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US5166326A Expired / Lapsed US ⏱️ 0.0 years remaining

Polymerizable metal-azo and metal-azomethine dyes

Assignee: 3M Co
•
Filing: 1991-03-11
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Granted: 1992-11-24
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Expires: 2011-03-11
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Abstract

Abstract Disclosed are metal-azo and metal-azomethine materials which are useful as monometric dyes which may be mordanted by polymerization. The inventive dyes contain a central metal; an azo containing ligand; and a ligand having a free-radically polymerizable group (not directly attached to the azo or azomethine containing ligand) bound to the metal, and optionally, a monodentate or bidentate ligand which satisfy the coordination requirements of the central metal. Also disclosed are homopolymers and copolymers of the metal-azo or metal azomethine dyes.

Inventors

  • 👤 Terrance P. Smith
  • 👤 David W. Malcomber
  • 👤 Mohammed A. Elmastry

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 11:16
CPC Classifications
C; C09; C09B; C09B56/00; C09B56/02; C09B62/00; C09B62/44; C09B62/465; C09B62/47; C09B62/477; C09B55/00; C09B69/00; C09B69/10

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 235 words
A polymerizable metal-azo or metal-azomethine dye, of the formula: wherein: Z 1 and Z 2 each independently represents an arene nucleus, with from 5 to 14 ring atoms each; G 1 and G 2 each independently represent a metal ligating group and further wherein G 1 and G 2 may be contained within or pendant from at least one of Z 1 and Z 2 ; R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, a sulfonyl group, a sulfoxyl group, an aryloxy group, a hydroxy group, a thioamido group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a sulfo group, a formyl group, an acyl group, a ureido group, or aryloxycarbonyl group, a silyl group, a carbonato group, or a sulfoalkoxy group; L 1 represents any 1°, 2°, or 3° nitrogen or 1°, 2°, or 3° phosphorus containing a vinyl group; L 2 represents a monodentate or polydentate ligand; X represents a nitrogen atom or a methine group; M is a divalent or polyvalent transition metal ion where the coordination number is at least four; and k, m, and n are whole numbers less than or equal to 3.
Claim 2
Dependent Claim 235 words
A polymerizable metal-azo or metal-azomethine dye, of the formula: wherein: Z 1 and Z 2 each independently represents an arene nucleus, with from 5 to 14 ring atoms each; G 1 and G 2 each independently represent a metal ligating group and further wherein G 1 and G 2 may be contained within or pendant from at least one of Z 1 and Z 2 ; R represents a hydrogen atom, a halogen atom, an alkyl group, an acylamino group, an alkoxy group, a sulfonamido group, an aryl group, a thiol group, an alkylthio group, an arylthio group, an alkylamino group, an arylamino group, an amino group, an alkoxycarbonyl group, an acyloxy group, a nitro group, a cyano group, a sulfonyl group, a sulfoxyl group, an aryloxy group, a hydroxy group, a thioamido group, a carbamoyl group, a sulfamoyl group, a carboxyl group, a sulfo group, a formyl group, an acyl group, a ureido group, or aryloxycarbonyl group, a silyl group, a carbonato group, or a sulfoalkoxy group; L 1 represents any 1°, 2°, or 3° nitrogen or 1°, 2°, or 3° phosphorus containing a vinyl group; L 2 represents a monodentate or polydentate ligand; X represents a nitrogen atom or a methine group; M is a divalent or polyvalent transition metal ion where the coordination number is at least four; and k, m, and n are whole numbers less than or equal to 3.
Claim 3
Dependent Claim 31 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 where Z 1 and Z 2 represent a heterocyclic or substituted heterocyclic nucleus or a carbocyclic or substituted carbocyclic aromatic nucleus.
Claim 4
Dependent Claim 26 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein at least one of Z 1 and Z 2 are arene nuclei containing only carbon.
Claim 5
Dependent Claim 31 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1, wherein G 1 and G are individually selected from the group consisting of oxygen, sulfur, amines, substituted amines, acylamido, and sulfonamido.
Claim 6
Dependent Claim 24 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein at least one of G 1 and G 2 is an oxygen atom.
Claim 7
Dependent Claim 16 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein L 1 is a vinylpyridine.
Claim 8
Dependent Claim 15 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein L 1 is 1-vinylimidazole.
Claim 9
Dependent Claim 16 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein L 1 is 4-vinyl-4'-methyl bipyridyl.
Claim 10
Dependent Claim 28 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein L 1 consists of a pyridine containing ligand which also contains a vinyl or an acrylate group.
Claim 11
Dependent Claim 15 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein L 1 is 4-vinylpyridine.
Claim 12
Dependent Claim 23 words
A polymerizable metal-azo or metal-azomethine dye according to claim 1 wherein M is selected from the group of chromium(III), nickel(II), palladium(II), and platinum(II).
Claim 13
Dependent Claim 14 words
A polymerizable metal-azo or metal-azo-methine dye according to claim 1 wherein M is chromium.

References Cited (Backward Citations)

US3756814A Cited
US4218367A Cited
US4605607A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-11-24 1996-05-25 1996-11-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-11-24 2000-05-25 2000-11-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-11-24 2004-05-25 2004-11-24 $7700.00 Window Closed / Lapsed

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