WO1997007089A1 - Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives - Google Patents
Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives Download PDFInfo
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- 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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- 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
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- 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
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- 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
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- 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
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- 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
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- 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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Abstract
Description
Amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von AminobernsteinsäurederivatenAmphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives
Die Erfindung betrifft amphiphile Verbindungen mit mehreren hydrophilen und hydrophoben Gruppen auf der Basis von Aminobernsteinsäurederivaten.The invention relates to amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives.
Als amphiphile Substanzen sind eine große Vielfalt an anionischen, katio¬ nischen, nichtionischen und zwitterionischen Verbindungen bekannt. Die weitaus meisten dieser Substanzen bestehen aus einer hydrophilen Kopfgruppe und wenigstens einem hydrophoben Teil.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.
Bei den amphiphilen Substanzen gibt es aus ökologischen Gründen, z. B. bezüglich der Verringerung des Verpackungs- und Transportaufwandes, die Notwendigkeit, immer größere Wirkung pro Masse an eingesetzter Substanz zu erzielen. Da eine Optimierung durch Mischung von amphiphilen Substanzen nur begrenzt weiterführt, sind neue amphiphile Substanzen mit einem höheren Wirkungsgrad erforderlich. Es müssen daher insbesondere Stoffe mit nied¬ rigeren kritischen Micellbildungskonzentrationen und/oder niedrigeren Ober- und Grenzflächenspannungen gefunden werden, um die Einsatzmengen an Wirk- Substanz deutlich reduzieren zu können. Zudem müssen sie leicht, am besten aus leicht zugänglichen Ausgangssubstanzen, erhältlich sein.In the case of 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.
Erste Lösungsansätze in Richtung auf leistungsfähigere amphiphile Sub¬ stanzen durch Verdoppelung eines Teils der Struktur (hydrophile Kopfgruppe, hydrophobe Gruppe) sind bereits bekannt. So können kationische grenzflächenaktive Verbindungen durch die Addition von langkettigen Al¬ kylhalogeniden an permethylierte AIkylendiamine erhalten werden [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].The first approaches towards more powerful amphiphilic substances by doubling part of the structure (hydrophilic head group, hydrophobic group) are already known. For example, 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].
Anionische grenzflächenaktive Verbindungen mit wenigstens zwei hydrophilen und wenigstens zwei hydrophoben Gruppen sind bisher auf der Basis von Diglycidylethem hergestellt worden (US 5 160450, JP 01304033, JP 4 124 165). Diglycidylether gelten jedoch als toxikologisch bedenklich und sind recht teuer. Darüber hinaus wird für ihre Herstellung Epichlor¬ hydrin verwendet, was zu großen Mengen an Reststoffen führt, so daß diese Verbindungen unter ökotoxikologischen wie auch ökonomischen Gesichtspunkten nicht mehr zeitgemäß sind.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). However, diglycidyl ethers are considered toxicologically unsafe and are quite expensive. In addition, 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.
Es bestand daher die Aufgabe, amphiphile Verbindungen aufzufinden, die we- nigstens zwei hydrophile und wenigstens zwei hydrophobe Gruppen aufweisen, gute Tensideigenschaften sowie einen hohen Wirkungsgrad zeigen, und aus technisch leicht verfügbaren Rohstoffen ohne großen Anfall von unerwünsch¬ ten Nebenprodukten hergestellt werden können.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.
Die Aufgabe wird erfindungsgemäß durch amphiphile N,N'-Dialkyl-N,N'-di- bernsteinsäurediester, die durch die Addition von N.N'-Dialkyldiaminen an zwei Äquivalente Maleinsäure und anschließende Veresterung mit Alkoholen oder Alkoholethoxylaten hergestellt werden können, gelöst.The object is achieved according to the invention by 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.
Bei den erfindungsgemäßen Verbindungen handelt es sich also um Verbindungen der allgemeinen Formel (I)The compounds according to the invention are therefore compounds of the general formula (I)
4 1 wobei R, R*, R", R R , M und M in der Formel (I) die im folgenden be- sehn*ebenen Bedeutungen haben:1 4 wherein R, R *, R ", RR, M and M in the formula (I) working below see * planar meanings:
R und R stehen unabhängig voneinander für einen unverzweigten oder ver- zweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 1 bis 22, vorzugsweise 6 bis 18, Kohlenstoffatomen. Es seien als Substituenten R und R im einzelnen die Reste 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-Oc- tadecyl, n-Nonadecyl, n-Eicosyl, n-Uneicosyl , n-Docosyl und ihre ver- zweigtkettigen Isomeren sowie die entsprechenden einfach, zweifach oder dreifach ungesättigten Reste genannt. 2 R bedeutet einen aliphatischen oder aromatischen, cyclischen oder acy- clischen Spacer mit 2 bis 16, vorzugsweise 2 bis 12 Kohlenstoffatomen und je 0 bis 6 Sauerstoff- und/oder Stickstoffatomen, der darüber hinaus noch verzweigt sein kann. M und M bedeutet ein Alkali-, Ammonium-, AIkanolammonium- oder 1/2 Erdalkaliion.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 and the corresponding mono-, di- or tri-unsaturated radicals. 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.
1 3 R und R stehen unabhängig voneinander für einen unverzweigten oder ver¬ zweigten, gesättigten oder ungesättigten Kohlenwasserstoffrest mit 1 bis 18, vorzugsweise 1 bis 6, Kohlenstoffatomen. Es seien als Substituenten R und R im einzelnen die Reste 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-Oc- tadecyl , und ihre verzweigtkettigen Isomeren sowie die entsprechenden einfach, zweifach oder dreifach ungesättigten Reste genannt.1 3 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.
Die erfindungsgemäßen amphiphilen Verbindungen zeichnen sich meist durch extrem niedrige kritische Micellbildungskonzentrationen (CMC) und sehr niedrige Oberflächen- und Grenzflächenspannungen (z. B. gegen Paraffin) aus, was auf ihre besondere Struktur - wenigstens zwei hydrophile Gruppen und wenigstens zwei hydrophobe Gruppen - zurückgeführt werden muß. Darüber hinaus weisen die meisten von ihnen ein recht hohes hydrophiles Suspen¬ diervermögen auf, das etwa auf halbem Wege zwischen dem konventioneller Tenside und dem des Pentanatriumtripolyphosphats liegt. Einige dieser Verbindungen sind extrem schnelle Netzmittel.The 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. In addition, most of them have a very high hydrophilic suspending capacity, which is about halfway between that of conventional surfactants and that of pentasodium tripolyphosphate. Some of these connections are extremely fast wetting agents.
Die amphiphilen Verbindungen gemäß dieser Erfindung eignen sich insbeson¬ dere als Emulgatoren, Demulgatoren, Detergenzien, Dispergatoren und Hydro- tropica sowie Antistatika in Industrie und Haushalt, beispielsweise auf den Gebieten Metallbearbeitung, Erzgewinnung, Oberflächenveredelung, Kunst- Stoffherstellung, Textilhilfsmittel, Waschen und Reinigen, insbesondere von Textilien oder von harten Oberflächen, Kosmetik, Medizin und Nahrungsmit¬ telverarbeitung und -Zubereitung.The 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.
Hierbei können sie mit allen gängigen anionischen, nichtionischen, katio- nischen und ampholytischen grenzflächenaktiven Substanzen kombiniert wer¬ den. Als Beispiele für nichtionische grenzflächenaktive Substanzen, die für eine Kombination eingesetzt werden können, seien Fettsäureglyceride, Fettsäurepolyglyceride, Fettsäureester, Ethoxylate höherer Alkohole, Po- lyoxyethylenfettsäureglyceride, Polyoxyethylenpropylenglykolfettsäureester, Polyoxyethylensorbitanfettsäureester, Polyoxyethylen-Rhizinusöl- oder gehärtete Rhizinusöl-Derivate, Polyoxyethylenlanolinderivate, Polyoxyethy- lenfettsäureamide, Polyoxyethylenalkylamine, Alkanolamine, Alkyl-aminoxide, Derivate von Eiweißhydrolysaten, Hydroxymischether, Alkylpolyglycoside und Alkylglucamide genannt. Als Beispiele für anionische grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien Seifen, Ethercarbonsäuren und deren Salze, Alkylsulfonate, α-Olefinsulfonate, α- Sulfofettsäurederivate, Sulfonate höherer Fettsäureester, höhere Alkohol- sulfate, Alkoholethersulfate, Hydroxymischethersulfate, Salze von Phosphatestern, Tauride, Isethionate, lineare Alkylbenzolsulfonate, Cumol- sulfonat, AI kyl aryl sulfonate, Sulfate der Polyoxyethylenfettsäureamide und Salze von Acylaminosäuren genannt.Here, they can be combined with all common anionic, nonionic, cationic and ampholytic surface-active substances. Examples of 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 sulfonates, α-olefin sulfonates, α-sulfofatty acid derivatives, sulfonates of higher fatty acid esters, higher alcohol sulfates, alcohol ether sulfates, hydroxyl mixed ether sulfates, salts of phosphate esters, taurides , Isethionates, linear alkylbenzenesulfonates, cumene sulfonates, alkyl aryl sulfonates, sulfates of polyoxyethylene fatty acid amides and salts of acylamino acids.
Als Beispiele für kationische gängige grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien AI kyl trimethyl ammonium¬ salze, Di alkyl dimethy lammoniumsalze, AI kyl dimethyl benzyl ammoniumsalze, Alkylpyridiniumsalze, Alkylisochinoliniumsalze, Benzethoniumchloride und kationische Acylaminosäurederivate genannt.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.
Als Beispiele für ampholytische grenzflächenaktive Substanzen, die für Kombinationen eingesetzt werden können, seien Aminosäuren, Betaine, Sul- fobetaine, Imidazolinderivate, Sojaöl1ipide und Lecithin genannt.Examples of ampholytic surface-active substances that can be used for combinations include amino acids, betaines, sulfobetaines, imidazoline derivatives, soybean oil lipids and lecithin.
Darüber hinaus können die erfindungsgemäßen amphiphilen Verbindungen auch für sich miteinander kombiniert werden.In addition, the amphiphilic compounds according to the invention can also be combined with one another.
Den erfindungsgemäßen amphiphilen Verbindungen können ebenfalls gängige Additive zugesetzt werden. Solche Additive werden speziell für eine For- mulierung ausgewählt und umfassen üblicherweise anorganische Salze, wie Natriumchlorid und -sulfat, sowie Builder, Hydrotropica, UV-Absorber, Weichmacher, Chelatbildner, Viskositätsmodifizierer und Riechstoffe.Common 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.
Die obengenannten Verbindungen lassen sich aus N,N'-dialkylierten Diaminen und zwei Äquivalenten Maleinsäure bei Temperaturen von 80 bis 180 °C herstellen. Nach der erfolgten zweifachen Addition an das Diamin erfolgt die Veresterung mit zwei Äquivalenten Alkohol oder Alkoholalkoxylat - hier¬ mit läßt sich die Hydrophilie der Produkte genau abstimmen - in Gegenwart eines Katalysators, vorzugsweise eines basischen Katalysators, bei Tempe¬ raturen von 60 bis 190 °C. Die Neutralisation erfolgt mit wäßrigen Alkali- oder Erdalkalihydroxiden oder wäßrigem Ammoniak oder Alkanolaminen. The above compounds can be prepared from N, N'-dialkylated diamines and two equivalents of maleic acid at temperatures from 80 to 180 ° C. After the addition to the diamine has been carried out twice, 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.
Claims
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 |
|---|---|---|---|
| DE19529767.9 | 1995-08-12 | ||
| DE19529767A DE19529767A1 (en) | 1995-08-12 | 1995-08-12 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on amino succinic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997007089A1 true WO1997007089A1 (en) | 1997-02-27 |
Family
ID=7769380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1996/003114 Ceased WO1997007089A1 (en) | 1995-08-12 | 1996-07-16 | Amphiphilic compounds with several hydrophilic and hydrophobic groups based on aminosuccinic acid derivatives |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU6699896A (en) |
| DE (1) | DE19529767A1 (en) |
| WO (1) | WO1997007089A1 (en) |
Cited By (4)
| 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 (en) | 1999-10-25 | 2009-02-04 | Laboratoire Theramex | Contraceptive medicament based on a progestative and oestrogen, method for producing the same, and use |
| CN106732168A (en) * | 2016-12-15 | 2017-05-31 | 钦州市钦南区科学技术情报研究所 | A kind of surface activator composition and preparation method thereof |
Citations (3)
| 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 (en) * | 1972-08-21 | 1974-03-07 | Ciba Geigy Ag | DIESTER AMINE ADDUCTS, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS SOFT HANDLING AGENTS |
| EP0590879A1 (en) * | 1992-10-02 | 1994-04-06 | Betz Europe, Inc. | Method and composition for inhibiting silica and silicate deposition |
-
1995
- 1995-08-12 DE DE19529767A patent/DE19529767A1/en not_active Withdrawn
-
1996
- 1996-07-16 AU AU66998/96A patent/AU6699896A/en not_active Abandoned
- 1996-07-16 WO PCT/EP1996/003114 patent/WO1997007089A1/en not_active Ceased
Patent Citations (3)
| 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 (en) * | 1972-08-21 | 1974-03-07 | Ciba Geigy Ag | DIESTER AMINE ADDUCTS, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS SOFT HANDLING AGENTS |
| EP0590879A1 (en) * | 1992-10-02 | 1994-04-06 | Betz Europe, Inc. | Method and composition for inhibiting silica and silicate deposition |
Non-Patent Citations (6)
| 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) * |
| ZH. OBSHCH. KHIM. (ZOKHA4,0044460X);85; VOL.55 (2); PP.253-6, KALININ. GOS. UNIV.;KALININ; USSR (SU) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2020236A1 (en) | 1999-10-25 | 2009-02-04 | Laboratoire Theramex | Contraceptive medicament based on a progestative and oestrogen, method for producing the same, and use |
| 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 (en) * | 2016-12-15 | 2017-05-31 | 钦州市钦南区科学技术情报研究所 | A kind of surface activator composition and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19529767A1 (en) | 1997-02-13 |
| AU6699896A (en) | 1997-03-12 |
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