Method of minimizing absorption of visible light in ink compositions comprising infrared-absorbing macrocyclic cyanine dyes
The present invention provides a method of minimizing absorption of visible light in an ink composition comprising an IR-absorbing metal cyanine dye, said method comprising preselecting said dye such that said metal has at least one axial ligand bound thereto, wherein said axial ligand comprises a moiety suitable for reducing intermolecular interactions between adjacent dye molecules. The method is especially suitable for use in connection with netpage and Hyperlabel systems.
1. A method of minimizing absorption of visible light in an ink composition comprising an IR-absorbing dye having a planar π-system, said method comprising preselecting said dye from a metal-cyanine complex of formula (I) or a cyanine compound of formula (II):
wherein
Q 1 , Q 2 , Q 3 and Q 4 are the same or different and are independently selected from a C 3-20 arylene group or a C 3-20 heteroarylene group, said C 3-20 arylene or C 3-20 heteroarylene group including at least one moiety suitable for reducing π-π interactions interactions:
M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO,
V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ) Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt:
A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR 3 , a hydrophilic ligand and/or a ligand suitable for reducing π-π interactions interactions:
R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and
R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy.
2. The method of claim 1 , wherein the π-π interactions interactions are reduced by steric repulsion.
3. The method of claim 1 , wherein the dye molecule comprises at least one moiety, which extends out of the plane of the planar π-system.
4. The method of claim 1 , wherein the π-π interactions interactions are reduced using a bridged cyclic group.
5. The method of claim 1 , wherein Q 1 , Q 2 , Q 3 and Q 4 are the same.
6. The method of claim 1 , wherein said moiety suitable for reducing π-π interactions interactions comprises a three-dimensional C 6-30 hydrocarbyl or C 6-30 hydrocarbylene group.
7. The method of claim 1 , wherein said moiety for reducing intermolecular interactions is a bridged cyclic group.
8. The method of claim 1 , wherein Q 1 , Q 2 , Q 3 and Q 4 are selected from an arylene or heteroarylene group of the formula:
wherein
R 1 and R 2 may be the same or different and are selected from hydrogen, hydroxyl, C 1-12 alkyl, C 1-12 alkyl bearing a hydrophilic or hydrophilizable group, C 1-12 alkoxy, C 1-12 alkoxy bearing a hydrophilic or hydrophilizable group, amino, C 1-12 alkylamino, di(C 1-12 alkyl)amino, halogen, cyano, thiol, C 1-12 alkylthio, nitro, carboxy, C 1-12 alkylcarbonyl, C 1-12 alkoxycarbonyl, C 1-12 alkylcarbonyloxy or C 1-12 alkylcarbonylamino; T is selected from a substituent comprising a polymeric chain or a C 6-30 hydrocarbyl group having three-dimensional structure;
W is a hydrophilic group;
E is selected from —OH, —O, C 1-6 alkyl, carboxy—C 1-6 alkyl, sulfo—C 1-6 alkyl, C 1-6 alkoxy, C 5-12 arylalkyl, C 1-6 alkylcarbonyl, C 5-12 arylalkylcarbonyl, C 1-6 alkoxycarbonyl or C 5-12 arylalkoxycarbonyl;
m is 0, 1 or 2;
n is 1 or 2; and
p is 0, 1 or 2.
9. The method of claim 8 , wherein R 1 and R 2 are selected from hydrogen or C 1-8 alkoxy.
10. The method of claim 8 , wherein W is selected from a substituent comprising a PEG chain; a substituent comprising an ammonium group; or a substituent comprising an acid group, including salts thereof.
11. The method of claim 8 , wherein W is —SO 3 H or a water-soluble salt thereof.
12. The method of claim 8 , wherein M is Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Al(A 1 ), Mn(A 1 ), Fe(A 1 ) or Sn(A 1 )(A 2 ).
13. The method of claim 12 , wherein A 1 and/or A 2 is a ligand of formula (IIIa)
wherein:
C 1 represents a core unit having two or more branching positions; each P 1 is independently selected from H, a hydrophilic moiety or a branched moiety;
g 1 is an integer from 2 to 8;
q 1 is 0 or an integer from 1 to 6; and
each p 1 is independently selected from 0 or an integer from 1 to 6.
14. The method of claim 13 , wherein C 1 is a C atom, an N atom, a Si atom, a C 1-8 alkyl residue, a C 3-8 cycloalkyl residue, or a phenyl residue.
15. The method of claim 13 , wherein A 1 and/or A 2 is a pentaerythritol derivative (A), a triethanolamine derivative (B), a phioroglucinol derivative (C), or a 3,5-dihydroxybenzyl alcohol derivative (D):
wherein is P 1 is as defined in claim 13 .
16. A method of minimizing absorption of visible light in an inkjet ink comprising an IR-absorbing having a planar π-system, said method comprising preselecting said dye from a metal-cyanine complex of formula (I) or a cyanine compound of formula (II):
wherein
Q 1 , Q 2 , Q 3 and Q 4 are the same or different and are independently selected from a C 3-20 arylene or a C 3-20 heteroarylene group, said C 3-20 arylene or C 3-20 heteroarylene group including at least one moiety suitable for reducing π-π interactions interactions:
M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO,
V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ) Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt:
A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR 3 , a hydrophilic ligand and/or a ligand suitable for reducing π-π interactions interactions:
R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and
R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy.
17. The method of claim 16 , wherein said inkjet ink furthur comprises a singlet oxygen quencher.
18. The method of claim 16 , wherein said inkjet ink is contained in an ink reservoir in fluid communication with a printhead of an inkjet printer.
19. The method of claim 18 , wherein said printhead comprises:
a plurality of nozzles;
a bubble forming chamber corresponding to each of the nozzles respectively, the bubble forming chambers adapted to contain ejectable liquid; and
a heater element disposed in each of the bubble forming chambers respectively, the heater element configured for thermal contact with the ejectable liquid; such that,
heating the heater element to a temperature above the boiling point of the ejectable liquid forms a gas bubble that causes the ejection of a drop of the ejectable liquid from the nozzle; wherein,
the heater element is suspended in the ink chamber such that during use at least a portion of the heater element is encircled by, and in direct contact with, the ejectable fluid.
20. The method of claim 16 , wherein said inkjet ink is contained in an ink cartridge.
21. A method of minimizing visible coloration of a substrate having an IR-absorbing dye disposed thereon, said method comprising preselecting said dye from a metal-cyanine complex of formula (I) or a cyanine compound of formula (II):
wherein
Q 1 , Q 2 , Q 3 and Q 4 are the same or different and are independently selected from a C 3-20 arylene or a C 3-20 heteroarylene group, said C 3-20 arylene or C 3-20 heteroarylene group including at least one moiety suitable for reducing π-π interactions interactions:
M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO,
V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ) Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt:
A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR 3 , a hydrophilic ligand and/or a ligand suitable for reducing π-π interactions interactions;
R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and
R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy.
22. The method of claim 21 , wherein said dye is disposed in the form of coded data.
23. The method of claim 22 , wherein said substrate comprises an interface surface and wherein the coded data is disposed over a substantial portion of said interface surface.
24. The method claim 21 , wherein said substrate is a paper sheet, a label, a tag, a packaging material or a product item.