Alkylated diphenyl ether compound and lubricating oil containing said compound

Patent metadata

Field	Value
Publication number	US-10487034-B2
Application number	US-201314401955-A
Country	US
Kind code	B2
Filing date	Oct 30, 2013
Priority date	Oct 31, 2012
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

A compound of the formula (2)

wherein R 3 is a hydrocarbon group having 12 or 14 carbon atoms which is mainly composed of any one of 1-methylundecyl, 1-ethyldecyl, 1-dodecyl, 1-methyltridecyl, 1-ethyldodecyl and 1-tetradecyl, and 30 to 40 mole % of the total benzylic carbons of R 3 being quaternary, R 4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R 3 and R 4 being quaternary, m and n are each a real number of 1.0≤m≤2.0, 1.0≤n≤2.0 and 2.0≤m+n≤3.0.

First claim

The invention claimed is:

1. A mixture consisting essentially of compounds having the formula (2)

wherein R 3 is a hydrocarbon group having 12 or 14 carbon atoms, and 30 to 40 mole % of the total benzylic carbons of R 3 being quaternary, R 4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R 3 and R 4 being quaternary, m and n are each a real number of 1.0≤m≤2.0, 1.0≤n≤2.0 and 2.0≤m+n≤3.0, and
monoalkylated diphenyl ether in an amount of about 0.1 to 5 mole % of the mixture.

2. A mixture consisting essentially of compounds having the formula (2) obtained by an addition reaction of diphenyl ether derivative of the formula (3) and a branched α-olefin of the formula (1) or its corresponding branched alkyl halide

wherein R 1 and R 2 are the same or different and are a hydrocarbon group having 4 to 12 carbon atoms, R 3 is a hydrocarbon group having 12 or 14 carbon atoms, and 30 to 40 mole % of the total benzylic carbons of R 3 being quaternary, R 4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R 3 and R 4 being quaternary, m and n are each a real number of 1.0≤m≤2.0, 1.0≤n≤2.0 and 2.0≤m+n≤3.0, and
monoalkylated diphenyl ether in an amount of about 0.1 to 5 mole % of the mixture.

3. The mixture as defined in claim 1 wherein the total of a ratio of the carbon at benzyl position of each R 3 and R 4 being quaternary is 45 to 95 mole %.

4. The mixture as defined in claim 1 wherein 50 to 90 mole % of the total benzylic carbons of each R 3 and R 4 is quaternary.

5. The mixture as defined in claim 1 wherein 50 to 65 mole % of the total benzylic carbons of each R 3 and R 4 is quaternary.

6. The mixture as defined in claim 1 wherein R 4 is 1-butyl-1-methylheptyl, 1-methyl-1-pentyloctyl, 1-hexyl-1-methylnonyl, 1-heptyl-1-methyldecyl, 1-methyl-1-octylundecyl or 1-decyl-1-methyltridecyl.

7. A lubricating oil containing the mixture of claim 1 .

8. A grease containing the mixture of claim 1 .

9. A grease composition as defined in claim 8 wherein the grease composition is used for bearing.

10. A mixture consisting essentially of compounds having formula (2) obtained by an addition reaction of diphenyl ether derivative of the formula (4) and an α-olefin of the formula (5) or (6)
wherein R 3 is a hydrocarbon group having 12 or 14 carbon atoms, and 30 to 40 mole % of the total benzylic carbons of R 3 being quaternary, R 4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R3 and R4 being quaternary, m and n are each a real number of 1.0≤m≤2.0, 1.0≤n≤2.0 and 2.0≤m+n≤3.0, and
monoalkylated diphenyl ether in an amount of about 0.1 to 5 mole % of the mixture.

11. The mixture as defined in claim 1 wherein 2.0≤m+n≤2.5.

12. The mixture as defined in claim 11 wherein 2.23≤m+n≤2.41.

13. A mixture consisting essentially of compounds having the formula (2)

wherein R 3 is a hydrocarbon group having 12 or 14 carbon atoms which is composed of any one of 1-methylundecyl, 1-ethyldecyl, 1-dodecyl, 1-methyltridecyl, 1-ethyldodecyl or 1-tetradecyl,
R 3 further comprises a hydrocarbon group having 12 or 14 carbon atoms wherein the benzylic carbon is quaternary, and 30 to 40 mole % of the total benzylic carbons of R 3 being quaternary,
R 4 is a branched hydrocarbon group having 16 to 20 carbon atoms, 42 to 100 mole % of the total benzylic carbons of each R 3 and R 4 being quaternary, m and n are each a real number of 1.0≤m≤2.0, 1.0≤n≤2.0 and 2.0≤m+n≤3.0, and
monoalkylated diphenyl ether in an amount of about 0.1 to 5 mole % of the mixture.

Assignees

• Moresco Corp

Inventors

• Hayashi Mayumi
• Maruyama Shingo

Classifications

• F16C33/6633

  Grease properties or compositions, e.g. rheological properties · CPC title

• C10M2207/0406

  used as base material · CPC title

• C07C43/275 Primary

  having all ether-oxygen atoms bound to carbon atoms of six-membered aromatic rings · CPC title

• C10M105/18

  Ethers, e.g. epoxides · CPC title