# US 10,501,573 B2 · Radiation curing composition

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- Number: US 10,501,573 B2
- Document ID: US10501573B2
- Status: Granted
- Kind: B2
- Application number: 16/073,113
- Filed: 2016-12-30
- Published: 2019-02-14
- Granted: 2019-12-10
- Earliest claimed: 2016-01-28
- Assignees: Perstorp AB
- Applicants: Perstorp AB
- Inventors: Stefan Lundmark; Pia Wennerberg
- Web page: https://patentgrep.com/patent/US10501573B2

## CPC

- C08G 63/13: containing two or more aromatic rings
- C08F 218/02: Esters of monocarboxylic acids
- C08F 220/04: Acids; Metal salts or ammonium salts thereof
- C08F 220/10: Esters
- C08G 63/08: Lactones or lactides
- C08G 63/52: Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G 63/78: Preparation processes
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D 131/02: Homopolymers or copolymers of esters of monocarboxylic acids
- C09J 131/02: Homopolymers or copolymers of esters of monocarboxylic acids
- C08K 3/30: Sulfur-, selenium- or tellurium-containing compounds
- C08K 5/1515: Three-membered rings
- C08K 5/1545: Six-membered rings
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

Disclosed is a radiation curable composition comprising 2-hydroxy-3-butenoic acid and/or at least one ester of 2-hydroxy-3-butenoic acid and at least one additional compound selected from radiation curable monomers, oligomers and polymers.

## Claims

### Claim 1

A radiation curable composition characterised in that it comprises 2-hydroxy-3-butenoic acid and/or at least one ester of 2-hydroxy-3-butenoic acid and at least one additional compound selected from radiation curable monomers, oligomers and polymers.

### Claim 2 (depends on 1)

A composition according to claim 1 characterised in that said ester of 2-hydroxy-3-butenoic acid is a methyl or ethyl ester.

### Claim 3 (depends on 2)

A composition according to claim 2 characterised in that said methyl or ethyl ester is methyl vinyl glycolate or ethyl vinyl glycolate.

### Claim 4 (depends on 1)

A composition according to claim 1 characterised in that said ester of 2-hydroxy-3-butenoic acid is an ester with 2-ethyl-heptanol, 2-propyl-heptanol, 5-hydroxy-1,3-dioxane, 5-hydroxymethyl-1,3-dioxane, or 5-hydroxyethyl-1,3-dioxane.

### Claim 5 (depends on 1)

A composition according to claim 1 characterised in that said ester of 2-hydroxy-3-butenoic acid is an ester with a hyperbranched dendritic polyol.

### Claim 6 (depends on 1)

A composition according to claim 1 characterised in that said ester of 2-hydroxy-3-butenoic acid is a mono or diester of a diol, a mono, di or triester of a triol, a mono, di, tri or tetraester of a tetrol, a mono, di, tri, tetra or pentaester of a pentol or a mono, di, tri, tetra, penta or hexaester of a hexol.

### Claim 7 (depends on 1)

A composition according to claim 1 characterised in that said additional compound is at least one acrylic, methacylic or crotonic ester having at least one carbon-carbon double bond.

### Claim 8 (depends on 7)

A composition according to claim 7 characterised in that said acrylic, methacrylic or crotonic ester is an ester with a hyperbranched dendritic polyol.

### Claim 9 (depends on 7)

A composition according to claim 7 characterised in that said acrylic, methacrylic or crotonic ester is a mono or diester of a diol, a mono, di or triester of a triol, a mono, di, tri or tetraester of a tetrol, a mono, di, tri, tetra or pentaester of a pentol or a mono, di, tri, tetra, penta or hexaester of a hexol.

### Claim 10 (depends on 1)

A composition according to claim 1 characterised in that said additional compound is at least one allyl or methallyl ether having at least one carbon-carbon double bond.

### Claim 11 (depends on 10)

A composition according to claim 10 characterised in that said allyl or methallyl ether is an ether with a hyperbranched dendritic polyol.

### Claim 12 (depends on 10)

A composition according to claim 10 characterised in that said allyl or methallyl ether is a mono or diether of a diol, a mono, di or triether of a triol, a mono, di, tri or tetraether of a tetrol, a mono, di, tri, tetra or pentaether of a pentol or a mono, di, tri, tetra, penta or hexaether of a hexol.

### Claim 13 (depends on 1)

A composition according to claim 1 characterised in that it additionally comprises at least one epoxy (meth)acrylate, amine modified epoxy (meth)acrylate, urethane (meth)acrylate, bisphenol A (meth)acrylate, polyester (meth)acrylate, polyether (meth)acrylate, amine modified polyether (meth)acrylate and/or acid functional (meth)acrylate.

### Claim 14 (depends on 1)

A composition according to claim 1 characterised in that it additionally comprises lauryl(meth)acrylate, nonylphenol (meth)acrylate, and/or alkoxylated nonylphenol (meth)acrylate, oxetane(meth)acrylate, cyano(meth)acrylate and/or tetrahydrofurfuryl (meth)acrylate, wherein the alkoxylated nonylphenol (meth)acrylate, oxetane(meth)acrylate, cyano(meth)acrylate and/or tetrahydrofurfuryl (meth)acrylate are selected from ethoxylated, propoxylated, and butoxylated nonylphenol (meth)acrylate, oxetane(meth)acrylate, cyano(meth)acrylate and tetrahydrofurfuryl (meth)acrylate.

### Claim 15 (depends on 1)

A composition according to claim 1 characterised in that it additionally comprise at least one vinyl monomer, oligomer or polymer, selected from vinylpyrrolidones, polyolefins, styrenes, vinyl halides, vinyl acetates, vinyl alcohols and acrylonitriles.

### Claim 16 (depends on 1)

A composition according to claim 1 characterised in that it additionally comprises at least one matting agent, flow/levelling agent, rheology modifying agent, dye and/or pigment.

### Claim 17 (depends on 1)

A composition according to claim 1 characterised in that it is a UV, IR and EB curable compositions.

### Claim 18 (depends on 1)

A composition according to claim 1 characterised in that it is a UV curable composition which additionally comprises at least one photoinitiator.

### Claim 19 (depends on 18)

A composition according to claim 18 characterised in that said photoinitiator is a free radical, cation or anion photoinitiator.

### Claim 20 (depends on 18)

A composition according to claim 18 characterised in that said photoinitiator is a sulphonium antimonate, a sulphonium fluoroantimonate, a sulphonium fluorophosphate, a sulphonium nitrate, a sulphonium triflate, an iodonium fluorophophate, a hydroxy(cyclo)alkylaryl ketone, a metallocene, a ketoprofen, a benzoin ether, a benzil ketal, an acetophenone, a benzophenone, an amino(cyclo)alkylphenone, an acylphosphine oxide, a benzoephenone, a thixantone, an anthraquinone and/or a camphorquinone.
