JPH03237195A - Additive for oil and oil containing the additive - Google Patents
Additive for oil and oil containing the additiveInfo
- Publication number
- JPH03237195A JPH03237195A JP19265690A JP19265690A JPH03237195A JP H03237195 A JPH03237195 A JP H03237195A JP 19265690 A JP19265690 A JP 19265690A JP 19265690 A JP19265690 A JP 19265690A JP H03237195 A JPH03237195 A JP H03237195A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- oil
- additive
- polymer
- molecular chain
- 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
- 239000000654 additive Substances 0.000 title claims abstract description 71
- 230000000996 additive effect Effects 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000003921 oil Substances 0.000 claims abstract description 28
- 239000000295 fuel oil Substances 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 239000010687 lubricating oil Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 abstract description 50
- 239000000178 monomer Substances 0.000 abstract description 28
- 150000002894 organic compounds Chemical class 0.000 abstract description 19
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 8
- 150000001342 alkaline earth metals Chemical group 0.000 abstract description 7
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical class N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 238000005461 lubrication Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- -1 vinylimidacillin Chemical compound 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 18
- 229920001577 copolymer Polymers 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 7
- 229920006158 high molecular weight polymer Polymers 0.000 description 7
- 229920005604 random copolymer Polymers 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 229920006318 anionic polymer Polymers 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000010802 sludge Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 239000002685 polymerization catalyst Substances 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 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
- UBDIXSAEHLOROW-BUHFOSPRSA-N (E)-7-Tetradecene Chemical compound CCCCCC\C=C\CCCCCC UBDIXSAEHLOROW-BUHFOSPRSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-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 group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- 150000000376 2-oxazolines Chemical class 0.000 description 2
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 239000010771 distillate fuel oil Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229920006132 styrene block copolymer Polymers 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- GVTLFGJNTIRUEG-ZHACJKMWSA-N (e)-n-(3-methoxyphenyl)-3-phenylprop-2-enamide Chemical compound COC1=CC=CC(NC(=O)\C=C\C=2C=CC=CC=2)=C1 GVTLFGJNTIRUEG-ZHACJKMWSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- WVAFEFUPWRPQSY-UHFFFAOYSA-N 1,2,3-tris(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1C=C WVAFEFUPWRPQSY-UHFFFAOYSA-N 0.000 description 1
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 1
- KWPVLUWTOJHTFX-UHFFFAOYSA-N 1,3,3-trimethylpyrrolidin-2-one Chemical compound CN1CCC(C)(C)C1=O KWPVLUWTOJHTFX-UHFFFAOYSA-N 0.000 description 1
- QUQZYDAVOUBILO-UHFFFAOYSA-N 1,3-bis(n-phenylanilino)propan-2-one Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)CC(=O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 QUQZYDAVOUBILO-UHFFFAOYSA-N 0.000 description 1
- NYCCIHSMVNRABA-UHFFFAOYSA-N 1,3-diethylimidazolidin-2-one Chemical compound CCN1CCN(CC)C1=O NYCCIHSMVNRABA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 description 1
- PGRNEGLBSNLPNP-UHFFFAOYSA-N 1,6-dichloro-3-methylhex-1-ene Chemical compound ClC=CC(C)CCCCl PGRNEGLBSNLPNP-UHFFFAOYSA-N 0.000 description 1
- HMIBQFXWSUBFTG-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]ethanone Chemical compound CCN(CC)C1=CC=C(C(C)=O)C=C1 HMIBQFXWSUBFTG-UHFFFAOYSA-N 0.000 description 1
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- FFGFDFCBRZLOIZ-UHFFFAOYSA-N 1-butylazetidin-2-one Chemical compound CCCCN1CCC1=O FFGFDFCBRZLOIZ-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- UZXXRFKXXJEKJA-UHFFFAOYSA-N 1-ethyl-3-methylimidazolidin-2-one Chemical compound CCN1CCN(C)C1=O UZXXRFKXXJEKJA-UHFFFAOYSA-N 0.000 description 1
- FHGCCHQDLUTAHS-UHFFFAOYSA-N 1-methoxy-3-phenylpiperidin-2-one Chemical compound O=C1N(OC)CCCC1C1=CC=CC=C1 FHGCCHQDLUTAHS-UHFFFAOYSA-N 0.000 description 1
- BSDATCTYWMFQCU-UHFFFAOYSA-N 1-methoxy-3-phenylpyrrolidin-2-one Chemical compound O=C1N(OC)CCC1C1=CC=CC=C1 BSDATCTYWMFQCU-UHFFFAOYSA-N 0.000 description 1
- QOEUNLQGZBSTBB-UHFFFAOYSA-N 1-methylazetidin-2-one Chemical compound CN1CCC1=O QOEUNLQGZBSTBB-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- ZZADUWYIVFFSJM-UHFFFAOYSA-N 1-naphthalen-1-ylazetidin-2-one Chemical compound O=C1CCN1C1=CC=CC2=CC=CC=C12 ZZADUWYIVFFSJM-UHFFFAOYSA-N 0.000 description 1
- VFOGRNUNUOKGPI-UHFFFAOYSA-N 1-naphthalen-1-ylpiperidin-2-one Chemical compound O=C1CCCCN1C1=CC=CC2=CC=CC=C12 VFOGRNUNUOKGPI-UHFFFAOYSA-N 0.000 description 1
- KDRONXZNFIQMDV-UHFFFAOYSA-N 1-naphthalen-1-ylpyrrolidin-2-one Chemical compound O=C1CCCN1C1=CC=CC2=CC=CC=C12 KDRONXZNFIQMDV-UHFFFAOYSA-N 0.000 description 1
- OPISVEPYALEQJT-UHFFFAOYSA-N 1-phenylazetidin-2-one Chemical compound O=C1CCN1C1=CC=CC=C1 OPISVEPYALEQJT-UHFFFAOYSA-N 0.000 description 1
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003571 thiolactams Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- SJDSOBWGZRPKSB-UHFFFAOYSA-N tricos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=C SJDSOBWGZRPKSB-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical group OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Lubricants (AREA)
Abstract
Description
【発明の詳細な説明】
(産業上の利用分野)
本発明は新規な燃料油用及び潤滑油用に適した油用添加
剤ならびにこの添加剤が添加された油に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a novel oil additive suitable for fuel oils and lubricating oils, and to oils to which this additive is added.
(従来の技術)
燃料油及び潤滑油はその用途に応じて多くの機能、特性
が要求される。これらの要求を満たすためには燃料油及
び潤滑油の基油に種々の添加剤を添加して基油の特性を
改良したり、機能を付与する必要がある。(Prior Art) Fuel oil and lubricating oil are required to have many functions and characteristics depending on their use. In order to meet these demands, it is necessary to add various additives to the base oil of fuel oils and lubricating oils to improve the properties of the base oil or to impart functions to the base oil.
例えば、軽油、A重油等の燃料油はn−パラフィンワッ
クス分を含有するため、冬期寒冷地に於いては、しばし
ばこのn−パラフィンワックス分の析出が起り、送油パ
イプの閉塞や内燃機関の燃料供給回路に設けられている
ストレーナ−の目詰りなど、低温下での燃料油の流動性
に大きな問題を起す。For example, fuel oils such as light oil and A heavy oil contain n-paraffin wax, so in cold winter regions, this n-paraffin wax often precipitates, causing blockage of oil pipes and damage to internal combustion engines. This causes major problems in the fluidity of fuel oil at low temperatures, such as clogging of the strainer installed in the fuel supply circuit.
この問題を解決するために、一般に低温流動性向上剤と
呼ばれる添加剤が使用される。この低温流動性向上剤と
しては、エチレン−酢酸ビニル共重合体をはじめ種々研
究され、提案されている。To solve this problem, additives commonly called cold flow improvers are used. Various types of low-temperature fluidity improvers have been studied and proposed, including ethylene-vinyl acetate copolymers.
例えば、特開昭54−157106号公報記載のエチレ
ン系不飽和ジカルボン酸とα−オレフィンとの共重合体
、特公昭50−15005号公報記載のエチレン系不飽
和ジカルボン酸とα−オレフィンとの共重合体の長鎖ア
ルコールエステル化物、また特開昭5481307号公
報記載のエチレン系不飽和ジカルボン酸とα−オレフィ
ンとの共重合体の脂肪族アミン変性物などが知られてい
る。しかしながら、これらの物質の添加効果は未だ充分
とは言い難い。For example, the copolymer of ethylenically unsaturated dicarboxylic acid and α-olefin described in JP-A-54-157106, and the copolymer of ethylenically unsaturated dicarboxylic acid and α-olefin described in JP-B-50-15005. Known are long-chain alcohol esters of polymers, and aliphatic amine-modified copolymers of ethylenically unsaturated dicarboxylic acids and α-olefins as described in JP-A-5481307. However, the effects of adding these substances are still far from being sufficient.
また、ガソリン等の燃料油に対する要求も、自動車等の
内燃機関の高性能化に伴って、ますます高度化されてき
た。その一つに、燃料系統の清浄化を目的としてポリブ
テニルこはく酸無水物、ポリアミンポリブテニルこはく
酸イミド、バリウムポリブテニル(チオ)ホスホネート
等が清浄分散剤やスラッジ分散剤として使用されている
。しかしながら、これらの添加剤は多量使用しなければ
効果がない問題がある。In addition, requirements for fuel oil such as gasoline have become increasingly sophisticated as the performance of internal combustion engines for automobiles and the like has improved. One example of these is polybutenyl succinic anhydride, polyamine polybutenyl succinimide, barium polybutenyl (thio)phosphonate, etc., which are used as cleaning dispersants and sludge dispersants for the purpose of cleaning fuel systems. However, there is a problem that these additives are ineffective unless used in large amounts.
潤滑油、例えば内燃機関のギアケースの油には油の粘度
指数を増すためにポリイソブチン、ポリメタクリレート
、ポリアルキルスチレン、部分水素化ブタジェン−スチ
レン共重合体あるいは非晶性エチレン−プロピレン共重
合体等の高分子物質が粘度指数向上剤として、また油の
中で生成したスラッジを油中に分散させギアケースの内
部を清潔に保つために多価金属のスルホン酸塩、有機リ
ン酸等が洗浄剤として、ポリブテニルこはく酸イえド、
ポリブテニルこはく酸エステル等が分散剤として添加さ
れている。Lubricating oils, such as gear case oils for internal combustion engines, contain polyisobutyne, polymethacrylate, polyalkylstyrene, partially hydrogenated butadiene-styrene copolymers, or amorphous ethylene-propylene copolymers to increase the viscosity index of the oil. Polymeric substances act as viscosity index improvers, and polyvalent metal sulfonates, organic phosphoric acids, etc. are used as cleaning agents to disperse sludge generated in the oil and keep the inside of the gear case clean. as polybutenyl succinate,
Polybutenyl succinate etc. are added as a dispersant.
所で、近時は粘度指数の向上と共にスラッジの分散をも
同時に行う添加剤としてマレイミド、ビニルイミダシリ
ン、ビニルピロリジン、ビニルピリジン等の(共)重合
体、グラフト重合体等も提案されているが、更に他の特
性、例えば、油に熱安定性を賦与するための酸化劣化防
止剤としての機能やスラッジ中の金属(油の酸化劣化を
促進する)を安定化する機能等の機能をも有する多機能
性の添加剤が求められている。Incidentally, recently, (co)polymers and graft polymers of maleimide, vinylimidacillin, vinylpyrrolidine, vinylpyridine, etc., have been proposed as additives that simultaneously improve the viscosity index and disperse sludge. However, it also has other properties, such as acting as an oxidative deterioration inhibitor to impart thermal stability to the oil and stabilizing metals in the sludge (which promote oxidative deterioration of the oil). There is a need for multifunctional additives that have the following properties.
(発明が解決しようとする諜H)
本発明等は以上の背景に鑑み、新規な油用添加剤、特に
燃料油及び潤滑油用としての添加剤を開発すべく鋭意研
究を重ねた結果、特定の官能性化合物が燃料油に対して
も潤滑油に対しても多機能性の添加剤として効果がある
ことを見い出し、本発明を完成するに到った。(Intelligence to be Solved by the Invention) In view of the above background, the present invention, etc. has been developed as a result of intensive research to develop new additives for oil, especially additives for fuel oil and lubricating oil. It was discovered that this functional compound is effective as a multifunctional additive for both fuel oil and lubricating oil, and the present invention was completed.
(課題を解決するための手段)
Φ
かかる本発明によれば、 C=N、、結合を/
有する原子団が分子鎖に結合した化合物を含むことを特
徴とする油用添加剤ならびに前記の化合物が添加された
油が提供される。(Means for Solving the Problem) Φ According to the present invention, there is provided an oil additive characterized in that it contains a compound in which an atomic group having/having a C=N bond is bonded to a molecular chain, and the above-mentioned compound. Provided with added oil.
以下、本発明の構成について説明する。The configuration of the present invention will be explained below.
(添加剤)
出
本発明の添加剤は該結合を有する原子団が分子鎖に結合
した化合物である。該結合はへテロ環構造中に存在する
場合とそうでない場合とがある。(Additive) The additive of the present invention is a compound in which an atomic group having the bond is bonded to a molecular chain. The bond may or may not be present in a heterocyclic structure.
該結合かへテロ環構造中に存在する化合物は、(1)分
子中に少なくとも1個の不飽和結合を有する化合物を用
いて、後述する化学反応により、下記の一般式で表わさ
れる原子団(ヘテロ環構造)(Ia)〜(IVb)
(1a)
(I b)
(Ila)
(IIb)
(I[Ia)
(IIIb)
R2
(IVa)
2
(IVb)
(式中のR,−R,は同一でも異なってもよく炭化水素
基を表わす。なお、R,−R3はハロゲン原子、ニトロ
基、エポキシ基、カルボキシル基、ヒドロキシエーテル
基、フェニル基等の置換基で少なくとも一部が置換され
ていてもよい。)ト分子鎖中に導入したもの(化合物A
)、(2)分子鎖中に下記の一般式(V) (Vl
)で示されるオキサジニウム塩またはオキサシリウム塩
単量体fAfLを有する重合体(化合物B)。The compound present in the bond or heterocyclic structure can be formed by (1) using a compound having at least one unsaturated bond in the molecule to form an atomic group ( Heterocyclic structure) (Ia) to (IVb) (1a) (Ib) (Ila) (IIb) (I[Ia) (IIIb) R2 (IVa) 2 (IVb) (R, -R, in the formula They may be the same or different and represent a hydrocarbon group.R and -R3 are at least partially substituted with a substituent such as a halogen atom, nitro group, epoxy group, carboxyl group, hydroxyether group, or phenyl group. ) introduced into the molecular chain (compound A
), (2) The following general formula (V) (Vl
) A polymer having an oxazinium salt or oxacillium salt monomer fAfL (compound B).
8
(V)オキサジニウム塩 (VJ)オキサシリウム塩(
式中R4〜R8は水素または炭化水素基を表わす。)
(3) リビングアニオン重合体の如きアルカリ金属
またはアルカリ土類金属が結合した重合体と特定の有機
化合物とを反応させて得られる分子鎖末端あるいは分子
鎖中に該結合を有する重合体(化合物C)等が含まれる
。8 (V) Oxazinium salt (VJ) Oxacillium salt (
In the formula, R4 to R8 represent hydrogen or a hydrocarbon group. ) (3) A polymer (compound) having the bond at the end or in the molecular chain obtained by reacting a polymer to which an alkali metal or alkaline earth metal is bonded, such as a living anionic polymer, with a specific organic compound. C) etc. are included.
桑皿剋生製造抜
(1)本発明の特定のへテロ環構造を有する化合物Aを
含有する添加剤は、分子鎖末端あるいは分子鎖中シテ炭
素−炭素二重結合または三重結合などの炭素−炭素不飽
和結合を有する化合物を原料として製造することができ
る。(1) The additive containing the compound A having a specific heterocyclic structure of the present invention has carbon-carbon atoms such as carbon-carbon double bonds or triple bonds at the end of the molecular chain or in the molecular chain. It can be produced using a compound having a carbon unsaturated bond as a raw material.
分子鎖末端に不飽和結合を有する原料化合物としては、
例えば、1−デセン、l−ドデセン、1−テトラデセン
、1−へキサデセン、l−エイコセン、1−トリデセン
などの長鎖アルキル基を有するα−オレフィン;低分子
量のポリエチレン、液状または低分子量ポリプロピレン
、α−オレフィンのオリゴマーなとの低分子量ポリマー
またはオリゴマー;ポリブテン、ポリイソブチレン、ポ
リエチレングリコールジメタクリラート、ポリエチレン
グリコールジアリラート、ポリプロピレングリコールジ
アリラート、ポリプロピレングリコールジメタクリレー
ト、ポリスチレンメタクリレート、ポリスチレンアリラ
ードなどのポリマーが挙げられる。As a raw material compound having an unsaturated bond at the end of the molecular chain,
For example, α-olefins having long chain alkyl groups such as 1-decene, l-dodecene, 1-tetradecene, 1-hexadecene, l-eicosene, 1-tridecene; low molecular weight polyethylene, liquid or low molecular weight polypropylene, α - Low molecular weight polymers or oligomers such as oligomers of olefins; polymers such as polybutene, polyisobutylene, polyethylene glycol dimethacrylate, polyethylene glycol diarylate, polypropylene glycol diarylate, polypropylene glycol dimethacrylate, polystyrene methacrylate, polystyrene allylad, etc. can be mentioned.
上記以外の分鎖中に不飽和結合を有する原料化合物とし
ては、例えば1.9−デカジエン、2,3−ジメチルブ
テン、2,5−へキサジエン、7−テトラデセン、トリ
コセン、2.4.4− )ツメチル−2−ペンテンなど
の−C=C−結合を有する有機化合物、またブタジェン
、イソプレン、ピペリレン、ジシクロペンタジェン、エ
チリデンノルボルネンの重合体または前記のモノマーと
ビニルモノマー、例えばスチレン、アクリロニトリル、
(メタ)アクリレート等との共重合体などの不飽和重合
体が挙げられる。共重合体としては、例えばスチレン−
ブタジェンランダム共重合体、スチレン−イソプレンラ
ンダム共重合体、アクリロニトリル−イソプレン共重合
体、スチレン−ブタジェンブロック共重合体(A−B型
、A−B−A型、B−A−B型等)、スチレン−イソプ
レンブロック共重合体(同左、Aはポリスチレンブロッ
ク、Bはポリブタジェンブロック又はポリイソプレンブ
ロックを示す)、アクリロニトリル−ブタジェン共重合
体、ブタジェン−メチルメタクリレート共重合体、これ
らの部分水素化物、エチレン−プロピレン−ジエンモノ
マー共重合体などが挙げられる。Examples of raw material compounds having unsaturated bonds in branch chains other than those mentioned above include 1.9-decadiene, 2,3-dimethylbutene, 2,5-hexadiene, 7-tetradecene, tricosene, 2.4.4- ) organic compounds having -C=C- bonds such as trimethyl-2-pentene, and also polymers of butadiene, isoprene, piperylene, dicyclopentadiene, ethylidenenorbornene or the monomers mentioned above and vinyl monomers, such as styrene, acrylonitrile,
Examples include unsaturated polymers such as copolymers with (meth)acrylate and the like. Examples of copolymers include styrene-
Butadiene random copolymer, styrene-isoprene random copolymer, acrylonitrile-isoprene copolymer, styrene-butadiene block copolymer (A-B type, A-B-A type, B-A-B type, etc.) ), styrene-isoprene block copolymer (same as left, A indicates polystyrene block, B indicates polybutadiene block or polyisoprene block), acrylonitrile-butadiene copolymer, butadiene-methyl methacrylate copolymer, partial hydrogen thereof and ethylene-propylene-diene monomer copolymers.
また−CミC−結合を有する化合物としては1−デイシ
ン、3,3−ジメチル−1−ブチイン、ヘブイン、ヘキ
シイン、1.8−ノナジイン、オクチインなどの有機化
合物が挙げられる。Examples of compounds having a -CmiC- bond include organic compounds such as 1-dicine, 3,3-dimethyl-1-butyine, heveine, hexine, 1,8-nonadiine, and octiine.
本発明で原料として使用できる化合物は、分子鎖に炭素
−炭素不飽和結合を有する化合物であればよく、分子量
についても、特に制限はなく、低分子有機化合物、オリ
ゴマーから高分子量の固体の重合体(例えば、数十万程
度の分子量を有する高分子量重合体)まで含まれる。The compound that can be used as a raw material in the present invention may be any compound having a carbon-carbon unsaturated bond in its molecular chain, and there is no particular restriction on the molecular weight, and it may range from low-molecular organic compounds, oligomers to high-molecular weight solid polymers. (For example, high molecular weight polymers having a molecular weight of about several hundred thousand).
本発明のへテロ環構造を有する化合物Aの製造方法につ
いては、特に限定されないが、代表的な製造方法のいく
つかを以下に記す。The method for producing the compound A having a heterocyclic structure of the present invention is not particularly limited, but some typical production methods are described below.
(i) 特開昭61−225202号公報開示の前記
分子鎖末端あるいは分子鎖中に炭素−炭素不飽和結合を
有する化合物に、ルイス酸の存在下に一般式Rq−CH
=N−R,o(式中Rq 、R,、は有機原子団を表わ
す)で示される有機化合物(I)と有機ハライドを反応
せしめる方法がある。(i) The compound having the carbon-carbon unsaturated bond at the end of the molecular chain or in the molecular chain disclosed in JP-A No. 61-225202 is treated with the general formula Rq-CH in the presence of a Lewis acid.
There is a method of reacting an organic compound (I) represented by =N-R,o (in the formula, Rq, R, represents an organic atomic group) with an organic halide.
有機化合物(1)としてはベンジリデンアニリン、ベン
ジリデンブチルアミンなどが、有機酸ノスライドとして
はアセチルクロライド、ベンゾイルクロライドなどが挙
げられる。Examples of the organic compound (1) include benzylideneaniline and benzylidenebutylamine, and examples of the organic acid nolide include acetyl chloride and benzoyl chloride.
ルイス酸としては、BF3、BF30(C,H3)、、
AlC1,、TtC/!、 、5nCI!a 、5
bC13、AgBF4などが挙げられる。Lewis acids include BF3, BF30(C,H3),
AlC1,,TtC/! , ,5nCI! a, 5
Examples include bC13 and AgBF4.
反応条件等は、特に限定されないが、通常、ベンゼン、
トルエン、シクロヘキサン等の不活性溶剤中、20〜8
0°Cで、1〜2時間程度反応させる。有機化合物(1
)および有機酸ハライドは、通常、不飽和化合物1モル
当り1〜1.5モル程度であり、ルイス酸は有機酸ハロ
イド1モル当り0.1〜1モル程度である。不飽和化合
物が重合体の場合には、有機化合物(1)および有機酸
ハロイドの使用量はそれぞれ重合体100重量部当り0
.1〜30重量部程度である(詳細は特開昭61225
202号公報を参照)。Reaction conditions are not particularly limited, but usually benzene,
In an inert solvent such as toluene or cyclohexane, 20 to 8
React at 0°C for about 1 to 2 hours. Organic compound (1
) and the organic acid halide are usually about 1 to 1.5 mol per mol of the unsaturated compound, and the Lewis acid is about 0.1 to 1 mol per mol of the organic acid halide. When the unsaturated compound is a polymer, the amount of organic compound (1) and organic acid halide used is 0 per 100 parts by weight of the polymer.
.. It is about 1 to 30 parts by weight (for details, see Japanese Patent Application Laid-open No. 61225
(See Publication No. 202).
(ii ) 前記の炭素−炭素不飽和結合を有する化
合物に、フリーゾルタラフッ触媒の存在下にNヒドロキ
シメチルア果ド化合物(N−メチロール化合物)を反応
せしめ、要すればさらにアルキルハライドやp−トルエ
ンスルホン酸メチル等を反応せしめてN−アルキル化を
はかる方法がある。(ii) The above-mentioned compound having a carbon-carbon unsaturated bond is reacted with an N-hydroxymethyl acetate compound (N-methylol compound) in the presence of a free sol Tarafluorocatalyst, and if necessary, an alkyl halide or p -There is a method of reacting with methyl toluenesulfonate or the like to achieve N-alkylation.
N−ヒドロキシメチルア果ド化合物は、アミド化合物と
アルデヒド化合物との反応物である。アルデヒド化合物
としてはホルマリン、ブチロアルデヒド、バレロアルデ
ヒド、およびベンズアルデヒドなど脂肪族、芳香族アル
デヒド等が用いられる。アミド化合物としては、アセト
アミド、ベンズアミド、メトキシベンズアミド、ニトロ
ベンズアミド、N−メチルベンズアミド、ブチロアごド
、フタルアミド酸、グルタル酸アミド等が挙げられる。An N-hydroxymethylaldehyde compound is a reaction product of an amide compound and an aldehyde compound. As the aldehyde compound, aliphatic and aromatic aldehydes such as formalin, butyroaldehyde, valeraldehyde, and benzaldehyde are used. Examples of the amide compound include acetamide, benzamide, methoxybenzamide, nitrobenzamide, N-methylbenzamide, butyroagodo, phthalamic acid, glutaric acid amide, and the like.
またN−メチロールアクリルアミドモノマーを一成分と
する共重合体等もN−ヒドメキシメチルアミド化合物と
して用いられる。A copolymer containing N-methylolacrylamide monomer as one component can also be used as the N-hydromexymethylamide compound.
アルキルハライドとしては、ベンジルブロマイド、ベン
ジルクロライド、ブロモヘキサン、ブロモプロパン、2
−クロロエチルエーテル、クロロメチルエーテル、クロ
ロペンタン等が主として用いられる。Examples of alkyl halides include benzyl bromide, benzyl chloride, bromohexane, bromopropane,
-Chloroethyl ether, chloromethyl ether, chloropentane, etc. are mainly used.
フリーゾルタラフッ触媒としては、一般に知られている
ものが使用可能である。その代表例は、金属または半金
属のハロゲン化物であって、例えば、B、 Af、
5iSP、、Ti、 V、 Fe、 Zn、 Mo、S
n。As the free sol cod fluorine catalyst, commonly known ones can be used. Typical examples thereof are metal or metalloid halides, such as B, Af,
5iSP, Ti, V, Fe, Zn, Mo, S
n.
Sb、 Te、 W等の元素、またはpo、 so□、
voなどの酸素−元素結合体のハロゲン化物もしくは有
機ハロゲン化物またはこれらの錯体などである。Elements such as Sb, Te, W, or po, so□,
These include halides of oxygen-element bonds such as vo, organic halides, and complexes thereof.
さらに具体的には、BF3 、BhO(CJs)z、B
CI!3、AlIC1,y 、TiCfa 、5nCj
!、 、FeC15、WCfi 、POCf、(CzH
s) zA j2などが挙げられる。More specifically, BF3, BhO(CJs)z, B
CI! 3, AlIC1,y, TiCfa, 5nCj
! , ,FeC15,WCfi,POCf,(CzH
s) zA j2, etc.
反応条件は、特に限定されない(この反応の詳細は、例
えばC,Giordanoらの5YNTFIESIS
、 92(1971)に示されている)。The reaction conditions are not particularly limited (details of this reaction can be found, for example, in the 5YNTFIESIS of C. Giordano et al.
, 92 (1971)).
(iii) 前記の炭素−炭素不飽和結合を有する化
合物に、1.3−双極子付加反応として知られているニ
トリルオキサイド、ニトリルイミン、ニトリルイリドを
不飽和結合と反応させた後、アルキルハライドやジメチ
ル硫酸等を反応せしめて、N−アルキル化をはかる方法
がある。(iii) After reacting the unsaturated bond with nitrile oxide, nitrile imine, or nitrile ylide, which is known as a 1.3-dipole addition reaction, to the above-mentioned compound having a carbon-carbon unsaturated bond, alkyl halide or There is a method of reacting with dimethyl sulfate or the like to achieve N-alkylation.
1.3−双極子付加反応については、Huisgenの
Anges、Chevs、、’i5.604 (163
)の論文に詳細が掲載されている。1. For the 3-dipole addition reaction, see Huisgen, Anges, Chevs, 'i5.604 (163
) details are published in the paper.
ニトルオキサイドによるイソオキサゾリン環の導入反応
に関しては、挙国、沼田らの文献(日本ゴム協会誌、
43 、996 (170)) ニ従かツタ。Regarding the introduction reaction of isoxazoline ring with nitroxide, see the literature of Kyokuni, Numata et al. (Japan Rubber Association Journal,
43, 996 (170)) ni tsuka ivy.
(1v) 前記の炭素−炭素不飽和結合を有する化合
物にハロヒドロキシイくノ化合物を無水炭素ナトリウム
のような脱HCI剤の存在化に反応せしめる。要すれば
、さらにアルキルハライドやジメチル硫酸等を反応せし
めてN−メチル化をはかる方法。ハロヒドロキシイミノ
化合物はT、L、G11christらのJ、C,S、
Cheap、 Commun、、1090(1979
)に記載されているα−ハロアセト化合物にヒドロキシ
ルアミン塩酸塩を反応させるか若しくはに、A、0g1
oblinらのJ、Org、Chem、 、 U、S、
S、R,±1370(1965)に記載されている。(1v) The above compound having a carbon-carbon unsaturated bond is reacted with a halohydroxy compound in the presence of an HCI removing agent such as anhydrous sodium carbonate. If necessary, a method of further reacting with an alkyl halide, dimethyl sulfate, etc. to achieve N-methylation. Halohydroxyimino compounds are T, L, J, C, S of Christ et al.
Cheap, Commun, 1090 (1979
), or by reacting hydroxylamine hydrochloride with the α-haloaceto compound described in A, 0g1
J, Org, Chem, U, S, of oblin et al.
S, R, ±1370 (1965).
合戊例に示したオレフィンとハロヒドロキシイミノ化合
物との反応によるオキサジン化合物の合成はT、L、1
i1christ らのJ、Chem、Soc、Per
kin Trans。The synthesis of an oxazine compound by the reaction of an olefin and a halohydroxyimino compound shown in the synthesis example is T, L, 1
J, Chem, Soc, Per of i1christ et al.
Kin Trans.
1 1275(1983)記載の方法に従った。1, 1275 (1983).
その他オキサジン化合物の合成はH,E、Zauggら
の5ynthesis、 85 (1984)、5yn
thesis、 182(1984)、5ynthes
is、 49 (1970)に詳しく延べられているの
で、合戒例に示した他の例はこれに従った。The synthesis of other oxazine compounds is described by H, E. Zaugg et al., 5ynthesis, 85 (1984), 5yn.
thesis, 182 (1984), 5ynthes
IS, 49 (1970), the other examples given in the example of the precepts followed this.
(2)本発明の特定のへテロ環構造を有する化合物Bを
含有する添加剤は、以下の方法により製造される。(2) The additive containing compound B having a specific heterocyclic structure of the present invention is produced by the following method.
(i)オキサジニウムイオンまたはオキサシリウムイオ
ンを分子内に有する重合性単量体を単独で、あるいは他
の重合性単量体と共に重合する。(i) A polymerizable monomer having an oxazinium ion or an oxacillium ion in its molecule is polymerized alone or together with other polymerizable monomers.
オキサジニウムイオンを分子内に有する重合性単量体と
しては、2−ビニル−2−オキサジニウムイオン、2−
ビニル−4−メチル−2−オキサジニウムイオン、2−
ビニル−4−エチル−2−オキサジニウムイオン、2−
イソプロペニル−2−オキサジニウムイオン、2−イソ
プロペニル−4−メチル−2−オキサジニウムイオン、
2−イソプロペニル−4−エチル−2−オキサジニウム
イオン、2−イソプロペニル−4,5−ジメチル−2−
オキサジニウムイオン等が挙げられる。対アニオンは特
に限定しないが塩を安定にするものが好ましい。Examples of the polymerizable monomer having an oxazinium ion in the molecule include 2-vinyl-2-oxazinium ion, 2-
vinyl-4-methyl-2-oxazinium ion, 2-
vinyl-4-ethyl-2-oxazinium ion, 2-
isopropenyl-2-oxazinium ion, 2-isopropenyl-4-methyl-2-oxazinium ion,
2-isopropenyl-4-ethyl-2-oxazinium ion, 2-isopropenyl-4,5-dimethyl-2-
Examples include oxazinium ion. The counter anion is not particularly limited, but one that stabilizes the salt is preferred.
オキサシリウムイオンを分子内に有する重合性単量体と
しては、2−ビニル−2−オキサツリウムイオン、2−
ビニル−4−メチル−2−オキサシリウムイオン、2−
ビニル−4−エチル−2オキサシリウムイオン、2−イ
ソプロペニル−2−オキサシリウムイオン、2−インプ
ロペニル−4−メチル−2−オキサシリウムイオン、2
イソプロペニル−4−エルチー2−オキサシリウムイオ
ン、2−イソプロペニル−4,5−ジメチル−2−オキ
サシリウムイオン等が挙げられる。対アニオンは特に限
定しないが塩を安定にするのが好ましい。Examples of polymerizable monomers having oxacillium ions in the molecule include 2-vinyl-2-oxaturium ions, 2-
Vinyl-4-methyl-2-oxacillium ion, 2-
Vinyl-4-ethyl-2oxacillium ion, 2-isopropenyl-2-oxacillium ion, 2-impropenyl-4-methyl-2-oxacillium ion, 2
Examples include isopropenyl-4-elti-2-oxacillium ion, 2-isopropenyl-4,5-dimethyl-2-oxacillium ion, and the like. Although the counter anion is not particularly limited, it is preferable to stabilize the salt.
これらの単量体とともに必要により使用される単量体と
しては、共重合しうるものであれば特に限定されず、例
えばスチレン、p−メチルスチレン、p−メトキシスチ
レン等のスチレン系モノマー;アクリル酸、アクリル酸
メチル、アクリル酸ブチル、アクリル酸ステアリル、メ
タアクリル酸、メタアクリル酸メチル等のアクリル酸あ
るいはメタクリル酸系モノマー;エチレン、プロピレン
、塩化ビニル、酢酸ビニル、アクリルア逅ド、アクリロ
ニトリル、N−ビニルピロリドン等が挙げられ、これら
の1種または2種以上が用いられる。Monomers used as necessary with these monomers are not particularly limited as long as they can be copolymerized, such as styrene monomers such as styrene, p-methylstyrene, and p-methoxystyrene; acrylic acid Acrylic acid or methacrylic acid monomers such as , methyl acrylate, butyl acrylate, stearyl acrylate, methacrylic acid, methyl methacrylate; ethylene, propylene, vinyl chloride, vinyl acetate, acryl oxide, acrylonitrile, N-vinyl Examples include pyrrolidone, and one or more of these may be used.
とくにエチレンやアクリン酸やメタアクリル酸の高級ア
ルコールエステル系モノマーが基油に溶は易いため好ま
しい。In particular, higher alcohol ester monomers such as ethylene, acrylic acid, and methacrylic acid are preferred because they are easily soluble in the base oil.
共重合する場合、前記のイオンを分子内に有する単量体
の使用量は全単量体混合物中0.01〜10重量%の範
囲である。0.01重量%未満では添加剤の効果は充分
でなく、また10重量%を超えて使用しても効果は飽和
する。好ましくは0.1〜5重量%である。In the case of copolymerization, the amount of the monomer having the above-mentioned ion in the molecule is in the range of 0.01 to 10% by weight based on the total monomer mixture. If the amount is less than 0.01% by weight, the effect of the additive will not be sufficient, and if it is used in excess of 10% by weight, the effect will be saturated. Preferably it is 0.1 to 5% by weight.
重合に用いる重合開始剤としては、通常に用いられる油
溶性の過酸化物系あるいはアゾ系開始剤が利用できる。As the polymerization initiator used for polymerization, commonly used oil-soluble peroxide-based or azo-based initiators can be used.
例えば、過酸化ベンゾイル、過酸化ラウロイル、メチル
エチルケトンパーオキサイド、キュメンハイドロパーオ
キサイド、t−ブチルハイドロパーオキサイド等の過酸
化物系開始剤、2.2゛−アゾビスイソブチロニトリル
、2,2゛−アゾビス−(2,4−ジメチルバレロニト
リル) 、2.2’−アゾビス−2,2,3−)リメチ
ルプチロニトリル、1.1’−アゾビス−(シクロへ牛
サンー1−カルボニトリル)、4.4’−3アゾビス−
4−シアノバレリン酸、ジメチル−2,2゛−アゾビス
イソブチレート等の過酸化物系開始剤がある。該重合開
始剤は、重合性単量体に対し、0.05〜10重量%使
用されるのが好ましい。For example, peroxide initiators such as benzoyl peroxide, lauroyl peroxide, methyl ethyl ketone peroxide, cumene hydroperoxide, t-butyl hydroperoxide, 2,2゛-azobisisobutyronitrile, 2,2゛-Azobis-(2,4-dimethylvaleronitrile), 2.2'-azobis-2,2,3-)limethylputyronitrile, 1.1'-azobis-(cyclohexane-1-carbonitrile) , 4.4'-3azobis-
There are peroxide-based initiators such as 4-cyanovaleric acid and dimethyl-2,2'-azobisisobutyrate. The polymerization initiator is preferably used in an amount of 0.05 to 10% by weight based on the polymerizable monomer.
重合溶剤としてはアセトニトリル、ニトロメタン、トル
エン、ベンゼン、キシレンなどが挙ケラれ、これらは単
独で又は混合して使用される。重合温度は通常−20°
C〜150°C1好ましくは0°C〜120°Cで行わ
れる。Examples of the polymerization solvent include acetonitrile, nitromethane, toluene, benzene, and xylene, which may be used alone or in combination. Polymerization temperature is usually -20°
It is carried out at a temperature of C to 150°C, preferably 0°C to 120°C.
重合体は上記のラジカル重合以外にも有機リチウム等の
アニオン重合触媒を用いるアニオン重合によっても製造
することができる。アニオン重合も常法に従えばよく、
特に制限されない。In addition to the radical polymerization described above, the polymer can also be produced by anionic polymerization using an anionic polymerization catalyst such as organolithium. Anionic polymerization can also be carried out using conventional methods.
There are no particular restrictions.
(11)オキサジン基またはオキサゾリン基を分子内に
有する重合性単量体の重合体中の該基の窒素原子を第4
級アンモニウム化することによって、オキサン摂ムイオ
ンまたはオキサシリウムイオンを含有する重合体が得ら
れる。(11) In a polymer of a polymerizable monomer having an oxazine group or an oxazoline group in the molecule, the nitrogen atom of the group is
A polymer containing oxane ions or oxacillium ions can be obtained by ammonium-forming.
オキサジン基を分子内に有する単量体としては2−ビニ
ル−2−オキサジン、2−イソプロペニル−2−オキサ
ジン、2−ビニル−4−メチル2−オキサジン、2−イ
ソプロペニル−4−メチル−2−オキサジン等が挙げら
れる。Examples of monomers having an oxazine group in the molecule include 2-vinyl-2-oxazine, 2-isopropenyl-2-oxazine, 2-vinyl-4-methyl 2-oxazine, and 2-isopropenyl-4-methyl-2 -Oxazine and the like.
オキサゾリン基を分子内に有する単量体としては2−ビ
ニル−2−オキサゾリン、2−イソプロペニル−2−オ
キサゾリン、2−ビニル−4−メチル−2−オキサゾリ
ン、2−イソプロペニル4−メチル−2−オキサゾリン
等が挙げられる。Examples of monomers having an oxazoline group in the molecule include 2-vinyl-2-oxazoline, 2-isopropenyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline, and 2-isopropenyl-4-methyl-2 -oxazoline and the like.
これらの単量体と共重合可能な単量体、重合方法に関し
ては上記の(i)の場合と同様である。The monomers copolymerizable with these monomers and the polymerization method are the same as in the case of (i) above.
重合体中の該基の窒素原子を第4級アンモニウム化する
方法はN−アルキル化剤によるアルキル化がある。A method for converting the nitrogen atom of the group in the polymer into a quaternary ammonium is alkylation using an N-alkylating agent.
N−アルキル化剤としてはメチルトシレート、アルキル
ハライド、ジメチル硫酸等が挙げられる。Examples of the N-alkylating agent include methyl tosylate, alkyl halide, dimethyl sulfate, and the like.
アルキル化反応は常法に従えばよく、特に制限されない
。重合体または共重合体内のイオン化された単量体単位
の含有量は0.01〜10重量%の範囲であり、好まし
くは0.1〜5重量%である。The alkylation reaction may be carried out according to a conventional method and is not particularly limited. The content of ionized monomeric units within the polymer or copolymer ranges from 0.01 to 10% by weight, preferably from 0.1 to 5% by weight.
上記の(i)、(ii)以外にもオキサシリウムイオン
を含有する重合体を製造する方法として、2−オキサゾ
リン、2−メチル−2−オキサゾリン、5−メチル−2
−オキサゾリン等の2−オキサゾリン類をカチオン重合
し、重合反応を求核反応性の溶媒で停止することによっ
て重合体鎖末端にオキサシリウムイオンが結合した重合
体を得る方法;カチオン重合触媒としてハロゲン原子、
スルホキシル基等のプロトン供与性基を有する重合体を
用いて2−オキサゾリン類を重合する方法等もある。In addition to the above (i) and (ii), methods for producing oxacillium ion-containing polymers include 2-oxazoline, 2-methyl-2-oxazoline, 5-methyl-2
- A method of cationically polymerizing 2-oxazolines such as oxazoline and terminating the polymerization reaction with a nucleophilic solvent to obtain a polymer in which oxacillium ions are bonded to the end of the polymer chain; a halogen atom is used as a cationic polymerization catalyst. ,
There is also a method of polymerizing 2-oxazolines using a polymer having a proton-donating group such as a sulfoxyl group.
(3)本発明の化合物Cを含有する添加剤は、アルカリ
金属及び/又はアルカリ土類金属が結合した重合体、す
なわちリビングアニオン重合体又は、アルカリ金属及び
/又はアルカリ土類金属を後反応により付加させた重合
体と、一般式
−C−N、で示される結合(式中Xは酸素又は1
オ)アルデヒド、N−置換アミノ(チオ)ケトン等とを
反応させ、反応生成物を加水分解することによって製造
することができる(詳細は特開昭58−162604号
公報、特開昭60−137913号公報を参照)。(3) The additive containing the compound C of the present invention is a polymer to which alkali metals and/or alkaline earth metals are bonded, that is, living anionic polymers, or alkali metals and/or alkaline earth metals are bonded by post-reaction. The added polymer is reacted with a bond represented by the general formula -C-N (where X is oxygen or 1 o)aldehyde, N-substituted amino(thio)ketone, etc., and the reaction product is hydrolyzed. (For details, see JP-A-58-162604 and JP-A-60-137913).
この方法で使用されるりとングアニオン重合体はアルカ
リ金属及び/又はアルカリ土類金属基材触媒等のアニオ
ン重合触媒により重合可能な単量体を重合して得られる
分子鎖の少なくとも一端に前記金属が結合した重合体(
オリゴマーから高分子量重合体を含む)である、また、
後反応(付加反応)により前記金属を付加させた重合体
(オリゴマーから高分子量重合体を含む)は分子鎖中に
二重結合を有する重合体に前記金属を公知の方法で付加
させることによって製造することができる。The anionic polymer used in this method is obtained by polymerizing monomers that can be polymerized with an anionic polymerization catalyst such as an alkali metal and/or alkaline earth metal-based catalyst, and the above-mentioned metal is present at at least one end of the molecular chain. Combined polymer (
(including oligomers to high molecular weight polymers), and
Polymers (including oligomers and high molecular weight polymers) to which the metals have been added through post-reactions (addition reactions) are produced by adding the metals to polymers having double bonds in their molecular chains using known methods. can do.
アニオン重合触媒により重合可能な単量体としては、1
.3−ブタジェン、イソプレン、1.3−ペンタジェン
、2.3−ジメチル−1,3−ブタジェン、1,3−ヘ
キサジエンなどの共役ジエン、スチレン、α−メチルス
チレン、ビニルトルエン、ビニルナフタレ硫黄原子)を
有する化合物、N−置換アミノ(チン、ジビニルベンゼ
ン、トリビニルベンゼン、ジビニルナフタレンなどの芳
香族ビニル化合物、アクリロニトリルなどの不飽和ニト
リル、(メタ)アクリル酸のエステル類、ビニルピリジ
ンなどが挙げられるが、これらに限定されるものではな
い。Monomers that can be polymerized with an anionic polymerization catalyst include 1
.. Conjugated dienes such as 3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethyl-1,3-butadiene, 1,3-hexadiene, styrene, α-methylstyrene, vinyltoluene, vinylnaphthalene (sulfur atom) N-substituted amino compounds, aromatic vinyl compounds such as divinylbenzene, trivinylbenzene, and divinylnaphthalene, unsaturated nitriles such as acrylonitrile, esters of (meth)acrylic acid, and vinylpyridine. It is not limited to.
重合体としては、これらの重合体及び共重合体が使用さ
れるが、具体的にはポリブタジェンゴム、ポリイソプレ
ンゴム、ブタジェン−イソプレンランダム及びブロック
共重合体、ブタジェン−スチレンランダム共重合体、ブ
タジェン−スチレンブロック共重合体(A−B型、A−
B−A型など。As the polymer, these polymers and copolymers are used, and specifically, polybutadiene rubber, polyisoprene rubber, butadiene-isoprene random and block copolymers, butadiene-styrene random copolymers, Butadiene-styrene block copolymer (A-B type, A-
B-A type etc.
A及びBは前記と同し)、イソプレン−スチレンブロッ
ク共重合体(同上)などが挙げられる。A and B are the same as above), isoprene-styrene block copolymer (same as above), and the like.
付加反応により前記金属を付加させるために使用される
重合体(オリゴマーから高分子量重合体を含む)は、前
記の金属基材触媒、Ziegler触媒などを用いた溶
液重合、レドックス型触媒等を用いた乳化重合など通常
の重合方法によって前記した共役ジエンモノマーあるい
は共役ジエンモノマーおよびこれと共重合可能なモノマ
ーとを重合又は共重合体させて得られるジエン系重合体
、具体的にはポリブタジェン、ポリイソプレン、ブタジ
ェン−スチレンランダム及びブロック共重合体、イソプ
レン−スチレンランダム及びブロック共重合体、ブタジ
ェン−イソプレンランダム及びブロック共重合体、ポリ
ペンタジェン、ブタジェン−ピペリレン共重合体、ブタ
ジェン−プロピレン交互共重合体、エチレン−プロピレ
ン−ジエンモノマー共重合体などが挙げられる。Polymers (including oligomers to high molecular weight polymers) used to add the metal by addition reaction can be polymerized using the aforementioned metal-based catalyst, solution polymerization using a Ziegler catalyst, etc., or polymerization using a redox type catalyst, etc. Diene-based polymers obtained by polymerizing or copolymerizing the above-mentioned conjugated diene monomers or conjugated diene monomers and monomers copolymerizable therewith by a normal polymerization method such as emulsion polymerization, specifically polybutadiene, polyisoprene, Butadiene-styrene random and block copolymers, isoprene-styrene random and block copolymers, butadiene-isoprene random and block copolymers, polypentadiene, butadiene-piperylene copolymers, butadiene-propylene alternating copolymers, ethylene -propylene-diene monomer copolymer and the like.
重合及び付加反応に使用される前記の金属を基材とする
重合触媒は、従来からアニオン重合に使用されている触
媒が使用でき、特に制限はない。The metal-based polymerization catalyst used in the polymerization and addition reaction is not particularly limited, and any catalyst conventionally used in anionic polymerization can be used.
アルカリ金属基材触媒としてはn−ブチルリチウム、5
ec−ブチルリチウムなどの炭素数2〜20個の有機リ
チウム化合物が代表例としてあげられる。As the alkali metal-based catalyst, n-butyllithium, 5
Representative examples include organic lithium compounds having 2 to 20 carbon atoms such as ec-butyllithium.
アルカリ土類金属基材触媒としては特開昭51−115
590号公報、特開昭52−9090 、17591
、30543 、48910゜98077号公報、特開
昭56−112916、.118403号公報、特開昭
57−100146号公報等に開示されているバリウム
、ストロンチウム、カルシウム等の化合物を主成分とす
る触媒系が挙げられるが、これに限定されない。重合反
応およびアルカリ金属及び/またはアルカリ土類金属付
加反応は従来からアニオン重合で使用されている炭化水
素剤またはテトラヒドロフラン、テトラヒドロビラン、
ジオキサンなどの該金属基材触媒を破壊しない溶剤中で
おこなわれる。As an alkaline earth metal-based catalyst, JP-A-51-115
Publication No. 590, JP-A-52-9090, 17591
, 30543, 48910°98077, JP-A-56-112916, . Examples include, but are not limited to, catalyst systems containing compounds such as barium, strontium, and calcium as main components disclosed in Japanese Patent Application Laid-open No. 118403 and Japanese Patent Application Laid-open No. 57-100146. The polymerization reaction and the alkali metal and/or alkaline earth metal addition reaction are carried out using hydrocarbon agents conventionally used in anionic polymerization, such as tetrahydrofuran, tetrahydrobilane,
It is carried out in a solvent that does not destroy the metal-based catalyst, such as dioxane.
オリゴマーから高分子量の重合体を製造するための該金
属基材触媒の使用量は通常単量体100g当り0.1〜
200ミリモルの範囲である。また付加反応においては
、付加すべき該金属の量によって相違はするが、通常重
合体100g当り0.1〜10ミリモル程度である。The amount of the metal-based catalyst used for producing high molecular weight polymers from oligomers is usually 0.1 to 100 g of monomer.
It is in the range of 200 mmol. In the addition reaction, the amount of the metal to be added varies depending on the amount of the metal to be added, but it is usually about 0.1 to 10 mmol per 100 g of the polymer.
重合は通常ランダマイザー及びビニル化剤としてのエー
テル化合物、アミン化合物、ホスフィン化合物等の極性
化合物の存在下に行われる。また、極性化合物は付加反
応の際にも通常使用される。Polymerization is usually carried out in the presence of polar compounds such as ether compounds, amine compounds, phosphine compounds, etc. as randomizers and vinylizing agents. Polar compounds are also commonly used in addition reactions.
重合及び付加反応の条件はこれらの常法の条件に従えば
よく、特に限定されない。The conditions for polymerization and addition reaction are not particularly limited as long as they follow the conditions of these conventional methods.
上記の方法等で得られるリビングアニオン重合体及び該
金属が付加した重合体と反応させる有機化合物は以下の
通りである。The living anionic polymer obtained by the above method and the organic compound to be reacted with the metal-added polymer are as follows.
を表わす)で示される原子団を有する化合物としてはN
−メチル−β−プロピオラクタム、N−を−ブチル−β
−プロピオラクタム、N−フェニル−β−プロピオラク
タム、N−メトキシフェニルβ−プロピオラクタム、N
−ナフチル−β−プロピオラクタム、N−メチル−2−
ピロリドン、N−t−ブチル−2−ピロリドン、N−フ
ェニルピロリドン、N−メトキシフェニル−2−ピロリ
ドン、N−ビニル−2−ピロリドン、N−ベンジル−2
−ピロリドン、N−ナフチル−2−ピロリドン、N−メ
チル−5−メチル−2−ピロリドン、N−t−ブチル−
5−メチル−2−ピロリドン、N−フェニル−5−メチ
ル−2−ピロリドン、N−メチル−3,3−ジメチル−
2−ピロリドン、N−t−ブチル−3,3−ジメチル−
2−ピロリドン、N−フェニル−3,3°−ジメチル−
2−ピロリドン、N−メチル−2−ピペリドン、N−t
−ブチル−2−ピペリドン、N−フェニル−2−ピペリ
ドン、N−メトキシフェニル−2−ピペリドン、N−ビ
ニル−2−ピペリドン、N−ベンジン−2−ピペリドン
、N−ナフチル−2−ピペリドン、N−メチル−3,3
゛−ジメチル−2−ピペリドン、N−フェニル−3,3
゛−ジメチル−2−ピペリドン、Nメチル−ε−カプト
ラクタム、N−フェニル−ε−カプトラクタム、N−メ
トキシフェニル−εカプトラクタム、N−ビニル−ε−
カプトラクタム、N−ベンジル−ε−カプトラクタム、
N−ナフチル−ε−カプトラクタム、N−メチル−ω−
ラウリロラクタム、N−フェニル−ω−ラウリロラクタ
ム、N−t−ブチル−ω−ラウリロラクタム、N−ビニ
ル−ω−ラウリロラクタム、N−ベンジル−ω−ラウリ
ロラクタム等のN−置換ラクタム類及びこれらの対応の
チオラクタム1s: 1.3−ジメチル−2−イミダゾ
リジノン、1.3−ジエチル−2−イミダゾリジノン、
1−メチル−3−エチル−2−イミダゾリジノン、1,
3−ジメチルエチレン尿素、1.3−ジフェニルエチレ
ン尿素、1,3−ジ−t−7’チルエチレン尿素、1.
3〜ジビニルエチレン尿素等のN−1F換環状尿素類及
び対応のN−置換環状チオ尿素類などが挙げられる。) as a compound having an atomic group represented by N
-Methyl-β-propiolactam, N-butyl-β
-Propiolactam, N-phenyl-β-propiolactam, N-methoxyphenyl β-propiolactam, N
-naphthyl-β-propiolactam, N-methyl-2-
Pyrrolidone, N-t-butyl-2-pyrrolidone, N-phenylpyrrolidone, N-methoxyphenyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, N-benzyl-2
-pyrrolidone, N-naphthyl-2-pyrrolidone, N-methyl-5-methyl-2-pyrrolidone, N-t-butyl-
5-methyl-2-pyrrolidone, N-phenyl-5-methyl-2-pyrrolidone, N-methyl-3,3-dimethyl-
2-pyrrolidone, Nt-butyl-3,3-dimethyl-
2-pyrrolidone, N-phenyl-3,3°-dimethyl-
2-pyrrolidone, N-methyl-2-piperidone, N-t
-Butyl-2-piperidone, N-phenyl-2-piperidone, N-methoxyphenyl-2-piperidone, N-vinyl-2-piperidone, N-benzine-2-piperidone, N-naphthyl-2-piperidone, N- Methyl-3,3
゛-Dimethyl-2-piperidone, N-phenyl-3,3
゛-Dimethyl-2-piperidone, N-methyl-ε-captractam, N-phenyl-ε-captractam, N-methoxyphenyl-ε-captractam, N-vinyl-ε-
captolactam, N-benzyl-ε-captolactam,
N-naphthyl-ε-captractam, N-methyl-ω-
N-substituted such as laurirolactam, N-phenyl-ω-laurirolactam, N-t-butyl-ω-laurirolactam, N-vinyl-ω-laurirolactam, N-benzyl-ω-laurirolactam, etc. Lactams and their corresponding thiolactams: 1,3-dimethyl-2-imidazolidinone, 1,3-diethyl-2-imidazolidinone,
1-methyl-3-ethyl-2-imidazolidinone, 1,
3-dimethylethyleneurea, 1,3-diphenylethyleneurea, 1,3-di-t-7'thylethyleneurea, 1.
Examples include N-1F substituted cyclic ureas such as 3-divinylethylene urea and corresponding N-substituted cyclic thioureas.
また、他の有機化合物としては、4−ジメチルアミノベ
ンゾフェノン、4−ジエチルアミノベンゾフェノン、4
−ジ−t−ブチルアミノベンゾフェノン、4−ジフェニ
ルベンゾフェノン、4.4’−ビス(ジメチルアミノ)
ベンゾフェノン、4.4’−ビス(ジエチルアミノ)ベ
ンゾフェノン、4.4”−ビス(ジ−t−ブチルアミノ
)ベンゾフェノン、4.4゛−ビス(ジフェニルアξ)
)ベンゾフェノン、4.4’−ビス(ジビニルアミノ)
ベンゾフェノン、4−ジメチルアミノアセトフェノン、
4−ジエチルアミノアセトフェノン、1,3−ビス(ジ
フェニルアミノ)−2−プロパノン、■、7−ビス(メ
チルエチルアミノ)−4−ヘプタノン等のN−置換アミ
ノケトン類及び対応のN−IF換アξノチオケトン類:
4−ジメチルアミノベンズアルデヒド、4−ジフェニル
アミノベンズアルデヒド、4−ジビニルアミノベンズア
ルデヒド等のN−7換アミノアルデヒド類及び対応のN
−置換アミノチオアルデヒド類が挙げられる。In addition, other organic compounds include 4-dimethylaminobenzophenone, 4-diethylaminobenzophenone, 4-dimethylaminobenzophenone, and 4-dimethylaminobenzophenone.
-di-t-butylaminobenzophenone, 4-diphenylbenzophenone, 4,4'-bis(dimethylamino)
Benzophenone, 4.4'-bis(diethylamino)benzophenone, 4.4"-bis(di-t-butylamino)benzophenone, 4.4"-bis(diphenylaξ)
) Benzophenone, 4,4'-bis(divinylamino)
Benzophenone, 4-dimethylaminoacetophenone,
N-substituted aminoketones such as 4-diethylaminoacetophenone, 1,3-bis(diphenylamino)-2-propanone, 7-bis(methylethylamino)-4-heptanone and the corresponding N-IF-converted ξ-nothioketones Kind:
N-7-substituted aminoaldehydes such as 4-dimethylaminobenzaldehyde, 4-diphenylaminobenzaldehyde, 4-divinylaminobenzaldehyde and the corresponding N
-substituted aminothioaldehydes.
これらの有機化合物の使用量は、重合体に結合している
該金属1モル当り通常0.05〜lOモルである。リビ
ングアニオン重合体等と有機化合物との反応は両者を溶
解する溶媒の溶液中で行われるが、反応は迅速に起るの
で、反応温度および反応時間は広範囲に選択できるが、
−船釣には室温乃至100°C1数秒乃至数時間である
。反応終了後、反応生成物を加水分解、例えば反応混合
物にメタノール、イソプロピルアルコール等のアルコー
ルを凝固剤として添加する方法、反応混合物をスチーム
ストリッピングに付すること等によって、分子鎖中に
; c = Nぐ 結合を有する原子団が結合した本
発明の添加剤が得られる。The amount of these organic compounds used is usually 0.05 to 10 mol per mol of the metal bonded to the polymer. The reaction between a living anionic polymer, etc. and an organic compound is carried out in a solution of a solvent that dissolves both, but since the reaction occurs rapidly, the reaction temperature and reaction time can be selected within a wide range.
- For boat fishing, the temperature ranges from room temperature to 100°C for several seconds to several hours. After the reaction is completed, the reaction product is hydrolyzed, for example, by adding alcohol such as methanol or isopropyl alcohol to the reaction mixture as a coagulant, or by subjecting the reaction mixture to steam stripping, etc.
; The additive of the present invention is obtained in which an atomic group having a c=Ng bond is bonded.
末端がLiのりピングアニオン重合体と有機化合物とし
ての4.4′−ビス(ジメチルアミノ)−ベンゾフェノ
ンとの反応を例示すると次のようになる。The following is an example of the reaction between an anionic polymer having a Li-terminated terminal and 4,4'-bis(dimethylamino)-benzophenone as an organic compound.
〜重合体鎖
よれシ悔会℃、そうイtjy)偽金09参正へ)9以上
説明した(1)及び(2)の方法で得られる添加剤は燃
料油、すなわち、40〜500℃の範囲の沸点を有する
石油中間留出燃料油(例えば、ガソリン、軽油、灯油、
ディーゼル燃料油、ジェット燃料油、A重油など)及び
潤滑油の添加剤として使用される。〜Polymer chain twisting regret ℃, so itjy) Counterfeit money 09 reference) 9 The additives obtained by the methods (1) and (2) explained above are fuel oil, that is, at 40 to 500℃. Petroleum middle distillate fuel oils with boiling points in the range (e.g. gasoline, diesel oil, kerosene,
It is used as an additive in diesel fuel oil, jet fuel oil, A heavy oil, etc.) and lubricating oils.
燃料油の添加剤として使用した場合には、分散剤及び低
温流動性改質剤(流動点降下剤)としての機能が発現さ
れる0本添加剤は燃料油に溶解する化合物の内から、上
記の機能が最大限に発揮される化合物または化合物の組
み合せを選択すればよく、化合物の種類は特に制限され
ない、同様に分子量についても制限はなく、低分子有機
化合物ないし高分子量の重合体まで含まれる。When used as an additive for fuel oil, it functions as a dispersant and a low-temperature fluidity modifier (pour point depressant). It is only necessary to select a compound or a combination of compounds that maximizes the function of the compound, and there are no particular restrictions on the type of compound. Likewise, there are no restrictions on the molecular weight, and it includes everything from low-molecular organic compounds to high-molecular weight polymers. .
添加剤中の該結合を含むヘテロ環又は該結合の数は添加
剤の分子量によって相違はあるが、通常、(重量平均分
子量)/(一分子当りの該ヘテロ環のかず又は該結合の
数)が200,000以下が好ましく、さらに好ましく
は100,000以下、より好ましくは100,000
以下である。但し、i、ooo以下となると効果は飽和
してしまう。The number of heterocycles containing the bond or the number of bonds in the additive varies depending on the molecular weight of the additive, but is usually (weight average molecular weight)/(number of the heterocycle or bond per molecule). is preferably 200,000 or less, more preferably 100,000 or less, more preferably 100,000
It is as follows. However, when i,ooo or less, the effect becomes saturated.
本添加剤の添加量は通常、燃料油に対してo、ooi重
量%以上、好ましくは0.01〜5重量%、さらに好ま
しくは0.01〜IIrf%添加される。The amount of this additive added is usually o, ooi% by weight or more, preferably 0.01 to 5% by weight, more preferably 0.01 to IIrf%, based on the fuel oil.
本添加剤は、他の添加剤、例えば、酸化防止剤、燃焼改
良剤、曇り防止剤、アンチノック剤、着色剤、灰分改質
剤、界面活性剤型添加剤等と併用することができる。This additive can be used in combination with other additives, such as antioxidants, combustion improvers, antifogging agents, antiknock agents, colorants, ash modifiers, surfactant type additives, and the like.
また、本発明の分散剤−低温流動性改質剤を燃料油に添
加する際には、あらかじめ稀釈溶剤、例えばケロセン、
軽質潤滑基材、重質芳香族ナフサ等に溶解させてから該
燃料油に混合することができる。In addition, when adding the dispersant-cold flow modifier of the present invention to fuel oil, a diluting solvent such as kerosene,
It can be dissolved in a light lubricating base material, heavy aromatic naphtha, etc. and then mixed into the fuel oil.
本発明の添加剤を滑剤油の添加剤として使用した場合に
は、粘度指数向上剤、低温流動性改質剤(流動点降下剤
)、清浄分散剤、酸化防止剤等の多機能が発現される。When the additive of the present invention is used as an additive for lubricant oil, it exhibits multiple functions such as a viscosity index improver, a low-temperature fluidity modifier (pour point depressant), a detergent dispersant, and an antioxidant. Ru.
潤滑油としては、鉱油系及び合成基(α−オレフィン系
、エステル系)を基油とする各種潤滑油、例えばエンジ
ン油(ガソリンおよびディーゼル用)、ギヤー油、ター
ビン油、作動油、ゴム配合油(プロセス油)、ワックス
類が挙げられる。Lubricating oils include various lubricating oils based on mineral oils and synthetic groups (α-olefins, esters), such as engine oils (for gasoline and diesel), gear oils, turbine oils, hydraulic oils, and rubber compounded oils. (process oil) and waxes.
本発明の添加剤は潤滑油に溶解する化合物の内から、上
記の機能が最大限に発揮される化合物または化合物の組
み合せを選択すればよく、化合物の種類は特に制限され
ない、同様に分子量についても制限はなく、低分子有機
化合物ないし高分子量の重合体まで含まれる。The additive of the present invention may be selected from compounds soluble in lubricating oil, or a combination of compounds that maximizes the above functions, and the type of compound is not particularly limited. There is no restriction, and it includes from low molecular weight organic compounds to high molecular weight polymers.
本発明の添加剤は潤滑油(基油)に対して通常0.00
1重量%以上、好ましくは0.001〜30重量%、さ
らに好ましくは0.01〜20重量%添加される。The additive of the present invention is usually 0.00% relative to lubricating oil (base oil).
It is added in an amount of 1% by weight or more, preferably 0.001 to 30% by weight, more preferably 0.01 to 20% by weight.
本発明の添加剤は、他の添加剤、例えば消泡剤、腐食防
止剤、極圧剤、油性向上剤等と併用することができる。The additive of the present invention can be used in combination with other additives, such as antifoaming agents, corrosion inhibitors, extreme pressure agents, oiliness improvers, and the like.
(実施例)
以下に実施例を挙げて本発明をさらに具体的に説明する
。なお、実施例及び比較例中の部及び%はとくに断りの
ないかぎり重量基準である。(Example) The present invention will be described in more detail with reference to Examples below. Note that parts and percentages in Examples and Comparative Examples are based on weight unless otherwise specified.
石油中間留出燃料油の低温流動性はJIS K−220
4の流動点及びJIS K−2288の目詰まり点(C
FPP)を用いた。また清浄分散性の評価はJIS K
−2514の潤滑油の酸化安定度試験に従ってワニス棒
に対するラッカーの付着状態にて評価した。The low temperature fluidity of petroleum middle distillate fuel oil is JIS K-220.
4 pour point and JIS K-2288 clogging point (C
FPP) was used. In addition, the evaluation of cleanliness and dispersibility is based on JIS K.
The adhesion state of the lacquer to the varnish rod was evaluated according to the lubricating oil oxidation stability test of No.-2514.
添加剤の製造例1
第1表に示す各重合体100gをベンゼン500111
に溶解し、攪拌機、内部加熱装置、蒸気コンデンサー及
び液体−固体供給入り口を備えた容器に入れ、攪拌しな
がら60℃まで加温した。第1表に示す試薬Aと試薬B
の各々0.1モルを添加し、約1時間反応させた(場合
によっては試薬Cを0.15モルを添加した)0次いで
少量のメタノールを添加し、反応を停止させた後、1j
!のメタノールに反応混合物を注ぎ、生成物を凝固させ
た。Additive production example 1 100g of each polymer shown in Table 1 was mixed with benzene 500111.
in a vessel equipped with a stirrer, an internal heating device, a vapor condenser and a liquid-solid feed inlet, and heated to 60° C. with stirring. Reagent A and Reagent B shown in Table 1
0.1 mol of each were added and reacted for about 1 hour (in some cases, 0.15 mol of reagent C was added). Then, a small amount of methanol was added to stop the reaction, and 1j
! The reaction mixture was poured into methanol to solidify the product.
得られた生成物は真空乾燥機にて乾燥した。得られた添
加剤を添加剤I〜■とする。The obtained product was dried in a vacuum dryer. The obtained additives are referred to as Additives I to ①.
添加剤の製造例2
内容a2j!のステンレン製重合反応器を洗浄、乾燥し
、乾燥窒素で置換した後、1.3−ブタジェン150g
、スチレン50g1ベンゼン820 g。Additive production example 2 Contents a2j! After cleaning and drying the stainless steel polymerization reactor and purging it with dry nitrogen, 150 g of 1,3-butadiene was added.
, 50 g of styrene and 820 g of benzene.
テトラメチルエチレンジアミン0.5ミリモル、n−ブ
チルリチウム(n−ヘキサン溶液)1.8−5リモルを
添加し、内容物を攪拌しながら40℃で1時間重合を行
った。0.5 mmol of tetramethylethylenediamine and 1.8-5 mmol of n-butyllithium (n-hexane solution) were added, and polymerization was carried out at 40° C. for 1 hour while stirring the contents.
重合反応終了後、N−メチルピロリドンを1.0ミリモ
ル添加し、10分間攪拌下に反応させた。After the polymerization reaction was completed, 1.0 mmol of N-methylpyrrolidone was added and reacted for 10 minutes with stirring.
次いで、2.6−ジーt−ブチル−p−クレゾール2.
0%メタノール溶液中に反応器中の内容物を注ぎ、生成
した重合体を凝固せしめた後、60℃、24時間減圧下
にて乾燥した。この重合体を添加剤■とする。Then 2.6-di-t-butyl-p-cresol2.
The contents of the reactor were poured into a 0% methanol solution to solidify the resulting polymer, which was then dried under reduced pressure at 60° C. for 24 hours. This polymer is referred to as additive (2).
また、N−メチルピロリドンを反応させない以外は上記
と同じ条件で重合体を製造した。これを添加剤■(*)
とする。Further, a polymer was produced under the same conditions as above except that N-methylpyrrolidone was not reacted. Add this as an additive■(*)
shall be.
添加剤IV、IV(*)は結合スチレン量25%、GP
Cで測定したポリスチレン換算の重量平均分子量は15
万であった。Additives IV and IV (*) have a bound styrene content of 25%, GP
The weight average molecular weight in terms of polystyrene measured at C is 15
It was 10,000.
添加剤の製造例3
第2表に示すα−オレフィンまたはポリブテンの各1モ
ルと300mfのベンゼンを、攪拌機、内部加熱装置、
蒸気コンデンサー、および液体一固体供給入口を備えた
容器に入れた。Additive Production Example 3 1 mol each of α-olefin or polybutene shown in Table 2 and 300 mf of benzene were mixed with a stirrer, an internal heating device,
It was placed in a vessel equipped with a vapor condenser, and a liquid-solid feed inlet.
第2表に示す試薬Aと試薬Bの各々1モルを添加し、4
5℃で約1時間反応を行った。メタノールを添加し反応
を停止させた。さらに、0.5〜llのメタノールを添
加し、冷蔵庫内で冷却し、得られた沈澱物をメタノール
で洗浄した後、乾燥して目的の添加剤を得た。これらを
添加剤V〜■とする。また反応出発物である第2表のα
−オレフィン、ポリブテンを添加剤V(*)〜■(*)
とする。Add 1 mol each of Reagent A and Reagent B shown in Table 2,
The reaction was carried out at 5°C for about 1 hour. Methanol was added to stop the reaction. Furthermore, 0.5 to 1 l of methanol was added, and the mixture was cooled in a refrigerator, and the resulting precipitate was washed with methanol and dried to obtain the desired additive. These are referred to as additives V to ■. Also, α in Table 2 which is a reaction starting material
- Additives V (*) to ■ (*) for olefins and polybutenes
shall be.
添加剤の製造例4
エチレン−プロピレン−ジエン共重合体(三井石油化学
社製X−4010,Ml、t、、 、100°C=10
)160gとベンゼン31のベンゼンを攪拌機、内部加
熱装置、蒸気コンデンサーおよび液体一固体供給入口を
備えた容器に入れた。ベンジリデンブチルア逅ン20ミ
リモル、アセチルクロリド20ミリモル、20ミリモル
をそれぞれベンゼン溶液として添加し、45℃で約1時
間反応を行なった。メタノールを添加し反応を停止させ
た。Additive production example 4 Ethylene-propylene-diene copolymer (Mitsui Petrochemical Co., Ltd. X-4010, Ml, t, , 100°C = 10
) and 31 g of benzene were placed in a vessel equipped with a stirrer, an internal heating device, a vapor condenser, and a liquid-solids feed inlet. 20 mmol of benzylidene butyl chloride, 20 mmol of acetyl chloride, and 20 mmol of acetyl chloride were added as benzene solutions, and the reaction was carried out at 45° C. for about 1 hour. Methanol was added to stop the reaction.
さらに、0.5〜11のメタノールを添加し、冷蔵庫内
で冷却し、得られ沈澱物をメタノールで洗浄した後、乾
燥して目的の添加剤を得た。これを添加剤■とする。ま
た出発物質を添加剤■(*)とする。Further, 0.5 to 11 methanol was added, cooled in a refrigerator, and the resulting precipitate was washed with methanol and dried to obtain the desired additive. This is called additive (■). Also, the starting material is an additive (*).
添加剤の製造例5
攪拌機、N2ガス導入管、還流冷却管および温度計を備
えたフラスコにN−メチル−イソプロペニルオキサシリ
ウムトシレート3部およびメタアクリル酸ステアレート
97部を溶解したトルエン250部を仕込んだ、さらに
ベンゾンノ(−オキサイド10部を添加した。N2ガス
を吹き込みな力くら80〜100℃に加熱し、この状態
で攪拌しながら5時間重合した。室温にもどして溶媒を
蒸発除去したのち、メタノール500部に注ぎ、凝固し
たのち乾燥して官能基としてオキサシリウムイオン構造
を有する重合体を得た。この重合体を添加剤Xとした。Additive Production Example 5 3 parts of N-methyl-isopropenyloxacillium tosylate and 97 parts of methacrylic acid stearate were dissolved in 250 parts of toluene in a flask equipped with a stirrer, N2 gas introduction tube, reflux condenser and thermometer. 10 parts of benzono(-oxide) was added.N2 gas was blown in and the mixture was heated to 80-100°C, and polymerization was carried out for 5 hours while stirring in this state.The mixture was returned to room temperature and the solvent was removed by evaporation. Thereafter, the mixture was poured into 500 parts of methanol, coagulated, and dried to obtain a polymer having an oxacillium ion structure as a functional group.This polymer was designated as Additive X.
得り重合体を一部クロロホルムに溶解し紫外・可視多波
長分光検出器(日本分光工社製MULTI−330)を
接続したGPCでポリマー成分の紫外可視スペクトルを
測定したところ、UVmax −310部mのオキサシ
リウムに帰因すると思われる吸収を得た。When the resulting polymer was partially dissolved in chloroform and the UV-visible spectrum of the polymer component was measured using GPC connected to a UV-visible multi-wavelength spectrometer (MULTI-330 manufactured by JASCO Corporation), UVmax was −310 parts m. Absorption that was attributed to oxacillium was obtained.
得られた重合体中にオキサシリウムイオン構造が含まれ
ていることが確認された。It was confirmed that the obtained polymer contained an oxacillium ion structure.
同様にして得た土チレン/ビニルオキサゾリン(97部
3重量比)共重合体100部をベンゼン300部溶解し
、メチルクロライド5部、ヨウ化ナトリウム1部を添加
して、還流下で12時間反応させた。得られた反応溶液
をメタノール1000部に注ぎ再沈したのち乾燥した。300 parts of benzene was dissolved in 100 parts of the similarly obtained clay tyrene/vinyl oxazoline (97 parts by weight) copolymer, 5 parts of methyl chloride and 1 part of sodium iodide were added, and the mixture was reacted under reflux for 12 hours. I let it happen. The obtained reaction solution was poured into 1,000 parts of methanol, reprecipitated, and then dried.
得れた重合体を一部クロロホルムに溶解し紫外・可視多
波長分光検出器(日本分光工社製MULTI−330)
を接続したGPCでポリマー成分の紫外可視スペクトル
を測定したところUVmax =31 On諺のオキサ
ツリウムに帰因すると思われる吸収を得た。得られた重
合体中にオ′キサ゛l” リウムイオン構造が含まれて
しすることか確認された。この重合体を添加剤XIとし
た。A portion of the obtained polymer was dissolved in chloroform, and a UV/visible multi-wavelength spectroscopic detector (MULTI-330 manufactured by JASCO Corporation) was used.
When the ultraviolet-visible spectrum of the polymer component was measured using a GPC connected to the UV max = 31 On, an absorption believed to be attributable to the proverbial oxathurium was obtained. It was confirmed that the obtained polymer contained an oxalium ion structure.This polymer was designated as Additive XI.
実施例1
添加剤の製造例1及び2で製造した添加剤■〜IV、I
V(*)を下記の燃料油に300ppm又は500pp
−添加し、低温流動性及び清浄分散性を評価した。結果
を第3表に示す。Example 1 Additives manufactured in Additive Production Examples 1 and 2 - IV, I
Add 300ppm or 500pp of V(*) to the following fuel oil.
- added to evaluate cold flowability and clean dispersibility. The results are shown in Table 3.
燃料油A:20%沸点268℃、90%沸点345℃、
軟点373℃
燃料油B:20%沸点22沸点221°海190
第3表より、本発明の燃料油添加剤が低温流動性改質剤
及び分散剤の機能を有する添加剤であることを示してい
る。Fuel oil A: 20% boiling point 268°C, 90% boiling point 345°C,
Soft point 373°C Fuel oil B: 20% boiling point 22 boiling point 221° sea 190 Table 3 shows that the fuel oil additive of the present invention is an additive that has the functions of a low-temperature fluidity modifier and a dispersant. ing.
実施例2
添加剤■〜XI及び■(*)〜■(*)のいずれか5部
を水素化精製されたパラフィン系鉱物油95部に添加し
た。得られた潤滑油の粘度指数(ν、■、)をJIS
K2283に従って、また剪断安定性をJPI−55−
29−88に準拠して超音波照射による粘度損失率(下
の式により算出)より評価した。Example 2 5 parts of any one of additives 1 to 1 and 2 (*) to 2 (*) were added to 95 parts of hydrorefined paraffinic mineral oil. The viscosity index (ν, ■,) of the obtained lubricating oil is determined by JIS
K2283 and shear stability JPI-55-
Evaluation was made based on the viscosity loss rate (calculated using the formula below) due to ultrasonic irradiation in accordance with 29-88.
Vo :超音波照射前の動粘度(cst)■、:超音波
照射後の動粘度(cst)以上の結果を第4表に示す。Vo: kinematic viscosity (cst) before ultrasonic irradiation (cst), kinematic viscosity (cst) after ultrasonic irradiation (cst) The results are shown in Table 4.
また、清浄分散性をJIS K2514に従いワニス棒
に対するラッカー付着度より評価した。結果を第5表に
示す。Further, the cleaning dispersibility was evaluated based on the degree of lacquer adhesion to the varnish rod according to JIS K2514. The results are shown in Table 5.
第
5
表
第4表より、本発明の潤滑油添加剤の使用により粘度指
数(V、1.)は著しく改善されることが分る。Table 5 From Table 4, it can be seen that the viscosity index (V, 1.) is significantly improved by using the lubricating oil additive of the present invention.
また、第5表より、本発明の潤滑油添加剤は優れた清浄
分散剤としての機能を有することが分る。Furthermore, Table 5 shows that the lubricating oil additive of the present invention has an excellent function as a detergent and dispersant.
試験後の潤滑油はいずれも黒褐色に変色しており、10
°Cの冷蔵庫に本発明例の潤滑油を1週間放置してもス
ラッジの沈降は全く認められなかったが、比較例の潤滑
油は1日後にスラッジが沈降した。All lubricating oils after the test had changed color to blackish brown and had a rating of 10
Even when the lubricating oil of the present invention was left in a refrigerator at °C for one week, no sludge sedimentation was observed, but the sludge of the comparative lubricating oil was sedimented after one day.
以上の結果は本発明の潤滑油添加剤が粘度指数向上剤及
び清浄分散剤の機能を有する多機能添加剤であることを
示している。The above results indicate that the lubricating oil additive of the present invention is a multifunctional additive having the functions of a viscosity index improver and a detergent/dispersant.
(発明の効果)
本発明の油用添加剤は、燃料油に対しては、従来技術に
比較して優れた低温流動性ならびに清浄分散性を付与す
るものである。また、潤滑油に対しては、粘度指数の向
上ならびに清浄分散性を付与する多機能性の添加剤であ
る。(Effects of the Invention) The oil additive of the present invention provides fuel oil with superior low-temperature fluidity and clean dispersibility as compared to the prior art. Furthermore, it is a multifunctional additive for lubricating oils that improves the viscosity index and imparts cleansing and dispersion properties.
従って、本発明の添加剤が添加された燃料油及び潤滑油
は従来のこれらの油と比較して上記の特性が著しく改善
される。Therefore, fuel oils and lubricating oils to which the additives of the present invention have been added have significantly improved properties as compared to conventional oils.
Claims (7)
原子団が分子鎖 に結合した化合物を含むことを特徴とする油用添加剤。(1) ▲ Contains mathematical formulas, chemical formulas, tables, etc. ▼ An oil additive characterized by containing a compound in which an atomic group with a bond is bonded to a molecular chain.
合物である請求項第(1)記載の添加剤。(2) The additive according to claim 1, wherein the compound is a compound having a heterocyclic structure containing the bond.
。(5) An oil to which the oil additive according to claim (1) is added.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19265690A JPH03237195A (en) | 1989-12-28 | 1990-07-20 | Additive for oil and oil containing the additive |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1-342197 | 1989-12-28 | ||
JP34219789 | 1989-12-28 | ||
JP19265690A JPH03237195A (en) | 1989-12-28 | 1990-07-20 | Additive for oil and oil containing the additive |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH03237195A true JPH03237195A (en) | 1991-10-23 |
Family
ID=26507450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP19265690A Pending JPH03237195A (en) | 1989-12-28 | 1990-07-20 | Additive for oil and oil containing the additive |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH03237195A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019099813A (en) * | 2017-11-29 | 2019-06-24 | インフィニューム インターナショナル リミテッド | Lubricating oil composition |
JP2019099808A (en) * | 2017-11-29 | 2019-06-24 | インフィニューム インターナショナル リミテッド | Lubricating oil additive |
-
1990
- 1990-07-20 JP JP19265690A patent/JPH03237195A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019099813A (en) * | 2017-11-29 | 2019-06-24 | インフィニューム インターナショナル リミテッド | Lubricating oil composition |
JP2019099808A (en) * | 2017-11-29 | 2019-06-24 | インフィニューム インターナショナル リミテッド | Lubricating oil additive |
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