Catalytically Active Radical Scavengers Based on Benzylic and Allylic Functionalities

A composition capable of limiting oxidative radical degradation catalytically via a benzylic hydrogen abstraction mechanism, comprising a polymer and an inhibitor of the formula:

• wherein n is a number from 0 to 1000;
• wherein X1 and Y1 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics;
• wherein the substitution on the aromatic ring can be ortho, meta, para or higher substituted benzene molecules;
• and
• wherein W1 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, amides, esters, carbonyls, epoxies, oxetanes, oxiranes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics.

Inhibitor of formula (1)

• wherein X1 and Y1 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics;
• wherein the substitution on the aromatic ring can be ortho, meta, para or higher substituted benzene molecules;
• and
• wherein W1 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, amides, esters, carbonyls, epoxies, oxetanes, oxiranes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics.

Process for preparing a polymer obtainable by polymerization of at least one ethylenically unsaturated monomer comprising:

• providing a reaction mixture comprising at least one ethylenically unsaturated monomer and optionally a solvent;
• polymerizing at least one ethylenically unsaturated monomer to form a (co)polymer;
• and
• adding the compound of formula (1) to the ethylenically unsaturated monomer:
• wherein X1 and Y1 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics;
• wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted benzene molecules;
• and
• wherein W1 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, amides, esters, carbonyls, epoxies, oxetanes, oxiranes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics,

A composition capable of limiting oxidative radical degradation catalytically via allylic hydrogen abstraction mechanism, comprising a polymer and an inhibitor of the formula:

• wherein X2 and Y2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings;
• wherein W2 is selected from the group consisting of oxygen, sulphur, nitrogen-containing groups and phosphor-containing groups;
• and
• wherein Z2 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, amino derivative or the corresponding salts (ligands), ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings.

Inhibitor of formula (2)

• wherein X2 and Y2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings;
• wherein W2 is selected from the group consisting of oxygen, sulphur, nitrogen-containing groups and phosphor-containing groups;
• and
• wherein Z2 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, amino derivative or the corresponding salts (ligands), ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings.

Process for preparing a polymer obtainable by polymerization of at least one ethylenically unsaturated monomer comprising:

• providing a reaction mixture comprising at least one ethylenically unsaturated monomer and optionally a solvent;
• polymerizing at least one ethylenically unsaturated monomer to form a (co)polymer;
• and
• adding the compound of formula (2) to the ethylenically unsaturated monomer:
• wherein X2 and Y2 are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings;
• wherein W2 is selected from the group consisting of oxygen, sulphur, nitrogen-containing groups and phosphor-containing groups;
• and
• wherein Z2 is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, substituted alkyls, substituted alkenyl, substituted alkynyl, substituted aryls, polycylic aromatics, substituted polycyclic aromatics, polar functional groups, alcohol, amines, amino derivative or the corresponding salts (ligands), ketones, aldehydes, ethers, carboxylic acids, sulfonates, sulfonic acids, phosphonic acids and heterocyclics, wherein the substitution on the aromatic ring can be ortho, meta, para and higher substituted aromatic rings.