IP Library Granted Patent US 7,579,064
Granted Patent B2
US 7,579,064 · App. 12/264,223 · Granted Aug 25, 2009

Substrate having IR-absorbing dye disposed thereon

Assignee: Silverbrook Research Pty Ltd
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Quick Facts
Patent No.
US 7,579,064
App. No.
12/264,223
Granted
Aug 25, 2009
Kind
B2
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 R 1 and R 2 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 ˜ ; Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 are selected from the group consisting of: phenyl, naphthyl, pyridyl, furanyl, pyrollyl and thiophenyl, each of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 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 arylalkoxy 18 , (OCH 2 CH 2 ) d OR d , cyano, halogen, amino, hydroxyl, thiol, —SR v , —NR u R v , nitro, phenyl, phenoxy ˜ , CO 2 R v ˜ , C(O)R v ˜ , OCOR v ˜ , SO 2 R v ˜ , OSO 2 R v ˜ , NHC(O)R v , ˜ CONR u R v ˜ , CONR u R 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 v are 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 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 is substituted with a sulfonic acid or a sulfonic acid salt.

Claims (34)

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

wherein

M is a metal group or is absent;

R 1 and R 2 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 ˜ ;

Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 are selected from the group consisting of: phenyl, naphthyl, pyridyl, furanyl, pyrollyl and thiophenyl, each of Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 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 arylalkoxy ˜ , (OCH 2 CH 2 ) d OR d , cyano, halogen, amino, hydroxyl, thiol, —SR v , —NR u R v , nitro, phenyl, phenoxy ˜ , CO 2 R v ˜ , C(O)R v ˜ , OCOR v ˜ , SO 2 R v ˜ , OSO 2 R v ˜ , NHC(O)R v , ˜ CONR u R v ˜ , CONR u R 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 v are 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 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 is substituted with a sulfonic acid or a sulfonic acid salt.

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 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 is substituted with —SO 3 Z;

wherein:

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

R m , R n , 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 Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , Ar 6 , Ar 7 and Ar 8 is substituted with a sulfonic acid or a sulfonic acid salt.

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

wherein:

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

R m , R n , 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.

11. The substrate of claim 10 , wherein each —SO 3 Z group is at a para position.

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

wherein:

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

R m , R n , 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; and

R 3 is selected from the group consisting of: C 1-12 alkyl, C 1-12 alkoxy, C 1-12 arylalkyl, C 1-12 arylalkoxy ˜ , (OCH 2 CH 2 ) d OR d , cyano, halogen, amino, hydroxyl, thiol, —SR v , —NR u R v , nitro, phenyl, phenoxy ˜ , CO 2 R v ˜ , C(O)R v ˜ , OCOR v ˜ , NHC(O)R v ˜ , CONR u R v and ˜ CONR u R v .

13. The substrate of claim 12 , wherein R 3 is C 1-6 alkyl or C 1-6 alkoxy.

14. The substrate of claim 1 , wherein M is SnCl 2 , Cu, v═O, or Ga(OH).

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

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2014
From: SILVERBROOK RESEARCH PTY LTD
To: BASF SE
Reel/Frame 033062/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2008
From: VONWILLER, SIMONE CHARLOTTE; RIDLEY, DAMON DONALD; INDUSEGARAM, SUTHARSINY; STARLING, SCOTT MATTHEW; GONZAGA, GRACIEL; SILVERBROOK, KIA
To: SILVERBROOK RESEARCH PTY LTD
Reel/Frame 021779/0559 →
Continuity (2)
Continuation 1117281500 · Jul 5, 2005
Related Publication 20090061179A1 · Mar 5, 2009