JPS6123203B2 - - Google Patents
Info
- Publication number
- JPS6123203B2 JPS6123203B2 JP52083244A JP8324477A JPS6123203B2 JP S6123203 B2 JPS6123203 B2 JP S6123203B2 JP 52083244 A JP52083244 A JP 52083244A JP 8324477 A JP8324477 A JP 8324477A JP S6123203 B2 JPS6123203 B2 JP S6123203B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- titanium
- ester
- component
- polymerization
- 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.)
- Expired
Links
- 239000010936 titanium Substances 0.000 claims description 49
- 229910052719 titanium Inorganic materials 0.000 claims description 48
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000011949 solid catalyst Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 22
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 21
- 150000002681 magnesium compounds Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 14
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- 229920000098 polyolefin Polymers 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004711 α-olefin Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 55
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 44
- 238000006116 polymerization reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- -1 ethylene, propylene Chemical group 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- QSSJZLPUHJDYKF-UHFFFAOYSA-N methyl 4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1 QSSJZLPUHJDYKF-UHFFFAOYSA-N 0.000 description 14
- 150000001733 carboxylic acid esters Chemical class 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 239000000843 powder Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 7
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 229920006125 amorphous polymer Polymers 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000037048 polymerization activity Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- CBJILYZAALBXKE-UHFFFAOYSA-N butyl 4-butylbenzoate Chemical compound CCCCOC(=O)C1=CC=C(CCCC)C=C1 CBJILYZAALBXKE-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ZPUKPAPWEWUPTC-UHFFFAOYSA-N ethyl 4-ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(CC)C=C1 ZPUKPAPWEWUPTC-UHFFFAOYSA-N 0.000 description 2
- NWPWRAWAUYIELB-UHFFFAOYSA-N ethyl 4-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(C)C=C1 NWPWRAWAUYIELB-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- WDYZSLQVKDHVME-UHFFFAOYSA-N propyl 4-ethylbenzoate Chemical compound CCCOC(=O)C1=CC=C(CC)C=C1 WDYZSLQVKDHVME-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000004819 silanols Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003613 toluenes Chemical class 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical group CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- HRAQMGWTPNOILP-UHFFFAOYSA-N 4-Ethoxy ethylbenzoate Chemical compound CCOC(=O)C1=CC=C(OCC)C=C1 HRAQMGWTPNOILP-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OLLPXZHNCXACMM-CMDGGOBGSA-N Propyl cinnamate Chemical compound CCCOC(=O)\C=C\C1=CC=CC=C1 OLLPXZHNCXACMM-CMDGGOBGSA-N 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001405 butyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- PFMFULUTMUJMMV-UHFFFAOYSA-N butyl 2-(dimethylamino)acetate Chemical compound CCCCOC(=O)CN(C)C PFMFULUTMUJMMV-UHFFFAOYSA-N 0.000 description 1
- HTYCJCQPUKZKTD-UHFFFAOYSA-N butyl 2-(n-phenylanilino)acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OCCCC)C1=CC=CC=C1 HTYCJCQPUKZKTD-UHFFFAOYSA-N 0.000 description 1
- ZHSXGLBHFVIEPT-UHFFFAOYSA-N butyl 4-ethylbenzoate Chemical compound CCCCOC(=O)C1=CC=C(CC)C=C1 ZHSXGLBHFVIEPT-UHFFFAOYSA-N 0.000 description 1
- YWPROEQSNYMONU-UHFFFAOYSA-N butyl 4-hexylbenzoate Chemical compound CCCCCCC1=CC=C(C(=O)OCCCC)C=C1 YWPROEQSNYMONU-UHFFFAOYSA-N 0.000 description 1
- UYGHRCCJWWYXMY-UHFFFAOYSA-N butyl 4-methylbenzoate Chemical compound CCCCOC(=O)C1=CC=C(C)C=C1 UYGHRCCJWWYXMY-UHFFFAOYSA-N 0.000 description 1
- ZSWLKXNXDKMQKK-UHFFFAOYSA-N butyl 4-octylbenzoate Chemical compound CCCCCCCCC1=CC=C(C(=O)OCCCC)C=C1 ZSWLKXNXDKMQKK-UHFFFAOYSA-N 0.000 description 1
- OHHIVLJVBNCSHV-KTKRTIGZSA-N butyl cinnamate Chemical compound CCCCOC(=O)\C=C/C1=CC=CC=C1 OHHIVLJVBNCSHV-KTKRTIGZSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XSBSXJAYEPDGSF-UHFFFAOYSA-N diethyl 3,5-dimethyl-1h-pyrrole-2,4-dicarboxylate Chemical compound CCOC(=O)C=1NC(C)=C(C(=O)OCC)C=1C XSBSXJAYEPDGSF-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- BGCNBOFPABQGNG-UHFFFAOYSA-N ethyl 2-(dimethylamino)acetate Chemical compound CCOC(=O)CN(C)C BGCNBOFPABQGNG-UHFFFAOYSA-N 0.000 description 1
- ATRXRURAIJZUOT-UHFFFAOYSA-N ethyl 2-(n-phenylanilino)acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OCC)C1=CC=CC=C1 ATRXRURAIJZUOT-UHFFFAOYSA-N 0.000 description 1
- NKAVJELRFJVPEE-UHFFFAOYSA-N ethyl 4-butylbenzoate Chemical compound CCCCC1=CC=C(C(=O)OCC)C=C1 NKAVJELRFJVPEE-UHFFFAOYSA-N 0.000 description 1
- GQRZXKALRVNWOI-UHFFFAOYSA-N ethyl 4-hexylbenzoate Chemical compound CCCCCCC1=CC=C(C(=O)OCC)C=C1 GQRZXKALRVNWOI-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FSMGSEAKDZNSAS-UHFFFAOYSA-N hexyl 4-butylbenzoate Chemical compound CCCCCCOC(=O)C1=CC=C(CCCC)C=C1 FSMGSEAKDZNSAS-UHFFFAOYSA-N 0.000 description 1
- WWCOVCJCTORFJV-UHFFFAOYSA-N hexyl 4-ethylbenzoate Chemical compound CCCCCCOC(=O)C1=CC=C(CC)C=C1 WWCOVCJCTORFJV-UHFFFAOYSA-N 0.000 description 1
- AWYIEWURDDNCJR-UHFFFAOYSA-N hexyl 4-hexylbenzoate Chemical compound CCCCCCOC(=O)C1=CC=C(CCCCCC)C=C1 AWYIEWURDDNCJR-UHFFFAOYSA-N 0.000 description 1
- PELWVATUYGIRES-UHFFFAOYSA-N hexyl 4-methylbenzoate Chemical compound CCCCCCOC(=O)C1=CC=C(C)C=C1 PELWVATUYGIRES-UHFFFAOYSA-N 0.000 description 1
- DXGRDPOKEXFGAO-UHFFFAOYSA-N hexyl 4-octylbenzoate Chemical compound CCCCCCCCC1=CC=C(C(=O)OCCCCCC)C=C1 DXGRDPOKEXFGAO-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- XJRYQLPELPLPHZ-UHFFFAOYSA-N methyl 4-butylbenzoate Chemical compound CCCCC1=CC=C(C(=O)OC)C=C1 XJRYQLPELPLPHZ-UHFFFAOYSA-N 0.000 description 1
- RNHXTCZZACTEMK-UHFFFAOYSA-N methyl 4-ethoxybenzoate Chemical compound CCOC1=CC=C(C(=O)OC)C=C1 RNHXTCZZACTEMK-UHFFFAOYSA-N 0.000 description 1
- CAABRJFUDNBRJZ-UHFFFAOYSA-N methyl 4-ethylbenzoate Chemical compound CCC1=CC=C(C(=O)OC)C=C1 CAABRJFUDNBRJZ-UHFFFAOYSA-N 0.000 description 1
- RTTGTHPEVMEHEK-UHFFFAOYSA-N methyl 4-hexylbenzoate Chemical compound CCCCCCC1=CC=C(C(=O)OC)C=C1 RTTGTHPEVMEHEK-UHFFFAOYSA-N 0.000 description 1
- NKSKNAWLKUQLNY-UHFFFAOYSA-N methyl 4-octylbenzoate Chemical compound CCCCCCCCC1=CC=C(C(=O)OC)C=C1 NKSKNAWLKUQLNY-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])([H])[H] 0.000 description 1
- WOHCEFXPFWWXKJ-UHFFFAOYSA-N octyl 4-butylbenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(CCCC)C=C1 WOHCEFXPFWWXKJ-UHFFFAOYSA-N 0.000 description 1
- PXGCAPRMDJWYHP-UHFFFAOYSA-N octyl 4-ethylbenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(CC)C=C1 PXGCAPRMDJWYHP-UHFFFAOYSA-N 0.000 description 1
- VBDCUVDAJYAVEK-UHFFFAOYSA-N octyl 4-hexylbenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(CCCCCC)C=C1 VBDCUVDAJYAVEK-UHFFFAOYSA-N 0.000 description 1
- MGRDBXFNMFBCLH-UHFFFAOYSA-N octyl 4-methylbenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C)C=C1 MGRDBXFNMFBCLH-UHFFFAOYSA-N 0.000 description 1
- QHJVVZLZLOACPN-UHFFFAOYSA-N octyl 4-octylbenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(CCCCCCCC)C=C1 QHJVVZLZLOACPN-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 239000001572 propyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- ZHDCHCTZRODSEN-HWKANZROSA-N propyl (e)-but-2-enoate Chemical compound CCCOC(=O)\C=C\C ZHDCHCTZRODSEN-HWKANZROSA-N 0.000 description 1
- SDRUOGAFMUPTQU-UHFFFAOYSA-N propyl 2-(dimethylamino)acetate Chemical compound CCCOC(=O)CN(C)C SDRUOGAFMUPTQU-UHFFFAOYSA-N 0.000 description 1
- KWGVHDSKXOIFNY-UHFFFAOYSA-N propyl 4-butylbenzoate Chemical compound CCCCC1=CC=C(C(=O)OCCC)C=C1 KWGVHDSKXOIFNY-UHFFFAOYSA-N 0.000 description 1
- CZICFNAHHIXSLR-UHFFFAOYSA-N propyl 4-hexylbenzoate Chemical compound CCCCCCC1=CC=C(C(=O)OCCC)C=C1 CZICFNAHHIXSLR-UHFFFAOYSA-N 0.000 description 1
- WEHMFTWWOGBHCR-UHFFFAOYSA-N propyl 4-methoxybenzoate Chemical compound CCCOC(=O)C1=CC=C(OC)C=C1 WEHMFTWWOGBHCR-UHFFFAOYSA-N 0.000 description 1
- LRNBWFXCDULFQF-UHFFFAOYSA-N propyl 4-methylbenzoate Chemical compound CCCOC(=O)C1=CC=C(C)C=C1 LRNBWFXCDULFQF-UHFFFAOYSA-N 0.000 description 1
- SKNREWLKHODPNM-UHFFFAOYSA-N propyl 4-octylbenzoate Chemical compound CCCCCCCCC1=CC=C(C(=O)OCCC)C=C1 SKNREWLKHODPNM-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 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
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8324477A JPS5418886A (en) | 1977-07-12 | 1977-07-12 | Production of olefin polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8324477A JPS5418886A (en) | 1977-07-12 | 1977-07-12 | Production of olefin polymer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14445577A Division JPS5418887A (en) | 1977-12-01 | 1977-12-01 | Preparation of olefin polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5418886A JPS5418886A (en) | 1979-02-13 |
| JPS6123203B2 true JPS6123203B2 (ko) | 1986-06-04 |
Family
ID=13796905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8324477A Granted JPS5418886A (en) | 1977-07-12 | 1977-07-12 | Production of olefin polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5418886A (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6444505U (ko) * | 1987-09-14 | 1989-03-16 |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55133408A (en) * | 1979-04-05 | 1980-10-17 | Sumitomo Chem Co Ltd | Polymerization of olefin |
| JPS55135105A (en) * | 1979-04-10 | 1980-10-21 | Mitsui Petrochem Ind Ltd | Titanium catalyst component for olefin polymerization |
| JPS5713777A (en) | 1980-06-30 | 1982-01-23 | Shunpei Yamazaki | Semiconductor device and manufacture thereof |
| US5859443A (en) * | 1980-06-30 | 1999-01-12 | Semiconductor Energy Laboratory Co., Ltd. | Semiconductor device |
| US6900463B1 (en) | 1980-06-30 | 2005-05-31 | Semiconductor Energy Laboratory Co., Ltd. | Semiconductor device |
| JPS57174803A (en) * | 1981-04-20 | 1982-10-27 | Masayasu Negishi | Surface light source device |
| JPS5950425A (ja) * | 1982-09-16 | 1984-03-23 | Mitsubishi Electric Corp | カラ−液晶表示装置 |
| JPS58116573A (ja) * | 1981-12-29 | 1983-07-11 | セイコーエプソン株式会社 | マトリックス表示装置の製造方法 |
| JPS5946686A (ja) * | 1982-09-09 | 1984-03-16 | セイコーエプソン株式会社 | 表示装置 |
| JPH0817494B2 (ja) * | 1983-04-25 | 1996-02-21 | セイコーエプソン株式会社 | マトリクス液晶表示体の駆動回路 |
| JPS59208577A (ja) * | 1983-05-12 | 1984-11-26 | セイコーエプソン株式会社 | カラ−表示装置 |
| JPS59210481A (ja) * | 1983-05-13 | 1984-11-29 | セイコーエプソン株式会社 | カラ−液晶表示装置 |
| JPS59211087A (ja) * | 1983-05-16 | 1984-11-29 | セイコーエプソン株式会社 | カラ−液晶画像表示装置の駆動方法 |
| JPS6044076U (ja) * | 1983-08-31 | 1985-03-28 | シャープ株式会社 | 表示装置用ライトボックス |
| JPS60134293A (ja) * | 1983-12-22 | 1985-07-17 | シャープ株式会社 | 液晶表示装置の駆動方法 |
| JPH0766122B2 (ja) * | 1983-09-30 | 1995-07-19 | セイコーエプソン株式会社 | 透過型液晶表示装置 |
| JPS60179723A (ja) * | 1984-02-27 | 1985-09-13 | Sharp Corp | 液晶プロジエクシヨン装置 |
| USRE36725E (en) * | 1984-10-22 | 2000-06-06 | Seiko Epson Corporation | Projection-type display device |
| JP2530303B2 (ja) * | 1984-10-22 | 1996-09-04 | ソニー株式会社 | デイスプレイ装置 |
| JP2815910B2 (ja) * | 1989-07-19 | 1998-10-27 | シャープ株式会社 | 投影形画像表示装置 |
| JPH0333721A (ja) * | 1990-02-22 | 1991-02-14 | Sanyo Electric Co Ltd | カラー液晶表示装置とその製造方法 |
| JPH0644825B2 (ja) * | 1990-06-01 | 1994-06-08 | セイコーエプソン株式会社 | 液晶表示装置 |
| JPH0321188A (ja) * | 1990-06-01 | 1991-01-29 | Seiko Epson Corp | 液晶表示装置 |
| JP2586195B2 (ja) * | 1990-08-30 | 1997-02-26 | セイコーエプソン株式会社 | 液晶表示装置 |
| JP2548677Y2 (ja) * | 1991-05-10 | 1997-09-24 | シャープ株式会社 | 液晶用照明装置 |
| JP2606619B2 (ja) * | 1995-12-26 | 1997-05-07 | セイコーエプソン株式会社 | 投写式表示装置 |
| JP2650183B2 (ja) * | 1996-04-08 | 1997-09-03 | セイコーエプソン株式会社 | 投写式表示装置 |
| JP2689975B2 (ja) * | 1996-04-08 | 1997-12-10 | セイコーエプソン株式会社 | 投写式表示装置 |
| JP2650184B2 (ja) * | 1996-04-08 | 1997-09-03 | セイコーエプソン株式会社 | 投写式表示装置 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52147688A (en) * | 1976-06-02 | 1977-12-08 | Mitsui Petrochem Ind Ltd | Preparation of polyolefin |
| JPS5340093A (en) * | 1976-09-27 | 1978-04-12 | Mitsui Petrochem Ind Ltd | Preparation of polyolefin |
-
1977
- 1977-07-12 JP JP8324477A patent/JPS5418886A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52147688A (en) * | 1976-06-02 | 1977-12-08 | Mitsui Petrochem Ind Ltd | Preparation of polyolefin |
| JPS5340093A (en) * | 1976-09-27 | 1978-04-12 | Mitsui Petrochem Ind Ltd | Preparation of polyolefin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6444505U (ko) * | 1987-09-14 | 1989-03-16 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5418886A (en) | 1979-02-13 |
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