Methods of making compounds and mixtures having antidegradant and antifatigue efficacy
View Patent ↗Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.
1. A method of making an antidegradant compound, the method comprising:
reacting a p-phenylenediamine corresponding to formula 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 R 1 and R 3 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 R 1 and R 3 are each independently selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; and
wherein R 1 and R 3 may optionally be bridged by a polymethylene group to form a cycloalkyl;
wherein when C=0 in R, R 1 is the same as R 3 ; and
wherein when C=1 in R, each of R 1 and R 3 is hydrogen.
2. The method of claim 1 , wherein the step of reacting the p-phenylenediamine with the dial 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, Al 2 O 3 , and TiO 2 .
5. The method of claim 1 , wherein the p-phenylenediamine comprises 4-aminodiphenylamine.
6. The method of claim 1 , wherein the diol comprises one or more of ethylene glycol, propylene glycol, butane dial 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).
11. 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).