IP Library Granted Patent US 11,401,418
Granted Patent B2
US 11,401,418 · App. 16/831,717 · Granted Aug 2, 2022

Method for producing aqueous polyimide precursor solution composition

Inventors: Takeshige Nakayama (Ube, JP); Tomonori Nakayama (Ube, JP); Susumu Takasaki (Ube, JP); Akira Kawabata (Ube, JP); Kenji Sonoyama (Ube, JP)
Assignee: Ube Industries, Ltd.
C08L79/00C08G73/1067C08G73/1071C08K5/3445H01G11/48H01M4/622H01M10/0525
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Quick Facts
Patent No.
US 11,401,418
App. No.
16/831,717
Granted
Aug 2, 2022
Kind
B2
Abstract

A method for producing an aqueous polyimide precursor solution composition includes reacting a tetracarboxylic dianhydride and a diamine in the presence of an imidazole, using water as a reaction solvent to provide an aqueous polyimide precursor solution composition. The polyamic acid and the imidazole are dissolved in the water. A concentration of the polyamic acid is 5 to 45 wt %, The imidazole is an imidazole having two or more alkyl groups as substituents. An amount of the imidazole is 1.6 moles or more per mole of the tetracarboxylic dianhydride, and a concentration of the imidazole compound based on a sum of the imidazole compound and the water is 9.47 wt % or less. The diamine component includes a diamine having a solubility in water at 25° C. of 0.1 g/L or more.

Claims (37)

1. A method for producing an aqueous polyimide precursor solution composition,

the method comprising reacting a tetracarboxylic acid component and a diamine component in water containing no organic solvent in a presence of an imidazole to form a polyamic acid,

wherein,

the polyamic acid and the imidazole are dissolved in the water,

the imidazole is an imidazole having two or more alkyl groups as substituents,

an amount of the imidazole is 1.6 mole or more per mole of the tetracarboxylic acid component,

the tetracarboxylic acid component comprises a tetracarboxylic dianhydride selected from the group consisting of 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,2′,3,3′-biphenyltetracarboxylic dianhydride, oxydiphthalic dianhydride, diphenylsulfone tetracarboxylic dianhydride, p-terphenyl tetracarboxylic dianhydride, m-terphenyl tetracarboxylic dianhydride, cyclobutane-1,2,3,4-tetracarboxylic dianhydride, and 1,2,4,5-cyclohexane tetracarboxylic dianhydride, and

the diamine component comprises an aromatic or alicyclic diamine having a solubility in water at 25° C. of 0.1 g/L or more.

2. The method for producing an aqueous polyimide precursor solution composition as claimed in claim 1 , wherein the imidazole is selected from the group consisting of 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 4-ethyl-2-methylimidazole, and 1-methyl-4-ethylimidazole.

3. The method for producing an aqueous polyimide precursor solution composition as claimed in claim 1 , wherein the polyamic acid has an inherent viscosity of 0.4 or more.

4. The method for producing an aqueous polyimide precursor solution composition as claimed in claim 1 , wherein

the polyamic acid comprises a repeating unit represented by the following formula (1),

wherein A represents a tetravalent group of an aromatic tetracarboxylic acid having two to three aromatic rings, from which carboxyl groups have been removed, and B represents a divalent group of an aromatic diamine having one to two aromatic rings and having a solubility in water at 25° C. of 0.1 g/L or more, from which amino groups have been removed.

5. The method for producing an aqueous polyimide precursor solution composition as claimed in claim 4 , wherein the “A” group in the formula (1) is any one or more of the groups represented by the following formulas (2) to (4), (6), and (7);

6. The method as claimed in claim 4 , wherein the “B” group in the formula (1) is any one or more of the groups represented by the following formulas (8) to (9);

7. A method for producing an aromatic polyimide seamless belt, comprising:

producing the aqueous polyimide precursor solution composition according to the method of claim 1 ; and

applying the aqueous polyimide precursor solution composition to a mold for forming a seamless belt; and

heating the aqueous polyimide precursor solution.

8. A method for producing an electrode, comprising

producing the aqueous polyimide precursor solution composition according to the method of claim 1 ; and

mixing the aqueous polyimide precursor solution composition and at least an electrode active material to form an electrode mixture paste,

applying the electrode mixture paste onto a current collector, and

heating the electrode mixture paste to remove a solvent and effect imidization.

9. A method for producing a flexible device which is a display device or a light-receiving device, comprising:

producing the aqueous polyimide precursor solution composition according to the method of claim 1 ; and

applying the aqueous polyimide precursor solution composition onto a carrier substrate, and then heating the composition to form a solid polyimide resin film;

forming a circuit on the polyimide resin film; and

separating the polyimide resin film on which the circuit is formed from the carrier substrate.

10. A method for producing an aqueous polyimide precursor solution composition,

the method comprising reacting a tetracarboxylic acid component and a diamine component in water containing no organic solvent in a presence of an imidazole at 50° C. or higher and 100° C. or lower to form a polyamic acid,

wherein,

the polyamic acid and the imidazole are dissolved in the water,

the imidazole is an imidazole having two or more alkyl groups as substituents,

an amount of the imidazole is 1.6 mole or more per mole of the tetracarboxylic acid component,

the tetracarboxylic acid component comprises a tetracarboxylic dianhydride,

the diamine component comprises an aromatic or alicyclic diamine having a solubility in water at 25° C. of 0.1 g/L or more.

Assignments (3)
CHANGE OF NAME Recorded Jul 14, 2023
From: UBE INDUSTRIES, LTD.
To: UBE CORPORATION
Reel/Frame 064275/0021 →
CHANGE OF NAME Recorded Mar 3, 2023
From: UBE INDUSTRIES LTD.
To: UBE CORPORATION
Reel/Frame 062953/0393 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 29, 2021
From: NAKAYAMA, TAKESHIGE; NAKAYAMA, TOMONORI; TAKASAKI, SUSUMU; KAWABATA, AKIRA; SONOYAMA, KENJI
To: UBE INDUSTRIES, LTD.
Reel/Frame 055751/0368 →