Antioxidants for overcoat layers and methods for making the same

Patent metadata

Field	Value
Publication number	US-9529286-B2
Application number	US-201314052471-A
Country	US
Kind code	B2
Filing date	Oct 11, 2013
Priority date	Oct 11, 2013
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

Antioxidants used for overcoat layers and processes for making the same. The present process for making the antioxidant has proven to be repeatable, cheaper, faster and safer than conventional processes. In particular, the present process uses a different solvent system where crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) is dissolved in methylethyl ketone at room temperature, followed by product precipitation in a warm mixture of ethanol and water.

First claim

What is claimed is:

1. A process for making purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) comprising:
dissolving crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) in a first solvent room temperature to form dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane);
heating a mixture of a second solvent and a third solvent to a temperature of about 50° C. or higher to form a warm co-solvent mixture;
adding the dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the warm co-solvent mixture in a drop-wise manner to form a precipitate mixture;
mixing the precipitate mixture;
cooling the precipitate mixture; and
drying the precipitate mixture to obtain the dried product comprising purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane), wherein the first, second and third solvents are not isopropanol.

2. The process of claim 1 , wherein the first solvent is selected from the group consisting of methylethyl ketone, acetone, pentanone, cyclohexanone, and mixtures thereof.

3. The process of claim 1 , wherein the second solvent is an alcohol.

4. The process of claim 1 , wherein the third solvent is water.

5. The process of claim 1 , wherein the first solvent is methyl ketone, the second solvent is ethanol and the third solvent is deionized water.

6. The process of claim 1 , wherein the step of dissolving crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) in the first solvent is performed at a temperature of from about 17 to about 28° C.

7. The process of claim 1 , wherein the step of adding the dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the warm co-solvent mixture is done at a rate of from about 5.0 g/min to about 130 g/min.

8. The process of claim 1 , wherein the step of heating the co-solvent mixture is done in a jacketed reactor.

9. The process of claim 1 , wherein the step of mixing the precipitate mixture is performed for from about 10 minutes to about 1 hour at a temperature of about 50° C. or higher.

10. The process of claim 9 , wherein the step of mixing the precipitate mixture is performed for about 10 minutes at a temperature of about 50° C.

11. The process of claim 1 , wherein a weight ratio of the amount of crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the amount of the first solvent used is from about 1.4:1 to about 1:1.

12. The process of claim 1 , wherein a ratio of the first solvent to the second solvent in the co-solvent mixture is from about 5:95 to about 95:5.

13. The process of claim 1 , wherein a product recovery yield of the purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) is about 85%.

14. The process of claim 1 , wherein the drying step is performed by vacuum filtration.

15. A process for making purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) comprising:
dissolving crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) in a first solvent at room temperature to form dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane);
heating a mixture of a second solvent and a third solvent to a temperature of from about 50° to about 65° C. to form a warm co-solvent mixture;
adding the dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the warm co-solvent mixture in a drop-wise manner to form a precipitate mixture;
mixing the precipitate mixture;
cooling the precipitate mixture; and
drying the precipitate mixture to obtain the dried product comprising purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane), wherein the purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) is of Type A polymorph, wherein the first, second and third solvents are not isopropanol.

16. The process of claim 15 , wherein the purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) is a white powder.

17. A process for making an overcoat layer for an imaging member comprising:
mixing together a melamine-formaldehyde crosslinking agent, a binder, a low surface energy compound, and an acid catalyst in a solvent to form an overcoat layer solution;
adding an antioxidant comprising purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the overcoat layer solution, the process of making the antioxidant comprising
dissolving crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) in a first solvent room temperature to form dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane),
heating a mixture of a second solvent and a third solvent to a temperature of from about 50° to about 65° C. to form a warm co-solvent mixture,
adding the dissolved crude bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) to the warm co-solvent mixture in a drop-wise manner to form a precipitate mixture,
mixing the precipitate mixture,
cooling the precipitate mixture, and
drying the precipitate mixture to obtain the dried product comprising purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane); and
drying the overcoat layer solution to yield an overcoat layer, wherein the first, second and third solvents are not isopropanol.

18. The process of claim 17 , wherein the overcoat layer has a thickness of from about 0.1 micrometer to about 10 micrometers.

19. The process of claim 17 , wherein the purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) is of Type A polymorph.

20. The process of claim 17 , wherein the purified bis(4-diethylamino-2-methylphenyl)-(4-diethylaminophenylmethane) has a high degree of crystallinity.

Assignees

• Xerox Corp

Inventors

• Mokhtari Mahya
• Saban Marko D

Classifications

• G03G5/14769 Primary

  Other polycondensates comprising nitrogen atoms with or without oxygen atoms in the main chain · CPC title

• B29L2009/00

  Layered products · CPC title

• C07C209/84

  Purification · CPC title

• B29K2105/0044

  Stabilisers, e.g. against oxydation, light or heat · CPC title

• B29C39/006

  Monomers or prepolymers (by reaction injection moulding B29C67/246) · CPC title