Comb polymers comprising imide functionality

Patent metadata

Field	Value
Publication number	US-11072677-B2
Application number	US-201816628331-A
Country	US
Kind code	B2
Filing date	Jul 12, 2018
Priority date	Jul 14, 2017
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

Selected comb polymers include specified amounts of macromonomer and imide functionalization. Further, a method is useful for the preparation of such comb polymers. Lubricant compositions including such comb polymers are useful for reducing wear and fuel consumption of lubricant compositions, especially of engine oil (EO) compositions.

First claim

The invention claimed is:

1. A grafted polyalkyl(meth)acrylate based comb polymer consisting of a base polymer A and units B which are grafted thereon, wherein the base polymer A comprises:
(a) 10% to 25% by weight of at least one repeating unit derived from an ester of (meth)acrylic acid and a hydroxylated hydrogenated polybutadiene;
(b) 0% to 2% by weight of at least one repeating unit derived from methyl (meth)acrylate;
(c) 60% to 80% by weight of at least one repeating unit derived from butyl (meth)acrylate;
(d) 0% to 16% by weight of at least one repeating unit derived from C 10-20 -alkyl (meth)acrylate; and
(e) 0% to 2% by weight of at least one repeating unit derived from a styrene monomer having 8 to 17 carbon atoms,
wherein an amount of each component (a) to (e) is based on a total composition of the grafted polyalkyl(meth)acrylate based comb polymer;
wherein the units B comprise at least one repeating unit prepared from:
(f) 1% to 2.5% by weight of at least one repeating unit derived from polar unsaturated monomer selected from the group consisting of maleic acid, maleic acid anhydride, methyl maleic acid anhydride, maleic acid monoester and maleic acid diester; and
(g) 2% to 5% by weight of at least one repeating unit derived from a primary amine of general formula (I)

wherein each R′ is independently selected from the group consisting of H and an alkyl radical having 1 to 9 carbon atoms, and
wherein the amount of each component (f) and (g) is based on the total composition of the grafted polyalkyl(meth)acrylate based comb polymer.

2. The rafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , comprising:
(a) 10 to 15% by weight of the ester of (meth)acrylic acid and the hydroxylated hydrogenated polybutadiene;
(b) 0% to 2% by weight of the methyl (meth)acrylate;
(c) 65% to 76% by weight of the butyl (meth)acrylate;
(d) 5% to 16% by weight of C 10-15 alkyl (meth)acrylate;
(e) 0% to 2% by weight of the at least one styrene monomer having 8 to 17 carbon atoms;
(f) 1% to 2.5% by weight of the at least one polar unsaturated monomer selected from the group consisting of maleic acid, maleic acid anhydride, methyl maleic acid anhydride, maleic acid monoester and maleic acid diester; and
(g) 2% to 5% by weight of the primary amine of the following general formula (I)

wherein each R′ independently selected from the group consisting of H and an alkyl radical having 1 to 9 carbon atoms.

3. The grafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , wherein the polar unsaturated monomer is maleic acid anhydride.

4. The grafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , wherein the primary amine of general formula (I) is N-phenyl-1,4-phenylenediamine.

5. The grafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , wherein the grafted polyalkyl(meth)acrylate based comb polymer has a weight-average molecular weight in the range of from 200,000 to 600,000 g/mol.

6. The rafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , wherein the hydroxylated hydrogenated polybutadiene has a number-average molecular weight M n to DIN 55672-1 of 4,000 to 6,000 g/mol.

7. The grafted polyalkyl(meth)acrylate based comb polymer according to claim 6 , wherein the number-average molecular weight M n to DIN 55672-1 is 4,500 to 5,000 g/mol.

8. A method for reducing friction losses of a lubricating oil composition, the method comprising:
adding the polyalkyl(meth)acrylate based comb polymer according to claim 1 to the lubricating oil composition.

9. The method according to claim 8 , wherein the lubricating oil composition is an engine oil composition.

10. The grafted polyalkyl(meth)acrylate based comb polymer according to claim 1 , wherein the butyl (meth)acrylate is n-butyl methacrylate, the C 10-20 -alkyl (meth)acrylate is C 12-14 -alkyl methacrylate, and the styrene monomer is styrene.

11. An additive composition, comprising:
(A) a first base oil selected from the group consisting of API Group III oils and mixtures thereof;
(B) a second base oil selected from the group consisting of API Group V base oils and mixtures thereof; and
(C) a polyalkyl(meth)acrylate based comb polymer consisting of a base polymer A and units B which is grafted thereon, wherein the base polymer A comprises:
(a) 10% to 25% by weight of at least one repeating unit derived from an ester of (meth)acrylic acid and a hydroxylated hydrogenated polybutadiene:
(b) 0% to 2% by weight of at least one repeating unit derived from methyl (meth)acrylate:
(c) 60% to 80% by weight of at least one repeating unit derived from butyl (meth)acrylate;
(d) 0% to 16% by weight of at least one repeating unit derived from C 10-20 -alkyl (meth)acrylate; and
(e) 0% to 2% by weight of at least one repeating unit derived from a styrene monomer having 8 to 17 carbon atoms,
wherein an amount of each component (a) to (e) is based on a total composition of the polyalkyl(meth)acrylate based comb polymer; and
wherein the units B comprise at least one repeating unit prepared from:
(f) 1% to 2.5% by weight of at least one repeating unit derived from a polar unsaturated monomer selected from the group consisting of maleic acid, maleic acid anhydride, methyl maleic acid anhydride, maleic acid monoester and maleic acid diester; and
(g) 2% to 5% by weight of at least one repeating unit derived from a primary amine of general formula (I)

wherein each R′ is independently selected from the group consisting of H and an alkyl radical having 1 to 9 carbon atoms, and

wherein the amount of each component (f) and (g) is based on the total composition of the polyalkyl(meth)acrylate based comb polymer.

12. The additive composition according to claim 11 , comprising:
(A) the first base oil selected from the group consisting of API Group III oils and mixtures thereof:
(B) the second base oil selected from the group consisting of API Group V base oils and mixtures thereof; and
(C) the polyalkyl(meth)acrylate based comb polymer consisting of the base polymer A and units B which is grafted thereon, wherein the base polymer A comprises:
(a) 10% to 15% by weight of at least one repeating unit derived from the an ester of (meth)acrylic acid and a hydroxylated hydrogenated polybutadiene;
(b) 0% to 2% by weight of at least one repeating unit derived from h methyl (meth)acrylate;
(c) 65% to 76% by weight of at least one repeating unit derived from the butyl (meth)acrylate;
(d) 5% to 16% by weight of at least one repeating unit derived from the C 10-20 -alkyl (meth)acrylate; and
(e) 0% to 2% by weight of at least one repeating unit derived from the styrene monomers having 8 to 17 carbon atoms,
wherein the amount of each component (a) to (e) is based on the total composition of the polyalkyl(meth)acrylate based comb polymer; and
wherein the units B comprise at least one repeating unit prepared from:
(f) 1% to 2.5% by weight of at least one repeating unit derived from the polar unsaturated monomer selected from the group consisting of maleic acid, maleic acid anhydride, methyl maleic acid anhydride, maleic acid monoester and maleic acid diester; and
(g) 2% to 5% by weight of at least one repeatin

Assignees

• Evonik Operations Gmbh

Inventors

• Schöller Katrin
• Holtzinger Jennifer
• Ziegler Fabian
• Schimossek Klaus
• Lauterwasser Frank

Classifications

• C10N2020/071

  Branched chain compounds · CPC title

• C08L2203/40

  used as motor oil additive · CPC title

• C10M2205/04

  containing aromatic monomers, e.g. styrene · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10M2209/084

  Acrylate; Methacrylate · CPC title