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WO2009099039A1 - Solution stabilisée de résine polyamideimide et son procédé de fabrication - Google Patents

Solution stabilisée de résine polyamideimide et son procédé de fabrication Download PDF

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Publication number
WO2009099039A1
WO2009099039A1 PCT/JP2009/051738 JP2009051738W WO2009099039A1 WO 2009099039 A1 WO2009099039 A1 WO 2009099039A1 JP 2009051738 W JP2009051738 W JP 2009051738W WO 2009099039 A1 WO2009099039 A1 WO 2009099039A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyamideimide resin
resin solution
glycidyl ether
acid
polyamideimide
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.)
Ceased
Application number
PCT/JP2009/051738
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English (en)
Japanese (ja)
Inventor
Cyuji Inukai
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.)
Toyobo Co Ltd
Original Assignee
Toyobo Co Ltd
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 Toyobo Co Ltd filed Critical Toyobo Co Ltd
Publication of WO2009099039A1 publication Critical patent/WO2009099039A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G73/14—Polyamide-imides
    • 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
    • C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
    • 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

Definitions

  • the present invention relates to a stabilized polyamideimide resin solution, and more particularly to a polyamideimide resin solution having improved storage stability at high temperatures.
  • Polyamideimide resins are usually polymerized in amide solvents such as N-methyl-2-pyrrolidone, N, N′-dimethylacetamide, N, N′-dimethylformamide and aprotic polar solvents such as ⁇ -butyrolactone.
  • amide solvents such as N-methyl-2-pyrrolidone, N, N′-dimethylacetamide, N, N′-dimethylformamide and aprotic polar solvents such as ⁇ -butyrolactone.
  • N, N′-dimethylacetamide has a lower boiling point than N-methyl-2-pyrrolidone and ⁇ -butyrolactone, it has advantages in that it is excellent in drying property when processing a polyamideimide resin solution and is inexpensive.
  • N, N′-dimethylacetamide when used as the polymerization solvent, there is a problem that the molecular weight tends to decrease during storage, Improvement of the storage stability of a polyamideimide solution polymerized with N, N′-dimethylacetamide has been desired.
  • the inventor of the present invention usually contains several tens of ppm to several hundreds of ppm of water in the solvent.
  • the solvent when added to the reaction vessel, some water may be mixed from the atmosphere.
  • the present inventors have found that moisture introduces an excessive amount of carboxyl groups into the polyamide-imide resin and lowers the molecular weight during storage, and as a result, the storage stability of the polyamide-imide resin solution decreases, leading to the present invention.
  • the present invention is as follows.
  • the present invention relates to an improvement in the storage stability of a polyamideimide resin solution.
  • the present invention is characterized in that a glycidyl ether compound is blended and reacted with a polyamideimide resin solution polymerized in N, N′-dimethylacetamide.
  • a polyamide-imide resin solution useful for an agent, a coating agent, and a film application is provided.
  • the present invention relates to a polyamideimide resin solution having improved storage stability.
  • it relates to improving the storage stability at high temperatures of polyamideimide resin solutions polymerized in N, N′-dimethylacetamide and having a high acid value.
  • the polyamide-imide resin used in the present invention is not particularly limited, and includes those synthesized from either a normal isocyanate method or an acid chloride method.
  • Trimellitic acid and its anhydrides and chlorides are mainly used as the acid component used in the production of polyamideimide resin.
  • pyromellitic acid, biphenyltetracarboxylic acid, biphenylsulfonetetracarboxylic acid, benzophenone Tetracarboxylic acids such as tetracarboxylic acid, biphenyl ether tetracarboxylic acid, ethene glycol bis trimellitate and propylene glycol bis trimellitate and their anhydrides, oxalic acid, adipic acid, malonic acid, sebacic acid, azelaic acid, dodecanedicarboxylic acid Acids, 1,4-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 4,4'-dicyclohexylmethanedicarboxylic acid, aliphatic dicarboxylic acids such as dimer acid, terephthalic
  • diamines (diisocyanates) used in the production of polyamideimide resins include aliphatic diamines such as ethylenediamine, propylenediamine, and hexamethylenediamine, and their diisocyanates, isophorone diamine, 1,4-cyclohexanediamine, 1,3-cyclohexanediamine, 4 , 4'dicyclohexylmethanediamine and the like, and diisocyanates thereof, m-phenylenediamine, p-phenylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'- Aromatic diamines such as diaminodiphenylsulfone, benzidine, o-tolidine, 2,4-tolylenediamine, 2,6-tolylenediamine, xylylenediamine, naphthalenediamine and their diiso Aneto and
  • Polyamideimide resin can copolymerize a diol component in addition to the acid component and amine (diisocyanate) component.
  • diol component include ethylene glycol, propylene glycol, tetremethylene glycol, butanediol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyester diol, and carbonate diol.
  • the polyamideimide resin solution of the present invention includes aprotic polar solvents such as N, N′-dimethylformamide, N, N′-dimethylacetamide, N-methyl-2-pyrrolidone and ⁇ -butyrolactone, isophorone, cyclohexanone, cyclopentanone, etc. It can be produced by stirring while heating at 60 ° C. to 200 ° C. in one or more solvents of aromatic hydrocarbons such as ketones and xylene.
  • aprotic polar solvents such as N, N′-dimethylformamide, N, N′-dimethylacetamide, N-methyl-2-pyrrolidone and ⁇ -butyrolactone, isophorone, cyclohexanone, cyclopentanone, etc. It can be produced by stirring while heating at 60 ° C. to 200 ° C. in one or more solvents of aromatic hydrocarbons such as ketones and xylene.
  • alkali metals such as sodium fluoride, potassium fluoride, sodium methoxide, amines such as triethylamine, diethanolamine, diazabicycloundecene, and catalysts such as dibutyltin dilaurate should be used. Can do.
  • the polyamideimide resin solution of the present invention is usually about 10 to 40% by weight of the polyamideimide resin with respect to the resin solution, but there is no particular limitation.
  • the polyamideimide resin solution produced in this way has a high moisture content in the solvent before polymerization, and particularly when N, N'-dimethylacetamide is used as the solvent, a polyamideimide resin having a high acid value is produced.
  • the storage stability of the polyamideimide resin solution is impaired. In particular, when the solvent contains 10% by weight or more of N, N′-dimethylacetamide, the storage stability of the polyamideimide resin solution tends to be impaired.
  • the storage stability decreases because in the case of the isocyanate method, a part of the acid anhydride is ring-opened by water in the solvent to form an amic acid, and the carboxyl derived from the amic acid It is presumed that the group promotes the decomposition of the adjacent amide bond. Further, in the case of the acid chloride method, it is presumed that molecular weight reduction occurs for the same reason when imidization of the amic acid is insufficient. Therefore, although the subject of the present invention depends on the molecular weight, it is particularly effective for a polyamideimide resin having an acid value of 150 eq / 10 6 g or more. Is also effective. In this case, the logarithmic viscosity is 0.2 dl / g or more.
  • the present invention is to improve storage stability by blending one or more glycidyl ethers with the polyamideimide resin solution having a high acid value.
  • glycidyl ether triethylamine, carbodiimide, and the like can be used, but glycidyl ether is most preferable because triethylamine has little stabilizing effect and carbodiimide has problems such as thickening and is difficult to use.
  • Examples of the glycidyl ether compound used in the present invention include ethyl glycidyl ether, butyl glycidyl ether, hexyl glycidyl ether, octyl glycidyl ether, aliphatic monoglycidyl ethers such as higher alcohol glycidyl ether, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether , Aliphatic diglycidyl ethers such as hexanediol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polyfunctional glycidyl ether such as glycerin triglycidyl ether, trimethylolpropane triglycidyl ether, phenyl glycidyl ether, etc.
  • Aromatic glycidyl ethers Butyl glycidyl ether and phenyl glycidyl ether monofunctional low boiling point is preferred. In the case of using a bifunctional or higher functional glycidyl ether compound, it is necessary to react under careful conditions so as not to gel. Since a bifunctional or higher functional glycidyl ether compound may be gelled, it is desirable to use a monofunctional glycidyl ether compound.
  • the addition amount of the glycidyl ether is preferably 0.5 to 20 times equivalent to the acid value of the polyamideimide resin, more preferably 1 to 15 times equivalent, still more preferably 3 to 10 times equivalent, most preferably 3 to 5 equivalents. If it is less than 0.5 times equivalent, the effect of the storage stability of the polyamideimide resin solution tends to be small. Moreover, even if it adds excessively, the effect beyond it will not be acquired, and various physical properties of subsequent polyamideimide resin, for example, film
  • the addition of the glycidyl ether compound is carried out in the latter half or after completion of the production of the polyamideimide resin solution, and the mixture is heated and stirred at room temperature or higher, preferably 50 ° C. or higher, more preferably 80 ° C. or higher, and most preferably 100 ° C. or higher. If it is less than 50 ° C., the reaction may not proceed easily.
  • the glycidyl ether compound reacts with the terminal of the polyamideimide, a carboxyl group present in the molecular chain.
  • the acid value of the polyamideimide resin after the reaction with the glycidyl ether compound is preferably 330 eq / 10 6 g or less, more preferably 250 eq / 10 6 g or less, and even more preferably 200 eq / 10 6 g or less.
  • carboxyl group which exists in the molecular chain of polyamideimide exists, there exists a tendency for solution stability to fall especially.
  • the polyamideimide resin solution with improved storage stability of the present invention can be used as a film, paint, ink, coating agent, adhesive or other vehicle, or as a processing agent for fibers, film, paper, etc. It is useful for coating agents and adhesives such as plastic films that need to be dried at low temperatures.
  • the polyamideimide resin solution of the present invention can be used as it is, a higher degree of water resistance, adhesion and heat resistance can be imparted by blending a crosslinking agent.
  • the crosslinking agent include phenol-formaldehyde resin, amino resin, polyfunctional epoxy resin, melamine-formaldehyde resin, polyfunctional isocyanate compound and the like.
  • a flame retardant, a pigment, dye, an antifoamer, an antistatic agent, a leveling agent, etc. can be mix
  • the measured values in the examples are values measured by the following method.
  • the solution viscosity, logarithmic viscosity, and acid value of the polyamideimide resin solution immediately after production produced in each Example and Comparative Example and the polyamideimide resin solution stored in the resin solution state at 40 ° C. for 1 month were examined.
  • the polyamideimide resin solution was stored in a sealed state in a metal can. Comparing the solution viscosity immediately after production and the solution viscosity after storage at 40 ° C.
  • a solution obtained by dissolving 0.5 g of a dry polymer in 100 ml of NMP was measured at 30 ° C. using an Ubbelohde viscosity tube.
  • the acid-polymerized polyamideimide resin solution was poured into water, re-precipitated, washed with water three times or more, and then dried at 60 ° C for 10 hours or more.
  • 0.125 g of the dried polymer was dissolved in 50 ml of N, N′-dimethylformamide and titrated with 1/50 N sodium methoxide in methanol using phenolphthalein as an indicator.
  • -Film strength and elastic modulus A film having a thickness of about 30 ⁇ m produced by applying and drying a resin solution was measured using a Tensilon made by Toyo Baldwin at room temperature at a pulling speed of 50 mm / min.
  • Example 1 In a flask equipped with a condenser, nitrogen inlet tube, and stirrer, trimellitic anhydride (TMA) 1 mol, diphenylmethane-4,4′-diisocyanate (MDI) 1.03 mol, potassium fluoride (KF) 0.01 Mole was dissolved in N, N′-dimethylacetamide (DMAc) so as to have a solid concentration of 30% by weight, and reacted at 100 ° C. for 1 hour and at 150 ° C. for 3 hours.
  • TMA trimellitic anhydride
  • MDI diphenylmethane-4,4′-diisocyanate
  • KF potassium fluoride
  • phenyl glycidyl ether is 300 equivalents, 600 equivalents, 900 equivalents per 10 6 g of polyamideimide resin solids, 1500 equivalents were added and heated and stirred at 100 ° C. for 2 hours.
  • Example 5 Using the same apparatus as described above, TMA 0.67 mol, dimer acid 0.2 mol, dicarboxyacrylonitrile-butadiene 0.03 mol, and MDI 1.02 mol were charged together with DMAc so that the solid concentration was 50% by weight. After reacting at 130 ° C. for 5 hours, after cooling to 100 ° C., it was diluted with xylene so that the solid content concentration was 30% by weight, and n-butyl glycidyl ether was 350 etc. per 10 6 g of polyamideimide resin solid content. An amount of 1650 equivalents was added and the mixture was heated and stirred at 100 ° C. for 2 hours.
  • Example 7 Using the same apparatus as described above, DMAc was added to 1 mol of TMA, 0.8 mol of o-tolidine diisocyanate, 0.2 mol of tolylene diisocyanate and 0.01 mol of diazabicycloundecene so that the solid content concentration was 20% by weight. The mixture was charged and reacted at 100 ° C. for 5 hours. Subsequently, 300 equivalents of phenyl glycidyl ether per 10 6 g of the solid resin was added at the same temperature and stirred for 2 hours.
  • Example 4 (Comparative Example 4) In Example 1, a polyamide-imide resin solution was obtained under the same conditions except that 130 equivalents of phenyl glycidyl ether was added per 10 6 g of the solid polyimide resin solid content.
  • Example 5 A polyamideimide resin solution was obtained under the same conditions as in Example 1 except that 7450 equivalents of phenylglycidyl ether per 10 6 g of the solid polyimide resin solid content was added. Although the solution viscosity after storage at 40 ° C. for 1 month did not decrease, the strength of the film was 76 MPa with respect to 110 MPa in Example 1, and the elastic modulus was greatly decreased to 1.5 GPa with respect to 2.8 GPa in Example 1. did.
  • the present invention relates to an improvement in the storage stability of a polyamideimide resin solution, and in particular, a polyamideimide resin solution polymerized in N, N′-dimethylacetamide is mixed with a glycidyl ether compound and reacted, and thus a paint, an adhesive
  • a polyamide-imide resin solution useful for an agent, a coating agent and a film application is provided.

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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)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une solution de résine polyamideimide qui présente une stabilité au stockage améliorée. L'invention concerne spécifiquement une solution de résine polyamideimide qui est fabriquée par ajout d'un composé d'éther glycidylique à une solution de résine polyamideimide qui a été polymérisée en N,N'-diméthylacétamide et mise en réaction du mélange. La solution selon l'invention est utile pour une peinture, un agent adhésif, une solution de revêtement ou un film. La stabilité au stockage d'une solution de résine polyamideimide peut être améliorée en ajoutant de préférence un composé d'éther glycidylique monofonctionnel à la solution de résine polyamideimide, de préférence en une quantité de 0,5 à 20 équivalents par rapport à l'indice d'acidité de la résine polyamideimide et en faisant réagir le mélange.
PCT/JP2009/051738 2008-02-07 2009-02-03 Solution stabilisée de résine polyamideimide et son procédé de fabrication Ceased WO2009099039A1 (fr)

Applications Claiming Priority (2)

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JP2008-027198 2008-02-07
JP2008027198 2008-02-07

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WO2009099039A1 true WO2009099039A1 (fr) 2009-08-13

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018032627A (ja) * 2016-08-22 2018-03-01 ユニチカ株式会社 蓄電素子電極用ポリアミドイミド溶液、蓄電素子電極の製造方法および蓄電素子電極
JP2020050875A (ja) * 2018-09-25 2020-04-02 ユニチカ株式会社 ポリアミドイミド溶液の製造方法および増粘ポリアミドイミド
JP2022079518A (ja) * 2017-08-01 2022-05-26 昭和電工マテリアルズ株式会社 不織布製造用ポリアミドイミド樹脂組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4923837B1 (fr) * 1970-07-09 1974-06-18
JPH09194566A (ja) * 1996-01-16 1997-07-29 Hitachi Chem Co Ltd 変性エポキシ樹脂の製造方法、その製造方法により得られる変性エポキシ樹脂を用いた接着剤及び接着剤フィルム
JP2001240670A (ja) * 2000-03-01 2001-09-04 Arakawa Chem Ind Co Ltd シラン変性ポリアミドイミド樹脂、その樹脂組成物及びその製造方法。
WO2002097532A1 (fr) * 2001-05-30 2002-12-05 Kaneka Corporation Composition de resine photosensible et reserve sous forme de film sec photosensible, film de protection photosensible comprenant cette derniere
JP2004281066A (ja) * 2003-03-12 2004-10-07 Toyota Motor Corp プロトン伝導性材料、プロトン伝導性材料膜、及び燃料電池
JP2006342335A (ja) * 2005-05-11 2006-12-21 Hitachi Chem Co Ltd ポリアミドイミドおよび樹脂組成物

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4923837B1 (fr) * 1970-07-09 1974-06-18
JPH09194566A (ja) * 1996-01-16 1997-07-29 Hitachi Chem Co Ltd 変性エポキシ樹脂の製造方法、その製造方法により得られる変性エポキシ樹脂を用いた接着剤及び接着剤フィルム
JP2001240670A (ja) * 2000-03-01 2001-09-04 Arakawa Chem Ind Co Ltd シラン変性ポリアミドイミド樹脂、その樹脂組成物及びその製造方法。
WO2002097532A1 (fr) * 2001-05-30 2002-12-05 Kaneka Corporation Composition de resine photosensible et reserve sous forme de film sec photosensible, film de protection photosensible comprenant cette derniere
JP2004281066A (ja) * 2003-03-12 2004-10-07 Toyota Motor Corp プロトン伝導性材料、プロトン伝導性材料膜、及び燃料電池
JP2006342335A (ja) * 2005-05-11 2006-12-21 Hitachi Chem Co Ltd ポリアミドイミドおよび樹脂組成物

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018032627A (ja) * 2016-08-22 2018-03-01 ユニチカ株式会社 蓄電素子電極用ポリアミドイミド溶液、蓄電素子電極の製造方法および蓄電素子電極
JP2022079518A (ja) * 2017-08-01 2022-05-26 昭和電工マテリアルズ株式会社 不織布製造用ポリアミドイミド樹脂組成物
JP7363945B2 (ja) 2017-08-01 2023-10-18 株式会社レゾナック 不織布製造用ポリアミドイミド樹脂組成物
JP2023174742A (ja) * 2017-08-01 2023-12-08 株式会社レゾナック 不織布形成材料及びその使用
JP7509512B2 (ja) 2017-08-01 2024-07-02 株式会社レゾナック 不織布製造用ポリアミドイミド樹脂組成物
JP2020050875A (ja) * 2018-09-25 2020-04-02 ユニチカ株式会社 ポリアミドイミド溶液の製造方法および増粘ポリアミドイミド
JP7389459B2 (ja) 2018-09-25 2023-11-30 ユニチカ株式会社 ポリアミドイミド溶液の製造方法および増粘ポリアミドイミド

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