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US 2006/0233741 A1Published application
Alkylated and polymeric macromolecular antioxidants and methods of making and using the same
AssigneePolnox Corporation
InventorsRajesh Kumar, Ashok Cholli
Life of this patent
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Abstract
Alkylated antioxidant macromolecules are represented by Structural Formula 1: wherein the variables are described herein. Also included are methods of making the molecules and methods of using the molecules as antioxidants.
Claims32
A compound represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M is an alkyl or
- each n and m are independently integers from 0 to 6;
- and
- each s, q and u are independently integers from 0 to 4;
- wherein M is not
- when X is
- —C(O)O— or —OC(O)—.
11 more elements
A polymer represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)—or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or
- wherein at least one R2 is
- each R′2 is independently -M′-X, an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- each Y is independently Q-W-Q′;
- each Q is independently an optionally substituted C1-C20 alkylene group;
- each Q′ is independently a bond or an optionally substituted C1-C20 alkylene group;
- each W is independently arylene, —O—, —S—, —NR′—, —N(OR′)—, —C(═N(OR′))—, —C(O)NR′—, —NR′C(O)—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —C(O)OC(O)—, or a bond;
- each M′ is independently —H, alkyl, or
- each n and m are independently integers from 0 to 6;
- each s, q and u are independently integers from 0 to 4;
- and
- r is an integer from 0 to 4.
15 more elements
A composition comprising compound one represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′′, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M is an alkyl or
- each n and m are independently integers from 0 to 6;
- each s, q and u are independently integers from 0 to 4;
- and compound two represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M′ is a —H, alkyl or
- each n and m are independently integers from 0 to 6;
- and
- each s, q and u are independently integers from 0 to 4.
19 more elements
A method of inhibiting oxidation in an oxidizable material comprising combining the oxidizable material with a compound represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M is an alkyl or
- each n and m are independently integers from 0 to 6;
- and
- each s, q and u are independently integers from 0 to 4;
- wherein M is not
- when X is —C(O)O— or —OC(O)—.
10 more elements
A method of inhibiting oxidation in an oxidizable material comprising combining the oxidizable material with a polymer represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or
- each R′2 is independently -M-X, an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or —;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- each Y is independently Q-W-Q′;
- each Q is independently an optionally substituted C1-C20 alkylene group;
- each Q′ is independently a bond or an optionally substituted C1-C20 alkylene group;
- each W is independently arylene, —O—, —S—, —NR′—, —N(OR′)—, —C(═N(OR′))—, —C(O)NR′—, —NR′C(O)—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —C(O)OC(O)—, or a bond;
- each M′ is independently —H, alkyl, or
- each n and m are independently integers from 0 to 6;
- each s, q and u are independently integers from 0 to 4;
- and
- r is an integer from 0 to 4.
14 more elements
A method of inhibiting oxidation in an oxidizable material comprising combining the oxidizable material with a composition comprising compound one represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M is an alkyl or
- each n and m are independently integers from 0 to 6;
- each s, q and u are independently integers from 0 to 4;
- and compound two represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M′ is a —H, alkyl or
- each n and m are independently integers from 0 to 6;
- and
- each s, q and u are independently integers from 0 to 4.
19 more elements
A method of making a compound represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CH═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- M is an alkyl or
- each n and m are independently integers from 0 to 6;
- and
- each s, q and u are independently integers from 0 to 4;
- comprising the steps of:
- a) alkylating a compound represented by the following structural formula:
- with a haloalkyl;
- and
- b) isolating the alkylated compound.
13 more elements
A method of making a polymer represented by the following Structural Formula:
- wherein:
- Z is —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —O—, —S—, —C(O)OC(O)— or a bond;
- each R′ is independently —H or optionally substituted alkyl;
- each R is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH, or
- each R1 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2 or —SH;
- each R2 is independently an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or
- each R′2 is independently -M-X, an optionally substituted alkyl, optionally substituted aryl, optionally substituted alkoxycarbonyl, optionally substituted ester, —OH, —NH2, —SH or —;
- X is —C(O)O—, —OC(O)—, —C(O)NR′—, —NR′C(O)—, —NR′—, —CR′═N—, —C(O)—, —O—, —S—, —NR′— or —C(O)OC(O)—;
- each Y is independently Q-W-Q′;
- each Q is independently an optionally substituted C1-C20 alkylene group;
- each Q′ is independently a bond or an optionally substituted C1-C20 alkylene group;
- each W is independently arylene, —O—, —S—, —NR′—, —N(OR′)—, —C(═N(OR′))—, —C(O)NR′—, —NR′C(O)—, —CR′═N—, —C(O)—, —C(O)O—, —OC(O)—, —C(O)OC(O)—, or a bond;
- each M′ is independently —H, alkyl, or
- each n and m are independently integers from 0 to 6;
- each s, q and u are independently integers from 0 to 4;
- and
- r is an integer from 0 to 4
- comprising the steps of:
- a) polymerizing a compound represented by the following structural formula:
- in the presence of an aldehyde;
- and
- b) isolating the polymer.
19 more elements
Dependencies are inferred from the claim text.