Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants

Patent metadata

Field	Value
Publication number	US-8987515-B2
Application number	US-201213681849-A
Country	US
Kind code	B2
Filing date	Nov 20, 2012
Priority date	Dec 13, 2011
Publication date	Mar 24, 2015
Grant date	Mar 24, 2015

Abstract

Radical initiated reactions of phenylenediamines with alkylated aromatic amines produce an antioxidant mixture containing cross reaction products of the phenylenediamines and alkylated aromatic amines which are useful, for example, as antioxidants, stabilizers, and antiozonants for lubricants, electronic chemicals, rubbers, urethanes and other polymer resins, crop protection, pharmaceuticals, dyes and toners.

First claim

What is claimed is:

1. An antioxidant comprising a mixture of cross products obtained by reacting
a) at least one phenylene diamine of formula I,

wherein R 1 is selected from the group consisting of C 1-12 alkyl, and C 7-18 aralkyl;
R 2 and R 3 are independently selected from the group consisting of H, C 1-12 alkyl, and C 7-18 aralkyl;
n is 0, 1 or 2 and R 8 is C 1-12 alkyl, wherein when n is 2, each R 8 may be the same or different; with
b) at least one diaryl amine of formula IV or V

wherein each R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of H, C 1-12 alkyl, C 7-18 aralkyl, phenyl, phenyl substituted by one or more C 1-12 alkyl groups,
in the presence of a molar excess of an initiator selected from organic peroxides and in the presence of a polyol ester.

2. The antioxidant according to claim 1 wherein n is 0.

3. The antioxidant according to claim 1 wherein
a) the at least one phenylene diamine of formula I is selected from the group consisting of compounds according to

wherein R 1 is selected from the group consisting of C 1-12 alkyl, C 7-18 aralkyl;
R 2 is selected from the group consisting of C 1-12 alkyl, C 7-18 aralkyl;
R 3 is selected from the group consisting of H, C 1-12 alkyl, C 7 - 18 aralkyl; and
b) the at least one diaryl amine is selected from the group consisting of compounds according to formula IV

wherein each R 4 , R 5 , R 6 and R 7 are independently selected from the group consisting of H, C 1-12 alkyl, C 7-18 aralkyl, phenyl, phenyl substituted by one or more C 1-12 alkyl groups, naphthyl and naphthyl substituted by one or more C 1-12 alkyl groups.

4. The antioxidant according to claim 3 comprising at least one cross product obtained from a reaction wherein at least one phenylene diamine of formula I, at least one diaryl amine of formula IV, and at least one polyol ester are reacted together into the same cross product.

5. The antioxidant according to claim 4 wherein R 1 and R 2 are independently alkyl groups of from 4 to 8 carbons, R 4 is an alkyl group of from 4 to about 12 carbons or an aralkyl group of 8 to 10 carbons, and R 5 and R 6 are H.

6. The antioxidant according to claim 3 wherein R 1 and R 2 are independently alkyl groups of from 4 to 8 carbons, R 4 is an alkyl group of from 4 to about 12 carbons or an aralkyl group of 8 to 10 carbons, and R 5 and R 6 are H.

7. The antioxidant according to claim 3 in the form of a concentrate comprising the mixture of cross products and a polyol ester.

8. The antioxidant according to claim 1 comprising co-oligomers formed by the reaction of one or more compounds of formula I and one or more compounds of formula IV or V.

9. The antioxidant according to claim 1 in the form of a concentrate comprising the mixture of cross products and a polyol ester.

Assignees

• Chemtura Corp

Inventors

• Rowland Robert G

Classifications

• C10N2070/02

  Concentrating of additives · CPC title

• C10N2030/10

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

• C10M159/12

  Reaction products · CPC title

• C10M2207/2835

  used as base material · CPC title

• C10M169/04

  Mixtures of base-materials and additives · CPC title