US4283475A
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Pentamethine thiopyrylium salts, process for production thereof, and photoconductive compositions containing said salts
Assignee: Fujifilm Holdings Corp
•
Filing: 1980-08-20
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Granted: 1981-08-11
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Expires: 2000-08-20
Abstract
Abstract 2,6-Di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salts, which are novel, colorless, transparent, having an adsorption in the far infrared to near infrared region and capable of imparting high sensitivity to photoconductive substance; process for producing the salts; and a photoconductive composition containing the salt.
Inventors
- 👤 Koichi Kawamura
- 👤 Harumi Katsuyama
- 👤 Hideo Sato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:28
CPC Classifications
C; C07; C07D; C07D335/00; C07D335/02; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0666; G03G5/0668; G03G5/067
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
38 words
A photoconductive composition comprising a photoconductive material and a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of chemical structural formula (I) ##STR8## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group.
Claim 2
Dependent Claim
38 words
A photoconductive composition comprising a photoconductive material and a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of chemical structural formula (I) ##STR8## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group.
Claim 3
Dependent Claim
11 words
The composition of claim 1 wherein X is a hydrogen atom.
Claim 4
Dependent Claim
56 words
The composition of claim 1 wherein X represents a substituted or unsubstituted straight or branched chain alkyl group having 1 to 15 carbon atoms, wherein the substituent is selected from the group consisting of an alkoxy group having 1 to 5 carbon atoms, a halogen atom and an aryl group having 6 to 15 carbon atoms.
Claim 5
Dependent Claim
52 words
The composition of claim 1 wherein X represents a substituted or unsubstituted aryl group having 6 to 11 carbon atoms and the substituent is selected from the group consisting of an alkoxy group having 1 to 5 carbon atoms, a halogen atom and an alkyl group having 1 to 5 carbon atoms.
Claim 6
Dependent Claim
30 words
The composition of claim 1 wherein X represents a hydrogen atom, a methyl group, an ethyl group, a phenyl group, a benzyl group, a chlorine atom or a bromine atom.
Claim 7
Dependent Claim
26 words
The composition of claim 1 wherein said photoconductive substance is at least one member selected from the group consisting of poly-N-vinylcarbazole, triarylamines polyarylmethanes and pyrazoline derivatives.
Claim 8
Dependent Claim
29 words
A 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the following formula ##STR9## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group.
Claim 9
Dependent Claim
29 words
A 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the following formula ##STR9## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group.
Claim 10
Dependent Claim
23 words
The thiopyrylium salt of claim 7 wherein Z.sup.⊖ represents an anion of a strong acid having a pKa of not more than 5.
Claim 11
Dependent Claim
24 words
The thiopyrylium salt of claim 7 wherein said anion is a chloride ion, bromide ion, perchlorate ion, tetrafluoroborate ion, p-toluenesulfonate ion or trifluoroacetate ion.
Claim 12
Dependent Claim
65 words
The thiopyrylium salt of claim 7 wherein X represents a hydrogen atom, a linear or branched alkyl group having 1 to 15 carbon atoms, or a linear or branched alkyl group having 1 to 15 carbon atoms and a substituent selected from the group consisting of alkoxy groups having 1 to 5 carbon atoms, halogen atoms and aryl groups having 6 to 15 carbon atoms.
Claim 13
Dependent Claim
52 words
The thiopyrylium salt of claim 7 wherein X is a substituted or unsubstituted aryl group having 6 to 11 carbon atoms, said substituent being selected from the group consisting of an alkoxy group having 1 to 5 carbon atoms, a halogen atom and an alkyl group having 1 to 5 carbon atoms.
Claim 14
Dependent Claim
31 words
The thiopyrylium salt of claim 7 wherein X represents a hydrogen atom, a methyl group, an ethyl group, a phenyl group, a benzyl group, a chlorine atom or a bromine atom.
Claim 15
Dependent Claim
18 words
The thiopyrylium salt of claim 1 wherein said halogen atom is a fluorine, chlorine, bromine or iodine atom.
Claim 16
Dependent Claim
79 words
A process for preparing a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the formula (I) ##STR10## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, which comprises reacting a 2,6-di-tert-butyl-4-methylthiopyrylium salt of chemical structural formula (II) ##STR11## wherein Z.sup.⊖ is as defined above, with a 1-phenylamino-3-phenylimino-1-propene of the formula (III) ##STR12## wherein X is as defined above, or with a salt derived from said compound of formula (III) and an acid.
Claim 17
Dependent Claim
79 words
A process for preparing a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the formula (I) ##STR10## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, which comprises reacting a 2,6-di-tert-butyl-4-methylthiopyrylium salt of chemical structural formula (II) ##STR11## wherein Z.sup.⊖ is as defined above, with a 1-phenylamino-3-phenylimino-1-propene of the formula (III) ##STR12## wherein X is as defined above, or with a salt derived from said compound of formula (III) and an acid.
Claim 18
Dependent Claim
25 words
The process of claim 14 wherein said acid forming said salt with the 1-phenylamino-3-phenylimino-1-propene is an acid having a pKa of not more than 4.
Claim 19
Dependent Claim
22 words
The process of claim 14 wherein said acid forming said salt with the 1-phenylamino-3-phenylimino-1-propene is hydrochloric acid, hydrobromic acid or sulfuric acid.
Claim 20
Dependent Claim
22 words
The process of claim 14 wherein the reaction is carried out in a carboxylic acid anhydride in the presence of a base.
Claim 21
Dependent Claim
11 words
The process of claim 17 wherein said base is an amine.
Claim 22
Dependent Claim
13 words
The process of claim 17 wherein said carboxylic acid anhydride is acetic anhydride.
Claim 23
Dependent Claim
14 words
The process of claim 14 wherein the reaction is carried out in an amine.
Claim 24
Dependent Claim
78 words
A process for preparing a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the formula (I) ##STR13## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group, which comprises reacting a 2,6-di-tert-butyl-4-methylthiopyrylium salt of the formula (II) ##STR14## wherein Z.sup.⊖ is as defined above, with a 1,1,3,3-tetraalkoxypropane of the formula (IV) (RO).sub.2 CHCHXCH(OR).sub.2 (IV) wherein X is as defined above, and R represents an alkyl group having 1 to 4 carbon atoms.
Claim 25
Dependent Claim
78 words
A process for preparing a 2,6-di-tert-butyl-4-[5-(2,6-di-tert-butyl-4H-thiopyran-4-ylidene)penta-1,3-dienyl]thiopyrylium salt of the formula (I) ##STR13## wherein Z.sup.⊖ represents an anion, and X represents a hydrogen atom, a halogen atom, an alkyl group or an aryl group, which comprises reacting a 2,6-di-tert-butyl-4-methylthiopyrylium salt of the formula (II) ##STR14## wherein Z.sup.⊖ is as defined above, with a 1,1,3,3-tetraalkoxypropane of the formula (IV) (RO).sub.2 CHCHXCH(OR).sub.2 (IV) wherein X is as defined above, and R represents an alkyl group having 1 to 4 carbon atoms.
Claim 26
Dependent Claim
26 words
The process of claim 21 wherein the reaction is carried out in a carboxylic acid or a carboxylic acid anhydride in the presence of an amine.
Claim 27
Dependent Claim
12 words
The process of claim 22 wherein said carboxylic acid is acetic acid.
Claim 28
Dependent Claim
14 words
The process of claim 22 wherein said carboxylic acid anhydride is acetic acid anhydride.
Claim 29
Dependent Claim
24 words
The process of claims 14 or 21 wherein Z.sup.⊖ represents an anion of a strong acid having a pKa of not more than 5.
Claim 30
Dependent Claim
25 words
The process of claims 14 or 21 wherein said anion is a chloride ion, bromide ion, perchlorate ion tetrafluoroborate ion, p-toluenesulfonate ion, or trifluoroacetate ion.
Claim 31
Dependent Claim
62 words
The process of claims 14 or 21 wherein X represents a hydrogen atom, a substituted or unsubstituted straight chain or branched chain alkyl group having 1 to 15 carbon atoms, and the substituent is selected from the group consisting of an alkoxy group having 1 to 5 carbon atoms, a halogen atom and an aryl group having 6 to 15 carbon atoms.
Claim 32
Dependent Claim
54 words
The process of claims 14 or 21 wherein X represents a substituted or unsubstituted aryl group having 6 to 11 carbon atoms, and said substituent is selected from the group consisting of an alkoxy group having 1 to 5 carbon atoms, a halogen atom and an alkyl group having 1 to 5 carbon atoms.
Claim 33
Dependent Claim
32 words
The process of claims 14 or 21 wherein X represents a hydrogen atom, a methyl group, an ethyl group, a phenyl group, a benzyl group, a chlorine atom or a bromine atom.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-10 | 1985-02-09 | 1985-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-10 | 1989-02-09 | 1989-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-10 | 1993-02-09 | 1993-08-11 | $7700.00 | Window Closed / Lapsed |