Oil soluble polymers
View Patent ↗(EN) The invention relates to a polymer comprising 50-100% by weight, with regard to the weight of the polymers, of repeating units, which are derived from one or more ethylenically unsaturated ester compounds of formula (I), in which R represents hydrogen or methyl; R 1 represents a linear or unbranched alkyl radical with 7 to 30 carbon atoms, and; R 2 and R 3 independently represent hydrogen or a group of formula —COOR′, wherein R′ represents hydrogen or an alkyl group with 7 to 30 carbon atoms. The polymer is a star polymer with 3 to 21 arms and at least 3 of the arms consist of at least 40% by weight, with regard to the weight of the arms, of repeating units, which are derived from one or more ethylenically unsaturated ester compounds of formula (I), in which R 1 represents a linear or unbranched alkyl radical with 7 to 30 carbon atoms, and; R 2 and R 3 independently represent hydrogen or a group of formula —COOR′, wherein R′ represents hydrogen or an alkyl group with 7 to 30 carbon atoms. The invention also relates to oil formulations comprising the inventive polymers. The inventive polymers having a high thickening action can be used, in particular, as viscosity modifiers, pour point depressants, dispersing agents and/or friction modifiers.
1. A polymer, comprising:
50-100% by weight, based on the weight of the polymer, of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (I)
in which R is hydrogen or methyl, R 1 is a linear or branched alkyl radical having from 7 to 30 carbon atoms, R 2 and R 3 are each independently hydrogen or a group of the formula —COOR′ in which R′ is hydrogen or an alkyl group having from 7 to 30 carbon atoms,
wherein the polymer is a star polymer having from 3 to 21 arms and at least 3 of the arms comprise at least 40% by weight, based on the weight of the arms, of repeat units which derive from one or more ethylenically unsaturated ester compounds of the formula (I)
in which R is hydrogen or methyl, R 1 is a linear or branched alkyl radical having from 7 to 30 carbon atoms, R 2 and R 3 are each independently hydrogen or a group of the formula —COOR′ in which R′ is hydrogen or an alkyl group having from 7 to 30 carbon atoms;
wherein the polymer is prepared by controlled polymerization proceeding from a polyfunctional initiator;
wherein the number of polymer arms depends on the number of functionalities of the initiator;
wherein the center of the star polymer has at most 50 carbon atoms;
wherein the star polymer has a polydispersity M w /M n in the range from 1.0 to 2.0; and
wherein the polymer has from 0.1 to 40% by weight of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (II)
in which R is hydrogen or methyl, R 4 is a linear or branched alkyl radical having from 1 to 6 carbon atoms, R 5 and R 6 are each independently hydrogen or a group of the formula —COOR″ in which R″ is hydrogen or an alkyl group having from 1 to 6 carbon atoms.
2. The polymer as claimed in claim 1 , wherein the polymer has a filterability of at least 90%, based on a projected filterability (stage 1) to ISO 13357-2.
3. The polymer as claimed in claim 1 , wherein the polymer has a filterability of at least 70%, based on the overall course of the filtration (stage 2) to ISO 13357-2.
4. The polymer as claimed in claim 1 , wherein the star polymer has from 5 to 12 arms.
5. The polymer as claimed in claim 1 , wherein the star polymer has a weight-average molecular weight M w in the range from 25 000 to 150 000 g/mol.
6. The polymer as claimed in claim 1 , wherein the star polymer has a polydispersity M w /M n in the range from 1.0 to 1.3.
7. The polymer as claimed in claim 1 , wherein the polymer has up to 30% by weight of repeat units which are derived from dispersing monomers (III).
8. The polymer as claimed in claim 7 , wherein the dispersing monomer is a dispersing (meth)acrylate based on an alcohol R 7 —OH or a (meth)acrylamide based on an amine R 7 —NR 8 —H, in that R 7 is independently a group which comprises from 2 to 200 carbon atoms and has at least one heteroatom and in that R 8 is independently hydrogen or a group having from 1 to 20 carbon atoms.
9. The polymer as claimed in claim 8 , wherein the R 7 radical comprises at least one group of the formula —OR 8 or —NR 8 R 8 , in which the R 8 radicals are each independently hydrogen or a group having from 1 to 20 carbon atoms.
10. The polymer as claimed in claim 8 , wherein the R 7 radical comprises at most 10 carbon atoms.
11. The polymer as claimed in claim 1 , wherein the star polymer has at least two blocks.
12. The polymer as claimed in claim 11 , wherein the star polymer has at least one lipophilic and one lipophobic block.
13. The polymer as claimed in claim 12 , wherein at least one lipophobic block has at least 50% by weight, based on the weight of the block, of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (II), dispersing oxygen and/or nitrogen-functionalized monomers (III) and/or further ethylenically unsaturated comonomers (IV).
14. The polymer as claimed in claim 12 , wherein the polymer, within a lipophobic block, displays lipophobic segments having an integer segment length greater than or equal to 3.
15. The polymer as claimed in claim 12 , wherein the lipophobic block is arranged in the first half of the corresponding arm, the center constituting the start, of a viscosity index-increasing star polymer.
16. The polymer as claimed in claim 12 , wherein the lipophobic block is arranged in the second half of the corresponding arm, the center constituting the start, of a viscosity index-increasing star polymer.
17. The polymer as claimed in claim 15 , wherein the polymer is arranged in the first half of the corresponding arm, the center constituting the start, of a lipophobic block comprising at least 50% by weight, based on the weight of the block, of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (II) and/or further comonomers (IV), and a lipophobic block which is derived from dispersing oxygen- and/or nitrogen-functionalized monomers (III) in the second half of the corresponding arm, the center constituting the start.
18. The process for preparing polymers as claimed in claim 1 , wherein polymer is prepared by controlled free-radical polymerization proceeding from a polyfunctional initiator.
19. The process as claimed in claim 1 , wherein the polymerization is performed in the presence of an oil and/or nonpolar solvent.
20. An oil formulation comprising star polymers as claimed in claim 1 .
21. The oil formulation as claimed in claim 20 , wherein the oil formulation comprises from 1 to 25% by weight of star polymers.
22. The oil formulation as claimed in claim 20 , wherein the PSSI to ASTM D5621 (ultrasound for 40 min) is less than or equal to 25.
23. The oil formulation as claimed in claim 20 , wherein the PSSI to DIN 51350 part 6 (20 h, tapered roller bearing) is less than or equal to 50.
24. The oil formulation as claimed in claim 20 , wherein the viscosity index can be adjusted in a controlled manner within the range from 0 to 300.
25. The oil formulation as claimed in claim 20 , wherein the oil formulation is a lubricant oil formulation.
26. The lubricant oil formulation as claimed in claim 25 , which comprises base oils of API group I, II, III, IV and/or group V.
27. The lubricant oil formulation as claimed in claim 26 , wherein the lubricant oil formulation comprises at least one additional additive which is not a star polymer.
28. The lubricant oil formulation as claimed in claim 27 , wherein the additional additive is a viscosity index improver, pour point improver, dispersant and/or friction modifier.
29. The lubricant oil formulation as claimed in claim 27 , wherein the additive is based on a linear polyalkyl (meth)acrylate having from 1 to 30 carbon atoms in the alcohol group.
30. A viscosity modifier, pour point improver, dispersant and/or friction modifier comprising a star polymer as claimed in claim 1 .
31. A polymer, comprising:
50-100% by weight, based on the weight of the polymer, of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (I)
in which R is hydrogen or methyl, R 1 is a linear or branched alkyl radical having from 7 to 30 carbon atoms, R 2 and R 3 are each independently hydrogen or a group of the formula —COOR′ in which R′ is hydrogen or an alkyl group having from 7 to 30 carbon atoms,
wherein the polymer is a star polymer having from 3 to 21 arms and at least 3 of the arms comprise at least 40% by weight, based on the weight of the arms, of repeat units which derive from one or more ethylenically unsaturated ester compounds of the formula (I)
in which R is hydrogen or methyl, R 1 is a linear or branched alkyl radical having from 7 to 30 carbon atoms, R 2 and R 3 are each independently hydrogen or a group of the formula —COOR′ in which R′ is hydrogen or an alkyl group having from 7 to 30 carbon atoms;
wherein the star polymer has a filterability of at least 90%, based on a projected filterability (stage 1) to ISO 13357-2;
wherein the star polymer has a filterability of at least 70%, based on the overall course of the filtration (stage 2) to ISO 13357-2;
wherein the star polymer has a weight-average molecular weight M w in the range from 25 000 to 150 000 g/mol;
wherein the star polymer has a polydispersity M w /M n in the range from 1.0 to 1.3; and
wherein the polymer has from 0.1 to 40% by weight of repeat units which are derived from one or more ethylenically unsaturated ester compounds of the formula (II)
in which R is hydrogen or methyl, R 4 is a linear or branched alkyl radical having from 1 to 6 carbon atoms, R 5 and R 6 are each independently hydrogen or a group of the formula —COOR″ in which R″ is hydrogen or an alkyl group having from 1 to 6 carbon atoms.