KR19990072192A - 회분식 반응기를 이용한 벌크 라디칼 중합 방법 - Google Patents
회분식 반응기를 이용한 벌크 라디칼 중합 방법 Download PDFInfo
- Publication number
- KR19990072192A KR19990072192A KR1019980704557A KR19980704557A KR19990072192A KR 19990072192 A KR19990072192 A KR 19990072192A KR 1019980704557 A KR1019980704557 A KR 1019980704557A KR 19980704557 A KR19980704557 A KR 19980704557A KR 19990072192 A KR19990072192 A KR 19990072192A
- Authority
- KR
- South Korea
- Prior art keywords
- mixture
- initiator
- temperature
- reaction
- initiators
- 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.)
- Ceased
Links
- 238000010526 radical polymerization reaction Methods 0.000 title description 18
- 239000000178 monomer Substances 0.000 claims abstract description 156
- 238000000034 method Methods 0.000 claims abstract description 81
- 230000008569 process Effects 0.000 claims abstract description 26
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 19
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims description 217
- 239000003999 initiator Substances 0.000 claims description 178
- 239000000203 mixture Substances 0.000 claims description 140
- 229920000642 polymer Polymers 0.000 claims description 131
- 238000006116 polymerization reaction Methods 0.000 claims description 97
- 150000003254 radicals Chemical class 0.000 claims description 62
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 53
- 238000010438 heat treatment Methods 0.000 claims description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 33
- 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
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 23
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 14
- 239000012986 chain transfer agent Substances 0.000 claims description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 claims description 7
- 230000003635 deoxygenating effect Effects 0.000 claims description 6
- 230000007423 decrease Effects 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 4
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=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
- 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 72
- 239000011541 reaction mixture Substances 0.000 description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 62
- 238000012360 testing method Methods 0.000 description 57
- 230000001070 adhesive effect Effects 0.000 description 43
- 239000000047 product Substances 0.000 description 43
- 239000000523 sample Substances 0.000 description 37
- 239000000853 adhesive Substances 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 239000002904 solvent Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 20
- 238000012546 transfer Methods 0.000 description 20
- 238000009826 distribution Methods 0.000 description 17
- 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 16
- 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 15
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- 239000004971 Cross linker Substances 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 12
- 238000011417 postcuring Methods 0.000 description 12
- -1 hydroxyalkyl acrylates Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 229910001220 stainless steel Inorganic materials 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 239000012943 hotmelt Substances 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000012086 standard solution Substances 0.000 description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
- MZHBJMCGUSCOJN-UHFFFAOYSA-N 2-[(2-cyanocyclohexyl)diazenyl]cyclohexane-1-carbonitrile Chemical compound N#CC1CCCCC1N=NC1C(C#N)CCCC1 MZHBJMCGUSCOJN-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 238000012662 bulk polymerization Methods 0.000 description 7
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 7
- 239000007863 gel particle Substances 0.000 description 7
- 238000004519 manufacturing process Methods 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
- 239000000654 additive Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000012470 diluted sample Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 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 4
- 239000010421 standard material Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 239000012491 analyte Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 238000006392 deoxygenation reaction Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 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
- 238000010926 purge Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 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
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000010558 suspension polymerization method Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 238000010408 sweeping Methods 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DIQZGCCQHMIOLR-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]prop-2-enoic acid;methane Chemical compound C.CC(C)(C)C1=CC(CC(=C)C(O)=O)=CC(C(C)(C)C)=C1O DIQZGCCQHMIOLR-UHFFFAOYSA-N 0.000 description 1
- PZYFAYMXLISRGL-UHFFFAOYSA-N 2-methylhexanenitrile Chemical compound CCCCC(C)C#N PZYFAYMXLISRGL-UHFFFAOYSA-N 0.000 description 1
- GWGNOHJASWDSAN-UHFFFAOYSA-N 2-tert-butyl-2-[(4-hydroxyphenyl)methyl]-3,3-dimethylbutanoic acid Chemical compound CC(C)(C)C(C(C)(C)C)(C(O)=O)CC1=CC=C(O)C=C1 GWGNOHJASWDSAN-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
- 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 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-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
- 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
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-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
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 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
- 230000004888 barrier function Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000009529 body temperature measurement Methods 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 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
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 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
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 230000007246 mechanism Effects 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005192 partition 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
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 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
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting 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
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000002000 scavenging effect 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
- 239000008247 solid mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000003797 telogen phase Effects 0.000 description 1
- WEHDCBONCFYXKK-UHFFFAOYSA-N tert-butyl 3-(4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CCC1=CC=C(O)C=C1 WEHDCBONCFYXKK-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
- 238000005979 thermal decomposition reaction Methods 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
- 230000007704 transition Effects 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)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8/572,310 | 1995-12-14 | ||
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| KR19990072192A true KR19990072192A (ko) | 1999-09-27 |
Family
ID=24287257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980704557A Ceased KR19990072192A (ko) | 1995-12-14 | 1996-11-12 | 회분식 반응기를 이용한 벌크 라디칼 중합 방법 |
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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100394365B1 (ko) * | 2000-10-18 | 2003-08-09 | (주) 고려물산 | 유화제가 첨가되지 않는 점착제 및 그 제조방법 |
| WO2010077487A3 (en) * | 2008-12-17 | 2010-08-26 | 3M Innovative Properties Company | Bulk polymerization of silicone-containing copolymers |
| KR20150144433A (ko) | 2014-06-16 | 2015-12-28 | 한경대학교 산학협력단 | 전처리된 순환골재를 이용하여 수용액 상에서 중금속을 제거하는 방법 |
Families Citing this family (208)
| 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 |
| US6107222A (en) * | 1997-12-01 | 2000-08-22 | 3M Innovative Properties Company | Repositionable sheets with a nonwoven web of pressure-sensitive adhesive fibers |
| US6133173A (en) * | 1997-12-01 | 2000-10-17 | 3M Innovative Properties Company | Nonwoven cohesive wrap |
| US6171985B1 (en) | 1997-12-01 | 2001-01-09 | 3M Innovative Properties Company | Low trauma adhesive article |
| US6102039A (en) | 1997-12-01 | 2000-08-15 | 3M Innovative Properties Company | Molded respirator containing sorbent particles |
| US6083856A (en) * | 1997-12-01 | 2000-07-04 | 3M Innovative Properties Company | Acrylate copolymeric 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 |
| US6624273B1 (en) | 1999-03-19 | 2003-09-23 | 3M Innovative Properties Company | Plasticized acrylics for pressure sensitive adhesive applications |
| US6855386B1 (en) | 1999-03-19 | 2005-02-15 | 3M Innovative Properties Company | Wet surface adhesives |
| 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 |
| US6518343B1 (en) | 1999-06-18 | 2003-02-11 | 3M Innovative Properties Company | Wet-stick adhesives, articles, and methods |
| US6441092B1 (en) | 1999-06-18 | 2002-08-27 | 3M Innovative Properties Company | Wet-stick adhesives |
| 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 |
| 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 |
| DE10153966B4 (de) * | 2001-05-09 | 2005-05-12 | List Ag | Verfahren zur Durchführung von Polymerisationsreaktionen |
| WO2003024373A1 (en) * | 2001-09-14 | 2003-03-27 | 3M Innovative Properties Company | Non-contact printing method for making a medical pressure sensitive adhesive article |
| US6893655B2 (en) | 2001-10-09 | 2005-05-17 | 3M Innovative Properties Co. | Transdermal delivery devices |
| US8323773B2 (en) | 2001-10-09 | 2012-12-04 | 3M Innovative Properties Company | Laminates with structured layers |
| US20030118970A1 (en) | 2001-12-21 | 2003-06-26 | 3M Innovative Properties Company | Removable dental models |
| AU2003300129A1 (en) * | 2003-01-04 | 2004-08-10 | 3M Innovative Properties Company | A vehicle battery pack insulator |
| 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 |
| KR100626436B1 (ko) * | 2003-11-13 | 2006-09-20 | 주식회사 엘지화학 | 난연성이 개선된 점착제 |
| JP2005146212A (ja) * | 2003-11-19 | 2005-06-09 | Three M Innovative Properties Co | 片面粘着テープ |
| US20050287360A1 (en) * | 2004-06-23 | 2005-12-29 | 3M Innovative Properties Company | Halogen free tapes & method of making same |
| 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 |
| US7291359B2 (en) * | 2004-08-18 | 2007-11-06 | 3M Innovative Properties Company | Method and apparatus for making an adhesive cleaning sheet |
| US7252855B2 (en) * | 2004-08-18 | 2007-08-07 | 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 |
| MX2007011553A (es) * | 2006-01-24 | 2007-11-08 | Intertape Polymer Corp | Polimerizacion de masa continua en un extrusor de rodillos planetarios. |
| 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 |
| US7463417B2 (en) | 2006-02-13 | 2008-12-09 | 3M Innovative Properties Company | Optical articles from curable compositions |
| US20070191506A1 (en) * | 2006-02-13 | 2007-08-16 | 3M Innovative Properties Company | Curable compositions for optical articles |
| WO2008027858A1 (en) * | 2006-08-30 | 2008-03-06 | Intertape Polymer Corp. | Recirculation loop reactor bulk polymerization process |
| 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 |
| JP5525819B2 (ja) * | 2006-11-07 | 2014-06-18 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | アクリルホットメルト接着剤 |
| US20080226702A1 (en) * | 2007-03-16 | 2008-09-18 | 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 |
| US8378046B2 (en) | 2007-10-19 | 2013-02-19 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US20090105437A1 (en) * | 2007-10-19 | 2009-04-23 | 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 |
| US9238762B2 (en) | 2007-11-08 | 2016-01-19 | 3M Innovative Properties Company | Optical adhesive with diffusive properties |
| WO2009152126A1 (en) * | 2008-06-09 | 2009-12-17 | 3M Innovative Properties Company | Acrylic pressure-sensitive adhesives with aziridine crosslinking agents |
| EP2307516B1 (en) * | 2008-07-28 | 2012-09-05 | Dow Corning Corporation | Composite article |
| 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 |
| 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 |
| WO2010144548A2 (en) | 2009-06-09 | 2010-12-16 | Regear Life Sciences, Inc. | Shielded diathermy applicator with automatic tuning and low incidental radiation |
| JP5608226B2 (ja) * | 2009-06-16 | 2014-10-15 | スリーエム イノベイティブ プロパティズ カンパニー | 剥離可能な接着物品 |
| KR101678714B1 (ko) | 2009-06-18 | 2016-11-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 고온 용융 감압 접착제의 제조 방법 |
| WO2011031442A2 (en) | 2009-08-28 | 2011-03-17 | 3M Innovative Properties Company | Polymerizable ionic liquid comprising multifunctional cation and antistatic coatings |
| EP2470509A2 (en) | 2009-08-28 | 2012-07-04 | 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 |
| US20120276317A1 (en) | 2009-12-08 | 2012-11-01 | Kiu-Yuen Tse | Optically diffusive adhesive and method of making the same |
| EP2515827A2 (en) | 2009-12-22 | 2012-10-31 | 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 |
| EP2542889B1 (en) * | 2010-03-03 | 2015-03-25 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
| JP5925131B2 (ja) | 2010-03-09 | 2016-05-25 | スリーエム イノベイティブ プロパティズ カンパニー | ディスプレイパネルを接合するための光学的に透明な熱活性化接着剤 |
| 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 |
| JP5881693B2 (ja) | 2010-06-29 | 2016-03-09 | スリーエム イノベイティブ プロパティズ カンパニー | アジリジニル含有化合物から生成されるグラフト化化合物 |
| EP2588535B1 (en) | 2010-06-29 | 2020-09-30 | 3M Innovative Properties Company | Aziridinyl-containing compounds |
| CN102959026B (zh) | 2010-06-30 | 2014-12-24 | 3M创新有限公司 | (甲基)丙烯酰压敏泡沫粘合剂 |
| 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 |
| CN103210001B (zh) | 2010-12-13 | 2015-06-24 | 3M创新有限公司 | 接枝共聚物和聚酰胺的共混物 |
| US8816004B2 (en) | 2010-12-14 | 2014-08-26 | 3M Innovative Properties Company | Oxazolinyl-containing polymers and grafted compounds prepared from the oxazolinyl-containing polymers |
| US9102774B2 (en) | 2010-12-21 | 2015-08-11 | 3M Innovative Properties Company | Polymers derived from secondary alkyl (meth)acrylates |
| EP2710519B1 (en) | 2011-05-20 | 2019-07-17 | Gemalto SA | Laser-personalized security articles |
| WO2012162041A2 (en) | 2011-05-20 | 2012-11-29 | 3M Innovative Properties Company | Laser-personalizable security articles |
| US8785517B2 (en) | 2011-05-25 | 2014-07-22 | 3M Innovative Properties Company | Pressure-sensitive adhesives with onium-epdxy crosslinking system |
| EP2723812B1 (en) | 2011-06-23 | 2016-04-13 | 3M Innovative Properties Company | Pressure-sensitive adhesives with onium-epoxy resin crosslinking system |
| CN103998549B (zh) | 2011-07-19 | 2016-10-12 | 3M创新有限公司 | 可热脱粘的粘合剂制品以及制备和使用此类制品的方法 |
| CN103890024B (zh) | 2011-09-12 | 2016-11-23 | 巴斯夫欧洲公司 | 接枝多元醇以及形成其的方法 |
| 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 |
| KR20140082768A (ko) | 2011-10-05 | 2014-07-02 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 미세구조화된 전사 테이프 |
| SG11201401666QA (en) | 2011-10-19 | 2014-10-30 | 3M Innovative Properties Co | Articles with thin melt coatings and methods for making same |
| KR20140092906A (ko) | 2011-11-18 | 2014-07-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 감압 접착제 조성물 |
| CN104144953A (zh) | 2012-02-29 | 2014-11-12 | 3M创新有限公司 | 作为潜在离子交联剂用于丙烯酸类压敏粘合剂的光产碱剂 |
| JP2015518504A (ja) | 2012-04-03 | 2015-07-02 | スリーエム イノベイティブ プロパティズ カンパニー | 光塩基発生剤を含む架橋性組成物 |
| EP2920265B1 (en) | 2012-11-16 | 2018-01-10 | 3M Innovative Properties Company | Adhesive including pendant (meth) acryloyl groups, article, and method |
| US9828532B2 (en) | 2012-11-19 | 2017-11-28 | 3M Innovation Properties Company | Crosslinkable and crosslinked compositions |
| CN104854140B (zh) * | 2012-12-14 | 2017-09-01 | 3M创新有限公司 | 利用电离辐射聚合烯键式不饱和材料的方法 |
| CN104837949A (zh) | 2012-12-14 | 2015-08-12 | 3M创新有限公司 | 通过使用电离辐射聚合烯键式不饱和材料来制备封装的粘弹性组合物的方法 |
| 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 |
| SG11201504889VA (en) | 2012-12-20 | 2015-07-30 | 3M Innovative Properties Co | Fluoropolymer composition including an oligomer having an ultraviolet absorbing group |
| JP6162959B2 (ja) * | 2013-01-16 | 2017-07-12 | 花王株式会社 | 非イオン性ポリマー |
| WO2014164000A1 (en) | 2013-03-13 | 2014-10-09 | 3M Innovative Properties Company | Adhesives comprising epoxy-acid crosslinked groups and methods |
| EP2970094B1 (en) | 2013-03-15 | 2018-12-19 | 3M Innovative Properties Company | Selective synthesis of 2-octyl acrylate by acid catalyzed esterification of 2-octanol and acrylic acid |
| WO2014143690A1 (en) | 2013-03-15 | 2014-09-18 | 3M Innovative Properties Company | Method for preparing (meth)acrylates of biobased alcohols and polymers thereof |
| BR112015023594A2 (pt) | 2013-03-15 | 2017-07-18 | 3M Innovative Properties Co | método para preparar (met)acrilatos de alcoóis de base biológica e polímeros dos mesmos |
| 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 |
| WO2014186169A1 (en) | 2013-05-14 | 2014-11-20 | 3M Innovative Properties Company | Adhesive composition |
| 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 |
| WO2014209574A1 (en) | 2013-06-25 | 2014-12-31 | 3M Innovative Properties Company | Moisture-curable composition, method of using, and composite article |
| 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 |
| KR20160111425A (ko) | 2014-01-17 | 2016-09-26 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 자가-습윤 접착제 에멀젼 조성물 |
| MX2016013042A (es) | 2014-04-04 | 2017-02-28 | 3M Innovative Properties Co | Adhesivos para superficie húmeda y seca. |
| EP3149053A1 (en) | 2014-05-29 | 2017-04-05 | 3M Innovative Properties Company | Acrylic adhesive composition with controlled molecular weight |
| WO2015200655A1 (en) | 2014-06-25 | 2015-12-30 | 3M Innovative Properties Company | Fluoropolymer composition including at least one oligomer |
| US11110689B2 (en) | 2014-06-25 | 2021-09-07 | 3M Innovative Properties Company | Pressure sensitive adhesive composition including ultraviolet light-absorbing oligomer |
| 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 |
| EP3240811B1 (en) | 2014-12-30 | 2018-11-28 | 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 |
| CN107207931B (zh) | 2014-12-30 | 2018-12-28 | 3M创新有限公司 | 水基压敏粘合剂组合物 |
| JP6359199B2 (ja) | 2015-02-18 | 2018-07-18 | スリーエム イノベイティブ プロパティズ カンパニー | 保護された光架橋剤由来のアクリル系接着剤組成物 |
| KR20170136572A (ko) | 2015-04-13 | 2017-12-11 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 가교결합을 위한 발광 다이오드를 사용하여 가교결합된 감압성 접착제의 제조 방법 |
| KR102024481B1 (ko) | 2015-06-03 | 2019-09-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 가요성 디스플레이용 조립체 층 |
| JP2018526470A (ja) | 2015-06-03 | 2018-09-13 | スリーエム イノベイティブ プロパティズ カンパニー | アクリル系可撓性アセンブリ層 |
| CN111500227B (zh) | 2015-06-04 | 2022-04-22 | 3M创新有限公司 | 可uv固化的环氧/丙烯酸酯粘合剂组合物 |
| US10519350B2 (en) | 2015-06-25 | 2019-12-31 | 3M Innovative Properties Company | Copolymer including ultraviolet light-absorbing group and compositions including the same |
| EP3344720B1 (en) | 2015-08-31 | 2020-10-14 | 3M Innovative Properties Company | Articles comprising (meth)acrylate pressure-sensitive adhesive with enhanced adhesion to wet surfaces |
| WO2017040074A1 (en) | 2015-08-31 | 2017-03-09 | 3M Innovative Properties Company | Negative pressure wound therapy dressings comprising (meth)acrylate pressure-sensitive adhesive with enhanced adhesion to wet surfaces |
| KR20180063165A (ko) | 2015-09-30 | 2018-06-11 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 경화성 및 경화된 접착제 조성물 |
| EP3156466B1 (en) | 2015-10-15 | 2020-11-25 | 3M Innovative Properties Company | Multilayer pressure sensitive adhesive foam tape for outdooor applications |
| EP3156465A1 (en) | 2015-10-15 | 2017-04-19 | 3M Innovative Properties Company | Multilayer pressure sensitive adhesive foam tape for outdooor applications |
| US10759991B2 (en) | 2015-11-18 | 2020-09-01 | 3M Innovative Properties Company | Copolymeric stabilizing carrier fluid for nanoparticles |
| WO2017112457A1 (en) | 2015-12-22 | 2017-06-29 | 3M Innovative Properties Company | Oxalate ester - polyamine thermosetting compositions |
| EP3394125B1 (en) | 2015-12-22 | 2020-04-29 | 3M Innovative Properties Company | Curable polymeric materials and methods of using same |
| 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 |
| KR102034615B1 (ko) | 2016-02-17 | 2019-10-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 안정화 불소화합물계 공중합체를 갖는 양자점 |
| US10947423B2 (en) | 2016-03-10 | 2021-03-16 | 3M Innovative Properties Company | Oil resistant adhesive |
| KR20190023095A (ko) | 2016-06-29 | 2019-03-07 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 중합성 이온 액체 조성물 |
| US11261351B2 (en) | 2016-08-12 | 2022-03-01 | 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 |
| JP7055972B2 (ja) | 2016-10-26 | 2022-04-19 | スリーエム イノベイティブ プロパティズ カンパニー | 架橋性組成物及び架橋された組成物 |
| US11492515B2 (en) | 2016-12-02 | 2022-11-08 | 3M Innovative Properties Company | Low dielectric optically clear adhesives for flexible electronic display |
| CN110023073B (zh) | 2016-12-02 | 2021-09-17 | 3M创新有限公司 | 多层粘合剂制品 |
| EP3336153B1 (en) | 2016-12-19 | 2020-11-25 | 3M Innovative Properties Company | Rubber-based multilayer pressure-sensitive adhesive assembly having low voc characteristics |
| US11920067B2 (en) | 2016-12-19 | 2024-03-05 | 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 |
| US10774245B2 (en) | 2017-05-12 | 2020-09-15 | 3M Innovative Properties Company | Adhesive tapes |
| WO2019005932A1 (en) | 2017-06-30 | 2019-01-03 | 3M Innovative Properties Company | ADHESIVES FOR WET AND DRY SURFACES |
| KR102543277B1 (ko) | 2017-06-30 | 2023-06-16 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 인쇄가능한 경화성 혼합물 및 경화된 조성물 |
| 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 |
| WO2019125995A1 (en) | 2017-12-18 | 2019-06-27 | 3M Innovative Properties Company | Phenolic resin composition comprising polymerized ionic groups, abrasive articles and methods |
| US20200332152A1 (en) | 2017-12-21 | 2020-10-22 | 3M Innovative Properties Company | Adhesive articles including a cushion layer and a discontinuous shell layer |
| WO2019123180A1 (en) | 2017-12-21 | 2019-06-27 | 3M Innovative Properties Company | Adhesive articles including a cushion layer and a continuous shell layer |
| EP3759190B1 (en) | 2018-02-28 | 2025-03-26 | 3M Innovative Properties Company | Adhesives comprising polymerized units of secondary hexyl (meth)acrylates |
| EP3775086B1 (en) | 2018-04-05 | 2022-09-14 | 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 |
| WO2020039294A1 (en) | 2018-08-22 | 2020-02-27 | 3M Innovative Properties Company | Curable compositions for pressure-sensitive adhesives |
| EP3613820A1 (en) | 2018-08-24 | 2020-02-26 | 3M Innovative Properties Company | Multilayer pressure-sensitive adhesive assembly |
| 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 |
| US20220259465A1 (en) | 2019-08-15 | 2022-08-18 | 3M Innovative Properties Company | Core-sheath filament with a thermally conductive pressure-sensitive adhesive core |
| US11725308B2 (en) | 2019-08-19 | 2023-08-15 | 3M Innovative Properties Company | Core-sheath filaments including crosslinkable and crosslinked adhesive compositions and methods of making the same |
| US20220315807A1 (en) | 2019-09-09 | 2022-10-06 | 3M Innovative Properties Company | Coextruded polymeric adhesive article |
| WO2021074001A1 (en) | 2019-10-16 | 2021-04-22 | Basf Coatings Gmbh | Super advanced controlled radical polymerization |
| WO2021099997A1 (en) | 2019-11-20 | 2021-05-27 | 3M Innovative Properties Company | Medical tapes with high optical clarity when over-taped |
| EP4061904B1 (en) | 2019-11-21 | 2025-05-21 | 3M Innovative Properties Company | Crosslinkable and crosslinked acrylic adhesive compositions |
| 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 |
| JP2024522258A (ja) | 2021-05-18 | 2024-06-12 | スリーエム イノベイティブ プロパティズ カンパニー | 架橋性組成物 |
| EP4347246A1 (en) | 2021-06-04 | 2024-04-10 | 3M Innovative Properties Company | Articles containing adhesive compositions exhibiting on-demand debonding behavior |
| 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 |
| WO2023084372A1 (en) | 2021-11-11 | 2023-05-19 | 3M Innovative 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 |
| WO2024047418A1 (en) | 2022-08-29 | 2024-03-07 | 3M Innovative Properties Company | Pressure sensitive adhesive compositions comprising polymerized amide monomers, articles, and methods |
| EP4594378A1 (en) * | 2022-11-18 | 2025-08-06 | Avery Dennison Corporation | Architectured polymers and related methods |
| WO2025012822A2 (en) | 2023-07-12 | 2025-01-16 | Solventum Intellectual Properties Company | Packaged pressure sensitive adhesives |
| WO2025062229A1 (en) | 2023-09-20 | 2025-03-27 | 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 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL88611C (enExample) * | 1951-09-10 | |||
| NL123955C (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 EP EP96939732A patent/EP0866810B1/en not_active Expired - Lifetime
- 1996-11-12 JP JP52204497A patent/JP3837458B2/ja not_active Expired - Lifetime
- 1996-11-12 AU AU76819/96A patent/AU7681996A/en not_active Abandoned
- 1996-11-12 CN CN96199944A patent/CN1209140A/zh active Pending
- 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 WO PCT/US1996/018503 patent/WO1997021736A1/en not_active Ceased
- 1996-11-12 KR KR1019980704557A patent/KR19990072192A/ko not_active Ceased
- 1996-11-12 CA CA002238366A patent/CA2238366A1/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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100394365B1 (ko) * | 2000-10-18 | 2003-08-09 | (주) 고려물산 | 유화제가 첨가되지 않는 점착제 및 그 제조방법 |
| WO2010077487A3 (en) * | 2008-12-17 | 2010-08-26 | 3M Innovative Properties Company | Bulk polymerization of silicone-containing copolymers |
| KR20110104040A (ko) * | 2008-12-17 | 2011-09-21 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 실리콘-함유 공중합체의 벌크 중합 |
| EP2373708A4 (en) * | 2008-12-17 | 2012-08-08 | 3M Innovative Properties Co | MASSEPOLYMERIZATION OF SILICONE-CONTAINING COPOLYMERS |
| US10465017B2 (en) | 2008-12-17 | 2019-11-05 | 3M Innovative Properties Company | Bulk polymerization of silicone-containing copolymers |
| US10723815B2 (en) | 2008-12-17 | 2020-07-28 | 3M Innovative Properties Company | Bulk polymerization of silicone-containing copolymers |
| KR20150144433A (ko) | 2014-06-16 | 2015-12-28 | 한경대학교 산학협력단 | 전처리된 순환골재를 이용하여 수용액 상에서 중금속을 제거하는 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000501764A (ja) | 2000-02-15 |
| BR9611919A (pt) | 1999-03-30 |
| JP3837458B2 (ja) | 2006-10-25 |
| EP0866810A1 (en) | 1998-09-30 |
| DE69619854D1 (de) | 2002-04-18 |
| CA2238366A1 (en) | 1997-06-19 |
| AU7681996A (en) | 1997-07-03 |
| US5753768A (en) | 1998-05-19 |
| DE69619854T2 (de) | 2002-10-02 |
| MX9804624A (es) | 1998-10-31 |
| US5986011A (en) | 1999-11-16 |
| EP0866810B1 (en) | 2002-03-13 |
| WO1997021736A1 (en) | 1997-06-19 |
| US5637646A (en) | 1997-06-10 |
| CN1209140A (zh) | 1999-02-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR19990072192A (ko) | 회분식 반응기를 이용한 벌크 라디칼 중합 방법 | |
| US8263718B2 (en) | Method of free radically polymerizing vinyl monomers | |
| EP0160394B1 (en) | Continuous free radical polymerization in a wiped-surface reactor | |
| KR101359775B1 (ko) | 비닐 단량체의 자유 라디칼 중합 방법 | |
| JPH03205415A (ja) | 紫外線により硬化可能な剤 | |
| JPH04226504A (ja) | オレフィン性不飽和モノマーからなるポリマー並びにこのポリマーの溶液及び感圧接着剤 | |
| TW354298B (en) | A process for making a polymer of acrylonitrile, methacrylonitrile and olefinically unsaturated monomers | |
| MXPA98004624A (en) | Polymerization in block by radicals using a reactor therefore | |
| Andrzejewska | Sulfur-containing polyacrylates: VI. Temperature effects on the photoinitiated polymerization of dimethacrylates | |
| CN116272762A (zh) | 一种丙烯酸酯类胶黏剂自动控制聚合装置及其使用方法 | |
| JP5136933B2 (ja) | アクリル共重合体の製造方法 | |
| WO1995003337A1 (en) | Photoinitiator compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 19980613 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20011109 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20040112 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20040322 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20040112 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |