Claims
- 1. A 2-(N-R-N-R.sup.1)amino-3-R.sup.2 -6-(N-R.sup.3 -N-R.sup.4)amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran having the formula ##STR17## wherein: R and R.sup.3 independently represent hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, C.sub.4 to C.sub.8 cycloalkyl, phenyl, phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo, benzyl, benzyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo, or ##STR18## in which R.sup.9 represents hydrogen, or non-tertiary C.sub.1 to C.sub.4 alkyl with the proviso that at least one of R and R.sup.3 is ##STR19## R.sup.1 represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, formyl, non-tertiary C.sub.2 to C.sub.4 acyl, benzoyl, benzoyl substituted in the benzene ring by one or two of halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro, phenylcarbamyl, naphthylcarbamyl, phenylsulfonyl, phenylsulfonyl substituted in the benzene ring by one or two of halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro, benzyl or benzyl substituted in the benzene ring by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C1 to C4 alkoxy or halo;
- R.sup.2 represents hydrogen, halo or non-tertiary C.sub.1 to C.sub.4 alkyl;
- R.sup.4 represents hydrogen, non-tertiary C.sub.1 to C.sub.4 alkyl, benzyl or benzyl substituted in the benzene ring by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo;
- R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached represent pyrrolidino, piperidino or morpholino;
- R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each independently represent hydrogen, halo, nitro or when R.sup.5, R.sup.8 and one of R.sup.6 and R.sup.7 are each hydrogen, the other of R.sup.6 and R.sup.7 represents COOY in which Y represents hydrogen or non-tertiary C.sub.1 to C.sub.18 alkyl.
- 2. A 2-[N-2-(R.sup.9 -pyridyl)ethyl-N-R.sup.1 ]amino-3-R.sup.2 -6-(N-R.sup.3 -N-R.sup.4)amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran according to claim 1 having the formula ##STR20## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each have the same respective meanings given in claim 1.
- 3. A compound according to claim 2 wherein R.sup.1 represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, formyl, non-tertiary C.sub.2 to C.sub.4 acyl, phenylcarbamyl, naphthylcarbamyl, benzyl or benzyl substituted in the benzene ring by one or two of halo, non-tertiary C.sub.1 to C.sub.4 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or nitro; R.sup.2 represents hydrogen or non-tertiary C.sub.1 to C.sub.4 alky; R.sup.3 represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, C.sub.4 to C.sub.8 cycloalkyl, phenyl or phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo; R.sup.4 represents hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached represent pyrrolidino, piperidino or morpholino; and R.sup.5 and R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen or when R.sup.5, R.sup.8 and one of R.sup.6 and R.sup.7 are each hydrogen the other of R.sup.6 and R.sup.7 represents COOY in which Y represents hydrogen or non-tertiary C.sub.1 to C.sub.18 alkyl.
- 4. A compound according to claim 3 wherein R.sup.1 represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl or benzyl; R.sup.3 and R.sup.4 each independently represent hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen.
- 5. A compound according to claim 4 selected from the group consisting of 2-[2-(2-pyridyl)ethyl]amino-6-diethylaminofluoran; 2-[2-(2-pyridyl)ethyl]amino-3-methyl-6-diethylaminofluoran; 2-[2-(4-pyridyl)ethyl]amino-3-methyl-6-diethylaminofluoran; 2-{N-ethyl-N-[2-(2-pyridyl)ethyl]}amino-6-diethylaminofluoran; and 2-{N-benzyl-N-[2-(2-pyridyl)ethyl]}amino-6-diethylaminofluoran.
- 6. A compound according to claim 3 wherein R.sup.1 represents hydrogen or non-tertiary C.sub.1 to C.sub.8 alkyl; R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached represent pyrrolidino, piperidino or morpholino; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen.
- 7. 2-[2-(2-Pyridyl)ethyl]amino-3-methyl-6-pyrrolidinofluoran according to claim 6.
- 8. A compound according to claim 3 wherein R.sup.1 represents formyl or non-tertiary C.sub.2 to C.sub.4 acyl; R.sup.3 and R.sup.4 each independently represent hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen.
- 9. A compound according to claim 2 selected from the group consisting of 2-{N-formyl-N-[2-(2-pyridyl)ethyl}amino-6-diethylaminofluoran; 2-{N-acetyl-N-[2-(2-pyridyl)ethyl]}amino-6-diethylaminofluoran; 2-{N-formyl-N-[2-(2-pyridyl)ethyl]}amino-3-methyl-6-diethylaminofluoran; and 2-{N-acetyl-N-[2-(2-pyridyl)ethyl]}amino-3-methyl-6-diethylaminofluoran.
- 10. A compound according to claim 3 wherein R.sup.1 represents phenylcarbamyl or naphthylcarbamyl; R.sup.3 and R.sup.4 each independently represent hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen.
- 11. A compound according to claim 10 selected from the group consisting of 2-{N-naphthylcarbamyl-N-[2-(2-pyridyl)ethyl]}amino-6-diethylaminofluoran; and 2-{N-naphthylcarbamyl-N-[2-(2-pyridyl)ethyl]}amino-3-methyl-6-diethylaminofluoran.
- 12. A compound according to claim 3 wherein R.sup.1 represents hydrogen or non-tertiary C.sub.1 to C.sub.8 alkyl; R.sup.3 and R.sup.4 each independently represent hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; and R.sup.5, R.sup.8 and one of R.sup.6 and R.sup.7 each represent hydrogen and the other of R.sup.6 and R.sup.7 represents COOY in which Y represents hydrogen or non-tertiary C.sub.1 to C.sub.18 alkyl.
- 13. A compound according to claim 12 selected from the group consisting of 2-[2-(2-pyridyl)ethyl]amino-3-methyl-6-diethylamino-5'/6'-carboxyfluoran; and 2-[2-(2-pyridyl)ethyl]amino-3-methyl-6-diethylamino-5'/6'-ethoxycarbonylfluoran.
- 14. A 2-(N-R-N-R.sup.1)amino-3-R.sup.2 -{6-[N-2-(R.sup.9 -pyridyl)ethyl]-N-R.sup.4 }amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran according to claim 1 having the formula ##STR21## wherein R, R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each have the same respective meanings given in claim 1.
- 15. A compound according to claim 14 wherein R represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, phenyl, phenyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo, benzyl or benzyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo; R.sup.1 represents hydrogen, non-tertiary C.sub.1 to C.sub.8 alkyl, benzyl or benzyl substituted by one or two of C.sub.1 to C.sub.3 alkyl, non-tertiary C.sub.1 to C.sub.4 alkoxy or halo; R.sup.2 represents hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; R.sup.4 represents hydrogen or non-tertiary C.sub.1 to C.sub.4 alkyl; and R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each represent hydrogen.
- 16. A compound according to claim 15 selected from the group consisting of 2-anilino-3-methyl-6-{N-methyl-N-[2-(2-pyridyl)ethyl]}aminofluoran and 2-anilino-6-{N-methyl-N-[2-(2-pyridyl)ethyl]}aminofluoran.
- 17. A pressure-sensitive carbonless duplicating system or thermal-responsive marking system comprising a support sheet coated with a layer containing as a color-forming substance a 2-(N-R-N-R.sup.1)amino-3-R.sup.2 -6-(N-R.sup.3 -N-R.sup.4)amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran according to claim 1 wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 each have the same respective meanings given in claim 1.
- 18. A pressure-sensitive carbonless duplicating system or thermal-responsive marking system comprising a support sheet coated with a layer containing as a color-forming substance a 2-{N-[2-(R.sup.9 -pyridyl)ethyl]-N-R.sup.1 }amino-3-R.sup.2 -6-(N-R.sup.3 -N-R.sup.4)amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran according to claim 2 wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each have the same respective meanings given in claim 2.
- 19. A pressure-sensitive carbonless duplicating system or thermal-responsive marking system according to claim 18 containing as a color-forming substance a compound selected from the group consisting of 2-[2-(2-pyridyl)ethyl]amino-6-diethylaminofluoran and 2-[2-(2-pyridyl)ethyl]amino-3-methyl-6-diethylaminofluoran.
- 20. A pressure-sensitive carbonless duplicating system or thermal-responsive marking system comprising a support sheet coated with a layer containing as a color-forming substance a 2-(N-R-N-R.sup.1)amino-3-R.sup.2 -6-{N-[2-(R.sup.9 -pyridyl)ethyl]-N-R.sup.4 }amino-4'-R.sup.5 -5'-R.sup.6 -6'-R.sup.7 -7'-R.sup.8 -fluoran according to claim 14 wherein R, R.sup.1, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 each have the same respective meanings given in claim 14.
- 21. A pressure-sensitive carbonless duplicating system or thermal-responsive marking system according to claim 20 containing as a color-forming substance a compound selected from the group consisting of 2-anilino-6-}N-methyl-N-[2-(2-pyridyl)ethyl]}aminofluoran and 2-anilino-3-methyl-6-{N-methyl-N-[2-(2-pyridyl)ethyl]}aminofluoran.
- 22. A pressure-sensitive carbonless duplicating system according to claim 17 comprising a support sheet coated on one side with a layer of pressure-rupturable microcapsules containing a liquid solution of the color-forming substance.
- 23. A thermal-responsive marking system according to claim 17 comprising a support sheet coated on one side with a layer containing a mixture of the color-forming substance and an acid developer arranged such that application of heat will produce a mark-forming reaction between the color-forming substance and the acidic developer.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a division of application Ser. No. 549,057, filed Nov. 7, 1983, now abandoned, which in turn is a continuation-in-part of our copending application Ser. No. 445,537, filed Nov. 30, 1982, and now U.S. Pat. No. 4,447,616.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3901918 |
Koga et al. |
Aug 1975 |
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Divisions (1)
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Number |
Date |
Country |
Parent |
549057 |
Nov 1983 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
445537 |
Nov 1982 |
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