Pennwalt Corporation

Wilbur H McKellin

Orville L Mageli

Antonio Joseph D'Angelo

William A Swarts

David C Noller

James R Kolczynski

A polyperoxyketal having at least one carboxy group--an acid, hydrocarbon ester, a metal ion, or as part of an anhydride. Illustrations are: n-Butyl .gamma.,.gamma.-bis-(t-butylperoxy) valerate and Barium .gamma.,.gamma.-bis(t-butylperoxy) valerate. These polyperoxyketals are vulcanizing agents for thermoplastic polymers such as rubber and ethylenepropylene rubber.

Polyperoxy compounds

A polyperoxyketal compound is provided having at least one carboxy group, a hydrocarbon ester. An example of this compound is n-butyl gamma,gamma-bis(t-butylperoxy)valerate. This polyperoxyketal compound is used as a vulcanizing agent for thermoplastic polymers such as rubber and ethylene-propylene rubber.

Compounds containing at least one keto group and at least one peroxy group, each peroxy oxygen being joined to a tertiary carbon atom. Examples: 2-Methyl-2-(t-butylperoxy)-4-pentanone. 2,6-Dimethyl-2,6-bis(t-butylperoxy)-4-heptanone. 3,5,5-Trimethyl-3-(t-butylperoxy)cyclohexanone. The compounds are prepared by the strong acid catalyzed addition of a tertiary hydroperoxide to an .alpha.,.beta.-unsaturated ketone. Illustration: Mesityl oxide and pinanyl hydroperoxide, in slight excess, were reacted at 0.degree. C. in the presence of 77% sulfuric acid; the reaction mix was stirred for 16 hours at 25.degree. C. Product 2-methyl-2-pinanyl-peroxy-4-pentanone was recovered.

Compounds by addition of hydroperoxides to .alpha., .beta.-unsaturated

Compounds containing at least one keto group and at least one peroxy group, each peroxy oxygen being joined to a tertiary carbon atom. Examples: 2-Methyl-2-(t-butylperoxy)-4-pentanone. 2,6-Dimethyl-2,6-bis(t-butylperoxy)-4-heptanone. 3,5,5-Trimethyl-3-(t-butylperoxy)cyclohexanone. The compounds are prepared by the strong acid catalyzed addition of a tertiary hydroperoxide to an .alpha.,.beta.-unsaturated ketone. Illustration: Mesityl oxide and pinanyl hydroperoxide, in slight excess, were reacted at 0.degree. C. in the presence of 77% sulfuric acid; the reaction mix was stirred for 16 hours at 25.degree. C. Product 2-methyl-2-pinanylperoxy-4-pentanone was recovered.

Compounds by addition of hydroperoxides to .alpha.-.beta.-unsaturated

A method of producing hydroxy-containing dialkyl peroxides of the formula ##STR1## by either heterogeneously catalytically reducing or homogeneously, non catalytically chemically reducing carbonyl-containing dialkyl peroxides of the formula ##STR2## R, R.sub.1, R.sub.2 and R.sub.3 are aliphatics. This invention also concerns novel hydroxy-containing dialkyl peroxide compounds having the structure of formula I.

Reduction of carbonyl-containing dialkyl peroxides to hydroxy-containing

Vulcanizable compositions containing a polyperoxyketal having at least one carboxy group as an acid, hydrocarbon ester, a metal ion salt or as part of an anhydride. Illustrations are rubber or ethylene-propylene rubber containing n-butyl .gamma., .gamma.-bis(t-butylperoxy) valerate, barium .gamma., .gamma.-bis(t-butylperoxy)valerate or .gamma., .gamma.-bis(t-butylperoxy) valeric acid anhydride. Also embodied are the cross-linked compositions and methods of crosslinking.

Vulcanizable and vulcanized compositions containing polyperoxide

A safe peroxide solution composition consisting essentially of a diacyl peroxide having 1-5 carbon atoms in each aliphatic group and an aliphatic hydrocarbon, ketone, ester, ether, or alcohol characterized by a vapor pressure substantially that of the peroxide. Example: Equal parts by weight of diacetyl peroxide and ethyl butyl ketone.

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Buffalo, NY, United States of America

Wilbur H McKellin