JP2009041020A - 重合失活剤としてのポリヒドロキシ化合物 - Google Patents
重合失活剤としてのポリヒドロキシ化合物 Download PDFInfo
- Publication number
- JP2009041020A JP2009041020A JP2008204752A JP2008204752A JP2009041020A JP 2009041020 A JP2009041020 A JP 2009041020A JP 2008204752 A JP2008204752 A JP 2008204752A JP 2008204752 A JP2008204752 A JP 2008204752A JP 2009041020 A JP2009041020 A JP 2009041020A
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- JP
- Japan
- Prior art keywords
- polyhydroxy compound
- compound
- polymerization
- polymerization mixture
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 147
- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 238000010791 quenching Methods 0.000 title abstract description 13
- 230000000171 quenching effect Effects 0.000 title abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 114
- 229920000642 polymer Polymers 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 36
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims description 99
- 239000003054 catalyst Substances 0.000 claims description 69
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 35
- -1 2-pentanediol Chemical compound 0.000 claims description 20
- 239000012967 coordination catalyst Substances 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 13
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 4
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
- CDAISMWEOUEBRE-UHFFFAOYSA-N inositol Chemical compound OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 2
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 2
- ZFECCYLNALETDE-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]propan-2-ol Chemical compound CC(O)CN(CCO)CCO ZFECCYLNALETDE-UHFFFAOYSA-N 0.000 claims description 2
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 claims description 2
- VRYALKFFQXWPIH-HSUXUTPPSA-N 2-deoxy-D-galactose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-HSUXUTPPSA-N 0.000 claims description 2
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 2
- PSJBSUHYCGQTHZ-UHFFFAOYSA-N 3-Methoxy-1,2-propanediol Chemical compound COCC(O)CO PSJBSUHYCGQTHZ-UHFFFAOYSA-N 0.000 claims description 2
- OYYXNGVBOWXTPN-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]propane-1,2-diol Chemical compound CC(C)N(C(C)C)CC(O)CO OYYXNGVBOWXTPN-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims description 2
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical class OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 claims description 2
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 claims description 2
- ZAQJHHRNXZUBTE-WUJLRWPWSA-N D-xylulose Chemical compound OC[C@@H](O)[C@H](O)C(=O)CO ZAQJHHRNXZUBTE-WUJLRWPWSA-N 0.000 claims description 2
- 239000004386 Erythritol Substances 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- PMMURAAUARKVCB-UHFFFAOYSA-N alpha-D-ara-dHexp Natural products OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 claims description 2
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- HXYCHJFUBNTKQR-UHFFFAOYSA-N heptane-1,2,3-triol Chemical compound CCCCC(O)C(O)CO HXYCHJFUBNTKQR-UHFFFAOYSA-N 0.000 claims description 2
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 claims description 2
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 claims description 2
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 claims description 2
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 claims description 2
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- CXEMWUYNUIKMNF-UHFFFAOYSA-N tert-butyl 4-chlorosulfonylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(S(Cl)(=O)=O)CC1 CXEMWUYNUIKMNF-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000811 xylitol Substances 0.000 claims description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims 1
- 150000002440 hydroxy compounds Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 31
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 28
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- 239000005060 rubber Substances 0.000 description 18
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
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Abstract
【解決手段】活性重合混合物を失活させるための方法であって、該方法は、活性重合混合物にポリヒドロキシ化合物を導入する工程を含む。ポリヒドロキシ化合物が、ジヒドロキシ化合物、トリヒドロキシ化合物、テトラヒドロキシ化合物及び多ヒドロキシ化合物よりなる群から選択され、又ポリヒドロキシ化合物が、脂肪族ポリヒドロキシ化合物、脂環族ポリヒドロキシ化合物及び芳香族ポリヒドロキシ化合物からなる群から選択される。
【選択図】なし
Description
この例では、実質的な連続バルク重合方法によって、1,3-ブタジエンを重合し、シス-1,4-ポリブタジエンとした。ニートの1,3-ブタジエン、0.0335Mのバーサチック酸ネオジム(NdV3)のへキサン溶液及び0.68Mのトリイソブチルアルミニウム(TIBA)のへキサン溶液を連続的に触媒熟成容器に供給し、ここで、10分間、三種類の成分を互いに接触させた。該触媒熟成容器には、内径が約1.1cmで且つ長さが約122mのコイル管が含まれており、該コイル管は、所望の滞留時間を提供するために十分に長く、また、その管内径は、流れ成分の乱流速度の分布を達成するものであった。1,3-ブタジエン、TIBA及びNdV3の熟成混合物を連続重合反応器に供給し、ここで、該混合物を0.070Mの二塩化エチルアルミニウム(EADC)のへキサン溶液の連続流れと混合した。該反応器は、高粘度重合体セメントを混合可能な機械攪拌機と、1,3-ブタジエンの蒸発/濃縮の割合を制御して反応器内のセメント温度を制御するのに用いる還流冷却器とを具えていた。特に、該冷却器への冷水の流れを制御することで、1,3-ブタジエン蒸発/濃縮の割合を維持し、反応器の等温操作を可能にする。上記した1,3-ブタジエン及び触媒の混合物は、反応器中29℃にて18分の平均滞留時間をかけ、その残留時間の間、1,3-ブタジエンを約10%の転化率まで重合した。得られた重合体セメントをプログレッシブキャビティポンプによって反応器から連続的に回収した。ここで、セメント中に、重合開始剤として用いた0.010MのN,N,N',N'-テトラメチルエチレンジアミン(TMEDA)のへキサン溶液の流れを導入して混合した。また、プログレッシブキャビティポンプは、重合反応器中の液面の制御に関与していた。プログレッシブキャビティポンプを通過した後、セメントをインラインミキサーに供給した。ここで、セメント中に、カップリング剤として用いた0.010Mのジ-n-オクチルスズビス(マレイン酸2-エチルヘキシル)(DOTBOM)のへキサン溶液の流れを導入して混合した。次いで、反応性重合体とカップリング剤との反応に適した滞留時間を提供する他の攪拌型反応器に、セメントを移送した。次に、残留している反応性重合体や触媒をいずれも非活性化させるため、エチレングリコールの流れを用いてセメントを失活させた。更に、1,3-ブタジエン中に溶解したIrganoxTM1076とIrganoxTM1520との混合物からなる酸化防止剤の流れを加えることで、セメントを安定させた。重合体から未反応単量体を取り除くため、脱揮発器に最終セメントを送った。得られた重合体は、押出機を用いることで脱揮発器から押し出された。
失活剤としてエチレングリコールの代わりに蒸留タル油を用い、上記例1と同様な実験を行った。蒸留タル油は、紙の製造に由来する生産物であり、長鎖カルボン酸の混合物を含む。使用した蒸留タル油のモル量は、各蒸留タル油分子が活性カルボキシ基を一つのみ含有するのに対し、各エチレングリコール分子は二つのヒドロキシ基を含有するので、例1で用いたエチレングリコールのモル量の2倍であった。押出機から出た重合体は、下記に示す特性を有していた。ML1+4=29.4、Mn=95,200、Mw=428,300、Mw/Mn=4.5、シス-1,4-結合=99.1%、トランス-1,4-結合=0.6%、1,2-結合=0.3%。
失活剤としてエチレングリコールの代わりに1,5-ペンタンジオールを用い、上記例1と同様な実験を行った。押出機から出た重合体は、下記に示す特性を有していた。ML1+4=39.3、Mn=93,400、Mw=381,900、Mw/Mn=4.1、シス-1,4-結合=99.0%、トランス-1,4-結合=0.7%、1,2-結合=0.3%。
例1及び例2において、失活剤としてエチレングリコール及び蒸留タル油をそれぞれ用いて製造した重合体サンプルを、カーボンブラックが充填されたゴムコンパウンドに用いて評価した。該ゴムコンパウンドの組成を表1に集約する。表の数値は、ゴム100重量部に対する重量部(phr)として表される。
失活剤としてエチレングリコールの代わりにn-ヘキサノールを用いて、上記例1と同様な実験を行った。n-ヘキサノールが低沸点であるため、再利用1,3-ブタジエンはn-ヘキサノールで汚染されていることが分かった。結果として、その重合は、再利用単量体供給中の水分の増加によって、次第に緩徐になった。
失活剤としてエチレングリコールの代わりに蒸留水を用いて、上記例1と同様な実験を行った。水が低沸点であるため、再利用1,3-ブタジエンは水で汚染されていることが分かった。結果として、その重合は、再利用単量体供給中の水分の増加によって、次第に緩徐になった。
Claims (5)
- 活性重合混合物を失活させるための方法であって、
活性重合混合物にポリヒドロキシ化合物を導入する工程を含むことを特徴とする方法。 - 重合体を製造するための方法であって、
(a)単量体と触媒とを導入し、溶媒を20重量%未満含む活性重合混合物を形成させる工程と、
(b)前記活性重合混合物にポリヒドロキシ化合物を加える工程と、
を含む方法であり、
前記触媒がアニオン重合開始剤又は配位触媒系を含み、また、前記ポリヒドロキシ化合物は、当量分子量が100g/モル未満で且つ沸点が180℃を超えることを特徴とする方法。 - 重合体を製造するための連続重合方法であって、
(a)単量体と触媒とを連続的に導入し、溶媒を20重量%未満含む活性重合混合物を形成させる工程と、
(b)前記単量体の少なくとも一部を第一領域内で重合させる工程と、
(c)連続的に、前記第一領域から前記活性重合混合物を取り出し、該混合物を第二領域に移送する工程と、
(d)前記第二領域内で前記活性重合混合物にポリヒドロキシ化合物を連続的に導入し、少なくとも部分的に失活している重合混合物を形成させる工程と
を含むことを特徴とする方法。 - 活性重合混合物にポリヒドロキシ化合物を導入することを含む方法によって製造した重合体。
- 前記ポリヒドロキシ化合物が、ジヒドロキシ化合物、トリヒドロキシ化合物、テトラヒドロキシ化合物及び多ヒドロキシ化合物よりなる群から選択され、又は前記ポリヒドロキシ化合物が、脂肪族ポリヒドロキシ化合物、脂環式ポリヒドロキシ化合物、脂環式ポリヒドロキシ化合物及び芳香族ポリヒドロキシ化合物よりなる群から選択され、又は前記ポリヒドロキシ化合物が、1,2-エタンジオール、1,2-プロパンジオール、1,3-プロパンジオール、2,3-ジメチル-2,3-ブタンジオール、2,2-ジメチル-1,3-プロパンジオール、1,2-ブタンジオール、1,3-ブタンジオール、1,4-ブタンジオール、2,3-ブタンジオール、1,2-ペンタンジオール、1,3-ペンタンジオール、1,4-ペンタンジオール、1,5-ペンタンジオール、2,3-ペンタンジオール、2,4-ペンタンジオール、1,2-ヘキサンジオール、1,5-ヘキサンジオール、1,6-ヘキサンジオール、2,5-ヘキサンジオール、ジエチレングリコール、トリエチレングリコール、ジプロピレングリコール、ジエタノールアミン、N-n-ブチルジエタノールアミン、N-t-ブチルジエタノールアミン、3-ジイソプロピルアミノ-1,2-プロパンジオール、1,2-シクロペンタンジオール、1,3-シクロペンタンジオール、1,2-シクロヘキサンジオール、1,3-シクロヘキサンジオール、1,4-シクロヘキサンジオール、3-メトキシ-1,2-プロパンジオール及びカテコールよりなる群から選択され、又は前記ポリヒドロキシ化合物が、1,2,3-プロパントリオール、2-ヒドロキシメチル-1,3-プロパンジオール、1,2,4-ブタントリオール、1,1,1-トリス(ヒドロキシメチル)エタン、1,2,6-ヘキサントリオール、1,1,1-トリス(ヒドロキシメチル)プロパン、1,2,3-ヘプタントリオール、1,3,5-シクロヘキサントリオール、ピロガロール、トリエタノールアミン、トリイソプロパノールアミン、1-[N,N-ビス(2-ヒドロキシエチル)アミノ]-2-プロパノール及び2-デオキシリボースよりなる群から選択され、又は前記ポリヒドロキシ化合物が、ペンタエリスリトール、エリスリトール、トレイトール、1,3-ジヒドロキシアセトン二量体、グリセルアルデヒド二量体、フコース、2-デオキシ-ガラクトース及び2-デオキシ-グルコースを含む群から選択され、又は前記ポリヒドロキシ化合物が、グルコース、アロース、アラビノース、リキソース、リボース、キシロース、キシルロース、ガラクトース、マンノース、タガトース、フルクトース、メリビオース、アラビトール、ヘキサヒドロキシシクロヘキサン、キシリトール、マンニトール及びソルビトールを含む群から選択されることを特徴とする請求項1、2、3又は4に記載の方法。
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JP2021531396A (ja) * | 2018-07-13 | 2021-11-18 | ビーエイエスエフ・ソシエタス・エウロパエアBasf Se | 安定なポリオキシメチレンコポリマー(cPOM)の製造方法 |
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JP5336124B2 (ja) | 2013-11-06 |
EP2022804A1 (en) | 2009-02-11 |
BRPI0803374A2 (pt) | 2009-04-07 |
CN102603939B (zh) | 2015-06-10 |
JP2014012844A (ja) | 2014-01-23 |
RU2476445C2 (ru) | 2013-02-27 |
ES2371296T3 (es) | 2011-12-29 |
CN101362808B (zh) | 2013-03-13 |
US20090043055A1 (en) | 2009-02-12 |
JP5747057B2 (ja) | 2015-07-08 |
EP2022804B1 (en) | 2011-09-21 |
RU2008132549A (ru) | 2010-02-20 |
US7879958B2 (en) | 2011-02-01 |
CN101362808A (zh) | 2009-02-11 |
KR20090014994A (ko) | 2009-02-11 |
ZA200806784B (en) | 2009-10-28 |
BRPI0803374B1 (pt) | 2019-03-26 |
KR101569934B1 (ko) | 2015-11-17 |
CN102603939A (zh) | 2012-07-25 |
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