Low viscosity, low volatility lubricating oil basestocks
View Patent ↗This disclosure provides low viscosity, low volatility alkylated siloxane compounds and alkylated alkoxy silane compounds. This disclosure also provides processes for producing the alkylated siloxane compounds and alkylated alkoxy silane compounds, and lubricating oil basestocks and lubricating oils containing one or more of the alkylated siloxane compounds or one or more of the alkylated alkoxy silane compounds. This disclosure further provides a method for improving one or more of solubility and dispersancy of polar additives and/or sludge in a lubricating oil by using as the lubricating oil a formulated oil containing one or more of the alkylated siloxane compounds or one or more of the alkylated alkoxy silane compounds.
1. A composition comprising one or more compounds represented by the formula:
R 1 —Si(R 3 ) 2 —O—Si(R 4 ) 2 —R 2 (1)
wherein R 1 and R 2 are the same or different and are the saturated residue of an olefin having from about 4 to about 40 carbon atoms; and each R 3 and R 4 are the same or different and are an alkyl group having from 1 to about 20 carbon atoms;
wherein the olefin is selected from the group consisting of an aromatic olefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and a heteroatom-containing olefin; and
wherein the composition has a viscosity (Kv 100 ) from about 2 to about 300 cst at 100° C., and a viscosity index (VI) from about −100 to about 300.
2. The composition of claim 1 wherein:
the aromatic olefin is selected from 2,4-dimethylstyrene, 2,5-dimethylstyrene, 4-tert-butyl styrene, 4-tert-butoxystyrene, 3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene, 4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene, 1-(trifluoromethyl)-4-vinylbenzene, 4-[N-(methylaminoethyl)aminomethyl]styrene, 4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol, ((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene, 2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methyl styrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene, 2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene, 1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene, 1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole, N-vinylphthalimide, and 4-(trifluoromethyl)styrene.
3. The composition of claim 1 wherein:
the cycloaliphatic olefin is selected from vinylcyclopentane, vinylcylcohexane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclododecene, cyclotetradecene, cyclohexadecene, cyclooctadecene, allylcyclohexane, 1,2,4-trivinylcyclohexane, and 5-vinyl-2-norbornene.
4. The composition of claim 1 wherein:
the vinyl ether is selected from ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, tetraethylene glycol methyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether, isooctyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether, cyclohexyl vinyl ether, 2,2,2-trifluoroethyl vinyl ether, 1,4-butanediol divinyl ether, di(ethylene glycol) divinyl ether, tri(ethylene glycol) divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, bis[4-(vinyloxy)butyl] isophthalate, bis[4-(vinyloxy)butyl] succinate, diethyl vinyl orthoformate, di(ethylene glycol) vinyl ether, ethylene glycol vinyl ether, and 1,4-butanediol vinyl ether.
5. The composition of claim 1 wherein:
the acrylate is selected from methyl acrylate, ethyl acrylate, hexyl acrylate, isooctyl acrylate, isodecyl acrylate, lauryl acrylate, octadecyl acrylate, di(ethylene glycol) 2-ethylhexyl ether acrylate, di(ethylene glycol) ethyl ether acrylate, ethylene glycol phenyl ether acrylate, 2-ethylhexyl acrylate, butyl acrylate, isobornyl acrylate, ethylene glycol methyl ether acrylate, 2-(dimethylamino)ethyl acrylate, 2-(diethylamino)ethyl acrylate, 3-(dimethylamino)propyl acrylate, pentafluorophenyl acrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, 4-acetoxyphenethyl acrylate, 4-allyloxy-2-hydroxybenzophenone, 2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate, 4-acryloylmorpholine, 4-tert-butylcyclohexyl acrylate, tetrahydrofurfutyl acrylate, 3,5,5-trimethylhexyl acrylate, di(trimethylolpropane) tetraacrylate, tris[2-(acryloyloxy)ethyl]isocyanurate, pentaerythritol tetraacrylate, 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-triacryloylhexahydro-1,3,5-triazine, 1,1,1,3,3,3-hexafluoroisopropyl acrylate, 9H-carbazole-9-ethyl acrylate, and 2-hydroxypropyl 2-(methacryloyloxy)ethyl phthalate.
6. The composition of claim 1 wherein:
the methacrylate is selected from methyl methacrylate, butyl methacrylate, tert-butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-(diethylamino)ethyl methacrylate, di(ethylene glycol) methyl ether methacrylate, lauryl methacrylate, stearyl methacrylate, isobornyl methacrylate, ethylene glycol phenyl ether methacrylate, phenyl methacrylate, cyclohexyl methacrylate, allyl methacrylate, vinyl methacrylate, benzyl methacrylate, 1,6-hexanediol dimethacrylate, bisphenol A dimethacrylate, bisphenol A glycerolate dimethacrylate, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl] ethyl methacrylate, cyclohexyl methacrylate, tetrahydrofurfutyl methacrylate, 2-(tert-butylamino)ethyl methacrylate, 2-(diisopropylamino)ethyl methacrylate, 2-N-morpholinoethyl methacrylate, 9H-carbazole-9-ethyl methacrylate, 1-naphthyl methacrylate, pentafluorophenyl methacrylate, 1-pyrenemethayl methacrylate, TEMPO methacrylate, and N-(triphenylmethyl)methacrylamide.
7. The composition of claim 1 wherein:
the vinyl ester is selected from vinyl acetate, vinyl propionate, vinyl valerate, vinyl butyrate, vinyl decanoate, vinyl stearate, vinyl cinnamate, allyl butyrate, vinyl pivalate, vinyl benzoate, vinyl 4-t-butylbenzoate, and allyl cinnamate.
8. The composition of claim 1 wherein:
the heteroatom-containing olefin is selected from N-methyl-N-vinylacetamide, N,N-dimethylacrylamide, 4-vinylpyridine, 2-vinylpyridine, 1-vinyl-2-pyrrolidinone, 1-vinyl-1,2,4-triazole, 1-vinylimidazole, N-vinylcaprolactone, 4-acryloylmorpholine, 5-vinyluracil, 4-acryloylmorpholine, N,N-dimethylacrylamide, 2-vinyl-1,3-dioxolane, acrolein diethyl acetal, acrolein dimethyl acetal, 4-vinyl-1,3-dioxolane-2-one, vinylbenzoic acid, 1-vinylbenzyl alcohol, vinyl trifluoroacetate, 1-vinyl cyclohexanole, vinyloxy trimethylsilane, vinyltrimethylsilane, allyl trimethylsilane, triphenyl(vinyl)silane, and 2-isopropenyl-2-oxazoline.
9. A process for preparing a composition comprising one or more compounds represented by the formula:
R 1 —Si(R 3 ) 2 —O—Si(R 4 ) 2 —R 2 (1)
wherein R 1 and R 2 are the same or different and are the saturated residue of an olefin having from about 4 to about 40 carbon atoms; and each R 3 and R 4 are the same or different and are an alkyl group having from 1 to about 20 carbon atoms;
wherein said process comprises reacting an alkyl siloxane with an olefin, in the presence of a catalyst, under reaction conditions sufficient to produce said composition;
wherein the alkyl siloxane has from about 4 to about 20 carbon atoms; and the olefin is selected from the group consisting of an aromatic olefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and a heteroatom-containing olefin; and
wherein the composition has a viscosity (Kv 100 ) from about 2 to about 300 cst at 100° C., and a viscosity index (VI) from about −100 to about 300.
10. The process of claim 9 wherein the alkyl siloxane comprises 1,1,3,3-tetramethyldisiloxane, hexaethoxydisiloxane, 1,3-didecyl-1,1,3,3-tetramethyl disiloxane, 1,3-didodecyl-1,1,3,3-tetramethyl disiloxane, 3-di(2-hexyldecyl)-1,1,3,3-tetramethyl disiloxane, 1,3-bis(3-(2-hydroxyethyoxy)propyl)tetramethyldisiloxane, 1,3-bis(hydroxypropyl)tetramethyldisiloxane, bis(methoxytriethyleneoxypropyl)tetramethyldisiloxane, 1,3-bis(trimethylsiloxy)1,3-dimethyldisiloxane, 1,3-bis(3-hydroxyisobutyl)tetramethyldisiloxane, or 1,3-diallyltetramethyldisiloxane.
11. The process of claim 9 wherein:
the aromatic olefin is selected from 2,4-dimethylstyrene, 2,5-dimethylstyrene, 4-tert-butyl styrene, 4-tert-butoxystyrene, 3,4-dimethoxystyrene, 4-acetoxystyrene, 1,3-diisopropenylbenzene, 4-ethoxystyrene, 2,3,4,5,6-pentafluorostyrene, 4-fluorostyrene, 1-(trifluoromethyl)-4-vinylbenzene, 4-[N-(methylaminoethyl)aminomethyl]styrene, 4-benzyloxy-3-methoxystyrene, 2-methoxy-4-vinylphenol, ((4-vinylphenyl)methylene)dibenzene, 1-vinylnaphthalene, 2-vinylnaphthalene, divinylbenzene, trivinylbenzene, styrene, 4-methyl styrene, 2-methyl styrene, 1-methyl styrene, 4-methoxystyrene, 2-methoxystyrene, 1-allyl-4-(trifluoromethyl)benzene, 9-vinylanthracene, 1,1-diphenylethylene, 2,3-dibenzyl-1,3-butadiene, 1-allyl-2-methylbenzene, dipentene, 4-vinylbiphenyl, 9-vinylcarbazole, N-vinylphthalimide, and 4-(trifluoromethyl)styrene.
12. The process of claim 9 wherein:
the cycloaliphatic olefin is selected from vinylcyclopentane, vinylcylcohexane, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, cyclododecene, cyclotetradecene, cyclohexadecene, cyclooctadecene, allylcyclohexane, 1,2,4-trivinylcyclohexane, and 5-vinyl-2-norbornene.
13. The process of claim 9 wherein:
the vinyl ether is selected from ethyl vinyl ether, propyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, dodecyl vinyl ether, tetraethylene glycol methyl vinyl ether, hexadecyl vinyl ether, octadecyl vinyl ether, isooctyl vinyl ether, t-butyl vinyl ether, phenyl vinyl ether, cyclohexyl vinyl ether, 2,2,2-trifluoroethyl vinyl ether, 1,4-butanediol divinyl ether, di(ethylene glycol) divinyl ether, tri(ethylene glycol) divinyl ether, 1,4-cyclohexanedimethanol divinyl ether, bis[4-(vinyloxy)butyl] isophthalate, bis[4-(vinyloxy)butyl] succinate, diethyl vinyl orthoformate, di(ethylene glycol) vinyl ether, ethylene glycol vinyl ether, and 1,4-butanediol vinyl ether.
14. The process of claim 9 wherein:
the acrylate is selected from methyl acrylate, ethyl acrylate, hexyl acrylate, isooctyl acrylate, isodecyl acrylate, lauryl acrylate, octadecyl acrylate, di(ethylene glycol) 2-ethylhexyl ether acrylate, di(ethylene glycol) ethyl ether acrylate, ethylene glycol phenyl ether acrylate, 2-ethylhexyl acrylate, butyl acrylate, isobornyl acrylate, ethylene glycol methyl ether acrylate, 2-(dimethylamino)ethyl acrylate, 2-(diethylamino)ethyl acrylate, 3-(dimethylamino)propyl acrylate, pentafluorophenyl acrylate, 1,6-hexanediol diacrylate, trimethylolpropane triacrylate, 4-acetoxyphenethyl acrylate, 4-allyloxy-2-hydroxybenzophenone, 2-(4-benzoyl-3-hydroxyphenoxy)ethyl acrylate, 4-acryloylmorpholine, 4-tert-butylcyclohexyl acrylate, tetrahydrofurfutyl acrylate, 3,5,5-trimethylhexyl acrylate, di(trimethylolpropane) tetraacrylate, tris[2-(acryloyloxy)ethyl]isocyanurate, pentaerythritol tetraacrylate, 1,3,5-triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-triacryloylhexahydro-1,3,5-triazine, 1,1,1,3,3,3-hexafluoroisopropyl acrylate, 9H-carbazole-9-ethyl acrylate, and 2-hydroxypropyl 2-(methacryloyloxy)ethyl phthalate.
15. The process of claim 9 wherein:
the methacrylate is selected from methyl methacrylate, butyl methacrylate, tert-butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-(diethylamino)ethyl methacrylate, di(ethylene glycol) methyl ether methacrylate, lauryl methacrylate, stearyl methacrylate, isobornyl methacrylate, ethylene glycol phenyl ether methacrylate, phenyl methacrylate, cyclohexyl methacrylate, allyl methacrylate, vinyl methacrylate, benzyl methacrylate, 1,6-hexanediol dimethacrylate, bisphenol A dimethacrylate, bisphenol A glycerolate dimethacrylate, 2-[3-(2H-benzotriazol-2-yl)-4-hydroxyphenyl] ethyl methacrylate, cyclohexyl methacrylate, tetrahydrofurfutyl methacrylate, 2-(tert-butylamino)ethyl methacrylate, 2-(diisopropylamino)ethyl methacrylate, 2-N-morpholinoethyl methacrylate, 9H-carbazole-9-ethyl methacrylate, 1-naphthyl methacrylate, pentafluorophenyl methacrylate, 1-pyrenemethayl methacrylate, TEMPO methacrylate, and N-(triphenylmethyl)methacrylamide.
16. The process of claim 9 wherein:
the vinyl ester is selected from vinyl acetate, vinyl propionate, vinyl valerate, vinyl butyrate, vinyl decanoate, vinyl stearate, vinyl cinnamate, allyl butyrate, vinyl pivalate, vinyl benzoate, vinyl 4-t-butylbenzoate, and allyl cinnamate.
17. The process of claim 9 wherein:
the heteroatom-containing olefin is selected from N-methyl-N-vinylacetamide, N,N-dimethylacrylamide, 4-vinylpyridine, 2-vinylpyridine, 1-vinyl-2-pyrrolidinone, 1-vinyl-1,2,4-triazole, 1-vinylimidazole, N-vinylcaprolactone, 4-acryloylmorpholine, 5-vinyluracil, 4-acryloylmorpholine, N,N-dimethylacrylamide, 2-vinyl-1,3-dioxolane, acrolein diethyl acetal, acrolein dimethyl acetal, 4-vinyl-1,3-dioxolane-2-one, vinylbenzoic acid, 1-vinylbenzyl alcohol, vinyl trifluoroacetate, 1-vinyl cyclohexanole, vinyloxy trimethylsilane, vinyltrimethylsilane, allyl trimethylsilane, triphenyl(vinyl)silane, and 2-isopropenyl-2-oxazoline.
18. A method for improving one or more of solubility and dispersancy of polar additives or sludge in a lubricating oil by using as the lubricating oil a formulated oil comprising a lubricating oil basestock as a major component, and a lubricating oil cobasestock as a minor component; wherein said lubricating oil cobasestock comprises one or more compounds represented by the formula:
R 1 —Si(R 3 ) 2 —O—Si(R 4 ) 2 —R 2 (1)
wherein R 1 and R 2 are the same or different and are the saturated residue of an olefin having from about 4 to about 40 carbon atoms; and each R 3 and R 4 are the same or different and are an alkyl group having from 1 to about 20 carbon atoms;
wherein the olefin is selected from the group consisting of an aromatic olefin, a cycloaliphatic olefin, a vinyl ether, an acrylate, a methacrylate, a vinyl ester, and a heteroatom-containing olefin; and
wherein the lubricating oil cobasestock has a viscosity (Kv 100 ) from about 2 to about 300 cst at 100° C., and a viscosity index (VI) from about −100 to about 300.