US3403102A - Lubricant containing phosphorus acid esters - Google Patents
Lubricant containing phosphorus acid esters Download PDFInfo
- Publication number
- US3403102A US3403102A US621136A US62113667A US3403102A US 3403102 A US3403102 A US 3403102A US 621136 A US621136 A US 621136A US 62113667 A US62113667 A US 62113667A US 3403102 A US3403102 A US 3403102A
- Authority
- US
- United States
- Prior art keywords
- acid
- phosphorus
- ester
- mole
- reaction
- 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 description 104
- 229910052698 phosphorus Inorganic materials 0.000 title description 104
- 239000011574 phosphorus Substances 0.000 title description 101
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 99
- 239000002253 acid Substances 0.000 title description 92
- 239000000314 lubricant Substances 0.000 title description 26
- -1 hydrocarbon radical Chemical group 0.000 description 106
- 235000014786 phosphorus Nutrition 0.000 description 99
- 239000000203 mixture Substances 0.000 description 91
- 238000006243 chemical reaction Methods 0.000 description 63
- 239000000376 reactant Substances 0.000 description 59
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 53
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 52
- 239000000047 product Substances 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 36
- 229930195733 hydrocarbon Natural products 0.000 description 36
- 239000004215 Carbon black (E152) Substances 0.000 description 34
- 235000011044 succinic acid Nutrition 0.000 description 34
- 238000000034 method Methods 0.000 description 33
- 239000003921 oil Substances 0.000 description 33
- 235000011007 phosphoric acid Nutrition 0.000 description 32
- 230000001050 lubricating effect Effects 0.000 description 28
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 26
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 26
- 239000010688 mineral lubricating oil Substances 0.000 description 26
- 239000001384 succinic acid Substances 0.000 description 26
- 229940014800 succinic anhydride Drugs 0.000 description 26
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 25
- 239000000654 additive Substances 0.000 description 25
- 150000008064 anhydrides Chemical class 0.000 description 24
- 239000002480 mineral oil Substances 0.000 description 23
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 22
- 235000010446 mineral oil Nutrition 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000003599 detergent Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229960003742 phenol Drugs 0.000 description 17
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000007513 acids Chemical class 0.000 description 15
- 150000004820 halides Chemical class 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 15
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 14
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- 150000005846 sugar alcohols Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 12
- 229920002367 Polyisobutene Polymers 0.000 description 11
- 229920000098 polyolefin Polymers 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000010687 lubricating oil Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052788 barium Inorganic materials 0.000 description 9
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 150000002924 oxiranes Chemical class 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 150000003444 succinic acids Chemical class 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- 150000003017 phosphorus Chemical class 0.000 description 7
- 239000010802 sludge Substances 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 150000003016 phosphoric acids Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- ITRFOBBKTCNNFN-UHFFFAOYSA-N tris(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound SP(S)(S)=S ITRFOBBKTCNNFN-UHFFFAOYSA-N 0.000 description 6
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- 229930195725 Mannitol Natural products 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 239000000594 mannitol Substances 0.000 description 5
- 235000010355 mannitol Nutrition 0.000 description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 150000003751 zinc Chemical class 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 241000158728 Meliaceae Species 0.000 description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- CETAGCPEESRQJY-UHFFFAOYSA-M [Zn+].CCCCCCCCOP([S-])(=S)OCCCCCCCC Chemical compound [Zn+].CCCCCCCCOP([S-])(=S)OCCCCCCCC CETAGCPEESRQJY-UHFFFAOYSA-M 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 description 4
- 159000000009 barium salts Chemical class 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 3
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000003900 succinic acid esters Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 230000000153 supplemental effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 2
- CEQLOSZEUFWFPN-UHFFFAOYSA-N 4-heptylbenzene-1,2-diol Chemical compound CCCCCCCC1=CC=C(O)C(O)=C1 CEQLOSZEUFWFPN-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 239000004129 EU approved improving agent Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 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 2
- 239000004305 biphenyl Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- IRXBNHGNHKNOJI-UHFFFAOYSA-N butanedioyl dichloride Chemical class ClC(=O)CCC(Cl)=O IRXBNHGNHKNOJI-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000881 depressing effect Effects 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- VDTIMXCBOXBHER-UHFFFAOYSA-N hydroxy-bis(sulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(S)=S VDTIMXCBOXBHER-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 2
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- QMMOXUPEWRXHJS-HYXAFXHYSA-N (z)-pent-2-ene Chemical compound CC\C=C/C QMMOXUPEWRXHJS-HYXAFXHYSA-N 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- PTYXPKUPXPWHSH-UHFFFAOYSA-N 1-(butyltetrasulfanyl)butane Chemical compound CCCCSSSSCCCC PTYXPKUPXPWHSH-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- NQRRNCDWJYBMJW-UHFFFAOYSA-N 2,5-dimethyloct-1-ene Chemical compound CCCC(C)CCC(C)=C NQRRNCDWJYBMJW-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
- OZYRJSLDVFWANY-UHFFFAOYSA-N 2-(3-dodecylphenyl)oxirane Chemical compound CCCCCCCCCCCCC1=CC=CC(C2OC2)=C1 OZYRJSLDVFWANY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IBWLXNDOMYKTAD-UHFFFAOYSA-N 2-(4-chlorophenyl)oxirane Chemical compound C1=CC(Cl)=CC=C1C1OC1 IBWLXNDOMYKTAD-UHFFFAOYSA-N 0.000 description 1
- RUZUMVNATYKTJJ-UHFFFAOYSA-N 2-(4-ethylphenyl)oxirane Chemical compound C1=CC(CC)=CC=C1C1OC1 RUZUMVNATYKTJJ-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AMGIIMBFJUUVJQ-UHFFFAOYSA-N 2-methyl-2-naphthalen-2-yloxetane Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C)CCO1 AMGIIMBFJUUVJQ-UHFFFAOYSA-N 0.000 description 1
- MRXPNWXSFCODDY-UHFFFAOYSA-N 2-methyl-2-phenyloxirane Chemical compound C=1C=CC=CC=1C1(C)CO1 MRXPNWXSFCODDY-UHFFFAOYSA-N 0.000 description 1
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- TXBZITDWMURSEF-UHFFFAOYSA-N 3,3-dimethylpent-1-ene Chemical compound CCC(C)(C)C=C TXBZITDWMURSEF-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HKKMQJBMGBURAB-UHFFFAOYSA-M C(C(C)C)C1=C(C=CC=C1)OP(OC1=C(C=CC=C1)CC(C)C)(=S)[S-].[Zn+] Chemical compound C(C(C)C)C1=C(C=CC=C1)OP(OC1=C(C=CC=C1)CC(C)C)(=S)[S-].[Zn+] HKKMQJBMGBURAB-UHFFFAOYSA-M 0.000 description 1
- XSRHZBURGWEGHH-UHFFFAOYSA-M C(CCCCCCCC)OP(OCCCCCCCCC)(=S)[S-].[Zn+] Chemical compound C(CCCCCCCC)OP(OCCCCCCCCC)(=S)[S-].[Zn+] XSRHZBURGWEGHH-UHFFFAOYSA-M 0.000 description 1
- AZHVHQBLKBATAX-UHFFFAOYSA-M C1(CCCCC1)OP(OC1CCCCC1)(=S)[S-].[Zn+] Chemical compound C1(CCCCC1)OP(OC1CCCCC1)(=S)[S-].[Zn+] AZHVHQBLKBATAX-UHFFFAOYSA-M 0.000 description 1
- VVYHQBHOFCSIRB-UHFFFAOYSA-N C1CCCCC1S(C1CCCCC1)=P(S)(O)OCCC1=CC=CC=C1 Chemical compound C1CCCCC1S(C1CCCCC1)=P(S)(O)OCCC1=CC=CC=C1 VVYHQBHOFCSIRB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 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 1
- 229930194542 Keto Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930045534 Me ester-Cyclohexaneundecanoic acid Natural products 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- WDZCJFZKULYAMW-UHFFFAOYSA-N [O-][N+](S)=O Chemical compound [O-][N+](S)=O WDZCJFZKULYAMW-UHFFFAOYSA-N 0.000 description 1
- UAHZTKVCYHJBJQ-UHFFFAOYSA-N [P].S=O Chemical compound [P].S=O UAHZTKVCYHJBJQ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- XKPXIMKPDMUIDN-UHFFFAOYSA-L barium(2+);2,3-didodecylbenzenesulfonate Chemical compound [Ba+2].CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1CCCCCCCCCCCC.CCCCCCCCCCCCC1=CC=CC(S([O-])(=O)=O)=C1CCCCCCCCCCCC XKPXIMKPDMUIDN-UHFFFAOYSA-L 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- SYFIMIPHNTZHIN-UHFFFAOYSA-N bis(2-methylpropoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)COP(S)(=S)OCC(C)C SYFIMIPHNTZHIN-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- VNBGVYNPGOMPHX-UHFFFAOYSA-N but-3-en-2-ylcyclohexane Chemical compound C=CC(C)C1CCCCC1 VNBGVYNPGOMPHX-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- FEXXLIKDYGCVGJ-UHFFFAOYSA-N butyl 8-(3-octyloxiran-2-yl)octanoate Chemical compound CCCCCCCCC1OC1CCCCCCCC(=O)OCCCC FEXXLIKDYGCVGJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- FSDSKERRNURGGO-UHFFFAOYSA-N cyclohexane-1,3,5-triol Chemical compound OC1CC(O)CC(O)C1 FSDSKERRNURGGO-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- XFAYHOVTJNPDJW-UHFFFAOYSA-N di(nonoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCOP(S)(=S)OCCCCCCCCC XFAYHOVTJNPDJW-UHFFFAOYSA-N 0.000 description 1
- SZXCCXFNQHQRGF-UHFFFAOYSA-N di(propan-2-yloxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)OP(S)(=S)OC(C)C SZXCCXFNQHQRGF-UHFFFAOYSA-N 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- IWHTZOQGVGHYQT-UHFFFAOYSA-N dicyclohexyloxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound C1CCCCC1OP(=S)(S)OC1CCCCC1 IWHTZOQGVGHYQT-UHFFFAOYSA-N 0.000 description 1
- GQCQJECYDYZWHI-UHFFFAOYSA-N didecoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCCOP(S)(=S)OCCCCCCCCCC GQCQJECYDYZWHI-UHFFFAOYSA-N 0.000 description 1
- GHKVUVOPHDYRJC-UHFFFAOYSA-N didodecyl hexanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCCCC GHKVUVOPHDYRJC-UHFFFAOYSA-N 0.000 description 1
- SPBMDAHKYSRJFO-UHFFFAOYSA-N didodecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)OCCCCCCCCCCCC SPBMDAHKYSRJFO-UHFFFAOYSA-N 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- VFXJDWTUUZBKKT-UHFFFAOYSA-N dihexoxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCOP(S)(=S)OCCCCCC VFXJDWTUUZBKKT-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- FRXGWNKDEMTFPL-UHFFFAOYSA-N dioctadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(=O)OCCCCCCCCCCCCCCCCCC FRXGWNKDEMTFPL-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TXGJTWACJNYNOJ-UHFFFAOYSA-N hexane-2,4-diol Chemical compound CCC(O)CC(C)O TXGJTWACJNYNOJ-UHFFFAOYSA-N 0.000 description 1
- MIMWEDULOWDYDY-UHFFFAOYSA-N hexoxy-hydroxy-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCOP(O)(S)=S MIMWEDULOWDYDY-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000010705 motor oil Substances 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 125000001117 oleyl 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])=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
- 229940113162 oleylamide Drugs 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- RWQFRHVDPXXRQN-UHFFFAOYSA-N phosphorus sesquisulfide Chemical compound P12SP3SP1P2S3 RWQFRHVDPXXRQN-UHFFFAOYSA-N 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- RQIITWKDTBNDJW-UHFFFAOYSA-N trichloro(diphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Cl)(Cl)(Cl)C1=CC=CC=C1 RQIITWKDTBNDJW-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- BEFUBHVQRFELBK-UHFFFAOYSA-N trihydroxy(diphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(O)C1=CC=CC=C1 BEFUBHVQRFELBK-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C10M2201/06—Metal compounds
- C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
-
- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
-
- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
-
- 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/32—Esters of carbonic acid
-
- 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
- C10M2207/40—Fatty vegetable or animal 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
-
- 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
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/08—Halogenated waxes
-
- 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
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/066—Arylene diamines
-
- 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
- C10M2215/08—Amides
-
- 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
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- 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
- C10M2215/26—Amines
-
- 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
- C10M2215/28—Amides; Imides
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
- C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
-
- 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
-
- 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
- C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
-
- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
-
- 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
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
-
- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
-
- 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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- 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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- 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
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/061—Metal salts
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/02—Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
-
- 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
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2225/04—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of macromolecualr compounds not containing phosphorus in the monomers
- C10M2225/041—Hydrocarbon polymers
-
- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2040/02—Bearings
-
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
-
- 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
- C10N2040/12—Gas-turbines
-
- 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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
-
- 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
- C10N2040/25—Internal-combustion engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol fueled engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/26—Two-strokes or two-cycle engines
-
- 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
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines
- C10N2040/28—Rotary engines
Definitions
- Lubricants especially lubricants for internal combustion engines and gears, are prepared by blending a lubricating oil and a phosphorus-containing ester. Such lubricants have improved oxidation resistance and detergent properties.
- the phosphorus-containing ester is prepared by reacting a polyhydric alcohol with both a high molecular weight substituted succinic reactant having at least about 50 aliphatic carbon atoms in the substituent and a phosphorus reactant which may be phosphorus pentoxide, phosphoric acid, or an alkyl ester of phosphoric acid.
- the preferred phosphorus-containing ester is illustrated by the product formed by reacting pentaerythritol first with a polyisobutene-substituted succinic anhydride and then with triphenylphosphite.
- This invention relates to novel compositions of matter and processes for preparing the same.
- this invention relates to compositions useful as plasticizers, detergents, anti-rust agents, emulsifiers, and additives in lubricating compositions, fuels, hydrocarbon oils, and power transmitting fluids.
- the polyhydroxy compounds from which the phosphorus-containing esters of this invention are derived include principally polyhydric alcohols and polyhydric phenols. They preferably contain less than about 30 carbon atoms.
- alkylene glyc-ols and poly(oxy-alkylene)glycols such as ethylene glycol, di(ethylene glycol), tri(ethylene glycol), di(propylene glycol), tri(butylene glycol), penta(ethylene glycol) and other poly(oxy-alkylene)glycols formed by the condensation of two or more moles of ethylene glycol, propylene glycol, octylene glycol, or a like glycol having up to about 12 carbon atoms in the alkylene radical.
- polyhydric alcohols include glycerol, pentaerythritol, 2,4-hexanediol, pinacol, erythritol, arabitol, sorbitol, mannitol, 1,2-cyclohexanediol, Xylylene glycol, and 1,3,5-cyclohexanetriol.
- the polyhydric phenols are exemplified by hydroquinone, resorcinol, 4-heptyl-1,2- di-hydroxy-benzene, 1,2 dihydroxy naphthalene, 4-polypropene (molecular weight of 1500)-substituted 1,2-dihydroxy-benzene, methyl-S-decyl-1,2-dihydroxy-naphthalene, and pyrogallol.
- Still other polyhydroxy compounds include the monoesters of glycerol, sorbitol, mannitol, or other higher polyhydroxy alcohols, such as mono-acetate of glycerol, mono-oleate of sorbitol mono-propionate of mannitol, or the like.
- interpolymers of an unsaturated alcohol with a copolymerizable olefinic substance such as styrene, vinyl ether, vinyl acetate, isobutene, butadiene, di-vinylbenzene or the like.
- the interpolymers contain two or more monomeric units derived from the unsaturated alcohol and thus constitute the Polyhydric alcohols contemplated for use in the process of this invention. Specific examples of such interpolymers are the copolymer of 5 moles of allyl alcohol and 1 mole of styrene having an average molecular weight of about 2500.
- the radical R in the formula of the polyhydroxy compounds designates a radical which is substantially hydrocarbon in character.
- the radical may be a hydrocarbon radical or a polar-substituted hydrocarbon radical.
- the radical may contain inert polar groups provided that such groups are not present in proportions sufiiciently large to alter significantly the hydrocarbon character of the radical.
- the polar groups are exemplified by chloro, bromo, keto, aldehyde, nitro, etc.
- the upper limit with respect to the proportion of such polar groups in a hydrocarbon radical is usually about based upon the weight of the hydrocarbon portion of the radical.
- an ether-containing hydrocarbon group may be used wherein the ether groups such as oxyalkylene or poly(oxy-alkylene) groups may contain as many as one oxygen atom for each two carbon atoms.
- the hydrocarbon-substituted succinic acid-producing compounds useful in preparing the phosphorus-containing esters may be the succinic acids, anhydrides, halides, or esters in which the hydrocarbon substituent contains at least about 50 aliphatic carbon atoms.
- the sources of the hydrocarbon substituent include principally the high molecular weight substantially saturated petroleum fractions and substantially saturated olefin polymers, particularly polymers of mono-olefins having from 2 to 30 carbon atoms.
- the especially useful polymers are the polymers of l-mono-olefins such as ethylene, propene, l-butene, isobutene, l-hexene, l-octene, 2-methyl-1- heptene, 3-cyclohexyl-1-butene, and 2-methyl-5-propyl-1- hexene.
- interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and polyolefins.
- Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene; isobutene with butadiene; propene with isoprene; ethylene with piperylene; isobutene with chloroprene; isobutene with p-methyl styrene; l-hexene with 1,3-hexadiene; l-octene with l-hexene; l-heptene with l-pentene; 3- methyl-l-butene with l-octene; 3,3-dimethyl-l-pentene with l-hexene; isobutene with styrene and piperylene; etc.
- the relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the final products derived from such interpolymers.
- the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about 80%, preferably at least about 95%, on a weight basis, of units derived from the aliphatic mono-olefins and no more than about 5% of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percentage of olefinic linkages should be less than about 2% of the total number of carbonto-carbon covalent linkages.
- interpolymers include the copolymer of 95% (by weight) of isobutene with 5% of styrene; the terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; the terpolymer of 95% of isobutene with 2% of l-butene and 3% of l-hexene; the terpolymer of of isobutene with 10% of l-pentene and 10% of l-octene; the copolymer of 80% of l-hexene and 20% of l-heptene; the terpolymer of of isobutene with 2% of cyclohexene and 8% of propene; and the copolymer of 80% of ethylene and 20% of propene.
- Another source of the hydrocarbon radical comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight White oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymers illustrated above or high molecular weight olefinic substances.
- olefin polymers having molecular weights of about 750-5000 are preferred.
- Higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 or higher have been found to impart viscosity index improving properties to the final products of this invention.
- the use of such higher molecular weight olefin polymers often is desirable.
- the hydrocarbon substituent in the succinic acid-producing compound likewise may contain inert polar groups.
- it may be a radical which is substantially hydrocarbon in character such as is referred to in the above description of the hydrocarbon radical R of the polyhydroxy compounds.
- the succinic acid-producing compounds useful in the above process are preferably substantially hydrocarbonsubstituted succinic acids and anhydrides. These succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as the olefin polymer described hereinabove. The reaction involves merely heating the two reactants at a temperature about 100- 200 C. The product from such a reaction is an alkenyl succinic anhydride. The alkenyl group may be hydrogenated to an alkyl group.
- the anhydride may be hydrolyzed by treatment with water or steam to the corresponding acid. Either the anhydride or the acid may be converted to the corresponding acid halide or ester by reaction with, e.g., phosphorus halide, phenols, or alcohols.
- hydrocarbons containing an activating polar substituent i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the above-illustrated reaction for preparing the succinic compounds.
- polar substituents may be illustrated by sulfide, disulfide, nitro, mercaptan, bromine, kctone, or aldehyde radicals.
- polar-substituted hydrocarbons examples include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc.
- Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range from about 100 C. to about 200 C.
- the acid halides of the succinic acids can be prepared by the reaction of the acids or their anhydrides with a halogenation agent such as phosphorus tri-bromide, phosphorus pentachloride or thionyl chloride.
- the esters of such acids can be prepared simply by the reaction of the acids or their anhydrides with an alcohol or a phenolic compound such as methanol, ethanol, octadecanol, cyclohexanol, phenol, naphthol, octylphenol, etc.
- the esterification is usually promoted by the use of an alkaline catalyst such as sodium hydroxide or sodium alkoxide or an acidic catalyst such as sulfuric acid.
- the nature of the alcoholic or phenolic portion of the ester radical appears to have little influence on the utility of such ester as reactant in the process described hereinabove.
- the phosphorus acid-producing reactants useful in the above process for forming the phosphorus-containing esters of this invention may be acids, anhydrides, esters, or halides.
- the phosphorus acids may be phosphoric acids and phosphorous acids including the oxyphosphorus acids, the thiophosphorus acids, as well as the mixed oxythiophosphorus acids (i.e., those containing both oxygen and sulfur).
- a phosphoric acid is used in a generic sense to denote the class consisting of phosphoric acid (H PO phosphorotetrathioic acid (H PS phosphoromonothioic acid (H PO S), phosphorodithioic acid (H PO S and phosphorotrithioic acid (H -POS).
- H PO phosphorotetrathioic acid H PS phosphoromonothioic acid (H PO S)
- H PO S phosphorodithioic acid
- H -POS phosphorotrithioic acid
- a phosphoromonothioic acid in which the sulfur atom is attached only to the phosphorus atom i.e., -P(S) (OH)
- a phosphorothionic acid i.e., -P(S) (OH)
- its isomer in which the sulfur atom is attached to both the phosphorus atom and a hydrogen atom i.e., --P(O)(S-H)
- dialkylphosphoric acids i.e., dialkyl esters of phosphoric acids
- dialkylphosphoric acids include dialkylphosphoric acid ((alkyl-O) 'P(O) (OH)); dialkylphosphorotetrathioic acid ((alkyl-S) P(S) (SH) 0,0-dialkylphosphorodithioic acid y )z H) O,S-dialkylphosphorodithionic acid ((alkyl-O)(alkyl-S)P(S)(OH)) O,S-dialkylphosphorodithiolic acid ((alkyl-O) (alkyl-S)'P(O) (SH) O,S-dialkylphosphorotrithioic acid
- the phosphorus acid anhydrides, esters, and halides likewise are useful for preparing the phosphorus-containing esters of this invention.
- the anhydrides of phosphorus acids are especially desirable. They are illustrated by phosphorus pentoxide, phosphorus pentasulfide, phosphorus heptasulfide, phosphorus sesquisulfide, and phos phorus oxysulfide.
- the anhydrides of organic phosphorus acids are exemplified by the anhydrides of diphenylphosphoric acid, etc.
- the halides of the phosphorus acids include, for instance, phosphorus trichloride, phosphorus pentachloride, phosphorothioic trichloride, phosphorus tribromide, diphenylphosphorus chloride, 0,0'-di(chlorophenyl)phosphorothioic chloride, 0,0'-diphenylphosphorothioic chloride, and diphenylphosphorus trichloride.
- the esters of the phosphorus acids may be the completely esterified acids or partially esterfied acids.
- the latter are also known as acidic esters, i.e., at least a portion of the acid is not esterified; they are illustrated by the monoor the di-esterified phosphoric or phosphorous acids.
- the ester portion may be derived from a hydrocarbon radical, usually one having less than about 30 and preferably from about 1 to about 24 aliphatic carbon atoms.
- the hydrocarbon radicals may contain inert polar groups such as are described previously.
- esters are, for example, methyl ester of phosphoric acid, dimethyl ester of phosphoric acid, trimethyl ester of phosphoric acid, O-methyl ester of phosphorothiolic acid, dicyclohexyl ester of phosphoric acid, 0,0-dicyc1ohexyl ester of phosphorodithioic acid, dicyclohexyl ester of phosphorotetrathioic acid, O-cyclohexyl-S-decyl ester of phosphoromonothioic acid, 0,0'-diphenyl ester of phosphoromonothiolic acid, triphenyl ester of phosphoric acid, triphenyl ester of phosphorus acid, tritolyl ester of phosphoric acid, dioctadecyl ester of phosphorus acid, trinaphthyl ester of phosphorus acid, trinaphthyl ester of phosphoric acid, 0,0'-dinaphth
- the esters of phosphoric acid and phosphorothioic acids are obtained by the reaction of phenol or an alcohol with phosphoric acid or a phosphorothioic acid, or an anhydride of the acid such as phosphorus pentoxide, phosphorus pentasulfide, or phosphorus oxysulfide.
- the reaction is usually carried out simply by mixing the reactants at a temperature above about 50 C., preferably between about C. and C.
- the esters of phosphoric acids tend to decompose at high temperatures. Thus it is often desirable to avoid prolonged exposure of the reaction mixture to temperatures above about 150 C.
- a solvent may be used in the reaction to facilitate mixing of the reactants and control of the reaction temperature.
- the solvent may be benzene, naphtha, chlorobenzene, mineral oil, kerosene, cyclohexane, or carbon tetrachloride.
- a solvent capable of forming a rela tively lowboiling azeotrope with water further aids the removal of water in the esterification of an alcohol or phenol with the phosphorus acid reactant.
- the relative amounts of the alcohol or phenol reactant and the acid reactant influence the nature of the ester obtained.
- the product will be a mixture of the mono-, di-, and tri-esters of the acid and such a mixture is desirable for use in this invention for reasons of economy.
- the reaction of an alcohol or phenol with phosphorus pentasulfide ordinarily results in 0,0'-diester of phosphorodithioic acid.
- Such reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide and may be carried out within the temperature range from about 50 C. to about 250 C.
- the preparation of 0,0'-di-n-hexylphosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about 100 C. for about 2 hours. Hydrogen sulfide is liberated and the residue is the defined acid.
- Treatment of the phosphorodithioic acid with water or steam removes one or both sulfur atoms and converts the product to the corresponding phosphoromonothioic acid or phosphoric acid.
- the esters of phosphorotetrathioic acid can be prepared by first the reaction of a mercaptan or thiophenol with PSCl or PSBr to produce an intermediate which is either a phosphorotrithioic halide or triester of phosphorotetrathioic acid and the subsequent reaction of the intermediate with hydrogen sulfide or sodium hydrosulfide.
- the esters of phosphorotrithioic acids are obtained by the treatment of the esters of the phosphorotetrathioic acids with water or steam.
- esters of phosphorous acids are obtained by the reaction of an alcohol or phenol With phosphorous acid or a phosphorus trihalide such as phosphorus tribromide or phosphorus trichloride and the above noted reaction usually requires carefully controlled conditions such as low temperature in order to give a substantial yield of the esters of phosphorous acids. Under other conditions the reaction of an alcohol or phenol with a phosphorus trihalide may result in a phosphonic acid or ester. Such esters are readily susceptible to rearrangement to phosphonic acids and esters.
- the reaction by which the phosphorus-containing esters of this invention are obtained can be effected simply by mixing a polyhydroxy reactant with the succinic acid-producing and the phosphorus acid-producing reactants at the desired temperature.
- the use of an inert solvent in the reaction is not necessary but often desirable, especially when a highly viscous or solid reactant is present in the reaction mixture.
- the inert solvent useful in the reaction may be a hydrocarbon such as benzene, toluene, naphtha, cyclohexane, n-hexane, or mineral oil.
- the reaction by which the phosphorus-containing esters of this invention are obtained may be carried out by mixing the polyhydric compound, the hydrocarbon-substituted succinic acid-producing compound, and the phosphOrus acid-producing compound at a temperature above about 100 C., preferably be ween about 125 C. and 250 C.
- the optimum reaction temperature depends to some extent upon the nature of the specific reactions used. For instance, where the succinic acid-producing compound and the phosphorus acid-producing compound are relatively reactive acids or anhydrides, the reaction temperature may be below about 200 C.
- the reaction temperature often will be 200 C. or higher.
- the maximum temperature for the process is determined by the decomposition point of the reaction mixture. It rarely exceeds 300 C.
- the product resulting from the process of this invention usually is a complex mixture of esters derived from the polyhydroxy reactant by the esterification of some of its hydroxy groups with the succinic acid-producing compound and some other hydroxy groups with the phosphorus acid-producing compounds.
- the product of this invention is a complex mixture of esters characterized by the presence of ester radicals of both succinic acid ester type and phosphorus acid ester type. The precise composition of the product is not fully understood. Consequently, the product is best described in terms of the process by which it is formed.
- composition of the product of this invention depends for the most part upon the relative proportions of the three reactants used in the process.
- the total amount of the succinic acid-producing reactant and the phosphorus acid-producing reactant to be used for each mole of the polyhydroxy reactant ordinarily ranges from about 0.5 mole to as many moles as the number of the hydroxy radicals within the molecular structure of the polyhydroxy reactant.
- the relative amounts of the succinic acid-producing reactant and the phosphorus acid-producing reactant ordinarily are such that they are within the range of molar ratios from about 0.1 :1 to about 10:1, respectively.
- a mixture of a succinic acidproducing reactant and a phosphorus acid-producing reactant in an amount such that the combined quantity of the two acid-producing reactants ranges from about 0.5 to about 5 moles and that the molar ratio of the succinic acid-producing reactant to the phosphorus acid-producing reactant ranges from about 0.1:1 to about 10:1.
- each mole of a tetrahydroxy reactant there may be employed from about 0.05 mole to about 3.6 moles of a succinic acid-producing reactant and from about 0.05 mole to about 3.6 moles of a phosphorus acidproducing reactant provided that the molar ratio of the succinic acid-producing reactant and the phosphorus acidproducing reactant be within the range of about 0.1:1 to about 10:1.
- the preferred amounts of the three reactants are such that 1 mole of the polyhydroxy reactant is used with from about 0.5 mole to about 1 mole of a succinic acid-producing reactant and from about 1 mole to 3 moles of a phosphorus acid-producing compound.
- a specific example of the preferred products of this invention is one obtained by the reaction of 1 mole of pentaerythritol with 1 mole of a succinic anhydride and 2 moles of a triaryl phosphite.
- the molecular weight may be the average molecular weight estimated from the elemental analysis of the mixture.
- the molecular weight of a succinic acid ester likewise may be estimated from the potential acidity as determined by its saponification number.
- the lower limit of about 0.5 mole for the combined quantities of the two acid-producing reactants per mole of the polyhydroxy reactant is based upon the stoichiometry for the esterification of only one of the hydroxy groups of the polyhydroxy reactant
- the upper limit of x number of moles for the combined quantities of the two acid-producing reactants per mole of the polyhydroxy reactant having x number of hydroxy groups is based upon the stoichiometry for the esterification of all of the hydroxy groups of the polyhydroxy reactant.
- a preferred mode of carrying out the process of this invention involves reacting a polyhydroxy reactant with the succinic acid-producing reactant to form a partially esterified intermediate and then reacting the intermediate With a phosphorus acid-producing reactant.
- the first step i.e., the formation of the partially esterified intermediate
- . 9 preferably eflfected at a temperature between about 100 C. and 200 C. and the second step, i.e., the reaction of the intermediate with the phosphorus reactant may be carried out at a temperature from about 80 C. to about 250 C.
- This particular mode of carrying out the process of this invention is preferred because the products resulting therefrom have been found to be especially useful for the purposes of this invention such as in hydrocarbon oil and lubricating compositions.
- Another alternative mode of carrying out the process of this invention involves first reacting polyhydroxy reactant with a phosphorus acid-producing reactant to form a partially esterified intermediate and then reacting the intermediate with the succinic acid-producing reactant.
- the process admits further variations in forming the intermediate of a polyhydroxy substance which has been partially esterified with a phosphorus acid.
- the reaction of phosphoric acid with an epoxide, particularly an alkylene oxide such as ethylene oxide, propylene oxide, hexylene oxide, or epichlorohydrin may result in a partially esterified glycol, i.e., a glycol having one free hydroxy group and one hydroxy group which has been converted to a phosphorus acid ester group by the esterification with phosphoric acid.
- a more specific example is found in the reaction of 1 mole of phosphoric acid with 3 moles of propylene oxide resulting in the formation of tri(hydroxypropyl) ester of phosphoric acid. This tri(hydroxypropyl) ester may then be used in reaction with a succinic acid-producing reactant in order to form the phosphorus-containing esters of this invention.
- esterification catalysts are useful for this purpose. They are illustrated by titanium tetrachloride, aluminum chloride, titanium tetrafiuoride, boron trifiuoride, aluminum tribromide, potassium ethoxide, sodium methoxide, calcium phenate, sodium hydroxide, calcium oxide, benzene sulfonic acid, toluene sulfonic acid, etc. A small amount such as 0.001% by weight of the catalyst often is sufiicient to promote esterification of the process of this invention. The amount of the catalyst may range up to about 1% by Weight of the process mixture.
- the product of this invention is formed by trans-esterification wherein one or both of the methyl radicals of the succinic reactant are replaced with radicals derived from the partially esterified glycerol intermediate and methanol is the by-product.
- the product of this invention is formed by transesterification wherein one or more of the phenyl radicals of triphenyl phosphite are replaced with the ester radicals derived from the partially esterified glycerol intermediate and phenol is the by-product.
- the latter may involve trans-esterification reactions including, e.g., the one illustrated as follows:
- R is a substantially hydrocarbon radical.
- the above phosphorus-containing ester may react further with the partially esterified glycerol to form more complex products such as polymeric substances.
- a succinic halide such as a polyisobutene-substituted succinic acid dichloride
- a phosphorus acid halide such as phosphorus pentoxide or phosphorus trichloride
- a succinic dichloride with ethylene glycol and phosphorus pentoxide may proceed as follows:
- a partially esterified pentaerythritol is prepared by adding 136 parts (by weight, 1 molar proportion) of pentaerythritol to a mixture of 1130 parts (1 molar proportion) of a polyisobutene-substituted succinic anhydride having an acid number of 99 (prepared by heating a chlorinated polyisobutene having a molecular weight of 900 and a chlorine content of 4.4% with 20% molar excess of maleic anhydride at 205 C.) and 830 parts of a mineral oil and heating the resulting mixture at C. for 5 hours and at 200-210 C. for 5 hours and filtering the product.
- the by-product (water) is distilled off during the heating.
- the filtrate is a 40% oil solution of the partially esterified ester intermediate.
- To 1020 parts of this filtrate there is added 310 parts (0.5 molar proportion for each, molar proportion of the pentaerythritol used) of triphenyl phosphite.
- the mixture is heated at 180-190 C. for 10 hours and then at 180 C./20 mm. whereupon 96 parts of phenol is distilled off as the byproduct of trans-esterification.
- the filtrate is a 33% oil solution of the phosphorus-containing ester having a phosphorus content of 2.5%.
- propylene glycol is prepared by adding dropwise propylene oxide to the above succinic acid (0.5 mole per mole of propylene oxide) at 80110 C., heating the resulting mixture to 100 C./7 mm., mixing the residue with an additional quantity of mineral oil to prepare a 50% oil solution and then filtering the oil solution.
- a mixture of 1733 parts of the above oil solution of the partially esterified propylene glycol and 91 parts of triphenylphosphite is heated at 150160 C. for 7.5 hours whereupon phenol (57 parts) is distilled off.
- the residue is diluted with mineral oil to form a 50% oil solution and filtered.
- the filtrate is an oil solution of a phosphorus-containing ester having a phosphorus content of 0.5%.
- EXAMPLE 3 The oil solution (1890 parts) of the partially esterified propylene glycol of Example 2 and phosphorus pentoxide (46 parts) are mixed at 23 C. The mixture is heated at 5060 C. for 7 /2 hours and then to 60 C./ mm. The mixture is filtered. The filtrate is an oil solution of a phosphorus-containing ester.
- EXAMPLE 4 A mixture of 670 parts of pentaerythritol and 2670 parts of the polyisobutene-substituted succinic anhydride of Example 1 (0.5 mole per mole of pentaerythritol) in 2194 parts of mineral oil is heated to 190 C. in 3 hours and then at 190200 C. for 8 hours. The mixture is blown with nitrogen for 0.5 hour and filtered. The filtrate is a 40% oil solution of a partially esterified pentaerythritol. To 2935 parts of the above solution and 1060 parts of mineral oil there is added 284 parts of phosphorus pentoxide (0.8 molar proportions for each molar proportion of the pentaerythritol used). The resulting mixture is heated at 115l20 C. for 5 hours and filtered. The filtrate is a oil solution of a phosphorus-containing ester having a phosphorus content of 1.2%.
- EXAMPLE 5 A mixture of 1 mole of ethylene glycol, 0.5 mole of phophorus pentoxide, and 0.5 mole of a polyisobutene (molecular weight of 60,000)-substituted succinic anhydride (having an acid number of 100 and prepared by the reaction of maleic anhydride and a chlorinated polyisobutene having a molecular weight of 60,000 and a chlorine content of 4.3% at 205 C.) in three times its volume of a mineral oil is prepared at C. and then heated at 120140 C. for 10 hours.
- a polyisobutene molecular weight of 60,000-substituted succinic anhydride (having an acid number of 100 and prepared by the reaction of maleic anhydride and a chlorinated polyisobutene having a molecular weight of 60,000 and a chlorine content of 4.3% at 205 C.) in three times its volume of a mineral oil is prepared at C. and then heated at 120140 C
- EXAMPLE 6 A mixture of 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of glycerol in twice the volume of the mixture of toluene is heated at the reflux temperature (100 C.) while water is removed by azeotropic distillation. To the residue there is added 0.5 mole of phosphorus pentasulfide and the resulting mixture is heated at 90110 C. for 4 hours. Toluene is then removed by vacuum distillation. The residue is a phosphorus-containing ester.
- EXAMPLE 8 A partially esterified propylene glycol is obtained by reacting 1 mole of phosphoric acid with 3.3 moles of propylene oxide while the by-product (water) is distilled 12; 01f. To 390 grams of this partially esterified propylene glycol there is added 200 grams of toluene and 1495 grams of the polyisobutene-substituted succinic anhydride of Example 1. The mixture is heated at 158163 C. for 8 hours and then at 160 C./1-2 mm. The residue is mixed with 1200 grams of mineral oil and heated to distill otf toluene. The residue is filtered. The filtrate is an oil solution of a phosphorus-containing ester having a phophorus content of 7.7%.
- EXAMPLE 9 A partially esterified sorbitol is prepared by heating at 110-150 C. 1 mole of sorbitol and 1 mole of phosphorus pentoxide. The intermediate is dissolved in white oil and mixed with 2.5 moles of the polyisobutene-substituted succinic anhydride of Example 1. The resulting mixture is heated at 200 C. for 7 hours and filtered.
- EXAMPLE 10 An olefin polymer-substituted succinic anhydride is obtained by heating 1.2 moles of maleic anhydride with 1 mole of a copolymer of mole percent of propylene and 25 mole percent of ethylene having an average molecular weight of 10,000 at 200-220 C. To a solution of the above anhydride in an equal weight of mineral oil, there is added at 25 C. 2 moles of neopentyl glycol and 1 mole of phosphorus acid. The mixture is heated to 120 C. for 2 hours and then at 120-180 C. for 5 hours whereupon water is removed by distillation. The residue is filtered. The filtrate is an oil solution of the phosphoruscontaining ester.
- EXAMPLE 11 A phosphorus-containing ester is prepared by the procedure of Example 10 from a reaction mixture of 0.1 mole of an isobutene-styrene copolymer (:5 by weight of isobutene to styrene, average molecular weight of 2000)-substituted succinic anhydride, 1 mole of di(ethylene glycol and 0.5 mole of phosphoric oxychloride.
- EXAMPLE 12 A phosphorus-containing ester is obtained by the procedure of Example 10 from a reaction mixture of 0.5 mole of the polyisobutene-substituted succinic anhydride of Example 1, 1 mole of tri(ethylene glycol), and 0.1 mole of dimethyl phosphite.
- EXAMPLE 13 A phosphorus-containing ester is obtained by the procedure of Example 10 from a reaction mixture of 1 mole of the polyisobutene-substituted succinic anhydride of Example 1, 0.5 mole of triethyl phosphite, and 1 mole of a copolymer of 5 moles of allyl alcohol and 1 mole of styrene having a molecular weight of 1100.
- EXAMPLE 14 A phosphorus-containing ester is obtained by heating at 150-180 C. a mixture of the partially esterified pentaerythritol (40% oil solution) and diphenylphosphorothioic chloride (2 moles per mole of pentaerythritol).
- EXAMPLE 15 A phosphorus-containing ester is obtained by first heating at 120-200 C. 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of mannitol monooleate to form a partially esterified mannitol intermediate and then heating at 200 C. the intermediate with 3 moles of di(heptylphenyl)phosphorus chloride (i.e., (C H C H O) PCl) in an equal volume of mineral oil.
- di(heptylphenyl)phosphorus chloride i.e., (C H C H O) PCl
- EXAMPLE 16 A phosphorus-containing ester is obtained by first heating at -180 C. 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of glycerol in 1000 grams of mineral oil and then heating 13 at 150-200' C. the above reaction mixture with 0.5 mole of the anhydride of diethylphosphoric acid (i.e.,
- EXAMPLE 17 A phosphorus-containing ester is prepared as follows: a partially esterified resorcinol (formed by heating at 100200 C. 0.75 mole of the polyisobutene-substituted succinic anhydride of Example 1 with 1 mole of resorcinol in 1000 grams of diphenyl ether as the diluent) and phosphorus pentoxide (0.1 mole per mole of resorcinol) areheated at 150160 C. for hours.
- a partially esterified resorcinol formed by heating at 100200 C. 0.75 mole of the polyisobutene-substituted succinic anhydride of Example 1 with 1 mole of resorcinol in 1000 grams of diphenyl ether as the diluent
- phosphorus pentoxide 0.1 mole per mole of resorcinol
- EXAMPLE 19 A phosphorus-containing ester is obtained by the procedure of Example 18 except that resorcinol is replaced on a molar basis with 4-heptyl-1,2-dihydroxybenzene.
- EXAMPLE 20 A phosphorus-containing ester is obtained by the procedure of Example 18 except that resorcinol is replaced on a molar basis with 1,2-dihydroxynaphthylene.
- the phosphorus-containing esters of this invention are useful for a wide variety of purposes including pesticides, plasticizers, rust-inhibiting agents for treatment of metals, corrosion-inhibiting agents, extreme pressure agents, antiwear agents, and detergents.
- a principal utility of such products is as additives in lubricants. It has been discovered in accordance with this invention that when used for such purpose their effectiveness to impart a specific property to a lubricant is closely related to the size of the hydrocarbon substituent in the hydrocarbon-substituted succinic acid-producing compounds from which the phosphorus-containing esters are derived. More particularly it has been found that products in which the substantially hydrocarbon substituent contains more than about 50 aliphatic carbon atoms are particularly effective for the purposes of this invention.
- the lubricating oils in which the substituted polyamines of this invention are useful as additives may be of synthetic, animal, vegetable, or mineral origin. Ordinarily mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di-Z-ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils, ranging in viscosity from about 40 Saybolt Universal Seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
- the concentration of the phosphorous-containing esters as additives in lubricants usually ranges from about 0.01% to about by weight.
- the optimum concentrations for a particular application depend to a large measure upon the type of service to which the lubricant is to be subjected.
- lubricants for use in gasoline internal combustion engines may contain from about 0.5 to about 10% of the additive
- lubricating compositions for use in gears and diesel engines may contain as much as or even more of the additive.
- Lubricants for use in the oil-fuel mixture for two-stroke engines may contain from about 1% to 10% of the additive.
- additives include, for example, supplemental detergents of the ashcontaining type, viscosity index improving agents, pour point depressing agents, anti-foam agents, extreme pressure agents, rust-inhibiting agents, and supplemental oxidation and corrosion-inhibiting agents.
- the ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride.
- olefin polymer e.g., polyisobutene having a molecular weight of 1000
- a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide,
- the term basic salt is used to designate the metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical.
- the commonly employed methods for preparing the basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50 C. and filtering the resulting mass.
- a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide
- Examples of compounds useful as the promoters include phenolic substances such as phenol, naphthol, alkylphenol, triophenol, sulfurized alkylphenol, and condensation products of formaldehyde With a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediamine, phenothiazine, phenyl beta-naphthylamine, and dodecylamine.
- a particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of water and carbonating the mixture at an elevated temperature such as 60-200 C.
- the preparation of a basic sulfonate detergent is illustrated as follows: A mixture of 490 parts (by weight) of a mineral oil, parts of water, 61 parts of heptylphenol, 340 parts of barium mahogany sulfonate, and 227 parts of barium oxide is heated at 100 C. for 0.5 hour and then to C. Carbon dioxide is then bubbled into the mixture until the mixture is substantially neutral. The mixture is filtered and the filtrate found to have a sulfate ash content of 25%.
- a polyisbutene having a molecular weight of 50,000 is mixed with 10% by weight of phosphorus pentasulfide at 200 C. for 6 hours.
- the resulting product is hydrolyzed by treatment'with steam at C. to produce an acidic intermediate.
- the acidic intermediate is then converted to a basic salt by mixing twice its volume of mineral oil, 2 moles of barium hydroxide and 0.7 mole of phenol and carbonating the mixture at 150 C. to produce a fluid product,
- the phosphorus-containing esters are especially adapted for use in combination with extreme pressure and corrosion-inhibiting additives such as metal dithiocarbamates, xanthates, the Group II metal phosphorodithioates and their epoxide adducts, hindered phenols, sulfurized cycloalkanes, di-alkyl polysulfides, sulfurized fatty esters, phosphosulfurized fatty esters, alkaline earth metal salts of alkylated phenols, dialkyl phosphites, triaryl phosphites, and esters of phosphorodithioic acids.
- Combinations of the phosphorus-containing esters of this invention with any of the above-mentioned additives are especially desirable for use in lubricants which must have superior extreme pressure and oxidation-inhibiting characteristics.
- the Group II metal phosphorodithioates are the salts of acids having the formula R SH in which R and R are substantially hydrocarbon radicals.
- the metals for forming such salts are exemplified by bar ium, calcium, strontium, zinc, and cadmium.
- the barium and zinc phosphorodithioates are especially preferred.
- the substantially hydrocarbon radicals in the phosphorodithioic acid are preferably low or medium molecular weight alkyl radicals and alkylphenyl radicals, i.e., those having from about 1 to about 30 carbon atoms in the alkyl group.
- Illustrative alkyl radicals include methyl, ethyl, isopropyl, isobutyl, n-butyl, sec-butyl, the various amyl alcohols, n-hexyl, methylisobutyl carbinyl, heptyl, 2-ethylhexyl, di' isobutyl, isooctyl, nonyl, behenyl, decyl, etc.
- Illustrative lower alkylphenyl radicals include butylphenyl, amylphenyl, di-amylphenyl, octylphenyl, etc.
- Cycloalkyl radicals likewise are useful and these include chiefly cyclohexyl and the lower alkyl-cyclohexyl radicals.
- Other substantially hydrocarbon radicals likewise are useful such as tetradecyl, octadecyl, eicosyl, butylnaphthyl, hexylnaphthyl, octylnaphthyl, cyclohexylphenyl, naphthenyl, etc.
- phosphorodithioic acids from which the Group II metal salts of this invention are prepared is well known. They are prepared by the reaction of phosphorus pentasulfide with an alcohol or phenol. The reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide, and may be carried out within the temperature range from about 50 C. to about 200 C.
- the preparation of 0,0-di-n-hexyl phosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about 100 C. for about 2 hours. Hydrogen sulfide is liberated and the residue is the defined acid.
- the preparation of the zinc or barium salt of this acid may be effected by reaction with zinc oxide or barium oxide. Simply mixing and heating these two reactants is sufficient to cause the reaction to take place and the resulting product is sufiiciently pure for the purpose of this invention.
- Especially useful Group II metal phosphorodithioates can be prepared from phosphorodithioic acids which in turn are prepared by the reaction of phosphorus pentasulfide with mixtures of alcohols.
- the use of such mixtures enables the utilization of cheaper alcohols which in themselves do not yield oil-soluble phosphorodithioic acids.
- a mixture of isopropyl and hexyl alcohols can be used to produce a very effective, oil-soluble metal phosphorodithioate.
- mixtures of simple phosphorodithioic (i.e., acids prepared from one alcohol) acids can be reacted with zinc axide or barium oxide to produce less expensive, oil-soluble salts.
- Another class of the phosphorothioate additives contemplated for use in the lubricating composition of this invention comprises the adducts of the metal phosphorodithioates described above with an epoxide.
- the metal phosphorodithioates useful in preparing such adducts are for the most part the zinc phosphorodithioates.
- the epoxides may be alkylene oxides or arylalkylene oxides.
- the arylalkylene oxides are exemplified by styrene oxide, p-ethylstyrene oxide, alpha-methylstyrene oxide, 3-betanaphthyl-1,3-butylene oxide, m-dodecylstyrene oxide, and p-chlorostyrene oxide.
- the alkylene oxides include principally the lower alkylene oxides in which the alkylene radical contains 6 or less carbon atoms.
- lower alkylene oxides examples include ethylene oxide, propylene oxide, 1,2-butene oxide, trimethylene oxide, tetramethylene oxide, butadiene monoepoxide, 1,2-hexene oxide, and propylene epichlorohydrin.
- epoxides useful herein include, for example, butyl 9,10-epoxy-stearate, ep-
- the adduct may be obtained by simply mixing the phosphorodithioate and the epoxide.
- the reaction is usually exothermic and may be carried out within wide temperature limits from about 0 C. to about 200 C. Because the reaction is exothermic it is best carried out by adding one reactant, usually the epoxide, in small increments to the other reactant in order to obtain convenient control of the temperature of the reaction.
- the reaction may be carried out in a solvent such as benzene, mineral oil, naphtha, or n-hexane.
- the chemical structure of the adduct is not known. More than one mole, sometimes as many as four moles, of the epoxide can be made to combine with the phosphorodithioate to form products useful herein. However, adducts obtained by the reaction of one mole of the phosphorodithioate with from about 0.25 mole ot about 1 mole of a lower alkylene oxide, particularly ethylene oxide and propylene oxide, have been found to b especially useful and therefore are preferred.
- the lubricating compositions may contain metal detergent additives in amounts usually within the range of about 0.1% to about 20% by weight. In some applications such as in lubricating marine diesel engines the lubircating compositions may contain as much as 30% of a metal detergent additive. They may contain other additives such as extreme pressure addition agents, viscosity index improving agents, and pour point depressing agents, each in amounts withint he range from about 0.1% to about 10%.
- EXAMPLE II SAE 30 mineral lubricating oil containing 0.75% of the product of Example 2 and 0.1% of phosphorus as the barium salt of di-n-nonylphosphorodithioic acid.
- EXAMPLE IV SAE mineral lubricating oil containing 0.1% of the product of Example 4 and 0.15% of the zinc salt of an equimolar mixture of di-cyclohexylphosphorodithioic acid and di-isobutyl phosphorodithioic acid.
- EXAMPLE VII SAE 10W-30 mineral lubricating oil containing 1.5% of the product of Example 2 and 0.05% of phosphorus as the zinc salt of a phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 60% (mole) of p-butylphenol and 40% (mole) of n-pentyl alcohol.
- EXAMPLE VIII SAE 50 mineral lubricating oil containing 3% of the product of Example 4 and 0.1% of phosphorus as the calcium salt of di-hexylphosphorodithioate.
- EXAMPLE XIII SAE 10 mineral lubricating oil containing 1.5% of the product of Example 19, 0.075% of phosphorus as the adduct obtained by heating zinc dinonylphosphorodithioate With 0.25 mole of 1,2-hexene oxide at 120 C., a sulfurized methyl ester of tall oil acid having a sulfur content of 6% of a polybutane viscosity index improver, 0.005% of a poly-(alkyl methacrylate) anti-foam agent, and 0.5% of lard oil.
- the utility of the phosphorus-containing esters of this invention as additives in lubricating compositions is illustrated by the results from an oxidation and detergency test in which a 350 cc. sample of a lubricant containing 0.001% of iron napthenate and 1.5 by Weight of the solvent-free additive to be tested is placed in a 2 x 15 (inches) borosilicate tube. A 1 /8 x 5% (inches) SAE 1020 steel panel is immersed in the test oil. The sample then is heated at 300 F. for a specified period while air is bubbled through it at the rate of 10 liters per hour.
- the oxidized sample is cooled to F., homogenized with 0.5 of water allowed to stand at room temperature for 24 hours, and then filtered through two layers of No. 1 Whatman filter paper at 20 MM. Hg pressure.
- the weight of the precipitate, washed with naptha and dried, is taken as a measure of the efiectiveness of the additive to inhibit oxidation and disperse the sludge formed during the test. The greater the weight of the precipitate the less effective the additive.
- the results of the test are indicated in the following Table I.
- the base oil of the lubricant sample employed in the test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal seconds at 100 F.
- TAB LE I Test result milligrams of sludge per 100 ml. of lubricant Hours of test
- the efficacy of the substituted polyamines of this invention as detergent additives in lubricants for diesel engines operated under relatively severe conditions is demonstrated by the results (Table II) of the CRC-L-l Engine test (also known as Caterpillar 1E test).
- the lubricating composition is used in the crankcase of a 4- stroke diesel engine having a compression ration of 15:1 operated for 120 hours under the following conditions: speed 100 r.p.m.; B.t.u. input per minute, 2900-3000; load, 20 brake horsepower; water jacket temperature, 175180 F.; oil temperature, l40l50 F.
- a diesel fuel having a sulfur content of either 1% or 0.4% is used.
- the lubricant is evaluated according to (1) the piston cleanliness (rating scale of 100, 100 being indicative of no deposit and being indicative of heavy deposits) and (2) the amount of ring filling.
- R is a hydrocarbon radical, a polar-substituted hydrocarbon radical having up to about 10% by weight of at least one polar substituent, or an ether-containing hydrocarbon radical and x is an integer greater than one with from about 0.5 to x moles of an acid-producing mixture of (A) a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters having up to about 18 aliphatic carbon atoms, and the anhydrides thereof having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and (B) a phosphorus acid-producing compound selected from the class consisting of phosphoric acids, phosphorous acids, and the halides, the esters having up to about 30 aliphatic carbon atoms, and the anhydrides thereof, the molar ratio of said succinic acid-producing compound to said phosphorus acid-producing compound being within the range of from about 0.1:1 to 10:1.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufficient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising the reaction of one mole of a polyhydric alcohol having up to about 8 hydroxy radicals with from about 0.5 to 8 moles of an acid-producing mixture of (A) an olefin polymer-substituted succinic anhydride in which the olefin polymer substituent has a molecular weight of from about 750 to 5000 and (B) a trihydrocarbon phosphite having up to about 30 carbon atoms in each hydrocarbon radical, the molar ratio of said succinic anhydride 20 to said phosphite being within the range of from about 0.1:1 to 10:1.
- the lubricating composition of claim 2 characterized further in that the polyhydric alcohol has from 3 to 6 hydroxy radicals.
- the lubricating composition of claim 2 characterized further in that the trihydrocarbon phosphite is triphenyl phosphite.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufficient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising the reaction at a temperature above about C.
- the lubricating composition of claim 1 characterized further in that the polyhydroxy compound is a poly (oxyalkylene) glycol.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufiicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising forming a partially esterified intermediate by the reaction at a temperature above about 100 C.
- R is a hydrocarbon radical, poly-substituted hydrocarbon radical having up to about 10% by weight of at least one polar substituent, or an ether-containing hydrocarbon radical and x is an integer greater than one with a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters having up to about 18 aliphatic carbon atoms, and the anhydrides thereof having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and reacting at a temperature above about 100 C.
- R is a hydrocarbon radical, poly-substituted hydrocarbon radical having up to about 10% by weight of at least one polar substituent, or an ether-containing hydrocarbon radical and x is an integer greater than one with a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters having up to about 18 aliphatic carbon atoms, and the anhydrides thereof having
- said intermediate with a phosphorus acid-producing compound selected from the class consisting of phosphoric acids, phosphorous acids, and the halides, the esters having up to about 30 aliphatic carbon atoms, and the anhydrides thereof, the total amount of said succinic acid producing compound and said phosphorus acid-producing compound being equal to from about 0.5 to x moles per mole of the polyhydroxy compound and the molar ratio of said succinic acid-producing compound to said phosphorus acid-producing compound being within the range of from about 0.1:1 to 10:1.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufiicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process com prising forming a partially esterified ester by the reaction at a temperature above about 100 C. of a polyhydric alcohol having from about 3 to 6 hydroxy radicals with an olefin polymer-substituted succinic anhydride in which the olefin polymer substituent has a molecular weight of from about 750 to 5000 and reacting at a temperature above about 100 C.
- said intermediate with a triaryl phosphite, the total amounts of said succinic anhydride and said phosphite being from about 0.5 to 3 moles per mole of the polyhydric alcohol and the molar ratio of said succinic anhydride to said phosphite being within the range of from about 0.1 :l to 10:1.
- the lubricating composition of claim 8 characterized further in that the polyhydric alcohol has four hydroxy radicals.
- the lubricating composition of claim 8 characterized further in that the olefin polymer-substituted succinic.
- anhydride is a polyisobutene-substituted succinic anhydride.
- the lubricating composition of claim 8 characterized further in that the triaryl phosphite is triphenyl phosphite.
- a lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, suflicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising forming a partially esterified intermediate by the reaction at a temperature above about 100 C. 1 mole of a tetrahydric alcohol having from about 4 to 12 carbon atoms with from about 0.5 to 1.5 moles of a polyisobutene-substituted succinic anhydride in which the polyisobutene substituent has a molecular weight of from about 750 to 5000 and reacting said intermediate at a temperature above about 100 C. from about 0.1 to 1 mole of a triaryl phosphite.
- the lubricating composition of claim 12 characterized further in that the tetrahydric alcohol is pentaerythritol.
- the lubricating composition of claim 12 characterized further in that the triaryl phosphite is triphenyl phosphite.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
Description
United States Patent Office 3,403,102 Patented Sept. 24, 1968 3,403,102 LUBRICANT CONTAINING PHOSPHORUS ACID ESTERS William M. Le Suer, Cleveland, Ohio, assignor to The Lubrizol Corporation, Wicklilfe, Ohio, a corporation of Ohio N Drawing. Original application May 17, 1963, Ser. No. 281,329, now Patent No. 3,325,567, dated June 13, 1967. Divided and this application Mar. 7, 1967, Ser. No. 621,136
14 Claims. (Cl. 25249.8)
ABSTRACT OF THE DISCLOSURE Lubricants, especially lubricants for internal combustion engines and gears, are prepared by blending a lubricating oil and a phosphorus-containing ester. Such lubricants have improved oxidation resistance and detergent properties. The phosphorus-containing ester is prepared by reacting a polyhydric alcohol with both a high molecular weight substituted succinic reactant having at least about 50 aliphatic carbon atoms in the substituent and a phosphorus reactant which may be phosphorus pentoxide, phosphoric acid, or an alkyl ester of phosphoric acid. The preferred phosphorus-containing ester is illustrated by the product formed by reacting pentaerythritol first with a polyisobutene-substituted succinic anhydride and then with triphenylphosphite.
This application is a division of c-opending application Ser. No. 281,329 filed May 17, 1963, now US. 3,325,567.
issued June 13, 1967.
This invention relates to novel compositions of matter and processes for preparing the same. In a more particular sense this invention relates to compositions useful as plasticizers, detergents, anti-rust agents, emulsifiers, and additives in lubricating compositions, fuels, hydrocarbon oils, and power transmitting fluids.
Deterioration of lubricating oils, especially mineral oils, has been a great concern in the formulation of lubricating compositions for use in internal combustion engines, transmissions, gears, etc. Deterioration of the oil results in the formation of products which are corrosive to the metal surfaces with which the oil comes into contact. It also results in the formation of products which agglomerate to form sludgeand varnish-like deposits. The deposits cause sticking of the moving metal parts and obstruct their free movement. They are a principal cause of malfunctioning and premature break-down of the equipment which the oil lubricates.
It is known that water is a common contaminant in the crankcase lubricant of an engine. It may result from the decomposition of the lubricating oil or come from the combustion chamber as a blow-by product of the burning of the fuel. The presence of water in the lubricant seems to promote the deposition of a mayonnaise-like sludge. This type of sludge is more objectionable because it clings tenaciously to metal surfaces and is not removed by oil filters. If the engine is operated under conditions such that the crankcase lubricant temperature is continuously high the water will be eliminated about as fast as it accumulates and only a very small amount of the mayonnaise-like sludge will be formed. On the other hand, if the crankcase lubricant temperature is intermittently high and low or consistently low the water will accumulate and a substantial quantity of the mayonnaiselike sludge will be deposited in the engine.
High operating temperatures are characteristic of an engine that is run consistently at a relatively high speed. However, where an automobile is used primarily for trips of short distance such as is characteristic of urban, home to work use, a significant portion of the operation occurs before the engine has reached its optimum high temperature. An ideal environment thus obtains for the accumulation of water in the lubricant. In this type of operation the problem of mayonnaise-like sludge has been especially troublesome. Its solution has been approached by the use in the lubricant of detergents such as metal phenates and sulfonates which have been known to be effective in reducing deposits in engines operated primarily at high temperatures. Unfortunately, such known detergents have not been particularly effective in solving the problems associated with low temperature operation particularly those problems which are associated with crankcase lubricants in engines operated at low or intermittently high and low temperatures.
It is accordingly a principal object of this invention to provide novel compositions of matter.
It is also an object of this invention to provide compositions which are suitable for use as additives in hydrocarbon oils.
It is also an object of this invention to provide compositions which are effective as additives in lubricating compositions.
It is another object of this invention to provide compositions eifective as detergents in lubricating compositions intended for use in engines operated at low or intermittently high and low temperatures.
It is another object of this invention to provide a process of preparing additives useful as additives in hydrocarbon oils and lubricating compositions.
It is another object of this invention to provide lubricating compositions.
It is further an object of this invention to provide fuel compositions.
These and other objects are attained in accordance with this invention by providing a process for preparing phosphorus-containing esters comprising the reaction of one mole of a polyhydroxy compound having the formula wherein R is a hydrocarbon radical and x is an integer greater than one with from about 0.5 to x moles of an acid-producing mixture of (A) a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters, and the anhydrides thereof having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and (B) a phosphorus acid-producing compound selected from the class consisting of phosphoric acids, phosphorus acids, and the halides, the esters, and the anhydrides thereof, the molar ratio of said succinic acid-producing compound to said phosphorus acid-producing compound being within the range of from about 0.1 :1 to 10:1.
The polyhydroxy compounds from which the phosphorus-containing esters of this invention are derived include principally polyhydric alcohols and polyhydric phenols. They preferably contain less than about 30 carbon atoms. The polyhydric alcohols having from about 2 to 12 carbon atoms and having from 2 to about 10 hydroxy radicals, preferably from 3 to 6 hydroxy radicals, are especially useful. They are illustrated by, for example, alkylene glyc-ols and poly(oxy-alkylene)glycols such as ethylene glycol, di(ethylene glycol), tri(ethylene glycol), di(propylene glycol), tri(butylene glycol), penta(ethylene glycol) and other poly(oxy-alkylene)glycols formed by the condensation of two or more moles of ethylene glycol, propylene glycol, octylene glycol, or a like glycol having up to about 12 carbon atoms in the alkylene radical. Other useful polyhydric alcohols include glycerol, pentaerythritol, 2,4-hexanediol, pinacol, erythritol, arabitol, sorbitol, mannitol, 1,2-cyclohexanediol, Xylylene glycol, and 1,3,5-cyclohexanetriol. The polyhydric phenols are exemplified by hydroquinone, resorcinol, 4-heptyl-1,2- di-hydroxy-benzene, 1,2 dihydroxy naphthalene, 4-polypropene (molecular weight of 1500)-substituted 1,2-dihydroxy-benzene, methyl-S-decyl-1,2-dihydroxy-naphthalene, and pyrogallol.
Still other polyhydroxy compounds include the monoesters of glycerol, sorbitol, mannitol, or other higher polyhydroxy alcohols, such as mono-acetate of glycerol, mono-oleate of sorbitol mono-propionate of mannitol, or the like. Also useful are the interpolymers of an unsaturated alcohol with a copolymerizable olefinic substance such as styrene, vinyl ether, vinyl acetate, isobutene, butadiene, di-vinylbenzene or the like. The interpolymers contain two or more monomeric units derived from the unsaturated alcohol and thus constitute the Polyhydric alcohols contemplated for use in the process of this invention. Specific examples of such interpolymers are the copolymer of 5 moles of allyl alcohol and 1 mole of styrene having an average molecular weight of about 2500.
The radical R in the formula of the polyhydroxy compounds designates a radical which is substantially hydrocarbon in character. The radical may be a hydrocarbon radical or a polar-substituted hydrocarbon radical. Thus, the radical may contain inert polar groups provided that such groups are not present in proportions sufiiciently large to alter significantly the hydrocarbon character of the radical. The polar groups are exemplified by chloro, bromo, keto, aldehyde, nitro, etc. The upper limit with respect to the proportion of such polar groups in a hydrocarbon radical is usually about based upon the weight of the hydrocarbon portion of the radical. In lieu of such a hydrocarbon group, an ether-containing hydrocarbon group may be used wherein the ether groups such as oxyalkylene or poly(oxy-alkylene) groups may contain as many as one oxygen atom for each two carbon atoms.
The hydrocarbon-substituted succinic acid-producing compounds useful in preparing the phosphorus-containing esters may be the succinic acids, anhydrides, halides, or esters in which the hydrocarbon substituent contains at least about 50 aliphatic carbon atoms. The sources of the hydrocarbon substituent include principally the high molecular weight substantially saturated petroleum fractions and substantially saturated olefin polymers, particularly polymers of mono-olefins having from 2 to 30 carbon atoms. The especially useful polymers are the polymers of l-mono-olefins such as ethylene, propene, l-butene, isobutene, l-hexene, l-octene, 2-methyl-1- heptene, 3-cyclohexyl-1-butene, and 2-methyl-5-propyl-1- hexene. Polymers of medial olefins, i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. They are illustrated by 2-butene, 3-pentene, and 4-octene.
Also useful are the interpolymers of the olefins such as those illustrated above with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and polyolefins. Such interpolymers include, for example, those prepared by polymerizing isobutene with styrene; isobutene with butadiene; propene with isoprene; ethylene with piperylene; isobutene with chloroprene; isobutene with p-methyl styrene; l-hexene with 1,3-hexadiene; l-octene with l-hexene; l-heptene with l-pentene; 3- methyl-l-butene with l-octene; 3,3-dimethyl-l-pentene with l-hexene; isobutene with styrene and piperylene; etc.
The relative proportions of the mono-olefins to the other monomers in the interpolymers influence the stability and oil-solubility of the final products derived from such interpolymers. Thus, for reasons of oil-solubility and stability the interpolymers contemplated for use in this invention should be substantially aliphatic and substantially saturated, i.e., they should contain at least about 80%, preferably at least about 95%, on a weight basis, of units derived from the aliphatic mono-olefins and no more than about 5% of olefinic linkages based on the total number of carbon-to-carbon covalent linkages. In most instances, the percentage of olefinic linkages should be less than about 2% of the total number of carbonto-carbon covalent linkages.
Specific examples of such interpolymers include the copolymer of 95% (by weight) of isobutene with 5% of styrene; the terpolymer of 98% of isobutene with 1% of piperylene and 1% of chloroprene; the terpolymer of 95% of isobutene with 2% of l-butene and 3% of l-hexene; the terpolymer of of isobutene with 10% of l-pentene and 10% of l-octene; the copolymer of 80% of l-hexene and 20% of l-heptene; the terpolymer of of isobutene with 2% of cyclohexene and 8% of propene; and the copolymer of 80% of ethylene and 20% of propene.
Another source of the hydrocarbon radical comprises saturated aliphatic hydrocarbons such as highly refined high molecular weight White oils or synthetic alkanes such as are obtained by hydrogenation of high molecular weight olefin polymers illustrated above or high molecular weight olefinic substances.
The use of olefin polymers having molecular weights of about 750-5000 is preferred. Higher molecular weight olefin polymers having molecular weights from about 10,000 to about 100,000 or higher have been found to impart viscosity index improving properties to the final products of this invention. The use of such higher molecular weight olefin polymers often is desirable. It will be noted that the hydrocarbon substituent in the succinic acid-producing compound likewise may contain inert polar groups. Thus, in this respect, it may be a radical which is substantially hydrocarbon in character such as is referred to in the above description of the hydrocarbon radical R of the polyhydroxy compounds.
The succinic acid-producing compounds useful in the above process are preferably substantially hydrocarbonsubstituted succinic acids and anhydrides. These succinic compounds are readily available from the reaction of maleic anhydride with a high molecular weight olefin or a chlorinated hydrocarbon such as the olefin polymer described hereinabove. The reaction involves merely heating the two reactants at a temperature about 100- 200 C. The product from such a reaction is an alkenyl succinic anhydride. The alkenyl group may be hydrogenated to an alkyl group. The anhydride may be hydrolyzed by treatment with water or steam to the corresponding acid. Either the anhydride or the acid may be converted to the corresponding acid halide or ester by reaction with, e.g., phosphorus halide, phenols, or alcohols.
In lieu of the olefins or chlorinated hydrocarbons, other hydrocarbons containing an activating polar substituent, i.e., a substituent which is capable of activating the hydrocarbon molecule in respect to reaction with maleic acid or anhydride, may be used in the above-illustrated reaction for preparing the succinic compounds. Such polar substituents may be illustrated by sulfide, disulfide, nitro, mercaptan, bromine, kctone, or aldehyde radicals. Examples of such polar-substituted hydrocarbons include polypropene sulfide, di-polyisobutene disulfide, nitrated mineral oil, di-polyethylene sulfide, brominated polyethylene, etc. Another method useful for preparing the succinic acids and anhydrides involves the reaction of itaconic acid with a high molecular weight olefin or a polar-substituted hydrocarbon at a temperature usually within the range from about 100 C. to about 200 C.
The acid halides of the succinic acids can be prepared by the reaction of the acids or their anhydrides with a halogenation agent such as phosphorus tri-bromide, phosphorus pentachloride or thionyl chloride. The esters of such acids can be prepared simply by the reaction of the acids or their anhydrides with an alcohol or a phenolic compound such as methanol, ethanol, octadecanol, cyclohexanol, phenol, naphthol, octylphenol, etc. The esterification is usually promoted by the use of an alkaline catalyst such as sodium hydroxide or sodium alkoxide or an acidic catalyst such as sulfuric acid. The nature of the alcoholic or phenolic portion of the ester radical appears to have little influence on the utility of such ester as reactant in the process described hereinabove.
The phosphorus acid-producing reactants useful in the above process for forming the phosphorus-containing esters of this invention may be acids, anhydrides, esters, or halides. The phosphorus acids may be phosphoric acids and phosphorous acids including the oxyphosphorus acids, the thiophosphorus acids, as well as the mixed oxythiophosphorus acids (i.e., those containing both oxygen and sulfur). Thus, a phosphoric acid is used in a generic sense to denote the class consisting of phosphoric acid (H PO phosphorotetrathioic acid (H PS phosphoromonothioic acid (H PO S), phosphorodithioic acid (H PO S and phosphorotrithioic acid (H -POS It should be noted that the acids containing both oxygen and sulfur may be further characterized according to the manner in which the oxygen or sulfur is attached to the phosphorus atom of the acid. The nomenclature used here follows essentially that proposed by the American Chemical and Engineering News, volume 30, No. 43, Oct. 27, 1952. According to this nomenclature, for instance, a phosphoromonothioic acid in which the sulfur atom is attached only to the phosphorus atom (i.e., -P(S) (OH)) is a phosphorothionic acid whereas its isomer in which the sulfur atom is attached to both the phosphorus atom and a hydrogen atom (i.e., --P(O)(S-H)) is a phosphorothiolic acid. Also according to this nomenclature, the inclusion of the thio analogs is admitted only when generic expressions are used and the specific designations such as dioctylphosphoric acid and diphenylphosphorous acid refer to oxy-compounds only, i.e., (octylO) P(O)'(OH) and (octyl-O) POH, respectively. To illustrate further phosphoric acid describes H PO whereas phosphoric,
acids may be the oxy and thio acids. Thus, dialkylphosphoric acids, i.e., dialkyl esters of phosphoric acids, include dialkylphosphoric acid ((alkyl-O) 'P(O) (OH)); dialkylphosphorotetrathioic acid ((alkyl-S) P(S) (SH) 0,0-dialkylphosphorodithioic acid y )z H) O,S-dialkylphosphorodithionic acid ((alkyl-O)(alkyl-S)P(S)(OH)) O,S-dialkylphosphorodithiolic acid ((alkyl-O) (alkyl-S)'P(O) (SH) O,S-dialkylphosphorotrithioic acid The phosphorus acid anhydrides, esters, and halides likewise are useful for preparing the phosphorus-containing esters of this invention. The anhydrides of phosphorus acids are especially desirable. They are illustrated by phosphorus pentoxide, phosphorus pentasulfide, phosphorus heptasulfide, phosphorus sesquisulfide, and phos phorus oxysulfide. The anhydrides of organic phosphorus acids are exemplified by the anhydrides of diphenylphosphoric acid, etc. The halides of the phosphorus acids include, for instance, phosphorus trichloride, phosphorus pentachloride, phosphorothioic trichloride, phosphorus tribromide, diphenylphosphorus chloride, 0,0'-di(chlorophenyl)phosphorothioic chloride, 0,0'-diphenylphosphorothioic chloride, and diphenylphosphorus trichloride.
The esters of the phosphorus acids may be the completely esterified acids or partially esterfied acids. The latter are also known as acidic esters, i.e., at least a portion of the acid is not esterified; they are illustrated by the monoor the di-esterified phosphoric or phosphorous acids. The ester portion may be derived from a hydrocarbon radical, usually one having less than about 30 and preferably from about 1 to about 24 aliphatic carbon atoms. The hydrocarbon radicals may contain inert polar groups such as are described previously. They are exemplified by methyl, ethyl, chloromethyl, o-chlorophenyl, p-bromophenyl, alpha-chloronaphthyl, beta-heptylnaphthyl, o,p-dimethoxyphenyl, tolyl, isobutyl, octadecyl, 4- chloro-2-hep-tadecyl, eicosyl, naphthyl, benzyl, chlorobenzyl, 2-pheny1ethyl, cyclohexyl, cyclopentyl, Z-methylcyclohexyl, the hydrocarbon radical derived from polypropene having a molecular weight of 1500, the hydrocarbon radical derived from polyisobutene having a molecular weight of 5000, behenyl, stearyl, oleyl, allyl, propargyl, o-heptylphenyl, 2,4,6-trirnethylphenyl, Z-mercaptophenyl, m-nitrophenyl, methoxytetraethoxy-methyl, 10- keto-l-octadecyl, polyisobutene (molecular weight of 1000)-substituted phenyl, xenyl, S-naphthyl-Z-decyl, l0- tolyl-l-stearyl, and 9,10-dichlorostearyl radical.
The commonly used esters are, for example, methyl ester of phosphoric acid, dimethyl ester of phosphoric acid, trimethyl ester of phosphoric acid, O-methyl ester of phosphorothiolic acid, dicyclohexyl ester of phosphoric acid, 0,0-dicyc1ohexyl ester of phosphorodithioic acid, dicyclohexyl ester of phosphorotetrathioic acid, O-cyclohexyl-S-decyl ester of phosphoromonothioic acid, 0,0'-diphenyl ester of phosphoromonothiolic acid, triphenyl ester of phosphoric acid, triphenyl ester of phosphorus acid, tritolyl ester of phosphoric acid, dioctadecyl ester of phosphorus acid, trinaphthyl ester of phosphorus acid, trinaphthyl ester of phosphoric acid, 0,0'-dinaphthyl ester of phosphoromonothionic acid, 0,0'-dinaphthyl ester of phosphorothiolic acid, di(heptylphenyl) ester of phosphoric acid, bis(dichlorophenyl) ester of phosphorous acid, S-benzyl ester of phosphoromonothiolic acid, S,S'- di(phenylethyl) ester of phosphorodithioic acid, O,S-didecyl ester of phosphorotrithiolic acid, S,S'-didodecyl ester of phosphorotrithiolic acid, diphenyl ester of phosphorotetrathioic acid, O-dodecyl-S-phenyl ester of phosphoromonothiolic acid, 0,0'-diisooctyl ester of phosphorodithioic acid, di(nitrophenyl) ester of phosphoric acid, 0,0'-di(nitrophenyl) ester of phosphorodithioic acid, 0,0'-di(methoxyphenyl) ester of phosphorodithioic acid, 0,0-di(methoxyphenyl) ester of phosphorodithioic acid, di(heptylphenyl-(OC H ester of phosphoric acid, di(methyl-(OC ;H ester of phosphoric acid, decyl octadecyl ester of phosphoric acid, di(4ketol-decyl) ester of phosphoric acid, di(polyisobutene (molecular weight of 1500)-substituted phenyl) ester of phosphoric acid, 0,0'-di(polypropene (molecular weight of 300)-substituted naphthyl) ester of phosphorodithioic acid, and oleyl ester of phosphoric acid.
The esters of phosphoric acid and phosphorothioic acids are obtained by the reaction of phenol or an alcohol with phosphoric acid or a phosphorothioic acid, or an anhydride of the acid such as phosphorus pentoxide, phosphorus pentasulfide, or phosphorus oxysulfide. The reaction is usually carried out simply by mixing the reactants at a temperature above about 50 C., preferably between about C. and C. In many instances, however, the esters of phosphoric acids tend to decompose at high temperatures. Thus it is often desirable to avoid prolonged exposure of the reaction mixture to temperatures above about 150 C. A solvent may be used in the reaction to facilitate mixing of the reactants and control of the reaction temperature. The solvent may be benzene, naphtha, chlorobenzene, mineral oil, kerosene, cyclohexane, or carbon tetrachloride. A solvent capable of forming a rela tively lowboiling azeotrope with water further aids the removal of water in the esterification of an alcohol or phenol with the phosphorus acid reactant. The relative amounts of the alcohol or phenol reactant and the acid reactant influence the nature of the ester obtained. For instance, equimolar amounts of an alcohol and phosphoric acid tend to result in the formation of a monoester of phosphoric acid whereas the use of a molar excess of the alcohol reactant in the reaction mixture tends to increase the proportion of the .diester or triester in the product. In
most instances the product will be a mixture of the mono-, di-, and tri-esters of the acid and such a mixture is desirable for use in this invention for reasons of economy.
The reaction of an alcohol or phenol with phosphorus pentasulfide ordinarily results in 0,0'-diester of phosphorodithioic acid. Such reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide and may be carried out within the temperature range from about 50 C. to about 250 C. Thus, the preparation of 0,0'-di-n-hexylphosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about 100 C. for about 2 hours. Hydrogen sulfide is liberated and the residue is the defined acid. Treatment of the phosphorodithioic acid with water or steam removes one or both sulfur atoms and converts the product to the corresponding phosphoromonothioic acid or phosphoric acid.
The esters of phosphorotetrathioic acid can be prepared by first the reaction of a mercaptan or thiophenol with PSCl or PSBr to produce an intermediate which is either a phosphorotrithioic halide or triester of phosphorotetrathioic acid and the subsequent reaction of the intermediate with hydrogen sulfide or sodium hydrosulfide. The esters of phosphorotrithioic acids are obtained by the treatment of the esters of the phosphorotetrathioic acids with water or steam.
The esters of phosphorous acids are obtained by the reaction of an alcohol or phenol With phosphorous acid or a phosphorus trihalide such as phosphorus tribromide or phosphorus trichloride and the above noted reaction usually requires carefully controlled conditions such as low temperature in order to give a substantial yield of the esters of phosphorous acids. Under other conditions the reaction of an alcohol or phenol with a phosphorus trihalide may result in a phosphonic acid or ester. Such esters are readily susceptible to rearrangement to phosphonic acids and esters.
The reaction by which the phosphorus-containing esters of this invention are obtained can be effected simply by mixing a polyhydroxy reactant with the succinic acid-producing and the phosphorus acid-producing reactants at the desired temperature. The use of an inert solvent in the reaction is not necessary but often desirable, especially when a highly viscous or solid reactant is present in the reaction mixture. The inert solvent useful in the reaction may be a hydrocarbon such as benzene, toluene, naphtha, cyclohexane, n-hexane, or mineral oil.
The reaction by which the phosphorus-containing esters of this invention are obtained may be carried out by mixing the polyhydric compound, the hydrocarbon-substituted succinic acid-producing compound, and the phosphOrus acid-producing compound at a temperature above about 100 C., preferably be ween about 125 C. and 250 C. The optimum reaction temperature depends to some extent upon the nature of the specific reactions used. For instance, where the succinic acid-producing compound and the phosphorus acid-producing compound are relatively reactive acids or anhydrides, the reaction temperature may be below about 200 C. On the other hand, if the acid-producing reactants are esters such as the dimethyl esters of hydrocarbon substituted succinic acids and triphenyl esters of phosphoric or phosphorous acids, the reaction temperature often will be 200 C. or higher. The maximum temperature for the process is determined by the decomposition point of the reaction mixture. It rarely exceeds 300 C.
The product resulting from the process of this invention usually is a complex mixture of esters derived from the polyhydroxy reactant by the esterification of some of its hydroxy groups with the succinic acid-producing compound and some other hydroxy groups with the phosphorus acid-producing compounds. Thus, the product of this invention is a complex mixture of esters characterized by the presence of ester radicals of both succinic acid ester type and phosphorus acid ester type. The precise composition of the product is not fully understood. Consequently, the product is best described in terms of the process by which it is formed.
The composition of the product of this invention depends for the most part upon the relative proportions of the three reactants used in the process. For reasons of utility and the stoichiometry of the esterification, the total amount of the succinic acid-producing reactant and the phosphorus acid-producing reactant to be used for each mole of the polyhydroxy reactant ordinarily ranges from about 0.5 mole to as many moles as the number of the hydroxy radicals within the molecular structure of the polyhydroxy reactant. Further, the relative amounts of the succinic acid-producing reactant and the phosphorus acid-producing reactant ordinarily are such that they are within the range of molar ratios from about 0.1 :1 to about 10:1, respectively. To illustrate, in reactions with one mole of a tetrahydroxy compound such as pentaerythritol, there may be employed a mixture of a succinic acidproducing reactant and a phosphorus acid-producing reactant in an amount such that the combined quantity of the two acid-producing reactants ranges from about 0.5 to about 5 moles and that the molar ratio of the succinic acid-producing reactant to the phosphorus acid-producing reactant ranges from about 0.1:1 to about 10:1. In other words, for each mole of a tetrahydroxy reactant there may be employed from about 0.05 mole to about 3.6 moles of a succinic acid-producing reactant and from about 0.05 mole to about 3.6 moles of a phosphorus acidproducing reactant provided that the molar ratio of the succinic acid-producing reactant and the phosphorus acidproducing reactant be within the range of about 0.1:1 to about 10:1. The preferred amounts of the three reactants are such that 1 mole of the polyhydroxy reactant is used with from about 0.5 mole to about 1 mole of a succinic acid-producing reactant and from about 1 mole to 3 moles of a phosphorus acid-producing compound. A specific example of the preferred products of this invention is one obtained by the reaction of 1 mole of pentaerythritol with 1 mole of a succinic anhydride and 2 moles of a triaryl phosphite.
It will be noted that where a reactant is a mixture of two or more individual compounds such as are exemplified by commercial polyhydric alcohols comprising a mixture of tri-, tetra-, penta-, or higher polyhydric alcohols, the molecular weight may be the average molecular weight estimated from the elemental analysis of the mixture. Similarly, in the case of a hydrocarbon-substituted succinic anhydride wherein the hydrocarbon substituent is derived from a mixture of, e.g., olefin polymers, the molecular weight is estimated from the acidity or potential acidity of the anhydride, i.e., it is taken to be twice the equivalent weight based upon the acid number as determinedby a standard procedure for determining the acidity of carboxylic acids or anhydride. The molecular weight of a succinic acid ester likewise may be estimated from the potential acidity as determined by its saponification number. It will be further noted that the lower limit of about 0.5 mole for the combined quantities of the two acid-producing reactants per mole of the polyhydroxy reactant is based upon the stoichiometry for the esterification of only one of the hydroxy groups of the polyhydroxy reactant whereas the upper limit of x number of moles for the combined quantities of the two acid-producing reactants per mole of the polyhydroxy reactant having x number of hydroxy groups is based upon the stoichiometry for the esterification of all of the hydroxy groups of the polyhydroxy reactant.
A preferred mode of carrying out the process of this invention involves reacting a polyhydroxy reactant with the succinic acid-producing reactant to form a partially esterified intermediate and then reacting the intermediate With a phosphorus acid-producing reactant. When the process is carried out in this manner the first step, i.e., the formation of the partially esterified intermediate, is
. 9 preferably eflfected at a temperature between about 100 C. and 200 C. and the second step, i.e., the reaction of the intermediate with the phosphorus reactant may be carried out at a temperature from about 80 C. to about 250 C. This particular mode of carrying out the process of this invention is preferred because the products resulting therefrom have been found to be especially useful for the purposes of this invention such as in hydrocarbon oil and lubricating compositions.
Another alternative mode of carrying out the process of this invention involves first reacting polyhydroxy reactant with a phosphorus acid-producing reactant to form a partially esterified intermediate and then reacting the intermediate with the succinic acid-producing reactant. In this regard, the process admits further variations in forming the intermediate of a polyhydroxy substance which has been partially esterified with a phosphorus acid. Thus, for instance, the reaction of phosphoric acid with an epoxide, particularly an alkylene oxide such as ethylene oxide, propylene oxide, hexylene oxide, or epichlorohydrin may result in a partially esterified glycol, i.e., a glycol having one free hydroxy group and one hydroxy group which has been converted to a phosphorus acid ester group by the esterification with phosphoric acid. A more specific example is found in the reaction of 1 mole of phosphoric acid with 3 moles of propylene oxide resulting in the formation of tri(hydroxypropyl) ester of phosphoric acid. This tri(hydroxypropyl) ester may then be used in reaction with a succinic acid-producing reactant in order to form the phosphorus-containing esters of this invention.
In some instances the formation of the phosphoruscontaining esters by the process of this invention is facilitated by the presence in the process of an esterification catalyst. The well-known esterification catalysts are useful for this purpose. They are illustrated by titanium tetrachloride, aluminum chloride, titanium tetrafiuoride, boron trifiuoride, aluminum tribromide, potassium ethoxide, sodium methoxide, calcium phenate, sodium hydroxide, calcium oxide, benzene sulfonic acid, toluene sulfonic acid, etc. A small amount such as 0.001% by weight of the catalyst often is sufiicient to promote esterification of the process of this invention. The amount of the catalyst may range up to about 1% by Weight of the process mixture.
It will be appreciated that when a succinic acid ester or a phosphorus acid ester is to react with a polyhydroxy reactant, the reaction is trans-esterification, i.e., the replacement of an ester radical derived from the polyhydroxy reactant for the ester radical originally present in the succinic or phosphorus acid ester reactant. For instance, where a di-methyl ester of a succinic acid is used in reaction with a partially esterified glycerol formed by the reaction of glycerol with phosphorus pentoxide, the product of this invention is formed by trans-esterification wherein one or both of the methyl radicals of the succinic reactant are replaced with radicals derived from the partially esterified glycerol intermediate and methanol is the by-product. When triphenyl phenyl phosphite is used in reaction with a partially esterified glycerol formed by the reaction of glycerol and a polyisobutene-substituted succinic acid, the product of this invention is formed by transesterification wherein one or more of the phenyl radicals of triphenyl phosphite are replaced with the ester radicals derived from the partially esterified glycerol intermediate and phenol is the by-product. The latter may involve trans-esterification reactions including, e.g., the one illustrated as follows:
wherein R is a substantially hydrocarbon radical. The above phosphorus-containing ester may react further with the partially esterified glycerol to form more complex products such as polymeric substances. Similarly, the use of a succinic halide (such as a polyisobutene-substituted succinic acid dichloride) or a phosphorus acid halide (such as phosphorus pentoxide or phosphorus trichloride) with a partially esterified polyhydroxy intermediate results in replacing the halide radical of the reactant with an ester radical derived from the partially esterified polyhydroxy intermediate. For instance, the reaction of a succinic dichloride with ethylene glycol and phosphorus pentoxide may proceed as follows:
The following examples illustrate the process of this invention.
EXAMPLE 1 A partially esterified pentaerythritol is prepared by adding 136 parts (by weight, 1 molar proportion) of pentaerythritol to a mixture of 1130 parts (1 molar proportion) of a polyisobutene-substituted succinic anhydride having an acid number of 99 (prepared by heating a chlorinated polyisobutene having a molecular weight of 900 and a chlorine content of 4.4% with 20% molar excess of maleic anhydride at 205 C.) and 830 parts of a mineral oil and heating the resulting mixture at C. for 5 hours and at 200-210 C. for 5 hours and filtering the product. The by-product (water) is distilled off during the heating. The filtrate is a 40% oil solution of the partially esterified ester intermediate. To 1020 parts of this filtrate, there is added 310 parts (0.5 molar proportion for each, molar proportion of the pentaerythritol used) of triphenyl phosphite. The mixture is heated at 180-190 C. for 10 hours and then at 180 C./20 mm. whereupon 96 parts of phenol is distilled off as the byproduct of trans-esterification. The filtrate is a 33% oil solution of the phosphorus-containing ester having a phosphorus content of 2.5%.
EXAMPLE 2 propylene glycol is prepared by adding dropwise propylene oxide to the above succinic acid (0.5 mole per mole of propylene oxide) at 80110 C., heating the resulting mixture to 100 C./7 mm., mixing the residue with an additional quantity of mineral oil to prepare a 50% oil solution and then filtering the oil solution. A mixture of 1733 parts of the above oil solution of the partially esterified propylene glycol and 91 parts of triphenylphosphite is heated at 150160 C. for 7.5 hours whereupon phenol (57 parts) is distilled off. The residue is diluted with mineral oil to form a 50% oil solution and filtered. The filtrate is an oil solution of a phosphorus-containing ester having a phosphorus content of 0.5%.
EXAMPLE 3 The oil solution (1890 parts) of the partially esterified propylene glycol of Example 2 and phosphorus pentoxide (46 parts) are mixed at 23 C. The mixture is heated at 5060 C. for 7 /2 hours and then to 60 C./ mm. The mixture is filtered. The filtrate is an oil solution of a phosphorus-containing ester.
EXAMPLE 4 A mixture of 670 parts of pentaerythritol and 2670 parts of the polyisobutene-substituted succinic anhydride of Example 1 (0.5 mole per mole of pentaerythritol) in 2194 parts of mineral oil is heated to 190 C. in 3 hours and then at 190200 C. for 8 hours. The mixture is blown with nitrogen for 0.5 hour and filtered. The filtrate is a 40% oil solution of a partially esterified pentaerythritol. To 2935 parts of the above solution and 1060 parts of mineral oil there is added 284 parts of phosphorus pentoxide (0.8 molar proportions for each molar proportion of the pentaerythritol used). The resulting mixture is heated at 115l20 C. for 5 hours and filtered. The filtrate is a oil solution of a phosphorus-containing ester having a phosphorus content of 1.2%.
EXAMPLE 5 A mixture of 1 mole of ethylene glycol, 0.5 mole of phophorus pentoxide, and 0.5 mole of a polyisobutene (molecular weight of 60,000)-substituted succinic anhydride (having an acid number of 100 and prepared by the reaction of maleic anhydride and a chlorinated polyisobutene having a molecular weight of 60,000 and a chlorine content of 4.3% at 205 C.) in three times its volume of a mineral oil is prepared at C. and then heated at 120140 C. for 10 hours.
EXAMPLE 6 EXAMPLE 7 A mixture of 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of glycerol in twice the volume of the mixture of toluene is heated at the reflux temperature (100 C.) while water is removed by azeotropic distillation. To the residue there is added 0.5 mole of phosphorus pentasulfide and the resulting mixture is heated at 90110 C. for 4 hours. Toluene is then removed by vacuum distillation. The residue is a phosphorus-containing ester.
EXAMPLE 8 A partially esterified propylene glycol is obtained by reacting 1 mole of phosphoric acid with 3.3 moles of propylene oxide while the by-product (water) is distilled 12; 01f. To 390 grams of this partially esterified propylene glycol there is added 200 grams of toluene and 1495 grams of the polyisobutene-substituted succinic anhydride of Example 1. The mixture is heated at 158163 C. for 8 hours and then at 160 C./1-2 mm. The residue is mixed with 1200 grams of mineral oil and heated to distill otf toluene. The residue is filtered. The filtrate is an oil solution of a phosphorus-containing ester having a phophorus content of 7.7%.
EXAMPLE 9 A partially esterified sorbitol is prepared by heating at 110-150 C. 1 mole of sorbitol and 1 mole of phosphorus pentoxide. The intermediate is dissolved in white oil and mixed with 2.5 moles of the polyisobutene-substituted succinic anhydride of Example 1. The resulting mixture is heated at 200 C. for 7 hours and filtered.
EXAMPLE 10 An olefin polymer-substituted succinic anhydride is obtained by heating 1.2 moles of maleic anhydride with 1 mole of a copolymer of mole percent of propylene and 25 mole percent of ethylene having an average molecular weight of 10,000 at 200-220 C. To a solution of the above anhydride in an equal weight of mineral oil, there is added at 25 C. 2 moles of neopentyl glycol and 1 mole of phosphorus acid. The mixture is heated to 120 C. for 2 hours and then at 120-180 C. for 5 hours whereupon water is removed by distillation. The residue is filtered. The filtrate is an oil solution of the phosphoruscontaining ester.
EXAMPLE 11 A phosphorus-containing ester is prepared by the procedure of Example 10 from a reaction mixture of 0.1 mole of an isobutene-styrene copolymer (:5 by weight of isobutene to styrene, average molecular weight of 2000)-substituted succinic anhydride, 1 mole of di(ethylene glycol and 0.5 mole of phosphoric oxychloride.
EXAMPLE 12 A phosphorus-containing ester is obtained by the procedure of Example 10 from a reaction mixture of 0.5 mole of the polyisobutene-substituted succinic anhydride of Example 1, 1 mole of tri(ethylene glycol), and 0.1 mole of dimethyl phosphite.
EXAMPLE 13 A phosphorus-containing ester is obtained by the procedure of Example 10 from a reaction mixture of 1 mole of the polyisobutene-substituted succinic anhydride of Example 1, 0.5 mole of triethyl phosphite, and 1 mole of a copolymer of 5 moles of allyl alcohol and 1 mole of styrene having a molecular weight of 1100.
EXAMPLE 14 A phosphorus-containing ester is obtained by heating at 150-180 C. a mixture of the partially esterified pentaerythritol (40% oil solution) and diphenylphosphorothioic chloride (2 moles per mole of pentaerythritol).
EXAMPLE 15 A phosphorus-containing ester is obtained by first heating at 120-200 C. 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of mannitol monooleate to form a partially esterified mannitol intermediate and then heating at 200 C. the intermediate with 3 moles of di(heptylphenyl)phosphorus chloride (i.e., (C H C H O) PCl) in an equal volume of mineral oil.
EXAMPLE 16 A phosphorus-containing ester is obtained by first heating at -180 C. 1 mole of the polyisobutene-substituted succinic anhydride of Example 1 and 1 mole of glycerol in 1000 grams of mineral oil and then heating 13 at 150-200' C. the above reaction mixture with 0.5 mole of the anhydride of diethylphosphoric acid (i.e.,
EXAMPLE 17 EXAMPLE 18 A phosphorus-containing ester is prepared as follows: a partially esterified resorcinol (formed by heating at 100200 C. 0.75 mole of the polyisobutene-substituted succinic anhydride of Example 1 with 1 mole of resorcinol in 1000 grams of diphenyl ether as the diluent) and phosphorus pentoxide (0.1 mole per mole of resorcinol) areheated at 150160 C. for hours.
EXAMPLE 19 A phosphorus-containing ester is obtained by the procedure of Example 18 except that resorcinol is replaced on a molar basis with 4-heptyl-1,2-dihydroxybenzene.
EXAMPLE 20 A phosphorus-containing ester is obtained by the procedure of Example 18 except that resorcinol is replaced on a molar basis with 1,2-dihydroxynaphthylene.
The phosphorus-containing esters of this invention are useful for a wide variety of purposes including pesticides, plasticizers, rust-inhibiting agents for treatment of metals, corrosion-inhibiting agents, extreme pressure agents, antiwear agents, and detergents.
A principal utility of such products is as additives in lubricants. It has been discovered in accordance with this invention that when used for such purpose their effectiveness to impart a specific property to a lubricant is closely related to the size of the hydrocarbon substituent in the hydrocarbon-substituted succinic acid-producing compounds from which the phosphorus-containing esters are derived. More particularly it has been found that products in which the substantially hydrocarbon substituent contains more than about 50 aliphatic carbon atoms are particularly effective for the purposes of this invention.
The lubricating oils in which the substituted polyamines of this invention are useful as additives may be of synthetic, animal, vegetable, or mineral origin. Ordinarily mineral lubricating oils are preferred by reason of their availability, general excellence, and low cost. For certain applications, oils belonging to one of the other three groups may be preferred. For instance, synthetic polyester oils such as didodecyl adipate and di-Z-ethylhexyl sebacate are often preferred as jet engine lubricants. Normally the lubricating oils preferred will be fluid oils, ranging in viscosity from about 40 Saybolt Universal Seconds at 100 F. to about 200 Saybolt Universal seconds at 210 F.
The concentration of the phosphorous-containing esters as additives in lubricants usually ranges from about 0.01% to about by weight. The optimum concentrations for a particular application depend to a large measure upon the type of service to which the lubricant is to be subjected. Thus, for example, lubricants for use in gasoline internal combustion engines may contain from about 0.5 to about 10% of the additive, whereas lubricating compositions for use in gears and diesel engines may contain as much as or even more of the additive. Lubricants for use in the oil-fuel mixture for two-stroke engines may contain from about 1% to 10% of the additive.
This invention contemplates also the presence of other additives in the lubricating compositions. Such additives include, for example, supplemental detergents of the ashcontaining type, viscosity index improving agents, pour point depressing agents, anti-foam agents, extreme pressure agents, rust-inhibiting agents, and supplemental oxidation and corrosion-inhibiting agents.
The ash-containing detergents are exemplified by oilsoluble neutral and basic salts of alkali or alkaline earth metals with sulfonic acids, carboxylic acids, or organic phosphorus acids characterized by at least one direct carbon-to-phosphorus linkage such as those prepared by the treatment of an olefin polymer (e.g., polyisobutene having a molecular weight of 1000) with a phosphorizing agent such as phosphorus trichloride, phosphorus heptasulfide, phosphorus pentasulfide, phosphorus trichloride and sulfur, white phosphorus and a sulfur halide, or phosphorothioic chloride. The most commonly used salts of such acids are those of sodium, potassium, lithium, calcium, magnesium, strontium, and barium.
The term basic salt is used to designate the metal salts wherein the metal is present in stoichiometrically larger amounts than the organic acid radical. The commonly employed methods for preparing the basic salts involves heating a mineral oil solution of an acid with a stoichiometric excess of a metal neutralizing agent such as the metal oxide, hydroxide, carbonate, bicarbonate, or sulfide at a temperature about 50 C. and filtering the resulting mass. The use of a promoter in the neutralization step to aid the incorporation of a large excess of metal likewise is known. Examples of compounds useful as the promoters include phenolic substances such as phenol, naphthol, alkylphenol, triophenol, sulfurized alkylphenol, and condensation products of formaldehyde With a phenolic substance; alcohols such as methanol, 2-propanol, octyl alcohol, Cellosolve, carbitol, ethylene glycol, stearyl alcohol, and cyclohexyl alcohol; amines such as aniline, phenylenediamine, phenothiazine, phenyl beta-naphthylamine, and dodecylamine. A particularly effective method for preparing the basic salts comprises mixing an acid with an excess of a basic alkaline earth metal neutralizing agent, a phenolic promoter compound, and a small amount of water and carbonating the mixture at an elevated temperature such as 60-200 C.
The preparation of a basic sulfonate detergent is illustrated as follows: A mixture of 490 parts (by weight) of a mineral oil, parts of water, 61 parts of heptylphenol, 340 parts of barium mahogany sulfonate, and 227 parts of barium oxide is heated at 100 C. for 0.5 hour and then to C. Carbon dioxide is then bubbled into the mixture until the mixture is substantially neutral. The mixture is filtered and the filtrate found to have a sulfate ash content of 25%.
The preparation of a basic barium salt of a phosphorus acid is illustrated as follows: A polyisbutene having a molecular weight of 50,000 is mixed with 10% by weight of phosphorus pentasulfide at 200 C. for 6 hours. The resulting product is hydrolyzed by treatment'with steam at C. to produce an acidic intermediate. The acidic intermediate is then converted to a basic salt by mixing twice its volume of mineral oil, 2 moles of barium hydroxide and 0.7 mole of phenol and carbonating the mixture at 150 C. to produce a fluid product,
The phosphorus-containing esters are especially adapted for use in combination with extreme pressure and corrosion-inhibiting additives such as metal dithiocarbamates, xanthates, the Group II metal phosphorodithioates and their epoxide adducts, hindered phenols, sulfurized cycloalkanes, di-alkyl polysulfides, sulfurized fatty esters, phosphosulfurized fatty esters, alkaline earth metal salts of alkylated phenols, dialkyl phosphites, triaryl phosphites, and esters of phosphorodithioic acids. Combinations of the phosphorus-containing esters of this invention with any of the above-mentioned additives are especially desirable for use in lubricants which must have superior extreme pressure and oxidation-inhibiting characteristics.
15 The Group II metal phosphorodithioates are the salts of acids having the formula R SH in which R and R are substantially hydrocarbon radicals. The metals for forming such salts are exemplified by bar ium, calcium, strontium, zinc, and cadmium. The barium and zinc phosphorodithioates are especially preferred. The substantially hydrocarbon radicals in the phosphorodithioic acid are preferably low or medium molecular weight alkyl radicals and alkylphenyl radicals, i.e., those having from about 1 to about 30 carbon atoms in the alkyl group. Illustrative alkyl radicals include methyl, ethyl, isopropyl, isobutyl, n-butyl, sec-butyl, the various amyl alcohols, n-hexyl, methylisobutyl carbinyl, heptyl, 2-ethylhexyl, di' isobutyl, isooctyl, nonyl, behenyl, decyl, etc. Illustrative lower alkylphenyl radicals include butylphenyl, amylphenyl, di-amylphenyl, octylphenyl, etc. Cycloalkyl radicals likewise are useful and these include chiefly cyclohexyl and the lower alkyl-cyclohexyl radicals. Other substantially hydrocarbon radicals likewise are useful such as tetradecyl, octadecyl, eicosyl, butylnaphthyl, hexylnaphthyl, octylnaphthyl, cyclohexylphenyl, naphthenyl, etc. Many substituted hydrocarbon radicals may also be used, e.g., chloropentyl, dichlorophenyl, and dichlorodecyL' The availability of the phosphorodithioic acids from which the Group II metal salts of this invention are prepared is well known. They are prepared by the reaction of phosphorus pentasulfide with an alcohol or phenol. The reaction involves four moles of the alcohol or phenol per mole of phosphorus pentasulfide, and may be carried out within the temperature range from about 50 C. to about 200 C. Thus the preparation of 0,0-di-n-hexyl phosphorodithioic acid involves the reaction of phosphorus pentasulfide with four moles of n-hexyl alcohol at about 100 C. for about 2 hours. Hydrogen sulfide is liberated and the residue is the defined acid. The preparation of the zinc or barium salt of this acid may be effected by reaction with zinc oxide or barium oxide. Simply mixing and heating these two reactants is sufficient to cause the reaction to take place and the resulting product is sufiiciently pure for the purpose of this invention.
Especially useful Group II metal phosphorodithioates can be prepared from phosphorodithioic acids which in turn are prepared by the reaction of phosphorus pentasulfide with mixtures of alcohols. The use of such mixtures enables the utilization of cheaper alcohols which in themselves do not yield oil-soluble phosphorodithioic acids. Thus a mixture of isopropyl and hexyl alcohols can be used to produce a very effective, oil-soluble metal phosphorodithioate. For the same reason mixtures of simple phosphorodithioic (i.e., acids prepared from one alcohol) acids can be reacted with zinc axide or barium oxide to produce less expensive, oil-soluble salts.
Another class of the phosphorothioate additives contemplated for use in the lubricating composition of this invention comprises the adducts of the metal phosphorodithioates described above with an epoxide. The metal phosphorodithioates useful in preparing such adducts are for the most part the zinc phosphorodithioates. The epoxides may be alkylene oxides or arylalkylene oxides. The arylalkylene oxides are exemplified by styrene oxide, p-ethylstyrene oxide, alpha-methylstyrene oxide, 3-betanaphthyl-1,3-butylene oxide, m-dodecylstyrene oxide, and p-chlorostyrene oxide. The alkylene oxides include principally the lower alkylene oxides in which the alkylene radical contains 6 or less carbon atoms. Examples of such lower alkylene oxides are ethylene oxide, propylene oxide, 1,2-butene oxide, trimethylene oxide, tetramethylene oxide, butadiene monoepoxide, 1,2-hexene oxide, and propylene epichlorohydrin. Other epoxides useful herein include, for example, butyl 9,10-epoxy-stearate, ep-
16 oxidzed soya bean oil, epoxidized tung oil, and epoxidized copolymer of styrene with butadiene.
The adduct may be obtained by simply mixing the phosphorodithioate and the epoxide. The reaction is usually exothermic and may be carried out within wide temperature limits from about 0 C. to about 200 C. Because the reaction is exothermic it is best carried out by adding one reactant, usually the epoxide, in small increments to the other reactant in order to obtain convenient control of the temperature of the reaction. The reaction may be carried out in a solvent such as benzene, mineral oil, naphtha, or n-hexane.
The chemical structure of the adduct is not known. More than one mole, sometimes as many as four moles, of the epoxide can be made to combine with the phosphorodithioate to form products useful herein. However, adducts obtained by the reaction of one mole of the phosphorodithioate with from about 0.25 mole ot about 1 mole of a lower alkylene oxide, particularly ethylene oxide and propylene oxide, have been found to b especially useful and therefore are preferred.
The lubricating compositions may contain metal detergent additives in amounts usually within the range of about 0.1% to about 20% by weight. In some applications such as in lubricating marine diesel engines the lubircating compositions may contain as much as 30% of a metal detergent additive. They may contain other additives such as extreme pressure addition agents, viscosity index improving agents, and pour point depressing agents, each in amounts withint he range from about 0.1% to about 10%.
The following examples are illustrative of the lubricating compositions of this invention (all percentages are by weight):
EXAMPLE I SAE 20 mineral lubricating oil containing 0.5% of the product of Example 1.
EXAMPLE II SAE 30 mineral lubricating oil containing 0.75% of the product of Example 2 and 0.1% of phosphorus as the barium salt of di-n-nonylphosphorodithioic acid.
EXAMPLE III SAE l0W30 mineral lubricating oil containing 0.4% of the product of Example 3.
EXAMPLE IV SAE mineral lubricating oil containing 0.1% of the product of Example 4 and 0.15% of the zinc salt of an equimolar mixture of di-cyclohexylphosphorodithioic acid and di-isobutyl phosphorodithioic acid.
EXAMPLE V SAE 30 mineral lubricating oil containing 2% of the product of Example 4.
EXAMPLE VI SAE 20W-30 mineral lubricating oil containing 5% of the product of Example 5.
EXAMPLE VII SAE 10W-30 mineral lubricating oil containing 1.5% of the product of Example 2 and 0.05% of phosphorus as the zinc salt of a phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with a mixture of 60% (mole) of p-butylphenol and 40% (mole) of n-pentyl alcohol.
EXAMPLE VIII SAE 50 mineral lubricating oil containing 3% of the product of Example 4 and 0.1% of phosphorus as the calcium salt of di-hexylphosphorodithioate.
1 7 EXAMPLE IX SAE 10W30 mineral lubricating oil containing 2% of the product of Example 2, 0.06% of phosphorus as zinc di-n-octylphosphorodithioate, and 1% of sulfate ash as barium mahogany sulfonate.
EXAMPLE X SAE 30 mineral lubricating oil containing 5% of the product of Example 10, 0.1% of phosphorus as the zinc salt of a mixture of equimolar amounts of di-isopropylphosphorodithioic acid, and di-n-decylphosphorodithioic acid, and 2.5% of sulfate ash as a basic barium detergent prepared by carbonating at 150 C. a mixture comprising mineral oil, barium di-dodecylbenzene sulfonate and 1.5 moles of barium hydroxide in the presence of a small amount of water and 0.7 mole of octylphenol as the promoter.
EXAMPLE XI SAE W-30 mineral lubricating oil containing 6% of the product of Example 17, 0.075% of phosphorus as zinc di-n-octylphosphorodithioate, and 5% of the barium salt of an acidic composition prepared by the reaction of 1000 parts of a polyisobutene having a molecular weight of 60,000 with 100 parts of phosphorus pentasulfide at 200 C. and hydrolyzing the product with steam at 150 C.
EXAMPLE XII SAE 10 mineral lubricating oil containing 2% of the product of Example 20, 0.075% of phosphorus as the adduct of zinc di-cyclohexylphosphorodithioate treated with 0.3 mole of ethylene oxide, 2% of a sulfurized sperm oil having a sulfur content of 10%, 3.5% of a poly-(alkyl methacrylate) viscosity index improver, 0.02% of a poly- (alkyl methacrylate) pour point depressant, 0.003% of a poly-(alkyl siloxane) anti-foam agent.
EXAMPLE XIII SAE 10 mineral lubricating oil containing 1.5% of the product of Example 19, 0.075% of phosphorus as the adduct obtained by heating zinc dinonylphosphorodithioate With 0.25 mole of 1,2-hexene oxide at 120 C., a sulfurized methyl ester of tall oil acid having a sulfur content of 6% of a polybutane viscosity index improver, 0.005% of a poly-(alkyl methacrylate) anti-foam agent, and 0.5% of lard oil.
EXAMPLE XIV SAE mineral lubricating oil containing 1.5% of the product of Example 2, 0.5% of di-dodecyl phosphite, 2% of the sulfurized sperm oil having a sulfur content of 9%, a basic calcium detergent prepared by carbonating a mixture comprising mineral oil, calcium mahogany sulfonate and 6 moles of calcium hydroxide in the presence of an equi-molar mixture (10% of the mixture) of methyl alcohol and n-butyl alcohol as the promoter at the reflux temperature.
EXAMPLE XV SAE 10 mineral lubricating oil containing of the product of Example 13, 0.07% of phosphorus as zinc dioctylphosphorodithioate, 2% of a barium detergent prepared by neutralizing with barium hydroxide the hydrolyzed reaction product of polypropylene (molecular weight 2000) with 1 mole of phosphorus pentasulfide and 1 mole of sulfur, 3% of a barium sulfonate detergent prepared by carbonating a mineral oil solution of mahogany acid, and 500% stoichiometrically excess amount of barium hydroxide in the presence of phenol as the promoter at 180 C., 3% of a supplemental ashless detergent prepared by copolymerizing a mixture of 95% (Weight) of decyl-methacrylate and 5% (weight) of diethylaminoethylacrylate.
EXAMPLE XVI SAE 80 mineral lubricating oil containing 2% of the product of Example 20, 0.1% of phosphorus as zinc di- 18 n-hexylphosphorodithioate, 10% of a chlorinated paraffin wax having a chlorine content of 40%, 2% of di-butyl tetrasulfide, 2% of sulfurized dipentene, 0.2% of oleyl amide, 0.003% of an anti-foam agent, 0.02% of a pour point depressant, and 3% of a viscosity index improver.
EXAMPLE XVII SAE 10 mineral lubricating oil containing 3% of the product of Example 3, 0.075% of phosphorus as the zinc salt of a phosphorodithioic acid prepared by the reaction of phosphorus pentasulfide with an equimolar mixture of n-butyl alcohol and dodecyl alcohol, 3% of a barium detergent prepared by carbonating a mineral oil solution containing 1 mole of sperm oil, 0.6 mole of octylphenol, 2 moles of barium oxide, and a small amount of water at 150 C.
EXAMPLE XVIII SAE 20 mineral lubricating oil containing 2% of the product of Example 12 and 0.07% of phosphorus as zinc di-n-octylphosphorodithioate.
EXAMPLE XIX SAE 30 mineral lubricating oil containing 3% of the product of Example 14 and 0.1% of phosphorus as zinc di-(isobutylphenyl)-phosphorodithioate.
EXAMPLE XX SAE 50 mineral lubricating oil containing 2% of the product of Example 9.
EXAMPLE XXI SAE mineral lubricating oil containing 3% of the product of Example 11 and 0.2% of phosphorus as the reaction product of 4 moles of turpentine with 1 mole of phosphorus pentasulfide.
EXAMPLE XXII SAE 90 mineral lubricating oil containing 3% of the product of Example 12 and 0.2% of 4,4-methylenebis- (2,6-di-tert-butylphenol) EXAMPLE XXIII SAE 30 mineral lubricating oil containing 2% of the product of Example 13 and 0.1% of phosphorus as phenylethyl di-cyclohexylphosphorodithioate.
EXAMPLE XXIV SAE 90 mineral lubricating oil containing 5% of the product of Example 1 and 1% of the calcium salt of the sulfurized phenol obtained by the reaction of 2 moles of heptylphenol with 1 mole of sulfur.
The above lubricants are merely illustrative and the scope of invention includes the use of all the additives previously illustrated as Well as others within the broad concept of this invention described herein.
The utility of the phosphorus-containing esters of this invention as additives in lubricating compositions is illustrated by the results from an oxidation and detergency test in which a 350 cc. sample of a lubricant containing 0.001% of iron napthenate and 1.5 by Weight of the solvent-free additive to be tested is placed in a 2 x 15 (inches) borosilicate tube. A 1 /8 x 5% (inches) SAE 1020 steel panel is immersed in the test oil. The sample then is heated at 300 F. for a specified period while air is bubbled through it at the rate of 10 liters per hour. The oxidized sample is cooled to F., homogenized with 0.5 of water allowed to stand at room temperature for 24 hours, and then filtered through two layers of No. 1 Whatman filter paper at 20 MM. Hg pressure. The weight of the precipitate, washed with naptha and dried, is taken as a measure of the efiectiveness of the additive to inhibit oxidation and disperse the sludge formed during the test. The greater the weight of the precipitate the less effective the additive. The results of the test are indicated in the following Table I. The base oil of the lubricant sample employed in the test is a Mid-Continent, conventionally refined mineral oil having a viscosity of about 200 Saybolt Universal seconds at 100 F.
TAB LE I Test result, milligrams of sludge per 100 ml. of lubricant Hours of test The efficacy of the substituted polyamines of this invention as detergent additives in lubricants for diesel engines operated under relatively severe conditions is demonstrated by the results (Table II) of the CRC-L-l Engine test (also known as Caterpillar 1E test). In this test, the lubricating composition is used in the crankcase of a 4- stroke diesel engine having a compression ration of 15:1 operated for 120 hours under the following conditions: speed 100 r.p.m.; B.t.u. input per minute, 2900-3000; load, 20 brake horsepower; water jacket temperature, 175180 F.; oil temperature, l40l50 F. A diesel fuel having a sulfur content of either 1% or 0.4% is used. The lubricant is evaluated according to (1) the piston cleanliness (rating scale of 100, 100 being indicative of no deposit and being indicative of heavy deposits) and (2) the amount of ring filling.
TABLE II Percent Piston Lubricant tested ring cleanliness filling rating (G) SAE 30 mineral lubricating oil containing 1.68% of the product of Example 1 1 97.0
wherein R is a hydrocarbon radical, a polar-substituted hydrocarbon radical having up to about 10% by weight of at least one polar substituent, or an ether-containing hydrocarbon radical and x is an integer greater than one with from about 0.5 to x moles of an acid-producing mixture of (A) a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters having up to about 18 aliphatic carbon atoms, and the anhydrides thereof having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and (B) a phosphorus acid-producing compound selected from the class consisting of phosphoric acids, phosphorous acids, and the halides, the esters having up to about 30 aliphatic carbon atoms, and the anhydrides thereof, the molar ratio of said succinic acid-producing compound to said phosphorus acid-producing compound being within the range of from about 0.1:1 to 10:1.
2. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufficient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising the reaction of one mole of a polyhydric alcohol having up to about 8 hydroxy radicals with from about 0.5 to 8 moles of an acid-producing mixture of (A) an olefin polymer-substituted succinic anhydride in which the olefin polymer substituent has a molecular weight of from about 750 to 5000 and (B) a trihydrocarbon phosphite having up to about 30 carbon atoms in each hydrocarbon radical, the molar ratio of said succinic anhydride 20 to said phosphite being within the range of from about 0.1:1 to 10:1.
3. The lubricating composition of claim 2 characterized further in that the polyhydric alcohol has from 3 to 6 hydroxy radicals.
4. The lubricating composition of claim 2 characterized further in that the trihydrocarbon phosphite is triphenyl phosphite.
5. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufficient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising the reaction at a temperature above about C. of one mole of a polyhydric alcohol having from about 3 to 6 hydroxy radicals with from about 0.5 to 3 moles of an acid-producing mixture of (A) a polyisobutene-substituted succinic anhydride in which the polyisobutene substituent has a molecular weight of from about 750 to 5000 and (B) a triaryl phosphite, the molar ratio of said succinic anhydride to said phosphite being within the range of from about 0.121 to 10:1.
6. The lubricating composition of claim 1 characterized further in that the polyhydroxy compound is a poly (oxyalkylene) glycol.
7. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufiicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising forming a partially esterified intermediate by the reaction at a temperature above about 100 C. of a polyhydroxy compound having the formula wherein R is a hydrocarbon radical, poly-substituted hydrocarbon radical having up to about 10% by weight of at least one polar substituent, or an ether-containing hydrocarbon radical and x is an integer greater than one with a succinic acid-producing compound selected from the class consisting of hydrocarbon-substituted succinic acids and the halides, the esters having up to about 18 aliphatic carbon atoms, and the anhydrides thereof having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and reacting at a temperature above about 100 C. said intermediate with a phosphorus acid-producing compound selected from the class consisting of phosphoric acids, phosphorous acids, and the halides, the esters having up to about 30 aliphatic carbon atoms, and the anhydrides thereof, the total amount of said succinic acid producing compound and said phosphorus acid-producing compound being equal to from about 0.5 to x moles per mole of the polyhydroxy compound and the molar ratio of said succinic acid-producing compound to said phosphorus acid-producing compound being within the range of from about 0.1:1 to 10:1.
8. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, sufiicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process com prising forming a partially esterified ester by the reaction at a temperature above about 100 C. of a polyhydric alcohol having from about 3 to 6 hydroxy radicals with an olefin polymer-substituted succinic anhydride in which the olefin polymer substituent has a molecular weight of from about 750 to 5000 and reacting at a temperature above about 100 C. said intermediate with a triaryl phosphite, the total amounts of said succinic anhydride and said phosphite being from about 0.5 to 3 moles per mole of the polyhydric alcohol and the molar ratio of said succinic anhydride to said phosphite being within the range of from about 0.1 :l to 10:1.
9. The lubricating composition of claim 8 characterized further in that the polyhydric alcohol has four hydroxy radicals.
10. The lubricating composition of claim 8 characterized further in that the olefin polymer-substituted succinic.
21 anhydride is a polyisobutene-substituted succinic anhydride.
11. The lubricating composition of claim 8 characterized further in that the triaryl phosphite is triphenyl phosphite.
12. A lubricating composition comprising a major proportion of a lubricating oil and a minor proportion, suflicient to improve detergency and oxidation stability, of a phosphorus containing ester prepared by the process comprising forming a partially esterified intermediate by the reaction at a temperature above about 100 C. 1 mole of a tetrahydric alcohol having from about 4 to 12 carbon atoms with from about 0.5 to 1.5 moles of a polyisobutene-substituted succinic anhydride in which the polyisobutene substituent has a molecular weight of from about 750 to 5000 and reacting said intermediate at a temperature above about 100 C. from about 0.1 to 1 mole of a triaryl phosphite.
13. The lubricating composition of claim 12 characterized further in that the tetrahydric alcohol is pentaerythritol.
14. The lubricating composition of claim 12 characterized further in that the triaryl phosphite is triphenyl phosphite.
References Cited UNITED STATES PATENTS 3,255,108 6/1966 Wiese 25256 XR 3,202,693 8/1965 Gaetner 4470 XR 3,288,714 11/1966 Osuch 252-56 DANIEL E. WYMAN, Primary Examiner.
W. H. CANNON, Assistant Examiner.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1054276D GB1054276A (en) | 1963-05-17 | ||
FR974704A FR1401507A (en) | 1963-05-17 | 1964-05-15 | Process for the production of esters containing phosphorus |
DE19641520211 DE1520211A1 (en) | 1963-05-17 | 1964-05-19 | Lubricant preparation |
US621136A US3403102A (en) | 1963-05-17 | 1967-03-07 | Lubricant containing phosphorus acid esters |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US281329A US3325567A (en) | 1963-05-17 | 1963-05-17 | Phosphorus esters and process |
US621136A US3403102A (en) | 1963-05-17 | 1967-03-07 | Lubricant containing phosphorus acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
US3403102A true US3403102A (en) | 1968-09-24 |
Family
ID=26960835
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US621136A Expired - Lifetime US3403102A (en) | 1963-05-17 | 1967-03-07 | Lubricant containing phosphorus acid esters |
Country Status (3)
Country | Link |
---|---|
US (1) | US3403102A (en) |
DE (1) | DE1520211A1 (en) |
GB (1) | GB1054276A (en) |
Cited By (93)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4072618A (en) * | 1976-08-27 | 1978-02-07 | Mobil Oil Corporation | Metal working lubricant |
US4321308A (en) * | 1975-02-07 | 1982-03-23 | The Lubrizol Corporation | Metal workpieces coated with ester-based hot melt metal working lubricants |
US4444649A (en) * | 1982-11-15 | 1984-04-24 | Union Oil Company Of California | Antifoulant for high temperature hydrocarbon processing |
US4589993A (en) * | 1982-12-27 | 1986-05-20 | Exxon Research & Engineering Co. | Power transmission shift fluids containing two-component friction modifier additive |
US4820432A (en) * | 1987-07-24 | 1989-04-11 | Exxon Chemical Patents Inc. | Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions |
US4863624A (en) * | 1987-09-09 | 1989-09-05 | Exxon Chemical Patents Inc. | Dispersant additives mixtures for oleaginous compositions |
US4866141A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same |
US4866140A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4866139A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterified dispersant additives useful in oleaginous compositions |
US4906394A (en) * | 1986-10-07 | 1990-03-06 | Exxon Chemical Patents Inc. | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions |
US4943382A (en) * | 1988-04-06 | 1990-07-24 | Exxon Chemical Patents Inc. | Lactone modified dispersant additives useful in oleaginous compositions |
US4954277A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same |
US4954276A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
EP0389967A2 (en) * | 1989-03-27 | 1990-10-03 | Aluminum Company Of America | Compositions useful as lubricants |
US4963275A (en) * | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
US4971711A (en) * | 1987-07-24 | 1990-11-20 | Exxon Chemical Patents, Inc. | Lactone-modified, mannich base dispersant additives useful in oleaginous compositions |
US5032320A (en) * | 1986-10-07 | 1991-07-16 | Exxon Chemical Patents Inc. | Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions |
US5059335A (en) * | 1989-02-08 | 1991-10-22 | The Lubrizol Corporation | Lubricants containing salts of hydroxyalkane phosphonic acids |
US5154843A (en) * | 1989-02-08 | 1992-10-13 | The Lubrizol Corporation | Hydroxyalkane phosphonic acids and derivatives thereof and lubricants containing the same |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
US5312554A (en) * | 1987-05-26 | 1994-05-17 | Exxon Chemical Patents Inc. | Process for preparing stable oleaginous compositions |
US5334319A (en) * | 1990-06-18 | 1994-08-02 | Tonen Corporation | Composition for hydraulic lubrication and coupling |
US5498809A (en) * | 1992-12-17 | 1996-03-12 | Exxon Chemical Patents Inc. | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
EP0713908A1 (en) | 1994-11-22 | 1996-05-29 | Ethyl Corporation | Power transmission fluids |
US5554310A (en) * | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
US5629434A (en) * | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5643859A (en) * | 1992-12-17 | 1997-07-01 | Exxon Chemical Patents Inc. | Derivatives of polyamines with one primary amine and secondary of tertiary amines |
US5646332A (en) * | 1992-12-17 | 1997-07-08 | Exxon Chemical Patents Inc. | Batch Koch carbonylation process |
US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US5767046A (en) * | 1994-06-17 | 1998-06-16 | Exxon Chemical Company | Functionalized additives useful in two-cycle engines |
EP0985725A2 (en) | 1998-09-08 | 2000-03-15 | Chevron Chemical Company LLC | Polyalkylene polysuccinimides and post-treated derivatives thereof |
US6051537A (en) * | 1985-07-11 | 2000-04-18 | Exxon Chemical Patents Inc | Dispersant additive mixtures for oleaginous compositions |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
US20050059561A1 (en) * | 2003-09-17 | 2005-03-17 | Nubar Ozbalik | Power transmitting fluids and additive compositions |
US20070078066A1 (en) * | 2005-10-03 | 2007-04-05 | Milner Jeffrey L | Lubricant formulations containing extreme pressure agents |
US20070105728A1 (en) * | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
US20070142660A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
US20070142659A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
US20090031614A1 (en) * | 2007-08-01 | 2009-02-05 | Ian Macpherson | Environmentally-Friendly Fuel Compositions |
EP2025737A1 (en) | 2007-08-01 | 2009-02-18 | Afton Chemical Corporation | Environmentally-friendly fuel compositions |
US20090071067A1 (en) * | 2007-09-17 | 2009-03-19 | Ian Macpherson | Environmentally-Friendly Additives And Additive Compositions For Solid Fuels |
US8299003B2 (en) | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
EP2933320A1 (en) | 2014-04-17 | 2015-10-21 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
EP2990469A1 (en) | 2014-08-27 | 2016-03-02 | Afton Chemical Corporation | Lubricant composition suitable for use in gasoline direct injection engines |
WO2017011689A1 (en) | 2015-07-16 | 2017-01-19 | Afton Chemical Corporation | Lubricants with titanium and/or tungsten and their use for improving low speed pre-ignition |
US9677026B1 (en) | 2016-04-08 | 2017-06-13 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
US9701921B1 (en) | 2016-04-08 | 2017-07-11 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
WO2017146867A1 (en) | 2016-02-25 | 2017-08-31 | Afton Chemical Corporation | Lubricants for use in boosted engines |
WO2017189277A1 (en) | 2016-04-26 | 2017-11-02 | Afton Chemical Corporation | Random copolymers of acrylates as polymeric friction modifiers, and lubricants containing same |
WO2017192202A1 (en) | 2016-05-05 | 2017-11-09 | Afton Chemical Corporaion | Lubricant compositions for reducing timing chain stretch |
WO2017192217A1 (en) | 2016-05-05 | 2017-11-09 | Afton Chemical Corporation | Lubricants for use in boosted engines |
WO2018111726A1 (en) | 2016-12-16 | 2018-06-21 | Afton Chemical Corporation | Multi-functional olefin copolymers and lubricating compositions containing same |
WO2018136136A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with calcium-containing detergents and their use for improving low-speed pre-ignition |
WO2018136137A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with calcium and magnesium-containing detergents and their use for improving low-speed pre-ignition and for corrosion resistance |
WO2018136138A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with overbased calcium and overbased magnesium detergents and method for improving low-speed pre-ignition |
US10214703B2 (en) | 2015-07-16 | 2019-02-26 | Afton Chemical Corporation | Lubricants with zinc dialkyl dithiophosphate and their use in boosted internal combustion engines |
EP3476923A1 (en) | 2017-10-25 | 2019-05-01 | Afton Chemical Corporation | Dispersant viscosity index improvers to enhance wear protection in engine oils |
US10280383B2 (en) | 2015-07-16 | 2019-05-07 | Afton Chemical Corporation | Lubricants with molybdenum and their use for improving low speed pre-ignition |
US10336959B2 (en) | 2015-07-16 | 2019-07-02 | Afton Chemical Corporation | Lubricants with calcium-containing detergent and their use for improving low speed pre-ignition |
US10377963B2 (en) | 2016-02-25 | 2019-08-13 | Afton Chemical Corporation | Lubricants for use in boosted engines |
US10421922B2 (en) | 2015-07-16 | 2019-09-24 | Afton Chemical Corporation | Lubricants with magnesium and their use for improving low speed pre-ignition |
EP3560966A2 (en) | 2018-04-25 | 2019-10-30 | Afton Chemical Corporation | Multifunctional branched polymers with improved low-temperature performance |
EP3578625A1 (en) | 2018-06-05 | 2019-12-11 | Afton Chemical Corporation | Lubricant composition and dispersants therefor having a beneficial effect on oxidation stability |
WO2020174454A1 (en) | 2019-02-28 | 2020-09-03 | Afton Chemical Corporation | Lubricating compositions for diesel particulate filter performance |
US10836976B2 (en) | 2018-07-18 | 2020-11-17 | Afton Chemical Corporation | Polymeric viscosity modifiers for use in lubricants |
EP3812445A1 (en) | 2019-10-24 | 2021-04-28 | Afton Chemical Corporation | Synergistic lubricants with reduced electrical conductivity |
EP3858954A1 (en) | 2020-01-29 | 2021-08-04 | Afton Chemical Corporation | Lubricant formulations with silicon-containing compounds |
EP3954753A1 (en) | 2020-08-12 | 2022-02-16 | Afton Chemical Corporation | Polymeric surfactants for improved emulsion and flow properties at low temperatures |
WO2022094557A1 (en) | 2020-10-30 | 2022-05-05 | Afton Chemical Corporation | Engine oils with low temperature pump ability |
EP4067463A1 (en) | 2021-03-30 | 2022-10-05 | Afton Chemical Corporation | Engine oils with improved viscometric performance |
EP4098723A1 (en) | 2021-06-04 | 2022-12-07 | Afton Chemical Corporation | Lubricating compositions for a hybrid engine |
WO2023004265A1 (en) | 2021-07-21 | 2023-01-26 | Afton Chemical Corporation | Methods of reducing lead corrosion in an internal combustion engine |
EP4124648A1 (en) | 2021-07-31 | 2023-02-01 | Afton Chemical Corporation | Engine oil formulations for low timing chain stretch |
US11572523B1 (en) | 2022-01-26 | 2023-02-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
WO2023141399A1 (en) | 2022-01-18 | 2023-07-27 | Afton Chemical Corporation | Lubricating compositions for reduced high temperature deposits |
WO2023159095A1 (en) | 2022-02-21 | 2023-08-24 | Afton Chemical Corporation | Polyalphaolefin phenols with high para-position selectivity |
WO2023212165A1 (en) | 2022-04-27 | 2023-11-02 | Afton Chemical Corporation | Additives with high sulfurization for lubricating oil compositions |
EP4282937A1 (en) | 2022-05-26 | 2023-11-29 | Afton Chemical Corporation | Engine oil formluation for controlling particulate emissions |
EP4306624A1 (en) | 2022-07-14 | 2024-01-17 | Afton Chemical Corporation | Transmission lubricants containing molybdenum |
EP4310162A1 (en) | 2022-07-15 | 2024-01-24 | Afton Chemical Corporation | Detergent systems for oxidation resistance in lubricants |
EP4317369A1 (en) | 2022-08-02 | 2024-02-07 | Afton Chemical Corporation | Detergent systems for improved piston cleanliness |
US11912955B1 (en) | 2022-10-28 | 2024-02-27 | Afton Chemical Corporation | Lubricating compositions for reduced low temperature valve train wear |
US11926804B1 (en) | 2023-01-31 | 2024-03-12 | Afton Chemical Corporation | Dispersant and detergent systems for improved motor oil performance |
WO2024073304A1 (en) | 2022-09-27 | 2024-04-04 | Afton Chemical Corporation | Lubricating composition for motorcycle applications |
EP4357442A1 (en) | 2022-09-21 | 2024-04-24 | Afton Chemical Corporation | Lubricating composition for fuel efficient motorcycle applications |
EP4368687A1 (en) | 2022-11-10 | 2024-05-15 | Afton Chemical Corporation | Corrosion inhibitor and industrial lubricant including the same |
EP4386070A1 (en) | 2022-12-09 | 2024-06-19 | Afton Chemical Corporation | Driveline and transmission fluids for low speed wear and scuffing |
EP4389859A2 (en) | 2022-12-20 | 2024-06-26 | Afton Chemical Corporation | Low ash lubricating compositions for controlling steel corrosion |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8407300D0 (en) * | 1984-03-21 | 1984-04-26 | Ici Plc | Surfactants |
CA2308554A1 (en) * | 1999-06-22 | 2000-12-22 | Scott D. Schwab | Phosphorylated thermal stability additives for distillate fuels |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3202693A (en) * | 1962-10-11 | 1965-08-24 | Monsanto Co | Succinate half-esters of alkylene glycol phosphate |
US3255108A (en) * | 1961-08-30 | 1966-06-07 | Lubrizol Corp | Water-in-oil emulsions containing succinic esters |
US3288714A (en) * | 1961-12-06 | 1966-11-29 | Monsanto Co | Lubricating oil compositions containing alkenyl succinic anhydrides |
-
0
- GB GB1054276D patent/GB1054276A/en active Active
-
1964
- 1964-05-19 DE DE19641520211 patent/DE1520211A1/en active Pending
-
1967
- 1967-03-07 US US621136A patent/US3403102A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3255108A (en) * | 1961-08-30 | 1966-06-07 | Lubrizol Corp | Water-in-oil emulsions containing succinic esters |
US3288714A (en) * | 1961-12-06 | 1966-11-29 | Monsanto Co | Lubricating oil compositions containing alkenyl succinic anhydrides |
US3202693A (en) * | 1962-10-11 | 1965-08-24 | Monsanto Co | Succinate half-esters of alkylene glycol phosphate |
Cited By (131)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4321308A (en) * | 1975-02-07 | 1982-03-23 | The Lubrizol Corporation | Metal workpieces coated with ester-based hot melt metal working lubricants |
US4072618A (en) * | 1976-08-27 | 1978-02-07 | Mobil Oil Corporation | Metal working lubricant |
US4444649A (en) * | 1982-11-15 | 1984-04-24 | Union Oil Company Of California | Antifoulant for high temperature hydrocarbon processing |
US4589993A (en) * | 1982-12-27 | 1986-05-20 | Exxon Research & Engineering Co. | Power transmission shift fluids containing two-component friction modifier additive |
US6051537A (en) * | 1985-07-11 | 2000-04-18 | Exxon Chemical Patents Inc | Dispersant additive mixtures for oleaginous compositions |
US6127321A (en) * | 1985-07-11 | 2000-10-03 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US6355074B1 (en) | 1985-07-11 | 2002-03-12 | Exxon Chemical Patents Inc | Oil soluble dispersant additives useful in oleaginous compositions |
US4963275A (en) * | 1986-10-07 | 1990-10-16 | Exxon Chemical Patents Inc. | Dispersant additives derived from lactone modified amido-amine adducts |
US4866141A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterfied or aminated additives useful in oleaginous compositions and compositions containing same |
US4954276A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4906394A (en) * | 1986-10-07 | 1990-03-06 | Exxon Chemical Patents Inc. | Lactone modified mono-or dicarboxylic acid based adduct dispersant compositions |
US4866139A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified, esterified dispersant additives useful in oleaginous compositions |
US4866140A (en) * | 1986-10-07 | 1989-09-12 | Exxon Chemical Patents Inc. | Lactone modified adducts or reactants and oleaginous compositions containing same |
US4954277A (en) * | 1986-10-07 | 1990-09-04 | Exxon Chemical Patents Inc. | Lactone modified, esterified or aminated additives useful in oleaginous compositions and compositions containing same |
US5032320A (en) * | 1986-10-07 | 1991-07-16 | Exxon Chemical Patents Inc. | Lactone modified mono- or dicarboxylic acid based adduct dispersant compositions |
US5788722A (en) * | 1986-10-16 | 1998-08-04 | Exxon Chemical Patents Inc | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous compositions |
US5756428A (en) * | 1986-10-16 | 1998-05-26 | Exxon Chemical Patents Inc. | High functionality low molecular weight oil soluble dispersant additives useful in oleaginous composition |
US5451333A (en) * | 1987-05-26 | 1995-09-19 | Exxon Chemical Patents Inc. | Haze resistant dispersant-detergent compositions |
US5312554A (en) * | 1987-05-26 | 1994-05-17 | Exxon Chemical Patents Inc. | Process for preparing stable oleaginous compositions |
US4971711A (en) * | 1987-07-24 | 1990-11-20 | Exxon Chemical Patents, Inc. | Lactone-modified, mannich base dispersant additives useful in oleaginous compositions |
US4820432A (en) * | 1987-07-24 | 1989-04-11 | Exxon Chemical Patents Inc. | Lactone-modified, Mannich base dispersant additives useful in oleaginous compositions |
US4863624A (en) * | 1987-09-09 | 1989-09-05 | Exxon Chemical Patents Inc. | Dispersant additives mixtures for oleaginous compositions |
US4943382A (en) * | 1988-04-06 | 1990-07-24 | Exxon Chemical Patents Inc. | Lactone modified dispersant additives useful in oleaginous compositions |
US5059335A (en) * | 1989-02-08 | 1991-10-22 | The Lubrizol Corporation | Lubricants containing salts of hydroxyalkane phosphonic acids |
US5154843A (en) * | 1989-02-08 | 1992-10-13 | The Lubrizol Corporation | Hydroxyalkane phosphonic acids and derivatives thereof and lubricants containing the same |
EP0389967A3 (en) * | 1989-03-27 | 1991-01-09 | Aluminum Company Of America | Compositions useful as lubricants |
EP0389967A2 (en) * | 1989-03-27 | 1990-10-03 | Aluminum Company Of America | Compositions useful as lubricants |
US5334319A (en) * | 1990-06-18 | 1994-08-02 | Tonen Corporation | Composition for hydraulic lubrication and coupling |
US5652201A (en) * | 1991-05-29 | 1997-07-29 | Ethyl Petroleum Additives Inc. | Lubricating oil compositions and concentrates and the use thereof |
EP0558835A1 (en) | 1992-01-30 | 1993-09-08 | Albemarle Corporation | Biodegradable lubricants and functional fluids |
US5663130A (en) * | 1992-12-17 | 1997-09-02 | Exxon Chemical Patents Inc | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
US5646332A (en) * | 1992-12-17 | 1997-07-08 | Exxon Chemical Patents Inc. | Batch Koch carbonylation process |
US5498809A (en) * | 1992-12-17 | 1996-03-12 | Exxon Chemical Patents Inc. | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant dispersant additives |
US5696064A (en) * | 1992-12-17 | 1997-12-09 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5698722A (en) * | 1992-12-17 | 1997-12-16 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5703256A (en) * | 1992-12-17 | 1997-12-30 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5717039A (en) * | 1992-12-17 | 1998-02-10 | Exxon Chemical Patents Inc. | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
US5554310A (en) * | 1992-12-17 | 1996-09-10 | Exxon Chemical Patents Inc. | Trisubstituted unsaturated polymers |
US5643859A (en) * | 1992-12-17 | 1997-07-01 | Exxon Chemical Patents Inc. | Derivatives of polyamines with one primary amine and secondary of tertiary amines |
US6030930A (en) * | 1992-12-17 | 2000-02-29 | Exxon Chemical Patents Inc | Polymers derived from ethylene and 1-butene for use in the preparation of lubricant disperant additives |
US5629434A (en) * | 1992-12-17 | 1997-05-13 | Exxon Chemical Patents Inc | Functionalization of polymers based on Koch chemistry and derivatives thereof |
US5767046A (en) * | 1994-06-17 | 1998-06-16 | Exxon Chemical Company | Functionalized additives useful in two-cycle engines |
EP0713908A1 (en) | 1994-11-22 | 1996-05-29 | Ethyl Corporation | Power transmission fluids |
EP0985725A2 (en) | 1998-09-08 | 2000-03-15 | Chevron Chemical Company LLC | Polyalkylene polysuccinimides and post-treated derivatives thereof |
US6627584B2 (en) | 2002-01-28 | 2003-09-30 | Ethyl Corporation | Automatic transmission fluid additive comprising reaction product of hydrocarbyl acrylates and dihydrocarbyldithiophosphoric acids |
US20070066498A1 (en) * | 2003-09-17 | 2007-03-22 | Nubar Ozbalik | Power transmitting fluids and additive compositions |
US20050059561A1 (en) * | 2003-09-17 | 2005-03-17 | Nubar Ozbalik | Power transmitting fluids and additive compositions |
US20070078066A1 (en) * | 2005-10-03 | 2007-04-05 | Milner Jeffrey L | Lubricant formulations containing extreme pressure agents |
US7928260B2 (en) | 2005-11-09 | 2011-04-19 | Afton Chemical Corporation | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US20070105728A1 (en) * | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
US20070142660A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Salt of a sulfur-containing, phosphorus-containing compound, and methods thereof |
US20070142237A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Lubricant composition |
US20070142659A1 (en) * | 2005-11-09 | 2007-06-21 | Degonia David J | Sulfur-containing, phosphorus-containing compound, its salt, and methods thereof |
US8299003B2 (en) | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
US20080319216A1 (en) * | 2005-11-09 | 2008-12-25 | Degonia David J | Salt of a Sulfur-Containing, Phosphorus-Containing Compound, And Methods Thereof |
EP2017329A1 (en) | 2007-05-04 | 2009-01-21 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
US20100152078A1 (en) * | 2007-05-04 | 2010-06-17 | Ian Macpherson | Environmentally-friendly lubricant compositions |
EP2420553A1 (en) | 2007-05-04 | 2012-02-22 | Afton Chemical Corporation | Environmentally-Friendly Lubricant Compositions |
US20080274921A1 (en) * | 2007-05-04 | 2008-11-06 | Ian Macpherson | Environmentally-Friendly Lubricant Compositions |
EP2025737A1 (en) | 2007-08-01 | 2009-02-18 | Afton Chemical Corporation | Environmentally-friendly fuel compositions |
US20090031614A1 (en) * | 2007-08-01 | 2009-02-05 | Ian Macpherson | Environmentally-Friendly Fuel Compositions |
US20090071067A1 (en) * | 2007-09-17 | 2009-03-19 | Ian Macpherson | Environmentally-Friendly Additives And Additive Compositions For Solid Fuels |
EP2933320A1 (en) | 2014-04-17 | 2015-10-21 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
US9657252B2 (en) | 2014-04-17 | 2017-05-23 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
EP2990469A1 (en) | 2014-08-27 | 2016-03-02 | Afton Chemical Corporation | Lubricant composition suitable for use in gasoline direct injection engines |
US10550349B2 (en) | 2015-07-16 | 2020-02-04 | Afton Chemical Corporation | Lubricants with titanium and/or tungsten and their use for improving low speed pre-ignition |
US10421922B2 (en) | 2015-07-16 | 2019-09-24 | Afton Chemical Corporation | Lubricants with magnesium and their use for improving low speed pre-ignition |
EP3943581A1 (en) | 2015-07-16 | 2022-01-26 | Afton Chemical Corporation | Lubricants with tungsten and their use for improving low speed pre-ignition |
US10214703B2 (en) | 2015-07-16 | 2019-02-26 | Afton Chemical Corporation | Lubricants with zinc dialkyl dithiophosphate and their use in boosted internal combustion engines |
US10336959B2 (en) | 2015-07-16 | 2019-07-02 | Afton Chemical Corporation | Lubricants with calcium-containing detergent and their use for improving low speed pre-ignition |
WO2017011689A1 (en) | 2015-07-16 | 2017-01-19 | Afton Chemical Corporation | Lubricants with titanium and/or tungsten and their use for improving low speed pre-ignition |
US10280383B2 (en) | 2015-07-16 | 2019-05-07 | Afton Chemical Corporation | Lubricants with molybdenum and their use for improving low speed pre-ignition |
WO2017146867A1 (en) | 2016-02-25 | 2017-08-31 | Afton Chemical Corporation | Lubricants for use in boosted engines |
EP3613831A1 (en) | 2016-02-25 | 2020-02-26 | Afton Chemical Corporation | Lubricants for use in boosted engines |
US10377963B2 (en) | 2016-02-25 | 2019-08-13 | Afton Chemical Corporation | Lubricants for use in boosted engines |
EP3228684A1 (en) | 2016-04-08 | 2017-10-11 | Afton Chemical Corporation | Lubricant compositions having improved frictional characteristics and methods of use thereof |
EP3243892A1 (en) | 2016-04-08 | 2017-11-15 | Afton Chemical Corporation | Lubricant compositions having improved frictional characteristics and methods of use thereof |
US9677026B1 (en) | 2016-04-08 | 2017-06-13 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
US9701921B1 (en) | 2016-04-08 | 2017-07-11 | Afton Chemical Corporation | Lubricant additives and lubricant compositions having improved frictional characteristics |
WO2017189277A1 (en) | 2016-04-26 | 2017-11-02 | Afton Chemical Corporation | Random copolymers of acrylates as polymeric friction modifiers, and lubricants containing same |
US10323205B2 (en) | 2016-05-05 | 2019-06-18 | Afton Chemical Corporation | Lubricant compositions for reducing timing chain stretch |
WO2017192202A1 (en) | 2016-05-05 | 2017-11-09 | Afton Chemical Corporaion | Lubricant compositions for reducing timing chain stretch |
US11155764B2 (en) | 2016-05-05 | 2021-10-26 | Afton Chemical Corporation | Lubricants for use in boosted engines |
WO2017192217A1 (en) | 2016-05-05 | 2017-11-09 | Afton Chemical Corporation | Lubricants for use in boosted engines |
WO2018111726A1 (en) | 2016-12-16 | 2018-06-21 | Afton Chemical Corporation | Multi-functional olefin copolymers and lubricating compositions containing same |
US10443558B2 (en) | 2017-01-18 | 2019-10-15 | Afton Chemical Corporation | Lubricants with calcium and magnesium-containing detergents and their use for improving low-speed pre-ignition and for corrosion resistance |
US10443011B2 (en) | 2017-01-18 | 2019-10-15 | Afton Chemical Corporation | Lubricants with overbased calcium and overbased magnesium detergents and method for improving low-speed pre-ignition |
WO2018136136A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with calcium-containing detergents and their use for improving low-speed pre-ignition |
WO2018136137A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with calcium and magnesium-containing detergents and their use for improving low-speed pre-ignition and for corrosion resistance |
US10370615B2 (en) | 2017-01-18 | 2019-08-06 | Afton Chemical Corporation | Lubricants with calcium-containing detergents and their use for improving low-speed pre-ignition |
WO2018136138A1 (en) | 2017-01-18 | 2018-07-26 | Afton Chemical Corporation | Lubricants with overbased calcium and overbased magnesium detergents and method for improving low-speed pre-ignition |
EP3476923A1 (en) | 2017-10-25 | 2019-05-01 | Afton Chemical Corporation | Dispersant viscosity index improvers to enhance wear protection in engine oils |
US10513668B2 (en) | 2017-10-25 | 2019-12-24 | Afton Chemical Corporation | Dispersant viscosity index improvers to enhance wear protection in engine oils |
EP3560966A2 (en) | 2018-04-25 | 2019-10-30 | Afton Chemical Corporation | Multifunctional branched polymers with improved low-temperature performance |
US11098262B2 (en) | 2018-04-25 | 2021-08-24 | Afton Chemical Corporation | Multifunctional branched polymers with improved low-temperature performance |
US11760953B2 (en) | 2018-04-25 | 2023-09-19 | Afton Chemical Corporation | Multifunctional branched polymers with improved low-temperature performance |
EP3578625A1 (en) | 2018-06-05 | 2019-12-11 | Afton Chemical Corporation | Lubricant composition and dispersants therefor having a beneficial effect on oxidation stability |
US11459521B2 (en) | 2018-06-05 | 2022-10-04 | Afton Chemical Coporation | Lubricant composition and dispersants therefor having a beneficial effect on oxidation stability |
US10836976B2 (en) | 2018-07-18 | 2020-11-17 | Afton Chemical Corporation | Polymeric viscosity modifiers for use in lubricants |
WO2020174454A1 (en) | 2019-02-28 | 2020-09-03 | Afton Chemical Corporation | Lubricating compositions for diesel particulate filter performance |
US11066622B2 (en) | 2019-10-24 | 2021-07-20 | Afton Chemical Corporation | Synergistic lubricants with reduced electrical conductivity |
EP3812445A1 (en) | 2019-10-24 | 2021-04-28 | Afton Chemical Corporation | Synergistic lubricants with reduced electrical conductivity |
EP3858954A1 (en) | 2020-01-29 | 2021-08-04 | Afton Chemical Corporation | Lubricant formulations with silicon-containing compounds |
EP4368689A1 (en) | 2020-08-12 | 2024-05-15 | Afton Chemical Corporation | Polymeric surfactants for improved emulsion and flow properties at low temperatures |
EP3954753A1 (en) | 2020-08-12 | 2022-02-16 | Afton Chemical Corporation | Polymeric surfactants for improved emulsion and flow properties at low temperatures |
WO2022094557A1 (en) | 2020-10-30 | 2022-05-05 | Afton Chemical Corporation | Engine oils with low temperature pump ability |
EP4067463A1 (en) | 2021-03-30 | 2022-10-05 | Afton Chemical Corporation | Engine oils with improved viscometric performance |
EP4098723A1 (en) | 2021-06-04 | 2022-12-07 | Afton Chemical Corporation | Lubricating compositions for a hybrid engine |
WO2023004265A1 (en) | 2021-07-21 | 2023-01-26 | Afton Chemical Corporation | Methods of reducing lead corrosion in an internal combustion engine |
EP4124648A1 (en) | 2021-07-31 | 2023-02-01 | Afton Chemical Corporation | Engine oil formulations for low timing chain stretch |
WO2023141399A1 (en) | 2022-01-18 | 2023-07-27 | Afton Chemical Corporation | Lubricating compositions for reduced high temperature deposits |
WO2023147258A1 (en) | 2022-01-26 | 2023-08-03 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
US11976250B2 (en) | 2022-01-26 | 2024-05-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
US11572523B1 (en) | 2022-01-26 | 2023-02-07 | Afton Chemical Corporation | Sulfurized additives with low levels of alkyl phenols |
WO2023159095A1 (en) | 2022-02-21 | 2023-08-24 | Afton Chemical Corporation | Polyalphaolefin phenols with high para-position selectivity |
US11976252B2 (en) | 2022-02-21 | 2024-05-07 | Afton Chemical Corporation | Polyalphaolefin phenols with high para-position selectivity |
WO2023212165A1 (en) | 2022-04-27 | 2023-11-02 | Afton Chemical Corporation | Additives with high sulfurization for lubricating oil compositions |
EP4282937A1 (en) | 2022-05-26 | 2023-11-29 | Afton Chemical Corporation | Engine oil formluation for controlling particulate emissions |
EP4306624A1 (en) | 2022-07-14 | 2024-01-17 | Afton Chemical Corporation | Transmission lubricants containing molybdenum |
US11970671B2 (en) | 2022-07-15 | 2024-04-30 | Afton Chemical Corporation | Detergent systems for oxidation resistance in lubricants |
EP4310162A1 (en) | 2022-07-15 | 2024-01-24 | Afton Chemical Corporation | Detergent systems for oxidation resistance in lubricants |
EP4317369A1 (en) | 2022-08-02 | 2024-02-07 | Afton Chemical Corporation | Detergent systems for improved piston cleanliness |
EP4357442A1 (en) | 2022-09-21 | 2024-04-24 | Afton Chemical Corporation | Lubricating composition for fuel efficient motorcycle applications |
WO2024073304A1 (en) | 2022-09-27 | 2024-04-04 | Afton Chemical Corporation | Lubricating composition for motorcycle applications |
EP4361235A1 (en) | 2022-10-28 | 2024-05-01 | Afton Chemical Corporation | Lubricating compositions for reduced low temperature valve train wear |
US11912955B1 (en) | 2022-10-28 | 2024-02-27 | Afton Chemical Corporation | Lubricating compositions for reduced low temperature valve train wear |
EP4368687A1 (en) | 2022-11-10 | 2024-05-15 | Afton Chemical Corporation | Corrosion inhibitor and industrial lubricant including the same |
EP4386070A1 (en) | 2022-12-09 | 2024-06-19 | Afton Chemical Corporation | Driveline and transmission fluids for low speed wear and scuffing |
EP4389859A2 (en) | 2022-12-20 | 2024-06-26 | Afton Chemical Corporation | Low ash lubricating compositions for controlling steel corrosion |
US11926804B1 (en) | 2023-01-31 | 2024-03-12 | Afton Chemical Corporation | Dispersant and detergent systems for improved motor oil performance |
Also Published As
Publication number | Publication date |
---|---|
DE1520211A1 (en) | 1969-07-17 |
GB1054276A (en) |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3403102A (en) | Lubricant containing phosphorus acid esters | |
US3533945A (en) | Lubricating oil composition | |
US3513093A (en) | Lubricant containing nitrogen-containing and phosphorus-containing succinic derivatives | |
US3502677A (en) | Nitrogen-containing and phosphorus-containing succinic derivatives | |
US4034038A (en) | Boron-containing esters | |
US3381022A (en) | Polymerized olefin substituted succinic acid esters | |
US3338832A (en) | Lubricating oil containing reaction product of certain acylated nitrogen containing intermediates and a boron compound | |
US3282955A (en) | Reaction products of acylated nitrogen intermediates and a boron compound | |
US3522179A (en) | Lubricating composition containing esters of hydrocarbon-substituted succinic acid | |
US3281428A (en) | Reaction product of certain acylated nitrogen containing intermediates and a boron compound | |
US3346493A (en) | Lubricants containing metal complexes of alkenyl succinic acid-amine reaction product | |
US3347790A (en) | Lubricating compositions containing metal salts of acids of phosphorus | |
US3197405A (en) | Phosphorus-and nitrogen-containing compositions and process for preparing the same | |
US3755501A (en) | Phosphate or phosphite esters of s-(2-hydroxyalkyl)phosphorodithioates | |
US3306908A (en) | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds | |
US3876550A (en) | Lubricant compositions | |
JPH0320438B2 (en) | ||
US3259579A (en) | Esters of dithiophosphoric acids and lubricating oil compositions containing same | |
US3197496A (en) | Polyphosphorus ester derivatives of o, o-dihydrocarbyl-s-hydroxylalkyl phosphorodithioates | |
US3325567A (en) | Phosphorus esters and process | |
US3267033A (en) | Lubricating composition having desirable frictional characteristics | |
US3201438A (en) | Method of producing a monoester of a hydrocarbyl thiophosphonic acid and a polyalkylene glycol | |
US4208357A (en) | Process for preparing phosphorus and sulfur containing amides and thioamides | |
US3337654A (en) | Oxyalkylenated hydroxyhydrocarbon thiophosphates | |
US3160593A (en) | Mineral oil compositions |