Substrate having IR-absorbing dye disposed thereon

• US 7,579,064 B2
• Filed: 11/03/2008
• Issued: 08/25/2009
• Est. Priority Date: 07/05/2005
• Status: Expired due to Fees

• Current Assignee: BASF SE
• Original Assignee: Silverbrook Research Pty Limited
• Inventors: Silverbrook, Kia, Indusegaram, Sutharsiny, Vonwiller, Simone Charlotte, Starling, Scott Matthew, Ridley, Damon Donald, Gonzaga, Graciel
• Primary Examiner(s): Klemanski; Helene
• Application Number:
  US12/264,223
• Publication Number:
  US 20090061179A1
• Time in Patent Office: 295 Days
• Field of Search: 106/31.49, 106/31.47, 428/195.1, 428/211.1, 540/122, 540/123, 540/124
• US Class Current: 428/195.1
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07F 9/005 Compounds of elements of Group 5 of the Periodic Table without metal-carbon linkages
• CPC Class Codes: C09B 47/0675 having oxygen or sulfur linked directly to the skeleton
• CPC Class Codes: C09B 47/24 Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
• CPC Class Codes: Y10T 428/24934 including paper layer

Abstract

A substrate having an IR-absorbing dye disposed thereon. The dye is a naphthalocyanine dye of formula (I):

wherein

• • M is a metal group or is absent
  • R¹and R² are independently selected from the group consisting of: hydrogen and C_1-12 alkoxy;
  • X is selected from the group consisting of: O, S and ^˜NH^˜;
  • Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and Ar⁸ are selected from the group consisting of: phenyl, naphthyl, pyridyl, furanyl, pyrollyl and thiophenyl, each of Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and Ar⁸ being optionally substituted with 1, 2, 3, 4 or 5 groups, each group being independently selected from the group consisting of: C_1-12 alkyl, C_1-12 alkoxy, C_1-12 arylalkyl, C_1-12 arylalkoxy¹⁸ , (OCH₂CH₂)_dOR^d, cyano, halogen, amino, hydroxyl, thiol, —SR^v, —NR^uR^v, nitro, phenyl, phenoxy^˜, CO₂R^v˜, C(O)R^v˜, OCOR^v˜, SO₂R^v˜, OSO₂R^v˜, NHC(O)R^v, ^˜CONR^uR^v˜, CONR^uR^v, sulfonic acid, sulfonic acid salt and sulfonamide;
  • d is an integer from 2 to 5000;
  • R^d is H, C_1-8 alkyl or C(O)C_1-8 alkyl; and
  • R^u and R^vare independently selected from the group consisting of: hydrogen, C_1-12 alkyl, phenyl or phenyl—C_1-8 alkyl;
  • and wherein at least one of Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and Ar⁸ is substituted with a sulfonic acid or a sulfonic acid salt.

Claims

1. A substrate having an IR-absorbing dye disposed thereon, where said dye is a naphthalocyanine dye of formula (I):

2. The substrate of claim 1, wherein said dye is printed on said substrate.

3. The substrate of claim 1, which is a selected from the group consisting of:

a label, a packaging material or a surface of a product item.

4. The substrate of claim 1, which is comprised of plastics or paper.

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

6. The substrate of claim 5, wherein said coded data is a position-coding pattern.

7. The substrate of claim 5, wherein said coded data is readable by an optical sensing device.

8. The substrate of claim 1, wherein at least one of Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and Ar⁸ is substituted with —

SO₃Z;

wherein;

Z is H, Li, Na, K or N⁺(R^m)(Rⁿ)(R^s)(R^t); and

R^m, Rⁿ, R^s, R^t 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.

9. The substrate of claim 1, wherein each of Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and Ar⁸ is substituted with a sulfonic acid or a sulfonic acid salt.

10. The substrate of claim 9, wherein said dye is of formula (III):

11. The substrate of claim 10, wherein each —

SO₃Z group is at a para position.

12. The substrate of claim 1, wherein said dye is of formula (IV):

13. The substrate of claim 12, wherein R³ is C_1-6 alkyl or C_1-6 alkoxy.

14. The substrate of claim 1, wherein M is SnCl₂, Cu, v═

O, or Ga(OH).

15. The substrate of claim 1, wherein said dye is contained in an inkjet ink.