EP3122829A1 - Nouveau solvant pour polyamide-imides et polyimides - Google Patents

Nouveau solvant pour polyamide-imides et polyimides

Info

Publication number
EP3122829A1
EP3122829A1 EP15711237.6A EP15711237A EP3122829A1 EP 3122829 A1 EP3122829 A1 EP 3122829A1 EP 15711237 A EP15711237 A EP 15711237A EP 3122829 A1 EP3122829 A1 EP 3122829A1
Authority
EP
European Patent Office
Prior art keywords
polyimides
polyamide
methoxy
dimethylpropanamide
imides
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Withdrawn
Application number
EP15711237.6A
Other languages
German (de)
English (en)
Inventor
Giovanna Biondi
Giovanni Loggi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Elantas Italia Srl
Original Assignee
Elantas Italia Srl
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Elantas Italia Srl filed Critical Elantas Italia Srl
Publication of EP3122829A1 publication Critical patent/EP3122829A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1003—Preparatory processes
    • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
    • C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
    • C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
    • 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
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • C08L2203/202—Applications use in electrical or conductive gadgets use in electrical wires or wirecoating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present invention relates to a novel solvent for polyamide-imides and polyimides as well as corresponding applications.
  • Polyamide-imides are known and described for example in US 3,554,984, DE 2,441,020, DE 25 56 523, DE 12 66 427 and DE 19 56 512.
  • Polyimides are also known and described for example in GB 898,651, US 3,207,728, EP 0 274 602, EP 0 274 121.
  • the high quality wire coating agents commonly used today are generally solutions of typical binders, such as polyamide-imides and polyimides in solvents, optionally in combination with commercial hydrocarbon blends.
  • the organic solvents with which polyamide-imides and polyimides are dissolved include amide solvents such as dimethylformamide, N, N-dimethylacetamide and N-methylpyrolidone (NMP). These solvents can be partially replaced by cosolvents.
  • amide solvents such as dimethylformamide, N, N-dimethylacetamide and N-methylpyrolidone (NMP).
  • NMP N-methylpyrolidone
  • NMP To dissolve polyamide-imides or polyimides, especially when they are wholly aromatic, NMP must normally be used.
  • the object of the present invention is therefore to find a new solvent or solvent mixture which is able to dissolve polyamide-irides and / or polyimides very well and no longer has the problems of the prior art solvents, nevertheless results should be achieved which are the same as those of the prior art State of the art equals.
  • compositions in particular wire enamels, and processes for their preparation, which contain polyamideimides and / or polyimides and which can be formulated without solvent as NMP.
  • room temperature means a temperature of 20 ° C. Temperature data are, unless stated otherwise, in degrees Celsius (° C.).
  • Wholly aromatic polyamide-imides or wholly-aromatic polyimides are those in which the individual constituent components all consist of aromatic compounds.
  • both polyamide-imides and polyimides can be excellently dissolved with this solvent.
  • the present invention is therefore the use of 3-methoxy-N, N-dimethyIpropanamid as a solvent for polyamide-imides, for polyimides, for mixtures of polyamide-imides and polyimides, and for compositions containing polyamide-imide, polyimide or mixtures of these resins.
  • the subject of the present invention is the use of 3-methoxy-N, N-dimethylpropanamide as a solvent for wire enamels whose binder component contains polyamide-imides and / or polyimides or from this consists.
  • co-solvent preferably at least 70% by weight of 3-methoxy-N, N-dimethylpropanamide and at most 30% by weight of co-solvent, more preferably at least 80% by weight of 3-methoxy-N, N-dimethylpropanamide and at most 20% by weight of co-cutting agent and more preferably at least 90% by weight of 3-methoxy-N, N-dimethylpropanamide and at most 10% by weight of co-solvent, the percentages in each case based on the total weight of 3-methoxy-N, N- dimethylpropanamide and cosolvents, the compositions being, in particular, wire enamels.
  • Not least object of the present invention is a process for the preparation of compositions, in particular wire enamels, by mixing the components, wherein the binder component polyamideimides and / or polyimides contains or consists of these, wherein as the solvent pure 3-methoxy-N, N-dimethylpropanamide or a mixture comprising at least 60% by weight of 3-methoxy-N, N-dimethylpropanamide and at most 40% by weight of extender, preferably at least 70% by weight of 3-methoxy-N, N-dimethylpropanamide and at most 30% by weight Coupling agents, more preferably at least 80% by weight
  • the present invention is applicable to any polyamide-imides and / or polyimides, since the inventive solvent
  • wholly aromatic polyamide-imides and / or polyimides are used in mixture with non-wholly aromatic polyamide-imides and / or polyimides.
  • Polyamide-imides and polyimides should be referred to by way of example:
  • the preparation of the polyamide-imides can be carried out, for example, in a known manner from polycarboxylic acids or their anhydrides in which two carboxyl groups are in the vicinal position and which must have at least one further functional group and polyamines having at least one primary, capable of imide bond amino group. Instead of the amine group, an isocyanate group can be used to form the imide ring.
  • the polyamide-imides can also be obtained by reacting polyamides, polyisocyanates containing at least two NCO groups, and cyclic dicarboxylic anhydrides containing at least one further condensable or additionable group.
  • the polyamide-imides from diisocyanates or diamines and dicarboxylic acids, if one of the components already contains an imide group.
  • a tricarboxylic anhydride can be reacted with a diprimary diamine to form the corresponding diimidocarboxylic acid which then reacts with a diisocyanate to form the polyamideimide.
  • tricarboxylic acids or their anhydrides in which the carboxyl groups are in the vicinal position.
  • the corresponding aromatic tricarboxylic acid anhydrides e.g. Trimelllthklareanhydrid, Naphthalintricarbonklareanhydride, Biphenyltricarbonklareanhydride and other tricarboxylic acids with two benzene nuclei in the molecule and two vicinal carboxyl groups, such as the examples listed in DE-OS 19 56 512, Very particularly preferably trimellitic anhydride is used.
  • the carboxylic anhydrides are reacted with diisocyanates in a suitable solvent, with elimination of carbon dioxide from the Anhydride imide structures are formed and from the carboxylic acid amide groups.
  • diisocyanates examples include trimethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, propylene diisocyanate, ethylethylene diisocyanate, 3,3,4-trimethylhexamethylene diisocyanate, 1,3-cyclopenthyl diisocyanate, 1,4-cyclohexyl diisocyanate, 1,2-cyclohexyl diisocyanate, 1,3-phenylene diisocyanate.
  • the imide structures can also be prepared by a reaction of the anhydride groups with diamines.
  • diamines As an amine component diprimary diamines can be used which are first reacted with two moles of polycarboxylic acid. These are then built up on the remaining free carboxyl groups with diisocyanates to polyamide-imides.
  • polyamide-imides and polyimides are well-known to the person skilled in the art, further detailed descriptions are unnecessary here. It is preferred in a variant of the present invention if the polyamide-imides and / or polyimides are completely aromatic.
  • co-solvents which may optionally be used in addition to 3-methoxy-N, N-dimethylpropanamide in the context of the present invention preferably consist of pure hydrocarbon compounds or mixtures thereof, i. other atoms besides carbon and hydrogen are present at most as technical impurities.
  • xylene preferably those selected from the group consisting of xylene, Solventnaphtha, toluene, ethylbenzene, cumene, Schwerbenzol, various types of Ci 0 -Ci3-aromatics, for example, the brand Solvesso (R) , various types of hydrocarbons, aromatic-rich Kohlertwasserstoffgemische, for example, the brand DeasoF , and mixtures thereof.
  • those selected from the group consisting of xylene, solvent naphtha, toluene, ethylbenzene, cumene, heavy benzene, C 10 -C 13 -aromatic mixtures, aromatic-rich hydrocarbon mixtures and mixtures thereof are used as diluents in the context of the present invention.
  • mixtures of xylene and solvent naphtha preferably in a ratio of 1: 1, are used as the extender.
  • up to 20% by weight of the cosolvent may be replaced by dimethylacetamide. Accordingly, instead of diluents in variants of the present invention, an extender / dimethylacetamide mixture of the weight ratios of 99: 1 to 80:20 can be used.
  • compositions of the present invention are especially NMP-free, i. the content of NMP is less than 1% by weight, preferably less than 0.5% by weight, in particular below detection limits.
  • compositions according to the invention may contain only polyamide-imides, only polyimides or any mixtures of these two.
  • the compositions according to the invention, in particular wire enamels may contain further constituents which are necessary or desired for the respective fields of use. These may be crosslinking agents, pigments and additives of various kinds, for example wetting agents, dispersing aids, stabilizers, etc.
  • the resulting mixture was allowed to react at 85 ° C for 5 hours. Thereafter, the mixture was cooled down to 50 ° C, and then 20 g of 3-methoxy-N, N-dimethylpropanamide, 50 g of dimethylacetamide and 200 g of aromatic hydrocarbons (1: 1 mixture of xylene and solvent naphtha) were added to the reaction mixture.
  • the resulting mixture was allowed to react for 5 hours at 85 ° C and then for 1 hour at an elevated temperature of 115 ° C.
  • the polyamideimide resin of Example 1 (RA1 1) was coated in a baking oven at temperatures of 500-550 ° C at a speed of 32 m / min on a copper wire of 0.71 mm diameter.
  • the polyamideimide resin of Example 2 (PAI 2) was coated in a baking oven at temperatures of 500-550 ° C. at a speed of 32 m / min on a copper wire having a diameter of 0.71 mm.
  • the layer thickness of the total applied insulation layer was about 65-75 pm.
  • the polyamideimide resin of Example 3 (PAI 3) was coated in a baking oven at temperatures of 500-550 ° C at a speed of 32 m / min on a copper wire of 0.71 mm diameter.
  • the layer thickness of the total applied insulation layer was about 65-75 pm.
  • Example 9 - Contour Wire 4 (KD 4): The polyimide resin of Example 4 (PI 4) was coated in a baking oven at temperatures of 500 - 550 ° C at a speed of 28 m / min on a copper wire with a diameter of 0.71 mm.
  • the layer thickness of the total applied insulation layer was about 60 - 65 ⁇ .
  • the polyimide resin of Example 5 (PI 5) was coated in a baking oven at temperatures of 500-550 ° C at a speed of 28 m / min on a copper wire of 0.71 mm diameter.
  • the layer thickness of the total applied insulating layer was about 60-65 ⁇ .
  • Annealing zone temperature 630 ° C
  • Rotary speed fan 2800 rpm
  • Nozzle sequence 0.75x2, 0.76x2, 0.77x2, 0.78x2, 0.79x2, 0.80x2, 0.81
  • the 3-methoxy-N, N-dimethylpropanamide-containing paints show the same property levels as the NMP-containing paints of the prior art.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Insulating Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation de 3-méthoxy-N,N-diméthylpropanamide comme solvant pour des polyamide-imides et/ou des polyimides, des compositions contenant du 3-méthoxy-N,N-diméthylpropanamide, des polyamide-imides et/ou des polyimides, ainsi que des procédés de préparation de telles compositions en utilisant du 3-méthoxy-N,N-diméthylpropanamide.
EP15711237.6A 2014-03-26 2015-03-24 Nouveau solvant pour polyamide-imides et polyimides Withdrawn EP3122829A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014104223.9A DE102014104223A1 (de) 2014-03-26 2014-03-26 Neues Lösemittel für Polyamidimide und Polyimide
PCT/EP2015/056191 WO2015144663A1 (fr) 2014-03-26 2015-03-24 Nouveau solvant pour polyamide-imides et polyimides

Publications (1)

Publication Number Publication Date
EP3122829A1 true EP3122829A1 (fr) 2017-02-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP15711237.6A Withdrawn EP3122829A1 (fr) 2014-03-26 2015-03-24 Nouveau solvant pour polyamide-imides et polyimides

Country Status (7)

Country Link
EP (1) EP3122829A1 (fr)
JP (1) JP2017517582A (fr)
KR (1) KR20160137986A (fr)
CN (1) CN106062107A (fr)
DE (1) DE102014104223A1 (fr)
TW (1) TW201540747A (fr)
WO (1) WO2015144663A1 (fr)

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EP3973018A1 (fr) * 2019-05-22 2022-03-30 AdvanSix Resins & Chemicals LLC Compositions polymères pour former un revêtement d'émail sur un fil
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JP7071669B2 (ja) 2020-07-09 2022-05-19 ダイキン工業株式会社 塗料組成物、塗膜及び塗装物品
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JP7593539B2 (ja) * 2020-09-14 2024-12-03 東特塗料株式会社 電気絶縁塗料及び電気絶縁被覆電線に有用なポリアミドイミド樹脂溶液の製法
EP4217413A1 (fr) 2020-09-22 2023-08-02 Elantas Europe Srl Composition d'émail pour fil métallique comprenant un polyamide-imide
EP4105261A1 (fr) 2021-06-14 2022-12-21 Evonik Fibres GmbH Nouvelles solutions de polyimide non toxiques
CN117280429A (zh) * 2021-08-24 2023-12-22 住友电气工业株式会社 绝缘电线
WO2023171679A1 (fr) 2022-03-08 2023-09-14 Ｋｊケミカルズ株式会社 Composition contenant un composé amide hautement sûr
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TW201540747A (zh) 2015-11-01
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DE102014104223A1 (de) 2015-10-01
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