IP Library Granted Patent US 8,293,690
Granted Patent B2
US 8,293,690 · App. 12/520,358 · Granted Oct 23, 2012

Dispersions of polymer oil additives

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,293,690
App. No.
12/520,358
Granted
Oct 23, 2012
Kind
B2
Abstract

The invention relates to dispersions comprising I) at least one polymer that is effective for mineral oils as a cold extrusion improver and is soluble in oil, II) at least one organic solvent that cannot be mixed with water, III) water, IV) at least one alkanolamine salt of a polycyclic carboxylic acid as a dispersing agent, and V) possibly at least one organic solvent that can be mixed with water.

Claims (56)

1. A dispersion comprising

I) at least one oil-soluble polymer effective as a cold flow improver for mineral oils,

II) at least one organic, water-immiscible solvent,

III) water,

IV) at least one alkanolamine salt of a polycyclic carboxylic acid and

V) optionally at least one water-miscible organic solvent.

2. The dispersion as claimed in claim 1 , in which the cold flow improver I is a copolymer of ethylene and at least one ethylenically unsaturated ester or ether or an alkene.

3. The dispersion as claimed in claim 1 , in which the cold flow improver is a homo- or copolymer of at least one ester of at least one ethylenically unsaturated carboxylic acid, said ester bearing C 10 -C 30 -alkyl radicals.

4. The dispersion as claimed in claim 2 , in which the ethylenically unsaturated ester is a vinyl ester.

5. The dispersion as claimed in claim 3 , in which the ethylenically unsaturated carboxylic acid is acrylic acid and/or methacrylic acid.

6. The dispersion as claimed in claim 1 , in which the cold flow improver is an ethylene copolymer grafted with ethylenically unsaturated esters and/or ethers.

7. The dispersion as claimed in claim 6 , wherein the ethylenically unsaturated ester is an ester of acrylic acid and/or methacrylic acid, said ester bearing C 10 -C 30 -alkyl radicals.

8. The dispersion as claimed in claim 1 , in which the cold flow improver is a homo- and copolymer of a-olefins having 3 to 30 carbon atoms.

9. The dispersion as claimed in claim 1 , in which the cold flow improver is a condensation product of at least one alkylphenol and at least one aldehyde or ketone.

10. The dispersion as claimed in claim 9 , in which the condensation product corresponds to the formula 6

in which R 13 is C 1 -C 200 -alkyl or C 2 -C 200 -alkenyl, and n is from 2 to 250.

11. The dispersion as claimed in claim 1 , in which the dispersant IV is preparable by neutralizing at least one polycyclic carboxylic acid with at least one alkanolamine.

12. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic acid derives from at least one polycyclic hydrocarbon which contains at least two five- and/or six-membered rings which are joined to one another via two preferably vicinal carbon atoms.

13. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic acid corresponds to the formula 8

where

X represents carbon atoms, or three carbon, nitrogen and/or oxygen, with the proviso that each of the structural units consisting of four X joined to one another consists either of 4 carbon atoms or 3 carbon atoms and one oxygen atom or one nitrogen atom,

R 19 , R 20 ,R 21 and R 22 are the same or different and are each a hydrogen atom or hydrocarbon groups, each of which is bonded to at least one atom of one of the two rings, these hydrocarbon groups are selected from the group consisting of:

alkyl groups having one to five carbon atoms,

aryl groups, and

hydrocarbon rings having five to six atoms, which optionally contain a heteroatom, such as nitrogen or oxygen, where the hydrocarbon ring is saturated or unsaturated, unsubstituted or substituted by an optionally olefinic aliphatic radical having one to four carbon atoms, where in each case two of the R 19 , R 20 , R 21 and R 22 radicals form such a hydrocarbon ring, and

Z is a carboxyl group or an alkyl radical bearing at least one carboxyl group.

14. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic acid corresponds to the formula (9):

in which

at most one X of each ring is a heteroatom, such as nitrogen or oxygen, and the other X atoms are carbon atoms,

R 19 , R 20 , R 21 and R 22 are the same or different and are each a hydrogen atom or hydrocarbon groups, each of which is bonded to at least one atom of one of the two rings, these hydrocarbon groups are selected from the group consisting of:

alkyl groups having one to five carbon atoms,

aryl groups, and

hydrocarbon rings having five to six atoms, which optionally contain a heteroatom, such as nitrogen or oxygen, where the hydrocarbon ring is saturated or unsaturated, unsubstituted or substituted by an optionally olefinic aliphatic radical having one to four carbon atoms, where in each case two of the R 19 , R 20 , R 21 and R 22 radicals form such a hydrocarbon ring, and

Z is bonded to at least one atom of at least one of the two rings and is a carboxyl group or an alkyl radical bearing at least one carboxyl group.

15. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic acid is an acid based on natural resins.

16. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic acid is a naphthenic acid.

17. The dispersion as claimed in claim 1 , in which the alkanolamine is a primary, secondary or tertiary amine which bears at least one alkyl radical substituted by a hydroxyl group.

18. The dispersion as claimed in claim 1 , in which the alkanolamine corresponds to the following formula 10:

NR 23 R 24 R 25   (10)

in which

R 23 is a hydrocarbon radical which bears at least one hydroxyl group and has 1 to 10 carbon atoms and

R 24 , R 25 are each independently hydrogen, an optionally substituted hydrocarbon radical having 1 to 50 carbon atoms, especially C 1 - to C 20 -alkyl, C 3 - to C 20 -alkenyl, C 6 - to C 20 -aryl, or R 23 , or

R 23 and R 24 or R 23 and R 25 together are a cyclic hydrocarbon radical interrupted by at least one oxygen atom.

19. The dispersion as claimed in claim 18 , in which the alkanolamine is a heterocyclic compound of the formula (10) in which R 23 and R 24 or R 23 and R 25 together are a cyclic hydrocarbon radical interrupted by at least one oxygen atom, and the remaining R 24 or R 25 radical is hydrogen, a lower alkyl radical having 1 to 4 carbon atoms or a group of the formula (11)

—(B—O) p —R 26   (11)

in which B is an alkylene radical having 2 or 3 carbon atoms and p is 1 or 2, and R 26 is hydrogen or a group of the formula —B—NH 2 .

20. The dispersion as claimed in claim 1 , in which the polycyclic carboxylic salt IV is used together with a coemulsifier.

21. The dispersion as claimed in claim 1 , in which the water-miscible solvent (V) has a dielectric constant of at least 3.

22. The dispersion as claimed in claim 1 , in which the water-miscible solvent (V) is selected from the group consisting of alcohols, glycols, poly(glycols), acetates, ketones and lactones.

23. The dispersion as claimed in claim 1 , which comprises

5-60% by weight of cold flow improver (I),

5-45% by weight of water-immiscible solvent (II),

5-60% by weight of water (III),

0.001-5% by weight of at least one alkanolamine salt of a polycyclic carboxylic acid (IV), and

0-40% by weight of water-miscible solvent (V).

24. The dispersion as claimed in claim 1 , further comprising a rheology-modifying substance which causes a yield point.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 1, 2024
From: CLARIANT INTERNATIONAL LTD
To: DORF KETAL ENERGY SERVICES LLC
Reel/Frame 068157/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 3, 2015
From: CLARIANT FINANCE (BVI) LIMITED
To: CLARIANT INTERNATIONAL LTD.
Reel/Frame 036949/0133 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 19, 2009
From: FEUSTEL, MICHAEL; KRULL, MATTHIAS; KAYSER, CHRISTOPH; LOEW, MARIO
To: CLARIANT FINANCE (BVI) LIMITED
Reel/Frame 022850/0619 →