Storage-stable pigmented formulations containing isocyanate groups and use thereof

Patent metadata

Field	Value
Publication number	US-12570864-B2
Application number	US-201916979218-A
Country	US
Kind code	B2
Filing date	Mar 14, 2019
Priority date	Mar 15, 2018
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

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.

First claim

The invention claimed is:

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.

Assignees

• Covestro Intellectual Property Gmbh & Co Kg
• Covestro Deutschland Ag

Inventors

• Tillack Joerg
• Achten Dirk
• Bach Monika
• Weber Achim
• Schuster Fabian

Classifications

• C09D11/38

  characterised by non-macromolecular additives other than solvents, pigments or dyes · CPC title

• C09D11/322

  Pigment inks · CPC title

• C08G18/798

  containing urethdione groups · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/73 Primary

  acyclic · CPC title