CN100350025C - 硼酸酯润滑油添加剂 - Google Patents
硼酸酯润滑油添加剂 Download PDFInfo
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- CN100350025C CN100350025C CNB2004800135198A CN200480013519A CN100350025C CN 100350025 C CN100350025 C CN 100350025C CN B2004800135198 A CNB2004800135198 A CN B2004800135198A CN 200480013519 A CN200480013519 A CN 200480013519A CN 100350025 C CN100350025 C CN 100350025C
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- CN
- China
- Prior art keywords
- carbon atoms
- phenyl
- oil
- butyl
- composition
- 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 - Fee Related
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- -1 Borate ester Chemical class 0.000 title claims description 166
- 239000003879 lubricant additive Substances 0.000 title description 2
- 239000000654 additive Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 239000010687 lubricating oil Substances 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 47
- 239000004327 boric acid Substances 0.000 claims description 45
- 239000003921 oil Substances 0.000 claims description 36
- 230000000996 additive effect Effects 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 230000003449 preventive effect Effects 0.000 claims description 9
- 239000000314 lubricant Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000002152 alkylating effect Effects 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical group CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 229940038384 octadecane Drugs 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000013530 defoamer Substances 0.000 claims description 3
- 230000000994 depressogenic effect Effects 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims description 2
- 235000006226 Areca catechu Nutrition 0.000 claims description 2
- 240000006240 Linum usitatissimum Species 0.000 claims description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 125000001802 myricyl 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])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 claims description 2
- 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 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 244000080767 Areca catechu Species 0.000 claims 1
- 239000000446 fuel Substances 0.000 abstract description 18
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 abstract 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical class OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000002585 base Substances 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 12
- 229960003742 phenol Drugs 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000005299 abrasion Methods 0.000 description 11
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 11
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 150000002430 hydrocarbons Chemical class 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000005864 Sulphur Substances 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940035422 diphenylamine Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000001050 lubricating effect Effects 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
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- 229910019142 PO4 Inorganic materials 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000010696 ester oil Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 241000534944 Thia Species 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005466 alkylenyl group Chemical group 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N beta-Tocopherol Natural products OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000005340 bisphosphate group Chemical group 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
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- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
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Abstract
公开了一种如通式(Ⅰ)和(Ⅱ)的硼酸酯和芳基硼酸酯，其中R1、R2和R3独立地是氢、1～24个碳原子的直链或支链的链烷基、2～24个碳原子的直链或支链的链烯基、5～12个碳原子的环烷基、6～10个碳原子的芳基、7～15个碳原子的芳烷基、7～15个碳原子的烷芳基；Ar是取代的或未取代的6～10个碳原子的芳基，以及R4和R5独立地如对R1所定义，还可以是羟基苯基或烷基化的羟基苯基，或者R4和R5与基团-OBO-一起形成取代的或未取代的5或6元环。该硼酸酯和芳基硼酸酯对于润滑油和燃料油作为抗磨剂、极压剂和摩擦改性添加剂是有效的。
Description
本发明的目的是由硼酸或芳基硼酸、2-羟乙基吡啶和碳氢醇得到的硼酸酯和芳基硼酸酯。此硼酸酯提供了无灰的、几乎无磷和无硫的抗磨、极压摩擦改性的润滑油和燃料油添加剂。
USP-4,382,006叙述了用作有机流体摩擦改性添加剂的乙氧基化胺及其硼酸衍生物。USP-4,406,802公开了混合醇硼酸酯、酰胺、胺、羟基酯、乙氧基化胺、乙氧基化酰胺和羟基烷基咪唑啉、羟基烯基烷基咪唑啉或烯基咪唑啉。
USP-4,389,322公开了作为减摩添加剂乙氧基化的胺及其硼酸酯加合物。USP-4,568,472提供了用于润滑介质的多功能添加剂，它们是混合乙氧基化胺和酰胺的硼酸酯、羟基烷基咪唑啉、水解的羟基烷基咪唑啉和羟基酯。
USP-4,492,642公开了作为硼化试剂与氨化碳氢环氧化物反应产物的润滑添加剂。
USP-4,892,670公开了通过伯胺或氨与环氧烷或环氧化物反应，然后立即或随后将此中间体与硼酸反应制备的含硼杂环化合物。该化合物适合作为润滑组合物的抗磨添加剂。
USP-4,741,848公开了通过羟基取代的酯、酰胺或酰亚胺与硼酸、三氧化硼、卤化硼、硼酰胺或硼酯反应制备的含硼化合物。此硼化合物被用作润滑油和燃料油的添加剂。
Yao，J和Dong，J.Lubr.Eng.1995，51(6)，475-8和Zheng，Z等在Wear 1998，222，134-144中叙述了在分子结构中含有氮的硼酸烷基酯。
已经发现，由2-羟乙基吡啶、硼酸和芳基硼酸以及碳氢醇得到的硼酸酯和芳基硼酸酯提供用于润滑油和燃料油的优异的抗磨、极压和摩擦改性添加剂。
公开的是如下通式的硼酸酯和芳基硼酸酯化合物。
其中，
R1、R2和R3独立地是氢、1～24个碳原子的直链或支链的链烷基、2～24个碳原子的直链或支链的链烯基、5～12个碳原子的环烷基、6～10个碳原子的芳基、7～15个碳原子的芳烷基、7～15个碳原子的烷芳基；
Ar是取代的或未取代的6～10个碳原子的芳基，以及
R4和R5独立地如对R1所定义，还可以是羟基苯基或烷基化的羟基苯基，或者
R4和R5与基团-OBO-一起形成取代的或未取代的5或6元环。
比如，R1、R2、R3、R4和R5独立地是氢或1～24个碳原子的直链或支链链烷基、6～10个碳原子的芳基或7～15个碳原子的烷芳基。
R4和R5独立地是比如正丁基、仲丁基、叔丁基、正十二烷基、正十八烷基、正辛基、异辛基、油基、硬脂基、正十四烷基、1-十六烷基、亚油基、亚麻基、植基、蜂花基、月桂基、肉豆蔻基、鲸蜡基、山嵛基、苯基、儿茶基、烷基化苯基或烷基化羟基苯基。
当R4和R5与基团-OBO-一起形成取代的或未取代的5或6元环时，取代基的例子是比如1～6个碳原子的烷基或羟基。该环可以被比如1～4个这样的基团取代。
烷基是直链或支链链状的，是比如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、正己基、正庚基、3-庚基、正辛基、2-乙基己基、正壬基、正癸基、十一烷基、正十二烷基、十三烷基、正十四烷基、十五烷基、正十六烷基、正十八烷基、正二十烷基、十七烷基、2-乙基丁基、1-甲基戊基、1，3-二甲基丁基、1，1，3，3-四甲基丁基、1-甲基己基、1-异庚基、1-甲基庚基、1，1，3-三甲基己基和1-甲基十一烷基。
烯基是直链或支链的链，是不饱和的烷基，比如是烯丙基、丙-2-烯基、丁-2-烯基、2-甲基丙-2-烯基、戊-2-烯基、己-2，4-二烯基、癸-10-烯基或二十-2-烯基。
环烷基是比如环戊基、甲基环戊基、二甲基环戊基、环己基、甲基环己基、二甲基环己基、三甲基环己基、叔丁基环己基、环癸基、金刚烷基、环十二烷基、环庚基或环辛基。
芳烷基是比如苄基、α-甲基苄基、α，α-二甲基苄基或2-苯基乙基。
芳基是比如苯基或萘基。取代的芳基是比如被1～4个1～16个碳原子的烷基或羟基取代的芳基。
烷芳基是比如o-、m-或p-甲基苯基、2，3-二甲基苯基、2，4-二甲基苯基、2，5-二甲基苯基、2，6-二甲基苯基、3，4-二甲基苯基、3，5-二甲基苯基、2-甲基-6-乙基苯基、4-叔丁基苯基、2-乙基苯基、2，6-二乙基苯基、2，4-二叔丁基苯基或2，6-二叔丁基-4-甲基苯基。
羟基苯基是比如3-羟基苯基。
烷基化的羟基苯基是比如单或二烷基化的3-羟基苯基，比如2-甲基-3-羟基苯基、4-甲基-3-羟基苯基、2-乙基-3-羟基苯基、4-乙基-3-羟基苯基、2-叔丁基-3-羟基苯基、4-叔丁基-3-羟基苯基、2-己基-3-羟基苯基、4-己基-3-羟基苯基、2，4-二甲基-3-羟基苯基、2-甲基-4-叔丁基-3-羟基苯基和其它相应的二烷基化的羟基苯基。这就是说，此化合物可用间苯二酚或烷基化的间苯二酚来制备。
按照一个优选的实施方案，本发明涉及通式(I)或通式(II)的化合物，它们选自二正十二烷-1-基硼酸-2-(吡啶-2-基)乙酯、正十八烷-1-基苯基硼酸-2-(吡啶-2-基)乙酯、正辛烷-1-基苯基硼酸-2-(吡啶-2-基)乙酯和正油-1-基苯基硼酸-2-(吡啶-2-基)乙酯。
该化合物是比如通过2-羟乙基吡啶、硼酸或芳基硼酸和碳氢醇的反应制备的。比如，该硼酸酯是在共沸除去水的条件下，通过2-羟乙基吡啶与硼酸和2当量碳氢醇的反应制备的。在一个典型的反应中，1eq.的2-(2-羟乙基)吡啶、2eq.的烷醇(比如直链或支链链的C4～C11烷基醇)和1eq.的硼酸在惰性溶剂中，在比如能够共沸除去水的条件下被一起加热。
在除去水的条件下，比如从2-(2-羟乙基)吡啶、芳基硼酸和1eq.的烷醇的反应类似地制备硼酸酯。
按照一个优选的实施方案，可以使用烷醇的混合物。
使用的溶剂是比如甲苯、二甲苯等。据设想，在适当的条件下可以不用溶剂进行反应。
碳氢醇是比如1-丁醇、仲丁醇、叔丁醇、1-十二烷醇、1-十八烷醇、1-辛醇、异辛醇、油醇、硬脂醇、1-十四烷醇、1-十六烷醇、亚油醇、亚麻醇、植醇、蜂花醇、月桂醇、肉豆蔻醇、鲸蜡醇、山嵛醇、苯酚、邻苯二酚、烷基酚、烷基化间苯二酚、乙二醇、丙二醇等。
芳基硼酸是比如苯基硼酸等。
本发明的目的还是一种具有改善抗磨性能的润滑组合物，该组合物含有
a)润滑油，以及
b)具有增强抗磨性量的至少一种通式(I)或(II)的化合物，其中R1、R2、R3、R4和R5如上面所定义。
按照本发明的润滑油是比如用于内燃机的润滑油。此油具有必需的润滑粘度。该油是比如矿物油或合成油以及它们的混合物。
按照本发明，脂类或其它固体润滑剂也是润滑油。
合成烃油包括比如鲸蜡烷的长链烷烃和烯烃聚合物，比如辛烷和癸烯的三聚体和四聚体。这样的合成油可以与1)酯油，比如具有大约2～20个碳原子的单羧酸的季戊四醇酯；2)聚二醇醚；3)聚甲醛和4)硅油相混合。在合成酯当中，有用的是从多元羧酸和单羟基醇制造的酯类。比如，由季戊四醇或其与二季戊四醇和三季戊四醇的混合物与含有1-20个碳原子的脂肪族单羧酸或这些羧酸的混合物制造的酯油。另外的例子是由三羟甲基丙烷和含有1～20个碳原子的脂肪族单羧酸或这些酸的混合物制造的酯油。
该润滑油还是原油、工业润滑油、馏分油、金属加工油和油脂。
对于本发明的硼酸酯和芳基硼酸酯添加剂，另一个用途是用于燃料油中，比如某些需要润滑性能的航空燃料等当中。该燃料是比如烃类石油馏分，比如发动机汽油、柴油燃料或燃料油。含有非烃类物质比如醇、醚、有机硝基化合物等的液体燃料组合物(比如甲醇、乙醇、二乙醚、甲乙醚、硝基甲烷等)也在本发明的范围内，比如来源于植物或矿物来源的液体燃料，比如来源于玉米、苜蓿、页岩和煤的液体燃料。作为一种或多种烃类燃料和一种或多种非烃类燃料混合物的燃料也在考虑之内。这样的混合物的例子是汽油和乙醇的组合以及柴油和醚的组合。
该添加剂给油提供了极压、抗磨和减摩的性能，在燃烧时，对于常用的小汽车催化转化器是无害的。
在油组合物中本发明的添加剂，其含量有利地为组合物总重量的比如大约0.01～大约20wt％。比如，基于组合物整体的重量，硼酸酯和芳基硼酸酯的含量为大约0.05～大约15wt％，大约0.1～大约10wt％，大约0.2-大约5wt％。比如，基于组合物整体的重量，硼酸酯和芳基硼酸酯的含量为大约0.1～大约20wt％，大约0.1～大约15wt％，大约0.1～大约5wt％。
据设想，在极其不利的条件下操作的润滑组合物中，比如在用于船舶柴油机的润滑组合物中，本发明的添加剂的含量可以直至该润滑组合物总重量的大约30wt％或更多。
在燃料组合物中本发明添加剂的含量是基于该燃料的大约1～大约50,000ppm。比如，添加剂的含量是基于燃料的大约4～大约5,000ppm。
按照本发明被稳定化的润滑油还可以包括其它的添加剂，添加这些添加剂是为了进一步改善这些配方的基本性能；这些添加剂包括抗氧剂、金属钝化剂、防锈剂、腐蚀抑制剂、粘度指数改善剂、极压剂、倾点降低剂、固态润滑剂、分散剂、清净剂、消泡剂、颜色稳定剂、另外的高压添加剂、破乳剂、抗磨添加剂和降低摩擦系数的添加剂。
基于该润滑油，在各种情况下这些添加剂通常的含量为大约0.01～10.0wt％。
下面的文字给出这些附加添加剂的例子
1.抗氧剂的例子：
1.1烷基化的一元酚，比如2，6-二叔丁基-4-甲基苯酚、2-丁基-4，6-二甲基苯酚、2，6-二叔丁基-4-乙基苯酚、2，6-二叔丁基-4-正丁基苯酚、2，6-二叔丁基-4-异丁基苯酚、2，6-二环戊基-4-甲基苯酚、2-(甲基环己基)-4，6-二甲基苯酚、2，6-二(十八烷基)-4-甲基苯酚、2，4，6-三环己基-苯酚、2，6-二叔丁基-4-甲氧基甲基苯酚、线形或侧链支链的壬基酚，比如2，6-二壬基-4-甲基苯酚、2，4-二甲基-6-(1’-甲基十一烷-1’-基)苯酚、2，4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚、2，4-二甲基-6-(1’-甲基十三烷-1’-基)苯酚或它们的混合物。
1.2烷硫基甲基苯酚，比如2，4-二辛硫基甲基-6-叔丁基苯酚、2，4-二辛硫基甲基-6-甲基苯酚、2，4-二辛硫基-6-乙基苯酚或2，6-二(十二烷硫基)甲基-4-壬基苯酚。
1.3氢醌和烷基化的氢醌，比如2，6-二叔丁基-4-甲氧基苯酚、2，5-二叔丁基-氢醌、2，5-二叔戊基氢醌、2，6-二苯基-4-十八烷氧基苯酚、2，6-二叔丁基氢醌、2，5-二叔丁基-4-羟基苯甲醚、3，5-二叔丁基-4-羟基苯甲醚、硬脂酸3，5-二叔丁基-4-羟基苯酯或己二酸二(3，5-二叔丁基-4-羟基苯基)酯。
1.4生育酚，比如α-、β-或γ-生育酚或它们的混合物(维生素E)
1.5羟基化的硫二苯基醚，比如2，2’-硫二(6-叔丁基-4-甲基苯酚)、2，2’-硫二(4-辛基苯酚)、4，4’-硫二(6-叔丁基-3-甲基苯酚)、4，4’-硫二(6-叔丁基-2-甲基苯酚)、4，4’-硫二(3，6二仲戊基苯酚)或4，4’-二(2，6-二甲基-4-羟基苯酚)二硫化物。
1.6亚烷基双酚，比如2，2’-亚甲基-二(6-叔丁基-4-甲基苯酚)、2，2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2，2’-亚甲基二(4-甲基-6-(α-甲基环己基)苯酚)、2，2’-亚甲基二(4-甲基-6-环己基苯酚)、2，2’-亚甲基二(6-壬基-4-甲基苯酚)、2，2’-亚甲基二(4，6-二叔丁基苯酚)、2，2’-亚乙基二(4，6-二叔丁基苯酚)、2，2’-亚乙基二(6-叔丁基-4-异丁基苯酚)、2，2’-亚甲基二(6-(α-甲基苄基)-4-壬基苯酚)、2，2’-亚甲基二(6-(α，α-二甲基苄基)-4-壬基苯酚)、4，4’-亚甲基二(2，6二叔丁基苯酚)、4，4’-亚甲基二(6-叔丁基-2-甲基苯酚)、1，1’-二(5-叔丁基-4-羟基-2-甲基苯酚)丁烷、2，6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1，1，3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷1，1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷硫基丁烷、乙二醇二(3，3-二(3’-叔丁基-4’-羟基苯基)丁酸酯)、二(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯、二(2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基)对苯二甲酸酯、1，1-二(3，5-二甲基-2-羟基苯基)丁烷、2，2-二(3，5-二叔丁基-4-羟基苯基)丙烷、2，2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷硫基丁烷或1，1，5，5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7 O-、N-和S-化合物，比如3，5，3’，5’-四叔丁基-4，4’-二羟基二苄基醚、4-羟基-3，5-二甲基苄硫基乙酸十八烷基酯、4-羟基-3，5-二叔丁基苄硫基乙酸十三烷基酯、三(3，5-二叔丁基)胺、二(4-叔丁基-3-羟基-2，6-二甲基苄基)二硫邻苯二甲酸酯、二(3，5-二叔丁基-4-羟基苄基)硫化物或3，5-二叔丁基-4-羟基苄硫基乙酸异辛酯。
1.8羟基苄基化的丙二酸酯，比如2，2-二(3，5-二叔丁基-2-羟基苄基)丙二酸二(十八烷基)酯、2-(3-叔丁基-4-羟基-5-甲基苄基)-丙二酸二(十八烷基)酯、巯乙基-2，2-二(3，5-二叔丁基-4-羟基苄基)丙二酸二(十二烷基)酯或2，2-二(3，5-二叔丁基-4-羟基苄基)丙二酸二(4-(1，1，3，3-四甲基丁基)苯基)酯。
1.9芳香族羟基苄基化合物，比如1，3，5-三(3，5-二叔丁基-4-羟基苄基)-2，4，6-三甲基苯、1，4-二(3，5-二叔丁基-4-羟基苄基)-2，3，5，6-四甲基苯或2，4，6-三(3，5-二叔丁基-4-羟基苄基)苯酚。
1.10三嗪化合物，比如2，4-二辛硫基-6-(3，5-二叔丁基-4-羟基苯胺基)1，3，5-三嗪、2-辛硫基-4，6-二(3，5-二叔丁基-4-羟基苯胺基)-1，3，5-三嗪、2-辛硫基-4，6-二(3，5-二叔丁基-4-羟基苯氧基)-1，3，5-三嗪、2，4，6-三(3，5-二叔丁基-4-羟基苯氧基)-1，2，3-三嗪、1，3，5-三(3，5-二叔丁基-4-羟基苄基)-异氰脲酸酯、1，3，5-三(4-叔丁基-3-羟基-2，6-二甲基苄基)异氰脲酸酯、2，4，6-三(3，5-二叔丁基-4-羟基苯基乙基)-1，3，5-三嗪、1，3，5-三(3，5-二叔丁基-4-羟基苯基丙基)六氢-1，3，5-三嗪或1，3，5三(3，5-二环己基-4-羟基苄基)异氰脲酸酯。
1.11膦酸苄酯，比如2，5-二叔丁基-4-羟基苄基膦酸二甲酯、3，5-二叔丁基-4-羟基苄基膦酸二乙酯、3，5-二叔丁基-4-羟基苄基膦酸二(十八烷基)酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二(十八烷基)酯或3，5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
1.12酰基氨基苯酚，比如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺或N-(3，5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13β-(3，5-二叔丁基-4-羟基苯基)丙酸酯、β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸、β-(3，5-二环己基-4-羟基苯基)丙酸、3，5-二叔丁基-4-羟基苯基乙酸、β-(5-叔丁基-4-羟基苯基)-3-硫代丁酸与单羟基或多羟基醇的酯，比如与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1，6-己二醇、1，9-壬二醇、乙二醇、1，2-丙二醇、新戊二醇、硫代乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰脲酸酯、N，N’-二(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2，6，7-三氧杂双环(2.2.2)辛烷、甘油或基于比如椰子油、葡籽油、葵花子油或油菜籽油的天然三甘油酯的酯交换产物。
1.14β-(3，5-二叔丁基-4-羟基苯基)丙酰胺，比如N，N’-二(3，5-二叔丁基-4-羟基苯基丙基)六亚甲基二胺、N，N’-二(3，5-二叔丁基-4-羟基苯基丙基)三亚甲基二胺或N，N’-二(3，5-二叔丁基-4-羟基苯基丙基)肼。
1.15抗坏血酸(维生素C)
1.16胺类抗氧剂，比如N，N’-二异丙基-p-亚苯基二胺、N，N’-二仲丁基-p-亚苯基二胺、N，N’-二(1，4-二甲基戊基)-p-亚苯基二胺、N，N’-二(1-乙基-3-甲基戊基)-p-亚苯基二胺、N，N’-二(1-甲基庚基)-p-亚苯基二胺、N，N’-二环己基-p-亚苯基二胺、N，N’-二苯基-p-亚苯基二胺、N，N’-二(萘-2-基)-p-亚苯基二胺、N-异丙基-N’-苯基-p-亚苯基二胺、N-(1，3-二甲基丁基)-N’-苯基-p-亚苯基二胺、N-(1-甲基庚基)-N’-苯基-p-亚苯基二胺、N-环己基-N’-苯基-p-亚苯基二胺、4-(p-甲苯磺酰胺基)二苯基胺、N，N’-二甲基-N，N’-二仲丁基-p-亚苯基二胺、二苯基胺、N-烯丙基苯基胺、4-异丙氧基-二苯基胺、N-苯基-1-萘基胺、N-(4-叔辛基苯基)-1-萘基胺、N-苯基-2-萘基胺、辛基化的二苯基胺，比如，p，p’-二叔辛基-二苯基胺、4-正丁基氨基苯酚、4-丁酰胺基苯酚、4-壬酰胺基苯酚、4-十二烷酰胺基苯酚、4-十八烷酰胺基苯酚、二(4-甲氧基苯基)胺、2，6-二叔丁基-4-二甲基氨基甲基苯酚、2，4’-二氨基二苯基甲烷、4，4’-二氨基-二苯基甲烷、N，N，N’N’-四甲基-4，4’-二氨基-二苯基甲烷、1，2-二((2-甲基苯基)氨基)乙烷、1，2-二(苯基氨基)丙烷、(o-甲苯基)双胍、二(4-(1’，3’-二甲基丁基)苯基)胺、叔辛基化的N-苯基-1-萘基胺，单烷基化和二烷基化的叔丁基/叔辛基-二苯基胺混合物、单烷基化和二烷基化的壬基二苯基胺的混合物、单烷基化和二烷基化的十二烷基二苯基胺的混合物、单烷基化和二烷基化的异丙基/异己基二苯基胺的混合物、单烷基化和二烷基化的叔丁基二苯基胺混合物、2，3-二氢-3，3-二甲基-4H-1，4-苯并噻嗪、酚噻嗪、单烷基化和二烷基化的叔丁基/叔辛基酚噻嗪混合物、单烷基化和二烷基化的叔辛基反射器混合物、N-烯丙基酚噻嗪、N，N，N’N’-四苯基-1，4-二氨基-丁-2-烯、N，N-二(2，2，6，6-四甲基哌啶-4-基)六亚甲基二胺、二(2，2，6，6-四甲基哌啶-4-基)癸二酸酯、2，2，6，6-四甲基哌啶-4-酮或2，2，6，6-四甲基哌啶-4-醇。
1.17脂肪族或芳香族亚磷酸酯、硫代二丙酸酯或硫代二乙酸酯或二硫代氨基甲酸盐或二硫代磷酸盐、2，2，12，12-四甲基-5，9-二羟基-3，7，1-三硫杂十三烷或2，2，15，15-四甲基-5-12-二羟基-3，7，10，14-四硫杂十六烷。
2.比如对于铜的金属钝化剂的例子是：
2.1苯并三唑及其衍生物，比如4-烷基或5-烷基苯并三唑(比如甲基苯并三唑)及其衍生物、4，5，6，7-四氢苯并三唑、5，5’-亚甲基二苯并三唑、苯并三唑或甲基苯并三唑的Mannich碱，比如1-(二(2-乙基己基)氨基甲基)甲基苯并三唑和1-(二(2-乙基己基)氨基甲基)1-苯并三唑；烷氧基烷基苯并三唑，比如1-(壬氧基甲基)苯并三唑、1-(1-丁氧基乙基)苯并三唑和1-(1-环己氧基丁基)甲基苯并三唑。
2.2 1，2，4-三唑及其衍生物，比如3-烷基(或芳基)-1，2，4-三唑、1，2，4-三唑的Mannich碱，比如1-(二(2-乙基己基)氨基甲基)-1，2，4-三唑；烷氧基烷基-1，2，4-三唑，比如1-(1-丁氧基乙基)-1，2，4-三唑；酰基化的3-氨基-1，2，4-三唑。
2.3咪唑衍生物，比如4，4’-亚甲基二(2-十一烷基-5-甲基咪唑)、二(N-甲基)咪唑-2-基)卡必醇辛基醚。
2.4含硫杂环化合物，比如2-巯基苯并噻唑、2，5-二巯基-1，3，4-噻二唑、2，5-二巯基-苯并噻二唑及其衍生物、3，5-二(二(2-乙基己基)氨基甲基)-1，3，4-噻二唑啉-2-酮，以及
2.5氨基化合物，比如亚水杨基亚丙基二胺、水杨基氨基胍及其盐。
3.防锈剂的例子是：
3.1有机酸，它们的酯、金属盐、胺盐和酸酐，比如烷基-和烯基琥珀酸及其与醇、二元醇或羟基羧酸的部分酯、烷基-和烯基琥珀酸、4-壬基苯氧基乙酸、烷氧基-和烷氧基乙氧基羧酸，比如十二烷氧基乙酸、十二烷氧基(乙氧基)乙酸的部分酰胺及其胺盐，以及N-油酰基肌氨酸、缩水山梨糖醇单油酸酯、萘酸铅、烯基琥珀酸酐，比如十二烯基琥珀酸酐、2-(2-羧基乙基)-1-十二烷基-3-甲基甘油及其盐，特别是钠盐和三乙醇胺盐。
3.2含氮化合物，比如：
3.2.1脂肪族或脂环族的伯胺、仲胺或叔胺以及有机酸和无机酸的胺盐，比如油溶性烷基铵羧酸盐，还有1-(N，N-二(2-羟乙基)氨基)-3-(4-壬基苯氧基)丙-2-醇；
3.2.2杂环化合物，比如取代的咪唑啉和唑啉、2-十七烯基-1-(2-羟乙基)-咪唑啉；
3.3含磷化合物，比如磷酸部分酯或膦酸部分酯的胺盐、二烷基二硫代磷酸锌；
3.4含硫化合物，比如二壬基萘磺酸钡、石油磺酸钙、烷硫基取代的脂肪族羧酸、脂肪族2-磺基羧酸酯及其盐；
3.5甘油衍生物，比如单油酸甘油酯、1-(烷基苯氧基)-3-(2-羟乙基)甘油、1-(烷基苯氧基)-3-(2，3-二羟丙基)甘油、2-羧基烷基-1，3-二烷基甘油；
4.粘度指数改良剂的例子是：
聚丙烯酸酯、乙烯基吡咯烷酮/甲基丙烯酸酯共聚物、聚乙烯基吡咯烷酮、聚丁烯、烯烃共聚物、苯乙烯/丙烯酸酯共聚物、聚醚；
5.倾点降低剂的例子是：
聚甲基丙烯酸酯、烷基化的萘衍生物；
6.分散剂/表面活性剂的例子是：
聚丁烯基琥珀酰胺或酰亚胺、聚丁烯基膦酸衍生物和碱式磺酸、苯酚和水杨酸的镁、钙和钡盐；
7.消泡剂的例子是：
硅油和polymethocrylen；
8.破乳剂的例子是：
聚醚多元醇和二壬基萘磺酸；
9.摩擦改性剂的例子是：
脂肪酸及其衍生物(即天然脂肪酸酯，比如单油酸甘油酯)、酰胺、酰亚胺和胺(即油基胺)，含硫有机二硫代氨基甲酸钼、含硫磷有机二硫代磷酸钼、基于分散剂的含硫氮有机钼化合物、钼的羧酸盐、钼-胺络合物、钼胺/醇/酰胺络合物和钼的原子簇化合物，TeflonTM和二硫化钼；
10.抗磨添加剂的例子是：
10.1含硫和/或磷和/或卤素化合物，比如硫化的烯烃和植物油、二烷基二硫代磷酸锌、磷酸三甲苯酯、磷酸三(羟基甲苯)酯、氯化石蜡、烷基和芳基二硫化物和三硫化物、磷酸单烷基酯和二烷基酯的胺盐、甲基磷酸的胺盐、二乙醇胺基甲基甲苯基三唑、二(2-乙基己基)-氨基甲基甲苯基三唑、2，5-二巯基-1，3，4-噻二唑衍生物、(二异丙氧基磷酰基硫酰基)硫代丙酸乙酯、硫代磷酸三苯酯、硫代磷酸三(烷基苯基)酯及其混合物(比如硫代磷酸三(异壬基苯基)酯)、硫代磷酸二苯基单壬基苯酯、硫代磷酸异丁基苯基二苯基酯、3-羟基-1，3-硫杂磷杂环丁烷-3-氧化物的十二烷基胺盐、三硫代磷酸5，5，5-三异辛基-2-乙酸酯、2-巯基苯并噻唑衍生物，比如1-N，N-二(2-乙基己基)-氨基甲基-2-巯基-1H-1，3-苯并噻唑和5-辛基硫代氨基甲酸乙氧羰基酯；
10.2二硫代磷酸而烃基酯金属盐，在此的金属是铝、铅、锡、锰、钴、镍、锌或铜，但最经常是锌。代表性的锌盐是二烷基二硫代磷酸锌，其结构如下：
这里R和R’各自独立地是C1～C20烷基、C5～C20烯基、C5～C12环烷基、C2～C13芳烷基或C6～C10芳基，比如R和R’独立地是C1～C12烷基；
10.3抗磨添加剂，如在USP-4,584,021、5,798,321、5,750,478、5,801,130、4,191,666、4,720,288、4,025,288、4,025,583和WO095/20512中所述，这些美国专利在此引作参考；比如多亚烷基胺的胺类，比如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、九亚乙基十胺和如在USP-4,267,063中所述的芳胺，此专利在此引作参考；含有特定胺和混合单磷酸和二磷酸的磷酸胺盐；该单和二磷酸的胺盐具有如下的结构式：
其中R27是氢、C1～C25的直链或支链烷基，它是未取代的或被一个或几个C1～C6烷氧基、饱和的非环或环状基团或芳基取代；
R28是C1～C25的直链或支链烷基，它是未取代的或被一个或几个C1～C6烷氧基、饱和的非环或环状基团或芳基取代；
R29是氢、C1～C25直链或支链的烷基、饱和或不饱和的非环或环状基团或芳基；以及是氢或C1～C12直链或支链烷基；和
R30和R31各自独立地是C1～C25直链或支链烷基、饱和或不饱和的非环或环状基团，或者芳基。R27和R28优选是直链或支链的C1～C12烷基，而R29、R10和R31优选是直链或支链的C1～C18烷基。
按照一个优选是实施方案，已经发现Irgalube349(CibaSpecialty Chemicals公司)是很有用的，特别是增强基础油的磨耗性能，它满足严格的军用性能规范；IRGALUBE 349具有如下的通式：
其中R33是正己基，R34是C11～C14支链的烷基，而且当x＝1时，y＝2；当x＝2时，y＝1；IRGALUBE 349是磷酸胺的混合物，CAS#80939-62-4。
10.4其它常用的抗磨添加剂是具有如下通式的化合物：
其中R1和R2各自独立地是C3～C18烷基、C5～C12环烷基、C5～C6环烷基甲基、C9～C10双环烷基甲基、C9～C10三环烷基甲基、苯基或C7～C24烷基苯基或一起是(CH3)2C(CH2)2；
R3是氢或甲基。按照一个优选的实施方案，使用IRGALUBE 353，即二硫代磷酸二烷基酯，CAS#268567-32-4。
除了硼酸酯和芳基硼酸酯以外，本燃料组合物可含有先有技术专业人员公知的其它添加剂。这包括比如四烷基铅化合物抗爆剂、比如卤代烷(比如二氯乙烷和二溴乙烷)的清净剂、比如磷酸三芳酯的防沉淀剂或沉淀改进剂、染料、某些改进剂、比如2，6-二叔丁基-4-甲基苯酚的抗氧剂、比如烷基化琥珀酸和琥珀酸酐的防锈剂、抑菌剂、防霉剂、金属钝化剂、破乳剂、上部气缸润滑剂和防冰剂。
可以用其本身是已知的方法将本硼酸酯和芳基硼酸酯加入到润滑油中。这些化合物都是易溶于油的。可以将它们直接添加到润滑油中，或者用实质上惰性，一般是液体的有机稀释剂，比如石脑油、苯、甲苯、二甲苯或一般是液态的油或燃料将其稀释形成浓缩添加剂或添加剂母料。这样的浓缩物一般含有大约10～大约90wt％的添加剂，可含有一种或几种另外的添加剂。可以以一部分添加包的形式加入此硼酸酯和芳基硼酸酯。
用下面的实施例进一步说明本发明。
实施例1
硼酸二正十二烷-1-基-2-(吡啶-2-基)乙酯
在装有磁性搅拌棒和固定有回流冷凝器的Dean-Stark管的500mL玻璃反应器中加入12.3g 2-(2-羟乙基)吡啶、37.2g 1-十二烷醇、6.2g硼酸和250mL甲苯。搅拌混合物并回流加热5小时，在此期间内除去大约5mL水，表明形成了酯。过滤溶液除去浑浊物，真空蒸馏除去溶剂，得到浅黄色油状物硼酸酯。
实施例2
苯基硼酸正十八烷-1-基-2-(吡啶-2-基)乙酯
在装有磁性搅拌棒和固定有回流冷凝器的Dean-Stark管的200mL玻璃反应器中加入5.69mL 2-(2-羟乙基)吡啶、13.7g 1-十八烷醇、6.29g苯基硼酸和150mL甲苯。搅拌混合物并回流加热16小时，在此期间内除去大约1.8mL水，表明形成了酯。过滤溶液除去浑浊物，真空蒸馏除去溶剂，得到23.4g浅黄色油状物，冷却将其固化为蜡状物。
实施例3
苯基硼酸正辛烷-1-基(吡啶-2-基)乙酯
在装有磁性搅拌棒和固定有回流冷凝器的Dean-Stark管的200mL玻璃反应器中加入5.69mL2-(2-羟乙基)吡啶、7.96g1-辛烷醇、6.29g苯基硼酸和150mL甲苯。搅拌混合物并回流加热16小时，在此期间内除去大约1.8mL水，表明形成了酯。过滤溶液除去浑浊物，真空蒸馏除去溶剂，得到16g粘性深黄色油状物。
实施例4
苯基硼酸正油-1-基(吡啶-2-基)乙酯
在装有磁性搅拌棒和固定有回流冷凝器的Dean-Stark管的200mL玻璃反应器中加入5.69mL 2-(2-羟乙基)吡啶、18.6mL油醇、6.29g苯基硼酸和150mL甲苯。搅拌混合物并回流加热16小时，在此期间内除去大约1.8mL水，表明形成了酯。过滤溶液除去浑浊物，真空蒸馏除去溶剂，得到24g粘性深黄色油状物。
实施例5
硼酸二正辛烷-1-基(吡啶-2-基)乙酯
在装有磁性搅拌棒和固定有回流冷凝器的Dean-Stark管的2000mL玻璃反应器中加入75.0g 2-(2-羟乙基)吡啶、158.7g 1-辛醇、61.8g硼酸和1500mL甲苯。搅拌混合物并回流加热18小时，在此期间内除去大约33mL水，表明形成了酯。过滤溶液除去浑浊物，真空蒸馏除去溶剂，通过烧结玻璃过滤得到的油状物，得到浅黄色油状物硼酸酯。
实施例6
抗磨性能
使用用销-盘附件改进的PCS仪器Mini-Traction机测定抗磨性能，在此仪器中保持固定的销(500×500μm)对着转动的盘，在恒定的温度加上固定的负荷。将由于从销上失去材料而造成销的移动作为磨耗的度量。测试的油是无硫、很低磷的汽车发动机油，除了没有抗磨添加剂以外是完全配方的。反应测试条件是10N的负荷，油温100℃。记录60min的磨耗数据，在此将平均磨耗率报道为磨耗曲线的线形回归斜率。报道的添加剂是基于配方油品的wt％。
| 油品 | 磨耗率 |
| 对照组(没有抗磨添加剂) | 279μm/h |
| +1.2％ZDDP | 3.0μm/h |
| +1％实施例1的化合物 | 5.7μm/h |
ZDDP是二烷基硫代磷酸锌-浓度1.2％的二价ZDDP提供0.1％的P。
实施例7
四球抗磨性测试
以在测试油中1.0wt％的浓度测试本发明硼酸酯的抗磨性能。测试油是无磷、很低硫的汽车发动机油，在配方中除了不添加抗磨添加剂以外是完全配方的。用四球磨耗测试仪按照ASTM D 1472的条件，使用40kg(392N)的负荷来测定抗磨性能。测量进行两次，用平均磨耗划痕直径(mm)报道为测试的结果。随着添加剂效果增大，测试结果的数值降低。
| 测试化合物 | 磨耗划痕直径 |
| 测试油(无抗磨添加剂) | 0.675 |
| 测试油(1％实施例1的化合物) | 0.65 |
| 测试油(1％实施例5的化合物) | 0.615 |
| 测试油(1％ZnDDP) | 0.61 |
Claims (10)
1.选自如下通式的硼酸酯或芳基硼酸酯
其中，
R1、R2和R3独立地是氢、1～24个碳原子的直链或支链的链烷基、2～24个碳原子的直链或支链的链烯基、5～12个碳原子的环烷基、6～10个碳原子的芳基、7～15个碳原子的芳烷基、7～15个碳原子的烷芳基；
Ar是取代的或未取代的6～10个碳原子的芳基，以及
R4和R5独立地是氢、1～24个碳原子的直链或支链的链烷基、2～24个碳原子的直链或支链的链烯基、5～12个碳原子的环烷基、6～10个碳原子的芳基、7～15个碳原子的芳烷基、7～15个碳原子的烷芳基，或者是羟基苯基或烷基化的羟基苯基，或者
R4和R5与基团-OBO-一起形成取代的或未取代的5或6元环。
2.按照权利要求1中所述的通式(I)或(II)的化合物，其中R1、R2、R3、R4和R5独立地是氢或1～24个碳原子的直链或支链链烷基、6～10个碳原子的芳基或7～15个碳原子的烷芳基。
3.按照权利要求1中所述的通式(I)或(II)的化合物，其中R4和R5独立地是正丁基、仲丁基、叔丁基、正十二烷基、正十八烷基、正辛基、异辛基、油基、硬脂基、正十四烷基、1-十六烷基、亚油基、亚麻基、植基、蜂花基、月桂基、肉豆蔻基、鲸蜡基、山嵛基、苯基、儿茶基、烷基化苯基或烷基化羟基苯基。
4.按照权利要求1的选自下面的通式(I)或(II)的化合物：二正十二烷-1-基硼酸-2-(吡啶-2-基)乙酯、正十八烷-1-基苯基硼酸-2-(吡啶-2-基)乙酯、正辛烷-1-基苯基硼酸-2-(吡啶-2-基)乙酯和正油-1-基苯基硼酸-2-(吡啶-2-基)乙酯。
5.包括如下成分的润滑油组合物：
a)润滑油，以及
b)具有增强耐磨量的至少一种按照权利要求1的通式(I)或(II)的化合物。
6.按照权利要求5的组合物，其中该润滑油是合成油或合成油与矿物油的混合物。
7.按照权利要求5的组合物，其中该润滑油是油脂或其它固体润滑剂。
8.按照权利要求5的组合物，其中基于整个组合物的组分b)的含量为0.2wt％～5wt％。
9.按照权利要求5的组合物，该组合物进一步含有选自下面的添加剂：抗氧剂、金属钝化剂、防锈剂、腐蚀抑制剂、粘度指数改善剂、极压剂、倾点降低剂、固态润滑剂、分散剂、清净剂、消泡剂、颜色稳定剂、另外的高压添加剂、破乳剂、抗磨添加剂和降低摩擦系数的添加剂。
10.按照权利要求5的组合物，该组合物是一种浓缩添加物，其中基于该整个组合物组分b)的含量为10～90wt％。
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| US7691794B2 (en) | 2006-01-04 | 2010-04-06 | Chemtura Corporation | Lubricating oil and fuel compositions |
| US8507417B2 (en) * | 2006-03-07 | 2013-08-13 | Exxonmobil Research And Engineering Company | Organomolybdenum-boron additives |
| WO2008065015A1 (en) * | 2006-11-27 | 2008-06-05 | Ciba Holding Inc. | Stabilised biodiesel fuel compositions |
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| CN101805659B (zh) * | 2010-04-12 | 2012-10-17 | 中国石油天然气股份有限公司 | 一种油井防偏磨用水基润滑剂 |
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| CN104178248A (zh) * | 2013-05-27 | 2014-12-03 | 天津市泽畅科技有限公司 | 一种添加在发动机油中的沉积物控制剂 |
| CN103601748B (zh) * | 2013-10-17 | 2016-11-02 | 上海交通大学 | 羟烷基化杂环硼酸酯及其制备方法、用途 |
| US9309205B2 (en) | 2013-10-28 | 2016-04-12 | Wincom, Inc. | Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures |
| FR3016885B1 (fr) * | 2014-01-27 | 2017-08-18 | Total Marketing Services | Copolymeres thermoassociatifs et echangeables, compositions les comprenant |
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| WO2016109275A1 (en) * | 2014-12-29 | 2016-07-07 | The Lubrizol Corporation | Synergistic rust inhibitor combination for lubricating grease |
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| WO2004104146A1 (en) | 2004-12-02 |
| ATE475703T1 (de) | 2010-08-15 |
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