IP Library Granted Patent US 8,668,747
Granted Patent B2
US 8,668,747 · App. 13/144,145 · Granted Mar 11, 2014

Aqueous dye dispersions

Inventors: Holger Lautenbach (Rheinfelden, DE); Rainer Hans Traber (Reinach, CH); Heidemarie Urbing (Uffheim, FR)
Assignee: BASF SE
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Quick Facts
Patent No.
US 8,668,747
App. No.
13/144,145
Granted
Mar 11, 2014
Kind
B2
Abstract

The present invention relates to storage stable aqueous dye dispersions, comprising (a) 2.0 to 30.0% by weight, based on the sum of (a), (b) and (c), of a dye of the formula (3) in which KK is a residue of a coupling component; (b) 0.1 to 20.0 % by weight, based on the sum of (a), (b) and (c), of at least one additive selected from the group consisting of wetting agents, dispersing agents, rheology modifiers, and preservatives; and (c) 50.0 to 97.9% by weight, based on the sum of (a), (b) and (c), of water. The invention moreover relates to a process for their preparation and the use thereof for the dyeing, in particular of paper.

Claims (33)

1. An aqueous anionic direct dye dispersion consisting of:

(a) 2.0 to 30.0% by weight, based on the sum of (a), (b) and (c), of an anionic direct dye of formula (3) shown below

in which

KK is derived of the formula

in which

Y 1 and Y 2 independently of one another are ═O, ═NH or ═N—C 1 -C 4 alkyl,

Y 3 is ═O, ═S, ═NH, ═N—C 1 -C 4 alkyl or ═N—CN and

R 3 and R 4 independently of one another are each hydrogen, substituted or unsubstituted C 1 -C 6 alkyl or substituted or unsubstituted phenyl;

(b) 0.1 to 20.0% by weight, based on the sum of (a), (b) and (c), of at least one additive selected from the group consisting of wetting agents, dispersing agents, rheology modifiers, and preservatives; and

(c) 50.0 to 97.9% by weight, based on the sum of (a), (b) and (c), of water.

2. The aqueous anionic direct dye dispersion of claim 1 , which consists of the dye of formula (3) in which KK is derived from a coupling component selected from the formulae

3. The aqueous anionic direct dye dispersion according to claim 1 , wherein the additive (b) is selected from the group consisting of rheology modifiers and preservatives.

4. The aqueous anionic direct dye dispersion of claim 3 , comprising at least one rheology modifier.

5. The aqueous anionic direct dye dispersion according to claim 1 , which consists of

(a) 10.0 to 20.0% by weight, based on the sum of (a), (b) and (c), of the dye of formula (3) in which KK is derived from a coupling component selected from the formulae

(b) 0.2 to 10.0% by weight, based on the sum of (a), (b) and (c), of at least one additive selected from the group consisting of wetting agents, dispersing agents, rheology modifiers, and preservatives; and

(c) 70.0 to 89.8% by weight, based on the sum of (a), (b) and (c), of water.

6. A process for the preparation of aqueous anionic direct dye dispersions, which comprises stirring a dye of formula (3), according to claim 1 , with at least one additive selected from the group consisting of wetting agents, dispersing agents, rheology modifiers, and preservatives; and water, and optionally, further additives.

7. A method of dyeing paper comprising the step of coating or dipping said paper or adding to a pulp suspension the aqueous anionic direct dye dispersion, according to claim 1 .

8. Paper, which has been dyed with an aqueous anionic direct dye dispersion, as defined in claim 1 .

9. The aqueous anionic direct dye dispersion of claim 1 , wherein

the wetting agent is selected from the group consisting of C 10 -oxoalcohol ethoxylates with 3-8 ethylene oxide units, C 10 — Guerbet alcohol ethoxylates with 3-8 ethylene oxide units, C 12-14 fatty alcohol ethoxylates with 3-8 ethylene oxide units, sodium salt of sulfonated oleic acid diisobutylamide, sodium salt of dibutyl naphthaline sulfonic acid, sodium di(2-ethylhexyl) sulfosuccinate and 2,4,7,9-tetramethyl-5-decyne-4,7-diol;

the dispersing agent is a naphthalene sulfonic acid condensation products or a polymer that adsorb to the dye particles and thus hinder that the surfaces of the dye particles come into close contact;

the rheology modifier is selected from the group consisting of polyacrylamides, polysaccharides, hydrophobically modified acrylic acid polymer, cross-linked hydrophilic acrylic polymer, carbopoles (high molecular weight acrylic acid polymers), carboxy methyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, alginates, polyethylene glycol, polyvinylalcohol, polyvinylpyrrolidone and polyurethane based systems;

the preservative is selected from the group consisting of 2-methyl-2H-isothiazol-3-one and 1,2-benzisothiazole-3(2H)-one, alone or in combination.

10. The aqueous anionic direct dye dispersion according to claim 1 , wherein the dye of formula (2) is selected from the free acids of C.I. Direct Yellow 137, C.I. Direct Yellow 147 or C.I. Direct Yellow 166 and the dispersions contain from between 5 to 20% by weight of dye.

11. The aqueous anionic direct dye dispersion according to claim 1 , wherein the dye of formula (3) is

12. The aqueous anionic direct dye dispersion according to claim 10 , wherein the

the wetting agent is selected from the group consisting of C 10 -oxoalcohol ethoxylates with 3-8 ethylene oxide units, C 10 — Guerbet alcohol ethoxylates with 3-8 ethylene oxide units, C 12-14 fatty alcohol ethoxylates with 3-8 ethylene oxide units, sodium salt of sulfonated oleic acid diisobutylamide, sodium salt of dibutyl naphthaline sulfonic acid, sodium di(2-ethylhexyl) sulfosuccinate and 2,4,7,9-tetramethyl-5-decyne-4,7-diol;

the dispersing agent is a naphthalene sulfonic acid condensation products or a polymer that adsorb to the dye particles and thus hinder that the surfaces of the dye particles come into close contact;

the rheology modifier is selected from the group consisting of polyacrylamides, polysaccharides, hydrophobically modified acrylic acid polymer, cross-linked hydrophilic acrylic polymer, carbopoles (high molecular weight acrylic acid polymers), carboxy methyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, alginates, polyethylene glycol, polyvinylalcohol, polyvinylpyrrolidone and polyurethane based systems;

the preservative is selected from the group consisting of 2-methyl-2H-isothiazol-3-one and 1,2-benzisothiazole-3(2H)-one, alone or in combination.

13. The aqueous anionic direct dye dispersion according to claim 11 , wherein the additive is a dispersing agent and is naphthalene sulfonic acid condensation product; or the additive is a rheology modifier and is selected from the group consisting of anionic polysaccharides, anionic polyacrylamides, hydrophobically modified acrylic acid polymers, cross-linked hydrophilic acrylic polymers, polyurethane based systems and sodium polyacrylates; or the additive is a preservative and is 2-methyl-2H-isothiazol-3-one or 1,2-benzisothiazole-3(2H)-one.

Assignments (12)
SECURITY INTEREST Recorded Nov 14, 2025
From: CHEM-AQUA, INC.; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; NCH CORPORATION; NCH LIFE SCIENCES LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073570/0838 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073564/0864 →
SECURITY AGREEMENT (NOTES) Recorded Oct 10, 2025
From: DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 073061/0885 →
RELEASE OF 2023 NOTES PATENT SECURITY INTERESTS Recorded Oct 10, 2025
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 073074/0198 →
SECURITY AGREEMENT (2024 NOTES) Recorded Jun 24, 2024
From: BIRKO CORPORATION; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE, LLC; SOLENIS TECHNOLOGIES, L.P.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 067824/0278 →
2023 NOTES PATENT SECURITY AGREEMENT Recorded Jul 7, 2023
From: BIRKO CORPORATION; SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC; DIVERSEY, INC.; DIVERSEY TASKI, INC.; INNOVATIVE WATER CARE GLOBAL CORPORATION
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
Reel/Frame 064225/0170 →
SECURITY AGREEMENT (ABL) Recorded Sep 14, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: BANK OF AMERICA, N.A, AS COLLATERAL AGENT
Reel/Frame 061432/0958 →
SECURITY AGREEMENT (NOTES) Recorded Sep 14, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
Reel/Frame 061432/0821 →
SECURITY AGREEMENT (TERM) Recorded Sep 13, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 061431/0851 →
SECURITY AGREEMENT (NOTES) Recorded Sep 13, 2022
From: SOLENIS TECHNOLOGIES, L.P.; INNOVATIVE WATER CARE, LLC
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
Reel/Frame 061431/0865 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: BASF SE
To: SOLENIS TECHNOLOGIES, L.P.
Reel/Frame 059206/0621 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2011
From: LAUTENBACH, HOLGER; TRABER, RAINER HANS; URBING, HEIDEMARIE
To: BASF SE
Reel/Frame 026739/0722 →
Priority Claims (1)
EP 09152097 · Feb 4, 2009 · regional
Continuity (1)
Related Publication 20110296632A1 · Dec 8, 2011