IP Library Granted Patent US 9,938,251
Granted Patent B2
US 9,938,251 · App. 15/123,418 · Granted Apr 10, 2018

Cyclic ketone peroxide composition

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Quick Facts
Patent No.
US 9,938,251
App. No.
15/123,418
Granted
Apr 10, 2018
Kind
B2
Abstract

A composition comprising at least two trimeric cyclic ketone peroxides: a trimeric cyclic methyl ethyl ketone peroxide (3MEK-cp) of formula (I) and at least one peroxide satisfying formula (II) wherein R 1 through R 3 are independently selected from alkyl and alkoxyalkyl groups, said groups having 2 to 5 carbon atoms, the total number of carbon plus oxygen atoms of R 1 −R 2 +R 3 is in the range 7-15, and the molar ratio of 3MEK-cp to the total amount of peroxides satisfying formula (II) being in the range of from 10:90 to 80:20.

Claims (21)

1. A composition comprising at least two trimeric cyclic ketone peroxides: a trimeric cyclic methyl ethyl ketone peroxide (3MEK-cp) of formula (I)

and at least one peroxide satisfying formula (II)

wherein R 1 through R 3 are independently selected from alkyl and alkoxyalkyl groups, said groups having 2 to 5 carbon atoms, the total number of carbon plus oxygen atoms of R 1 +R 2 +R 3 is in the range 7-15, and the molar ratio of 3MEK-cp to the total amount of peroxides satisfying formula (II) being in the range of from 10:90 to 80:20.

2. The composition according to claim 1 wherein R 1 through R 3 are alkyl groups having 2 to 5 carbon atoms, the total number of carbon atoms of R 1 +R 2 +R 3 is in the range 7-15.

3. The composition according to claim 2 wherein the alkyl groups are linear alkyl groups.

4. The composition according to claim 1 wherein the molar ratio of 3MEK-cp to the total amount of peroxides satisfying formula (II) is in the range of from 40:60 to 80:20.

5. The composition according to claim 1 wherein the composition further comprises a diluent in an amount of 45-85 wt %, based on the weight of the composition.

6. The composition according to claim 1 wherein the total amount of trimeric cyclic ketone peroxides according to formulae (I) and (II) is in the range 15-55 wt %, based on the weight of the composition.

7. The composition according to claim 1 wherein at least one of the peroxides satisfying formula (II) is 3,6-diethyl-3,6,9-trimethyl-9-(n-propyl)-1,2,4,5,7,8-hexaoxonane.

8. The composition according to claim 1 wherein at least one of the peroxides satisfying formula (II) is 3-ethyl-3,6,9-trimethyl-6,9-di(n-propyl)-1,2,4,5,7,8-hexaoxonane.

9. The composition according to claim 1 wherein at least one of the peroxides satisfying formula (II) is 3,6,9-tri(n-propyl)-3,6,9-trimethyl-1,2,4,5,7,8-hexaoxonane.

10. A process for preparing a cyclic ketone peroxide composition, the method comprising reacting, in the presence of acid, hydrogen peroxide with a mixture of ketones comprising methyl ethyl ketone (MEK) and at least one ketone of formula CH 3 —C(═O)—R wherein R is an alkyl group with 3 to 5 carbon atoms or an alkoxyalkyl group with 2 to 5 carbon atoms, the molar ratio of MEK to the total amount of ketones of formula CH 3 —C(═O)—R being in the range 25:75 to 95:5.

11. The process according to claim 10 , wherein R is an alkyl group.

12. The process according to claim 11 , wherein R is n-propyl.

13. The process according to claim 10 , wherein the molar ratio of MEK to the total amount of ketones of formula CH 3 —C(═O)—R is in the range of from 50:50 to 70:30.

14. A peroxide composition obtained by the process of claim 10 .

15. The process of claim 13 wherein R is an alkyl group with 3 to 5 carbon atoms.

16. The process of claim 13 wherein R is n-propyl.

17. The peroxide composition of claim 14 wherein R is an alkyl group with 3 to 5 carbon atoms.

18. The peroxide composition of claim 14 wherein R is n-propyl.

19. The peroxide composition of claim 14 wherein the molar ratio of MEK to the total amount of ketones of formula CH 3 —C(═O)—R is in the range of from 50:50 to 70:30.

Assignments (3)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 25, 2016
From: VAN DER SCHUUR, JAN MARTIJN; NUYSINK, JOHAN; MILLET, RENAUD CHARLES JOSEPH; FISCHER, BART
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 040120/0694 →