WO1998024400A2 - Utilisation de derives de bis(acide dicarboxylique)diaminoalkylene comme agents complexants biodegradables pour des ions de metaux alcalino-terreux et de metaux lourds - Google Patents

Utilisation de derives de bis(acide dicarboxylique)diaminoalkylene comme agents complexants biodegradables pour des ions de metaux alcalino-terreux et de metaux lourds Download PDF

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Publication number
WO1998024400A2
WO1998024400A2 PCT/EP1997/006764 EP9706764W WO9824400A2 WO 1998024400 A2 WO1998024400 A2 WO 1998024400A2 EP 9706764 W EP9706764 W EP 9706764W WO 9824400 A2 WO9824400 A2 WO 9824400A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
metal ions
alkaline earth
active ingredient
compositions
Prior art date
Application number
PCT/EP1997/006764
Other languages
German (de)
English (en)
Other versions
WO1998024400A3 (fr
Inventor
Karin Sperling
Birgit Potthoff-Karl
Thomas Greindl
Original Assignee
Basf 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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1998024400A2 publication Critical patent/WO1998024400A2/fr
Publication of WO1998024400A3 publication Critical patent/WO1998024400A3/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
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/51—Chelating agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/04—Depilatories

Definitions

  • the invention relates to active ingredient compositions, in particular cosmetics, light stabilizers or vitamin compositions.
  • the invention further relates to the use of bis (dicarboxylic acid) diaminoalkylene derivatives.
  • Material compositions in particular cosmetics, light stabilizers or vitamin compositions usually contain organic complexing agents. These complexing agents are intended to complex the alkaline earth metal or heavy metal ions contained in the material compositions in order to prevent their oxidizing effect on active substances which are sensitive to oxidation, such as vitamin E, retinol and others. Commonly used complexing agents are ethylenediaminotetraacetic acid (EDTA), ethylenediaminetetraethylenephosphonic acid (EDTMP), diethylenetetraminepentaethylenephosphonic acid (DTBMP) or other aminopolycarboxylic acids.
  • EDTA ethylenediaminotetraacetic acid
  • ETMP ethylenediaminetetraethylenephosphonic acid
  • DTBMP diethylenetetraminepentaethylenephosphonic acid
  • R 1 and R 2 are H, a C to C 8 alkyl or a C 2 -C 8 alkenyl
  • M denotes hydrogen, alkali metal, alkaline earth metal, ammonium or substituted ammonium in the corresponding stoichiometric amounts
  • n each represent numbers from 0 to 6 and
  • a j is an alkylene radical with 2 or 3 carbon atoms, which is optionally unsubstituted or on one, two or all C atoms, single or double with a hydroxy, a C j -Cg alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 8 cycloalkenyl, C 6 - 12 aryl, C 7 - 20 alkylaryl, C 5 - 11 hetaryl, and / or C 6 - 20 alkylhetaryl is substituted.
  • the object of the invention is to provide active ingredient compositions, in particular cosmetics, light stabilizers or vitamin compositions, which serve as complexing agents for alkaline earth metal or heavy metal ions in the active ingredient compositions and contribute to the stabilization of the oxidation-sensitive active ingredients, they also having an improved biological content compared to the known compositions Degradability should have.
  • active substance compositions in particular cosmetics, light stabilizers or vitamin compositions, which contain one or more compounds of the formula I below
  • R 1 and R 2 are H, a C r to C 8 alkyl or a C 2 -C 8 alkenyl
  • M denotes hydrogen, alkali metal, alkaline earth metal, ammonium or substituted ammonium in the corresponding stoichiometric amounts
  • n each represent numbers from 0 to 6 and
  • a j is an alkylene radical with 2 or 3 carbon atoms, which is optionally unsubstituted or on one, two or all C atoms, single or double with a hydroxy, a C r C 6 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 8 cycloalkenyl, C 6 - 12 aryl, C 7 - 20 alkylaryl, C 5 - 11 hetaryl, and / or C 6 - 20 alkylhetaryl is substituted.
  • the invention relates to the use of bis (dicarboxylic acid) diaminoalkylene derivatives of the abovementioned formula I as complexing agents for alkaline earth metal and heavy metal ions in active substance compositions, in particular cosmetics, light stabilizers, vitamin compositions and for stabilizing active substances which are sensitive to oxidation.
  • compounds of the formula I used are those in which R 1 and / or R 2 are H and / or —CH 3 , n and / or m 0, 1 1 or 2 and / or A.
  • j represent ethylene, propylene or 2-hydroxypropylene radicals.
  • Active substance compositions and the uses according to the invention for stabilizing oxidation-sensitive active substances in material compositions gen, especially cosmetics, light stabilizers or vitamin compositions, are used as compound I ethylenediaminosuccmat (EDDS), (2-hydroxypropylene) -l, 3-diaminosuccinate (HPDDS) or ethylenediaminoglutamate (EDDG).
  • EDDS ethylenediaminosuccmat
  • HPDDS 3-diaminosuccinate
  • EDDG ethylenediaminoglutamate
  • their alkali metal, ammonium and / or substituted ammonium salts can be used or can be contained in the active ingredient composition.
  • Particularly suitable salts of this type are the sodium, potassium or ammonium salts; Of these, in turn, the tetrasodium, tetrakalium or tetraammonium salt and organic tetraamine salts with a tertiary nitrogen atom are particularly preferred.
  • the base on which the organic amine salts are based are tertiary amines, such as trialkylamines having 1 to 4 carbon atoms in the alkyl radical, for example trimethylamine or triethylamine, or trialkanolamines having 2 or 3 carbon atoms in the alkanol radical, preferably triethanolamine, tri-n-propanolamine or triisopropanolamine in question.
  • tertiary amines such as trialkylamines having 1 to 4 carbon atoms in the alkyl radical, for example trimethylamine or triethylamine, or trialkanolamines having 2 or 3 carbon atoms in the alkanol radical, preferably triethanolamine, tri-n-propanolamine or triisopropanolamine in question.
  • the compounds of the formula I contained in the active compound compositions according to the invention are used in an amount of 0.01 to 1% by weight, preferably 0.05 to 0.5% by weight. They are contained in the active ingredient compositions in addition to components commonly used in cosmetics, such as dispersants, surface-active substances, preservatives, dyes or enzymes.
  • At least two asymmetric carbon atoms are formed in the synthesis of the compounds used according to the invention.
  • starting substances used such as naturally occurring chiral substances such as L-aspartic acid, or stereoselectively prepared starting materials or racemic substances, such as D, L-aspartic acid, or about achiral compounds such as maleic acid
  • dependent reaction conditions such as using stereoselective Catalysts or chiral auxiliaries, as well as any separations made after the synthesis, such as crystallization, chromatographic separation or optical cleavage, are obtained in this way optically pure products or mixtures of optical isomers.
  • the optical isomers can be enantiomers, diastereomers or meso compounds.
  • the effectiveness of the compounds of the formula I used as complexing agents in the active compound compositions according to the invention is independent of their stereochemistry.
  • the biodegradability depends to a large extent on the stereochemistry of the compound.
  • the (S.S) isomer of EDDS can be biodegraded quickly and completely, while the racemic mixture is only partially biodegraded. Therefore, the compounds present on the chiral atom in the S configuration are preferably substances present in the active compound compositions according to the invention.
  • the compounds used according to the invention are themselves degradable by the process already known in the prior art, for example by reacting amino acids such as aspartic acid or glutamic acid with dibromoethane or dichloroethane or dibromo-2-propanol or dichloro-2-propanol (S, S ) - Receive connections.
  • the only partially degradable racemates are obtained by reacting maleic anhydride with ethylenediamine to EDDS, glutamic acid with 1,2-dibromoethane to EDDG and by converting maleic anhydride with 2-hydroxy-1,3-dibromopropane to HPDDS.
  • Viscosity approx. 5000 mPa-s pH value: approx. 7

Abstract

L'invention concerne une composition de principes actifs, notamment un agent cosmétique, un agent de protection solaire ou une composition vitaminée, qui contient un ou plusieurs composés de la formule (I), en particulier une composition de principes actifs contenant comme composé de la formule (I), du diaminosuccinate d'éthylène (EDDS), du diaminoglutamate d'éthylène (EDDG) ou du (2-hydroypropylène)-1,3-diaminosuccinate (HPDDS). L'invention concerne en outre l'utilisation de dérivés de bis(acide carboxylique) diaminoalkylène) de la formule (I) comme agents complexants pour des ions de métaux alcalino-terreux et de métaux lourds dans des compositions de principes actifs, notamment des agents cosmétiques, des agents de protection solaire, des compositions vitaminées et pour stabiliser des principes actifs sensibles à l'oxydation.
PCT/EP1997/006764 1996-12-03 1997-12-03 Utilisation de derives de bis(acide dicarboxylique)diaminoalkylene comme agents complexants biodegradables pour des ions de metaux alcalino-terreux et de metaux lourds WO1998024400A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19650102.4 1996-12-03
DE1996150102 DE19650102A1 (de) 1996-12-03 1996-12-03 Verwendung von Bis(dicarbonsäure)diaminoalkylen-Derivaten als biologisch abbaubare Komplexbildner für Erdalkali- und Schwermetallionen

Publications (2)

Publication Number Publication Date
WO1998024400A2 true WO1998024400A2 (fr) 1998-06-11
WO1998024400A3 WO1998024400A3 (fr) 1998-07-16

Family

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Application Number Title Priority Date Filing Date
PCT/EP1997/006764 WO1998024400A2 (fr) 1996-12-03 1997-12-03 Utilisation de derives de bis(acide dicarboxylique)diaminoalkylene comme agents complexants biodegradables pour des ions de metaux alcalino-terreux et de metaux lourds

Country Status (2)

Country Link
DE (1) DE19650102A1 (fr)
WO (1) WO1998024400A2 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999053892A1 (fr) * 1998-04-20 1999-10-28 Matthew Miller Compositions depilatoires comprenant des agents de chelation
FR2870726A1 (fr) * 2004-05-28 2005-12-02 Oreal Composition pour le traitement de matieres keratiniques comprenant un compose polycarboxylique particulier et un agent reducteur, et procedes la mettant en oeuvre
US10973744B2 (en) 2016-06-30 2021-04-13 The Procter And Gamble Company Conditioner composition comprising a chelant
US11166894B2 (en) 2016-06-30 2021-11-09 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11246816B2 (en) 2016-06-30 2022-02-15 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11458085B2 (en) 2016-06-30 2022-10-04 The Procter And Gamble Company Hair care compositions for calcium chelation
US11786447B2 (en) 2016-06-30 2023-10-17 The Procter & Gamble Company Conditioner composition comprising a chelant

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2870723B1 (fr) * 2004-05-28 2006-07-28 Oreal Composition pour le traitement de matieres keratiniques comprenant un compose polycarboxylique particulier et un polyol particulier et procedes la mettant en oeuvre

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2288812A (en) * 1994-04-26 1995-11-01 Procter & Gamble Cleansing compositions
WO1996019119A1 (fr) * 1994-12-22 1996-06-27 The Procter & Gamble Company Compositions a base de silicone
WO1996019194A1 (fr) * 1994-12-22 1996-06-27 The Procter & Gamble Company Compositions a base de silicone
WO1997002010A1 (fr) * 1995-07-05 1997-01-23 The Procter & Gamble Company Composition bactericide
WO1997024107A1 (fr) * 1995-12-29 1997-07-10 The Procter & Gamble Company Compositions pour teintures capillaires
EP0796842A2 (fr) * 1996-03-19 1997-09-24 Unilever Plc Agents séquestrants à base d'aspartate/cystéate d'éthylène, procédé pour leur préparation et compositions détergentes les contenant
DE19620644A1 (de) * 1996-05-22 1997-11-27 Ciba Geigy Ag Verwendung von stickstoffhaltigen Komplexbildnern zur Desodorierung und antimikrobiellen Behandlung der Haut und textilen Fasermaterialien
WO1998004237A1 (fr) * 1996-07-25 1998-02-05 The Procter & Gamble Company Compositions de shampooing
WO1998004241A2 (fr) * 1996-07-25 1998-02-05 The Procter & Gamble Company Compositions pour shampooing

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2288812A (en) * 1994-04-26 1995-11-01 Procter & Gamble Cleansing compositions
WO1996019119A1 (fr) * 1994-12-22 1996-06-27 The Procter & Gamble Company Compositions a base de silicone
WO1996019194A1 (fr) * 1994-12-22 1996-06-27 The Procter & Gamble Company Compositions a base de silicone
WO1997002010A1 (fr) * 1995-07-05 1997-01-23 The Procter & Gamble Company Composition bactericide
WO1997024107A1 (fr) * 1995-12-29 1997-07-10 The Procter & Gamble Company Compositions pour teintures capillaires
EP0796842A2 (fr) * 1996-03-19 1997-09-24 Unilever Plc Agents séquestrants à base d'aspartate/cystéate d'éthylène, procédé pour leur préparation et compositions détergentes les contenant
DE19620644A1 (de) * 1996-05-22 1997-11-27 Ciba Geigy Ag Verwendung von stickstoffhaltigen Komplexbildnern zur Desodorierung und antimikrobiellen Behandlung der Haut und textilen Fasermaterialien
WO1998004237A1 (fr) * 1996-07-25 1998-02-05 The Procter & Gamble Company Compositions de shampooing
WO1998004241A2 (fr) * 1996-07-25 1998-02-05 The Procter & Gamble Company Compositions pour shampooing

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999053892A1 (fr) * 1998-04-20 1999-10-28 Matthew Miller Compositions depilatoires comprenant des agents de chelation
FR2870726A1 (fr) * 2004-05-28 2005-12-02 Oreal Composition pour le traitement de matieres keratiniques comprenant un compose polycarboxylique particulier et un agent reducteur, et procedes la mettant en oeuvre
US10973744B2 (en) 2016-06-30 2021-04-13 The Procter And Gamble Company Conditioner composition comprising a chelant
US11166894B2 (en) 2016-06-30 2021-11-09 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11246816B2 (en) 2016-06-30 2022-02-15 The Procter And Gamble Company Shampoo compositions comprising a chelant
US11458085B2 (en) 2016-06-30 2022-10-04 The Procter And Gamble Company Hair care compositions for calcium chelation
US11786447B2 (en) 2016-06-30 2023-10-17 The Procter & Gamble Company Conditioner composition comprising a chelant

Also Published As

Publication number Publication date
DE19650102A1 (de) 1998-06-04
WO1998024400A3 (fr) 1998-07-16

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