Method for curing a radically curable resin

• US 9,751,994 B2
• Filed: 12/09/2014
• Issued: 09/05/2017
• Est. Priority Date: 12/12/2013
• Status: Expired due to Fees

• Current Assignee: Akzo Nobel Chemicals International B.V. (Nouryon BV)
• Original Assignee: Akzo Nobel Chemicals International B.V. (Nouryon BV)
• Inventors: Van Den Berg, Michel, Talma, Auke Gerardus
• Primary Examiner(s): Boyle, Robert C
• Application Number:
  US15/100,511
• Publication Number:
  US 20160297936A1
• Time in Patent Office: 1,001 Days
• CPC Class Codes: C08J 2331/04 Homopolymers or copolymers of vinyl acetate
• CPC Class Codes: C08J 2333/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08J 2367/06 Unsaturated polyesters
• CPC Class Codes: C08J 3/02 Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
• CPC Class Codes: C08J 3/095 Oxygen containing compounds
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08K 5/0091 Complexes with metal-heteroatom-bonds
• CPC Class Codes: C08K 5/06 Ethers; Acetals; Ketals; Ortho-esters
• CPC Class Codes: C08K 5/14 Peroxides
• CPC Class Codes: C08K 5/521 Esters of phosphoric acids, e.g. of H3PO4
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08L 35/02 Homopolymers or copolymers of esters C08L35/06, C08L35/08 take precedence
• CPC Class Codes: C08L 67/06 Unsaturated polyesters

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

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.

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

6. 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 R^l 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.

7. 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.

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

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

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

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.

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

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

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