Hydrophilizable and hydrophilic cyanine dyes
The present invention provides an IR-absorbing dye of formula (I) or (II): wherein Q 1 , Q 2 , Q 3 and Q 4 are the same or different and are independently selected from a C 3-20 heteroarylene group comprising at least one N atom; M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO, Zr(A 1 )(A 2 ), VO, V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ), Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt; A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen, —OR 3 , a hydrophilic ligand and/or a ligand suitable for reducing cofacial interactions; R 3 is a selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy. Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.
1. A water-dispersible IR-absorbing dye for a water-based inkjet ink, said dye being of formula (I) or (II):
wherein Q 1 , Q 2 , Q 3 and Q 4 are selected from a heteroarylene group of the formula:
wherein
R 1 and R 2 may be the same or different and are selected from hydrogen, hydroxyl or C 1-12 alkoxy;
T is selected from a substituent comprising a polymeric chain or a C 1-30 hydrocarbyl group;
W is a hydrophilic group;
E is selected from —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 or C 5-12 arylalkoxycarbonyl;
m is 0, 1 or 2;
n is 0, 1 or 2;
p is 0, 1 or 2;
M is selected from Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Mg, Al(A 1 ), TiO, Ti(A 1 )(A 2 ), ZrO Zr(A 1 )(A 2 ), VO, V(A 1 )(A 2 ), Mn, Mn(A 1 ), Fe, Fe(A 1 ), Co, Ni, Cu, Zn, Sn, Sn(A 1 )(A 2 ), Pb, Pb(A 1 )(A 2 ), Pd and Pt;
A 1 and A 2 are axial ligands, which may be the same or different, and are selected from —OH, halogen or —OR 3 ;
R 3 is a selected from C 1-12 alkyl C 5-12 aryl, C 5-12 arylalkyl or Si(R x )(R y )(R z ); and
R x , R y and R z may be the same or different and are selected from C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-2 alkoxy, C 5-12 aryloxy or C 5-12 arylalkoxy.
2. The dye of claim 1 , wherein Q 1 , Q 2 , Q 3 and Q 4 are the same.
3. The dye of claim 1 , wherein M is Si(A 1 )(A 2 ), Ge(A 1 )(A 2 ), Ga(A 1 ), Al(A 1 ), Mn(A 1 ), Fe(A 1 ) or Sn(A 1 )(A 2 ).
4. The dye of claim 1 , wherein R 1 and R 2 are selected from hydrogen or C 1-8 alkoxy.
5. The dye of claim 1 , wherein Q 1 , Q 2 , Q 3 and Q 4 are selected from a heteroarylene group of the formula (ii) or (iv), and E is C 1-6 alkyl.
6. The dye of claim 1 , wherein W is selected from a substituent comprising a PEG chain; a substituent comprising an ammonium group; a substituent comprising an acid group, including salts thereof; a substituent comprising a sulfonamide group.
7. The dye of claim 1 , wherein W is —SO 3 H or a water-soluble salt thereof.
8. The dye of claim 1 , wherein m and p are 0.