DE2408591A1 - Oligo-epoxy-succinic acids, prepn. from alkyl epoxy-succinate - and used as builders in detergents and moisture retainers in cosmetics - Google Patents

Oligo-epoxy-succinic acids, prepn. from alkyl epoxy-succinate - and used as builders in detergents and moisture retainers in cosmetics

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Publication number
DE2408591A1
DE2408591A1 DE19742408591 DE2408591A DE2408591A1 DE 2408591 A1 DE2408591 A1 DE 2408591A1 DE 19742408591 DE19742408591 DE 19742408591 DE 2408591 A DE2408591 A DE 2408591A DE 2408591 A1 DE2408591 A1 DE 2408591A1
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Prior art keywords
epoxy
detergents
water
acid
oligoepoxysuccinic
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Pending
Application number
DE19742408591
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German (de)
Inventor
Gerhard Dipl Chem Dr Borggrefe
Peter Dipl Chem Dr Lorenz
Rainer Dipl Chem Dr Osberghaus
Edmund Dipl Chem Dr Schmadel
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19742408591 priority Critical patent/DE2408591A1/en
Publication of DE2408591A1 publication Critical patent/DE2408591A1/en
Pending legal-status Critical Current

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    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/362—Polycarboxylic 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
    • 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
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2089—Ether acids-salts 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

Oligoepoxysuccinic acids (I) of formula: -(CH(COOX)- CH(COOX)-O)-n (in which n = 2-100, pref. 3-8; X is H or a water-solubilising cation) are prepd. by polymsg. the epoxy-succinate of a lower monohydric alcohol, pref. MeOH, with catalytic amts. of a Lewis acid, opt. in an inert solvent (II) and hydrolysing the polymsn. prod., after removing (II). (I) esp. their alkali salts, are used (as builders) in a concn. of 5-95 wt. % w.r.t. the water- and/or solvent-free prepn., in washing agents and detergents contg. other substance(s) with detergent action. (I) can also be used as moisture retainers in cosmetics for the skin. (I) bind Ca ions, are biologically degradable and are harmless to aquatic life, e.g. fish adn daphnia.

Description

"Oligoepoxybernsteinsäure" Die Erfindung betrifft als neue Substanz die Oligoepoxybernsteirisäure, ein Verfahren zu ihrer erstellung sowie ihre Verwendung, insbesondere als Gerüststoff in Wasch-und Reinigungsmitteln. "Oligoepoxysuccinic Acid" The invention relates to a novel substance oligoepoxysuccinic acid, a process for its preparation and its use, in particular as a builder in detergents and cleaning agents.

Die Ol.igoepoxybernsteinsäure ist gekennzeichnet durch die Formel index n eine Zahl von 2 - 100, vorzugsweise 3 - 8, und X Wasserstoff oder ein wasserlöslichmachendes Kation bedeuten.The oligoepoxysuccinic acid is characterized by the formula index n is a number from 2-100, preferably 3-8, and X is hydrogen or a water-solubilizing cation.

Als wasserlöslichmachendes Kation kommt insbesondere ein Alkalimetallion, Ammonium oder ein Kation von primären, sekundären oder tertiären Aminen bzw. Alkylolaminen mit höchstens 2 C-Atomen pro Alkylrest bzw. höchstens 3 C-Atomen pro Alkylolrest in Betracht.In particular, an alkali metal ion is used as the water-solubilizing cation, Ammonium or a cation of primary, secondary or tertiary amines or alkylolamines with a maximum of 2 carbon atoms per alkyl radical or a maximum of 3 carbon atoms per alkylol radical into consideration.

Das Verfahren zur Herstellung der Oligoepoxybernsteinsäure ist dadurch gekennzeichnet, daß man den Epoxybernsteinsäureester eines niederen einwertigen Alkohols, vorzugsweise den Methylester, gegebenenfalls in einem inerten Lösungsmittel mit katalytischen Mengen einer Lewis-Säure polymerisiert und, gegebenenfalls nach Abziehen des Lösungsmittels' das Polymerisationsprodukt verseift.The process for making the oligoepoxysuccinic acid is thereby characterized in that the epoxysuccinic acid ester of a lower monovalent Alcohol, preferably the methyl ester, optionally in an inert solvent polymerized with catalytic amounts of a Lewis acid and, optionally after Stripping off the solvent 'saponifies the polymerization product.

Das Reaktionsprodukt wird zweckmäßigerweise in Form des Alkalisalzes isoliert. Gegebenenfalls kann die freie Carbonsäure aus dem Salz gewonnen werden, beispielsweise dadurch, daß man die Verseifungslösung mit einem Kationenaustauscher behandelt und anschließend unter vermindertem Druck einengt.The reaction product is conveniently in the form of the alkali salt isolated. If necessary, the free carboxylic acid can be obtained from the salt, for example by the fact that the saponification solution with a cation exchanger treated and then concentrated under reduced pressure.

Die Oligoepoxybernsteinsäure und ihre wasserlöslichen, Calciumionen bindenden Salze eignen sich als Gerüststoffe für Wasch-und Reinigungsmittel. Die neuen Stoffe sind-biologisch abbaubar und unschädlich für die Wasserlebewesen, beispielsweise für Fische und Daphnien. Die Oligoepoxybernsteinsäure eignet sfch auch als Feuchthaltemittel für Hautkosmetika.The oligoepoxysuccinic acid and its water-soluble calcium ions binding salts are suitable as builders for detergents and cleaning agents. the new substances are biodegradable and harmless to aquatic life, for example for fish and daphnia. The oligoepoxysuccinic acid is also suitable as a humectant for skin cosmetics.

Der zur Herstellung der Oligoepoxybernsteinsäure bevorzugt verwendete cis-Epoxybernsteinsäuremethylester ist bekannt (F. Bohlmann und H. Jastrow, Chem. Berichte 95, 1746 (1962).The one preferably used for the preparation of the oligoepoxysuccinic acid cis-Epoxysuccinic acid methyl ester is known (F. Bohlmann and H. Jastrow, Chem. Reports 95, 1746 (1962).

Die Verbindung läßt sich auf einfache Weise durch Verestern der nach G. Payne und P. Williams, J. Org. Chem. 24, 54 (1959) hergestellten cis-Epoxybernsteinsäure gewinnen. Die Polymerisationsreaktion wird katalysiert durch Lewis-Säuren, wie z.B.The connection can be made in a simple manner by esterifying the G. Payne and P. Williams, J. Org. Chem. 24, 54 (1959) to win. The polymerization reaction is catalyzed by Lewis acids, e.g.

Bortrifluorid, Bortrifluorid-Ntherat, Zinntetrachlorid, Aluminiumtrichlorid oder Antimonpentachlorid. Je nach dem welcher Katalysator für die Polymerisation verwendet wird, besitzen die Reaktionsprodukte als Endgruppen Hydroxy-, Alkoxy- oder Halogenreste; die Reaktionsprodukte können jedoch auch ringförmig sein.Boron trifluoride, boron trifluoride etherate, tin tetrachloride, aluminum trichloride or antimony pentachloride. Depending on which catalyst for the polymerization is used, the reaction products have hydroxyl, alkoxy or halogen radicals; however, the reaction products can also be ring-shaped.

Die Erfindung betrifft weiter Wasch- und Reinigungsmittel, die in fester Form, als Pasten, Dispersionen oder Lösungen vorliegen und einen Gehalt an mindestens einer weiteren reinigend wirkenden Substanz aufweisen, und die, bezogen auf die wasser- und/oder lösungsmittelfreien Präparate, 5 - 95 Gew.-% der oben definierten Oligoepoxybernsteinsäure, insbesondere deren Alkalisalze, enthalten.The invention further relates to detergents and cleaning agents that are used in solid form, as pastes, dispersions or solutions and a content of have at least one further substance with a cleaning effect, and the, related on the water- and / or solvent-free preparations, 5 - 95% by weight of the above-defined Oligoepoxysuccinic acid, in particular its alkali metal salts, contain.

Die Wasch- und Reinigungsmittel enthalten außer den als Gerüstsubstanzen dienenden, Calciumionen bindenden Oligoepoxysuccinaten meist eine Tensidkomponente, bestehend aus anionischen und/oder zwitterionischen und/oder nichtionischen Tensiden, und gegebenenfalls noch andere anorganische und/oder organische Gerüstsubstanzen und/oder eine Bleichkomponente. Als übliche Zusätze kommen z.B. Schaumstabilisatoren, nichttensidartige Schauminhibitoren, Textilweichmacher, Schmutzträger, Aufheller, Antimikrobika, Enzyme, Farb- und Duftstoffe in Betracht.The detergents and cleaning agents also contain as structural substances serving, calcium ion binding oligoepoxysuccinates usually a surfactant component, consisting of anionic and / or zwitterionic and / or nonionic surfactants, and optionally other inorganic and / or organic builder substances and / or a bleach component. Typical additives include foam stabilizers, non-surfactant foam inhibitors, fabric softeners, dirt carriers, brighteners, Antimicrobials, enzymes, dyes and fragrances into consideration.

Beispiel 1 p Vom cis-Epoxybernsteinsäuredimethylester wurden 312 g (1,95 Mol) unter Stickstoffatmosphäre bei 40 OC unter Rühren mit 10 g Bortrifluorid-Ntherat versetzt. Es fand eine exotherme Reaktion statt, bei der sich das Gemisch dunkelbraun färbte und viskos wurde. Nach 48 Stunden Reaktionszeit, während der zwei weitere gleiche Portionen des Katalysators zugefügt worden waren, wurde die hochviskose Masse in Chloroform aufgenommen, die Lösung mit Wasser gewaschen, getrocknet und eingeengt. Von der verbleibenden Masse wurden die niedrig siedenden Anteile bis 220 OC / 0,2 Torr abdestilliert. Vom so erhaltenen glasartigen hellbraunen Rückstand wurde ein mittleres Molekulargewicht von 542 ermittelt. 108 g dieser Substanz wurden mit 60 g Natriumhydroxid in 400 ml Methanol und 60 ml wasser während 3 Stunden unter Rückfluß gekocht. Die Lösung wurde eingeengt und über einen sauren Ionenaustauscher (Lewatit S 100) gegeben und das Eluat mit Aktivkohle entfärbt. Nach dem Eindampfen zur Trockne wurde ein farbloses Öl erhalten, aus dem nach Neutralisation mit Natronlauge das Reaktionsprodukt als Natriumsalzin Form eines weißen Pulvers erhalten wurde.Example 1 p 312 g of dimethyl cis-epoxysuccinate were obtained (1.95 mol) under a nitrogen atmosphere at 40 ° C. with stirring with 10 g of boron trifluoride etherate offset. An exothermic reaction took place in which the mixture turned dark brown colored and became viscous. After 48 hours of reaction time, during the two more equal portions of the catalyst had been added, the highly viscous one The mass was taken up in chloroform, the solution was washed with water, dried and constricted. Of the remaining mass, the low-boiling portions were up to 220 OC / 0.2 Torr distilled off. From the glass-like light brown residue obtained in this way an average molecular weight of 542 was determined. 108 g of this substance were with 60 g of sodium hydroxide in 400 ml of methanol and 60 ml of water for 3 hours Refluxed. The solution was concentrated and passed through an acidic ion exchanger (Lewatit S 100) given and the eluate decolorized with activated charcoal. After evaporation to dryness a colorless oil was obtained, from which after neutralization with sodium hydroxide solution the reaction product was obtained as the sodium salt in the form of a white powder.

Beispiel 2 Die Polymerisation wurde bei 28 OC durchgeführt; die übrigen Verfahrensbedingungen waren die gleichen wie in Beispiel 1.Example 2 The polymerization was carried out at 28 ° C; the remaining Process conditions were the same as in Example 1.

Das so erhaltene Oligomere besaß ein mittleres Molekulargewicht von 708.The oligomer thus obtained had an average molecular weight of 708

Claims (3)

PatentansprücheClaims 1. Oligoepoxybernsteinsäure, gekennzeichnet durch die Formel in der n eine Zahl von 2 - 100, vorzugsweise 3 - 8, und X Wasserstoff oder ein wasserlöslichmachendes Kation bedeuten.1. Oligoepoxysuccinic acid, characterized by the formula in which n is a number from 2-100, preferably 3-8, and X is hydrogen or a water-solubilizing cation. 2. Verfahren zur Herstellung der Oligoepoxybernsteinsä.ure nach Anspruch 1, dadurch gekennzeichnet, daß man den Epoxybernsteinsäureester eines niederen einwertigen Alkohols, vorzugsweise den Methylester, gegebenenfalls in einem inerten Lösungsmittel mit katalytischen Mengen einer Lewis-Säure polymerisiert undtgegebenenfalls nach Abziehen des Lösungsmittels, das Polymerisationsprodukt verseift.2. A process for the preparation of the Oligoepoxybernsteinsä.ure according to claim 1, characterized in that the epoxysuccinic acid ester of a lower monovalent Alcohol, preferably the methyl ester, optionally in an inert solvent polymerized with catalytic amounts of a Lewis acid and, if necessary, after Stripping off the solvent, the polymerization product is saponified. 3. Wasch- und Reinigungsmittel mit einem Gehalt an mindestens einer weiteren reinigend wirkenden Substanz, dadurch gekennzeichnet, daß sie, bezogen auf die wasser- und/oder lösungsmittelfreien Präparate, 5 - 95 Gew.-% der Oligoepoxybernsteinsäure nach Anspruch 1 und 2, insbesondere deren Alkalisalze, -enthalten.3. Detergents and cleaning agents with a content of at least one another substance with a cleaning effect, characterized in that it is related on the water- and / or solvent-free preparations, 5 - 95% by weight of the oligoepoxysuccinic acid according to claims 1 and 2, in particular their alkali salts.
DE19742408591 1974-02-22 1974-02-22 Oligo-epoxy-succinic acids, prepn. from alkyl epoxy-succinate - and used as builders in detergents and moisture retainers in cosmetics Pending DE2408591A1 (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0075166A1 (en) * 1981-09-11 1983-03-30 Hoechst Aktiengesellschaft Polymeric ethylene oxide-propylene oxide or ethylene oxide-butylene oxide ether carboxylic acids, process for their preparation and their use
US4524009A (en) * 1984-01-31 1985-06-18 A. E. Staley Manufacturing Company Detergent builder
US4654159A (en) * 1985-06-24 1987-03-31 The Procter & Gamble Company Ether hydroxypolycarboxylate detergency builders
EP0266723A1 (en) * 1986-11-05 1988-05-11 Hoechst Aktiengesellschaft Process for the preparation of 1-hydroxy-3-oxapentane-1,2,4,5-tetracarboxylic acid, of 3,6-dioxa-octane-1,2,4,5,7,8-hexacarboxylic acid, of their salts and their mixtures
US4846650A (en) * 1985-12-06 1989-07-11 The Procter & Gamble Company Oral compositions and methods for reducing dental calculus
US5028415A (en) * 1987-08-17 1991-07-02 The Procter & Gamble Company Oral compositions and method for reducing dental calculus
US5062962A (en) * 1990-05-04 1991-11-05 Betz Laboratories, Inc. Methods of controlling scale formation in aqueous systems
US5139702A (en) * 1991-10-24 1992-08-18 W. R. Grace & Co.-Conn. Naphthylamine polycarboxylic acids
US5147555A (en) * 1990-05-04 1992-09-15 Betz Laboratories, Inc. Methods of controlling scale formation in aqueous systems
US5183590A (en) * 1991-10-24 1993-02-02 W. R. Grace & Co.-Conn. Corrosion inhibitors
EP0668344A2 (en) 1994-02-11 1995-08-23 BK LADENBURG GmbH, Gesellschaft für chemische Erzeugnisse Detergent composition containing polyepoxy succinic acid
EP1020485A2 (en) * 1999-01-05 2000-07-19 National Starch and Chemical Investment Holding Corporation Polyether hydroxycarboxylate copolymers

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0075166A1 (en) * 1981-09-11 1983-03-30 Hoechst Aktiengesellschaft Polymeric ethylene oxide-propylene oxide or ethylene oxide-butylene oxide ether carboxylic acids, process for their preparation and their use
US4524009A (en) * 1984-01-31 1985-06-18 A. E. Staley Manufacturing Company Detergent builder
US4654159A (en) * 1985-06-24 1987-03-31 The Procter & Gamble Company Ether hydroxypolycarboxylate detergency builders
US4846650A (en) * 1985-12-06 1989-07-11 The Procter & Gamble Company Oral compositions and methods for reducing dental calculus
EP0266723A1 (en) * 1986-11-05 1988-05-11 Hoechst Aktiengesellschaft Process for the preparation of 1-hydroxy-3-oxapentane-1,2,4,5-tetracarboxylic acid, of 3,6-dioxa-octane-1,2,4,5,7,8-hexacarboxylic acid, of their salts and their mixtures
US5028415A (en) * 1987-08-17 1991-07-02 The Procter & Gamble Company Oral compositions and method for reducing dental calculus
US5062962A (en) * 1990-05-04 1991-11-05 Betz Laboratories, Inc. Methods of controlling scale formation in aqueous systems
US5147555A (en) * 1990-05-04 1992-09-15 Betz Laboratories, Inc. Methods of controlling scale formation in aqueous systems
US5139702A (en) * 1991-10-24 1992-08-18 W. R. Grace & Co.-Conn. Naphthylamine polycarboxylic acids
US5183590A (en) * 1991-10-24 1993-02-02 W. R. Grace & Co.-Conn. Corrosion inhibitors
EP0668344A2 (en) 1994-02-11 1995-08-23 BK LADENBURG GmbH, Gesellschaft für chemische Erzeugnisse Detergent composition containing polyepoxy succinic acid
EP1020485A2 (en) * 1999-01-05 2000-07-19 National Starch and Chemical Investment Holding Corporation Polyether hydroxycarboxylate copolymers
EP1020485A3 (en) * 1999-01-05 2001-10-31 National Starch and Chemical Investment Holding Corporation Polyether hydroxycarboxylate copolymers

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