US2384577A - Esters - Google Patents
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- Publication number
- US2384577A US2384577A US524922A US52492244A US2384577A US 2384577 A US2384577 A US 2384577A US 524922 A US524922 A US 524922A US 52492244 A US52492244 A US 52492244A US 2384577 A US2384577 A US 2384577A
- Authority
- US
- United States
- Prior art keywords
- sodium
- dichloride
- parts
- methylene
- dibromide
- 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
- 150000002148 esters Chemical class 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- -1 alkylene dithiocarbamates Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- QNTARNCGFNQQRP-UHFFFAOYSA-N 5-carbamothioylsulfanylpentyl carbamodithioate Chemical compound NC(=S)SCCCCCSC(N)=S QNTARNCGFNQQRP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- IULVMSRZVAOLEB-UHFFFAOYSA-N azepane-1-carbodithioic acid Chemical compound SC(=S)N1CCCCCC1 IULVMSRZVAOLEB-UHFFFAOYSA-N 0.000 description 1
- MRVHGCMXWNDJBQ-UHFFFAOYSA-N benzyl carbamodithioate Chemical compound NC(=S)SCC1=CC=CC=C1 MRVHGCMXWNDJBQ-UHFFFAOYSA-N 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- PEEFBAYDEKJSPE-UHFFFAOYSA-N dicyclohexylcarbamodithioic acid Chemical compound C1CCCCC1N(C(=S)S)C1CCCCC1 PEEFBAYDEKJSPE-UHFFFAOYSA-N 0.000 description 1
- SVEFOVSCPCGMJS-UHFFFAOYSA-N dimethylcarbamothioylsulfanylmethyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SCSC(=S)N(C)C SVEFOVSCPCGMJS-UHFFFAOYSA-N 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QTBJMPHMDBGPKY-UHFFFAOYSA-L magnesium;n,n-dibutylcarbamodithioate Chemical compound [Mg+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC QTBJMPHMDBGPKY-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ICNCMCHAPLUNBG-UHFFFAOYSA-N propyl carbamodithioate Chemical compound CCCSC(N)=S ICNCMCHAPLUNBG-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- DVHOMPKWTYENNE-UHFFFAOYSA-M sodium;morpholine-4-carbodithioate Chemical compound [Na+].[S-]C(=S)N1CCOCC1 DVHOMPKWTYENNE-UHFFFAOYSA-M 0.000 description 1
- DVAUUBZODGVYMT-UHFFFAOYSA-M sodium;n-butylcarbamodithioate Chemical compound [Na+].CCCCNC([S-])=S DVAUUBZODGVYMT-UHFFFAOYSA-M 0.000 description 1
- RJAXVDQEAVACNL-UHFFFAOYSA-M sodium;n-cyclohexylcarbamodithioate Chemical compound [Na+].[S-]C(=S)NC1CCCCC1 RJAXVDQEAVACNL-UHFFFAOYSA-M 0.000 description 1
- PBOZLWAJUOCHAY-UHFFFAOYSA-M sodium;n-ethyl-n-phenylcarbamodithioate Chemical compound [Na+].CCN(C([S-])=S)C1=CC=CC=C1 PBOZLWAJUOCHAY-UHFFFAOYSA-M 0.000 description 1
- PZFBFVVXYPHDJH-UHFFFAOYSA-M sodium;n-methyl-n-phenylcarbamodithioate Chemical compound [Na+].[S-]C(=S)N(C)C1=CC=CC=C1 PZFBFVVXYPHDJH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
Definitions
- This invention relates to allwlene dithiocarbamates and to their preparation.
- This invention has as an object the production of new and useful compositions of matter.
- a further object is the preparation of alkylene dithiocarbamates.
- Other objects will appear hereinafter.
- R and R1 are selected from the class consisting or hydrogen, hydrocarbon radicals which, together jointly with the nitrogen, form a heterocycllc ring and R2 is a bivalent acyclic hydrocarbon radical.
- Acycllc dihaloalkanes which are operative in the process of this invention, in addition to methylene dichloride, include methylene dibromide, ethylene dichloride, ethylene dibromide, ethylene dilodide, trimethylene dibromide, hexamethylene dichloride, decamethylene dibromide and ethylidene dichloride.
- Solvents other than ethyl alcohol can be used as the medium for the-preparation of the alkylene dithiocarbamates. These include alcohols such as methyl alcohol, propyl alcohol, and isobutyl alcohol; ketones such as acetone and methyl ethyl ketone; ethers suchas diethyl ether, dibutyl ether and dioxane; and hydrocarbons such as petroleum ether, benzene and toluene.
- alcohols such as methyl alcohol, propyl alcohol, and isobutyl alcohol
- ketones such as acetone and methyl ethyl ketone
- ethers suchas diethyl ether, dibutyl ether and dioxane
- hydrocarbons such as petroleum ether, benzene and toluene.
- the reaction is generally carried out at a temperature within the range of 25 to 0. However, it'is convenient to operate at the boilins point of the solvent used as the reaction medium.
- the products of this invention are useful for various commercial purposes. They may be used as harmaceutical and pest-control agents, e. g., insecticides, fungicides, moth-proofing agents, and as additive agents for elastomers.
- harmaceutical and pest-control agents e. g., insecticides, fungicides, moth-proofing agents, and as additive agents for elastomers.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Sept. 11, 1945 ESTEBS John C. Thomas, Wilmington, Del., assignor to E. l. du Pont de Nemours & Company, Wilmington, Del., a corporation of Delaware No Drawing. Application March 3, 1944, Serial No. 524,922
1 Claim.
This invention relates to allwlene dithiocarbamates and to their preparation.
This invention has as an object the production of new and useful compositions of matter. A further object is the preparation of alkylene dithiocarbamates. Other objects will appear hereinafter.
These objects are accomplished by the following invention which comprises reacting a salt of a dithiocarbamic acid with a dlhalo acyclic hydrocarbon as more fully described hereinafter.
The products of this invention are represented by the following formula wherein not more than one hydrogen is attached to each nitrogen, i. e., at least two valences of each nitrogen are attached to carbon, R and R1 are selected from the class consisting or hydrogen, hydrocarbon radicals which, together jointly with the nitrogen, form a heterocycllc ring and R2 is a bivalent acyclic hydrocarbon radical.
The more detailed practice of the invention is illustrated by the following example wherein parts given are by weight. There are, of course, many forms or the invention other than this specific embodiment.
Example A mixture of 188 parts of. sodium dimethyldithiocarbamate and 85 parts of methylene dichloride in 520 parts of ethyl alcohol was refiuxed with stirring for two hours- The reaction mixture was then cooled in an ice bath and the solution filtered. The solid reaction product was twice washed with ethyl alcohol and then washed thoroughly with water. There was obtained 127 parts of methylene bis-dimethyldithiocarbamate, melting at 154 C. Anaylsis: Calculated for C-1HuNzS4: N, 11.03; found: N, 11.02.
Although the invention is illustrated by the reaction of sodium dimethyldithiocarbamate with methylene dichloride, it is applicable to salts or dithiocarbamic acids in general. Ex-
propyldithiocarbamate,
yldithiocarbamate,
amples of other salts of dithiocarbamic acids which are operative include sodium methyldithiocarbamate, sodium butyldithiocarbamate, sodium cyclohexyldithiocarbamate, sodium phensodium benzyldithiocarbamate, zinc diethyldithiocarbamate, magnesium dibutyldithiocarbamate, potassium diisosodium dicyclohexyldithiocarbamate, sodium ethylphenyldithiocarbamate, sodium dibenzyldlthiocarbamate, sodium pentamethylenedithiocarbamate, sodium hexamethylenedithiocarbamate, sodium methylphenyldithiocarbamate and sodium 4-morpholinecarbodithioate.
Acycllc dihaloalkanes which are operative in the process of this invention, in addition to methylene dichloride, include methylene dibromide, ethylene dichloride, ethylene dibromide, ethylene dilodide, trimethylene dibromide, hexamethylene dichloride, decamethylene dibromide and ethylidene dichloride.
Solvents other than ethyl alcohol can be used as the medium for the-preparation of the alkylene dithiocarbamates. These include alcohols such as methyl alcohol, propyl alcohol, and isobutyl alcohol; ketones such as acetone and methyl ethyl ketone; ethers suchas diethyl ether, dibutyl ether and dioxane; and hydrocarbons such as petroleum ether, benzene and toluene.
The reaction is generally carried out at a temperature within the range of 25 to 0. However, it'is convenient to operate at the boilins point of the solvent used as the reaction medium.
The products of this invention are useful for various commercial purposes. They may be used as harmaceutical and pest-control agents, e. g., insecticides, fungicides, moth-proofing agents, and as additive agents for elastomers.
As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that this invention is not limited to the specific embodiments thereof except as defined in the appended claim.
What is claimed is:
Methylene bisldimethyldithiocarbamate) JOHN C. THOMAS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US524922A US2384577A (en) | 1944-03-03 | 1944-03-03 | Esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US524922A US2384577A (en) | 1944-03-03 | 1944-03-03 | Esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2384577A true US2384577A (en) | 1945-09-11 |
Family
ID=24091193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US524922A Expired - Lifetime US2384577A (en) | 1944-03-03 | 1944-03-03 | Esters |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2384577A (en) |
Cited By (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501191A (en) * | 1945-07-31 | 1950-03-21 | Goodrich Co B F | N, n'-polythioamines as pesticides |
| US3046189A (en) * | 1957-05-18 | 1962-07-24 | Merck Ag E | Nematocidal agents |
| US3050552A (en) * | 1959-01-30 | 1962-08-21 | Rohm & Haas | Stable anhydrous disodium ethylene bisdithiocarbamate |
| US3202571A (en) * | 1959-04-13 | 1965-08-24 | Vondelingen Plaat Bv | New fungicidal compounds |
| US3852065A (en) * | 1970-05-14 | 1974-12-03 | Oce Van Der Grinten Nv | Photoconductive bisphenyl thiocompounds linked by bridging organic group |
| US3876550A (en) * | 1974-04-15 | 1975-04-08 | Lubrizol Corp | Lubricant compositions |
| US3885039A (en) * | 1971-08-20 | 1975-05-20 | M & I Chemicals Inc | Antifouling compositions |
| US3950534A (en) * | 1973-08-01 | 1976-04-13 | Nippon Soda Company, Ltd. | Fungicidal composition containing 2-(N-n-butylcarbamoylthio) ethyl N1 -n-butyl-thiocarbamate |
| US4011230A (en) * | 1973-01-12 | 1977-03-08 | American Cyanamid Company | Dithiocarbamate ester bactericides and fungicides |
| US4297295A (en) * | 1976-09-17 | 1981-10-27 | Stauffer Chemical Company | N-(Benzenesulfonyl) thiocarbamates-herbicidal antidotes |
| US4356025A (en) * | 1979-12-31 | 1982-10-26 | Stauffer Chemical Company | N-(Benzenesulfonyl) thiocarbamates - herbicidal antidotes |
| WO1992005837A1 (en) * | 1990-10-05 | 1992-04-16 | Eastman Kodak Company | Dichloromethane abatement |
| US6599865B1 (en) | 2002-07-12 | 2003-07-29 | Ethyl Corporation | Effective antioxidant combination for oxidation and deposit control in crankcase lubricants |
| US20060205615A1 (en) * | 2005-03-14 | 2006-09-14 | Esche Carl K Jr | Additives and lubricant formulations for improved antioxidant properties |
| US20070111907A1 (en) * | 2005-11-16 | 2007-05-17 | Esche Carl K Jr | Additives and lubricant formulations for providing friction modification |
| US20070135317A1 (en) * | 2005-12-12 | 2007-06-14 | Tze-Chi Jao | Nanosphere additives and lubricant formulations containing the nanosphere additives |
| US20070132274A1 (en) * | 2005-12-09 | 2007-06-14 | Lam William Y | Titanium-containing lubricating oil composition |
| US20070149418A1 (en) * | 2005-12-22 | 2007-06-28 | Esche Carl K Jr | Additives and lubricant formulations having improved antiwear properties |
| US20070254820A1 (en) * | 2006-04-28 | 2007-11-01 | Tze-Chi Jao | Diblock monopolymers as lubricant additives and lubricant formulations containing same |
| US20080132432A1 (en) * | 2006-12-01 | 2008-06-05 | Mathur Naresh C | Additives and lubricant formulations for providing friction modification |
| US20080161213A1 (en) * | 2007-01-03 | 2008-07-03 | Tze-Chi Jao | Nanoparticle additives and lubricant formulations containing the nanoparticle additives |
| DE102008009042A1 (en) | 2007-05-08 | 2008-11-13 | Afton Chemical Corp. | Additive and lubricant formulations for improved phosphorus retention properties |
| US20080280796A1 (en) * | 2007-05-08 | 2008-11-13 | Guinther Gregory H | Additives and lubricant formulations for improved catalyst performance |
| US20090069205A1 (en) * | 2007-09-10 | 2009-03-12 | Devlin Mark T | Additives and lubricant formulations having improved antiwear properties |
| US20090111722A1 (en) * | 2007-10-25 | 2009-04-30 | Guinther Gregory H | Engine wear protection in engines operated using ethanol-based fuel |
| US7615519B2 (en) | 2004-07-19 | 2009-11-10 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
| EP2135925A1 (en) | 2008-06-18 | 2009-12-23 | Afton Chemical Corporation | Method for making a titanium-containing lubricant additive |
| US20100035774A1 (en) * | 2008-08-08 | 2010-02-11 | Afton Chemical Corporation | Lubricant additive compositions having improved viscosity index increase properties |
| US7682526B2 (en) | 2005-12-22 | 2010-03-23 | Afton Chemical Corporation | Stable imidazoline solutions |
| US20100144563A1 (en) * | 2008-12-09 | 2010-06-10 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
| EP2251401A2 (en) | 2009-05-15 | 2010-11-17 | Afton Chemical Corporation | Lubricant formulations and methods |
| US20100292112A1 (en) * | 2009-05-14 | 2010-11-18 | Afton Chemical Corporation | Extended drain diesel lubricant formulations |
| EP2261311A1 (en) | 2009-06-10 | 2010-12-15 | Afton Chemical Corporation | Lubricating method and composition for reducing engine deposits |
| WO2011119918A1 (en) | 2010-03-25 | 2011-09-29 | R.T. Vanderbilt Company, Inc. | Ultra low phosphorus lubricant compositions |
| EP2489637A1 (en) | 2011-02-17 | 2012-08-22 | Afton Chemical Corporation | Cerium oxide nanoparticle additives and lubricant formulations containing the nanoparticle additives |
| US8377856B2 (en) | 2009-05-14 | 2013-02-19 | Afton Chemical Corporation | Extended drain diesel lubricant formulations |
| WO2013182581A1 (en) | 2012-06-06 | 2013-12-12 | Evonik Oil Additives Gmbh | Fuel efficient lubricating oils |
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-
1944
- 1944-03-03 US US524922A patent/US2384577A/en not_active Expired - Lifetime
Cited By (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501191A (en) * | 1945-07-31 | 1950-03-21 | Goodrich Co B F | N, n'-polythioamines as pesticides |
| US3046189A (en) * | 1957-05-18 | 1962-07-24 | Merck Ag E | Nematocidal agents |
| US3050552A (en) * | 1959-01-30 | 1962-08-21 | Rohm & Haas | Stable anhydrous disodium ethylene bisdithiocarbamate |
| US3202571A (en) * | 1959-04-13 | 1965-08-24 | Vondelingen Plaat Bv | New fungicidal compounds |
| US3852065A (en) * | 1970-05-14 | 1974-12-03 | Oce Van Der Grinten Nv | Photoconductive bisphenyl thiocompounds linked by bridging organic group |
| US3885039A (en) * | 1971-08-20 | 1975-05-20 | M & I Chemicals Inc | Antifouling compositions |
| US4011230A (en) * | 1973-01-12 | 1977-03-08 | American Cyanamid Company | Dithiocarbamate ester bactericides and fungicides |
| US3950534A (en) * | 1973-08-01 | 1976-04-13 | Nippon Soda Company, Ltd. | Fungicidal composition containing 2-(N-n-butylcarbamoylthio) ethyl N1 -n-butyl-thiocarbamate |
| US3876550A (en) * | 1974-04-15 | 1975-04-08 | Lubrizol Corp | Lubricant compositions |
| US4297295A (en) * | 1976-09-17 | 1981-10-27 | Stauffer Chemical Company | N-(Benzenesulfonyl) thiocarbamates-herbicidal antidotes |
| US4356025A (en) * | 1979-12-31 | 1982-10-26 | Stauffer Chemical Company | N-(Benzenesulfonyl) thiocarbamates - herbicidal antidotes |
| WO1992005837A1 (en) * | 1990-10-05 | 1992-04-16 | Eastman Kodak Company | Dichloromethane abatement |
| US6599865B1 (en) | 2002-07-12 | 2003-07-29 | Ethyl Corporation | Effective antioxidant combination for oxidation and deposit control in crankcase lubricants |
| US7615519B2 (en) | 2004-07-19 | 2009-11-10 | Afton Chemical Corporation | Additives and lubricant formulations for improved antiwear properties |
| US20060205615A1 (en) * | 2005-03-14 | 2006-09-14 | Esche Carl K Jr | Additives and lubricant formulations for improved antioxidant properties |
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