IP Library Granted Patent US 7,456,212
Granted Patent B2
US 7,456,212 · App. 10/543,606 · Granted Nov 25, 2008

Storage stable cyclic ketone peroxide compositions

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Quick Facts
Patent No.
US 7,456,212
App. No.
10/543,606
Granted
Nov 25, 2008
Kind
B2
Abstract

The present invention relates to peroxide compositions comprising one or more cyclic ketone peroxides, one or more dialkyl peroxides, and, optionally, one or more conventional phlegmatisers. These compositions are safe and storage stable. In addition, the invention also pertains to the use of such compositions in polymerization and (co)polymer modification processes.

Claims (24)

1. A cyclic ketone peroxide polymerization initiator composition comprising:

one or more cyclic ketone peroxides of formula (I)

wherein R 1 -R 6 are independently selected from the group consisting of hydrogen, linear or branched C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 6 -C 20 aryl, C 7 -C 20 aralkyl and C 7 -C 20 alkaryl, and each of R 1 -R 6 may be optionally substituted with one or more groups selected from hydroxy, C 1 -C 20 alkoxy, linear or branched C 1 -C 20 alkyl, C 6 -C 20 aryloxy, halogen, ester, carboxy, nitrile, and amido, and whereby each of the combination of groups R 1 and R 2, R 3 and R 4, and R 5 and R 6, together with the carbon to which each combination of groups is attached may optionally form a cyclic moiety; and

one or more dialkyl peroxides according to formula R 7 —O—O—R 8 (II), wherein R 7 and R 5 are independently selected from the group consisting of unsubstituted, linear or branched C 4 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 6 -C 20 aryl, C 7 -C 20 aralkyl, and C 7 -C 20 alkaryl, wherein

the composition does not form explosive crystals when stored at −25° C. for 24 hours.

2. A cyclic ketone peroxide polymerization initiator composition comprising: one or more cyclic ketone peroxides of formula (I)

wherein R 1 -R 6 are independently selected from the group consisting of hydrogen, linear or branched C 1 -.C 20 alkyl, C 3 -C 20 cycloalkyl, C 6 -C 20 aryl, C 7 -C 20 aralkyl and C 7 -C 20 alkaryl, and each of R 1 -R 6 may be optionally substituted with one or more groups selected from hydroxy, C 1 -C 20 alkoxy, linear or branched C 1 -C 20 alky 1, C 6 -C 20 aryloxy, halogen, ester, carboxy, nitrile, and amido; and

one or more dialkyl peroxides according to formula R 7 —O—O—R 8 (II), wherein R 7 and R 8 are independently selected from the group consisting of unsubstituted, linear or branched C 4 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 6 -C 20 aryl, C 7 -C 20 aralkyl, and C 7 -C 20 alkaryl, wherein

the composition does not form explosive crystals when stored at −25° C. for 24 hours.

3. A composition according to claim 1 , further comprising one or more conventional phlegmatisers (diluents).

4. A composition according to claim 1 wherein the active oxygen content attributable to the cyclic ketone peroxide is below 6 wt. %, based on the total weight of the cyclic ketone peroxide composition.

5. A composition according to claim 1 wherein the cyclic ketone peroxide is selected from the group consisting of cyclic ketone peroxides derived from acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl amyl ketone, methyl isoamyl ketone, cyclohexanone, and mixtures thereof.

6. A composition according to claim 1 , wherein R 7 and R 8 of the dialkyl peroxide according to formula R 7 —O—O—R 8 (II) are independently selected from the group consisting of C 4 -C 12 alkyl moieties.

7. A composition according to claim 1 , wherein at least one of R 7 and R 8 of the dialkyl peroxide according to formula R 7 —O—O—R 8 (II) is selected from the group consisting of branched C 4 -C 12 alkyl moieties, preferably wherein both R 7 and R 8 of the dialkyl peroxide according to formula R 7 —O—O—R 8 (II) are independently selected from the group consisting of branched C 4 -C 12 alkyl moieties.

8. A composition according to claim 1 , wherein the dialkyl peroxide according to formula R 7 —O—O—R 8 (II) is di(tert-butyl) peroxide or di(tert-amyl) peroxide.

9. A cyclic ketone peroxide polymerization initiator composition comprising one or more cyclic ketone peroxides selected from a group of cyclic ketone peroxides derived from cyclopentanone, cyclohexanone, 2-methyl cyclohexanone, and 3,3,5-trimethyl cyclohexanone; and

one or more dialkyl peroxides according to formula R 7 —O—O—R 8 (II), wherein R 7 and R 8 are independently selected from the group consisting of substituted or unsubstituted, linear or branched C 4 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 6 -C 20 aryl, C 7 -C 20 aralkyl, and C 7 -C 20 alkaryl, and wherein

the composition does not form explosive crystals when stored at −25° C. for 24 hours.

10. The cyclic ketone peroxide polymerization initiator composition according to claim 1 , wherein, after the storage at −25° C. of 24 hours, explosive crystals are not formed upon the addition of seed crystals, and no growth of the seed crystals occurs following an additional 24 hours of storage at −25° C.

11. The cyclic ketone peroxide polymerization initiator composition according to claim 1 , wherein the composition is free of crystals following the addition of seed crystals and the additional 24 hours of storage at −25° C.

12. The cyclic ketone peroxide polymerization initiator composition according to claim 2 , wherein, after the storage at −25° C. of 24 hours, explosive crystals are not formed upon the addition of seed crystals, and no growth of the seed crystals occurs following an additional 24 hours of storage at −25° C.

13. The cyclic ketone peroxide polymerization initiator composition according to claim 12 , wherein the composition is free of crystals following the addition of seed crystals and the additional 24 hours of storage at −25° C.

14. The cyclic ketone peroxide polymerization initiator composition according to claim 9 , wherein, after the storage at −25° C. of 24 hours, explosive crystals are not formed upon the addition of seed crystals, and no growth of the seed crystals occurs following an additional 24 hours of storage at −25° C.

15. The cyclic ketone peroxide polymerization initiator composition according to claim 14 , wherein the composition is free of crystals following the addition of seed crystals and the additional 24 hours of storage at −25° C.

Assignments (3)
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 Nov 13, 2017
From: AKZO NOBEL N.V.
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 044427/0759 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2005
From: VAN DEN BERG, ROLF HENDRIK; FISCHER, BART; HOOGESTEGER, FRANS JOHANNES; PUT, SIMON
To: AKZO NOBEL N.V.
Reel/Frame 017323/0042 →