CA2295654C - Process for producing hyperbranched polymers - Google Patents
Process for producing hyperbranched polymers Download PDFInfo
- Publication number
- CA2295654C CA2295654C CA002295654A CA2295654A CA2295654C CA 2295654 C CA2295654 C CA 2295654C CA 002295654 A CA002295654 A CA 002295654A CA 2295654 A CA2295654 A CA 2295654A CA 2295654 C CA2295654 C CA 2295654C
- Authority
- CA
- Canada
- Prior art keywords
- monomer
- weight
- reactor
- minutes
- methacrylate
- 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 - Fee Related
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- 238000000034 method Methods 0.000 title claims abstract description 46
- 229920000587 hyperbranched polymer Polymers 0.000 title claims abstract description 36
- 239000000178 monomer Substances 0.000 claims abstract description 146
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 230000000977 initiatory effect Effects 0.000 claims abstract description 5
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 85
- 229920000642 polymer Polymers 0.000 claims description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 28
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 10
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical group CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000002904 solvent Substances 0.000 description 28
- 239000000499 gel Substances 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000003999 initiator Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000010526 radical polymerization reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- -1 3-methoxybutyl Chemical group 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 238000000149 argon plasma sintering Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000003708 ampul Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003550 marker Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 3
- 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 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 2
- GQEKAPMWKCXNCF-UHFFFAOYSA-N 2,2-bis(ethenyl)-1,4-dioxane Chemical compound C=CC1(C=C)COCCO1 GQEKAPMWKCXNCF-UHFFFAOYSA-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
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-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
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 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
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 238000012722 thermally initiated polymerization Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical class OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ARKHCBWJALMQJO-NXEZZACHSA-N (1S,2S)-1,2-bis(ethenyl)cyclohexane Chemical compound C=C[C@@H]1CCCC[C@H]1C=C ARKHCBWJALMQJO-NXEZZACHSA-N 0.000 description 1
- ARKHCBWJALMQJO-AOOOYVTPSA-N (1r,2s)-1,2-bis(ethenyl)cyclohexane Chemical compound C=C[C@@H]1CCCC[C@@H]1C=C ARKHCBWJALMQJO-AOOOYVTPSA-N 0.000 description 1
- BWTMTZBMAGYMOD-UHFFFAOYSA-N (2,2,3,3,4,4,5,5-octafluoro-6-prop-2-enoyloxyhexyl) prop-2-enoate Chemical compound C=CC(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C BWTMTZBMAGYMOD-UHFFFAOYSA-N 0.000 description 1
- OIEASXSLJCRESE-UHFFFAOYSA-N (2,2,3,3-tetrafluoro-1-prop-2-enoyloxybutyl) prop-2-enoate Chemical compound CC(F)(F)C(F)(F)C(OC(=O)C=C)OC(=O)C=C OIEASXSLJCRESE-UHFFFAOYSA-N 0.000 description 1
- JMMVHMOAIMOMOF-UHFFFAOYSA-N (4-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=C(OC(=O)C=C)C=C1 JMMVHMOAIMOMOF-UHFFFAOYSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 1
- XVSBDEPLEQHLTE-UHFFFAOYSA-N 1,1-bis(ethenoxy)cyclohexane Chemical compound C=COC1(OC=C)CCCCC1 XVSBDEPLEQHLTE-UHFFFAOYSA-N 0.000 description 1
- GPHWXFINOWXMDN-UHFFFAOYSA-N 1,1-bis(ethenoxy)hexane Chemical compound CCCCCC(OC=C)OC=C GPHWXFINOWXMDN-UHFFFAOYSA-N 0.000 description 1
- HIYIGPVBMDKPCR-UHFFFAOYSA-N 1,1-bis(ethenoxymethyl)cyclohexane Chemical compound C=COCC1(COC=C)CCCCC1 HIYIGPVBMDKPCR-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- UHHCYAAVGADGGP-UHFFFAOYSA-N 1,2-bis(ethenyl)cyclobutane Chemical compound C=CC1CCC1C=C UHHCYAAVGADGGP-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 1
- LFYMIRQGCLQTGU-UHFFFAOYSA-N 1-(1-prop-2-enoylpiperazin-2-yl)prop-2-en-1-one Chemical compound C=CC(=O)C1CNCCN1C(=O)C=C LFYMIRQGCLQTGU-UHFFFAOYSA-N 0.000 description 1
- UXKQGJYFPNFUJY-UHFFFAOYSA-N 1-(2-methylbutan-2-yldiazenyl)cyclohexane-1-carbonitrile Chemical compound CCC(C)(C)N=NC1(C#N)CCCCC1 UXKQGJYFPNFUJY-UHFFFAOYSA-N 0.000 description 1
- CARZNHSZGXCIJM-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)OC(=O)C(C)=C CARZNHSZGXCIJM-UHFFFAOYSA-N 0.000 description 1
- JZLGFDCTQXFHGL-UHFFFAOYSA-N 1-(butyldiazenyl)cyclohexane-1-carbonitrile Chemical compound CCCCN=NC1(C#N)CCCCC1 JZLGFDCTQXFHGL-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- KFQPRNVTVMCYEH-UHFFFAOYSA-N 1-amino-3-(4-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CN)C=C1 KFQPRNVTVMCYEH-UHFFFAOYSA-N 0.000 description 1
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 1
- FWTVCFLAJJDTLG-UHFFFAOYSA-N 1-ethenyl-4-[(4-ethenylphenyl)methyl]benzene Chemical compound C1=CC(C=C)=CC=C1CC1=CC=C(C=C)C=C1 FWTVCFLAJJDTLG-UHFFFAOYSA-N 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2455—Stationary reactors without moving elements inside provoking a loop type movement of the reactants
- B01J19/2465—Stationary reactors without moving elements inside provoking a loop type movement of the reactants externally, i.e. the mixture leaving the vessel and subsequently re-entering it
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/02—Polymerisation in bulk
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00054—Controlling or regulating the heat exchange system
- B01J2219/00056—Controlling or regulating the heat exchange system involving measured parameters
- B01J2219/00058—Temperature measurement
- B01J2219/0006—Temperature measurement of the heat exchange medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00164—Controlling or regulating processes controlling the flow
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/906,140 | 1997-08-05 | ||
| US08/906,140 US5986020A (en) | 1997-08-05 | 1997-08-05 | Process for producing hyperbranched polymers |
| PCT/US1998/016199 WO1999007754A1 (en) | 1997-08-05 | 1998-08-04 | Process for producing hyperbranched polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2295654A1 CA2295654A1 (en) | 1999-02-18 |
| CA2295654C true CA2295654C (en) | 2006-05-16 |
Family
ID=25421991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002295654A Expired - Fee Related CA2295654C (en) | 1997-08-05 | 1998-08-04 | Process for producing hyperbranched polymers |
Country Status (12)
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5986020A (en) * | 1997-08-05 | 1999-11-16 | Campbell; J. David | Process for producing hyperbranched polymers |
| CZ302849B6 (cs) * | 1998-03-12 | 2011-12-14 | Lucite International Uk Limited | Zpusob prípravy rozpustného rozvetveného polymeru, tento polymer, náterová kompozice obsahující tento polymer, lisovaný polymerní výrobek obsahující tento polymer a použití tohoto polymeru |
| US6806301B2 (en) * | 1998-11-30 | 2004-10-19 | Flint Ink Corporation | Lithographic printing inks |
| US6140392A (en) * | 1998-11-30 | 2000-10-31 | Flint Ink Corporation | Printing inks |
| US6638995B1 (en) * | 1998-11-30 | 2003-10-28 | Flint Ink Corporation | Printing inks |
| FR2791990A1 (fr) * | 1999-04-06 | 2000-10-13 | Oreal | Composition cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation notamment en capillaire |
| FR2791986A1 (fr) | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| US6946525B2 (en) | 1999-04-06 | 2005-09-20 | L'oreal S.A. | Composition comprising polymers having a star structure, the polymers, and their use |
| FR2791988A1 (fr) * | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique ou pharmaceutique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| FR2791987A1 (fr) | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| FR2791989A1 (fr) | 1999-04-06 | 2000-10-13 | Oreal | Composition notamment cosmetique comprenant des polymeres ayant une structure en etoiles, lesdits polymeres et leur utilisation |
| AU6089600A (en) * | 1999-07-14 | 2001-02-05 | Johnson Polymer, Inc. | Process for the continuous production of gel free polymers, and powder and liquid coating applications containing gel free polymers |
| ATE315052T1 (de) | 1999-07-14 | 2006-02-15 | Johnson Polymer Inc | Verfahren zur kontinuierlichen herstellung von epoxy - (meth)acryl - styrolpolymeren und ihre verwendung in beschichtungsmassen |
| US6605680B1 (en) | 2000-04-07 | 2003-08-12 | Eastman Chemical Resins, Inc. | Low color, aromatic modified C5 hydrocarbon resins |
| DE10035119A1 (de) | 2000-07-19 | 2002-01-31 | Basf Ag | Teilverzweigte Polymere |
| US20020020669A1 (en) * | 2000-07-28 | 2002-02-21 | Kim Yung K. | Silicone derivatized macromolecules |
| EP1367080A1 (en) | 2002-05-29 | 2003-12-03 | Hycail B.V. | Hyperbranched poly(hydroxycarboxylic acid) polymers |
| AU2003204606A1 (en) * | 2002-06-14 | 2004-01-15 | Rohm And Haas Company | Water-based adhesives |
| US6840175B2 (en) | 2002-11-20 | 2005-01-11 | Flint Ink Corporation | Lithographic printing method using a single fluid ink |
| JP3999746B2 (ja) * | 2003-05-19 | 2007-10-31 | ローム アンド ハース カンパニー | ポリマーナノ粒子の高固形分調製方法 |
| US20050080209A1 (en) * | 2003-10-08 | 2005-04-14 | Blankenship Robert Mitchell | Continuous production of crosslinked polymer nanoparticles |
| US6982309B2 (en) * | 2003-12-19 | 2006-01-03 | Fina Technology, Inc. | Synthesis of branched styrenic copolymers with p-t-butylstyrene |
| ATE547442T1 (de) | 2004-04-02 | 2012-03-15 | Nexttec Gmbh | Verfahren zur herstellung eines verbundsorptionsmaterials für die chromatographische trennung von biopolymeren |
| US7504466B2 (en) * | 2004-11-04 | 2009-03-17 | Rohm And Haas Company | High solids preparation of crosslinked polymer particles |
| DE602006007947D1 (de) * | 2005-01-25 | 2009-09-03 | Lg Chemical Ltd | Thermisch härtbare harzzusammensetzung mit verlängerter lagerungsstabilität und guten hafteigenschaften |
| US8192695B2 (en) * | 2005-05-04 | 2012-06-05 | Fina Technology, Inc. | Reactor apparatus having reduced back mixing |
| US7511101B2 (en) * | 2005-05-13 | 2009-03-31 | Fina Technology, Inc. | Plug flow reactor and polymers prepared therewith |
| TWI379849B (en) * | 2005-09-20 | 2012-12-21 | Eternal Chemical Co Ltd | Radiation-curable alkoxy silanized hyperbranched polyester acrylates and preparation thereof |
| US8163443B2 (en) * | 2006-03-09 | 2012-04-24 | Nippon Steel Chemical Co., Ltd. | Photosensitive resin composition for volume phase hologram recording and optical information recording medium using the same |
| US8231973B2 (en) * | 2006-06-13 | 2012-07-31 | 3M Innovative Properties Company | Fluoro(meth)acrylate polymer composition suitable for low index layer of antireflective film |
| US7615283B2 (en) * | 2006-06-13 | 2009-11-10 | 3M Innovative Properties Company | Fluoro(meth)acrylate polymer composition suitable for low index layer of antireflective film |
| US10435639B2 (en) | 2006-09-05 | 2019-10-08 | Cerion, Llc | Fuel additive containing lattice engineered cerium dioxide nanoparticles |
| WO2008030813A1 (en) * | 2006-09-05 | 2008-03-13 | Cerion Technology, Inc. | Method of conditioning an internal combustion engine |
| US8883865B2 (en) | 2006-09-05 | 2014-11-11 | Cerion Technology, Inc. | Cerium-containing nanoparticles |
| WO2008124265A2 (en) * | 2007-04-09 | 2008-10-16 | Dow Global Technologies, Inc. | Capped polyester polyol lubricant composition |
| US8221574B2 (en) | 2007-04-26 | 2012-07-17 | Csd, Llc | Top coating for indoor and outdoor temporary removable graphics and system and method for making, applying and removing such graphics |
| US20080268140A1 (en) | 2007-04-26 | 2008-10-30 | Csd, Inc. | Temporary removable solvent based protective coating |
| KR20110005682A (ko) * | 2008-01-30 | 2011-01-18 | 제론 코포레이션 | 줄기 세포 유래 심근세포 배양용 합성 표면 |
| CN101939362A (zh) * | 2008-01-30 | 2011-01-05 | 杰龙公司 | 用于培养干细胞衍生的少突胶质细胞前体细胞的合成表面 |
| WO2009149225A2 (en) * | 2008-06-06 | 2009-12-10 | Avery Dennison Corporation | Temporary outdoor graphic film |
| US7919640B2 (en) * | 2008-12-30 | 2011-04-05 | Fina Technology, Inc. | Synthesis with metal methacrylates as comonomers |
| US20100168357A1 (en) * | 2008-12-30 | 2010-07-01 | Fina Technology, Inc. | Branched Ionomers with Metal Methacrylates as Comonomers |
| US7919641B2 (en) * | 2008-12-30 | 2011-04-05 | Fina Technology, Inc. | Synthesis of styrene-soluble ionic comonomer |
| KR20110122122A (ko) * | 2009-01-12 | 2011-11-09 | 바스프 에스이 | 고탄성 연질 폴리우레탄 폼 |
| CN102549033A (zh) | 2009-09-30 | 2012-07-04 | 巴斯夫欧洲公司 | 烷氧基化聚合物 |
| JP5658607B2 (ja) * | 2010-03-31 | 2015-01-28 | 新日鉄住金化学株式会社 | 多分岐型超高分子量体を含有するスチレン系樹脂組成物の製造方法およびその組成物 |
| TWI507425B (zh) * | 2010-06-14 | 2015-11-11 | Nippon Steel & Sumikin Chem Co | An ultraviolet-curing resin composition for use in an ink-jet printing method, and an optical element |
| SG11201400246SA (en) * | 2011-08-30 | 2014-03-28 | Chevron Phillips Chemical Co | Hyperbranched polymers and methods of making and using same |
| JP5858705B2 (ja) * | 2011-09-26 | 2016-02-10 | 新日鉄住金化学株式会社 | 高分岐型超高分子量体を含有するスチレン系樹脂組成物の製造方法およびその組成物 |
| JP5913919B2 (ja) * | 2011-11-09 | 2016-04-27 | 新日鉄住金化学株式会社 | 高分岐型ゴム変性スチレン系樹脂組成物及びシート |
| JP5913917B2 (ja) * | 2011-11-09 | 2016-04-27 | 新日鉄住金化学株式会社 | 高分岐型発泡用スチレン系樹脂組成物 |
| JP5913918B2 (ja) * | 2011-11-09 | 2016-04-27 | 新日鉄住金化学株式会社 | 高分岐型板状押出発泡体用スチレン系樹脂組成物 |
| JP5930667B2 (ja) * | 2011-11-09 | 2016-06-08 | 新日鉄住金化学株式会社 | 高分岐型フィルム用スチレン系樹脂組成物及びスチレン系樹脂フィルム |
| JP5930668B2 (ja) * | 2011-11-09 | 2016-06-08 | 新日鉄住金化学株式会社 | インジェクションブロー成形品の製造方法 |
| JP5930666B2 (ja) * | 2011-11-09 | 2016-06-08 | 新日鉄住金化学株式会社 | 高分岐型二軸延伸シート用スチレン系樹脂組成物及び二軸延伸シート |
| CN102807631A (zh) * | 2012-08-15 | 2012-12-05 | 罗吉尔 | 管道式连续聚合反应法 |
| WO2014197421A1 (en) | 2013-06-05 | 2014-12-11 | Biotime, Inc. | Compositions and methods for induced tissue regeneration in mammalian species |
| US10143661B2 (en) | 2013-10-17 | 2018-12-04 | Cerion, Llc | Malic acid stabilized nanoceria particles |
| US11078462B2 (en) | 2014-02-18 | 2021-08-03 | ReCyte Therapeutics, Inc. | Perivascular stromal cells from primate pluripotent stem cells |
| US10240127B2 (en) | 2014-07-03 | 2019-03-26 | ReCyte Therapeutics, Inc. | Exosomes from clonal progenitor cells |
| TW201710411A (zh) * | 2015-06-09 | 2017-03-16 | P2I有限公司 | 塗層 |
| CA3202332A1 (en) | 2015-12-07 | 2017-06-15 | Agex Therapeutics, Inc. | Methods for the re-derivation of diverse pluripotent stem cell-derived brown fat cells |
| US9869018B2 (en) * | 2016-04-26 | 2018-01-16 | Taiwan Semiconductor Manufacturing Co., Ltd. | Solid precursor delivery method using liquid solvent for thin film deposition |
| CN106065053A (zh) * | 2016-06-13 | 2016-11-02 | 江苏大学 | 一种超支化聚二乙烯基苯多臂共聚物的合成方法 |
| KR102406946B1 (ko) * | 2020-07-16 | 2022-06-10 | 한국화학연구원 | 항균 하이퍼브랜치드 고분자 및 이를 이용한 항균 구형 활성탄 |
| CN112574428B (zh) * | 2020-12-16 | 2022-04-12 | 济南大学 | 一种超支化型含氟硅耐高温脱模剂及其应用 |
| CN114426675B (zh) * | 2021-12-17 | 2023-04-07 | 湖北康创科技有限公司 | 一种超支化阳离子聚合物乳液及其在污泥脱水上的应用 |
| CN114539642A (zh) * | 2022-01-18 | 2022-05-27 | 宁波伏龙同步带有限公司 | 一种机器人用的高性能双面齿覆带及其制备方法 |
| CN115466358B (zh) * | 2022-09-30 | 2024-12-10 | 中南民族大学 | 一种无溶剂水溶性氯化聚丙烯的制备方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE571473A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-12-17 | |||
| DE2936235C2 (de) * | 1978-09-09 | 1984-08-09 | Asahi Kasei Kogyo K.K., Osaka | Monovinylbenzol-Polyvinylbenzol-Copolymerisat, Verfahren zur Herstellung und dessen Verwendung |
| DE3026831A1 (de) * | 1980-07-16 | 1982-02-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von copolymerisaten auf basis von monovinylaromaten und ethylenisch ungesaettigten carbonsaeuren und deren verwendung von oberflaechenverguetungsmittel |
| EP0068024B2 (en) * | 1981-01-09 | 1996-02-07 | S.C. Johnson & Son, Inc. | Process for continuous bulk copolymerization of vinyl monomers |
| US4414370A (en) * | 1981-01-09 | 1983-11-08 | S. C. Johnson & Son, Inc. | Process for continuous bulk copolymerization of vinyl monomers |
| US5631329A (en) * | 1990-08-27 | 1997-05-20 | Dendritech, Inc. | Process for producing hyper-comb-branched polymers |
| SE9103077D0 (sv) * | 1991-10-22 | 1991-10-22 | Neste Oy | Omaettad etensampolymer och saett foer framstaellning daerav |
| DE4306384A1 (de) * | 1993-03-02 | 1994-09-08 | Basf Ag | Chlorfreie, nicht-trocknende Isobuten-Dien-Copolymere |
| JPH09502212A (ja) * | 1993-09-01 | 1997-03-04 | モービル・オイル・コーポレイション | 非共役ジエンからの新しい閉環重合ポリマー |
| US5484866A (en) * | 1993-11-09 | 1996-01-16 | Mobil Oil Corporation | Concentrates of a highly branched polymer and functional fluids prepared therefrom |
| FR2714384B1 (fr) * | 1993-12-29 | 1996-02-02 | Atochem Elf Sa | Copolymère bloc étoile d'un monomère vinylaromatique et d'un diène conjugué, son procédé d'obtention, et les compositions comprenant ledit copolymère et du polystyrène cristal. |
| US5414062A (en) * | 1994-03-10 | 1995-05-09 | Rohm And Haas Company | Method for reduction of aqueous phase polymer formation in suspension polymerization |
| US5508366A (en) * | 1994-10-18 | 1996-04-16 | S. C. Johnson & Son, Inc. | Continuous production of reduced gel content hydroxylated addition polymers |
| US5587441A (en) * | 1994-11-08 | 1996-12-24 | Cornell Research Foundation, Inc. | Hyperbranched polymers from AB monomers |
| US5767211A (en) * | 1996-05-02 | 1998-06-16 | E. I. Du Pont De Nemours And Company | Synthesis of multi-functional hyperbranched polymers by polymerization of di-or tri-vinyl monomers in the presence of a chain transfer catalyst |
| US5986020A (en) * | 1997-08-05 | 1999-11-16 | Campbell; J. David | Process for producing hyperbranched polymers |
-
1997
- 1997-08-05 US US08/906,140 patent/US5986020A/en not_active Expired - Lifetime
-
1998
- 1998-08-04 CN CNB988077205A patent/CN1294163C/zh not_active Expired - Lifetime
- 1998-08-04 WO PCT/US1998/016199 patent/WO1999007754A1/en active IP Right Grant
- 1998-08-04 EP EP98939197A patent/EP1001998B1/en not_active Expired - Lifetime
- 1998-08-04 AU AU87674/98A patent/AU747995B2/en not_active Ceased
- 1998-08-04 KR KR1020007001176A patent/KR100551187B1/ko not_active Expired - Lifetime
- 1998-08-04 CA CA002295654A patent/CA2295654C/en not_active Expired - Fee Related
- 1998-08-04 AT AT98939197T patent/ATE227312T1/de not_active IP Right Cessation
- 1998-08-04 DE DE69809247T patent/DE69809247T2/de not_active Expired - Lifetime
- 1998-08-04 JP JP2000506251A patent/JP4538573B2/ja not_active Expired - Lifetime
-
1999
- 1999-02-04 TW TW087112913A patent/TW505661B/zh active
- 1999-09-03 US US09/389,821 patent/US6265511B1/en not_active Expired - Lifetime
-
2000
- 2000-02-04 MX MXPA00001295 patent/MXPA00001295A/es unknown
-
2001
- 2001-06-04 US US09/873,634 patent/US6627720B2/en not_active Expired - Lifetime
-
2003
- 2003-08-14 MX MXPA03007260A patent/MXPA03007260A/es active IP Right Grant
- 2003-09-09 US US10/658,498 patent/US20040048987A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001512752A (ja) | 2001-08-28 |
| JP4538573B2 (ja) | 2010-09-08 |
| EP1001998B1 (en) | 2002-11-06 |
| WO1999007754A1 (en) | 1999-02-18 |
| KR20010022585A (ko) | 2001-03-26 |
| EP1001998A1 (en) | 2000-05-24 |
| CA2295654A1 (en) | 1999-02-18 |
| US5986020A (en) | 1999-11-16 |
| MXPA03007260A (es) | 2005-09-08 |
| MXPA00001295A (es) | 2000-10-31 |
| US6265511B1 (en) | 2001-07-24 |
| CN1294163C (zh) | 2007-01-10 |
| US6627720B2 (en) | 2003-09-30 |
| DE69809247D1 (de) | 2002-12-12 |
| KR100551187B1 (ko) | 2006-02-13 |
| US20040048987A1 (en) | 2004-03-11 |
| TW505661B (en) | 2002-10-11 |
| CN1265680A (zh) | 2000-09-06 |
| MX217863B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2003-12-01 |
| ATE227312T1 (de) | 2002-11-15 |
| AU747995B2 (en) | 2002-05-30 |
| US20010039316A1 (en) | 2001-11-08 |
| AU8767498A (en) | 1999-03-01 |
| DE69809247T2 (de) | 2003-07-24 |
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