CA1306757C - Sulfurized olefins - Google Patents

Sulfurized olefins

Info

Publication number: CA1306757C
Authority: CA; Canada
Prior art keywords: sulfur; additive product; olefin; lubricant composition; psi
Prior art date: 1985-04-08
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

Application number

CA000505756A

Other languages

English (en)

French (fr)

Inventor

Frank William Adis

Andrew Gene Horodysky

Angeline Baird Cardis

Henry Ashjian

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

Priority date (The priority date 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 date listed.)

1985-04-08

Filing date

1986-04-03

Publication date

1992-08-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24897173&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA1306757(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1986-04-03 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1992-08-25 Application granted granted Critical

1992-08-25 Publication of CA1306757C publication Critical patent/CA1306757C/en

2009-08-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001336 alkenes Chemical class 0.000 title claims abstract description 36
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 37
238000006243 chemical reaction Methods 0.000 claims abstract description 29
239000000314 lubricant Substances 0.000 claims abstract description 26
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 26
-1 hydrocarbyl olefin Chemical class 0.000 claims abstract description 17
239000000446 fuel Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 36
239000000654 additive Substances 0.000 claims description 35
229910052717 sulfur Inorganic materials 0.000 claims description 32
239000011593 sulfur Substances 0.000 claims description 32
238000000034 method Methods 0.000 claims description 31
230000000996 additive effect Effects 0.000 claims description 25
239000003921 oil Substances 0.000 claims description 20
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
230000001050 lubricating effect Effects 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 11
239000004519 grease Substances 0.000 claims description 10
239000000376 reactant Substances 0.000 claims description 10
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 8
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 8
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 8
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 7
KXPHJGWRCICEDH-UHFFFAOYSA-N 1-sulfanylidene-3h-dithiole Chemical class S=S1SCC=C1 KXPHJGWRCICEDH-UHFFFAOYSA-N 0.000 claims description 7
125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000002480 mineral oil Substances 0.000 claims description 6
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 5
239000005077 polysulfide Substances 0.000 claims description 5
229920001021 polysulfide Polymers 0.000 claims description 5
150000008117 polysulfides Polymers 0.000 claims description 5
FAMJUFMHYAFYNU-JTQLQIEISA-N (4r)-1-methyl-4-propan-2-ylcyclohexene Chemical compound CC(C)[C@@H]1CCC(C)=CC1 FAMJUFMHYAFYNU-JTQLQIEISA-N 0.000 claims description 4
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 4
DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 claims description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 4
229960000892 attapulgite Drugs 0.000 claims description 4
IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 claims description 4
239000004927 clay Substances 0.000 claims description 4
229940087305 limonene Drugs 0.000 claims description 4
235000001510 limonene Nutrition 0.000 claims description 4
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 4
229910052625 palygorskite Inorganic materials 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 4
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 3
235000010446 mineral oil Nutrition 0.000 claims description 3
238000005580 one pot reaction Methods 0.000 claims description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 9
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 6
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 6
229940043279 diisopropylamine Drugs 0.000 claims 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims 2
239000005069 Extreme pressure additive Substances 0.000 abstract description 2
239000007866 anti-wear additive Substances 0.000 abstract description 2
230000009972 noncorrosive effect Effects 0.000 abstract description 2
239000000047 product Substances 0.000 description 30
230000000052 comparative effect Effects 0.000 description 14
239000012530 fluid Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
241001061127 Thione Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
239000003599 detergent Substances 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
239000012208 gear oil Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000010687 lubricating oil Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000344 soap Substances 0.000 description 2
GQGTXJRZSBTHOB-UHFFFAOYSA-N 1-phenoxy-4-(4-phenoxyphenoxy)benzene Chemical class C=1C=C(OC=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 GQGTXJRZSBTHOB-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002367 Polyisobutene Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
230000007423 decrease Effects 0.000 description 1
UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000003879 lubricant additive Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000006259 organic additive Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
VWSUVZVPDQDVRT-UHFFFAOYSA-N phenylperoxybenzene Chemical class C=1C=CC=CC=1OOC1=CC=CC=C1 VWSUVZVPDQDVRT-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000013022 venting Methods 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
- C10M135/04—Hydrocarbons
- 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
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Liquid Carbonaceous Fuels (AREA)

CA000505756A 1985-04-08 1986-04-03 Sulfurized olefins Expired - Lifetime CA1306757C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US721,251		1976-09-08
US72125185A	1985-04-08	1985-04-08

Publications (1)

Publication Number	Publication Date
CA1306757C true CA1306757C (en)	1992-08-25

Family

ID=24897173

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000505756A Expired - Lifetime CA1306757C (en)	1985-04-08	1986-04-03	Sulfurized olefins

Country Status (7)

Country	Link
EP (1)	EP0201197B1 (de)
JP (1)	JPS61233092A (de)
AT (1)	ATE54663T1 (de)
AU (1)	AU578353B2 (de)
CA (1)	CA1306757C (de)
DE (1)	DE3672675D1 (de)
ZA (1)	ZA862362B (de)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2021224A1 (en) *	1989-08-03	1991-02-04	Scott Anthony Culley	Sulfurized olefin polymers soluble in polyalphaolefin lubricant oils
FR2712824B1 (fr) *	1993-11-26	1996-02-02	Inst Francais Du Petrole	Procédé de régénération de catalyseur.
FR2727427B1 (fr) *	1994-11-28	1997-04-25	Inst Francais Du Petrole	Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence d'alkyleneglycols ou de derives d'alkyleneglycols et d'hydroxydes de metaux alcalins ou alcalino-terreux, leur preparation et leur utilisation
FR2727425A1 (fr) *	1994-11-28	1996-05-31	Inst Francais Du Petrole	Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence d'eau et d'hydroxyde alcalin ou alcalino-terreux, leur preparation et leur utilisation
EP0714970A1 (de) *	1994-11-28	1996-06-05	Institut Français du Pétrole	Mit elementarem Schwefel sulfurierte olefinische Kohlenwasserstoffe in Gegenwart von Alkali- oder Erdalkalimetallhydroxiden und Glykolen, Polyglykolen oder ihre Alkylether und/oder Wasser
FR2729154A1 (fr) *	1995-01-10	1996-07-12	Inst Francais Du Petrole	Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence de carbonate ou d'hydrogenocarbonate alcalin, leur preparation et leurs utilisations
US5849677A (en) *	1995-12-27	1998-12-15	Exxon Chemical Patents Inc	Sulfurized olefin composition and its method of preparation
FR2808272B1 (fr)	2000-04-28	2002-06-14	Atofina	Procede de fabrication d'olefines sulfurees
FR2808273B1 (fr)	2000-04-28	2002-06-14	Atofina	Procede de fabrication d'olefines sulfurees
US6884855B2 (en) *	2003-01-30	2005-04-26	Chevron Oronite Company Llc	Sulfurized polyisobutylene based wear and oxidation inhibitors
RU2423413C2 (ru) *	2009-07-15	2011-07-10	Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран	Способ получения серусодержащей присадки
WO2014118073A1 (en) *	2013-01-29	2014-08-07	Basf Se	Polysulfide polyols, their production and use in the synthesis of polyurethanes
WO2016064615A1 (en) *	2014-10-24	2016-04-28	The University Of Tulsa	Sulfur-limonene polysulfide
CN104844772B (zh) *	2015-04-28	2017-11-10	中科院广州化学有限公司	一种具有可溶性的单质硫/脂环烯烃共聚物及其制备方法
DE202021002910U1 (de)	2021-09-08	2021-11-26	Metall-Chemie Technologies Gmbh	Limonensulfid
CN115873185B (zh) *	2022-10-26	2025-08-26	常州大学	一种含硫聚合物及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2237625A (en) *	1938-10-07	1941-04-08	Sharples Solvents Corp	Sulphurization of sulphur-containing organic conpounds
US3703504A (en) *	1970-01-12	1972-11-21	Mobil Oil Corp	Process for producing sulfurized olefins
US3703505A (en) *	1970-08-31	1972-11-21	Mobil Oil Corp	Preparation of sulfurized olefins
US3796661A (en) *	1971-07-19	1974-03-12	Texaco Inc	Sulfurized triisobutylene
GB1599288A (en) *	1977-07-22	1981-09-30	Cooper & Co Ltd Edwin	Sulphurized olefins and their use as lubricant additives
US4153563A (en) *	1978-05-24	1979-05-08	Mobil Oil Corporation	Lubricant compositions containing benzotriazole-allyl sulfide reaction products
JPS5538820A (en) *	1978-09-09	1980-03-18	Lubrizol Corp	Producing lubricant composition* adding agent concentrate material * and sulfide composition
US4331564A (en) *	1980-10-15	1982-05-25	Ferro Corporation	Catalyzing the sulfurization of olefins by tertiary phosphines, and an oil based material containing an additive amount of a sulfurized olefin so produced
CA1208208A (en) *	1982-05-07	1986-07-22	Kirk E. Davis	Sulfurized olefin-containing compositions

1986
- 1986-03-27 ZA ZA862362A patent/ZA862362B/xx unknown
- 1986-04-03 CA CA000505756A patent/CA1306757C/en not_active Expired - Lifetime
- 1986-04-04 JP JP61078085A patent/JPS61233092A/ja active Pending
- 1986-04-04 DE DE8686302488T patent/DE3672675D1/de not_active Expired - Lifetime
- 1986-04-04 AT AT86302488T patent/ATE54663T1/de not_active IP Right Cessation
- 1986-04-04 EP EP86302488A patent/EP0201197B1/de not_active Expired - Lifetime
- 1986-04-08 AU AU55730/86A patent/AU578353B2/en not_active Ceased

Also Published As

Publication number	Publication date
AU578353B2 (en)	1988-10-20
ZA862362B (en)	1987-11-25
ATE54663T1 (de)	1990-08-15
JPS61233092A (ja)	1986-10-17
EP0201197A1 (de)	1986-11-12
DE3672675D1 (de)	1990-08-23
EP0201197B1 (de)	1990-07-18
AU5573086A (en)	1986-10-16

Legal Events

Date	Code	Title	Description
1999-08-25	MKLA	Lapsed

Publication	Publication Date	Title
CA1270816A (en)	1990-06-26	Sulfurized olefins as antiwear/extreme pressure additives for lubricants and fuels and compositions thereof
CA1306757C (en)	1992-08-25	Sulfurized olefins
US5338468A (en)	1994-08-16	Sulfurized olefins
EP0215610B1 (de)	1991-04-10	Sulfurierte Olefine als Antiverschleissadditive und Zusammensetzungen davon
US5135670A (en)	1992-08-04	Sulfurized olefin extreme pressure/antiwear additives and compositions thereof
US4900460A (en)	1990-02-13	Sulfurized olefin adducts of dihydrocarbyl phosphates and phosphites and lubricant compositions containing same
US4175043A (en)	1979-11-20	Metal salts of sulfurized olefin adducts of phosphorodithioic acids and organic compositions containing same
US3878117A (en)	1975-04-15	Novel benzothiazyl disulfides, their preparation and use as lubricant additives
US4563302A (en)	1986-01-07	Sulfurized olefin process
JPH0446319B2 (de)	1992-07-29
US4207195A (en)	1980-06-10	Sulfurized olefin adducts of dihydrocarbyl phosphites and lubricant compositions containing same
US4152275A (en)	1979-05-01	Sulfurized olefin adducts of phosphorodithioic acids and organic compositions containing same
AU600983B2 (en)	1990-08-30	Olefin polysulfide compositions their manufacture and use as additives for lubricants
US4212753A (en)	1980-07-15	Reaction products of sulfurized olefin adducts of phosphorodithioic acids and organic compositions containing same
US4906391A (en)	1990-03-06	Reaction products of olefins, sulfur and phosphorus pentasulfide and lubricant compositions thereof
CA1276005C (en)	1990-11-06	Lubricating compositions
US5133889A (en)	1992-07-28	Polysulfurized olefin compositions, their preparation and use as additives in lubricants
EP0420453A1 (de)	1991-04-03	Schwefelgekoppelte alkylabgeleitete Merkaptobenzothiazol-Addukte als multifunktionelle verschleissschützende Zusätze und diese enthaltende Zusammensetzungen
US2703318A (en)	1955-03-01	Stabilized sulfur-containing additives for lubricants
US4929253A (en)	1990-05-29	Sulfurized olefin - glycerol monooleate adducts and lubricant compositions containing same
US5205948A (en)	1993-04-27	Sulfurized olefin-glycerol monooleate adducts and lubricant compositions containing same
US5679626A (en)	1997-10-21	Ethylenic hydrocarbons sulphurized by elemental sulphur in the presence of alkali or alkaline-earth metal hydroxices and in the presence of glycols or polyglcols, or their alkyl ethers, and or water
US5006271A (en)	1991-04-09	Organosulfur adducts as multifunctional additives for lubricating oils and fuels and as multifunctional lubricants
EP0411861B1 (de)	1993-03-31	Zu Polyalphaolefin-Schmierölen lösliche sulfurizierte Olefinpolymere
US4200546A (en)	1980-04-29	Metal salt treated sulfurized olefins and organic compositions containing same