SG183665A1 - Low sulfur metal detergent-dispersants - Google Patents
Low sulfur metal detergent-dispersants Download PDFInfo
- Publication number
- SG183665A1 SG183665A1 SG2012056180A SG2012056180A SG183665A1 SG 183665 A1 SG183665 A1 SG 183665A1 SG 2012056180 A SG2012056180 A SG 2012056180A SG 2012056180 A SG2012056180 A SG 2012056180A SG 183665 A1 SG183665 A1 SG 183665A1
- Authority
- SG
- Singapore
- Prior art keywords
- alkali metal
- process according
- reaction product
- alkaline earth
- alkyl group
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 104
- 239000011593 sulfur Substances 0.000 title claims abstract description 100
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 100
- 229910052751 metal Inorganic materials 0.000 title claims description 50
- 239000002184 metal Substances 0.000 title claims description 50
- 239000002270 dispersing agent Substances 0.000 title abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 110
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 109
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 101
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 90
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 89
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000010687 lubricating oil Substances 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 239000002585 base Substances 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 49
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 40
- 239000003921 oil Substances 0.000 claims description 37
- -1 sulfur halides Chemical class 0.000 claims description 31
- 239000002199 base oil Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 22
- 239000001569 carbon dioxide Substances 0.000 claims description 20
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 20
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 16
- 239000011591 potassium Substances 0.000 claims description 16
- 229910052700 potassium Inorganic materials 0.000 claims description 16
- 239000011575 calcium Substances 0.000 claims description 15
- 230000001050 lubricating effect Effects 0.000 claims description 15
- 238000005260 corrosion Methods 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 230000003472 neutralizing effect Effects 0.000 claims description 14
- 229910052791 calcium Inorganic materials 0.000 claims description 12
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 238000002485 combustion reaction Methods 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 239000003513 alkali Substances 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 abstract description 19
- 235000019198 oils Nutrition 0.000 description 36
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000008096 xylene Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000007797 corrosion Effects 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 235000011941 Tilia x europaea Nutrition 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000004571 lime Substances 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 230000020477 pH reduction Effects 0.000 description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
- 239000000920 calcium hydroxide Substances 0.000 description 6
- 235000011116 calcium hydroxide Nutrition 0.000 description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 229960001860 salicylate Drugs 0.000 description 6
- 229960004889 salicylic acid Drugs 0.000 description 6
- 239000013049 sediment Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000021523 carboxylation Effects 0.000 description 5
- 238000006473 carboxylation reaction Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003873 salicylate salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004706 metal oxides Chemical group 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- MAAUYFIROALKRY-UHFFFAOYSA-N 6-hydroxy-7-thiabicyclo[4.1.0]hepta-2,4-diene-1-carboxylic acid Chemical class C1=CC=CC2(C(=O)O)C1(O)S2 MAAUYFIROALKRY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000692870 Inachis io Species 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 description 2
- 238000004517 catalytic hydrocracking Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
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- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
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- 230000000979 retarding effect Effects 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- ADZWPLHWCUCTFM-UHFFFAOYSA-N 18,18,18-trichlorooctadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(Cl)(Cl)Cl ADZWPLHWCUCTFM-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical class C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- AZZWZMUXHALBCQ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(CC=2C=C(C)C(O)=C(C)C=2)=C1 AZZWZMUXHALBCQ-UHFFFAOYSA-N 0.000 description 1
- LJKQIQSBHFNMDV-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1S2 LJKQIQSBHFNMDV-UHFFFAOYSA-N 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011275 tar sand Substances 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 208000007004 trichohepatoenteric syndrome Diseases 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/52—Base number [TBN]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/192,757 US7956022B2 (en) | 2005-07-29 | 2005-07-29 | Low sulfur metal detergent-dispersants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG183665A1 true SG183665A1 (en) | 2012-09-27 |
Family
ID=37564325
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012056180A SG183665A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
| SG2012056214A SG183666A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
| SG200605090A SG129426A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
| SG200900619-8A SG149884A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012056214A SG183666A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
| SG200605090A SG129426A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
| SG200900619-8A SG149884A1 (en) | 2005-07-29 | 2006-07-28 | Low sulfur metal detergent-dispersants |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7956022B2 (https=) |
| EP (3) | EP1754699A3 (https=) |
| JP (2) | JP5390062B2 (https=) |
| CA (1) | CA2551702A1 (https=) |
| SG (4) | SG183665A1 (https=) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7956022B2 (en) * | 2005-07-29 | 2011-06-07 | Chevron Oronite Company Llc | Low sulfur metal detergent-dispersants |
| EP2048218A1 (en) | 2007-10-09 | 2009-04-15 | Infineum International Limited | A lubricating oil composition |
| ITMI20072290A1 (it) * | 2007-12-06 | 2009-06-07 | Itea Spa | Processo di combustione |
| EP2135926A1 (en) | 2008-05-20 | 2009-12-23 | Infineum International Limited | Marine engine lubrication |
| EP2123739B1 (en) | 2008-05-20 | 2017-09-27 | Infineum International Limited | Marine engine lubrication |
| ES2641591T3 (es) | 2008-05-20 | 2017-11-10 | Infineum International Limited | Lubricación de motor marino |
| DE102009034984A1 (de) | 2008-09-11 | 2010-07-01 | Infineum International Ltd., Abingdon | Detergens |
| DE102009034983A1 (de) * | 2008-09-11 | 2010-04-29 | Infineum International Ltd., Abingdon | Verfahren zum Vermindern von Asphaltenablagerung in einem Motor |
| KR101662350B1 (ko) | 2009-04-07 | 2016-10-04 | 인피늄 인터내셔날 리미티드 | 선박용 엔진의 윤활 |
| EP2365049B1 (en) | 2009-08-24 | 2013-04-03 | Infineum International Limited | Use of a lubricating additive |
| EP2447346B1 (en) | 2010-10-28 | 2014-03-05 | Infineum International Limited | Marine engine lubrication |
| GB2496732B (en) | 2011-11-17 | 2014-03-12 | Infineum Int Ltd | Marine engine lubrication |
| EP2634240B1 (en) | 2012-03-01 | 2018-06-06 | Infineum International Limited | Methode for the lubrication of a marine engine |
| US9206373B2 (en) | 2012-08-17 | 2015-12-08 | Afton Chemical Corporation | Calcium neutral and overbased mannich and anhydride adducts as detergents for engine oil lubricants |
| US9790330B2 (en) * | 2012-10-28 | 2017-10-17 | Polym Technology Corporation | Method for forming conjugated heteroaromatic homopolymer and copolymer, and products thereof |
| ES2712955T3 (es) | 2012-11-02 | 2019-05-16 | Infineum Int Ltd | Lubricación de motor marino |
| US8772209B2 (en) | 2012-11-20 | 2014-07-08 | Chevron Oronite Company Lls | Process for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition |
| EP2735603B1 (en) | 2012-11-21 | 2016-06-08 | Infineum International Limited | Marine engine lubrication |
| US9102896B2 (en) * | 2012-12-17 | 2015-08-11 | Chevron Japan Ltd. | Fuel economical lubricating oil composition for internal combustion engines |
| DK2765179T3 (en) | 2013-02-07 | 2017-01-09 | Infineum Int Ltd | Lubrication to a marine engine |
| ES2658621T3 (es) | 2013-07-09 | 2018-03-12 | Infineum International Limited | Lubricación de motor marino |
| SG10201802384QA (en) | 2013-09-23 | 2018-05-30 | Chevron Japan Ltd | A Fuel Economy Engine Oil Composition |
| ES2646051T3 (es) | 2013-09-24 | 2017-12-11 | Infineum International Limited | Lubricación de motores marinos |
| US9567554B2 (en) * | 2014-01-10 | 2017-02-14 | General Electric Company | Apparatus, method, and solvent for cleaning turbine components |
| US10364404B2 (en) | 2014-12-04 | 2019-07-30 | Infineum International Limited | Marine engine lubrication |
| US9879202B2 (en) | 2014-12-04 | 2018-01-30 | Infineum International Limited | Marine engine lubrication |
| EP3029133B1 (en) | 2014-12-04 | 2017-03-15 | Infineum International Limited | Marine engine lubrication |
| US10487288B2 (en) | 2015-09-16 | 2019-11-26 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
| US11168280B2 (en) | 2015-10-05 | 2021-11-09 | Infineum International Limited | Additive concentrates for the formulation of lubricating oil compositions |
| PL3421576T3 (pl) | 2017-06-30 | 2020-08-24 | Infineum International Limited | Sposób przeciwdziałania zanieczyszczeniu podczas rafinacji |
| EP3877490A1 (en) | 2018-11-09 | 2021-09-15 | Total Marketing Services | Compound comprising polyamine, carboxylate and boron functionalities and its use as a lubricant additive |
| JP2022512951A (ja) | 2018-11-09 | 2022-02-07 | トータル・マーケティング・サービシーズ | アミン官能基、カルボン酸塩官能基、およびホウ素官能基を含む化合物とその潤滑剤添加剤としての使用 |
| CN111349461B (zh) | 2018-12-20 | 2023-08-29 | 英菲诺姆国际有限公司 | 油防结垢和/或防沥青质附聚法 |
| CN111349480B (zh) | 2018-12-20 | 2024-02-23 | 英菲诺姆国际有限公司 | 烃船用燃料油 |
| CN114929846B (zh) | 2019-11-07 | 2024-05-14 | 道达尔能量联动技术公司 | 包含多胺、酸性官能团和硼官能团的化合物及其作为润滑剂添加剂的用途 |
| ES2994164T3 (en) | 2021-11-15 | 2025-01-20 | Infineum Int Ltd | Improvements in marine fuels |
| EP4303287A1 (en) | 2022-07-06 | 2024-01-10 | Infineum International Limited | Lubricating oil compositions |
| US20240301274A1 (en) | 2023-03-10 | 2024-09-12 | Infineum International Limited | Asphaltene deposition control |
| WO2026055108A1 (en) | 2024-09-03 | 2026-03-12 | Chevron Oronite Company Llc | Method and use of a lubricating oil compositions for preventing or reducing pre-ignition in hydrogen fueled engines |
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| US2256443A (en) | 1940-03-08 | 1941-09-16 | Socony Vacuum Oil Co Inc | Lubricant composition and improving agent therefor |
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| ATE106442T1 (de) | 1989-02-25 | 1994-06-15 | Bp Chemicals Additives | Verfahren zur herstellung eines zusatzkonzentrats für schmieröle. |
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| JPH06264084A (ja) * | 1993-03-12 | 1994-09-20 | Cosmo Sogo Kenkyusho:Kk | ヒドロキシアルキル安息香酸およびアルキルフェノールのアルカリ土類金属塩硫化混合物系極圧清浄剤ならびにその製法 |
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| FR2717491B1 (fr) * | 1994-03-17 | 1996-06-07 | Chevron Chem Sa | Additifs détergents-dispersants pour huiles lubrifiantes du type alkylsalicylates-alkylphénates, alcalino-terreux, sulfurisés et suralcalinisés. |
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| US6569818B2 (en) | 2000-06-02 | 2003-05-27 | Chevron Oronite Company, Llc | Lubricating oil composition |
| JP3722484B2 (ja) * | 2000-06-02 | 2005-11-30 | シェブロンテキサコジャパン株式会社 | 潤滑油組成物 |
| EP1236791A1 (en) * | 2001-02-16 | 2002-09-04 | Infineum International Limited | Overbased detergent additives |
| US6784143B2 (en) * | 2001-05-11 | 2004-08-31 | Infineum International Ltd. | Lubricating oil composition |
| AU2003256807A1 (en) * | 2002-07-23 | 2004-02-09 | Crompton Corporation | Engine oil comprising overbased salicylates based on styrenated salicylic acid |
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| US20040235682A1 (en) * | 2003-05-22 | 2004-11-25 | Chevron Oronite Company Llc | Low emission diesel lubricant with improved corrosion protection |
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| US8188020B2 (en) * | 2003-12-22 | 2012-05-29 | Chevron Oronite S.A. | Lubricating oil composition containing an alkali metal detergent |
| US7956022B2 (en) * | 2005-07-29 | 2011-06-07 | Chevron Oronite Company Llc | Low sulfur metal detergent-dispersants |
| US7951760B2 (en) * | 2005-07-29 | 2011-05-31 | Chevron Oronite S.A. | Overbased alkali metal alkylhydroxybenzoates having low crude sediment |
| US8030258B2 (en) * | 2005-07-29 | 2011-10-04 | Chevron Oronite Company Llc | Overbased alkaline earth metal alkylhydroxybenzoates having low crude sediment |
| JP5079407B2 (ja) * | 2007-06-28 | 2012-11-21 | シェブロンジャパン株式会社 | 省燃費ディーゼルエンジン潤滑用潤滑油組成物 |
-
2005
- 2005-07-29 US US11/192,757 patent/US7956022B2/en not_active Expired - Fee Related
-
2006
- 2006-07-10 CA CA002551702A patent/CA2551702A1/en not_active Abandoned
- 2006-07-10 EP EP06253600A patent/EP1754699A3/en not_active Withdrawn
- 2006-07-10 EP EP10181769A patent/EP2295405A1/en not_active Withdrawn
- 2006-07-10 EP EP10181771A patent/EP2316823A1/en not_active Withdrawn
- 2006-07-28 SG SG2012056180A patent/SG183665A1/en unknown
- 2006-07-28 SG SG2012056214A patent/SG183666A1/en unknown
- 2006-07-28 SG SG200605090A patent/SG129426A1/en unknown
- 2006-07-28 SG SG200900619-8A patent/SG149884A1/en unknown
- 2006-07-28 JP JP2006207005A patent/JP5390062B2/ja not_active Expired - Fee Related
-
2013
- 2013-07-29 JP JP2013156410A patent/JP2014001219A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2316823A1 (en) | 2011-05-04 |
| JP2007039457A (ja) | 2007-02-15 |
| US7956022B2 (en) | 2011-06-07 |
| JP2014001219A (ja) | 2014-01-09 |
| EP1754699A3 (en) | 2007-04-25 |
| SG129426A1 (en) | 2007-02-26 |
| JP5390062B2 (ja) | 2014-01-15 |
| SG183666A1 (en) | 2012-09-27 |
| CA2551702A1 (en) | 2007-01-29 |
| EP1754699A2 (en) | 2007-02-21 |
| US20070027057A1 (en) | 2007-02-01 |
| SG149884A1 (en) | 2009-02-27 |
| EP2295405A1 (en) | 2011-03-16 |
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