Polyamic acid composition with improved adhesion and polyimide cured product comprising the same

Patent metadata

Field	Value
Publication number	US-2026062517-A1
Application number	US-202519314374-A
Country	US
Kind code	A1
Filing date	Aug 29, 2025
Priority date	Aug 30, 2024
Publication date	Mar 5, 2026
Grant date	—

Abstract

The present invention provides a polyamic acid composition comprising a dianhydride monomer and a diamine monomer as polymerization units, wherein the diamine monomer comprises a first diamine monomer, a second diamine monomer, and a third diamine monomer, the second diamine monomer is a flexible diamine monomer having three or more benzene rings, and the third diamine monomer is represented by Chemical Formula 1. The polyamic acid composition of the present disclosure may have excellent adhesion and adherence to wires h as copper, and thus may have excellent usability as an insulating coating material for an electric wire, etc.

First claim

1 . A polyamic acid composition comprising a dianhydride monomer and a diamine monomer as polymerization units,
wherein the diamine monomer comprises a first diamine monomer, a second diamine monomer, and a third diamine monomer, the second diamine monomer is a flexible diamine monomer having three or more benzene rings, and the third diamine monomer is represented by the following Chemical Formula 1:

in Chemical Formula 1 above,
A is unsubstituted or substituted, and is selected from hydrogen, halogen, C1-C6 alkyl, phenyl, (C1-C6 alkylene)-(C3-C5 heteroaryl), (C1-C6 alkylene)-COOH, or —OH, wherein the substitution means substitution with halogen, C1-C3 alkyl, C1-C3 haloalkyl or oxo (═O).

2 . The polyamic acid composition of claim 1 , wherein the first diamine monomer is a diamine having two or fewer benzene rings.

3 . The polyamic acid composition of claim 2 , wherein the first diamine monomer comprises at least one selected from the group consisting of 1,4-diaminobenzene (or paraphenylenediamine, PDA, PPD), 1,3-diaminobenzene, 2,4-diaminotoluene, 2,6-diaminotoluene, 3,5-diaminobenzoic acid (DABA), 4,4′-diaminodiphenyl ether (or oxydianiline, ODA), 3,4′-diaminodiphenyl ether, 3,3′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane(methylenediamine), 3,3′-diaminodiphenylmethane, 3,4′-diaminodiphenylmethane, 3,3′-dimethyl-4,4′-diaminodiphenylmethane, 3,3′,5,5′-tetramethyl-4,4′-diaminodiphenylmethane, 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl, 3,3′-dicarboxy-4,4′-diaminodiphenylmethane, 4,4′-diaminobenzanilide, 3,3′-dichlorobenzidine, 3,3′-dimethylbenzidine (or o-tolidine), 2,2′-dimethylbenzidine (or m-tolidine), 3,3′-dimethoxybenzidine, 2,2′-dimethoxybenzidine, 3,3′-diaminodiphenylsulfide, 3,4′-diaminodiphenylsulfide, 4,4′-diaminodiphenylsulfide, 3,3′-diaminodiphenylsulfone, 3,4′-diaminodiphenylsulfone, 4,4′-diaminodiphenylsulfone, 3,3′-diaminobenzophenone, 4,4′-diaminobenzophenone, 3,3′-diamino-4,4′-dichlorobenzophenone, 3,3′-diamino-4,4′-dimethoxybenzophenone, 2,2-bis(3-aminophenyl) propane, 2,2-bis(4-aminophenyl) propane, 2,2-bis(3-aminophenyl)-1,1,1,3,3,3-hexafluoropropane, 2,2-bis(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropane, 3,3′-diaminodiphenylsulfoxide, 3,4′-diaminodiphenylsulfoxide, and 4,4′-diaminodiphenylsulfoxide.

4 . The polyamic acid composition of claim 1 , wherein the second diamine monomer comprises at least one selected from the group consisting of 1,3-bis(3-aminophenyl)benzene, 1,3-bis(4-aminophenyl)benzene, 1,4-bis(3-aminophenyl)benzene, 2,2-bisaminophenoxyphenylpropane (BAPP), 1,3-bis(4-aminophenoxy)benzene (TPE-R), 1,4-bis(3-aminophenoxy)benzene (TPE-Q), 1,3-bis(3-aminophenoxy)-4-trifluoromethylbenzene, 3,3′-diamino-4-(4-phenyl)phenoxybenzophenone, 3,3′-diamino-4,4′-di(4-phenylphenoxy)benzophenone, 1,3-bis(3-aminophenylsulfide)benzene, 1,3-bis(4-aminophenylsulfide)benzene, 1,4-bis(4-aminophenylsulfide)benzene, 1,3-bis(3-aminophenylsulfone)benzene, 1,3-bis(4-aminophenylsulfone)benzene, 1,4-bis(4-aminophenylsulfone)benzene, 1,3-bis[2-(4-aminophenyl) isopropyl]benzene, 1,4-bis[2-(3-aminophenyl) isopropyl]benzene, 1,4-bis[2-(4-aminophenyl) isopropyl]benzene, 3,3′-bis(3-aminophenoxy)biphenyl, 3,3′-bis(4-aminophenoxy)biphenyl, 4,4′-bis(3-aminophenoxy)biphenyl, 4,4′-bis(4-aminophenoxy)biphenyl, bis[3-(3-aminophenoxy)phenyl]ether, bis[3-(4-aminophenoxy)phenyl]ether, bis[4-(3-aminophenoxy)phenyl]ether, bis[4-(4-aminophenoxy)phenyl]ether, bis[3-(3-aminophenoxy)phenyl]ketone, bis[3-(4-aminophenoxy)phenyl]ketone, bis[4-(3-aminophenoxy)phenyl]ketone, bis[4-(4-aminophenoxy)phenyl]ketone, bis[3-(3-aminophenoxy)phenyl]sulfide, bis[3-(4-aminophenoxy)phenyl]sulfide, bis[4-(3-aminophenoxy)phenyl]sulfide, bis[4-(4-aminophenoxy)phenyl]sulfide, bis[3-(3-aminophenoxy)phenyl]sulfone, bis[3-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]sulfone, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[3-(3-aminophenoxy)phenyl]methane, bis[3-(4-aminophenoxy)phenyl]methane, bis[4-(3-aminophenoxy)phenyl]methane, bis[4-(4-aminophenoxy)phenyl]methane, 2,2-bis[3-(3-aminophenoxy)phenyl]propane, 2,2-bis[3-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-(3-aminophenoxy)phenyl]propane, 2,2-bis[3-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[3-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, 2,2-bis[4-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, and 2,2-bis[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane (BDAF).

5 . The polyamic acid composition of claim 1 , wherein the A is hydrogen, fluoro (F), chloro (Cl), bromo (Br), methyl, ethyl, propyl, phenyl, (C1-C6 alkylene)-imidazolyl, (C1-C6 alkylene)-COOH, or —OH, and
the A is unsubstituted or substituted with at least one or more methyl, ethyl, trifluoromethyl, or oxo (═O).

6 . The polyamic acid composition of claim 1 , wherein the third diamine monomer comprises at least one selected from the group consisting of 1,3,5-triazine-2,4-diamine, 6-chloro-1,3,5-triazine-2,4-diamine, 4,6-diamino-1,3,5-triazin-2-ol, 6-methyl-1,3,5-triazine-2,4-diamine, 6-phenyl-1,3,5-triazine-2,4-diamine, 6-[2-(2-methylimidazol-1-yl)ethyl]-1,3,5-triazine-2,4-diamine, and 4-(4,6-diamino-1,3,5-triazin-2-yl)-4-oxobutanoic acid.

7 . The polyamic acid composition of claim 1 , wherein the diamine monomer comprises 50 to 98 mol % of the first diamine monomer, based on 100 mol % of the total amount of the diamine monomer.

8 . The polyamic acid composition of claim 1 , wherein the diamine monomer comprises 1 to 25 mol % of the second diamine monomer, based on 100 mol % of the total amount of the diamine monomer.

9 . The polyamic acid composition of claim 1 , wherein the diamine monomer comprises 1 to 25 mol % of the third diamine monomer, based on 100 mol % of the total amount of the diamine monomer.

10 . The polyamic acid composition of claim 1 , wherein the dianhydride monomer comprises at least one selected from the group consisting of pyromellitic dianhydride (PMDA), biphenyl tetracarboxylic dianhydride (BPDA), 3,3′,4,4′-benzophenone tetracarboxylic dianhydride (BTDA), oxidiphthalic dianhydride (ODPA), diphenylsulfone-3,4,3′,4′-tetracarboxylic dianhydride (DSDA), bis(3,4-dicarboxyphenyl) sulfide dianhydride, 2,2-bis(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropane dianhydride, 2,3,3′,4′-benzophenonetetracarboxylic dianhydride, bis(3,4-dicarboxyphenyl) methane dianhydride, 2,2-bis(3,4-dicarboxyphenyl) propane dianhydride, p-phenylenebis(trimellitic monoester acid anhydride), p-biphenylenebis(trimellitic monoester acid anhydride), m-terphenyl-3,4,3′,4′-tetracarboxylic dianhydride, p-terphenyl-3,4,3′,4′-tetracarboxylic dianhydride, 1,3-bis(3,4-dicarboxyphenoxy)benzene dianhydride, 1,4-bis(3,4-dicarboxyphenoxy)benzene dianhydride, 1,4-bis(3,4-dicarboxyphenoxy)biphenyl dianhydride, 2,2-bis[(3,4-dicarboxy phenoxy)phenyl]propane dianhydride (BPADA), 2,3,6,7-naphthalene tetracarboxylic acid dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride, and 4,4′-(2,2-hexafluoroisopropylidene)diphthalic acid dianhydride.

11 . The polyamic acid composition of claim 1 , wherein the polyamic acid composition after curing has a crosscut adhesion of 5B or higher according to ASTM D 3359 standard.

12 . The polyamic acid composition of claim 1 , wherein the polyamic acid composition after curing has a tensile strength of 95 MPa or more, a modulus of 2.0 GPa or more, and an elongation of 3% or more.

13 . The polyamic acid composition of claim 1 , wherein the polyamic acid composition after curing has a glass transition temperature of 300° C. or higher,
a temperature (Td) at which 1% weight loss occurs of 340° C. or highe

Assignees

• Pi Advanced Mat Co Ltd

Inventors

• Moon Gyeong Min
• Yoo Cheol Hun
• We Jung Hoon
• Park Se Joo
• Lee Ik Sang

Classifications

• C09J179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08K9/06

  with silicon-containing compounds · CPC title

• C08K3/36

  Silica · CPC title

• C08G73/1071

  Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain · CPC title