JP2004526796A - ポプコーンポリマーの成長阻止 - Google Patents
ポプコーンポリマーの成長阻止 Download PDFInfo
- Publication number
- JP2004526796A JP2004526796A JP2002585360A JP2002585360A JP2004526796A JP 2004526796 A JP2004526796 A JP 2004526796A JP 2002585360 A JP2002585360 A JP 2002585360A JP 2002585360 A JP2002585360 A JP 2002585360A JP 2004526796 A JP2004526796 A JP 2004526796A
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- Prior art keywords
- tert
- group
- phenol
- composition
- hindered
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- Pending
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- 229920000642 polymer Polymers 0.000 title description 47
- 235000002017 Zea mays subsp mays Nutrition 0.000 title description 41
- 241000482268 Zea mays subsp. mays Species 0.000 title description 41
- 230000005764 inhibitory process Effects 0.000 title description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 84
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims abstract description 60
- 150000002989 phenols Chemical class 0.000 claims abstract description 44
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 diene compound Chemical class 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 238000012546 transfer Methods 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 150000002443 hydroxylamines Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 7
- 238000000034 method Methods 0.000 claims description 23
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 19
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 claims description 18
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 17
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 15
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 claims description 15
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 15
- 150000001993 dienes Chemical class 0.000 claims description 15
- 239000004250 tert-Butylhydroquinone Substances 0.000 claims description 15
- 235000019281 tert-butylhydroquinone Nutrition 0.000 claims description 15
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 claims description 11
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims description 10
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- RRUADNNEIGVWSQ-UHFFFAOYSA-N n-ethyl-n-methylhydroxylamine Chemical compound CCN(C)O RRUADNNEIGVWSQ-UHFFFAOYSA-N 0.000 claims description 8
- VDUIPQNXOQMTBF-UHFFFAOYSA-N n-ethylhydroxylamine Chemical compound CCNO VDUIPQNXOQMTBF-UHFFFAOYSA-N 0.000 claims description 8
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 claims description 8
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims description 7
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 230000001747 exhibiting effect Effects 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 5
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 claims description 5
- KDBZVULQVCUNNA-UHFFFAOYSA-N 2,5-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C)C(O)=C1 KDBZVULQVCUNNA-UHFFFAOYSA-N 0.000 claims description 5
- WKTFRVMBYLDVOK-UHFFFAOYSA-N 2,5-dipentylbenzene-1,4-diol Chemical compound CCCCCC1=CC(O)=C(CCCCC)C=C1O WKTFRVMBYLDVOK-UHFFFAOYSA-N 0.000 claims description 5
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 claims description 5
- VQQLTEBUMLSLFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VQQLTEBUMLSLFJ-UHFFFAOYSA-N 0.000 claims description 5
- FKWOGPPGVRDIRZ-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=CC=C1O FKWOGPPGVRDIRZ-UHFFFAOYSA-N 0.000 claims description 5
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 claims description 5
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- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 claims description 5
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 claims description 5
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 claims description 5
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 5
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 229960000990 monobenzone Drugs 0.000 claims description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 5
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 5
- KRZIKXRXQZBATP-UHFFFAOYSA-N 2,3,4,5-tetramethylquinoline Chemical compound C1=CC(C)=C2C(C)=C(C)C(C)=NC2=C1 KRZIKXRXQZBATP-UHFFFAOYSA-N 0.000 claims description 4
- PHWAJJWKNLWZGJ-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Br)=C(O)C(Br)=C1 PHWAJJWKNLWZGJ-UHFFFAOYSA-N 0.000 claims description 4
- WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical compound C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 claims description 4
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 4
- XEZLAJRZQNKEOJ-UHFFFAOYSA-N n-pentylhydroxylamine Chemical compound CCCCCNO XEZLAJRZQNKEOJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940032094 squalane Drugs 0.000 claims description 4
- 229940031439 squalene Drugs 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
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- 239000002904 solvent Substances 0.000 description 7
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- 238000012360 testing method Methods 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000895 extractive distillation Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 2
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- 239000005061 synthetic rubber Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- FOTIRCKWBGLFNQ-UHFFFAOYSA-N 1-methyl-5-[(1-methyltetrazol-5-yl)disulfanyl]tetrazole Chemical compound CN1N=NN=C1SSC1=NN=NN1C FOTIRCKWBGLFNQ-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- SEEZWGFVHCMHJF-UHFFFAOYSA-N 2-nitrosophenol Chemical class OC1=CC=CC=C1N=O SEEZWGFVHCMHJF-UHFFFAOYSA-N 0.000 description 1
- GQOCPYOUNQYQQM-UHFFFAOYSA-N 4-butan-2-yl-2,6-dibutylphenol Chemical compound CCCCC1=CC(C(C)CC)=CC(CCCC)=C1O GQOCPYOUNQYQQM-UHFFFAOYSA-N 0.000 description 1
- WSGDRFHJFJRSFY-UHFFFAOYSA-N 4-oxo-TEMPO Chemical compound CC1(C)CC(=O)CC(C)(C)N1[O] WSGDRFHJFJRSFY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
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- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
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- 239000007857 degradation product Substances 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
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- 150000005673 monoalkenes Chemical class 0.000 description 1
- XSKVWWRICSVZOV-UHFFFAOYSA-N n-benzyl-n-phenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)CC1=CC=CC=C1 XSKVWWRICSVZOV-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
- 239000002683 reaction inhibitor Substances 0.000 description 1
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- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2001/013969 WO2002088055A1 (en) | 2001-04-30 | 2001-04-30 | Inhibition of popcorn polymer growth |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004526796A true JP2004526796A (ja) | 2004-09-02 |
| JP2004526796A5 JP2004526796A5 (enExample) | 2011-08-18 |
Family
ID=21742543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002585360A Pending JP2004526796A (ja) | 2001-04-30 | 2001-04-30 | ポプコーンポリマーの成長阻止 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1383722B1 (enExample) |
| JP (1) | JP2004526796A (enExample) |
| KR (1) | KR20040058112A (enExample) |
| DE (1) | DE60125067T2 (enExample) |
| ES (1) | ES2274886T3 (enExample) |
| WO (1) | WO2002088055A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007137782A (ja) * | 2005-11-15 | 2007-06-07 | Hakuto Co Ltd | 汚れ防止方法 |
| JP4824038B2 (ja) * | 2005-01-18 | 2011-11-24 | ヨチュン・エヌシーシー・カンパニー・リミテッド | １，３−ブタジエンの重合防止剤及びこれを投入する１，３−ブタジエンの重合防止方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8440099B2 (en) | 2007-12-19 | 2013-05-14 | Air Products And Chemicals, Inc. | Stabilizers for the stabilization of unsaturated hydrocarbon-based precursor |
| US7968001B2 (en) | 2007-12-19 | 2011-06-28 | Air Products And Chemicals, Inc. | Stabilizers for the stabilization of unsaturated hydrocarbon-based precursor |
| EP2233505A1 (en) | 2009-03-23 | 2010-09-29 | Total Petrochemicals Research Feluy | Stabilised compositions comprising olefins |
| CN104364276B (zh) * | 2012-06-14 | 2017-06-09 | 安格斯化学公司 | 烷基羟胺化合物以及它们在速止自由基聚合中的应用 |
| WO2014052212A1 (en) * | 2012-09-28 | 2014-04-03 | Dow Global Technologies Llc | Alkyl hydroxylamine compounds and their use for shortstopping free radical polymerizations |
| EP3026101A1 (en) | 2014-11-26 | 2016-06-01 | Borealis AG | Wash oil for use as an antifouling agent in gas compressors |
| EP4212604A1 (en) * | 2022-01-13 | 2023-07-19 | TotalEnergies One Tech | Stabilised compositions comprising olefins |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49124001A (enExample) * | 1973-03-30 | 1974-11-27 | ||
| JPS63223003A (ja) * | 1987-03-13 | 1988-09-16 | Tokai Denka Kogyo Kk | ポツプコ−ンポリマ−の生成抑制法 |
| JPH0673105A (ja) * | 1992-08-25 | 1994-03-15 | Dainippon Ink & Chem Inc | 液状重合防止剤組成物 |
| WO1999044972A1 (en) * | 1998-03-03 | 1999-09-10 | Nippon Zeon Co., Ltd. | Polymerization-inhibiting composition, polymerization inhibitor and method for inhibiting polymerization |
| WO2000014039A1 (en) * | 1998-09-09 | 2000-03-16 | Baker Hughes Incorporated | Styrene monomer polymerization inhibition using substituted dihydroxyarenes and nitroxides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0240297A1 (en) * | 1986-04-01 | 1987-10-07 | Betz Europe, Inc. | Inhibiting polymerization of vinyl aromatic compounds |
| EP0594341B1 (en) * | 1992-10-21 | 1997-01-22 | Betz Europe, Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US5396005A (en) * | 1994-01-19 | 1995-03-07 | Betz Laboratories, Inc. | Compositions and methods for inhibiting polymerization of ethlenically unsaturated monomers |
| US5446220A (en) * | 1994-08-24 | 1995-08-29 | Betz Laboratories, Inc. | Methods for inhibiting vinyl aromatic monomer polymerization |
-
2001
- 2001-04-30 JP JP2002585360A patent/JP2004526796A/ja active Pending
- 2001-04-30 ES ES01932793T patent/ES2274886T3/es not_active Expired - Lifetime
- 2001-04-30 WO PCT/US2001/013969 patent/WO2002088055A1/en not_active Ceased
- 2001-04-30 EP EP01932793A patent/EP1383722B1/en not_active Expired - Lifetime
- 2001-04-30 DE DE60125067T patent/DE60125067T2/de not_active Expired - Lifetime
- 2001-04-30 KR KR10-2003-7014202A patent/KR20040058112A/ko not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49124001A (enExample) * | 1973-03-30 | 1974-11-27 | ||
| JPS63223003A (ja) * | 1987-03-13 | 1988-09-16 | Tokai Denka Kogyo Kk | ポツプコ−ンポリマ−の生成抑制法 |
| JPH0673105A (ja) * | 1992-08-25 | 1994-03-15 | Dainippon Ink & Chem Inc | 液状重合防止剤組成物 |
| WO1999044972A1 (en) * | 1998-03-03 | 1999-09-10 | Nippon Zeon Co., Ltd. | Polymerization-inhibiting composition, polymerization inhibitor and method for inhibiting polymerization |
| WO2000014039A1 (en) * | 1998-09-09 | 2000-03-16 | Baker Hughes Incorporated | Styrene monomer polymerization inhibition using substituted dihydroxyarenes and nitroxides |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4824038B2 (ja) * | 2005-01-18 | 2011-11-24 | ヨチュン・エヌシーシー・カンパニー・リミテッド | １，３−ブタジエンの重合防止剤及びこれを投入する１，３−ブタジエンの重合防止方法 |
| JP2007137782A (ja) * | 2005-11-15 | 2007-06-07 | Hakuto Co Ltd | 汚れ防止方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1383722B1 (en) | 2006-12-06 |
| DE60125067T2 (de) | 2007-05-03 |
| ES2274886T3 (es) | 2007-06-01 |
| EP1383722A1 (en) | 2004-01-28 |
| KR20040058112A (ko) | 2004-07-03 |
| DE60125067D1 (de) | 2007-01-18 |
| WO2002088055A1 (en) | 2002-11-07 |
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