TW550269B - Process for the preparation of macromers - Google Patents
Process for the preparation of macromers Download PDFInfo
- Publication number
- TW550269B TW550269B TW087112914A TW87112914A TW550269B TW 550269 B TW550269 B TW 550269B TW 087112914 A TW087112914 A TW 087112914A TW 87112914 A TW87112914 A TW 87112914A TW 550269 B TW550269 B TW 550269B
- Authority
- TW
- Taiwan
- Prior art keywords
- methacrylate
- acrylate
- acrylic
- reactor
- monomer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title description 19
- 239000000178 monomer Substances 0.000 claims abstract description 102
- 238000006243 chemical reaction Methods 0.000 claims abstract description 72
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 4
- -1 n-butyl ethyl Chemical group 0.000 claims description 31
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- 230000002079 cooperative effect Effects 0.000 claims description 10
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical group CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 4
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 3
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 claims description 3
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical group CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 3
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 2
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 2
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 claims description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 2
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 3
- 229940017219 methyl propionate Drugs 0.000 claims 3
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 claims 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims 2
- GCIHZDWTJCGMDK-UHFFFAOYSA-N (2-methylphenyl) prop-2-enoate Chemical compound CC1=CC=CC=C1OC(=O)C=C GCIHZDWTJCGMDK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims 1
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims 1
- FEUFEGJTJIHPOF-UHFFFAOYSA-N 2-butyl acrylic acid Chemical compound CCCCC(=C)C(O)=O FEUFEGJTJIHPOF-UHFFFAOYSA-N 0.000 claims 1
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 claims 1
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 claims 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims 1
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 claims 1
- NWKKCUWIMOZYOO-UHFFFAOYSA-N 3-methoxybutyl 2-methylprop-2-enoate Chemical compound COC(C)CCOC(=O)C(C)=C NWKKCUWIMOZYOO-UHFFFAOYSA-N 0.000 claims 1
- ULYIFEQRRINMJQ-UHFFFAOYSA-N 3-methylbutyl 2-methylprop-2-enoate Chemical compound CC(C)CCOC(=O)C(C)=C ULYIFEQRRINMJQ-UHFFFAOYSA-N 0.000 claims 1
- ASLOMEPLDWVVRG-UHFFFAOYSA-N 3-phenylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=CC1=CC=CC=C1 ASLOMEPLDWVVRG-UHFFFAOYSA-N 0.000 claims 1
- 229920001651 Cyanoacrylate Polymers 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- VEPKQEUBKLEPRA-UHFFFAOYSA-N VX-745 Chemical compound FC1=CC(F)=CC=C1SC1=NN2C=NC(=O)C(C=3C(=CC=CC=3Cl)Cl)=C2C=C1 VEPKQEUBKLEPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 238000011437 continuous method Methods 0.000 claims 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims 1
- OUGJKAQEYOUGKG-UHFFFAOYSA-N ethyl 2-methylidenebutanoate Chemical compound CCOC(=O)C(=C)CC OUGJKAQEYOUGKG-UHFFFAOYSA-N 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- JDTXSWGCYBOHDZ-UHFFFAOYSA-N n-(9h-fluoren-1-yl)prop-2-enamide Chemical compound C1C2=CC=CC=C2C2=C1C(NC(=O)C=C)=CC=C2 JDTXSWGCYBOHDZ-UHFFFAOYSA-N 0.000 claims 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 claims 1
- 229940090181 propyl acetate Drugs 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 239000003999 initiator Substances 0.000 abstract description 22
- 125000003118 aryl group Chemical group 0.000 abstract description 15
- 238000002156 mixing Methods 0.000 abstract description 9
- 230000000977 initiatory effect Effects 0.000 abstract description 3
- 150000003254 radicals Chemical class 0.000 abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
- 229920000642 polymer Polymers 0.000 description 22
- 239000011159 matrix material Substances 0.000 description 19
- 238000011049 filling Methods 0.000 description 18
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 12
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 12
- 238000012546 transfer Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 230000000379 polymerizing effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 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
- 230000007423 decrease Effects 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000012691 depolymerization reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000012722 thermally initiated polymerization Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- CWWYEELVMRNKHZ-UHFFFAOYSA-N 2,3-dimethylbut-2-enamide Chemical compound CC(C)=C(C)C(N)=O CWWYEELVMRNKHZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- FURRSXHPLKQVIR-UHFFFAOYSA-N 2-methoxybutyl prop-2-enoate Chemical compound CCC(OC)COC(=O)C=C FURRSXHPLKQVIR-UHFFFAOYSA-N 0.000 description 1
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 description 1
- QFQGEGZHVVKSEK-UHFFFAOYSA-N 2-phenylbutanimidamide Chemical compound CCC(C(N)=N)C1=CC=CC=C1 QFQGEGZHVVKSEK-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- SLIKGQHGNXRQIP-UHFFFAOYSA-N 3-ethoxy-3-oxoprop-1-ene-2-sulfonic acid Chemical compound CCOC(=O)C(=C)S(O)(=O)=O SLIKGQHGNXRQIP-UHFFFAOYSA-N 0.000 description 1
- KWFQLEGOEWMCCK-UHFFFAOYSA-N 3-ethyl-1h-pyridin-2-one Chemical compound CCC1=CC=CNC1=O KWFQLEGOEWMCCK-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- NPYMXLXNEYZTMQ-UHFFFAOYSA-N 3-methoxybutyl prop-2-enoate Chemical compound COC(C)CCOC(=O)C=C NPYMXLXNEYZTMQ-UHFFFAOYSA-N 0.000 description 1
- WJEZKKYHLLOIGR-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate 2-methylprop-2-enoic acid Chemical compound C(C=C)(=O)OCCC(C)C.C(C(=C)C)(=O)O WJEZKKYHLLOIGR-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- MUPJJZVGSOUSFH-UHFFFAOYSA-N 4-(2-cyanoethyl)-4-nitroheptanedinitrile Chemical compound N#CCCC([N+](=O)[O-])(CCC#N)CCC#N MUPJJZVGSOUSFH-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
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- VLKMIPHLVWYOTQ-UHFFFAOYSA-N 5,6-dihydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCC(O)CO VLKMIPHLVWYOTQ-UHFFFAOYSA-N 0.000 description 1
- YSTHDPLWNNHMES-UHFFFAOYSA-N C(C)NC(C(=C)C1=CC=CC=2C3=CC=CC=C3CC12)=O Chemical compound C(C)NC(C(=C)C1=CC=CC=2C3=CC=CC=C3CC12)=O YSTHDPLWNNHMES-UHFFFAOYSA-N 0.000 description 1
- DOAXOKNATSCGEU-UHFFFAOYSA-N CNC(C(=C)C1=CC=CC=2C3=CC=CC=C3CC12)=O Chemical compound CNC(C(=C)C1=CC=CC=2C3=CC=CC=C3CC12)=O DOAXOKNATSCGEU-UHFFFAOYSA-N 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- 108010088842 Fibrinolysin Proteins 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CVXHBROPWMVEQO-UHFFFAOYSA-N Peroxyoctanoic acid Chemical compound CCCCCCCC(=O)OO CVXHBROPWMVEQO-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- ZGJVTOHMNLDNNU-UHFFFAOYSA-N acetic acid;heptanoic acid Chemical compound CC(O)=O.CCCCCCC(O)=O ZGJVTOHMNLDNNU-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CVUNPKSKGHPMSY-UHFFFAOYSA-N ethyl 2-chloroprop-2-enoate Chemical compound CCOC(=O)C(Cl)=C CVUNPKSKGHPMSY-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229940001501 fibrinolysin Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- TZILQVJDAVFKLE-UHFFFAOYSA-N hexan-3-yl 2-methylprop-2-enoate Chemical compound CCCC(CC)OC(=O)C(C)=C TZILQVJDAVFKLE-UHFFFAOYSA-N 0.000 description 1
- ZHUXMBYIONRQQX-UHFFFAOYSA-N hydroxidodioxidocarbon(.) Chemical compound [O]C(O)=O ZHUXMBYIONRQQX-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 238000000710 polymer precipitation Methods 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
-
- 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
-
- 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
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/12—Esters of monohydric alcohols or phenols
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)
- Macromonomer-Based Addition Polymer (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polymerisation Methods In General (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/906,141 US6388026B1 (en) | 1997-08-05 | 1997-08-05 | Process for the preparation of macromers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW550269B true TW550269B (en) | 2003-09-01 |
Family
ID=25421992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087112914A TW550269B (en) | 1997-08-05 | 1999-02-06 | Process for the preparation of macromers |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6388026B1 (enExample) |
| EP (1) | EP1001994B1 (enExample) |
| JP (1) | JP4237935B2 (enExample) |
| KR (1) | KR100573637B1 (enExample) |
| CN (1) | CN1114622C (enExample) |
| AT (1) | ATE235516T1 (enExample) |
| AU (1) | AU735802B2 (enExample) |
| CA (1) | CA2295590C (enExample) |
| DE (1) | DE69812638T2 (enExample) |
| MX (1) | MX218562B (enExample) |
| PH (1) | PH11998001991B1 (enExample) |
| TW (1) | TW550269B (enExample) |
| WO (1) | WO1999007755A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6730763B1 (en) * | 2000-03-29 | 2004-05-04 | Toagosei Co., Ltd. | Composition |
| EP1207173A1 (en) | 2000-11-15 | 2002-05-22 | Eastman Chemical Company | Waterborne acrylic modified alkyd |
| WO2002057354A2 (en) * | 2001-01-19 | 2002-07-25 | Exxonmobil Chemical Patents Inc. | Ethylene alkyl acrylate copolymers with improved heat resistance |
| WO2002074822A1 (en) * | 2001-03-15 | 2002-09-26 | Toagosei Co., Ltd. | Process for producing copolymer |
| JP4001108B2 (ja) * | 2001-07-03 | 2007-10-31 | 東亞合成株式会社 | 硬化物及び塗膜の製造方法 |
| JP2003301005A (ja) * | 2002-04-09 | 2003-10-21 | Daicel Chem Ind Ltd | 架橋性ビニル重合体及びその製造方法 |
| US7585924B2 (en) | 2002-07-11 | 2009-09-08 | E. I. Du Pont De Nemours And Company | Pressurized high temperature polymerization process and polymerization system used therein |
| CN100343284C (zh) * | 2002-12-25 | 2007-10-17 | 三菱丽阳株式会社 | 乙烯基类聚合物、乙烯基类聚合物的制造方法、热固化性被覆用组合物和涂料 |
| US20050003094A1 (en) * | 2003-07-02 | 2005-01-06 | Grady Michael Charles | Thermally initiated polymerization process |
| US20060079624A1 (en) * | 2004-10-08 | 2006-04-13 | Hildeberto Nava | Crosslinkable polymer systems |
| US20060173142A1 (en) * | 2005-02-01 | 2006-08-03 | Hildeberto Nava | Functionalized thermosetting resin systems |
| US20100105847A1 (en) | 2006-01-24 | 2010-04-29 | Intertape Polymer Corp. | Plug flow bulk polymerization of vinyl monomers |
| US7906598B2 (en) * | 2006-08-30 | 2011-03-15 | Intertape Polymer Corp. | Recirculation loop reactor bulk polymerization process |
| EP2057197B1 (en) * | 2006-08-30 | 2011-07-20 | Intertape Polymer Corp. | Recirculation loop reactor bulk polymerization process |
| JP5347115B2 (ja) * | 2007-04-24 | 2013-11-20 | 綜研化学株式会社 | 粘着剤の製造方法 |
| DE102013226502A1 (de) | 2013-12-18 | 2015-06-18 | Tesa Se | Verfahren zur Herstellung kurzkettiger Makromoleküle auf Styrolbasis |
| US11485699B2 (en) | 2016-07-06 | 2022-11-01 | Synthomer Adhesive Technologies Llc | (Meth)acrylic oligomers |
| US12258495B2 (en) | 2018-12-28 | 2025-03-25 | Saint-Gobain Performance Plastics Corporation | Adhesive composition and methods of forming the same |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2593399A (en) * | 1949-11-19 | 1952-04-22 | Monsanto Chemicals | Mass polymerization of styrene at 285u deg. c. |
| BE571473A (enExample) * | 1957-12-17 | |||
| FR1206795A (fr) * | 1958-05-16 | 1960-02-11 | Resines Et Vernis Artificiels | Procédé de polymérisation en masse continue de dérivés vinyliques |
| US4117235A (en) * | 1971-09-23 | 1978-09-26 | Owens-Illinois, Inc. | Novel preparation of novel low molecular weight, liquid polymer |
| US4276432A (en) * | 1973-07-18 | 1981-06-30 | Celanese Corporation | Low molecular weight acrylates or methacrylates and methods for their preparation |
| DE3026973A1 (de) * | 1980-07-16 | 1982-01-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastisch verarbeitbaren copolymerisaten |
| US4414370A (en) | 1981-01-09 | 1983-11-08 | S. C. Johnson & Son, Inc. | Process for continuous bulk copolymerization of vinyl monomers |
| US4529787A (en) | 1982-06-15 | 1985-07-16 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| JPS60133007A (ja) | 1983-12-20 | 1985-07-16 | Toagosei Chem Ind Co Ltd | マクロモノマ−の製造方法 |
| US4546160A (en) | 1984-02-29 | 1985-10-08 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| US4680352A (en) | 1985-03-01 | 1987-07-14 | E. I. Du Pont De Nemours And Company | Cobalt (II) chelates as chain transfer agents in free radical polymerizations |
| US4600755A (en) | 1985-04-03 | 1986-07-15 | Ppg Industries, Inc. | Free radical initiated polymerization of polymerizable ethylenically unsaturated monomer component in the presence of hydrogen peroxide |
| US5324879A (en) | 1985-12-03 | 1994-06-28 | Commonwealth Scientific And Industrial Research Organisation | Oligomerization process |
| JPS62232408A (ja) | 1986-04-03 | 1987-10-12 | Toagosei Chem Ind Co Ltd | 片末端に官能基を有するアクリル系ポリマ−の製造法 |
| US5028677A (en) | 1986-09-23 | 1991-07-02 | E. I. Du Pont De Nemours And Company | Novel macromonomer compositions |
| JP2847242B2 (ja) | 1988-04-21 | 1999-01-13 | 東亞合成株式会社 | カルボキシル基含有マクロモノマーの製造方法 |
| US5100980A (en) | 1990-02-06 | 1992-03-31 | Rohm And Haas Company | Process for efficient molecular weight control in copolymerization |
| JPH04108808A (ja) | 1990-08-28 | 1992-04-09 | Toagosei Chem Ind Co Ltd | マクロモノマーの製造方法 |
| JPH04119526A (ja) | 1990-09-10 | 1992-04-21 | Hitachi Electron Eng Co Ltd | ディスク移載装置 |
| US5268437A (en) | 1992-01-22 | 1993-12-07 | Rohm And Haas Company | High temperature aqueous polymerization process |
| CA2088129A1 (en) * | 1992-02-06 | 1993-08-07 | Fritz Erdmann Kempter | Continuous polymerization of vinyl monomers |
| JPH05247117A (ja) | 1992-03-10 | 1993-09-24 | Toagosei Chem Ind Co Ltd | マクロモノマー及びその製造方法 |
| JP3087793B2 (ja) | 1992-04-14 | 2000-09-11 | 東亞合成株式会社 | マクロモノマー及びその製造方法 |
| US5264530A (en) | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| JP3395291B2 (ja) | 1993-11-05 | 2003-04-07 | 住友化学工業株式会社 | メタクリル系重合体の製造方法 |
| CA2151112A1 (en) | 1994-06-13 | 1995-12-14 | Michael Bennett Freeman | High temperature polymerization process and products therefrom |
| US5587431A (en) | 1995-04-21 | 1996-12-24 | E. I. Du Pont De Nemours And Company | Synthesis of terminally unsaturated oligomers |
-
1997
- 1997-08-05 US US08/906,141 patent/US6388026B1/en not_active Expired - Lifetime
-
1998
- 1998-08-04 CA CA002295590A patent/CA2295590C/en not_active Expired - Fee Related
- 1998-08-04 JP JP2000506252A patent/JP4237935B2/ja not_active Expired - Lifetime
- 1998-08-04 DE DE69812638T patent/DE69812638T2/de not_active Expired - Lifetime
- 1998-08-04 KR KR1020007001175A patent/KR100573637B1/ko not_active Expired - Lifetime
- 1998-08-04 WO PCT/US1998/016198 patent/WO1999007755A2/en not_active Ceased
- 1998-08-04 AU AU88979/98A patent/AU735802B2/en not_active Expired
- 1998-08-04 AT AT98940784T patent/ATE235516T1/de not_active IP Right Cessation
- 1998-08-04 EP EP98940784A patent/EP1001994B1/en not_active Expired - Lifetime
- 1998-08-04 CN CN98807722A patent/CN1114622C/zh not_active Expired - Lifetime
- 1998-08-04 PH PH11998001991A patent/PH11998001991B1/en unknown
-
1999
- 1999-02-06 TW TW087112914A patent/TW550269B/zh not_active IP Right Cessation
-
2000
- 2000-02-04 MX MXPA00001294 patent/MX218562B/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1001994A2 (en) | 2000-05-24 |
| US6388026B1 (en) | 2002-05-14 |
| JP4237935B2 (ja) | 2009-03-11 |
| EP1001994B1 (en) | 2003-03-26 |
| CA2295590C (en) | 2005-07-05 |
| JP2001512753A (ja) | 2001-08-28 |
| DE69812638T2 (de) | 2004-03-18 |
| AU8897998A (en) | 1999-03-01 |
| KR20010022584A (ko) | 2001-03-26 |
| DE69812638D1 (de) | 2003-04-30 |
| CN1265677A (zh) | 2000-09-06 |
| WO1999007755A2 (en) | 1999-02-18 |
| ATE235516T1 (de) | 2003-04-15 |
| MXPA00001294A (es) | 2000-10-31 |
| AU735802B2 (en) | 2001-07-12 |
| CN1114622C (zh) | 2003-07-16 |
| CA2295590A1 (en) | 1999-02-18 |
| PH11998001991B1 (en) | 2003-10-10 |
| MX218562B (es) | 2004-01-09 |
| WO1999007755A3 (en) | 1999-06-24 |
| KR100573637B1 (ko) | 2006-04-26 |
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| GD4A | Issue of patent certificate for granted invention patent | ||
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