Polyamide materials based on unsaturated carboxylic acids and amines

• US 20050043506A1
• Filed: 08/24/2004
• Published: 02/24/2005
• Est. Priority Date: 09/27/2000
• Status: Abandoned Application

• Current Assignee: The Michigan Biotechnology Institute
• Original Assignee: The Michigan Biotechnology Institute
• Inventors: Taylor, Andrew C., Danzig, Morris, Huang, Zhi Heng, Wright, Stacy C., McDonald, William F.
• Application Number:
  US10/924,490
• Publication Number:
  US 20050043506A1
• Time in Patent Office: Days
• US Class Current: 528/420
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/24 containing ingredients to enhance the sticking of the active ingredients
• CPC Class Codes: A01N 25/34 Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
• CPC Class Codes: A01N 59/16 Heavy metals; Compounds thereof
• CPC Class Codes: A01N 59/20 Copper
• CPC Class Codes: C08G 18/603 Polyamides
• CPC Class Codes: C08G 69/02 Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 69/04 Preparatory processes
• CPC Class Codes: C08G 69/08 derived from amino-carboxylic acids
• CPC Class Codes: C08G 69/14 Lactams
• CPC Class Codes: C08G 69/26 derived from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 69/265 from at least two different diamines or at least two different dicarboxylic acids
• CPC Class Codes: C08K 3/08 Metals
• CPC Class Codes: C08K 3/24 Acids; Salts thereof C08K3/16 takes precedence
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 77/00 Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 77/02 Polyamides derived from omega-amino carboxylic acids or from lactams thereof C08L77/10 takes precedence
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

A polyamide and a process for preparing the polyamide are disclosed. The process comprises reacting in a reaction mixture a monomer selected from unsaturated carboxylic acids, esters of unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, and mixtures thereof, and a first amine to form an intermediate reaction product in the reaction mixture, wherein the first amine is selected from RR₁NH, RNH₂, RR₁NH₂⁺, RNH₃⁺, and mixtures thereof, wherein R and R₁, can be the same or different and each contain between about 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, and phosphorus and combinations thereof, and reacting the intermediate reaction product and a second amine to form a polyamide, wherein the second amine is selected from R₂R₃NH, R₂NH₂, R₂R₃NH₂⁺, R₂NH₃⁺and mixtures thereof wherein R₂ and R₃ can be the same or different and each contain between about 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, and phosphorus and combinations thereof, wherein multiple of the R, R₁, R₂, and R₃ are in vertically aligned spaced relationship along a backbone formed by the polyamide. In one version of the invention, the monomer is selected from maleic anhydride, maleic acid esters, and mixtures thereof. In another version of the invention, the first amine is an alkylamine, such as tetradecylamine, and the second amine is a polyalkylene polyamine, such as pentaethylenehexamine. In yet another version of the invention, the first amine and the second amine are olefinic or acetylenic amines, such as the reaction products of an alkyldiamine and an acetylenic carboxylic acid. The first amine and the second amine may be the same or different depending on the desired polyamide polymer structure.

Claims

1. A crosslinked polyamide material formed from a mixture of a crosslinking agent and a polyamide material,

wherein the polyamide material comprises a polymer formed from a mixture comprising:

(a) a monomer selected from unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids, and mixtures thereof; and

(b) one or more amines selected from polyalkylene polyamines and amines having the formula R—

NH₂ or R₁RNH wherein the R and R₁groups contain between 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, phosphorus, and combinations thereof;

wherein at least one of the selected amines includes at least two amino groups and at least one of the selected amines is an alkyl amine.

2. The polyamide material of claim 1 wherein the monomer includes unsaturated dicarboxylic acids, esters of unsaturated dicarboxylic acids, anhydrides of unsaturated dicarboxylic acids, or a mixture thereof.

3. The polyamide material of claim 1 wherein the monomer includes maleic anhydride, maleic acid ester, or a mixture thereof.

4. The polyamide material of claim 1 wherein the alkyl amine is unsubstituted and has a carbon chain length of C₆-C₅₀.

5. The polyamide material of claim 1 wherein the selected amine includes at least one polyalkylene polyamine.

6. The polyamide material of claim 1 wherein the monomer includes maleic anhydride, maleic acid ester, or a mixture thereof;

and the amine includes at least one alkyl amine that is unsubstituted and has a carbon chain length of C₆-C₅₀ and at least one polyalkylene polyamine.

7. A polymeric material comprising a polyamide formed from a reaction mixture comprising:

(a) a monomer selected from unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids, and mixtures thereof; and

(b) one or more amines selected from polyalkylene polyamines and amines having the formula R—

NH₂ or R₁RNH wherein the R and R₁ groups contain between 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, phosphorus, and combinations thereof, wherein at least one of the selected amines includes at least two amino groups and at least one of the selected amines is an alkyl amine.

8. The polyamide material of claim 7 further comprising a transition element.

9. The polyamide material of claim 7 further comprising metal powder.

10. The polyamide material of claim 7 wherein the monomer includes maleic anhydride, maleic acid ester, or a mixture thereof;

and the selected amine includes a polyalkylene polyamine.

11. The polyamide material of claim 8 wherein the polyamide material is conductive.

12. The polyamide material of claim 9 wherein the polyamide material is conductive.

13. A crosslinked polyamide material formed from a mixture of a crosslinking agent and a polyamide material,

wherein the polyamide material comprises:

(A) a polymer formed from a mixture comprising;

(1) a monomer selected from unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids, and mixtures thereof; and

(2) one or more amines selected from polyalkylene polyamines and amines having the formula R—

NH₂ or R₁RNH wherein the R and R₁ groups contain between 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, phosphorus, and combinations thereof, wherein at least one of the selected amines includes at least two amino groups; and

(B) a transition metal.

14. A polyamide material comprising:

(A) a polyamide formed from a reaction mixture comprising;

(1) a monomer selected from unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids, and mixtures thereof; and

(2) one or more amines selected from polyalkylene polyamines and amines having the formula R—

NH₂ or R₁RNH wherein the R and R₁ groups contain between 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, phosphorus, and combinations thereof, wherein at least one of the selected amines includes at least two amino groups; and

(B) a transition metal.

15. A polyamide coated article comprising:

a substrate; and

a coating on a surface of the substrate, wherein the coating comprises a crosslinked polyamide material comprising a polymer formed from a reaction mixture comprising;

(a) a monomer selected from unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, esters of unsaturated carboxylic acids, and mixtures thereof; and

(b) one or more amines selected from polyalkylene polyamines and amines having the formula R—

NH₂ or R₁RNH wherein the R and R₁ groups contain between 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, phosphorus, and combinations thereof, wherein at least one of the selected amines includes at least two amino groups and at least one of the selected amines is an alkyl amine.