US4749796A
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Xanthene derivative and a production process of the same
Assignee: Hodogaya Chemical Co Ltd
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Filing: 1985-12-06
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Granted: 1988-06-07
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Expires: 2005-12-06
Abstract
Abstract This invention relates to a xanthene derivative that develops color on oxidation, so that it is favorably used for a photoresist, a PS plate or a proofing agent. The xanthene derivative, which has the following structural formula (I), is produced by putting a fluoran derivative represented by the following structural formula (II) to an esterification reaction and then to a reduction reaction. <IMAGE> (I) <IMAGE> (II) In the above formulae R1 and R2 independently stand for hydrogen, an alkyl radical with 1 to 8 carbon atoms, a tetrahydrofurfuryl radical, a substitued or an unsubstituted phenyl radical, a substituted or an unsubstituted benzyl radical or a cyclic alkyl radical; in addition, R1 and R2 are able to form a ring in pairs. R3 and R6 independently stand for hydrogen, chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical. R4 and R5 independently stand for hydrogen, chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical, a lower alkoxyalkyl radical, a substituted or an unsubstituted phenyl radical, a substituted or an unsubstituted benzyl radical, an amino radical, a N-substituted or N,N-substituted amino radical or a cyclic alkyl radical; in addition, R3 and R4, R4 and R5, and R5 and R6 are able to form a ring in pairs respectively. R7 stands for an alkyl radical, a substituted or an unsubstituted phenyl radical or a substituted or an unsubstituted benzyl radical. X stands for hydrogen, chlorine, fluorine, bromine, a nitro radical, a lower alkyl radical or a lower alkylamino radical; and n stands for an integer from 1 to 4 inclusive.
Inventors
- 👤 Hideyuki Sensui
- 👤 Michihiro Gonda
- 👤 Toshio Obara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:57
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/09; G03F7/105; C; C07; C07D; C07D311/00; C07D311/02; C07D311/78; C07D311/80; C07D311/82
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
355 words
A xanthene derivative represented by the structural formula (I) ##STR50## which is colorless or only slightly colored, is stable in air and develops colour on oxidation wherein R 1 and R 2 independently stand for hydrogen, an alkyl radical with 1 to 8 carbon atoms, a tetrahydrofurfuryl radical, a phenyl radical, a benzyl radical or a cyclic alkyl radical; in addition, R 1 and R 2 are able to form a ring in pairs; R 3 and R 6 independently stand for hydrogen, chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical; R 4 stands for hydrogen, chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical, a lower alkoxyalkyl radical, a phenyl radical, a benzyl radical or a cyclic alkyl radical; R 5 stands for hydrogen, chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical, a lower alkoxyalkyl radical, a phenyl radical, a benzyl radical, an amino radical, or a cyclic alkyl radical; R 7 stands for an alkyl radical, a phenyl radical or a benzyl radical, when any one of R 1 , R 2 , R 4 , R 5 or R 7 is a phenyl radical or a benzyl radical the phenyl radical and benzene radical may be unsubstituted or may be substituted by chlorine, fluorine, lower alkyl radical or lower alkoxy radical and when R 5 is an amino radical the amino radical may be unsubstituted or may be N-substituted or N,N-disubstituted with a substituent selected from the group consisting of a lower alkyl radical, unsubstituted phenyl radical, a phenyl radical substituted with chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical or an acetyl radical, an unsubstituted benzyl radical and a benzyl radical substituted with chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical; in addition, R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 are able to form a ring in pairs respectively, X stands for hydrogen, chlorine, fluorine, bromine, a nitro radical, a lower alkyl radical or a lower alkylamino radical; and n stands for an integer from 1 to 4 inclusive.
Claim 2
Dependent Claim
355 words
A xanthene derivative represented by the structural formula (I) ##STR50## which is colorless or only slightly colored, is stable in air and develops colour on oxidation wherein R 1 and R 2 independently stand for hydrogen, an alkyl radical with 1 to 8 carbon atoms, a tetrahydrofurfuryl radical, a phenyl radical, a benzyl radical or a cyclic alkyl radical; in addition, R 1 and R 2 are able to form a ring in pairs; R 3 and R 6 independently stand for hydrogen, chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical; R 4 stands for hydrogen, chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical, a lower alkoxyalkyl radical, a phenyl radical, a benzyl radical or a cyclic alkyl radical; R 5 stands for hydrogen, chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical, a lower alkoxyalkyl radical, a phenyl radical, a benzyl radical, an amino radical, or a cyclic alkyl radical; R 7 stands for an alkyl radical, a phenyl radical or a benzyl radical, when any one of R 1 , R 2 , R 4 , R 5 or R 7 is a phenyl radical or a benzyl radical the phenyl radical and benzene radical may be unsubstituted or may be substituted by chlorine, fluorine, lower alkyl radical or lower alkoxy radical and when R 5 is an amino radical the amino radical may be unsubstituted or may be N-substituted or N,N-disubstituted with a substituent selected from the group consisting of a lower alkyl radical, unsubstituted phenyl radical, a phenyl radical substituted with chlorine, fluorine, a lower alkyl radical, a lower alkoxy radical or an acetyl radical, an unsubstituted benzyl radical and a benzyl radical substituted with chlorine, fluorine, a lower alkyl radical or a lower alkoxy radical; in addition, R 3 and R 4 , R 4 and R 5 , and R 5 and R 6 are able to form a ring in pairs respectively, X stands for hydrogen, chlorine, fluorine, bromine, a nitro radical, a lower alkyl radical or a lower alkylamino radical; and n stands for an integer from 1 to 4 inclusive.
Claim 3
Dependent Claim
188 words
The xanthene derivative of the structural formula (I) according to claim 1 wherein R 1 and R 2 , independently, represent hydrogen, methyl, ethyl, propyl, butyl, pentyl, isopentyl, hexyl, heptyl, octyl, tetrahydrofurfuryl, phenyl, o-, m-, or p-tolyl, xylyl, benzyl or cyclohexyl; R 3 and R 6 , independently, represent hydrogen, chlorine, fluorine, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy or butoxy; R 4 represents hydrogen, chlorine, fluorine, methyl, ethyl, butyl, pentyl, isopentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, ethoxyethyl, ethoxymethyl, methoxyethyl, phenyl, o-, m-, or p-tolyl, xylyl, or benzyl; R 5 represents hydrogen, chlorine, fluorine, methyl, ethyl, butyl, pentyl, isopentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, ethoxyethyl, ethoxymethyl, methoxyethyl, phenyl, o-, m-, or p-tolyl, xylyl, or benzyl, o-, m-, or p-chlorobenzyl, amino, methylamino, ethylamino, propylamino, butylamino, phenylamino, o-, m-, or p-chlorophenylamino, tetrahydrofurfurylamino, benzyl-amino, o-, m-, or p-chlorobenzylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, diphenylamino di(o-, m-, or p-chlorophenyl)-amino, ditetrahydrofurfurylamino, dibenzylamino or di(o-, m-, or p-chlorophenyl)amino; R 7 represents methyl, ethyl, propyl, butyl, phenyl, o-, m-, or p-chlorophenyl, benzyl, or o-, m-, or p-chlorobenzyl; and X represents hydrogen, chlorine, fluorine, bromine, nitro, methyl, ethyl, propyl, butyl, diethylamino, or dimethylamino.
Claim 4
Dependent Claim
18 words
The xanthene derivative represented by the structural formula (I) as set forth in claim 1 which is 2-(2-chlorophenyl)-amino-6-N,N-dibutyl-amino-9-(2-methoxycarbonyl)-phenylxanthene.
Claim 5
Dependent Claim
18 words
The xanthene derivative represented by the structural formula (I) as set forth in claim 1 which is 2-N,N-dibenzylamino-6-N,N-diethylamino-9-(2-methoxycarbonyl)-phenylxanthene.
Claim 6
Dependent Claim
18 words
The xanthene derivative represented by the structural formula (I) as set forth in claim 1 which is benzo-6-N,N-diethylamino-9-(2-methoxycarbonyl)-phenylxanthene.
Claim 7
Dependent Claim
18 words
The xanthene derivative represented by the structural formula (I) as set forth in claim 1 which is 2-(2-chlorophenyl)-amino-6-N,N-diethylamino-9-(2-methoxycarbonyl)phenylxanthene.
Claim 8
Dependent Claim
17 words
The xanthene derivative represented by the structural formula (I) set forth in claim 1 which is 2-anilino-3-methyl-6-N-methyl-N-cyclohexylamino-9-(2-methoxycarbonyl)-phenylxanthene.
Claim 9
Dependent Claim
56 words
A production process of a xanthene derivative represented by the structural formula (I) as set forth in claim 1, which is characterized by subjecting a fluoran derivative represented by the structural formula (II) ##STR51## wherein R 1 -R 6 , X and n are as defined, to an esterification reaction and then to a reduction reaction.
Claim 10
Dependent Claim
35 words
A production process of a xanthene derivative according to claim 8 in which said esterification reaction is made between said fluoran derivative and an alcohol or a phenol derivative in the presence of an acid.
Claim 11
Dependent Claim
30 words
A production process of a xanthene derivative according to claim 8 in which said esterification reaction is made between said fluoran derivative and an alkyl halide or a dialkyl sulfate.
Claim 12
Dependent Claim
25 words
A production process of a xanthene derivative according to claim 8 in which sodium borohydride is used in said reduction reaction as a reducing agent.
Claim 13
Dependent Claim
31 words
A production process of a xanthene derivative according to claim 8 in which platinum oxide, palladium on carbon, or Raney nickel is used in said reduction reaction as a reducing agent.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1991-06-07 | 1991-12-07 | 1992-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-06-07 | 1995-12-07 | 1996-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-06-07 | 1999-12-07 | 2000-06-07 | $7700.00 | Window Closed / Lapsed |