Polyamide copolymers having 2,5-furan dicarboxamide units

Patent metadata

Field	Value
Publication number	US-2016145388-A1
Application number	US-201414900402-A
Country	US
Kind code	A1
Filing date	Jun 20, 2014
Priority date	Jun 21, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

Polyamide copolymers, and methods of making and using polyamide copolymers, having 2,5-furan dicarboxamide units are disclosed herein. Such polymers can be useful for engineering thermoplastics having advantageous physical and/or chemical properties.

First claim

What is claimed is:

1 . A polyamide copolymer comprising at least one alkylene 2,5-furan dicarboxamide unit, with the proviso that the copolymer does not comprise —(CH 2 ) 10 — alkylene units.

2 . The polyamide copolymer of claim 1 wherein the at least one alkylene 2,5-furan dicarboxamide unit is of the formula:

wherein k=6-9 or 11-30.

3 . The polyamide copolymer of claim 1 , wherein the copolymer further comprises at least one alkylene terephthalamide unit.

4 . The polyamide copolymer of claim 3 wherein the at least one alkylene terephthalamide unit is of the formula:

wherein m=6-9 or 11-30.

5 . The polyamide copolymer claim 1 , wherein the copolymer further comprises at least one alkylene adipamide unit.

6 . The polyamide copolymer of claim 5 wherein the at least one alkylene adipamide unit is of the formula:

wherein n=6-9 or 11-30.

7 . The polyamide copolymer of claim 1 , wherein the polyamide copolymer has a difference between melting temperature (T m ) and crystallization temperature (T c ) of at most 50° C.;
wherein the crystallization temperature (T c ) is taken as the maximum of the crystallization exotherm of a differential scanning calorimetry (DSC) thermogram obtained by cooling the polyamide copolymer from 300° C. to 25° C. at 20° C. per minute; and
wherein the melting temperature (T m ) is taken as the maximum of the melting endotherm of a differential scanning calorimetry (DSC) thermogram obtained by subsequently heating the polyamide copolymer from 25° C. to the molten state at 20° C. per minute.

8 . The polyamide copolymer of claim 7 wherein the difference between melting temperature (T m ) and crystallization temperature (T c ) is at most 40° C.

9 . The polyamide copolymer of claim 7 wherein the difference between melting temperature (T m ) and crystallization temperature (T c ) is at most 30° C.

10 . The polyamide copolymer of claim 1 , wherein all the amide units in the copolymer include the same diamine fragment.

11 . A method of fabricating an article comprising:
providing a polyamide copolymer according to claim 1 ; and melt processing the polyamide copolymer under conditions effective to form the article.

12 . The method of claim 11 wherein conditions effective comprise one or more of injection molding, compression molding, transfer molding, and extrusion.

13 . A polyamide copolymer comprising at least one alkylene 2,5-furan dicarboxamide unit and at least one alkylene adipamide unit.

14 . The polyamide copolymer of claim 13 wherein the at least one alkylene 2,5-furan dicarboxamide unit is of the formula:

wherein k=6-30.

15 . The polyamide copolymer of claim 13 wherein the at least one alkylene adipamide unit is of the formula:

wherein n=6 to 30.

16 . The polyamide copolymer of claim 13 , wherein the copolymer further comprises at least one alkylene terephthalamide unit.

17 . The polyamide copolymer of claim 16 wherein the at least one alkylene terephthalamide unit is of the formula:

wherein m=6-30.

18 . The polyamide copolymer of claim 13 , wherein the polyamide copolymer has a difference between melting temperature (T m ) and crystallization temperature (T c ) of at most 50° C.;
wherein the crystallization temperature (T c ) is taken as the maximum of the crystallization exotherm of a differential scanning calorimetry (DSC) thermogram obtained by cooling the polyamide copolymer from 300° C. to 25° C. at 20° C. per minute; and
wherein the melting temperature (T m ) is taken as the maximum of the melting endotherm of a differential scanning calorimetry (DSC) thermogram obtained by subsequently heating the polyamide copolymer from 25° C. to the molten state at 20° C. per minute.

19 . The polyamide copolymer of claim 18 wherein the difference between melting temperature (T m ) and crystallization temperature (T c ) is at most 40° C.

20 . The polyamide copolymer of claim 18 wherein the difference between melting temperature (T m ) and crystallization temperature (T c ) is at most 30° C.

21 . The polyamide copolymer of claim 13 , wherein all the amide units in the copolymer include the same diamine fragment.

22 . A method of fabricating an article comprising:
providing a polyamide copolymer according to claim 13 ; and melt processing the polyamide copolymer under conditions effective to form the article.

23 . The method of claim 22 wherein conditions effective comprise one or more of injection molding, compression molding, transfer molding, and extrusion.

24 . A method of preparing a polyamide copolymer, the method comprising:
providing a copolyamide prepolymer comprising alkylene 2,5-furan dicarboxamide repeat units, with the proviso that the copolyamide prepolymer does not comprise —(CH 2 ) 10 — alkylene units; and heating the copolyamide prepolymer under conditions effective to form the polyamide copolymer.

25 . The method of claim 24 wherein the copolyamide prepolymer further comprises alkylene terephthalamide repeat units.

26 . The method of claim 24 wherein the copolyamide prepolymer further comprises alkylene adipamide repeat units.

27 . A method of preparing a polyamide copolymer, the method comprising:
providing a copolyamide prepolymer comprising alkylene 2,5-furan dicarboxamide repeat units and alkylene adipamide repeat units; and heating the copolyamide prepolymer under conditions effective to form the polyamide copolymer.

28 . The method of claim 27 wherein the copolyamide prepolymer further comprises alkylene terephthalamide repeat units.

Assignees

• Chisholm Bret Ja
• Samanta Satyabrata
• Ndsu Res Foundation

Inventors

• Chisholm Bret Ja
• Samanta Satyabrata

Classifications

• C08G69/26

  derived from polyamines and polycarboxylic acids · CPC title

• C08G63/181

  Acids containing aromatic rings · CPC title

• C08G69/28

  Preparatory processes · CPC title

• C08L77/06

  Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence) · CPC title

• C08G69/265 Primary

  from at least two different diamines or at least two different dicarboxylic acids · CPC title