Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-03-13
1998-09-15
Reamer, James H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549357, 549435, C07D32500
Patent
active
058081100
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to cyclic ketone peroxide formulations and to the use of these cyclic ketone peroxide formulations for the modification of (co)polymers.
BACKGROUND OF THE INVENTION
Several formulations of ketone peroxides are known from the prior art. For example, British Patent 827,511 discloses formulations of ketone peroxides in paraffinic diesel oil. These formulations may include cyclic ketone peroxides though the goal of this publication is to minimize the amount of cyclic peroxide present in the compositions and thus such compositions contain only minor amounts of cyclic ketone peroxides.
British Patent 912,061 discloses formulations of ketone peroxides in dimethyl phthalate and paraffinic diesel oil. Again, formulations containing only minor amounts of cyclic ketone peroxides are disclosed.
British Patent 1,072,728 discloses stabilized ketone peroxide compositions formulated in safety solvents which are selected from alcohols and glycols. Such compositions optionally contain diluents other than the safety solvents, such diluents being phthalate esters. These ketone peroxide formulations also contain only minor proportions of cyclic ketone peroxides.
U.S. Pat. No. 3,649,546 relates to non-hazardous ketone peroxide polymerization initiators wherein ketone peroxides are formulated in esters with boiling points in the range of 140.degree.-250.degree. C. Such compositions may also contain other diluents which are often incorporated into ketone peroxide compositions. Again, these ketone peroxide formulations contain only minor amounts of cyclic ketone peroxides.
U.S. Pat. No. 3,867,461 also relates to non-hazardous ketone peroxide compositions. These compositions are desensitized with a heat-desensitizing solvent having a boiling point between 185.degree.-225.degree. C. and a stabilizer selected from vinyl pyrrolidone and polyvinyl pyrrolidone. The ketone peroxides contained in these compositions are primarily non-cyclic ketone peroxides.
U.S. Pat. No. 4,299,718 relates to peroxide mixtures which comprise ketone peroxides formulated in a solvent, optionally with a phlegmatizer. Again, these compositions comprise only minor amounts of cyclic ketone peroxides present as an impurity in the composition.
Finally, European Patent Application EP-A-0209181 relates generally to desensitized ketone peroxide compositions which contain, as a desensitizing agent, 2,2,4-trimethyl-1,3-pentanediol diisobutyrate and the use of these ketone peroxide compositions to manufacture foundry cores or moulds. These ketone peroxides are also predominantly non-cyclic.
Until now, ketone peroxides were primarily employed in the curing of unsaturated polyester resins. In this application, it is desirable to minimize the quantity of cyclic ketone peroxide present in the composition as is taught by British Patent 827,511 since these peroxides are considered to be less active for this application.
The present inventors have unexpectedly found that cyclic ketone peroxide formulations possess a high activity in (co)polymer modification processes despite the fact that it was thought that these peroxides were less active than their non-cyclic counterparts.
Accordingly, it is the primary object of the present invention to provide safe, storage stable cyclic ketone peroxide formulations which can be employed in (co)polymer modification processes. This and other objects of the invention will be apparent from the summary and detailed descriptions which follow.
SUMMARY OF THE INVENTION
In a first aspect, the present invention relates to a transportable, storage stable peroxide composition which comprises 1.0-90% by weight of one or more cyclic ketone peroxides selected from peroxides represented by the formulae I-III: ##STR1## wherein R.sub.1 -R.sub.10 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 cycloalkyl, C.sub.6 -C.sub.20 aryl, C.sub.7 -C.sub.20 aralkyl and C.sub.7 -C.sub.20 alkaryl, which groups may include linear or branched alkyl moi
REFERENCES:
patent: 3003000 (1961-10-01), Milas
patent: 3649546 (1972-03-01), McCloskey et al.
patent: 3867461 (1975-02-01), Leveskis et al.
patent: 4271279 (1981-06-01), Pastorino et al.
patent: 4299718 (1981-11-01), Conti et al.
International Search Report, dated Oct. 5, 1995.
Uhlmann 3rd Edition, (1962) Vo. 13, Peroxyde, organische, pp. 256-257.
Journal of American Chemical Society, vol. 81,, pp. 5824-5826 (1959).
Houben-Weyl Methoden de Organische Chemie, E13, vol. 1, p. 736, English translation attached 2 pages. (1973).
Organic Peroxides, Wiley-Interscience, vol. III, pp. 67-87. (1978).
Bekendam Gerrit
Hogt Andreas Herman
Meijer John
Torenbeek Reinder
Akzo Nobel nv
Mancini Ralph J.
Reamer James H.
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