# US 5,710,210 A · Process for polymer reactions with functionalized peroxides

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- Number: US 5,710,210 A
- Document ID: US5710210A
- Status: Granted
- Kind: A
- Application number: 08/465,899
- Filed: 1995-06-06
- Granted: 1998-01-20
- Earliest claimed: 1990-09-05
- Assignees: Elf Atochem North America, Inc.
- Inventors: Daryl L. Stein
- Web page: https://patentgrep.com/patent/US5710210A

## CPC

- C08G 18/86: by peroxides
- C07C 409/38: the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids
- C08F 283/01: on to unsaturated polyesters {(C08F283/004 takes precedence)}
- C07C 2601/14: The ring being saturated
- C07C 2602/42: the bicyclo ring system containing seven carbon atoms
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

Novel functionalized peroxides which may be used as crosslinking, grafting and curing agents, initiators for polymerization reactions and as monomers for condensation polymerizations to form peroxy-containing polymers, which in turn can be used to prepare block and graft copolymers, have the following Formula I: ##STR1## R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, X, Y.sup.1, Y.sup.2, Y.sup.3, Z.sup.1, Z.sup.2, x, y and z are as defined in the Summary of the Invention. The compounds of Formula I may be prepared by reacting hydroxy-containing tertiary hydroperoxides with diacid halides, phosgene, dichloroformates, diisocyanates, anhydrides and lactones to form the functionalized peroxides. These reaction products may be further reacted, if desired, with dialcohols, diamines, aminoalcohols, epoxides, epoxy alcohols, epoxy amines, diacid halides, dichloroformates and diisocyanates to form additional functionalized peroxides.

## Claims

### Claim 1

A process for curing an elastomer resin, comprising heating an elastomer resin without unsaturation and about 0,001% by weight to about 10% by weight of a peroxide compound at a temperature effective to cure the elastomer resin, the peroxide compound having the following Formula I: ##STR36## wherein R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 18 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 12 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 12 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 18 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical having the following Formula II: ##STR37## with the proviso that when X is a direct bond, R.sup.6 is not a tertiary alkyl diradical;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or the substituted or unsubstituted diradical having the Formula II;
R.sup.4 and R.sup.5 are independently a substituted or unsubstituted alkyl radical of 1 to 10 carbons;
R.sup.8 is a direct bond, --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.O)--NH-- or a substituted or unsubstituted alkyl diradical of 1 to 6 carbons;
X is a direct bond;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.O)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.O)--O--, --O--C(.dbd.O)--NH--, --NH--C(.dbd.O)--NH, --C(.dbd.O)--C(.dbd.O)--, --O--C(.dbd.O)--C(.dbd.O)--O--, --NH--C(.dbd.O)--C(.dbd.O)--NH--, --NH--C(.dbd.O)--C(.dbd.O)--O-- or --O--C(.dbd.O)--C(.dbd.O)--NH--;
Z.sup.1 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR38## H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 -- or R.sup.11 --O--C(.dbd.O)--;
Z.sup.2 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, ##STR39## or H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 --; R.sup.9 and R.sup.10 are independently hydrogen or a substituted or unsubstituted alkyl radical of 1 to 4 carbons;
R.sup.11 is an alkyl radical of 1-4 carbons, benzyl or phenyl;
t, x, y and z are independently 0 or 1;
w is an integer from 1 to 12; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 or R.sup.10 are independently one or more of chloro, bromo, fluoro, cyano, amino, sulfo, carboxy, nitro, alkoxy of 1 to 12 carbons, alkylamino of 1 to 12 carbons, acyloxy of 1 to 12 carbons, alkenoyloxy of 3 to 12 carbons, alkenoylamino of 3 to 12 carbons, aroyloxy of 7 to 15 carbons, aroylamino of 7 to 15 carbons, phthalimido, alkoxycarbonyloxy of 2 to 13 carbons, alkoxycarbonylamino of 2 to 13 carbons, alkenyloxycarbonyloxy of 3 to 12 carbons, alkenyloxycarbonylamino of 3 to 12 carbons, aryloxycarbonyloxy of 7 to 15 carbons, alkylaminocarbonyloxy of 2 to 13 carbons, arylaminocarbonyloxy of 7 to 15 carbons, aralkylaminocarbonyloxy of 7 to 16 carbons, alkylsulfonyloxy of 1 to 8 carbons, alkylsulfonylamino of 1 to 8 carbons, arylsulfonylamino of 6 to 11 carbons or epoxyalkoxycarbonyl of 2 to 13 carbons.

### Claim 2 (depends on 1)

The process according to claim 1 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 10 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 12 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 10 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 10 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 8 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 8 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 12 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR40## or R.sup.11 --O--C(.dbd.O)--; Z.sup.2 is O.dbd.C.dbd.N-- or ##STR41## and substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently one or two of chloro, bromo, amino, carboxy, alkoxy of 1 to 6 carbons, acyloxy of 2 to 5 carbons, alkenoyloxy of 3 to 5 carbons or aroyloxy of 7 to 10 carbons.

### Claim 3 (depends on 1)

The process according to claim 1 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 6 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 7 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 8 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 8 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 4 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is an alkyl diradical of 1 to 8 carbons;
R.sup.4 and R.sup.5 are independently alkyl of 1 to 3 carbons;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --C(.dbd.O)--O-- or --O--C(.dbd.O)--;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)-- or HO--C(.dbd.O)--;
Z.sup.2 is O.dbd.C.dbd.N-- or Cl--C(.dbd.O)--; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently chloro, carboxy, alkoxy of 1 to 4 carbons, acyloxy of 2 to 3 carbons or alkenoyloxy of 3 to 5 carbons.

### Claim 4 (depends on 1)

The process according to claim 1 wherein the peroxide compound is ##STR42##

### Claim 5

A process for crosslinking an olefin polymer, comprising heating a non-crosslinked olefin polymer and about 0.001% by weight to about 10% by weight of a peroxide compound at a temperature effective to crosslink the olefin polymer, the peroxide compound having the following Formula I: ##STR43## wherein R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 18 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 12 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 12 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 18 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical having the following Formula II: ##STR44## with the proviso that when X is a direct bond, R.sup.6 is not a tertiary alkyl diradical;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or the substituted or unsubstituted diradical having the Formula II;
R.sup.4 and R.sup.5 are independently a substituted or unsubstituted alkyl radical of 1 to 10 carbons;
R.sup.8 is a direct bond, --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.O)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.O)--NH-- or a substituted or unsubstituted alkyl diradical of 1 to 6 carbons;
X is a direct bond;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.O)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.O)--O--, --O--C(.dbd.O)--NH--, --NH--C(.dbd.O)--NH, --C(.dbd.O)--C(.dbd.O)--, --O--C(.dbd.O)--C(.dbd.O)--O--, --NH--C(.dbd.O)--C(.dbd.O)--NH--, --NH--C(.dbd.O)--C(.dbd.O)--O-- or --O--C(.dbd.O)--C(.dbd.O)--NH--;
Z.sup.1 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR45## H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 -- or R.sup.11 --O--C(.dbd.O)--;
Z.sup.2 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, ##STR46## or H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 --; R.sup.9 and R.sup.10 are independently hydrogen or a substituted or unsubstituted alkyl radical of 1 to 4 carbons;
R.sup.11 is an alkyl radical of 1-4 carbons, benzyl or phenyl;
t, x, y and z are independently 0 or 1;
w is an integer from 1 to 12; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 or R.sup.10 are independently one or more of chloro, bromo, fluoro, cyano, amino, sulfo, carboxy, nitro, alkoxy of 1 to 12 carbons, alkylamino of 1 to 12 carbons, acyloxy of 1 to 12 carbons, alkenoyloxy of 3 to 12 carbons, alkenoylamino of 3 to 12 carbons, aroyloxy of 7 to 15 carbons, aroylamino of 7 to 15 carbons, phthalimido, alkoxycarbonyloxy of 2 to 13 carbons, alkoxycarbonylamino of 2 to 13 carbons, alkenyloxycarbonyloxy of 3 to 12 carbons, alkenyloxycarbonylamino of 3 to 12 carbons, aryloxycarbonyloxy of 7 to 15 carbons, alkylaminocarbonyloxy of 2 to 13 carbons, arylaminocarbonyloxy of 7 to 15 carbons, aralkylaminocarbonyloxy of 7 to 16 carbons, alkylsulfonyloxy of 1 to 8 carbons, alkylsulfonylamino of 1 to 8 carbons, arylsulfonylamino of 6 to 11 carbons or epoxyalkoxycarbonyl of 2 to 13 carbons.

### Claim 6 (depends on 5)

The process according to claim 5 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 10 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 12 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 10 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 10 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 8 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 8 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 12 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR47## or R.sup.11 --O--C(.dbd.O)--; Z.sup.2 is O.dbd.C.dbd.N-- or ##STR48## and substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently one or two of chloro, bromo, amino, carboxy, alkoxy of 1 to 6 carbons, acyloxy of 2 to 5 carbons, alkenoyloxy of 3 to 5 carbons or aroyloxy of 7 to 10 carbons.

### Claim 7 (depends on 5)

The process according to claim 5 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 6 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 7 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 8 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 8 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 4 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is an alkyl diradical of 1 to 8 carbons;
R.sup.4 and R.sup.5 are independently alkyl of 1 to 3 carbons;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --C(.dbd.O)--O-- or --O--C(.dbd.O)--;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)-- or HO--C(.dbd.O)--;
Z.sup.2 is O.dbd.C.dbd.N-- or Cl--C(.dbd.O)--; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently chloro, carboxy, alkoxy of 1 to 4 carbons, acyloxy of 2 to 3 carbons or alkenoyloxy of 3 to 5 carbons.

### Claim 8 (depends on 5)

The process according to claim 5 wherein the peroxide compound is ##STR49##

### Claim 9

A process for reducing the molecular weight of a propylene polymer and modifying the molecular weight distribution of a propylene polymer comprising heating a propylene polymer selected from the group consisting of polypropylene polymers and propylene copolymers and about 0.001% by weight to about 5% by weight of a peroxide compound at a temperature effective to reduce the molecular weight and to modify the molecular weight distribution of the propylene polymer, the peroxide compound having the following Formula I; ##STR50## wherein R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 18 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 12 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 12 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 18 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical having the following Formula II: ##STR51## with the proviso that when X is a direct bond, R.sup.6 is not a tertiary alkyl diradical;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 18 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 18 carbons, a substituted or unsubstituted naphthyl diradical or the substituted or unsubstituted diradical having the Formula II;
R.sup.4 and R.sup.5 are independently a substituted or unsubstituted alkyl radical of 1 to 10 carbons;
R.sup.8 is a direct bond, --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.O)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.)--NH-- or a substituted or unsubstituted alkyl diradical of 1 to 6 carbons;
X is a direct bond;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --O--, --S--, --S(.dbd.O).sub.2 --, --C(.dbd.O)--, --C(.dbd.O)--O--, --O--C(.dbd.O)--, --O--C(.dbd.O)--O--, --NH--C(.dbd.O)--, --C(.dbd.O)--NH--, --NH--C(.dbd.O)--O--, --O--C(.dbd.O)--NH--, --NH--C(.dbd.O)--NH, --C(.dbd.O)--C(.dbd.O)--, --O--C(.dbd.O)--C(.dbd.O)--O--, --NH--C(.dbd.O)--C(.dbd.O)--NH--, --NH--C(.dbd.O)--C(.dbd.O)--O-- or --O--C(.dbd.O)--C(.dbd.O)--NH--;
Z.sup.1 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR52## H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 -- or R.sup.11 --O--C(O.dbd.)--;
Z.sup.2 is H.sub.2 N--, O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, Br--C(.dbd.O)--, ##STR53## or H.sub.2 N--C(R.sup.9)(R.sup.10)--(CH.sub.2).sub.w --Y.sup.1 --; R.sup.9 and R.sup.10 are independently hydrogen or a substituted or unsubstituted alkyl radical of 1 to 4 carbons;
R.sup.11 is an alkyl radical of 1-4 carbons, benzyl or phenyl;
t, x, y and z are independently 0 or 1;
w is an integer from 1 to 12; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 or R.sup.10 are independently one or more of chloro, bromo, fluoro, cyano, amino, sulfo, carboxy, nitro, alkoxy of 1 to 12 carbons, alkylamino of 1 to 12 carbons, acyloxy of 1 to 12 carbons, alkenoyloxy of 3 to 12 carbons, alkenoylamino of 3 to 12 carbons, aroyloxy of 7 to 15 carbons, aroylamino of 7 to 15 carbons, phthalimido, alkoxycarbonyloxy of 2 to 13 carbons, alkoxycarbonylamino of 2 to 13 carbons, alkenyloxycarbonyloxy of 3 to 12 carbons, alkenyloxycarbonylamino of 3 to 12 carbons, aryloxycarbonyloxy of 7 to 15 carbons, alkylaminocarbonyloxy of 2 to 13 carbons, arylaminocarbonyloxy of 7 to 15 carbons, aralkylaminocarbonyloxy of 7 to 16 carbons, alkylsulfonyloxy of 1 to 8 carbons, alkylsulfonylamino of 1 to 8 carbons, arylsulfonylamino of 6 to 11 carbons or epoxyalkoxycarbonyl of 2 to 13 carbons.

### Claim 10 (depends on 9)

The process according to claim 9 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 10 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 12 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 10 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 10 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 8 carbons, a substituted or unsubstituted alkynyl diradical of 2 to 8 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is a substituted or unsubstituted alkyl diradical of 1 to 12 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons, a substituted or unsubstituted naphthyl diradical or a substituted or unsubstituted diradical of Formula II;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)--, HO--C(.dbd.O)--, ##STR54## or R.sup.11 --O--C(.dbd.O)--; Z.sup.2 is O.dbd.C.dbd.N-- or ##STR55## and substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently one or two of chloro, bromo, amino, carboxy, alkoxy of 1 to 6 carbons, acyloxy of 2 to 5 carbons, alkenoyloxy of 3 to 5 carbons or aroyloxy of 7 to 10 carbons.

### Claim 11 (depends on 9)

The process according to claim 9 wherein, in Formula I for the peroxide compound,
R.sup.1, R.sup.2, R.sup.6 and R.sup.7 are independently a substituted or unsubstituted alkyl diradical of 1 to 6 carbons, a substituted or unsubstituted cycloalkyl diradical of 5 to 7 carbons, a substituted or unsubstituted bicycloalkyl diradical of 7 to 8 carbons, a substituted or unsubstituted bicycloalkenyl diradical of 7 to 8 carbons, a substituted or unsubstituted alkenyl diradical of 2 to 4 carbons, a substituted or unsubstituted aralkyl diradical of 7 to 12 carbons or a substituted or unsubstituted diradical of Formula II;
R.sup.3 is an alkyl diradical of 1 to 8 carbons;
R.sup.4 and R.sup.5 are independently alkyl of 1 to 3 carbons;
Y.sup.1, Y.sup.2 and Y.sup.3 are independently --C(.dbd.O)--O-- or --O--C(.dbd.O)--;
Z.sup.1 is O.dbd.C.dbd.N--, Cl--C(.dbd.O)-- or HO--C(.dbd.O)--;
Z.sup.2 is O.dbd.C.dbd.N-- or Cl--C(.dbd.O)--; and
substituents for any of R.sup.1, R.sup.2, R.sup.3, R.sup.6 and R.sup.7 are independently chloro, carboxy, alkoxy of 1 to 4 carbons, acyloxy of 2 to 3 carbons or alkenoyloxy of 3 to 5 carbons.

### Claim 12 (depends on 9)

The process according to claim 9 wherein the peroxide compound is ##STR56##