Hygromorphic polymers and copolymers having humidity-driven motility

Patent metadata

Field	Value
Publication number	US-10457780-B2
Application number	US-201815910094-A
Country	US
Kind code	B2
Filing date	Mar 2, 2018
Priority date	Mar 11, 2016
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

New diamine monomers bearing sulfone terminated pendant groups, as well as methods for making the same, are provided. The diamine monomers are useful toward making polyamide, polyimide, and poly(amide-imide) polymers and copolymers, which possess hygromorphic properties and demonstrate humidity driven motility.

First claim

What is claimed is:

1. A polymer comprising:
a diamine portion derived from an aryl diamine monomer comprising a sulfone moiety and having a general chemical formula:

wherein W is selected from the group consisting of O, NH, and NR 1 ;
wherein R 1 and R 2 are independently selected from the group consisting of substituted or unsubstituted C1-C7 alkyl groups and unsubstituted phenyl groups;
and wherein the polymer is selected from the group consisting of a polyamide, a polyimide, and a poly(amide-imide).

2. The polymer of claim 1 , wherein the polyimide is selected from the group consisting of an ester-sulfone-containing polyimide and an amide-sulfone-containing polyimide, the polymer having a general chemical formula:

wherein when W is O, then the moiety is an ester-sulfone, and when W is NH or NR, then the moiety is an amide-sulfone,
wherein

 is selected from the group consisting of

and
wherein n represents a degree of polymerization.

3. The polymer of claim 1 , wherein the polyamide is selected from the group consisting of an ester-sulfone-containing polyamide and an amide-sulfone-containing polyamide, the polymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

and
wherein n represents a degree of polymerization.

4. The polymer of claim 1 , wherein the poly(amide-imide) is selected from the group consisting of an ester-sulfone-containing poly(amide-imide) and an amide-sulfone-containing poly(amide-imide), the polymer having a general formula:

wherein n represents a degree of polymerization.

5. The polymer of claim 1 , wherein the poly(amide-imide) is selected from the group consisting of an ester-sulfone-containing poly(amide-imide) and an amide-sulfone-containing poly(amide-imide), the polymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

and
wherein n represents a degree of polymerization.

6. The polymer of claim 1 , wherein the poly(amide-imide) is selected from the group consisting of an ester-sulfone-containing poly(amide-imide) and an amide-sulfone-containing poly(amide-imide), the polymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

and
wherein n represents a degree of polymerization.

7. A copolymer composition comprising complementary monomer portions of
a first monomer portion comprising a sulfone terminated pendant group and having a general chemical formula:

and
a second monomer portion comprising at least one carboxylic acid or carboxamide terminated pendant group and having a general chemical formula:

wherein W is selected from the group consisting of O, NH, and NR 1 ;
wherein R 1 and R 2 are independently selected from the group consisting of substituted or unsubstituted C1-C7 alkyl groups, and substituted or unsubstituted phenyl groups;
and wherein the copolymer is selected from the group consisting of a polyamide copolymer, a polyimide copolymer, and a poly(amide-imide) copolymer.

8. The copolymer composition of claim 7 , wherein the copolymer is a polyimide copolymer comprising complementary portions of the sulfone terminated pendant group and the at least one carboxylic acid or carboxamide terminated pendant group, the polyimide copolymer having a general chemical formula:

wherein

 is selected from the group consisting of

and
n represents a degree of polymerization; and wherein x is in a range of about 0.01 to about 0.99.

9. The copolymer composition of claim 7 , wherein the copolymer is a polyamide copolymer comprising complementary portions of a sulfone terminated pendant group and at least one carboxylic acid or carboxamide terminated pendant group, the polyamide copolymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

and
wherein n represents a degree of polymerization, and wherein x is in a range of about 0.01 to about 0.99.

10. The copolymer composition of claim 7 , wherein the copolymer is a poly(amide-imide) copolymer comprising complementary portions of a sulfone terminated pendant group and at least one carboxylic acid or carboxamide terminated pendant group, the poly(amide-imide) copolymer having a general chemical formula:

wherein n represents a degree of polymerization; and wherein x is in a range of about 0.01 to about 0.99.

11. The copolymer composition of claim 7 , wherein the copolymer is a poly(amide-imide) copolymer comprising complementary portions of a sulfone terminated pendant group and at least one carboxylic acid or carboxamide terminated pendant group, the copolymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

and
wherein n represents a degree of polymerization; and wherein x is in a range of about 0.01 to about 0.99.

12. The copolymer composition of claim 7 , wherein the copolymer is a poly(amide-imide) copolymer composition comprising complementary portions of a sulfone terminated pendant group and at least one carboxylic acid or carboxamide terminated pendant group, the copolymer having a general chemical formula:

wherein Ar′ is selected from the group consisting of

Assignees

• Us Gov Air Force
• Us Air Force

Inventors

• Tan Loon-Seng
• Wang David Huabin
• Vaia Richard A
• Buskohl Philip R
• Mckenzie Ruel

Classifications

• C08G73/1067

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C07C229/56

  with amino and carboxyl groups bound in ortho-position · CPC title

• C07C317/40

  Y being a hydrogen or a carbon atom · CPC title

• C07C317/44

  having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton · CPC title