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US4820846A Expired / Lapsed US ⏱️ 0.0 years remaining

Triarylmethane compounds, their preparation and use as photoconductive systems

Assignee: 3M Co
•
Filing: 1983-09-12
•
Granted: 1989-04-11
•
Expires: 2003-09-12
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Abstract

Abstract Compounds which are useful as sensitizers of photoconductors, having the general formula: <IMAGE> (I) in which: like symbols represent identical substituents, at least 4 of R1 to R9 represent hydrogen atoms and the remaining R1 to R9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group, or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulfonic acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group or a tertiary amino group in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two such groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R1 to R9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, R10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus containing 5 or 6 members in the ring at least one of which is O, N or S, or an aromatic ring of the formula: <IMAGE> in which: R11 to R15 independently represent a hydrogen or halogen atom, an alkyl, substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R11 to R15 may additionally represent an aldehyde or acetyl group, or a dialkylamino group, up to two of R11 to R15 may additionally represent a cyano, carboxy, alkoxycarbonyl, sulfonic acid or nitro group, and any two adjacent R11 to R15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.

Inventors

  • 👤 D. E. Brown
  • 👤 Kenneth Reynolds

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 15:13
CPC Classifications
C; C09; C09B; C09B11/00; C09B11/04; C09B11/26; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0622; G03G5/0644; G03G5/0661

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 323 words
A compound of the general formula: ##STR10## in which: like symbols represent identical substituents, at least 4 of R 1 to R 9 represent hydrogen atoms and the remaining R 1 to R 9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group, or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulfonic acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group or a tertiary amino group in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two such groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R 1 to R 9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicylic, aromatic or heterocyclic ring, R 10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus containing 5 or 6 members in the ring at least one of which is O, N or S, or an aromatic ring of the formula: ##STR11## in which: R 11 to R 15 independently represent a hydrogen or halogen atom, an alkyl, substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R 11 to R 15 may additionally represent an aldehyde or acetyl group, or a dialkylamino group, up to two of R 11 to R 15 may additionally represent a cyano, carboxy, alkoxycarbonyl, sulfonic acid or nitro group, and any two adjacent R 11 to R 15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.
Claim 2
Dependent Claim 323 words
A compound of the general formula: ##STR10## in which: like symbols represent identical substituents, at least 4 of R 1 to R 9 represent hydrogen atoms and the remaining R 1 to R 9 pairs of groups independently represent: (i) hydrogen, an alkyl group having from 1 to 18 carbon atoms, a substituted alkyl group, or an aryl or substituted aryl group, (ii) a halogen atom, a cyano group, a carboxy or alkoxycarbonyl group, a hydroxy group, an alkoxy group, a nitro group or a sulfonic acid group, providing that not more than two such groups (ii) are present in each ring, (iii) an acylamino group, a secondary acylamino group or a tertiary amino group in which the pendant substituent groups on the nitrogen atom are alkyl, aryl or aralkyl, providing not more than two such groups (iii) may be present in each benzocarbazole ring, and (iv) any two groups R 1 to R 9 on adjacent carbon atoms in a ring may represent the necessary atoms to complete a fused alicylic, aromatic or heterocyclic ring, R 10 represents an alkyl or substituted alkyl group, an aralkyl group, or an aryl or substituted aryl group, Ar represents a heteroaromatic nucleus containing 5 or 6 members in the ring at least one of which is O, N or S, or an aromatic ring of the formula: ##STR11## in which: R 11 to R 15 independently represent a hydrogen or halogen atom, an alkyl, substituted alkyl, an aryl or substituted aryl, hydroxy, alkoxy or aryloxy group, one of R 11 to R 15 may additionally represent an aldehyde or acetyl group, or a dialkylamino group, up to two of R 11 to R 15 may additionally represent a cyano, carboxy, alkoxycarbonyl, sulfonic acid or nitro group, and any two adjacent R 11 to R 15 groups may represent the necessary atoms to complete a fused alicyclic, aromatic or heterocyclic ring, and X represents an anion.
Claim 3
Dependent Claim 17 words
A compound as claimed in claim 1, characterized in that X represents chloride, bromide or trifluoromethane sulfonate.
Claim 4
Dependent Claim 15 words
A compound as claimed in claim 1, characterized in that X represents tetrafluoroborate or perchlorate.
Claim 5
Dependent Claim 18 words
A compound as claimed in claim 1, characterized in that R 1 to R 9 are each hydrogen.
Claim 6
Dependent Claim 14 words
A compound as claimed in claim 1, characterized in that R 10 is ethyl.
Claim 7
Dependent Claim 21 words
A compound as claimed in claim 1, characterized in that at least three of R 11 to R 15 are hydrogen.
Claim 8
Dependent Claim 19 words
A compound as claimed in claim 1, characterized in that R 13 is dialkylamino, alkoxy or NO 2 .
Claim 9
Dependent Claim 64 words
A method of preparing a dye as claimed in claim 1, characterized in that bis(benzo[a]carbazol-5-yl)aryl methane is converted to the desired compound in accordance with the reaction scheme: ##STR12## in which R 1 to R 10 and Ar are as defined in claim 1, by oxidation utilizing lead tetra-acetate in the presence of acetic acid and/or trifluoroacetic acid or by photolysis in chloroform solution.
Claim 10
Dependent Claim 48 words
A photosensitive element comprising a support the surface of which is electrically conducting or is made electrically conductive by the provision of a conductive layer, the electrically conductive surface having coated thereon a photosensitive layer comprising a photoconductive material and as a sensitizer a compound of claim 1.
Claim 11
Dependent Claim 33 words
A photosensitive element as claimed in claim 9, characterized in that said compound is present in an effective sensitizing amount in the range of 0.01 to 10% by weight of the photosensitive layer.
Claim 12
Dependent Claim 17 words
A photosensitive element as claimed in claim 10, in which the photosensitive layer comprises a bis(benzo[a]carbazol-5-yl)aryl methane.
Claim 13
Dependent Claim 17 words
A photosensitive element as claimed in claim 11, in which the photosensitive layer comprises a bis(benzo[a]carbazol-5-yl)phenyl methane.
Claim 14
Dependent Claim 17 words
A photosensitive element as claimed in claim 9, in which the photosensitive layer comprises a bis[benzo[a]carbazol-5-yl)aryl methane.
Claim 15
Dependent Claim 17 words
A photosensitive element as claimed in claim 10, in which the photosensitive layer comprises a bis(benzo[a]carbazol-5-yl)phenyl methine.
Claim 16
Dependent Claim 18 words
A compound as claimed in claim 2, characterized in that R 1 to R 9 are each hydrogen.
Claim 17
Dependent Claim 18 words
A compound as claimed in claim 3, characterized in that R 1 to R 9 are each hydrogen.
Claim 18
Dependent Claim 14 words
A compound as claimed in claim 2, characterized in that R 10 is ethyl.
Claim 19
Dependent Claim 14 words
A compound as claimed in claim 3, characterized in that R 10 is ethyl.
Claim 20
Dependent Claim 21 words
A compound as claimed in claim 17, characterized in that at least three of R 11 to R 15 are hydrogen.
Claim 21
Dependent Claim 21 words
A compound as claimed in claim 18, characterized in that at least three of R 11 to R 15 are hydrogen.

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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) 1992-04-10 1992-10-10 1993-04-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-04-10 1996-10-10 1997-04-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-04-10 2000-10-10 2001-04-11 $7700.00 Window Closed / Lapsed

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