Formaldehyde free crosslinking compositions

Patent metadata

Field	Value
Publication number	US-10457776-B2
Application number	US-201615780276-A
Country	US
Kind code	B2
Filing date	Dec 23, 2016
Priority date	Dec 30, 2015
Publication date	Oct 29, 2019
Grant date	Oct 29, 2019

Abstract

The present invention relates to reaction products H of at least one cyclic urea U, at least one multifunctional aldehyde A and at least one polyol P, process for preparing thereof and compositions comprising thereof.

First claim

The invention claimed is:

1. A reaction product H of at least one cyclic urea U, at least one multifunctional aldehyde A and at least one polyol P,
wherein the at least one polyol P is selected from the group consisting of hexanediol, 2-methyl-1,3-propanediol (MP diol), 2-ethyl-1,2-hydroxymethyl-1,3-propanediol, trimethylol propane (TMP), tris (hydroxymethyl) ethane (THME), cyclohexanedimethanol (CHDM), neopentyl glycol (NPG), trimethylpentanediol, dimethylolpropionic acid (DMPA) and pentaerythritol.

2. The reaction product H according to claim 1 , wherein the at least one polyol P is selected from the group consisting of 2-methyl-1,3-propanediol, 2-ethyl-1,2-hydroxymethyl-1,3-propanediol, trimethylol propane and 1,6 hexanediol.

3. The reaction product H according to claim 1 , wherein the at least one polyol P is 2-methyl-1,3-propanediol.

4. The reaction product H according to claim 1 , wherein the reaction product H is obtained in the presence of at least one acid catalyst C.

5. The reaction product H according to claim 4 , wherein the at least one acid catalyst C is an organic acid catalyst.

6. The reaction product H according to claim 4 , wherein the at least one acid catalyst C is selected from the group consisting of citric acid, succinic acid, lactic acid, tartaric acid and any mixtures thereof.

7. The reaction product H according to claim 4 , wherein the at least one acid catalyst C is citric acid.

8. The reaction product H according to claim 1 , wherein the ratio of the amount of reacted polyol P to the amount of the at least one cyclic urea U is at least 0.01 mol/mol.

9. The reaction product H according to claim 1 , wherein the at least one cyclic urea U is selected from the group consisting of ethylene urea, 1,3-propylene urea, 1,2-propylene urea, 1,4-butylene urea, glycoluril and any mixtures thereof.

10. The reaction product H according to claim 1 , wherein the at least one multifunctional aldehyde A is selected from the group consisting of glyoxal, malonic dialdehyde, succinic dialdehyde, glutaric dialdehyde and any mixtures thereof.

11. The reaction product H according to claim 1 , which is non-etherified or etherified.

12. A process for preparing the reaction product H according to claim 1 , comprising the step of:
a) mixing at least one cyclic urea U with at least one multifunctional aldehyde A in order to effect an addition reaction in the presence of at least one base B, which does not react with any of the multifunctional aldehyde A, the cyclic urea U, and the reaction product H, and at least one polyol P.

13. The process according to claim 12 , wherein the ratio of the amount of substance of the at least one multifunctional aldehyde A to the amount of substance of the at least one cyclic urea U is comprised within the range of between 0.8:1 and 1.4:1 molar equivalents.

14. The process according to claim 12 , wherein the ratio of the amount of substance of the at least one polyol P to the amount of substance of the at least one cyclic urea U is comprised within the range of between 0.01:1 and 1:1 molar equivalents.

15. A process for preparing the reaction product H according to claim 1 , comprising the steps of:
a) mixing at least one cyclic urea U with at least one multifunctional aldehyde A in order to effect an addition reaction in the presence of at least one base B, which does not react with any of the multifunctional aldehyde A, the cyclic urea U, and the reaction product H, and then
b), admixing at least one polyol P to the at least one cyclic urea U, the at least one multifunctional aldehyde A and the at least one base B.

16. The process according to claim 12 , wherein at least one acid catalyst C is admixed.

17. A coating composition comprising the reaction product H according to claim 1 .

18. The coating composition according to claim 17 , further comprising at least one crosslinkable resin and optionally water and/or optionally at least one organic solvent.

19. The coating composition according to claim 18 , wherein the at least one crosslinkable resin is an oligomeric or polymeric material having at least one functional group having active hydrogen atoms, wherein the functional group is selected from the group consisting of hydroxyl functional groups, acid functional groups, carboxylic acid functional groups, amide functional groups, amino functional groups, imino functional groups, imide functional groups, mercaptan functional groups, phosphine functional groups and carbamate functional groups.

20. The coating composition according to claim 17 , which is a waterborne coating composition.

21. The coating composition according to claim 18 , which is a waterborne coating composition using hydroxy functional acrylic resins with sulphonic acid groups incorporated in the polymer as the crosslinkable resin.

22. The coating composition according to claim 17 , which further comprises a catalyst CB selected from:
an acid catalyst selected from the group consisting of organic sulphonic acids, organic phosphonic acids, organic sulphonimides, organic carboxylic acids and Lewis acids,
salts of Lewis acids, or
complexes of Lewis acids.

23. A method of use of the reaction product H according to claim 1 as a crosslinker comprising applying the reaction product H to a substrate.

24. The method according to claim 23 , comprising admixing the reaction product H with at least one crosslinkable resin and optionally with water and/or optionally with at least one organic solvent, homogenizing and applying the homogenized mixture to the substrate.

25. The method according to claim 23 , wherein the substrate is selected from the group consisting of plastics, thermoplastics, thermosets, wood, fabricated wood, ceramics, glass, leather, textiles, tyre cord, rubber objects, paper, cardboard, plaster, concrete, metal, metallized circuit boards, semiconductor surfaces, displays, and packagings for electronic circuitry.

Assignees

• Allnex Netherlands Bv

Inventors

• Treasurer Urvee Y
• Wilde Zachary
• Flood Lawrence
• Quinn Sarah
• Brogan Colin
• Gupta Ram

Classifications

• C08G12/424

  of polycondensates based on heterocyclic compounds · CPC title

• C08G12/26 Primary

  with heterocyclic compounds · CPC title

• C09D161/32 Primary

  Modified amine-aldehyde condensates · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08G71/02 Primary

  Polyureas · CPC title