JPH0229684B2 - - Google Patents
Info
- Publication number
- JPH0229684B2 JPH0229684B2 JP58174029A JP17402983A JPH0229684B2 JP H0229684 B2 JPH0229684 B2 JP H0229684B2 JP 58174029 A JP58174029 A JP 58174029A JP 17402983 A JP17402983 A JP 17402983A JP H0229684 B2 JPH0229684 B2 JP H0229684B2
- Authority
- JP
- Japan
- Prior art keywords
- high cis
- polyisoprene
- polymerization
- polybutadiene
- aqueous dispersion
- 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 - Lifetime
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 54
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 38
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 claims description 32
- 239000003054 catalyst Substances 0.000 claims description 23
- 229920001195 polyisoprene Polymers 0.000 claims description 22
- 239000005062 Polybutadiene Substances 0.000 claims description 21
- 239000002612 dispersion medium Substances 0.000 claims description 21
- 229920002857 polybutadiene Polymers 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 238000012674 dispersion polymerization Methods 0.000 claims description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 12
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 10
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 claims description 8
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical group CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 6
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 6
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 claims description 4
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001282 iso-butane Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 3
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 claims 1
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims 1
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 47
- 229920003193 cis-1,4-polybutadiene polymer Polymers 0.000 description 39
- 239000006185 dispersion Substances 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- 239000002270 dispersing agent Substances 0.000 description 17
- 239000002609 medium Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- LOVYCUYJRWLTSU-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n,n-diethylethanamine Chemical compound CCN(CC)CCOC1=CC=C(Cl)C(Cl)=C1 LOVYCUYJRWLTSU-UHFFFAOYSA-N 0.000 description 6
- UVPKUTPZWFHAHY-UHFFFAOYSA-L 2-ethylhexanoate;nickel(2+) Chemical compound [Ni+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O UVPKUTPZWFHAHY-UHFFFAOYSA-L 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241001495453 Parthenium argentatum Species 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 6
- 238000012662 bulk polymerization Methods 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000004062 sedimentation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000010557 suspension polymerization reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 244000286663 Ficus elastica Species 0.000 description 2
- 241000221020 Hevea Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920004940 NATSYN® Polymers 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012457 nonaqueous media Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- -1 poly(vinyl alcohol) Polymers 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- RLPGDEORIPLBNF-UHFFFAOYSA-N 2,3,4-trimethylpentane Chemical compound CC(C)C(C)C(C)C RLPGDEORIPLBNF-UHFFFAOYSA-N 0.000 description 1
- YACTXGRTJNKUDC-UHFFFAOYSA-N 2-hydroxybenzaldehyde;nickel Chemical compound [Ni].OC1=CC=CC=C1C=O.OC1=CC=CC=C1C=O YACTXGRTJNKUDC-UHFFFAOYSA-N 0.000 description 1
- SFXNZFATUMWBHR-UHFFFAOYSA-N 2-morpholin-4-yl-2-pyridin-3-ylacetonitrile Chemical compound C=1C=CN=CC=1C(C#N)N1CCOCC1 SFXNZFATUMWBHR-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical class O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- VNBCIRBFLBYHCW-UHFFFAOYSA-L 7,7-dimethyloctanoate;nickel(2+) Chemical compound [Ni+2].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O VNBCIRBFLBYHCW-UHFFFAOYSA-L 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000005063 High cis polybutadiene Substances 0.000 description 1
- 241001247355 Landolphia Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001495454 Parthenium Species 0.000 description 1
- AVFIYMSJDDGDBQ-UHFFFAOYSA-N Parthenium Chemical compound C1C=C(CCC(C)=O)C(C)CC2OC(=O)C(=C)C21 AVFIYMSJDDGDBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- HFRDIOLOKCMOCE-UHFFFAOYSA-K [B+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound [B+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 HFRDIOLOKCMOCE-UHFFFAOYSA-K 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005234 alkyl aluminium group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- DLSKLEKYCFINLO-UHFFFAOYSA-N benzaldehyde;trifluoroborane Chemical compound FB(F)F.O=CC1=CC=CC=C1 DLSKLEKYCFINLO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- FJIABHSGECXHBM-UHFFFAOYSA-L decanoate;nickel(2+) Chemical compound [Ni+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O FJIABHSGECXHBM-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HRXSKIOIHQEGAI-UHFFFAOYSA-M diethylalumanylium;fluoride Chemical compound CC[Al](F)CC HRXSKIOIHQEGAI-UHFFFAOYSA-M 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- KRWWZDVIEFSIOT-UHFFFAOYSA-N ethenyl acetate;furan-2,5-dione Chemical compound CC(=O)OC=C.O=C1OC(=O)C=C1 KRWWZDVIEFSIOT-UHFFFAOYSA-N 0.000 description 1
- RSLGLAVKNHUDGW-UHFFFAOYSA-N ethyl benzoate;trifluoroborane Chemical compound FB(F)F.CCOC(=O)C1=CC=CC=C1 RSLGLAVKNHUDGW-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- GAIQJSWQJOZOMI-UHFFFAOYSA-L nickel(2+);dibenzoate Chemical compound [Ni+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAIQJSWQJOZOMI-UHFFFAOYSA-L 0.000 description 1
- DVTHIMLUHWEZOM-UHFFFAOYSA-L nickel(2+);octanoate Chemical compound [Ni+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O DVTHIMLUHWEZOM-UHFFFAOYSA-L 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 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
- 238000012360 testing method Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 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
- C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F136/02—Homopolymers 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
- C08F136/04—Homopolymers 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 conjugated
- C08F136/06—Butadiene
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
- Y10S526/903—Monomer polymerized in presence of transition metal containing catalyst and hydrocarbon additive affecting polymer properties of catalyst activity
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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US419649 | 1982-09-20 | ||
| US06/419,649 US4418185A (en) | 1982-09-20 | 1982-09-20 | Process for nonaqueous dispersion polymerization of butadiene in the presence of high cis-1,4-polyisoprene as a polymeric dispersing agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5978215A JPS5978215A (ja) | 1984-05-07 |
| JPH0229684B2 true JPH0229684B2 (OSRAM) | 1990-07-02 |
Family
ID=23663137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58174029A Granted JPS5978215A (ja) | 1982-09-20 | 1983-09-20 | 重合物分散剤の高シス−１，４−ポリイソプレン存在下に於けるブタジエンの非水分散重合方法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4418185A (OSRAM) |
| JP (1) | JPS5978215A (OSRAM) |
| CA (1) | CA1228450A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7006181B2 (en) | 1990-03-23 | 2006-02-28 | Matsushita Electric Industrial Co., Ltd. | Data processing apparatus |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4985505A (en) * | 1981-05-01 | 1991-01-15 | Mobil Oil Corporation | Process of dispersion polymerization of butadiene in propane or butane |
| JPS63308009A (ja) * | 1987-05-01 | 1988-12-15 | モービル・オイル・コーポレーション | ブタジエンの分散重合方法 |
| US5270395A (en) * | 1987-05-01 | 1993-12-14 | Basf Corporation | Process of dispersion polymerization of butadiene in propane or butane |
| US5171790A (en) * | 1990-04-04 | 1992-12-15 | The United States Of America As Represented By The Secretary Of The Navy | Elastomer blend for sound and vibration damping |
| US5531916A (en) * | 1990-10-03 | 1996-07-02 | E. I. Du Pont De Nemours And Company | Hydrofluorocarbon cleaning compositions |
| US5171902A (en) * | 1990-10-11 | 1992-12-15 | E. I. Du Pont De Nemours And Company | Saturated linear polyfluorohydrocarbons, processes for their production, and their use in cleaning compositions |
| US5268122A (en) * | 1991-08-28 | 1993-12-07 | E. I. Du Pont De Nemours And Company | Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions |
| US5196137A (en) * | 1991-10-01 | 1993-03-23 | E. I. Du Pont De Nemours And Company | Azeotropic composition of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, cis-1,2-dichloroethylene or 1,1-dichlorethane |
| US5250208A (en) * | 1992-04-02 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions |
| US5194170A (en) * | 1992-04-02 | 1993-03-16 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and either tran-1,2-dichloroethylene, cis 1,2-dichloroethylene, or 1-1 dichloroethane |
| US5688431A (en) * | 1994-09-29 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| US5562855A (en) * | 1994-09-29 | 1996-10-08 | E. I. Du Pont De Nemours And Company | Octafluorobutane compositions |
| WO2004037412A1 (ja) * | 2002-10-28 | 2004-05-06 | Idemitsu Kosan Co., Ltd. | 三フッ化ホウ素またはその錯体の回収・リサイクル方法 |
| CN103626926B (zh) * | 2012-08-21 | 2016-03-30 | 中国石油化工股份有限公司 | 一种聚丁二烯接枝异戊橡胶及其制备方法和硫化胶及混炼胶 |
| CN103172789A (zh) * | 2012-12-14 | 2013-06-26 | 万达集团股份有限公司 | 镍系低门尼高顺式1，4-聚丁二烯橡胶的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4098980A (en) * | 1976-06-24 | 1978-07-04 | The Goodyear Tire & Rubber Company | Non-aqueous dispersion polymerization of conjugated diolefins |
-
1982
- 1982-09-20 US US06/419,649 patent/US4418185A/en not_active Expired - Lifetime
-
1983
- 1983-09-06 CA CA000436070A patent/CA1228450A/en not_active Expired
- 1983-09-20 JP JP58174029A patent/JPS5978215A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7006181B2 (en) | 1990-03-23 | 2006-02-28 | Matsushita Electric Industrial Co., Ltd. | Data processing apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| US4418185A (en) | 1983-11-29 |
| CA1228450A (en) | 1987-10-20 |
| JPS5978215A (ja) | 1984-05-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0805823B1 (en) | Vapor phase synthesis of rubbery polymers | |
| JPH0229684B2 (OSRAM) | ||
| US4098980A (en) | Non-aqueous dispersion polymerization of conjugated diolefins | |
| US4452960A (en) | Process for nonaqueous dispersion polymerization of butadiene in the presence of polymeric dispersing agents | |
| BRPI0812683B1 (pt) | Processo para a preparação de um polidieno, sistema catalítico e cis-1,4-polidieno | |
| JPS61268706A (ja) | ブタジエン重合体又は共重合体の製造法 | |
| JPH072807B2 (ja) | ブタジエン重合体又は共重合体の製法 | |
| US3135725A (en) | Process of polymerizing conjugated diolefins with a cobalt salt-hydrocarbyl aluminumcompound catalyst | |
| JPH0730135B2 (ja) | ブタジエン重合体又は共重合体の製法 | |
| US4508881A (en) | Process for nonaqueous dispersion polymerization of butadiene in the presence of polymeric dispersing agents | |
| EP0106785B1 (en) | Process for nonaqueous dispersion polymerization of butadiene in the presence of carbonylated polymeric dispersing agents | |
| US4424324A (en) | Process for nonaqueous dispersion polymerization of butadiene | |
| NL8700380A (nl) | Werkwijze voor het in de massa polymeriseren van butadieen. | |
| EP0115833A1 (en) | Polyolefin polymerization process and catalyst | |
| US4503159A (en) | Polyolefin polymerization process and catalyst | |
| JPS6126604A (ja) | ポリオレフインの重合方法及び重合触媒の製造方法 | |
| US5859156A (en) | Vapor phase synthesis of rubbery polymers | |
| US3317437A (en) | Process for the production of alfin catalysts | |
| US3114744A (en) | Polymerization of isoprene to trans-1, 4-polyisoprene with a vcl3-ti (or)4-air3 catalst | |
| US4199474A (en) | Catalysts for polymerizing olefins | |
| Stille et al. | Polymerization of phenyl‐substituted butadienes by metal alkyl catalysts | |
| US3642734A (en) | Polymerization process | |
| US3062796A (en) | Production of synthetic elastomers | |
| US3031424A (en) | Polymer recovery process | |
| JPS6152170B2 (OSRAM) |