JP2003505540A5 - - Google Patents
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- Publication number
- JP2003505540A5 JP2003505540A5 JP2001511497A JP2001511497A JP2003505540A5 JP 2003505540 A5 JP2003505540 A5 JP 2003505540A5 JP 2001511497 A JP2001511497 A JP 2001511497A JP 2001511497 A JP2001511497 A JP 2001511497A JP 2003505540 A5 JP2003505540 A5 JP 2003505540A5
- Authority
- JP
- Japan
- Prior art keywords
- functional
- methacrylate
- acrylate
- high temperature
- reactor
- 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.)
- Granted
Links
- 239000000178 monomer Substances 0.000 description 67
- 238000000034 method Methods 0.000 description 45
- 238000006116 polymerization reaction Methods 0.000 description 38
- 229920000642 polymer Polymers 0.000 description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 239000008199 coating composition Substances 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 4
- 239000007863 gel particle Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical group CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- -1 i-amyl acrylate Chemical compound 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- LBHPSYROQDMVBS-UHFFFAOYSA-N (1-methylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCCC1 LBHPSYROQDMVBS-UHFFFAOYSA-N 0.000 description 1
- CJCGDEYGAIPAEN-UHFFFAOYSA-N (1-methylcyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1(C)CCCCC1 CJCGDEYGAIPAEN-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 description 1
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RUZXDTHZHJTTRO-UHFFFAOYSA-N 7-amino-4h-1,4-benzoxazin-3-one Chemical compound N1C(=O)COC2=CC(N)=CC=C21 RUZXDTHZHJTTRO-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- OXOPJTLVRHRSDJ-SNAWJCMRSA-N [(e)-but-2-enyl] 2-methylprop-2-enoate Chemical compound C\C=C\COC(=O)C(C)=C OXOPJTLVRHRSDJ-SNAWJCMRSA-N 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- RNOOHTVUSNIPCJ-UHFFFAOYSA-N butan-2-yl prop-2-enoate Chemical compound CCC(C)OC(=O)C=C RNOOHTVUSNIPCJ-UHFFFAOYSA-N 0.000 description 1
- KGVITRZHZPHLOI-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCOC(=O)C(C)=C KGVITRZHZPHLOI-UHFFFAOYSA-N 0.000 description 1
- WRAABIJFUKKEJQ-UHFFFAOYSA-N cyclopentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCC1 WRAABIJFUKKEJQ-UHFFFAOYSA-N 0.000 description 1
- BTQLDZMOTPTCGG-UHFFFAOYSA-N cyclopentyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCC1 BTQLDZMOTPTCGG-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35435099A | 1999-07-14 | 1999-07-14 | |
| US09/354,350 | 1999-07-14 | ||
| PCT/US2000/018970 WO2001005841A1 (en) | 1999-07-14 | 2000-07-12 | Process for the continuous production of gel free polymers, and powder and liquid coating applications containing gel free polymers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009261845A Division JP2010043284A (ja) | 1999-07-14 | 2009-11-17 | ゲル不含ポリマーの連続的製造方法ならびにゲル不含ポリマーを含む粉体および液体コーティング材料 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003505540A JP2003505540A (ja) | 2003-02-12 |
| JP2003505540A5 true JP2003505540A5 (https=) | 2007-08-16 |
| JP4944326B2 JP4944326B2 (ja) | 2012-05-30 |
Family
ID=23392931
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001511497A Expired - Fee Related JP4944326B2 (ja) | 1999-07-14 | 2000-07-12 | ゲル不含ポリマーの連続的製造方法ならびにゲル不含ポリマーを含む粉体および液体コーティング材料 |
| JP2009261845A Pending JP2010043284A (ja) | 1999-07-14 | 2009-11-17 | ゲル不含ポリマーの連続的製造方法ならびにゲル不含ポリマーを含む粉体および液体コーティング材料 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009261845A Pending JP2010043284A (ja) | 1999-07-14 | 2009-11-17 | ゲル不含ポリマーの連続的製造方法ならびにゲル不含ポリマーを含む粉体および液体コーティング材料 |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1203029B1 (https=) |
| JP (2) | JP4944326B2 (https=) |
| KR (2) | KR100686670B1 (https=) |
| CN (1) | CN1198850C (https=) |
| AT (1) | ATE282049T1 (https=) |
| AU (1) | AU6089600A (https=) |
| CA (1) | CA2378031C (https=) |
| DE (1) | DE60015768T2 (https=) |
| ES (1) | ES2231223T3 (https=) |
| MX (1) | MXPA02000471A (https=) |
| PT (1) | PT1203029E (https=) |
| TW (2) | TWI232870B (https=) |
| WO (1) | WO2001005841A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2004058826A1 (ja) | 2002-12-25 | 2006-04-27 | 三菱レイヨン株式会社 | ビニル系重合体、ビニル系重合体の製造方法、熱硬化性被覆用組成物、及び塗料 |
| WO2006048708A2 (ja) * | 2004-10-08 | 2006-05-11 | Basf Coatings Japan Ltd. | 塗料用水酸基含有樹脂組成物、塗料組成物、塗装仕上げ方法及び塗装物品 |
| CN100491407C (zh) * | 2005-01-12 | 2009-05-27 | 中国石油化工股份有限公司 | 均匀悬浮液的连续加料装置 |
| PL2098575T3 (pl) | 2008-03-04 | 2011-02-28 | Akzo Nobel Coatings Int Bv | Proszek powłokowy zawierający związki akrylowe z epoksydowymi grupami funkcyjnymi oraz powłoki proszkowe oporne na korozję nitkową wykonane z takiego proszku |
| US7737238B2 (en) * | 2008-03-04 | 2010-06-15 | Anderson Development Co. | Resin suitable for powder coating compositions |
| DE102009046922A1 (de) | 2009-11-20 | 2011-05-26 | Evonik Röhm Gmbh | Substanzpolymerisation von (Meth)acrylat-Copolymeren, die im Wässrig-alkalischen löslich sind |
| RU2444529C1 (ru) * | 2010-07-13 | 2012-03-10 | Учреждение Российской академии наук Институт физики им. Л.В. Киренского Сибирского отделения РАН (ИФ СО РАН) | Устройство для направленной полимеризации |
| CN109632572B (zh) * | 2018-12-25 | 2021-03-30 | 山西霍家长化合成橡胶有限公司 | Pdva油漆聚合终点判定方法 |
| JP7016485B2 (ja) * | 2019-12-11 | 2022-02-07 | 三菱瓦斯化学株式会社 | 化合物及びその製造方法、樹脂組成物、樹脂シート、多層プリント配線板、並びに半導体装置 |
| US20240117107A1 (en) * | 2020-12-15 | 2024-04-11 | Toyobo Mc Corporation | Polyester resin |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5423370B2 (https=) * | 1974-03-25 | 1979-08-13 | ||
| JPS5474891A (en) * | 1977-11-29 | 1979-06-15 | Asahi Chem Ind Co Ltd | Continous preparation of copolymer having crosslinkable functional group |
| JPS5853901A (ja) * | 1981-09-28 | 1983-03-30 | Nitto Electric Ind Co Ltd | アクリル酸アルキルエステル系ポリマ−の製造方法 |
| US4529787A (en) * | 1982-06-15 | 1985-07-16 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| IT1164238B (it) * | 1983-05-25 | 1987-04-08 | Anic Spa | Procedimento per la polimerizzazione del butadiene |
| CA2020166A1 (en) * | 1989-07-07 | 1991-01-08 | Jonathan T. Martz | Polymers for high gloss coatings |
| DE3924618A1 (de) * | 1989-07-26 | 1991-01-31 | Basf Lacke & Farben | Ueberzugsmittel auf der basis von carboxylgruppenhaltigen polymeren und epoxidgruppenhaltigen vernetzern, verfahren zur herstellung des ueberzugsmittels sowie seine verwendung |
| JPH06100605A (ja) * | 1992-09-18 | 1994-04-12 | Sanyo Chem Ind Ltd | アクリル系樹脂の製法 |
| DE4435950A1 (de) * | 1994-10-07 | 1996-04-11 | Hoechst Ag | Copolymerisate mit cyclischen oder polycyclischen Monomeren mit einer speziellen Isomerenverteilung und deren Einsatz in Beschichtungsmitteln |
| US5508366A (en) * | 1994-10-18 | 1996-04-16 | S. C. Johnson & Son, Inc. | Continuous production of reduced gel content hydroxylated addition polymers |
| US5986020A (en) * | 1997-08-05 | 1999-11-16 | Campbell; J. David | Process for producing hyperbranched polymers |
| DE19752747A1 (de) * | 1997-11-28 | 1999-06-24 | Herberts Gmbh | Verfahren zur Herstellung von Glycidyl(meth)acrylat-Copolymeren |
| MXPA02000469A (es) * | 1999-07-14 | 2004-05-21 | Johnson Polymer Inc | Proceso para la produccion continua de polimeros epoxi-(met) acrilico-estireno y su uso en revestimiento. |
-
2000
- 2000-07-12 WO PCT/US2000/018970 patent/WO2001005841A1/en not_active Ceased
- 2000-07-12 JP JP2001511497A patent/JP4944326B2/ja not_active Expired - Fee Related
- 2000-07-12 EP EP00947253A patent/EP1203029B1/en not_active Expired - Lifetime
- 2000-07-12 AT AT00947253T patent/ATE282049T1/de not_active IP Right Cessation
- 2000-07-12 KR KR1020027000414A patent/KR100686670B1/ko not_active Expired - Lifetime
- 2000-07-12 KR KR1020027000413A patent/KR100686669B1/ko not_active Expired - Fee Related
- 2000-07-12 AU AU60896/00A patent/AU6089600A/en not_active Abandoned
- 2000-07-12 CA CA002378031A patent/CA2378031C/en not_active Expired - Fee Related
- 2000-07-12 ES ES00947253T patent/ES2231223T3/es not_active Expired - Lifetime
- 2000-07-12 MX MXPA02000471A patent/MXPA02000471A/es active IP Right Grant
- 2000-07-12 CN CNB008102333A patent/CN1198850C/zh not_active Expired - Fee Related
- 2000-07-12 PT PT00947253T patent/PT1203029E/pt unknown
- 2000-07-12 DE DE60015768T patent/DE60015768T2/de not_active Expired - Lifetime
- 2000-10-17 TW TW089114107A patent/TWI232870B/zh not_active IP Right Cessation
- 2000-10-17 TW TW089114126A patent/TWI268935B/zh not_active IP Right Cessation
-
2009
- 2009-11-17 JP JP2009261845A patent/JP2010043284A/ja active Pending
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