Lubricant Additives

156 Lubricant Additives: Chemistry and Applications

FIGURE 5.9 Manufacture of polyamines.

H 2 C=CH 2 + CI 2 CICH 2 CH 2 CI CICH 2 CH 2 NH 2

CICH 2 CH 2 NH 2

CICH 2 CH 2 CI

NH 3

NH 3

NH 2 CH 2 CH 2 NHCH 2 CH 2 NH 2 NH 2 CH 2 CH 2 NH 2

NH 2 CH 2 CH 2 N

Ethylene Ethylenedichloride Chloroethylamine

Diethylenetriamine Ethylenediamine

NH

Aminoethylpiperazine

FIGURE 5.10 Amine–anhydride reaction products. (Based on Harrison, J.J., Ruhe, R., Jr., William, R., U.S.
Patent 5,625,004, April 29, 1997.)

(a) Primary amine

(b) Secondary amine

(c) Tertiary amine

Polyisobutenyl

Polyisobutenyl

Polyisobutenyl

+ RNH 2

+ R 2 NH

+ R 3 N

Polyisobutenyl

Polyisobutenyl

Polyisobutenyl

Imide

Amide

Salt

O

O

O

O

O

O

NR

O

O

NR 2

NR 2

O

O

OH

NR 2

O

O

NR 2

O NHR 3

O

O

− +

inhibiting and antiwear moieties have been reported in the patent literature [77,96,97]. Dispersant
polymers containing oxidation-inhibiting moieties are commercially available from Texaco Chemi-
cal Company now part of Ethyl Petroleum Additives Company. As the examples show, grafting
usually allows the introduction of the connecting group in the dispersant polymers at the same time
as the polar moiety.