US3108966A - Lubricant containing copper corrosion inhibitor - Google Patents
Lubricant containing copper corrosion inhibitor Download PDFInfo
- Publication number
- US3108966A US3108966A US51277A US5127760A US3108966A US 3108966 A US3108966 A US 3108966A US 51277 A US51277 A US 51277A US 5127760 A US5127760 A US 5127760A US 3108966 A US3108966 A US 3108966A
- Authority
- US
- United States
- Prior art keywords
- copper corrosion
- thioether
- carbon atoms
- esters
- corrosion inhibitor
- 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
- 239000000314 lubricant Substances 0.000 title claims description 15
- 238000005260 corrosion Methods 0.000 title description 22
- 230000007797 corrosion Effects 0.000 title description 22
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title description 20
- 229910052802 copper Inorganic materials 0.000 title description 20
- 239000010949 copper Substances 0.000 title description 20
- 239000003112 inhibitor Substances 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 4
- 150000003568 thioethers Chemical class 0.000 claims description 4
- -1 thioether esters Chemical class 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 150000007970 thio esters Chemical class 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- RLGKZWXCACVYRU-UHFFFAOYSA-N (2-methoxycarbonylphenoxy)boronic acid Chemical compound COC(=O)C1=CC=CC=C1OB(O)O RLGKZWXCACVYRU-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric 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
- 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
- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; 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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
Definitions
- This invention relates to additives for synthetic base ester type lubricants. More particularly, this invention is directed to additives that inhibit copper corrosion in sulfurcontaining synthetic oils.
- the copper corrosion problem encountered with the use of the thioether ester lubricants is further complicated by the fact that known copper corrosion inhibitors have proven unsuccessful in inhibiting copper corrosion encountered with the thioether ester base lubricants.
- the advantage of the present invention is that the additives herein disclosed when incorporated in the thioether ester base lubricants materially reduce and in most cases eliminate the copper corrosion which is caused by these thio esters, thereby making such synthetic lubricants available for general use without the problem of encountering copper corrosion.
- esters of hydrocarbyl carboxylic acids containing at least one thioether linkage are broadly described as esters of hydrocarbyl carboxylic acids containing at least one thioether linkage. They are high molecular weight materials of lubricating oil characteristics derived from alcohols, which are usually aliphatic alcohols containing one or more hydroxyl radicals and carboxylic acids, which are usually aliphatic acids containing one or more carboxylic acid radicals and containing one or more thioether linkages. eral formula:
- R is a divalent aliphatic hydrocarby-l radical containing 1 to 14 carbon atoms, but may also be thioether monoacids of the formula:
- RSRCOOH wherein R is a monovalent hydrocarbyl radical containing 1 to 14 or more carbon atoms and R is a divalent radical as previously defined.
- the acid moiety of these thioether esters usually contain 6 to 18 carbon atoms, preferably from 6to 14.
- the aliphatic alcohols from which the thioether esters are formed usually contain at least 4
- the thioether acids usually have the gen- 7 "ice carbon atoms and up to 20 or more carbon atoms. Alcohols containing 6 to 18 carbon atoms are most commonly used.
- Ether alcohols such as C H -O-C H OH and C H --O-C H -O-CH CH -OH or thioether alcohols such as C H SC H OH may also be used in the formation of the aliphatic thioether diesters of organic dicarboxylic acids making up the lubricating base in the composition of the present invention.
- alkyl esters of aliphatic thioether dicarboxylic acids have the following general formula:
- R is a divalent aliphatic hydrocarbyl radical containing from 1 to 18 carbon atoms and preferably from 2 to l4carb1on atoms, and R is a monovalen-t hydrocar-byl radical containing 3 to 12 carbon atoms and preferably 3 to 8 carbon atoms.
- di-2-ethylhexylthiodibutyrate di-isooctyl thiodibutyrate
- di-2-ethylhexyl-/3,/3-thiodipropionate di-isooctyl-Bfi thiodipropionate
- di-2,2,4-trimethylpentyl thiodibntyrate di-2-ethylhexylthiodibutyrate, di-isooctyl thiodibutyrate, di-2-ethylhexyl-/3,/3-thiodipropionate
- di-isooctyl-Bfi thiodipropionate di-2,2,4-trimethylpentyl thiodibntyrate.
- An example of one method of preparing such aliphatic esters of thioether acids is by refluxing the acids with an excess of the appropriate alcohols in the presence of a water entrainer.
- the inhibitors for copper corrosion used in the present invention are borate esters having the following general formula:
- R may be either the same or different organic radicals selected from the group consisting of alkyl, aryl, alkaryl, aralkyl and halo, nitro and carbonyl substitutes thereof, containing 6 to 15 carbon atoms.
- the inmate inhibitors of the present invention are usually present in an amount of from about 0.5 to 5.0 weight percent with concentrations of between 1.0 and 3.0 weight percent being preferred.
- Examples of the copper corrosion inhibitors of the present invention are di-(nonylphenyl) mono-o-nitrophenyl borate, di-(nonylphenyl) mono-o-formylphenyl bonate, mono-nonylphenyl di-p-chlorophenyl borate, di-(nonylphenyl) mono-o-acetylphenyl bonate, tri-o-carbomethoxyphenyl borate, di-p-tertiary-butylphenyl mono-o-carbomethoxyphenyl borate.
- Finished lubricant compositions containing the anticorrcsive additive of the present invention may also contain other well-known additives such as VI improvers, anti-oxidants, extreme pressure additives, and anti-foam agents.
- bomb copper corrosion test which is a rather severe test, described in military specification MIL-C7118A, Federal Specification VV-L79153 14 a an accelerated test, designed to evaluate lubricants under high temperature oxidizing conditions.
- the results of the bomb copper corrosion test are listed below in Table I.
- crys a s. 6..-. Di-Z-ethylhcxylthio-dibutyrate N, N -disalicylidene -1- Z-dieminopro 0 Black Black stain Do.
- yl borate 1. y w. 8..- Di-2-ethylhexyl -fl, 3 -thiodipropio- Dti;(ninylphenyl)mono-o-nitrophenyl 0 Unchanged Unchanged Do.
- a lubricating composition consisting essentially of a synthetic thioether ester base lubricant having the following general formula:
- R is a divalent aliphatic hydrocarbyl radical containing from 1 to 18 carbon atoms and R is a monovalent hydrocarbyl radical containing 3 to 12 carbon atoms and a copper corrosion inhibitor having the following general formula:
- a lubricating composition consisting essentially of a synthetic thioet-her ester base lubricant having the following general formula:
- R is a divalent hydrocarbyl radical containing from 1 to 18 carbon atoms and R is a monovalent hydro carbyl radical containing from 3 to 12 carbon atoms and 0.5 to 5 .0 weight percent of di-p-tertiarybutylphenyl monoo-carbomethoxyphenyl borate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
United States Patent 3,108,966 LUBRICANT CONTAINING COPPER CORROSION INHIBITOR James G. Dadura, Fishkill, William Raymond Siegart, Wappingers Falls, Norman R. Odell, Fishkill, and Clemence J. Henry, Newburgh, N.Y., assignors to Texaco Inc, New York, N.Y., a corporation of Delaware N0 Drawing. Filed Aug. 23, 1960, Ser. No. 51,277
3 Claims. (Cl. 252-463) This invention relates to additives for synthetic base ester type lubricants. More particularly, this invention is directed to additives that inhibit copper corrosion in sulfurcontaining synthetic oils.
It has been found that some sulfur-containing ester base lubricants, such as thiodibutyra-te esters compare favorably with other well known and well used ester base lubricants, such as sebacate esters of equivalent molecular Weight, with respect to viscosity and viscosity-temperature properties. It has also been found that the thioether esters are considerably less volatile than the standard lu bricating esters. Howeventhese sulfur-containing thioether ester base oils cause considerable copper corrosion, whereas the other well known and well used non-sulfurcontaining ester base lubricants have shown no such corrosion problems, and because of this the use of the thioether esters, at present, is strictly limited. The copper corrosion problem encountered with the use of the thioether ester lubricants is further complicated by the fact that known copper corrosion inhibitors have proven unsuccessful in inhibiting copper corrosion encountered with the thioether ester base lubricants. The advantage of the present invention is that the additives herein disclosed when incorporated in the thioether ester base lubricants materially reduce and in most cases eliminate the copper corrosion which is caused by these thio esters, thereby making such synthetic lubricants available for general use without the problem of encountering copper corrosion.
The thio esters to which the corrosion inhibitors of the present invention are added are broadly described as esters of hydrocarbyl carboxylic acids containing at least one thioether linkage. They are high molecular weight materials of lubricating oil characteristics derived from alcohols, which are usually aliphatic alcohols containing one or more hydroxyl radicals and carboxylic acids, which are usually aliphatic acids containing one or more carboxylic acid radicals and containing one or more thioether linkages. eral formula:
wherein R is a divalent aliphatic hydrocarby-l radical containing 1 to 14 carbon atoms, but may also be thioether monoacids of the formula:
RSRCOOH wherein R is a monovalent hydrocarbyl radical containing 1 to 14 or more carbon atoms and R is a divalent radical as previously defined. The acid moiety of these thioether esters usually contain 6 to 18 carbon atoms, preferably from 6to 14. The aliphatic alcohols from which the thioether esters are formed usually contain at least 4 The thioether acids usually have the gen- 7 "ice carbon atoms and up to 20 or more carbon atoms. Alcohols containing 6 to 18 carbon atoms are most commonly used. Ether alcohols such as C H -O-C H OH and C H --O-C H -O-CH CH -OH or thioether alcohols such as C H SC H OH may also be used in the formation of the aliphatic thioether diesters of organic dicarboxylic acids making up the lubricating base in the composition of the present invention.
The alkyl esters of aliphatic thioether dicarboxylic acids have the following general formula:
wherein R is a divalent aliphatic hydrocarbyl radical containing from 1 to 18 carbon atoms and preferably from 2 to l4carb1on atoms, and R is a monovalen-t hydrocar-byl radical containing 3 to 12 carbon atoms and preferably 3 to 8 carbon atoms. Examples of these are the following: di-2-ethylhexylthiodibutyrate, di-isooctyl thiodibutyrate, di-2-ethylhexyl-/3,/3-thiodipropionate, di-isooctyl-Bfi thiodipropionate, and di-2,2,4-trimethylpentyl thiodibntyrate.
An example of one method of preparing such aliphatic esters of thioether acids is by refluxing the acids with an excess of the appropriate alcohols in the presence of a water entrainer.
The inhibitors for copper corrosion used in the present invention are borate esters having the following general formula:
wherein R may be either the same or different organic radicals selected from the group consisting of alkyl, aryl, alkaryl, aralkyl and halo, nitro and carbonyl substitutes thereof, containing 6 to 15 carbon atoms.
The inmate inhibitors of the present invention are usually present in an amount of from about 0.5 to 5.0 weight percent with concentrations of between 1.0 and 3.0 weight percent being preferred.
Examples of the copper corrosion inhibitors of the present invention are di-(nonylphenyl) mono-o-nitrophenyl borate, di-(nonylphenyl) mono-o-formylphenyl bonate, mono-nonylphenyl di-p-chlorophenyl borate, di-(nonylphenyl) mono-o-acetylphenyl bonate, tri-o-carbomethoxyphenyl borate, di-p-tertiary-butylphenyl mono-o-carbomethoxyphenyl borate.
Finished lubricant compositions containing the anticorrcsive additive of the present invention may also contain other well-known additives such as VI improvers, anti-oxidants, extreme pressure additives, and anti-foam agents.
The effectiveness of the anti-corrosive additive of the present invention was demonstrated in the bomb copper corrosion test, which is a rather severe test, described in military specification MIL-C7118A, Federal Specification VV-L79153 14 a an accelerated test, designed to evaluate lubricants under high temperature oxidizing conditions. The results of the bomb copper corrosion test are listed below in Table I.
Table 1 Appearance 7 Ex. Base oil Additive(s) (weight percent) gsi. Rating top Sample Strip 1.-.. Di-n-octylisosebacate Unchanged No stain Pass. 2.-.. Di-2-ethylhexyl-tLB-thiodipr0pio- 29 Solid; yellow brown Brown stain above Fail.
nate. and green. interface. 3.... Diisooctylthio-dibutyrate 0 Green Dark brovm stain... Do. 4..-. Di-2,2,4-trimethyl-pentylthiodibu- 0 .d0 do Do.
tyrato. 5..-. Diisooctyl-Bfi thio dipropionate..... Zinc dialkyldithio-phosphate (2.7).... 94 Yellov: llWith white do Do.
crys a s. 6..-. Di-Z-ethylhcxylthio-dibutyrate N, N -disalicylidene -1- Z-dieminopro 0 Black Black stain Do.
pane 7.. -r..do Di-(nonylphenyl)-mono-o formylphen 0 Light brownish Light brown stain. Pass.
yl borate 1. y w. 8..- Di-2-ethylhexyl -fl, 3 -thiodipropio- Dti;(ninylphenyl)mono-o-nitrophenyl 0 Unchanged Unchanged Do.
na ora e 9..-. Di-Z-ethylhexylthio-dibutyrate Di-p-tertiarybutylphenyl mono-o-car- 0 Yellow Light gray stain- Do.
bomethoxyphenyl borate.
From the above data it can be seen that while synthetic ester base oils do not cause copper corrosion (Example 1) the uninhibited thio esters do cause much copper corrosion (Examples 2, 3 and 4). In addition, the above data demonstrate that conventional copper corrosion inhibitors are ineifective in preventing copper corrosion by the thio esters (Examples 5 and 6) whereas When the inhibitors of the present invention are added without conventional copper corrosion inhibitor they all pass the bomb copper corrosion test (Examples 7-9).
We claim:
1. A lubricating composition consisting essentially of a synthetic thioether ester base lubricant having the following general formula:
wherein R is a divalent aliphatic hydrocarbyl radical containing from 1 to 18 carbon atoms and R is a monovalent hydrocarbyl radical containing 3 to 12 carbon atoms and a copper corrosion inhibitor having the following general formula:
2. A lubricating composition consisting essentially of a synthetic thioet-her ester base lubricant having the following general formula:
wherein R is a divalent hydrocarbyl radical containing from 1 to 18 carbon atoms and R is a monovalent hydro carbyl radical containing from 3 to 12 carbon atoms and 0.5 to 5 .0 weight percent of di-p-tertiarybutylphenyl monoo-carbomethoxyphenyl borate.
R References Cited in the file of this patent I UNITED STATES PATENTS g 2,160,917 Shoemaker et al. June 6, 1939 2,559,521 Smith et a1 July 3, 1951 wherein two of said R"s represent alkylphenyl radicals 2,961,443 Ashby et a1 Nov. 22, 1960 each having from 6 to 15' carbon atoms and the third R" represents a radical selected from the group consisting of formylphenyl and oarbomethoxyphenyl radicals having from 6 to 15 carbon atoms, said inhibitor being present in an amount between 0.5 and 5.0 weight percent.
OTHER REFERENCES K'alichev-sky et al.: Chemical Refining of Petroleum, publ. by Reinhold Publishing Corp, New York, N.Y., 1942, pp. 398-400,
Claims (1)
1. A LUBRICATING COMPOSITION CONSISTING ESSENTIALLY OF A SYNTHETIC THIOETHER ESTER BASE LUBRICANT HAVING THE FOLLOWING GENERAL FORMULA.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51277A US3108966A (en) | 1960-08-23 | 1960-08-23 | Lubricant containing copper corrosion inhibitor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51277A US3108966A (en) | 1960-08-23 | 1960-08-23 | Lubricant containing copper corrosion inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3108966A true US3108966A (en) | 1963-10-29 |
Family
ID=21970323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US51277A Expired - Lifetime US3108966A (en) | 1960-08-23 | 1960-08-23 | Lubricant containing copper corrosion inhibitor |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3108966A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200074A (en) * | 1963-05-20 | 1965-08-10 | Texaco Inc | Lubricating compositions containing borate ester-amine complexes |
| US3303130A (en) * | 1965-11-02 | 1967-02-07 | Gulf Research Development Co | Lubricant compositions containing organo mercaptoalkyl borates |
| US3755178A (en) * | 1971-07-29 | 1973-08-28 | Monsanto Co | Compositions comprising boron compounds and polyphenyl thioethers |
| US3755175A (en) * | 1971-07-29 | 1973-08-28 | Monsanto Co | Compositions comprising boron compounds and polyphenyl thioethers |
| JPS52103590A (en) * | 1976-01-30 | 1977-08-30 | Sanyo Chemical Ind Ltd | Fiber treating agent |
| JPS52103591A (en) * | 1976-01-30 | 1977-08-30 | Sanyo Chemical Ind Ltd | Fiber treating agent |
| US5033415A (en) * | 1987-06-22 | 1991-07-23 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
| US2559521A (en) * | 1948-11-27 | 1951-07-03 | Standard Oil Dev Co | Synthetic lubricant |
| US2961443A (en) * | 1957-04-10 | 1960-11-22 | Ethyl Corp | Organic compounds of boron |
-
1960
- 1960-08-23 US US51277A patent/US3108966A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160917A (en) * | 1937-06-10 | 1939-06-06 | Standard Oil Co | Lubricant |
| US2559521A (en) * | 1948-11-27 | 1951-07-03 | Standard Oil Dev Co | Synthetic lubricant |
| US2961443A (en) * | 1957-04-10 | 1960-11-22 | Ethyl Corp | Organic compounds of boron |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3200074A (en) * | 1963-05-20 | 1965-08-10 | Texaco Inc | Lubricating compositions containing borate ester-amine complexes |
| US3303130A (en) * | 1965-11-02 | 1967-02-07 | Gulf Research Development Co | Lubricant compositions containing organo mercaptoalkyl borates |
| US3755178A (en) * | 1971-07-29 | 1973-08-28 | Monsanto Co | Compositions comprising boron compounds and polyphenyl thioethers |
| US3755175A (en) * | 1971-07-29 | 1973-08-28 | Monsanto Co | Compositions comprising boron compounds and polyphenyl thioethers |
| JPS52103590A (en) * | 1976-01-30 | 1977-08-30 | Sanyo Chemical Ind Ltd | Fiber treating agent |
| JPS52103591A (en) * | 1976-01-30 | 1977-08-30 | Sanyo Chemical Ind Ltd | Fiber treating agent |
| JPS559115B2 (en) * | 1976-01-30 | 1980-03-07 | ||
| JPS559114B2 (en) * | 1976-01-30 | 1980-03-07 | ||
| US5033415A (en) * | 1987-06-22 | 1991-07-23 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
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