Meta-stable state nitrogen-containing polymer

• US 8,772,412 B2
• Filed: 12/29/2011
• Issued: 07/08/2014
• Est. Priority Date: 12/29/2010
• Status: Active Grant

• Current Assignee: Industrial Technology Research Institute
• Original Assignee: Industrial Technology Research Institute
• Inventors: Tsai, Li-Duan, Lin, Yueh-Wei, Cheng, Cheng-Liang, Pan, Jing-Pin, Wang, Tsung-Hsiung, Fang, Chia-Chen
• Primary Examiner(s): Truong, Duc
• Application Number:
  US13/339,386
• Publication Number:
  US 20120172558A1
• Time in Patent Office: 922 Days
• Field of Search: 525/326.7, 525/327.1, 525/328.2, 525/328.4, 525/329.4, 525/540, 528/423
• US Class Current: 525/326.7
• CPC Class Codes: C08F 222/404 substituted imides comprising oxygen other than the carboxy oxygen
• CPC Class Codes: C08F 222/406 substituted imides comprising nitrogen other than the imide nitrogen
• CPC Class Codes: C08F 222/408 substituted imides comprising other heteroatoms

Abstract

A meta-stable state nitrogen-containing polymer formed by reacting Compound (A) and Compound (B) is described. Compound (A) is a monomer having a reactive terminal functional group. Compound (B) is a heterocyclic amino aromatic derivative as an initiator. The molar ratio of Compound (A) to Compound (B) is from 10:1 to 1:10. The meta-stable state nitrogen-containing polymer has a variance less than 2% in its narrow molecular weight distribution after being retained at 55° C. for one month.

Claims

1. A meta-stable state nitrogen-containing polymer comprising a reaction product of reactants of a Compound (A) and a Compound (B), wherein the Compound (A) is a monomer with a reactive terminal functional group, the Compound (B) is a heterocyclic amino aromatic derivative as an initiator, and a molar ratio of the Compound (A) to the Compound (B) is from 10:

1 to 1;

10, wherein the Compound (B) is gradually added, in batches at multiple times, into a mixture solution of Compound (A)/solvent system at a reaction temperature for thermal polymerization.

2. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the Compound (B) is represented by one of Formula (I) to Formula (9):

3. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the Compound (B) comprises imidazole, an imidazole derivative, pyrrole, an pyrrole derivative, pyridine, 4-tert-butylpyridine, 3-butylpyridine, 4-dimethylaminopyridine, 2,4,6-triamino-1,3,5,-triazine, 2,4-dimethyl-2-imidazoline, pyridazine, pyrimidine, pyrazine, or a combination thereof.

4. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the Compound (A) comprises a maleimide, poly(ethylene glycol)dimethacrylate, bis[[4-[(vinyloxy)methyl]cyclohexyl]methyl]isophthalate), triallyl trimellitate, or a combination thereof,

wherein the maleimide is represented by one of Formula (10) to Formula (13):

5. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the Compound (A) comprises 4,4′

-diphenylmethane bismaleimide, oligomer of phenylmethane maleimide, m-phenylene bismaleimide, 2,2′

-bis[4-(4-maleimidophenoxy)phenyl]propane, 3,3′

-dimethyl-5,5′

-diethyl-4,4′

-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6′

-bismaleimide-(2,2,4-trimethyl)hexane, 4,4′

-diphenylether bismaleimide, 4,4′

-diphenylsulfone bismaleimide, 1,3-bis(3-maleimidophenoxy)-phenyl)-hexafluoropropane, 2,2-bis(p-maleimidophenyl)-hexafluoropropane, 1,8-bis-maleimidodiethylene glycol, tris(2-maleimidoethyl)amine, poly(ethylene glycol(11)) 4-maleimidophenyl methyl diether terminated, 4-maleimidophenol, 4-maleimido-benzenesulfonic acid, poly(ethylene glycol(11)) 2-maleimidoethyl methyl diether terminated, 2-maleimido propylene glycol 1-(2-methoxyethyl)ether, ethylene glycol 2-maleimidopropyl methyl diether, or poly(dimethsiloxane)bis(3-maleimido-propyl-dimethyl silyl) terminated.

6. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the molar ratio of the Compound (A) to the Compound (B) is from 1:

1 to 5;

1.

7. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the meta-stable state nitrogen-containing polymer is a narrow polydispersity polymer.

8. The meta-stable state nitrogen-containing polymer according to claim 7, wherein the meta-stable state nitrogen-containing polymer has a polydispersity index of 0.9-1.7.

9. The meta-stable state nitrogen-containing polymer according to claim 7, wherein the meta-stable state nitrogen-containing polymer has a GPC peak time of 19-24 minutes.

10. The meta-stable state nitrogen-containing polymer according to claim 1, wherein the meta-stable state nitrogen-containing polymer is re-induced to react at a temperature of 120-220°

C., to convert the meta-stable state nitrogen-containing polymer into a macromolecular polymer completely.