IP Library Granted Patent US 11,407,868
Granted Patent B2
US 11,407,868 · App. 16/832,337 · Granted Aug 9, 2022

Method for producing aqueous polyimide precursor solution composition

Inventors: Takeshige Nakayama (Ube, JP); Susumu Takasaki (Ube, JP); Tomonori Nakayama (Ube, JP); Kensuke Hiroshige (Ube, JP)
Assignee: Ube Industries, Ltd.
C08J5/18B29C39/006B29C39/38C08G73/10C08K5/3445C08L79/08B29K2079/08B29K2105/0002B29K2105/0073B29L2031/3475C08J2379/08Y10T428/31721
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Quick Facts
Patent No.
US 11,407,868
App. No.
16/832,337
Granted
Aug 9, 2022
Kind
B2
Abstract

A method for producing an aqueous polyimide precursor solution includes forming a polyamic acid by the reaction of a tetracarboxylic acid component and a diamine component in water without organic solvent together with an imidazole in an amount of 1.6 mole or more per mole of the tetracarboxylic acid component of the polyamic acid.

Claims (33)

1. A method for producing an aqueous polyimide precursor solution composition, 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 comprising a repeating unit represented by the following formula (1),

wherein,

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

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

the tetracarboxylic acid component comprises at least one selected from the group consisting of an aromatic tetracarboxylic dianhydride containing no fluorine group, an aliphatic tetracarboxylic dianhydride, and aromatic tetracarboxylic dianhydride containing a fluorine group; the aromatic tetracarboxylic dianhydride containing no fluorine group being selected from the group consisting of 3,3′,4,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,2′,3,3′-biphenyltetracarboxylic dianhydride, 4,4′-oxydiphthalic dianhydride, diphenylsulfone tetracarboxylic dianhydride, p-terphenyl tetracarboxylic dianhydride, and m-terphenyl tetracarboxylic dianhydride, and

the diamine component comprises at least one selected from the group consisting of an aromatic diamine containing no fluorine group and having a solubility in water at 25° C. of 0.1 g/L or more, an aliphatic diamine having a molecular weight of 500 or less and selected from the group consisting of alicyclic diamine, 1,6-hexamethylene diamine and 1,10-decamethylene diamine, and an aromatic diamine containing a fluorine group, and

wherein,

(i) not less than 50 mol % of the tetracarboxylic dianhydride component is the aliphatic tetracarboxylic dianhydride, and/or the aromatic tetracarboxylic dianhydride containing a fluorine group, and not more than 50 mol %, including 0 mol %, of the tetracarboxylic dianhydride component is the aromatic tetracarboxylic dianhydride containing no fluorine group, or

(ii) not less than 50 mol % of the tetracarboxylic dianhydride component is the aromatic tetracarboxylic dianhydride containing no fluorine group, and not less than 50 mol % of the diamine component is the aliphatic diamine having a molecular weight of 500 or less, and/or the aromatic diamine containing a fluorine group, and not more than 50 mol %, including 0 mol %, of the diamine component is an aromatic diamine containing no fluorine group and having a solubility in water at 25° C. of 0.1 g/L or more,

wherein

A represents a tetravalent group derived from the tetracarboxylic acid component and B represents a divalent group derived from the diamine component.

2. The method for producing an aqueous polyimide precursor solution composition according to 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 according to claim 1 , wherein the polyamic acid has an inherent viscosity of 0.4 or more.

4. A method for producing a polyimide comprising producing the aqueous polyimide precursor solution composition according to the method of claim 1 ; and

heating the aqueous polyimide precursor solution composition.

5. The method for producing a polyimide as claimed in claim 4 , wherein the polyimide has a light transmittance at 400 nm of 60% or more when the polyimide is formed into a film having a thickness of 10 μm.

6. The method for producing a polyimide as claimed in claim 4 , wherein the polyimide has a total light transmittance of 80% or more when the polyimide is formed into a film having a thickness of 10 μm.

7. 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.

8. A method for producing an aqueous polyimide precursor solution composition, 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 comprising a repeating unit represented by the following formula (1),

wherein,

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

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

the tetracarboxylic acid component comprises at least one selected from the group consisting of an aromatic tetracarboxylic dianhydride containing no fluorine group, an aliphatic tetracarboxylic dianhydride, and aromatic tetracarboxylic dianhydride containing a fluorine group, and

the diamine component comprises at least one selected from the group consisting of an aromatic diamine containing no fluorine group and having a solubility in water at 25° C. of 0.1 g/L or more, an aliphatic diamine having a molecular weight of 500 or less and selected from the group consisting of alicyclic diamine, 1,6-hexamethylene diamine and 1,10-decamethylene diamine, and an aromatic diamine containing a fluorine group, and

wherein,

not less than 50 mol % of the tetracarboxylic dianhydride component is the aliphatic tetracarboxylic dianhydride, and/or the aromatic tetracarboxylic dianhydride containing a fluorine group, and not more than 50 mol %, including 0 mol %, of the tetracarboxylic dianhydride component is the aromatic tetracarboxylic dianhydride containing no fluorine group, and/or not less than 50 mol % of the diamine component is the aliphatic diamine having a molecular weight of 500 or less, and/or the aromatic diamine containing a fluorine group, and not more than 50 mol %, including 0 mol %, of the diamine component is an aromatic diamine containing no fluorine group and having a solubility in water at 25° C. of 0.1 g/L or more,

wherein

A represents a tetravalent group derived from the tetracarboxylic acid component and B represents a divalent group derived from the diamine component.

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 Jul 16, 2020
From: NAKAYAMA, TAKESHIGE; TAKASAKI, SUSUMU; NAKAYAMA, TOMONORI; HIROSHIGE, KENSUKE
To: UBE INDUSTRIES, LTD.
Reel/Frame 053228/0663 →