82965452 CLAIMS 1. Asymmetrical 2,5-disubstituted-1,4 ...
82965452
CLAIMS
What is claimed is:
1. Asymmetrical 2,5-disubstituted-1,4-diaminobenzenes.
2. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1 comprising 2,5—dinitro—substituted—1,4—diaminobenzenes.
10
3. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1 comprising 2,5-dialkylamino-substituted -1,4-diaminobenzenes.
4. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1
having the general formula
15
where R1 and R2 are different.
5. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 4,
wherein R1 and R2 are each selected from the group consisting of R3NH—, 2O
R4R5N—, R60—, and R7S—, where R3, R4, R5‘ R6, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear
lower aliphatic groups, cyclic aliphatic groups, homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof. 25
82965452
6. A coupling product of 2,5-disubstituted-1 ,4-diaminobenzene derivatives with a coupler.
7. The coupling product of claim 6, wherein the 2,5-disubstituted-1,4-
diaminobenzenes comprise 2,5-dinitro-substituted-1,4-diaminobenzenes.
8. The coupling product of claim 6, wherein the 2,5-disubstituted-1,4-
diaminobenzenes comprise 2,5—dialkylamino—substituted—1,4—diaminobenzenes.
10
9. The coupling product of claim 6, wherein the coupler is selected from the group consisting of blue, red, and yellow-green couplers.
10. The coupling product of claim 9, wherein the blue couplers are 1,3diaminobenzene derivatives with the ability to couple at the 2,4-positions relative 15
to the amino groups, the blue couplers being selected from the group consisting of N- and O-hydroxyethyl derivatives, dimeric couplers, and heterocyclic compounds.
11. The coupling product of claim 9, wherein the red couplers are 20
selected from the group consisting of 3-aminophenol, 5-amin02-methyl-phenol, and 1-naphthol.
12. The coupling product of claim 9, wherein the yellow-green couplers are selected from the group consisting of resorcinol, 4-cholroresorcinol, 25
benzodioxoles, 2-methylresorcinol, and their derivatives.
13. The coupling product of claim 6 having the general formula
82965452
where R1 and R2 are different and R1 and R2 are each selected from the group consisting of R3NH-, R4R5N-, RsO-, and R78-, where R3, R4, R5‘ R5, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear lower aliphatic groups, cyclic aliphatic groups, homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof.
10
14. A process for preparing 2,5—disubstituted—1,4—diaminobenzenes, the process including: providing 2,5-difluoro-1,4-dinitrobenzene; reacting 2,5-difluoro-1,4-dinitrobenzene with a first amine or a first
alcohol or a first thiol to form a mono-substituted product; and reacting the mono-substituted product with a second amine or a
15
second alcohol or a second thiol, respectively, to form a 2,5-disubstituted-1,4dinitrobenzene.
15. The process of claim 14 further including: reduction of the 2,5—disubstituted—1,4—dinitrobenzene to form a 2,5—
2O
disubstituted-1,4-diaminobenzene.
16. The process of claim 14, wherein the first amine and the second amine are the same or different, wherein the first alcohol and the second alcohol are the 25
same or different, and wherein the first thiol and the second thiol are the same or
different.
82965452
17. The process of claim 16, wherein the first amine and the second amine
are each selected from the group consisting of primary amines and secondary amines.
18. The process of claim 14, wherein the process of providing 2,5-difluoro-
1,4-dinitrobenzene includes: reacting 2,5—difluoroaniline with acetic anhydride to form N—(2,5— difluorophenyl)acetamide; 10
nitrating the N-(2,5-dif|uorophenyl)acetamide to form N-(2,5difluoro-4-nitrophenyl)acetamide; deprotecting the N-(2,5-difluoro-4-nitrophenyl)acetamide to form 2,5-difluoro-4-nitroaniline having an amino group in the 1 position; and oxidizing the amino group to the corresponding nitro group to form
15
2,5-difluoro-1,4-dinitrobenzene.
19. The process of claim 14 wherein the 2,5—disubstituted—1 ,4—
diaminobenzenes have the general formula
2O
where R1 and R2 are the same or different and R1 and R2 are each selected from the group consisting of R3NH-, R4R5N-, R50-, and R7S-, where R3, R4, R5, R5, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear lower aliphatic groups, cyclic aliphatic groups,
25
homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof.
CLAIMS
What is claimed is:
1. Asymmetrical 2,5-disubstituted-1,4-diaminobenzenes.
2. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1 comprising 2,5—dinitro—substituted—1,4—diaminobenzenes.
10
3. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1 comprising 2,5-dialkylamino-substituted -1,4-diaminobenzenes.
4. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 1
having the general formula
15
where R1 and R2 are different.
5. The asymmetrical 2,5-disubstituted-1,4-diaminobenzenes of claim 4,
wherein R1 and R2 are each selected from the group consisting of R3NH—, 2O
R4R5N—, R60—, and R7S—, where R3, R4, R5‘ R6, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear
lower aliphatic groups, cyclic aliphatic groups, homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof. 25
82965452
6. A coupling product of 2,5-disubstituted-1 ,4-diaminobenzene derivatives with a coupler.
7. The coupling product of claim 6, wherein the 2,5-disubstituted-1,4-
diaminobenzenes comprise 2,5-dinitro-substituted-1,4-diaminobenzenes.
8. The coupling product of claim 6, wherein the 2,5-disubstituted-1,4-
diaminobenzenes comprise 2,5—dialkylamino—substituted—1,4—diaminobenzenes.
10
9. The coupling product of claim 6, wherein the coupler is selected from the group consisting of blue, red, and yellow-green couplers.
10. The coupling product of claim 9, wherein the blue couplers are 1,3diaminobenzene derivatives with the ability to couple at the 2,4-positions relative 15
to the amino groups, the blue couplers being selected from the group consisting of N- and O-hydroxyethyl derivatives, dimeric couplers, and heterocyclic compounds.
11. The coupling product of claim 9, wherein the red couplers are 20
selected from the group consisting of 3-aminophenol, 5-amin02-methyl-phenol, and 1-naphthol.
12. The coupling product of claim 9, wherein the yellow-green couplers are selected from the group consisting of resorcinol, 4-cholroresorcinol, 25
benzodioxoles, 2-methylresorcinol, and their derivatives.
13. The coupling product of claim 6 having the general formula
82965452
where R1 and R2 are different and R1 and R2 are each selected from the group consisting of R3NH-, R4R5N-, RsO-, and R78-, where R3, R4, R5‘ R5, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear lower aliphatic groups, cyclic aliphatic groups, homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof.
10
14. A process for preparing 2,5—disubstituted—1,4—diaminobenzenes, the process including: providing 2,5-difluoro-1,4-dinitrobenzene; reacting 2,5-difluoro-1,4-dinitrobenzene with a first amine or a first
alcohol or a first thiol to form a mono-substituted product; and reacting the mono-substituted product with a second amine or a
15
second alcohol or a second thiol, respectively, to form a 2,5-disubstituted-1,4dinitrobenzene.
15. The process of claim 14 further including: reduction of the 2,5—disubstituted—1,4—dinitrobenzene to form a 2,5—
2O
disubstituted-1,4-diaminobenzene.
16. The process of claim 14, wherein the first amine and the second amine are the same or different, wherein the first alcohol and the second alcohol are the 25
same or different, and wherein the first thiol and the second thiol are the same or
different.
82965452
17. The process of claim 16, wherein the first amine and the second amine
are each selected from the group consisting of primary amines and secondary amines.
18. The process of claim 14, wherein the process of providing 2,5-difluoro-
1,4-dinitrobenzene includes: reacting 2,5—difluoroaniline with acetic anhydride to form N—(2,5— difluorophenyl)acetamide; 10
nitrating the N-(2,5-dif|uorophenyl)acetamide to form N-(2,5difluoro-4-nitrophenyl)acetamide; deprotecting the N-(2,5-difluoro-4-nitrophenyl)acetamide to form 2,5-difluoro-4-nitroaniline having an amino group in the 1 position; and oxidizing the amino group to the corresponding nitro group to form
15
2,5-difluoro-1,4-dinitrobenzene.
19. The process of claim 14 wherein the 2,5—disubstituted—1 ,4—
diaminobenzenes have the general formula
2O
where R1 and R2 are the same or different and R1 and R2 are each selected from the group consisting of R3NH-, R4R5N-, R50-, and R7S-, where R3, R4, R5, R5, and R7 are each independently selected from the group consisting of substituted and unsubstituted hydrocarbon groups containing from 1 to 24 carbon atoms, branched aliphatic groups, linear lower aliphatic groups, cyclic aliphatic groups,
25
homocyclic aryl groups, heterocyclic aryl groups, substituted derivatives thereof, and combinations thereof.
