WO1997021736A1 - Bulk radical polymerization using a batch reactor - Google Patents
Bulk radical polymerization using a batch reactor Download PDFInfo
- Publication number
- WO1997021736A1 WO1997021736A1 PCT/US1996/018503 US9618503W WO9721736A1 WO 1997021736 A1 WO1997021736 A1 WO 1997021736A1 US 9618503 W US9618503 W US 9618503W WO 9721736 A1 WO9721736 A1 WO 9721736A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mixture
- initiator
- temperature
- reaction
- ofthe
- Prior art date
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000012421 spiking Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000003797 telogen phase Effects 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000003643 water by type Substances 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
- C08F2/00—Processes of polymerisation
- C08F2/02—Polymerisation in bulk
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)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU76819/96A AU7681996A (en) | 1995-12-14 | 1996-11-12 | Bulk radical polymerization using a batch reactor |
EP96939732A EP0866810B1 (en) | 1995-12-14 | 1996-11-12 | Bulk radical polymerization using a batch reactor |
KR1019980704557A KR19990072192A (en) | 1995-12-14 | 1996-11-12 | Bulk Radical Polymerization Process Using Batch Reactor |
JP52204497A JP3837458B2 (en) | 1995-12-14 | 1996-11-12 | Radical bulk polymerization using a batch reactor. |
DE69619854T DE69619854T2 (en) | 1995-12-14 | 1996-11-12 | Radical bulk polymerization using a batch reactor |
BR9611919A BR9611919A (en) | 1995-12-14 | 1996-11-12 | Process for free radical polymerization of vinyl monomers and pressure sensitive adhesive |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/572,310 | 1995-12-14 | ||
US08/572,310 US5637646A (en) | 1995-12-14 | 1995-12-14 | Bulk radical polymerization using a batch reactor |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997021736A1 true WO1997021736A1 (en) | 1997-06-19 |
Family
ID=24287257
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/018503 WO1997021736A1 (en) | 1995-12-14 | 1996-11-12 | Bulk radical polymerization using a batch reactor |
Country Status (10)
Country | Link |
---|---|
US (3) | US5637646A (en) |
EP (1) | EP0866810B1 (en) |
JP (1) | JP3837458B2 (en) |
KR (1) | KR19990072192A (en) |
CN (1) | CN1209140A (en) |
AU (1) | AU7681996A (en) |
BR (1) | BR9611919A (en) |
CA (1) | CA2238366A1 (en) |
DE (1) | DE69619854T2 (en) |
WO (1) | WO1997021736A1 (en) |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2376872A1 (en) * | 1977-01-06 | 1978-08-04 | Pennwalt Corp | POLYMERIZATION PROCESS USING DIPEROXYCETALS AS FINISHING CATALYSTS |
JPS5887171A (en) * | 1981-11-18 | 1983-05-24 | Sekisui Chem Co Ltd | Production of acrylic pressure-sensitive adhesive |
EP0489318A1 (en) * | 1990-12-04 | 1992-06-10 | BASF Aktiengesellschaft | Mass and suspension polymers based on methyl methacrylate |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE513431A (en) * | 1951-09-10 | |||
NL127637C (en) * | 1959-07-03 | 1900-01-01 | ||
US3821330A (en) * | 1969-12-22 | 1974-06-28 | Du Pont | Continuous polymerization of acrylics |
US3842059A (en) * | 1971-02-22 | 1974-10-15 | M Chiang | Acrylate and methacrylate terminated polystyrene macromolecular monomers having a substantially uniform molecular weight distribution |
US3786116A (en) * | 1972-08-21 | 1974-01-15 | Cpc International Inc | Chemically joined,phase separated thermoplastic graft copolymers |
US4181752A (en) * | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
DE2613352B2 (en) * | 1976-03-29 | 1980-08-07 | Basf Ag, 6700 Ludwigshafen | Process for the production of impact-resistant modified styrene polymers |
AT356380B (en) * | 1977-11-17 | 1980-04-25 | Vianova Kunstharz Ag | METHOD FOR PRODUCING POLYMERISATES BY RADICALLY INITIATED SUBSTANCE POLYMERIZATION |
DE2839563A1 (en) * | 1978-09-12 | 1980-03-27 | Hoechst Ag | METHOD FOR CONTINUOUS MASS POLYMERIZATION OF ALKENYL FLAVORS |
IT1198338B (en) * | 1980-07-02 | 1988-12-21 | Montedison Spa | PROCESS FOR PRODUCING COPOLYMERS OF VINYL-AROMATIC MONOMERS WITH ETHYLENICALLY UNSATURATED NITRILS |
US4530979A (en) * | 1983-06-15 | 1985-07-23 | The Dow Company | Continuous polymerization of water-miscible polymers |
US4619979A (en) * | 1984-03-28 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Continuous free radial polymerization in a wiped-surface reactor |
US4843134A (en) * | 1984-03-28 | 1989-06-27 | Minnesota Mining And Manufacturing Company | Acrylate pressure-sensitive adhesives containing insolubles |
US4732808A (en) * | 1985-11-14 | 1988-03-22 | Minnesota Mining And Manufacturing Company | Macromer reinforced pressure sensitive skin adhesive sheet material |
US4737559A (en) * | 1986-05-19 | 1988-04-12 | Minnesota Mining And Manufacturing Co. | Pressure-sensitive adhesive crosslinked by copolymerizable aromatic ketone monomers |
US4983668A (en) * | 1987-11-25 | 1991-01-08 | Aristech Chemical Corporation | Polymer partculates for molding and the like |
EP0625998B1 (en) * | 1992-02-10 | 1996-06-05 | Minnesota Mining And Manufacturing Company | Radiation crosslinked elastomers |
US5244926A (en) * | 1992-06-16 | 1993-09-14 | The Dow Chemical Company | Preparation of ion exchange and adsorbent copolymers |
US5319030A (en) * | 1992-07-23 | 1994-06-07 | Chevron Research And Technology Company | One-step process for the preparation of alkenyl succinic anhydride |
US5252662A (en) * | 1992-09-25 | 1993-10-12 | Avery Dennison Corporation | Low viscosity acrylic hot melt adhesives |
DE4235789A1 (en) * | 1992-10-23 | 1994-05-05 | Basf Ag | Continuous degassing of thermoplastic polymer melt or soln. - contg. monomer and opt. thermally decomposed free radical initiator by using adiabatic heat of polymerisation for vaporisation |
DE4235785A1 (en) * | 1992-10-23 | 1994-05-11 | Basf Ag | Continuous polymerisation of olefinic monomers - uses a tubular reactor contg. a special temp.-controlled section followed by an adiabatic section discharging into a vacuum degassing chamber |
US5373074A (en) * | 1993-02-12 | 1994-12-13 | Isp Investments Inc. | Free radical solution polymerization of vinylpyrrolidone |
JPH06239905A (en) * | 1993-02-15 | 1994-08-30 | Mitsubishi Rayon Co Ltd | Sheet production of methacrylic polymer |
JP3395291B2 (en) * | 1993-11-05 | 2003-04-07 | 住友化学工業株式会社 | Method for producing methacrylic polymer |
US5637646A (en) * | 1995-12-14 | 1997-06-10 | Minnesota Mining And Manufacturing Company | Bulk radical polymerization using a batch reactor |
US5653968A (en) * | 1996-03-21 | 1997-08-05 | The Proctor & Gamble Company | Rinse-off hair care compositions |
-
1995
- 1995-12-14 US US08/572,310 patent/US5637646A/en not_active Expired - Lifetime
-
1996
- 1996-11-12 DE DE69619854T patent/DE69619854T2/en not_active Expired - Lifetime
- 1996-11-12 KR KR1019980704557A patent/KR19990072192A/en not_active Application Discontinuation
- 1996-11-12 JP JP52204497A patent/JP3837458B2/en not_active Expired - Lifetime
- 1996-11-12 CN CN96199944A patent/CN1209140A/en active Pending
- 1996-11-12 WO PCT/US1996/018503 patent/WO1997021736A1/en not_active Application Discontinuation
- 1996-11-12 BR BR9611919A patent/BR9611919A/en not_active Application Discontinuation
- 1996-11-12 CA CA002238366A patent/CA2238366A1/en not_active Abandoned
- 1996-11-12 AU AU76819/96A patent/AU7681996A/en not_active Abandoned
- 1996-11-12 EP EP96939732A patent/EP0866810B1/en not_active Expired - Lifetime
-
1997
- 1997-01-14 US US08/782,363 patent/US5753768A/en not_active Expired - Lifetime
- 1997-06-06 US US08/870,724 patent/US5986011A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2376872A1 (en) * | 1977-01-06 | 1978-08-04 | Pennwalt Corp | POLYMERIZATION PROCESS USING DIPEROXYCETALS AS FINISHING CATALYSTS |
JPS5887171A (en) * | 1981-11-18 | 1983-05-24 | Sekisui Chem Co Ltd | Production of acrylic pressure-sensitive adhesive |
EP0489318A1 (en) * | 1990-12-04 | 1992-06-10 | BASF Aktiengesellschaft | Mass and suspension polymers based on methyl methacrylate |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014093139A1 (en) | 2012-12-14 | 2014-06-19 | 3M Innovative Properties Company | Method of polymerizing ethylenically-unsaturated materials using ionizing radiation |
EP2931757B1 (en) * | 2012-12-14 | 2020-04-01 | 3M Innovative Properties Company | Method of polymerizing ethylenically-unsaturated materials using ionizing radiation |
WO2017123488A1 (en) | 2016-01-13 | 2017-07-20 | 3M Innovative Properties Company | Pressure-sensitive adhesive composition and article thereof |
Also Published As
Publication number | Publication date |
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KR19990072192A (en) | 1999-09-27 |
JP3837458B2 (en) | 2006-10-25 |
BR9611919A (en) | 1999-03-30 |
MX9804624A (en) | 1998-10-31 |
EP0866810A1 (en) | 1998-09-30 |
JP2000501764A (en) | 2000-02-15 |
US5986011A (en) | 1999-11-16 |
CN1209140A (en) | 1999-02-24 |
US5637646A (en) | 1997-06-10 |
DE69619854D1 (en) | 2002-04-18 |
EP0866810B1 (en) | 2002-03-13 |
DE69619854T2 (en) | 2002-10-02 |
US5753768A (en) | 1998-05-19 |
AU7681996A (en) | 1997-07-03 |
CA2238366A1 (en) | 1997-06-19 |
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