Crosslinkable composition comprising a latent base catalyst and latent base catalyst compositions

Patent metadata

Field	Value
Publication number	US-9718988-B2
Application number	US-201414246267-A
Country	US
Kind code	B2
Filing date	Apr 7, 2014
Priority date	Oct 7, 2011
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

A crosslinkable composition including at least one crosslinkable component that is crosslinkable under the action of a base catalyst, a first carbonate salt according to a first formula as latent base crosslinking catalyst, and a second carbonate salt according to a second formula as potlife extender, wherein the second carbonate is present in an amount of at least 5 mole % and preferably at most 500 mole % relative to the molar amount of the first carbonate. Further disclosed are catalyst compositions composed of the first and second carbonate salts, to the use of the catalyst composition as base catalyst system in crosslinkable compositions and the crosslinkable compositions, in particular coating compositions comprising the catalyst composition.

First claim

What is claimed is:

1. A crosslinkable composition comprising
a. 0.1-99 wt % of at least one crosslinkable component that is crosslinkable under the action of a base catalyst, all wt % herein being relative to the crosslinkable composition,
b. a first carbonate salt according to Formula 1 as latent base crosslinking catalyst,

wherein X + represents a non-acidic cation and wherein R is hydrogen, alkyl, or aralkyl group, wherein non-acidic means a pKa of at least 11.5 relative to water, and
c. a second carbonate salt according to Formula 2 as potlife extender:

 wherein Y is N or P and wherein each R′ is hydrogen, a substituted or unsubstituted alkyl, aryl or aralkyl group, and R is hydrogen, alkyl, or aralkyl group, wherein the second carbonate is present in an amount of at least 5 mole % and at most 500 mole % relative to the molar amount of the first carbonate, and wherein the cation of the second carbonate salt has a pKa of less than 11.5 relative to water.

2. The crosslinkable composition according to claim 1 , wherein the latent base crosslinking catalyst is present in an amount of 0.001-0.3 meq/g solids, meq latent base relative to dry total weight of the crosslinkable composition.

3. The crosslinkable composition according to claim 1 , further comprising 0.1-70 wt % of an organic solvent wherein at least 0.5 wt %, relative to total weight of the crosslinkable composition, is a primary alcohol.

4. The crosslinkable composition according to claim 1 , further comprising 0.1-10 wt % water.

5. The crosslinkable composition according to claim 1 , further comprising 0.1-70 wt % of an organic carbonate component according to formula RO—C(═O)O—R wherein R is an alkyl.

6. The crosslinkable composition according to claim 1 , wherein the at least one crosslinkable component comprises reactive components A and B, each comprising at least 2 reactive groups, wherein the at least 2 reactive groups of component A are acidic protons C—H in activated methylene or methine groups and the at least 2 reactive groups of component B are activated unsaturated groups C═C.

7. The crosslinkable composition according to claim 6 , wherein the reactive component A is a malonate or a acetoacetate or a acetylacetone, or mixtures thereof, and wherein the component B comprises an unsaturated acryloyl or maleate functional group.

8. The crosslinkable composition according to claim 7 , wherein the reactive component A comprises at least 50 mole % malonate.

9. A coating composition comprising the crosslinkable composition according to claim 1 , and additional binders, coating additives or fillers.

10. A method for preparing a cross-linked coating comprising applying a layer of the crosslinkable coating composition according to claim 9 on a substrate and curing the coating composition by evaporation of carbon dioxide from the layer.

11. A catalyst composition for use as a latent base catalyst system in crosslinkable compositions, composed of
a. A latent base catalyst, wherein said latent base catalyst is a first carbonate salt according to Formula 1:

 wherein X + represents a non-acidic cation and wherein R is hydrogen, alkyl, or aralkyl group, wherein non-acidic means a pKa of at least 11.5 relative to water, and
b. a potlife extender, wherein said potlife extender is a second carbonate salt according to Formula 2:

 wherein Y is N or P, wherein each R′ is hydrogen, a substituted or unsubstituted alkyl, aryl or aralkyl group, and wherein R is hydrogen, alkyl, or aralkyl group, wherein the second carbonate is present in an amount of at least 5 mole % and at most 500 mole % relative to the molar amount of the first carbonate, and wherein the cation of the second carbonate salt has a pKa of less than 11.5 relative to water and an organic solvent in an amount of 0.1-99.8 wt %, wherein at least part of the organic solvent is a primary alcohol.

12. The catalyst composition according to claim 11 , further comprising an organic carbonate component according to formula RO—C(═O)O—R wherein R is an alkyl.

13. The catalyst composition according to claim 11 , wherein the cation X + is a quaternary ammonium or phosphonium carbonate salt according to formula 3,

wherein Y represents N or P, and wherein each R″ is a same or different alkyl, aryl or aralkyl group.

14. The catalyst composition according to claim 11 , wherein the anions of the first and second carbonate salts are bicarbonate, methocarbonate or ethocarbonate.

15. The catalyst composition according to claim 11 , wherein the cation in the second carbonate salt is a protonated amine, protonated ammonia or a protonated volatile tertiary amine, and wherein the anion in the second carbonate is a bicarbonate or an alkylcarbonate.

16. The catalyst composition according to claim 11 , wherein the second carbonate salt is ammonium bicarbonate NH 4 HCO 3 or a bicarbonate of a protonated volatile tertiary amine.

17. The catalyst composition according to claim 11 , further comprising as a catalyst storage stability improver an organic carbonate component according to formula RO—C(═O)O—R wherein R is an alkyl, wherein the molar ratio of this organic carbonate component to the first carbonate salt is 0.01-50.

18. The catalyst composition according to claim 11 , further comprising water in amount between 0.1-10 wt % relative to total weight of the catalyst composition.

19. The catalyst composition of claim 11 , comprising
a. 0.1-50 wt % of the first carbonate salt
b. 0.1-50 wt % of the second carbonate salt and,
c. 0.1-99.8 wt % of the organic solvent.

20. A method for curing a coating composition comprising the catalyst composition according to claim 11 as a crosslinking catalyst, wherein said method comprises curing the coating composition at a temperature between 0 and 80° C.

Assignees

• Nuplex Resins Bv
• Allnex Netherlands Bv

Inventors

• Brinkhuis Richard Hendrikus Gerrit
• Buser Antonius Johannes Wilhelmus
• Schutyser Jan Andre Josef
• Gessner Michael Antony

Classifications

• C08K5/04

  Oxygen-containing compounds {(C08K5/0091 takes precedence)} · CPC title

• B01J31/0268

  Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous · CPC title

• B01J31/0239

  Quaternary ammonium compounds · CPC title

• C09D167/00 Primary

  Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers · CPC title

• B01J31/0205

  comprising carbonyl groups or oxygen-containing derivatives, e.g. acetals, ketals, cyclic peroxides · CPC title