Methods of making compounds and mixtures having antidegradant and antifatigue efficacy

Patent metadata

Field	Value
Publication number	US-10160845-B2
Application number	US-201715618291-A
Country	US
Kind code	B2
Filing date	Jun 9, 2017
Priority date	Dec 22, 2015
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.

First claim

The invention claimed is:

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).

Assignees

• Eastman Chem Co

Inventors

• Boone Matthew Allen
• Fields Jr Donald L
• Ignatz-Hoover Frederick

Classifications

• C10N2030/08

  Resistance to extreme temperature · CPC title

• C10N2030/10

  Inhibition of oxidation, e.g. anti-oxidants · CPC title

• C07C209/18

  with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C10L2230/08

  Inhibitors · CPC title

• C10M133/12

  having amino groups bound to a carbon atom of a six-membered aromatic ring · CPC title