Macromonomers containing polyisobutene groups, and homopolymers or copolymers thereof

Patent metadata

Field	Value
Publication number	US-11174333-B2
Application number	US-201716322612-A
Country	US
Kind code	B2
Filing date	Jul 26, 2017
Priority date	Aug 5, 2016
Publication date	Nov 16, 2021
Grant date	Nov 16, 2021

Abstract

The present invention describes novel macromonomers containing polyisobutene groups and homo- or copolymers thereof.

First claim

The invention claimed is:

1. A process for preparing
a compound (A) of the formula (I)

in which
R 1 to R 5 are each independently selected from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyloxy and C 5 -C 3500 -polyisobutyl and C 5 -C 3500 -polyisobutenyl,
R is an alkylene group having 2 to 10 carbon atoms,
R 6 is hydrogen or methyl,
R 7 is hydrogen, methyl or COOR 8 ,
R 8 is hydrogen or C 1 -C 20 -alkyl and
n is a positive integer from 1 to 50,
with the proviso that
at least one of the R 1 to R 5 radicals is a C 5 -C 3500 -polyisobutyl or C 5 -C 3500 -polyisobutenyl,
and is derived from polyisobutene having a content of terminal double bonds of at least 50 mol %, based on the total number of polyisobutene macromolecules,

wherein phenols of the formula

are reacted with alkylene carbonates of the formula

followed by a decarboxylation and subsequent esterification with (meth)acrylic acid, crotonic acid, fumaric acid, maleic acid or maleic anhydride, or by transesterification with (meth)acrylic esters, crotonic esters, fumaric esters or maleic esters.

2. The process as claimed in claim 1 , wherein the alkylene carbonate is selected from the group consisting of 1,2-ethylene carbonate, 1,3-propylene carbonate and 1,2-propylene carbonate.

3. The process as claimed in claim 1 , wherein the stoichiometry of 1 to 2 mol of carbonate:1 mol of phenol.

4. The process as claimed in claim 2 , wherein the stoichiometry of 1.2 to 1.5 mol of carbonate:1 mol of phenol.

5. The process as claimed in claim 1 , wherein the catalyst is selected from the group consisting of an inorganic salt, tertiary amine, triphenylphosphine, lithium hydride and organic stannate.

6. The process as claimed in claim 1 , wherein the reaction is carried out at a temperature of 70 to 200° C.

7. The process as claimed in claim 1 , wherein the reaction is carried out at a temperature of 150 to 170° C.

8. The process as claimed in claim 1 , wherein the esterification with (meth)acrylic anhydride in the presence of at least one basic catalyst.

9. The process as claimed in claim 1 , wherein the transesterification with C 1 -4 alkyl ester is a methyl ester, ethyl ester, n-propyl ester, isopropyl ester, n-butyl ester, sec-butyl ester, isobutyl ester or tert-butyl ester.

10. A fuel additive or a lubricant additive which comprises a copolymer comprising, in polymerized form,
at least one compound (A) of the formula (I)

in which
R 1 to R 5 are each independently selected from the group consisting of hydrogen, C 1 -C 20 -alkyl, C 1 -C 20 -alkyloxy and C 5 -C 3500 -polyisobutyl and C 5 -C 3500 -polyisobutenyl,
R is an alkylene group having 2 to 10 carbon atoms,
R 6 is hydrogen or methyl,
R 7 is hydrogen, methyl or COOR 8 ,
R 8 is hydrogen or C 1 -C 2 O-alkyl and
n is a positive integer from 1 to 50,
with the proviso that
at least one of the R 1 to R 5 radicals is a C 5 -C 3500 -polyisobutyl or C 5 -C 3500 -polyisobutenyl,
and is derived from polyisobutene having a content of terminal double bonds of at least 50 mol %, based on the total number of polyisobutene macromolecules,
and at least one monomer (B) selected from the group consisting of
(B1) (meth)acrylates other than (A),
(B3) alkyl vinyl ethers
(B4) styrene and α-methylstyrene and
(B7) (meth)acrylamides.

11. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the monomer (B1) is methyl (meth)acrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, n-decyl (meth)acrylate, n-dodecyl (meth)acrylate, n-tetradecyl (meth)acrylate, n-hexadecyl (meth)acrylate, n-heptadecyl (meth)acrylate), n-octadecyl (meth)acrylate, n-eicosyl (meth)acrylate, 2-ethylhexyl (meth)acrylate and 2-propylheptyl (meth)acrylate, particular preference to methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate and 2-ethylhexyl (meth)acrylate.

12. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the proportions of compound (A) in the polymer in polymerized form is at least 1% by weight.

13. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the proportions of compound (A) in the polymer in the polymerized form is at least 1% by weight up to 100% by weight but without 100% (the homopolymer).

14. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the molecular weight as listed in mass-average molecular weight Mw of the polymers obtained is 5,000 g/mol or more.

15. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the molecular weight as listed in mass-average molecular weight Mw of the polymers obtained is 5,000 g/mol up to 1,000,000 g/mol.

16. The fuel additive or the lubricant additive as claimed in claim 10 , wherein exactly one of the R 1 to R 5 radicals is C8-C3500-polyisobutyl or C8-C3500-polyisobutenyl.

17. The fuel additive or the lubricant additive as claimed in claim 10 , wherein R 3 is a C8-C3500-polyisobutyl or C8-C3500-polyisobutenyl radical and the other radicals are not.

18. The fuel additive or the lubricant additive as claimed in claim 10 , wherein the R 1 to R 5 radicals that are not a polyisobutyl or polyisobutenyl radical are selected from the group consisting of hydrogen, methyl and tert-butyl.

19. The fuel additive or the lubricant additive as claimed in claim 10 , wherein R is selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,2-butylene, 1-phenyl-1,2-ethylene and 2-phenyl-1,2-ethylene.

20. The fuel additive or the lubricant additive as claimed in claim 10 , wherein n is 1.

Assignees

• Basf Se

Inventors

• Misske Andrea
• Thomas Anja
• Fleckenstein Christoph
• Fleischhaker Friederike
• Csihony Szilard
• Gerst Matthias
• Moebius Stephan
• Licht Ulrike
• Schwarz Andreas
• Neuhaus Eric

Classifications

• C08F220/30

  containing aromatic rings in the alcohol moiety · CPC title

• C08F120/30

  containing aromatic rings in the alcohol moiety · CPC title

• C08F290/046

  Polymers of unsaturated carboxylic acids or derivatives thereof · CPC title

• C08F2/22 Primary

  Emulsion polymerisation · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title