IP Library Granted Patent US 7,553,359
Granted Patent B2
US 7,553,359 · App. 11/596,941 · Granted Jun 30, 2009

Stable liquid formulations of anionic dyes

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,553,359
App. No.
11/596,941
Granted
Jun 30, 2009
Kind
B2
Abstract

The present invention concerns concentrated aqueous solutions of anionic disazo dyes, comprising salts and or the free acids of anionic dyes of the formula and 2-(2-butoxyethoxy) ethanol wherein the substituents are each as defined in claim 1 and the use of these solutions for dyeing and/or printing hydroxyl-containing substrates and for producing inkjet inks.

Claims (30)

1. A concentrated aqueous solution, comprising the salt or the free acid or mixtures thereof, of at least one anionic dye of the formula

wherein

D is a radical of the formula (a)

wherein

R 1 , R 2 , R 3 , are independently H; C 1-4 alkyl; C 1-4 alkoxy, —SO 3 H; —OH or —CN; or independently —SO 2 —Y or —O—Y, wherein Y is an unsubstituted C 1-4 -alkenyl group or an unsubstituted C 1-4 alkyl group or wherein Y is an NC—, HO—, HOSO 3 —, halogen-substituted C 1-4 -alkenyl group or an NC—, HO—, HOSO 3 —, halogen-substituted C 1-4 alkyl group or Y is —NR 11 R 12 wherein R 11 and R 12 are independently H, C 1-4 alkyl or substituted C 1-4 alkyl or combine with the interjacent nitrogen to form a five- or six-membered ring optionally comprising one or two or three heteroatoms, in which case the heterocyclic ring is unsubstituted or the heterocyclic ring is substituted by one or two C 1-4 alkyl groups,

or D is a bicyclic ring system unsubstituted or substituted with C 1-4 alkoxy, —SO 3 H; —OH or —CN; or independently —SO 2 —Y or —O—Y, wherein Y is an unsubstituted C 1-4 -alkenyl group or an unsubstituted C 1-4 alkyl group or wherein Y is an NC—, HO—, HOSO 3 —, halogen-substituted C 1-4 -alkenyl group or an NC—, HO—, HOSO 3 —, halogen-substituted C 1-4 alkyl group or Y is —NR 11 R 12 where R 11 and R 12 are each as defined above, wherein each of the rings are, optionally, and independently a five-membered or six-membered ring, wherein the five- or six-membered rings, optionally include one or two or three heteroatoms and this bicyclic ring system is not further substituted by substituents attached via azo groups, and

M is a bridging phenyl group unsubstituted or substituted by C 1-4 alkyl, C 1-4 alkoxy, hydroxyl, carboxyl, sulpho, cyano or halogen,

and

when n=1, B is hydrogen, an unsubstituted aryl radical, a substituted aryl radical, or a substituted triazine derivative of the formula

wherein X 1 and X 2 are independently unsubstituted amine —NH 2 or substituted amine —NR 21 R 22 wherein R 21 and R 22 are independently: H, C 1-4 alkyl or substituted C 1-4 alkyl, or combine with the interjacent nitrogen to form a five- or six-membered ring optionally comprising one or two or three heteroatoms, in which case the heterocyclic ring is unsubstituted or the heterocyclic ring is substituted by one or two C 1-4 alkyl groups

or when n=2, B is a bridge of the formula

or a bridge of the formula

where X 1 is defined above

and 2-(2-butoxyethoxy) ethanol.

2. A concentrated aqueous solution according to claim 1 , wherein the at least one dye of the formula I is a dye of the formula I′

3. A concentrated aqueous solution according to claim 1 , wherein

D is a radical of the formula (a′)

wherein

R 1 , R 2 , R 3 , are independently H; C 1-4 alkyl C 1-4 alkoxy; —SO 3 H; —OH or —CN;

M is a bridging phenyl group unsubstituted or substituted by C 1-4 alkyl, C 1-4 alkoxy; sulpho, carboxyl, or hydroxyl and

B is H, an unsubstituted phenyl group or substituted phenyl group or a substituted triazine derivative of the formula

where X 1 and X 2 are independently as defined above and n=1.

4. A concentrated aqueous solution according to claim 1 , wherein the concentrated aqueous solution comprises 5% to 40% by weight of the at least one dye of the formula I, 5-40% by weight of 2-(2-butoxyethoxy) ethanol and 20% to 90% by weight of water.

5. A concentrated aqueous solution according to claim 1 , wherein the concentrated aqueous solution comprises 5% to 40% by weight of the at least one dye of the formula I, 5% to 40% by weight of 2-(2-butoxyethoxy) ethanol, 3-10% by weight of a water-soluble organic solubilizer and 10% to 88% by weight of water.

6. A concentrated aqueous solution according to claim 1 , wherein the concentrated aqueous solution comprises 10% to 30% by weight of the at least one dye of the formula I, 10% to 30% by weight of 2-(2-butoxyethoxy) ethanol, 3-6% by weight of a water-soluble organic solubilizer and 34% to 77% by weight of water.

7. An inkjet ink comprising at least one concentrated aqueous solution according to claim 1 .

8. A method for dyeing and/or printing a hydroxyl-containing substrate comprising the step of contacting at least one concentrated aqueous solution according to claim 1 with the hydroxyl-containing substrate.

9. A hydroxyl-containing substrate dyed and/or printed by the process according to claim 8 .

10. A hydroxyl-containing substrate according to claim 9 wherein the hydroxyl-containing substrate is paper.

11. A method for producing an inkjet ink, comprising the step of combining a concentrated aqueous solution according to claim 1 , with at least one additional chemical and/or water.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2016
From: CLARIANT FINANCE (BVI) LIMITED
To: ARCHROMA IP GMBH
Reel/Frame 039103/0455 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2006
From: BERENGUER, JORDI; HASEMANN, LUDWIG; BOSCH, JOAN; BASOLAS, SUSANA
To: CLARIANT FINANCE (BVI) LIMITED
Reel/Frame 018602/0696 →