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Process for preparation of polyaminotriazines

Imported: 23 Feb '17 | Published: 22 Oct '02

Kenji Kimura, Shinya Tanaka, Manji Sasaki

USPTO - Utility Patents

Abstract

Polyaminotriazines represented by formula (I) can be prepared by conducting a reduction alkylamination of a tetramethylpiperidone with a diamine represented by formula (IIb), NH

2—R—NH

2, in the presence of a hydrogenating catalyst, removing the catalyst upon completion of the reaction to obtain an unrefined crude product (A); and, conducting a polycondensation reaction of the unrefined crude product (A) and a dichlorotriazine in an aromatic solvent and in the presence of an inorganic base.

Claims

1. A process for preparing a polyaminotriazine represented by the formula (I):

wherein

NH

2—R—NH

2

2. A process according to claim 1, wherein the amount of the dichlorotriazine of the formula (III) is from 0.75 to about 1 mole per 1 mole of the diamine of the formula (IIb).

3. A process according to claim 1, wherein the amount of the dichlorotriazine of the formula (III) is from 0.8 to 0.9 mole per 1 mole of the diamine of the formula (IIb).

4. A process according to claim 1, wherein the crude product (A) is obtained by (i) conducting a reaction between a tetramethylpiperidone of the formula (IIa) and a dimaine of the formula (IIb) at about 50° C. to about 100° C. in the absence of a solvent while distilling off water, (ii) conducting a reduction alkylamination of the resulting product with hydrogen in the presence of a catalyst selected from the group consisting of platinum, palladium and Raney nickel to obtain a crude product containing catalyst, and (iii) thereafter, separating out said catalyst to obtain said crude product (A).

5. A process according to claim 1, wherein the crude product (A) is obtained by (i) conducting a reduction alkylamination of a tetramethylpiperidone of the formula (IIa) with a diamine of the formula (IIb) in the presence of a catalyst selected from the group consisting of platinum, palladium and Raney nickel, and in the presence of a solvent selected from the group consisting of methanol, ethanol, propanol and a mixture of any thereof with water, and, (ii) filtering off the catalyst and distilling off the solvent from (i).

6. A process according to claim 1, wherein the reduction alkylamination is conducted in the presence of 0.001 to 0.04 weight % of platinum or palladium at a temperature of from 40° C. to 140° C.

7. A process according to claim 1, wherein the reduction alkylamination is conducted in the presence of 0.1 to 30 weight % of Raney nickel, based on the tetramethylpiperidone of the formula (IIa), at a temperature of from 100° C. to 180° C.

8. A process according to claim 1, wherein the polycondensation reaction is conducted at an elevated pressure, by adding a solution of the dichlorotriazine represented by formula (III) in an aromatic solvent to a mixture of the crude product (A) and, as the inorganic base, a 50% aqueous solution of sodium hydroxide or potassium hydroxide while maintaining a temperature in the range of 145° C. to 200° C.

9. A process according to claim 1, wherein the polycondensation reaction is conducted at atmospheric pressure by adding a solution of the dichlorotriazine represented by formula (III) in an aromatic solvent to a mixture of the crude product (A) and, as the inorganic base, solid sodium hydroxide or potassium hydroxide which is kept at 145° C. to 190° C. while distilling off water and a part of the aromatic solvent.

10. A process according to claim 9, wherein the amount of the solvent present in the polycondensation is 0.1 to 1 weight part per 1 weight part of the crude product (A).

11. A process according to claim 9, wherein the mixture of the crude product (A) and solid sodium hydroxide or potassium hydroxide is kept at 155° C. to 180° C.

12. A process according to claim 9 or 11, wherein the amount of the solvent in the polycondensation is 0.2-0.8 weight part per 1 weight part of the crude product (A).

13. A process according to claim 1, wherein R

1 is hydrogen or methyl, R is straight chain alkylene having 2-12 carbon atoms and Q is —NHR

4 or —NR

4R

5.

14. A process according to claim 13, wherein Q is —NHR

4.

15. A process according to claim 14, wherein R

1 is hydrogen, R is hexamethylene and Q is 1,1,3,3-tetramethylbutylamino.

16. A process according to claim 1, wherein said inorganic base is sodium hydroxide or potassium hydroxide.

17. A process according to claim 1, or wherein said inorganic base is sodium hydroxide or potassium hydroxide, and said inorganic base is present in an amount of 2 to 3 moles per 1 mole of the dichlorotriazine of the formula (III).