SUBSTRATE HAVING IR-ABSORBING DYE WITH BRANCHED AXIAL LIGANDS

• US 20100233499A1
• Filed: 05/24/2010
• Published: 09/16/2010
• Est. Priority Date: 08/09/2004
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Hall, Lachlan Everett, Silverbrook, Kia, Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Fielder, Simon, Lapstun, Paul, Ridley, Damon Donald, Sintic, Maxine
• Granted Patent: US 7,946,626 B2
• Time in Patent Office: Days
• US Class Current: 428/537.500
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09D 11/32 characterised by colouring agents
• CPC Class Codes: Y10T 428/31993 Of paper

Abstract

A substrate having an IR-absorbing dye disposed thereon. The IR-absorbing dye is a metal phthalocyanine dye having branched axial ligands. The branched axial ligands minimize interaction between π systems of adjacent dye molecules, and assist in reducing absorption of visible wavelengths.

Claims

1. A substrate having an IR-absorbing dye disposed thereon, said IR-absorbing dye being a metal-cyanine complex of formula (I):

wherein

Q¹, Q², Q³ and Q⁴ are the same or different and are independently selected from the group consisting of;

a C_3-20 arylene group and a C_3-20 heteroarylene group;

M is selected from the group consisting of;

Ti(A¹)(A²), Zr(A¹)(A²), V(A¹)(A²), Si(A¹)(A²), Ge(A¹)(A²), Ga(A¹), Al(A¹), Mn(A¹), Fe(A¹), Sn(A¹)(A²) and Pb(A¹)(A²); and

A¹ and A² may be the same or different and are axial ligands of formula (IIIa)

wherein;

G represents a core unit having two or more branching positions;

g¹ is an integer from 2 to 8;

q¹ is 0 or an integer from 1 to 6;

each p¹ is independently selected from 0 or an integer from 1 to 6; and

each L is independently selected from the group consisting of;

H;

(CH₂CH₂O)_vR⁶, wherein v is an integer from 2 to 5000 and R⁶ is H, C_1-6 alkyl or C(O)C_1-8 alkyl;

SO₃Z;

PO₃Z₂;

C_1-12 alkyl-CO₂Z;

C_1-12 alkyl-SO₃Z;

C_1-12-alkyl-PO₃Z₂;

C_1-12 alkyl-OSO₃Z;

C_1-12-alkyl-OPO₃Z₂; and

C_1-12-alkyl-N⁺(R^a)(R^b)(R^c);

C_1-12 alkyl-J,

and wherein;

Z is H, Li⁺, Na⁺, K⁺ or NH₄;

R^a, R^b, R^c may be the same or different and are independently selected from the group consisting of;

H, C_1-8 alkyl, C_6-12 arylalkyl and C_6-12 aryl; and

J is pyridinium, imidazolinium or pyrrolinium.

2. The substrate of claim 1, wherein said dye is disposed in the form of coded data.

3. The substrate of claim 2 comprising an interface surface and wherein the coded data is disposed over a substantial portion of said interface surface.

4. The substrate of claim 1, which is a paper sheet, a label, a tag, a packaging material or a product item.

5. The substrate of claim 1, wherein Q¹, Q², Q³ and Q⁴ are the same.

6. The substrate of claim 1, wherein G 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.

7. The substrate of claim 1, wherein g is 2, 3 or 4.

8. The substrate of claim 1, wherein A¹ and/or A² is a pentaerythritol derivative of formula (A), a triethanolamine derivative of formula (B), a phloroglucinol derivative of formula (C), or a 3,5-dihydroxybenzyl alcohol derivative of formula (D):

wherein is L is as defined in claim 1.

9. The substrate of claim 1, wherein Q¹, Q², Q³ and Q⁴ are selected from an arylene or heteroarylene group of the formula:

wherein

R¹ and R² may be the same or different and are selected from the group consisting of;

from hydrogen, hydroxyl, C_1-12 alkyl, C_1-12 alkoxy, 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 a C_1-30 hydrocarbyl group;

E is selected from the group consisting of;

—

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 and C_5-12 arylalkoxycarbonyl;

m is 0, 1 or 2;

n is 0, 1 or 2;

p is 0, 1 or 2; and

W is a hydrophilic group selected from the group consisting of;

a PEG chain;

an ammonium group;

a sulfonic acid group and salts thereof; and

a sulfonamide group.

10. The substrate of claim 9, wherein R¹ and R² are selected from the group consisting of:

hydrogen and C_1-8 alkoxy.