Process for the preparation of a crosslinker composition
View Patent ↗This invention is directed to a process for the preparation of a crosslinker composition, comprising the steps of providing a mixture of an aliphatic alcohol A having at least one hydroxyl group and from 1 to 10 carbon atoms, with at least one multifunctional aldehyde C having at least two aldehyde groups —CHO to form a mixture AC, heating the mixture AC to convert at least a part of the multifunctional aldehyde C to its hemiacetal or to its acetal to form a mixture (AC)′, adding to the mixture (AC)′ least one cyclic urea U or the educts to produce the said cyclic urea U in situ, which cyclic urea U has at least one unsubstituted >NH group, and reacting the mixture thus obtained to form a chemical bond between the nitrogen atom of the at least one unsubstituted >NH group of the at least one cyclic urea U5 and the carbon atom of the least one aldehyde group —CHO of the multifunctional aldehyde C, and coating compositions comprising the said crosslinker composition.
1. A process for the preparation of a crosslinker composition, comprising the steps of
providing a mixture of an aliphatic alcohol A having at least one hydroxyl group and from 1 to 10 carbon atoms, with at least one multifunctional aldehyde C having at least two aldehyde groups —CHO to form a mixture AC,
heating the mixture AC to convert at least a part of the multifunctional aldehyde C to its hemiacetal or to its acetal to form a mixture (AC)′,
adding to the mixture (AC)′ at least one cyclic urea U or the educts to produce the said cyclic urea U in situ, which cyclic urea U has at least one unsubstituted >NH group, and reacting the mixture thus obtained to form a chemical bond between the nitrogen atom of the at least one unsubstituted >NH group of the at least one cyclic urea U, and the carbon atom of the least one aldehyde group —CHO of the multifunctional aldehyde C,
wherein boric acid H 3 BO 3 is added to the mixture AC, or to the mixture (AC)′, or to both mixtures AC and (AC)′.
2. The process of claim 1 , which further comprises reacting, after the last step of claim 1 , the reaction product obtained in the said last step of claim 1 with the aliphatic alcohol A, whereby at least a part of the hydroxyl groups of the said alcohol A is converted to ether groups.
3. The process of claim 1 , wherein the at least one cyclic urea U is selected from the group U1 consisting of ethylene urea, 4-hydroxyethylene urea, 4,5-dihydroxy ethylene urea, and glycoluril, and from the group U2 consisting of the ureas U1 which additionally have at least one substituent R on at least one of the nitrogen or carbon atoms of the said ureas U1, with the proviso that at least one nitrogen atom is unsubstituted, and the substituent R is selected from the group consisting of linear, branched and cyclic alkyl groups having from 1 to 10 carbon atoms.
4. The process of claim 1 , wherein the at last one cyclic urea U is formed in situ by reaction of a urea, a di-urea or a polyurea having one, two or more than two groups of the structure —NH—CO—NH— in their molecules with a polyfunctional aldehyde having more than one aldehyde groups per molecule.
5. The process of claim 1 , wherein a mixture of ethylene urea and 4,5-dihydroxyethylene urea is used as the at least one cyclic urea U.
6. The process of claim 1 , wherein glyoxal is used as multifunctional aldehyde C.
7. The process of claim 1 wherein the amount of boric acid H 3 BO 3 which is added to the mixture AC, or to the mixture (AC)′ or to both mixtures AC and (AC)′, measured as the ratio of the amount of substance n B of boric acid H 3 BO 3 to the sum n G of the amounts of substance of glyoxal, of the hemiacetal of glyoxal, and of the acetal of glyxal, is from 0.5% to 25%.
8. A coating composition comprising a binder resin B which has functional groups selected from the group consisting of hydroxyl groups and carboxylic acid groups, and a crosslinking composition prepared by the process of claim 1 .
9. A coating composition comprising a binder resin B which has functional groups selected from the group consisting of hydroxyl groups and carboxylic acid groups, and a crosslinking composition prepared by the process of claim 2 .
10. The coating composition of claim 8 wherein the binder resin B is selected from the group consisting of hydroxyfunctional alkyd resins, hydroxyfunctional acrylic resins, hydroxyfunctional polyurethane resins, and hydroxyfunctional epoxy resins, as well as mixtures thereof.
11. The coating composition of claim 8 wherein the binder resin B is present in the form of an aqueous dispersion.
12. A method of use of the coating composition of claim 8 comprising adding thereto a catalyst selected from the group consisting of organic sulphonic acids, applying the mixture thus prepared to a substrate by spraying, brushing, dipping, or with a doctor blade.
13. The method of claim 12 wherein the coating composition and catalyst are applied to a substrate selected from the group consisting of paper, cardboard, textiles, leather, wood, plastics, and metals.
14. The process of claim 1 wherein the amount of boric acid H 3 BO 3 which is added to the mixture AC, or to the mixture (AC)′ or to both mixtures AC and (AC)′, measured as the ratio of the amount of substance n B of boric acid H 3 BO 3 to the sum n G of the amounts of substance of glyoxal, of the hemiacetal of glyoxal, and of the acetal of glyxal, is from 1% to 20%.
15. The process of claim 1 wherein the amount of boric acid H 3 BO 3 which is added to the mixture AC, or to the mixture (AC)′ or to both mixtures AC and (AC)′, measured as the ratio of the amount of substance n B of boric acid H 3 BO 3 to the sum n G of the amounts of substance of glyoxal, of the hemiacetal of glyoxal, and of the acetal of glyxal, is from 3% to 15%.