CN1511167A - Low-molecular and high-molecular emulsifiers, particularly based on polyisobutylene, and mixtures thereof - Google Patents
Low-molecular and high-molecular emulsifiers, particularly based on polyisobutylene, and mixtures thereof Download PDFInfo
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- CN1511167A CN1511167A CNA02810580XA CN02810580A CN1511167A CN 1511167 A CN1511167 A CN 1511167A CN A02810580X A CNA02810580X A CN A02810580XA CN 02810580 A CN02810580 A CN 02810580A CN 1511167 A CN1511167 A CN 1511167A
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- polyisobutenyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 42
- 229920002367 Polyisobutene Polymers 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 13
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 13
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 6
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims abstract description 6
- 239000000839 emulsion Substances 0.000 claims description 45
- 239000000446 fuel Substances 0.000 claims description 39
- -1 isobutenyl unit Chemical group 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 19
- 230000000996 additive effect Effects 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000012141 concentrate Substances 0.000 claims description 14
- 239000000314 lubricant Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 229920000768 polyamine Polymers 0.000 claims description 13
- 239000007762 w/o emulsion Substances 0.000 claims description 13
- 238000005260 corrosion Methods 0.000 claims description 10
- 230000007797 corrosion Effects 0.000 claims description 10
- 239000002816 fuel additive Substances 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 239000003879 lubricant additive Substances 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 239000002283 diesel fuel Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000004945 emulsification Methods 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 3
- 230000003641 microbiacidal effect Effects 0.000 claims description 3
- 229940124561 microbicide Drugs 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 239000011572 manganese Substances 0.000 description 39
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 34
- 239000003795 chemical substances by application Substances 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 14
- 150000003443 succinic acid derivatives Chemical class 0.000 description 14
- 229920002266 Pluriol® Polymers 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002199 base oil Substances 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 238000007872 degassing Methods 0.000 description 6
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 229920002368 Glissopal ® Polymers 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229960000890 hydrocortisone Drugs 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 4
- 229960001231 choline Drugs 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229920001983 poloxamer Polymers 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical group OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 3
- 238000006418 Brown reaction Methods 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002605 large molecules Chemical class 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 2
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical class CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003139 biocide Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005553 drilling Methods 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229940040145 liniment Drugs 0.000 description 2
- 239000000865 liniment Substances 0.000 description 2
- 239000002855 microbicide agent Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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- 230000003068 static effect Effects 0.000 description 2
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- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 1
- RIJVOTKRVIPNIZ-UHFFFAOYSA-N 1-[4-(2-aminoethyl)piperazin-1-yl]propan-2-ol Chemical compound CC(O)CN1CCN(CCN)CC1 RIJVOTKRVIPNIZ-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N 2,2,4,6,6-pentamethylheptane Chemical compound CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 1
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- GKVINAFHJXHVDS-UHFFFAOYSA-N 2-[1-(3-aminopropyl)piperidin-4-yl]ethanol Chemical class NCCCN1CCC(CCO)CC1 GKVINAFHJXHVDS-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 241001465754 Metazoa Species 0.000 description 1
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
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- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/08—Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F110/04—Monomers containing three or four carbon atoms
- C08F110/08—Butenes
- C08F110/10—Isobutene
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- C08F8/00—Chemical modification by after-treatment
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C09K23/16—Amines or polyamines
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- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
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- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
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Abstract
The invention relates to low-molecular and high-molecular diblock emulsifiers, particularly based on polyisobutylene, of general formulas (Ia) and (Ib), and to mixtures thereof, whereby: L<a> represents a polyisobutylene group having a numerical average molecular weight Mn ranging from 300 to 1000; L<b> represents a polyisobutylene group having a numerical average molecular weight Mn ranging from 2000 to 20000; -A- represents -O-, -N(H)- or N(R<1>)-; M<+> represents H<+>, an alkali metal ion, 0.5 alkaline-earth metal ions or NH4<+>, whereby in NH4<+>, one or more H's can be substituted by alkyl radicals; R represents a linear or branched saturated hydrocarbon radical, which supports at least one substituent selected from the group consisting of OH, NH2 or NH3<+> and optionally supports one or more C(O)H groups while optionally containing one or more non-adjacent -O- and/or secondary amines and/or tertiary amines and, in the NH2 or NH3<+> groups, one or more H's can be substituted by alkyl radicals, and; R<1> represents a linear or branched saturated hydrocarbon radical, which optionally supports one or more substituents selected from the group consisting of OH, NH2, NH3<+> or C(O)H while optionally containing one or more non-adjacent -O- and/or secondary amines and/or tertiary amines and, in the NH2 or NH3<+> groups, one or more H's can be substituted by alkyl radicals, and the proportion of A-R on the compound of general formula (Ib) equals at least 20 wt. %.
Description
The present invention relates to lower molecular weight and high-molecular weight compound, especially based on the compound of polyisobutene, and their mixture, they are suitable as the emulsifying agent of water-in-oil emulsion, relate to the preparation method and the emulsion itself of this compounds.
The invention still further relates to that this compounds acts as a fuel and lubricant additive and, and relate to fuel, lubricant, fuel additive concentrate and the slip additive enriched material and liquid, aqueous that contains this novel cpd as the purposes of corrosion inhibiting additive in liquid, aqueous.
Various types of compounds with emulsifying property are open in the prior art.Especially, the derivative of the succinyl oxide of polyisobutenyl replacement is used for various application.
For example, US-A 4,225, and 447 have described the water-in-oil type emulsion as lubricant, and it contains succinyl oxide (the number-average molecular weight M that preferably has 300-3000 gram/mole that thiazolinyl (for example polyisobutenyl) replaces
n), the succinic diamide of an alkali metal salt of the succsinic acid of alkenyl substituted or alkaline earth salt or alkenyl substituted is as emulsifying agent, when needed, be used in combination with the salt of resinous acid.
EP-A 0 156 572 has described the purposes that is used to prepare water-in-oil-type or emulsion oil-in-water based on the anionic surface active substances of the succinic acid derivative of polyisobutenyl replacement, and this material preferably has the number-average molecular weight M of 400-5000 gram/mole
nAnd has an anionic group.Suitable anionic group is phosphate radical, phosphonate radical, sulfate radical, sulfonate radical and carboxymethyl.
In the application number of on January 25th, 2000 application is that the applicant of 100 03 105.6 German patent application has been described the act as a fuel purposes of the emulsifying agent in the water-in type emulsion of alkoxylate polyisobutene.These alkoxylate polyisobutene can be by general formula R-(CH
2)
n-(O-A)
m-OH describes.Here, R is the polyisobutene with weight-average molecular weight of 300-2300, preferred 500-2000.A is the alkylidene group with 2-8 carbon atom.M is the number of 1-200, and it makes the alkoxylate polyisobutene contain 0.2-1.5 alkylene oxide unit through selecting, and preferred 0.5 alkylene oxide unit is with each C
4The unit meter; N is 0 and 1.
The application number of on July 28th, 2000 application is that the applicant of 100 36 956.1 German patent application has especially been described general formula R
1R
2NR
3Acid amides as the purposes of the emulsifying agent in the water-in-oil emulsion, wherein R
3Be monocarboxylic acid or polycarboxylic acyl group, R
1Especially derive autohemagglutination 1-butylene, poly-2-butylene or polyisobutene or their mixture, R
2Can be polyalkylenepolyamines or polyalkylene imine group.
WO 00/15740 has described the water-in-fuel emulsion, it contains two kinds of succinic acid derivatives as emulsifying agent, for example alkanolamine, polyamines or polyvalent alcohol connect these two kinds of derivatives via linking agent, and by for example polyisobutenyl replacement of alkyl, in one embodiment, a kind of succinic acid derivative contains the polyisobutenyl of 8-25 carbon atom, and another kind of succinic acid derivative contains the polyisobutenyl of 50-400 carbon atom.
GB-A 2,157, and 744 disclose drilling fluid, and it contains the grafting or the segmented copolymer of poly carboxylic acid and polyoxyethylene glycol simultaneously, and contain succinyl oxide (the number-average molecular weight M that preferably has 400-5000 that replaces from polyisobutenyl
n) and the compound that makes of polyvalent alcohol, preferred polyamines, hydroxycarboxylic acid or amino alcohol.
US4,708,753 have described the water-in-fuel emulsion, and it contains the amine salt of single salt of succsinic acid and amine or disalt or monomester succinate as emulsifying agent.These salt are by alkanolamine, polyamines, low polyalcohols or polyvalent alcohol and by C
20-C
500The succinyl oxide that alkyl (for example polyisobutenyl) replaces reacts and forms.In example, only described and had the succsinic acid of polyisobutenyl that number-average molecular weight is 950-1700 or those salt of its monoesters.The antifriction additive of fuel and lubricant and emulsifying agent is disclosed in the prior art.
Therefore, US5,858,029 have described antifriction liniment, the especially general formula R of fuel and lubricant
1(O (R
2)-)
aNH (CO)-R
3The compound of-OH, wherein R
1Be C
1-to C
60-alkyl, R
2Be C
1-to C
4-alkylidene group, a are the integers of 1-12, R
3Be C
1-to C
4The alkylidene group of-alkylidene group or replacement or cycloalkylidene, this compound is as the antifriction liniment.In addition, the succinimide that polyisobutenyl replaces can be used as dispersion agent and exists, and polyalkenes amine such as polyisobutene amine can be used as tensio-active agent and exist.
Disclosed in the prior art above-claimed cpd has the various shortcomings with regard to preparation and/or product performance.For some compounds, in synthetic, can generate the by product of different yields, unless they are removed otherwise the feasible constant viscosity that is difficult to obtain this emulsifying agent.Shortcoming also may reside in the preparation of emulsion: the stability of this emulsion is usually not enough, so be separated between the shelf lives.Therefore, in order to form stable emulsion, employed emulsifying agent must use with high density.
Therefore needing can be as emulsifying agent and the compound that does not have this type of shortcoming.Especially in the field of water-in-fuel emulsion, need such emulsifying agent, they can form more stable emulsion and allow fuel combustion as far as possible completely in addition and be substantially free of residue.
The purpose of this invention is to provide can be as other compound of the emulsifying agent in the water-in-oil emulsion.
We have found that this purpose can realize by general formula (Ia) and compound (Ib),
L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 300-1000,
L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-20000,
-A-is-O-,-N (H)-or-N (R
1)-,
M
+Be H
+, alkalimetal ion, 0.5 alkaline-earth metal ions or NH
4 +, NH wherein
4 +In one or more H can be replaced by alkyl,
R is the saturated hydrocarbyl of straight or branched, and it has at least one and is selected from OH, NH
2And NH
3 +Substituting group and contain one or more C (O) group when needed and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
R
1Be the saturated hydrocarbyl of straight or branched, when needed, it has one or more OH of being selected from, NH
2, NH
3 +And the substituting group of C (O) H and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
In general formula (Ia) or compound (Ib), the ratio of A-R is at least 20 weight %.
Wherein formula (Ia) compound of hydrophilic radical A-R ratio low (for example 5.2-15.2 weight %) is that itself is known, is described among GB-A 2157744 and the US4708753.But, wherein do not recognize the advantageous property that under the new compound situation of A-R ratio 〉=20 weight %, occurs as emulsifying agent.
Described novel cpd can use separately, also can be used as emulsifying agent in water-in-oil emulsion with the form of mixture.Can prepare emulsion more stable when using conventional emulsifier like this.Particularly, the compound of formula (Ib) can be used as two block emulsifying agents, connects via linking agent, wherein oleophylic block L
aOr L
bBe connected on the linking agent succsinic acid hydrophilic block R or R by the covalency C-C
1Be connected on the described linking agent by ester or amido linkage.
Preferred formula (Ia) compound is such, wherein:
-L
aBe that number-average molecular weight Mn is the polyisobutenyl of 350-950, particularly 350-650, and/or
-L
aBe polymolecularity≤3.0, be preferably the polyisobutenyl of 1.1-2.5, preferred especially 1.1-2.0, and/or
-in the compound of general formula (Ia), the ratio of A-R is at least 25 weight %, particularly 35-60 weight %, and/or
-R is by [CH
2-CH
2-X], [CH (CH
3)-CH
2-X] and/or [CH
2-CH (CH
3)-X] the unit composition, wherein X is O or NH.
Preferred formula (Ib) compound is such, wherein:
-L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-12000, particularly 2300-5000, and/or
-L
bBe polymolecularity≤3.0, be preferably the polyisobutenyl of 1.1-2.5, preferred especially 1.1-2.0, and/or
-in the compound of general formula (Ib), the ratio of A-R is at least 25 weight %, particularly 35-60 weight %, and/or
-R is by [CH
2-CH
2-X], [CH (CH
3)-CH
2-X] and/or [CH
2-CH (CH
3)-X] the unit composition, wherein X is O or NH.
Particularly preferred general formula (Ia) or (Ib) compound be such, wherein A is-O-, and R is the oligopolymer of oxyethane and/or propylene oxide or the monoradical of polymkeric substance, perhaps R is the monoradical of the segmented copolymer of oxyethane and propylene oxide.
Especially effectively emulsifying agent is such general formula (Ia) compound, wherein L
aBe that number-average molecular weight Mn is the polyisobutenyl of 350-950, particularly 350-650, this polyisobutenyl has when needed≤3.0, be preferably 1.1-2.5, preferred especially 1.1-2.0 polymolecularity.Have been found that if used emulsifying agent is the mixture that contains following component, then can reduce the total amount that is used to prepare the required emulsifying agent of stable emulsion,
(a) be no more than at least a formula (Ia) compound of 99 weight %, preferred 98-80 weight %, preferred especially 97-85 weight %,
(b) at least a formula (Ib) compound of at least 1 weight %, preferred 2-20 weight %, preferred especially 3-15 weight %,
L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 300-1000, L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-20000,
-A-is-O-,-N (H)-or-N (R
1)-,
M
+Be H
+, alkalimetal ion, 0.5 alkaline-earth metal ions or NH
4 +, NH wherein
4 +In one or more H can be replaced by alkyl,
R is the saturated hydrocarbyl of straight or branched, and it has at least one and is selected from OH, NH
2And NH
3 +Substituting group and contain one or more C (O) H group when needed and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
R
1Be the saturated hydrocarbyl of straight or branched, when needed, it has one or more OH of being selected from, NH
2, NH
3 +And the substituting group of C (O) H and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
In the compound of general formula (Ia), the ratio of A-R is at least 10 weight % and in general formula (Ib) compound, and the ratio of A-R is at least 20 weight %.
Effectively emulsifier mixture not only uses formula (Ia) compound with at least 20 weight % hydrophilic segments, and uses formula (Ia) compound with at least 10 weight % hydrophilic segments to obtain.
Preferred model mixture is such, and it also contains at least a formula (Ia) compound that is no more than 99 weight %, preferred 98-80 weight %, preferred especially 97-85 weight %, wherein L except containing at least a formula (Ib) compound
aBe that number-average molecular weight Mn is the polyisobutenyl of 350-950, particularly 350-650, and/or in general formula (Ia) compound, the ratio of A-R is at least 15 weight %, preferably at least 20 weight %, especially preferably at least 25 weight %, very particularly preferably 35-60 weight %.
Other preferred model mixture is such, and it also contains at least a formula (Ib) compound of at least 1 weight %, preferred 2-20 weight %, preferred especially 3-15 weight %, wherein L except containing at least a formula (Ia) compound
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-12000, particularly 2300-5000, and/or in general formula (Ib) compound, the ratio of A-R is at least 25 weight %, particularly 35-60 weight %.
The invention still further relates to a kind of preparation formula (Ia) or (Ib) method of compound.Wherein, polyisobutene and rich horse diacid chloride, fumaric acid, Malaysia diacid chloride, maleic anhydride or toxilic acid reaction, preferably with maleic anhydride or the reaction of Malaysia diacid chloride, preferred especially and maleic anhydride reaction, obtain formula (IIa), (IIb) or succinic acid derivative (IIc)
L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 300-1000, L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-20000.
This reaction is undertaken by well known to a person skilled in the art method, for example with DE-A 195 19042, DE-A 43 19 671 and DE-A 43 19 672 in polyisobutene and maleic anhydride response class seemingly.
The number-average molecular weight Mn of gained succinyl oxide derivative (being replaced by polyisobutenyl) can be characterized by saponification value [mg KOH/g material].
The succinic acid derivative of formula (IIa) and replacement (IIb) is then according to well known to a person skilled in the art method and polar reaction agent ROH or RR
1The NH reaction, wherein R is the straight or branched saturated hydrocarbyl, it has at least one and is selected from OH, NH
2And NH
3 +Substituting group and contain one or more C (O) H group when needed and contain when needed one or more non-conterminous-O-and/or secondary amine and/or tertiary amine, wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
R
1Be the saturated hydrocarbyl of straight or branched, when needed, it has one or more OH of being selected from, NH
2, NH
3 +And the substituting group of C (O) H and contain when needed one or more non-conterminous-O-and/or secondary amine and/or tertiary amine, wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl.
Replacing the alkyl of H atom can be C
1-C
4Alkyl.
Suitable polar reaction agent ROH and RR
1The example of NH is alkanolamine, polyamines, low polyalcohols, polyvalent alcohol, oligo alkylene glycols, polyalkylene glycol and carbohydrate and carbohydrate.Other polar reaction agent can be oxyethane and/or propylene oxide.It is preferred reacting with polyoxyethylene glycol, polypropylene glycol, its (block) multipolymer, oxyethane or propylene oxide.For preparation low-molecular-weight formula (Ia) compound, and the reaction between alkanolamine (for example two-or trolamine, three (methylol) aminomethane and salt thereof), low polyalcohols (for example sorbyl alcohol and tetramethylolmethane) or carbohydrate and the carbohydrate also is preferred.And the reaction between three (methylol) aminomethane, choline, carbohydrate and the polyoxyethylene glycol is to be particularly preferred for preparation formula (Ia) compound.
Select the amount of polar reaction agent, make that in general formula (Ia) or compound (Ib) ratio of hydrophilic radical A-R is at least 20 weight %, preferably at least 25 weight %, especially preferably 35-60 weight %.Wherein hydrophilic radical formula (Ia) compound that accounts for 10-20 weight % also can be by described method preparation.In reaction, the succinic acid derivative (IIa) that replaces, (IIb) or (IIc) with alkanolamine, polyamines, hang down the ratio normally 1 between polyalcohols, polyvalent alcohol, oligo alkylene glycols or the polyalkylene glycol: (0.75-2), preferred 1: (0.8-1.2), preferred especially 1: 1.In the reaction of oxyethane and/or propylene oxide, select the amount of oxyethane and/or propylene oxide according to the chain length of required hydrophilic radical A-R.
Wherein A be-O-and R be the monoradical of the oligopolymer of oxyethane and/or propylene oxide or polymkeric substance or ethylene oxide/propylene oxide segmented copolymer monoradical formula (Ia) or (Ib) succinic acid derivative (IIa) that compound can be by making polyoxyethylene glycol, polypropylene glycol or its (block) multipolymer and replacement, (IIb) or (IIc) reaction obtain and the succinic acid derivative (IIa) by making oxyethane and/or propylene oxide and replacement, (IIb) or (IIc) react and obtain.
Succinic acid derivative (IIa) by making replacement, (IIb) or (IIc) and described polar reaction agent reaction have obtained monomester succinate or mono succinate acid amides.When using alkanolamine, hydroxyl and/or amino react, thereby obtain the mixture of monomester succinate and mono succinate acid amides usually.If use Malaysia diacid chloride or rich horse diacid chloride as raw material, then C (O) the Cl group that still exists after described reaction is hydrolyzed into CO
2The H group.The free CO that in monomester succinate and mono succinate acid amides, exists
2The H group then with NH
3, amine or an alkali metal salt or alkaline-earth metal reactant salt, obtain corresponding amine, an alkali metal salt or alkaline earth salt.These salt are formula (Ia) or compound (Ib), wherein M
+Be H
+, alkalimetal ion, 0.5 alkaline-earth metal ions or NH
4 +, NH wherein
4 +In one or more H can be replaced by alkyl.Be applicable to that salifiable amine is to have straight chain C
1-C
4Alkyl or side chain C
3-C
6The primary amine of alkyl, secondary amine and tertiary amine.These alkyl also can be replaced by one or more hydroxyls.Suitable alkylamine is for example diethylamide, diisopropylamine, Trimethylamine, single-, two-and three-thanomin and three (methylol) aminomethane.
In general, number-average molecular weight Mn is 300-1000, preferred 350-950, especially preferably the polyisobutene of 350-650 is used for the compound of preparation formula (Ia).
In general, number-average molecular weight Mn is 2000-20000, preferred 2000-12000, especially preferably the polyisobutene of 2300-5000 is used for the compound of preparation formula (Ib).
In the polyisobutene in number-average molecular weight Mn is in described scope, those with high vinylidene content are preferred uses.In the context of the present invention, this is understood that to refer to 〉=70 moles of %, preferred 〉=80 moles %, the vinylidene of preferred 〉=85 moles of % especially.
Having number-average molecular weight Mn in above-mentioned scope, high vinylidene content and those polyisobutene of homogeneous polymer skeleton structure is preferred especially uses.In this article, they are interpreted as referring to those polyisobutene of being made up of at least 80 weight %, preferred at least 90 weight %, preferred especially at least 95 weight % iso-butylene unit.
Have number-average molecular weight Mn in this scope, high vinylidene content and uniformly the polyisobutene of skeleton structure and polymolecularity≤3.0, preferred 1.1-2.5, preferred especially 1.1-2.0 be particularly preferred.Polymolecularity is understood that to refer to the ratio Mw/Mn of weight-average molecular weight Mw and number-average molecular weight Mn.
Have the number-average molecular weight Mn in this scope and form by the iso-butylene unit basically and polyisobutene with high vinylidene content for example can obtain from BASF AG with trade(brand)name Glissopal , as Mn is 1000 Glissopal 1000, and Mn is that 550 Glissopal V33 and Mn are 2300 Glissopal 2300.
Be applicable to that alkanolamine, the polyamines for preparing novel cpd, the example that hangs down polyalcohols, polyvalent alcohol and polyalkylene glycol are described among the WO 00/15740.
The example of alkanolamine is a monoethanolamine, diethanolamine, 2-amino-1-butanols, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1, ammediol, 2-amino-2-ethyl-1, ammediol, N-(2-hydroxypropyl)-N '-(2-aminoethyl) piperazine, three (methylol) aminomethane, 2-amino-1-butanols, β-(2-hydroxyl-oxethyl) ethylamine, glycosamine, glucosamine, 4-amino-3-hydroxy-3-methyl-1-butylene, N-(3-aminopropyl)-4-(2-hydroxyethyl) piperidines, 2-amino-6-methyl-6 enanthol, 5-amino-1-amylalcohol, N-(2-hydroxyethyl)-1, the 3-diaminopropanes, 1,3-diamino-2-hydroxy propane, N-(2-hydroxyethyl)-quadrol, N, N-two (2-hydroxyethyl) quadrol, N-(2-hydroxyethoxy ethyl) quadrol, 1-(2-hydroxyethyl) piperazine, the diethylenetriamine that single hydroxypropyl replaces, the tetren that dihydroxypropyl replaces, and N-(3-hydroxyl butyl)-four ethylene diamines.
Also can use the salt of described alkanolamine.In these salt, one or more H atoms that are connected with the N atom can be by straight chain C
1-C
6Alkyl or side chain C
3-C
6Alkyl replaces.As an example, can mention choline.
Suitable polyamines is a polyalkylenepolyamines for example, for example multi-methylene polyamine, polyethylene polyamine, many propylidene polyamines, many butylidenes polyamines and many pentylidene polyamines, referring to Ethylene Amines inKirk Othmer ' s Encyclopedia of Chemical Technology, the 2nd edition, the 7th volume, the 22-37 page or leaf, Interscience Publishers, New York 1965.
Suitable oligomeric pure and mild polyvalent alcohol is for example 1,2-butyleneglycol, 2,3-dimethyl-2,3-butyleneglycol, 2,3-hexylene glycol, 1,2-cyclohexanediol, (single-, two-) tetramethylolmethane, 1,7-and 2,4-heptanediol, 1,2,3-, 1,2,4-, 1,2,5-and 2,3,4-hexanetriol, 1,2,3-and 1,2, the 4-trihydroxybutane, 2,2,6,6-four (methylol) hexalin, decamethylene-glycol, 2-methylol-2-methyl isophthalic acid, ammediol, 2-methylol-2-ethyl-1, ammediol, sorbyl alcohol, mannitol and inositol.In addition, C
5-and C
6-sugared for example glucose and fructose also are suitable for.
(oligomeric) aklylene glycol be for example (three-, four-, five-and six-) ethylene glycol, (three-, four-, five-and six) propylene glycol and (three-, four-, five-and six-) butyleneglycol.
Polyalkylene glycol is for example polytetrahydrofuran, polyoxyethylene glycol and polypropylene glycol.Preferred polyalkylene glycol is polyoxyethylene glycol and polypropylene glycol.Number-average molecular weight Mn is that the polyoxyethylene glycol of 300-5000, preferred 300-2000, preferred especially 500-1500 and polypropylene glycol and segmented copolymer thereof are preferred especially the uses.
These polyoxyethylene glycol for example obtain from BASF AG with trade(brand)name Pluriol E, for example number-average molecular weight Mn is 300 Pluriol E 300, number-average molecular weight Mn is 600 Piuriol E 600, number-average molecular weight Mn is 4000 Pluriol E 4000, and number-average molecular weight Mn is 5000 Pluriol E 5000.The polyethylene/polypropylene glycol segmented copolymer for example obtains from BASF AG with trade(brand)name Pluronic PE, for example number-average molecular weight Mn be 1900 and ethylene oxide content be the Pluronic PE 3500 of 50 weight %.
If in emulsion oil-in-water, use novel cpd and/or model mixture, then can obtain stable micella.This can for example realize by action of ultrasonic waves.In addition, novel cpd and/or model mixture can use in every way, for example act as a fuel and lubricant in additive, as the corrosion inhibiting additive in liquid, aqueous, and as the inorganic and dispersion agent organic solid dispersion.In addition, novel cpd and/or model mixture can be as the tensio-active agents of washing and cleaning prescription.Contain polyoxyethylene glycol unit price group and be particularly suitable for stable inorganic and organic solid dispersion as formula (Ib) high-molecular weight compounds of hydrophilic block.
Novel cpd and/or model mixture also are suitable as the emulsifying agent of water-in-oil emulsion, wherein by plant, animal or synthetic oil or lipogenesis oil phase.These emulsion applications are at makeup or pharmaceutical field.These oil or fatty example are the Witepsol W-S 55 and the diol ester of lauric acid, tetradecanoic acid, stearic acid, palmitinic acid, oleic acid, linoleic acid plus linolenic acid.
Novel cpd and/or model mixture particularly advantageously are made of in the water-in-oil emulsion of oil phase fuel or lightweight or heavy fuel oil (HFO) therein and are used as emulsifying agent.All conventional fuel can use, for example diesel-fuel, Fuel Petroleum and kerosene.Diesel-fuel is preferred the use.
In general, the purification of novel cpd and intermediate thereof is dispensable; Only in application-specific, for example when these compounds were used as emulsifying agent in the water-in-oil emulsion of makeup or pharmaceutical field, purification can be necessary.
The present invention relates to novel cpd and/or model mixture purposes in preparation water-in-oil emulsion process, and relate to water-in-oil emulsion itself as emulsifying agent.Novel water-in-oil emulsion generally contains the oil of 95-60 weight %, the water of 3-35 weight % and at least a novel cpd and/or at least a model mixture of 0.2-10 weight %.
New-type fuel water-in type emulsion also can contain one or more C
1-C
4-alcohol and/or monoethylene glycol, especially monoethylene glycol.Employed C
1-C
4The amount of-alcohol and/or monoethylene glycol is 5-50 weight %, based on the amount meter of water.For example, by adding one or more C
1-C
4-alcohol and/or monoethylene glycol keep the temperature range of emulsion-stabilizing to broaden.
This New-type fuel water-in type emulsion has high stability and good efficiency in combustion processes.Can also obtain good waste gas value, the emission of cigarette ash and NOx significantly reduces, especially in diesel motor.Can realize substantially completely the burning with no residue, and in the part of combustion unit deposition not on injection nozzle, piston, ring groove, valve and the cylinder head for example.
Except mentioned component, water-in-fuel emulsion according to the present invention can have additional component.These are for example additional emulsifying agents, and as sodium lauryl sulphate, quaternary ammonium salt is ammonium nitrate for example, alkyl glycoside, Yelkin TTS, polyglycol ether and ester, single oleic acid sorbitan esters, stearate and ricinoleate, C
13-oxo process alcohol ethoxylate and alkylphenol ethoxylate, and the segmented copolymer of oxyethane and propylene oxide are as the Pluronic rank that obtains from BASF AG.Single oleic acid sorbitan esters, C
13-oxo process alcohol ethoxylate and alkylphenol ethoxylate, for example octyl group-and nonyl phenol ethoxylate is preferably used as additional emulsifying agent.
One or more above-mentioned additional emulsifiers are preferred for this novel water-in-fuel emulsion with the binding substances of novel cpd and/or its mixture.
If use these additional emulsifiers, then they are to use based on the 0.5-5 weight % of total composition, the amount of preferred 1-2.5 weight %.Select the amount of additional emulsifiers, make the total amount of emulsifying agent can not surpass amount for the 0.2-10 weight % of novel cpd and/or the independent indication of its mixture.
For the preparation of novel water-in-oil emulsion, selected novel cpd and/or model mixture mix with oil, water and additional, optional available component, and emulsification in a manner known way.For example, this emulsification can be in the rotor mixing tank, utilizes mixing nozzle or carries out by means of ultrasonic probe.When the mixing nozzle of disclosed that type in the BASF AG German patent application that uses at the application number 198 56 604 on December 8th, 1998, obtain good especially result.The water-in-oil emulsion of cosmetic field can be according to preparing with the same mode of water-in-fuel emulsion.
Except surfactivity, interfacial activity and emulsifying property, this novel cpd and/or model mixture also have the oilness of improvement and suppress the corrosive effect.And they improve the wear resisting property of liquid.Therefore this novel cpd and/or model mixture are used as lubricant, fuel and liquid, aqueous additive, as radiator liquid or drilling fluid and cutting fluid.This application has constituted theme of the present invention equally.
This novel cpd and/or model mixture can directly be added in the fuel and lubricant with other component.Perhaps, this novel cpd and/or model mixture can at first mix to obtain fuel or lubricant additive concentrates with other component.These New-type fuels or lubricant additive concentrates can be added in fuel or the lubricant with undiluted form or after with one or more solvents or carrier oil dilution.The interpolation of dilute form is preferred.
Contain fuel, lubricant, fuel additive concentrate and lubricant additive concentrates and the liquid, aqueous same formation theme of the present invention and the explanation in more detail below of novel cpd and/or model mixture.
Except common component, this New-type fuel generally also contains at least a novel cpd and/or model mixture, and its content is based on the 10-5000ppm of total amount meter, preferred 20-2000ppm.
Novel lubricant contains liquid state, semi-solid state or the solid lubricant of 90-99.9 weight %, preferred 95-99.5 weight % and at least a novel cpd and/or the model mixture of 0.1-10 weight %, preferred 0.5-5 weight % usually, based on total amount.
Except common component, New-type fuel multifunctional additive for lubricating oils and lubricant additive concentrates also contain at least a novel cpd and/or model mixture, its content is 0.1-80 weight %, 0.5-60 weight % especially, based on the enriched material gross weight.
The common ingredients that is used for fuel or fuel additive concentrate is the additive that for example has detergent action, as in the applicant's of the application number 100 36 956.1 on July 28th, 2000 German patent application (14 pages are risen), in the applicant's of the application number 100 03 105.6 on January 25th, 2000 German patent application and described in the applicant's of application number PCT/EP/01/00496 the PCT patent application.Wherein said additive and the additional fuel additive of wherein describing with polar group have constituted the application's a part equally, therefore introduce for reference here.
This New-type fuel and fuel additive concentrate also can contain fuel dope, as at for example European patent application EP-A 0 277 345,0 356 725,0 476 485,0 484 736,0 539 821,0 543225,0 548 617,0 561 214,0 567 810 and 0 568 873, German patent application DE-A 3,942 860, and 43 09 074,43 09 271,43 13 088,44 12 489,44 25 834,195 25 938,196 06 845,196 06 846,196 15 404,196 06 844,196 16 569,196 18 270,196 14 349 and WO-A 96/03479 described in.
Additional common ingredients is for example additional corrosion inhibitor, antioxidant, and stablizer, static inhibitor, organometallic compound, anti-wear agent, marker and cetane number improver, FLOW IMPROVERS, biocides is as glutaraldehyde or oxalic dialdehyde.The consumption of this biocides is normally in the 0.01-3 weight % based on the enriched material gross weight.
The example of additional corrosion inhibitor is that this salt tends to form film based on those of the ammonium salt of organic carboxyl acid class, or those of the heterocyclic aromatic hydrocarbon of using based on the corrosion protection of non-ferrous metal.
The example of stablizer is based on amine, as Ursol D, dicyclohexylamine or their derivative, or based on phenols, as 2,4-DI-tert-butylphenol compounds or 3, those of 5-di-t-butyl-4-hydroxyphenylpropionic acid.
The example of organometallic compound is ferrocene or methyl cyclopentadienyl-manganese three carboxides.
The example of cetane number improver is an organic C
2-C
10-nitric ether is as nitric acid 2-(ethyl hexyl) ester be used for the inorganic cetane number improver of water, as ammonium nitrate.Nitric acid 2-(ethyl hexyl) ester and ammonium nitrate are preferred the uses.The consumption of this cetane number improver is normally based on the 0.05-5 weight % of enriched material gross weight meter.
The suitable solvent that is used for New-type fuel and lubricant additive concentrates is aliphatic series and aromatic hydrocarbon, as solvent naphtha, Permethyl 99A., Mihagol (a kind of C
10-C
12The cuts of alkane), fuel and lubricant itself and carrier oil.
The carrier oil that is used to dilute fuel additive concentrate and lubricant additive concentrates equally is a mineral carrier oil (base oil) for example, especially those of viscosity grade Solvent Neutral (SN) 100-500, with based on the synthetic vectors oil of polyolefine, (gathering) ester, (alkylphenol-initiation) polyethers or (aliphatic series) (alkylphenol-initiation) polyetheramine with based on the carrier oil of alkoxylate long-chain alcohol or phenols.The example of specially suitable synthetic vectors oil is based on those of polyolefine, preferably based on polyisobutene with based on those of poly-alpha olefins, has the number-average molecular weight Mn of 400-1800.Polyoxyethylene, polyoxytrimethylene, polyoxybutylene and their mixture also are suitable carriers oil.Other suitable carriers oil and carrier oil mixture for example are described among DE-A 38 38 918, DE-A 38 26608, DE-A 41 42 241, DE-A 43 09 074, US 4,877,416 and the EP-A 0 452 328.
New aqueous liquid contains this novel cpd and/or model mixture, combines with additional general corrosion inhibitor when needed, normally based on about 1-10 weight % of total amount meter.
The following examples are used to illustrate the present invention.
Embodiment
Embodiment 1: general formula (Ia) and (Ib) preparation of compound
The composition of prepared compound is shown in Table 1.
Employed polyisobutene is the Glissopal that obtains from BASF AG, and its number-average molecular weight Mn is 380-8400, and vinylidene endgroup content＞70 mole %, polymolecularity Mw/Mn are 1.15-1.8, and the polymer backbone structure contains 85% iso-butylene unit.This polyisobutene is as the raw material that synthesizes the succinyl oxide (PIBSA=polyisobutylene succinic anhydride) that is replaced by polyisobutenyl.
Used polyoxyethylene glycol is the Pluriol E that obtains from BASF AG, and its number-average molecular weight Mn is 3000-5000.Used polyethylene/polypropylene glycol multipolymer is the Pluronic PE 3500 that obtains from BASF AG, and its number-average molecular weight Mn is 1900, and ethylene oxide content is 50 weight %.
Used solvent is heptane, Mihagol (a kind of C
10-C
12The cuts of alkane is from Wintershall) and Solvesso 150 (a kind of aromatic hydrocarbons mixture is from ExxonMobilChemical).
Used ion-exchanger is the ion-exchanger that obtains with trade(brand)name Ambossol from Clariant.
Polyisobutene is carried out the operation that maleinization obtains corresponding succinyl oxide carry out, for example be described among DE-A 195 19 042, DE-A 43 19 671 and the DE-A 43 19 672 according to the known method method.
The compound of gained is by acid number, hydroxyl value, viscosity and/or IR spectral characterization.Hydroxyl value is used high boiling solvent and is proofreaied and correct this solvent and measure, that is, the hydroxyl value of detection compound in each solvent is extrapolated to pure substance then.At low boiling point solvent for example under the situation of heptane, remove by distillation and to desolvate, and measure the hydroxyl value of pure substance.
Viscosity is measured according to DIN 51562.
Table 1: the formula (Ia) or (Ib) composition of compound
| Compound | ???Glissopal ?Mn??????Mw/Mn | The hydrolysis value of PIBSA | The polar reaction agent |
| A | ?550?????1.23 | ???148 | ?(HO-CH 2-CH 2-) 2NH |
| B | ?550?????1.23 | ???148 | ?(HO-CH 2) 3-CNH 2 |
| C | ?750?????1.31 | ???120 | The D-sorbyl alcohol |
| D | ?380?????1.15 | ???210 | ?PluriolE300 |
| E | ?550?????1.23 | ???147 | Pluriol E300 and (HO-CH 2-CH 2-) 2NH |
| F | ?1000????1.31 | ???95 | ?PluriolE600 |
| G | ?2300????1.52 | ???40 | ?PluriolE1500 |
| H | ?5200????1.38 | ???18.3 | ?PluriolE4000 |
| I | ?8400????1.45 | ???12.0 | ?PluriolE5000 |
| J | ?1000????1.31 | ???95 | ?(HO-CH 2-CH 2-) 2NH |
| K | ?1000????1.31 | ???95 | ?PluronicE3500 |
| L | ?550?????1.31 | ???148 | Choline |
| M | ?1000????1.31 ?2300????1.52 | ???95 ???40 | Monoethylene glycol |
The preparation of compd A:
In the 1L four neck flasks of being furnished with agitator, dropping funnel and thermopair, add the PIBSA550 of 250g, be heated to 90 ℃.In 5 minutes, be metered into the 67g diethanolamine via dropping funnel.This mixture is heated to 130 ℃ or 170 ℃ gradually.After 2 hours, filter brown reaction product 170 ℃ of maintenances in 100 ℃.
The preparation of compd B:
The Solvesso 150 of PIBSA550, the 650g of adding 525g and the Tutofusin tris (TRIS) of 175g in the 2L four neck flasks of being furnished with agitator, distillation bridge and thermopair.This mixture is heated to 130 ℃ or 170 ℃ gradually.The water that discharges is removed by nitrogen gas stream; Reaction times is 3 hours.Proofread and correct this solvent, recording hydroxyl value is 250.
The preparation of Compound C:
In the 1L four neck flasks of being furnished with agitator, distillation bridge and thermopair, add the PIBSA750 of 310g and the D-sorbyl alcohol of 60g.This mixture is heated to 160 ℃ or 220 ℃ gradually.The water that discharges is removed by nitrogen gas stream; 220 ℃ keep 3 hours after, dilute filtered while hot with the Mihagol of 200g.Obtain xanchromatic sticky product solution (65%).
The preparation of Compound D:
The Pluriol E300 that adds 350g in the 2L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 380 in the 350g heptane of 650g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.Decompression (350 millibars) distills out heptane in this process.After 3 hours, obtain yellow product 140 ℃ of maintenances, viscosity is 105mm
2/ s (100 ℃); Hydroxyl value is 70; Acid number is 73; IR: at 1735cm
-1Strong bands of a spectrum (ester) are arranged.
The preparation of compd E:
The Pluriol E300 that adds 300g in the 2L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 550 in the 450g heptane of 750g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.Decompression (350 millibars) distills out heptane in this process.After 3 hours, be added dropwise to the 105g diethanolamine 140 ℃ of maintenances in 95 ℃.95 ℃ keep 20 minutes again after, filtered while hot yellowish brown product.Hydroxyl value is 55; IR: at 1736cm
-1Strong bands of a spectrum (ester) are arranged.
The preparation of compound F 17-hydroxy-corticosterone:
The Pluriol E600 that adds 400g in the 2L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 1000 in the 450g heptane of 790g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.Decompression (350 millibars) distills out heptane in this process.After 3 hours, obtaining viscosity is 1650mm 140 ℃ of maintenances
2The yellow product of/s (100 ℃).Hydroxyl value is 43; Acid number is 40; IR: at 1734cm
-1Strong bands of a spectrum (ester) are arranged.
The preparation of compound G:
The Plurioi E1500 that adds 150g in the 1L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 2300 in 300gMihagol of 280g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.After 3 hours, obtain the highly viscous solution of xanchromatic 140 ℃ of maintenances.Its viscosity is 1750mm
2/ s, 100 ℃; Hydroxyl value is 9; Acid number is 8.1; IR: at 1736cm
-1Bands of a spectrum are arranged.
The preparation of compound H:
The Pluriol E4000 that adds 150g in the 1L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 5200 in 300gMihagol of 250g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.After 3 hours, obtain cream-coloured wax 140 ℃ of maintenances.Its hydroxyl value is 4.3; Acid number is 3.5; IR: at 1736cm
-1Bands of a spectrum (ester) are arranged.
The preparation of Compound I:
According to the similar mode of compound H, (basic: reactive PIB 8400 from PIBSA; Mw/Mn=1.45) and Pluriol E5000 synthesize.Separating the product that obtains is milky wax (60% concentration in Mihagol); IR: at 1737cm
-1
The preparation of comparative example 1 compound J
According to the similar mode of compd A, (basic: reactive PIB 1000 from PIBSA 1000; Mw/Mn=1.31) and diethanolamine synthesize (also referring to US4708753).Separating the product that obtains is brown highly viscous liquid, and its wetting ability A-R content is lower than compd A.
The preparation of compound K:
According to the similar mode of compound F 17-hydroxy-corticosterone, (basic: reactive PIB 1000 from PIBSA 1000; Mw/Mn=1.31) and Pluriol PE3500 synthesize.Separating the product that obtains is tenne highly viscous liquid.Its viscosity is 2100mm
2/ s; 100 ℃.
The preparation of compound L:
The choline methanol solution (from Fluka) of 45% concentration of adding 75g and the Mihagol of 150g in the 1L four neck flasks of being furnished with agitator, dropping funnel and thermopair.Remove methyl alcohol in 50 ℃ of decompressions (50 millibars) (45 minutes) then.The PIBSA 550 of 200g is metered in this suspension, and in 15 minutes with this mixture heating up to 90 ℃.After 60 minutes, temperature is elevated to 170 ℃, restir 2 hours.Filter brown reaction product in 100 ℃.
Be used for the preparation of comparative example 2 compound M:
The PIBSA 1000 of PIBSA2300, the 200g of adding 300g and the Mihagol of 200g are heated to 95 ℃ in the 1L four neck flasks of being furnished with agitator, dropping funnel and thermopair.Be metered into 17.2g ethylene glycol in 95 ℃.With this mixture heating up to 130 ℃, and under this temperature restir 3 hours.Filter brown reaction product in 100 ℃.
According to the 34th page Embodiment C-1 preparation comparative example's 2 emulsifying agent among the WO00/15740.
Be used for the preparation of comparative example 3 compound N:
(according to carrying out with the similar mode of compound F 17-hydroxy-corticosterone.But the A-R content of compound F 17-hydroxy-corticosterone is 35.3%, and the content of the hydrophilic segment A-R in the compound N is 15.4%)
The Pluriol E200 that adds 100g in the 2L four neck flasks of being furnished with agitator, dropping funnel and thermopair is in 30 minutes, under reduced pressure in 90 ℃ of degassings.In 5 minutes, the solution of PIBSA 1000 in the 450g heptane of 590g is metered in 80 ℃ via dropping funnel.This mixture is heated to 110 ℃ or 140 ℃ gradually.Decompression (350 millibars) distills out heptane in this process.After 3 hours, obtaining viscosity is 1450mm 140 ℃ of maintenances
2The amber product of/s (100 ℃).
Embodiment 2: the preparation of water-in-fuel emulsion
The preparation or the composition of fuel mixture are listed in the table 2.
Wetting ability or water soluble ingredient are dissolved in aqueous phase in advance, and lipophilic ingredients is dissolved in the diesel oil.In 15 minutes, use Ultra-Turrax (Jahnke and Kunkel laboratory equipment T25) with the speed of 2400rpm with this mixture of 500g and 100ml water homogenizing.The described similar mode of DE-A198 56 604 (on December 8th, 1998 submitted) according to the applicant is carried out the industrial-scale production and the engine test of emulsion, uses mixing nozzle here.Pressure in mixing equipment is 50-200 crust, preferred 120 crust (before orifice plate), and total conversion rate is 12kg/h.
Table 2: the composition of emulsion
*Used microbicide is or oxalic dialdehyde or glutaraldehyde.
In embodiment 1,2,6 and 7, use the compound of novel low molecular weight amount, in embodiment 3,4 and 5, use the model mixture of lower molecular weight and high-molecular weight compounds.
| Embodiment compound (weight %) | ????1 | ????2 | ????3 | ????4 | ????5 | ????6 | ????7 | Comparative Examples 1 | Comparative Examples 2 | Comparative Examples 3 |
| ??A | ????1.4 | ????- | ????- | ????- | ????1.5 | ????- | ????- | ????- | ????- | ????- |
| ??B | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- |
| ??C 13The oxo process alcohol ethoxylate has 5 [CH 2-CH 2-O-] unit | ????0.2 | ????0.2 | ????- | ????- | ????- | ????0.2 | ????0.3 | ????0.3 | ????0.3 | ????0.3 |
| Alkylphenol ethoxylate | ????0.2 | ????- | ????0.2 | ????0.3 | ????0.3 | ????- | ????- | ????- | ????- | ????- |
| ??C | ????- | ????- | ????- | ????1.3 | ????- | ????- | ????- | ????- | ????- | ????- |
| ??D | ????- | ????- | ????1.5 | ????- | ????- | ????- | ????0.5 | ????- | ????- | ????- |
| ??E | ????- | ????- | ????- | ????- | ????- | ????1.8 | ????- | ????- | ????- | ????- |
| ??F | ????- | ????0.3 | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- |
| ??G | ????- | ????- | ????0.2 | ????- | ????0.3 | ????- | ????- | ????- | ????- | ????- |
| ??H | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- |
| ??I | ????- | ????- | ????- | ????0.4 | ????- | ????- | ????- | ????- | ????- | ????- |
| ??J | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????1.8 | ????- | ????- |
| ??K | ????- | ????- | ????- | ????- | ????- | ????- | ????1.0 | ????- | ????- | ????- |
| ??L | ????- | ????1.6 | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- |
| ??M | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????1.7 | ????- |
| ??N | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????- | ????1.7 |
| Diesel oil (EN 590) | ????76.3 | ????76.0 | ????76.1 | ????76.2 | ????76.0 | ????76.5 | ????76.2 | ????76.0 | ????76.1 | ????76.1 |
| Water | ????20 | ????20 | ????20 | ????15 | ????20 | ????15 | ????20 | ????15 | ????15 | ????15 |
| Methyl alcohol | ????- | ????- | ????- | ????2 | ????- | ????3 | ????- | ????- | ????- | ????- |
| Ethylene glycol | ????- | ????- | ????- | ????3 | ????- | ????2 | ????- | ????5 | ????5 | ????5 |
| Microbicide * | ????0.4 | ????0.4 | ????0.5 | ????0.3 | ????0.4 | ????- | ????0.5 | ????0.4 | ????0.4 | ????0.4 |
| ??NH 4NO 3 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 | ????1.5 |
Embodiment 3: the stability of research water-in-fuel emulsion
The size of water droplet detects with physics mode by laser diffraction (X3,2 values) with Malvern Mastersizer 2000 (from Malvern InstrumentsGmbH.).For example at Terence Allen, Particle Size Measurement, the 1st volume has been described detection method in the 5th edition (Kluwer Academic Publishers, Dordrecht, Netherlands, 1999).According in esse size-grade distribution, except laser diffractometry, other method for example dynamic light scattering, single-particle counting and ultrasonic-attenuation method also is suitable.
The size of water droplet is measuring of quality of the emulsion.Water droplet size is more little, and emulsion is just good more or stable more.The analog value of water droplet size (X3,2 values) is listed in the table 3.Table 3 has shown that a part of emulsion has comparison than the remarkable littler drop size of emulsion when using novel cpd and model mixture.From the stability data that stores measuring as seen, drop size is a kind of means of weighing the room temperature stability of emulsion really.Emulsion with big drop size also has the relatively poor shelf lives.
Table 3: the drop size of water-in-fuel emulsion and stability
| Embodiment | ??1 | ??2 | ??3 | ??4 | ??5 | ??6 | ??7 | Comparative Examples 1 | Comparative Examples 2 | Comparative Examples 3 |
| Drop size (X3,2 values) [μ m] | ??2.9 | ??2.2 | ??1.0 | ??3.1 | ??2.5 | ??3.2 | ??2.7 | ????5.4 | ??6.2 | ??6.8 |
| Store experiment (room temperature) *[% emulsion] | ??86 | ??＞95 | ??＞95 | ??91 | ??89 | ??79 | ??77 | ????61 | ??58 | ??49 |
| Store experiment (70 ℃) **[% emulsion] | ??91 | ??100 | ??100 | ??89 | ??93 | ??80 | ??82 | ????73 | ??75 | ??69 |
| Store experiment (20 ℃) **[% emulsion] | ??- | ??65 | ??- | ??91 | ??95 | ??89 | ??- | ????62 | ??64 | ??63 |
* 12 weeks;
*1 week
In 20 ℃ (12 weeks) with in addition in the stability that in static state storage experiment, detects emulsion under the situation of change temperature (20 ℃ and 70 ℃, each 1 week).For this reason, adding this emulsion in 100 milliliters of graduated cylinders step by step, its quality is visual assessment under the described conditions.
Compare with the emulsifying agent (comparative example) that uses prior art, it is significant observing the improvement of shelf lives in some cases under the situation of using New-type emulsifier and its mixture.Carry out-20 ℃ storage experimental evaluation then in room temperature.Emulsion according to embodiment 2 is more even after heating, also is like this during even without adding frostproofer (for example monoethylene glycol).Otherwise, after heating or even i.e. breakdown of emulsion during heating occurs being separated.
New Emulsion with according to WO00/15740 (Embodiment C-1,34 pages, Comparative Examples 2) emulsion is compared, and proves that the combination of lower-molecular-weight component and high molecular weight component obtains corresponding bridge joint compound, and this causes than the remarkable worse emulsifying agent of the model mixture of isolated compound.
Embodiment 4: new (I) compound is as antirust and purposes anti-wear additive
The iron plate of 20 * 40mm in the emulsion that immersion (similar to ASTM D-665) prepares, stores 24 hours in 40 ± 1 ℃ then with 40 μ m granulated glass sphere sandblasts in embodiment 2.After 24 hours, observe the situation that iron plate gets rusty.Here:
++ expression is not got rusty;
+ 0 expression has rusty stain slightly;
-0 expression is got rusty above 25% of test piece area;
--expression is got rusty above 50% of test piece area;
As shown in table 4, in some cases, when using novel cpd, rusty stain is only arranged slightly as corrosion inhibiting additive.By contrast, when using C
13During the oxo process alcohol ethoxylate, occurring getting rusty above on 50% the test piece area.
Embodiment 5: purposes and the wear resisting property thereof of new (I) compound in fuel
In each case, the compound dissolution shown in the table in diesel oil, do not add additive (Miro, Karlsruhe).The concentration of additive in diesel oil is 75ppm.Wear resisting property is measured by HFRR experiment (experiment of high-frequency roller bar), carries out according to ISO 12156-1.Detect the length of gained groove, be used to weigh abrasive conditions.Groove is short more, and the wear protection performance of the additive that is added is good more.The diesel oil that does not contain additive is used for comparison.As shown in table 4, novel cpd has anti-wear effect.
Table 4:
| Additive | Trench length [μ m] | Corrosion |
| Compd B | ????380 | ????+0 |
| Compound C | ????490 | ????-0 |
| Compound D | ????315 | ????+0 |
| Compd E | ????295 | ????++ |
| Compound F 17-hydroxy-corticosterone | ????320 | ????++ |
| Compound G | ????420 | ????+0 |
| Compound J | ????495 | ????-0 |
| Additive-free | ????605 | ????-- |
Claims (16)
1. general formula (Ia) or compound (Ib),
L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 300-1000,
L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-20000,
-A-is-O-,-N (H)-or-N (R
1)-,
M
+Be H
+, alkalimetal ion, 0.5 alkaline-earth metal ions or NH
4 +, NH wherein
4 +In one or more H can be replaced by alkyl,
R is the saturated hydrocarbyl of straight or branched, and it has at least one and is selected from OH, NH
2And NH
3 +Substituting group and contain one or more C (O) group when needed and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
R
1Be the saturated hydrocarbyl of straight or branched, when needed, it has one or more OH of being selected from, NH
2, NH
3 +And the substituting group of C (O) H and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
In general formula (Ia) or compound (Ib), the ratio of A-R is at least 20 weight %.
2. according to the compound of claim 1, L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 350-950, particularly 350-650, and L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-12000, particularly 2300-5000.
3. according to the compound of claim 1 or 2, L wherein
aAnd L
bEach naturally polymolecularity≤3.0, be preferably the polyisobutenyl of 1.1-2.5, preferred especially 1.1-2.0.
4. according to each compound among the claim 1-3, wherein L
aAnd L
bThe polyisobutenyl that each is made up of at least 80 weight % isobutenyl unit naturally.
5. according to each compound among the claim 1-4, wherein in general formula (Ia) or compound (Ib), the ratio of A-R is at least 25 weight %, particularly 35-60 weight %.
6. according to each compound among the claim 1-5, wherein A is-O-, and R is the oligopolymer of oxyethane and/or propylene oxide or the monoradical of polymkeric substance, and perhaps R is the monoradical of the segmented copolymer of oxyethane and propylene oxide.
7. mixture that contains following component:
(a) be no more than at least a formula (Ia) compound of 99 weight %, preferred 98-80 weight %, preferred especially 97-85 weight %,
(b) at least a formula (Ib) compound of at least 1 weight %, preferred 2-20 weight %, preferred especially 3-15 weight %,
L wherein
aBe that number-average molecular weight Mn is the polyisobutenyl of 300-1000, L
bBe that number-average molecular weight Mn is the polyisobutenyl of 2000-20000,
-A-is-O-,-N (H)-or-N (R
1)-,
M
+Be H
+, alkalimetal ion, 0.5 alkaline-earth metal ions or NH
4 +, NH wherein
4 +In one or more H can be replaced by alkyl,
R is the saturated hydrocarbyl of straight or branched, and it has at least one and is selected from OH, NH
2And NH
3 +Substituting group and contain one or more C (O) H group when needed and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
R
1Be the saturated hydrocarbyl of straight or branched, when needed, it has one or more OH of being selected from, NH
2, NH
3 +And the substituting group of C (O) H and contain when needed one or more non-conterminous-O-, and/or secondary amine and/or tertiary amine are wherein at NH
2-or NH
3 +One or more H in the group can be replaced by alkyl and
In the compound of general formula (Ia), the ratio of A-R is at least 10 weight % and in the compound of general formula (Ib), and the ratio of A-R is at least 20 weight %.
8. according to the mixture of claim 7, wherein in formula (Ia) compound, the ratio of A-R is at least 15 weight %, preferably at least 20 weight %, especially preferably at least 25 weight %, 35-60 weight % very particularly preferably, and/or in formula (Ib) compound, the ratio of A-R is at least 25 weight %, particularly 35-60 weight %.
9. according to the mixture of claim 7 or 8, L wherein
aAnd L
bThe polyisobutenyl that each is made up of at least 80 weight % isobutenyl unit naturally.
10. one kind prepares each the formula (Ia) and (Ib) method of compound of claim 1-6, wherein polyisobutene and rich horse diacid chloride, fumaric acid, Malaysia diacid chloride, toxilic acid or maleic anhydride reaction, the reaction product of gained and oxyethane, propylene oxide, alkanolamine, polyamines, low polyalcohols, polyvalent alcohol, oligo alkylene glycols, polyalkylene glycol, carbohydrate or sugar reaction, when needed, the free hydroxyl group of existence is by NH
3, amine or an alkali metal salt or alkaline earth salt change into corresponding salt.
11. according among the claim 1-6 each formula (Ia) and/or (Ib) compound and/or according to each mixture among the claim 7-9 in fuel, lubricant or fuel dope and lubricant additive concentrates as surfactant, as emulsifying agent, as the wear resistance additive, as oiliness additive or as corrosion inhibiting additive, or in liquid, aqueous as the purposes of corrosion inhibiting additive.
12. according to the purposes of claim 11, wherein said compound and/or mixture are used as emulsifying agent in the preparation of water-in-oil emulsion, particularly water-in-fuel emulsion, or as the tensio-active agent in industry and make up washing and the cleaning batching.
13. fuel, lubricant, fuel additive concentrate, lubricant additive concentrates or liquid, aqueous, contain among the with good grounds claim 1-6 each formula (Ia) and/or (Ib) compound and/or according to each mixture among the claim 7-9, preferred fuel water-in type emulsion, the fuel that contains 60-95 weight %, preferred diesel oil, the water of 3-35 weight % and as the 0.2-10 weight % of emulsifying agent, one or more of preferred 0.5-5 weight % are according to each formula (Ia) and/or (Ib) compound and/or according to each mixture among the claim 7-9 of claim 1-6.
14. washing or cleaning batching contain among the with good grounds claim 1-6 each formula (Ia) and/or (Ib) compound and/or according to each mixture among the claim 7-9.
15., wherein, also have one or more other emulsifying agents, preferred single oleic acid sorbitan ester, C except one or more formulas (Ia) and/or (Ib) the compound according to the emulsion of claim 13
13Oxo process alcohol ethoxylate or alkylphenol ethoxylate, and/or one or more microbicides, preferred NH
4NO
3And/or oxalic dialdehyde, preferred especially oxalic dialdehyde.
16. a method of producing the emulsion of claim 13 or 15 wherein is mixed with each other each component, and according to known mode emulsification itself, preferably carries out in mixing nozzle.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10125158.0 | 2001-05-22 | ||
| DE10125158A DE10125158A1 (en) | 2001-05-22 | 2001-05-22 | Low and high molecular weight emulsifiers, in particular on bases of polyisobutylene, and mixtures thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1511167A true CN1511167A (en) | 2004-07-07 |
Family
ID=7685881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA02810580XA Pending CN1511167A (en) | 2001-05-22 | 2002-05-17 | Low-molecular and high-molecular emulsifiers, particularly based on polyisobutylene, and mixtures thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040154216A1 (en) |
| EP (1) | EP1404726A2 (en) |
| JP (1) | JP2004531614A (en) |
| CN (1) | CN1511167A (en) |
| AU (1) | AU2002338977A1 (en) |
| CA (1) | CA2448033A1 (en) |
| DE (1) | DE10125158A1 (en) |
| WO (1) | WO2002094889A2 (en) |
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| GB201413355D0 (en) * | 2014-07-28 | 2014-09-10 | Innospec Ltd | Compositons and methods |
| KR101904585B1 (en) * | 2015-02-17 | 2018-10-08 | 주식회사 엘지화학 | Modified isobutylen-isoprene rubber, method of producing the same and cured product |
| DE212016000150U1 (en) * | 2015-07-24 | 2018-03-16 | Basf Se | Corrosion inhibitors for fuels and lubricants |
| EP3371271B1 (en) * | 2015-11-02 | 2022-01-05 | The Lubrizol Corporation | Lubricant for water based drilling fluid |
| GB201705091D0 (en) * | 2017-03-30 | 2017-05-17 | Innospec Ltd | Compositions and methods and uses relating thereto |
| EP3940045A4 (en) * | 2019-03-14 | 2022-12-14 | NOF Corporation | Lubricating oil additive, lubricating oil additive composition, and lubricating oil composition containing these |
| CN115895752A (en) | 2021-09-30 | 2023-04-04 | 中国石油化工股份有限公司 | Antiwear additive, preparation method thereof and application thereof in oil products |
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| DE1271877B (en) * | 1963-04-23 | 1968-07-04 | Lubrizol Corp | Lubricating oil |
| GB1543359A (en) * | 1976-10-28 | 1979-04-04 | Shell Int Research | Esterification of hydrocarbyl-substituted succinic anhydrides |
| US4225447A (en) * | 1979-01-08 | 1980-09-30 | Mobil Oil Corporation | Emulsifiable lubricant compositions |
| US4368133A (en) * | 1979-04-02 | 1983-01-11 | The Lubrizol Corporation | Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives |
| US4708753A (en) * | 1985-12-06 | 1987-11-24 | The Lubrizol Corporation | Water-in-oil emulsions |
| GB2231873A (en) * | 1989-03-10 | 1990-11-28 | Shell Int Research | Lubricating compositions |
| HU211439B (en) * | 1993-12-16 | 1996-02-28 | Veszpremi Egyetem | Ash-free detergent-dispergant polymer type additive composition and process for preparing thereof |
| US5712348A (en) * | 1996-03-13 | 1998-01-27 | E. I. Du Pont De Nemours And Company | Maleic acid copolymers with fluorinated thioether end-cap |
| CA2272654C (en) * | 1996-11-22 | 2005-08-23 | Clariant Gmbh | Additives for inhibiting gas hydrate formation |
| US5858029A (en) * | 1997-01-13 | 1999-01-12 | Mobil Oil Corporation | Friction reducing additives for fuels and lubricants |
| US6372855B1 (en) * | 1998-08-31 | 2002-04-16 | The Yokohama Rubber Co., Ltd. | Polymer containing isobutylene as repeating unit and rubber composition containing the same |
-
2001
- 2001-05-22 DE DE10125158A patent/DE10125158A1/en not_active Withdrawn
-
2002
- 2002-05-17 US US10/478,476 patent/US20040154216A1/en not_active Abandoned
- 2002-05-17 WO PCT/EP2002/005516 patent/WO2002094889A2/en not_active Application Discontinuation
- 2002-05-17 JP JP2002592363A patent/JP2004531614A/en not_active Withdrawn
- 2002-05-17 CN CNA02810580XA patent/CN1511167A/en active Pending
- 2002-05-17 EP EP02750949A patent/EP1404726A2/en not_active Withdrawn
- 2002-05-17 AU AU2002338977A patent/AU2002338977A1/en not_active Abandoned
- 2002-05-17 CA CA002448033A patent/CA2448033A1/en not_active Abandoned
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102892830A (en) * | 2010-05-12 | 2013-01-23 | 巴斯夫欧洲公司 | Emulsions of polyisobutenes, substance and process |
| CN106929112A (en) * | 2015-12-30 | 2017-07-07 | 中国石油化工股份有限公司 | A kind of method for improving low-sulfur diesel-oil wear resistence |
| CN110462006A (en) * | 2017-03-30 | 2019-11-15 | 因诺斯佩克有限公司 | Method and purposes |
| CN110520508A (en) * | 2017-03-30 | 2019-11-29 | 因诺斯佩克有限公司 | Method and purposes |
| CN110536954A (en) * | 2017-03-30 | 2019-12-03 | 因诺斯佩克有限公司 | Method and purposes |
| CN110536953A (en) * | 2017-03-30 | 2019-12-03 | 因诺斯佩克有限公司 | Prevent the method and purposes of deposit in engine |
| CN110582555A (en) * | 2017-03-30 | 2019-12-17 | 因诺斯佩克有限公司 | Method and use for preventing deposits in an engine |
| CN110621763A (en) * | 2017-03-30 | 2019-12-27 | 因诺斯佩克有限公司 | Compositions and methods and uses related thereto |
| AU2018247097B2 (en) * | 2017-03-30 | 2022-12-15 | Innospec Limited | Method and use |
| CN110621763B (en) * | 2017-03-30 | 2023-08-08 | 因诺斯佩克有限公司 | Compositions and methods and uses related thereto |
| CN110028998A (en) * | 2018-01-12 | 2019-07-19 | 雅富顿化学公司 | For the emulsifier in lubricating oil |
| CN110028998B (en) * | 2018-01-12 | 2022-11-18 | 雅富顿化学公司 | Emulsifier for use in lubricating oils |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004531614A (en) | 2004-10-14 |
| US20040154216A1 (en) | 2004-08-12 |
| CA2448033A1 (en) | 2002-11-28 |
| WO2002094889A3 (en) | 2003-11-27 |
| AU2002338977A1 (en) | 2002-12-03 |
| DE10125158A1 (en) | 2002-12-05 |
| WO2002094889A2 (en) | 2002-11-28 |
| EP1404726A2 (en) | 2004-04-07 |
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