EP0308914B1 - Alkenyl-succinic esters containing amino groups - Google Patents
Alkenyl-succinic esters containing amino groups Download PDFInfo
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- EP0308914B1 EP0308914B1 EP88115534A EP88115534A EP0308914B1 EP 0308914 B1 EP0308914 B1 EP 0308914B1 EP 88115534 A EP88115534 A EP 88115534A EP 88115534 A EP88115534 A EP 88115534A EP 0308914 B1 EP0308914 B1 EP 0308914B1
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- European Patent Office
- Prior art keywords
- alkenyl
- alkyl
- weight
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- parts
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- Legal status (The legal status 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 status listed.)
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Classifications
-
- 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
- D06M13/402—Amides imides, sulfamic acids
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- preparation agents When manufacturing synthetic fibers, it is absolutely necessary to apply so-called preparation agents to the fiber surface.
- the main task of these preparation agents is to avoid thread-metal friction, but also to adjust thread-thread friction and to prevent electrostatic charging.
- texturing polyester threads for example, the threads are passed through a spindle at high speed and then over heating sections to fix the bulk. Due to the high temperatures (above 200 ° C) the preparation agents are thermally decomposed or sublime, sit on the heating units and crack to solid black residues, which disturb the further texturing process. Therefore, the systems have to be shut down at regular intervals and the heating units have to be cleaned mechanically from the residues, which both causes costs and can be detrimental to the health of the workers assigned to cleaning. Therefore, there is great interest in thermostable lubricants that only form liquid residues on the heating units that are emulsifiable with water and can therefore be easily removed.
- EP-A-149 549 discloses copper salts of alkenyl-substituted succinic acid alkyl half-esters and their use as lubricant additives.
- alkenylsuccinic acid esters containing amino groups described below are suitable as fiber preparation agents and are distinguished by improved thermal stability.
- the invention thus relates to alkenylsuccinic acid esters of the formulas containing amino groups wherein R is linear or branched C1-C20-, preferably C5-C15-alkyl, R1 hydroxy-C2-C6-alkyl or C1-C4-alkyl, R2 methyl or ethyl, R3 C6-C20-, preferably C12-C18-alkyl or C6-C20-, preferably C12-C18 alkenyl, A -C2H4- or -C3H7- and n represent a number from 1 to 10, preferably from 3 to 8.
- alkenyl succinic acids of the formula or preferably their anhydrides first with about one mole of an amine of the formula and the resulting alkenylsuccinic acid half-ester with about one mole of an oxalkylated alcohol of the formula R3 (OA) n -OH implements.
- the alkenylsuccinic anhydrides are obtained by reacting ⁇ -olefins with maleic anhydride at temperatures around 200 ° C.
- Linear or branched olefins such as tripropylene (i-non) or tetrapropylene (i-dodecene) can be used for this reaction.
- the oxyalkylated fatty alcohols are prepared by known processes by adding ethylene oxide or propylene oxide to the underlying alcohols.
- the reaction of the alkenylsuccinic anhydrides with the aliphatic amino compounds takes place at temperatures from 20 to 120 ° C., preferably at 60 to 100 ° C.
- the 2nd stage, i.e. the esterification of the free carboxy group with the fatty alcohol oxyethylate is carried out at temperatures from 140 to 260 ° C, preferably at temperatures from 160 to 200 ° C with acid catalysis.
- the acids used for this can be inorganic compounds such as sulfuric acid, phosphoric acid, phosphorous acid etc. or organic acids such as p-toluenesulfonic acid or acidic ion exchangers.
- the amounts required for this depend on the type of acid, they are between 0.1 to 3% by weight, preferably 0.5 to 1.5% by weight.
- the water of reaction is separated off by distillation until an acid number below 10 is reached.
- the two stages of the reaction can be carried out both in the presence and in the absence of a solvent.
- Inert organic solvents with a high boiling point such as decalin or chlorinated aromatic hydrocarbons, are suitable as solvents.
- the alkenyl succinic acid esters according to the invention are used as preparation components for the preparation of fibers made of polyester, polyamide, polyacrylonitrile, polyolefins and Aramid fibers.
- lubricants such as mineral oils or ester oils, for example hexadecyl stearate
- they can be used, inter alia, in combination with emulsifiers based on ethoxylated fatty alcohols or in conjunction with antistatic agents, thread-locking agents.
- Their proportion in the filament preparations can range from 90 to 10%, preferably 60 to 30%.
- the requirements for preparation on the fiber generally range from 0.1 to 2%, preferably 0.3 to 1.2% by weight.
- alkenylsuccinic acid esters have the advantage that they are thermostable and that the residues of these compounds are liquid under the conditions under which they are used in textile fiber production and can therefore be easily removed.
- Example 2 The procedure is as described in Example 1, except that 50 g of i-nonenylsuccinic anhydride are used instead of n-dodecenylsuccinic anhydride. About 45 g of a light brown liquid with a pH of 7 are obtained.
- Example 2 The procedure is as described in Example 2, except that instead of 21.6 parts by weight of N, N-diethylethanolamine, 25 parts by weight of N, N-dimethylbutanolamine are used. About 193 parts by weight of a light brown, viscous oil with a pH of 7 are obtained.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Liquid Crystal Substances (AREA)
- Lubricants (AREA)
Description
Bei der Herstellung von Synthesefasern ist es unbedingt notwendig, sogenannte Präparationsmittel auf der Faseroberfläche aufzubringen. Diese Präparationsmittel haben in der Hauptsache die Aufgabe, die Faden-Metallreibung zu vermeiden, aber auch die Faden-Fadenreibung einzustellen und die elektrostatische Aufladung zu verhindern. Bei der Texturierung von Polyesterfäden beispielsweise werden die Fäden mit hoher Geschwindigkeit durch eine Spindel und anschließend über Heizstrecken geführt, um den Bausch zu fixieren. Durch die hohen Temperaturen (oberhalb 200°C) werden die Präparationsmittel aber thermisch zersetzt oder sublimieren ab, setzen sich auf die Heizaggregate und werden zu festen schwarzen Rückständen gecrackt, die den weiteren Texturierprozeß empfindlich stören. Deshalb müssen die Anlagen in regelmäßigen Abständen abgestellt werden und die Heizeinheiten mechanisch von den Rückständen gereinigt werden, was sowohl Kosten verursacht, als auch eine gesundheitliche Beeinträchtigung der mit der Reinigung beauftragten Arbeiter bedeuten kann. Deshalb besteht ein großes Interesse an thermostabilen Gleitmitteln, die auf den Heizaggregaten lediglich flüssige Rückstände bilden, die mit Wasser emulgierbar sind und somit leicht entfernt werden können.When manufacturing synthetic fibers, it is absolutely necessary to apply so-called preparation agents to the fiber surface. The main task of these preparation agents is to avoid thread-metal friction, but also to adjust thread-thread friction and to prevent electrostatic charging. When texturing polyester threads, for example, the threads are passed through a spindle at high speed and then over heating sections to fix the bulk. Due to the high temperatures (above 200 ° C) the preparation agents are thermally decomposed or sublime, sit on the heating units and crack to solid black residues, which disturb the further texturing process. Therefore, the systems have to be shut down at regular intervals and the heating units have to be cleaned mechanically from the residues, which both causes costs and can be detrimental to the health of the workers assigned to cleaning. Therefore, there is great interest in thermostable lubricants that only form liquid residues on the heating units that are emulsifiable with water and can therefore be easily removed.
Ähnliche Probleme mit Zersetzungsprodukten von Präparationsmitteln bestehen für die Bandstraßen zum Herstellen technischer Fäden (Reifencorde, Förderbänder).Similar problems with decomposition products of preparation agents exist for the belt lines for the production of technical threads (tire cords, conveyor belts).
Aus DD-A-16 287 ist der Einsatz von substituierten Aminoxiden in verschleißmindernd wirkenden Faserpräparationsmitteln für schnellgesponnene Polyesterendlosfäden bekannt.From DD-A-16 287 the use of substituted amine oxides in wear-reducing fiber preparation agents for rapidly spun polyester filaments is known.
In US-A-3 497 550 werden Alkanolaminhalbester der Maleinsäure, Itaconsäure und Zitronensäure sowie deren Verwendung zur Herstellung von Klebstoffen beschrieben.US Pat. No. 3,497,550 describes alkanolamine half-esters of maleic acid, itaconic acid and citric acid and their use for the production of adhesives.
Die EP-A-149 549 offenbart Kupfersalze von alkenylsubstituierten Bernsteinsäurealkylhalbester und deren Verwendung als Schmierstoffzusätze.EP-A-149 549 discloses copper salts of alkenyl-substituted succinic acid alkyl half-esters and their use as lubricant additives.
Es wurde nun gefunden, daß die im folgenden beschriebenen, Aminogruppen enthaltenden Alkenylbernsteinsäureester als Faserpräparationsmittel geeignet sind und sich durch eine verbesserte Thermostabilität auszeichnen.It has now been found that the alkenylsuccinic acid esters containing amino groups described below are suitable as fiber preparation agents and are distinguished by improved thermal stability.
Gegenstand der Erfindung sind somit Aminogruppen enthaltende Alkenylbernsteinsäureester der Formeln
worin R lineares oder verzweigtes C₁-C₂₀-, vorzugsweise C₅-C₁₅-Alkyl, R₁ Hydroxy-C₂-C₆-Alkyl oder C₁-C₄-Alkyl, R₂ Methyl oder Ethyl, R₃ C₆-C₂₀-, vorzugsweise C₁₂-C₁₈-Alkyl oder C₆-C₂₀-, vorzugsweise C₁₂-C₁₈-Alkenyl, A -C₂H₄- oder -C₃H₇- und n eine Zahl von 1 bis 10, vorzugsweise von 3 bis 8 bedeuten.The invention thus relates to alkenylsuccinic acid esters of the formulas containing amino groups
wherein R is linear or branched C₁-C₂₀-, preferably C₅-C₁₅-alkyl, R₁ hydroxy-C₂-C₆-alkyl or C₁-C₄-alkyl, R₂ methyl or ethyl, R₃ C₆-C₂₀-, preferably C₁₂-C₁₈-alkyl or C₆-C₂₀-, preferably C₁₂-C₁₈ alkenyl, A -C₂H₄- or -C₃H₇- and n represent a number from 1 to 10, preferably from 3 to 8.
Diese Verbindungen werden hergestellt indem man Alkenylbernsteinsäuren der Formel
oder vorzugsweise deren Anhydride zunächst mit ungefähr einem Mol eines Amins der Formel
umsetzt und den dabei erhaltenen Alkenylbernsteinsäurehalbester mit ungefähr einem Mol eines oxalkylierten Alkohole der Formel
R₃(OA)n-OH
umsetzt.These compounds are made by using alkenyl succinic acids of the formula
or preferably their anhydrides first with about one mole of an amine of the formula
and the resulting alkenylsuccinic acid half-ester with about one mole of an oxalkylated alcohol of the formula
R₃ (OA) n -OH
implements.
Die Alkenylbernsteinsäureanhydride erhält man durch Umsetzung von α-Olefinen mit Maleinsäureanhydrid bei Temperaturen um 200°C. Für diese Reaktion können lineare oder verzweigte Olefine eingesetzt werden, wie Tripropylen (i-Nonen) oder Tetrapropylen (i-Dodecen). Die oxalkylierten Fettalkohole werden nach bekannten Verfahren durch Addition von Ethylenoxid oder Propylenoxid an die zugrundeliegenden Alkohole hergestellt.The alkenylsuccinic anhydrides are obtained by reacting α-olefins with maleic anhydride at temperatures around 200 ° C. Linear or branched olefins such as tripropylene (i-non) or tetrapropylene (i-dodecene) can be used for this reaction. The oxyalkylated fatty alcohols are prepared by known processes by adding ethylene oxide or propylene oxide to the underlying alcohols.
Die Umsetzung der Alkenylbernsteinsäureanhydride mit den aliphatischen Aminoverbindungen erfolgt bei Temperaturen von 20 bis 120°C vorzugsweise bei 60 bis 100°C. Die 2. Stufe, d.h. die Veresterung der freien Carboxygruppe mit dem Fettalkoholoxäthylat, wird bei Temperaturen von 140 bis 260°C, vorzugsweise bei Temperaturen von 160 bis 200°C unter Säurekatalyse durchgeführt. Die dafür eingesetzten Säuren können anorganische Verbindungen wie Schwefelsäure, Phosphorsäure, phosphorige Säure etc. sein oder organische Säuren wie p-Toluolsulfonsäure oder saure Ionentauscher. Die dafür benötigten Mengen hängen von der Art der Säure ab, sie liegen zwischen 0,1 bis 3 Gew.-%, vorzugsweise 0,5 bis 1,5 Gew.-%. Das Reaktionswasser wird destillativ abgetrennt, bis eine Säurezahl unter 10 erreicht ist. Die beiden Stufen der Reaktion können sowohl in Anwesenheit als auch in Abwesenheit eines Lösemittels durchgeführt werden. Als Lösemittel kommen hierbei inerte organische Lösemittel mit hohem Siedepunkt in Frage wie etwa Dekalin oder chlorierte aromatische Kohlenwasserstoffe.The reaction of the alkenylsuccinic anhydrides with the aliphatic amino compounds takes place at temperatures from 20 to 120 ° C., preferably at 60 to 100 ° C. The 2nd stage, i.e. the esterification of the free carboxy group with the fatty alcohol oxyethylate is carried out at temperatures from 140 to 260 ° C, preferably at temperatures from 160 to 200 ° C with acid catalysis. The acids used for this can be inorganic compounds such as sulfuric acid, phosphoric acid, phosphorous acid etc. or organic acids such as p-toluenesulfonic acid or acidic ion exchangers. The amounts required for this depend on the type of acid, they are between 0.1 to 3% by weight, preferably 0.5 to 1.5% by weight. The water of reaction is separated off by distillation until an acid number below 10 is reached. The two stages of the reaction can be carried out both in the presence and in the absence of a solvent. Inert organic solvents with a high boiling point, such as decalin or chlorinated aromatic hydrocarbons, are suitable as solvents.
Die erfindungsgemäßen Alkenylbernsteinsäureester werden als Präparationskomponenten für das Präparieren von Fasern aus Polyester, Polyamid, Polyacrylnitril, Polyolefinen und Aramidfasern, eingesetzt. Sie können an Stelle der üblichen Gleitmittel, wie z.B. Mineralöle oder Esteröle, z.B. Hexadecylstearat u.a. in Kombination mit Emulgatoren auf Basis oxethylierter Fettalkohole oder in Verbindung mit Antistatika, Fadenschlußmittel eingesetzt werden. Ihr Anteil in den Filamentpräparationen kann von 90 bis 10 %, vorzugsweise 60 bis 30 % reichen. Die Auflagen an Präparation auf die Faser reichen im allgemeinen von 0,1 bis 2 %, vorzugsweise 0,3 bis 1,2 Gew.-%.The alkenyl succinic acid esters according to the invention are used as preparation components for the preparation of fibers made of polyester, polyamide, polyacrylonitrile, polyolefins and Aramid fibers. Instead of the usual lubricants, such as mineral oils or ester oils, for example hexadecyl stearate, they can be used, inter alia, in combination with emulsifiers based on ethoxylated fatty alcohols or in conjunction with antistatic agents, thread-locking agents. Their proportion in the filament preparations can range from 90 to 10%, preferably 60 to 30%. The requirements for preparation on the fiber generally range from 0.1 to 2%, preferably 0.3 to 1.2% by weight.
Diese Alkenylbernsteinsäureester haben den Vorteil, daß sie thermostabil sind und daß die Rückstände dieser Verbindungen unter den Bedingungen, unter denen sie bei der Textilfaserherstellung eingesetzt werden, flüssig sind und somit leicht entfernt werden können.These alkenylsuccinic acid esters have the advantage that they are thermostable and that the residues of these compounds are liquid under the conditions under which they are used in textile fiber production and can therefore be easily removed.
Die folgenden Beispiele sollen die Erfindung erläutern, ohne sie jedoch einzuschränken.The following examples are intended to illustrate the invention without, however, restricting it.
In einem 250 ml Gefäß mit Rührer, Innenthermometer und Kurzwegdestillationsaufsatz wurden 53,38 Gewichtsteile n-Dodecenyl-bernsteinsäureanhydrid bei ca. 50°C aufgeschmolzen, und man läßt 18 Gewichtsteile N,N-Dimethylethanolamin unter Rühren und Stickstoffspülung in 30 Min. bei 50 bis 55°C zutropfen. Die dickflüssige Emulsion wird bei 50°C 4,5 Stunden gerührt, bis im Dünnschichtchromatogramm kein Anhydrid mehr nachweisbar ist. Man kühlt auf 30°C ab und gibt 86,3 Gewichtsteile eines Cocosfettalkoholoxäthylates (mit 5 Ethylenoxydeinheiten), 1,2 Gewichtsteile Borsäure reinst und 1,7 Gewichtsteile hypophosphorige Säure (50%ig) zu. Bei 150 bis 155°C wird 4 Stunden unter Stickstoffspülung gerührt, wobei insgesamt 4 ml Wasser abdestillieren. Anschließend destilliert man im Vakuum innerhalb von 3 Stunden bei einer Temperatur zwischen 130 bis 155°C noch 8 Gewichtsteile der Ausgangsverbindung ab und erhält 146 Gewichtsteile einer hellbraunen, gießbaren Verbindung mit einem pH (1 % in Wasser) von 6 bis 7.53.38 parts by weight of n-dodecenyl succinic anhydride were melted at about 50 ° C. in a 250 ml vessel with a stirrer, internal thermometer and short-path distillation attachment, and 18 parts by weight of N, N-dimethylethanolamine were left with stirring and nitrogen purge in 30 minutes at 50 to Add dropwise 55 ° C. The viscous emulsion is stirred at 50 ° C for 4.5 hours until no more anhydride can be detected in the thin layer chromatogram. It is cooled to 30 ° C. and 86.3 parts by weight of a coconut fatty alcohol ethylate (with 5 ethylene oxide units), 1.2 parts by weight of pure boric acid and 1.7 parts by weight of hypophosphorous acid (50%) are added. At 150 to 155 ° C is stirred for 4 hours under a nitrogen purge, a total of 4 ml of water distilling off. 8 parts by weight of the starting compound are then distilled off in vacuo at a temperature between 130 to 155 ° C. and 146 parts by weight of a light brown, pourable compound having a pH (1% in water) of 6 to 7 are obtained.
Man verfährt wie in Beispiel 1 beschrieben, nur verwendet man anstelle von n-Dodecenylbernsteinsäureanhydrid 50 g i-Nonenylbernsteinsäureanhydrid. Man erhält ca. 45 g einer hellbraunen Flüssigkeit mit einem pH von 7.The procedure is as described in Example 1, except that 50 g of i-nonenylsuccinic anhydride are used instead of n-dodecenylsuccinic anhydride. About 45 g of a light brown liquid with a pH of 7 are obtained.
In einem 500 ml Gefäß mit Rührer, Innenthermometer und Kurzwegdestillationsaufsatz werden 70 Gewichtsteile n-Octadecenylbernsteinsäureanhydrid in 150 Volumenteile Tetralin gelöst und unter Rühren und Stickstoffüberleitung werden 21,6 Gewichtsteile N,N-Diethylethanolamin innerhalb von 30 Minuten bei 35°C zugetropft. Man läßt innerhalb von 4 Stunden bei 50°C ausreagieren, kühlt auf Raumtemperatur ab und versetzt mit 107 Gewichtsteilen Stearylalkohol mit 6 Mol Ethylenoxyd und 3 Gewichtsteilen p-Toluolsulfonsäure. Innerhalb von 2 Stunden werden bei 160 bis 180°C ca. 4 ml Wasser abdestilliert, dann wird das Tetralin in Wasserstrahlvakuum bei 160°C abdestilliert und zurückgewonnen. Man erhält ca. 190 Gewichtsteile eines hellbraunen, viskosen Öles mit einem pH von 7.In a 500 ml vessel with stirrer, internal thermometer and short path distillation attachment, 70 parts by weight of n-octadecenylsuccinic anhydride are dissolved in 150 parts by volume of tetralin, and 21.6 parts by weight of N, N-diethylethanolamine are added dropwise at 35 ° C. in the course of 30 minutes with stirring. The mixture is left to react within 4 hours at 50 ° C., cooled to room temperature and mixed with 107 parts by weight of stearyl alcohol 6 moles of ethylene oxide and 3 parts by weight of p-toluenesulfonic acid. About 4 ml of water are distilled off at 160 to 180 ° C within 2 hours, then the tetralin is distilled off at 160 ° C in a water jet vacuum and recovered. About 190 parts by weight of a light brown, viscous oil with a pH of 7 are obtained.
Man verfährt wie im Beispiel 2 beschrieben, nur verwendet man anstelle 21,6 Gewichtsteile N,N-Diethylethanolamin 25 Gewichtsteile N,N-Dimethylbutanolamin. Man erhält ca. 193 Gewichtsteile eines hellbraunen, viskosen Öles mit einem pH von 7.The procedure is as described in Example 2, except that instead of 21.6 parts by weight of N, N-diethylethanolamine, 25 parts by weight of N, N-dimethylbutanolamine are used. About 193 parts by weight of a light brown, viscous oil with a pH of 7 are obtained.
Die nach Beispiel 1 bis 4 erhaltenen Verbindungen haben folgende Struktur:
Thermotest: Von folgenden Substanzen werden in ein Alu-Schälchen 1 g eingewogen, auf 220°C 24 Stunden erhitzt und der Verlust bestimmt:
- a) Mineralöl (Viskosität bei 20°C: 300 mPas)
- b) Pentaerythrittetradecylat
- c) Produkt nach Beispiel 1
- d) Produkt nach Beispiel 2
- e) Produkt nach Beispiel 3
- f) Produkt nach Beispiel 4
a + b: Vergleiche
c - f: erfindungsgemäß
- a) mineral oil (viscosity at 20 ° C: 300 mPas)
- b) pentaerythritol tetradecylate
- c) Product according to Example 1
- d) Product according to Example 2
- e) Product according to Example 3
- f) Product according to Example 4
a + b: compare
c - f: according to the invention
Diese Werte wurden nach der Methode bestimmt, wie in der DE-OS 23 55 675 angegeben und zwar bei einer Meßgeschwindigkeit von 25 m/min (erster Wert) und 100 m/min (zweiter Wert).These values were determined by the method as specified in DE-OS 23 55 675, namely at a measuring speed of 25 m / min (first value) and 100 m / min (second value).
Claims (3)
- A compound of the general formulae
- A process for preparing a compound as claimed in claim 1, which comprises reacting an alkenylsuccinic acid of the formula
R₃(OA)n-OH
where R, R₁, R₂, R₃, A and n are as defined in claim 1. - The use of the compound as claimed in claim 1 as a spin finish agent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873732340 DE3732340A1 (en) | 1987-09-25 | 1987-09-25 | AMINO GROUPS CONTAINING ALKENYL AMBERSTEIC ACID ESTERS |
| DE3732340 | 1987-09-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0308914A2 EP0308914A2 (en) | 1989-03-29 |
| EP0308914A3 EP0308914A3 (en) | 1989-11-23 |
| EP0308914B1 true EP0308914B1 (en) | 1993-06-30 |
Family
ID=6336870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88115534A Expired - Lifetime EP0308914B1 (en) | 1987-09-25 | 1988-09-22 | Alkenyl-succinic esters containing amino groups |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4883495A (en) |
| EP (1) | EP0308914B1 (en) |
| JP (1) | JPH0196157A (en) |
| DE (2) | DE3732340A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032145A (en) * | 1987-04-20 | 1991-07-16 | Mobil Oil Corporation | Low temperature fluidity improver and compositions thereof |
| JPH0412161A (en) * | 1990-05-01 | 1992-01-16 | Mazda Motor Corp | Intake device of engine |
| US5427589A (en) * | 1993-03-03 | 1995-06-27 | Springs Industries, Inc. | Method for dyeing fibrous materials |
| US5437690A (en) * | 1994-05-25 | 1995-08-01 | Springs Industries, Inc. | Method for dyeing fibrous materials and dye assistant relating to the same |
| EP1559500B1 (en) | 2004-01-29 | 2011-08-17 | Siemens Aktiengesellschaft | Method and device for mechanical working of a hollow component |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497550A (en) * | 1966-11-07 | 1970-02-24 | Kendall & Co | Polymerizable monomers,copolymers thereof and adhesive made therefrom |
| US4185485A (en) * | 1978-06-30 | 1980-01-29 | Mobil Oil Corporation | Lubricant compositions for can forming |
| US4435297A (en) * | 1978-09-27 | 1984-03-06 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines |
| DD160287A1 (en) * | 1981-04-30 | 1983-05-25 | Juergen Peschel | WEAR-REDUCING PRAEPARATION FOR FAST-SPONGED PIGMENTED POLYESTER DISSOLVED FAIRS |
| US4552677A (en) * | 1984-01-16 | 1985-11-12 | The Lubrizol Corporation | Copper salts of succinic anhydride derivatives |
| DE3526601A1 (en) * | 1985-07-25 | 1987-01-29 | Hoechst Ag | OXALKYLATED POLYESTERAMINE, METHOD FOR THE PRODUCTION AND USE THEREOF |
-
1987
- 1987-09-25 DE DE19873732340 patent/DE3732340A1/en not_active Withdrawn
-
1988
- 1988-09-21 US US07/247,277 patent/US4883495A/en not_active Expired - Fee Related
- 1988-09-22 EP EP88115534A patent/EP0308914B1/en not_active Expired - Lifetime
- 1988-09-22 JP JP63236664A patent/JPH0196157A/en active Pending
- 1988-09-22 DE DE8888115534T patent/DE3882106D1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4883495A (en) | 1989-11-28 |
| DE3732340A1 (en) | 1989-04-13 |
| EP0308914A2 (en) | 1989-03-29 |
| JPH0196157A (en) | 1989-04-14 |
| DE3882106D1 (en) | 1993-08-05 |
| EP0308914A3 (en) | 1989-11-23 |
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