ZA200900082B - Process for producing polydienes - Google Patents

Process for producing polydienes Download PDF

Info

Publication number: ZA200900082B
Authority: ZA; South Africa
Prior art keywords: ether; neodymium; butyl; lanthanide; tolyl
Prior art date: 2007-12-31

Application number

ZA200900082A

Other languages

English (en)

Inventor

Steven Luo

Kevin M Mccauley

Jason T Poulton

Original Assignee

Bridgestone Corp

Priority date (The priority date 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 date listed.)

2007-12-31

Filing date

2009-01-05

Publication date

2009-12-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40473703&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200900082(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2009-01-05 Application filed by Bridgestone Corp filed Critical Bridgestone Corp

2009-12-30 Publication of ZA200900082B publication Critical patent/ZA200900082B/en

Links

238000000034 method Methods 0.000 title claims description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 44
-1 p-tolyl t-butyl ether Chemical compound 0.000 claims description 31
229910052747 lanthanoid Inorganic materials 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 21
150000002601 lanthanoid compounds Chemical class 0.000 claims description 19
239000002168 alkylating agent Substances 0.000 claims description 18
229940100198 alkylating agent Drugs 0.000 claims description 18
150000002602 lanthanoids Chemical class 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
150000001993 dienes Chemical class 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 17
239000000178 monomer Substances 0.000 claims description 16
238000006116 polymerization reaction Methods 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
230000000379 polymerizing effect Effects 0.000 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical group COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 3
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims 3
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
150000001983 dialkylethers Chemical group 0.000 claims 2
150000001987 diarylethers Chemical class 0.000 claims 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
150000002170 ethers Chemical class 0.000 claims 2
229920000570 polyether Polymers 0.000 claims 2
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims 2
TZGIRWVSWPFWBP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxymethylbenzene Chemical compound CC(C)(C)OCC1=CC=CC=C1 TZGIRWVSWPFWBP-UHFFFAOYSA-N 0.000 claims 1
NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 claims 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims 1
CHHASAIQKXOAOX-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-2,2-dimethylpropane Chemical compound CC(C)(C)COCC(C)(C)C CHHASAIQKXOAOX-UHFFFAOYSA-N 0.000 claims 1
KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 claims 1
AGARRLZBNOJWLG-UHFFFAOYSA-N 1-butoxy-4-methylbenzene Chemical compound CCCCOC1=CC=C(C)C=C1 AGARRLZBNOJWLG-UHFFFAOYSA-N 0.000 claims 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
LTSWUFKUZPPYEG-UHFFFAOYSA-N 1-decoxydecane Chemical compound CCCCCCCCCCOCCCCCCCCCC LTSWUFKUZPPYEG-UHFFFAOYSA-N 0.000 claims 1
BQMLWEKOSHSOFT-UHFFFAOYSA-N 1-ethoxy-2,2-dimethylpropane Chemical compound CCOCC(C)(C)C BQMLWEKOSHSOFT-UHFFFAOYSA-N 0.000 claims 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims 1
KIAMPLQEZAMORJ-UHFFFAOYSA-N 1-ethoxy-2-[2-(2-ethoxyethoxy)ethoxy]ethane Chemical compound CCOCCOCCOCCOCC KIAMPLQEZAMORJ-UHFFFAOYSA-N 0.000 claims 1
RQUBQBFVDOLUKC-UHFFFAOYSA-N 1-ethoxy-2-methylpropane Chemical compound CCOCC(C)C RQUBQBFVDOLUKC-UHFFFAOYSA-N 0.000 claims 1
WSWPHHNIHLTAHB-UHFFFAOYSA-N 1-ethoxy-4-methylbenzene Chemical compound CCOC1=CC=C(C)C=C1 WSWPHHNIHLTAHB-UHFFFAOYSA-N 0.000 claims 1
PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 claims 1
UJEGHEMJVNQWOJ-UHFFFAOYSA-N 1-heptoxyheptane Chemical compound CCCCCCCOCCCCCCC UJEGHEMJVNQWOJ-UHFFFAOYSA-N 0.000 claims 1
BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 claims 1
ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims 1
CYXMOAZSOPXQOD-UHFFFAOYSA-N 1-methyl-2-(2-methylphenoxy)benzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1C CYXMOAZSOPXQOD-UHFFFAOYSA-N 0.000 claims 1
FDLFMPKQBNPIER-UHFFFAOYSA-N 1-methyl-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(C)C=CC=2)=C1 FDLFMPKQBNPIER-UHFFFAOYSA-N 0.000 claims 1
SVNGWCNCUFTQNX-UHFFFAOYSA-N 1-methyl-4-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=C(C)C=C1 SVNGWCNCUFTQNX-UHFFFAOYSA-N 0.000 claims 1
YWYHGNUFMPSTTR-UHFFFAOYSA-N 1-methyl-4-(4-methylphenoxy)benzene Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C)C=C1 YWYHGNUFMPSTTR-UHFFFAOYSA-N 0.000 claims 1
BYCXSXPCTRWKRR-UHFFFAOYSA-N 1-methyl-4-octoxybenzene Chemical compound CCCCCCCCOC1=CC=C(C)C=C1 BYCXSXPCTRWKRR-UHFFFAOYSA-N 0.000 claims 1
ZHNNNPIVFOUVOO-UHFFFAOYSA-N 1-methyl-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(C)C=C1 ZHNNNPIVFOUVOO-UHFFFAOYSA-N 0.000 claims 1
QLTKVDKXTKKJOX-UHFFFAOYSA-N 1-methyl-4-propoxybenzene Chemical compound CCCOC1=CC=C(C)C=C1 QLTKVDKXTKKJOX-UHFFFAOYSA-N 0.000 claims 1
DKZRLCHWDNEKRH-UHFFFAOYSA-N 1-nonoxynonane Chemical compound CCCCCCCCCOCCCCCCCCC DKZRLCHWDNEKRH-UHFFFAOYSA-N 0.000 claims 1
AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 claims 1
FVNIMHIOIXPIQT-UHFFFAOYSA-N 2-methoxybutane Chemical compound CCC(C)OC FVNIMHIOIXPIQT-UHFFFAOYSA-N 0.000 claims 1
ONNUYWHIJSKABC-UHFFFAOYSA-N 2-methylpropoxybenzene Chemical compound CC(C)COC1=CC=CC=C1 ONNUYWHIJSKABC-UHFFFAOYSA-N 0.000 claims 1
ADHMUPZYLITZIH-UHFFFAOYSA-N 2-methylpropoxymethylbenzene Chemical compound CC(C)COCC1=CC=CC=C1 ADHMUPZYLITZIH-UHFFFAOYSA-N 0.000 claims 1
HYDWALOBQJFOMS-UHFFFAOYSA-N 3,6,9,12,15-pentaoxaheptadecane Chemical compound CCOCCOCCOCCOCCOCC HYDWALOBQJFOMS-UHFFFAOYSA-N 0.000 claims 1
YHCCCMIWRBJYHG-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane Chemical compound CCCCC(CC)COCC(CC)CCCC YHCCCMIWRBJYHG-UHFFFAOYSA-N 0.000 claims 1
FSSNZZBDEOYMMZ-UHFFFAOYSA-N 4-chloro-1h-pyrrolo[2,3-b]pyridin-5-ol Chemical compound OC1=CN=C2NC=CC2=C1Cl FSSNZZBDEOYMMZ-UHFFFAOYSA-N 0.000 claims 1
AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 claims 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
239000004721 Polyphenylene oxide Substances 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 claims 1
MAYUYFCAPVDYBQ-UHFFFAOYSA-N butoxymethylbenzene Chemical compound CCCCOCC1=CC=CC=C1 MAYUYFCAPVDYBQ-UHFFFAOYSA-N 0.000 claims 1
BYUYRWRYAISPPF-UHFFFAOYSA-N cyclobutyloxycyclobutane Chemical compound C1CCC1OC1CCC1 BYUYRWRYAISPPF-UHFFFAOYSA-N 0.000 claims 1
OCDXZFSOHJRGIL-UHFFFAOYSA-N cyclohexyloxycyclohexane Chemical compound C1CCCCC1OC1CCCCC1 OCDXZFSOHJRGIL-UHFFFAOYSA-N 0.000 claims 1
BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 claims 1
NUFBGJAEANEZKW-UHFFFAOYSA-N cyclopropyloxycyclopropane Chemical group C1CC1OC1CC1 NUFBGJAEANEZKW-UHFFFAOYSA-N 0.000 claims 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 claims 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims 1
ZLRROLLKQDRDPI-UHFFFAOYSA-L disodium;4,5-dihydroxybenzene-1,3-disulfonate;hydrate Chemical group O.[Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ZLRROLLKQDRDPI-UHFFFAOYSA-L 0.000 claims 1
ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 claims 1
NXZJVIKVJAKQOU-UHFFFAOYSA-N octoxymethylbenzene Chemical compound CCCCCCCCOCC1=CC=CC=C1 NXZJVIKVJAKQOU-UHFFFAOYSA-N 0.000 claims 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 1
ZYNMJJNWXVKJJV-UHFFFAOYSA-N propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=CC=C1 ZYNMJJNWXVKJJV-UHFFFAOYSA-N 0.000 claims 1
NTUCQKRAQSWLOP-UHFFFAOYSA-N propan-2-yloxymethylbenzene Chemical compound CC(C)OCC1=CC=CC=C1 NTUCQKRAQSWLOP-UHFFFAOYSA-N 0.000 claims 1
RPTKMZRQBREOMV-UHFFFAOYSA-N propoxymethylbenzene Chemical compound CCCOCC1=CC=CC=C1 RPTKMZRQBREOMV-UHFFFAOYSA-N 0.000 claims 1
HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims 1
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims 1
229910052779 Neodymium Inorganic materials 0.000 description 33
QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 25
125000001183 hydrocarbyl group Chemical group 0.000 description 12
238000012662 bulk polymerization Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
125000000392 cycloalkenyl group Chemical group 0.000 description 8
150000002901 organomagnesium compounds Chemical class 0.000 description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
150000007942 carboxylates Chemical group 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 6
150000004703 alkoxides Chemical group 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000000962 organic group Chemical group 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
125000004437 phosphorous atom Chemical group 0.000 description 4
229910052710 silicon Inorganic materials 0.000 description 4
239000010703 silicon Substances 0.000 description 4
125000003107 substituted aryl group Chemical group 0.000 description 4
125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
239000004568 cement Substances 0.000 description 3
150000002739 metals Chemical class 0.000 description 3
150000002902 organometallic compounds Chemical class 0.000 description 3
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
229910000722 Didymium Inorganic materials 0.000 description 2
241000224487 Didymium Species 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 2
238000010528 free radical solution polymerization reaction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
150000002798 neodymium compounds Chemical class 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 2
229940049964 oleate Drugs 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000012991 xanthate Substances 0.000 description 2
WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 1
MBULCFMSBDQQQT-UHFFFAOYSA-N (3-carboxy-2-hydroxypropyl)-trimethylazanium;2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound C[N+](C)(C)CC(O)CC(O)=O.[O-]C(=O)C1=CC(=O)NC(=O)N1 MBULCFMSBDQQQT-UHFFFAOYSA-N 0.000 description 1
BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
VQCPDMARLUVHOA-UHFFFAOYSA-N (4-methylphenyl)-(2-methylpropyl)alumane Chemical compound C1(=CC=C(C=C1)[AlH]CC(C)C)C VQCPDMARLUVHOA-UHFFFAOYSA-N 0.000 description 1
NTIWOYZPHSWEAP-UHFFFAOYSA-M (4-methylphenyl)-(2-methylpropyl)alumanylium;chloride Chemical compound [Cl-].CC(C)C[Al+]C1=CC=C(C)C=C1 NTIWOYZPHSWEAP-UHFFFAOYSA-M 0.000 description 1
JBMXTJBHVMDDQY-UHFFFAOYSA-N (4-methylphenyl)-octylalumane Chemical compound C1(=CC=C(C=C1)[AlH]CCCCCCCC)C JBMXTJBHVMDDQY-UHFFFAOYSA-N 0.000 description 1
MYSJAUGCDQAHMZ-UHFFFAOYSA-M (4-methylphenyl)-octylalumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]C1=CC=C(C)C=C1 MYSJAUGCDQAHMZ-UHFFFAOYSA-M 0.000 description 1
SVJIEGOVQBGOSU-UHFFFAOYSA-N (4-methylphenyl)-propan-2-ylalumane Chemical compound C1(=CC=C(C=C1)[AlH]C(C)C)C SVJIEGOVQBGOSU-UHFFFAOYSA-N 0.000 description 1
YFZPXQNLKWVZMW-UHFFFAOYSA-M (4-methylphenyl)-propan-2-ylalumanylium;chloride Chemical compound [Cl-].CC(C)[Al+]C1=CC=C(C)C=C1 YFZPXQNLKWVZMW-UHFFFAOYSA-M 0.000 description 1
PRPLGWFQYUPYBN-UHFFFAOYSA-N (4-methylphenyl)-propylalumane Chemical compound C1(=CC=C(C=C1)[AlH]CCC)C PRPLGWFQYUPYBN-UHFFFAOYSA-N 0.000 description 1
CHQIVLGTNKFHEO-UHFFFAOYSA-M (4-methylphenyl)-propylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]C1=CC=C(C)C=C1 CHQIVLGTNKFHEO-UHFFFAOYSA-M 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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238000006555 catalytic reaction Methods 0.000 description 1
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LDYLHMQUPCBROZ-UHFFFAOYSA-N diethyl(methoxy)alumane Chemical compound [O-]C.CC[Al+]CC LDYLHMQUPCBROZ-UHFFFAOYSA-N 0.000 description 1
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CCOCQIOIKQPQSR-UHFFFAOYSA-M diethylalumanylium;octadecanoate Chemical compound CC[Al+]CC.CCCCCCCCCCCCCCCCCC([O-])=O CCOCQIOIKQPQSR-UHFFFAOYSA-M 0.000 description 1
YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
JTGUKNQMNXAFIS-UHFFFAOYSA-K diheptylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC.CCCCCCCP([O-])(=O)CCCCCCC JTGUKNQMNXAFIS-UHFFFAOYSA-K 0.000 description 1
AXEOTJPPNKRJOQ-UHFFFAOYSA-K dihexyl phosphate;neodymium(3+) Chemical compound [Nd+3].CCCCCCOP([O-])(=O)OCCCCCC.CCCCCCOP([O-])(=O)OCCCCCC.CCCCCCOP([O-])(=O)OCCCCCC AXEOTJPPNKRJOQ-UHFFFAOYSA-K 0.000 description 1
MWNKMBHGMZHEMM-UHFFFAOYSA-N dimethylalumanylium;ethanolate Chemical compound CCO[Al](C)C MWNKMBHGMZHEMM-UHFFFAOYSA-N 0.000 description 1
IRGBBLIJYFWRJM-UHFFFAOYSA-M dimethylalumanylium;hexanoate Chemical compound C[Al+]C.CCCCCC([O-])=O IRGBBLIJYFWRJM-UHFFFAOYSA-M 0.000 description 1
SIWKOPAOOWDWHQ-UHFFFAOYSA-M dimethylalumanylium;phenoxide Chemical compound C[Al](C)OC1=CC=CC=C1 SIWKOPAOOWDWHQ-UHFFFAOYSA-M 0.000 description 1
DEYSFYUFFGZQQG-UHFFFAOYSA-K dioctadecylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCP([O-])(=O)CCCCCCCCCCCCCCCCCC DEYSFYUFFGZQQG-UHFFFAOYSA-K 0.000 description 1
GNPSMYTXIPVJDU-UHFFFAOYSA-N dioctylalumane Chemical compound C(CCCCCCC)[AlH]CCCCCCCC GNPSMYTXIPVJDU-UHFFFAOYSA-N 0.000 description 1
QRQUTSPLBBZERR-UHFFFAOYSA-M dioctylalumanylium;chloride Chemical compound CCCCCCCC[Al](Cl)CCCCCCCC QRQUTSPLBBZERR-UHFFFAOYSA-M 0.000 description 1
UZSAHKACJKVKEK-UHFFFAOYSA-K dioctylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC.CCCCCCCCP([O-])(=O)CCCCCCCC UZSAHKACJKVKEK-UHFFFAOYSA-K 0.000 description 1
CMISOYBKHBNISI-UHFFFAOYSA-K dipentylphosphinate;neodymium(3+) Chemical compound [Nd+3].CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC.CCCCCP([O-])(=O)CCCCC CMISOYBKHBNISI-UHFFFAOYSA-K 0.000 description 1
BUHQQXGTFKPOJT-UHFFFAOYSA-K diphenyl phosphate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1.C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 BUHQQXGTFKPOJT-UHFFFAOYSA-K 0.000 description 1
HIVRDDZUKVNKAO-UHFFFAOYSA-N diphenylalumane Chemical compound C1(=CC=CC=C1)[AlH]C1=CC=CC=C1 HIVRDDZUKVNKAO-UHFFFAOYSA-N 0.000 description 1
QJXQMMHNTBZSOF-UHFFFAOYSA-K diphenylphosphinate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 QJXQMMHNTBZSOF-UHFFFAOYSA-K 0.000 description 1
XOCWTYIVWYOSGQ-UHFFFAOYSA-N dipropylalumane Chemical compound C(CC)[AlH]CCC XOCWTYIVWYOSGQ-UHFFFAOYSA-N 0.000 description 1
ZMXPNWBFRPIZFV-UHFFFAOYSA-M dipropylalumanylium;chloride Chemical compound [Cl-].CCC[Al+]CCC ZMXPNWBFRPIZFV-UHFFFAOYSA-M 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
OAGKEKIEPNLLIS-UHFFFAOYSA-N ethanolate neodymium(3+) Chemical compound [Nd+3].CC[O-].CC[O-].CC[O-] OAGKEKIEPNLLIS-UHFFFAOYSA-N 0.000 description 1
JXVBWSROJSOQFU-UHFFFAOYSA-N ethanolate;methylaluminum(2+) Chemical compound CCO[Al](C)OCC JXVBWSROJSOQFU-UHFFFAOYSA-N 0.000 description 1
GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 1
XGAIERUWZADBAO-UHFFFAOYSA-N ethoxy-bis(2-methylpropyl)alumane Chemical compound CCO[Al](CC(C)C)CC(C)C XGAIERUWZADBAO-UHFFFAOYSA-N 0.000 description 1
REMDLFHXTIFOIT-UHFFFAOYSA-K ethoxymethanedithioate neodymium(3+) Chemical compound [Nd+3].CCOC([S-])=S.CCOC([S-])=S.CCOC([S-])=S REMDLFHXTIFOIT-UHFFFAOYSA-K 0.000 description 1
UABOHUHCGKGGOJ-UHFFFAOYSA-N ethyl(dimethoxy)alumane Chemical compound [O-]C.[O-]C.CC[Al+2] UABOHUHCGKGGOJ-UHFFFAOYSA-N 0.000 description 1
ODAHSCRBAKWZPS-UHFFFAOYSA-L ethyl(diphenoxy)alumane Chemical compound CC[Al+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ODAHSCRBAKWZPS-UHFFFAOYSA-L 0.000 description 1
SMCMEVQBOQDRPJ-UHFFFAOYSA-N ethyl(diphenyl)alumane Chemical compound C=1C=CC=CC=1[Al](CC)C1=CC=CC=C1 SMCMEVQBOQDRPJ-UHFFFAOYSA-N 0.000 description 1
NEPIVOURWZEXGS-UHFFFAOYSA-N ethyl-bis(4-methylphenyl)alumane Chemical compound C=1C=C(C)C=CC=1[Al](CC)C1=CC=C(C)C=C1 NEPIVOURWZEXGS-UHFFFAOYSA-N 0.000 description 1
UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
XDFDJBOEIDRBBG-UHFFFAOYSA-N fluoro hypofluorite;neodymium Chemical compound [Nd].FOF XDFDJBOEIDRBBG-UHFFFAOYSA-N 0.000 description 1
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
238000001879 gelation Methods 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
MUCJTVYXMIQXNE-UHFFFAOYSA-L hexanoate;methylaluminum(2+) Chemical compound [Al+2]C.CCCCCC([O-])=O.CCCCCC([O-])=O MUCJTVYXMIQXNE-UHFFFAOYSA-L 0.000 description 1
KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
WRYKIHMRDIOPSI-UHFFFAOYSA-N magnesium;benzene Chemical compound [Mg+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 WRYKIHMRDIOPSI-UHFFFAOYSA-N 0.000 description 1
IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
KJJBSBKRXUVBMX-UHFFFAOYSA-N magnesium;butane Chemical compound [Mg+2].CCC[CH2-].CCC[CH2-] KJJBSBKRXUVBMX-UHFFFAOYSA-N 0.000 description 1
LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
RVOYYLUVELMWJF-UHFFFAOYSA-N magnesium;hexane Chemical compound [Mg+2].CCCCC[CH2-].CCCCC[CH2-] RVOYYLUVELMWJF-UHFFFAOYSA-N 0.000 description 1
LZFCBBSYZJPPIV-UHFFFAOYSA-M magnesium;hexane;bromide Chemical compound [Mg+2].[Br-].CCCCC[CH2-] LZFCBBSYZJPPIV-UHFFFAOYSA-M 0.000 description 1
GBRJQTLHXWRDOV-UHFFFAOYSA-M magnesium;hexane;chloride Chemical compound [Mg+2].[Cl-].CCCCC[CH2-] GBRJQTLHXWRDOV-UHFFFAOYSA-M 0.000 description 1
WCFJMDWWJOCLSJ-UHFFFAOYSA-N magnesium;methanidylbenzene Chemical compound [Mg+2].[CH2-]C1=CC=CC=C1.[CH2-]C1=CC=CC=C1 WCFJMDWWJOCLSJ-UHFFFAOYSA-N 0.000 description 1
QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
DQZLQYHGCKLKGU-UHFFFAOYSA-N magnesium;propane Chemical compound [Mg+2].C[CH-]C.C[CH-]C DQZLQYHGCKLKGU-UHFFFAOYSA-N 0.000 description 1
CBNHBSGOXOSEAO-UHFFFAOYSA-N methanolate neodymium(3+) Chemical compound [Nd+3].[O-]C.[O-]C.[O-]C CBNHBSGOXOSEAO-UHFFFAOYSA-N 0.000 description 1
NEMYBHYAISOMTI-UHFFFAOYSA-N methanolate;2-methylpropylaluminum(2+) Chemical compound [O-]C.[O-]C.CC(C)C[Al+2] NEMYBHYAISOMTI-UHFFFAOYSA-N 0.000 description 1
DKUIXLPCCDROFD-UHFFFAOYSA-N methanolate;methylaluminum(2+) Chemical compound [O-]C.[O-]C.[Al+2]C DKUIXLPCCDROFD-UHFFFAOYSA-N 0.000 description 1
BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 description 1
PQYRGTGTFRXFEN-UHFFFAOYSA-N methoxy-bis(2-methylpropyl)alumane Chemical compound CC(C)C[Al](OC)CC(C)C PQYRGTGTFRXFEN-UHFFFAOYSA-N 0.000 description 1
DQLIEGFPDMCSLJ-UHFFFAOYSA-K methoxymethanedithioate neodymium(3+) Chemical compound [Nd+3].COC([S-])=S.COC([S-])=S.COC([S-])=S DQLIEGFPDMCSLJ-UHFFFAOYSA-K 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052590 monazite Inorganic materials 0.000 description 1
UEYXOBGKUHPHQO-UHFFFAOYSA-K n,n-di(propan-2-yl)carbamate;neodymium(3+) Chemical compound [Nd+3].CC(C)N(C(C)C)C([O-])=O.CC(C)N(C(C)C)C([O-])=O.CC(C)N(C(C)C)C([O-])=O UEYXOBGKUHPHQO-UHFFFAOYSA-K 0.000 description 1
SQUOJZZETZQEOF-UHFFFAOYSA-K n,n-di(propan-2-yl)carbamodithioate;neodymium(3+) Chemical compound [Nd+3].CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S SQUOJZZETZQEOF-UHFFFAOYSA-K 0.000 description 1
YUUKWVLDUDNKDT-UHFFFAOYSA-K n,n-dibenzylcarbamate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1CN(C(=O)[O-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=O)[O-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=O)[O-])CC1=CC=CC=C1 YUUKWVLDUDNKDT-UHFFFAOYSA-K 0.000 description 1
XXBGWCVWYRXRMO-UHFFFAOYSA-K n,n-dibenzylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 XXBGWCVWYRXRMO-UHFFFAOYSA-K 0.000 description 1
NOTLJNJGENTSBY-UHFFFAOYSA-K n,n-dibutylcarbamate;neodymium(3+) Chemical compound [Nd+3].CCCCN(C([O-])=O)CCCC.CCCCN(C([O-])=O)CCCC.CCCCN(C([O-])=O)CCCC NOTLJNJGENTSBY-UHFFFAOYSA-K 0.000 description 1
UKJJHVZVXZCPRF-UHFFFAOYSA-K n,n-dibutylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC UKJJHVZVXZCPRF-UHFFFAOYSA-K 0.000 description 1
VIZYOIUGCRJUHQ-UHFFFAOYSA-K n,n-diethylcarbamate;neodymium(3+) Chemical compound [Nd+3].CCN(CC)C([O-])=O.CCN(CC)C([O-])=O.CCN(CC)C([O-])=O VIZYOIUGCRJUHQ-UHFFFAOYSA-K 0.000 description 1
SZBUPRSARRAZQN-UHFFFAOYSA-K n,n-diethylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S.CCN(CC)C([S-])=S SZBUPRSARRAZQN-UHFFFAOYSA-K 0.000 description 1
HATKMJSGRRQFMU-UHFFFAOYSA-K n,n-dimethylcarbamate;neodymium(3+) Chemical compound [Nd+3].CN(C)C([O-])=O.CN(C)C([O-])=O.CN(C)C([O-])=O HATKMJSGRRQFMU-UHFFFAOYSA-K 0.000 description 1
DXENBISLKDEHAN-UHFFFAOYSA-K n,n-dimethylcarbamodithioate;neodymium(3+) Chemical compound [Nd+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S DXENBISLKDEHAN-UHFFFAOYSA-K 0.000 description 1
LIOPISMUTXUKFO-UHFFFAOYSA-K neodymium(3+) pentanoate Chemical compound [Nd+3].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O LIOPISMUTXUKFO-UHFFFAOYSA-K 0.000 description 1
IDIGCVOPRGKSDP-UHFFFAOYSA-K neodymium(3+) phenylmethoxymethanedithioate Chemical compound [Nd+3].[S-]C(=S)OCc1ccccc1.[S-]C(=S)OCc1ccccc1.[S-]C(=S)OCc1ccccc1 IDIGCVOPRGKSDP-UHFFFAOYSA-K 0.000 description 1
QUFRWNPMZBKODL-UHFFFAOYSA-K neodymium(3+) propan-2-yloxymethanedithioate Chemical compound [Nd+3].CC(C)OC([S-])=S.CC(C)OC([S-])=S.CC(C)OC([S-])=S QUFRWNPMZBKODL-UHFFFAOYSA-K 0.000 description 1
IQILFJXGSRKIIW-UHFFFAOYSA-N neodymium(3+) triazide Chemical compound [Nd+3].[N-]=[N+]=[N-].[N-]=[N+]=[N-].[N-]=[N+]=[N-] IQILFJXGSRKIIW-UHFFFAOYSA-N 0.000 description 1
AAIPJXDONHAQHJ-UHFFFAOYSA-K neodymium(3+) tricarbamate Chemical class [Nd+3].NC([O-])=O.NC([O-])=O.NC([O-])=O AAIPJXDONHAQHJ-UHFFFAOYSA-K 0.000 description 1
FJWHSHNHTPHETF-UHFFFAOYSA-N neodymium(3+) tricyanide Chemical compound [Nd+3].[C-]#N.[C-]#N.[C-]#N FJWHSHNHTPHETF-UHFFFAOYSA-N 0.000 description 1
HCOLBMWNEVUKDB-UHFFFAOYSA-K neodymium(3+) trithiocyanate Chemical compound [Nd+3].[S-]C#N.[S-]C#N.[S-]C#N HCOLBMWNEVUKDB-UHFFFAOYSA-K 0.000 description 1
MPKWOMQKNIDCKY-UHFFFAOYSA-K neodymium(3+);2-nonylphenolate Chemical compound [Nd+3].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] MPKWOMQKNIDCKY-UHFFFAOYSA-K 0.000 description 1
SIINVGJQWZKNSJ-UHFFFAOYSA-K neodymium(3+);octadecanoate Chemical compound [Nd+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O SIINVGJQWZKNSJ-UHFFFAOYSA-K 0.000 description 1
MHJIJZIBANOIDE-UHFFFAOYSA-K neodymium(3+);prop-2-enoate Chemical compound [Nd+3].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C MHJIJZIBANOIDE-UHFFFAOYSA-K 0.000 description 1
HZHUIQPXRWTHNF-UHFFFAOYSA-N neodymium(3+);propan-2-olate Chemical compound [Nd+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HZHUIQPXRWTHNF-UHFFFAOYSA-N 0.000 description 1
HPCGPGSYNUPEKZ-UHFFFAOYSA-K neodymium(3+);tribenzoate Chemical compound [Nd+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 HPCGPGSYNUPEKZ-UHFFFAOYSA-K 0.000 description 1
LBWLQVSRPJHLEY-UHFFFAOYSA-K neodymium(3+);tribromide Chemical compound Br[Nd](Br)Br LBWLQVSRPJHLEY-UHFFFAOYSA-K 0.000 description 1
SXSPKVLHGFYNGI-UHFFFAOYSA-K neodymium(3+);tricarbamodithioate Chemical class [Nd+3].NC([S-])=S.NC([S-])=S.NC([S-])=S SXSPKVLHGFYNGI-UHFFFAOYSA-K 0.000 description 1
AARCLZBTVAUMJK-UHFFFAOYSA-K neodymium(3+);triformate Chemical compound [Nd+3].[O-]C=O.[O-]C=O.[O-]C=O AARCLZBTVAUMJK-UHFFFAOYSA-K 0.000 description 1
DKSXWSAKLYQPQE-UHFFFAOYSA-K neodymium(3+);triiodide Chemical compound I[Nd](I)I DKSXWSAKLYQPQE-UHFFFAOYSA-K 0.000 description 1
TZNZEEADHYGQQO-UHFFFAOYSA-K neodymium(3+);triphenoxide Chemical compound [Nd+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 TZNZEEADHYGQQO-UHFFFAOYSA-K 0.000 description 1
ATINCSYRHURBSP-UHFFFAOYSA-K neodymium(iii) chloride Chemical compound Cl[Nd](Cl)Cl ATINCSYRHURBSP-UHFFFAOYSA-K 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000005474 octanoate group Chemical group 0.000 description 1
JXRJZEIFKKYMBS-UHFFFAOYSA-N octyl(phenyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCCCCCCC JXRJZEIFKKYMBS-UHFFFAOYSA-N 0.000 description 1
KMKBWZXSKDYZDZ-UHFFFAOYSA-M octyl(phenyl)alumanylium;chloride Chemical compound [Cl-].CCCCCCCC[Al+]C1=CC=CC=C1 KMKBWZXSKDYZDZ-UHFFFAOYSA-M 0.000 description 1
SOEVKJXMZBAALG-UHFFFAOYSA-N octylalumane Chemical compound CCCCCCCC[AlH2] SOEVKJXMZBAALG-UHFFFAOYSA-N 0.000 description 1
RBLGTYCOUOIUNY-UHFFFAOYSA-L octylaluminum(2+);dichloride Chemical compound CCCCCCCC[Al](Cl)Cl RBLGTYCOUOIUNY-UHFFFAOYSA-L 0.000 description 1
125000001117 oleyl 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])=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])[H] 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
QDUCABQBSRSYCO-UHFFFAOYSA-N phenyl(propan-2-yl)alumane Chemical compound C1(=CC=CC=C1)[AlH]C(C)C QDUCABQBSRSYCO-UHFFFAOYSA-N 0.000 description 1
CUIJJJLOSZSJRO-UHFFFAOYSA-M phenyl(propan-2-yl)alumanylium;chloride Chemical compound [Cl-].CC(C)[Al+]C1=CC=CC=C1 CUIJJJLOSZSJRO-UHFFFAOYSA-M 0.000 description 1
ZKGDHJAHOGRQEP-UHFFFAOYSA-N phenyl(propyl)alumane Chemical compound C1(=CC=CC=C1)[AlH]CCC ZKGDHJAHOGRQEP-UHFFFAOYSA-N 0.000 description 1
AAQNAPUTWYBWOV-UHFFFAOYSA-M phenyl(propyl)alumanylium;chloride Chemical compound [Cl-].CCC[Al+]C1=CC=CC=C1 AAQNAPUTWYBWOV-UHFFFAOYSA-M 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
ZYTJPPRBIGGXRO-UHFFFAOYSA-N propan-2-ylalumane Chemical compound C(C)(C)[AlH2] ZYTJPPRBIGGXRO-UHFFFAOYSA-N 0.000 description 1
OBRKWFIGZSMARO-UHFFFAOYSA-N propylalumane Chemical compound [AlH2]CCC OBRKWFIGZSMARO-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
238000004064 recycling Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
MCWWHQMTJNSXPX-UHFFFAOYSA-N tribenzylalumane Chemical compound C=1C=CC=CC=1C[Al](CC=1C=CC=CC=1)CC1=CC=CC=C1 MCWWHQMTJNSXPX-UHFFFAOYSA-N 0.000 description 1
SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
ZIYNWDQDHKSRCE-UHFFFAOYSA-N tricyclohexylalumane Chemical compound C1CCCCC1[Al](C1CCCCC1)C1CCCCC1 ZIYNWDQDHKSRCE-UHFFFAOYSA-N 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
XRADHEAKQRNYQQ-UHFFFAOYSA-K trifluoroneodymium Chemical compound F[Nd](F)F XRADHEAKQRNYQQ-UHFFFAOYSA-K 0.000 description 1
ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
JOJQVUCWSDRWJE-UHFFFAOYSA-N tripentylalumane Chemical compound CCCCC[Al](CCCCC)CCCCC JOJQVUCWSDRWJE-UHFFFAOYSA-N 0.000 description 1
JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
QDHQENQYSFSSQA-UHFFFAOYSA-N tris(1-methylcyclopentyl)alumane Chemical compound C1CCCC1(C)[Al](C1(C)CCCC1)C1(C)CCCC1 QDHQENQYSFSSQA-UHFFFAOYSA-N 0.000 description 1
MYWRONRUDLXRGX-UHFFFAOYSA-N tris(2,2-dimethylpropyl)alumane Chemical compound CC(C)(C)C[Al](CC(C)(C)C)CC(C)(C)C MYWRONRUDLXRGX-UHFFFAOYSA-N 0.000 description 1
ZHRAFNQICZNWIK-UHFFFAOYSA-N tris(2,6-dimethylphenyl)alumane Chemical compound CC1=CC=CC(C)=C1[Al](C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C ZHRAFNQICZNWIK-UHFFFAOYSA-N 0.000 description 1
FHAOCGKAMRAFMM-UHFFFAOYSA-N tris(2-ethylhexyl)alumane Chemical compound CCCCC(CC)C[Al](CC(CC)CCCC)CC(CC)CCCC FHAOCGKAMRAFMM-UHFFFAOYSA-N 0.000 description 1
WSITXTIRYQMZHM-UHFFFAOYSA-N tris(4-methylphenyl)alumane Chemical compound C1=CC(C)=CC=C1[Al](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WSITXTIRYQMZHM-UHFFFAOYSA-N 0.000 description 1
RTAKQLTYPVIOBZ-UHFFFAOYSA-N tritert-butylalumane Chemical compound CC(C)(C)[Al](C(C)(C)C)C(C)(C)C RTAKQLTYPVIOBZ-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000003911 water pollution Methods 0.000 description 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/902—Monomer polymerized in bulk in presence of transition metal containing catalyst

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Polymerisation Methods In General (AREA)
Polymerization Catalysts (AREA)

ZA200900082A 2007-12-31 2009-01-05 Process for producing polydienes ZA200900082B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US11/967,549 US7741418B2 (en)	2007-12-31	2007-12-31	Process for producing polydienes

Publications (1)

Publication Number	Publication Date
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Country Status (9)

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US (2)	US7741418B2 (de)
EP (1)	EP2075267B1 (de)
JP (1)	JP5249746B2 (de)
KR (1)	KR101612954B1 (de)
CN (1)	CN101475655B (de)
BR (1)	BRPI0806041B1 (de)
ES (1)	ES2437117T3 (de)
RU (1)	RU2499803C2 (de)
ZA (1)	ZA200900082B (de)

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US7741418B2 (en) *	2007-12-31	2010-06-22	Bridgestone Corporation	Process for producing polydienes

2007
- 2007-12-31 US US11/967,549 patent/US7741418B2/en active Active
2008
- 2008-12-26 JP JP2008335142A patent/JP5249746B2/ja not_active Expired - Fee Related
- 2008-12-26 RU RU2008151961/04A patent/RU2499803C2/ru active
- 2008-12-29 BR BRPI0806041-0A patent/BRPI0806041B1/pt active IP Right Grant
- 2008-12-30 ES ES08254180.6T patent/ES2437117T3/es active Active
- 2008-12-30 EP EP08254180.6A patent/EP2075267B1/de not_active Not-in-force
- 2008-12-30 KR KR1020080136787A patent/KR101612954B1/ko not_active Expired - Fee Related
- 2008-12-31 CN CN200810192996.5A patent/CN101475655B/zh not_active Expired - Fee Related
2009
- 2009-01-05 ZA ZA200900082A patent/ZA200900082B/en unknown
2010
- 2010-06-15 US US12/815,841 patent/US7977437B2/en active Active

Also Published As

Publication number	Publication date
BRPI0806041A2 (pt)	2011-08-16
US20090171046A1 (en)	2009-07-02
EP2075267A3 (de)	2009-08-12
CN101475655B (zh)	2015-06-17
EP2075267A2 (de)	2009-07-01
RU2008151961A (ru)	2010-07-10
JP5249746B2 (ja)	2013-07-31
ES2437117T3 (es)	2014-01-09
CN101475655A (zh)	2009-07-08
US7977437B2 (en)	2011-07-12
KR101612954B1 (ko)	2016-04-15
RU2499803C2 (ru)	2013-11-27
US7741418B2 (en)	2010-06-22
KR20090073986A (ko)	2009-07-03
BRPI0806041B1 (pt)	2022-08-16
JP2009185280A (ja)	2009-08-20
EP2075267B1 (de)	2013-10-30
US20100273963A1 (en)	2010-10-28

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