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US 10,611,719 B2Granted
Methods of making compounds and mixtures having antidegradant and antifatigue efficacy
AssigneeEastman Chemical Company
InventorsMatthew Allen Boone, Donald L. Fields, Jr., Frederick Ignatz-Hoover
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Abstract
Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a dicarbonyl to thereby obtain a diimine, which is reduced to obtain mixtures comprising the antidegradant compound.
Claims13
A method of making an antidegradant compound, the method comprising:
- reacting a p-phenylenediamine corresponding to formula IV:
- wherein X is selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen;
- with a dicarbonyl corresponding to formula II:
- 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 thereby obtain a diimine;
- and
- reducing the diimine to thereby obtain a mixture comprising the antidegradant compound according to formula I:
- 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.
8 more elements
Dependencies are inferred from the claim text.