US2992083A - Liquid hydrocarbon power fuel containing cyanoalkylpolysiloxanes as foam depressors - Google Patents
Liquid hydrocarbon power fuel containing cyanoalkylpolysiloxanes as foam depressors Download PDFInfo
- Publication number
- US2992083A US2992083A US852219A US85221959A US2992083A US 2992083 A US2992083 A US 2992083A US 852219 A US852219 A US 852219A US 85221959 A US85221959 A US 85221959A US 2992083 A US2992083 A US 2992083A
- Authority
- US
- United States
- Prior art keywords
- foam
- hydrocarbon
- fuel
- fuels
- cyanoalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000446 fuel Substances 0.000 title claims description 57
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 34
- 229930195733 hydrocarbon Natural products 0.000 title claims description 30
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 26
- 239000006260 foam Substances 0.000 title description 29
- 239000007788 liquid Substances 0.000 title description 8
- -1 POLYSILOXANE Polymers 0.000 claims description 45
- 229920001296 polysiloxane Polymers 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 20
- 238000005187 foaming Methods 0.000 claims description 5
- 230000006835 compression Effects 0.000 claims description 2
- 238000007906 compression Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000012530 fluid Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000013530 defoamer Substances 0.000 description 6
- 239000002518 antifoaming agent Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/28—Organic compounds containing silicon
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B3/00—Engines characterised by air compression and subsequent fuel addition
- F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition
Definitions
- the present invention relates to fuel compositions and more particularly to hydrocarbon fuel compositions having reduced foaming properties. Specifically, the present invention relates to the incorporation of certain cyanoal- 'kyl-substituted siloxanes as foam inhibitors in hydrocarbon power fuel com-positions to reduce the foaming tendency of such compositions and to the resulting fuel compositions containing such foam inhibitiors.
- liquid hydrocarbons particullarly low vapor pressure fuels
- froth and foam when agitated in the presence of air or gases.
- the volume of foam or froth produced isniany times the initial volume 'of the liquid hydrocarbon.
- various conventional antifoam agents such as polyglycols and morpholine, have been used in hydrocarbons with varying degrees of success and liquid organopolysiloxanes have been used inliquid hydrocarbons including oils with good results.
- cyanoa-lkyl polysiloxanes corresponding to the following average formula are highly effective as foam inhibitors when added to hydrocarbon power fuel compositions, such as internal combustion and jet fuel compositionsi wherein R is a monovalent hydrocarbon group and a halogenated monavalent hydrocarbon group such as aryl, particularly phenyl, chlorophenyl, tolyl, diphenyl, napht-hyl, etc.; aliphatic such as alkyl, chloroalkyl, alkenyl and alkynyl, particularly methyl, ethyl, propyl, butyl, chlorobutyl, pentyl, vinyl, allyl, butenyl, propynyl, butynyl, and wherein R is preferably a lower alkyl, such as methyl, and wherein m is an integer equalto from 1 to 5 and is preferably 2, and wherein a is equal to 0.001 to 1.0, and
- a particularly preferred group of the above described cyanoalkyl polysiloxane antifoam agents of the present invention comprises polysiloxanes wherein the range of cyanoalkyl groups or a is between about .05 to'.99 and b is between about 1.01 to 1.98.
- the cyanoalkyl polysiloxanes of the present invention have also proved to be superior to the conventional organopolysiloxane fluids as foam depressors for hydrocarbon power fuels, including spark ignition fuels, such as aviation fuels, and jet ignit-ion fuels.
- Classification JP-4-low vapor pressure type, wide cut gasoline type. IP-5--high flash point, kerosene type.
- the present invention results in hydrocarbon fuel compositions having markedly reduced foaming properties by the production of a mixture of a hydrocarbon power fuel and a cyanoalkyl-substituted polysiloxane corresponding to Formula 1 wherein the cyanoalkyl-substituted polysiloxane is present in a range of at least 10 parts to 10,000 parts by weight per million parts of the fuel.
- cyanoalkyl polysiloxane compounds that are employed in the practice of the present invention can be further defined as polysiloxane fluids that include one or more of the following cyanoalkyl-silicon linked units:
- the fluids employed in the practice of the present invention can be exemplified by condensation products of cyanoethyl siloxane, cyanopropylrsiloxane, cyanoethylmethyl siloxane, cyanoethyldimethyl siloxane, cyanoethylethyl siloxane, cyanoethylphenyl siloxane, cyanopropylmethyl siloxane, with hydrocarbon-substituted siloxanes like dimethyl siloxane, methyl siloxane, trimethyl siloxane, diphenyl siloxane, methylphenyl siloxane, diet-hyl siloxane and dimethylphenyl siloxane.
- a cyanoalkyl-substituted polysiloxane is initially added at the desired concentration to a suitable hydrocarbon fuel either directly or dissolved in an organic solvent.
- the mixture can then be agitated to uniformly disperse the defoamer throughout the mixture according to methods known in the art.
- Another satisfactory procedure is to add the defoamer to the fuel while the latter is being agitated with an inert gas so as to suppress foam rise or, if desired, completely to eliminate foam according to the concentration of the defoamer added.
- the amounts of the added cyanoalkyl-substituted siloXane are initially added at the desired concentration to a suitable hydrocarbon fuel either directly or dissolved in an organic solvent.
- Suitable organic solvents that can be employed with the cyanoalkylsiloxane defoamers of the present invention include, for example, gasoline, naphtha, toluene and benzene.
- the oil was then filtered and devolatilized at 200 to 215 C. at 1.5 mm. for 2 hours. Analysis of this oil showed it to contain 3.05 percent nitrogen which corresponds to a ratio of about 5.9 silicon atoms per fl-cyanoethyl radical.
- a series of cyanoalkyl-substituted polysiloxane fluids were made according to the above procedure for use in the examples below, to illustrate the practice of the invention.
- the fluids prepared, designated A, B and C corresponded to the following average range of composition, where in each substituted siloxane grouping the cyano-substituted polysiloxane chain is expressed in mole percent:
- Example 2 The procedure of Example 1 was repeated except Fluid B was substituted at the same concentration, as shown in Example 1. The foam dropped immediately and then built up to about inch. There was no buildup of foam with time.
- EXAMPLE 3 A similar procedure was employed with Fluid C as in Example 1, and the concentration of fluid was also 100 parts of inhibitor per million parts of fuel. As soon as the defoamer was added the foam dropped completely, and there was no rebuild of foam over an extended period of time.
- Nitrogen was bubbled into a cylinder containing JP-4, as in Exmaple 1, and a 1 percent solution of Fluid B in toluene was added in amounts approximating 100 parts of fluid per million parts of fuel. The foam fell immediately and completely disappeared although the nitrogen flow continued for over thirty minutes.
- EXAMPLE 5 A similar procedure was employed as in Example 4, but the amount of the 1 percent solution of Fluid B in toluene that was added was decreased to one half. The foam gradually rose to about Ms inch but there was no perceptible increase in height with time.
- hydrocarbons derived from both petroleum processing and coal hydrogenation can be particularly designated as spark ignition fuels such as aviation fuels, compression ignition fuels, such as diesel fuels, and jet ignition fuels containing blends of naphthas, paraflins and kerosene respectively.
- R is a member selected from the group consisting of monovalent hydrocarbon groups and halogenated monovalent hydrocarbon groups and m is an integer equal to from 1 to 5, a is from 0.001. to 1, and b is from 1.001 to 2, and the sum of a and b is equal to 2.001 to 3, said polysiloxane being present in the range of parts to 10,000 parts by weight per million parts of fuel.
- hydrocarbon fuel composition in accordance with claim 1 wherein the hydrocarbon power fuel is a jet ignition fuel having a minimum evaporation of about 20 percent at about 140 C. and a minimum evaporation of about percent at about 245 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US852219A US2992083A (en) | 1959-11-12 | 1959-11-12 | Liquid hydrocarbon power fuel containing cyanoalkylpolysiloxanes as foam depressors |
| GB36410/60A GB964329A (en) | 1959-11-12 | 1960-10-24 | Fuel composition |
| DEG30882A DE1122764B (de) | 1959-11-12 | 1960-11-08 | Schaumverhuetungsmittel fuer Kohlenwasserstoff-Kraftstoffe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US852219A US2992083A (en) | 1959-11-12 | 1959-11-12 | Liquid hydrocarbon power fuel containing cyanoalkylpolysiloxanes as foam depressors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2992083A true US2992083A (en) | 1961-07-11 |
Family
ID=25312767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US852219A Expired - Lifetime US2992083A (en) | 1959-11-12 | 1959-11-12 | Liquid hydrocarbon power fuel containing cyanoalkylpolysiloxanes as foam depressors |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2992083A (de) |
| DE (1) | DE1122764B (de) |
| GB (1) | GB964329A (de) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3233986A (en) * | 1962-06-07 | 1966-02-08 | Union Carbide Corp | Siloxane-polyoxyalkylene copolymers as anti-foam agents |
| US3384600A (en) * | 1964-11-20 | 1968-05-21 | Nalco Chemical Co | Novel compositions and their use in preventing and inhibiting foam |
| US4690688A (en) * | 1985-03-29 | 1987-09-01 | Dow Corning, Ltd. | Foam control |
| US4781728A (en) * | 1985-04-29 | 1988-11-01 | Union Oil Company Of California | Octane enhancers for fuel compositions |
| US4854938A (en) * | 1987-05-08 | 1989-08-08 | Dow Corning, Ltd. | Removal of water haze from distillate fuel |
| US5032144A (en) * | 1985-04-29 | 1991-07-16 | Union Oil Company Of California | Octane enhancers for fuel compositions |
| US5397367A (en) * | 1993-11-19 | 1995-03-14 | Dow Corning Corporation | Middle distillate hydrocarbon foam control agents from cross-linked organopolysiloxane-polyoxyalkyenes |
| US5435811A (en) * | 1993-11-19 | 1995-07-25 | Dow Corning Corporation | Middle distillate hydrocarbon foam control agents from alkymethylsiloxanes |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2724698A (en) * | 1950-12-01 | 1955-11-22 | Exxon Research Engineering Co | Lubricating oil anti-foaming agent |
| US2837551A (en) * | 1955-12-23 | 1958-06-03 | Union Carbide Corp | Process for producing beta-cyanoethyltrichlorosilane |
| US2860153A (en) * | 1957-04-25 | 1958-11-11 | Dow Corning | Method of preparing beta-cyanoethyltrichlorosilane |
| US2906767A (en) * | 1957-03-20 | 1959-09-29 | Dow Corning | Organosilicon nitriles |
-
1959
- 1959-11-12 US US852219A patent/US2992083A/en not_active Expired - Lifetime
-
1960
- 1960-10-24 GB GB36410/60A patent/GB964329A/en not_active Expired
- 1960-11-08 DE DEG30882A patent/DE1122764B/de active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2724698A (en) * | 1950-12-01 | 1955-11-22 | Exxon Research Engineering Co | Lubricating oil anti-foaming agent |
| US2837551A (en) * | 1955-12-23 | 1958-06-03 | Union Carbide Corp | Process for producing beta-cyanoethyltrichlorosilane |
| US2906767A (en) * | 1957-03-20 | 1959-09-29 | Dow Corning | Organosilicon nitriles |
| US2860153A (en) * | 1957-04-25 | 1958-11-11 | Dow Corning | Method of preparing beta-cyanoethyltrichlorosilane |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3233986A (en) * | 1962-06-07 | 1966-02-08 | Union Carbide Corp | Siloxane-polyoxyalkylene copolymers as anti-foam agents |
| US3384600A (en) * | 1964-11-20 | 1968-05-21 | Nalco Chemical Co | Novel compositions and their use in preventing and inhibiting foam |
| US4690688A (en) * | 1985-03-29 | 1987-09-01 | Dow Corning, Ltd. | Foam control |
| US4781728A (en) * | 1985-04-29 | 1988-11-01 | Union Oil Company Of California | Octane enhancers for fuel compositions |
| US5032144A (en) * | 1985-04-29 | 1991-07-16 | Union Oil Company Of California | Octane enhancers for fuel compositions |
| US4854938A (en) * | 1987-05-08 | 1989-08-08 | Dow Corning, Ltd. | Removal of water haze from distillate fuel |
| US5397367A (en) * | 1993-11-19 | 1995-03-14 | Dow Corning Corporation | Middle distillate hydrocarbon foam control agents from cross-linked organopolysiloxane-polyoxyalkyenes |
| US5435811A (en) * | 1993-11-19 | 1995-07-25 | Dow Corning Corporation | Middle distillate hydrocarbon foam control agents from alkymethylsiloxanes |
Also Published As
| Publication number | Publication date |
|---|---|
| GB964329A (en) | 1964-07-22 |
| DE1122764B (de) | 1962-01-25 |
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