Sulfonated dye salts having improved stability
A salt of a sulfonated dye modulates a stability of the dye, particularly its ozonefastness. The salt comprises an organic cation selected from the group consisting of: a first organic cation having a positive charge delocalized between a nitrogen atom and at least one other heteroatom; a second organic cation having a positive charge delocalized between a nitrogen atom and at least two other atoms; and a third organic cation of formula (A): wherein: R p , R q and R r are each independently selected from a C 1-6 alkyl group; s is 0, 1, 2 or 3; and Ar is a C 6-12 aryl group or C 3-12 heteroaryl group.
1. A salt of a sulfonated dye, said salt modulating a stability of said dye, wherein said salt comprises at least one phosphazene cation of formula (C):
wherein:
R 15 , R 16 and R 17 are each independently selected from the group consisting of: C 6-12 aryl, C 5-12 heteroaryl; N(R 20 )(R 21 ) and —N═P[N(R 22 ) 2 ] 3 ;
R 18 and R 19 are each independently selected from the group consisting of: H and C 1-8 alkyl; or R 18 and R 19 are together: ═P(Ph) 3 ;
R 20 and R 21 are each independently selected from the group consisting of: H and C 1-8 alkyl; or R 20 and R 21 are together joined to form a nitrogen-containing C 5-10 heterocycloalkyl group; and
R 22 is C 1-6 alkyl.
2. The salt of claim 1 , wherein said salt modulates an ozonefastness of said dye.
3. The salt of claim 1 , wherein said dye is a phthalocyanine dye.
4. The salt of claim 1 , wherein said dye is an IR-absorbing dye.
5. The salt of claim 1 , wherein said salt is of formula (I):
wherein:
Q 1 , Q 2 , Q 3 and Q 4 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 (H 2 ) or a metal selected from the group consisting of: 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 l and A 2 are axial ligands, which may be the same or different, and are selected from the group consisting of: —OH, halogen, —OR 3 , —OC(O)R 4 and —O(CH 2 CH 2 O) e R e wherein e is an integer from 2 to 10 and R e is H, C 1-8 alkyl or C(O)C 1-8 alkyl;
R 3 is selected from the group consisting of: C 1-20 alkyl, C 5-12 aryl, C 5-20 arylalkyl and Si(R x )(R y )(R z );
R 4 is selected from the group consisting of: —C 1-20 alkyl, C 5-12 aryl and C 5-20 arylalkyl;
R x , R y and R z are the same or different and are selected from the group consisting of: C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy and C 5-12 arylalkoxy; and
Z 1 + , Z 2 + , Z 3 + and Z 4 + may be the same or different and are each the phosphazene cation of formula (C) as defined in claim 1 .
6. The salt of claim 1 , wherein said salt is of formula (II):
wherein
M is (H 2 ) or a metal selected from the group consisting of: 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 l is an axial ligand selected from the group consisting of: —OH, halogen, —OR 3 , —OC(O)R 4 and O(CH 2 CH 2 O) e R e wherein e is an integer from 2 to 10 and R e is H, C 1-8 alkyl or C(O)C 1-8 alkyl;
R 3 is selected from the group consisting of: C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl and Si(R x )(R y )(R z );
R 4 is selected from the group consisting of: C 1-12 alkyl, C 5-12 aryl and C 5-12 arylalkyl;
R x , R y and R z may be the same or different and are selected from the group consisting of: C 1-12 alkyl, C 5-12 aryl, C 5-12 arylalkyl, C 1-12 alkoxy, C 5-12 aryloxy and C 5-12 arylalkoxy; and
Z 1 + , Z 2 + , Z 3 + and Z 4 + may be the same or different and are each the phosphazene cation of formula (C) as defined in claim 1 .
7. The salt of claim 6 , wherein M is Ga(OH).
8. A substrate having the salt according to claim 1 disposed thereon or therein.
9. The substrate of claim 8 , wherein said substrate is paper.
10. A printing ink comprising the salt according to claim 1 .