# US 4,395,361 A · Catalysts for oxygen-initiated free-radical polymerization reactions

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- Number: US 4,395,361 A
- Document ID: US4395361A
- Status: Granted
- Kind: A
- Application number: 06/290,908
- Filed: 1981-08-07
- Granted: 1983-07-26
- Earliest claimed: 1981-08-07
- Assignees: The Procter & Gamble Company
- Inventors: David J. Eickhoff; Medford D. Robbins
- Web page: https://patentgrep.com/patent/US4395361A

## CPC

- C08F 4/28: Oxygen or compounds releasing free oxygen (redox systems C08F4/40)
- C08F 4/00: Polymerisation catalysts
- C08F 4/80: selected from iron group metals or platinum group metals
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A class of new oxygen-activated free-radical polymerization catalysts, comprising specifically-defined autoxidizable cyclic hydrocarbons together with cobalt(II) compounds, is disclosed. A method of catalyzing an oxygen-initiated free-radical polymerization reaction using these catalysts is also disclosed.

## Claims

### Claim 1

A stabilized oxidation catalyst comprising a mixture of (a) a storage stabilizer having the formula ##STR25## and (b) an oxidation catalyst consisting essentially of: (1) an autoxidizable component having the formula ##STR26## and mixtures thereof, wherein each R.sub.3 is hydrogen, methyl, phenyl or COOH; R.sub.4 is C.sub.1 -C.sub.20 alkyl or alkenyl; and n is from about 1 to 10; and (2) a peroxide-decomposing transition metal catalyst.

### Claim 2 (depends on 1)

A stabilized oxidation catalyst according to claim 1 wherein the transition metal catalyst is a cobalt(II) compound.

### Claim 3 (depends on 2)

A stabilized oxidation catalyst according to claim 2 wherein the autoxidizable component is selected from the group consisting of ##STR27## and mixtures thereof.

### Claim 4 (depends on 3)

A stabilized oxidation catalyst according to claim 3 wherein the cobalt(II) compound is selected from the group consisting of cobalt(II) salts of carboxylic acids and a 2,4-pentanedione complex of cobalt(II).

### Claim 5 (depends on 4)

A stabilized oxidation catalyst according to claim 4 wherein the cobalt(II) compound is selected from the group consisting of cobalt(II) dipivaloylmethane, cobalt(II) acetylacetonate, cobalt(II) acetate, cobalt(II) decanoate, cobalt(II) naphthenate, and mixtures thereof.

### Claim 6 (depends on 4)

A stabilized oxidation catalyst according to claim 4 wherein the mole ratio of autoxidizable component to cobalt(II) compound is from about 5 to about 5,000.

### Claim 7 (depends on 2)

A stabilized oxidation catalyst according to claim 2 which contains from about 0.05% to about 20% of the storage stabilizer and from about 80% to about 99.95% of the oxidation catalyst.

### Claim 8

An oxidation catalyst for oxygen-initiated free-radical polymerization reactions consisting essentially of: (1) an autoxidizable component having the formula ##STR28## and mixtures thereof, wherein each R.sub.3 is hydrogen, methyl, or COOH; R.sub.4 is C.sub.1 -C.sub.20 alkyl; and n is from about 1 to 10; and (2) a peroxide-decomposing transition metal catalyst.

### Claim 9 (depends on 8)

An oxidation catalyst according to claim 8 wherein the transition metal catalyst is a cobalt(II) compound.

### Claim 10 (depends on 9)

An oxidation catalyst according to claim 9 wherein the autoxidizable component is selected from the group consisting of ##STR29## and mixtures thereof.

### Claim 11 (depends on 10)

An oxidation catalyst according to claim 10 wherein the cobalt(II) compound is selected from the group consisting of cobalt(II) dipivaloylmethane, cobalt(II) acetylacetonate, cobalt(II) acetate, cobalt(II) decanoate, cobalt(II) naphthenate, and mixtures thereof.

### Claim 12 (depends on 10)

An oxidation catalyst according to claim 10 wherein the mole ratio of autoxidizable component to cobalt(II) compound is from about 5 to about 5,000.