US2096905A - Lubricating oil of high oiliness and resistance to oxidation - Google Patents
Lubricating oil of high oiliness and resistance to oxidation Download PDFInfo
- Publication number
- US2096905A US2096905A US37302A US3730235A US2096905A US 2096905 A US2096905 A US 2096905A US 37302 A US37302 A US 37302A US 3730235 A US3730235 A US 3730235A US 2096905 A US2096905 A US 2096905A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- oxidation
- oil
- resistance
- small quantity
- 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
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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
Definitions
- the present invention relates to improved lubricating oils, ,especially to oils of higher re ment in one respect is detrimental in the other.
- the aromatic ring may be phenolic or of the l0- condensed form such as naphthalene or anthracene and the alkylated aromatic rings may also be used. Hydroxyl or amino groups may be present on the ring without .detrimentally afiecting the value of the compounds. Often indeed it is 35 found to be improved by their presence.
- the aromatic-sulpho-radlcal may be present in the alcoholic or the acidic portion of the ester molecule and more than one of these groups is oftendesirable.
- the alcoholic portion of the i0 ester may be an aromatic alcohol or phenol or it may be an aliphatic radical containing a substituted sulpho-aromatic group. It may be mo'iiohydric or polyhydric aswill be illustrated below.
- the acidic portion of the ester molecule may 15 contain the sulpho-arom'atic group whether or not such a group is a part of the. alcoholic radical.
- Mono or poly basic acids may be employed.
- esters are for the most part freely soluble in lubricating oils, but only relatively small quantitles are necessary for the present purposes.
- a gen-absorption is determined at 15 minute intervals by notingv the volume; of the undissolved oxygen.
- Animproved lubricant comprising a lubricoating oil and a small quantity of an ester containing :ai sulphur atom directly connected to an aromatic group and being a'compound'selected' a from the class consisting of aromatic disulphides, a i
- An improved lubricant comprising a mineral lubricating oil' and a small quantity of an estera containing an aromatic-mercapto group.
- An improved lubricant comprising a lubrieating oil and a small quantity of an ester containing an esterified mercapto-phenol.
- An improved lubricant comprising a hy:-
- clrocarbon lubricating oil and a small quantity E P- a ;8.:
- An' improved lubricant comprising a lubricating oil and a small quantity of an esterifie disulphide of a phenolic compound.
- An improvedlubricant comprising a disulphide of aphenol.
- I 10 An improved lubricant comprising a lubrian aromatic thio-ether group.
- Anwimprovedlubricant comprising a lubrieating oilland a small quantity of an esterified' phenolic compound with a thin-ether group.
- An improved lubricant comprising a lubrieating oil aind'a' small quantity of an esterifled' phenol containinga thio-ether group'., a I y l 13; An improved lubricant comprising a lubricating oil and a small quantity of an esterified diphenol thio-ether.
- An improved lubricant comprising a. lubrieating oil and a small quantity of esterified alkyl diphenol thio-ether.
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
Patented Oct. 26, 1937 NITE STATES PATENT OFFICE LUBRICATING OIL OF HIGH OILINESS AND RESISTANCE T OXIDATION I Eugene Lieber, Linden, N. 1., assignor to seamiard Oil Development Company, a corporation of Delaware No Drawing.
14 Claim.
The present invention relates to improved lubricating oils, ,especially to oils of higher re ment in one respect is detrimental in the other.
In the present instance, a new class of lubricating oil improvers is disclosed which simultane- .5 ously works an improvement in the oil both in respect to resistance to oxidation and to its oiliness value.
The particular class of substances which has been discovered at this time comprises the 'esters and tellurium directly attached to an aromatic ring. Sulphur may be combined with the rings as mercaptan, disulphide or monosulphide, that is to say, thioether is quite efiective when utilized in any of these threeforms. These groups will be included in the term sulpho-aromatic groups but it will be understood that equivalents of the sulfur atom are included.
The aromatic ring may be phenolic or of the l0- condensed form such as naphthalene or anthracene and the alkylated aromatic rings may also be used. Hydroxyl or amino groups may be present on the ring without .detrimentally afiecting the value of the compounds. Often indeed it is 35 found to be improved by their presence.
The aromatic-sulpho-radlcal may be present in the alcoholic or the acidic portion of the ester molecule and more than one of these groups is oftendesirable. The alcoholic portion of the i0 ester may be an aromatic alcohol or phenol or it may be an aliphatic radical containing a substituted sulpho-aromatic group. It may be mo'iiohydric or polyhydric aswill be illustrated below.
4 The acidic portion of the ester molecule may 15 contain the sulpho-arom'atic group whether or not such a group is a part of the. alcoholic radical. Mono or poly basic acids may be employed.
, In order more explicitly to disclose the type of compounds which fall within the class dis- 50 closed above, the following formulae are given,
which contain sulphur or its equivalents, selenium Application August 22, 1935, Serial No. 37,302
but it will be understood that these are merely illustrations and are in no way limitative.
T I s-O-ons-oocmmm s-GdocoJn-m The esters are for the most part freely soluble in lubricating oils, but only relatively small quantitles are necessary for the present purposes. As
little as .01% is sufficient to greatly reduce the rate of oxidation of the oil, but more is usually preferred, say from .5 to 1% or even 2% or 5% or more may be desired to obtain the greatest oiliness values. I
Experiment I I I To an SAE 50 hydrocarbon lubricating oil is added .5% of an'acetic acid ester of iii-tertiary butyl diphenol sulphide. Runs were made on. the
oil blank sample which did not contain these /sub tances' and on thejble'nd, using the Mou y machine and 'method as' described on page 47 in the National Petroleum Newsof Novemberll, I
oxidation, 'The blendedand unblended samples were subjected toan oxidation test'in which oxy- The -oil;blend wasverystable in respect to gen was bubbled through the sample in a con t'inuous circulatory stream at a fixed rate while the sample was held; at 200 C. The rate of oily:
a gen-absorption is determined at 15 minute intervals by notingv the volume; of the undissolved oxygen. W
I 1 v I Oxidation rataatZOO 0. cc. cl 0, Samples absorbed [15 min. interval [10 I ccusample Blankin LEE-213+?! Blended 30r-3 1-,%,29 a t l The present' invention is not limited to any theory of the improving agents nor to any parx ticular agent mentioned in the disclosure, but
only'to the following claims in w hich it is de- '2. An improved lubricant comprising a lubri eating oil and a' small quantity of an ester con,-
, taming a sulphur atom directlyconnected to an aromatic group.
' 8. Animproved lubricant comprising a lubricoating oil and a small quantity of an ester containing :ai sulphur atom directly connected to an aromatic group and being a'compound'selected' a from the class consisting of aromatic disulphides, a i
mercaptans and thio-ethers' 4. An improved lubricant comprising a mineral lubricating oil' and a small quantity of an estera containing an aromatic-mercapto group.
- 5. An improved lubricant comprising a petro-, I
15 I ester containing an esterified mercapto-phenolic V leum lubricating oil and a small quantity of an compound.
,6. An improved lubricant comprisinga lubrieating oil and a small quantity of an ester containing an esterified mercapto-phenol. I I I a "I. An improved lubricant comprising a hy:-
clrocarbon lubricating oil: and a small quantity E P- a ;8.: An' improved lubricant comprising a lubricating oil and a small quantity of an esterifie disulphide of a phenolic compound. y
9. An improvedlubricantcomprising a disulphide of aphenol. I 10; An improved lubricant comprising a lubrian aromatic thio-ether group. a 11. Anwimprovedlubricant comprising a lubrieating oilland a small quantity of an esterified' phenolic compound with a thin-ether group. v
a 12; An improved lubricant comprising a lubrieating oil aind'a' small quantity of an esterifled' phenol containinga thio-ether group'., a I y l 13; An improved lubricant comprising a lubricating oil and a small quantity of an esterified diphenol thio-ether.
14. An improved lubricant comprising a. lubrieating oil and a small quantity of esterified alkyl diphenol thio-ether.
EUGENE LIEBER.
lubrieating oil and'a small quantity of an esterified a a of. an ester containing an aromatic disulphide .cating oil and a'small quantity of an ester with I
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL44036D NL44036C (en) | 1935-08-22 | ||
| US37302A US2096905A (en) | 1935-08-22 | 1935-08-22 | Lubricating oil of high oiliness and resistance to oxidation |
| GB19527/36A GB466075A (en) | 1935-08-22 | 1936-07-14 | Improved lubricants |
| FR808657D FR808657A (en) | 1935-08-22 | 1936-07-24 | Lubricating oil |
| DEST55106D DE748243C (en) | 1935-08-22 | 1936-08-01 | lubricant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37302A US2096905A (en) | 1935-08-22 | 1935-08-22 | Lubricating oil of high oiliness and resistance to oxidation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2096905A true US2096905A (en) | 1937-10-26 |
Family
ID=21893603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US37302A Expired - Lifetime US2096905A (en) | 1935-08-22 | 1935-08-22 | Lubricating oil of high oiliness and resistance to oxidation |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2096905A (en) |
| DE (1) | DE748243C (en) |
| FR (1) | FR808657A (en) |
| GB (1) | GB466075A (en) |
| NL (1) | NL44036C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423865A (en) * | 1944-02-28 | 1947-07-15 | Shell Dev | Anticorrosive |
| US2451037A (en) * | 1941-05-13 | 1948-10-12 | Texas Co | Lubricating oil |
| US2885420A (en) * | 1956-01-27 | 1959-05-05 | Du Pont | Stabilization of organic isocyanates |
| WO2001051155A1 (en) | 2000-01-07 | 2001-07-19 | Mattel, Inc. | Toy slot track racing vehicles |
-
0
- NL NL44036D patent/NL44036C/xx active
-
1935
- 1935-08-22 US US37302A patent/US2096905A/en not_active Expired - Lifetime
-
1936
- 1936-07-14 GB GB19527/36A patent/GB466075A/en not_active Expired
- 1936-07-24 FR FR808657D patent/FR808657A/en not_active Expired
- 1936-08-01 DE DEST55106D patent/DE748243C/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451037A (en) * | 1941-05-13 | 1948-10-12 | Texas Co | Lubricating oil |
| US2423865A (en) * | 1944-02-28 | 1947-07-15 | Shell Dev | Anticorrosive |
| US2885420A (en) * | 1956-01-27 | 1959-05-05 | Du Pont | Stabilization of organic isocyanates |
| WO2001051155A1 (en) | 2000-01-07 | 2001-07-19 | Mattel, Inc. | Toy slot track racing vehicles |
Also Published As
| Publication number | Publication date |
|---|---|
| NL44036C (en) | |
| GB466075A (en) | 1937-05-21 |
| DE748243C (en) | 1944-10-31 |
| FR808657A (en) | 1937-02-12 |
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