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US4404271A Expired / Lapsed US ⏱️ 0.0 years remaining

Metal complexes for use in developers for electrostatic images, charge control function

Assignee: Orient Chemical Industries Ltd
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Filing: 1981-12-11
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Granted: 1983-09-13
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Expires: 2001-12-11
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Abstract

Abstract A complex system for developing electrostatic images, and particularly a toner which contains a metal complex represented by the formula <IMAGE> wherein a or b is a benzene ring moiety or cyclohexene ring moiety with or without C4-C9 alkyl substituents, R1 and R2 are each hydrogen, C4-C9 alkyl or a substituent which may be in the form of a benzene ring moiety or cyclohexene ring moiety with or without C4-C9 alkyl substituents, provided that both R1 and R2 are not hydrogen at the same time, Me is Cr, Co or Fe, and X is a counter ion such as hydrogen or sodium. The metal complex has good compatibility with the resin component of the toner and is substantially colorless, imparting outstanding durability to the toner.

Inventors

  • 👤 Yoji Kawagishi
  • 👤 Yukihiko Ishida
  • 👤 Kazuhiro Ishikawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 15:55
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/04; C07F15/045; C07F11/00; C07F11/005; C07F15/06; C07F15/065; G; G03; G03G; G03G9/00; G03G9/08; G03G9/097; G03G9/09783; Y; Y10; Y10S; Y10S430/00; Y10S430/001; Y10S430/105

Claims Analysis

Total Claims: 33
Claim 1
Independent Claim 136 words
A toner composition for developing electrostatic images in the form of an admixture of a toner resin and a charge control agent comprising a metal complex having the formula ##STR5## wherein a or b, only one of which is present, is a corresponding fused benzene or cyclohexene ring moiety which is optionally substituted with a least one alkyl substituent having 4 to 9 carbon atoms, R 1 and R 2 are hydrogen or alkyl substituents having 4 to 9 carbon atoms or together form a corresponding fused benzene or cyclohexene ring moiety which is optionally substituted with at least one alkyl substituent having 4 to 9 carbon atoms, provided that both R 1 and R 2 are not hydrogen at the same time, Me is Cr, Co or Fe, and X is a corresponding counter ion.
Claim 2
Dependent Claim 136 words
A toner composition for developing electrostatic images in the form of an admixture of a toner resin and a charge control agent comprising a metal complex having the formula ##STR5## wherein a or b, only one of which is present, is a corresponding fused benzene or cyclohexene ring moiety which is optionally substituted with a least one alkyl substituent having 4 to 9 carbon atoms, R 1 and R 2 are hydrogen or alkyl substituents having 4 to 9 carbon atoms or together form a corresponding fused benzene or cyclohexene ring moiety which is optionally substituted with at least one alkyl substituent having 4 to 9 carbon atoms, provided that both R 1 and R 2 are not hydrogen at the same time, Me is Cr, Co or Fe, and X is a corresponding counter ion.
Claim 3
Dependent Claim 27 words
The composition according to claim 1, wherein the charge control agent is present in a charge control effective amount for controlling the charge of the toner resin.
Claim 4
Dependent Claim 14 words
The composition according to claim 2, wherein a coloring agent is also present therein.
Claim 5
Dependent Claim 15 words
The composition according to claim 1, wherein the metal complex is a symmetrical metal complex.
Claim 6
Dependent Claim 15 words
The composition according to claim 1, wherein the metal complex is an asymmetrical metal complex.
Claim 7
Dependent Claim 10 words
The composition according to claim 1, wherein Me is chromium.
Claim 8
Dependent Claim 10 words
The composition according to claim 1, wherein Me is cobalt.
Claim 9
Dependent Claim 10 words
The composition according to claim 1, wherein Me is iron.
Claim 10
Dependent Claim 19 words
The composition according to claim 1, wherein X is selected from the group consisting of hydrogen and alkali metal.
Claim 11
Dependent Claim 10 words
The composition according to claim 1, wherein X is hydrogen.
Claim 12
Dependent Claim 10 words
The composition according to claim 1, wherein X is sodium.
Claim 13
Dependent Claim 37 words
The composition according to claim 1, wherein a or b, only one of which is present, is a corresponding fused benzene ring moiety and R 1 and R 2 together form a corresponding fused benzene ring moiety.
Claim 14
Dependent Claim 15 words
The composition according to claim 12, wherein the metal complex is a symmetrical metal complex.
Claim 15
Dependent Claim 38 words
The composition according to claim 1, wherein a or b, only one of which is present, is a corresponding fused benzene ring moiety, R 1 is hydrogen and R 2 is alkyl having 4 to 9 carbon atoms.
Claim 16
Dependent Claim 67 words
The composition according to claim 1, wherein a or b, only one of which is present, is a corresponding fused benzene ring moiety which is substituted with at least one alkyl substituent having 4 to 9 carbon atoms, and R 1 and R 2 together form a corresponding fused benzene ring moiety which is substituted with at least one alkyl substituent having 4 to 9 carbon atoms.
Claim 17
Dependent Claim 15 words
The composition according to claim 15, wherein the metal complex is a symmetrical metal complex.
Claim 18
Dependent Claim 37 words
The composition according to claim 1, wherein a or b, only one of which is present, is a corresponding fused cyclohexene ring moiety, and R 1 and R 2 together form a corresponding fused cyclohexene ring moiety.
Claim 19
Dependent Claim 15 words
The composition according to claim 17, wherein the metal complex is a symmetrical metal complex.
Claim 20
Dependent Claim 24 words
The composition according to claim 1, wherein a coloring agent is also present therein, and the composition is in finely divided intimately intermixed form.
Claim 21
Dependent Claim 241 words
A toner composition for developing electrostatic images in the form of an admixture of a toner resin and a charge control agent comprising a metal complex having the formula ##STR6## wherein R is selected from the group consisting of a corresponding unsubstituted or C 4 to C 9 alkyl substituted fused benzene or cyclohexene ring moiety which is in a position vicinally ortho or meta to the oxygen linkage to Me and remote from the carbonyloxy linkage to Me, R 1 and R 2 are selected from the group consisting of hydrogen or C 4 to C 9 alkyl or together form a corresponding unsubstituted or C 4 to C 9 alkyl substituted fused benzene or cyclohexene ring moiety, provided that both R 1 and R 2 are not hydrogen at the same time, Me is a metal selected from the group consisting of chromium, cobalt and iron, and X is a corresponding counter ion, said metal complex being substantially colorless as well as capable of negatively charging toner resins for developing electrostatic images, and constituting the substantially equimolar reaction product, with a corresponding compound containing the metal Me, of substantially one molar equivalent of a first member selected from the group consisting of a corresponding hydroxy-naphthoic acid and a corresponding tetrahydro-hydroxy-naphthoic acid, and substantially one molar equivalent of a second member selected from the group consisting of a corresponding salicylic acid, a corresponding hydroxynaphthoic acid and a corresponding tetrahydro-hydroxy-naphthoic acid.
Claim 22
Dependent Claim 241 words
A toner composition for developing electrostatic images in the form of an admixture of a toner resin and a charge control agent comprising a metal complex having the formula ##STR6## wherein R is selected from the group consisting of a corresponding unsubstituted or C 4 to C 9 alkyl substituted fused benzene or cyclohexene ring moiety which is in a position vicinally ortho or meta to the oxygen linkage to Me and remote from the carbonyloxy linkage to Me, R 1 and R 2 are selected from the group consisting of hydrogen or C 4 to C 9 alkyl or together form a corresponding unsubstituted or C 4 to C 9 alkyl substituted fused benzene or cyclohexene ring moiety, provided that both R 1 and R 2 are not hydrogen at the same time, Me is a metal selected from the group consisting of chromium, cobalt and iron, and X is a corresponding counter ion, said metal complex being substantially colorless as well as capable of negatively charging toner resins for developing electrostatic images, and constituting the substantially equimolar reaction product, with a corresponding compound containing the metal Me, of substantially one molar equivalent of a first member selected from the group consisting of a corresponding hydroxy-naphthoic acid and a corresponding tetrahydro-hydroxy-naphthoic acid, and substantially one molar equivalent of a second member selected from the group consisting of a corresponding salicylic acid, a corresponding hydroxynaphthoic acid and a corresponding tetrahydro-hydroxy-naphthoic acid.
Claim 23
Dependent Claim 14 words
The composition according to claim 20, wherein a coloring agent is also present therein.
Claim 24
Dependent Claim 15 words
The composition according to claim 20, wherein the metal complex is a symmetrical metal complex.
Claim 25
Dependent Claim 15 words
The composition according to claim 20, wherein the metal complex is an asymmetrical metal complex.
Claim 26
Dependent Claim 19 words
The composition according to claim 20, wherein X is selected from the group consisting of hydrogen and alkali metal.
Claim 27
Dependent Claim 14 words
The composition according to claim 20, wherein Me is chromium and X is hydrogen.
Claim 28
Dependent Claim 30 words
The composition according to claim 20, wherein R is a corresponding unsubstituted fused benzene ring moiety, and R 1 and R 2 together form a corresponding fused benzene ring moiety.
Claim 29
Dependent Claim 30 words
The composition according to claim 20, wherein R is a corresponding unsubstituted fused benzene ring moiety, R 1 is hydrogen and R 2 is C 4 to C 9 alkyl.
Claim 30
Dependent Claim 44 words
The composition according to claim 20, wherein R is a a corresponding C 4 to C 9 alkyl substituted fused benzene ring moiety, and R 1 and R 2 together form a corresponding C 4 to C 9 alkyl substituted fused benzene ring moiety.
Claim 31
Dependent Claim 31 words
The composition according to claim 20, wherein R is a corresponding unsubstituted fused cyclohexene ring moiety, and R 1 and R 2 together form a corresponding unsubstituted fused cyclohexene ring moiety.
Claim 32
Dependent Claim 36 words
The composition according to claim 19, wherein the charge control agent is present in a charge control effective amount of substantially between about 0.1 to 10 parts by weight per 100 parts of the toner resin.
Claim 33
Dependent Claim 26 words
The composition according to claim 19 wherein the toner composition is admixed with a finely divided carrier therefor to provide a developer for developing electrostatic images.

References Cited (Backward Citations)

US3320169A Cited
US3826747A Cited
US3991226A Cited
US4024084A Cited
US4206064A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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