US3404090A - Water base lubricant - Google Patents
Water base lubricant Download PDFInfo
- Publication number
- US3404090A US3404090A US615924A US61592467A US3404090A US 3404090 A US3404090 A US 3404090A US 615924 A US615924 A US 615924A US 61592467 A US61592467 A US 61592467A US 3404090 A US3404090 A US 3404090A
- Authority
- US
- United States
- Prior art keywords
- composition
- water
- thione
- alkyl
- lubricity
- 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 24
- 239000000314 lubricant Substances 0.000 title description 10
- 239000000203 mixture Substances 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- -1 aliphatic radical Chemical class 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- 239000012267 brine Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NVHNGVXBCWYLFA-UHFFFAOYSA-N 1,3-diazinane-2-thione Chemical compound S=C1NCCCN1 NVHNGVXBCWYLFA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002528 anti-freeze Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- XCWPBWWTGHQKDR-UHFFFAOYSA-N 1,3-dithiolane-2-thione Chemical compound S=C1SCCS1 XCWPBWWTGHQKDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 125000002511 behenyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 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
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000010835 comparative analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002173 cutting fluid Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000006259 organic additive Substances 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M173/00—Lubricating compositions containing more than 10% water
- C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
-
- 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
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/12—Polysaccharides, e.g. cellulose, biopolymers
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
-
- 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
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2050/01—Emulsions, colloids, or micelles
Definitions
- This invention pertains to a composition comprising an N-secondary-aliphatic-hexahydropyrimidine-2-thione, and a bis(Z-hydroxyethyl) aliphatic amine oxide; and a process utilizing said composition for imparting lubricity to aqueous systems.
- organic oils are not completely satisfactory.
- secondary oil recovery systems wherein 'water is pumped into the ground to force oil to the surface, there is a tendency for oil lubricants to plate out upon the pump.
- oils when oils are used as cutting fluids, considerable time is often spent in removing the oils from the product.
- organic oils may present a fire hazard, they often form emulsions, and they may not be compatible with other additives to the water systems.
- organic oils, such as mineral oil tend to lose lubricity under certain light and pressure conditions.
- a specific embodiment of our invention may be exemplified by the composition comprising (A) N-(C- -C secalkyl)hexahydropyrimidine-Z-thione and (B) bis(2-hydroxyethyl)cocoamine oxide. While substantial synergistic lubricity is exhibited when the proportions by weight of component (A) to component (B) of this composition range from about 1:5 to about 5:1, particularly desirable results are obtained as the proportions approach 1:1, such as at 3:1, 1:3, 2:1, 1:2 and 1:1. It will be understood that proportions outside this range will exhibit some degree of lubricity.
- a preferred concentration of the pyrimidine thione and amine oxide composition is about 50 to parts of the composition per million parts of water, and the upper limits of this concentration do not appear critical.
- Illustrative amine oxides having utility as one component in our composition have the structure FORMULA I CH CH OH CHgCHzOH wherein R is an aliphatic hydrocarbon radical containing from 6 to 22 carbon atoms. R may be straight or branched chain, saturated or unsaturated groups such as octyl, nonyl, N-(C -C sec-alkyl), dodecyl, tridecyl, tetradecyl, pentadecyl, N-(C C sec-alkyl), hexadecyl, octadecyl, octadecenyl, octadecatrienyl, docosyl, eicosyl, and mixtures of radicals such as are derived from naturally occurring glycerides such as coconut oil, tallow, soybean oil and the like.
- R is an aliphatic hydrocarbon radical containing from 6 to 22 carbon atoms.
- R may be straight or branche
- Coconut oil contains a mixture of saturated and unsaturated aliphatic hydrocarbon radicals from C to C and is primarily N-dodecyl.
- Tallow contains a saturated and unsaturated mixture from C to C primarily N-hexadecyl, N-octadecyl and octadecenyl.
- Soybean contains a saturated and unsaturated mixture from G to C primarily octadecenyl and octadecadienyl.
- the preparation of useful bis(Z-hydroxyethyl) aliphatic amine oxides may be by the reaction with an excess of hydrogen peroxide as is known in the art.
- N-sec-alkyl hexahydropyrimidine-Z-thiones useful as the second component of our synergistic combination have the structure FORMULA II wherein R is an individual or mixed chain length N-secondary-alkyl radical having from 6 to 15 carbon atoms.
- R is an individual or mixed chain length N-secondary-alkyl radical having from 6 to 15 carbon atoms.
- These compounds may be prepared by reacting a thiocarbonyl group containing compound, such as carbon disulfide, thiophosgene, ethylene trithiocarbonate, and the like materials, with a long chain diamine in a mutual solvent, such as methanol, ethanol, isopropanol, butanol, chloroform, ethylene chloride, carbon tetrachloride, ether and the like materials at temperatures of to 80 C.
- Some useful diamines for this preparation have the following structure:
- additives may be included in the water system.
- low molecular weight glycols or alcohols such as ethylene glycol, propylene glycol, etc., or methanol, ethanol, etc.
- Carboxymethyl cellulose, alginates, etc. may be added as thickeners.
- water corrosion inhibitors may be added.
- the foregoing additives are compatible with the water base lubricant. If desired, they may be omitted.
- Example I Equimolar amounts of a mixture of long chain C to C secondary-alkyl diamines and carbon disullide ar admixed with cooling and stirring while both are dissolved in ethanol.
- the ethanol solution of each comprises a 50% by weight solution.
- a temperature of 30 C. is utilized as the reaction temperature.
- a mixture of N-(C -C secalkyl) 1,3 propanediamine N dithiocarbamic acids is formed.
- the acids ar then removed from the alcoholic media by evaporation and heated at a temperature of 115 C. to cause evolution of H 8. This causes cyclization to N (C -C sec alkyl)hexahydropyrimidine 2- thione.
- Example II A convenient and meaningful method of measuring water soluble lubricity is by means of a Baroid extreme pressure mud tester, which is similar to a Timken wear tester.
- a standard evaluation procedure is followed where in the test cup and the test block are weighed to the nearest rng.; then the test cup is mounted on the beveled ring located on the bottom of the belt driven shaft and the test block is mounted at the bottom of the shaft connected to the torque arm.
- the sample container is filled with approximately 200 ml. of a brine solution or tap water with the desired amount of the chemical to be evaluated. After the sample cup is positioned so that the test cup and test block are covered with fluid, the motor is started and the machine allowed to run 5 minutes with no load applied. The load test evaluation is then started at lb.
- the wear test evaluation is the same evaluation initially, with a continuation of running the machine at 140 lb. load for minutes. At the end of the evaluation test periods, the test cup and block are removed, rinsed, and reweighed. The weight loss (amount of wear) indicates the efficiency of the lubricant. If galling or seizing occurs during the evaluation, the machine is stopped.
- the brine solution used in some of the evaluations following herein consisted of water, 10.5% sodium chloride, 9.4% calcium chloride, 0.06% magnesium chloride, 0.02% ferric chloride, and 0.02% sodium sulfate.
- Aromox C/ 12 is bis(Z-hydroxyethyl)cocoamine oxide
- Aromox T/ 12 is bis(2-hydroxyethyl)tallowamine oxide
- NL-7 PTU is N-(C C sec-alkyl)hexahydropyrimidine- Z-thione
- NL-ll PTU is N-(C C sec-alkyl)hexahydropyrimidine-Z-thione.
- Example III Illustrative proportions and concentrations showing the enhanced water base lubricity of the composition are set forth in the following additional load test results obtained by the procedures of Example II:
- a composition comprising an N-secondary-aliphaticl1exahydropyrimidine-Z-thione wherein the secondaryaliphatic radical contains from 6 to 15 carbon atoms and a bis(2-hydroxyethyl) aliphatic amine oxide wherein the aliphatic radical contains from 6 to 22 carbon atoms, and in which the proportions by weight of the pyrimidine thione to the amine oxide range from about 1:5 to about 5:1, said composition displaying synergistic lubricity when used with water in a concentration of at least 20 ppm.
- composition of claim 1 in which said pyrimidine thione is N-(C C sec-alkyl)-hexahydropyrirnidine-2- thione and said amine oxide is bis(2-hydroxyethyl)cocoamine oxide and said proportion is about 2:1.
- composition of claim 1 in which said composition displays synergistic lubricity when used with brine in a concentration of at least 20 p.p.m.
- composition of claim 3 in which said pyrimidine thione is N-(Cq-Cg sec-alkyl)hexahydropyrimidine-Z-thione and said amine oxide is bis(2-hydroxyethyl)cocoamine oxide and said proportion is about 1:2.
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- Lubricants (AREA)
Description
United States Patent 3,404,090 WATER BASE LUBRICANT Roy J. Betty, Chicago, Ill., and Robert E. Malec, Birmiugham, Mich., assignors to Armour and Company, Chicago, 111., a corporation of Delaware No Drawing. Feb. 14, 1967, Ser. No. 615,924 4 Claims. (Cl. 252-475) ABSTRACT OF THE DISCLOSURE A pyrimidine thione and amine oxide composition for use as a Water base lubricant and a process for imparting lubricity to aqueous systems.
BACKGROUND OF THE INVENTION This invention pertains to a composition comprising an N-secondary-aliphatic-hexahydropyrimidine-2-thione, and a bis(Z-hydroxyethyl) aliphatic amine oxide; and a process utilizing said composition for imparting lubricity to aqueous systems.
In various fields where lubricants are required, it has been found that organic oils are not completely satisfactory. For example, in secondary oil recovery systems, wherein 'water is pumped into the ground to force oil to the surface, there is a tendency for oil lubricants to plate out upon the pump. Further, when oils are used as cutting fluids, considerable time is often spent in removing the oils from the product. In addition, organic oils may present a fire hazard, they often form emulsions, and they may not be compatible with other additives to the water systems. Also organic oils, such as mineral oil, tend to lose lubricity under certain light and pressure conditions.
Recently, a water base lubricant comprising water and bis(Z-hydroxyethyl) aliphatic amine oxides has been disclosed.
SUMMARY OF II-IE INVENTION We have discovered that combining bis(2-hydroxyethyl) aliphatic amine oxides with N-secondary-aliphatic hexahydropyrimidine-Z-thiones results in a composition exhibiting synergistic water soluble lubricity. We were surprised to find that this combination imparts water soluble lubricant properties greater than Would be expected if the compounds acted independently when used at the same total quantitative amounts. It should be understood that synergistic activity is a relatively rare and unexpected occurrence. Further, our synergistic composition is noninflammable and is compatible with organic additives such as antifreeze materials, corrosion inhibitors, thickeners, and other desirable additives to the water. In addition, organic oils may be omitted from our process for imparting lubricity to water systems, thereby there is no danger of rancidity, forming of sludge or other degradation products.
3,404,090 Patented Oct. 1, 1968 DETAILED DESCRIPTION OF THE INVENTION A specific embodiment of our invention may be exemplified by the composition comprising (A) N-(C- -C secalkyl)hexahydropyrimidine-Z-thione and (B) bis(2-hydroxyethyl)cocoamine oxide. While substantial synergistic lubricity is exhibited when the proportions by weight of component (A) to component (B) of this composition range from about 1:5 to about 5:1, particularly desirable results are obtained as the proportions approach 1:1, such as at 3:1, 1:3, 2:1, 1:2 and 1:1. It will be understood that proportions outside this range will exhibit some degree of lubricity.
In another embodiment of our invention, we introduce into water at least 20 parts, per million parts of water by weight, of (A) an N-sec-alkyl-hexahydropyrimidinc-2- thione wherein the secondary-alkyl radical contains from 6 to 15 carbon atoms and (B) a bis(Z-hydroxyethyl) aliphatic amine oxide wherein the aliphatic radical contains from 6 to 22 carbon atoms, the proportions of (A) to (B) being as illustrated for the composition set forth hereinabove. A preferred concentration of the pyrimidine thione and amine oxide composition is about 50 to parts of the composition per million parts of water, and the upper limits of this concentration do not appear critical. We may use 500 parts of the amine oxide-pyrimidine thione compositions, or more, per million parts of water.
Illustrative amine oxides having utility as one component in our composition have the structure FORMULA I CH CH OH CHgCHzOH wherein R is an aliphatic hydrocarbon radical containing from 6 to 22 carbon atoms. R may be straight or branched chain, saturated or unsaturated groups such as octyl, nonyl, N-(C -C sec-alkyl), dodecyl, tridecyl, tetradecyl, pentadecyl, N-(C C sec-alkyl), hexadecyl, octadecyl, octadecenyl, octadecatrienyl, docosyl, eicosyl, and mixtures of radicals such as are derived from naturally occurring glycerides such as coconut oil, tallow, soybean oil and the like. Coconut oil contains a mixture of saturated and unsaturated aliphatic hydrocarbon radicals from C to C and is primarily N-dodecyl. Tallow contains a saturated and unsaturated mixture from C to C primarily N-hexadecyl, N-octadecyl and octadecenyl. Soybean contains a saturated and unsaturated mixture from G to C primarily octadecenyl and octadecadienyl.
The preparation of useful bis(Z-hydroxyethyl) aliphatic amine oxides may be by the reaction with an excess of hydrogen peroxide as is known in the art.
Exemplary N-sec-alkyl hexahydropyrimidine-Z-thiones useful as the second component of our synergistic combination have the structure FORMULA II wherein R is an individual or mixed chain length N-secondary-alkyl radical having from 6 to 15 carbon atoms. These compounds may be prepared by reacting a thiocarbonyl group containing compound, such as carbon disulfide, thiophosgene, ethylene trithiocarbonate, and the like materials, with a long chain diamine in a mutual solvent, such as methanol, ethanol, isopropanol, butanol, chloroform, ethylene chloride, carbon tetrachloride, ether and the like materials at temperatures of to 80 C. Some useful diamines for this preparation have the following structure:
FORMU LA II I H II]: RI IC Hz 0 Hz 0 Hr-N-H wherein R is a secondary alkyl radical having from 6 to carbon atoms. Initially, the dithiocarbamic acid inner salt is formed which, upon further heating at 90 to 200 C. gives olT hydrogen sulfide with formation of the cyclic hexahydropyrimidine-2-thione.
When the composition has been prepared as above described, other additives may be included in the water system. For example, low molecular weight glycols or alcohols, such as ethylene glycol, propylene glycol, etc., or methanol, ethanol, etc., may be added as antifreeze materials. Carboxymethyl cellulose, alginates, etc. may be added as thickeners. Similarly, water corrosion inhibitors may be added. The foregoing additives are compatible with the water base lubricant. If desired, they may be omitted.
Comparative evaluations of the amine oxides and pyrimidine thiones as described herein show that these compounds exhibit greater lubricity in combination than would be expected if the compounds acted independently. A specific comparison is set out in the accompanying examples, which are illustrative of our composition and process.
Example I Equimolar amounts of a mixture of long chain C to C secondary-alkyl diamines and carbon disullide ar admixed with cooling and stirring while both are dissolved in ethanol. The ethanol solution of each comprises a 50% by weight solution. A temperature of 30 C. is utilized as the reaction temperature. A mixture of N-(C -C secalkyl) 1,3 propanediamine N dithiocarbamic acids is formed. The acids ar then removed from the alcoholic media by evaporation and heated at a temperature of 115 C. to cause evolution of H 8. This causes cyclization to N (C -C sec alkyl)hexahydropyrimidine 2- thione.
Example II A convenient and meaningful method of measuring water soluble lubricity is by means of a Baroid extreme pressure mud tester, which is similar to a Timken wear tester. A standard evaluation procedure is followed where in the test cup and the test block are weighed to the nearest rng.; then the test cup is mounted on the beveled ring located on the bottom of the belt driven shaft and the test block is mounted at the bottom of the shaft connected to the torque arm. The sample container is filled with approximately 200 ml. of a brine solution or tap water with the desired amount of the chemical to be evaluated. After the sample cup is positioned so that the test cup and test block are covered with fluid, the motor is started and the machine allowed to run 5 minutes with no load applied. The load test evaluation is then started at lb. load and taken up to 140 lb. load in 20 lb. increments at 5 minute intervals. The wear test evaluation is the same evaluation initially, with a continuation of running the machine at 140 lb. load for minutes. At the end of the evaluation test periods, the test cup and block are removed, rinsed, and reweighed. The weight loss (amount of wear) indicates the efficiency of the lubricant. If galling or seizing occurs during the evaluation, the machine is stopped. The brine solution used in some of the evaluations following herein consisted of water, 10.5% sodium chloride, 9.4% calcium chloride, 0.06% magnesium chloride, 0.02% ferric chloride, and 0.02% sodium sulfate.
Illustrative results comparing a known water soluble lubricant and certain of the components of this invention, individually and combined, are set forth in Table I. The chemicals designated in the table are defined as follows:
Aromox C/ 12 is bis(Z-hydroxyethyl)cocoamine oxide Aromox T/ 12 is bis(2-hydroxyethyl)tallowamine oxide NL-7 PTU is N-(C C sec-alkyl)hexahydropyrimidine- Z-thione NL-ll PTU is N-(C C sec-alkyl)hexahydropyrimidine-Z-thione.
TABLE I Chemical Concentration, Wear in mg.
p.p.m. weight loss Load test in brine:
Standard 1 300 41. 3 200 10. 8 Aromox C/12 1 8 555 0 25. 7 7 PTU 50 13.9 NL-ll PTU 19.8 Aromox O/12 100 1 and 2. 2 NL- PTU 50 1 Load test in tapwater:
Aromox 0/12 200 55.5 NL-7 PTU 100 30.0 Aromox 0/12 100 and 10.2 NL-7 PTU 50 Wear test in brine:
Aromox 0/12 100 and 2.1 NL-7 PTU 50 A water base lubricating product primarily containing a methyl ester of alpha sulio stcaric acid.
Example III Illustrative proportions and concentrations showing the enhanced water base lubricity of the composition are set forth in the following additional load test results obtained by the procedures of Example II:
While in the foregoing specification, we have described specific compositions and procedures in considerable detail for the purpose of illustrating our invention, those skilled in the art will appreciate that variations can be made without departing from the spirit and scope of our invention; and therefore, it is not intended to be limited except as indicated in the appended claims.
We claim:
1. A composition comprising an N-secondary-aliphaticl1exahydropyrimidine-Z-thione wherein the secondaryaliphatic radical contains from 6 to 15 carbon atoms and a bis(2-hydroxyethyl) aliphatic amine oxide wherein the aliphatic radical contains from 6 to 22 carbon atoms, and in which the proportions by weight of the pyrimidine thione to the amine oxide range from about 1:5 to about 5:1, said composition displaying synergistic lubricity when used with water in a concentration of at least 20 ppm.
2. The composition of claim 1 in which said pyrimidine thione is N-(C C sec-alkyl)-hexahydropyrirnidine-2- thione and said amine oxide is bis(2-hydroxyethyl)cocoamine oxide and said proportion is about 2:1.
3. The composition of claim 1 in which said composition displays synergistic lubricity when used with brine in a concentration of at least 20 p.p.m.
4. The composition of claim 3 in which said pyrimidine thione is N-(Cq-Cg sec-alkyl)hexahydropyrimidine-Z-thione and said amine oxide is bis(2-hydroxyethyl)cocoamine oxide and said proportion is about 1:2.
6 References Cited UNITED STATES PATENTS 3,108,071 10/1963 Harker 25247 X 3,346,495 10/1967 Malec et a1. 252-49.3
PATRICK P. GARVIN, Primary Examiner. W. H. CANNON. Assistant Examiner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US615924A US3404090A (en) | 1967-02-14 | 1967-02-14 | Water base lubricant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US615924A US3404090A (en) | 1967-02-14 | 1967-02-14 | Water base lubricant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3404090A true US3404090A (en) | 1968-10-01 |
Family
ID=24467338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US615924A Expired - Lifetime US3404090A (en) | 1967-02-14 | 1967-02-14 | Water base lubricant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3404090A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901815A (en) * | 1974-06-05 | 1975-08-26 | Texaco Inc | Synthetic aircraft turbine oil |
| EP0137057A1 (en) * | 1983-08-12 | 1985-04-17 | Diversey Wyandotte Inc. | Conveyor track lubricant composition employing phosphate esters and method of using same |
| US5935913A (en) * | 1998-10-16 | 1999-08-10 | Uniroyal Chemical Company, Inc. | Cyclic thiourea additives for lubricants |
| US20040029744A1 (en) * | 2002-08-07 | 2004-02-12 | Ravindranath Mukkamala | Cyclic thioamides as additives for lubricating oils |
| US20040053792A1 (en) * | 2000-06-23 | 2004-03-18 | Wederell Christopher William | Conveyor lubricant |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108071A (en) * | 1959-05-08 | 1963-10-22 | Commercial Solvents Corp | Non-corrosive lubricating compositions |
| US3346495A (en) * | 1964-08-20 | 1967-10-10 | Armour & Co | Water base lubricants |
-
1967
- 1967-02-14 US US615924A patent/US3404090A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3108071A (en) * | 1959-05-08 | 1963-10-22 | Commercial Solvents Corp | Non-corrosive lubricating compositions |
| US3346495A (en) * | 1964-08-20 | 1967-10-10 | Armour & Co | Water base lubricants |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3901815A (en) * | 1974-06-05 | 1975-08-26 | Texaco Inc | Synthetic aircraft turbine oil |
| EP0137057A1 (en) * | 1983-08-12 | 1985-04-17 | Diversey Wyandotte Inc. | Conveyor track lubricant composition employing phosphate esters and method of using same |
| US5935913A (en) * | 1998-10-16 | 1999-08-10 | Uniroyal Chemical Company, Inc. | Cyclic thiourea additives for lubricants |
| US20040053792A1 (en) * | 2000-06-23 | 2004-03-18 | Wederell Christopher William | Conveyor lubricant |
| US20040029744A1 (en) * | 2002-08-07 | 2004-02-12 | Ravindranath Mukkamala | Cyclic thioamides as additives for lubricating oils |
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