DE69732310T2 - Halogenierte acrylate und davon abgeleitete polymere - Google Patents
Halogenierte acrylate und davon abgeleitete polymere Download PDFInfo
- Publication number
- DE69732310T2 DE69732310T2 DE69732310T DE69732310T DE69732310T2 DE 69732310 T2 DE69732310 T2 DE 69732310T2 DE 69732310 T DE69732310 T DE 69732310T DE 69732310 T DE69732310 T DE 69732310T DE 69732310 T2 DE69732310 T2 DE 69732310T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- groups
- halogenated
- aliphatic
- acrylates
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims description 65
- 229920000642 polymer Polymers 0.000 title claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 94
- 239000000178 monomer Substances 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 33
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000003682 fluorination reaction Methods 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 13
- 229920000058 polyacrylate Polymers 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 7
- 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
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical group ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
- -1 Perfluoroalkyl alcohols Chemical class 0.000 description 63
- 239000000203 mixture Substances 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 48
- 239000000460 chlorine Substances 0.000 description 45
- 230000003287 optical effect Effects 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
- 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 25
- 239000011541 reaction mixture Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 21
- 239000004971 Cross linker Substances 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 229920001519 homopolymer Polymers 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000010521 absorption reaction Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 17
- 229920000728 polyester Polymers 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 13
- 238000002835 absorbance Methods 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 239000013307 optical fiber Substances 0.000 description 13
- 239000000835 fiber Substances 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 11
- 150000002576 ketones Chemical class 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 125000004386 diacrylate group Chemical group 0.000 description 10
- 238000004817 gas chromatography Methods 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 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
- 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 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000005292 vacuum distillation 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
- 239000002244 precipitate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000002390 rotary evaporation Methods 0.000 description 7
- 238000004611 spectroscopical analysis Methods 0.000 description 7
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 150000001298 alcohols Chemical group 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
- 238000004821 distillation Methods 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 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 5
- 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-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
- 239000011521 glass Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 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
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 150000002170 ethers Chemical class 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
- 239000012044 organic layer Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 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 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
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 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
- 238000005253 cladding Methods 0.000 description 3
- 238000000576 coating method Methods 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
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 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
- 239000003999 initiator Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 239000012071 phase Substances 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
- 230000008707 rearrangement Effects 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- FYCOZPGUWKTYNJ-UHFFFAOYSA-N trimethyl-(2,3,4,5,6-pentafluorophenoxy)silane Chemical compound C[Si](C)(C)OC1=C(F)C(F)=C(F)C(F)=C1F FYCOZPGUWKTYNJ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UHYATKVUEBHMBJ-UHFFFAOYSA-N (2,3,4,6-tetrafluoro-5-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound FC1=C(F)C(OC(=O)C=C)=C(F)C(OC(=O)C=C)=C1F UHYATKVUEBHMBJ-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
- 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
- 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 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
- DXMNIUZVFLURQX-UHFFFAOYSA-N 2,2-difluoro-1,1-bis(2,3,4,5,6-pentafluorophenyl)-2-[1,1,2,2-tetrafluoro-2-(1,1,2,2,2-pentafluoroethoxy)ethoxy]ethanol Chemical compound FC=1C(F)=C(F)C(F)=C(F)C=1C(C(F)(F)OC(F)(F)C(F)(F)OC(F)(F)C(F)(F)F)(O)C1=C(F)C(F)=C(F)C(F)=C1F DXMNIUZVFLURQX-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
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 0 C=*C1(CCCCC1)O Chemical compound C=*C1(CCCCC1)O 0.000 description 2
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- QBMYBKGCWVRRGV-UHFFFAOYSA-N [2,4,5-tribromo-3,6-di(prop-2-enoyloxy)phenyl] prop-2-enoate Chemical compound BrC1=C(Br)C(OC(=O)C=C)=C(OC(=O)C=C)C(Br)=C1OC(=O)C=C QBMYBKGCWVRRGV-UHFFFAOYSA-N 0.000 description 1
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
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- 230000003301 hydrolyzing effect Effects 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
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- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 description 1
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
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- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
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- 229920006295 polythiol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
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- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000008028 secondary esters Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
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- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- 229960002622 triacetin Drugs 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 US6005137A (en) | 1997-06-10 | 1997-06-10 | Halogenated acrylates and polymers derived therefrom |
| US872235 | 1997-06-10 | ||
| PCT/US1997/017437 WO1998056749A1 (en) | 1997-06-10 | 1997-09-29 | Halogenated acrylates and polymers derived therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69732310D1 DE69732310D1 (de) | 2005-02-24 |
| DE69732310T2 true DE69732310T2 (de) | 2005-12-22 |
Family
ID=25359127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69732310T Expired - Lifetime DE69732310T2 (de) | 1997-06-10 | 1997-09-29 | Halogenierte acrylate und davon abgeleitete polymere |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6005137A (enExample) |
| 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10257711B4 (de) * | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6005137A (en) * | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
| US6306563B1 (en) | 1999-06-21 | 2001-10-23 | Corning Inc. | Optical devices made from radiation curable fluorinated compositions |
| US6555288B1 (en) | 1999-06-21 | 2003-04-29 | Corning Incorporated | Optical devices made from radiation curable fluorinated compositions |
| WO2001096952A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Multicolor imaging using multiphoton photochemical processes |
| WO2001096915A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Microfabrication of organic optical elements |
| US7060419B2 (en) * | 2000-06-15 | 2006-06-13 | 3M Innovative Properties Company | Process for producing microfluidic articles |
| US6852766B1 (en) | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| DE60139620D1 (de) | 2000-06-15 | 2009-10-01 | 3M Innovative Properties Co | Methode und gerät zur erzielung wiederholter multiphotonabsorption |
| US7790353B2 (en) | 2000-06-15 | 2010-09-07 | 3M Innovative Properties Company | Multidirectional photoreactive absorption method |
| AU2001268465A1 (en) | 2000-06-15 | 2001-12-24 | 3M Innovative Properties Company | Multiphoton curing to provide encapsulated optical elements |
| US6514434B1 (en) | 2000-06-16 | 2003-02-04 | Corning Incorporated | Electro-optic chromophore bridge compounds and donor-bridge compounds for polymeric thin film waveguides |
| US6444830B1 (en) | 2000-06-16 | 2002-09-03 | Corning Incorporated | Electron acceptors for polymeric thin film waveguide media |
| US6584266B1 (en) | 2000-06-16 | 2003-06-24 | Corning Incorporated | Chromophores for polymeric thin films and optical waveguides and devices comprising the same |
| WO2002016517A2 (en) | 2000-08-18 | 2002-02-28 | 3M Innovative Properties Company | Fluoroalkyl (meth)acrylate copolymer coating compositions |
| CN1237395C (zh) * | 2000-12-27 | 2006-01-18 | 三井化学株式会社 | 薄膜和薄膜的制造方法以及薄膜用粘合剂 |
| US6929899B2 (en) | 2001-01-25 | 2005-08-16 | E. I. Du Pont De Nemours And Company | Fluorinated photopolymer composition and waveguide device |
| US7078445B2 (en) * | 2001-02-01 | 2006-07-18 | E. I. Du Pont De Nemours And Company | Photosensitive acrylate composition and waveguide device |
| US6689844B2 (en) * | 2001-05-29 | 2004-02-10 | Rohmax Additives Gmbh | Process for synthesis of polymer compositions with reduced halogen content, polymer composition with reduced halogen content as well as use of this composition |
| US20040012872A1 (en) * | 2001-06-14 | 2004-01-22 | Fleming Patrick R | Multiphoton absorption method using patterned light |
| KR100898877B1 (ko) * | 2002-02-04 | 2009-05-25 | 시바 홀딩 인크 | 고도로 플루오르화된 단량체 내의 플루오르화 광개시제 |
| JP4222120B2 (ja) * | 2002-10-07 | 2009-02-12 | Ｊｓｒ株式会社 | 光導波路形成用感光性樹脂組成物および光導波路 |
| AU2003285106A1 (en) * | 2002-11-01 | 2004-06-07 | Cargill, Incorporated | Process for preparation of 1,3-propanediol |
| JP2004240122A (ja) * | 2003-02-05 | 2004-08-26 | Fuji Photo Film Co Ltd | プラスチック光ファイバケーブルおよび製造方法 |
| US20060056031A1 (en) * | 2004-09-10 | 2006-03-16 | Capaldo Kevin P | Brightness enhancement film, and methods of making and using the same |
| US6833391B1 (en) | 2003-05-27 | 2004-12-21 | General Electric Company | Curable (meth)acrylate compositions |
| TWI254717B (en) * | 2003-08-06 | 2006-05-11 | Chung Shan Inst Of Science | Method for the preparation of pentafluorophenylacrylate polymer |
| US7271283B2 (en) * | 2003-08-29 | 2007-09-18 | General Electric Company | High refractive index, UV-curable monomers and coating compositions prepared therefrom |
| JP2005140909A (ja) * | 2003-11-05 | 2005-06-02 | Omron Corp | 光学部品 |
| KR101129883B1 (ko) * | 2004-05-26 | 2012-03-28 | 제이에스알 가부시끼가이샤 | 미세 패턴 형성용 수지 조성물 및 미세 패턴 형성 방법 |
| US7341784B2 (en) * | 2004-09-10 | 2008-03-11 | General Electric Company | Light management film and its preparation and use |
| US20080286580A1 (en) * | 2004-09-14 | 2008-11-20 | Maria Petrucci-Samija | Polymeric Optical Waveguide |
| US20080293903A1 (en) * | 2004-09-14 | 2008-11-27 | Maria Petrucci-Samija | Optical Organic Polymer |
| WO2006034011A1 (en) * | 2004-09-14 | 2006-03-30 | E.I. Dupont De Nemours And Company | Process for preparing an optical organic polymer |
| US7264872B2 (en) * | 2004-12-30 | 2007-09-04 | 3M Innovative Properties Company | Durable high index nanocomposites for AR coatings |
| US7491441B2 (en) * | 2004-12-30 | 2009-02-17 | 3M Innovative Properties Company | High refractive index, durable hard coats |
| US7297810B2 (en) * | 2004-12-30 | 2007-11-20 | 3M Innovative Properties Company | High refractive index monomers for optical applications |
| US7262230B2 (en) * | 2005-01-21 | 2007-08-28 | Lumera Corporation | Process of preparing crosslinked, low loss polymers with tunable refractive indices |
| US7231127B2 (en) * | 2005-01-21 | 2007-06-12 | Lumera Corporation | Waveguide devices with low loss clads and tunable refractive indices |
| US8435610B2 (en) * | 2006-05-05 | 2013-05-07 | Japan Science And Technology Agency | Copolymer of (meth)acrylic ester, composition, optical element and electric member |
| US8791254B2 (en) * | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US20080145545A1 (en) * | 2006-12-15 | 2008-06-19 | Bret Ja Chisholm | Metal oxide and sulfur-containing coating compositions, methods of use, and articles prepared therefrom |
| US8179034B2 (en) | 2007-07-13 | 2012-05-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode display and lighting devices |
| US20090015142A1 (en) | 2007-07-13 | 2009-01-15 | 3M Innovative Properties Company | Light extraction film for organic light emitting diode display devices |
| KR101004984B1 (ko) * | 2007-08-03 | 2011-01-04 | 도오꾜오까고오교 가부시끼가이샤 | 불소 함유 화합물, 액침 노광용 레지스트 조성물 및레지스트 패턴 형성 방법 |
| JP5150327B2 (ja) * | 2007-08-03 | 2013-02-20 | 東京応化工業株式会社 | 液浸露光用レジスト組成物およびレジストパターン形成方法 |
| JP2009098658A (ja) * | 2007-09-25 | 2009-05-07 | Fujifilm Corp | 光学フィルム、偏光板、及び画像表示装置 |
| JP5303142B2 (ja) * | 2007-11-30 | 2013-10-02 | 東京応化工業株式会社 | 含フッ素化合物、含フッ素高分子化合物、液浸露光用レジスト組成物およびレジストパターン形成方法 |
| US7981986B2 (en) * | 2008-04-29 | 2011-07-19 | 3M Innovative Properties Company | Optical films comprising fluorenol (meth)acrylate monomer |
| US20090275720A1 (en) * | 2008-04-30 | 2009-11-05 | 3M Innovative Properties Company | Ortho-benzylphenol mono(meth)acrylate monomers suitable for microstructured optical films |
| US7957621B2 (en) | 2008-12-17 | 2011-06-07 | 3M Innovative Properties Company | Light extraction film with nanoparticle coatings |
| TWI503334B (zh) * | 2009-02-19 | 2015-10-11 | Jsr Corp | 聚合物及敏輻射線性組成物、及單體 |
| WO2012022388A1 (de) * | 2010-07-22 | 2012-02-23 | Merck Patent Gmbh | Polymerstabilisierte flüssigkristallmedien und anzeigen |
| US9182662B2 (en) * | 2012-02-15 | 2015-11-10 | Rohm And Haas Electronic Materials Llc | Photosensitive copolymer, photoresist comprising the copolymer, and articles formed therefrom |
| WO2016064674A1 (en) * | 2014-10-21 | 2016-04-28 | Saint-Gobain Performance Plastics Corporation | Support for a flexible oled |
| CN107250097B (zh) * | 2015-02-16 | 2020-08-07 | 中央硝子株式会社 | 含氟α-酮羧酸酯类的实用制造方法 |
| SG11201810474SA (en) | 2016-05-27 | 2018-12-28 | 3M Innovative Properties Co | Oled display with improved color uniformity |
| JP7040864B2 (ja) | 2016-10-28 | 2022-03-23 | スリーエム イノベイティブ プロパティズ カンパニー | ナノ構造化物品 |
| KR101965194B1 (ko) * | 2017-07-12 | 2019-04-03 | 이화여자대학교 산학협력단 | 불소계 모노머 및 올리고머 화합물, 광중합형 조성물, 및 이들을 이용한 소수성 필름 |
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| CN109534968B (zh) * | 2018-11-15 | 2022-07-08 | 广东广山新材料股份有限公司 | 一种不饱和氟碳化合物及其制备方法和应用 |
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| US12161013B2 (en) | 2019-09-18 | 2024-12-03 | 3M Innovative Properties Company | Articles including nanostructured surfaces and enclosed voids, and methods of making same |
| US12464939B2 (en) | 2020-08-28 | 2025-11-04 | 3M Innovative Properties Company | Articles including nanostructured surfaces and enclosed voids, methods of making same, and optical elements |
| JP2023109483A (ja) * | 2022-01-27 | 2023-08-08 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、及び、化合物 |
| KR102898751B1 (ko) * | 2022-10-21 | 2025-12-11 | 주식회사 트리엘 | 신규한 아크릴계 화합물 및 이를 포함하는 저유전 코팅액 조성물 |
| KR102784676B1 (ko) * | 2024-01-17 | 2025-03-21 | 주식회사 트리엘 | 대면적 코팅을 위한 잉크젯용 포토레지스트 조성물 및 이의 제조방법 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE621655A (enExample) * | 1961-09-20 | |||
| US3981928A (en) * | 1962-10-30 | 1976-09-21 | Minnesota Mining And Manufacturing Company | Perfluorotertiaryalkyl ethers |
| US3321515A (en) * | 1963-04-24 | 1967-05-23 | Du Pont | Method of making fluorinated carbonyl compounds |
| US3520863A (en) * | 1965-06-24 | 1970-07-21 | Allied Chem | Novel acrylic monomers,polymers and intermediates |
| US3723507A (en) * | 1965-06-24 | 1973-03-27 | Allied Chem | Perfluoro cycloalkyl acrylates |
| US3544535A (en) * | 1965-07-26 | 1970-12-01 | Allied Chem | Novel carbinol and derivatives thereof |
| DE1668395C3 (de) * | 1966-07-11 | 1978-06-15 | Montecatini Edison S.P.A., Mailand (Italien) | Perfluorierte Ketone und Verfahren zu deren Herstellung |
| FR1547223A (fr) * | 1966-12-17 | 1968-11-22 | Dynamit Nobel Ag | Procédé de préparation d'esters phényliques |
| US4010212A (en) * | 1970-04-13 | 1977-03-01 | Minnesota Mining And Manufacturing Company | Perfluorotertiaryalkyl ethers |
| US3668223A (en) * | 1970-08-19 | 1972-06-06 | Merck & Co Inc | 2-oxo-3-benzoxepins |
| JPS5023019B1 (enExample) * | 1970-12-14 | 1975-08-05 | ||
| US5132455A (en) * | 1982-03-31 | 1992-07-21 | Exfluor Research Corporation | Method for synthesizing perfluorinated ether compounds via polyesters |
| DE3678146D1 (de) * | 1985-12-25 | 1991-04-18 | Tosoh Corp | Halogen enthaltende polyacrylat-derivate. |
| DE3620050A1 (de) * | 1986-06-14 | 1987-12-17 | Hoechst Ag | Substituierte (alpha)-fluoracrylsaeurephenylester |
| US5045397A (en) * | 1987-02-13 | 1991-09-03 | Hughes Aircraft Company | Optical adhesive system having low refractive index |
| DE3707923A1 (de) * | 1987-03-12 | 1988-09-22 | Hoechst Ag | Transparente thermoplastische formmasse |
| FR2623510B1 (fr) * | 1987-11-20 | 1992-10-23 | Ecole Nale Superieure Chimie | Polymeres a base d'halo et de methacrylates de pentafluorophenyle et leur application a la realisation de fibres optiques, de photoresists positifs, de verres organiques et de resines pour disques optiques |
| US5236919A (en) | 1989-02-28 | 1993-08-17 | Imperial Chemical Industries Plc | Quinoxalinyl derivatives suitable for use in leukotriene mediated disease |
| JP2854669B2 (ja) * | 1990-04-27 | 1999-02-03 | 株式会社 日立製作所 | 光伝送体とそれを用いた光伝送システムおよびエンジンの制御システム |
| US5136117A (en) | 1990-08-23 | 1992-08-04 | Battelle Memorial Institute | Monomeric recovery from polymeric materials |
| US5384374A (en) * | 1991-01-11 | 1995-01-24 | Minnesota Mining And Manufacturing Company | Curing fluorocarbon elastomers |
| US5223593A (en) * | 1991-08-08 | 1993-06-29 | Minnesota Mining And Manufacturing Company | Fluorine containing plastic optical fiber cores |
| DE59306756D1 (de) * | 1992-03-07 | 1997-07-24 | Minnesota Mining & Mfg | Verfahren zum Herstellen von Bauelementen für Lichtwellenleiternetze und nach diesem Verfahren hergestellte Bauelemente |
| US5420359A (en) * | 1992-12-11 | 1995-05-30 | Minnesota Mining And Manufacturing Company | Chlorofluoroether compositions and preparation thereof |
| US5350497A (en) * | 1993-05-21 | 1994-09-27 | E. I. Du Pont De Nemours And Company | Production of perfluoro(alkyl vinyl ethers) |
| US5343544A (en) * | 1993-07-02 | 1994-08-30 | Minnesota Mining And Manufacturing Company | Integrated optical fiber coupler and method of making same |
| US5466877A (en) * | 1994-03-15 | 1995-11-14 | Minnesota Mining And Manufacturing Company | Process for converting perfluorinated esters to perfluorinated acyl fluorides and/or ketones |
| US6005137A (en) * | 1997-06-10 | 1999-12-21 | 3M Innovative Properties Company | Halogenated acrylates and polymers derived therefrom |
-
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 JP JP50235299A patent/JP4065932B2/ja not_active Expired - Fee Related
- 1997-09-29 DE DE69732310T patent/DE69732310T2/de not_active Expired - Lifetime
- 1997-09-29 EP EP97909884A patent/EP1009729B1/en not_active Expired - Lifetime
- 1997-09-29 WO PCT/US1997/017437 patent/WO1998056749A1/en not_active Ceased
- 1997-09-29 AU AU47392/97A patent/AU4739297A/en not_active Abandoned
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1999
- 1999-08-23 US US09/379,156 patent/US6313245B1/en not_active Expired - Fee Related
- 1999-08-24 US US09/382,300 patent/US6288266B1/en not_active Expired - Fee Related
-
2001
- 2001-05-01 US US09/846,739 patent/US6362379B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10257711B4 (de) * | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69732310D1 (de) | 2005-02-24 |
| CN1125030C (zh) | 2003-10-22 |
| JP2002514259A (ja) | 2002-05-14 |
| US6313245B1 (en) | 2001-11-06 |
| KR100597970B1 (ko) | 2006-07-13 |
| WO1998056749A1 (en) | 1998-12-17 |
| US6362379B2 (en) | 2002-03-26 |
| US6005137A (en) | 1999-12-21 |
| AU4739297A (en) | 1998-12-30 |
| CN1259932A (zh) | 2000-07-12 |
| EP1009729A1 (en) | 2000-06-21 |
| US6288266B1 (en) | 2001-09-11 |
| EP1009729B1 (en) | 2005-01-19 |
| KR20010013585A (ko) | 2001-02-26 |
| JP4065932B2 (ja) | 2008-03-26 |
| US20010037028A1 (en) | 2001-11-01 |
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