US3632619A - Alkyl-substituted disiloxanes - Google Patents
Alkyl-substituted disiloxanes Download PDFInfo
- Publication number
- US3632619A US3632619A US14183A US3632619DA US3632619A US 3632619 A US3632619 A US 3632619A US 14183 A US14183 A US 14183A US 3632619D A US3632619D A US 3632619DA US 3632619 A US3632619 A US 3632619A
- Authority
- US
- United States
- Prior art keywords
- disiloxanes
- alkyl
- formula
- novel
- lubricants
- 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 abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract 1
- -1 alkyl radical Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004610 Internal Lubricant Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- HFDVRLIODXPAHB-UHFFFAOYSA-N alpha-tetradecene Natural products CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004512 die casting Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 229920001778 nylon Polymers 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid 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
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C10M2227/04—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 having a silicon-to-carbon bond, e.g. organo-silanes
Definitions
- the present invention relates to novel disiloxanes. More particularly, these disiloxanes are of the formula in which each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms and each R is independently selected from the group consisting of methyl and phenyl radicals.
- Silicone chemistry has reached a stage of detailed development. Most of the technology is focused on the monomeric silanes and on higher polymeric siloxanes, such as used for lubricants or elastomers. Relatively little effort has been expended in the area of disiloxanes, the polysiloxanes containing the least number of silicon atoms.
- the higher alkyl substituted disiloxane of the invention includes and mixtures thereof.
- An alternate method involves the preparation of RR (CH SiCl by the reaction of HR'(CH )SiCl with the described unsaturated hydrocarbon in the presence of chloroplatinic acid and subsequent hydrolysis of the product chlorosilane to obtain the disiloxane. Conventional hydrolysis techniques are utilized.
- the disiloxanes containing the shorter chain alkyl substituents are low viscosity fluids at room temperatures, while the higher alkyl substituted compounds are solid waxy materials.
- the disiloxanes of the invention exhibit much greater resistance to gelling at elevated temperatures. This high temperature stability is a particular advantage in applications, such as die casting, where buildup of the lubricant or release agent is undesirable.
- the novel disiloxanes function as internal lubricants when used as additives for thermal plastic materials, such as nylon, providing greater ease of extrusion of such materials.
- the (Cgf-Czg)(CH3)2SiOSi(CH3)2(C22-C2g) species is especially preferred in that it not only provides internal lubrication but significantly improves the impact strength of polyamide extrusions at the one weight percent additive level.
- EXAMPLE 1 A 3-liter flask fitted with a mechanical stirrer, thermometer, addition funnel and condenser was charged with 1357 grams (6.92 mols) of l-tetradecene. To this, was added 0.2 milliliter of a chloroplatinic acid solution (0.1 molar chloroplatinic acid in isopropanol). The solution was stirred and heated to C. and 421.8 grams (3.18 mols) of H(CH SiOSi(CH H was added slowly from the addition funnel at a rate suflicient to keep the reaction temperature at C. The reaction was exothermic. When all the disiloxane had been added, the solution temperature was maintained at 120 overnight while stirring to complete the reaction.
- a chloroplatinic acid solution 0.1 molar chloroplatinic acid in isopropanol
- the reaction product was stripped at a temperature of 204 C./0.4 mm. Hg of hydrogen to remove the unreacted olefin.
- the product was cooled, treated with activated carbon and filtered to obtain 1419 grams of C H (CH SiOSi(CH C I-I disiloxane Was a clear water-white fluid having a viscosity of 20.2 cs. at 77 F., a flash point of 475 F. and a freezing point of 18 C.
- EXAMPLE 2 A five-liter flask, fitted with mechanical stirrer, thermometer, reflux condenser and addition funnel was charged with 1855 grams (6.5 mols) of a normal alpha olefin fraction containing species having from 22-28 inclusive carbon atoms and 0.5 milliliter of 0.1 molar chloroplatinic acid in isopropanol. This mixture was heated to C. while stirring moderately and 360 grams of H(CH SiOSi(CH H was added at such a rate that the exotherm from the reaction was maintained at a temperature from 125 to 150 C.
- reaction product was stripped at 260 under vacuum to remove the unreacted olefin. It was then cooled, treated with activated carbon and filtered to obtain a mixture product of the formula 22 45 2s 57) 3 zsiosi 3 2( z2 45 2a 57) which was a white waxy material having a melting point of 35-45 C.
- Disiloxanes of the formula 1a s7( a)2 3)2 1a a'1 and (C16H33"'C20H41) 3 asiosi 3 2 1s a3 20 41) were produced by reacting the corresponding alpha-olefin with the disiloxane utilizing the above described method.
- This chlorosilane adduct can be hydrolyzed by the addition of water to yield a low viscosity fluid of the formula C14H29(C6H5) 3) 3) s) 14 29- EXAMPLE 4
- the lubrication properties and gel times of the various disiloxanes were determined by the 4-ball method in which a /2 inch steel ball is rotated against three stationary /2 inch steel balls at a rate of 1200 r.p.m. at a temperature of 167 F. for 30 minutes under loads of 4, and 40 kilograms. At the end of this time, the length and width of the scar formed on each stationary ball is measured and the average of these six measurements is taken as the wear scar diameter. The smaller the wear scar, the better the lubricant.
- the gel times an indication of stability at high temperatures, were determined by placing 10 grams of the disiloxane contained in a 50 ml. beaker in an air circulating oven at 450 F. and recording the time necessary to eifect gellation of the fluid.
- each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms; and each R is independently selected from the group consisting of methyl and phenyl radicals.
- each R is a methyl radical and R is selected from the group consisting of alkyl radicals having from 22-28 carbon atoms, and mixtures thereof.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Silicon Polymers (AREA)
- Lubricants (AREA)
Abstract
NOVEL DISILOXANES OF THE FORMULA RR''(CH3)SIOSI(CH3)R''R IN WHICH R IS AN ALKYL RADICAL OF FROM 14 TO 30 CARBON ATOMS AND R'' IS A METHYL OR PHENYL RADICAL, HAVE UTILITY AS LUBRICANTS AND RELEASE AGENTS.
Description
United States Patent ()1 hoe 3,632,619 Patented Jan. 4, 1972 US. Cl. 260448.2 R 4 Claims ABSTRACT OF THE DISCLOSURE Novel disiloxanes of the formula RR'(CH )SiOSi(CH )RR in which R is an alkyl radical of from 14 to 30 carbon atoms and R is a methyl or phenyl radical, have utility as lubricants and release agents.
The present invention relates to novel disiloxanes. More particularly, these disiloxanes are of the formula in which each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms and each R is independently selected from the group consisting of methyl and phenyl radicals.
Silicone chemistry has reached a stage of detailed development. Most of the technology is focused on the monomeric silanes and on higher polymeric siloxanes, such as used for lubricants or elastomers. Relatively little effort has been expended in the area of disiloxanes, the polysiloxanes containing the least number of silicon atoms.
By the practice of the present invention, there is provided a class of novel disiloxanes which have utility as lubricants and release agents.
The higher alkyl substituted disiloxane of the invention includes and mixtures thereof.
The novel disiloxanes of the invention can be prepared by reacting H(R)CH SiOSiCH (R)H with unsaturated hydrocarbons of the formula CH=CH (CH CH or with mixtures of such hydrocarbons in the presence of a platinum catalyst such as chloroplatinic acid. An alternate method involves the preparation of RR (CH SiCl by the reaction of HR'(CH )SiCl with the described unsaturated hydrocarbon in the presence of chloroplatinic acid and subsequent hydrolysis of the product chlorosilane to obtain the disiloxane. Conventional hydrolysis techniques are utilized.
The disiloxanes containing the shorter chain alkyl substituents (C C are low viscosity fluids at room temperatures, while the higher alkyl substituted compounds are solid waxy materials. As compared to longer chain polymeric siloxanes, the disiloxanes of the invention exhibit much greater resistance to gelling at elevated temperatures. This high temperature stability is a particular advantage in applications, such as die casting, where buildup of the lubricant or release agent is undesirable.
In addition to being lubricants in the normal sense of the word, as used on moving metal surfaces, the novel disiloxanes function as internal lubricants when used as additives for thermal plastic materials, such as nylon, providing greater ease of extrusion of such materials. The (Cgf-Czg)(CH3)2SiOSi(CH3)2(C22-C2g) species is especially preferred in that it not only provides internal lubrication but significantly improves the impact strength of polyamide extrusions at the one weight percent additive level.
The following examples are illustrative, and are not intended to limit the invention which is properly delineated in the claims.
EXAMPLE 1 A 3-liter flask fitted with a mechanical stirrer, thermometer, addition funnel and condenser was charged with 1357 grams (6.92 mols) of l-tetradecene. To this, was added 0.2 milliliter of a chloroplatinic acid solution (0.1 molar chloroplatinic acid in isopropanol). The solution was stirred and heated to C. and 421.8 grams (3.18 mols) of H(CH SiOSi(CH H was added slowly from the addition funnel at a rate suflicient to keep the reaction temperature at C. The reaction was exothermic. When all the disiloxane had been added, the solution temperature was maintained at 120 overnight while stirring to complete the reaction.
The reaction product was stripped at a temperature of 204 C./0.4 mm. Hg of hydrogen to remove the unreacted olefin. The product was cooled, treated with activated carbon and filtered to obtain 1419 grams of C H (CH SiOSi(CH C I-I disiloxane Was a clear water-white fluid having a viscosity of 20.2 cs. at 77 F., a flash point of 475 F. and a freezing point of 18 C.
EXAMPLE 2 A five-liter flask, fitted with mechanical stirrer, thermometer, reflux condenser and addition funnel was charged with 1855 grams (6.5 mols) of a normal alpha olefin fraction containing species having from 22-28 inclusive carbon atoms and 0.5 milliliter of 0.1 molar chloroplatinic acid in isopropanol. This mixture was heated to C. while stirring moderately and 360 grams of H(CH SiOSi(CH H was added at such a rate that the exotherm from the reaction was maintained at a temperature from 125 to 150 C.
After the addition was complete, the reaction mixture was heated at C. overnight to complete the reaction.
The reaction product was stripped at 260 under vacuum to remove the unreacted olefin. It was then cooled, treated with activated carbon and filtered to obtain a mixture product of the formula 22 45 2s 57) 3 zsiosi 3 2( z2 45 2a 57) which was a white waxy material having a melting point of 35-45 C.
Disiloxanes of the formula 1a s7( a)2 3)2 1a a'1 and (C16H33"'C20H41) 3 asiosi 3 2 1s a3 20 41) were produced by reacting the corresponding alpha-olefin with the disiloxane utilizing the above described method.
EXAMPLE 3 When equimolar amounts of C H (CH )SiClH and tetradecene-l are reacted at about C. in the presence of chloroplatinic acid a higher alkyl substituted silane of the formula C H (C H (CH )SiCl is obtained. This chlorosilane adduct can be hydrolyzed by the addition of water to yield a low viscosity fluid of the formula C14H29(C6H5) 3) 3) s) 14 29- EXAMPLE 4 The lubrication properties and gel times of the various disiloxanes were determined by the 4-ball method in which a /2 inch steel ball is rotated against three stationary /2 inch steel balls at a rate of 1200 r.p.m. at a temperature of 167 F. for 30 minutes under loads of 4, and 40 kilograms. At the end of this time, the length and width of the scar formed on each stationary ball is measured and the average of these six measurements is taken as the wear scar diameter. The smaller the wear scar, the better the lubricant.
The gel times, an indication of stability at high temperatures, were determined by placing 10 grams of the disiloxane contained in a 50 ml. beaker in an air circulating oven at 450 F. and recording the time necessary to eifect gellation of the fluid.
The disiloxanes tested were:
Results are as follows:
Disiloxane No.1 No.2 No.3 No.4
Viscosity (cs.at 210F.) 3.9 5.6 6.0 8.7 Wear-scar (mm.) at load I 40kg 1.52 1.23 1.51 1.08 Geltlme(hrs.) 24-40 48 52 These data demonstrate that the disiloxanes of the invention are good lubricants. When compared to a gel time 4 of 11 hours for (CH SiO[C H -,(CH )SiO] Si(CH the high temperature stability of the novel disiloxanes is apparent.
Reasonable modification and variation are within the scope of the invention which is directed to novel disiloxanes.
That which is claimed is:
1. An organosilicon composition of the formula RR CH SiOSi CH R'R in which each R is independently selected from the group consisting of alkyl radicals having from 14 to 30 inclusive carbon atoms; and each R is independently selected from the group consisting of methyl and phenyl radicals.
2. The composition of claim 1 in which each R is a methyl radical.
3. The composition of claim 1 in which R is a phenyl radical.
4. The compound of claim 1 in which each R is a methyl radical and R is selected from the group consisting of alkyl radicals having from 22-28 carbon atoms, and mixtures thereof.
References Cited UNITED STATES PATENTS 2,451,664 10/1948 Daudt 260448.2 R 2,469,888 5/1948 Patnode 260448.2 R 2,486,162 10/1949 Hyde 260-448.2 R X 2,489,139 11/1949 Hyde et a1 260448.2 R 2,521,673 9/1950 Britton et a1. 260-4482 R X 2,992,263 7/1961 Brown 260-4482 R TOBIAS E. LEVOW, Primary Examiner P. F. SHAVER, Assistant Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1418370A | 1970-02-25 | 1970-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3632619A true US3632619A (en) | 1972-01-04 |
Family
ID=21763997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14183A Expired - Lifetime US3632619A (en) | 1970-02-25 | 1970-02-25 | Alkyl-substituted disiloxanes |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3632619A (en) |
| JP (1) | JPS4832547B1 (en) |
| BE (1) | BE763364A (en) |
| DE (1) | DE2109051C3 (en) |
| FR (1) | FR2079015A5 (en) |
| GB (1) | GB1282839A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756052A (en) * | 1971-12-27 | 1973-09-04 | Dow Corning | Metal working lubricant |
| US4564467A (en) * | 1982-12-31 | 1986-01-14 | Exxon Research And Engineering Co. | Oil composition |
| US5232693A (en) * | 1992-03-09 | 1993-08-03 | Dow Corning Corporation | Method of treating dry skin |
| US5738857A (en) * | 1993-03-02 | 1998-04-14 | Wacker-Chemie Gmbh | Cosmetic compositions comprising organosiloxanes |
| US20060241266A1 (en) * | 2003-02-05 | 2006-10-26 | Lucile Gambut-Garel | Method for the production of polymethylvinylsiloxane resins wtih recycling of volatile oligoorganosiloxanes |
| WO2015153004A3 (en) * | 2014-03-31 | 2016-02-25 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51111665U (en) * | 1975-03-07 | 1976-09-09 |
-
1970
- 1970-02-25 US US14183A patent/US3632619A/en not_active Expired - Lifetime
- 1970-10-22 JP JP45092462A patent/JPS4832547B1/ja active Pending
-
1971
- 1971-02-24 FR FR7106301A patent/FR2079015A5/fr not_active Expired
- 1971-02-24 BE BE763364A patent/BE763364A/en unknown
- 1971-02-25 DE DE2109051A patent/DE2109051C3/en not_active Expired
- 1971-04-19 GB GB20316/71A patent/GB1282839A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3756052A (en) * | 1971-12-27 | 1973-09-04 | Dow Corning | Metal working lubricant |
| US4564467A (en) * | 1982-12-31 | 1986-01-14 | Exxon Research And Engineering Co. | Oil composition |
| US5232693A (en) * | 1992-03-09 | 1993-08-03 | Dow Corning Corporation | Method of treating dry skin |
| US5738857A (en) * | 1993-03-02 | 1998-04-14 | Wacker-Chemie Gmbh | Cosmetic compositions comprising organosiloxanes |
| US20060241266A1 (en) * | 2003-02-05 | 2006-10-26 | Lucile Gambut-Garel | Method for the production of polymethylvinylsiloxane resins wtih recycling of volatile oligoorganosiloxanes |
| US7750077B2 (en) * | 2003-02-05 | 2010-07-06 | Bluestar Silicones France | Method for the production of polymethylvinylsiloxane resins with recycling of volatile oligoorganosiloxanes |
| WO2015153004A3 (en) * | 2014-03-31 | 2016-02-25 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
| US9822326B2 (en) | 2014-03-31 | 2017-11-21 | Exxonmobil Research And Engineering Company | Low viscosity, low volatility lubricating oil basestocks |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2079015A5 (en) | 1971-11-05 |
| DE2109051C3 (en) | 1974-06-27 |
| DE2109051B2 (en) | 1973-11-15 |
| BE763364A (en) | 1971-08-24 |
| GB1282839A (en) | 1972-07-26 |
| DE2109051A1 (en) | 1971-09-09 |
| JPS4832547B1 (en) | 1973-10-06 |
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