WO2003057662A2 - Disuccinate d'éthylènediamine acylé - Google Patents

Disuccinate d'éthylènediamine acylé Download PDF

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Publication number
WO2003057662A2
WO2003057662A2 PCT/EP2002/014705 EP0214705W WO03057662A2 WO 2003057662 A2 WO2003057662 A2 WO 2003057662A2 EP 0214705 W EP0214705 W EP 0214705W WO 03057662 A2 WO03057662 A2 WO 03057662A2
Authority
WO
WIPO (PCT)
Prior art keywords
weight
acylated
ethylenediamine disuccinate
agents
cleaning agents
Prior art date
Application number
PCT/EP2002/014705
Other languages
German (de)
English (en)
Other versions
WO2003057662A3 (fr
Inventor
Hans-Christian Raths
Ansgar Behler
Original Assignee
Cognis Deutschland Gmbh & Co. Kg
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 Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Publication of WO2003057662A2 publication Critical patent/WO2003057662A2/fr
Publication of WO2003057662A3 publication Critical patent/WO2003057662A3/fr

Links

Classifications

    • 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
    • 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
    • C07C233/45—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 carboxyl groups
    • C07C233/46—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—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 carboxyl 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
    • 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
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the invention relates to acylated ethylenediammine succinates as new surfactants and their use in surface-active preparations, such as washing, rinsing and / or cleaning agents and cosmetic and / or pharmaceutical cleaning agents.
  • Surface-active preparations especially those that come into regular contact with human skin, such as Shampoos or hand dishwashing detergents usually contain a proportion of particularly mild surfactants in addition to other active substances.
  • the selection of the surface-active components is chosen in such a way that a good balance between technical suitability for use and cosmetic skin tolerance is found. In many known formulations, however, very mild formulations are often offered which do not have satisfactory cleaning and foaming properties.
  • the object of the present invention was to provide new compounds which not only have good skin tolerance but also good application properties, such as. e.g. Have foam properties. At the same time, these compounds are said to be readily biodegradable due to the increasing environmental pollution.
  • the present invention relates to an acylated ethylenediamine disuccinate of the formula (I)
  • X is alkali, alkaline earth or ammonium and preferably alkali and Y is H or X and preferably X.
  • acylated ethylenediamine disuccinates in particular acylated trisodium ethylenediamine disuccinate, not only have good skin tolerance but also good foaming properties compared to other surfactants.
  • these new compounds are readily biodegradable and can be easily synthesized.
  • these compounds have complexing properties and are therefore suitable as builders, for example for binding calcium ions and the like in surface-active preparations.
  • acylated ethylenediamine disuccinates can be prepared by the customary methods for acylating amino functions, for example using the traditional “Schotten-Baumann” method from ethylenediamine disuccinate and acid halide. Accordingly, acylated ethylenediamine disuccinates, preferably acylated trisodium ethylenediamine disuccinate, are all compounds in the context of the invention which are obtained by acylation of ethylenediamine disuccinates of the formula (II).
  • X is alkali, alkaline earth or ammonium and preferably alkali and Y is H or X and preferably X, with fatty acid halides of the formula (III),
  • R 1 for a saturated or unsaturated and / or branched or unbranched C5 to C29 alkyl group or an aromatic radical and preferably for a saturated or unsaturated and / or branched or unbranched C7 to C21 and in particular Cn to Ci7 Alkyl group, and Z represents choir, bromine or iodine and preferably chlorine, can be obtained by the customary acylation processes known from the prior art.
  • Z represents choir, bromine or iodine and preferably chlorine
  • Octanoyl chloride, nonanoyl chloride, decanoyl chloride, undecanoyl chloride, lauroyl chloride, tridecanoyl chloride, myristoyl chloride, palmitoyl chloride, stearoyl chloride, oleoyl chloride and also mixtures thereof are preferably used as acid halides.
  • the acylated ethylenediamine disuccinates thus produced have a degree of acylation of 60 to 95, preferably 70 to 80 and in particular 80 to 90%.
  • the acylated ethylenediamine disuccinates according to the invention can be adjusted to any concentration by adding water, the water content being 20 to 80, preferably 25 to 60 and in particular 30 to 50% by weight.
  • acylated ethylenediamine disuccinates according to the invention can be used in surface-active agents, such as preferably detergents, dishwashing detergents and cleaning agents, and also cosmetic and / or pharmaceutical cleaning agents, preferably in amounts of 0.05 to 40, preferably 0.5 to 30% by weight, based on the active substance content -.
  • surface-active preparations are preferably to be understood as detergents, dishwashing detergents and cleaning agents as well as cosmetic and / or pharmaceutical cleaning agents and in particular cosmetic and / or pharmaceutical cleaning agents.
  • These surface-active preparations can be used as further auxiliaries and additives, pearlescent waxes, consistency agents, thickeners, superfatting agents, stabilizers, silicone compounds, fats, waxes, lecithins, phospholipids, antioxidants, deodorants, antiperspirants, antidandruff agents, swelling agents, tyrosine inhibitors, hydrotropes, solubilizers, hydrotropes, Preservatives, perfume oils, dyes, surfactants as well as other typical ingredients, such as those found in washing-up detergents and cleaning agents.
  • Cosmetic and / or pharmaceutical preparations are preferably oral and dental care products, hair shampoos, hair lotions, foam baths, shower baths, creams, gels, lotions, alcoholic and aqueous / alcoholic solutions and emulsions
  • the agents according to the invention can preferably be used in the surface-active preparations as surfactants with cleaning and foaming properties. Accordingly, further objects of the invention are directed to the use of the agents according to the invention in surface-active preparations and preferably in detergents, dishwashing detergents and cleaning agents as well as cosmetic and / or pharmaceutical cleaning agents.
  • Typical cosmetic and / or pharmaceutical cleaning agents preferably have the following composition - based on the active substance content:
  • Typical liquid washing and rinsing agents, cleaning agents preferably have the following composition - based on the active substance content -:
  • Production Example 1 Production of lauroyl ethylenediamine disuccinate, Na salt (C12-EDDS)
  • the mixture is stirred for a further 2 hours at 20 to 25 ° C., then heated for another 2 hours to 60 to 80 ° C. and, after the reaction mixture has cooled, is brought to a pH of approx on.
  • aqueous mixtures of acylated ethylenediamine disuccinates are prepared in accordance with preparation examples 1 and 2 and the foam volume is determined in accordance with DIN standard 53 902, part 1 (1 g of active substance / l; 20 ° C.; 0 ° dH; pH 6.0 ).
  • the foam is generated by beating the liquid sample in a standing cylinder with a horizontally aligned perforated plate attached to a handle for 30 seconds. The resulting foam volume is measured immediately after completion of the shaving, as well as after 5, 10 and 20 minutes.
  • Table 1 Foam measurements of aqueous acylated ethylenediamine disuccinates (EDDS) compared to APG, FAES and ACG
  • acylated ethylenediamine disuccinates were compared to Na-dodecyl sulfate (SDS), C ⁇ / Ci4 + 2EO-sulfate (FAES), N-cocoylglutamate (ACG) and coconut amidopropyl betaine (CAPB) in the RBC ("Red Blood Cell") -Test checked.
  • SDS Na-dodecyl sulfate
  • FES C ⁇ / Ci4 + 2EO-sulfate
  • ACG N-cocoylglutamate
  • CAPB coconut amidopropyl betaine
  • the RBC test enables the rapid determination of the acute cytotoxic potential of surfactants (Lso) in vitro.
  • the test can also be used to determine the denaturing effect of a test substance (denaturation index - DI).
  • the irritation potential of a test substance can be expressed by the quotient L50 / DI [Pape and Hoppe, Drug Res. 40, 498-502

Landscapes

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

Abstract

L'invention concerne un disuccinate d'éthylènediamine acylé de formule (I), dans laquelle R1 représente un groupe alkyle C5 à C29 saturé ou non saturé et/ou ramifié ou non ramifié ou un résidu aromatique, X représentant alcali, une base alcalinoterreuse ou ammonium et Y représentant H ou X.
PCT/EP2002/014705 2002-01-11 2002-12-21 Disuccinate d'éthylènediamine acylé WO2003057662A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10200726.8 2002-01-11
DE2002100726 DE10200726A1 (de) 2002-01-11 2002-01-11 Acyliertes Ethylendiaminsuccinat

Publications (2)

Publication Number Publication Date
WO2003057662A2 true WO2003057662A2 (fr) 2003-07-17
WO2003057662A3 WO2003057662A3 (fr) 2003-10-02

Family

ID=7711843

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/014705 WO2003057662A2 (fr) 2002-01-11 2002-12-21 Disuccinate d'éthylènediamine acylé

Country Status (2)

Country Link
DE (1) DE10200726A1 (fr)
WO (1) WO2003057662A2 (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3483984B2 (ja) * 1995-04-18 2004-01-06 カネボウ株式会社 化粧料
JP3576416B2 (ja) * 1998-06-03 2004-10-13 カネボウ株式会社 新規アミド化合物
JP2000169439A (ja) * 1998-12-07 2000-06-20 Kanebo Ltd ２鎖２親水基含有陰イオン界面活性剤の中間体
JP3576417B2 (ja) * 1998-12-11 2004-10-13 カネボウ株式会社 新規アミド化合物及びその製造方法
JP4354594B2 (ja) * 1999-11-22 2009-10-28 花王株式会社 被覆顔料及びそれを含有する化粧料

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; retrieved from STN Database accession no. 126:190765 XP002241338 & JP 09 002931 A (KANEBO) 7. Januar 1997 (1997-01-07) *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; retrieved from STN Database accession no. 132:166511 XP002241337 & JP 2000 053625 A (KANEBO) 22. Februar 2000 (2000-02-22) *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; retrieved from STN Database accession no. 133:177492 XP002241336 & JP 2000 229924 A (KANEBO) 22. August 2000 (2000-08-22) *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; retrieved from STN Database accession no. 133:32094 XP002241339 & JP 2000 169439 A (KANEBO) 20. Juni 2000 (2000-06-20) *
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; retrieved from STN Database accession no. 135:9826 XP002241340 & JP 2001 146557 A (KANEBO) 29. Mai 2001 (2001-05-29) *

Also Published As

Publication number Publication date
DE10200726A1 (de) 2003-07-24
WO2003057662A3 (fr) 2003-10-02

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