# US 8,784,548 B2 · Phthalocyanines and naphthalocyanines with near-IR absorptions for inkjet inks

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- Number: US 8,784,548 B2
- Document ID: US8784548B2
- Status: Granted
- Kind: B2
- Application number: 13/383,718
- Filed: 2009-07-31
- Published: 2012-06-07
- Granted: 2014-07-22
- Earliest claimed: 2009-07-31
- Assignees: Hewlett-Packard Development Company, L.P.
- Applicants: Sivapackia Ganapathiappan; Jayprakash Bhatt
- Inventors: Sivapackia Ganapathiappan; Jayprakash Bhatt
- Web page: https://patentgrep.com/patent/US8784548B2

## CPC

- C09B 7/00: Indigoid dyes
- C09B 47/18: Obtaining compounds having oxygen atoms directly bound to the phthalocyanine skeleton
- C09B 47/24: Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B 69/108: {containing a phthalocyanine dye}
- C09D 11/328: characterised by dyes
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprises at least one complexed unit. Each unit comprises a phthalocyanine or a naphthalocyanine moiety and, optionally, a metal atom complexed thereto and, if present, having a valency of from 1 to 5, with two valencies complexed to the phthalocyanine ring or the naphthalocyanine ring. Each unit has two linker moieties on opposite sides or adjacent sides of the unit, wherein water-soluble groups are present on at least one of the linkers, on the metal atom, and optionally on the phthalocyanine or naphthalocyanine moiety.

## Claims

### Claim 1

A water-soluble phthalocyanine dye or naphthalocyanine dye with near-infrared absorption comprising at least one complexed unit, each unit comprising a phthalocyanine or a naphthalocyanine moiety and, optionally, a metal atom complexed thereto, each metal atom, if present, having a valency of from 1 to 5, with two valencies complexed to the phthalocyanine ring or the naphthalocyanine ring, each unit having two linker moieties on opposite sides or adjacent sides of the unit, wherein water-soluble groups are present in at least one of the linkers between the phthalocyanine or naphthalocyanine moiety and optionally on the phthalocyanine or naphthalocyanine moiety, wherein at least one linker moiety is bonded to a second phthalocyanine or naphthalocyanine moiety.

### Claim 2 (depends on 1)

The dye of claim 1 comprising up to 50 complexed units.

### Claim 3 (depends on 1)

The dye of claim 1 wherein the metal atom is present and the dye further includes at least one water-soluble group complexed to the metal atom.

### Claim 4 (depends on 1)

The dye of claim 1 wherein the dye further includes water-soluble groups on the phthalocyanine or the naphthalocyanine moiety.

### Claim 5 (depends on 4)

The dye of claim 4 wherein the water-soluble groups are selected from the group consisting of carboxylate, amides, imidazoles, poly(ethylene glycols), amines and sulfonates.

### Claim 6 (depends on 1)

The dye of claim 1 wherein the linker is on opposites sides of each unit to provide a linear polymer, wherein the linker is on three sides of each unit to provide a branched polymer, or wherein the linker is on four sides of each unit to provide a network structure.

### Claim 7 (depends on 1)

The dye of claim 1 wherein either the linker moiety comprises —X—, where X is CH2 or CO, and wherein the water-soluble group is a sulfonate, bonded to a neighboring X group in an adjacent unit or the linker moiety comprises -D-X—CH2—, where D is a single bond or CH2 and X is O or NH, and wherein the water-soluble group is a sulfonate, bonded between the D group of one complexed unit and a neighboring D group in an adjacent unit.

### Claim 8 (depends on 7)

The dye of claim 7 wherein the linker moiety comprises —X and the dye is selected from the group consisting of phthalocyanine dyes and naphthalocyanine dyes having water-soluble axial ligands having a general structure given by any of Formulae (I)-(VI):
where:
X═O, NH, CH2 or CO;
Y=halogen, OH, OCOR; COOZ, SO3Z, PO3Z, NR4+, O(CH2CH2O)mCH3; m=1 to 500;
Z═H or monovalent metal ions;
R═H, alkyl or substituted alkyl;
the number of Y groups depends upon the valency of the metal atom M;
M=either metal-free or any metal from the Periodic Table with valency 1 to 5;
M′=H, Li, Na, K, Rb or Cs; and
n=1 to 50.

### Claim 9 (depends on 7)

The dye of claim 7 wherein the linker moiety comprises -D-X—CH2— and the dye is selected from the group consisting of phthalocyanines and naphthalocyanines having extended conjugation and water-soluble axial ligands having a general structure given by any of Formulae (IX)-(XIV):
where:
X═O or NH;
Y=halogen, OH, OCOR; COOZ, SO3Z, PO3Z, NR4+, O(CH2CH2O)mCH3; m=1 to 500;
Z═H or monovalent metal ions;
D=single bond, CO or CH2;
R═H, alkyl or substituted alkyl;
the number of Y groups depends upon the valency of the metal atom M;
M=either metal-free or any metal from the Periodic Table with valency of 1 to 5;
M′=H, Li, Na, K, Rb or Cs; and
n=1 to 50.

### Claim 10 (depends on 8)

The dye of claim 8 wherein Z is selected from the group consisting of Na+, K+ and NR4+.

### Claim 11 (depends on 8)

The dye of claim 8 wherein the number of Y groups on the metal atom is one if M is trivalent, two if M is tetravalent, or three if M is quintavalent.

### Claim 12 (depends on 8)

The dye of claim 8 wherein M is copper, indium, gallium, thallium, germanium, tin, antimony, bismuth, cobalt, nickel, silicon, titanium, titanyl, vanadium, vanadyl, chromium, manganese, yttrium, scandium, zirconium, niobium, molybdenum, ruthenium, rhodium, hafnium, tantalum, zinc, manganese, magnesium, beryllium, aluminum, and bismuth.

### Claim 13 (depends on 12)

The dye of claim 12 wherein M is indium, gallium, or thallium.

### Claim 14 (depends on 9)

The dye of claim 9 wherein Z is selected from the group consisting of Na+, K+ and NR4+.

### Claim 15 (depends on 9)

The dye of claim 9 wherein the number of Y groups on the metal atom is one if M is trivalent, two if M is tetravalent, or three if M is quintavalent.

### Claim 16 (depends on 9)

The dye of claim 9 wherein M is copper, indium, gallium, thallium, germanium, tin, antimony, bismuth, cobalt, nickel, silicon, titanium, titanyl, vanadium, vanadyl, chromium, manganese, yttrium, scandium, zirconium, niobium, molybdenum, ruthenium, rhodium, hafnium, tantalum, zinc, manganese, magnesium, beryllium, aluminum, and bismuth.

### Claim 17 (depends on 16)

The dye of claim 16 wherein M is indium, gallium, or thallium.

### Claim 18 (depends on 1)

An inkjet ink formulation comprising:
(a) an aqueous vehicle;
(b) at least one dye or pigment; and
(c) the dye of claim 1.