High-viscosity alpha-olefin copolymer compositions and methods of making and using the same
View Patent ↗Copolymers of alpha-olefins are generally disclosed, including methods of making such copolymers. In some embodiments, copolymers of alpha-olefins and certain unsaturated ester compounds are also disclosed, including methods of making such copolymers. Lubricant compositions including copolymers of alpha-olefins are also disclosed, as well as methods of using such compositions in certain lubricant applications.
1. A composition, comprising:
a copolymer comprising constitutional units formed from two or more monomers, the two or more monomers comprising
a first monomer, which is 1-dodecene, and
a second monomer, which is an α-ester-alk-ω-ene molecule;
where the mole-to-mole ratio of the first monomer to the second monomer is from 2:1 to 5:1; and
where the composition has a kinematic viscosity at 100° C. of 25 to 200 centistokes.
2. The composition of claim 1 , where the second monomer is a compound of formula (I):
wherein
R 1 is C 1-12 alkyl, which is optionally substituted one or more times by substituents selected independently from R 2 ;
R 2 is halogen, —OH, C 1-6 alkoxy, —NH 2 , —NH(C 1-6 alkyl), —N(C 1-6 alkyl) 2 , C 1-6 haloalkyl, or C 1-6 haloalkoxy; and
X 1 is C 1-24 alkylene or C 2-24 alkenylene, each of which is optionally substituted one or more times by substituents selected independently from R 2 .
3. The composition of claim 2 , where R l is methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, isoamyl, neopentyl, hexyl, octyl, or 2-ethylhexyl.
4. The composition of claim 3 , where R 1 is methyl, ethyl, or isopropyl.
5. The composition of claim 4 , where R 1 is methyl.
6. The composition of claim 2 , where X 1 is —(CH 2 ) 7 —or —(CH 2 ) 9 —.
7. The composition of claim 6 , where X 1 is —(CH 2 ) 7 —.
8. The composition of claim 1 , where the composition has a kinematic viscosity at 100° C. of 25 to 150 centistokes.
9. The composition of claim 1 , where the copolymer is formed by free radical polymerization.
10. The composition of claim 9 , where the free radical polymerization is carried out in the presence of a free radical initiator.
11. The composition of claim 10 where the polymerization initiator is a peroxide, a persulfate, a hydroperoxide, a perester, an azo compound, a photoinitiator, or a combination thereof.
12. The composition of claim 11 , wherein the polymerization initiator is an organic peroxide.
13. The composition of claim 12 , where the organic peroxide is di-tert-butyl peroxide, di-tert-amyl peroxide, or a combination thereof.
14. A lubricant composition, comprising:
a composition of claim 1 .
15. A method for making a lubricant composition, the method comprising:
providing a composition of claim 1 and a diluent, where the diluent is miscible with the composition; and
mixing the composition and the diluent to form a diluted composition.
16. A method of making an alpha-olefin copolymer composition, comprising:
providing a composition of claim 1 ; and
at least partially hydrogenating the copolymers in the composition.
17. A method of making an alpha-olefin copolymer composition, comprising:
providing a composition of claim 1 ; and
transesterifying the copolymers by reacting the copolymers with one or more alcohols.
18. The composition of claim 1 , wherein the second monomer is methyl 9-decenoate.