WO2015134129A2 - Emulsifier components and methods of using the same - Google Patents
Emulsifier components and methods of using the same Download PDFInfo
- Publication number
- WO2015134129A2 WO2015134129A2 PCT/US2015/013177 US2015013177W WO2015134129A2 WO 2015134129 A2 WO2015134129 A2 WO 2015134129A2 US 2015013177 W US2015013177 W US 2015013177W WO 2015134129 A2 WO2015134129 A2 WO 2015134129A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrocarbyl
- acylating agent
- substituted acylating
- substituted
- additive
- Prior art date
Links
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 47
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 168
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 147
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 136
- 239000000654 additive Substances 0.000 claims abstract description 97
- 230000000996 additive effect Effects 0.000 claims abstract description 82
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 78
- 125000000524 functional group Chemical group 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 85
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 73
- 150000001412 amines Chemical class 0.000 claims description 62
- 229930195733 hydrocarbon Natural products 0.000 claims description 50
- 150000002430 hydrocarbons Chemical class 0.000 claims description 50
- 239000004215 Carbon black (E152) Substances 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002243 precursor Substances 0.000 claims description 14
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 claims description 13
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 12
- RSPWVGZWUBNLQU-FOCLMDBBSA-N 3-[(e)-hexadec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCC\C=C\C1CC(=O)OC1=O RSPWVGZWUBNLQU-FOCLMDBBSA-N 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 6
- 229920002367 Polyisobutene Polymers 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 description 67
- 239000003921 oil Substances 0.000 description 39
- 235000019198 oils Nutrition 0.000 description 39
- 125000002947 alkylene group Chemical group 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 125000001931 aliphatic group Chemical group 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000839 emulsion Substances 0.000 description 20
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 19
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- 239000003513 alkali Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229910021529 ammonia Inorganic materials 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 10
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000012530 fluid Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 150000003141 primary amines Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 229940012017 ethylenediamine Drugs 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 150000003512 tertiary amines Chemical class 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001339 alkali metal compounds Chemical class 0.000 description 6
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 235000011044 succinic acid Nutrition 0.000 description 6
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229920001281 polyalkylene Polymers 0.000 description 5
- 150000003444 succinic acids Chemical class 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000002015 acyclic group Chemical group 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 150000004885 piperazines Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- CYOIAXUAIXVWMU-UHFFFAOYSA-N 2-[2-aminoethyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCN(CCO)CCO CYOIAXUAIXVWMU-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Natural products NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 150000004886 thiomorpholines Chemical class 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 2
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PSVJDFLPZZXFDU-UHFFFAOYSA-N cyclohexen-1-amine Chemical class NC1=CCCCC1 PSVJDFLPZZXFDU-UHFFFAOYSA-N 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical class NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- OQGVPWWLCUMRCI-UHFFFAOYSA-N cyclopenten-1-amine Chemical class NC1=CCCC1 OQGVPWWLCUMRCI-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 150000002518 isoindoles Chemical class 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- LSICDRUYCNGRIF-UHFFFAOYSA-N n,n-dimethylheptan-1-amine Chemical compound CCCCCCCN(C)C LSICDRUYCNGRIF-UHFFFAOYSA-N 0.000 description 1
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 1
- AMAADDMFZSZCNT-UHFFFAOYSA-N n,n-dimethylnonan-1-amine Chemical compound CCCCCCCCCN(C)C AMAADDMFZSZCNT-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- IDFANOPDMXWIOP-UHFFFAOYSA-N n,n-dimethylpentan-1-amine Chemical compound CCCCCN(C)C IDFANOPDMXWIOP-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical class CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- 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
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
- C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
- C10M2207/127—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids polycarboxylic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/24—Emulsion properties
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
Definitions
- This invention relates to an additive comprising a functional group derived from a first hydro carbyl -substituted acylating agent and a functional group derived from a second hydrocarbyl-substituted acylating agent, where the functional groups are coupled by a functional group derived from an an alkylene glycol, and in certain embodiments a linear alkylene glycol.
- the invention also relates to an emulsifier component prepared by a process that utilizes the described additive and converts it to an emulsifier component by reacting it with a neutralizing component.
- the invention also relates to a process of making the described emulsifier component, and a method of customizing an emulsifier component in a composition by using the described additive and the described process for converting it to the described emulsifier component.
- Hydrocarbyl-substituted carboxylic acylating agents having at least about 30 aliphatic carbon atoms in the substituent are known as additives in normally liquid fuels and lubricants.
- acylating agents include the polyisobutenyl-substituted succinic acids and anhydrides.
- the use of such carboxylic acylating agents as additives in normally liquid fuels and lubricants is disclosed in U.S. Pat. Nos. 3,288,714 and 3,346,354.
- acylating agents are also useful as intermediates for preparing additives for use in normally liquid fuels and lubricants as described in U.S. Pat.
- U.S. Pat. No. 3,216,936 describes nitrogen-containing dispersants for use in lubricants which are obtained by the reaction of an alkylene amine with an acidic mixture consisting of a hydrocarbon-substituted succinic acid having at least about 50 aliphatic carbon atoms in the hydrocarbon substituent and an aliphatic monocarboxylic acid.
- the aliphatic monocarboxylic acids are described as including saturated and unsaturated acids such as acetic acid, dodecanoic acid, oleic acid, naphthenic acid, formic acid, etc. Acids having 12 or more aliphatic carbon atoms, particularly stearic acid and oleic acid, are described as being especially useful.
- U.S. Pat. No. 4,642,330 discloses dispersant salt compositions made by reacting phosphorus-free carboxylic solubilizers with sulfonic acid-free organic acids or mineral acids.
- the carboxylic solubilizer is the reaction product of a polycarboxylic acid acylating agent having at least one hydrocarbon-based substituent of at least 8 to 500 carbon atoms with at least one poly (alky leneamine).
- the reference indicates that these dispersant salt compositions have good thermal stability when mixed with a surfactant or a hydrophilic organic solvent, and that they can be used with aqueous solutions to disperse various fillers including carbon black and to solubilize various fluids.
- Nitrogen-containing, phosphorus-free carboxylic solubilizers useful in water based functional fluids are disclosed in U.S. Pat. Nos. 4,329,249; 4,368, 133; 4,435,297; 4,447,348; and 4,448,703. These solubilizers are made by reacting (I) at least one carboxylic acid acylating agent having at least one hydrocarbyl substituent of from about 12 to about 500 carbon atoms with (II) at least one (a) N-(hydroxyl- substituted hydrocarbyl) amine, (b) hydroxyl-substituted poly(hydrocarbyloxy) analog of said amine (a), or (c) mixtures of (a) and (b).
- acylating agents include the substituted succinic acids or anhydrides, such as polyisobutenyl-substituted succinic anhydride, and that the amines that are useful include the primary, secondary and tertiary alkanol amines, such as diethylethanolamine and mixtures of diethylethanolamine and ethanolamine. These solubilizers are useful in dispersing oil-soluble, water-insoluble functional additives in water-based functional fluids. [0008] U.S. Pat. No.
- salt compositions comprising: (A) at least one salt moiety derived from (A)(1) at least one high-molecular weight polycarboxylic acylating agent, said acylating agent (A)(1) having at least one hydrocarbyl substituent having an average of from about 20 to about 500 carbon atoms, and (A)(II) ammonia, at least one amine, at least one alkali or alkaline earth metal, and/or at least one alkali or alkaline earth metal compound; (B) at least one salt moiety derived from (B)(1) at least one low-molecular weight polycarboxylic acylating agent, said acylating agent (B)(1) optionally having at least one hydrocarbyl substituent having an average of up to about 18 carbon atoms, and (B)(II) ammonia, at least one amine, at least one alkali or alkaline earth metal, and/or at least one alkali or alkaline earth metal compound; said components (A) at least one salt mo
- U.S. Pat. No. 4,828,633 discloses emulsion explosives based upon the emulsifier of U.S. Pat. No. 5,047, 175.
- U.S. Pat. No. 5,422,024 provides for aqueous oil-in-water emulsion functional fluids comprising water, an oil and an emulsifying quantity of a salt composition
- a salt composition comprising: (A) at least one salt moiety derived from (A)(1) at least one high-molecular weight polycarboxylic acylating agent, said acylating agent (A)(1) having at least one hydrocarbyl substituent having an average of from about 20 to about 200 carbon atoms, and (A)(II) ammonia, at least one amine, at least one alkali or alkaline earth metal, and/or at least one alkali or alkaline earth metal compound; (B) at least one salt moiety derived from (B)(1) at least one low- molecular weight polycarboxylic acylating agent, said acylating agent (B)(1) optionally having at least one hydrocarbyl substituent having an average of average of up to about 18 carbon atoms, and (B
- the disclosed technology provides an additive comprising (i) a functional group derived from a first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from a second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled by a functional group derived from an alkylene glycol such as a linear alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl- substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms.
- the invention further provides the described additive where the first hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight greater than 400. In some embodiments, long chain hydrocarbon has a number average molecular weight greater than 450, at least 500, at least 750, or even at least 800.
- a "monounsaturated carboxylic acid” refers to a carboxylic acid that contains one ethylenic unsaturation, that is, not counting the carbonyl double bond.
- the invention further provides the described additive where the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 400.
- the polyisobutylene succinic anhydride has a polyisobutylene group with a number average molecular weight greater than 450, at least 500, at least 750, or even at least 800.
- the invention further provides the described additive wherein the second hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight less than 400 or less than 280 or less than 250.
- long chain hydrocarbon has a number average molecular weight from 100 to 400, or from 200 to 400, or from 200 to 280, or from 200 to 250, or from 300 to 400, or even from 300 to 350, or even about 322.
- the invention further provides the described additive wherein the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride.
- the alkylene glycol comprises a glycol having of the general formula HO— f-(C(R)) x -0- ⁇ m -H wherein each R is independently H or an alkyl group of 1 to 6 carbon atoms each x is independently an integer from 2 to 10 and m is an integer from 1 to 10. That is, some or all of the R groups may be H and the remainder (if any) of the R groups may be said alkyl groups. In certain embodiments disclosed herein, one or more of the R groups may be methyl groups. In certain embodiments throughout this document, the number of carbon atoms in the glycol of the foregoing structure will be less than 400, or less than 200, or less than 100, or 2 to 50, or 2 to 10, or 2 or 3.
- the alkylene glycol is a linear alkylene glycol, and in some embodiments it comprises ethylene glycol.
- the invention further provides the described additive wherein the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 750; wherein the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride; and wherein the alkylene glycol comprises ethylene glycol.
- the invention further provides an emulsifier component prepared by a process comprising the steps of: Step (I) reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an additive comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled by a functional group derived from said alkylene glycol;
- the invention further provides the emulsifier component described above where said neutralizing component comprises an alkali or alkaline earth-metal base or an amine.
- Suitable amines include NaOH, KOH, monoethanolamine, diethanolamine, triethanolamine, methyl diethanolamine, dimethylethanolamine, butylethanolamine, butyl diethanolamine, octyl diethanolamine, cyclohexyl diethanolamine, monoisopropanolamine, diispropanolamine, triispropanolamine, diglycolamine, l -amino-2-methyl-l-propanol, 3-amino-4-octanol, dicylcohexyl- amine, octylamine, and any combinations thereof.
- the invention further provides a process of making an emulsifier component comprising the steps of: Step (I) reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an intermediate (which may also be referred to throughout this document as an additive) comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled
- the invention further provides the describe process wherein the first hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight greater than 400; and wherein the second hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight less than 400 or less than 280; wherein the (optionally linear) alkylene glycol comprises a glycol having of the general formula HO—
- the invention further provides the describe process wherein the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 750; wherein the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride; and wherein the alkylene glycol comprises ethylene glycol.
- the invention further provides a method of customizing an emulsifier component in a composition said method comprising the steps of: Step (I) preparing an additive by reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an additive comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled by a
- the invention further provides the described method wherein the first hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a mono unsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight greater than 400; and wherein the second hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight less than 400 or less than 280; and wherein the alkylene glycol comprises a glycol having of the general formula HO— [-(CH 2 ) x -0-J m -H wherein each R is independently H or an alkyl group of 1 to 6 carbon atoms each x is independently an integer from 2 to 10 and m is an integer from 1 to 10.
- the disclosed technology provides an additive comprising (i) a functional group derived from a first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from a second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled by a functional group derived from an alkylene glycol which may be either a branched or a linear alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms.
- the first hydrocarbyl-substituted acylating agent and the second hydrocarbyl-substituted acylating agent, from which the functional groups (i) and (ii) are derived, may also be described as carboxylic acylating agents and may be aliphatic or aromatic, polycarboxylic acids or acid-producing compounds.
- carboxylic acylating agent is intended to include carboxylic acids as well as acid-producing derivatives thereof such as anhydrides, esters, acyl halides and mixtures thereof, unless otherwise specifically stated.
- the acylating agents may contain polar substituents provided that the polar substituents are not present in portions sufficiently large to alter significantly the hydrocarbon character of the acylating agent.
- Typical suitable polar substituents include halo, such as chloro and bromo, oxo, oxy, formyl, sulfenyl, sulfinyl, thio, nitro, etc.
- Such polar substituents if present, preferably do not exceed about 10% by weight of the total weight of the hydrocarbon portion of the acylating agent, exclusive of the carboxyl groups.
- Examples of low molecular weight polycarboxylic acids include dicarboxylic acids and derivatives such as maleic acid, maleic anhydride, chloromaleic anhydride, malonic acid, succinic acid, succinic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, azelaic acid, sebacic acid, glutaconic acid, citraconic acid, itaconic acid, allyl succinic acid, cetyl malonic acid, tetrapropylene-substituted succinic anhydride, etc. Lower alkyl esters of these acids can also be used.
- both the first hydrocarbyl-substituted acylating agent and the second hydrocarbyl-substituted acylating agents are hydrocarbyl substituted succinic acids and anhydrides.
- the hydrocarbyl succinic acylating agents may contain polar substituents provided that the polar substituents are not present in portions sufficiently large to alter significantly the hydrocarbon character of the acylating agent.
- Typical suitable polar substituents include halo, such as chloro and bromo, oxo, oxy, formyl, sulfenyl, sulfinyl, thio, nitro, etc.
- Such polar substituents, if present, preferably do not exceed about 10% by weight of the total weight of the hydrocarbon portion of the acylating agent, exclusive of the carboxyl groups.
- the high-molecular weight polycarboxylic acylating agents i.e. the first hydrocarbyl-substituted acylating agent which comprises a hydrocarbyl substituent group containing at least 20 carbon atoms
- the high-molecular weight polycarboxylic acylating agents are well known in the art and have been described in detail, for example, in U.S. Pat. Nos. 3,215,707; 3,231 ,587; 3,288,714; 3,346,354; 3,912,764; 41 10,349; and 4,234,435; and British Patent 1 ,492,337. These patents are incorporated herein by reference.
- hydrocarbyl groups of the first and second hydrocarbyl-substituted acylating agents are not overly limited so long as they meet the requirements described herein.
- Especially useful hydrocarbyl groups comprising polymers of 1 - mono-olefins such as ethylene, propene, 1 -butene, isobutene, 1 -hexene, 1 -octene, 2- methyl-l-heptene, 3 -cyclohexyl- 1 -butene, and 2-methyl-5 -propyl- 1-hexene.
- Polymers of medial olefins i.e., olefins in which the olefinic linkage is not at the terminal position, likewise are useful. These are exemplified by 2-butene, 3- pentene, and 4-octene. Interpolymers of 1 -mono-olefins such as illustrated above with each other and with other interpolymerizable olefinic substances such as aromatic olefins, cyclic olefins, and polyolefins, are also useful.
- Such interpolymers include for example, those prepared by polymerizing isobutene with styrene, isobutene with butadiene, propene with isoprene, propene with isobutene, ethylene with piperylene, isobutene with chloroprene, isobutene with p -methyl -styrene, 1 - hexene with 1 ,3-hexadiene, 1 -octene with 1-hexene, 1 -heptene with 1 -pentene, 3- methyl- 1-butene with 1 -octene, 3, 3 -dimethyl- 1-pentene with 1 -hexene, isobutene with styrene and piperylene, etc.
- the interpolymers contemplated for use in preparing the acylating agents of this invention are preferably substantially aliphatic and substantially saturated, that is, they should contain at least about 80% and preferably about 95%, on a weight basis, of units derived from aliphatic mono-olefins. Preferably, they will contain no more than about 5% olefinic linkages based on the total number of the carbon-to-carbon covalent linkages present.
- the polymers are obtained by the polymerization of a C4 refinery stream having a butene content of about 35% to about 75%) by weight and an isobutene content of about 30%> to about 60%> by weight.
- These polyisobutenes preferably contain predominantly (that is, greater than about 80% of the total repeat units) isobutene repeat units of the configuration -CH 2 C(CH 3 ) 2 -.
- the hydrocarbons and ethylenically unsaturated hydrocarbons used in the preparation of the higher molecular weight succinic acylating agents may have up to about 200 carbon atoms per molecule.
- Some acylating agents are those containing hydrocarbyl groups of from about 20 to about 150, or from 30 to about 120, or from about 50 to about 80 carbon atoms.
- the hydrocarbyl-substituted succinic acids and the anhydride may prepared by reacting maleic anhydride with a high molecular weight olefin.
- the hydrocarbyl-substituted succinic anhydrides may be hydrolyzed by treatment with water or steam to the corresponding acid and either the anhydride or the acid may be converted to the corresponding acid or ester.
- the hydrocarbyl group of the first hydrocarbyl-substituted acylating agent may contain from about 20 to about 200 carbon atoms, from about 30 to about 150 carbon atoms, from about 50 to about 200 carbon atoms, or even from about 70 to about 80 carbon atoms.
- the second hydrocarbyl-substituted acylating agent which may also be referred to as the low molecular weight succinic acylating agents can be prepared in essentially the same manner as the high molecular weight materials.
- its hydrocarbyl group is an aliphatic or alicyclic hydrocarbyl group with less than about 10% of its carbon-to-carbon bonds being unsaturated. Its hydrocarbyl can be derived from olefins of from 2 to about 18 carbon atoms with alpha-olefms being particularly useful.
- olefins examples include ethylene, propylene, 1- butene, isobutene, 1-pentene, 2-methyl-l -butene, 3 -methyl- 1 -butene, 1-hexene, 1- heptene, 1-octene, styrene, 1-nonene, 1-decene, 1-undecene, 1-dodecene, 1-tridecene, 1-tetradecene, 1-pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene.
- alpha olefin fractions such as C 12-18 alpha- olefins, C I 2- 16 alpha-olefins, C I 4- 14 16 alpha-olefins, C I 4- 18 alpha-olefins, and C I 6- 18 alpha-olefins, are particularly useful. These commercial alpha-olefin fractions also usually include minor amounts of alpha-olefins outside the given ranges. As is the case for the high molecular weight materials, the unsaturated material or optionally chlorinated analog is reacted with maleic acid or maleic anhydride. The production of such substituted succinic acids and their derivatives is well known to those of skill in the art and need not be discussed in detail herein.
- the first hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight greater than 400. In some embodiments, long chain hydrocarbon has a number average molecular weight greater than 450, at least 500, at least 750, or even at least 800. In some embodiments, the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 400. In some embodiments, the polyisobutylene succinic anhydride has a number average molecular weight greater than 450, at least 500, at least 750, or even at least 800.
- the second hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight less than 400 or less than 280.
- long chain hydrocarbon has a number average molecular weight from 100 to 400, or from 200 to 400, or from 300 to 400, or even from 300 to 350, or even about 322, or 100 to less than 280.
- the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride.
- the functional groups (i) and (ii) described above are coupled by a functional group derived from an alkylene glycol.
- This third functional group acts as a bridge between the low and the high molecular weight functional groups derived from the acylating agents described above.
- the low and high molecular weight agents may be mixed together, and are reacted with the bridging molecule.
- the reaction is such that the predominant species in the reaction mixture is the product in which the alkylene glycol acts as a bridge between a first hydrocarbyl- substituted acylating agent and a second hydrocarbyl-substituted acylating agent.
- low and high molecular weight agents may be reacted sequentially with the alkylene glycol.
- the species comprising a first hydrocarbyl-substituted acylating agent and a second hydrocarbyl-substituted acylating agent molecule linked by an alkylene glycol greatly predominates over the other species.
- any compound having (i) two or more primary amino groups, (ii) two or more secondary amino groups, (iii) at least one primary amino group and at least one secondary amino group, (iv) at least two hydroxyl groups, or (v) at least one primary or secondary amino group and at least one hydroxyl group may be used as a linking group.
- an alkylene glycol such as, in some embodiments, a linear alkylene glycol, provides the best results, i.e. the most customizable additive.
- the alkylene glycols useful in the invention may also be referred to generally as polyols, and includes those compounds of the general formula: R ⁇ OH) !!! wherein R 1 is a divalent organic group joined to the -OH groups through carbon-to-oxygen bonds (that is, -COH wherein the carbon is not part of a carbonyl group) and m is 2.
- R ⁇ OH a divalent organic group joined to the -OH groups through carbon-to-oxygen bonds
- m is 2.
- These alcohols are be aliphatic and in some embodiments contain not more than about 40, or not more than about 20 carbon atoms.
- Alcohols useful in this invention include alkylene glycols with the alkylene group containing from about 2 to 10 or 2 to 8 carbon atoms. They may also include polyoxyalkylene glycol, that is, materials represented by HO—
- ethylene glycol diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, dibutylene glycol, tributylene glycol, and other alkylene glycols and polyoxyalkylene glycols in which the alkylene groups contain from 2 to about 8 carbon atoms.
- Polyoxyalkylene glycols which are copolymers of different alkylene oxide units may also be used, such as copolymers of ethylene glycol and propylene glycols such as 1 ,2- or 1 ,3 -propylene glycol.
- the linear alkylene glycol comprises a poly(ethylene glycol), a poly(l ,3-propylene glycol) or a copolymer of ethylene glycol and 1 ,3-propylene glycol.
- one or more linking compounds is used in combination with linear alkylene glycols described herein.
- additional linker may include any compound having (i) two or more primary amino groups, (ii) two or more secondary amino groups, (iii) at least one primary amino group and at least one secondary amino group, (iv) at least two hydroxyl groups, or (v) at least one primary or secondary amino group and at least one hydroxyl group may be used as a linking group.
- the linking compounds contains the alkylene glycols described herein, and is essentially free of, or even completely free of, any other linking compounds.
- the described additive wherein the alkylene glycol comprises a glycol having of the general formula HO(CH 2 ) x OH wherein x is an integer from 2 to 10.
- the alkylene glycol comprises ethylene glycol.
- the invention further provides the described additive wherein the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 750; wherein the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride; and wherein the alkylene glycol comprises ethylene glycol.
- the first hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight greater than 400; and the second hydrocarbyl-substituted acylating agent comprises the reaction product of a long chain hydrocarbon with a monounsaturated carboxylic acid; wherein said long chain hydrocarbon has a number average molecular weight less than 400 or less than 280; and the alkylene glycol comprises a glycol having of the general formula HO—
- the first hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride having a number average molecular weight greater than 750; the second hydrocarbyl-substituted acylating agent comprises hexadecenyl succinic anhydride; and the alkylene glycol comprises ethylene glycol.
- the Emulsifier Component is the Emulsifier Component
- the invention further provides an emulsifier component prepared by a process that allows for the customization of the emulsifier.
- the emulsifier component is prepared by: Step (I) reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an additive comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl- substituted acylating agent, where the functional groups (i) and (ii) are coupled
- Step (II) by providing said additive for use as an emulsifier component precursor, it is meant that the emulsifier component precursor (which may also be referred to as the additive) is handled like a conventional emulsifier component would be. However, in the case of the emulsifier component precursor, it is converted into the specific emulsifier component of a downstream party's choice, for example, a finished fluid blender and/or user, who follows Step (III) and convert the additive to an emulsifier component by reacting said additive with a neutralizing component.
- the emulsifier component precursor which may also be referred to as the additive
- the emulsifier component precursor is converted into the specific emulsifier component of a downstream party's choice, for example, a finished fluid blender and/or user, who follows Step (III) and convert the additive to an emulsifier component by reacting said additive with a neutralizing component.
- providing said additive for use as an emulsifier component precursor involves using, storing, transporting, selling, blending, and/or otherwise handing the additive before it is converted into the emulsifier component.
- the emulsifier component precursor is transported and/or stored after the additive is formed, but before the additive is converted to the emulsifier component.
- the neutralizing components used to form the emulsifier components described above are not overly limited. Typically, the resulting emulsifier component is in the form of a salt.
- the emulsifier components may be formed from mixtures of one or more neutralizing components. In some embodiments, a single kind of neutralizing component is used. In other embodiments, a mixture of two or more neutralizing components are used.
- the metals useful as neutralizing components include the alkali and alkaline earth-metals that may be found in metal bases.
- the amines useful as neutralizing components in preparing the salt compositions of the invention include ammonia, and the primary amines, secondary amines and hydroxyamines. In addition to ammonia, the primary amines, secondary amines and hydroxyamines, the amines useful as neutralizing components also include primary and secondary monoamines, and tertiary mono- and polyamines.
- Useful primary and secondary monoamines include aliphatic, cycloaliphatic and aromatic monoamines.
- the tertiary amines are analogous to the primary amines, secondary amines and hydroxyamines with the exception that they can be either monoamines or polyamines and the hydrogen atoms in the H-N ⁇ or -NH 2 groups are replaced by hydrocarbyl groups.
- Useful polyamines include are characterized by the presence within their structure of at least two -NH 2 groups, at least two >NH groups, or at least one -NH 2 group and at least one >NH group.
- These polyamines can be aliphatic, cycloaliphatic, aromatic or heterocyclic, including aliphatic-substituted aromatic, aliphatic-substituted cycloaliphatic, aliphatic-substituted heterocyclic, cyclo- aliphatic-substituted aliphatic, cycloaliphatic-substituted aromatic, cycloaliphatic- substituted heterocyclic, aromatic-substituted aliphatic, aromatic-substituted cycloaliphatic, aromatic-substituted heterocyclic, heterocyclic-substituted aliphatic, heterocyclic-substituted aliphatic, heterocyclic-substituted aliphatic and heterocyclic-substituted aromatic
- These amines may be saturated or unsaturated. If unsaturated, the amine is preferably free from acetylenic unsaturation. These amines may also contain non- hydrocarbon substituents or groups as long as these groups do not significantly interfere with the reaction. Such non-hydrocarbon substituents or groups include lower alkoxy, lower alkyl, mercapto, nitro, and interrupting groups such as -O- and -S-.
- the polyamines include aliphatic, cycloaliphatic and aromatic polyamines analogous to the aliphatic, cycloaliphatic and aromatic monoamines described below except for the presence within their structure of at least one additional >NH or -NH 2 group.
- Aliphatic monoamines include mono-aliphatic and di-aliphatic-substituted amines wherein the aliphatic groups can be saturated or unsaturated and straight or branched chain. Thus, they are primary or secondary aliphatic amines. Such amines include, for example, mono- and di-alkyl-substituted amines, mono- and di-alkenyl- substituted amines, and amines having one N-alkenyl substituent and one N-alkyl substituent, and the like. The total number of carbon atoms in these aliphatic monoamines preferably does not exceed about 40 and usually does not exceed about 20 carbon atoms.
- Such monoamines include ethylamine, di- ethylamine, n-butylamine, di-n-butylamine, allylamine, isobutylamine, cocoamine, stearylamine, laurylamine, methyllaurylamine, oleylamine, N-methyl-octylamine, dodecylamine, octadecylamine, and the like.
- cycloaliphatic-substituted aliphatic amines examples include 2-(cyclohexyl)-ethylamine, benzylamine, phenylethylamine, and 3-(furylpropyl) amine.
- Cycloaliphatic monoamines are those monoamines wherein there is one cycloaliphatic substituent attached directly to the amino nitrogen through a carbon atom in the cyclic ring structure.
- Examples of cycloaliphatic monoamines include cyclohexylamines, cyclopentylamines, cyclohexenylamines, cyclopentenylamines, N-ethyl-cyclohexylamines, dicyclohexylamines, and the like.
- Examples of aliphatic-substituted, aromatic-substituted, and heterocyclic-substituted cyclo- aliphatic monoamines include propyl-substituted cyclohexylamines, phenyl- substituted cyclopentylamines and pyranyl-substituted cyclohexylamine.
- Aromatic monoamines include those monoamines wherein a carbon atom of the aromatic ring structure is attached directly to the amino nitrogen.
- the aromatic ring will usually be a mononuclear aromatic ring (i.e., one derived from benzene) but can include fused aromatic rings, especially those derived from naphthalene.
- Examples of aromatic monoamines include aniline, di(para- methylphenyl) amine, naphthylamine, N-(n-butyl) aniline, and the like.
- aliphatic-substituted, cycloaliphatic-substituted, and heterocyclic-substituted aromatic monoamines include para-ethoxyaniline, paradodecylamine, cyclohexyl- substituted naphthylamine and thienyl-substituted aniline.
- Heterocyclic polyamines can also be used.
- the terminology "heterocyclic polyamine” is intended to describe those heterocyclic amines containing at least two primary amino groups, at least two secondary amino groups, or at least one of each, and at least one nitrogen as a heteroatom in the heterocyclic ring.
- the hetero-N atom in the ring can be a tertiary amino nitrogen; that is, one that does not have hydrogen attached directly to the ring nitrogen.
- the hetero-N atom can be one of the secondary amino groups; that is, it can be a ring nitrogen with hydrogen directly attached to it.
- Heterocyclic amines can be saturated or unsaturated and can contain various substituents such as nitro, alkoxy, alkyl mercapto, alkyl, alkenyl, aryl, alkaryl, or aralkyl substituents. Generally, the total number of carbon atoms in the substituents will not exceed about 20. Heterocyclic amines can contain heteroatoms other than nitrogen, especially oxygen and sulfur. Obviously they can contain more than one nitrogen heteroatom. The 5- and 6- membered heterocyclic rings are preferred.
- heterocyclic polyamines are the aziridines, azetidines, azolidines, tetra- and di-hydro pyridines, pyrroles, indoles, piperidines, imidazoles, di- and tetrahydroimidazoles, piperazines, isoindoles, purines, morpholines, thiomorpholines, N-aminoalkylmorpholines, N-aminoalkylthio- morpholines, N-aminoalkylpiperazines, N,N'-di-aminoalkylpiperazines, azepines, azocines, azonines, aquelnes and tetra-, di- and perhydro-derivatives of each of the above and mixtures of two or more of these heterocyclic amines.
- Useful heterocyclic polyamines are the saturated 5- and 6-membered heterocyclic polyamines containing only nitrogen, oxygen and/or sulfur in the hetero ring, especially the piperidines, piperazines, thiomorpholines, morpholines, pyrrolidines, and the like. Usually the aminoalkyl substituents are substituted on a nitrogen atom forming part of the hetero ring. Specific examples of such heterocyclic amines include N-aminoethylpiperazine and N,N'-diaminoethylpiperazine.
- Hydrazine and substituted-hydrazines can also be used.
- the substituents which may be present on the hydrazine include alkyl, alkenyl, aryl, aralkyl, alkaryl, and the like.
- the substituents are alkyl, especially lower alkyl, phenyl, and substituted phenyl such as lower alkoxy-substituted phenyl or lower alkyl- substituted phenyl.
- substituted hydrazines are methylhydrazine, N,N-dimethylhydrazine, ⁇ , ⁇ '-dimethylhydrazine, phenyl- hydrazine, N-phenyl-N'-ethylhydrazine, N-(para-tolyl)-N'-(n-butyl)-hydrazine, N- (para-nitrophenyl)-hydrazine, N-(para-nitrophenyl)-N-methylhydrazine, N,N'-di- (para-chlorophenol)-hydrazine, N-phenyl-N'-cyclohexylhydrazine, and the like.
- branched polyalkylene polyamines suitable for use in this invention are branched polyalkylene polyamines.
- the branched polyalkylene polyamines are polyalkylene polyamines wherein the branched group is a side chain containing on the average at least one nitrogen-bonded aminoalkylene group per nine amino units present on the main chain; for example, 1 -4 of such branched chains per nine units on the main chain, but preferably one side chain unit per nine main chain units.
- these polyamines contain at least three primary amino groups and at least one tertiary amino group.
- amines may be expressed by the formula: NH 2 -(R-NH) x -
- R is an alkylene group such as ethylene, propylene, butylene and other homologs (both straight chained and branched), etc., but preferably ethylene; and x, y and z are integers; x is in the range of from about 4 to about 24 or more, preferably from about 6 to about 18; y is in the range of from 1 to about 6 or more, preferably from 1 to about 3; and z is in the range of from zero to about 6, preferably from zero to about 1.
- the x and y units may be sequential, alternative, orderly or randomly distributed.
- a useful class of such polyamines includes those of the formula: NH 2 -f-(R-N(H)) 5 -N(R)(R-NH 2 )-(R- N(H)) 2 - - n -H wherein n is an integer in the range of from 1 to about 20 or more, preferably in the range of from 1 to about 3, and R is preferably ethylene, but may be propylene, butylene, etc. (straight chained or branched).
- U.S. Pat. Nos. 3,200, 106 and 3,259,578 are incorporated herein by reference for their disclosures relative to said polyamines.
- Suitable polyamines also include polyoxyalkylene polyamines, e.g., polyoxyalkylene diamines and polyoxyalkylene triamines, having average molecular weights ranging from about 200 to about 4000, preferably from about 400 to 2000.
- polyoxyalkylene polyamines include those amines represented by the formula: NH 2 -Alkylene-(0-Alkylene) m -NH 2 wherein m has a value of from about 3 to about 70, preferably from about 10 to about 35.
- the alkylene groups may be straight or branched chains and contain from 1 to about 7 carbon atoms, and usually from 1 to about 4 carbon atoms.
- the various alkylene groups present within the above formulae may be the same or different.
- Useful polyoxyalkylene polyamines include the polyoxyethylene and polyoxypropylene diamines and the polyoxypropylene triamines having average molecular weights ranging from about 200 to about 2000.
- the polyoxyalkylene polyamines are commercially available from the Texaco under the trade name "Jeffamine.”
- U.S. Pat. Nos. 3,804,763 and 3,948,800 are incorporated herein by reference for their disclosure of such polyoxyalkylene polyamines.
- Useful polyamines are the alkylene polyamines, including the polyalkylene polyamines, as described in more detail hereafter.
- the alkylene polyamines include those conforming to the formula: (R)(R)N-(Alkylene-N(R)) n -R' wherein n is from 1 to about 10, preferably from 1 to about 7; each R and R' is independently a hydrogen atom, a hydrocarbyl group or a hydroxy-substituted hydrocarbyl group having up to about 700 carbon atoms, preferably up to about 100 carbon atoms, more preferably up to about 50 carbon atoms, more preferably up to about 30 carbon atoms, with the proviso that at least one of R and at least one of R' are hydrogen; and the "Alkylene" group has from about 1 to about 18 carbon atoms, preferably from 1 to about 4 carbon atoms, with the preferred Alkylene being ethylene or propylene.
- Useful alkylene polyamines are those wherein each R and each R' is hydrogen with the ethylene polyamines, and mixtures of ethylene polyamines being particularly preferred.
- alkylene polyamines include methylene polyamines, ethylene polyamines, butylene polyamines, propylene polyamines, pentylene polyamines, hexylene polyamines, heptylene polyamines, etc. The higher homologs of such amines and related aminoalkyl-substituted piperazines are also included.
- Alkylene polyamines that are useful include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, propylene diamine, trimethylene diamine, hexamethylene diamine, decamethylene diamine, octamethylene diamine, di(heptamethylene) triamine, tripropylene tetramine, tetraethylene pentamine, trimethylene diamine, pentaethylene hexamine, di(trimethylene) triamine, N-(2-aminoethyl) piperazine, l ,4-bis(2-aminoethyl) piperazine, and the like. Higher homologs as are obtained by condensing two or more of the above -illustrated alkylene amines are useful as amines in this invention as are mixtures of two or more of any of the aforedescribed polyamines.
- Ethylene polyamines such as those mentioned above, are described in detail under the heading "Diamines and Higher Amines, Aliphatic” in The Encyclopedia of Chemical Technology, Third Edition, Kirk-Othmer, Volume 7, pp. 580-602, a Wiley-Interscience Publication, John Wiley and Sons, 1979, these pages being incorporated herein by reference.
- Such compounds are prepared most conveniently by the reaction of an alkylene chloride with ammonia or by reaction of an ethylene imine with a ring-opening reagent such as ammonia, etc. These reactions result in the production of the somewhat complex mixtures of alkylene polyamines, including cyclic condensation products such as piperazines.
- Alkoxylated alkylene polyamines e.g., N,N-l(diethanol)-ethylene diamine
- Such polyamines can be made by reacting alkylene amines (e.g., ethylenediamine) with one or more alkylene oxides (e.g., ethylene oxide, octadecene oxide) of two to about 20 carbons.
- alkylene oxide-alkanol amine reaction products can also be used such as the products made by reacting the aforedescribed primary, secondary or tertiary alkanol amines with ethylene, propylene or higher epoxides in a 1 : 1 or 1 :2 molar ratio. Reactant ratios and temperatures for carrying out such reactions are known to those skilled in the art.
- alkoxylated alkylene polyamines include N-(2- hydroxyethyl) ethylene diamine, N,N-bis(2-hydroxyethyl)-ethylene-diamine, l -(2- hydroxyethyl) piperazine, mono(hydroxypropyl)-substituted diethylene triamine, di(hydroxypropyl)-substituted tetraethylene pentamine, N-(3 -hydro xybutyl)-tetra- methylene diamine, etc. Higher homologs obtained by condensation of the above- illustrated hydroxy alkylene polyamines through amino groups or through hydroxy groups are likewise useful.
- Useful hydroxyamines can be primary or secondary amines. They can also be tertiary amines provided said tertiary amines also contain at least two hydroxyl groups. These hydroxyamines contain at least two >NH groups, at least two -NH 2 groups, at least one -OH group and at least one >NH or -NH 2 group, or at least two -OH groups.
- hydroxy amine and “aminoalcohol” describe the same class of compounds and, therefore, can be used interchangeably.
- the hydroxyamines can be primary or secondary alkanol amines or mixtures thereof.
- Such amines can be represented, respectfully, by the formulae: (H)(R)N-R'-OH wherein R is a hydrocarbyl group of one to about eight carbon atoms or hydroxylsubstituted hydrocarbyl group of two to about eight carbon atoms and R' is a divalent hydrocarbyl group of about two to about 18 carbon atoms.
- the group -R'-OH in such formulae represents the hydroxyl-substituted hydrocarbyl group.
- R' can be an acyclic, alicyclic or aromatic group.
- R' is an acyclic straight or branched alkylene group such as an ethylene, 1 ,2-propylene, 1 ,2- butylene, 1 ,2-octadecylene, etc. group.
- R is a lower alkyl group of up to seven carbon atoms.
- the primary or secondary alkanol amines may contain slightly larger R and R' groups, and may contain up to about 40 carbon atoms.
- the hydroxyamines can also be ether N-(hydroxy-substituted hydrocarbyl)amines. These are hydroxyl-substituted poly(hydrocarbyloxy) analogs of the above-described primary and secondary alkanol amines (these analogs also include hydroxyl-substituted oxyalkylene analogs).
- Such N-(hydroxyl-substituted hydrocarbyl) amines can be conveniently prepared by reaction of epoxides with aforedescribed amines and can be represented by the formulae: H 2 N-R'-OH and (H)(R)N-R'-OH wherein x is a number from about 2 to about 15 and R and R' are as described above.
- polyamine analogs of these hydroxy amines can also be used.
- alkoxylated alkylene polyamines e.g., N,N-(diethanol)-ethylene diamine
- Such polyamines can be made by reacting alkylene amines (e.g., ethylenediamine) with one or more alkylene oxides (e.g., ethylene oxide, octadecene oxide) of two to about 20 carbons.
- Similar alkylene oxide-alkanol amine reaction products can also be used such as the products made by reacting the aforedescribed primary or secondary alkanol amines with ethylene, propylene or higher epoxides in a 1 : 1 or 1 :2 molar ratio. Reactant ratios and temperatures for carrying out such reactions are known to those skilled in the art.
- alkoxylated alkylene polyamines include N-(2- hydroxyethyl) ethylene diamine, N,N-bis(2-hydroxyethyl) ethylene diamine, l -(2- hydroxyethyl) piperazine, mono(hydroxypropyl)-substituted diethylene triamine, di(hydroxypropyl)-substituted tetraethylene pentamine, N-(3 -hydro xybutyl)- tetramethylene diamine, etc. Higher homologs obtained by condensation of the above-illustrated hydroxyalkylene polyamines through amino groups or through hydroxy groups are likewise useful.
- N-(hydroxyl-substituted hydrocarbyl) amines examples include mono-, di-, and triethanol amine, diethylethanol amine, di-(3-hydroxyl propyl) amine, N-(3-hydroxyl butyl) amine, N-(4-hydroxyl butyl) amine, N,N-di-(2- hydroxyl propyl) amine, N-(2-hydroxyl ethyl) morpholine and its thio analog, N-(2- hydroxyl ethyl) cyclohexyl amine, N-3 -hydro xyl cyclopentyl amine, o-, m- and p- aminophenol, N-(hydroxyl ethyl) piperazine, N,N'-di(hydroxyl ethyl) piperazine, and the like.
- hydroxyamines are the hydroxy-substituted primary amines described in U.S. Pat. No. 3,576,743 by the general formula R a -NH 2 wherein R a is a monovalent organic group containing at least one alcoholic hydroxy group.
- R a is a monovalent organic group containing at least one alcoholic hydroxy group.
- the total number of carbon atoms in R a preferably does not exceed about 20.
- Hydro xy- substituted aliphatic primary amines containing a total of up to about 10 carbon atoms are useful.
- the polyhydroxy-substituted alkanol primary amines wherein there is only one amino group present i.e., a primary amino group
- alkanol primary amines correspond to R a -NH 2 wherein R a is a mono- or polyhydroxy-substituted alkyl group.
- hydroxy- substituted primary amines include 2-amino-l-butanol, 2-amino-2-methyl-l- propanol, p-(beta- hydro xyethyl)-aniline, 2-amino-l-propanol, 3-amino-l-propanol, 2-amino-2-methyl- 1 ,3 -propanediol, 2-amino-2-ethyl-l,3-propanediol, N-(beta- hydroxypropyl)-N'-(beta-aminoethyl)-piperazine, tris-(hydroxymethyl) amino methane (also known as trismethylolamino methane), 2-amino-l-butanol, ethanolamine, beta-(beta-hydroxyethoxy)-ethyl amine, glucamine, glusoamine, 4- amino -3 -hydroxy-3 -methyl- 1-butene
- Hydroxyalkyl alkylene polyamines having one or more hydroxyalkyl substituents on the nitrogen atoms are also useful.
- Useful hydroxyalkyl-substituted alkylene polyamines include those in which the hydroxyalkyl group is a lower hydroxyalkyl group, i.e., having less than eight carbon atoms.
- hydroxyalkyl-substituted polyamines examples include N-(2-hydroxyethyl) ethylene diamine, N,N-bis(2-hydroxyethyl) ethylene diamine, l -(2-hydroxyethyl)-piperazine, monohydroxypropyl-substituted diethylene triamine, dihydroxypropylsubstituted tetraethylene pentamine, N-(3 -hydro xybutyl) tetramethylene diamine, etc.
- Higher homologs as are obtained by condensation of the above -illustrated hydroxy alkylene polyamines through amino groups or through hydroxy groups are likewise useful. Condensation through amino groups results in a higher amine accompanied by removal of ammonia and condensation through the hydroxygroups results in products containing ether linkages accompanied by removal of water.
- Useful tertiary amines include be aliphatic, cycloaliphatic, aromatic or heterocyclic, including aliphatic-substituted aromatic, aliphatic-substituted cycloaliphatic, aliphatic-substituted heterocyclic, cycloaliphatic-substituted aromatic, cycloaliphatic-substituted heterocyclic, aromatic-substituted aliphatic, aromatic-substituted cycloaliphatic, aromatic- substituted heterocyclic, heterocyclic-substituted aliphatic, heterocyclic-substituted aliphatic, heterocyclic-substituted cycloaliphatic and heterocyclic-substituted aromatic amines.
- tertiary amines may be saturated or unsaturated. If unsaturated, the amine is preferably free from acetylenic unsaturation.
- the tertiary amines may .also contain non-hydrocarbon substituents or groups as long as these groups do not significantly interfere with the reaction.
- Such non-hydrocarbon substituents or groups include lower alkoxy, lower alkyl, mercapto, nitro, and interrupting groups such as -O- and -S- (e.g., as in such groups as -CH2CH2-X-CH2CH2- where X is -O- or -S-).
- the monoamines can be represented by the formula N(R )(R )(R )
- R , R , and R are the same or different hydrocarbyl groups.
- R , R , and R are the same or different hydrocarbyl groups.
- R , R , and R are the same or different hydrocarbyl groups.
- R and R J are independently hydrocarbyl groups of from 1 to about 20 carbon atoms.
- Examples of useful tertiary amines include trimethyl amine, triethyl amine, tripropyl amine, tributyl amine, monomethyldiethylamine, monoethyldimethyl amine, dimethylpropyl amine, dimethylbutyl amine, dimethylpentyl amine, dimethylhexyl amine, dimethylheptyl amine, dimethyloctyl amine, dimethylnonyl amine, dimethyldecyl amine, dimethylphenyl amine, N,N- dioctyl-l-octanamine, N,N-di-dodecyl-l-dodecanamine tricoco amine, trihydrogenated tallow amine, N-methyldihydrogenated tallow amine, N,N- dimethyl-l -dodecanamine, N,N-dimethyl-l-tetradecanamine, N N-dimethyl-1- hex amine
- Useful tertiary alkanol amines are represented by the formula (R)(R)N-R'-OH wherein each R is independently a hydrocarbyl group of one to about eight carbon atoms or hydro xyl- substituted hydrocarbyl group of two to about eight carbon atoms and R' is a divalent hydrocarbyl group of about two to about 18 carbon atoms.
- the group -R'-OH in such formula represents the hydro xyl- substituted hydrocarbyl group.
- R' can be an acyclic, alicyclic or aromatic group.
- R' is an acyclic straight or branched alkylene group such as an ethylene, 1 ,2-propylene, 1 ,2-butylene, 1 ,2-octadecylene, etc. group.
- R groups can be joined by a direct carbon-to-carbon bond or through a heteroatom (e.g., oxygen, nitrogen or sulfur) to form a 5-, 6-, 7- or 8- membered ring structure.
- heterocyclic amines include N- (hydroxyl lower alkyl)-morpholines, thiomorpholines, -piperidines, -oxazolidines, -thiazolidines and the like.
- each R is a lower alkyl group of up to seven carbon atoms.
- the hydro xyamines can also be an ether N-(hydroxy- substituted hydrocarbyl)amine. These are hydroxyl-substituted poly- (hydrocarbyloxy) analogs of the above described hydroxy amines (these analogs also include hydroxyl-substituted oxyalkylene analogs).
- Such N-(hydroxyl- substituted hydrocarbyl) amines can be conveniently prepared by reaction of epoxides with the amines described above and can be represented by the formula: (R)(R)N-(R'-0) x H wherein x is a number from about 2 to about 15 and R and R' are as described above.
- Useful polyamines include the alkylene polyamines discussed above as well as alkylene polyamines with only one or no hydrogens attached to the nitrogen atoms.
- the alkylene polyamines useful as neutralizing components include those conforming to the formula: (R)(R)N-(R'-0) x -H wherein x is from 1 to about 10, from 1 to about 7; each R is independently a hydrogen atom, a hydrocarbyl group or a hydroxy-substituted hydrocarbyl group having up to about 700 carbon atoms, preferably up to about 100 carbon atoms, more preferably up to about 50 carbon atoms, more preferably up to about 30 carbon atoms; and the "Alkylene" group has from about 1 to about 18 carbon atoms, preferably from 1 to about 4 carbon atoms, with the preferred Alkylene being ethylene or propylene.
- the alkali and alkaline earth metals that are useful as neutralizing components can be any alkali or alkaline earth metal.
- the alkali metals are preferred.
- Sodium and potassium are particularly preferred.
- the alkali and alkaline earth metal compounds that are useful include, for example, the oxides, hydroxides and carbonates. Sodium hydroxide and potassium hydroxide are particularly preferred.
- the invention further provides a process of making the described emulsifier component.
- the process comprises the steps of: Step (I) reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl- substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an additive comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl-substituted acylating agent, where the functional groups (i) and (ii) are coupled by a functional group derived from said alkylene glycol;
- the process may be described as initially reacting the first hydrocarbyl-substituted acylating agent and the second hydrocarbyl- substituted acylating agent the alkylene glycol to form an additive, and thereafter providing the additive, as described above, to an end use who may then use the additive to form the emulsifier component of his/her choosing by reacting said intermediate with the neutralizing component to form the desired salt.
- the ratio of reactants utilized in the preparation of either the additive (and/or the emulsifier component precursor) emulsifier component may be varied over a wide range.
- each equivalent of each of the acylating agents at least about one equivalent of alkylene glycol is used.
- From about 0.1 to about 2 equivalents or more of neutralizing component are used for each equivalent of components acylating agents, respectively.
- the upper limit of alkylene glycol is about 2 equivalents of alkylene glycol for each equivalent of acylating agents.
- the ratio of equivalents of acylating agents is about 0.5 to about 2, with about 1 : 1 being preferred.
- Preferred amounts of the reactants are about 2 equivalents of the alkylene glycol and from about 0.1 to about 2 equivalents of each of neutralizing component for each equivalent of each acylating agent.
- the number of equivalents of the acylating agents depends on the total number of carboxylic functions present in each. In determining the number of equivalents for each of the acylating agents, those carboxyl functions which are not capable of reacting as a carboxylic acid acylating agent are excluded. In general, however, there is one equivalent of acylating agent for each carboxy group in these acylating agents. For example, there would be two equivalents in an anhydride derived from the reaction of one mole of olefin polymer and one mole of maleic anhydride. Conventional techniques are readily available for determining the number of carboxyl functions (e.g., acid number, saponification number) and, thus, the number of equivalents of each of the acylating agents can be readily determined by one skilled in the art.
- An equivalent weight of a polyamine is the molecular weight of the polyamine divided by the total number of nitrogens present in the molecule where tertiary amino groups are counted.
- ethylene diamine has an equivalent weight equal to one-half of its molecular weight
- diethylene triamine has an equivalent weight equal to one-third its molecular weight.
- the equivalent weight of a commercially available mixture of polyalkylene polyamine can be determined by dividing the atomic weight of nitrogen (14) by the %N contained in the polyamine; thus, a polyamine mixture having a %N of 34 would have an equivalent weight of 41.2.
- An equivalent weight of ammonia or a monoamine is its molecular weight.
- An equivalent weight of polyhydric alcohol is its molecular weight divided by the total number of hydroxyl groups present in the molecule.
- an equivalent weight of ethylene glycol is one-half its molecular weight.
- An equivalent weight of a hydroxyamine would be its molecular weight divided by the total number of nitrogen groups present in the molecule.
- dimethylethanolamine would have an equivalent weight equal to its molecular weight; ethanolamine would also have an equivalent weight equal to its molecular weight.
- An equivalent weight of an alkali or alkaline earth metal is its molecular weight.
- An equivalent weight of an alkali or alkaline earth metal compound is its molecular weight divided by the number of alkali or alkaline earth metal atoms present in the molecule.
- the acylating agents can be reacted with the alkylene glycol according to conventional ester and/or amide forming techniques. This normally involves heating acylating agents with the alkylene glycol optionally in the presence of a normally liquid, substantially inert, organic liquid solvent/diluent.
- the reactions between the additive and the neutralizing component are carried out under salt forming conditions using conventional techniques.
- the components are mixed together and heated to a temperature in the range of about 20°C up to the decomposition temperature of the reaction component and/or product having the lowest such temperature, optionally, in the presence of a normally liquid, substantially inert organic liquid solvent/diluent, until the desired product has formed.
- the invention further provides a method and/or use of the additive described above as part of a process of customizing an emulsifier component in a composition.
- This method and/or use includes the steps of: Step (I) preparing an additive by reacting a first hydrocarbyl-substituted acylating agent, a second hydrocarbyl-substituted acylating agent, and an (optionally linear) alkylene glycol; wherein the first hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing at least 20 carbon atoms; and wherein the second hydrocarbyl-substituted acylating agent comprises a hydrocarbyl substituent group containing less than 20 carbon atoms; resulting in an additive comprising (i) a functional group derived from said first hydrocarbyl-substituted acylating agent and (ii) a functional group derived from said second hydrocarbyl-substituted acylating
- the emulsion components described herein may be used to make functional compositions such as oil-in-water emulsions which comprise a continuous water phase, a discontinuous organic phase, the emulsifying composition, and additives related to the function to be performed by the functional fluid.
- the discontinuous organic phase is preferably present at a level of at least about 1% by weight, more preferably in the range of from about 1 % to about 50% by weight, more preferably in the range of from about 1% to about 20% by weight based on the total weight of emulsion.
- the continuous water phase is preferably present at a level of about 99% by weight, more preferably at a level in the range of from about 50%> to about 99% by weight, more preferably from about 80%> to about 99%) by weight based on the total weight of said emulsion.
- the salt compositions of the invention are preferably present at a level in the range of from about 1 % to about 100%) by weight, more preferably from about 20%> to about 80%> by weight based on the total weight of the organic phase.
- the oil can include most liquid hydrocarbons, for example, paraffinic, olefinic, naphthenic, aromatic, saturated or unsaturated hydrocarbons.
- the oil is a water-immiscible, emulsifiable hydrocarbon that is either liquid at room temperature. Oils from a variety of sources, including natural and synthetic oils and mixtures thereof may be used.
- Natural oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as solvent-refined or acid-refined mineral oils of the paraffinic, naphthenic, or mixed paraffin-naphthenic types. Oils derived from coal or shale are also useful.
- Synthetic oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins e.g., polybutylenes, polypropylenes, propylene -isobutylene copolymers, chlorinated polybutylenes; alkyl benzenes, e.g., dodecylbenzenes, tetradecylbenzenes, dinonyl- benzenes, di-(2-ethylhexyl) benzenes, and the like.
- hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins e.g., polybutylenes, polypropylenes, propylene -isobutylene copolymers, chlorinated polybutylenes; alkyl benzenes, e.g., dodecylbenzenes, t
- Another suitable class of synthetic oils that can be used comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2- ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, pentaerythritol, etc.).
- dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acid, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic
- esters include dibutyl adipate, di(2-ethylhexyl)-sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2- ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2- ethylhexanoic acid, and the like.
- Esters useful as synthetic oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylol propane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
- Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils comprise another class of useful oils. These include tetraethyl-silicate, tetraisopropylsilicate, tetra-(2-ethylhexyl)-silicate, tetra-(4-methylhexyl)-silicate, tetra (p-tert-butylphenyl) -silicate,hexyl-(4-methyl-2- pentoxy)-di-siloxane, poly(methyl)-siloxanes, poly-(methylphenyl)-siloxanes, etc.
- liquid esters of phosphorus-containing acid e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.
- polymeric tetrahydrofurans and the like.
- Unrefined, refined and rerefined oils (and mixtures of each with each other) of the type disclosed hereinabove can be used.
- Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment.
- a shale oil obtained directly from a retorting operation a petroleum oil obtained directly from distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
- Refined oils are similar to the unrefined oils except that they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those of skill in the art such as solvent extraction, distillation, acid or base extraction, filtration, percolation, etc.
- Rere fined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed toward removal of spent additives and oil breakdown products.
- Examples of useful oils include a white mineral oil available from Witco Chemical Company under the trade designation KAYDOL; a white mineral oil available from Shell under the trade designation ONDINA; and a mineral oil available from Pennzoil under the trade designation N-750-HT.
- Optional additional materials may be incorporated in the composition of the present invention.
- Typical finished compositions may include lubricity agents, anti-wear agents, dispersants, corrosion inhibitors, other surfactants, and the like.
- the emulsions of the present invention are shelf stable, which means they exhibit shelf stability of at least six months and typically one year or more.
- a preferred method for making the emulsions of the invention comprises the steps of (1) mixing the emulsifier with the oil phase, (2) mixing the additives with the oil phase, (3) stirring the oil phase with the water phase to form a oil-in- water emulsion.
- Mixing of the oil with the appropriate additives may be conducted in any suitable mixing apparatus. Any type of apparatus capable of either low or high shear mixing may be used to mix the oil and water phases to prepare these oil- in- water emulsions.
- each chemical component described is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, that is, on an active chemical basis, unless otherwise indicated.
- each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, byproducts, derivatives, and other such materials which are normally understood to be present in the commercial grade.
- hydrocarbyl substituent or "hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifi- cally, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. Examples of hydrocarbyl groups include:
- hydrocarbon substituents that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring);
- aliphatic e.g., alkyl or alkenyl
- alicyclic e.g., cycloalkyl, cycloalkenyl
- aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring);
- substituted hydrocarbon substituents that is, substituents containing non- hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
- hetero substituents that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms and encompass substituents as pyridyl, furyl, thienyl and imidazolyl.
- Heteroatoms include sulfur, oxygen, and nitrogen.
- no more than two, or no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; alternatively, there may be no non-hydrocarbon substituents in the hydrocarbyl group.
- a preformed salt emulsifier component is prepared in a reaction vessel by adding 33.33 pbw of 1000 Mn highly reacted polyisobutylene succinic anhydride, 28.41 pbw of hexadecenyl succinic anhydride, and 23.15 pbw ISO 22 mineral oil. The mixture is heated to 99°C under a nitrogen purge. Then 3.87 pbw of ethylene glycol is slowly added to the reaction vessel and the resulting mixture is held at about 99°C for 4 hours. The reaction mixture is cooled to 68°C before adding 1 1.24 pbw dimethylethanolamine. The following reaction is held below 93°C. The amine salted product is then cooled to ambient temperature.
- An unsalted ester acid emulsifier component is prepared in the lab.
- 40.45 parts by weight (pbw) of 1000 number average molecular weight (Mn) highly reacted polyisobutylene succinic anhydride, 34.83 pbw of hexadecenyl succinic anhydride, and 20.00 pbw ISO 22 mineral oil are mixed and heated to 135°C under a nitrogen purge. Then 4.72 pbw of ethylene glycol is slowly added to the reaction vessel and the resulting mixture is held at about 135°C for 4 hours. The resulting unsalted product is then cooled to ambient temperature and collected.
- Each additive package is then used to prepare an emulsion.
- Each emulsion sample is prepared by adding water so that the concentration of the additive package is the same in each emulsion sample (5% by weight).
- Each emulsion sample is shaken vigorously shaken in a graduated cylinder and then allowed to stand for 24 hours before being rating for stability, by measuring the amount, or percent, of oil visible in the sample, and the amount, or percent, of cream visible in the sample. The less oil and cream visible, the more stable the emulsion, and so the more effective the additive package, and so the emulsifier additive.
- a formulation is considered acceptable for use if it has 0% or a trace of oil and no more than 0.5% cream after 24 hours.
- the transitional term "comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, un-recited elements or method steps.
- the term also encompass, as alternative embodiments, the phrases “consisting essentially of and “consisting of,” where “consisting of excludes any element or step not specified and “consisting essentially of permits the inclusion of additional un-recited elements or steps that do not materially affect the basic and novel characteristics of the composition or method under consideration.
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Abstract
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US15/246,624 US20170022443A1 (en) | 2014-03-05 | 2015-01-28 | Emulsifier components and methods of using the same |
EP15705414.9A EP3114195A2 (en) | 2014-03-05 | 2015-01-28 | Emulsifier components and methods of using the same |
CN201580022317.8A CN106232783A (en) | 2014-03-05 | 2015-01-28 | Emulsifier component and using method thereof |
CA2942145A CA2942145A1 (en) | 2014-03-05 | 2015-01-28 | Emulsifier components and methods of using the same |
KR1020167027233A KR20160128406A (en) | 2014-03-05 | 2015-01-28 | Emulsifier components and methods of using the same |
JP2016555589A JP2017510438A (en) | 2014-03-05 | 2015-01-28 | Emulsifier component and method of using the same |
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US201461948071P | 2014-03-05 | 2014-03-05 | |
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US (1) | US20170022443A1 (en) |
EP (1) | EP3114195A2 (en) |
JP (1) | JP2017510438A (en) |
KR (1) | KR20160128406A (en) |
CN (1) | CN106232783A (en) |
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CN112410095A (en) * | 2020-12-01 | 2021-02-26 | 浙江可思克高新材料股份有限公司 | Preparation method of lubricant |
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US10479953B2 (en) * | 2018-01-12 | 2019-11-19 | Afton Chemical Corporation | Emulsifier for use in lubricating oil |
Citations (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892786A (en) | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3163603A (en) | 1963-12-11 | 1964-12-29 | Lubrizol Corp | Amide and imide derivatives of metal salts of substituted succinic acids |
US3172892A (en) | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3189544A (en) | 1962-12-19 | 1965-06-15 | Shell Oil Co | Non-ash-containing lubricating oil composition |
US3200106A (en) | 1960-08-04 | 1965-08-10 | Petrolite Corp | Derivatives of branched polyalkylene-polyamines |
US3215707A (en) | 1960-06-07 | 1965-11-02 | Lubrizol Corp | Lubricant |
US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
US3231587A (en) | 1960-06-07 | 1966-01-25 | Lubrizol Corp | Process for the preparation of substituted succinic acid compounds |
US3235503A (en) | 1963-03-28 | 1966-02-15 | Chevron Res | Lubricant containing alkylene polyamine reaction product |
US3259578A (en) | 1960-08-04 | 1966-07-05 | Petrolite Corp | Lubricating compositions |
US3272746A (en) | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
US3288714A (en) | 1961-12-06 | 1966-11-29 | Monsanto Co | Lubricating oil compositions containing alkenyl succinic anhydrides |
US3306908A (en) | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3306907A (en) | 1963-04-29 | 1967-02-28 | Standard Oil Co | Process for preparing n n-di |
US3331776A (en) | 1962-10-04 | 1967-07-18 | Shell Oil Co | Lubricating oil composition |
US3346354A (en) | 1963-07-02 | 1967-10-10 | Chvron Res Company | Long-chain alkenyl succinic acids, esters, and anhydrides as fuel detergents |
US3374174A (en) | 1966-04-12 | 1968-03-19 | Lubrizol Corp | Composition |
US3379515A (en) | 1965-04-09 | 1968-04-23 | Eddie G. Lindstrom | High molecular weight imide substituted polymers as fuel detergents |
US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
US3413104A (en) | 1964-12-10 | 1968-11-26 | Chevron Res | Imides of olefin-maleic anhydride copolymers as diesel fuel additives |
US3450715A (en) | 1965-04-09 | 1969-06-17 | Chevron Res | N-hydrocarbon succinimidyl polymers |
US3454607A (en) | 1969-02-10 | 1969-07-08 | Lubrizol Corp | High molecular weight carboxylic compositions |
US3455728A (en) | 1965-10-04 | 1969-07-15 | Inland Steel Co | Centrifugal spray coating methods and apparatus |
US3476686A (en) | 1968-06-04 | 1969-11-04 | Sinclair Research Inc | Ashless lubricating oil detergents |
US3513095A (en) | 1967-02-20 | 1970-05-19 | Texaco Inc | Lubricating oil composition of improved dispersancy,viscosity index and shear stability |
US3523768A (en) | 1965-04-28 | 1970-08-11 | Chevron Res | Ester modified polymers as fuel dispersants |
US3576743A (en) | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
US3630904A (en) | 1968-07-03 | 1971-12-28 | Lubrizol Corp | Lubricating oils and fuels containing acylated nitrogen additives |
US3632511A (en) | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
US3639242A (en) | 1969-12-29 | 1972-02-01 | Lubrizol Corp | Lubricating oil or fuel containing sludge-dispersing additive |
US3697428A (en) | 1969-04-01 | 1972-10-10 | Lubrizol Corp | Additives for lubricants and fuels |
US3708522A (en) | 1969-12-29 | 1973-01-02 | Lubrizol Corp | Reaction products of high molecular weight carboxylic acid esters and certain carboxylic acid acylating reactants |
US3755169A (en) | 1970-10-13 | 1973-08-28 | Lubrizol Corp | High molecular weight carboxylic acid acylating agents and the process for preparing the same |
US3804763A (en) | 1971-07-01 | 1974-04-16 | Lubrizol Corp | Dispersant compositions |
US3836470A (en) | 1973-05-14 | 1974-09-17 | Lubrizol Corp | Lubricants and fuels containing ester-containing compositions |
FR2223415A1 (en) | 1973-03-30 | 1974-10-25 | Mobil Oil | |
US3862981A (en) | 1971-07-08 | 1975-01-28 | Rhone Progil | New lubricating oil additives |
US3912764A (en) | 1972-09-29 | 1975-10-14 | Cooper Edwin Inc | Preparation of alkenyl succinic anhydrides |
US3936480A (en) | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
US3948909A (en) | 1974-06-26 | 1976-04-06 | Toa Nenryo Kogyo Kabushiki Kaisha | Ashless detergent dispersant for hydrocarbon oils |
US3950341A (en) | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
GB1492337A (en) | 1975-05-29 | 1977-11-16 | Lubrizol Corp | Process for making succinic acid acylating agents |
US4110349A (en) | 1976-06-11 | 1978-08-29 | The Lubrizol Corporation | Two-step method for the alkenylation of maleic anhydride and related compounds |
US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
US4329249A (en) | 1978-09-27 | 1982-05-11 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines and lubricants or functional fluids containing the same |
US4368133A (en) | 1979-04-02 | 1983-01-11 | The Lubrizol Corporation | Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives |
US4435297A (en) | 1978-09-27 | 1984-03-06 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines |
US4447348A (en) | 1981-02-25 | 1984-05-08 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4448703A (en) | 1981-02-25 | 1984-05-15 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4471091A (en) | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4642330A (en) | 1984-12-27 | 1987-02-10 | The Lubrizol Corporation | Dispersant salts |
US4828633A (en) | 1987-12-23 | 1989-05-09 | The Lubrizol Corporation | Salt compositions for explosives |
US5047175A (en) | 1987-12-23 | 1991-09-10 | The Lubrizol Corporation | Salt composition and explosives using same |
US5422024A (en) | 1993-12-08 | 1995-06-06 | The Lubrizol Corporation | Aqueous functional fluids |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6648929B1 (en) * | 1998-09-14 | 2003-11-18 | The Lubrizol Corporation | Emulsified water-blended fuel compositions |
EP1684895B1 (en) * | 2003-11-12 | 2008-06-04 | The Lubrizol Corporation | Emulsifier blend replacement for natural sodium sulfonates in metalworking applications |
-
2015
- 2015-01-28 KR KR1020167027233A patent/KR20160128406A/en not_active Application Discontinuation
- 2015-01-28 CN CN201580022317.8A patent/CN106232783A/en not_active Withdrawn
- 2015-01-28 CA CA2942145A patent/CA2942145A1/en not_active Abandoned
- 2015-01-28 EP EP15705414.9A patent/EP3114195A2/en not_active Withdrawn
- 2015-01-28 US US15/246,624 patent/US20170022443A1/en not_active Abandoned
- 2015-01-28 JP JP2016555589A patent/JP2017510438A/en active Pending
- 2015-01-28 WO PCT/US2015/013177 patent/WO2015134129A2/en active Application Filing
Patent Citations (58)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892786A (en) | 1956-02-03 | 1959-06-30 | California Research Corp | Lubricant composition |
US3341542A (en) | 1959-03-30 | 1967-09-12 | Lubrizol Corp | Oil soluble acrylated nitrogen compounds having a polar acyl, acylimidoyl or acyloxy group with a nitrogen atom attached directly thereto |
US3219666A (en) | 1959-03-30 | 1965-11-23 | Derivatives of succinic acids and nitrogen compounds | |
US3172892A (en) | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3215707A (en) | 1960-06-07 | 1965-11-02 | Lubrizol Corp | Lubricant |
US3231587A (en) | 1960-06-07 | 1966-01-25 | Lubrizol Corp | Process for the preparation of substituted succinic acid compounds |
US3200106A (en) | 1960-08-04 | 1965-08-10 | Petrolite Corp | Derivatives of branched polyalkylene-polyamines |
US3259578A (en) | 1960-08-04 | 1966-07-05 | Petrolite Corp | Lubricating compositions |
US3087936A (en) | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3288714A (en) | 1961-12-06 | 1966-11-29 | Monsanto Co | Lubricating oil compositions containing alkenyl succinic anhydrides |
US3331776A (en) | 1962-10-04 | 1967-07-18 | Shell Oil Co | Lubricating oil composition |
US3189544A (en) | 1962-12-19 | 1965-06-15 | Shell Oil Co | Non-ash-containing lubricating oil composition |
US3235503A (en) | 1963-03-28 | 1966-02-15 | Chevron Res | Lubricant containing alkylene polyamine reaction product |
US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
US3306907A (en) | 1963-04-29 | 1967-02-28 | Standard Oil Co | Process for preparing n n-di |
US3346354A (en) | 1963-07-02 | 1967-10-10 | Chvron Res Company | Long-chain alkenyl succinic acids, esters, and anhydrides as fuel detergents |
US3163603A (en) | 1963-12-11 | 1964-12-29 | Lubrizol Corp | Amide and imide derivatives of metal salts of substituted succinic acids |
US3306908A (en) | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3216936A (en) | 1964-03-02 | 1965-11-09 | Lubrizol Corp | Process of preparing lubricant additives |
US3413104A (en) | 1964-12-10 | 1968-11-26 | Chevron Res | Imides of olefin-maleic anhydride copolymers as diesel fuel additives |
US3379515A (en) | 1965-04-09 | 1968-04-23 | Eddie G. Lindstrom | High molecular weight imide substituted polymers as fuel detergents |
US3450715A (en) | 1965-04-09 | 1969-06-17 | Chevron Res | N-hydrocarbon succinimidyl polymers |
US3523768A (en) | 1965-04-28 | 1970-08-11 | Chevron Res | Ester modified polymers as fuel dispersants |
US3455728A (en) | 1965-10-04 | 1969-07-15 | Inland Steel Co | Centrifugal spray coating methods and apparatus |
US3272746A (en) | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
US3374174A (en) | 1966-04-12 | 1968-03-19 | Lubrizol Corp | Composition |
US3513095A (en) | 1967-02-20 | 1970-05-19 | Texaco Inc | Lubricating oil composition of improved dispersancy,viscosity index and shear stability |
US3476686A (en) | 1968-06-04 | 1969-11-04 | Sinclair Research Inc | Ashless lubricating oil detergents |
US3630904A (en) | 1968-07-03 | 1971-12-28 | Lubrizol Corp | Lubricating oils and fuels containing acylated nitrogen additives |
US3454607A (en) | 1969-02-10 | 1969-07-08 | Lubrizol Corp | High molecular weight carboxylic compositions |
US3697428A (en) | 1969-04-01 | 1972-10-10 | Lubrizol Corp | Additives for lubricants and fuels |
US3576743A (en) | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
US3632511A (en) | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
US3639242A (en) | 1969-12-29 | 1972-02-01 | Lubrizol Corp | Lubricating oil or fuel containing sludge-dispersing additive |
US3708522A (en) | 1969-12-29 | 1973-01-02 | Lubrizol Corp | Reaction products of high molecular weight carboxylic acid esters and certain carboxylic acid acylating reactants |
US3755169A (en) | 1970-10-13 | 1973-08-28 | Lubrizol Corp | High molecular weight carboxylic acid acylating agents and the process for preparing the same |
US3804763A (en) | 1971-07-01 | 1974-04-16 | Lubrizol Corp | Dispersant compositions |
US3948800A (en) | 1971-07-01 | 1976-04-06 | The Lubrizol Corporation | Dispersant compositions |
US3936480A (en) | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
US3862981A (en) | 1971-07-08 | 1975-01-28 | Rhone Progil | New lubricating oil additives |
US3912764A (en) | 1972-09-29 | 1975-10-14 | Cooper Edwin Inc | Preparation of alkenyl succinic anhydrides |
FR2223415A1 (en) | 1973-03-30 | 1974-10-25 | Mobil Oil | |
US3950341A (en) | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
US3836470A (en) | 1973-05-14 | 1974-09-17 | Lubrizol Corp | Lubricants and fuels containing ester-containing compositions |
US3948909A (en) | 1974-06-26 | 1976-04-06 | Toa Nenryo Kogyo Kabushiki Kaisha | Ashless detergent dispersant for hydrocarbon oils |
GB1492337A (en) | 1975-05-29 | 1977-11-16 | Lubrizol Corp | Process for making succinic acid acylating agents |
US4110349A (en) | 1976-06-11 | 1978-08-29 | The Lubrizol Corporation | Two-step method for the alkenylation of maleic anhydride and related compounds |
US4435297A (en) | 1978-09-27 | 1984-03-06 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines |
US4329249A (en) | 1978-09-27 | 1982-05-11 | The Lubrizol Corporation | Carboxylic acid derivatives of alkanol tertiary monoamines and lubricants or functional fluids containing the same |
US4234435A (en) | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
US4368133A (en) | 1979-04-02 | 1983-01-11 | The Lubrizol Corporation | Aqueous systems containing nitrogen-containing, phosphorous-free carboxylic solubilizer/surfactant additives |
US4447348A (en) | 1981-02-25 | 1984-05-08 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4448703A (en) | 1981-02-25 | 1984-05-15 | The Lubrizol Corporation | Carboxylic solubilizer/surfactant combinations and aqueous compositions containing same |
US4471091A (en) | 1982-08-09 | 1984-09-11 | The Lubrizol Corporation | Combinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same |
US4642330A (en) | 1984-12-27 | 1987-02-10 | The Lubrizol Corporation | Dispersant salts |
US4828633A (en) | 1987-12-23 | 1989-05-09 | The Lubrizol Corporation | Salt compositions for explosives |
US5047175A (en) | 1987-12-23 | 1991-09-10 | The Lubrizol Corporation | Salt composition and explosives using same |
US5422024A (en) | 1993-12-08 | 1995-06-06 | The Lubrizol Corporation | Aqueous functional fluids |
Non-Patent Citations (1)
Title |
---|
KIRK-OTHMER: "The Encyclopedia of Chemical Technology", vol. 7, 1979, WILEY-INTERSCIENCE PUBLICATION, JOHN WILEY AND SONS, article "Diamines and Higher Amines, Aliphatic", pages: 580 - 602 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112410095A (en) * | 2020-12-01 | 2021-02-26 | 浙江可思克高新材料股份有限公司 | Preparation method of lubricant |
Also Published As
Publication number | Publication date |
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KR20160128406A (en) | 2016-11-07 |
EP3114195A2 (en) | 2017-01-11 |
CA2942145A1 (en) | 2015-09-11 |
CN106232783A (en) | 2016-12-14 |
JP2017510438A (en) | 2017-04-13 |
WO2015134129A3 (en) | 2016-03-24 |
US20170022443A1 (en) | 2017-01-26 |
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