Colorless water-soluble organic luminophores and intermediates thereof
View Patent ↗Benzazole substituted aminobenzenesulfonate derivatives of formula (A) (wherein X, Q and M are as defined in the specification) are useful as components of water-soluble fluorescent inks and dyes invisible in day-light. Novel intermediates for the above compounds are also disclosed.
1. A compound of formula (A)
wherein
X is O or S,
Q is
R 1 and R 2 are each independently
—NHCH 2 COOM, —N(CH 2 COOM) 2 or Cl,
with the proviso that at least one of R 1 and R 2 is other than Cl;
and
M is Na, K or NH 4 .
2. The compound of claim 1 wherein X is O and Q is
3. The compound of claim 1 wherein X is S and Q is
4. The compound of claim 1 which is selected from the group consisting of:
disodium salt of 4-[4-chloro-6-(3-sulfophenylamino)-1,3,5-triazin-2-ylamino]-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
pentapotassium salt of 4-{4,6-bis-[di(carboxymethyl)amino]-1,3,5-triazin-2-ylamino}-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
disodium salt of 4-{4-[2-(benzo[d]thiazol-2-yl)-4-sulfophenylamino]-6-chloro-1,3,5-triazin-2-ylamino}-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
disodium salt of 4-{4-[2-(benzo[d]thiazol-2-yl)-4-sulfophenylamino]-6-morpholino-1,3,5-triazin-2-ylamino}-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
disodium salt of 4-(4-carboxymethylamino-6-chloro-1,3,5-triazin-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
disodium salt of 4-[4-(3-sulfophenylamino)-6-morpholino-1,3,5-triazin-2-ylamino]-3-(benzo[d]thiazol-2-yl)benzenesulfonic acid;
trisodium salt of 4-[4,6-bis(carboxymethylamino)-1,3,5-triazin-2-ylamino]-3-(benzo[d]-thiazol-2-yl)benzenesulfonic acid;
disodium salt of 4-[4-chloro-6-(3-sulfophenylamino)-1,3,5-triazin-2-ylamino]-3-(benzo[d]oxazol-2-yl)benzenesulfonic acid; and
triammonium salt of 4-{4-chloro-6-[di(carboxymethyl)amino]-1,3,5-triazin-2-yl-amino}-3-(benzo[d]oxazol-2-yl)benzenesulfonic acid.
5. A water-soluble luminophore colorless under visible light, a water-soluble fluorescent ink, a water-soluble dye invisible in daylight, or a microbiological stain, said luminophore, ink, dye, or stain comprising the compound of claim 1 .
6. A compound of the formula (A′)
wherein
X′ is O or S,
Q′ is
R 1′ and R 2′ are simultaneously Cl; and
M′ is H, Na, K or NH 4 .
7. The compound of claim 6 , wherein X′ is O.
8. The compound of claim 6 , wherein M′ is Na, K or NH 4 .