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US 2006/0189824 A1Published application
Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis, performances and applications
AssigneePolnox Corporation
InventorsRajesh Kumar, Suizhou Yang, Vijayendra Kumar, Ashok Cholli
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Abstract
Disclosed are compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I) and their use in inhibiting oxidation in an oxidizable material.
Claims42
A compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- u is an integer from 1 to 4;
- and
- with the proviso that when n is 1, then either ring C is not:
- s is not 0, or R″ is not —H.
13 more elements
A method of producing a compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- and
- u is an integer from 1 to 4;
- comprising:
- a) combining a phenol derivative, an amine and an aldehyde in the presence of a solvent, wherein the phenol derivative comprises at least one unsubstituted ring-carbon atom;
- b) refluxing the combination of step a) to produce the compound;
- and
- c) isolating the compound.
16 more elements
A method of producing a compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- and
- u is an integer from 1 to 4;
- comprising:
- a) combining a amino-phenol derivative with an amine in the presence of a solvent;
- b) relfuxing the combination of step a) to produce the compound;
- and
- c) isolating the compound.
16 more elements
A method of producing a compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- R* is —H or an optionally substituted alkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- o is an integer from 0 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- and
- u is an integer from 1 to 4;
- comprising:
- a) combining a phenolic-carbonyl derivative represented by the following structural formula:
- with an amine in the presence of a solvent;
- b) relfuxing the combination of step a) to produce a schiff's base;
- c) reducing the schiff's base with a reducing agent to produce the compound;
- and
- d) isolating the compound.
20 more elements
A method of producing a compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- and
- u is an integer from 1 to 4;
- comprising:
- a) combining a formaldehyde-sodium bisulfite adduct with an amine in aqueous media to produce a methylsulfonate sodium salt;
- b) displacing the sulfonate group of the methylsulfonate sodium salt via nucleophilic displacement with a sodium or potassium salt of a phenol derivative, in an aqueous media, wherein the nucleophilic displacement is catalyzed base to produce the compound;
- and
- b) isolating the compound.
16 more elements
A method of preventing oxidation in an oxidizable material, comprising combining the oxidizable material with a compound represented by the following structural formula:
- wherein:
- each Ra is independently an optionally substituted alkyl;
- each Rb is independently an optionally substituted alkyl;
- each Rc is independently an optionally substituted alkyl or an optionally substituted alkoxycarbonyl;
- Rx is —H or an optionally substituted alkyl;
- Ry is —H or an optionally substituted alkyl;
- each R′ is independently —H or an optionally substituted alkyl;
- R″ is —H, an optionally substituted alkyl, an optionally substituted aryl or an optionally substituted aralkyl;
- n is an integer from 1 to 10;
- m is an integer from 1 to 10;
- s is an integer from 0 to 5;
- t is an integer from 0 to 4;
- and
- u is an integer from 1 to 4.
11 more elements
Dependencies are inferred from the claim text.