Water-dispersible modified polyisocyanates

Patent metadata

Field	Value
Publication number	US-2024010783-A1
Application number	US-202118044632-A
Country	US
Kind code	A1
Filing date	Sep 29, 2021
Priority date	Sep 30, 2020
Publication date	Jan 11, 2024
Grant date	—

Abstract

The invention relates to a water-dispersible modified polyisocyanate and use thereof, especially as a crosslinking component in water-soluble or water-dispersible coating compositions. The water-dispersible modified polyisocyanate can be obtained by the reaction of a system comprising a water-dispersible polyisocyanate and an isocyanate-reactive component; wherein the viscosity of the water-dispersible modified polyisocyanate is 3000 mPa·s-11000 mPa·s, which is measured with a MV-DIN rotor according to DIN EN ISO 3219:1994-10 at 23° C. and a shear rate of 10 s −1 . The modified polyisocyanate according to the present invention has good manual stirring behavior and good dispersibility, and the coating formed by the coating composition containing the modified polyisocyanate has high gloss and good transparency.

First claim

1 . A water-dispersible modified polyisocyanate comprising a reaction product of a system comprising
a. a water-dispersible polyisocyanate; and b. an isocyanate-reactive component; wherein the water-dispersible modified polyisocyanate comprises structures of formula I, II and III:

wherein X is selected from O, S, NR 9 and CR 10 R 11 ; wherein R 9 , R 10 and R 11 may be identical or different and represent hydrogen or organic groups inert to isocyanate groups; and the ratio of moles of the carbon atoms in the carbonyl group of formula I to the sum of moles of the structures of formula II and III calculated according to carbon NMR spectrum is 0.005-0.24; and the viscosity of the water-dispersible modified polyisocyanate is 3000 mPa·s to 11000 mPa·s, measured with a MV-DIN rotor in accordance with DIN EN ISO 3219:1994-10 at 23° C. and at a shear rate of 10 s −1 .

2 . The water-dispersible modified polyisocyanate according to claim 1 , wherein the component a) water-dispersible polyisocyanate has:
A. an average isocyanate functionality of at least 1.8; B. a number average molecular weight of 700 g/mol-1000 g/mol; C. a molecular weight distribution of 1.1-1.6; D. a viscosity of 500 mPa·s-6000 mPa·s; E. an isocyanate group content of 4.0% by weight to 26% by weight, relative to the total weight of the water-dispersible polyisocyanate; F. a sulfonate group content of 0.1% by weight to 7.7% by weight, relative to the total weight of the water-dispersible polyisocyanate; or G. a combination of any two or more of A to F.

3 . The water-dispersible modified polyisocyanate according to claim 1 , wherein the component b) isocyanate-reactive component is one or more of water and compounds having a structure of formula IV:

wherein Y is selected from O, N, S and O—CO, a is an integer greater than or equal to 1, b is an integer greater than or equal to 1, and R 1 is an organic group that is inert to isocyanate groups.

4 . The water-dispersible modified polyisocyanate according to claim 3 , wherein Y in the compound having the structure of formula IV is an oxygen atom, a is 1, and b is ≥2.

5 . The water-dispersible modified polyisocyanate according to claim 3 , wherein the compound having the structure of formula IV comprises one or more of a polyacid with a molecular weight of 40 g/mol-1000 g/mol, a polyamine with a molecular weight of 40 g/mol-1000 g/mol, a polythiol with a molecular weight of 40 g/mol-1000 g/mol, a hydroxy alcohol with a molecular weight of 40 g/mol-1000 g/mol, and a polyhydroxy polymer with a molecular weight of 200 g/mol-5000 g/mol.

6 . The water-dispersible modified polyisocyanate according to claim 1 , wherein the water-dispersible modified polyisocyanate has:
i. an average isocyanate functionality of at least 1.5; ii. a number average molecular weight of 700 g/mol-1200 g/mol; iii. a molecular weight distribution of 1.2-2.0; iv. an isocyanate group content of 4.0% by weight to 23% by weight, relative to the total weight of the water-dispersible modified polyisocyanate; v. a sulfonate group content of 0.1% by weight to 7.5% by weight, relative to the total weight of the water-dispersible modified polyisocyanate; vi. a total amount of molecules with a number average molecular weight greater than 2700 g/mol of 3.0% by weight to 20% by weight, relative to the total weight of the water-dispersible modified polyisocyanate; vii. a content of ethylene oxide units bonded into a polyether chain of the modified polyisocyanate of not more than 19.5% by weight, relative to the total weight of the water-dispersible modified polyisocyanate; or viii. a combination of any two or more of i to vii.

7 . The water-dispersible modified polyisocyanate according to claim 1 , wherein the ratio of moles of the carbon atoms in the carbonyl group of formula I to the sum of moles of the structures of formula II and III calculated according to carbon NMR spectrum is 0.005-0.15.

8 . The water-dispersible modified polyisocyanate according to claim 1 , wherein:
a. the water-dispersible polyisocyanate has
A. an average isocyanate functionality of at least 1.8;
B. a number average molecular weight of 700 g/mol-1000 g/mol;
C. a molecular weight distribution of 1.1-1.6;
D. a viscosity of 500 mPa·s-6000 mPa·s;
E. an isocyanate group content of 4.0% by weight to 26% by weight, relative to the total weight of the water-dispersible polyisocyanate; and
F. a sulfonate group content of 0.1% by weight to 7.7% by weight, relative to the total weight of the water-dispersible polyisocyanate; and
b. the isocyanate-reactive component comprises one or more of water and a hydroxy alcohol with a molecular weight of 40 g/mol-1000 g/mol.

9 . A method for preparing the water-dispersible modified polyisocyanate according to claim 1 , comprising mixing the component a) water-dispersible polyisocyanate or a component for preparing the water-dispersible polyisocyanate with the component b) isocyanate-reactive component in any manner.

10 . (canceled)

11 . A coating composition, an adhesive or a sealant comprising the water-dispersible modified polyisocyanate according to claim 1 .

12 . A substrate coated with the coating composition, the adhesive or the sealant according to claim 11 .

13 . (canceled)

14 . A method for preparing an aqueous two-component coating composition, comprising mixing an aqueous hydroxy resin dispersion, optionally an auxiliary and optionally an additive in any manner to obtain a mixture, and mixing and manually stirring the water-dispersible modified polyisocyanate according to claim 1 with the mixture to obtain the aqueous two-component coating composition.

15 . A product comprising a substrate and a coating formed by applying an aqueous two-component coating composition comprising an aqueous hydroxy resin dispersion, the water-dispersible modified polyisocyanate according to claim 1 , optionally an auxiliary agent and optionally an additive to the substrate.

16 . A polyisocyanate blocked by a blocking agent and prepared from the water-dispersible modified polyisocyanate according to claim 1 .

17 . A polyurethane prepared from the water-dispersible modified polyisocyanate according to claim 1 .

18 . A crosslinking component in a water-soluble or water-dispersible coating composition, adhesive or sealant or a crosslinking component in a water-soluble or water-dispersible aqueous two-component coating composition that is prepared from the water-dispersible modified polyisocyanate according to claim 1 .

Assignees

• Covestro Deutschland Ag

Inventors

• Liu Hao
• Ma Yaguang
• Xu Na
• Xia Tian
• Danielmeier Karsten
• Pires Raul
• Laas Hans-Josef

Classifications

• C08G18/7893

  having three nitrogen atoms in the ring · CPC title

• C08G18/7843

  containing urethane groups · CPC title

• C08G18/7887

  having two nitrogen atoms in the ring · CPC title

• C08G18/7875

  containing heterocyclic rings having at least one nitrogen atom in the ring · CPC title

• C08G18/706 Primary

  the liquid medium being water · CPC title