Phthalocyanine, naphthalocyanine, and bridged phthalocyanine/naphthalocyanine dyes and inks containing the same

1. A dye comprising a phthalocyanine dye represented by one of the general structures I to VIII, a naphthalocyanine dye represented by one of the general structures IX to XIV, or a bridged phthalocyanine/naphthalocyanine dye represented by one of the general structures XV to XVII:

wherein:

R is H, alkyl substituted alkyl, or SO 3 M 1 ;

M 1 is H, monovalent cations, or NR 4 4 + ;

OR can be replaced by a halogen;

R 1 is H, alkyl, or substituted alkyl or aryl with carbons from 1 to 50;

R 2 is H;

n is 1 to 5000;

R 3 is a divalent linking group;

M is a monovalent, a divalent, a trivalent, a tetravalent or a pentavalent metal ion or transition metal ion;

X is H, alkyl, substituted alkyl, aryl, substituted aryl, SO 3 M 1 , OH, OCOR 2 ; COOM 1 , PO 3 M 1 2 , NR 4 4 + Y − , or O(CH 2 CH 2 O) m CH 3 wherein m=1 to 500, where at least one of the X in the dye is sulfonate, phosphate or polyethylene glycol, where Y is independently selected from the group consisting of: a halide, sulfate, sulfonate, OH − , and OSO 3 − ; and

R 4 is H, alkyl, substituted alkyl, aryl, or substituted aryl.

2. The dye of claim 1 , wherein the dye is a phthalocyanine dye represented by one of the general structures I to VIII.

3. The dye of claim 2 , wherein the phthalocyanine dye is selected from the group consisting of:

and mixtures thereof.

4. The dye of claim 1 , wherein the dye is a naphthalocyanine dye represented by one of the general structures IX to XIV.

5. The dye of claim 4 , wherein the naphthalocyanine dye is selected from the group consisting of

and mixtures thereof.

6. The dye of claim 1 , wherein the dye is a bridged phthalocyanine/naphthalocyanine dye represented by one of the general structures XV to XVII.

7. The dye of claim 6 , wherein the bridged phthalocyanine/naphthalocyanine dye is selected from the group consisting of

and mixtures thereof.

8. The dye of claim 1 , wherein R is hydrogen.

9. The dye of claim 1 , wherein OR is replaced by a halogen.

10. The dye of claim 1 , wherein for R 1 or R 2 , the number of carbon atoms of the alkyl or aryl group is from 1 to 30.

11. The dye of claim 1 , wherein R 1 is, independently, an alkyl group, having the formula C n H 2n+1 , wherein n ranges from 1 to 8.

12. The dye of claim 1 , wherein n is 1 to 500.

13. The dye of claim 1 , wherein M is a metal selected from the group consisting of Mg, Zn, Cd, Hg, Al, Ga, In, Tl, Si, Ge, Sn, Pb, P, As, Sb, Bi, Sc, Y, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, and Au.

14. The dye of claim 1 , wherein the metal M is In.

15. The dye of claim 1 , wherein the metal M is Cu.

16. The dye of claim 1 , wherein X is SO 3 M 1 ; M 1 is independently selected from the group consisting of H and a monovalent metal cation, wherein the monovalent metal cation is independently selected from the group consisting of Na + , K + and NR 4 + , wherein R 4 is independently selected from the group consisting of H, an alkyl group, a substituted alkyl group, an aryl group and a substituted aryl group.

17. The dye of claim 1 , wherein X is SO 3 Na.

18. The dye of claim 1 , wherein R 3 is selected from the group consisting of CH 2 , CH 2 CH 2 , CO, O, NH, S, SO 2 , SO 2 NH, COO, CONH, and combinations thereof.

19. An inkjet ink comprising a liquid vehicle and at least one dye as in claim 1 , wherein the dye is either soluble or dispersed in the inkjet ink.

20. A detection system, comprising:

a near infrared (NIR) illumination source;

an ink-jet ink of claim 19 ; and

a NIR sensor that detects absorption of the dye in the ink-jet ink illuminated by the NIR illumination source.