# US 9,751,994 B2 · Method for curing a radically curable resin

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- Number: US 9,751,994 B2
- Document ID: US9751994B2
- Status: Granted
- Kind: B2
- Application number: 15/100,511
- Filed: 2014-12-09
- Published: 2016-10-13
- Granted: 2017-09-05
- Earliest claimed: 2013-12-12
- Assignees: Akzo Nobel Chemicals International B.V.
- Applicants: Akzo Nobel Chemicals International B.V.
- Inventors: Michel Van Den Berg; Auke Gerardus Talma
- Web page: https://patentgrep.com/patent/US9751994B2

## CPC

- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08J 3/02: Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J 3/095: {Oxygen containing compounds}
- C08K 5/0091: {Complexes with metal-heteroatom-bonds}
- C08K 5/06: Ethers; Acetals; Ketals; Ortho-esters
- C08K 5/14: Peroxides
- C08K 5/521: Esters of phosphoric acids, e.g. of H3PO4
- C08J 2331/04: Homopolymers or copolymers of vinyl acetate
- C08J 2333/10: Homopolymers or copolymers of methacrylic acid esters
- C08J 2367/06: Unsaturated polyesters
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

Method for curing a radically curable resin by adding to said resin an organic peroxide and a metal-bearing polymer, said metal-bearing polymer comprising functional groups that coordinate to a metal selected from the group consisting of Cu, Mn, Fe, and V and form a complex together with said metal and a complexing agent.

## Claims

### Claim 1

A method for curing a radically curable resin, the method comprising adding to said resin an organic peroxide and a metal-bearing polymer, said metal-bearing polymer comprising functional groups that coordinate to a Cu, Mn, Fe, or V metal and form a complex together with said metal and a complexing agent, wherein the radically curable resin is an unsaturated polyester resin or a vinyl ester resin.

### Claim 2 (depends on 1)

The method according to claim 1 wherein the metal is Cu, Fe, or V.

### Claim 3

A two-component composition comprising a first component and a second component, the first component comprising a radically curable resin and a metal-bearing polymer comprising functional groups that coordinate to a Cu, Mn, Fe, or V metal and form a complex together with said metal and a complexing agent, the second component comprising an organic peroxide, wherein the radically curable resin is an unsaturated polyester resin or a vinyl ester resin.

### Claim 4 (depends on 3)

The two component composition according to claim 3 wherein the peroxide is an organic hydroperoxides, a ketone peroxide, a peroxycarbonate, or a peroxyester.

### Claim 5 (depends on 3)

The two component composition according to claim 3 wherein the metal is selected Cu, Fe, and or V.

### Claim 6 (depends on 1)

The method according to claim 1 wherein the metal-bearing polymer is added to the resin in the form of an accelerator solution suitable for forming a redox couple with a peroxide, the accelerator solution comprising:
at least one solvent selected from compounds with the formulae P(R)3, P(R)3═O, and HO—(—CH2—C(R1)2—(CH2)m—O—)n—R2, wherein each R is independently selected from hydrogen, alkyl with 1 to 10 carbon atoms, and alkoxy groups with 1 to 10 carbon atoms, each Rl is independently selected from the group consisting of hydrogen, alkyl groups with 1-10 carbon atoms, and hydroxyalkyl groups with 1 to 10 carbon atoms, n=1-10, m=0 or 1, and R2 is hydrogen or an alkyl group with 1-10 carbon atoms, and
a metal-bearing polymer, said metal-bearing polymer comprising functional groups that coordinate to a metal selected from the group consisting of Cu, Mn, Fe, and V and form a complex together with said metal and a complexing agent.

### Claim 7 (depends on 1)

The method according to claim 1 comprising providing a two-component composition comprising a first component and a second component, the first component comprising a radically curable resin and a metal-bearing polymer comprising functional groups that coordinate to a Cu, Mn, Fe, or V metal and form a complex together with said metal and a complexing agent, the second component comprising an organic peroxide, and mixing the first component with the second component, wherein the radically curable resin is an unsaturated polyester resin or a vinyl ester resin.

### Claim 8 (depends on 4)

The two component composition according to claim 4 wherein the metal is Cu, Fe, or V.

### Claim 9 (depends on 6)

The method according to claim 6 wherein the metal content of said metal-bearing polymer is in the range 0.01-15 wt %.

### Claim 10 (depends on 6)

The method according to claim 6, wherein the metal is selected Cu, Fe, or V.

### Claim 11 (depends on 7)

The method according to claim 7 wherein the organic peroxide is an organic hydroperoxide, a ketone peroxide, a peroxycarbonate, or a peroxyester.