Compounds and mixtures with antidegradant and antifatigue efficacy and compositions including such compounds
View Patent ↗Antidegradant compounds are disclosed, and methods of making them, that are represented by the formula I: wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen. Also disclosed are diimine intermediates corresponding to formula III: wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen. These intermediates themselves exhibit antidegradant activity.
1. An antidegradant compound represented by formula I:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen.
2. The compound of claim 1 , wherein each X is hydrogen.
3. The compound of claim 1 , wherein each X is methyl.
4. A method of making the antidegradant compound of claim 1 , comprising:
reacting, a p-phenylenediamine corresponding to formula IV:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen,
with a dicarbonyl corresponding to formula
to thereby obtain a diimine; and
reducing or hydrogenating the diimine to obtain a mixture that includes the antidegradant compound.
5. The method of claim 4 , wherein the p-phenylenediamine is reacted with the dicarbonyl in the presence of an acid catalyst.
6. A method of making the antidegradant compound of claim 1 , comprising:
reacting a p-phenylenediamine corresponding to formula IV:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen,
with a diol corresponding to formula V:
to thereby obtain a diimine; and
reducing or hydrogenating the diimine to obtain a mixture that includes the antidegradant compound according to formula I.
7. The method of claim 6 , wherein the p-phenylenediamine is reacted with the dicarbonyl in the presence of an acid catalyst.
8. A method of making the antidegradant compound of claim 1 , comprising:
reacting a p-phenylenediamine corresponding to formula IV:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen,
with one or more of:
a dial corresponding to formula V;
or
a dicarbonyl corresponding to formula II:
to thereby obtain a diimine; and
reducing or hydrogenating the diimine to obtain a mixture that includes the antidegradant compound according to formula I.
9. The method of claim 8 , wherein the p-phenylenediamine is reacted with the diol or the dicarbonyl in the presence of an acid catalyst.
10. A diimine corresponding to formula III:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen.
11. A method of making the diimine of claim 10 , comprising:
reacting a p-phenylenediamine corresponding to formula IV:
wherein each X is independently selected from the group consisting of ethyl, methyl, or hydrogen,
with one or more of:
a diol corresponding to formula V:
or
a dicarbonyl corresponding to formula II:
to thereby obtain the diimine.