Modified amino resins

Patent metadata

Field	Value
Publication number	US-10179829-B2
Application number	US-201615355534-A
Country	US
Kind code	B2
Filing date	Nov 18, 2016
Priority date	Mar 23, 2012
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

This invention relates to products H made by reaction of a cyclic alkyleneurea U, at least one multifunctional aldehyde A2, and at least one of (a) an aminoplast former M that is not the same as the cyclic alkyleneurea U, and (b) a monofunctional aldehyde A1, which product H is optionally etherified by reaction of at least a part of the hydroxyl groups formed by addition reaction of N—H groups and aldehyde groups, with an alcohol having from one to ten carbon atoms, and wherein glyoxal is present in the at least one multifunctional aldehyde A2, to processes for their preparation, and to a method of use thereof in coating compositions.

First claim

The invention claimed is:

1. A reaction product of at least one multifunctional aldehyde A2 with at least one melamine derivative that has at least one alkoxycarbonyl group attached to one or more of nitrogen atoms that do not form a part of the ring, formed by a reaction of an aldehyde group of the multifunctional aldehyde A2 with either an amino group of the at least one melamine derivative, or a carbamoyl group in the at least one melamine derivative, or both.

2. The reaction product of claim 1 , wherein the at least one multifunctional aldehyde A2 obeys the formula OHC—R″—CHO, wherein R″ is be a direct bond or a divalent radical that is a linear, branched, or cyclic aliphatic divalent radical and has from one to forty carbon atoms, or an aliphatic divalent radical that is linear, branched, or cyclic and has from one to thirty-nine carbon atoms, which radical carries at least one additional aldehyde group CHO.

3. The reaction product of claim 1 , wherein the at least one multifunctional aldehyde A2 is selected from the group consisting of glyoxal, malonaldehyde, succinaldehyde, glutaraldehyde, adipaldehyde, 2-methoxymethyl-2,4-dimethylpentane-1,5-dial, cyclohexane-1,3-dial, cyclohexane-1,4-dial, and dialdehydes derived from dimer fatty acids.

4. The reaction product of claim 1 , wherein the at least one melamine derivative is selected from the group consisting of bis-(alkoxycarbamoyl)-monoaminotriazine and mono-(alkoxy-carbamoyl)diamino-triazine.

5. The reaction product of claim 1 which has four alkoxycarbamoyl groups and is formed by a reaction of one molecule of a difunctional aldehyde with two molecules of a bis-(alkoxycarbamoyl)-mono-aminotriazine.

6. The reaction product of claim 1 which has at least one chain-pendant alkoxycarbamoyl groups and is formed by a reaction of a difunctional aldehyde with a mono-(alkoxy-carbamoyl) diamino-triazine.

7. The reaction product of claim 1 , wherein the at least one melamine derivative is bis-(butoxy-carbonylamino)monoamino-triazine.

8. The reaction product according to claim 1 , wherein the at least one multifunctional aldehyde A2 is glyoxal.

9. A method of use of the reaction product of claim 1 in a coating composition comprising admixing the reaction product to a crosslinkable resin, to form a coating composition,
wherein the crosslinkable resin is an oligomeric or polymeric material having at least one functional group selected from the group consisting of hydroxy functional groups, acid functional groups, carboxyl functional groups, amide functional groups, amino functional groups, imino functional groups, mercaptan functional groups, phosphine functional groups, and carbamate functional groups.

10. The method of use of the reaction product according to claim 9 , wherein the crosslinkable resin is an oligomeric or polymeric material having at least one functional group selected from the group consisting of have hydroxy functional groups, amino functional groups, mercaptan functional groups, phosphine functional groups, and carboxyl functional groups.

11. A process to make the reaction product of claim 1 comprising the following steps:
A) charging the at least one multifunctional aldehyde A2,
B) admixing the at least one melamine derivative,
C) optionally, adding an alcohol R 1 —OH, and etherifying under acid conditions, and optionally, removing at least one of water and unreacted alcohol R 1 —OH,
D) further optionally, after step C), adding a further quantity of an alcohol R 2 —OH and etherifying under acid conditions, optionally, removing at least one of water and unreacted alcohol R 2 —OH,
where R 1 is selected from the group consisting of linear, branched, and cyclic alkyl groups having from one to ten carbon atoms, and optionally at least one olefinic unsaturation, and R 2 is selected from the group consisting of linear, branched, and cyclic alkyl groups having from one to ten carbon atoms, and optionally at least one olefinic unsaturation, and further optionally, at least one further hydroxyl group, wherein no two hydroxyl groups may be on the same carbon atom, and if R 1 is different from R 2 , the number of carbon atoms of R 1 is smaller than the number of carbon atoms of R 2 by at least one.

Assignees

• Allnex Ip Sarl
• Allnex Netherlands Bv

Inventors

• Gupta Ram B
• Treasurer Urvee Y
• Flood Lawrence A
• Lawless Barry A

Classifications

• C08L61/26

  of aldehydes with heterocyclic compounds · CPC title

• C08G12/28

  with substituted diazines, diazoles or triazoles · CPC title

• C08G12/043

  with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24 · CPC title

• C09D167/08

  Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids · CPC title

• C08G12/32

  Melamines · CPC title