DE4136079A1 - Rapid post-condensn. of (co)polyamide(s) for hot melt adhesives - by reactive coupling in the melt with di:isocyanate in the presence of isocyanate capping agent - Google Patents
Rapid post-condensn. of (co)polyamide(s) for hot melt adhesives - by reactive coupling in the melt with di:isocyanate in the presence of isocyanate capping agentInfo
- Publication number
- DE4136079A1 DE4136079A1 DE19914136079 DE4136079A DE4136079A1 DE 4136079 A1 DE4136079 A1 DE 4136079A1 DE 19914136079 DE19914136079 DE 19914136079 DE 4136079 A DE4136079 A DE 4136079A DE 4136079 A1 DE4136079 A1 DE 4136079A1
- Authority
- DE
- Germany
- Prior art keywords
- polyamides
- oligo
- isocyanate
- diisocyanate
- polyamide
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/60—Polyamides or polyester-amides
- C08G18/603—Polyamides
-
- 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
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/28—Preparatory processes
-
- 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
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyamides (AREA)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur schnellen Aufkondensation von Oligo- und/oder (Co-)Polyamiden in der Schmelze, die zur Fadenbildung, zur Spitzgußverarbeitung, als Extrusionstype und als Schmelzkleber eingesetzt werden können.The invention relates to a method for the rapid condensation of Oligo- and / or (co-) polyamides in the melt, which are used for thread formation, for injection molding, as an extrusion type and as a hot melt adhesive can be used.
Polyamide werden in großen Mengen in reiner Form oder modifiziert zu Fasern, Kunststoff-Formteilen, Folien sowie als Hilfsstoff in einer Vielzahl von Anwendungen wie z. B. Schmelzkleber eingesetzt. Die Poly amidsynthese erfolgt aus Lactamen über kationische, hydrolytische und anionische Aufbaureaktionen sowie über Polykondensation von Diami nen mit Dicarbonsäuren, Aminocarbonsäuren oder Derivaten davon (Vieh weg, Müller; Kunststoff-Handbuch, Bd.VI, S. 11 ff., Carl-Hanser-Verlag München, 1966).Large quantities of polyamides are added in pure form or modified Fibers, molded plastic parts, foils and as an auxiliary in one Variety of applications such as B. hot melt adhesive used. The poly Amide synthesis takes place from lactams via cationic, hydrolytic and anionic build-up reactions and via polycondensation of diami with dicarboxylic acids, aminocarboxylic acids or derivatives thereof (cattle away, miller; Kunststoff-Handbuch, Vol.VI, p. 11 ff., Carl-Hanser-Verlag Munich, 1966).
Bei den Synthesen werden verfahrensbedingt Polymerisationsgrade/Mo lekulargewichte erreicht, die kommerziellen Ansprüchen genügen. Höhere Molekulargewichte werden z. B. über thermische Nachpolykondensation in der Festphase realisiert.Depending on the process, degrees of polymerization / Mo reached molecular weights that meet commercial requirements. Higher Molecular weights are e.g. B. via thermal post-polycondensation in the solid phase.
In der DE-OS 38 31 707 werden ein Verfahren zur beschleunigten Poly amidherstellung während der Schmelzepolykondensation unter Verwendung von Aminocaprolactam und/oder Lysinkomponenten und unter Zusatz von Katalysatoren, sowie auch eine beschleunigte Festphasen-Nachpolykon densation der katalysatorhaltigen (Co-)Polyamide und die nach Verfah ren hergestellten Polyamide beschrieben.In DE-OS 38 31 707 a method for accelerated poly amide production during melt polycondensation using of aminocaprolactam and / or lysine components and with the addition of Catalysts, as well as an accelerated solid-phase post polycon densification of the catalyst-containing (co) polyamides and the process Ren produced polyamides described.
Die DE-OS 38 31 708 beschreibt ein Verfahren zur Festphasen-Nachpoly kondensation von (Co-)Polyamiden, welche geringe Mengen an Lysin-Kom ponenten und dazu etwa äquivalente Mengen einer Polycarbonsäure einge baut enthalten. Es werden in verkürzter Reaktionszeit thermoplastisch verformbare, leicht verzweigte, aliphatische (Co-)Polyamide mit erhöh ter Schmelzeviskosität und ausgeprägter Strukturviskosität erhalten.DE-OS 38 31 708 describes a method for solid phase post poly condensation of (co) polyamides, which contain small amounts of lysine com components and about equivalent amounts of a polycarboxylic acid builds included. It becomes thermoplastic in a shorter reaction time malleable, slightly branched, aliphatic (co) polyamides with increased ter melt viscosity and pronounced structural viscosity.
Um entsprechende Eigenschaften zu erreichen, sind trotzdem Reaktions zeiten bis zu mehreren Stunden notwendig. Die Polyamide werden in die ser zweiten, energieintensiven Verfahrensstufe thermisch über einen längeren Zeitraum belastet.In order to achieve appropriate properties, there are still reactions times of up to several hours are necessary. The polyamides are in the ser second, energy-intensive process stage thermally via a for a long period of time.
Ziel der Erfindung ist es, ein einfaches Verfahren zur schnellen Auf kondensation von Oligo- und/oder (Co-)Polyamiden in der Schmelze zu entwickeln, das im Rühr-(Kessel-)Reaktor und/oder im (Reaktions-)Ex truder durchführbar ist.The aim of the invention is to provide a simple method for quick on condensation of oligo- and / or (co-) polyamides in the melt develop that in the stirred (boiler) reactor and / or in the (reaction) Ex truder is feasible.
Der Erfindung liegt die Aufgabe zugrunde, über eine definierte, schnelle Kopplungsreaktion Oligo- und/oder (Co-)Polyamide in Schmelze nach einem neuartigen Verfahren aufzukondensieren.The invention is based on the object, via a defined rapid coupling reaction of oligo- and / or (co-) polyamides in the melt to condense using a novel process.
Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß thermoplastisch verarbeitbare Oligo- und/oder (Co-)Polyamide mit mindestens einer freien Amino- und/oder Carbonsäure-Endgruppe unter Zugabe eines Iso cyanatgruppen-Verkappungsmittels von 0,1 bis 10 Masse-%, bezogen auf das eingesetzte Oligo- und/oder (Co-)Polyamid, in der Schmelze mit Diisocyanat in reiner Form oder im Gemisch mit anderen Diisocyanaten in geschmolzenem, gas-, dampf- oder aerosolförmigen Zustand oder in einem inerten Lösungsmittel gelöst oder dispers verteilt unter guter Vermischung des Diisocyanats in der Oligo- und/oder (Co-)Polyamid- Schmelze umgesetzt werden. Eine homogene Fein-Verteilung ohne größere Konzentrationsunterschiede an oder in der Thermoplast-Schmelze (Ober fläche) ist erforderlich. Vorteilhaft ist es, thermoplastisch verar beitbare Oligo- und/oder (Co-)Polyamide im Verhältnis pro Äquivalent an freier Amino- und/oder Carbonsäure-Endgruppen im Oligo- und/oder (Co-)Polyamid zu 0,1 bis 2 Äquivalenten an Isocyanat-Gruppen der als Kopplerkomponente eingesetzten Diisocyanate umzusetzen. Dadurch werden definiert aufkondensierte (Co-)Polyamide mit einstellbaren linearen und/oder verzweigten bis zu vernetzten Strukturen in einer Zeitspanne von 0,1 bis 10 Minuten hergestellt.According to the invention the object is achieved in that thermoplastic Processable oligo- and / or (co-) polyamides with at least one free amino and / or carboxylic acid end group with the addition of an iso cyanate group capping agent from 0.1 to 10 mass%, based on the oligo- and / or (co-) polyamide used in the melt with Diisocyanate in pure form or in a mixture with other diisocyanates in the molten, gaseous, vapor or aerosol state or in dissolved in an inert solvent or dispersed with good Mixing of the diisocyanate in the oligo- and / or (co-) polyamide Melt are implemented. A homogeneous fine distribution without major Differences in concentration on or in the thermoplastic melt (upper area) is required. It is advantageous to process them thermoplastic Processable oligo- and / or (co-) polyamides in the ratio per equivalent at free amino and / or carboxylic acid end groups in the oligo and / or (Co) polyamide to 0.1 to 2 equivalents of isocyanate groups as Implement coupler component used diisocyanates. This will defines condensed (co) polyamides with adjustable linear and / or branched up to networked structures in a period of time made from 0.1 to 10 minutes.
Das Isocyanatgruppen-Verkappungsmittel wird in Substanz (100 Masse-%) oder in einer Menge von 99,99 bis 0,01 Masse-%, bezogen auf die einge setzte Menge an Isocyanatgruppen-Verkappungsmittel, in einem, vorzugs weise inerten, Lösungsmittel gelöst, vor dem Einsatz oder gleichzeitig mit der Diisocyanat-Kopplerkomponente zugegeben. Als Isocyanatgruppen- Verkappungsmittel werden Alkohole und/oder Lactame, vorzugsweise 1C- bis 6C-Alkohole oder Epsilon-Caprolactam, verwendet.The isocyanate group capping agent is in bulk (100% by mass) or in an amount of 99.99 to 0.01 mass%, based on the set amount of isocyanate group capping agent, in one, preferred wise inert, solvent dissolved, before use or simultaneously added with the diisocyanate coupler component. As isocyanate group Capping agents are alcohols and / or lactams, preferably 1C- to 6C alcohols or epsilon-caprolactam used.
Lineare oder nur wenig verzweigte, aufkondensierte (Co-)Polyamide ent stehen bei einem Umsetzungsverhältnis von einem Äquivalent an Amino- und/oder Carbonsäure-Endgruppen im Oligo- und/oder (Co-)Polyamid zu 0,3 bis 1,1, vorzugsweise von 0,7 bis 1,0, Äquivalenten an Isocyanat gruppen der eingesetzten Kopplerkomponente. Linear or only slightly branched, condensed (co) polyamides are at a conversion ratio of one equivalent of amino and / or carboxylic acid end groups in the oligo- and / or (co-) polyamide 0.3 to 1.1, preferably from 0.7 to 1.0, equivalents of isocyanate groups of the coupler components used.
Gleichmäßig verzweigte oder vernetzte, aufkondensierte (Co-)Polyamide werden bei einem Umsetzungsverhältnis von einem Äquivalent an Amino und/oder Carbonsäure-Endgruppen im Oligo- und/oder (Co-)Polyamid zu größer als 1,1 Äquivalenten an Isocyanat-Gruppen der eingesetzten Kopplerkomponente erhalten.Uniformly branched or cross-linked, condensed (co) polyamides with a conversion ratio of one equivalent of amino and / or carboxylic acid end groups in the oligo- and / or (co-) polyamide greater than 1.1 equivalents of isocyanate groups used Get coupler component.
Die erhaltenen (Co-)Polyamide weisen eine höhere Lösungsviskosität und eine höhere Schmelzeviskosität auf.The (co) polyamides obtained have a higher solution viscosity and a higher melt viscosity.
Der Vorteil des Verfahrens besteht in einer kurzen Zeitspanne, die für die Aufkondensation im Anschluß an die Synthese oder während der Ver arbeitung erforderlich ist.The advantage of the method is that it takes a short time the condensation following the synthesis or during the Ver work is required.
Gegenstand der Erfindung sind auch die nach dem genannten Verfahren hergestellten (Co-)Polyamide sowie ihre Verwendung zur Herstellung von Fasern, Folien oder Formkörpern und als Schmelzkleber.The invention also relates to the processes mentioned Manufactured (co) polyamides and their use for the production of Fibers, foils or moldings and as a hot melt adhesive.
Nachstehend soll die Erfindung an mehreren Ausführungsbeispielen näher erläutert werden.The invention is to be explained in more detail below in terms of several exemplary embodiments are explained.
In einem ZSK-30/Werner & Pfleiderer werden zu 4 kg/h PA-6 (MW = 22600) bei 300 U/min in der ersten Stufe 250 mmol/h n-Butanol zuge setzt und anschließend in einer zweiten Stufe der Koppler in einer Menge vonIn a ZSK-30 / Werner & Pfleiderer, PA-6 (MW = 22600) at 300 rpm in the first stage added 250 mmol / h n-butanol sets and then in a second stage the coupler in one a lot of
-a) 90 mmol/h MDI (Diphenylmethan-4ß4′-diisocyanat) in Toluen
-b) 180 mmol/h MDI in Toluen-a) 90 mmol / h MDI (diphenylmethane-4ß4'-diisocyanate) in toluene
-b) 180 mmol / h MDI in toluene
in die Schmelze zudosiert. Die Schmelze wird vor der Düse vakuument gast. Neben dem Drehmomentanstieg wurden folgende Werte für die rela tive Lösungsviskosität ηrel (konz. H2SO4, 25°C, 200 mg/20ml) erhal ten:metered into the melt. The melt is vacuumed in front of the nozzle. In addition to the torque increase, the following values for the relative solution viscosity ηrel (conc. H 2 SO 4 , 25 ° C, 200 mg / 20ml) were obtained:
- PA-6 ohne Kopplerkomponente (mit n-Butanol-Zusatz) ηrel = 2,49
- Versuch a) PA-6 (Gmmol) : Koppler (mmol) = 1 : 0,5 ηrel = 2,96
- Versuch b) PA-6 (Gmmol) : Koppler (mmol) = 1 : 1 ηrel = 3,45
- PA-6 without coupler component (with n-butanol addition) η rel = 2.49
- Experiment a) PA-6 (gmmol): coupler (mmol) = 1: 0.5 η rel = 2.96
- Experiment b) PA-6 (gmmol): coupler (mmol) = 1: 1 η rel = 3.45
In einem ZSK-30/Werner & Pfleiderer werden zu 4 kg/h PA-6 (MW = 22600) bei 300 U/min in der ersten Stufe 250 mmol/h ε-Caprolac tam zugesetzt und anschließend der Koppler in einer Menge vonIn a ZSK-30 / Werner & Pfleiderer, PA-6 (MW = 22600) at 300 rpm in the first stage 250 mmol / h ε-Caprolac tam added and then the coupler in an amount of
-a) 90 mmol/h MDI in Toluen
-b) 180 mmol/h MDI in Toluen-a) 90 mmol / h MDI in toluene
-b) 180 mmol / h MDI in toluene
in die Schmelze zudosiert. Die Schmelze wird vor der Düse vakuument gast. Neben dem Drehmomentanstieg wurden folgende ηrel-Werte (konz. H2SO4; 25°C, 200 mg/ 20 ml) erhalten:metered into the melt. The melt is vacuumed in front of the nozzle. In addition to the increase in torque, the following ηrel values (conc. H 2 SO 4 ; 25 ° C, 200 mg / 20 ml) were obtained:
- PA-6 ohne Kopplerkomponente (mit ε-Caprolactam-Zusatz)
ηrel = 2,55
- Versuch a) PA-6 (Gmmol) : Koppler (mmol) = 1 : 0,5 ηrel = 3 12
- Versuch b) PA-6 (Gmmol) : Koppler (mmol) = 1 : 1 ηrel = 3,83- PA-6 without coupler component (with ε-caprolactam addition) η rel = 2.55
- Experiment a) PA-6 (gmmol): coupler (mmol) = 1: 0.5 η rel = 3 12
- Experiment b) PA-6 (gmmol): coupler (mmol) = 1: 1 η rel = 3.83
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19914136079 DE4136079A1 (en) | 1991-10-30 | 1991-10-30 | Rapid post-condensn. of (co)polyamide(s) for hot melt adhesives - by reactive coupling in the melt with di:isocyanate in the presence of isocyanate capping agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19914136079 DE4136079A1 (en) | 1991-10-30 | 1991-10-30 | Rapid post-condensn. of (co)polyamide(s) for hot melt adhesives - by reactive coupling in the melt with di:isocyanate in the presence of isocyanate capping agent |
Publications (1)
Publication Number | Publication Date |
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DE4136079A1 true DE4136079A1 (en) | 1993-05-06 |
Family
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Family Applications (1)
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DE19914136079 Withdrawn DE4136079A1 (en) | 1991-10-30 | 1991-10-30 | Rapid post-condensn. of (co)polyamide(s) for hot melt adhesives - by reactive coupling in the melt with di:isocyanate in the presence of isocyanate capping agent |
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DE (1) | DE4136079A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3553113A1 (en) | 2018-04-13 | 2019-10-16 | L. Brüggemann GmbH & Co. KG | Method for controlling the molecular structure of polyamides |
-
1991
- 1991-10-30 DE DE19914136079 patent/DE4136079A1/en not_active Withdrawn
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3553113A1 (en) | 2018-04-13 | 2019-10-16 | L. Brüggemann GmbH & Co. KG | Method for controlling the molecular structure of polyamides |
WO2019197679A1 (en) | 2018-04-13 | 2019-10-17 | L. Brüggemann Gmbh & Co. Kg | Method for controlling the molecular structure of polyamides |
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