Oxidized polyethylene compounds and methods of making the same
AssigneeThe Regents of the University of California
InventorsJohn F. Hartwig, Liye Chen
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Abstract
Disclosed herein, inter alia, are oxidized polyethylene compounds and compositions and methods of making the same.
Claims42
A method of making an oxidized polyethylene, comprising mixing a polyethylene, a metal catalyst, and an oxidizing agent;
- wherein
- the oxidized polyethylene comprises a first oxidized subunit, a second oxidized subunit, and a non-oxidized subunit;
- the polyethylene comprises a non-oxidized subunit;
- the first oxidized subunit has the formula:
- the second oxidized subunit has the formula:
- the non-oxidized subunit has the formula:
- the ratio of the first and second oxidized subunits to the non-oxidized subunit in the oxidized polyethylene is from 1:
- 10,000 to 1:5;
- the oxidized polyethylene has a number average molecular weight from 150 Da to 20,000,000 Da;
- and
- wherein the metal catalyst is not a manganese porphyrin catalyst or an iron porphyrin catalyst,
- wherein a sum of a chloride subunit of formula
- and an ester subunit of formula
- of the oxidized polyethylene is less than about 6% of a sum of the first oxidized subunit and the second oxidized subunit of the oxidized polyethylene.
An oxidized polyethylene in a vessel comprising an oxidized polyethylene and one or more additional compounds selected from the groups consisting of:
- (i) a metal catalyst;
- (ii) an oxidizing agent;
- (iii) a reducing agent;
- (iv) a polyethylene;
- and (v) a hydroxylated polyethylene;
- wherein
- the oxidized polyethylene comprises a first oxidized subunit, a second oxidized subunit, and a non-oxidized subunit;
- the polyethylene comprises a non-oxidized subunit;
- the hydroxylated polyethylene comprises a second oxidized subunit and a non-oxidized subunit;
- the first oxidized subunit has the formula:
- the second oxidized subunit has the formula:
- the non-oxidized subunit has the formula:
- the ratio of the first and second oxidized subunits to the non-oxidized subunit in the oxidized polyethylene is from 1:
- 10,000 to 1:5;
- the oxidized polyethylene has a number average molecular weight from 150 Da to 20,000,000 Da;
- the hydroxylated polyethylene has a number average molecular weight from 150 Da to 20,000,000 Da;
- wherein the metal catalyst is not a manganese porphyrin catalyst or an iron porphyrin catalyst;
- and
- wherein a sum of a chloride subunit of formula
- and an ester subunit of formula
- of the oxidized polyethylene is less than about 6% of a sum of the first oxidized subunit and the second oxidized subunit of the oxidized polyethylene.
The oxidized polyethylene in a vessel of claim 16, wherein the ratio of the first and second oxidized subunits to the non-oxidized subunit in the oxidized polyethylene is from 1:1000 to 1:10.
The oxidized polyethylene in a vessel of claim 16, wherein the ratio of the first oxidized subunit to the second oxidized subunit in the oxidized polyethylene is about 1:1.
The oxidized polyethylene in a vessel of claim 16, wherein the oxidized polyethylene has a number average molecular weight from 300 Da to 2,000,000 Da.
The oxidized polyethylene in a vessel of claim 22, wherein the metal catalyst is.
The oxidized polyethylene in a vessel of claim 22, wherein the metal catalyst is.
An oxidized polyethylene, comprising a first oxidized subunit, a second oxidized subunit, and a non-oxidized subunit;
- the first oxidized subunit has the formula:
- the second oxidized subunit has the formula:
- the non-oxidized subunit has the formula:
- the ratio of the first and second oxidized subunits to the non-oxidized subunit is from 1:10,000 to 1:5;
- and
- the oxidized polyethylene has a number average molecular weight from 150 Da to 20,000,000 Da.
The oxidized polyethylene of claim 32, wherein the ratio of the first and second oxidized subunits to the non-oxidized subunit is from 1:1000 to 1:10.
The oxidized polyethylene of claim 32, wherein the ratio of the first oxidized subunit to the second oxidized subunit is about 1:1.
The oxidized polyethylene of claim 32, wherein the oxidized polyethylene has a number average molecular weight from 300 Da to 2,000,000 Da.
A mixture of polymers comprising an oxidized polyethylene of claim 32 and a second polymer.
The mixture of polymers of claim 36, wherein the second polymer is a high-density polyethylene, a low-density polyethylene, or a linear low-density polyethylene.
The cross-linked polymer of claim 38, wherein W1 is —O— or —NH—.
The cross-linked polymer of claim 38, wherein W1 is —O—.
The cross-linked polymer of claim 38, wherein W2 is —O— or —NH—.
The cross-linked polymer of claim 38, wherein W2 is —O—.
The cross-linked polymer of claim 38, wherein
- L101 is —C(O)—, —NHC(O)—, —C(O)NH—, or —Si(R101)2—;
- L102 is an unsubstituted alkylene;
- L103 is —C(O)—, —NHC(O)—, —C(O)NH—, or —Si(R103)2—;
- and
- R101 and R103 are independently halogen, —OH, —NH2, or substituted or unsubstituted heteroalkylene.
The cross-linked polymer of claim 43, wherein R101 and R103 are each independently —Cl or —OH.
The mixture of polymers of claim 46, wherein the second polymer is a high-density polyethylene, a low-density polyethylene, or a linear low-density polyethylene.
Dependencies are inferred from the claim text.