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1. (WO2018226376) METHODS OF MAKING COMPOUNDS AND MIXTURES HAVING ANTIDEGRADANT AND ANTIFATIGUE EFFICACY
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CLAIMS

1 . A method of making an antidegradant compound, the method

comprising:

reacting a p-phenylenediamine corresponding to formula IV:


IV

wherein each X is independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen;

with a diol corresponding to formula II:


wherein each R is independently selected from the group consisting of (i) substituted or unsubstituted alkyl with C = 0 to 12 inclusive, (ii) substituted or unsubstituted aryl, and (iii) substituted and unsubstituted alkylaryl; and

wherein R1 and R3 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen, to thereby obtain a mixture comprising the antidegradant compound according to formula I:


wherein each R is independently selected from the group consisting of (i) substituted or unsubstituted alkyl with C = 0 to 12 inclusive, (ii) substituted or unsubstituted aryl, and (iii) substituted and unsubstituted alkylaryl;

wherein each X is independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen;

wherein R1 and R3 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; and

wherein R1 and R3 may optionally be bridged by a polymethylene group to form a cycloalkyl;

wherein when C=0 in R, R1 is the same as R3; and wherein when C=1 in R, each of R1 and R3 is hydrogen.

2. The method claim 1 , wherein the step of reacting the p-phenylenediamine with the diol is carried out in the presence of a metal catalyst.

3. The method of claim 2, wherein the metal catalyst comprises one or more of a homogeneous and a heterogeneous metal catalyst.

4. The method of claim 2, wherein the metal catalyst comprises a ligand-functionalized homogeneous or solid-supported heterogeneous catalyst based on one or more of ruthenium, iridium, platinum, palladium, tin, iron, AI2O3, and

5. The method of claim 1 , wherein the p-phenylenediamine comprises 4-amino-p-phenylene diamine.

6. The method of claim 1 , wherein the diol comprises one or more of ethylene glycol, propylene glycol, butane diol or octane-1 ,8-diol.

7. The method of claim 1 , wherein the antidegradant compound comprises N,N'-(octane-1 ,8-diyl)bis(N-phenylbenzene-1 ,4-diamine).

8. The method of claim 1 , wherein the antidegradant compound comprises N,N'-(ethane-1 ,2-diyl)bis(N-phenylbenzene-1 ,4-diamine).

9. The method of claim 1 , wherein the antidegradant compound comprises N,N'-(1 ,4-phenylenebis(ethane-1 ,1 -diyl))bis(N-phenylbenzene-1 ,4-diamine).

10. The method of claim 1 , wherein the antidegradant compound comprises N,N'-(1 ,3-phenylenebis(ethane-1 ,1 -diyl))bis(N-phenylbenzene-1 ,4-diamine).

1 1 . The method of claim 1 , wherein the antidegradant compound comprises (N,N',N,N')-N,N'-(1 ,4-phenylenebis(ethan-1 -yl-1 -ylidene))bis(N-phenylbenzene-1 ,4-diamine).

12. The method of claim 1 , wherein the antidegradant compound comprises (N,N',N,N')-N,N'-(1 ,3-phenylenebis(ethan-1 -yl-1 -ylidene))bis(N-phenylbenzene-1 ,4-diamine).