WO1989004358A2 - Compositions and lubricants and functional fluids containing same - Google Patents

Info

Publication number

WO1989004358A2

WO1989004358A2 PCT/US1988/003723 US8803723W WO8904358A2 WO 1989004358 A2 WO1989004358 A2 WO 1989004358A2 US 8803723 W US8803723 W US 8803723W WO 8904358 A2 WO8904358 A2 WO 8904358A2

Authority

WO

WIPO (PCT)

Prior art keywords

formula

composition

groups

group

carbon atoms

Prior art date

1987-11-05

Links

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• PatentScope
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• 239000000203 mixture Substances 0.000 title claims abstract description 201
• 239000000314 lubricant Substances 0.000 title claims abstract description 45
• 239000012530 fluid Substances 0.000 title claims abstract description 41
• -1 basic metal salt Chemical class 0.000 claims abstract description 255
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 158
• 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 133
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 103
• 239000011593 sulfur Substances 0.000 claims abstract description 99
• 150000001875 compounds Chemical class 0.000 claims abstract description 71
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 70
• 229910052751 metal Inorganic materials 0.000 claims abstract description 52
• 239000002184 metal Substances 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 150000002148 esters Chemical class 0.000 claims abstract description 38
• 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 37
• 239000011574 phosphorus Substances 0.000 claims abstract description 37
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 36
• 230000002378 acidificating effect Effects 0.000 claims abstract description 33
• 239000012990 dithiocarbamate Substances 0.000 claims abstract description 30
• 150000002894 organic compounds Chemical class 0.000 claims abstract description 29
• 150000001408 amides Chemical class 0.000 claims abstract description 27
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
• DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims abstract description 26
• 230000007935 neutral effect Effects 0.000 claims abstract description 26
• 239000006078 metal deactivator Substances 0.000 claims abstract description 24
• 229910052728 basic metal Inorganic materials 0.000 claims abstract description 23
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 22
• 229910052796 boron Inorganic materials 0.000 claims abstract description 19
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 18
• 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 16
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
• 229910052725 zinc Inorganic materials 0.000 claims abstract description 14
• 239000011701 zinc Substances 0.000 claims abstract description 14
• 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
• 150000002739 metals Chemical class 0.000 claims abstract description 12
• 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
• 229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
• 150000002596 lactones Chemical class 0.000 claims abstract description 11
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 10
• 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 10
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 10
• 229910052802 copper Inorganic materials 0.000 claims abstract description 10
• 239000010949 copper Substances 0.000 claims abstract description 10
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 10
• 238000009833 condensation Methods 0.000 claims abstract description 7
• 230000005494 condensation Effects 0.000 claims abstract description 7
• 125000000743 hydrocarbylene group Chemical group 0.000 claims abstract description 7
• 239000002253 acid Substances 0.000 claims description 99
• 125000003118 aryl group Chemical group 0.000 claims description 77
• 150000001412 amines Chemical class 0.000 claims description 53
• 238000000034 method Methods 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 44
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 43
• 125000001931 aliphatic group Chemical group 0.000 claims description 34
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 31
• 239000012964 benzotriazole Substances 0.000 claims description 27
• 239000002270 dispersing agent Substances 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 239000007795 chemical reaction product Substances 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
• 239000001301 oxygen Substances 0.000 claims description 23
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 20
• 239000011734 sodium Substances 0.000 claims description 19
• 229910052708 sodium Inorganic materials 0.000 claims description 19
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 19
• 239000003085 diluting agent Substances 0.000 claims description 18
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 15
• 239000011575 calcium Substances 0.000 claims description 15
• 229910052791 calcium Inorganic materials 0.000 claims description 15
• 230000008569 process Effects 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 13
• 239000011777 magnesium Substances 0.000 claims description 13
• 229910052749 magnesium Inorganic materials 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 10
• 150000001639 boron compounds Chemical class 0.000 claims description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 claims description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
• 150000001565 benzotriazoles Chemical class 0.000 claims description 9
• 238000005859 coupling reaction Methods 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
• MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 claims description 7
• 239000012141 concentrate Substances 0.000 claims description 7
• 230000008878 coupling Effects 0.000 claims description 7
• 238000010168 coupling process Methods 0.000 claims description 7
• 229940072082 magnesium salicylate Drugs 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000006024 2-pentenyl group Chemical group 0.000 claims description 6
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
• 229910052788 barium Inorganic materials 0.000 claims description 6
• 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 claims description 6
• 125000001326 naphthylalkyl group Chemical group 0.000 claims description 6
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 239000011591 potassium Substances 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
• 150000001555 benzenes Chemical class 0.000 claims description 4
• 229910052744 lithium Inorganic materials 0.000 claims description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
• 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
• 150000002790 naphthalenes Chemical class 0.000 claims description 2
• 239000002243 precursor Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
• WFFOAQQKQLMGGW-UHFFFAOYSA-N [hydroxy(mercapto)thiophosphoryl]amine Chemical compound NP(O)(S)=S WFFOAQQKQLMGGW-UHFFFAOYSA-N 0.000 claims 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
• 229960004889 salicylic acid Drugs 0.000 claims 1
• RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims 1
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims 1
• DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 1
• 239000000654 additive Substances 0.000 abstract description 12
• 239000012208 gear oil Substances 0.000 abstract description 3
• 238000006243 chemical reaction Methods 0.000 description 139
• 239000003795 chemical substances by application Substances 0.000 description 58
• 150000007513 acids Chemical class 0.000 description 54
• 239000000376 reactant Substances 0.000 description 49
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
• 239000000047 product Substances 0.000 description 42
• 229930195733 hydrocarbon Natural products 0.000 description 37
• 239000003921 oil Substances 0.000 description 37
• 235000019198 oils Nutrition 0.000 description 37
• 239000003599 detergent Substances 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
• 150000002430 hydrocarbons Chemical class 0.000 description 32
• 150000001735 carboxylic acids Chemical class 0.000 description 31
• 239000004215 Carbon black (E152) Substances 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 27
• 150000001336 alkenes Chemical class 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
• 150000003460 sulfonic acids Chemical class 0.000 description 26
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 24
• 150000001299 aldehydes Chemical class 0.000 description 24
• 150000002576 ketones Chemical class 0.000 description 24
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
• 125000001424 substituent group Chemical group 0.000 description 19
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 229910052799 carbon Inorganic materials 0.000 description 18
• 239000000543 intermediate Substances 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• 239000002904 solvent Substances 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 16
• 150000004659 dithiocarbamates Chemical class 0.000 description 16
• 239000000463 material Substances 0.000 description 15
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 15
• 229920000768 polyamine Polymers 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
• 150000008064 anhydrides Chemical class 0.000 description 13
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 12
• PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
• 150000002989 phenols Chemical class 0.000 description 12
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
• 150000001721 carbon Chemical group 0.000 description 11
• 239000003112 inhibitor Substances 0.000 description 11
• 229920000642 polymer Polymers 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
• 150000001298 alcohols Chemical class 0.000 description 10
• 239000003208 petroleum Substances 0.000 description 10
• 229920000098 polyolefin Polymers 0.000 description 10
• 150000003464 sulfur compounds Chemical class 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
• 230000001050 lubricating effect Effects 0.000 description 9
• LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• 229920002367 Polyisobutene Polymers 0.000 description 8
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 8
• NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 8
• 239000004519 grease Substances 0.000 description 8
• 150000001261 hydroxy acids Chemical class 0.000 description 8
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
• 238000002156 mixing Methods 0.000 description 8
• 150000003141 primary amines Chemical class 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• 239000002562 thickening agent Substances 0.000 description 8
• 239000005977 Ethylene Substances 0.000 description 7
• 229930040373 Paraformaldehyde Natural products 0.000 description 7
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 7
• 239000012298 atmosphere Substances 0.000 description 7
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
• 235000014113 dietary fatty acids Nutrition 0.000 description 7
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
• 239000000194 fatty acid Substances 0.000 description 7
• 229930195729 fatty acid Natural products 0.000 description 7
• 125000000468 ketone group Chemical group 0.000 description 7
• 239000002480 mineral oil Substances 0.000 description 7
• 235000010446 mineral oil Nutrition 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• 150000007524 organic acids Chemical class 0.000 description 7
• 229920002866 paraformaldehyde Polymers 0.000 description 7
• 235000019271 petrolatum Nutrition 0.000 description 7
• 150000003852 triazoles Chemical class 0.000 description 7
• KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
• 150000001447 alkali salts Chemical class 0.000 description 6
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 229920001577 copolymer Polymers 0.000 description 6
• 239000007822 coupling agent Substances 0.000 description 6
• LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
• 238000005886 esterification reaction Methods 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 150000004665 fatty acids Chemical class 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 125000000623 heterocyclic group Chemical group 0.000 description 6
• 239000010687 lubricating oil Substances 0.000 description 6
• 238000004519 manufacturing process Methods 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
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