DE2512201A1 - Dicarbonsaeurederivate, verfahren zu ihrer herstellung und diese als additiv enthaltende schmiermittel und treibstoffe - Google Patents
Dicarbonsaeurederivate, verfahren zu ihrer herstellung und diese als additiv enthaltende schmiermittel und treibstoffeInfo
- Publication number
- DE2512201A1 DE2512201A1 DE19752512201 DE2512201A DE2512201A1 DE 2512201 A1 DE2512201 A1 DE 2512201A1 DE 19752512201 DE19752512201 DE 19752512201 DE 2512201 A DE2512201 A DE 2512201A DE 2512201 A1 DE2512201 A1 DE 2512201A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- reaction product
- oil
- dicarboxylic acid
- oxazoline
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 9
- 239000000446 fuel Substances 0.000 title claims description 7
- 239000000654 additive Substances 0.000 title description 34
- 239000000314 lubricant Substances 0.000 title description 19
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 32
- -1 mono-unsaturated dicarboxylic acid compound Chemical class 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 27
- 239000007795 chemical reaction product Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000003502 gasoline Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000008064 anhydrides Chemical class 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000010688 mineral lubricating oil Substances 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001734 carboxylic acid salts Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 150000005673 monoalkenes Chemical class 0.000 claims description 3
- 150000002918 oxazolines Chemical class 0.000 claims description 3
- 150000003751 zinc Chemical class 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 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 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- 239000003921 oil Substances 0.000 description 46
- 239000010802 sludge Substances 0.000 description 32
- 239000002270 dispersing agent Substances 0.000 description 30
- 239000012141 concentrate Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- 230000000996 additive effect Effects 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 229940014800 succinic anhydride Drugs 0.000 description 20
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 14
- 150000001414 amino alcohols Chemical class 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 229920002367 Polyisobutene Polymers 0.000 description 10
- 229920000098 polyolefin Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000001991 dicarboxylic acids Chemical class 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 8
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 5
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012208 gear oil Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
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- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45525074A | 1974-03-27 | 1974-03-27 | |
US49478974A | 1974-08-05 | 1974-08-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2512201A1 true DE2512201A1 (de) | 1975-10-09 |
Family
ID=27037789
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752512201 Granted DE2512201A1 (de) | 1974-03-27 | 1975-03-20 | Dicarbonsaeurederivate, verfahren zu ihrer herstellung und diese als additiv enthaltende schmiermittel und treibstoffe |
DE19752534921 Pending DE2534921A1 (de) | 1974-03-27 | 1975-08-05 | Verfahren zur herstellung einer detergensverbindung |
DE19752534922 Withdrawn DE2534922A1 (de) | 1974-03-27 | 1975-08-05 | Verfahren zur herstellung von detergentien |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752534921 Pending DE2534921A1 (de) | 1974-03-27 | 1975-08-05 | Verfahren zur herstellung einer detergensverbindung |
DE19752534922 Withdrawn DE2534922A1 (de) | 1974-03-27 | 1975-08-05 | Verfahren zur herstellung von detergentien |
Country Status (6)
Country | Link |
---|---|
AU (1) | AU8366075A (nl) |
BE (1) | BE827198A (nl) |
DE (3) | DE2512201A1 (nl) |
FR (3) | FR2265771B1 (nl) |
GB (3) | GB1483681A (nl) |
NL (3) | NL182220C (nl) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2740535A1 (de) * | 1976-09-24 | 1978-03-30 | Exxon Research Engineering Co | Kohlenwasserstoffloesliche alkyllaktonoxazoline, verfahren zu ihrer herstellung und ihre verwendung in kohlenwasserstoffen als antirost- und/oder schlammdispergiermittel |
US4113639A (en) * | 1976-11-11 | 1978-09-12 | Exxon Research & Engineering Co. | Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound |
US4203900A (en) | 1977-01-03 | 1980-05-20 | The Dow Chemical Company | Process for preparing 2-oxazolines |
EP0016660A1 (en) * | 1979-03-26 | 1980-10-01 | Exxon Research And Engineering Company | Thio-bis-(hydrocarbon-bisoxazolines) and analogs, process for their preparation and their use as oleaginous additives |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4017406A (en) * | 1975-05-01 | 1977-04-12 | Exxon Research And Engineering Company | Carboxylate half esters of 1-aza-3,7-dioxabicyclo[3.3.0] oct-5-yl methyl alcohols, their preparation and use as additives for oleaginous compositions |
DE2747608A1 (de) | 1976-10-28 | 1978-05-03 | Ciba Geigy Ag | Wirksame fluessigkeitszusammensetzung |
US4116876A (en) * | 1977-01-28 | 1978-09-26 | Exxon Research & Engineering Co. | Borated oxazolines as varnish inhibiting dispersants in lubricating oils |
NZ188418A (en) * | 1977-10-03 | 1981-02-11 | Mobil Oil Corp | Lubricants containing oil and an oxazoline |
CA1133490A (en) * | 1978-09-18 | 1982-10-12 | Jack Ryer | Molybdenum complexes of ashless oxazoline dispersants as friction reducing antiwear additives for lubricating oils |
US4443611A (en) * | 1978-12-05 | 1984-04-17 | The Dow Chemical Company | Liquid phase preparation of 2-H-2-oxazolines and 2-substituted-2-oxazolines |
US4292184A (en) | 1979-03-26 | 1981-09-29 | Exxon Research & Engineering Co. | Thio-bis-(hydrocarbon-bisoxazolines) as oleaginous additives for lubricants and fuels |
IT1193212B (it) * | 1979-08-10 | 1988-06-15 | Anic Spa | Additivi disperdenti per lubrificanti e metodo per la loro preparazione |
US4263153A (en) * | 1979-10-11 | 1981-04-21 | Exxon Research & Engineering Co. | Oxazoline containing dispersants stabilized against oxidation with sulfur and fuels and lubricants containing same |
US4374032A (en) * | 1980-03-28 | 1983-02-15 | Mobil Oil Corporation | Lubricant composition containing borated oxazoline friction reducer |
US4295983A (en) * | 1980-06-12 | 1981-10-20 | Ethyl Corporation | Lubricating oil composition containing boronated N-hydroxymethyl succinimide friction reducers |
US4354029A (en) | 1981-11-30 | 1982-10-12 | The Dow Chemical Company | Preparation of 2-substituted-2-oxazolines with organic zinc salt catalysts |
GB2123429A (en) * | 1982-05-22 | 1984-02-01 | Orobis Ltd | Phosphorus-containing polymeric lubricant additives |
GB8407300D0 (en) * | 1984-03-21 | 1984-04-26 | Ici Plc | Surfactants |
US6299655B1 (en) * | 1985-03-14 | 2001-10-09 | The Lubrizol Corporation | Diesel fuel compositions |
US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
US5294233A (en) * | 1989-02-10 | 1994-03-15 | Nippon Zeon Co., Ltd. | Additive for organic medium or thermoplastic polymer |
EP0388921A3 (en) * | 1989-03-22 | 1992-12-16 | Nippon Zeon Co., Ltd. | Additive for organic solvent or thermoplastic polymer |
AU674052B2 (en) * | 1993-05-24 | 1996-12-05 | Lubrizol Corporation, The | Pour point depressant treated fatty acid esters as biodegradable, combustion engine fuels |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1062253B (de) * | 1957-06-29 | 1959-07-30 | Hoechst Ag | Verfahren zur Herstellung von aether- bzw. thioaether- und carbon-saeureamidgruppenhaltigen Verbindungen |
DE1099263B (de) * | 1958-02-26 | 1961-02-09 | Standard Oil Co | Motortreibstoff auf Leichtbenzinbasis |
GB984409A (en) * | 1962-09-28 | 1965-02-24 | Shell Int Research | Lubricant additives and lubricants containing them |
GB1031130A (en) * | 1964-03-19 | 1966-05-25 | Shell Int Research | Preparation of ashless lubricant additives, additives thus prepared and lubricants containing them |
DE2029524A1 (de) * | 1969-06-16 | 1970-12-23 | The Dow Chemical Co., Midland, Mich. (V.St.A.) | Di-2-oxazin- und Di-2-oxazolinverbindungen, ihr Herstellungsverfahren und Polymerisate daraus |
US3576743A (en) * | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
DE1720006A1 (de) * | 1968-03-01 | 1971-05-19 | Bayer Ag | Verfahren zur Herstellung von Oxazolinen |
US3632511A (en) * | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
DE1695599A1 (de) * | 1967-02-02 | 1972-01-20 | Pan American Tung Res And Dev | Polymerisatbildende Zusammensetzung und galvanische Abscheidung desselben |
DE2204249A1 (de) * | 1971-02-03 | 1972-08-10 | Commissariat a lEnergie Atomique, Paris; Institut Francais du Petrole des Carburants et Lubrifiants, Rueil-Malmaison; (Frankreich) | Neue Verbindungen zur Herstellung von Kompositionen für durch Bestrahlung härtbare Überzüge |
DE2311387A1 (de) * | 1972-03-13 | 1973-09-27 | Commissariat Energie Atomique | Ungesaettigte ester von polyhydroxybis-oxazolinen, ihre herstellung und verwendung |
DE2220413A1 (de) * | 1972-04-26 | 1973-11-15 | Huels Chemische Werke Ag | 2-aminoalkylsubstituierte cyclische imidsaeureester und verfahren zu deren herstellung |
-
1975
- 1975-03-14 GB GB10718/75A patent/GB1483681A/en not_active Expired
- 1975-03-14 GB GB41931/76A patent/GB1483682A/en not_active Expired
- 1975-03-20 DE DE19752512201 patent/DE2512201A1/de active Granted
- 1975-03-25 FR FR7509342A patent/FR2265771B1/fr not_active Expired
- 1975-03-26 BE BE154781A patent/BE827198A/xx not_active IP Right Cessation
- 1975-03-27 NL NLAANVRAGE7503722,A patent/NL182220C/nl not_active IP Right Cessation
- 1975-08-04 NL NL7509290A patent/NL7509290A/nl not_active Application Discontinuation
- 1975-08-04 GB GB32519/75A patent/GB1513178A/en not_active Expired
- 1975-08-04 AU AU83660/75A patent/AU8366075A/en not_active Expired
- 1975-08-04 NL NL7509289A patent/NL7509289A/nl unknown
- 1975-08-05 DE DE19752534921 patent/DE2534921A1/de active Pending
- 1975-08-05 FR FR7524411A patent/FR2281422A1/fr active Granted
- 1975-08-05 FR FR7524412A patent/FR2281423A1/fr active Granted
- 1975-08-05 DE DE19752534922 patent/DE2534922A1/de not_active Withdrawn
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1062253B (de) * | 1957-06-29 | 1959-07-30 | Hoechst Ag | Verfahren zur Herstellung von aether- bzw. thioaether- und carbon-saeureamidgruppenhaltigen Verbindungen |
DE1099263B (de) * | 1958-02-26 | 1961-02-09 | Standard Oil Co | Motortreibstoff auf Leichtbenzinbasis |
GB984409A (en) * | 1962-09-28 | 1965-02-24 | Shell Int Research | Lubricant additives and lubricants containing them |
GB1031130A (en) * | 1964-03-19 | 1966-05-25 | Shell Int Research | Preparation of ashless lubricant additives, additives thus prepared and lubricants containing them |
DE1695599A1 (de) * | 1967-02-02 | 1972-01-20 | Pan American Tung Res And Dev | Polymerisatbildende Zusammensetzung und galvanische Abscheidung desselben |
DE1720006A1 (de) * | 1968-03-01 | 1971-05-19 | Bayer Ag | Verfahren zur Herstellung von Oxazolinen |
US3576743A (en) * | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
DE2029524A1 (de) * | 1969-06-16 | 1970-12-23 | The Dow Chemical Co., Midland, Mich. (V.St.A.) | Di-2-oxazin- und Di-2-oxazolinverbindungen, ihr Herstellungsverfahren und Polymerisate daraus |
US3632511A (en) * | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
DE2204249A1 (de) * | 1971-02-03 | 1972-08-10 | Commissariat a lEnergie Atomique, Paris; Institut Francais du Petrole des Carburants et Lubrifiants, Rueil-Malmaison; (Frankreich) | Neue Verbindungen zur Herstellung von Kompositionen für durch Bestrahlung härtbare Überzüge |
DE2311387A1 (de) * | 1972-03-13 | 1973-09-27 | Commissariat Energie Atomique | Ungesaettigte ester von polyhydroxybis-oxazolinen, ihre herstellung und verwendung |
DE2220413A1 (de) * | 1972-04-26 | 1973-11-15 | Huels Chemische Werke Ag | 2-aminoalkylsubstituierte cyclische imidsaeureester und verfahren zu deren herstellung |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2740535A1 (de) * | 1976-09-24 | 1978-03-30 | Exxon Research Engineering Co | Kohlenwasserstoffloesliche alkyllaktonoxazoline, verfahren zu ihrer herstellung und ihre verwendung in kohlenwasserstoffen als antirost- und/oder schlammdispergiermittel |
US4113639A (en) * | 1976-11-11 | 1978-09-12 | Exxon Research & Engineering Co. | Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound |
US4203900A (en) | 1977-01-03 | 1980-05-20 | The Dow Chemical Company | Process for preparing 2-oxazolines |
EP0016660A1 (en) * | 1979-03-26 | 1980-10-01 | Exxon Research And Engineering Company | Thio-bis-(hydrocarbon-bisoxazolines) and analogs, process for their preparation and their use as oleaginous additives |
Also Published As
Publication number | Publication date |
---|---|
AU8366175A (en) | 1977-02-10 |
BE827198A (fr) | 1975-09-26 |
FR2281422B1 (nl) | 1978-10-20 |
NL7509289A (nl) | 1976-02-09 |
FR2281423B3 (nl) | 1978-03-24 |
FR2265771A1 (nl) | 1975-10-24 |
GB1513178A (en) | 1978-06-07 |
NL7509290A (nl) | 1976-02-09 |
GB1483682A (en) | 1977-08-24 |
AU8366075A (en) | 1977-02-10 |
FR2281423A1 (fr) | 1976-03-05 |
FR2281422A1 (fr) | 1976-03-05 |
FR2265771B1 (nl) | 1980-06-20 |
DE2534922A1 (de) | 1976-02-26 |
GB1483681A (en) | 1977-08-24 |
DE2534921A1 (de) | 1976-02-26 |
NL182220B (nl) | 1987-09-01 |
AU7922775A (en) | 1976-09-23 |
NL7503722A (nl) | 1975-09-30 |
NL182220C (nl) | 1988-02-01 |
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8364 | No opposition during term of opposition |