GB1569730A - 0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it - Google Patents
0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it Download PDFInfo
- Publication number
- GB1569730A GB1569730A GB24607/78A GB2460778A GB1569730A GB 1569730 A GB1569730 A GB 1569730A GB 24607/78 A GB24607/78 A GB 24607/78A GB 2460778 A GB2460778 A GB 2460778A GB 1569730 A GB1569730 A GB 1569730A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- lubricating oil
- carboethoxyethyl
- phosphorodithioate
- 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
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 10
- 239000000203 mixture Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 11
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- NFPBWZOKGZKYRE-UHFFFAOYSA-N 2-propan-2-ylperoxypropane Chemical compound CC(C)OOC(C)C NFPBWZOKGZKYRE-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- 239000005069 Extreme pressure additive Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000010722 industrial gear oil Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2223/047—Thioderivatives not containing metallic elements
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/02—Bearings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
Description
(54) O ;O-DIISOPROPYL-S-(CARBOETHOXYETHYL)PHOSPHORODITHIOATE
AND LUBRICATING OIL COMPOSITIONS CONTAINING IT
(71) We CIBA-GEIGY AG, a Swiss Body Corporate, of Basle, Switzerland, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:
In the British Patent Application No. 4296/70, which was published on August 31, 1972, as Patent Specification No. 1 287 331, a class of phosphorodithioates was claimed having the general formula I XiCO-CH(R)-CH2-S-P(S) (OR1) (OR2) Z I wherein R is hydrogen or an alkyl radical containing from 1 to 3 carbon atoms, R1 and R2 are the same or different and are hydrocarbyl radicals, containing from 1 to 20 carbon atoms unsubstituted or substituted by one or more halogen atoms or alkoxy groups, Z is an integer from 1 to 6, and X is an alkoxy radical derived from an aliphatic alcohol having from 2 to 20 carbon atoms and containing from 1 to 6 hydroxyl groups. This patent specification was amended under Section 29 of the Patent Act 1949 and subsequently reprinted on 19th
April 1973. The patent now claims a compound having the above formula I where R is hydrogen or an alkyl radical containing from 1 to 3 carbon atoms, R1 and R2 are the same or different and are hydrocarbyl radicals containing from 1 to 20 carbon atoms unsubstituted or substituted by one or more halogen atoms or alkoxy groups, Z is an integer from 2 to 6, and X is an alkoxy radical derived from an aliphatic alcohol having from 2 to 20 carbon atoms and containing from 2 to 6 hydroxyl groups. The compounds are claimed to be useful as antioxidants and extreme pressure additives for lubricants.
It has now been found that one particular compound of formula I wherein Z is 1, shows interesting properties as an oil additive, this compound being 0,0-diisopropyl-S-(2-carbo ethoxyethyl -phosphorodithioate.
Therefore the instant invention relates to the compound of the formula II (iso-C3H7O)2P(S)-S-CH2CH2COOC2Hs II as well as to compositions comprising a lubricating oil and the compound of formula II in an amount of 0.1 to 5% by weight based on the weight of the lubricating oil.
The compound of formula II is a new chemical compound which may be prepared by the addition of ethyl acrylate to 0,0-diisopropyl phosphorodithioic acid.
The lubricating oil may be a mineral oil or a synthetic oil or a mixture of both types of oil.
It may further contain other additives which are conventionally used to improve the oil properties, such as metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, or other antioxidants and extreme pressure additives. Preferably, the compound of formula II is present in an amount of 0.1 to 3% by weight based on the weight of the lubricating oil.
The lubricating oil compositions containing the compound of formula II show excellent friction modifying characteristics and outstanding anticorrosive properties in contact with iron, silver, brass, copper or similar metals. Therefore such lubricating oil compositions are highly useful as industrial gear oils, hydraulic oils, slideway lubricants, metal working oils, or engine oils and for the manufacture of lubricating greases.
The following Examples further illustrate the invention.
Example 1
621.6 g of phosphorus pentasulfide and 1392 g of toluene are charged to a 4 1-vessel and heated to 800C with agitation. 672 g of isopropanol are added dropwise within 90 minutes at this temperature. The evolved hydrogen sulfide is absorbed in a wash bottle filled with
NaOH solution. The reaction is continued at 80"C until all P255 has reacted and a clear solution is obtained which contains 0,0-diisopropyl-phosphorodithioic acid. 504 g of ethyl acrylate is then added dropwise at 80"C within 90 minutes and heating is continued for 3 hours. The reaction mixture is cooled to room temperature and filtered. The filtrate is washed with aqueous sodium carbonate solution and afterwards with water to neutrality.
The washed toluene solution is dried over Na2SO4 and after filtration the solvent is removed in a rotating vacuum evaporator.
The residue (1554 g) is an amber oil showing an analytical content of 9,9% phosphorus and 20,5% sulfur. The theoretical values for 0,0-diisopropyl-S-(2-carboethoxyethyl)phosphoro-dithioate are 9,87% P and 20,38% S.
The yield is 98% based on the used ethyl acrylate.
Example 2
To show the extreme pressure properties and anti-wear properties the compound of formula II was tested in a 4-Ball Lubricant Testing Apparatus using 500-Solvent neutral (a mineral oil) as oil base. The tests were carried out according to IP 239 or DIN 51 530 by measuring the Initial Seizure Load (ISL), the Weld Load (WL) and the Wear Scar
Diameter (WSD) when a load of either 70 Kg or 40 Kg has been applied for 1 hour.
ISL WL WSD
Oil with additive 60 kg 160 kg 70 kg 40 kg
2.4 mm 0.85 mm
Oil with 1% by weight of compound of formula 100 kg 240 kg 0.8 mm 0.35 mm
Example 3
According to DIN 51 354 the extreme pressure characteristics for gear oils were tested in a FZG-apparatus using 150-Solvent neutral (mineral oil) by measuring the failure load stage (Schadens-Kraftstufe):
Without additive failure load stage 6 0.5% b.w. compound of formula II ,, > 12 0.25% b.w. compound of formula II " 12
Example 4
On an IAE Gear Machine the extreme pressure characteristics were measured according to IP 166, test condition B (pinion speed 4000 revolutions per minute, test oil temperature 70"C, test oil flow 1 pint per minute) using 500-Solvent neutral (a mineral oil). The failure loads were as follows:
Without additive 50 lb failure load 0.25% b.w. compound 125 lb failure load of formula II
From Examples 2, 3 and 4 it is clear that the compound of formula II significantly
enhances the load carrying ability (extreme pressure activity) of the mineral oil.
Claims (6)
1. A compound having the formula II
(iso-C3H7O)2 P(S)-S-CH2-CH2-COOC2Hs II
2. A process of preparing a compound having the formula II which comprises adding ethyl acrylate to 0,0-diisopropyl phosphorodithioic acid.
3. A process as claimed in claim 2 substantially as described in Example 1. 1.
4. A compound having the formula II whenever prepared by a process according to claim 2 or claim 3.
5. A composition comprising a lubricating oil and the compound of formula II in an amount of 0.1 to 5% by weight based on the weight of the lubricating oil.
6. A composition as claimed in claim 5 substantially as described in any of Examples 2 to 4.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24607/78A GB1569730A (en) | 1978-05-30 | 1978-05-30 | 0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it |
| NL7904137A NL7904137A (en) | 1978-05-30 | 1979-05-25 | A DITHIOPHOSPHORIC ACID EESTER AND ITS USE AS AN ADDITIVE FOR LUBRICATING OIL. |
| DE19792921620 DE2921620A1 (en) | 1978-05-30 | 1979-05-28 | A NEW DITHIOPHOSPHORIC ACID ESTER AND ITS USE AS A LUBRICANT ADDITIVE |
| IT23111/79A IT1121528B (en) | 1978-05-30 | 1979-05-29 | DI-THIO-PHOSPHORIC ACID ESTER AND ITS USE AS AN ADDITIVE FOR LUBRICANT OILS |
| FR7913610A FR2427338A2 (en) | 1978-05-30 | 1979-05-29 | NEW PHOSPHORODITHIOATE AND ITS USE AS AN ADDITIVE FOR LUBRICANTS |
| BE0/195444A BE876605A (en) | 1978-05-30 | 1979-05-29 | NEW PHOSPHORODITHIOATE AND ITS USE AS AN ADDITIVE FOR LUBRICANTS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24607/78A GB1569730A (en) | 1978-05-30 | 1978-05-30 | 0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1569730A true GB1569730A (en) | 1980-06-18 |
Family
ID=10214329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24607/78A Expired GB1569730A (en) | 1978-05-30 | 1978-05-30 | 0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE876605A (en) |
| DE (1) | DE2921620A1 (en) |
| FR (1) | FR2427338A2 (en) |
| GB (1) | GB1569730A (en) |
| IT (1) | IT1121528B (en) |
| NL (1) | NL7904137A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734210A (en) * | 1985-07-30 | 1988-03-29 | Ciba-Geigy Corporation | Additives for lubricant compositions |
| US4808324A (en) * | 1986-04-04 | 1989-02-28 | Lonza Ltd. | Lubricant system for sheet and section rolling mills |
| US4965005A (en) * | 1987-09-17 | 1990-10-23 | Ciba-Geigy Corporation | Aminomethyl derivatives of monothiocarbamates and dithiocarbamates as additives for lubricants |
| US5346635A (en) * | 1993-06-03 | 1994-09-13 | Material Innovation, Inc. | Low and light ash oils |
| WO1995010584A1 (en) * | 1993-10-12 | 1995-04-20 | Behrooz Khorramian | Low and light ash lubricating oils |
| US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
| US6660695B2 (en) * | 2002-03-15 | 2003-12-09 | Infineum International Ltd. | Power transmission fluids of improved anti-shudder properties |
| EP1871861B1 (en) | 2005-04-08 | 2020-01-15 | The Lubrizol Corporation | Additive system for lubricants |
| EP4438699A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Antiwear system for improved copper corrosion |
| EP4438701A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Antiwear system for improved copper corrosion |
| CN119060089A (en) * | 2024-09-06 | 2024-12-03 | 青岛市资源化学与新材料研究中心 | A dialkyl dithiophosphate compound and its preparation method and application as grease additive |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772405A (en) * | 1985-08-26 | 1988-09-20 | Ciba-Geigy Corporation | Lubricant compositions which contain sulfur-containing phenol derivatives, and novel sulfur-containing phenol derivatives |
| CH668265A5 (en) * | 1985-09-09 | 1988-12-15 | Lonza Ag | METHOD FOR THE PRODUCTION OF LUBRICANTS IN POWDERED TO PASTOESE FORM. |
| US5271854A (en) * | 1986-09-23 | 1993-12-21 | Lonza Ltd. | High temperature lubricant containing carboxylated styrene-butadiene latex |
| CH674096A5 (en) * | 1988-01-19 | 1990-04-30 | Lonza Ag | |
| CH674477A5 (en) * | 1988-03-30 | 1990-06-15 | Lonza Ag | |
| US5099667A (en) * | 1989-06-16 | 1992-03-31 | Lonza Ltd. | System for suspending and applying solid lubricants to tools or work pieces |
| FR2789084B1 (en) * | 1999-01-28 | 2001-03-09 | Lorraine Laminage | OIL-IN-WATER EMULSION COMPRISING AT LEAST ONE LUBRICATION ADDITIVE |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2645657A (en) * | 1949-03-30 | 1953-07-14 | Standard Oil Dev Co | Thiophosphate esters |
-
1978
- 1978-05-30 GB GB24607/78A patent/GB1569730A/en not_active Expired
-
1979
- 1979-05-25 NL NL7904137A patent/NL7904137A/en not_active Application Discontinuation
- 1979-05-28 DE DE19792921620 patent/DE2921620A1/en not_active Ceased
- 1979-05-29 FR FR7913610A patent/FR2427338A2/en active Granted
- 1979-05-29 BE BE0/195444A patent/BE876605A/en not_active IP Right Cessation
- 1979-05-29 IT IT23111/79A patent/IT1121528B/en active
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4734210A (en) * | 1985-07-30 | 1988-03-29 | Ciba-Geigy Corporation | Additives for lubricant compositions |
| US4808324A (en) * | 1986-04-04 | 1989-02-28 | Lonza Ltd. | Lubricant system for sheet and section rolling mills |
| US4965005A (en) * | 1987-09-17 | 1990-10-23 | Ciba-Geigy Corporation | Aminomethyl derivatives of monothiocarbamates and dithiocarbamates as additives for lubricants |
| US5346635A (en) * | 1993-06-03 | 1994-09-13 | Material Innovation, Inc. | Low and light ash oils |
| US5439605A (en) * | 1993-06-03 | 1995-08-08 | Khorramian; Behrooz A. | Phosphorus and phosphours-free low and light ash lubricating oils |
| WO1995010584A1 (en) * | 1993-10-12 | 1995-04-20 | Behrooz Khorramian | Low and light ash lubricating oils |
| US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
| US6660695B2 (en) * | 2002-03-15 | 2003-12-09 | Infineum International Ltd. | Power transmission fluids of improved anti-shudder properties |
| EP1871861B1 (en) | 2005-04-08 | 2020-01-15 | The Lubrizol Corporation | Additive system for lubricants |
| EP4438699A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Antiwear system for improved copper corrosion |
| EP4438701A1 (en) * | 2023-03-31 | 2024-10-02 | Afton Chemical Corporation | Antiwear system for improved copper corrosion |
| JP2024146889A (en) * | 2023-03-31 | 2024-10-15 | アフトン・ケミカル・コーポレーション | Anti-wear systems for improved copper corrosion |
| CN119060089A (en) * | 2024-09-06 | 2024-12-03 | 青岛市资源化学与新材料研究中心 | A dialkyl dithiophosphate compound and its preparation method and application as grease additive |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2427338A2 (en) | 1979-12-28 |
| DE2921620A1 (en) | 1979-12-13 |
| BE876605A (en) | 1979-11-29 |
| IT7923111A0 (en) | 1979-05-29 |
| IT1121528B (en) | 1986-04-02 |
| FR2427338B2 (en) | 1982-05-28 |
| NL7904137A (en) | 1979-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |