IP Library Granted Patent US 10,131,776
Granted Patent B2
US 10,131,776 · App. 13/395,165 · Granted Nov 20, 2018

Composition to improve cold flow properties of fuel oils

Inventors: Ronny Sondjaja (Bandung, ID); Rene Koschabek (Weinheim, DE); Markus Weber (Brensbach, DE); Jane Benito (Bataan, PH); Jian Mike Liu (Singapore, SG); Torsten Stoehr (Frankfurt, DE)
Assignee: EVONIK OIL ADDITIVES GmbH
C08L33/04C08F218/08C08F220/14C08L31/04C08L33/08C08L33/10C10L1/143C10L1/146C10L10/14C10L1/19C10L1/1963C10L1/1973C10L2200/0476
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Quick Facts
Patent No.
US 10,131,776
App. No.
13/395,165
Granted
Nov 20, 2018
Kind
B2
Abstract

The present invention describes a composition comprising at least one polyalkyl(meth)acrylate polymer having a number average molecular weight Mn of from 1000 to 10000 g/mol and a polydispersity Mw/Mn of from 1 to 8 and at least one ethylene vinyl acetate copolymer comprising units being derived from at least one alkyl (meth)acrylate having 1 to 30 carbon atoms in the alkyl residue. The composition is useful as cold flow improver in fossil fuel oil and or biodiesel fuel oil.

Claims (44)

1. A composition, comprising:

at least 90% by weight of the composition of a biodiesel fuel oil; and

from 0.1 to 0.50% by weight of a copolymer mixture, comprising:

i) a polyalkyl(meth)acrylate polymer having a number average molecular weight Mn of from 1000 to 10000 g/mol and a polydispersity Mw/Mn of from 1 to 8; and

ii) an ethylene vinyl acetate copolymer comprising in polymerized form an alkyl (meth)acrylate having 1 to 30 carbon atoms in the alkyl residue;

wherein

the ethylene vinyl acetate copolymer is a graft copolymer comprising an ethylene vinyl acetate copolymer as a graft base and the alkyl (meth)acrylate having 1 to 30 carbon atoms in the alkyl residue as a graft layer;

a weight ratio of the polyalkyl(meth)acrylate polymer i) to the ethylene vinyl acetate copolymer ii) is in the range of from 15:1 to 1:1;

the polyalkyl(meth)acrylate polymer comprises:

(a) 0 to 40% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (I):

wherein

R is hydrogen or methyl, and

R 1 is a linear, branched or cyclic alkyl residue with 1 to 6 carbon atoms,

(b) at least 10% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (II):

wherein

R is hydrogen or methyl, and

R 2 is a linear, branched or cyclic alkyl residue with 7 to 15 carbon atoms, and

(c) 0 to 40% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (III):

wherein

R is hydrogen or methyl, and

R 3 is a linear, branched or cyclic alkyl residue with 16-40 carbon atoms;

the ethylene vinyl acetate copolymer comprises in polymerized form 0.5 to 60 weight % of vinyl acetate; and

the alkyl (meth)acrylate having 1 to 30 carbon atoms in the alkyl residue as the graft layer comprises in polymerized form from 30 to 90 weight % of an alkyl (meth)acrylate having 7 to 15 carbon atoms in the alkyl residue.

2. The composition of claim 1 , wherein said polyalkyl(meth)acrylate polymer i) comprises at least 50% by weight of polymerized units derived from the alkyl (meth)acrylate monomers of formula (II).

3. The composition of claim 1 , wherein the polydispersity Mw/Mn of said polyalkyl(meth)acrylate polymer i) is in the range of from 1.1 to 5.

4. The composition of claim 1 , wherein said polyalkyl(meth)acrylate polymer i) further comprises in polymerized form a hydroxyl-containing monomer, a (meth)acrylate of an ether alcohol, or a mixture thereof.

5. The composition of claim 1 , wherein said ethylene vinyl acetate copolymer ii) comprises in polymerized form from 2 to 30 weight % of vinyl acetate.

6. The composition of claim 1 , wherein said ethylene vinyl acetate copolymer ii) comprises in polymerized form from 1 to 60 weight % of ethylene.

7. The composition of claim 1 , wherein said ethylene vinyl acetate copolymer ii) further comprises in polymerized form up to 20 weight % of at least one additional comonomer.

8. The composition of claim 1 , wherein said ethylene vinyl acetate copolymer ii) has a number average molecular weight Mn of from 1000 to 120 000 g/mol.

9. The composition of claim 1 , wherein the alkyl (meth)acrylate having 1 to 30 carbon atoms in the alkyl residue as graft layer comprises in polymerized form from 60 to 80 weight % of an alkyl (meth)acrylate having 7 to 15 carbon atoms in the alkyl residue.

10. The composition of claim 1 , wherein a weight ratio of graft base to graft layer in said ethylene vinyl acetate copolymer ii) is in the range of from 1:1 to 1:8.

11. The composition of claim 1 , further comprising a mineral oil.

12. The composition of claim 1 , wherein said biodiesel fuel oil comprises a fatty acid ester derived from a monohydric alcohol having 1 to 4 carbon atoms.

13. The composition of claim 12 , wherein said biodiesel oil comprises at least 10% by weight of a fatty acid ester derived from methanol, ethanol, or both, and a saturated fatty acid.

14. The composition of claim 1 , wherein the copolymer mixture consists of i) and ii).

15. The composition of claim 1 , wherein the polyalkyl(meth)acrylate polymer comprises 0.1 to 30% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (I).

16. The composition of claim 1 , wherein the polyalkyl(meth)acrylate polymer comprises 25 to 100% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (II).

17. The composition of claim 1 , wherein the polyalkyl(meth)acrylate polymer comprises 0.1 to 30% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (III).

18. The composition of claim 1 , wherein the polyalkyl(meth)acrylate polymer comprises:

0.5 to 20% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (I);

70 to 99% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (II); and

0.5 to 20% by weight of polymerized units derived from one or more alkyl(meth)acrylate monomers of formula (III).

19. The composition of claim 1 , which comprises at least 98% by weight of the composition of a biodiesel fuel oil.

Assignments (4)
MERGER Recorded Jan 8, 2020
From: EVONIK OIL ADDITIVES GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 051505/0590 →
CHANGE OF NAME Recorded Jan 8, 2020
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051505/0797 →
CHANGE OF NAME Recorded Dec 1, 2015
From: EVONIK ROHMAX ADDITIVES GMBH
To: EVONIK OIL ADDITIVES GMBH
Reel/Frame 037175/0522 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2012
From: SONDJAJA, RONNY; KOSCHABEK, RENE; WEBER, MARKUS; BENITO, JANE; LIU, JIAN MIKE; STOEHR, TORSTEN
To: EVONIK ROHMAX ADDITIVES GMBH
Reel/Frame 027869/0668 →
Priority Claims (1)
EP 09171400 · Sep 25, 2009 · regional
Continuity (1)
Related Publication 20120174474A1 · Jul 12, 2012