IP Library Granted Patent US 11,965,054
Granted Patent B2
US 11,965,054 · App. 17/429,664 · Granted Apr 23, 2024

Storage-stable pigmented isocyanate group-containing formulations with isocyanate group-containing grinding resin and use thereof

Inventors: Joerg Tillack (Solingen, DE); Dirk Achten (Leverkusen, DE); Achim Weber (Altbach, DE); Fabian Schuster (Leverkusen, DE)
Assignee: Covestro Intellectual Property GmbH & Co. KG
C08G18/02C08G18/0847C08G18/73C08G18/7621C08G18/792C09D7/41C09D175/04
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Quick Facts
Patent No.
US 11,965,054
App. No.
17/429,664
Granted
Apr 23, 2024
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 isocyanate group-containing grinding 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 preparation of such formulations and to the use thereof.

Claims (25)

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

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

b. 0% to 99% by weight of at least one isocyanate group-containing component which has free isocyanate groups;

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

d. 0.1% to 35% by weight of at least one isocyanate group-containing grinding resin comprising free isocyanate groups; and

e. 0% to 80% by weight solvents,

in each case based on a total amount of the formulation, with the sum of all constituents

in the formulation not exceeding 100% by weight,

wherein the formulation after storage at 50° C. over a period of at least 3 days exhibits a rise in viscosity of less than 500%, based on a starting viscosity of the formulation which is determined as of 1 hour after combining all of the components, wherein the viscosity determination is carried out in each case at 20° C. at a shear rate of 500 [ 1/s], wherein a molar ratio of the sum of all isocyanate groups of the isocyanate group-containing formulation to a sum of all isocyanate-reactive groups which are not isocyanate groups in the formulation is at least 8:1, wherein the isocyanate group-containing grinding resin d. has a viscosity in a range from 100 to 5000 mPas, and wherein the isocyanate group-containing grinding resin d. is selected from the group consisting of 1,4-iisocyanatobutane (BDI), 1,5-diisocyanatopentane (PDI), 1,6-diisocyanatohexane (HDI), 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and/or 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and/or 1,4-bis(isocyanatomethyl)benzene (XDI), 1,3- and/or 1,4-bis(1-isocyanato-1-methylethyl)benzene (TMXDI), 2,4- and/or 2,6-diisocyanatotoluene (TDI), 2,4′- and/or 4,4′-diisocyanatodiphenylmethane (MDI), 1,5-diisocyanatonaphthalene, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane, 2,4′- and/or 4,4′-diisocyanatodicyclohexylmethane (H12MDI), a mixture of at least two of these, and optionally oligomers and reaction products of these.

2. The formulation as claimed in claim 1 , wherein the isocyanate group-containing component b. is selected from the group consisting of 1,4-diisocyanatobutane (BDI), 1,5-diisocyanatopentane (PDI), 1,6-diisocyanatohexane (HDI), 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and/or 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and/or 1,4-bis(isocyanatomethyl)benzene (XDI), 1,3- and/or 1,4-bis(1-isocyanato-1-methylethyl)benzene (TMXDI), 2,4- and/or 2,6-diisocyanatotoluene (TDI), 2,4′- and/or 4,4′-diisocyanatodiphenylmethane (MDI), 1,5-diisocyanatonaphthalene, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 1-isocyanato-1-methyl-4(3)-isocyanatomethylcyclohexane, 2,4′- and/or 4,4′-diisocyanatodicyclohexylmethane (H12MDI), a mixture of at least two of these, and optionally oligomers and reaction products of these.

3. The formulation as claimed in claim 1 , wherein the isocyanate group-containing component b. and the isocyanate group-containing grinding resin d. comprise aliphatic or cycloaliphatic isocyanates or mixtures of these.

4. The formulation as claimed in claim 1 , wherein the formulation has at least one of the following properties at room temperature:

(A) a starting viscosity in a range from 1 to 200 mPas;

(B) a starting viscosity in a range from 30 to 1000 mPas;

(C) a starting viscosity in a range from 50 to 2000 mPas;

(D) a starting viscosity in a range from 1000 to 100 000 mPas;

(E) a content of isocyanate groups of less than 60% by weight, and greater than 3%, based on a total amount of the formulation.

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

6. A method of coating a substrate surface to obtain a coated object, comprising applying the storage-stable, isocyanate group-containing formulation of claim 1 to at least a portion of the substrate surface.

7. A coated object obtained as claimed in claim 6 .

8. The object as claimed in claim 6 , wherein the material of the object comprises textile, wood, plastic, glass, ceramic, carbon, metal, or a combination of at least two of these.

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

10. A method of preparing a storage-stable, isocyanate group-containing formulation according to claim 1 , comprising preparing the formulation with the grinding resin comprising the at least one isocyanate group-containing resin comprising free isocyanate groups.

11. The formulation as claimed in claim 4 , wherein the formulation has one of the properties selected from (A) to (D) in combination with property (E).

12. The formulation as claimed in claim 1 , wherein the formulation comprises the solvents e., and the isocyanate group-containing grinding resin d. comprises 1,6-diisocyanatohexane (HDI) and optionally oligomers and reaction products of these.

Assignments (4)
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 21, 2021
From: WEBER, ACHIM; SCHUSTER, FABIAN
To: FRAUNHOFER GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG EV
Reel/Frame 057542/0224 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 21, 2021
From: FRAUNHOFER GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E.V.
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 057542/0263 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 21, 2021
From: TILLACK, JOERG; ACHTEN, DIRK
To: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
Reel/Frame 057542/0559 →
Priority Claims (1)
EP 19159968 · Feb 28, 2019 · regional
Continuity (1)
Related Publication 20220106427A1 · Apr 7, 2022
Cited By (1)
US 12,570,864