EP1590390A1 - Procede pour preparer des resines de polyamidimide stables au stockage, et agents de revetement qui les contiennent - Google Patents

Procede pour preparer des resines de polyamidimide stables au stockage, et agents de revetement qui les contiennent

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Publication number
EP1590390A1
EP1590390A1 EP04703101A EP04703101A EP1590390A1 EP 1590390 A1 EP1590390 A1 EP 1590390A1 EP 04703101 A EP04703101 A EP 04703101A EP 04703101 A EP04703101 A EP 04703101A EP 1590390 A1 EP1590390 A1 EP 1590390A1
Authority
EP
European Patent Office
Prior art keywords
group
carbon atoms
din
straight
chain
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Withdrawn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
EP04703101A
Other languages
German (de)
English (en)
Inventor
Guenter Stevens
Heinz Herlinger
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.)
Altana Electrical Insulation GmbH
Original Assignee
Altana Electrical Insulation GmbH
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 Altana Electrical Insulation GmbH filed Critical Altana Electrical Insulation GmbH
Publication of EP1590390A1 publication Critical patent/EP1590390A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/343—Polycarboxylic acids having at least three carboxylic acid groups
    • C08G18/345—Polycarboxylic acids having at least three carboxylic acid groups having three carboxylic acid groups
    • 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
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings

Definitions

  • the present invention relates to a process for the preparation of storage-stable polyamideimide resins and polyamideimide coating compositions which have increased stability both during storage and during application, in particular with respect to water and moisture.
  • Polyamide imides have already been described frequently in the literature as resin components in wire enamels. Examples of this are the polyamideimides described in DE 2 203 153, EP 0 315 925 or DE 1 720 356.
  • DE 2 203 153 Another possibility for improving the storage stability was mentioned in DE 2 203 153 and consists in the use of mixtures of aromatic diamines such as e.g. 2,4'- and 4,4'-diaminodiphenyl oxide (Example 1 in DE 2 203 153), or of mixtures of 4,4'-diamino-diphenyl-methane with 4,4'-diamino-3,3'-dimethyl - diphenyl methane. Mixtures of the isocyanate components such as 4,4'-diisocyanatodiphenylmethane together with technical tolylene diisocyanate were also used (example 6 of DE 2 203 153).
  • aromatic diamines such as e.g. 2,4'- and 4,4'-diaminodiphenyl oxide
  • 4,4'-diamino-diphenyl-methane 4,4'-diamino-3,3'-dimethyl - di
  • polyamideimides can be adjusted by adding monocarboxylic acids such as formic acid, acetic acid or aromatic acids such as benzoic acid, which should preferably react with the active centers of the polyamideimides.
  • All of the above polyamideimide coating compositions and resins are unstable under storage and use conditions, especially in the presence of relatively high humidity and temperature.
  • the aim of the present invention was therefore to convert as far as possible all reactive centers of the polyamideimides into groups which prevent crosslinking of the linear polymer in the presence of water or moist air.
  • suitable reactive centers in polyamideimides are suitable.
  • the prevention of crosslinking is all the more important since even a few crosslinkings of the monomer units of the polymer can bring about a strong increase in the viscosity of the polymer solution.
  • the object of the present invention was therefore to provide an economical process for the preparation of storage-stable polyamideimide resins and coating compositions which does not have the disadvantages mentioned above.
  • This object was achieved by providing a process for the preparation of storage-stable polyamideimide resins, characterized in that the centers of the polyamideimide resin which are reactive towards moisture are reacted with one or more compounds of the following general formula (I)
  • R is a straight-chain or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aralkyl group or an aryl group and
  • R 2 represents a straight-chain or branched alkyl group having 1 to 6 carbon atoms, an aralkyl group or an aryl group or
  • Catalyst selected from the group consisting of "organometallic catalysts and tertiary amines" and is carried out at temperatures above 50 ° C.
  • R 2 and R 1 form a cycloalkyl radical having 4 to 5 carbon atoms
  • one of the methylene groups of the cycloalkyl radical being replaced by oxygen or an NR 3 group can be replaced and wherein R 3 represents a straight-chain or branched alkyl group having 1 to 3 carbon atoms.
  • morpholine, piperidine and N-methylpiperazine are preferred.
  • the process according to the invention is preferably carried out in the presence of at least one catalyst from the group of the organometallic compounds and / or the tertiary amines.
  • Organometallic catalysts based on tin, zinc, bismuth or cobalt are particularly suitable, dibutyltin dilaurate in particular having good catalytic properties.
  • Amines can be used as catalysts both those which are completely inert when using the process according to the invention, and also those which, in addition to their catalytic action, can be incorporated into the coating compositions.
  • the latter also include butyraldehyde-aniline condensation products such as Vulkazit ® 576 (Bayer AG, Leverkusen).
  • a process for the production of storage-stable polyamideimide coating compositions which makes use of the process according to the invention for the production of storage-stable polyamideimide resins in that additional coating composition components are added before, during or after the production of the storage-stable polyamideimide resins, and the other coating composition components are not present participate in the implementation.
  • the process according to the invention can thus be carried out in such a way that the reaction to be carried out in the production of the storage-stable coating agent between the moisture-reactive centers of the polyamideimide and the compounds of the general formula (I) is first carried out in the absence of further coating agent components only with the polyamideimide and the admixture further coating agent components are made later. However, it is also possible to carry out this reaction in the presence of further coating agent components which do not interfere with the reaction.
  • H ⁇ R 1 implemented so the catalyzed reaction takes place at elevated temperatures, as the comparison between the paint 12 of the invention with comparative paint 2 shows.
  • the invention further relates to the storage-stable coating compositions obtainable by the process according to the invention.
  • trimellitic anhydride 223.12 g of trimellitic anhydride are dissolved in 547.52 g of N-methylpyrrolidone while heating to 70 to 75 ° C., so that a clear solution is obtained.
  • the mixture is then cooled to 40 ° C. and 6.07 g of 100% formic acid are mixed in. 293.52 g of 4,4'-diisocyanatodiphenylmethane (MDI) are slowly added and thereby dissolved. It is important to ensure that the temperature does not exceed 45 ° C. 33.09 g of N-methylpyrrolidone are then added.
  • the mixture is then stirred at 40 to 45 ° C for 1 hour and heated to 85 ° C within 2 hours.
  • the temperature is slowly increased further to a maximum of 145 ° C.
  • the viscosity is determined several times until the desired resin viscosity is reached.
  • the viscosity is determined using an outlet viscometer (DIN cup 4 mm) according to DIN 53211 and is approx. 110 s at a concentration of 90 g resin per 60 N-methylpyrrolidone at 20 ° C.
  • the NCO content is checked using conventional methods.
  • the reaction is stopped. 1000 g of a polyamideimide resin solution are obtained.
  • the preparation of the polyamide-imide resin 2 corresponds to that of the polyamide-imide resin 1 except that in place of 293.52 g of 4,4'-diisocyanatodiphenylmethane 293.52 g Suprasec ® 1004, an isomer mixture of 2,4'- and 4, 4'-Diisocyanatodiphenylmethane in a concentration ratio of approx. 1: 3 from Huntsmann International LLC. , are used.
  • 705.43 g of the polyamideimide resin used in coating 1 were mixed at a temperature of 125 ° C with 35.0 g of morpholine and 2.5 g Vulkazit 576 ® and stirred for 1h. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26.5 g of dimethylacetamide.
  • 705.43 g of the polyamideimide resin used in lacquer 1 are mixed with 49.2 g of morpholine and 2.5 g of vulcanized 576 ® at a temperature of 125 ° C. and stirred for 1 hour. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26.5 g of dimethylacetamide.
  • 705.43 g of the polyamideimide resin used in lacquer 1 are mixed at a temperature of 125 ° C. with 20.9 g of isobutanol and 2.5 g of vulcanized 576 ® and stirred for 1 hour. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26.5 g of dimethylacetamide.
  • 705.43 g of the polyamideimide resin used in lacquer 1 are mixed at a temperature of 125 ° C. with 28.3 g of N-methylpiperaine and 2.5 g of vulcanized 576 ® and stirred for 1 hour. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26.5 g of dimethylacetamide.
  • Paint data solids content (lg / 1 h / 180 ° C) of 35.7% viscosity of 2330 mPa.s at 23 ° C
  • Paint data solids content (1 g / 1 h / 180 ° C) of 34.7% viscosity of 2250 mPa.s at 23 ° C
  • 705.43 g of the polyamideimide resin used in lacquer 1 are mixed with 28.3 g of cyclohexanol and 2.5 g of vulcanized 576 ® at a temperature of 125 ° C. and stirred for 1 hour. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26.5 g of dimethylacetamide.
  • 705.43 g of the polyamideimide resin used in lacquer 1 are mixed with 33.9 g of methyl diglycol and 2.5 g of vulcanized 576 ® at a temperature of 125 ° C. and stirred for 1 hour. The mixture is then diluted with 179.38 g of xylene, 55.69 g of N-methylpyrrolidone and 26 5 g of dimethylacetamide.
  • 70.17.43 g of the polyamideimide resin from Example 1 are mixed with 34.17 g of N-methylbenzylamine and 5 g of dibutyltin dilaurate at a temperature of 125 ° C. and 1 hour touched.
  • the mixture is then diluted with 205.38 g of xylene, 110.69 g of N-methylpyrrolidone and 30.5 g of dimethylacetamide.
  • Paint data solids content (1 g / 1 h / 180 ° C) of 35.3% viscosity of 2300 mPa.s at 23 ° C
  • the method for checking the residual activity of the polyamideimide coating compositions according to the invention and the polyamideimide lacquers represents a further aspect of the present invention.
  • the method described below makes it possible for the first time to reliably determine the storage stability by bypassing a lengthy test which takes several weeks ,
  • the process is not restricted to certain primary diamines or organic solvents, nor to certain reaction temperatures.
  • the reaction itself can take place at room temperature, but is accelerated by increasing the temperature.
  • a system-specific window can be set by simply varying parameters such as temperature, solvent or diamine, which provides results within a few minutes that correlate well with the results that were previously only available after several weeks of storage using conventional methods.
  • the examination method according to the invention is explained by way of example on the basis of the investigation of the storage stability of the polyamideimide coating compositions according to the invention.
  • the system used consists of the Haake VT 550 viscometer and the PK 5/1 ° cone plate measuring system. As a comparison, the times are measured which lead to a viscosity of 60 Pa.s due to the reaction between the remaining reactive centers of the respective polyamideimides.
  • Table 1 shows an overview of the differences between paints 1 to 13 and comparative paints 1 and 2, where “+” means that the respective component is contained in the polyamideimide resin or the paint.
  • Table 2 shows the properties of the polyamideimide resin solutions and the paints applied.
  • the reduced residual reactivity can be seen for all paints according to the invention, in particular for paints 4 and 5.
  • the lacquers 1 to 5 and the comparative lacquers 1 and 2 were applied by means of the usual wire lacquer coating method as an overcoat with a THEIC-modified polyester imide as the base lacquer on 0.8 mm copper wire.
  • the base coat was applied in six passes and the overcoat in four passes.
  • the application data of the paints and comparative paints are shown in Table 3.

Landscapes

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

Abstract

La présente invention concerne un procédé pour préparer des résines de polyamidimide, les centres des résines de polyamidimide, réactifs à l'humidité, étant convertis avec un ou plusieurs composés de formule générale H-X-R<1>, dans laquelle: dans le cas où X = oxygène, R<1> est un groupe alkyle à chaîne linéaire ou ramifié comprenant de 1 à 6 atomes de carbone, un groupe cycloalkyle comprenant de 3 à 6 atomes de carbone ou un groupe aralkyle, et dans le cas où X = NR<2>, R<1> est un groupe alkyle à chaîne linéaire ou ramifié comprenant de 1 à 6 atomes de carbone, un groupe cycloalkyle comprenant de 3 à 6 atomes de carbone ou un groupe aralkyle ou un groupe aryle, et R<2> est un groupe alkyle à chaîne linéaire ou ramifié comprenant de 1 à 6 atomes de carbone, un groupe aralkyle ou un groupe aryle, ou bien R<1> et R<2> forment ensemble un radical cycloalkyle comprenant 4 ou 5 groupes méthylène, un groupe méthylène pouvant être remplacé par de l'oxygène ou un groupe NR<3> dans lequel R<3> est un groupe alkyle à chaîne linéaire ou ramifié comprenant 1 à 3 atomes de carbone. L'invention a également pour objet des agents de revêtement polyamidimide qui sont produits grâce au procédé de l'invention.
EP04703101A 2003-01-30 2004-01-17 Procede pour preparer des resines de polyamidimide stables au stockage, et agents de revetement qui les contiennent Withdrawn EP1590390A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10303635A DE10303635A1 (de) 2003-01-30 2003-01-30 Verfahren zur Herstellung lagerstabiler Polyamidimid-Harze und Überzugsmittel, die diese enthalten
DE10303635 2003-01-30
PCT/EP2004/000333 WO2004067596A1 (fr) 2003-01-30 2004-01-17 Procede pour preparer des resines de polyamidimide stables au stockage, et agents de revetement qui les contiennent

Publications (1)

Publication Number Publication Date
EP1590390A1 true EP1590390A1 (fr) 2005-11-02

Family

ID=32797288

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04703101A Withdrawn EP1590390A1 (fr) 2003-01-30 2004-01-17 Procede pour preparer des resines de polyamidimide stables au stockage, et agents de revetement qui les contiennent

Country Status (4)

Country Link
US (1) US7820768B2 (fr)
EP (1) EP1590390A1 (fr)
DE (1) DE10303635A1 (fr)
WO (1) WO2004067596A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111925722A (zh) * 2020-07-31 2020-11-13 湖北琼霸防水科技有限公司 一种耐磨防水涂料及其制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130027963A1 (en) 2010-04-16 2013-01-31 Maarten Marinus Johannes Wilhelmus Van Herpen Textile product having a lighting function and method for the production thereof
CN102190955A (zh) * 2011-04-06 2011-09-21 丹阳四达化工有限公司 一种混合溶剂制备聚酰胺酰亚胺漆包线漆的方法

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US3803100A (en) * 1966-12-29 1974-04-09 Sumitomo Electric Industries Method for preparing soluble polyamideimides
AT270224B (de) 1967-03-20 1969-04-25 Beck & Co Ag Dr Verfahren zur Herstellung von neuen thermostabilen, linearen Polyamidimiden
AT311516B (de) 1971-03-02 1973-11-26 Beck & Co Ag Dr Verfahren zur Herstellung stabile Lacklösungen ergebender linearer Polyamidimide
FR2222402B1 (fr) * 1973-03-19 1976-06-11 Rhone Poulenc Ind
US3884880A (en) * 1973-09-21 1975-05-20 Phelps Dodge Magnet Wire Corp Modified amide-imide resins and method of making the same
JPS5313222B2 (fr) 1973-12-14 1978-05-09
JPS511595A (en) 1974-06-19 1976-01-08 Showa Electric Wire & Cable Co Denkizetsuentoryono seizohoho
JPS606366B2 (ja) * 1978-12-11 1985-02-18 日立化成工業株式会社 ポリアミドイミド樹脂および水溶性ポリアミドイミド樹脂の製造法
DE3249544C2 (de) * 1981-11-06 1985-07-11 Hitachi Chemical Co., Ltd., Tokio/Tokyo Isolierter Draht
US4374221A (en) * 1981-11-17 1983-02-15 Essex Group, Inc. High solids polyamide-imide magnet wire enamel
FR2622892B1 (fr) 1987-11-10 1995-01-13 Alsthom Vernis a base de polyamide-imide modifie,son procede de fabrication,et conducteur electrique isole a l'aide d'un tel vernis
JPH08291252A (ja) * 1995-04-21 1996-11-05 Hitachi Ltd ポリイミド前駆体ワニス及びそれを用いた電子装置
DE10041943A1 (de) 2000-08-25 2002-03-14 Schenectady Int Inc Polyamidimidharzlösung und ihre Verwendung zur Herstellung von Drahtlacken
US7569634B2 (en) * 2002-02-14 2009-08-04 The Glidden Company Curable adhesive composition, adhesive kit and method of adhering substrates

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See references of WO2004067596A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111925722A (zh) * 2020-07-31 2020-11-13 湖北琼霸防水科技有限公司 一种耐磨防水涂料及其制备方法

Also Published As

Publication number Publication date
DE10303635A1 (de) 2004-12-02
US20060025543A1 (en) 2006-02-02
WO2004067596A1 (fr) 2004-08-12
US7820768B2 (en) 2010-10-26

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