US2295192A - Lubricating composition and modified addition agents for the same - Google Patents
Lubricating composition and modified addition agents for the same Download PDFInfo
- Publication number
- US2295192A US2295192A US363018A US36301840A US2295192A US 2295192 A US2295192 A US 2295192A US 363018 A US363018 A US 363018A US 36301840 A US36301840 A US 36301840A US 2295192 A US2295192 A US 2295192A
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- United States
- Prior art keywords
- phosphatides
- hydrogenated
- reaction product
- lubricants
- addition agents
- 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
- 239000000203 mixture Substances 0.000 title description 5
- 230000001050 lubricating effect Effects 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 description 22
- 239000000314 lubricant Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 9
- 239000010687 lubricating oil Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910001092 metal group alloy Inorganic materials 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- -1 pyridine Chemical class 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical class CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 229940042472 mineral oil Drugs 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2221/041—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds involving sulfurisation of macromolecular compounds, e.g. polyolefins
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/10—Phosphatides, e.g. lecithin, cephalin
Definitions
- the present invention relates to lubricating oils containing addition agents for use in automotive engines and to methods for modifying certain addition agents so that theirundesirable q'ua1i-.- ties may be removed, thereby gaining the full benefit of the desirable rualities.
- An object of the present invention is to improve the properties of the oilsby modifying the addition agents either before addition to the lubricant or in situ.
- the present invention relates to such addition agents as phosphatides and.
- neutralization may be carried out by various neuphatides, but also by the unsaturation of the phosphatides and the commercial mixtures thereof.
- the phosphatides may be hydrogenated and then neutralized. Afterhaving treated the phosphatides in this manner they are better suited for use as addition agents to lubricating oils.
- the hydrogenation of the phosphatides may be carried out by any well-known processes provided the conditions are not so severe as to affect adversely the phosphatides by decomposing them.
- the phosphatidic material In order to facilitate handling of the phosphatlde during the hydrogenation and the neutralization step it is sometimes desirable to dilute the phosphatidic material with mineral oil, preferably in the proportion of, 1 part material to 1 part or more. of mineral-oil.
- the phosphatides are neutralized simply'by I mixing them with one of the aforementioned neutralizing agents for, several hours either at room temperature or at temperaturesfrom 80? F. to about 300 If desired, the. phosphatide or neutralizing agentmay be added to the oil first and then theother'added so'the reaction will take place in situ.
- organic base such as pyridine, pyridine derivatives, the tetra alkyl ammonium hydroxides, hy-
- droxylamines primary, secondary and tertiaryamines or the amines prepared from various oils such as cocoanut oil.
- the amines may have. the following general formulae RANCH, RzN, RzNH, RNHz, (OI-IR) 3N, R'NHR, or RNB: wherein R and R represents an alkyl, alkylene, aryl or aralkyl radical.
- a small quantity preferably from about 0.01% to about 5% is added to the oil, with the result that the oxidation stability and the detergent properties of theoil are improved, at least to the same extent as when unmodified phosphatide is added to the oil, but with'the additional advantage that no corrosion of the metal alloy bearing surfaces occurs, 'and early sludge formation is minimized. Furthermore, the antioxidant effect is improved.
- sulfur-type inhibitors such as sulfurized olefin polymers, organic phosphites
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkyl amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures below about 300 F.
- An addition agent for-lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkylolamine at temperatures below about 300 F.
- a lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
- a lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an alkyl amine 'at temperatures below about 300 F.
- a lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures below about 300 F.
- a lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an alkylolamine at tempera-' tures below about 300 F.
- a lubricant comprising a. lubricating oil and from about 0.01% to about 5% of the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures within the approximate range of F. to 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkyl amine at temperatures within the approximate range of 80 F. to 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures within the approximate range of 80 F. to 300 F.
- An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkylolamine at temperatures within the approximate range of 80 F. to 300 F.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
UNITED STATES PATENT? ene LUBRICATING comosrrron m MODI- rmn annrrron AGENTS'FOR 'rnn same Maurice H. Arveson, FlossmoonIlL, assignor to Standard Oil Company, Chicago, 111., a. comration of Indiana No Drawing.. Application October 26, 1940, I Serial No. 363,018
16 Claims.
The present invention relates to lubricating oils containing addition agents for use in automotive engines and to methods for modifying certain addition agents so that theirundesirable q'ua1i-.- ties may be removed, thereby gaining the full benefit of the desirable rualities.
An object of the present invention is to improve the properties of the oilsby modifying the addition agents either before addition to the lubricant or in situ. n
More particularly the present invention relates to such addition agents as phosphatides and.
' to oils improves the quality thereof by preventing ring sticking and by acting as detergents and antioxidants. It has been found, however, that while certain qualities of the lubricant are improved by these addition agents, certain other undesirable properties appear. In the case of the phosphatides it has been found that early sludge is often formed and that certain metal alloy bearing surfaces are corroded, particularly leadcontaining bearings. These adverse effects are believed to be caused not only by the acidic properties of the phosphatides or the fatty oils occurring in the commercial mixtures of the phosthe elements and groupspf elements in the compound, but are' also caused by the presence of double. bonds which-occur in the phosphatides as well as the commercial mixtures of thesame.
' The presence of double-bonds in a compound rapidly leads to the development of acidic properties in the compound on oxidation. It is evident, therefore, that the-hydrogenation of phosphatides and the subsequent neutralization thereof 'produces a product which is particularly suitable for use as an addition agent in lubricating/oils. The
. neutralization may be carried out by various neuphatides, but also by the unsaturation of the phosphatides and the commercial mixtures thereof.
In order to overcome the above-mentioned undesirable effects of the phosphatides they may be hydrogenated and then neutralized.. Afterhaving treated the phosphatides in this manner they are better suited for use as addition agents to lubricating oils.
The exact nature of the reactions involved in both the hydrogenation and neutralization steps is not clear. The fact that the unmodified phosphatides cause corrosion of various metal alloy bearing surfaces and tend to form early sludge is probably due to the fact that the phosphatides exhibit acidic properties. These acidic properties are not only caused by the nature and position of 55 ,tralizing agents such as ammonia orzby the use of amines including both the alkyl and alkylolamines and aromatic amines such as pyridine,
quinoline and their derivatives. It is believed that the ammonium, or amine salts of I the commercial phosphatides are formed. Theamount of organic base used in the neutralization maybe varied from 50% to 100%, or even an excess of of the phosphatide may'be 'used.
organic base, ranging up to 200% of the acidity The hydrogenation of the phosphatides may be carried out by any well-known processes provided the conditions are not so severe as to affect adversely the phosphatides by decomposing them.
It is preferred, however, to carry out the hydro genati'on by the relatively low temperature, fat
hydrogenation technique using, for example, I nickel formate as catalyst. Several methods for v hydrogenating commercial phosphatides are described in Chemie und Technologie de Fette und Fett Produkte. Hefter-Schonfeld, 2nd edition,' vol. 1, page 508. An additional method isalso described in Jour. Agr. Chem. Soc., Japan, vol. 9, pp. 728 to 732. (Reviewed in Chemical Abstracts, vol. 27, p. 5563.) Obviously; the hydrogenation step will not only saturatethe phosphatides per se but also the free fats andfatty acids which accompany the phosphatides in the commercial mixtures.
In order to facilitate handling of the phosphatlde during the hydrogenation and the neutralization step it is sometimes desirable to dilute the phosphatidic material with mineral oil, preferably in the proportion of, 1 part material to 1 part or more. of mineral-oil.
.The phosphatides are neutralized simply'by I mixing them with one of the aforementioned neutralizing agents for, several hours either at room temperature or at temperaturesfrom 80? F. to about 300 If desired, the. phosphatide or neutralizing agentmay be added to the oil first and then theother'added so'the reaction will take place in situ.
organic base such as pyridine, pyridine derivatives, the tetra alkyl ammonium hydroxides, hy-
droxylamines, primary, secondary and tertiaryamines or the amines prepared from various oils such as cocoanut oil. The amines may have. the following general formulae RANCH, RzN, RzNH, RNHz, (OI-IR) 3N, R'NHR, or RNB: wherein R and R represents an alkyl, alkylene, aryl or aralkyl radical.
Specifically (CH11)4NOH, (CH3)3N, (C4H9)3N. (CsHs) 3N, (C2H5) zNH, (CsHr) zNH, (CsHe) NHz, CraHsJNHa, CsHsNI-Iz, (OHC2H4) 3N, and CsH5N(CH3)2 have been found to be satisfactory;
After the phosphatidic material has been hydrogenated and subsequently neutralized, a small quantity, preferably from about 0.01% to about 5% is added to the oil, with the result that the oxidation stability and the detergent properties of theoil are improved, at least to the same extent as when unmodified phosphatide is added to the oil, but with'the additional advantage that no corrosion of the metal alloy bearing surfaces occurs, 'and early sludge formation is minimized. Furthermore, the antioxidant effect is improved.
Although the foregoing description has referred primarily to lubricating -oils, other lubricants, such as grease, derive the same benefits from the modified phosphatides and are therefore contemplated in the present invention.
Furthermore, it is possible and sometimes advantageous to add other well-known addition agents, for example, sulfur-type inhibitors such as sulfurized olefin polymers, organic phosphites;
etc., to the oil.
I claim:
1. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
2. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkyl amine at temperatures below about 300 F.
3. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures below about 300 F.
4. An addition agent for-lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkylolamine at temperatures below about 300 F.
5. An addition agent for lubricants as claimed in claim 1 wherein the hydrogenated phosphatidic material comprises hydrogenated lecithin and hydrogenated cephalin.
6. An addition agent for lubricants as claimed in claim 1 wherein the hydrogenated phosphatidic material comprises hydrogenated lecithin.
7. An addition agent for lubricants as claimed in claim 1 wherein the hydrogenated phosphatidic material comprises hydrogenated cephalin.
8. A lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
9. A lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an alkyl amine 'at temperatures below about 300 F.
10. A lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures below about 300 F.
11. A lubricant comprising a lubricating oil and the reaction product of a hydrogenated phosphatidic material and an alkylolamine at tempera-' tures below about 300 F.
12. A lubricant comprising a. lubricating oil and from about 0.01% to about 5% of the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures below about 300 F.
13. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an organic amine at temperatures within the approximate range of F. to 300 F.
14. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkyl amine at temperatures within the approximate range of 80 F. to 300 F.
15. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an aromatic amine at temperatures within the approximate range of 80 F. to 300 F.
16. An addition agent for lubricants comprising the reaction product of a hydrogenated phosphatidic material and an alkylolamine at temperatures within the approximate range of 80 F. to 300 F.
' MAURICE H. ARVESON.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363018A US2295192A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agents for the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363018A US2295192A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agents for the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2295192A true US2295192A (en) | 1942-09-08 |
Family
ID=23428438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US363018A Expired - Lifetime US2295192A (en) | 1940-10-26 | 1940-10-26 | Lubricating composition and modified addition agents for the same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2295192A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870179A (en) * | 1954-08-10 | 1959-01-20 | American Lecithin Co | Hydrogenation of phosphatides |
| US4753742A (en) * | 1986-03-14 | 1988-06-28 | Mallet & Company, Inc. | Lubricating oils for dough dividers and the like and methods of using said oils |
| EP0386923A1 (en) * | 1989-03-09 | 1990-09-12 | Exxon Chemical Patents Inc. | Hydrogenated lecithin for friction and flow properties |
| US5487839A (en) * | 1991-04-18 | 1996-01-30 | The Lubrizol Corporation | Grease compositions |
| US5487838A (en) * | 1991-04-18 | 1996-01-30 | The Lubrizol Corporation | Reaction products of a boron compound and a phospholipid, and lubricant and aqueous fluids containing same |
| US5503866A (en) * | 1995-01-17 | 1996-04-02 | Mallet And Company, Inc. | Releasing compositions for food contact surfaces |
| US20050288195A1 (en) * | 2004-06-23 | 2005-12-29 | Heenan David F | Lubricant formulations for sheet metal processing |
-
1940
- 1940-10-26 US US363018A patent/US2295192A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870179A (en) * | 1954-08-10 | 1959-01-20 | American Lecithin Co | Hydrogenation of phosphatides |
| US4753742A (en) * | 1986-03-14 | 1988-06-28 | Mallet & Company, Inc. | Lubricating oils for dough dividers and the like and methods of using said oils |
| EP0386923A1 (en) * | 1989-03-09 | 1990-09-12 | Exxon Chemical Patents Inc. | Hydrogenated lecithin for friction and flow properties |
| US5135669A (en) * | 1989-03-09 | 1992-08-04 | Exxon Chemical Patents Inc. | Hydrogenated lecithin for friction and flow properties |
| US5487839A (en) * | 1991-04-18 | 1996-01-30 | The Lubrizol Corporation | Grease compositions |
| US5487838A (en) * | 1991-04-18 | 1996-01-30 | The Lubrizol Corporation | Reaction products of a boron compound and a phospholipid, and lubricant and aqueous fluids containing same |
| US5503866A (en) * | 1995-01-17 | 1996-04-02 | Mallet And Company, Inc. | Releasing compositions for food contact surfaces |
| US20050288195A1 (en) * | 2004-06-23 | 2005-12-29 | Heenan David F | Lubricant formulations for sheet metal processing |
| WO2006000084A1 (en) * | 2004-06-23 | 2006-01-05 | Novelis Inc. | Lubricant formulations for sheet metal processing |
| US7569525B2 (en) | 2004-06-23 | 2009-08-04 | Novelis Inc. | Lubricant formulations for sheet metal processing |
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