iron deficient plants" XP002013682 *
FIZIOL. BIOKHIM. KUL'T. RAST. (FBKRAT,05329310);89; VOL.21 (6); PP.593-7, KALININ STATE UNIV.;KALININ; USSR (SU) *
PROC. CONF. COORD. CHEM. (PCCHDB,01399535);91; VOL.13TH,; PP.77-8, TVER STATE UNIV.;DEP. INORG. CHEM.; TVER; 170000; USSR (SU) *
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2020236A1 (fr) 1999-10-25 2009-02-04 Laboratoire Theramex Médicament contraceptif à base d'un progestatif et d'un estrogéne, son mode de préparation et son utilisation
US6586365B2 (en) 2000-10-06 2003-07-01 Monsanto Technology, Llc Method for reducing pest damage to corn by treating transgenic corn seeds with clothianidin pesticide
US6593273B2 (en) 2000-10-06 2003-07-15 Monsanto Technology Llc Method for reducing pest damage to corn by treating transgenic corn seeds with pesticide
CN106732168A (zh) * 2016-12-15 2017-05-31 钦州市钦南区科学技术情报研究所 一种表面活性剂组合物及其制备方法

Also Published As

Publication number Publication date
DE19529767A1 (de) 1997-02-13
AU6699896A (en) 1997-03-12

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