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US4368329A Expired / Lapsed US ⏱️ 0.0 years remaining

Process of preparing thiopyrylium sensitizing dyes

Assignee: 3M Co
•
Filing: 1981-02-27
•
Granted: 1983-01-11
•
Expires: 2001-02-27
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Abstract

Abstract A method of preparing a compound of the general formula: ##STR1## in which: R 1 and R 2 independently represent a hydrogen atom, an alkyl or substituted alkyl group, an aryl or substituted aryl group, an aralkyl or substituted aralkyl group, a cycloaliphatic or substituted cycloaliphatic group or a heterocyclic or substituted heterocyclic group providing R 1 and R 2 do not both represent cyclic groups of aromatic nature, or R 1 and R 2 together may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 3 , R 4 , R 5 and R 6 independently represent a hydrogen atom or any substituent providing the sum of their σ p constants has a value of less than +0.5, or R 3 and R 4 and/or R 5 and R 6 may represent the necessary atoms to complete an alicyclic or aromatic ring, R 3 and R 2 and/or R 1 and R 6 may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 7 and R 9 independently represent a hydrogen atom or any carbon linked substituent containing up to 16 carbon atoms, R 8 and R 10 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or any two adjacent substituents R 7 , R 8 , R 9 and R 10 together may complete an alicyclic or aromatic ring, and X - represents an anion, comprising reacting an amine of the general formula: ##STR2## in which R 1 to R 6 are as defined above, with a thiopyrylium salt of the general formula: ##STR3## in which X - and R 7 to R 10 are as defined above, to yield the desired compound. The compounds of formula (I), many of which are new, are useful as sensitizers or photoconductors.

Inventors

  • 👤 Alan R. Katritzky
  • 👤 Basil J. Graphakos
  • 👤 Girard A. F. Lhommet
  • 👤 Kenneth Reynolds

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 15:43
CPC Classifications
C; C07; C07D; C07D335/00; C07D335/02; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0622; G03G5/0624; G03G5/0635; G03G5/0637; G03G5/0644; G03G5/0661

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 285 words
A method of preparing a compound of the general formula: ##STR10## in which: R 1 and R 2 independently represent a hydrogen atom, an alkyl or substituted alkyl group, an aryl or substituted aryl group, an aralkyl or substituted aralkyl group, a cycloaliphatic or substituted cycloaliphatic group or a heterocyclic or substituted heterocyclic group providing R 1 and R 2 do not both represent cyclic groups of aromatic nature, or R 1 and R 2 together may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 3 , R 4 , R 5 and R 6 independently represent a hydrogen atom or any substituent providing the sum of their σ p constants has a value of less than ±0.5, or R 3 and R 4 and/or R 5 and R 6 may represent the necessary atoms to complete an alicyclic or aromatic ring, R 3 and R 2 and/or R 1 and R 6 may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 7 and R 9 independently represent a hydrogen atom or any carbon linked substituent containing up to 16 carbon atoms, R 8 and R 10 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or any two adjacent substituents R 7 , R 8 , R 9 and R 10 together may complete an alicyclic or aromatic ring, and X - represents an anion, comprising reacting an amine of the general formula: ##STR11## in which R 1 to R 6 are as defined above, with a thiopyrylium salt of the general formula: ##STR12## in which X - and R 7 and R 10 are as defined above, to yield the desired compound.
Claim 2
Independent Claim 285 words
A method of preparing a compound of the general formula: ##STR10## in which: R 1 and R 2 independently represent a hydrogen atom, an alkyl or substituted alkyl group, an aryl or substituted aryl group, an aralkyl or substituted aralkyl group, a cycloaliphatic or substituted cycloaliphatic group or a heterocyclic or substituted heterocyclic group providing R 1 and R 2 do not both represent cyclic groups of aromatic nature, or R 1 and R 2 together may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 3 , R 4 , R 5 and R 6 independently represent a hydrogen atom or any substituent providing the sum of their σ p constants has a value of less than ±0.5, or R 3 and R 4 and/or R 5 and R 6 may represent the necessary atoms to complete an alicyclic or aromatic ring, R 3 and R 2 and/or R 1 and R 6 may represent the necessary atoms to complete a non-aromatic heterocyclic ring, R 7 and R 9 independently represent a hydrogen atom or any carbon linked substituent containing up to 16 carbon atoms, R 8 and R 10 independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or any two adjacent substituents R 7 , R 8 , R 9 and R 10 together may complete an alicyclic or aromatic ring, and X - represents an anion, comprising reacting an amine of the general formula: ##STR11## in which R 1 to R 6 are as defined above, with a thiopyrylium salt of the general formula: ##STR12## in which X - and R 7 and R 10 are as defined above, to yield the desired compound.
Claim 3
Dependent Claim 41 words
A method as claimed in claim 1, in which R, R 4 , R 5 and R 6 independently represent a hydrogen atom or other substituent such that the sum of their σ p constants has a value less than ±0.4.
Claim 4
Dependent Claim 32 words
A method as claimed in claim 1 in which R 3 , R 4 , R 5 and R 6 are independently selected from H, alkyl, alkoxy, halogen and NH 2 .
Claim 5
Independent Claim 52 words
A method as claimed in claims 1, 2 or 3, in which R 1 and R 2 are independently selected from H, CH 3 , C 2 H 5 , C 6 H 5 , C 6 H 5 CH 2 , cyclo-C 6 H 11 and CH 2 CH 2 OH.
Claim 6
Dependent Claim 30 words
A method as claimed in claim 4 in which R 3 and R 2 and/or R 1 and R 6 comprise the atoms necessary to complete a non-aromatic heterocyclic ring.
Claim 7
Dependent Claim 24 words
A method as claimed in claim 1, in which R 8 =R 10 =H and R 7 =R 9 =C 6 H 5 .
Claim 8
Dependent Claim 24 words
A method as claimed in claim 4, in which R 8 =R 10 =H and R 7 =R 9 =C 6 H 5 .
Claim 9
Dependent Claim 16 words
A method as claimed in claim 1, which is conducted in a solvent at elevated temperature.

References Cited (Backward Citations)

US4315983A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-01-10 1986-07-12 1987-01-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-01-10 1990-07-12 1991-01-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-01-10 1994-07-12 1995-01-11 $7700.00 Window Closed / Lapsed

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