US2215590A - Lubricating composition - Google Patents
Lubricating composition Download PDFInfo
- Publication number
- US2215590A US2215590A US32380A US3238035A US2215590A US 2215590 A US2215590 A US 2215590A US 32380 A US32380 A US 32380A US 3238035 A US3238035 A US 3238035A US 2215590 A US2215590 A US 2215590A
- Authority
- US
- United States
- Prior art keywords
- oils
- oil
- esters
- phthalate
- ester
- 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 15
- 230000001050 lubricating effect Effects 0.000 title description 5
- 239000003921 oil Substances 0.000 description 28
- 150000002148 esters Chemical class 0.000 description 23
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 11
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 2
- MXOGJBKTZBIWOT-UHFFFAOYSA-N 2-phenoxycarbonylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)OC1=CC=CC=C1 MXOGJBKTZBIWOT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- HCHHNNBICUNCTE-UHFFFAOYSA-N bis(2-phenoxyethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCCOC=2C=CC=CC=2)C=1C(=O)OCCOC1=CC=CC=C1 HCHHNNBICUNCTE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 239000010727 cylinder oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XIKIUQUXDNHBFR-UHFFFAOYSA-N monobenzyl phthalate Chemical class OC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 XIKIUQUXDNHBFR-UHFFFAOYSA-N 0.000 description 1
- CXJOEMLCEGZVPL-UHFFFAOYSA-N monoisopropyl phthalate Chemical compound CC(C)OC(=O)C1=CC=CC=C1C(O)=O CXJOEMLCEGZVPL-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 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 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/284—Esters of aromatic monocarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/285—Esters of aromatic polycarboxylic acids
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/288—Partial esters containing free carboxyl groups
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl groups
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
- C10N2040/135—Steam engines or turbines
-
- 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—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- the present invention relates to lubricating compositions and to methods for producing the same, and more specifically to a lubricant capable of carrying heavy loads and of reducing friction.
- a lubricant capable of carrying heavy loads and of reducing friction.
- Lubricants especially the oils for modern motor vehicles, have within recent years been subjected to conditions of load, speed and the like never before encountered. It has been long realized that hydrocarbon oils are not naturally endowed with ideal properties for severe service. For example, they do not possess oiliness .or
- mineral oils are greatly improved, particularly in respect to carbonforming tendencies, load carrying capacity or oiliness and tendencies toward oxidation by the addition of relatively small amounts of certain materials.
- The. materials which are added are included within the broad class of phthalic acid compounds and among these esters are also included those of isophthalic and terephthalic acids as well as the simple derivatives such as the alkylation products.
- various. acids are preferably esterified with various alcohols and among these the simple aliphatic alcohols may be' used such as methyl, ethyl, the propyl, the butyl and the amyl alcohols and these are for many purposes the most satisfactory, although the higher alcoholic esters are also quite useful such as the phthalates of cetyl, lauryl, octadecyl, oleyl and the like.
- Esters of aromatic alcohols or phenols may also be included such as phenyl, cresyl or benzyl phthalates and especially the alkylated phenyl phthalates.
- the mono alkyl esters are satisfactory but for most purposes the dialkyl esters are preferable such as diethyl, dibutyl or dicresyl phthalates, and among the alcohols the monohydric groups are to be preferred, although polyhydric alcoholic esters such as those of glycol and glycerol may be included.
- phthalic esters which may be employed are butyl benzyl phthalate, glycol ether phtha- (Cl. 252-57) lates, dibutoxy ethyl phthalate, di (beta phenoxyethyl) phthalate, di (betabutoxy ethyl) glycol di-phthalate, hydrogenated phthalates, and the like.
- These agents may be added to the lubricating oils for use in automobile engines or in steam cylinder oils, various industrial lubricants and the like, or they may be included as ingredients in grease compositions such as are adapted for use where a higher degree of oiliness is required than is ordinarily offered by the common greases now available.
- oils for example those derived from paraflinic, napthenic or asphalt base crudes such as may be refined by the ordinary methods of refining now commonly in use and they also may be used as addition agents to oils which have been refined by special processes such as solvent extraction, hydrogenation or the like.
- the base stocks should be well refined and of a good quality and while the particular compositions made up with mineral oils alone are of especial value, particularly for motor lubrication, it should be understood that other ingredients such as soaps maybe added even to such large proportions as to solidify the oil.
- the addition agents may be psed in straight mineral oils or they may be added to blended oils which contain other ingredients, for example,
- pour inhibitors As examples of the new compositions, the following may be considered:
- ExampleI The lubricating oil selected for the following SEARCH ROOM 2,215,590; q
- Example II The oxidation rates of the various samples listed in Example I were determined by passing oxygen at a definite and uniform rate through a cyclic path which includes a container in which inch pounds.
- Example I shows the oxidation rates of the various samples in.
- Example III In order to show the oiliness properties runs were made with the samples shown in Example I, on the Mougey machine according to the meth- 0d of Mougey and Almen, National Petroleum News, November 11, 1933, page 47.
- the pin in these particular tests was steel and the bushings aluminum.
- Example V I Tetrahydro phthalic acid is produced by reac-v tion of maleic anhydride and butadiene under known conditions. The product was then esterifled with isopropyl alcohol. To an S. A. E. 20 grade lubricating oil 20% -of this ester is added. Sligh tests and oxidation rate tests were then the base oil and the blend. The Sligh tests were made in the usual manner; and the according to the method of The results are as follows:
- a lubricating composition containing a major proportion of a viscous hydrocarbon lubrieating oil and a minor proportion of a phthalic ester.
- a lubricant comprising a viscous hydrocar-. bon lubricating oil and a minor quantity up to about 10% of an ester of phthalicacid.
- composition according to claim 2 in which Q 0 iii .the ester is a dialkyl ester derived from mono- 6.
- composition according to claim 2 in which hydric alcohols and phthalic acid. the ester is dibutyl phthalate.
- composition according to claim 2 in which '7.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
lit. 2x21511598 Patented Sept. 24, 1940 UNITED STATES oss Reference LUBRIOATING C'OMPO SITION George M. Maverick, Elizabeth, N. J., assignor to StandardOil Development Company, a corporation of Delaware No Drawing. Application July 20, 1935,
' Serial No. 32,380
.7 Claims.
The present invention relates to lubricating compositions and to methods for producing the same, and more specifically to a lubricant capable of carrying heavy loads and of reducing friction. The nature of the composition and its ingredients will be fully understood from the following description.
Lubricants, especially the oils for modern motor vehicles, have within recent years been subjected to conditions of load, speed and the like never before encountered. It has been long realized that hydrocarbon oils are not naturally endowed with ideal properties for severe service. For example, they do not possess oiliness .or
lubricating properties to so high a degree as might be desired. They tend to deteriorate by oxidation and sludge formation and while there are now no satisfactory substitutes for them, it is highly desirable to improve the natural oils in respect to these properties. While hydrocarbon lubricants are adequate at the present time, it is very desirable to further increase loads and speeds and improved oils must be found to meet' this demand.
In the present invention mineral oils are greatly improved, particularly in respect to carbonforming tendencies, load carrying capacity or oiliness and tendencies toward oxidation by the addition of relatively small amounts of certain materials. The. materials which are added are included within the broad class of phthalic acid compounds and among these esters are also included those of isophthalic and terephthalic acids as well as the simple derivatives such as the alkylation products.
These various. acids are preferably esterified with various alcohols and among these the simple aliphatic alcohols may be' used such as methyl, ethyl, the propyl, the butyl and the amyl alcohols and these are for many purposes the most satisfactory, although the higher alcoholic esters are also quite useful such as the phthalates of cetyl, lauryl, octadecyl, oleyl and the like. Esters of aromatic alcohols or phenols may also be included such as phenyl, cresyl or benzyl phthalates and especially the alkylated phenyl phthalates. The mono alkyl esters are satisfactory but for most purposes the dialkyl esters are preferable such as diethyl, dibutyl or dicresyl phthalates, and among the alcohols the monohydric groups are to be preferred, although polyhydric alcoholic esters such as those of glycol and glycerol may be included.
Other phthalic esters which may be employed are butyl benzyl phthalate, glycol ether phtha- (Cl. 252-57) lates, dibutoxy ethyl phthalate, di (beta phenoxyethyl) phthalate, di (betabutoxy ethyl) glycol di-phthalate, hydrogenated phthalates, and the like.
The materials mentioned above 'are added to the oils in amounts ranging from up to 10%, although for most purposes about 2% is quite satisfactory. They are quite effective for the purposes outlined above in this concentration although for. some special uses relatively large amounts may be desirable.
These agents may be added to the lubricating oils for use in automobile engines or in steam cylinder oils, various industrial lubricants and the like, or they may be included as ingredients in grease compositions such as are adapted for use where a higher degree of oiliness is required than is ordinarily offered by the common greases now available.
The esters first described, as stated before, may
be added to any types of lubricating, oils, for example those derived from paraflinic, napthenic or asphalt base crudes such as may be refined by the ordinary methods of refining now commonly in use and they also may be used as addition agents to oils which have been refined by special processes such as solvent extraction, hydrogenation or the like. The base stocks should be well refined and of a good quality and while the particular compositions made up with mineral oils alone are of especial value, particularly for motor lubrication, it should be understood that other ingredients such as soaps maybe added even to such large proportions as to solidify the oil.
The addition of as much as 10% of the phthalic esters reduces the viscosity of the oilblend and moreover changes an S. A. E. 30 grade to 20 but such oils have considerably greater oiliness than the unblended oils of greater viscosity and there is no danger in using a 20 blend where a 30 unblended oil was previously used.
An oil having viscosity of 550 and 64.2 seconds Saybolt respectively at 100 and 210 F. when blended with 10% dibutyl phthalate showed viscosities of 374 and 56 seconds at 100 and 210? F.-
respectively.
' The addition agents may be psed in straight mineral oils or they may be added to blended oils which contain other ingredients, for example,
pour inhibitors, anti-oxidants, dyes, thickeners 50 I and the-like. As examples of the new compositions, the following may be considered:
ExampleI The lubricating oil selected for the following SEARCH ROOM 2,215,590; q
comrosmcms.
tests is an S. A. E. 20 base stock of good quality. One sample of this oil is used as a blank and to other samples the various phthalic acid esters have been added. The table below shows some of the physical properties of these oils:
Sample No. min
1 Hydrocarbon lubricating oil. 1620 2 Same +l% dimcthyl phthalate. 09 8. 4 1380 3 Same +l% dicthyl phthalate. 06 6. 7 1020 03 5. 0 1620 Example II The oxidation rates of the various samples listed in Example I were determined by passing oxygen at a definite and uniform rate through a cyclic path which includes a container in which inch pounds.
perature of 200 C- The oxygen bubbles through, oil and at intervals of 15 minutes the amount of oxygen absorbed is determined by difference from the volume remaining. The table below shows the oxidation rates of the various samples in. Example I:
Oxidation rate at 200 0.,
Sample cc. 03/10 cc. Sample/15 minutes m 1 Hydrocarbon oil (i2 93 56 2 Same+l% dimethyl phthalatc. 28 59 59 34 3 Same+l% diethyl phtha-late 37 53 40 39 40 49 43 42 4 Same-H7 dibutyl phthalate The rate of oxidation is considerably reduced by the addition of the phthalic esters.
Example III In order to show the oiliness properties runs were made with the samples shown in Example I, on the Mougey machine according to the meth- 0d of Mougey and Almen, National Petroleum News, November 11, 1933, page 47. The pin in these particular tests was steel and the bushings aluminum.
Mougey test Samples Weights Final carried friction 1 Hydrocarbon oil L l7 Sheared 2 Same+1% dimcthyl phthalate. 25 29 3 Same+l% diethyl phthalato p 25 23 4 Same+1% dibutyl phthalate 25 23 The samples conta' ing the esters carried the full 25 weights, the highest load called for by the. test, and at the low frictional values of 23 to 29 Example I V- In practical operation in automotive engines 'the oils containing phtha c esters showed valuable properties. Comparative tests were made on a Universal -engine, one run on an unblended S. A. E. 30 oil and the other with the same oil truss iiBTBlBflCB part of a prior application December 20, 1933;
' was 7.7 grams or 52 grams/pound of oil.
Similar tests in a Chevrolet engine gave 14.9 grams of carbon (total) for the 10% dibutyl phthalate blend or 4.0 grams/pound ofoil as against 18.8 grams total or 5.9 grams/pound of oil for unblended hydrocarbon lubricant used.
Example V I Tetrahydro phthalic acid is produced by reac-v tion of maleic anhydride and butadiene under known conditions. The product was then esterifled with isopropyl alcohol. To an S. A. E. 20 grade lubricating oil 20% -of this ester is added. Sligh tests and oxidation rate tests were then the base oil and the blend. The Sligh tests were made in the usual manner; and the according to the method of The results are as follows:
oxidation rate test Example 11 above.
Oxidation rate,
cc. 01/10 cc. Samplo Shgh Sample/l5 min.@
/ Unblended oil 38.0 629356 Oil+.2% tetrahydro isopropyl phthalate 33. 8 -8147 The Sligh value is decreased and the initial oxidation raised although it soon becomes lower.
- Example VI The same oils described in Example V were tested for frictional characteristics in the Almen machine in steel to steel bearings with the following result:
E. 20+tetrahydro isopropyl pbthalato 7 The blended sample carried more than twice SEARCH ii the weight of the unblended oilv before breakdown.
The present is a continuation in Ser. No. 703,213 filed application This invention is not to be limited by any theory of the improvement which is wrought by the particular composition nor by any specific esters or oils but only by the following claims in which it is desired to claim all novelty inherent in the invention.
I claim:
1. A lubricating composition containing a major proportion of a viscous hydrocarbon lubrieating oil and a minor proportion of a phthalic ester.
2. A lubricant comprising a viscous hydrocar-. bon lubricating oil and a minor quantity up to about 10% of an ester of phthalicacid.
3. Lubricant according to claim 2 in which the ester is a monohydric alcoholic ester of phthalic acid. Y
4. Composition according to claim 2 in which Q 0 iii .the ester is a dialkyl ester derived from mono- 6. Composition according to claim 2 in which hydric alcohols and phthalic acid. the ester is dibutyl phthalate.
5. Composition according to claim 2 in which '7. Composition according to claim 2 in which /2 to 10% of a dialkyl ester of phthalic acid is the dialkyl ester is used, the ester being prepared 5 used, the alkyl groups being selected from the from a higher alcohol and phthalic acid. 5
lower alkyl radicals. GEORGE M. MAVERICK.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32380A US2215590A (en) | 1935-07-20 | 1935-07-20 | Lubricating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32380A US2215590A (en) | 1935-07-20 | 1935-07-20 | Lubricating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2215590A true US2215590A (en) | 1940-09-24 |
Family
ID=21864652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US32380A Expired - Lifetime US2215590A (en) | 1935-07-20 | 1935-07-20 | Lubricating composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2215590A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2430857A (en) * | 1942-07-14 | 1947-11-18 | California Research Corp | Foam inhibited oil |
| US2450435A (en) * | 1944-04-06 | 1948-10-05 | Bennett H Levenson | Polymers of vinyl chloride plasticized with a dioctyl phthalate and liquid petrolatum |
| US2454825A (en) * | 1948-11-30 | Viscosity reduction of petroleum | ||
| US2530804A (en) * | 1948-10-08 | 1950-11-21 | Automatic Elect Lab | Lubricating compound |
| US3108961A (en) * | 1959-12-21 | 1963-10-29 | Pure Oil Co | Improved anti-wear lubricating composition |
| US3151082A (en) * | 1961-09-05 | 1964-09-29 | Dow Chemical Co | Polyphenyl ether stabilizers |
| US3294500A (en) * | 1954-05-15 | 1966-12-27 | Bayer Ag | Fuel for internal combustion engines |
| DE1234205B (en) * | 1964-08-26 | 1967-02-16 | Metallgesellschaft Ag | Process for the production of low molecular weight olefins by thermal cracking of hydrocarbons |
| US3320041A (en) * | 1963-09-12 | 1967-05-16 | Union Oil Co | Jet fuel containing anti-wear aromatic diester |
| US3359302A (en) * | 1962-03-05 | 1967-12-19 | Celanese Corp | Bis (p-phenylphenyl) diphenate |
| US3542687A (en) * | 1967-09-29 | 1970-11-24 | Eastman Kodak Co | Compositions and processes for cleaning bearings |
| US3974081A (en) * | 1974-07-31 | 1976-08-10 | Exxon Research And Engineering Company | Biodegradable seal swell additive with low toxicity properties for automatic transmission fluids, power transmission fluids and rotary engine oil applications |
-
1935
- 1935-07-20 US US32380A patent/US2215590A/en not_active Expired - Lifetime
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454825A (en) * | 1948-11-30 | Viscosity reduction of petroleum | ||
| US2430857A (en) * | 1942-07-14 | 1947-11-18 | California Research Corp | Foam inhibited oil |
| US2450435A (en) * | 1944-04-06 | 1948-10-05 | Bennett H Levenson | Polymers of vinyl chloride plasticized with a dioctyl phthalate and liquid petrolatum |
| US2530804A (en) * | 1948-10-08 | 1950-11-21 | Automatic Elect Lab | Lubricating compound |
| US3294500A (en) * | 1954-05-15 | 1966-12-27 | Bayer Ag | Fuel for internal combustion engines |
| US3108961A (en) * | 1959-12-21 | 1963-10-29 | Pure Oil Co | Improved anti-wear lubricating composition |
| US3151082A (en) * | 1961-09-05 | 1964-09-29 | Dow Chemical Co | Polyphenyl ether stabilizers |
| US3359302A (en) * | 1962-03-05 | 1967-12-19 | Celanese Corp | Bis (p-phenylphenyl) diphenate |
| US3320041A (en) * | 1963-09-12 | 1967-05-16 | Union Oil Co | Jet fuel containing anti-wear aromatic diester |
| DE1234205B (en) * | 1964-08-26 | 1967-02-16 | Metallgesellschaft Ag | Process for the production of low molecular weight olefins by thermal cracking of hydrocarbons |
| US3542687A (en) * | 1967-09-29 | 1970-11-24 | Eastman Kodak Co | Compositions and processes for cleaning bearings |
| US3974081A (en) * | 1974-07-31 | 1976-08-10 | Exxon Research And Engineering Company | Biodegradable seal swell additive with low toxicity properties for automatic transmission fluids, power transmission fluids and rotary engine oil applications |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2134736A (en) | Lubricant | |
| US2215590A (en) | Lubricating composition | |
| US3180832A (en) | Oil compositions containing anti-wear additives | |
| US2158096A (en) | Lubricant | |
| US2353558A (en) | Addition agent for lubricating oil and method of making same | |
| US4664821A (en) | Lubricant additive concentrate containing isomerized jojoba oil | |
| US2203102A (en) | Lubricant | |
| US2179067A (en) | Lubricant | |
| US2344886A (en) | Lubricant composition | |
| US2326140A (en) | Lubricant | |
| US2149857A (en) | Oiliness agent in lubricating oils | |
| US3248327A (en) | Lubricating composition | |
| US2198851A (en) | Compounded lubricating oil | |
| US2122940A (en) | Lubricant | |
| US2813829A (en) | Grease compositions having improved yield, load bearing capacity, and low temperature properties | |
| US2113752A (en) | Lubricating oil | |
| US2289509A (en) | Lubricant | |
| US2119718A (en) | Lubricating oil | |
| US2173117A (en) | Lubricant | |
| US2231301A (en) | Lubricating composition | |
| US2243420A (en) | Lubricating composition | |
| US2268234A (en) | Lubricant | |
| US3032502A (en) | Lubricant compositions | |
| US2246059A (en) | Composition of matter | |
| US2211163A (en) | Lubricating oil composition |