Patent number: 7470315
Abstract: A naphthalocyanine dye of formula (I) is provided: wherein M is a metal group or is absent; R1 and R2 are independently selected from hydrogen or C1-12 alkoxy; X is selected from O, S or —NH—; Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7 and Ar8 are selected from phenyl, naphthyl, pyridyl, furanyl, pyrollyl, thiophenyl, each of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7 and Ar8 being optionally substituted with 1, 2, 3, 4 or 5 groups, the or each group being independently selected from C1-12 alkyl, C1-12 alkoxy, C1-12 arylalkyl, C1-12 arylalkoxy, —(OCH2CH2)dORd, cyano, halogen, amino, hydroxyl, thiol, —SRv, —NRuRv, nitro, phenyl, phenoxy, —CO2Rv, —C(O)Rv, —OCORv, —SO2Rv, —OSO2Rv, —NHC(O)Rv, —CONRuRv, —CONRuRv, sulfonic acid, sulfonic acid salt and sulfonamide; d is an integer from 2 to 5000; Rd is H, C1-8 alkyl or C(O)C1-8 alkyl; and Ru and Rv are independently selected from hydrogen, C1-12 alkyl, phenyl or phenyl-C1-8 alkyl.
Type:
Grant
Filed:
July 5, 2005
Date of Patent:
December 30, 2008
Assignee:
Silverbrook Research Pty Ltd
Inventors:
Simone Charlotte Vonwiller, Damon Donald Ridley, Sutharsiny Indusegaram, Scott Matthew Starling, Graciel Gonzaga, Kia Silverbrook
Patent number: 7153956
Abstract: The present invention provides an IR-absorbing dye of formula (I) or (II) wherein R10, R13, R20, R23, R30, R33, R40 and R43 are independently selected from a C1-12 alkyl group bearing a hydrophilic or hydrophilizable group; R11, R12, R21, R22, R31, R32, R41 and R42 are independently selected from H or a C1-30 hydrocarbyl group, or each of R11/R12, R21/R22, R31/R32, and R41/R42 are together joined to form a C3-30 hydrocarbylene group; M is selected from Si(A1)(A2), Ge(A1)(A2), Ga(A1), Mg, Al(A1), TiO, Ti(A1)(A2), ZrO, Zr(A1)(A2), VO, V(A1)(A2), Mn, Mn(A1), Fe, Fe(A1), Co, Ni, Cu, Zn, Sn, Sn(A1)(A2), Pb, Pb(A1)(A2), Pd and Pt; A1 and A2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR3, a hydrophilic ligand and/or a ligand suitable for reducing intermolecular interactions; R3 is a selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); and Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl
Type:
Grant
Filed:
August 9, 2004
Date of Patent:
December 26, 2006
Assignee:
Silverbrook Research Pty Ltd
Inventors:
Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Graciel Gonzaga, Kia Silverbrook, Paul Lapstun
Patent number: 7138391
Abstract: The present invention provides an IR-absorbing dye of formula (I) or (II): wherein Q1, Q2, Q3 and Q4 are the same or different and are independently selected from a C3-20 heteroarylene group comprising at least one N atom; M is selected from Si(A1)(A2), Ge(A1)(A2), Ga(A1), Mg, Al(A1), TiO, Ti(A1)(A2), ZrO, Zr(A1)(A2), VO, V(A1)(A2), Mn, Mn(A1), Fe, Fe(A1), Co, Ni, Cu, Zn, Sn, Sn(A1)(A2), Pb, Pb(A1)(A2), Pd and Pt; A1 and A2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR3, a hydrophilic ligand and/or a ligand suitable for reducing cofacial interactions; R3 is a selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl or Si(Rx)(Ry)(Rz); and Rx, Ry and Rz may be the same or different and are selected from C1-12 alkyl, C5-12 aryl, C5-12 arylalkyl, C1-12 alkoxy, C5-12 aryloxy or C5-12 arylalkoxy. Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.
Type:
Grant
Filed:
August 9, 2004
Date of Patent:
November 21, 2006
Assignee:
Silverbrook Research Pty Ltd
Inventors:
Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Graciel Gonzaga, Kia Silverbrook, Paul Lapstun
Patent number: 7122076
Abstract: The present invention provides an IR-absorbing naphthalocyanine dye of formula (I): wherein M is selected from Si(A1)(A2), Ge(A1)(A2), Ga(A1), Mg, Al(A1), TiO, Ti(A1)(A2), ZrO, Zr(A1)(A2), Vo, V(A1)(A2), Mn, Mn(A1), Fe, Fe(A1), Co, Ni, Cu, Zn, Sn, Sn(A1)(A2), Pb, Pb(A1)(A2), Pd and Pt; A1 and A2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR3, a hydrophilic ligand and/or a ligand suitable for reducing cofacial interactions; R1 and R2 are selected from H or C1-12alkoxy; R3 is selected from C1-12alkyl, C5-12aryl, C5-12arylalkyl or Si(Rx)(Ry)(Rz); and Rx, Ry and Rz may be the same or different and are selected from C1-12alkyl, C5-12aryl, C5-12arylalkyl, C1-12 alkoxy, C5-12aryloxy or C5-12arylalkoxy; W is a hydrophilic group; n1 is 0, 1, 2 or 3; n2 is 0, 1, 2 or 3; n3 is 0, 1, 2 or 3; n4 is 0, 1, 2 or 3; provided that at least one of n1, n2, n3 or n4 is greater than 0. Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.
Type:
Grant
Filed:
August 9, 2004
Date of Patent:
October 17, 2006
Assignee:
Silverbrook Research Pty Ltd
Inventors:
Simone Charlotte Vonwiller, Scott Matthew Starling, Damon Donald Ridley, Lachlan Everett Hall, Simon Fielder, Sutharsiny Indusegaram, Kia Silverbrook, Paul Lapstun