GB938118A - Organic liquids having increased electrical conductivity - Google Patents
Organic liquids having increased electrical conductivityInfo
- Publication number
- GB938118A GB938118A GB18466/60A GB1846660A GB938118A GB 938118 A GB938118 A GB 938118A GB 18466/60 A GB18466/60 A GB 18466/60A GB 1846660 A GB1846660 A GB 1846660A GB 938118 A GB938118 A GB 938118A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acid
- salt
- ester
- ratio
- 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
Links
- 239000007788 liquid Substances 0.000 title abstract 2
- -1 alkylated hydroxy aryl carboxylic acid Chemical class 0.000 abstract 15
- 150000002148 esters Chemical class 0.000 abstract 14
- 229920001577 copolymer Polymers 0.000 abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 6
- 150000002430 hydrocarbons Chemical class 0.000 abstract 6
- 239000000178 monomer Substances 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 229910052751 metal Inorganic materials 0.000 abstract 5
- 239000002184 metal Substances 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 4
- 229910052804 chromium Inorganic materials 0.000 abstract 4
- 239000011651 chromium Substances 0.000 abstract 4
- 229930195733 hydrocarbon Natural products 0.000 abstract 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 4
- 229960004889 salicylic acid Drugs 0.000 abstract 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract 3
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 150000001844 chromium Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 abstract 3
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 abstract 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- 239000004711 α-olefin Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- QMQSEPCBZKJYBC-UHFFFAOYSA-N 2-ethenyl-3-ethylpyridine Chemical compound CCC1=CC=CN=C1C=C QMQSEPCBZKJYBC-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- NJRSUYBRIPYQFO-UHFFFAOYSA-L calcium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Ca+2].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC NJRSUYBRIPYQFO-UHFFFAOYSA-L 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 239000003502 gasoline Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 239000006078 metal deactivator Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000003209 petroleum derivative Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
Classifications
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- D—TEXTILES; PAPER
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- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
- D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
- D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
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- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B50/00—Formazane dyes; Tetrazolium dyes
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- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
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- 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
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- 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
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- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
- C10L1/189—Carboxylic acids; metal salts thereof having at least one carboxyl group bound to an aromatic carbon atom
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
- C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
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- C10L1/18—Organic compounds containing oxygen
- C10L1/192—Macromolecular compounds
- C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/197—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
- C10L1/1973—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
- C10L1/2283—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles containing one or more carbon to nitrogen double bonds, e.g. guanidine, hydrazone, semi-carbazone, azomethine
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- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
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- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2366—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amine groups
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- 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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2368—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing heterocyclic compounds containing nitrogen in the ring
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
- C10L1/2437—Sulfonic acids; Derivatives thereof, e.g. sulfonamides, sulfosuccinic acid esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The electrical conductivity of liquid hydrocarbons is increased by the addition of (a) a salt of a metal of atomic number 21-29 and an aromatic carboxylic acid or a sulphonic acid, the salt having a molecular weight of at least 200 and (b) an oil-soluble nitrogen containing copolymer, at least one of the monomers having an aliphatic chain of at least 8 carbon atoms, the copolymer having a molecular weight of 5,000 to 2,500,000 and a nitrogen content of 0,1-8% by weight, the weight ratio of copolymer (b) to the metal content of the salt (a) being 20-5,000:1. The hydrocarbon may be a petroleum distillate boiling in the range -40 to 375 DEG C., e.g. gasoline, kerosine or jet fuel. The metal salt (a) may be of chromium, vanadium, iron, cobalt, or manganese, preferably in a trivalent state, and a petroleum or naphthalene sulphonic acid, a sulphonated dialkyl ester of an aliphatic dicarboxylic acid or an alkylated hydroxy aryl carboxylic acid, especially alkylated salicylic acids. The latter are preferred having a C8+ alkyl substituent and the salt may be neutral or basic and contain minor amounts of the corresponding alkylated phenol. The concentration of the salt may be 1 X 10-3 to 1 X 10-9 gram atom of metal per litre of hydrocarbon. Calcium dioctylsulphosuccinate or similar synergist may also be added in an amount of 1 X 10-9 to 1 X 10-4 mol. per litre. Suitable copolymers are (1) of a nitrogen-free monomer having a C8-C18 aliphatic hydrocarbon side chain and a monomer containing a basic amino group, the copolymer containing 0,1-3,5% by weight basic amino nitrogen, e.g. lauryl methacrylate, styrene, diethylaminoethyl methacrylate in the ratio 45:45:10 (described in U.S.A. Specification 2,737,452); (2) of an N-vinyl-2-pyrrolidone (5-35%) and an acrylic ester of a C8+ alcohol, the ratio of N-vinyl-2-pyrrolidone to methacrylate preferably being 1:5 or 6 (described in Belgian Specification 550,442 and Canadian Specification 560,549); (3) a copolymer of a C10+ alphaolefin and an acrylic ester of a C1-3 alcohol in which at least 10% of the ester groupings have been amidized with a compound containing a -NR2 or -CONR2 (R=hydrocarbon) group (described in U.S.A. Specification 2,800,452); (4) of (a) an oil-solubilizing compound having an ethylenic linkage and a C4-C30 aliphatic carbon chain and (b) an amide of an alpha, beta-unsaturated C3-C6 carboxylic acid (if (a) contains less than 8 carbon atoms a third C8+, component is also incorporated), the mol. ratio of (a) to (b) being 1-15:1 (described in Specification 759,517); (5) of a vinyl pyridine and an ester of an acrylic acid and a C10X aliphatic alcohol; preferably a mixture of two different esters is used, the esters being derived from alcohols differing by at least 4 carbon atoms and present in a mol. ratio of one to the other of 1:10 to 10:1 and there also being present an ester of an acrylic acid and a C1-C6 alkanol; the mol. ratio of vinylpyridine to esters may be 1:15 to 2:1 and the lower ester may form 10-75% mol. of the total esters (described in U.S.A. Specification 2,839,512). Many suitable vinylpyridines, acids and alcohols and specific combinations are given. Optionally a metal deactivator may be added, preferably containing the structure: <FORM:0938118/III/1> in which R is a C1-C4 alkylene group, e.g. N,N1-disalicylidene-1,2-propanediamine or bis 1-acetonyl-ethylidene) ethanediamine added in an amount of 1-1,000 gram mols per gram atom of metal in the conductivity additive.ALSO:The following oil-soluble copolymers having a molecular weight of 5,000-2,500,000 and a nitrogen content of 0,1-8% by weight in which at least one of the monomers contains an aliphatic chain of at least 8 carbon atoms are described:- (1) A nitrogen-free monomer having a C8-C18 aliphatic hydrocarbon side chain and a monomer containing a basic amino group, the copolymer containing 0,1-3,5% by wt. basic amino nitrogen, e.g. lauryl methacrylate/styrene/diethylaminoethyl methacrylate in the ratio 45:45:10 (U.S.A. Specification 2,737,452). (2) An N-vinyl-2-pyrrolidone (5-35%) and an acrylate or methacrylate of a C8+ alcohol (Belgian Specification 550,442 and Canadian Specification 560,549). (3) A C10+ alpha olefin and an acrylic ester of a C1-C3 alcohol in which at least 10% of the ester groupings have been amidized with a compound containing a -NR2 or -CONR2 (R=hydrocarbon) group (U.S.A. Specification 2,800,452). (4) A vinyl pyridine and an ester of an acrylic acid with a C10+ alcohol. Preferably a mixture of two esters is used derived from alcohols differing by at least 4 carbon atoms and in a mol. ratio of one to the other of 1:10 to 10:1 and there is preferably also present an acrylic ester of a C1-C6 alkanol forming 10-75% mol. of the total esters. The mol. ratio of vinyl pyridine to esters may be 1:15 to 2:1 (U.S.A. Specification 2,839,512). Many specific combinations are specified and examples given of the preparation of copolymers of stearyl and lauryl methacrylate with methyl or butyl methacrylate and methyl or ethyl vinyl pyridine in various ratios.ALSO:The preparation of chromium alkyl salicylates containing at least one C8 + alkyl group is described. Alkyl salicylic acid or an alkali metal salt thereof is first prepared by (a) alkylating salicylic acid with an olefin in the presence of 90-98% sulphuric acid, boron trifluoride or zinc chloride, (b) subjecting a nuclear acylated salicylic acid to a Clemmenson reduction with zinc and hydrochloric acid or, preferably (c) alkylating a phenol, forming the alkali metal phenate and carboxylating with carbon dioxide by the Kolbe method; alkyl salicylic acid is separated from unconverted phenate and by-products by acidifying and extracting with ammonia or neutralizing the acid only with alkali metal hydroxide. From a water-alcohol solution of alkyl phenols and alkyl salicylic acid the former can be extracted with pentane. The chromium salt is obtained by treating the alkali metal salt in a hydrocarbon or alcohol with an alcoholic solution of an inorganic chromium salt. For this purpose there may be used pure alkali metal alkyl salicylate or the carboxylated product containing alkyl phenol or the latter treated with alkali metal hydroxide to form the phenate or treated with double the amount necessary to form the phenate. The resulting chromium salt is respectively pure or contains alkyl phenol, chromium alkyl phenate or chromium alkyl phenate and an excess of bound chromium hydroxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US816039A US3013868A (en) | 1959-05-27 | 1959-05-27 | Liquid hydrocarbon compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
GB938118A true GB938118A (en) | 1963-10-02 |
Family
ID=25219541
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB18466/60A Expired GB938118A (en) | 1959-05-27 | 1960-05-25 | Organic liquids having increased electrical conductivity |
Country Status (6)
Country | Link |
---|---|
US (1) | US3013868A (en) |
BE (1) | BE591230A (en) |
DE (1) | DE1279267B (en) |
FR (1) | FR1269640A (en) |
GB (1) | GB938118A (en) |
NL (2) | NL120317C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0771782A1 (en) * | 1995-11-01 | 1997-05-07 | BP Chemicals (Additives) Limited | Salicylic acid alkylation |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL103681C (en) * | 1959-05-28 | |||
NL126094C (en) * | 1960-12-30 | |||
US3256073A (en) * | 1963-03-22 | 1966-06-14 | Cities Service Oil Co | Liquid hydrocarbon compositions having antistatic properties |
US3250113A (en) * | 1963-11-27 | 1966-05-10 | Shell Oil Co | Expendable pipeline plug |
BE731123A (en) * | 1968-04-11 | 1969-10-06 | ||
US3807977A (en) * | 1972-06-30 | 1974-04-30 | Du Pont | Antistatic additive compositions |
US3995097A (en) * | 1975-09-15 | 1976-11-30 | Phillips Petroleum Company | Prevention of fouling in polymerization reactors |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2737452A (en) * | 1952-04-07 | 1956-03-06 | Du Pont | Stabilized fuel oils |
BE525410A (en) * | 1952-12-30 | |||
NL97884C (en) * | 1954-07-12 | |||
US2839512A (en) * | 1955-12-30 | 1958-06-17 | Shell Dev | Vinylpyridine long chain acrylic ester copolymers and their preparation |
-
0
- NL NL251969D patent/NL251969A/xx unknown
- NL NL120317D patent/NL120317C/xx active
-
1959
- 1959-05-27 US US816039A patent/US3013868A/en not_active Expired - Lifetime
-
1960
- 1960-05-25 FR FR828239A patent/FR1269640A/en not_active Expired
- 1960-05-25 GB GB18466/60A patent/GB938118A/en not_active Expired
- 1960-05-25 BE BE591230A patent/BE591230A/xx unknown
- 1960-05-25 DE DES68679A patent/DE1279267B/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0771782A1 (en) * | 1995-11-01 | 1997-05-07 | BP Chemicals (Additives) Limited | Salicylic acid alkylation |
Also Published As
Publication number | Publication date |
---|---|
US3013868A (en) | 1961-12-19 |
BE591230A (en) | 1960-11-25 |
DE1279267B (en) | 1968-10-03 |
FR1269640A (en) | 1961-08-18 |
NL120317C (en) | |
NL251969A (en) |
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