Polyimides comprising substituted benzidines

• US 5,071,997 A
• Filed: 07/20/1989
• Issued: 12/10/1991
• Est. Priority Date: 07/20/1989
• Status: Expired due to Term

• Current Assignee: University of Akron
• Original Assignee: University of Akron
• Inventors: Harris, Frank W.
• Primary Examiner(s): Welsh, Maurice J.
• Assistant Examiner(s): Hightower, P. Hampton
• Application Number:
  US07/382,435
• Time in Patent Office: 873 Days
• Field of Search: 528/353, 528/125, 528/126, 528/128, 528/172, 528/351
• US Class Current: 528/353
• CPC Class Codes: B01D 71/64 Polyimides; Polyamide-imides; Polyester-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C08G 73/10 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C08G 73/1039 comprising halogen-containing substituents
• CPC Class Codes: C08G 73/1042 Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
• CPC Class Codes: C08G 73/1064 containing sulfur
• CPC Class Codes: C08G 73/1067 Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
• CPC Class Codes: C08G 73/1071 Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: Y10T 428/2969 Polyamide, polyimide or polyester
• CPC Class Codes: Y10T 428/31721 Of polyimide

Abstract

A new class of polyimides and copolyimides made from substituted benzidines and aromatic dianhydrides and other aromatic diamines. The polyimides obtained with said diamines are distinguished by excellent thermal, excellent solubility, excellent electrical properties such as very low dielectric constants, excellent clarity and mechanical properties making the polyimides ideally suited as coating materials for microelectronic apparatii, as membranes for selective molecular or gas separation, as fibers in molecular composites, as high tensile strength, high compression strength fibers, as film castable coatings, or as fabric components.

Claims

1. A polyimide which consists of 1 to 100 mole percent of the structural elements of the formula (II) ##STR10## where R is a tetravalent organic radical, each A is selected from the group consisting of a halogenated alkyl group, an aryl group and a substituted-aryl group.

2. A polyimide according to claim 1 wherein A is a halogenated alkyl group.

3. A polyimide according to claim 2 wherein said halogenated alkyl group is trifluoromethyl.

4. A polyimide according to claim 1 wherein said polymer consists of 100 mole percent of repeat unit formula (II).

5. A polyimide according to claim 4 wherein A is a halogenated alkyl group.

6. A polyimide according to claim 5 wherein said halogenated alkyl group is trifluoromethyl.

7. A polyimide according to claim 1 wherein said polyimide is characterized by complete solubility in m-cresol or NMP, by UV transparency from about 65% to about 100% at 375 nm, and by a 5% weight loss at a temperature from about 500°

C. to about 600°

C.

8. A polyimide according to claim 4 wherein said polyimide is characterized by complete solubility in m-cresol or NMP, by UV transparency from about 65% to about 100% at 375 nm, by low dielectric constant, and by excellent thermal stability as evidenced by a 5% weight loss at a temperature from about 500°

C. to about 600°

C.

9. A polyimide of claim 1 characterized by the ability to be drawn to form fibers of high tensile strength, excellent resistance to fibrillation, high compressive strength and high temperature stability, said fiber being oriented in at least one direction by being drawn at least two times and being crystalline in the drawing direction and partially or wholly non-crystalline in the direction perpendicular to the drawing direction.

10. A film formed from a polyimide consisting of 1 to 100 mole percent of repeat units of formula (II) ##STR11## where R is a tetravalent organic radical, each A is selected from the group consisting of a halogenated alkyl group, an aryl group and a substituted-aryl group, said polyimide characterized by complete solubility in m-cresol, by UV transparency from about 65% to about 100% at 375 nm, a low dielectric constant, and by excellent thermal stability as evidenced by a 5% weight loss at a temperature from about 500°

C. to about 600°

C.

11. A polyimide according to claim 10 wherein A is a halogenated alkyl group.

13. A polyimide according to claim 10 wherein said polymer consists of 100 mole percent of percent unit formula (II).

14. A polyimide according to claim 13 wherein A is a halogenated alkyl group.

15. A polyimide according to claim 14 wherein said halogenated alkyl group is trifluoromethyl.

12. A polyimide according to claim 69 wherein said halogenated alkyl group is trifluoromethyl.

16. A fiber formed from a polyimide consisting of 1 to 100 mole percent of repeat units of formula (II) ##STR12## where R is a tetravalent organic radical, each A is selected from the group consisting of a halogenated alkyl group, an aryl group and a substituted-aryl group, said polyimide characterized by complete solubility in m-cresol, by UV transparency from about 65% to about 100% at 375 nm, a low dielectric constant, and by excellent thermal stability as evidenced by a 5% weight loss at a temperature from about 500°

C. to about 600°

C., said fiber oriented in one direction by being drawn at least two times in said direction and being characterized by high tensile strength in the draw direction, excellent resistance to fibrillation, a high degree of crystallinity in the drawing direction and partially or entirely non-crystalline in a direction perpendicular to the drawing direction.

17. A polyimide according to claim 16 wherein A is a halogenated alkyl group.

18. A polyimide according to claim 17 wherein said halogenated alkyl group is trifluoromethyl.

19. A polyimide according to claim 16 wherein said polymer consists of 100 mole percent of repeat unit formula (II).

20. A polyimide according to claim 19 wherein A is a halogenated alkyl group.

21. A polyimide according to claim 20 wherein said halogenated alkyl group is trifluoromethyl.

22. An elastomeric or resinous fiber composite comprising fibers of a polyimide consisting of 1 to 100 mole percent of repeat units of formula (II) ##STR13## where R is a tetravalent organic radical, each A is selected from the group consisting of a halogenated alkyl group, an aryl group and a substituted-aryl group, said polyimide characterized by complete solubility in m-cresol, by UV transparency from about 65% to about 100% at 375 nm, a low dielectric constant, and excellent thermal stability as evidenced by a 5% weight loss at a temperature from about 500°

C. to about 600°

C., said fiber oriented in one direction by being drawn at least two times in said direction and being characterized by high tensile strength in the draw direction, excellent resistance to fibrillation, a high degrees of crystallinity in the drawing direction and partially or entirely non-crystalline in a direction perpendicular to the drawing direction.