DE3932912A1 - Synthetic polyamide(s) for plastics, inks and lacquers - Google Patents
Synthetic polyamide(s) for plastics, inks and lacquersInfo
- Publication number
- DE3932912A1 DE3932912A1 DE3932912A DE3932912A DE3932912A1 DE 3932912 A1 DE3932912 A1 DE 3932912A1 DE 3932912 A DE3932912 A DE 3932912A DE 3932912 A DE3932912 A DE 3932912A DE 3932912 A1 DE3932912 A1 DE 3932912A1
- Authority
- DE
- Germany
- Prior art keywords
- synthetic polyamides
- parts
- acid
- dicarboxylic acid
- sterically hindered
- Prior art date
- 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
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyamides (AREA)
Abstract
Description
Es wurde gefunden, daß sich synthetische Polyamide, die im Molekül sterisch gehinderte Aminogruppen enthalten, ausgezeichnet zur Verbesserung der Anfärbbarkeit von synthetischen Polyamiden mit sauren Farbstoffen, als Lichtstabilisatoren für Kunststoffe und als Farbstoffträger (Ankerfunktion) für das Einfärben von lösungsmittelfreien und lösungsmittelhaltigen Polymeren und Drucktinten eignen.It has been found that synthetic polyamides are present in the molecule contain sterically hindered amino groups, excellent for improvement the dyeability of synthetic polyamides with acid dyes, as light stabilizers for plastics and as dye carrier (Anchor function) for the coloring of solvent-free and solvent-containing Polymers and printing inks are suitable.
Unter Resten mit sterisch gehinderten Aminogruppen sind im allgemeinen alle cyklischen Reste zu verstehen, die eine Gruppierung der Formel -C(Alkyl)₂-NH-C(Alkyl)₂- aufweisen, wobei das Wasserstoffatom durch einen Alkyl- oder Acylrest substituiert sein kann und die Alkylreste 1 bis 4 Kohlenstoffatome enthalten.Among radicals with sterically hindered amino groups are in general to understand all cyclic residues that are a grouping of the formula -C (alkyl) ₂-NH-C (alkyl) ₂-, wherein the hydrogen atom by a Alkyl or acyl radical may be substituted and the alkyl radicals 1 to 4 Contain carbon atoms.
Vorzugsweise enthalten die neuen synthetischen Polyamide (bzw. oligomeren Amide) pro Molekül etwa 5 bis 200, vorzugsweise 10 bis 50 sterisch gehinderte Aminogruppen, das heißt, daß die Zahl der sterisch gehinderten Aminogruppen durch Kontrolle des Polymerisationsgrades (Kettenabbruch) festgelegt wird, bzw. daß bei der Herstellung pro 10 Mol Dicarbonsäure, bzw. Diamin (bzw. pro 20 Mol Lactam) etwa 0,1 bis 5 Mol einer polykondensierbaren Verbindung mit einer oder zwei sterisch gehinderten Aminogruppen eingesetzt werden. Dabei muß natürlich die eingesetzte Menge Diamin (ohne sterisch gehindertes Amin) entsprechend reduziert werden, bzw. ganz wegfallen, wenn das sterisch gehinderte Amin Bestandteil eines Diamins ist, bzw. muß die Menge Dicarbonsäure entsprechend (wenn nötig auf Null) reduziert werden, wenn das sterisch gehinderte Amin Bestandteil einer Dicarbonsäureverbindung ist. Preferably, the new synthetic polyamides (or oligomeric Amides) per molecule about 5 to 200, preferably 10 to 50 sterically hindered Amino groups, that is, the number of sterically hindered Amino groups by controlling the degree of polymerization (chain termination) or that in the preparation per 10 moles of dicarboxylic acid, or diamine (or per 20 mol lactam) about 0.1 to 5 moles of a polycondensable Compound with one or two sterically hindered amino groups be used. Of course, the amount used Diamine (without sterically hindered amine) can be reduced accordingly, or completely eliminated if the hindered amine is part of a Diamins is, or must the amount of dicarboxylic acid accordingly (if necessary to zero) when the hindered amine is an ingredient a dicarboxylic acid compound.
Die Herstellung der neuen Polyamide erfolgt durch Polykondensation eines Moläquivalents einer zur Polykondensation geeigneten Dicarbonsäure oder eines funktionellen Derivats einer solchen Dicarbonsäure, mit einem Moläquivalent eines zur Polykondensation geeigneten Diamins oder durch Polykondensation eines geeigneten Lactams, wobei ein Teil oder alle der Dicarbonsäuremoleküle, und/oder der Diaminomoleküle, beziehungsweise der Lactammoleküle einen Substituenten mit einer oder zwei sterisch gehinderten Aminogruppen trägt.The preparation of the new polyamides is carried out by polycondensation of a Molar equivalent of a suitable for polycondensation dicarboxylic acid or a functional derivative of such a dicarboxylic acid, with one molar equivalent a suitable for polycondensation diamine or by polycondensation of a suitable lactam, where some or all of the dicarboxylic acid molecules, and / or the diaminomolecules, or the Lactam molecules have a substituent with one or two sterically hindered Carries amino groups.
Als funktionelle Dicarbonsäurederivate sind vorzugsweise die Ester mit niedrigmolekularen Alkoholen oder, z. B. im Fall von Poly-(meta- oder para-phenylen-iso- oder -terephthalamid), die Säurehalogenide, vorzugsweise das Dicarbonsäuredichlorid, zu verstehen. Die Polykondensationsreaktionen werden analog zu den bekannten, bei entsprechenden Polykondensationen angewendeten Bedingungen durchgeführt.As functional dicarboxylic acid derivatives are preferably the esters with low molecular weight alcohols or, for. B. in the case of poly (meta- or para-phenylene iso- or terephthalamide), the acid halides, preferably dicarboxylic acid dichloride. The polycondensation reactions be analogous to the known, in corresponding polycondensations conditions applied.
Beispiele für Diaminoverbindungen die eine oder zwei sterisch gehinderte Gruppen als Substituenten tragen, sind 1,3-Diamino-5-(2′,2′,6′,6′-tetramethylpiperidyl- 4′)-benzoesäureamid, 4-(2′,2′,6′,6′-Tetramethylpiperidyl- 4′-amino)-anilin (hergestellt durch Kondensation von 4-Chlor-nitrobenzol mit 2,2,6,6-Tetraalkyl-4-aminopiperidyl und Reduktion der Nitrogruppe), 2,4-Bis-(amino-C2-20-alkylamino)-6-(2′,2′,6′,6′-tetramethylpiperidyl-4′- amino)-triazin, N,N′-ω-Bis-(2′,2′,6′,6′-tetramethylpiperidyl-4′-amino)- C2-20-alkylen.Examples of diamino compounds bearing one or two sterically hindered groups as substituents are 1,3-diamino-5- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4') - benzoic acid amide, 4- (2 ', 2 ', 6', 6'-tetramethylpiperidyl-4'-amino) -aniline (prepared by condensation of 4-chloro-nitrobenzene with 2,2,6,6-tetraalkyl-4-aminopiperidyl and reduction of the nitro group), 2, 4-bis- (amino-C 2-20 -alkylamino) -6- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) triazine, N, N'-ω-bis ( 2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amino) - C 2-20 alkylene.
Die mit Isophthalsäure hergestellten Polyamide sind in einer Reihe von organischen Lösungsmitteln relativ leicht löslich, die mit Terephthalsäure hergestellten Polyamide sind in allen organischen Lösungsmitteln unlöslich (sie lösen sich in konz. Schwefelsäure).The polyamides prepared with isophthalic acid are in a series of organic solvents relatively easily soluble with terephthalic acid produced polyamides are in all organic solvents insoluble (they dissolve in concentrated sulfuric acid).
Die neuen synthetischen Polyamide werden im allgemeinen in Mengen zwischen 1 und 10 Gewichtsprozent, vorzugsweise von 2 bis 5 Gewichtsprozent, den synthetischen Polyamiden (zur Verbesserung der Anfärbbarkeit) und den lösungsmittelfreien Polymeren (als Lichtstabilisatoren) zugesetzt, was vorzugsweise durch Mischen in der Schmelze des betreffenden Kunststoffs geschieht. Bei lösungsmittelhaltigen Polymeren und Drucktinten wendet man die gleichen Mengen, aber bezogen auf die Trockensubstanzen an.The new synthetic polyamides are generally in quantities between 1 and 10 weight percent, preferably from 2 to 5 weight percent, synthetic polyamides (to improve dyeability) and the solvent-free polymers (as light stabilizers) added, preferably by mixing in the melt of the relevant Plastic happens. For solvent-containing polymers and Printing inks apply the same amounts, but based on the dry substances.
In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.In the following examples, the parts parts by weight and the Percentages by weight. The temperatures are in degrees Celsius specified.
In 206 Teilen wasserfreiem 1-Methyl-2-pyrrolidon werden 14,5 Teile 3,5-Diaminobenzoesäure-2′,2′,6′,6′-tetramethylpiperidyl-4′-amid (hergestellt durch Kondensation von 3,5-Dinitrobenzoesäure mit 2,2,6,6-Tetramethyl-4-aminopiperidyl und Reduktion der Nitrogruppen) gelöst, auf 0 bis +5° gekühlt und portionsweise, im Verlauf einer Stunde, mit 10,15 Teilen Isophthalsäuredichlorid versetzt. Man rührt sodann 2 Stunden bei 20-25° und 6 Stunden bei 100°, destilliert das 1-Methyl-2-pyrrolidon unter vermindertem Druck ab, verrührt die erhaltene viskose Masse in 250 Teilen Aceton, wobei sich ein hellbeiger Niederschlag bildet, der durch Filtration vom Aceton abgetrennt wird. Der Rückstand wird in 200 Teilen 2prozentiger Natronlauge bei Raumtemperatur verrührt, abfiltriert, mit 200 Teilen Wasser in vier Portionen neutral gewaschen und bei 80° unter einem Vakuum von ca. 50 Pa getrocknet. Das Molekulargewicht des so erhaltenen Polyamids ist ca. 6400, sein Schmelzpunkt liegt über 300°.In 206 parts of anhydrous 1-methyl-2-pyrrolidone become 14.5 parts 3,5-diaminobenzoic acid-2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amide (prepared by condensation of 3,5-dinitrobenzoic acid with 2,2,6,6-tetramethyl-4-aminopiperidyl and reduction of nitro groups) dissolved, cooled to 0 to + 5 ° and in portions, in the course of a Hour, mixed with 10.15 parts of isophthalic acid dichloride. Man stirs then 2 hours at 20-25 ° and 6 hours at 100 °, the distilled 1-methyl-2-pyrrolidone under reduced pressure, the resulting mixture is stirred viscous mass in 250 parts of acetone, resulting in a light beige precipitate forms, which is separated by filtration from acetone. The The residue is dissolved in 200 parts of 2% sodium hydroxide solution at room temperature stirred, filtered off, with 200 parts of water in four portions neutral washed and dried at 80 ° under a vacuum of about 50 Pa. The Molecular weight of the polyamide thus obtained is about 6400, its melting point is over 300 °.
Man verfährt wie im Beispiel 1 angegeben, an Stelle der 14,5 Teile 3,5-Diaminobenzoesäure-2′,2′,6′,6′-tetramethylpiperidyl-4-amid werden aber 15,1 Teile 3,5-Diaminobenzoesäure-1′,2′,2′,6′,6′-pentamethylpiperidyl- 4′-amid eingesetzt. Man erhält so ein Polyamid mit ganz ähnlichen Eigenschaften wie das gemäß Beispiel 1 hergestellte Polyamid.The procedure is as in Example 1, instead of 14.5 parts 3,5-diaminobenzoic acid-2 ', 2', 6 ', 6'-tetramethylpiperidyl-4-amide but 15.1 parts of 3,5-diaminobenzoic acid 1 ', 2', 2 ', 6', 6'-pentamethylpiperidyl 4'-amide used. This gives a polyamide with whole similar properties as the polyamide prepared according to Example 1.
Man verfährt wie im Beispiel 1 angegeben, setzt aber an Stelle des dort angegebenen Diamins 12,35 Teile 4-(2′,2′,6′,6′-Tetramethylpiperidyl-4′- amino)-anilin (hergestellt durch Kondensation von p-Chloranilin mit 2,2,6,6-Tetramethyl-4-aminopiperidin) bzw. 13,05 Teile 4-(1′,2′,2′,6′, 6′-Pentamethylpiperidyl-4′-amino)-anilin ein. Man erhält so ebenfalls erfindungsgemäß verwendbare Polyamide. The procedure is as given in Example 1, but instead of there 12.35 parts of 4- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'- amino) -aniline (prepared by condensation of p-chloroaniline with 2,2,6,6-tetramethyl-4-aminopiperidine) or 13.05 parts 4- (1 ', 2', 2 ', 6', 6'-pentamethylpiperidyl-4'-amino) -aniline. You get as well Polyamides usable according to the invention.
Man verfährt wie in den Beispielen 1 bis 4 angegeben, verwendet aber an Stelle des Isophthalsäuredichlorids dieselbe Menge Terephthalsäuredichlorid.The procedure is as given in Examples 1 to 4, but used on Isophthalic acid chloride is the same amount of terephthalic acid dichloride.
Man verfährt wie in den Beispielen 1 bis 4 angegeben, verwendet aber an
Stelle der dort angegebenen Diamine jeweils ein Gemisch aus 2,82 Teilen
m-Phenylendiamin und
Bsp. 9 5,8 Teilen des Amins gemäß Bsp. 1,
Bsp. 10 6,04 Teilen des Amins gemäß Bsp. 2,
Bsp. 11 4,94 Teilen des Amins gemäß Bsp. 3 bzw.
Bsp. 12 5,22 Teilen des Amins gemäß Bsp. 4.The procedure is as given in Examples 1 to 4, but in place of the diamines indicated therein in each case a mixture of 2.82 parts of m-phenylenediamine and
Ex. 9 5.8 parts of the amine according to Ex. 1,
Ex. 10 6.04 parts of the amine according to Ex. 2,
Ex. 11. 4.94 parts of the amine according to Ex. 3 and
Ex. 12 5.22 parts of the amine according to Ex. 4.
Man verfährt wie in den Beispielen 5 bis 8 angegeben, verwendet jedoch die Diamin-Mischungen gemäß den Beispielen 9 bis 12.The procedure is as given in Examples 5 to 8, but used the diamine mixtures according to Examples 9 to 12.
11,07 Teile Trichlortriazin werden auf übliche Weise mit 13,92 Teilen Hexamethylendiamin und 9,36 Teilen 2,2,6,6-Tetramethyl-4-aminopiperidin zur Verbindung der Formel11.07 parts of trichlorotriazine are in the usual manner with 13.92 parts Hexamethylenediamine and 9.36 parts of 2,2,6,6-tetramethyl-4-aminopiperidine to the compound of the formula
kondensiert. Diese Verbindung wird auf übliche Weise gereinigt, und getrocknet.condensed. This compound is purified in the usual way, and dried.
22,9 Teile dieser Verbindung werden sodann auf übliche Weise mit 7,3 Teilen Adipinsäure bis zu einem Polymerisationsgrad von etwa 35 kondensiert. 22.9 parts of this compound are then in the usual way with 7.3 Share adipic acid condensed to a degree of polymerization of about 35.
Analog zur Arbeitsweise des Beispiels 17 können auch 19,7 Teile Hexamethylen- N,N′-di-(2′,2′,6′,6′-tetramethylpiperidyl-4′-amin) und 7,3 Teile Adipinsäure bis zu einem Polymerisationsgrad von etwa 25 kondensiert werden.Analogously to the procedure of Example 17, 19.7 parts of hexamethylene N, N'-di- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amine) and 7.3 parts Adipic acid condensed to a degree of polymerization of about 25 become.
Analog zur Arbeitsweise des Beispiels 1 werden 19,7 Teile Hexamethylen- N,N′-di-(2′,2′,6′,6′-tetramethylpiperidyl-4′-amin) und 10,15 Teile Isophthalsäuredichlorid polykondensiert und rein dargestellt.Analogously to the procedure of Example 1, 19.7 parts of hexamethylene N, N'-di- (2 ', 2', 6 ', 6'-tetramethylpiperidyl-4'-amine) and 10.15 parts Isophthalic acid polycondensed and pure.
98 Teile Nylon-6-Granulat werden mit 2 Teilen des Produkts gemäß Beispiel 1 in einem Pulvermischer (Rhoenrad) 1 Stunde gemischt und anschließend in einem Labor-Extruder (Type MARIS TM 33 V/32 D) unter den folgenden Bedingungen behandelt und zu Fasern versponnen:98 parts of nylon 6 granules are mixed with 2 parts of the product according to Example 1 mixed in a powder mixer (Rhoenrad) for 1 hour and then in a laboratory extruder (type MARIS TM 33 V / 32 D) among the treated and spun into fibers as follows:
Die so erhaltenen Fasern können tel quel oder nach Verarbeitung zu Garnen, Geweben oder Gewirken wie für Polyamidfasermaterial üblich, mit den geeigneten sauren Farbstoffen, z. B. den Farbstoffen C.I. Acid Red 216, Acid Violet 66, Acid Yellow 155, Acid Blue 230, Acid Red 129, Acid Yellow 184, Acid Red 119 oder Acid Blue nach bekannten Verfahren gefärbt oder bedruckt werden.The fibers obtained in this way can be added to the product or after processing Yarns, woven or knitted fabrics as usual for polyamide fiber material, with the appropriate acidic dyes, eg. B. the dyes C.I. Acid red 216, Acid Violet 66, Acid Yellow 155, Acid Blue 230, Acid Red 129, Acid Yellow 184, Acid Red 119 or Acid Blue stained by known methods or printed.
Die so erhaltenen Färbungen zeichnen sich durch ihre erhöhte Farbtiefe (gegenüber einer gleichen Färbung auf nicht modifiziertem Poly-ε-caprolactam), Brillanz, Licht- und Naßechtheiten aus.The resulting dyeings are characterized by their increased color depth (compared to a same coloration on unmodified Poly-ε-caprolactam), brilliance, light and wet fastness.
Claims (5)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3932912A DE3932912A1 (en) | 1989-10-03 | 1989-10-03 | Synthetic polyamide(s) for plastics, inks and lacquers |
| EP90913413A EP0461206B1 (en) | 1989-09-09 | 1990-09-06 | Synthetic polyamides and their salts |
| PCT/EP1990/001495 WO1991003511A1 (en) | 1989-09-09 | 1990-09-06 | Synthetic polyamides and their salts |
| DE69007092T DE69007092T2 (en) | 1989-09-09 | 1990-09-06 | SYNTHETIC POLYAMIDES AND THEIR SALTS. |
| JP2512371A JP3041823B2 (en) | 1989-09-09 | 1990-09-06 | Synthetic polyamides and their salts |
| US08/247,132 US5470921A (en) | 1989-09-09 | 1994-05-20 | Synthetic polyamides and their salts |
| HK34797A HK34797A (en) | 1989-09-09 | 1997-03-20 | Synthetic polyamides and their salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3932912A DE3932912A1 (en) | 1989-10-03 | 1989-10-03 | Synthetic polyamide(s) for plastics, inks and lacquers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3932912A1 true DE3932912A1 (en) | 1991-04-11 |
Family
ID=6390705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3932912A Withdrawn DE3932912A1 (en) | 1989-09-09 | 1989-10-03 | Synthetic polyamide(s) for plastics, inks and lacquers |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3932912A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995028443A1 (en) * | 1994-04-15 | 1995-10-26 | Basf Aktiengesellschaft | Inherently light- and heat-stabilized polyamides |
| DE19537614A1 (en) * | 1995-10-09 | 1997-04-10 | Inventa Ag | Polycaprolactam with a new chain control |
| DE102005023419A1 (en) * | 2005-05-20 | 2006-11-23 | Ems-Chemie Ag | Polyamide oligomers and their use |
| WO2007128715A1 (en) * | 2006-05-04 | 2007-11-15 | Clariant International Ltd | Process for improved and controlled dyeability of polyamide-6 fibers |
| US7910652B2 (en) | 2005-05-20 | 2011-03-22 | Ems-Chemie Ag | Polyamide molding materials with an improved flowability, the production thereof and its use |
| DE19745099B4 (en) * | 1997-10-11 | 2014-11-06 | Lurgi Zimmer Gmbh | Use of an additive having chain regulating and stabilizing properties in the production of polycaprolactam |
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-
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| WO1995028443A1 (en) * | 1994-04-15 | 1995-10-26 | Basf Aktiengesellschaft | Inherently light- and heat-stabilized polyamides |
| DE19537614A1 (en) * | 1995-10-09 | 1997-04-10 | Inventa Ag | Polycaprolactam with a new chain control |
| DE19537614C3 (en) * | 1995-10-09 | 2003-10-02 | Inventa Ag | Polycaprolactam with a new chain control |
| DE19745099B4 (en) * | 1997-10-11 | 2014-11-06 | Lurgi Zimmer Gmbh | Use of an additive having chain regulating and stabilizing properties in the production of polycaprolactam |
| DE102005023419A1 (en) * | 2005-05-20 | 2006-11-23 | Ems-Chemie Ag | Polyamide oligomers and their use |
| DE102005023419B4 (en) * | 2005-05-20 | 2007-02-22 | Ems-Chemie Ag | Polyamide oligomers and their use |
| US7786222B2 (en) | 2005-05-20 | 2010-08-31 | Ems-Chemie Ag | Polyamide oligomers and their use |
| US7910652B2 (en) | 2005-05-20 | 2011-03-22 | Ems-Chemie Ag | Polyamide molding materials with an improved flowability, the production thereof and its use |
| US8138259B2 (en) | 2005-05-20 | 2012-03-20 | Ems-Chemie Ag | Polyamide molding materials with an improved flowability, the production thereof and its use |
| WO2007128715A1 (en) * | 2006-05-04 | 2007-11-15 | Clariant International Ltd | Process for improved and controlled dyeability of polyamide-6 fibers |
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