Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2003-02-04
2004-04-27
Davis, Brian (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S282000, C562S030000, C562S400000, C556S410000, C516S144000, C516S145000, C516S152000, C516S153000, C516S181000, C516S186000
Reexamination Certificate
active
06727388
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to chemical compounds.
2. Background
Demulsifying agents break emulsions of polar solutes like water, and non-polar solvents like oil. They are used in functional fluids (such as, but not limited to, metal removal fluids, greases, rust and oxidation fluids, hydraulic oils, compressor oils, fuels and transformer fluids) to inhibit formation of emulsions, break emulsions that have developed, and to inhibit corrosion.
Among their industrial uses, demulsifiers are commonly used to dehydrate and desalt crude oil during refinement. Typically, in order to remove sedimentation found in crude oil, crude oil is treated with soda ash and water. This salt and water, unless removed, will cause problems in distillation columns. The salt will foul the heat exchangers and the water may vaporize, possibly causing an explosion. To remove the salt and water, the crude oil is treated with demulsifying agents.
In the closed, harsh environment of hydraulic systems, demulsifiers must be effective at high temperatures, often in excess of 300° C. Failure of a demulsifier in a hydraulic system may lead to catastrophic failure. Demulsifiers are also frequently put to use in hydraulic systems to prevent corrosion. In the presumed mechanism of corrosion inhibition, the demulsifier adsorbs on the metal surface forming a protective film against polar solutes. More preferably still, demulsifiers in such systems are ashless to avoid clogging filters and orifices. Calcium sulfonates, though not ashless, are common demulsifiers in hydraulic systems.
Demulsifiers are added to fuel systems to prevent water from interfering with the combustion process. Like in hydraulic systems, demulsifiers used in fuel systems should preferably be ashless to avoid deposits.
In their broadest conception, demulsifiers are made out of amphiphilic compounds. See Kwetkat et al., U.S. Pat. No. 5,997,610. The hydrophilic portion of a demulsifier may contain formally charged residues—e.g. cationic, anionic, zwiterionic residues—or it may contain uncharged, polarized residues. The hydrophobic portion of a demulsifier may include long alkyl functional groups (>7 carbons), alkyl aryl functional groups, petroleum derivatives or even polysiloxane functional groups.
In many applications an effective demulsifier should also be ashless, low foaming, effective over a broad range of temperatures, have a low viscosity, and inhibit corrosion. Such ashless demulsifiers may be based upon amine sulfonates, amine sulfates, amine phosphates, and amine carboxylates.
Two tests are used in the art to predict the general effectiveness of a compound as a demulsifier and corrosion inhibitor, the ASTM D-1401 and ASTM D-665 tests. A description of these tests may be found in the Annual Book of ASTM Standards, Vol. 05.01, incorporated herein. ASTM D-1401 tests the relative speed and extent of demulsification between different demulsifiers. ASTM D-665 tests the relative corrosion protection afforded by different demulsifiers.
The ASTM D-1401 test procedure calls for the mixing of 40 mL of an oil phase and 40 mL of an aqueous phase (typically deionized water), followed by a period to allow the phases to separate. The demulsifier concentration is not specified in the ASTM method, and through experience, 5% of the demulsifier in the oil provides adequate results. The results to ASTM D-1401 are usually expressed in the form O/W/E (T), where the O is the volume of the organic layer, W is the volume of the aqueous layer, E is the volume of the emulsion layer, and T is the time in 5 minute increments up to 60 minutes.
For comparison of demulsifiers, we defined Relative Performance by measuring the time to complete separation in one-minute intervals. If separation did not occur within 60 minutes, then the value reported was >60.
The ASTM D-665 test procedure determines if rust spots appear on a steel rod after 24 hours being immersed in a mixture of 300 mL of oil and 30 mL of DI water (Part A) or synthetic sea water (Part B). Through experience, a “Pass” for part A at the low treat level of 0.005% demonstrates good efficacy as a corrosion inhibitor.
In addition to above-mentioned general qualities, a demulsifier should have the best possible ASTM D-1401 score. Additionally, good ASTM D-655 performance is desirable.
DEFINITIONS
1. Functional Fluids: A fluid formulated to accomplish a defined goal or combination of goals, such as, but not limited to, cooling, lubrication, corrosion protection, energy transfer, hydraulic action, combustion, or providing a dielectric medium.
2. Emulsion: A mixture of two or more immiscible liquids, consisting of droplets in a continuous phase.
3. Ashless: A compound not containing any metallic elements.
4. Amphiphilic: Any compound consisting of at least one lyophobic portion and at least one lyophilic portion.
5. Lyophilic Portion: That part of a molecule having a relative attraction to the solvent.
6. Lyophobic Portion: That part of a molecule having a relative repulsion to the solvent.
7. Hydrophilic Portion: The lyophilic portion when water is the solvent.
8. Hydrophobic Portion: The lyophobic portion when water is the solvent.
9. Alkyl Functional group: Any saturated or unsaturated, branched or unbranched hydrocarbon chain.
10. C
8
-C
24
Alkyl Functional Group: An alkyl functional group consisting of from 8 to 24 carbons.
11. Aryl Functional Group: An aromatic ring or rings, such as, but not limited to benzene, toluene, xylene, naphthalene, or diphenyl oxide.
12. Alkyl Aryl Functional Group: An aryl functional group attached to one or more alkyl functional groups.
13. Alkyl Amine: An amine that contains one or more alkyl functional groups.
14. Alkyl Sulfonic Acid: A sulfonic acid with an alkyl functional group.
15. Alkyl Aryl Sulfonic Acid: A sulfonic acid with an alkyl aryl functional group.
16. Di-Alkyl Aryl Sulfonic Acid: A sulfonic acid with an aryl functional group that is attached to two alkyl functional groups.
17. Cocoyl Functional Group: A member of the set of linear, saturated or unsaturated hydrocarbon chains from 8 to 20 carbons.
18. Cocoyl Amines: An amine that contains one or more cocoyl functional groups.
19. Mono-Cocoyl Amine: An amine that contains one cocoyl functional group.
20. Di-Cocoyl Amine: An amine that contains two cocoyl functional groups.
21. Tri-Cocoyl Amine: An amine that contains three cocoyl functional groups.
22. Methyl, Di-Cocoyl Amine: A tertiary amine with one methyl functional group and two cocoyl functional groups.
23. Di-methyl, Cocoyl Amine: A tertiary amine with one cocoyl functional group and two methyl functional groups.
24. Polysiloxane Functional Group: A functional group containing a branched or unbranched silicon-oxygen backbone.
25. C
8
-C
60
Alkyl Aryl Functional Group: An alkyl aryl functional group where the alkyl functional groups have a combined total of 8 to 60 carbon atoms.
26. Mono-C
8
-C
24
Alkyl Benzene: A benzene ring that is attached to an alkyl functional group of 8 to 24 carbons.
27. Mono-C
8
-C
24
Alkyl Toluene: A toluene ring that is attached to an alkyl functional group of 8 to 24 carbons.
28. Mono-C
8
-C
24
Alkyl Xylene: A xylene ring is attached to an alkyl functional group of 8 to 24 carbons.
29. Di-C
8
-C
24
Alkyl Toluene: A toluene ring that is attached to two alkyl functional groups of 8 to 24 carbons each.
30. Di-C
8
-C
24
Alkyl Benzene: A benzene ring that is attached to two alkyl functional groups of 8 to 24 carbons each.
31. Organic System: Any organic solvent, oil, or combination of solvents, oils, and solutes.
32. Paraffinic Oil: A petroleum fraction that is predominately saturated hydrocarbons, commonly characterized by having a viscosity index greater than 100.
33. Naphthenic Oil: A petroleum fraction that contains some degree of unsaturation, commonly characterized by having a viscosity index less than 100.
34. Ester: An organic compound with one or more ester functional groups.
35. Mineral Oil: A petroleum fraction that is commonly obtained after the removal of compou
Davis Brian
Perkins Coie LLP
Pilot Chemical Holdings, Inc.
Wise Michael J.
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