JP2015529724A - ジエンを含む3元系弾性共重合体及びその製造方法 - Google Patents
ジエンを含む3元系弾性共重合体及びその製造方法 Download PDFInfo
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- JP2015529724A JP2015529724A JP2015528412A JP2015528412A JP2015529724A JP 2015529724 A JP2015529724 A JP 2015529724A JP 2015528412 A JP2015528412 A JP 2015528412A JP 2015528412 A JP2015528412 A JP 2015528412A JP 2015529724 A JP2015529724 A JP 2015529724A
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- elastic copolymer
- ternary elastic
- copolymer
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- GSWJFFUYMFTTNK-UHFFFAOYSA-N 6-ethylocta-1,5-diene Chemical compound CCC(CC)=CCCC=C GSWJFFUYMFTTNK-UHFFFAOYSA-N 0.000 description 1
- GFDIPZYKPMOUJP-UHFFFAOYSA-N 6-ethylocta-1,6-diene Chemical compound CCC(=CC)CCCC=C GFDIPZYKPMOUJP-UHFFFAOYSA-N 0.000 description 1
- KUFDSEQTHICIIF-UHFFFAOYSA-N 6-methylhepta-1,5-diene Chemical compound CC(C)=CCCC=C KUFDSEQTHICIIF-UHFFFAOYSA-N 0.000 description 1
- VLBCYLMKVRFERM-UHFFFAOYSA-N 6-methylocta-1,5-diene Chemical compound CCC(C)=CCCC=C VLBCYLMKVRFERM-UHFFFAOYSA-N 0.000 description 1
- DHBQJICESILRNK-UHFFFAOYSA-N 6-methylocta-1,6-diene Chemical compound CC=C(C)CCCC=C DHBQJICESILRNK-UHFFFAOYSA-N 0.000 description 1
- QNJMAPUHMGDDBE-UHFFFAOYSA-N 9-methyldec-1-ene Chemical compound CC(C)CCCCCCC=C QNJMAPUHMGDDBE-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- KPPKCFWQLGMBEU-UHFFFAOYSA-N CC(=CCC=C)CC.CC(C=C)(C=CC)C Chemical compound CC(=CCC=C)CC.CC(C=C)(C=CC)C KPPKCFWQLGMBEU-UHFFFAOYSA-N 0.000 description 1
- FUFIQUBFNROIQK-UHFFFAOYSA-N CC(C=CC1C2C=CC(C1)C2)CCC Chemical compound CC(C=CC1C2C=CC(C1)C2)CCC FUFIQUBFNROIQK-UHFFFAOYSA-N 0.000 description 1
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- GCGVWUITRHFOJS-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC.OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC.OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F GCGVWUITRHFOJS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
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- 235000021355 Stearic acid Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
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- QQZWQOQLMGMKDC-UHFFFAOYSA-N [4-[tert-butyl(dimethyl)silyl]-2,3,5,6-tetrafluorophenoxy]boronic acid Chemical compound CC(C)(C)[Si](C)(C)C1=C(F)C(F)=C(OB(O)O)C(F)=C1F QQZWQOQLMGMKDC-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052795 boron group element Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005626 carbonium group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
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- 229920006037 cross link polymer Polymers 0.000 description 1
- OJOSABWCUVCSTQ-UHFFFAOYSA-N cyclohepta-2,4,6-trienylium Chemical compound C1=CC=C[CH+]=C[CH]1 OJOSABWCUVCSTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- GQRCDUBMGNBKOX-UHFFFAOYSA-N deca-1,8-diene Chemical compound CC=CCCCCCC=C GQRCDUBMGNBKOX-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- MYBJXSAXGLILJD-UHFFFAOYSA-N diethyl(methyl)alumane Chemical compound CC[Al](C)CC MYBJXSAXGLILJD-UHFFFAOYSA-N 0.000 description 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 1
- MWNKMBHGMZHEMM-UHFFFAOYSA-N dimethylalumanylium;ethanolate Chemical compound CCO[Al](C)C MWNKMBHGMZHEMM-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SHGOGDWTZKFNSC-UHFFFAOYSA-N ethyl(dimethyl)alumane Chemical compound CC[Al](C)C SHGOGDWTZKFNSC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007863 gel particle Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- BQBCXNQILNPAPX-UHFFFAOYSA-N methoxy(dimethyl)alumane Chemical compound [O-]C.C[Al+]C BQBCXNQILNPAPX-UHFFFAOYSA-N 0.000 description 1
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 description 1
- OXQMIXBVXHWDPX-UHFFFAOYSA-N n,n,2-trimethylpropan-2-amine Chemical compound CN(C)C(C)(C)C OXQMIXBVXHWDPX-UHFFFAOYSA-N 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- WFVLGDMOCAFNNS-UHFFFAOYSA-N n,n-di(tetradecyl)tetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(CCCCCCCCCCCCCC)CCCCCCCCCCCCCC WFVLGDMOCAFNNS-UHFFFAOYSA-N 0.000 description 1
- IQSLPSKHVSSQOH-UHFFFAOYSA-N n,n-dibutyldecan-1-amine Chemical compound CCCCCCCCCCN(CCCC)CCCC IQSLPSKHVSSQOH-UHFFFAOYSA-N 0.000 description 1
- YEVRYVXXLRUQBJ-UHFFFAOYSA-N n,n-dibutyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(CCCC)CCCC YEVRYVXXLRUQBJ-UHFFFAOYSA-N 0.000 description 1
- XJEPUDKDCKLTSL-UHFFFAOYSA-N n,n-didodecylaniline Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)C1=CC=CC=C1 XJEPUDKDCKLTSL-UHFFFAOYSA-N 0.000 description 1
- LYYLWJOKAQADDU-UHFFFAOYSA-N n,n-dihexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC LYYLWJOKAQADDU-UHFFFAOYSA-N 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
- BUHHOHWMNZQMTA-UHFFFAOYSA-N n,n-dioctadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC BUHHOHWMNZQMTA-UHFFFAOYSA-N 0.000 description 1
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 1
- KCMTVIZYKDBFFS-UHFFFAOYSA-N n-hexadecyl-n-methylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCC KCMTVIZYKDBFFS-UHFFFAOYSA-N 0.000 description 1
- KUFYUMSBZMUWAN-UHFFFAOYSA-N n-methyl-n-tetradecyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCC KUFYUMSBZMUWAN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- LTOZDDGSTSOOCJ-UHFFFAOYSA-N tetradeca-1,12-diene Chemical compound CC=CCCCCCCCCCC=C LTOZDDGSTSOOCJ-UHFFFAOYSA-N 0.000 description 1
- NDUUEFPGQBSFPV-UHFFFAOYSA-N tri(butan-2-yl)alumane Chemical compound CCC(C)[Al](C(C)CC)C(C)CC NDUUEFPGQBSFPV-UHFFFAOYSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- PYLGJXLKFZZEBJ-UHFFFAOYSA-N tricyclopentylalumane Chemical compound C1CCCC1[Al](C1CCCC1)C1CCCC1 PYLGJXLKFZZEBJ-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-O tridecylazanium Chemical compound CCCCCCCCCCCCC[NH3+] ABVVEAHYODGCLZ-UHFFFAOYSA-O 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical compound CB(C)C WXRGABKACDFXMG-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
- ZMPKTELQGVLZTD-UHFFFAOYSA-N tripropylborane Chemical compound CCCB(CCC)CCC ZMPKTELQGVLZTD-UHFFFAOYSA-N 0.000 description 1
- XDSSGQHOYWGIKC-UHFFFAOYSA-N tris(2-methylpropyl)borane Chemical compound CC(C)CB(CC(C)C)CC(C)C XDSSGQHOYWGIKC-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
- OLFPYUPGPBITMH-UHFFFAOYSA-N tritylium Chemical compound C1=CC=CC=C1[C+](C=1C=CC=CC=1)C1=CC=CC=C1 OLFPYUPGPBITMH-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—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
- C08F236/20—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 unconjugated
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/16—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
- C08F210/18—Copolymers of ethene with alpha-alkenes, e.g. EP rubbers with non-conjugated dienes, e.g. EPT rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
i)GPCで測定した重量平均分子量が100,000乃至500,000であり、
ii)ムーニー粘度計(1+4+2@125℃)で測定したムーニー粘度(ML)とムーニー緩和面積(MLR)が下記の一般式1を満足する3元系弾性共重合体を提供する。
R1乃至R13は互いに同一であるか異なり、それぞれ独立的に水素;炭素数1乃至20のアルキルラジカル;炭素数2乃至20のアルケニルラジカル;炭素数6乃至20のアリールラジカル;シリルラジカル;炭素数7乃至20のアルキルアリールラジカル;炭素数7乃至20のアリールアルキルラジカル;またはヒドロカルビルで置換された4族金属のメタロイドラジカルであり;前記R1乃至R13のうちの隣接する相異なる2つのグループは炭素数1乃至20のアルキルまたは炭素数6乃至20のアリールラジカルを含むアルキリジンラジカルによって互いに連結されて脂肪族環または芳香族環を形成することができ;
Mは4族遷移金属であり;
Q1及びQ2は互いに同一であるか異なり、それぞれ独立的にハロゲンラジカル;炭素数1乃至20のアルキルラジカル;炭素数2乃至20のアルケニルラジカル;炭素数6乃至20のアリールラジカル;炭素数7乃至20のアルキルアリールラジカル;炭素数7乃至20のアリールアルキルラジカル;炭素数1乃至20のアルキルアミドラジカル;炭素数6乃至20のアリールアミドラジカル;または炭素数1乃至20のアルキリデンラジカルである。
i)GPCで測定した重量平均分子量が100,000乃至500,000であり、
ii)ムーニー粘度計(1+4+2@125℃)で測定したムーニー粘度(ML)とムーニー緩和面積(MLR)が下記の一般式1を満足する3元系弾性共重合体が提供される。
R1乃至R13は互いに同一であるか異なり、それぞれ独立的に水素;炭素数1乃至20のアルキルラジカル;炭素数2乃至20のアルケニルラジカル;炭素数6乃至20のアリールラジカル;シリルラジカル;炭素数7乃至20のアルキルアリールラジカル;炭素数7乃至20のアリールアルキルラジカル;またはヒドロカルビルで置換された4族金属のメタロイドラジカルであり;前記R1乃至R13のうちの隣接する相異なる2つのグループは炭素数1乃至20のアルキルまたは炭素数6乃至20のアリールラジカルを含むアルキリジンラジカルによって互いに連結されて脂肪族環または芳香族環を形成することができ;
Mは4族遷移金属であり;
Q1及びQ2は互いに同一であるか異なり、それぞれ独立的にハロゲンラジカル;炭素数1乃至20のアルキルラジカル;炭素数2乃至20のアルケニルラジカル;炭素数6乃至20のアリールラジカル;炭素数7乃至20のアルキルアリールラジカル;炭素数7乃至20のアリールアルキルラジカル;炭素数1乃至20のアルキルアミドラジカル;炭素数6乃至20のアリールアミドラジカル;または炭素数1乃至20のアルキリデンラジカルである。
Rは互いに同一であるか異なり、それぞれ独立的にハロゲン;炭素数1乃至20の炭化水素;またはハロゲンで置換された炭素数1乃至20の炭化水素であり;nは2以上の整数であり;
下記の実施例で第1及び第2遷移金属化合物としては、それぞれ[(1,2,3,4−テトラヒドロキノリン−8−イル)テトラメチルシクロペンタジエニル−エタ5,カッパ−N]チタニウムジメチル([(1,2,3,4−Tetrahydroquinolin−8−yl)tetramethylcyclopentadienyl−eta5,kapa−N]titanium dimethyl)及び[(2−メチルインドリン−7−イル)テトラメチルシクロペンタジエニル−エタ5,カッパ−N]チタニウムジメチル([(2−Methylindolin−7−yl)tetramethylcyclopentadienyl−eta5,kapa−N]titanium dimethyl)を用い、助触媒化合物としてはN,N−ジメチルアニリニウムテトラキス(ペンタフルオロフェニル)ボレート及びトリイソブチルアルミニウムを使用した。前記第1及び第2遷移金属化合物は韓国特許登録第0,976、131号の実施例2及び14と同様な方法で製造して使用しており、前記助触媒化合物はこのような韓国特許登録第0,820,542号の実施例9で使用されたものと同一な助触媒化合物を製造して使用した。
2L圧力反応器を用いて、連続的にエチレン、プロピレン及び5−エチリデン−2−ノルボルネンの3元共重合反応を行った。前記反応器の下部から重合溶媒としてヘキサンを時間当り6.7kgの供給速度で連続投入し、反応器の上部から連続的に重合溶液を取り出した。
メタロセン触媒で製造された商用化されたEPDMゴムであるDOW Nordel4570を比較例1の3元系弾性共重合体とし、DOW Nordel4640を比較例2の3元系弾性共重合体とし、DOW Nordel4725を比較例3の3元系弾性共重合体とした。
ムーニー粘度とMLRはASTM D1646−04によってムーニー粘度計(モンサント(Monsanto)社のMV2000装備モデル)を使用して、酸化防止剤(Irganox 1076)処理した共重合体サンプルをプレスモールドを用いてシートとして製作し、これを125℃ 1+4+2条件下で1分間余熱し、4分間ムーニー粘度を測定し、2分間ムーニー緩和を測定した。
ASTM2230によるガーベイダイ(Garvey Die)押出方法によって押出加工性を評価した。ガーベイダイ押出テストのためのサンプルは次のように製造した。実施例1、2と比較例1、2で製造された共重合体100重量部に対してパラフィンオイル75重量部、カーボンブラック125重量部、ZnO5重量部、ステアリン酸1重量部を用いてパレル社のバンバリーミキサー1.6Lを用いてローター回転数60rpmで6分間100乃至120℃で混練した。そして、混練された配合物をガーベイダイ押出機を通じてダイ温度105℃でローター回転数45または60rpmに変化させて押出させ、ASTM2230によって表面と周縁特性を評価した。実施例1、2と比較例1、2のガーベイダイ試験結果を表3に示し、実施例1と比較例1の各共重合体のガーベイダイ押出物の表面写真を図3、図4に示した。
Claims (6)
- 4族遷移金属触媒の存在下に得られた、40乃至70重量%のエチレン、15乃至55重量%の炭素数3乃至20のアルファオレフィン及び0.5乃至20重量%のジエンの共重合体であって、
i)GPCで測定した重量平均分子量が100,000乃至500,000であり、
ii)ムーニー粘度計(1+4+2@125℃)で測定したムーニー粘度(ML)とムーニー緩和面積(MLR)が下記の一般式1を満足する、3元系弾性共重合体:
[一般式1]
[MLR/(ML)2]*100≧8 - MLR/MLが3以上である、請求項1に記載の3元系弾性共重合体。
- ムーニー粘度(ML)が20MU以上である、請求項1に記載の3元系弾性共重合体。
- 0.840乃至0.895g/cm3の密度を有する請求項1に記載の3元系弾性共重合体。
- 2乃至4の分子量分布を有する請求項1に記載の3元系弾性共重合体。
- アルファオレフィンは、プロピレン、1−ブテン、1−ヘキセン及び1−オクテンからなる群より選択された1種以上であり、ジエンは5−エチリデン−2−ノルボルネン、5−メチレン−2−ノルボルネン、及び4−ヘキサジエンからなる群より選択された1種以上である請求項1に記載の3元系弾性共重合体。
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WO2023190320A1 (ja) * | 2022-03-31 | 2023-10-05 | 株式会社大阪ソーダ | アクリルゴム、アクリルゴム含有組成物及びゴム架橋物 |
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