# US 10,767,074 B2 · Process for the manufacture of a crosslinkable composition

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- Number: US 10,767,074 B2
- Document ID: US10767074B2
- Status: Granted
- Kind: B2
- Application number: 15/563,952
- Filed: 2016-04-15
- Published: 2018-05-10
- Granted: 2020-09-08
- Earliest claimed: 2015-04-17
- Assignees: Allnex Netherlands B.V.
- Applicants: Allnex Netherlands B.V.
- Inventors: Elwin Aloysius Cornelius Adrianus De Wolf; Ferry Ludovicus Thys; Richard Hendrikus Gerrit Brinkhuis; Nicole Mangnus-Verhagen; Antonius Johannes Wilhelmus Buser
- Web page: https://patentgrep.com/patent/US10767074B2

## CPC

- C09D 167/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence)
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C09D 17/008: {Titanium dioxide}
- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D 167/06: Unsaturated polyesters having carbon-to-carbon unsaturation
- C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence)
- C08J 2467/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08J2467/06 takes precedence)
- C08L 2205/025: containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
- C08L 2312/00: Crosslinking
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The invention relates to a process for the preparation of a RMA crosslinkable composition comprising at least one crosslinkable component comprising 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 and base catalyst C and one or more N—H group containing reactivity moderating component D that are also a Michael addition donor reactable with component B under the action of catalyst C, characterized in that the one or more reactivity moderating components D have a melting temperature above 60° C. and is first dissolved in one or more crosslinkable components comprising reactive components A or B and the obtained pre-dissolved product is later mixed with other components of the RMA crosslinkable composition.

## Claims

### Claim 1

A process for the preparation of a RMA crosslinkable composition comprising at least one crosslinkable component comprising 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 and base catalyst C and one or more N—H group containing reactivity moderating component D that are also a Michael addition donor reactable with component B under the action of catalyst C, characterized in that the one or more reactivity moderating components D have a melting temperature above 60° C. and is first dissolved in one or more crosslinkable components comprising reactive components A or B and the obtained pre-dissolved product is later mixed with other components of the RMA crosslinkable composition and wherein component D is dissolved in the one or more crosslinkable component comprising reactive components A or B at a temperature above its melting temperature.

### Claim 2 (depends on 1)

The process of claim 1, wherein component D is dissolved in the one or more crosslinkable component comprising reactive components A at a temperature above the melting temperature of reactivity moderating component D.

### Claim 3 (depends on 1)

The process of claim 1, wherein the crosslinkable component is a polymer chosen from the group of polyesters, polyurethanes, polyacrylates, epoxy resins, polyamides and polyvinyl resins, which contains reactive components A or B in the main chain, pendant, terminal or combinations thereof.

### Claim 4 (depends on 1)

The process of claim 1, wherein the crosslinkable components are polymeric components with a weight average molecular weight Mw of at least 250 gr/mol.

### Claim 5 (depends on 1)

The process of claim 1, wherein the crosslinkable component is a polymer comprising reactive component A or B or both and is synthesised at a temperature above the melting temperature of component D and wherein component D is added directly after the synthesis of said polymer and dissolved therein before cooling to a temperature below the melting temperature of the component D.

### Claim 6 (depends on 5)

The process of claim 5, wherein the crosslinkable component is a polyester comprising reactive components A which is synthesised by forming a polyester polymer using reactive component A as monomer or by transesterification of polyester polymer with a reactive component A.

### Claim 7 (depends on 1)

The process of claim 1, wherein reactive component A is malonate or acetoacetate and reactive component B is acryloyl.

### Claim 8 (depends on 1)

The process of claim 1, wherein the N—H group in component D has a pKa (defined in aqueous environment) of at least one unit less than that of the C—H groups in component A.

### Claim 9 (depends on 1)

The process of claim 1, wherein the pKa of the N—H group in component D is lower than 13.

### Claim 10 (depends on 1)

The process of claim 1, wherein component D comprises a molecule containing the N—H as part of a group —(C═O)—NH—(C═O)—, or of a group —NH—(O═S═O)— or a heterocycle in which the nitrogen of the N—H group is contained in a heterocyclic ring.

### Claim 11 (depends on 1)

The process of claim 1, wherein component D is selected from the group consisting of a substituted or unsubstituted succinimide, phthalimide, glutarimide, hydantoin, triazole, pyrazole, imidazole and uracil or mixtures thereof.

### Claim 12 (depends on 1)

The process of claim 1, wherein component D is present in an amount between 0.1 and 10 wt %, relative to the total amount of component D and the amount of the one or more crosslinkable components comprising reactive component A or B.

### Claim 13 (depends on 1)

The process of claim 1, wherein component D is present in such amount that the amount of N—H groups in component D is no more than 30 mole %, relative to C—H donor groups from component A present in the crosslinkable polymer.