JP5956919B2 - エチレン−α−オレフィン−非共役ポリエン共重合体 - Google Patents
エチレン−α−オレフィン−非共役ポリエン共重合体 Download PDFInfo
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- JP5956919B2 JP5956919B2 JP2012272054A JP2012272054A JP5956919B2 JP 5956919 B2 JP5956919 B2 JP 5956919B2 JP 2012272054 A JP2012272054 A JP 2012272054A JP 2012272054 A JP2012272054 A JP 2012272054A JP 5956919 B2 JP5956919 B2 JP 5956919B2
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- Prior art keywords
- ethylene
- olefin
- weight
- norbornene
- nonconjugated polyene
- Prior art date
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- 239000005977 Ethylene Substances 0.000 claims description 29
- 239000004711 α-olefin Substances 0.000 claims description 25
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
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- 239000000203 mixture Substances 0.000 description 36
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- 239000000243 solution Substances 0.000 description 16
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- 238000000034 method Methods 0.000 description 15
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
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- 238000010438 heat treatment Methods 0.000 description 9
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- 239000011593 sulfur Substances 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
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- 239000001257 hydrogen Substances 0.000 description 8
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- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 7
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
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- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
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- 239000004902 Softening Agent Substances 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000003712 anti-aging effect Effects 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002685 polymerization catalyst Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- NWPQAENAYWENSD-UHFFFAOYSA-N 5-butylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CCCC)CC1C=C2 NWPQAENAYWENSD-UHFFFAOYSA-N 0.000 description 2
- INYHZQLKOKTDAI-UHFFFAOYSA-N 5-ethenylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C=C)CC1C=C2 INYHZQLKOKTDAI-UHFFFAOYSA-N 0.000 description 2
- UZOALLLGRUBVIH-UHFFFAOYSA-N 5-hept-5-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCC=CC)CC1C=C2 UZOALLLGRUBVIH-UHFFFAOYSA-N 0.000 description 2
- WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 2
- XHBNZTYPSQZAIY-UHFFFAOYSA-N 5-oct-7-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCCCCC=C)CC1C=C2 XHBNZTYPSQZAIY-UHFFFAOYSA-N 0.000 description 2
- RZTQYTKFARGVKP-UHFFFAOYSA-N 5-pent-4-enylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCCC=C)CC1C=C2 RZTQYTKFARGVKP-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 231100000987 absorbed dose Toxicity 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 239000011701 zinc Substances 0.000 description 2
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- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
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- JFZBUNLOTDDXNY-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)propoxy]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)OCC(C)OC(=O)C(C)=C JFZBUNLOTDDXNY-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
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- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940052367 sulfur,colloidal Drugs 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003784 tall oil Substances 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
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- PZKZVLYBWITYEF-UHFFFAOYSA-L zinc;n,n-diethylcarbamothioate Chemical compound [Zn+2].CCN(CC)C([O-])=S.CCN(CC)C([O-])=S PZKZVLYBWITYEF-UHFFFAOYSA-L 0.000 description 1
- LAGTXXPOZSLGSF-UHFFFAOYSA-L zinc;n-butyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCCCN(C([S-])=S)C1=CC=CC=C1.CCCCN(C([S-])=S)C1=CC=CC=C1 LAGTXXPOZSLGSF-UHFFFAOYSA-L 0.000 description 1
- KMNUDJAXRXUZQS-UHFFFAOYSA-L zinc;n-ethyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCN(C([S-])=S)C1=CC=CC=C1.CCN(C([S-])=S)C1=CC=CC=C1 KMNUDJAXRXUZQS-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 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
- 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
-
- 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
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/06—Propene
-
- 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
- Y10S526/905—Polymerization in presence of transition metal containing catalyst in presence of hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Description
ゴムホースに用いられる原料ゴムとして、例えば、特許文献1、2には、エチレン−α−オレフィン−非共役ポリエン共重合体が記載されている。
かかる状況のもと、本発明が解決しようとする課題は、ロール混練加工性と押出加工性に優れたエチレン−α−オレフィン−非共役ポリエン共重合体を提供することにある。
(A):極限粘度[η]が0.5〜1.8dl/gである。
(B):エチレン単位の含有量とα−オレフィン単位の含有量との総量を100モル%とするとき、エチレン単位の含有量が50〜90モル%であり、α−オレフィン単位の含有量が50〜10モル%である。
(C):よう素価が1〜50である。
(D):100℃および1000cpmでのtanδに対する100℃および2cpmでのtanδの比が1.0〜1.7である。
(E):数平均分子量に対するZ−平均分子量の比が15〜25であり、数平均分子量に対する重量平均分子量の比が3〜5である。
エチレン−α−オレフィン−非共役ポリエン共重合体のα−オレフィンとしては、好ましくは、炭素原子数3〜20のα−オレフィンであり、プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、1−ヘプテン、1−オクテン、1−ノネン、1−デセン等の直鎖状α−オレフィン;3−メチル−1−ブテン、3−メチル−1−ペンテン、4−メチル−1−ペンテン等の分岐状α−オレフィンがあげられる。これらは、1種以上使用される。
α−オレフィンとしては、好ましくは、プロピレン、1−ブテンであり、より好ましくはプロピレンである。
(a)バナジウム化合物の使用量に対する有機アルミニウム化合物の使用量のモル比(有機アルミニウム化合物のモル数/バナジウム化合物のモル数)が0.1〜2.0である。
(b)重合温度が50〜80℃である。
(c)重合反応器に供給される水素の量が、重合反応器に供給される溶媒の量1kgあたり、0.001〜0.1NLである。
(d)重合反応器に供給されるバナジウム化合物の量が、重合反応器に供給される溶媒100重量部あたり、0.02〜0.2重量部である。
)0.5Cl2.5、VO(O(n-C7H15))0.5Cl2.5、VO(O(n-C8H17))0.5Cl2.5、VO(OCH3)0.8Cl2.2、VO(OC2H5)0.8Cl2.2、VO(O(n-C3H7))0.8Cl2.2、VO(O(n-C4H9))0.8Cl2.2、VO(O(n-C5H11))0.8Cl2.2、VO(O(n-C6H13))0.8Cl2.2、VO(O(n-C7H15))0.8Cl2.2、VO(O(n-C8H17))0.8Cl2.2、VO(OCH3)Cl2、VO(OC2H5)Cl2、VO(O(n-C3H7))Cl2、VO(O(n-C4H9))Cl2、VO(O(n-C5H11))Cl2、VO(O(n-C6H13))Cl2、VO(O(n-C7H15))Cl2、VO(O(n-C8H17))Cl2、VO(OCH3)1.5Cl0.5、VO(OC2H5)1.5Cl0.5、VO(O(n-C3H7))1.5Cl0.5、VO(O(n-C4H9))1.5Cl0.5、VO(O(n-C5H11))1.5Cl0.5、VO(O(n-C6H13))1.5Cl0.5、VO(O(n-C7H15))1.5Cl0.5、VO(O(n-C8H17))1.5Cl0.5、等のVO(OR)mCln[式中、Rは炭素原子数1〜10のアルキル基を表し、mおよびnは、m+n=3、0≦m<3および0<n≦3を充足する数である。]で表される化合物をあげることができる。好ましくは、VOCl3、VO(OC2H5)0.5Cl2.5、VO(OC2H5)0.8Cl2.2、VO(OC2H5)Cl2、VO(OC2H5)1.5Cl0.5等のVO(OC2H5)rCls[式中、rおよびsは、r+s=3、1≦r<3および0<s≦2を充足する数である。]で表される化合物であり、より好ましくはVOCl3である。
(1)エチレン単位量およびプロピレン単位量
共重合体をホットプレス機により厚み約0.1mmのフィルムに成形し、赤外分光光度計(日本分光工業社製 IR−810)により該フィルムの赤外吸収スペクトルを測定した。該赤外吸収スペクトルから、文献(赤外吸収スペクトルによるポリエチレンのキャラクタリゼーション 高山、宇佐美 等著 及び Die Makromolekulare Chemie,177,461(1976)Mc Rae,M.A.,MadamS,W.F.等著)記載の方法に従って、エチレン単位量およびプロピレン単位量を求めた。
共重合体をホットプレス機により厚み約0.5mmのフィルムに成形した。赤外分光光度計により該フィルムの5−エチリデン−2−ノルボルネン由来のピーク(1688cm-1の吸収ピーク)の強度を測定した。該ピーク強度から二重結合のモル含量を求め、該モル含量からヨウ素価を算出した。
ゲル・パーミエイション・クロマトグラフ(GPC)法によって、下記の条件(1)〜(9)で、共重合体のZ−平均分子量(Mz)と数平均分子量(Mn)及び重量平均分子量(Mw)を測定し、Mz/Mn及びMw/Mnを求めた。
(1)装置:Waters製150C
(2)分離カラム:昭和電工社製Shodex Packed ColumnA−80M (3)測定温度:140℃
(4)キャリア:オルトジクロロベンゼン
(5)流量:1.0mL/分
(6)試料濃度:約1mg/1mL
(7)試料注入量:400μL
(8)検出器:示差屈折
(9)分子量標準物質:標準ポリスチレン
ウベローデ型粘度計を用い、135℃のテトラリン溶液中で極限粘度を測定した。
粘弾性測定装置(ALPHA TECHNOLOGIES社製 RUBBER PROCESS ANALYZER RPA2000P)を用い、温度100℃、歪み13.95%で、周波数を変更して、共重合体のtanδ(せん断損失弾性率とせん断貯蔵弾性率の比:せん断損失弾性率/せん断貯蔵弾性率)を測定した。周波数が2cpmでのtanδと周波数が1000cpmでのtanδの比を算出した。
実施例及び比較例における重合体組成物の調製の工程(2)において、ロール混練時のバギングの発生の有無を観察した。バギングの発生が無いものを『良』、バギングの発生があるものを『不良』と評価した。
L/D=16の45mmφベント式押出機(中田造機社製)に、押出ダイとしてASTM D2230−90の5.2 Die−ASTM Extrusion Dieに規定のガーベタイプ押出ダイ(Garvey−type extrusion die)をセットし、スクリュー温度40℃、シリンダー温度60℃、ダイ温度80℃、スクリュー回転数60rpmにて、重合体組成物をダイから押出し、重合体組成物の押出速度(cm/min)を測定した。当該速度が速いほど、押出加工性に優れる。なお、押し出された細長い重合体組成物の単位時間(min)あたりの長さ(cm)を押出速度(cm/min)とした。
(共重合体の調製)
攪拌機を備えたステンレススチール製の重合槽の温度を60℃に保ち、当該重合槽に、単位時間・重合槽の単位容積あたり、ヘキサンを0.461kg/(hr・L)、エチレンを31.6g/(hr・L)、プロピレンを169g/(hr・L)の速度で供給した。VOCl3を230mg/(hr・L)、エチルアルミニウムセスキクロライド(EASC)を341mg/(hr・L)、水素を0.013NL/(hr・L)の速度で重合槽に供給した。更に5−エチリデン−2−ノルボルネンを2.8g/(hr・L)の速度で重合槽に供給した。
重合槽からは、重合槽内の重合溶液の量が一定となるように、重合溶液を抜き出した。
抜き出した重合溶液から溶媒を除去して、共重合体(以下、EPDM−Aと記す。)を得た。
EPDM−Aを分析したところ、EPDM−Aのエチレン単位量/プロピレン単位量(モル比)は0.61/0.39であり、ヨウ素価は14.4(g/100g重合体)であり、Mz/Mnは19.1、Mw/Mnは4.2、極限粘度は1.60dl/g、tanδ(100℃,2cpm)/tanδ(100℃,1000cpm)は1.40であった。
工程(1)
100重量部のEPDM−Aと、5重量部の酸化亜鉛と、1重量部のステアリン酸と、90重量部のFEFカーボンブラック(旭カーボン社製 旭60G)と、5重量部のパラフィン系オイル(出光興産社製 ダイアナPW380)と、2重量部のポリエチレングリコール(PEG4000)と、2重量部の加工助剤(シル+ザイラッハ社製 ストラクトールWB212)と、1重量部の2−メルカプトベンゾイミダゾール(住友化学社製 スミライザーMB)とをバンバリーミキサーで混練して、混練物を得た。混練においては、混練開始時のバンバリーミキサーの温度を80℃とし、ローター回転数を60rpmとし、混練時間を5分間とした。
上記混練物と、該混練物中のEPDM−A 100重量部あたり、5重量部のα,α’−ビス(t−ブチルペロキシ)ジイソプロピルベンゼン(日油社製 ペロキシモンF(40)有効成分60%)、0.5重量部のイオウとを、ロール温度50℃の8インチの一対のロールであって、オープンロール(関西ロール社製)により、ロールギャップ4mmにて回転速度フロントロール15rpm、バックロール18rpmの条件でバックロール側に巻きつけながら混練して、重合体組成物を得、そして、重合体組成物のロール混練加工性を評価した。次に、該重合体組成物の押出加工性を評価した。評価結果を表1に示す。
(共重合体の調製)
攪拌機を備えたステンレススチール製の重合槽の温度を60℃に保ち、当該重合槽に、単位時間・重合槽の単位容積あたり、ヘキサンを1.13kg/(hr・L)、エチレンを30.0g/(hr・L)、プロピレンを160g/(hr・L)の速度で供給した。VOCl3を266mg/(hr・L)、エチルアルミニウムセスキクロライド(EASC)を399mg/(hr・L)、水素を0.001NL/(hr・L)の速度で重合槽に供給した。更に5−エチリデン−2−ノルボルネンを9.2g/(hr・L)の速度で重合槽に供給した。
重合槽からは、重合槽内の重合溶液の量が一定となるように、重合溶液を抜き出した。抜き出した重合溶液から溶媒を除去して、共重合体(以下、EPDM−Bと記す。)を得た。
EPDM−Bを分析したところ、EPDM−Bのエチレン単位量/プロピレン単位量(モル比)は0.62/0.38であり、ヨウ素価は25.1(g/100g重合体)であり、Mz/Mnは17.4、Mw/Mnは4.0、極限粘度は1.41dl/g、tanδ(100℃,2cpm)/tanδ(100℃,1000cpm)は1.51であった。
EPDM−AにかえてEPDM−Bを用いた以外は、実施例1の「重合体組成物の調製」と同様にして、重合体組成物を調製し、該重合体組成物のロール混練加工性と押出加工性を評価した。該重合体組成物の評価結果を表1に示す。
(共重合体の調製)
攪拌機を備えたステンレススチール製の温度を60℃に保った重合槽に、単位時間・重合槽の単位容積あたり、ヘキサンを0.458kg/(hr・L)、エチレンを32.3g/(hr・L)、プロピレンを173g/(hr・L)の速度で供給した。VOCl3を140mg/(hr・L)、エチルアルミニウムセスキクロライド(EASC)を307mg/(hr・L)、水素を0.010NL/(hr・L)の速度で重合槽に供給した。更に5−エチリデン−2−ノルボルネンを1.9g/(hr・L)の速度で重合槽に供給した。
重合槽からは、重合槽内の重合溶液の量が一定となるように、重合溶液を抜き出した。
抜き出した重合溶液から溶媒を除去して、共重合体(以下、EPDM−Cと記す。)を得た。
EPDM−Cを分析したところ、EPDM−Cのエチレン単位量/プロピレン単位量(モル比)は0.61/0.39であり、ヨウ素価は9.6(g/100g重合体)であり、Mz/Mnは13.4、Mw/Mnは3.8、極限粘度は1.75dl/g、tanδ(100℃,2cpm)/tanδ(100℃,1000cpm)は1.65であった。
EPDM−AにかえてEPDM−Cを用いた以外は、実施例1の「重合体組成物の調製」と同様にして、重合体組成物を調製し、該重合体組成物のロール混練加工性と押出加工性を評価した。該重合体組成物の評価結果を表1に示す。
(共重合体の調製)
攪拌機を備えたステンレススチール製の温度を55℃に保った重合槽に、単位時間・重合槽の単位容積あたり、ヘキサンを0.458kg/(hr・L)、エチレンを32.4g/(hr・L)、プロピレンを173g/(hr・L)の速度で供給した。VOCl3を108mg/(hr・L)、エチルアルミニウムセスキクロライド(EASC)を237mg/(hr・L)、水素を0.028NL/(hr・L)の速度で重合槽に供給した。更に5−エチリデン−2−ノルボルネンを1.9g/(hr・L)の速度で重合槽に供給した。
重合槽からは、重合槽内の重合溶液の量が一定となるように、重合溶液を抜き出した。
抜き出した重合溶液から溶媒を除去して、共重合体(以下、EPDM−Dと記す。)を得た。
EPDM−Dを分析したところ、EPDM−Dのエチレン単位量/プロピレン単位量(モル比)は0.61/0.39であり、ヨウ素価は10.3(g/100g重合体)であり、Mz/Mnは11.5、Mw/Mnは3.2、極限粘度は1.65dl/g、tanδ(100℃,2cpm)/tanδ(100℃,1000cpm)は1.96であった。
EPDM−AにかえてEPDM−Dを用いた以外は、実施例1の「重合体組成物の調製」と同様にして、重合体組成物を調製し、該重合体組成物のロール混練加工性と押出加工性を評価した。該重合体組成物の評価結果を表1に示す。
(共重合体の調製)
攪拌機を備えたステンレススチール製の温度を45℃に保った重合槽に、単位時間・重合槽の単位容積あたり、ヘキサンを0.458kg/(hr・L)、エチレンを32.3g/(hr・L)、プロピレンを173g/(hr・L)の速度で供給した。VOCl3を58.4mg/(hr・L)、エチルアルミニウムセスキクロライド(EASC)を128mg/(hr・L)、水素を0.076NL/(hr・L)の速度で重合槽に供給した。更にジシクロペンタジエンを2.1g/(hr・L)の速度で重合槽に供給した。
重合槽からは、重合槽内の重合溶液の量が一定となるように、重合溶液を抜き出した。
抜き出した重合溶液から溶媒を除去して、共重合体(以下、EPDM−Eと記す。)を得た。
EPDM−Eを分析したところ、EPDM−Eのエチレン単位量/プロピレン単位量(モル比)は0.62/0.38であり、ヨウ素価は9.5(g/100g重合体)であり、Mz/Mnは10.6、Mw/Mnは3.4、極限粘度は1.52dl/g、tanδ(100℃,2cpm)/tanδ(100℃,1000cpm)は1.78であった。
EPDM−AにかえてEPDM−Eを用いた以外は、実施例1の「重合体組成物の調製」と同様にして、重合体組成物を調製し、該重合体組成物のロール混練加工性と押出加工性を評価した。該重合体組成物の評価結果を表1に示す。
Claims (2)
- 下記要件(A)、(B)、(C)、(D)及び(E)を充足するエチレン−α−オレフィン−非共役ポリエン共重合体。
(A):極限粘度[η]が0.5〜1.8dl/gである。
(B):エチレン単位の含有量とα−オレフィン単位の含有量との総量を100モル%とするとき、エチレン単位の含有量が50〜90モル%であり、α−オレフィン単位の含有量が50〜10モル%である。
(C):よう素価が1〜50である。
(D):100℃および1000cpmでのtanδに対する100℃および2cpmでのtanδの比(tanδ(100℃,2cpm)/tanδ(100℃,1000cpm))が1.0〜1.7である。
(E):数平均分子量に対するZ−平均分子量の比(Mz/Mn)が15〜25であり、数平均分子量に対する重量平均分子量の比が3〜5である。 - α−オレフィンがプロピレンであり、非共役ポリエンが、5−アルキリデン−2−ノルボルネンおよび5−アルケニル−2−ノルボルネンからなる化合物群から選ばれる少なくとも1種の化合物である請求項1に記載のエチレン−α−オレフィン−非共役ポリエン共重合体。
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