DE1284014B - Schmieroel - Google Patents
SchmieroelInfo
- Publication number
- DE1284014B DE1284014B DEM61680A DEM0061680A DE1284014B DE 1284014 B DE1284014 B DE 1284014B DE M61680 A DEM61680 A DE M61680A DE M0061680 A DEM0061680 A DE M0061680A DE 1284014 B DE1284014 B DE 1284014B
- Authority
- DE
- Germany
- Prior art keywords
- ketone
- methyl
- polybutenyl
- succinimido
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 6
- -1 succinimidoimidazolidine Chemical compound 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 11
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 9
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002461 imidazolidines Chemical class 0.000 description 4
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Chemical compound CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- GSNKRSKIWFBWEG-UHFFFAOYSA-N 3-ethylpentan-2-one Chemical compound CCC(CC)C(C)=O GSNKRSKIWFBWEG-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- BSABBBMNWQWLLU-UHFFFAOYSA-N lactaldehyde Chemical compound CC(O)C=O BSABBBMNWQWLLU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- FWWQKRXKHIRPJY-UHFFFAOYSA-N octadecanal Chemical compound CCCCCCCCCCCCCCCCCC=O FWWQKRXKHIRPJY-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XGQJZNCFDLXSIJ-UHFFFAOYSA-N pentadecanal Chemical compound CCCCCCCCCCCCCCC=O XGQJZNCFDLXSIJ-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 2
- BGEHHAVMRVXCGR-UHFFFAOYSA-N tridecanal Chemical compound CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 2
- DPCMFIRORYQTCL-NSCUHMNNSA-N (Z)-4-Hexenal Chemical compound C\C=C\CCC=O DPCMFIRORYQTCL-NSCUHMNNSA-N 0.000 description 1
- NRXZYQITMVTQIB-BQYQJAHWSA-N (e)-dec-3-enal Chemical compound CCCCCC\C=C\CC=O NRXZYQITMVTQIB-BQYQJAHWSA-N 0.000 description 1
- GXANMBISFKBPEX-ONEGZZNKSA-N (e)-hex-3-enal Chemical compound CC\C=C\CC=O GXANMBISFKBPEX-ONEGZZNKSA-N 0.000 description 1
- ICPZCFJMCZRIPY-SNAWJCMRSA-N (e)-oct-4-enal Chemical compound CCC\C=C\CCC=O ICPZCFJMCZRIPY-SNAWJCMRSA-N 0.000 description 1
- WUCQRXWCJPCWTQ-NSCUHMNNSA-N (e)-pent-3-enal Chemical compound C\C=C\CC=O WUCQRXWCJPCWTQ-NSCUHMNNSA-N 0.000 description 1
- JPJOOTWNILDNAW-UHFFFAOYSA-N 1-cyclobutylethanone Chemical compound CC(=O)C1CCC1 JPJOOTWNILDNAW-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 description 1
- OXVISHZELPRKFQ-UHFFFAOYSA-N 2,2,3-trichlorobutanal Chemical compound CC(Cl)C(Cl)(Cl)C=O OXVISHZELPRKFQ-UHFFFAOYSA-N 0.000 description 1
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- UQHUGDVZNYJETO-UHFFFAOYSA-N 2-ethylhex-3-enal Chemical compound CCC=CC(CC)C=O UQHUGDVZNYJETO-UHFFFAOYSA-N 0.000 description 1
- XYYMFUCZDNNGFS-UHFFFAOYSA-N 2-methylheptan-3-one Chemical compound CCCCC(=O)C(C)C XYYMFUCZDNNGFS-UHFFFAOYSA-N 0.000 description 1
- QSHJLBQLQVSEFV-UHFFFAOYSA-N 3,3-dimethylpentan-2-one Chemical compound CCC(C)(C)C(C)=O QSHJLBQLQVSEFV-UHFFFAOYSA-N 0.000 description 1
- QXHRQZNDMYRDPA-UHFFFAOYSA-N 3,4-dimethylpentan-2-one Chemical compound CC(C)C(C)C(C)=O QXHRQZNDMYRDPA-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- GYWYASONLSQZBB-UHFFFAOYSA-N 3-methylhexan-2-one Chemical compound CCCC(C)C(C)=O GYWYASONLSQZBB-UHFFFAOYSA-N 0.000 description 1
- CAVUEALRYKNYRW-UHFFFAOYSA-N 3-methylhexane-2,4-dione Chemical compound CCC(=O)C(C)C(C)=O CAVUEALRYKNYRW-UHFFFAOYSA-N 0.000 description 1
- QSFGGYJTGKYFML-UHFFFAOYSA-N 3-methylpent-4-en-2-one Chemical compound C=CC(C)C(C)=O QSFGGYJTGKYFML-UHFFFAOYSA-N 0.000 description 1
- AZASWMGVGQEVCS-UHFFFAOYSA-N 4,4-dimethylpentan-2-one Chemical compound CC(=O)CC(C)(C)C AZASWMGVGQEVCS-UHFFFAOYSA-N 0.000 description 1
- QUMSUJWRUHPEEJ-UHFFFAOYSA-N 4-Pentenal Chemical compound C=CCCC=O QUMSUJWRUHPEEJ-UHFFFAOYSA-N 0.000 description 1
- XUPXMIAWKPTZLZ-UHFFFAOYSA-N 4-methylhexan-2-one Chemical compound CCC(C)CC(C)=O XUPXMIAWKPTZLZ-UHFFFAOYSA-N 0.000 description 1
- USLRUYZDOLMIRJ-UHFFFAOYSA-N 5-Hexenal Chemical compound C=CCCCC=O USLRUYZDOLMIRJ-UHFFFAOYSA-N 0.000 description 1
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- VBCIOOKAKHGVMI-UHFFFAOYSA-N 5-methylhex-5-en-2-one Chemical compound CC(=C)CCC(C)=O VBCIOOKAKHGVMI-UHFFFAOYSA-N 0.000 description 1
- WDMOXLRWVGEXJV-UHFFFAOYSA-N 8-methylnonanal Chemical compound CC(C)CCCCCCC=O WDMOXLRWVGEXJV-UHFFFAOYSA-N 0.000 description 1
- UMHJEEQLYBKSAN-UHFFFAOYSA-N Adipaldehyde Chemical compound O=CCCCCC=O UMHJEEQLYBKSAN-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000006001 Methyl nonyl ketone Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N Undecanal Natural products CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IWJMQXOBCQTQCF-UHFFFAOYSA-N but-3-enal Chemical compound C=CCC=O IWJMQXOBCQTQCF-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZNWNWEHQFXOPGK-UHFFFAOYSA-N decanedial Chemical compound O=CCCCCCCCCC=O ZNWNWEHQFXOPGK-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- WFSXUTWNNVIIIG-ZPUQHVIOSA-N glutaconaldehyde Chemical compound O\C=C\C=C\C=O WFSXUTWNNVIIIG-ZPUQHVIOSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- SILICPHIUHBJGQ-UHFFFAOYSA-N hept-1-en-4-one Chemical compound CCCC(=O)CC=C SILICPHIUHBJGQ-UHFFFAOYSA-N 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical compound CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 description 1
- NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- JGEMYUOFGVHXKV-UPHRSURJSA-N malealdehyde Chemical compound O=C\C=C/C=O JGEMYUOFGVHXKV-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 1
- OADYBSJSJUFUBR-UHFFFAOYSA-N octanedial Chemical compound O=CCCCCCCC=O OADYBSJSJUFUBR-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 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
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- LUUDAJQADHSYHX-UHFFFAOYSA-N tridecanedial Chemical compound O=CCCCCCCCCCCCC=O LUUDAJQADHSYHX-UHFFFAOYSA-N 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N60/00—Superconducting devices
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/48—Isomerisation; Cyclisation
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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- C—CHEMISTRY; METALLURGY
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Description
Alkenylbernsteinsäureimide sind als Schmierölzusätze
hinreichend bekannt. Sie haben jedoch den Nachteil, daß sie zur Bildung ölunlöslicher Oxydationsprodukte
neigen, die störende Ablagerungen, beispielsweise in Verbrennungsmotoren, verursachen.
Es wurde gefunden, daß dieser Nachteil beseitigt wird, wenn man einem Schmieröl ein l-Polyalkenylsuccinimidoimidazolidin
der Formel
O Il |
S. | f | CH2- | -NH | I | |
R-CH | Il — Cn |
\ N — / |
||||
/ | ||||||
CH; | 1 Ϊ O |
|||||
-CH- | ||||||
R1 | ||||||
H2C-
— CH2 — CH — N
R1
R1
R1
-CH
C-R2
R3
worin R ein Olefinpolymerisat mit einem Molekulargewicht von 500 bis 2500 und χ eine ganze Zahl von
0 bis 3 ist und, wenn η = 1, R1 Wasserstoff und/oder einen niederen Alkylrest bedeutet, R2 und R3 Wasserstoff,
Alkyl, Alkenyl und/oder Haloalkyl und, wenn η = 2, R2 nur Wasserstoff und/oder niederes Alkyl
und R3 Alkylen oder Alkenylen von 1 bis 16 Kohlenstoffatomen
ist, zusetzt.
Die Imidazoline werden hergestellt durch Umsetzen
(a) eines Alkenylbernsteinsäureanhydrids oder der Säure derselben,
(b) eines Polyäthylenamins, dargestellt durch die Struktur
H2N
ptt /"1U TvTU CU
,
35
CH — NH — CH2 — CH-NH2
R1 Rj
und
(c) einer Carbonyl enthaltenden Verbindung, d. h. eines Aldehyds oder Ketons, dargestellt durch
die Struktur
oder eines Dialdehyds oder Diketons, dargestellt durch die Struktur
O O
V^ £-1 K^
1x4
rc
worin R, R1, R2, R3, R4, χ und Z die gleiche Bedeutung
haben. Die verwendeten Molverhältnisse von (a): (b): (c) können ungefähr 1:1:1, um mono-Imidazolidine
herzustellen, und ungefähr 2:.2:1, um bis-Imidazolidine herzustellen, haben. Normalerweise
werden (b) und (c) umgesetzt, um ein Zwischenproduktimidazolidin herzustellen, welches mit (a)
umgesetzt wird, um die Verbindungen dieser Erfindung herzustellen. Um ein .Reaktionsmedium zu
schaffen und das Entfernen des Wassers der Reaktion zu erleichtern, kann ein Kohlenwasserstofflösungsmittel,
z.B. Toluol oder Xylol, verwendet werden.
Ebenso kann ein mineralisches öl als Reaktionsmedium entweder allein oder zusammen mit einem
Kohlenwasserstofflösungsmittel verwendet werden. Geeignete Temperaturen zur Herstellung von Imidazolidinen
bei atmosphärischem Druck liegen im Bereich von 100 bis 175° C, und es kann im Falle
eines Mineralölreaktionsmediums Vakuum verwendet werden, um unter ungefähr den gleichen Temperaturen
zu arbeiten.
Die Alkenylbernsteinsäureanhydride werden nach den üblichen Methoden hergestellt.
Polyäthylenamine sind z. B. Diäthylentriamin, Di-(methyläthylen) - triamin, Triäthylentetramin, Tri-(methyläthylen)-tetramin,
Tri-(äthyläthylen)-tetramin, Tetraäthylenpentamin und Pentaäthylenhexamin.
Carbonyl und Dicarbonyl enthaltende Verbindungen sind z. B.
Aldehyde, wie Formaldehyd, Acetaldehyd, Propionaldehyd, n-Butyraldehyd, Isobutyraldehyd,
η - Valeraldehyd, Isovaleraldehyd, Pivaldehyd, alpha - Methylbutyraldehyd, Caproaldehyd,
tert. Butylacetaldehyd, Heptaldehyd, Pelagonaldehyd,Nonaldehyd, Capraldehyd, Lauraldehyd,
Tridecanal, Myristaldehyd, Pentadecanal, Palmitaldehyd, Heptodecanal, Stearaldehyd; substituierte
Aldehyde, wie Chloracetaldehyd, Chloral, Butylchloral, Trifluoracetaldehyd, Aldol, 2-Hydroxypropionaldehyd;
ungesättigte Aldehyde, wie Methacrolein, Acrolein, Crotonaldehyd, 3-Butenal,
3- und 4-Pentenal, 3-, 4- und 5-Hexenal, 4-Octenal, 2-Äthyl-3-hexenal, 3-Decenal, wobei
solche, in denen die ungesättigte Stelle nicht in 2-, 3-Stellung ist, oft bevorzugt werden;
Ketone, wie Aceton, Methyl-äthyl-keton, Methylpropyl-keton,
Methyl-isopropyl-keton, Methylbutyl-keton,
Methyl-isobutyl-keton, Methylsek. butyl - keton, Methyl - tert. butyl - keton,
Methyl - cyclobutyl - keton, Methyl - neopentylketon, Methyl-tert.amyl-keton, Methyl-n-amylketon,
Methyl - hexyl - keton, Methyl - cyclohexyl-keton, Methyl-n-heptyl-keton, Methyln-octyl-keton,
Methyl-nonyl-keton, Methyldecyl-keton,
Diäthyl-keton, Di-n-propyl-keton, Diisopropyl - keton, Äthyl - isopropyl - keton,
Äthyl - η - propyl - keton, Äthyl - tert. butyl - keton, Äthyl - η - butyl - keton, tert. Butyl - isopropylketon,
η - Propyl - isopropyl - keton, η - Propyltert.butyl-keton,
Diisobutyl-keton, 2-Decanon; substituierte Ketone, wie 3- und 4-Methyl-2-hexanon,
3,4 - Dimethyl - 2 - pentanon, 3 - Äthyl-2-pentanon;
ungesättigte Ketone, wie Allylaceton,
2- und 3-Methyl-l-penten-4-on, l-Hepten-4-on, 3-Methyl-l-hexen-S-on, 5-Methyl-5-hexen-2-on;
oder
a) Aldehyde, wie Glyoxal, Malonaldehyd, Succinaldehyd, Glutaraldehyd, Adipaldehyd, Pimelaldehyd,
Suberaldehyd, Azelaldehyd, Sebacaldehyd, Brassaldehyd, Brassylaldehyd, Rocellaldehyd;
ungesättigte di-Aldehyde, wie Malealdehyd, Glutaconaldehyd;
b) Ketone, wie Diacetyl, Acetylaceton, Acetonylaceton, 2,3-Hexandion, 2,4-Heptandion, 3-Methyl-2,4-hexandion,
2,5-Hexandion, 2,3-Octandion.
Ein detailliertes allgemeines Herstellungsverfahren der Imidazolidine dieser Erfindung verläuft wie folgt:
In einem Reaktionskolben wurden 23,3 g Tetraäthylenpentamin (0,1234 Mol) und ungefähr 80 ml
Toluol eingebracht. Unter Rühren wurden dann 8,9 g n-Butyraldehyd (0,1234 Mol) langsam eingebracht
und das sich ergebende Gemisch am Rückfluß ungefähr 2 Stunden erhitzt, wobei das durch die
Reaktion gebildete Wasser entfernt wurde.
Nach Abkühlen wurden 169 Teile (0,1234MoI)
eines Polybutenylbernsteinsäureanhydrids (Alkenylrest mit einem Durchschnittsmolekulargewicht von
ungefähr 980) in 100-ml Toluol langsam eingebracht,
und das Gemisch wurde am Rückfluß ungefähr 2 Stunden unter Entfernung des Wassers erhitzt.
Das Toluol wurde im Vakuum abgestreift, 1 - [8 - (Polybutenylbernsteinimido) - 3,6 - diazaoctyl]-2-propylimidazolidin
blieben zurück.
In der Tabelle I bedeutet:.
DETA = Diäthylentriamin,
TETA = Triäthylentetramin und
TEPA = Tetraäthylenpentamin.
TETA = Triäthylentetramin und
TEPA = Tetraäthylenpentamin.
Alkenylanteil des | Polyäthylen- | Carbonyl enthaltende | Molar verhältnis |
Produkt | |
Bei- | Alkenylbernsteinsäure- anhydrids (a) |
amin (b) | Verbindung (c) | (a):(b):(c) | |
spiel | (Molekulargewicht der | ||||
Alkenylgruppe) | TEPA | Formaldehyd | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | |
Polybutenyl (980) | 3,6-diazaoctyl]-imidazolidin | ||||
TEPA | Acetaldehyd | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
3 | Polybutenyl (980) | 3,6-diazaoctyl]-2-methyl- | |||
imidazolidin | |||||
TEPA | Isodecylaldehyd | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
4 | Polybutenyl (980) | 3,6-diazaoctyl]-2-nonyl- | |||
imidazolidin | |||||
DETA | Glutaraldehyd | 2:2:1 | Trimethylen-bis-[l -(8-(poly- | ||
5 | Polybutenyl (1190) | butenylsuccinimido)-3,6-diaza- | |||
octyl)-2-imidazolidin] | |||||
TEPA | Aceton | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
6 | Polybuteny] (980) | 3,6-diazaoctyl]-2-dimethyl- | |||
imidazolidin | |||||
TEPA | Cyclohexanon | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
7 | Polybutenyl (980) | 3,6-diazaoctyl]-1,4-diazaspiro- | |||
[4,,5]-decan | |||||
DETA | Acetylaceton | 2:2:1 | 2,2'-Methylen-bis-[l-((8-poly- | ||
8 | Polybutenyl (980) | butenylsuccinimido)-3,6-diaza- | |||
octyl)-imidazolidin] | |||||
DETA | Glutaraldehyd | 2:2:1 | Trimethylen-bis-[l-(2-(poly- | ||
9 | Polybutenyl (1315) | butenylsuccinimido)-äthyl)- | |||
2-imidazolidin] | |||||
TEPA | n-Butyraldehyd | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
10 | Polybutenyl (1315) | 3,6-diazaoctyl]-2-propyl- | |||
imidazolidin | |||||
DETA | n-Butyraldehyd | 1:1:1 | 1 -[2-(Polybutenylsuccinimido)- | ||
11 | Polybutenyl (980) | äthyl]-2-propylimidazolidin | |||
DETA | 2-Propenal | 1:1:1 | 1 -[2-(Polybutenylsuccinimido)- | ||
12 | Polybutenyl (980) | äthyl]-2-vinylimidazolidin | |||
TETA | 2-Methyl-2-pro- | 1:1:1 | 1 -[5-(Polybutenylsuccinimido)- | ||
13 | Polybutenyl (980) | penal | 3-azapentyl]-2-(/3-allyl)- | ||
imidazolidin | |||||
TEPA | 2-Butenal | 1:1:1 | 1 -[8-(Polybutenylsuccinimido)- | ||
14 | Polybutenyl (980) | 3,6-diazaoctyl]-2-propenyl- | |||
imidazoüdin | |||||
Als Basisschmieröle werden natürliche oder synthetische öle verwendet.
Die Imidazolidine und bis-Imidazolidine dieser
Erfindung werden diesen Schmierölen in Mengen von 0,05 bis 25 Gewichtsprozent zugesetzt.
Die Wirksamkeit der Imidazolidine dieser Erfindung, welche Niedertemperatur - Reinigungseigenschaften
verleihen, wird durch die Ergebnisse eines Reinigungsversuchs erläutert, der in der Literatur als
»Lackablagerungstest« bezeichnet wird und darin to besteht, daß abgebrannte Gasolindämpfe durch eine
Probe einer Zubereitung in einem geeigneten Behälter unter Kontrollbedingungen durchgeleitet werden, wonach
die Probe in einem Ofen gealtert wird. Die Ablagerungsmenge wird dann durch Auswaschen
des Öls mit Hexan bestimmt. Eine Kontrollzubereitung wird in gleicher Weise behandelt. Die Menge
der vorhandenen Ablagerungen, wenn das Untersuchungsreinigungsmittel verwendet wird, im Vergleich
zu der Menge der Ablagerungen, die vorhanden sind, wenn kein Reinigungsmittel verwendet wird,
wird als Prozent der Ablagerungsverringerung aufgezeigt. Bei Verwenden des oben angegebenen Versuchs
wurden die in der untenstehenden Tabelle II dargestellten Ergebnisse erhalten.
R-CH CS
CH.-C-
Additiv . | Gewichts | Lackablagerungs test prozentuale |
prozent | Verringerung | |
Produkt von Beispiel 1 ... | 2 | 100 |
Produkt von Beispiel 2 ... | 2 | 92 |
Produkt von Beispiel 3 ... | 2 | 94 |
Produkt von Beispiel 4... | 2 | 100 |
Produkt von Beispiel 5 ... | 2 | 69 |
Produkt von Beispiel 6 ... | 2 | 90 |
Produkt von Beispiel 7 ... | 2 | 94 |
Produkt von Beispiel 8... | 2 | 98 |
Produkt von Beispiel 9 ... | 2 | 69 |
Produkt von Beispiel 10 .. | 1 | 99 |
Produkt von Beispiel 11.. | 2 | 98 |
Claims (1)
- Patentanspruch:Schmieröl, gekennzeichnet durch einen Gehall an l-Polyalkenylsuccinimidoimidazolidin der FormelN —CH2-CH-NH H2C-
-CH2-CH-NR1C-R1 CHR2R3worin R ein Olefinpolymerisat mit einem Molekulargewicht von 500 bis 2500 und .v eine ganze Zahl von 0 bis 3 ist und, wenn η = 1. R1 Wasserstoff und oder einen niederen Alkylrest bedeutet.R2 und R3 Wasserstoff, Alkyl, Alkenyl und/oder Haloalkyl und, wenn η = 2, R2 nur Wasserstoff und'oder niederes Alkyl und R3 Alkylen oder Alkenylen von 1 bis 16 Kohlenstoffatomen ist.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29648963A | 1963-07-22 | 1963-07-22 | |
US312292A US3280034A (en) | 1963-07-22 | 1963-09-30 | Alkenylsuccinimido alkyl-substituted imidazolidines and related materials |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1284014B true DE1284014B (de) | 1968-11-28 |
Family
ID=26969680
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEM61680A Pending DE1284014B (de) | 1963-07-22 | 1964-07-10 | Schmieroel |
Country Status (7)
Country | Link |
---|---|
US (1) | US3280034A (de) |
BE (1) | BE650770A (de) |
DE (1) | DE1284014B (de) |
ES (1) | ES302190A1 (de) |
IL (1) | IL21746A (de) |
NL (1) | NL6408242A (de) |
SE (1) | SE317083B (de) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3415750A (en) * | 1963-10-04 | 1968-12-10 | Monsanto Co | Imidazolines having polyalkenylsuccinimido-containing substituents |
US3497334A (en) * | 1963-12-16 | 1970-02-24 | Mobil Oil Corp | Liquid hydrocarbon combustion fuels |
US3390086A (en) * | 1964-12-29 | 1968-06-25 | Exxon Research Engineering Co | Sulfur containing ashless disperant |
US3369021A (en) * | 1966-03-07 | 1968-02-13 | Lubrizol Corp | Preparation of lubricant additives with reduced odor |
US3445386A (en) * | 1967-01-13 | 1969-05-20 | Mobil Oil Corp | Detergent compositions |
US4579675A (en) * | 1983-11-09 | 1986-04-01 | Texaco Inc. | N-substituted enaminones and oleaginous compositions containing same |
CA1339530C (en) * | 1987-05-18 | 1997-11-04 | Antonio Gutierrez | Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants |
US4839072A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts |
US4839073A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate and substituted acetate adducts as compatibilizer additives in lubricating oil compositions |
US4906252A (en) * | 1987-05-18 | 1990-03-06 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in fuel oil compositions |
US4839071A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adducts as dispersants in lubricating oil compositions |
US4839070A (en) * | 1987-05-18 | 1989-06-13 | Exxon Chemical Patents Inc. | Polyolefinic succinimide polyamine alkyl acetoacetate adduct dispersants |
US5273668A (en) * | 1989-01-30 | 1993-12-28 | Exxon Chemical Patents Inc. | Oil soluble dispersant additives modified with bis-keto/thioketo compounds |
US5158696A (en) * | 1989-01-30 | 1992-10-27 | Exxon Chemical Patents Inc. | Oil soluble dispersant additives modified with bis-keto/thioketo compounds |
GB8911732D0 (en) | 1989-05-22 | 1989-07-05 | Ethyl Petroleum Additives Ltd | Lubricant compositions |
US5646098A (en) * | 1990-07-23 | 1997-07-08 | Exxon Chemical Patents Inc | Carbonyl containing compounds and their derivatives as multi-functional fuel and lube additives |
IL107810A0 (en) * | 1992-12-17 | 1994-02-27 | Exxon Chemical Patents Inc | Functionalized polymers and processes for the preparation thereof |
US5650536A (en) * | 1992-12-17 | 1997-07-22 | Exxon Chemical Patents Inc. | Continuous process for production of functionalized olefins |
US5643859A (en) * | 1992-12-17 | 1997-07-01 | Exxon Chemical Patents Inc. | Derivatives of polyamines with one primary amine and secondary of tertiary amines |
US5646332A (en) * | 1992-12-17 | 1997-07-08 | Exxon Chemical Patents Inc. | Batch Koch carbonylation process |
US5767046A (en) * | 1994-06-17 | 1998-06-16 | Exxon Chemical Company | Functionalized additives useful in two-cycle engines |
US6043199A (en) * | 1997-08-26 | 2000-03-28 | Exxon Research And Engineering Co. | Corrosion inhibiting additive combination for turbine oils |
DE60135889D1 (de) * | 2000-03-17 | 2008-11-06 | Hitachi Ltd | Bildanzeigevorrichtung |
US7947636B2 (en) | 2004-02-27 | 2011-05-24 | Afton Chemical Corporation | Power transmission fluids |
US7563314B2 (en) * | 2005-11-30 | 2009-07-21 | Xerox Corporation | Ink carriers containing nanoparticles, phase change inks including same and methods for making same |
US7655084B2 (en) * | 2005-12-12 | 2010-02-02 | Xerox Corporation | Carbon black inks and method for making same |
US7786209B2 (en) * | 2006-10-27 | 2010-08-31 | Xerox Corporation | Nanostructured particles, phase change inks including same and methods for making same |
US20080098930A1 (en) * | 2006-11-01 | 2008-05-01 | Xerox Corporation | Colorant dispersant |
US8123344B2 (en) * | 2008-08-04 | 2012-02-28 | Xerox Corporation | Ink carriers containing surface modified nanoparticles, phase change inks including same, and methods for making same |
US8029861B2 (en) * | 2008-09-23 | 2011-10-04 | Xerox Corporation | Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same |
US8177897B2 (en) * | 2008-11-17 | 2012-05-15 | Xerox Corporation | Phase change inks containing graphene-based carbon allotrope colorants |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1254094A (fr) * | 1960-03-29 | 1961-02-17 | Lubrizol Corp | Additifs exempts de métaux pour lubrifiants |
FR1265085A (fr) * | 1959-08-24 | 1961-06-23 | California Research Corp | Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2877179A (en) * | 1956-03-26 | 1959-03-10 | Cities Service Res & Dev Co | Composition for and method of inhibiting corrosion of metals |
FR1265086A (fr) * | 1959-08-24 | 1961-06-23 | California Research Corp | Compositions d'huiles lubrifiantes renfermant des alkényl succinimides de la tétraéthylène pentamine |
US3131150A (en) * | 1961-04-12 | 1964-04-28 | California Research Corp | Lubricating oil compositions containing n-substituted alkenyl succinimides in combination with polyamines |
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 |
-
1963
- 1963-09-30 US US312292A patent/US3280034A/en not_active Expired - Lifetime
-
1964
- 1964-07-10 DE DEM61680A patent/DE1284014B/de active Pending
- 1964-07-17 NL NL6408242A patent/NL6408242A/xx unknown
- 1964-07-17 ES ES302190A patent/ES302190A1/es not_active Expired
- 1964-07-20 BE BE650770D patent/BE650770A/xx unknown
- 1964-07-21 SE SE8876/64A patent/SE317083B/xx unknown
- 1964-07-22 IL IL21746A patent/IL21746A/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1265085A (fr) * | 1959-08-24 | 1961-06-23 | California Research Corp | Compositions d'huiles lubrifiantes renfermant des n-dialkylaminoalkyl alkényl succinimides |
FR1254094A (fr) * | 1960-03-29 | 1961-02-17 | Lubrizol Corp | Additifs exempts de métaux pour lubrifiants |
Also Published As
Publication number | Publication date |
---|---|
SE317083B (de) | 1969-11-10 |
NL6408242A (de) | 1965-01-25 |
BE650770A (de) | 1964-11-16 |
US3280034A (en) | 1966-10-18 |
IL21746A (en) | 1968-05-30 |
ES302190A1 (es) | 1964-09-16 |
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