JP4065932B2 - ハロゲン化アクリレート類およびそれから誘導されるポリマー - Google Patents
ハロゲン化アクリレート類およびそれから誘導されるポリマー Download PDFInfo
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- JP4065932B2 JP4065932B2 JP50235299A JP50235299A JP4065932B2 JP 4065932 B2 JP4065932 B2 JP 4065932B2 JP 50235299 A JP50235299 A JP 50235299A JP 50235299 A JP50235299 A JP 50235299A JP 4065932 B2 JP4065932 B2 JP 4065932B2
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- halogenated
- groups
- aliphatic
- acrylate
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- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims description 64
- 229920000642 polymer Polymers 0.000 title claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 92
- 239000000178 monomer Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000002723 alicyclic group Chemical group 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000002576 ketones Chemical class 0.000 claims description 14
- 229920000058 polyacrylate Polymers 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 59
- -1 acrylate ester Chemical class 0.000 description 55
- 239000000243 solution Substances 0.000 description 47
- 239000011541 reaction mixture Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 230000003287 optical effect Effects 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 32
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 239000004971 Cross linker Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 229920001519 homopolymer Polymers 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 239000013307 optical fiber Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- VFFZWTDBYPCUAS-UHFFFAOYSA-N [2,4,6-tribromo-3,5-di(prop-2-enoyloxy)phenyl] prop-2-enoate Chemical compound BrC1=C(OC(=O)C=C)C(Br)=C(OC(=O)C=C)C(Br)=C1OC(=O)C=C VFFZWTDBYPCUAS-UHFFFAOYSA-N 0.000 description 11
- 238000002835 absorbance Methods 0.000 description 11
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000002390 rotary evaporation Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000003682 fluorination reaction Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 7
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- RFOWDPMCXHVGET-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) prop-2-enoate Chemical compound FC1=C(F)C(F)=C(OC(=O)C=C)C(F)=C1F RFOWDPMCXHVGET-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 125000004386 diacrylate group Chemical group 0.000 description 5
- 229920006254 polymer film Polymers 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 230000008961 swelling Effects 0.000 description 5
- AAGIVLUPOJJGAC-UHFFFAOYSA-N (2,4,6-trichloro-3,5-difluorophenyl) prop-2-enoate Chemical compound FC1=C(Cl)C(F)=C(Cl)C(OC(=O)C=C)=C1Cl AAGIVLUPOJJGAC-UHFFFAOYSA-N 0.000 description 4
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 4
- FVXWNUUQRAHIRN-UHFFFAOYSA-N 2,4,6-tribromobenzene-1,3,5-triol Chemical compound OC1=C(Br)C(O)=C(Br)C(O)=C1Br FVXWNUUQRAHIRN-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DPQWHWXSRDXSJJ-UHFFFAOYSA-N (2,3,4,5-tetrabromo-6-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound BrC1=C(Br)C(Br)=C(OC(=O)C=C)C(OC(=O)C=C)=C1Br DPQWHWXSRDXSJJ-UHFFFAOYSA-N 0.000 description 3
- RWEQEWKAJFTONV-UHFFFAOYSA-N 1,3,4,5,6,7,8-heptafluoronaphthalen-2-ol Chemical compound FC1=C(F)C(F)=C(F)C2=C(F)C(O)=C(F)C(F)=C21 RWEQEWKAJFTONV-UHFFFAOYSA-N 0.000 description 3
- KGCDGLXSBHJAHZ-UHFFFAOYSA-N 1-chloro-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Cl)C(F)=C1F KGCDGLXSBHJAHZ-UHFFFAOYSA-N 0.000 description 3
- YUMDTEARLZOACP-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluorocyclohexan-1-one Chemical compound FC1(F)C(=O)C(F)(F)C(F)(F)C(F)(F)C1(F)F YUMDTEARLZOACP-UHFFFAOYSA-N 0.000 description 3
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 229920006125 amorphous polymer Polymers 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000005594 diketone group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- MGZZFXSKGIIXLF-UHFFFAOYSA-N (1,3,4,5,6,7,8-heptafluoronaphthalen-2-yl) prop-2-enoate Chemical compound FC1=C(OC(=O)C=C)C(F)=C(F)C2=C(F)C(F)=C(F)C(F)=C21 MGZZFXSKGIIXLF-UHFFFAOYSA-N 0.000 description 2
- HPNOUFWYZBRBHA-UHFFFAOYSA-N (2,4,6-tribromo-3-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound BrC1=CC(Br)=C(OC(=O)C=C)C(Br)=C1OC(=O)C=C HPNOUFWYZBRBHA-UHFFFAOYSA-N 0.000 description 2
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 2
- IAMTVSBHRDQLQU-UHFFFAOYSA-N 1,1,1,3,3-pentafluoro-3-[1,2,2,2-tetrafluoro-1-[1,1,2,2-tetrafluoro-2-(trifluoromethoxy)ethoxy]ethoxy]propan-2-one Chemical compound FC(F)(F)OC(F)(F)C(F)(F)OC(F)(C(F)(F)F)OC(F)(F)C(=O)C(F)(F)F IAMTVSBHRDQLQU-UHFFFAOYSA-N 0.000 description 2
- RKIMETXDACNTIE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorocyclohexane Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F RKIMETXDACNTIE-UHFFFAOYSA-N 0.000 description 2
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- QIVTYBYAOIZVJM-UHFFFAOYSA-N 1,2,3,4-tetrafluoro-5,6-bis[(2-methylpropan-2-yl)oxy]benzene Chemical class CC(C)(C)OC1=C(F)C(F)=C(F)C(F)=C1OC(C)(C)C QIVTYBYAOIZVJM-UHFFFAOYSA-N 0.000 description 2
- HJGLRKGSIAWDBK-UHFFFAOYSA-N 1,2-dichloro-1-(1,2-dichloro-1,2,2-trifluoroethoxy)-1,2,2-trifluoroethane Chemical class FC(F)(Cl)C(F)(Cl)OC(F)(Cl)C(F)(F)Cl HJGLRKGSIAWDBK-UHFFFAOYSA-N 0.000 description 2
- QPXZZPSKCVNHFW-UHFFFAOYSA-N 1,3,5-trichloro-2,4,6-trifluorobenzene Chemical compound FC1=C(Cl)C(F)=C(Cl)C(F)=C1Cl QPXZZPSKCVNHFW-UHFFFAOYSA-N 0.000 description 2
- FEVKLWKZMWXKJU-UHFFFAOYSA-N 1-(3,5-dichloro-2,4,6-trifluorophenyl)-2,2,3,3,4,4,5,5,6,6-decafluorocyclohexan-1-ol Chemical compound FC=1C(Cl)=C(F)C(Cl)=C(F)C=1C1(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F FEVKLWKZMWXKJU-UHFFFAOYSA-N 0.000 description 2
- VJQYOYATIGTMRY-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6-decafluoro-1-(trichloromethyl)cyclohexan-1-ol Chemical compound ClC(Cl)(Cl)C1(O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F VJQYOYATIGTMRY-UHFFFAOYSA-N 0.000 description 2
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/22—Esters containing halogen
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/872,235 | 1997-06-10 | ||
| US08/872,235 US6005137A (en) | 1997-06-10 | 1997-06-10 | Halogenated acrylates and polymers derived therefrom |
| PCT/US1997/017437 WO1998056749A1 (en) | 1997-06-10 | 1997-09-29 | Halogenated acrylates and polymers derived therefrom |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002514259A JP2002514259A (ja) | 2002-05-14 |
| JP2002514259A5 JP2002514259A5 (enExample) | 2005-06-16 |
| JP4065932B2 true JP4065932B2 (ja) | 2008-03-26 |
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| EP (1) | EP1009729B1 (enExample) |
| JP (1) | JP4065932B2 (enExample) |
| KR (1) | KR100597970B1 (enExample) |
| CN (1) | CN1125030C (enExample) |
| AU (1) | AU4739297A (enExample) |
| DE (1) | DE69732310T2 (enExample) |
| WO (1) | WO1998056749A1 (enExample) |
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| US6005137A (en) * | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| US6555288B1 (en) | 1999-06-21 | 2003-04-29 | Corning Incorporated | Optical devices made from radiation curable fluorinated compositions |
| US6306563B1 (en) | 1999-06-21 | 2001-10-23 | Corning Inc. | Optical devices made from radiation curable fluorinated compositions |
| WO2001096961A2 (en) | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Multipass multiphoton absorption method and apparatus |
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| US6852766B1 (en) | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| JP4965052B2 (ja) * | 2000-06-15 | 2012-07-04 | スリーエム イノベイティブ プロパティズ カンパニー | 3次元光学素子の加工方法 |
| WO2001096958A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Process for producing microfluidic articles |
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| DE60118576T2 (de) | 2000-08-18 | 2006-11-02 | 3M Innovative Properties Co., Saint Paul | Fluoro(meth)acrylatecopolymer-beschichtungsmassen |
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| WO2020212777A1 (en) | 2019-04-18 | 2020-10-22 | 3M Innovative Properties Company | Organic light emitting diode display with color-correction component |
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| KR102784676B1 (ko) * | 2024-01-17 | 2025-03-21 | 주식회사 트리엘 | 대면적 코팅을 위한 잉크젯용 포토레지스트 조성물 및 이의 제조방법 |
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-
1997
- 1997-06-10 US US08/872,235 patent/US6005137A/en not_active Expired - Fee Related
- 1997-09-29 KR KR1019997011592A patent/KR100597970B1/ko not_active Expired - Fee Related
- 1997-09-29 CN CN97182296A patent/CN1125030C/zh not_active Expired - Fee Related
- 1997-09-29 DE DE69732310T patent/DE69732310T2/de not_active Expired - Lifetime
- 1997-09-29 AU AU47392/97A patent/AU4739297A/en not_active Abandoned
- 1997-09-29 WO PCT/US1997/017437 patent/WO1998056749A1/en not_active Ceased
- 1997-09-29 JP JP50235299A patent/JP4065932B2/ja not_active Expired - Fee Related
- 1997-09-29 EP EP97909884A patent/EP1009729B1/en not_active Expired - Lifetime
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- 1999-08-24 US US09/382,300 patent/US6288266B1/en not_active Expired - Fee Related
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2001
- 2001-05-01 US US09/846,739 patent/US6362379B2/en not_active Expired - Fee Related
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|---|---|
| US6362379B2 (en) | 2002-03-26 |
| AU4739297A (en) | 1998-12-30 |
| US6005137A (en) | 1999-12-21 |
| CN1259932A (zh) | 2000-07-12 |
| WO1998056749A1 (en) | 1998-12-17 |
| EP1009729B1 (en) | 2005-01-19 |
| KR100597970B1 (ko) | 2006-07-13 |
| DE69732310T2 (de) | 2005-12-22 |
| US6313245B1 (en) | 2001-11-06 |
| JP2002514259A (ja) | 2002-05-14 |
| CN1125030C (zh) | 2003-10-22 |
| EP1009729A1 (en) | 2000-06-21 |
| US20010037028A1 (en) | 2001-11-01 |
| US6288266B1 (en) | 2001-09-11 |
| KR20010013585A (ko) | 2001-02-26 |
| DE69732310D1 (de) | 2005-02-24 |
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