IP Library Granted Patent US 12,570,864
Granted Patent B2
US 12,570,864 · App. 16/979,218 · Granted Mar 10, 2026

Storage-stable pigmented formulations containing isocyanate groups and use thereof

Inventors: Joerg Tillack (Solingen, DE); Dirk Achten (Leverkusen, DE); Monika Bach (Leinenfelden-Echterdingen, DE); Achim Weber (Altbach, DE); Fabian Schuster (Leverkusen, DE)
Assignee: Covestro Deutschland AG
C09D11/102C08G18/544C08G18/73C08G18/792C08G18/798C09D11/322C09D11/38
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Quick Facts
Patent No.
US 12,570,864
App. No.
16/979,218
Granted
Mar 10, 2026
Kind
B2
Abstract

The invention relates to storage-stable pigmented formulations containing isocyanate groups, comprising at least one pigment a., at least one component b. containing isocyanate groups, at least one wetting agent and/or dispersant c., at least one grind resin d. and optionally solvents, wherein the formulation has a viscosity increase of less than 500% after storage at 50° C. over a period of at least 3 days. The invention also relates to the production of such formulations and to the use thereof.

Claims (38)

1 . A storage-stable, isocyanate group-containing formulation comprising the components:

a. at least one pigment,

b. 59.2% to 92.1% by weight of at least one isocyanate group-containing component based on a total weight of the storage-stable, isocyanate group-containing formulation,

c. at least one wetting agent and/or dispersant,

d. at least one grinding resin, and

e. optionally solvents,

wherein the storage-stable, isocyanate group-containing formulation after storage at 50° C. over a period of at least 14 days exhibits a rise in viscosity of less than 300%, based on a starting viscosity of the storage-stable, isocyanate group-containing formulation,

wherein the storage-stable, isocyanate group-containing formulation comprises at least one component having at least one isocyanate-reactive group, wherein a molar ratio of isocyanate groups of component b to a sum of all isocyanate-reactive groups in the storage-stable, isocyanate group-containing formulation is at least 11:1.

2 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , comprising

a. 0.01% to 45% by weight of the at least one pigment;

b. 59.2% to 92.1% by weight of the at least one isocyanate group-containing component;

c. 0.01% to 20% by weight of the at least one wetting agent and/or dispersant;

d. 0.1% to 30% by weight of the at least one grinding resin; and

e. 0% to 80% by weight of the solvents;

in each case based on a total weight of the storage-stable, isocyanate group-containing formulation, with a sum of all constituents in the storage-stable, isocyanate group-containing formulation not exceeding 100% by weight.

3 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the isocyanate group-containing component b comprises 1,4-diisocyanatobutane, 1,5-diisocyanatopentane, 1,6-diisocyanatohexane, 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- or 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- or 1,4-bis(isocyanatomethyl)benzene, 1,3- or 1,4-bis(1-isocyanato-1-methylethyl)benzene, 2,4- or 2,6-diisocyanatotoluene, 2,4′- or 4,4′-diisocyanatodiphenylmethane, 1,5-diisocyanatonaphthalene, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane, 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane, 2,4′- or 4,4′-diisocyanatodicyclohexylmethane, optionally oligomers or reaction products of these, or a mixture of at least two of these.

4 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the isocyanate group-containing component b consists of aliphatic or cycloaliphatic isocyanates.

5 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the storage-stable, isocyanate group-containing formulation has at least one of the following properties (A)-(D) at room temperature:

(A) a starting viscosity in a range from 1 to 200 mPa·s;

(B) a starting viscosity in a range from 30 to 1000 mPa·s;

(C) a starting viscosity in a range from 50 to 2000 mPa·s;

(D) a starting viscosity in a range from 1000 to 100,000 mPa·s;

wherein the storage-stable, isocyanate group-containing formulation additionally has the following property: (E) a content of isocyanate groups of less than 60% by weight, based on a total weight of the storage-stable, isocyanate group-containing formulation.

6 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the storage-stable, isocyanate group-containing formulation exhibits a rise in particle size of less than 500% on storage at 50° C. and standard pressure over a period of 3 days, as compared to an original particle size of the storage-stable, isocyanate group-containing formulation, based on Z average measured by dynamic light scattering, wherein the Z-average represents an intensity-weighted harmonic mean of a hydrodynamic diameter.

7 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the grinding resin d comprises monoalcohols or polyalcohols, monothiols or polythiols, monoamines or polyamines, condensation resins originating from a polyaldol reaction, or a mixture of at least two of these.

8 . The storage-stable, isocyanate group-containing formulation as claimed in claim 1 , wherein the molar ratio of isocyanate groups of component b to the sum of all isocyanate-reactive groups in the storage-stable, isocyanate group-containing formulation is at least 20:1.

9 . A method for coating of substrate surfaces, comprising applying the storage-stable, isocyanate group-containing formulation of claim 1 to a substrate surface to obtain a coated object.

10 . The coated object obtained as claimed in claim 9 .

11 . An ink, comprising the storage-stable, isocyanate group-containing formulation of claim 1 .

12 . A method of digital printing, comprising applying the ink of claim 11 to a substrate surface.

13 . A printed object obtained using the storage-stable, isocyanate group-containing formulation as claimed in claim 1 as an ink.

14 . The printed object as claimed in claim 13 , wherein a material of the object comprises textile, wood, plastic, glass, ceramic, carbon, metal, or a combination of at least two of these.

15 . A process for preparing a storage-stable, isocyanate group-containing formulation at least comprising:

i. dispersing at least one pigment in at least one grinding resin in the presence of at least one wetting agent and/or dispersant, to obtain a pigment dispersion,

ii. optionally diluting the pigment dispersion with solvent,

iii. mixing the pigment dispersion with 59.2% to 92.1% by weight of an isocyanate group-containing component based on a total weight of the storage-stable, isocyanate group-containing formulation and at least one component having at least one isocyanate-reactive group to obtain the storage-stable, isocyanate group-containing formulation,

wherein a ratio of a sum of isocyanate groups to a sum of all isocyanate-reactive groups in the storage-stable, isocyanate group-containing formulation is at least 11:1,

wherein the storage-stable, isocyanate group-containing formulation after storage at 50° C. over a period of at least 14 days exhibits a rise in viscosity of less than 300%, based on a starting viscosity of the storage-stable, isocyanate group-containing formulation.

Assignments (3)
MERGER Recorded Oct 29, 2024
From: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 069272/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2020
From: TILLACK, JOERG; ACHTEN, DIRK; BACH, MONIKA; WEBER, ACHIM; SCHUSTER, FABIAN
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 053719/0427 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2020
From: COVESTRO DEUTSCHLAND AG
To: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
Reel/Frame 053719/0442 →
Priority Claims (1)
EP 18162062 · Mar 15, 2018 · regional
Continuity (1)
Related Publication 20200407576A1 · Dec 31, 2020
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