DE69619854T2 - Radikalishe Massepolymerisation unter Verwendung eines diskontinuierlichen Reaktors - Google Patents
Radikalishe Massepolymerisation unter Verwendung eines diskontinuierlichen ReaktorsInfo
- Publication number
- DE69619854T2 DE69619854T2 DE69619854T DE69619854T DE69619854T2 DE 69619854 T2 DE69619854 T2 DE 69619854T2 DE 69619854 T DE69619854 T DE 69619854T DE 69619854 T DE69619854 T DE 69619854T DE 69619854 T2 DE69619854 T2 DE 69619854T2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- initiator
- reaction
- temperature
- polymerization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000012662 bulk polymerization Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 207
- 239000003999 initiator Substances 0.000 claims description 174
- 239000000178 monomer Substances 0.000 claims description 148
- 239000000203 mixture Substances 0.000 claims description 144
- 229920000642 polymer Polymers 0.000 claims description 125
- 238000006116 polymerization reaction Methods 0.000 claims description 100
- 238000000034 method Methods 0.000 claims description 79
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 54
- 230000008569 process Effects 0.000 claims description 49
- 238000010438 heat treatment Methods 0.000 claims description 38
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 36
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 32
- 238000010526 radical polymerization reaction Methods 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000003431 cross linking reagent Substances 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- 239000012986 chain transfer agent Substances 0.000 claims description 15
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 5
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 230000007423 decrease Effects 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002432 hydroperoxides Chemical class 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- CUXGDKOCSSIRKK-UHFFFAOYSA-N 7-methyloctyl prop-2-enoate Chemical compound CC(C)CCCCCCOC(=O)C=C CUXGDKOCSSIRKK-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000011541 reaction mixture Substances 0.000 description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 62
- 238000012360 testing method Methods 0.000 description 46
- 239000000523 sample Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- 230000001070 adhesive effect Effects 0.000 description 32
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 150000003254 radicals Chemical class 0.000 description 29
- 239000000853 adhesive Substances 0.000 description 24
- 230000001965 increasing effect Effects 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 20
- 238000009826 distribution Methods 0.000 description 18
- 238000012546 transfer Methods 0.000 description 18
- -1 unsaturated acrylate ester Chemical class 0.000 description 16
- LTYBJDPMCPTGEE-UHFFFAOYSA-N (4-benzoylphenyl) prop-2-enoate Chemical compound C1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 LTYBJDPMCPTGEE-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 13
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 13
- 238000013022 venting Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229910001220 stainless steel Inorganic materials 0.000 description 9
- 239000010935 stainless steel Substances 0.000 description 9
- 239000012943 hotmelt Substances 0.000 description 8
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000007863 gel particle Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000012644 addition polymerization Methods 0.000 description 6
- 239000012790 adhesive layer Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000012496 blank sample Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000012470 diluted sample Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 3
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004831 Hot glue Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000003926 acrylamides Chemical class 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000007720 emulsion polymerization reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000011417 postcuring Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000010557 suspension polymerization reaction Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- AQWSFUIGRSMCST-UHFFFAOYSA-N 3-pyridin-3-ylsulfonyl-5-(trifluoromethyl)chromen-2-one Chemical compound N1=CC(=CC=C1)S(=O)(=O)C=1C(OC2=CC=CC(=C2C=1)C(F)(F)F)=O AQWSFUIGRSMCST-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009529 body temperature measurement Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 239000002683 reaction inhibitor Substances 0.000 description 2
- 229920013730 reactive polymer Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- UUGXDEDGRPYWHG-UHFFFAOYSA-N (dimethylamino)methyl 2-methylprop-2-enoate Chemical compound CN(C)COC(=O)C(C)=C UUGXDEDGRPYWHG-UHFFFAOYSA-N 0.000 description 1
- POJPQMDDRCILHJ-UHFFFAOYSA-N 1,1,1,2,2,2-hexabromoethane Chemical compound BrC(Br)(Br)C(Br)(Br)Br POJPQMDDRCILHJ-UHFFFAOYSA-N 0.000 description 1
- WQIONEQXRNRAST-UHFFFAOYSA-N 1-(4-benzoylphenyl)prop-2-en-1-one Chemical compound C1=CC(C(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 WQIONEQXRNRAST-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- MZHBJMCGUSCOJN-UHFFFAOYSA-N 2-[(2-cyanocyclohexyl)diazenyl]cyclohexane-1-carbonitrile Chemical compound N#CC1CCCCC1N=NC1C(C#N)CCCC1 MZHBJMCGUSCOJN-UHFFFAOYSA-N 0.000 description 1
- MXALMAQOPWXPPY-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid Chemical compound CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O MXALMAQOPWXPPY-UHFFFAOYSA-N 0.000 description 1
- VMBCPYVGCMYCPI-UHFFFAOYSA-N 2-oxo-3-sulfanylpropanal Chemical compound SCC(=O)C=O VMBCPYVGCMYCPI-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- XKGQTCNJAXCVCL-UHFFFAOYSA-N 3-(3,5-ditert-butylphenyl)-2-hydroxybut-3-enoic acid Chemical compound CC(C)(C)C1=CC(C(=C)C(O)C(O)=O)=CC(C(C)(C)C)=C1 XKGQTCNJAXCVCL-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 229920001875 Ebonite Polymers 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MHPUGCYGQWGLJL-UHFFFAOYSA-N dimethyl pentanoic acid Natural products CC(C)CCCC(O)=O MHPUGCYGQWGLJL-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 238000007757 hot melt coating Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 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
- 230000006855 networking Effects 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007719 peel strength test Methods 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
- 239000002861 polymer material Substances 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
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000000135 prohibitive effect Effects 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
- 238000010926 purge Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 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
- 238000012421 spiking Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent 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)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/572,310 US5637646A (en) | 1995-12-14 | 1995-12-14 | Bulk radical polymerization using a batch reactor |
| PCT/US1996/018503 WO1997021736A1 (en) | 1995-12-14 | 1996-11-12 | Bulk radical polymerization using a batch reactor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69619854D1 DE69619854D1 (de) | 2002-04-18 |
| DE69619854T2 true DE69619854T2 (de) | 2002-10-02 |
Family
ID=24287257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69619854T Expired - Lifetime DE69619854T2 (de) | 1995-12-14 | 1996-11-12 | Radikalishe Massepolymerisation unter Verwendung eines diskontinuierlichen Reaktors |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US5637646A (enExample) |
| EP (1) | EP0866810B1 (enExample) |
| JP (1) | JP3837458B2 (enExample) |
| KR (1) | KR19990072192A (enExample) |
| CN (1) | CN1209140A (enExample) |
| AU (1) | AU7681996A (enExample) |
| BR (1) | BR9611919A (enExample) |
| CA (1) | CA2238366A1 (enExample) |
| DE (1) | DE69619854T2 (enExample) |
| WO (1) | WO1997021736A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10153966B4 (de) * | 2001-05-09 | 2005-05-12 | List Ag | Verfahren zur Durchführung von Polymerisationsreaktionen |
Families Citing this family (212)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637646A (en) * | 1995-12-14 | 1997-06-10 | Minnesota Mining And Manufacturing Company | Bulk radical polymerization using a batch reactor |
| US6274688B1 (en) * | 1997-07-28 | 2001-08-14 | Kaneka Corporation | Functional groups-terminated vinyl polymers |
| US6171985B1 (en) | 1997-12-01 | 2001-01-09 | 3M Innovative Properties Company | Low trauma adhesive article |
| US6083856A (en) * | 1997-12-01 | 2000-07-04 | 3M Innovative Properties Company | Acrylate copolymeric fibers |
| US6102039A (en) * | 1997-12-01 | 2000-08-15 | 3M Innovative Properties Company | Molded respirator containing sorbent particles |
| US6133173A (en) * | 1997-12-01 | 2000-10-17 | 3M Innovative Properties Company | Nonwoven cohesive wrap |
| US6107222A (en) * | 1997-12-01 | 2000-08-22 | 3M Innovative Properties Company | Repositionable sheets with a nonwoven web of pressure-sensitive adhesive fibers |
| US6720387B1 (en) | 1998-02-18 | 2004-04-13 | 3M Innovative Properties Company | Hot-melt adhesive compositions comprising acidic polymer and basic polymer blends |
| US6103152A (en) | 1998-07-31 | 2000-08-15 | 3M Innovative Properties Co. | Articles that include a polymer foam and method for preparing same |
| US6198016B1 (en) | 1998-12-01 | 2001-03-06 | 3M Innovative Properties Company | Wet skin adhesive article |
| US6280822B1 (en) | 1999-01-11 | 2001-08-28 | 3M Innovative Properties Company | Cube corner cavity based retroeflectors with transparent fill material |
| US6855386B1 (en) | 1999-03-19 | 2005-02-15 | 3M Innovative Properties Company | Wet surface adhesives |
| US6624273B1 (en) | 1999-03-19 | 2003-09-23 | 3M Innovative Properties Company | Plasticized acrylics for pressure sensitive adhesive applications |
| US6232366B1 (en) | 1999-06-09 | 2001-05-15 | 3M Innovative Properties Company | Pressure sensitive conductive adhesive having hot-melt properties and biomedical electrodes using same |
| US6441114B1 (en) | 1999-06-11 | 2002-08-27 | 3M Innovative Properties Company | Adhesives for use on fluorine-containing or polycarbonate surfaces |
| DE69932952T2 (de) | 1999-06-18 | 2007-04-26 | 3M Innovative Properties Co., St. Paul | Faservliese, klebstoffartikel und herstellungsverfahren |
| US6441092B1 (en) | 1999-06-18 | 2002-08-27 | 3M Innovative Properties Company | Wet-stick adhesives |
| US6518343B1 (en) | 1999-06-18 | 2003-02-11 | 3M Innovative Properties Company | Wet-stick adhesives, articles, and methods |
| US6403703B1 (en) | 1999-08-27 | 2002-06-11 | Rohm And Haas Company | Polymeric compositions from acrylic and unsaturated carboxyl monomers |
| US6656307B2 (en) | 1999-11-24 | 2003-12-02 | 3M Innovative Properties Company | Method of making signs having metalized cube corner sheeting |
| AU4458000A (en) | 1999-12-20 | 2001-07-03 | 3M Innovative Properties Company | Acidic polymer-based thermosettable psas, methods of their use, and thermoset adhesives therefrom |
| US6340719B1 (en) | 1999-12-29 | 2002-01-22 | 3M-Innovative Properties Company | Crosslinking process |
| US6379791B1 (en) | 2000-02-08 | 2002-04-30 | 3M Innovative Properties Company | Compatibilized pressure-sensitive adhesives |
| US6503621B1 (en) | 2000-02-08 | 2003-01-07 | 3M Innovative Properties Company | Pressure sensitive adhesives and articles including radial block and acrylic polymers |
| EP1130605A1 (de) * | 2000-03-01 | 2001-09-05 | Wermelinger AG | Verfahren zur Herstellung eines Hochspannungsverbundisolators, Hochspannungsisolator sowie Kunststoff zur Verwendung in dem Verfahren, und Verfahren zur Herstellung eines nicht-zylindrischen Bauteils |
| US6497949B1 (en) | 2000-08-11 | 2002-12-24 | 3M Innovative Properties Company | Adhesive blends comprising hydrophilic and hydrophobic pressure sensitive adhesives |
| US6435873B1 (en) | 2000-10-10 | 2002-08-20 | 3M Innovative Properties Company | Medication delivery devices |
| KR100394365B1 (ko) * | 2000-10-18 | 2003-08-09 | (주) 고려물산 | 유화제가 첨가되지 않는 점착제 및 그 제조방법 |
| US6883908B2 (en) | 2001-01-08 | 2005-04-26 | 3M Innovative Properties Company | Methods and compositions for ink jet printing of pressure sensitive adhesive patterns or films on a wide range of substrates |
| US7078582B2 (en) | 2001-01-17 | 2006-07-18 | 3M Innovative Properties Company | Stretch removable adhesive articles and methods |
| US6894204B2 (en) | 2001-05-02 | 2005-05-17 | 3M Innovative Properties Company | Tapered stretch removable adhesive articles and methods |
| EP1424972A1 (en) * | 2001-09-14 | 2004-06-09 | 3M Innovative Properties Company | Non-contact printing method for making a medical pressure sensitive adhesive article |
| US8323773B2 (en) | 2001-10-09 | 2012-12-04 | 3M Innovative Properties Company | Laminates with structured layers |
| US6893655B2 (en) | 2001-10-09 | 2005-05-17 | 3M Innovative Properties Co. | Transdermal delivery devices |
| US20030118970A1 (en) | 2001-12-21 | 2003-06-26 | 3M Innovative Properties Company | Removable dental models |
| KR20050092033A (ko) * | 2003-01-04 | 2005-09-16 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 차량 배터리 팩 단열체 |
| US7927703B2 (en) * | 2003-04-11 | 2011-04-19 | 3M Innovative Properties Company | Adhesive blends, articles, and methods |
| US6864322B2 (en) | 2003-06-20 | 2005-03-08 | 3M Innovative Properties Company | Linerless double-sided pressure sensitive adhesive tape |
| US7691437B2 (en) * | 2003-10-31 | 2010-04-06 | 3M Innovative Properties Company | Method for preparing a pressure-sensitive adhesive |
| TW200535205A (en) * | 2003-11-13 | 2005-11-01 | Lg Chemical Ltd | Adhesives having advanced flame-retardant property |
| JP2005146212A (ja) * | 2003-11-19 | 2005-06-09 | Three M Innovative Properties Co | 片面粘着テープ |
| US20050287362A1 (en) * | 2004-06-23 | 2005-12-29 | 3M Innovative Properties Company | Halogen free tapes & method of making same |
| US20050287361A1 (en) * | 2004-06-23 | 2005-12-29 | 3M Innovative Properties Company | Halogen free tapes & method of making same |
| US20050287360A1 (en) * | 2004-06-23 | 2005-12-29 | 3M Innovative Properties Company | Halogen free tapes & method of making same |
| US7252855B2 (en) * | 2004-08-18 | 2007-08-07 | 3M Innovative Properties Company | Method and apparatus for making an adhesive cleaning sheet |
| US7291359B2 (en) * | 2004-08-18 | 2007-11-06 | 3M Innovative Properties Company | Method and apparatus for making an adhesive cleaning sheet |
| US20060127463A1 (en) * | 2004-12-15 | 2006-06-15 | Nugara Peter N | Composite structure including a low vinyl acetate layer |
| US20060138693A1 (en) * | 2004-12-29 | 2006-06-29 | Tuman Scott J | Method and apparatus for making a cleaning sheet |
| US7329839B2 (en) * | 2005-04-25 | 2008-02-12 | Palmer Jeffery W | Cover for a candle warmer |
| US7442438B2 (en) * | 2005-05-04 | 2008-10-28 | 3M Innovative Properties Company | Wet and dry stick adhesive, articles, and methods |
| JP4890800B2 (ja) * | 2005-06-29 | 2012-03-07 | スリーエム イノベイティブ プロパティズ カンパニー | 透明波長選択性再帰反射体 |
| US7989573B2 (en) * | 2005-12-16 | 2011-08-02 | 3M Innovative Properties Company | Method of free radically polymerizing vinyl monomers |
| US20070136967A1 (en) * | 2005-12-20 | 2007-06-21 | 3M Innovative Properties Company | Adhesive wipe |
| US7968661B2 (en) * | 2005-12-28 | 2011-06-28 | 3M Innovative Properties Company | Method of free radically polymerizing vinyl monomers |
| CN101309935A (zh) * | 2006-01-24 | 2008-11-19 | 居间胶带聚合物公司 | 在行星式辊筒挤出机内连续本体聚合 |
| 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 |
| US20070191506A1 (en) * | 2006-02-13 | 2007-08-16 | 3M Innovative Properties Company | Curable compositions for optical articles |
| US7463417B2 (en) | 2006-02-13 | 2008-12-09 | 3M Innovative Properties Company | Optical articles from curable compositions |
| ATE516877T1 (de) * | 2006-08-30 | 2011-08-15 | Intertape Polymer Corp | Massenpolymerisierungsverfahren für einen rückführungskreislaufreaktor |
| US20080071056A1 (en) * | 2006-09-14 | 2008-03-20 | Borst Joseph P | Method of forming a graft polyol and polyurethane article formed from the graft polyol |
| US7385020B2 (en) * | 2006-10-13 | 2008-06-10 | 3M Innovative Properties Company | 2-octyl (meth)acrylate adhesive composition |
| EP2079812B1 (en) * | 2006-11-07 | 2017-09-13 | Henkel AG & Co. KGaA | Acrylic hot melt adhesives |
| WO2008115811A2 (en) * | 2007-03-16 | 2008-09-25 | Endo Pharmaceuticals, Inc. | Transdermal delivery form disposal systems and methods |
| US7947366B2 (en) * | 2007-03-19 | 2011-05-24 | 3M Innovative Properties Company | Adhesive sheet article |
| US8334037B2 (en) | 2007-05-11 | 2012-12-18 | 3M Innovative Properties Company | Multi-layer assembly, multi-layer stretch releasing pressure-sensitive adhesive assembly, and methods of making and using the same |
| US20090105437A1 (en) * | 2007-10-19 | 2009-04-23 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US8378046B2 (en) | 2007-10-19 | 2013-02-19 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| KR101545365B1 (ko) * | 2007-10-30 | 2015-08-18 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 고 굴절률 접착제 |
| CN101910340B (zh) | 2007-11-08 | 2013-04-24 | 3M创新有限公司 | 具有漫射性质的光学粘合剂 |
| CN102057006B (zh) * | 2008-06-09 | 2013-06-19 | 3M创新有限公司 | 具有氮丙啶交联剂的丙烯酸类压敏粘合剂 |
| CN102137908B (zh) * | 2008-07-28 | 2013-10-30 | 陶氏康宁公司 | 复合制品 |
| KR20110055730A (ko) * | 2008-09-17 | 2011-05-25 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 확산 특성을 갖는 광학 접착제 |
| US8765217B2 (en) | 2008-11-04 | 2014-07-01 | Entrotech, Inc. | Method for continuous production of (meth)acrylate syrup and adhesives therefrom |
| US7838110B2 (en) * | 2008-12-02 | 2010-11-23 | 3M Innovative Properties Company | Aziridine-functional photoactive crosslinking compounds |
| CN102300888B (zh) * | 2008-12-17 | 2014-09-17 | 3M创新有限公司 | 含有机硅的共聚物的本体聚合 |
| EP2226369A1 (en) | 2009-03-05 | 2010-09-08 | 3M Innovative Properties Company | Adhesive article comprising an acrylic foam layer |
| US8329079B2 (en) | 2009-04-20 | 2012-12-11 | Entrochem, Inc. | Method and apparatus for continuous production of partially polymerized compositions and polymers therefrom |
| US8489201B2 (en) | 2009-06-09 | 2013-07-16 | Regear Life Sciences, Inc. | Shielded diathermy applicator with automatic tuning and low incidental radiation |
| WO2010147822A1 (en) * | 2009-06-16 | 2010-12-23 | 3M Innovative Properties Company | Debondable adhesive article |
| CN102803363B (zh) | 2009-06-18 | 2014-12-24 | 3M创新有限公司 | 制备热熔性压敏粘合剂的方法 |
| JP5781075B2 (ja) | 2009-08-28 | 2015-09-16 | スリーエム イノベイティブ プロパティズ カンパニー | 多官能性カチオンを含む重合性イオン性液体及び静電気防止コーティング |
| US8816029B2 (en) | 2009-08-28 | 2014-08-26 | 3M Innovative Properties Company | Compositions and articles comprising polymerizable ionic liquid mixture, and methods of curing |
| US8148471B2 (en) * | 2009-11-23 | 2012-04-03 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with aziridinyl-epoxy crosslinking system |
| CN102648259B (zh) | 2009-12-08 | 2015-04-29 | 3M创新有限公司 | 光漫射粘合剂及其制备方法 |
| WO2011087621A2 (en) | 2009-12-22 | 2011-07-21 | 3M Innovative Properties Company | Curable dental compositions and articles comprising polymerizable ionic liquids |
| CN102108133B (zh) * | 2009-12-23 | 2014-12-10 | 3M创新有限公司 | (甲基)丙烯酰基-氮丙啶交联剂和粘合剂聚合物 |
| CN102127183B (zh) | 2010-01-20 | 2014-08-20 | 3M创新有限公司 | 可交联的丙烯酸酯粘合剂聚合物组合物 |
| EP2889625B1 (en) * | 2010-03-03 | 2016-09-14 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
| CN102792218B (zh) | 2010-03-09 | 2016-02-03 | 3M创新有限公司 | 用于粘合显示面板的热活化光学透明粘合剂 |
| US8137807B2 (en) * | 2010-03-26 | 2012-03-20 | 3M Innovative Properties Company | Pressure-sensitive adhesives derived from 2-alkyl alkanols |
| JP6177126B2 (ja) | 2010-05-18 | 2017-08-09 | スリーエム イノベイティブ プロパティズ カンパニー | 重合性イオン液体組成物 |
| EP2588514B1 (en) | 2010-06-29 | 2015-03-18 | 3M Innovative Properties Company | Grafted compounds formed from aziridinyl-containing compounds |
| CN102985449B (zh) | 2010-06-29 | 2015-08-12 | 3M创新有限公司 | 含氮丙啶基的化合物 |
| KR101866588B1 (ko) | 2010-06-30 | 2018-06-11 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | (메트)아크릴로일 감압 폼 접착제 |
| ES2428722T3 (es) | 2010-09-03 | 2013-11-11 | 3M Innovative Properties Company | Método para aplicar una tira alargada al marco de la puerta de un vehículo |
| KR101772730B1 (ko) | 2010-12-13 | 2017-08-29 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 그래프팅된 공중합체와 폴리아미드의 블렌드 |
| WO2012082487A2 (en) | 2010-12-14 | 2012-06-21 | 3M Innovative Properties Company | Oxazolinyl-containing polymers and grafted compounds prepared from the oxazolinyl-containing polymers |
| CN103237824B (zh) | 2010-12-21 | 2015-07-22 | 3M创新有限公司 | 衍生自仲烷基(甲基)丙烯酸酯的聚合物 |
| WO2012162041A2 (en) | 2011-05-20 | 2012-11-29 | 3M Innovative Properties Company | Laser-personalizable security articles |
| EP2710519B1 (en) | 2011-05-20 | 2019-07-17 | Gemalto SA | Laser-personalized security articles |
| US8785517B2 (en) | 2011-05-25 | 2014-07-22 | 3M Innovative Properties Company | Pressure-sensitive adhesives with onium-epdxy crosslinking system |
| WO2012177337A1 (en) | 2011-06-23 | 2012-12-27 | 3M Innovative Properties Company | Pressure-sensitive adhesives with onium-epoxy resin crosslinking system |
| JP6062938B2 (ja) | 2011-07-19 | 2017-01-18 | スリーエム イノベイティブ プロパティズ カンパニー | 熱剥離可能な接着剤物品並びにその製造方法及び使用方法 |
| EP2756019B1 (en) | 2011-09-12 | 2019-04-10 | Basf Se | Graft polyol and method of forming the same |
| EP2573150A1 (en) | 2011-09-26 | 2013-03-27 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive films with pressure-sensitive adhesives comprising (meth)acrylate esters of 2-alkyl alkanols |
| CN103030720B (zh) * | 2011-09-30 | 2015-02-11 | 中国石油化工股份有限公司 | 一种间歇液相本体法生产聚丙烯的设备和方法 |
| EP2764066A4 (en) | 2011-10-05 | 2015-05-27 | 3M Innovative Properties Co | MICROSTRUCTURED TRANSFER BELTS |
| TWI588226B (zh) | 2011-10-19 | 2017-06-21 | ３Ｍ新設資產公司 | 具有薄熔體塗覆之物件及彼等之製造方法 |
| JP6223989B2 (ja) | 2011-11-18 | 2017-11-01 | スリーエム イノベイティブ プロパティズ カンパニー | 感圧性接着剤組成物 |
| WO2013130238A1 (en) | 2012-02-29 | 2013-09-06 | 3M Innovative Properties Company | Photobase generators as latent ionic crosslinkers for acrylic pressure-sensitive adhesives |
| US9217050B2 (en) | 2012-04-03 | 2015-12-22 | 3M Innovative Properties Company | Crosslinkable composition comprising photobase generators |
| CN107641486B (zh) | 2012-11-16 | 2021-04-02 | 3M创新有限公司 | 包含(甲基)丙烯酰基侧基的粘合剂、制品和方法 |
| CN104797673B (zh) * | 2012-11-19 | 2016-10-19 | 3M创新有限公司 | 可交联组合物和交联组合物 |
| BR112015014099A2 (pt) | 2012-12-14 | 2017-07-11 | 3M Innovative Properties Co | método de fabricação de composições viscoelásticas embaladas pela polimerização de materiais etilenicamente insaturados com o uso de radiação ionizante |
| KR102213696B1 (ko) | 2012-12-14 | 2021-02-08 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 이온화 방사선을 사용하여 에틸렌계 불포화 재료를 중합하는 방법 |
| EP2746356B1 (en) | 2012-12-19 | 2018-03-14 | 3M Innovative Properties Company | Adhesive tape roll, its method of manufacture and its use for making weatherseal strips |
| JP6632378B2 (ja) | 2012-12-20 | 2020-01-22 | スリーエム イノベイティブ プロパティズ カンパニー | 紫外線吸収基を有するオリゴマーを含むフルオロポリマー組成物 |
| JP6162959B2 (ja) * | 2013-01-16 | 2017-07-12 | 花王株式会社 | 非イオン性ポリマー |
| US20150368524A1 (en) | 2013-03-13 | 2015-12-24 | 3M Innovative Properties Company | Adhesives comprising epoxy-acid crosslinked groups and methods |
| US9908837B2 (en) | 2013-03-15 | 2018-03-06 | 3M Innovative Properties Company | Method for preparing (meth)acrylates of biobased alcohols and polymers thereof |
| BR112015023718B1 (pt) | 2013-03-15 | 2020-10-13 | 3M Innovative Properties Company | método para produzir acrilato de 2-octila e método de fabricação de um adesivo |
| WO2014143690A1 (en) | 2013-03-15 | 2014-09-18 | 3M Innovative Properties Company | Method for preparing (meth)acrylates of biobased alcohols and polymers thereof |
| CN103145910B (zh) * | 2013-03-27 | 2014-09-17 | 苏州双象光学材料有限公司 | 双引发聚合pmma的生产工艺 |
| CN105247003B (zh) | 2013-05-14 | 2017-03-29 | 3M创新有限公司 | 粘合剂组合物 |
| EP2803712A1 (en) | 2013-05-17 | 2014-11-19 | 3M Innovative Properties Company | Multilayer Pressure Sensitive Adhesive Assembly |
| EP2818348B1 (en) | 2013-06-24 | 2018-11-07 | 3M Innovative Properties Company | Taped seal construction |
| JP6478988B2 (ja) | 2013-06-25 | 2019-03-06 | スリーエム イノベイティブ プロパティズ カンパニー | 湿気硬化性組成物、使用法、及び複合物品 |
| US20150083341A1 (en) | 2013-09-25 | 2015-03-26 | 3M Innovative Properties Company | Heat detachable adhesive constructions, articles made therefrom and method of use thereof |
| EP3077428B1 (en) | 2013-12-04 | 2020-09-16 | 3M Innovative Properties Company | Optically clear high refractive index adhesives |
| CN105916885A (zh) | 2014-01-17 | 2016-08-31 | 3M创新有限公司 | 自润湿粘合剂乳液组合物 |
| WO2015153987A1 (en) | 2014-04-04 | 2015-10-08 | 3M Innovative Properties Company | Wet and dry surface adhesives |
| WO2015183782A1 (en) | 2014-05-29 | 2015-12-03 | 3M Innovative Properties Company | Acrylic adhesive composition with controlled molecular weight |
| KR20150144433A (ko) | 2014-06-16 | 2015-12-28 | 한경대학교 산학협력단 | 전처리된 순환골재를 이용하여 수용액 상에서 중금속을 제거하는 방법 |
| US11110689B2 (en) | 2014-06-25 | 2021-09-07 | 3M Innovative Properties Company | Pressure sensitive adhesive composition including ultraviolet light-absorbing oligomer |
| JP6294513B2 (ja) | 2014-06-25 | 2018-03-14 | スリーエム イノベイティブ プロパティズ カンパニー | 少なくとも１つのオリゴマーを含むフルオロポリマー組成物 |
| WO2016093206A1 (ja) * | 2014-12-09 | 2016-06-16 | 積水フーラー株式会社 | 紫外線硬化型ポリマー及びこれを含む紫外線硬化型ホットメルト粘着剤 |
| US10414954B2 (en) | 2014-12-30 | 2019-09-17 | 3M Innovative Properties Company | Water-based pressure-sensitive adhesive compositions |
| US9890301B2 (en) | 2014-12-30 | 2018-02-13 | 3M Innovative Properties Company | Water-based pressure-sensitive adhesive compositions |
| JP6258565B1 (ja) | 2014-12-30 | 2018-01-10 | スリーエム イノベイティブ プロパティズ カンパニー | 水性感圧接着剤組成物 |
| EP3259290B1 (en) | 2015-02-18 | 2018-12-12 | 3M Innovative Properties Company | Acrylic adhesive composition from protected photocrosslinking agents |
| US10920116B2 (en) | 2015-04-13 | 2021-02-16 | 3M Innovative Properties Company | Method of preparing crosslinked pressure-sensitive adhesives using a light-emitting diode for crosslinking |
| CN107683313B (zh) | 2015-06-03 | 2021-02-05 | 3M创新有限公司 | 用于柔性显示器的组件层 |
| CN108064202B (zh) | 2015-06-03 | 2020-09-25 | 3M创新有限公司 | 基于丙烯酸的柔性组件层 |
| CN107709497B (zh) | 2015-06-04 | 2020-07-17 | 3M创新有限公司 | 可uv固化的环氧/丙烯酸酯粘合剂组合物 |
| EP3313906B1 (en) | 2015-06-25 | 2020-08-05 | 3M Innovative Properties Company | Copolymer including ultraviolet light-absorbing group and compositions including the same |
| KR20180035926A (ko) | 2015-08-31 | 2018-04-06 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 습윤 표면에 대한 접착력이 향상된 (메트)아크릴레이트 감압 접착제를 포함하는 물품 |
| JP6875378B2 (ja) | 2015-08-31 | 2021-05-26 | スリーエム イノベイティブ プロパティズ カンパニー | 湿潤表面に対する接着力が高められた（メタ）アクリレート感圧接着剤を含む陰圧閉鎖創傷療法被覆材 |
| US10941321B2 (en) | 2015-09-30 | 2021-03-09 | 3M Innovative Properties Company | Curable and cured adhesive compositions |
| EP3156465A1 (en) | 2015-10-15 | 2017-04-19 | 3M Innovative Properties Company | Multilayer pressure sensitive adhesive foam tape for outdooor applications |
| EP3156466B1 (en) | 2015-10-15 | 2020-11-25 | 3M Innovative Properties Company | Multilayer pressure sensitive adhesive foam tape for outdooor applications |
| WO2017087170A1 (en) | 2015-11-18 | 2017-05-26 | 3M Innovative Properties Company | Copolymeric stabilizing carrier fluid for nanoparticles |
| US10232078B2 (en) | 2015-12-22 | 2019-03-19 | 3M Innovative Properties Company | Curable polymeric materials and methods of using same |
| JP6847956B2 (ja) | 2015-12-22 | 2021-03-24 | スリーエム イノベイティブ プロパティズ カンパニー | オキサレートエステル−ポリアミン熱硬化性組成物 |
| US9701875B1 (en) | 2015-12-28 | 2017-07-11 | 3M Innovative Properties Company | Adhesive compositions and articles, and methods of making and using the same |
| CN105505263B (zh) | 2016-01-13 | 2017-12-05 | 3M创新有限公司 | 压敏胶组合物及其制品 |
| US10899961B2 (en) | 2016-02-17 | 2021-01-26 | 3M Innovative Properties Company | Quantum dots with stabilizing fluorochemical copolymers |
| US10947423B2 (en) | 2016-03-10 | 2021-03-16 | 3M Innovative Properties Company | Oil resistant adhesive |
| EP3478666B1 (en) | 2016-06-29 | 2020-07-29 | 3M Innovative Properties Company | Polymerizable ionic liquid compositions |
| EP3497175B1 (en) | 2016-08-12 | 2022-05-04 | 3M Innovative Properties Company | Wet and dry surface adhesives |
| TWI610991B (zh) * | 2016-08-26 | 2018-01-11 | 長興材料工業股份有限公司 | 可熱聚合的組成物以及由此形成之組成液 |
| WO2018075275A1 (en) | 2016-10-20 | 2018-04-26 | 3M Innovative Properties Company | Photoinitiators with protected carbonyl group |
| CN109890927B (zh) | 2016-10-26 | 2021-09-24 | 3M创新有限公司 | 可交联组合物和交联组合物 |
| US11492515B2 (en) | 2016-12-02 | 2022-11-08 | 3M Innovative Properties Company | Low dielectric optically clear adhesives for flexible electronic display |
| KR102492572B1 (ko) | 2016-12-02 | 2023-01-30 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 다층 접착 물품 |
| EP3336153B1 (en) | 2016-12-19 | 2020-11-25 | 3M Innovative Properties Company | Rubber-based multilayer pressure-sensitive adhesive assembly having low voc characteristics |
| EP3555222B1 (en) | 2016-12-19 | 2023-03-29 | 3M Innovative Properties Company | Adhesive compositions and articles |
| EP3336154B1 (en) | 2016-12-19 | 2020-05-20 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive assembly having low voc characteristics |
| US20190352544A1 (en) | 2016-12-22 | 2019-11-21 | 3M Innovative Properties Company | Phase separated pressure-sensitive adhesive compositions |
| EP3388457B1 (en) | 2017-04-13 | 2020-01-15 | 3M Innovative Properties Company | Pressure-sensitive adhesive compositions |
| KR102528806B1 (ko) | 2017-05-12 | 2023-05-03 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 접착 테이프 |
| TWI786141B (zh) | 2017-06-30 | 2022-12-11 | 美商3M新設資產公司 | 可印刷可固化混合物及經固化組成物 |
| CN110799613A (zh) | 2017-06-30 | 2020-02-14 | 3M创新有限公司 | 干湿表面粘合剂 |
| JP6347341B1 (ja) * | 2017-08-09 | 2018-06-27 | 積水フーラー株式会社 | 紫外線硬化型アクリル系ポリマー及びその製造方法並びに紫外線硬化型ホットメルト接着剤 |
| US12104094B2 (en) | 2017-12-18 | 2024-10-01 | 3M Innovative Properties Company | Phenolic resin composition comprising polymerized ionic groups, abrasive articles and methods |
| EP3728504B1 (en) | 2017-12-21 | 2022-01-26 | 3M Innovative Properties Company | Adhesive articles including a cushion layer and a continuous shell layer |
| WO2019123181A1 (en) | 2017-12-21 | 2019-06-27 | 3M Innovative Properties Company | Adhesive articles including a cushion layer and a discontinuous shell layer |
| US11661536B2 (en) | 2018-02-28 | 2023-05-30 | 3M Innovative Properties Company | Adhesives comprising polymerized units of secondary hexyl (meth)acrylates |
| WO2019193514A1 (en) | 2018-04-05 | 2019-10-10 | 3M Innovative Properties Company | Gel adhesive comprising crosslinked blend of polydiorganosiloxane and acrylic polymer |
| EP3569669A1 (en) | 2018-05-14 | 2019-11-20 | 3M Innovative Properties Company | Method of manufacturing an electronic control device |
| EP3569622B1 (en) | 2018-05-14 | 2021-01-06 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive assembly |
| CN112218927A (zh) | 2018-06-01 | 2021-01-12 | 3M创新有限公司 | 丙烯酸-环氧树脂粘合剂组合物 |
| JP2021534308A (ja) | 2018-08-22 | 2021-12-09 | スリーエム イノベイティブ プロパティズ カンパニー | 感圧接着剤用硬化性組成物 |
| EP3613820A1 (en) | 2018-08-24 | 2020-02-26 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive assembly |
| CN113227286A (zh) | 2018-12-27 | 2021-08-06 | 3M创新有限公司 | 多层粘合剂和制品 |
| CN111548739B (zh) * | 2019-02-11 | 2022-03-01 | 3M创新有限公司 | 紫外光固化胶粘剂 |
| EP3715432A1 (en) | 2019-03-27 | 2020-09-30 | 3M Innovative Properties Company | Pressure-sensitive adhesive composition with transparency characteristics |
| EP3983458B1 (en) | 2019-06-14 | 2024-08-21 | 3M Innovative Properties Company | Polymers derived from a (meth)acrylate macromer, adhesive compositions, and articles |
| WO2021028795A1 (en) | 2019-08-15 | 2021-02-18 | 3M Innovative Properties Company | Core-sheath filament with a thermally conductive pressure-sensitive adhesive core |
| CN114269974A (zh) | 2019-08-19 | 2022-04-01 | 3M创新有限公司 | 包含可交联和交联粘合剂组合物的皮芯长丝及其打印方法 |
| CN114341291A (zh) | 2019-09-09 | 2022-04-12 | 3M创新有限公司 | 共挤出聚合物粘合剂制品 |
| MX2022003731A (es) | 2019-10-16 | 2022-05-02 | Basf Coatings Gmbh | Polimerizacion radicalica controlada superavanzada. |
| EP4061901A1 (en) | 2019-11-20 | 2022-09-28 | 3M Innovative Properties Company | Medical tapes with high optical clarity when over-taped |
| CN114729250A (zh) | 2019-11-21 | 2022-07-08 | 3M创新有限公司 | 可交联和经交联组合物 |
| JP7300982B2 (ja) * | 2019-12-26 | 2023-06-30 | 三井住友建設株式会社 | コンクリートの発熱特性試験装置及び発熱特性試験方法 |
| EP3885419A1 (en) | 2020-03-23 | 2021-09-29 | 3M Innovative Properties Company | Pressure sensitive adhesive having low voc characteristics |
| EP3970965A1 (en) | 2020-09-17 | 2022-03-23 | 3M Innovative Properties Company | Multilayer construction with damping properties |
| EP3992232A1 (en) | 2020-10-30 | 2022-05-04 | 3M Innovative Properties Company | Foamable precursor of a microcellular foamed polymeric composition |
| WO2022096967A1 (en) | 2020-11-03 | 2022-05-12 | 3M Innovative Properties Company | Crosslinkable and crosslinked compositions |
| EP4086322A1 (en) | 2021-05-06 | 2022-11-09 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive foam tape |
| KR20240008840A (ko) | 2021-05-18 | 2024-01-19 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 가교결합성 조성물 |
| JP2024522538A (ja) | 2021-06-04 | 2024-06-21 | スリーエム イノベイティブ プロパティズ カンパニー | オンデマンド剥離挙動を示す接着剤組成物を含有する物品 |
| CN113527557B (zh) * | 2021-08-30 | 2022-07-12 | 天能化工有限公司 | 一种氯乙烯单体悬浮聚合等温水平行入料的方法 |
| US20260152674A1 (en) | 2021-11-11 | 2026-06-04 | Solventum Intellectual Properties Company | Adhesives for Wet or Dry Adhesion |
| EP4448669A1 (en) | 2021-12-16 | 2024-10-23 | 3M Innovative Properties Company | Adhesive film, adhesive system, and related processes |
| CN119790116A (zh) | 2022-08-29 | 2025-04-08 | 3M创新有限公司 | 包含聚合酰胺单体的压敏粘合剂组合物、制品和方法 |
| EP4594378A1 (en) * | 2022-11-18 | 2025-08-06 | Avery Dennison Corporation | Architectured polymers and related methods |
| CN121464194A (zh) | 2023-07-12 | 2026-02-03 | 舒万诺知识产权公司 | 封装压敏粘合剂 |
| EP4780905A1 (en) | 2023-09-20 | 2026-07-29 | 3M Innovative Properties Company | Patterned adhesive |
| WO2025191374A1 (en) | 2024-03-14 | 2025-09-18 | Solventum Intellectual Properties Company | Adhesive articles including a metal layer |
| WO2025229502A1 (en) | 2024-04-29 | 2025-11-06 | 3M Innovative Properties Company | Curable compositions, cured compositions, and related method |
| WO2026022641A1 (en) | 2024-07-26 | 2026-01-29 | 3M Innovative Properties Company | Multilayer optically clear adhesive |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE513431A (enExample) * | 1951-09-10 | |||
| NL127637C (enExample) * | 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 (de) * | 1976-03-29 | 1980-08-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von schlagfest modifizierten Styrolpolymerisaten |
| US4130700A (en) * | 1977-01-06 | 1978-12-19 | Pennwalt Corporation | Polymerization process using diperoxy ketals as finishing catalysts |
| AT356380B (de) * | 1977-11-17 | 1980-04-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von polymerisaten durch radikalisch initiierte substanzpoly- merisation |
| DE2839563A1 (de) * | 1978-09-12 | 1980-03-27 | Hoechst Ag | Verfahren zur kontinuierlichen massepolymerisation von alkenylaromaten |
| IT1198338B (it) * | 1980-07-02 | 1988-12-21 | Montedison Spa | Processo per produrre copolimeri di monomeri vinil-aromatici con nitrili etilenicamente insaturi |
| JPS5887171A (ja) * | 1981-11-18 | 1983-05-24 | Sekisui Chem Co Ltd | アクリル系感圧性接着剤の製造方法 |
| US4530979A (en) * | 1983-06-15 | 1985-07-23 | The Dow Company | Continuous polymerization of water-miscible polymers |
| US4843134A (en) * | 1984-03-28 | 1989-06-27 | Minnesota Mining And Manufacturing Company | Acrylate pressure-sensitive adhesives containing insolubles |
| US4619979A (en) * | 1984-03-28 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Continuous free radial polymerization in a wiped-surface reactor |
| 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 |
| DE4038625A1 (de) * | 1990-12-04 | 1992-06-11 | Basf Ag | Substanz- und suspensionspolymerisate auf der basis von methylmethacrylat |
| JP3174337B2 (ja) * | 1992-02-10 | 2001-06-11 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | 放射線架橋型エラストマー |
| 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 (de) * | 1992-10-23 | 1994-05-05 | Basf Ag | Verfahren zur Entfernung von flüchtigen Bestandteilen aus Polymeren |
| DE4235785A1 (de) * | 1992-10-23 | 1994-05-11 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Polymerisation |
| US5373074A (en) * | 1993-02-12 | 1994-12-13 | Isp Investments Inc. | Free radical solution polymerization of vinylpyrrolidone |
| JPH06239905A (ja) * | 1993-02-15 | 1994-08-30 | Mitsubishi Rayon Co Ltd | メタクリル系板状重合体の製造方法 |
| 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 |
| 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 JP JP52204497A patent/JP3837458B2/ja not_active Expired - Lifetime
- 1996-11-12 EP EP96939732A patent/EP0866810B1/en not_active Expired - Lifetime
- 1996-11-12 WO PCT/US1996/018503 patent/WO1997021736A1/en not_active Ceased
- 1996-11-12 KR KR1019980704557A patent/KR19990072192A/ko not_active Ceased
- 1996-11-12 CN CN96199944A patent/CN1209140A/zh active Pending
- 1996-11-12 CA CA002238366A patent/CA2238366A1/en not_active Abandoned
- 1996-11-12 DE DE69619854T patent/DE69619854T2/de not_active Expired - Lifetime
- 1996-11-12 BR BR9611919A patent/BR9611919A/pt not_active Application Discontinuation
- 1996-11-12 AU AU76819/96A patent/AU7681996A/en not_active Abandoned
-
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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10153966B4 (de) * | 2001-05-09 | 2005-05-12 | List Ag | Verfahren zur Durchführung von Polymerisationsreaktionen |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0866810A1 (en) | 1998-09-30 |
| MX9804624A (es) | 1998-10-31 |
| US5986011A (en) | 1999-11-16 |
| DE69619854D1 (de) | 2002-04-18 |
| US5753768A (en) | 1998-05-19 |
| WO1997021736A1 (en) | 1997-06-19 |
| AU7681996A (en) | 1997-07-03 |
| EP0866810B1 (en) | 2002-03-13 |
| US5637646A (en) | 1997-06-10 |
| BR9611919A (pt) | 1999-03-30 |
| JP2000501764A (ja) | 2000-02-15 |
| KR19990072192A (ko) | 1999-09-27 |
| JP3837458B2 (ja) | 2006-10-25 |
| CA2238366A1 (en) | 1997-06-19 |
| CN1209140A (zh) | 1999-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3837458B2 (ja) | バッチ反応器を用いるラジカル塊重合 | |
| DE2724360C3 (de) | Verfahren zur Herstellung von thermoplastischen Formmassen auf Basis von Vinylpolymerisaten | |
| DE69334127T2 (de) | Herstellung von vernetzbaren polymeren mittels makromonomer-chain-transfer-agentien | |
| DE69433242T2 (de) | Heterogene polymerisation in kohlendioxid | |
| DE1570757C3 (de) | Verfahren zur Herstellung von Dispersionen von vernetzbaren Additionspolymeren in Kohlenwasserstoffen | |
| DE69526938T2 (de) | Thermisch durch freie Radikale härtende Klebstoffe, Härtungsverfahren und dadurch hergestellte Gegenstände | |
| DE4213964A1 (de) | Waessrige polymerisatdispersionen | |
| DE3631826A1 (de) | Herstellung eines methylmethacrylat-copolymerisats | |
| EP0752270A2 (de) | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Polymeren | |
| DE1240286B (de) | Verfahren zur kontinuierlichen Emulsions-polymerisation olefinisch ungesaettigter Verbindungen | |
| DE1900112B2 (de) | Verfahren zur kontinuierlichen Polymerisation von Vinylmonomeren | |
| DE2559260B2 (de) | Verfahren zur Modifizierung von Polyvinylidenfluorid | |
| EP0656374B1 (de) | Polymethacrylat-Formmasse mit hoher Wärmeformbeständigkeit und hoher Stabilität gegen thermischen Abbau | |
| DE1299421B (de) | Verfahren zur kontinuierlichen Loesungspolymerisation von Methacrylsaeureestern | |
| DE3042471C2 (enExample) | ||
| DE2801221A1 (de) | Kontinuierliches giessverfahren fuer fluessige polymerisierbare massen | |
| EP0463525B1 (de) | Verfahren zur Herstellung von Polymerisaten aus olefinisch ungesättigten Monomeren sowie Lösungen von Polymerisaten aus olefinisch ungesättigten Monomeren | |
| DE69216194T2 (de) | Plastisolzusammensetzungen | |
| DE69919829T2 (de) | Acrylische druckempfindliche Klebstoff-Zusammensetzung und Verfahren zu ihrer Herstellung | |
| DE4440219A1 (de) | Verfahren zur Herstellung von Copolymerisaten aus Alkylmethacrylat, Vinylaromaten und Maleinsäureanhydrid | |
| DE1645196A1 (de) | Block-Loesungsmittel-Polymerisationsverfahren fuer ABS-Polymere | |
| DE2322886C2 (de) | Verfahren zur Regelung der Polymerteilchengröße bei der Emulsionspolymerisation | |
| DE3026973A1 (de) | Verfahren zur herstellung von thermoplastisch verarbeitbaren copolymerisaten | |
| DE2843759A1 (de) | Verfahren zur kontinuierlichen herstellung eines prepolymersirups und dessen verwendung | |
| EP0374709B1 (de) | Verfahren zur kontinuierlichen Herstellung von flüssigkeitsabsorbierenden, vernetzten Polymeren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |