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US 5,304,649 AGranted
Hydroxy-peroxides useful as polymerization initiators
AssigneeElf Atochem North America, Inc.
InventorsJose Sanchez, Arthur L. Baron
Life of this patent
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Abstract
Novel hydroxy peroxides of the Structure A HO--R.sub.11 --X--OO--R (A) [wherein R--, --R.sub.11 -- and --X-- are as defined in the Summary of the Invention Section], having 10 hour half-life temperatures of 85.degree.-100.degree. C., the processes for their preparation, and the use of these novel compositions in curing of unsaturated polyester resins and in initiating polymerization of ethylenically unsaturated monomers.
Claims7
A hydroxy-peroxide having Structure A:
- HO--R.sub.11 --X--OO--R (A)
- wherein X is a direct bond or the diradical:
- ##STR21## and wherein:
- I. when X is a direct bond:
- R is selected from the structures:
- ##STR22## wherein:
- R.sub.1 is a lower alkyl radical of 1 to 4 carbons, an alkoxy radical of 1 to 4 carbons, a phenyl radical, an acyloxy radical of 2 to 8 carbons, a t-alkylperoxycarbonyl radical of 5 to 9 carbons, hydroxy, fluoro, chloro or bromo, R'.sub.1 is H or is selected from the same radicals as R.sub.1, and may be the same as or different than R.sub.1 ;
- n is 0 or 1;
- R.sub.2 is a substituted or unsubstituted alkyl radical of 1 to 18 carbons, substituents being one or more alkyl radicals of 1 to 6 carbons, t-alkylperoxy radicals of 4 to 8 carbons, alkoxy radicals of 1 to 6 carbons, aryloxy radicals of 6-10 carbons, hydroxy, chloro, bromo or cyano;
- or R.sub.2 is a substituted or unsubstituted cycloalkyl radical of 5 to 12 carbons, a substituted or unsubstituted 4-piperidinyl radical, or a substituted or unsubstituted 1,3-dioxan-5-yl radical, with substituents for the cycloalkyl, piperidinyl or dioxanyl radicals being one or more lower alkyl radicals of 1 to 4 carbons, or R.sub.2 is the radical:
- ##STR23## wherein z is 0 or 1, R.sub.a, R.sub.b and R.sub.c are the same or different and are H or alkyl radicals of 1 to 8 carbons, or R.sub.a and R.sub.b can be connected forming together with the carbon atoms to which they are attached a substituted or unsubstituted ring containing 5-12 carbons, substitutuents being one or more alkyl radicals of 1 to 5 carbons or phenyl radicals;
- R.sub.22 is a substituted or unsubstituted alkylene diradical of 2 to 3 carbons, substituents being one or more lower alkyl radicals of 1 to 4 carbons, or a substituted or unsubstituted 1,2-phenylene diradical, substituents being one or more lower alkyl radicals of 1 to 4 carbons, chloro, bromo, nitro or carboxy;
- R.sub.3 is a lower alkyl radical of 1 to 4 carbons, or the two R.sub.3 radicals can be connected together forming together with the carbon atom to which they are attached a ring containing 5 to 6 carbons;
- R.sub.4 is a lower alkyl radical of 1 to 4 carbons;
- the R.sub.11 diradical is the structure, ##STR24## wherein R.sub.5 is a lower alkyl radical of 1 to 4 carbons;
- and
- R.sub.33 is a substituted or unsubstituted alkylene diradical of 2 to 4 carbons, substituents being one or more lower alkyl radicals of 1 to 4 carbons, with the proviso that when n is 0 and R.sub.33 is an alkylene diradical of 2 carbon atoms substituted with methyl on the C atom alpha to the hydroxy group, R.sub.2 is not an unsubstituted alkyl radical of 1 to 9 carbon atoms or an alkyl radical of 1 to 9 carbon atoms substituted with one or more lower alkyl radicals of 1 to 6 carbon atoms;
- and
- II. when X is the diradical:
- ##STR25## Y is oxy or --NR.sub.6 --, wherein R.sub.6 is H or a substituted or unsubstituted alkyl radical of 1 to 8 carbons, substituents being one or more lower alkyl radicals of 1 to 4 carbons or hydroxy, and R.sub.22 is as defined above;
- R is a substituted or unsubstituted t-alkyl radical of 4 to 12 carbons, a cumyl radical, or a cumyl radical substituted with lower alkyl radicals said lower alkyl radicals totaling 1 to 4 carbon atoms, substituents for the t-alkyl radical being lower alkyl radicals of 1 to 4 carbons or a t-alkylperoxy radical of 4 to 8 carbons;
- and
- R.sub.11 is a substituted or unsubstituted alkylene diradical of 2 to 8 carbons, substituents being one or more lower alkyl radicals of 1 to 4 carbons, lower hydroxyalkyl radicals of 1 to 4 carbons or hydroxy.
20 more elements
Dependencies are inferred from the claim text.