Non-etherified reaction product of a cyclic urea and a multifunctional aldehyde

Patent metadata

Field	Value
Publication number	US-10647870-B2
Application number	US-201816204209-A
Country	US
Kind code	B2
Filing date	Nov 29, 2018
Priority date	Sep 30, 2010
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

The invention relates to a coating composition comprising a reaction product UA of at least one multifunctional aldehyde A with at least one cyclic urea U, and a crosslinkable resin having at least one kind of functional groups selected from the group consisting of hydroxyl functional groups, acid functional groups, amide functional groups, amino functional groups, imino functional groups, mercaptan functional groups, phosphine functional groups, and carbamate functional groups, characterised in that the degree of etherification, measured as the ratio «(13 O—R)/«(U) of the amount of substance n(—O—R) of alkoxy groups as substituents of the aldehyde carbon atoms of the multifunctional aldehyde chemically bound in the reaction product UA to the amount of substance «(U) of cyclic urea U chemically bound in the reaction products, is less than 0.01 mol/mol, and to a process for the preparation of the reaction product UA.

First claim

The invention claimed is:

1. A process for making a non-etherified reaction product UA of at least one multifunctional aldehyde A and at least one cyclic urea U, wherein the ratio of the amount of substance of aldehyde groups n(—CHO) in the multifunctional aldehyde A and the amount of substance of amide groups n(—CO—NH) in the cyclic urea U is 1.0 mol/mol≤n(—CHO)/n(—CO—NH)≤1.30 mol/mol, characterised in that the reaction of U and A is conducted in the presence of a solvent which does not have functional groups that are reactive with the said at least one multifunctional aldehyde A or the said at least one cyclic urea U, or the non-etherified reaction product UA, and that the degree of etherification, measured as the ratio n(—O—R)/n(U) of the amount of substance n(—O—R) of alkoxy groups as substituents of the aldehyde carbon atoms of the multifunctional aldehyde chemically bound in the reaction product UA to the amount of substance n(U) of cyclic urea U chemically bound in the reaction products, is less than 0.01 mol/mol.

2. The process of claim 1 wherein the at least one multifunctional aldehyde A is provided as a solution in water.

3. The process of claim 1 wherein the at least one cyclic urea U is provided as a solution in water.

4. The process of claim 1 wherein both the at least multifunctional aldehyde A and the at least one cyclic urea U are provided as a solution in water.

5. The process of claim 1 wherein water is removed completely or partially after or during the reaction.

6. The process of claim 1 wherein the reaction product is dried to yield a powder.

7. The process of claim 1 characterised in that the cyclic urea U is purified before reaction with the multifunctional aldehyde by one or more processes selected from the group consisting of recrystallisation, extraction, complexation, adsorption and ion exchange reactions, distillation, sublimation, and melt crystallisation.

8. A reaction product UA made by the process of claim 1 .

9. A process for making a non-etherified reaction product UA of at least one multifunctional aldehyde A and at least one cyclic urea U, wherein the ratio of the amount of substance of aldehyde groups n(—CHO) in the multifunctional aldehyde A and the amount of substance of amide groups n(—CO—NH) in the cyclic urea U is 1.0 mol/mol≤n(—CHO)/n(—CO—NH)≤1.30 mol/mol, characterised in that the process comprises at least two steps, wherein in the first step the amount of multifunctional aldehyde A used is between 20% and 80% of the total amount, and that after the first step, in at least one further step, further quantities of multifunctional aldehyde A are added and reacted with the reaction mixture formed in the previous step, and that the degree of etherification, measured as the ratio n(—O—R)/n(U) of the amount of substance n(—O—R) of alkoxy groups as substituents of the aldehyde carbon atoms of the multifunctional aldehyde chemically bound in the reaction product UA to the amount of substance n(U) of cyclic urea U chemically bound in the reaction products, is less than 0.01 mol/mol.

10. The process of claim 9 wherein a solvent which does not have functional groups that are reactive with the said at least one multifunctional aldehyde A or the said at least one cyclic urea U, or the non-etherified reaction product UA is added to the reaction mixture for the first step.

11. The process of claim 9 wherein a solvent which does not have functional groups that are reactive with the said at least one multifunctional aldehyde A or the said at least one cyclic urea U, or the non-etherified reaction product UA is added to the reaction mixture after the first step.

Assignees

• Allnex Netherlands Bv

Inventors

• Gupta Ram
• Flood Lawrence
• Treasurer Urvee
• Lawless Barry
• Brogan Colin

Classifications

• C09D161/24

  with urea or thiourea · CPC title

• C08G12/36 Primary

  Ureas; Thioureas · CPC title

• C08G12/12 Primary

  Ureas; Thioureas · CPC title

• C09D133/02 Primary

  Homopolymers or copolymers of acids; Metal or ammonium salts thereof · CPC title

• C09D161/26

  of aldehydes with heterocyclic compounds · CPC title