Polyimides

Patent metadata

Field	Value
Publication number	US-11061327-B2
Application number	US-201716084306-A
Country	US
Kind code	B2
Filing date	Oct 25, 2017
Priority date	Nov 1, 2016
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

Abstract

A polyimide polymer that includes the reaction product of: (a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib),(b) at least one diamine of Structure (II),(c) at least one tetracarboxylic acid dianhydride, and optionally (d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group. Each variable in the above formulas is defined in the specification.

First claim

What is claimed is:

1. A polyimide polymer, comprising the reaction product of components (a), (b), (c), and optionally (d), wherein components (a), (b), (c), and (d) are:
(a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):

(b) at least one diamine of Structure (IIa):

wherein
each of z 3 and z 4 , independently, is an integer ranging from 0 to 4;
R 15 is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, a substituted or unsubstituted phenyl group, or —R 22 —C(R 23 )═C(R 24 R 25 ), in which R 22 is —(CH 2 ) z 6 —; each of R 23 , R 24 and R 25 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, or a substituted or unsubstituted phenyl group; and z 6 is an integer from 0 to 4;
R 16 is —(CH 2 ) z 5 —, in which z 5 is an integer from 1 to 4;
each of R 17 , R 18 , and R 19 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, a substituted or unsubstituted phenyl group; and
each R 20 and each R 21 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group or a halogen atom,
(c) at least one tetracarboxylic acid dianhydride, and optionally,
(d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group, wherein the first functional group reactive to an amine is selected from the group consisting of an anhydride group, an acid halide group, an epoxy group, and an isocyanate group and the first functional group reactive to an anhydride is selected from the group consisting of an amino group, a hydroxyl group, and a thiol group,
wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14 , independently, is H, a substituted or unsubstituted linear C 1 -C 6 alkyl group, a substituted or unsubstituted branched C 3 -C 6 alkyl group, or a substituted or unsubstituted C 5 -C 8 cycloalkyl group, and
wherein a substituted alkyl, alkenyl, alkynyl, cycloalkyl, or hydrocarbon group comprises a substituent selected from the group consisting of C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 1 -C 20 heterocycloalkyl, C 1 -C 20 heterocycloalkenyl, C 1 -C 10 alkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, C 1 -C 10 alkylamino, C 1 -C 20 dialkylamino, arylamino, diarylamino, C 1 -C 10 alkylsulfonamino, arylsulfonamino, C 1 -C 10 alkylimino, arylimino, C 1 -C 10 alkylsulfonimino, arylsulfonimino, hydroxyl, halo, thio, C 1 -C 10 alkylthio, arylthio, C 1 -C 10 alkylsulfonyl, arylsulfonyl, amidino, guanidine, ureido, cyano, nitro, nitroso, azido, acyl, carbamate, thioacyl, acyloxy, carboxyl, and carboxylic ester.

2. The polymer of claim 1 , wherein component (a) is at least one diamine of Structure (Ia).

3. The polymer of claim 2 , wherein the amino group on the indane ring in Structure (Ia) is at the 5 position and the other amino group in Structure (Ia) is at the 4 position.

4. The polymer of claim 3 , wherein each of R 1 , R 2 , and R 3 is CH 3 and each of R 4 and R 5 is H.

5. The polymer of claim 1 , wherein each of z 3 and z 4 is 0.

6. The polymer of claim 5 , wherein R 15 is a hydrogen atom or an unsubstituted linear C 1 -C 4 alkyl.

7. The polymer of claim 1 , wherein the diamine of Structure (IIa) is

8. The polymer of claim 1 , wherein the tetracarboxylic acid dianhydride is selected from the group consisting of:

9. The polymer of claim 1 , wherein the molar ratio of components (a) and (b) to component (c) ranges from 1.01 and 1.4.

10. The polymer of claim 1 , wherein the molar ratio of components (a) and (b) to component (c) ranges from 0.8 and 0.99.

11. A polyamic acid polymer, comprising the reaction product of components (a), (b), (c), and optionally (d), wherein components (a), (b), (c), and (d) are:
(a) at least one diamine selected from the group consisting of a diamine of Structure (Ia) and a diamine of Structure (Ib):

(b) at least one diamine of Structure (IIa):

wherein
each of z 3 and z 4 , independently, is an integer ranging from 0 to 4;
R 15 is a hydrogen atom, a substituted or unsubstituted linear or branched C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, a substituted or unsubstituted phenyl group, or —R 22 —C(R 23 )═C(R 24 R 25 ), in which R 22 is —(CH 2 ) z 6 —; each of R 23 , R 24 and R 25 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, or a substituted or unsubstituted phenyl group; and z 6 is an integer from 0 to 4;
R 16 is —(CH 2 ) z 5 —, in which z 5 is an integer from 1 to 4;
each of R 17 , R 18 , and R 19 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group, a substituted or unsubstituted phenyl group; and
each R 20 and each R 21 , independently, is a hydrogen atom, a substituted or unsubstituted linear C 1 -C 4 alkyl group, a substituted or unsubstituted branched C 3 -C 4 alkyl group, a substituted or unsubstituted C 5 -C 8 cycloalkyl group or a halogen atom,
(c) at least one tetracarboxylic acid dianhydride, and optionally,
(d) at least one compound containing a first functional group reactive with an amine or an anhydride and at least one second functional group selected from the group consisting of a substituted or unsubstituted alkenyl group and a substituted or unsubstituted alkynyl group, wherein the first functional group reactive to an amine is selected from the group consisting of an anhydride group, an acid halide group, an epoxy group, and an isocyanate group and the first functional group reactive to an anhydride is selected from the group consisting of an amino group, a hydroxyl group, and a thiol group,
wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , R 12 , R 13 , and R 14 , independently, is H, a substituted or unsubstituted linear C 1 -C 6 alkyl group, a substituted or unsubstituted branched C 3 -C 6 alkyl group, or a substituted or unsubstituted C 5 -C 8 c

Assignees

• Fujifilm Electronic Mat Usa Inc

Inventors

• Reinerth William A
• De Binod B
• Malik Sanjay
• Sakamuri Raj
• Dimov Ognian N
• Naiini Ahmad A

Classifications

• H10W74/47

  comprising organic materials, e.g. plastics or resins · CPC title

• C08G73/14 Primary

  Polyamide-imides · CPC title

• C08L79/08

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

• G03F7/0387 Primary

  Polyamides or polyimides · CPC title

• C09D179/08

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