KR20110136850A - 에너지-경화성 조성물에 유용한 사이클릭 카바메이트 화합물 - Google Patents
에너지-경화성 조성물에 유용한 사이클릭 카바메이트 화합물 Download PDFInfo
- Publication number
- KR20110136850A KR20110136850A KR1020117023944A KR20117023944A KR20110136850A KR 20110136850 A KR20110136850 A KR 20110136850A KR 1020117023944 A KR1020117023944 A KR 1020117023944A KR 20117023944 A KR20117023944 A KR 20117023944A KR 20110136850 A KR20110136850 A KR 20110136850A
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- KR
- South Korea
- Prior art keywords
- cyclic carbamate
- acrylate
- formula
- aliphatic
- compound
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 121
- -1 Cyclic Carbamate Compounds Chemical class 0.000 title claims abstract description 92
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 46
- 239000000976 ink Substances 0.000 claims abstract description 21
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 239000000853 adhesive Substances 0.000 claims abstract description 8
- 230000001070 adhesive effect Effects 0.000 claims abstract description 8
- 229940123973 Oxygen scavenger Drugs 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 47
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 38
- 125000001931 aliphatic group Chemical group 0.000 claims description 32
- 238000001723 curing Methods 0.000 claims description 32
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 29
- 150000003254 radicals Chemical class 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 17
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 16
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 229920000570 polyether Chemical group 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
- 238000003776 cleavage reaction Methods 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 12
- 230000007017 scission Effects 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000006845 Michael addition reaction Methods 0.000 claims description 10
- 238000010894 electron beam technology Methods 0.000 claims description 10
- 125000005647 linker group Chemical group 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical group P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JJFFNQSUUAIWHB-UHFFFAOYSA-N carbamic acid;prop-2-enoic acid Chemical compound NC(O)=O.OC(=O)C=C JJFFNQSUUAIWHB-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 2
- PZRBEFHNJXWNAM-UHFFFAOYSA-N 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1CCOC1=O PZRBEFHNJXWNAM-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002966 varnish Substances 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000009472 formulation Methods 0.000 description 19
- 239000000463 material Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 12
- VCVICWZSSHBMCO-UHFFFAOYSA-N 1,3-oxazolidin-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1NCCO1 VCVICWZSSHBMCO-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 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 7
- 239000000284 extract Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 150000003141 primary amines Chemical group 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- 210000003813 thumb Anatomy 0.000 description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 5
- 239000012958 Amine synergist Substances 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- GOXNUYXRIQJIEF-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,3-oxazolidin-2-one Chemical compound OCCN1CCOC1=O GOXNUYXRIQJIEF-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012949 free radical photoinitiator Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- VUEZBQJWLDBIDE-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidin-2-one Chemical compound C=CN1CCOC1=O VUEZBQJWLDBIDE-UHFFFAOYSA-N 0.000 description 2
- HIBSYUPTCGGRSD-UHFFFAOYSA-N 3-prop-2-enoyl-1,3-oxazolidin-2-one Chemical compound C=CC(=O)N1CCOC1=O HIBSYUPTCGGRSD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CC(OCCCCCOC(CCC(CCCN(CCC(OCCN(CCO1)C1=O)=*)CCC(OCC*(CCO1)C1=O)=O)CCC(OCCC(CCO1)C1=O)=O)=O)=O Chemical compound CC(OCCCCCOC(CCC(CCCN(CCC(OCCN(CCO1)C1=O)=*)CCC(OCC*(CCO1)C1=O)=O)CCC(OCCC(CCO1)C1=O)=O)=O)=O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 239000003999 initiator Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
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- 239000013067 intermediate product Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
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- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 description 1
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 description 1
- RZTOEFCZAWZFQU-UHFFFAOYSA-N 1-(2-oxo-1,3-oxazolidin-3-yl)propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)CN1CCOC1=O RZTOEFCZAWZFQU-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KNUUQQVISASUMX-UHFFFAOYSA-N 1H-pyrrol-2-yloxysilane Chemical compound [SiH3]OC1=CC=CN1 KNUUQQVISASUMX-UHFFFAOYSA-N 0.000 description 1
- SOBZYRBYGDVKBB-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO.OCC(CO)(CO)CO SOBZYRBYGDVKBB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical compound IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 description 1
- NLFPADOUBJFWCR-UHFFFAOYSA-N C(C=C)(=O)O.OCCN1C(OC(C1)C)=O Chemical compound C(C=C)(=O)O.OCCN1C(OC(C1)C)=O NLFPADOUBJFWCR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000004743 Polypropylene Chemical group 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical class CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XRMBQHTWUBGQDN-UHFFFAOYSA-N [2-[2,2-bis(prop-2-enoyloxymethyl)butoxymethyl]-2-(prop-2-enoyloxymethyl)butyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CC)COCC(CC)(COC(=O)C=C)COC(=O)C=C XRMBQHTWUBGQDN-UHFFFAOYSA-N 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
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- OEPYYJQFSXOYAX-UHFFFAOYSA-N dioxazolidin-4-one;piperazine Chemical compound C1CNCCN1.O=C1COON1 OEPYYJQFSXOYAX-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
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- 125000006308 propyl amino group Chemical group 0.000 description 1
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- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- GLBXJBWNPRCFCY-UHFFFAOYSA-N tert-butyl 2-silyloxypyrrole-1-carboxylate Chemical class CC(C)(C)OC(=O)N1C=CC=C1O[SiH3] GLBXJBWNPRCFCY-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/66—Additives characterised by particle size
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15993009P | 2009-03-13 | 2009-03-13 | |
| US61/159,930 | 2009-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110136850A true KR20110136850A (ko) | 2011-12-21 |
Family
ID=42225085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117023944A Withdrawn KR20110136850A (ko) | 2009-03-13 | 2010-03-11 | 에너지-경화성 조성물에 유용한 사이클릭 카바메이트 화합물 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9428471B2 (https=) |
| EP (1) | EP2406239B1 (https=) |
| JP (1) | JP5731413B2 (https=) |
| KR (1) | KR20110136850A (https=) |
| CN (1) | CN102348696B (https=) |
| CA (1) | CA2754712A1 (https=) |
| ES (1) | ES2605472T3 (https=) |
| WO (1) | WO2010103281A1 (https=) |
| ZA (1) | ZA201106470B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105431497A (zh) * | 2013-08-12 | 2016-03-23 | 巴斯夫欧洲公司 | 包含n-乙烯基噁唑烷酮的喷墨印刷油墨 |
| EP3230886B1 (en) * | 2014-12-09 | 2021-11-17 | Cronus Cyber Technologies Ltd. | Operating system fingerprint detection |
| CN114292212B (zh) * | 2016-08-10 | 2024-07-05 | 阿科玛法国公司 | 含有环状结构基元、氨基甲酸酯/脲基连接单元和可自由基聚合的官能团的化合物 |
| MX2023001334A (es) | 2020-07-31 | 2023-03-06 | Sun Chemical Corp | Composiciones de tinta curables por energia autoiniciada. |
| BR112023001426A2 (pt) | 2020-09-10 | 2023-03-28 | Sun Chemical Corp | Composições de tinta curáveis por energia do led |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905690A (en) | 1959-09-22 | Vinylation of oxazolidinones | ||
| US2818362A (en) | 1954-05-18 | 1957-12-31 | American Cyanamid Co | N-vinyl-2-oxazolidone and polymerization products thereof and method of making |
| US3268485A (en) | 1963-05-01 | 1966-08-23 | Dow Chemical Co | Polymers of 3-(2-hydroxyalkyl) oxazolidinone acrylates and methacrylates |
| US4675374A (en) * | 1984-03-26 | 1987-06-23 | Gus Nichols | Solventless polymeric composition reaction product of (1) adduct of amine and acrylate with (2) polyacrylate |
| US4639472A (en) | 1984-12-17 | 1987-01-27 | The Dow Chemical Company | N-vinyl-2-oxazolidinones as reactive diluents in actinic radiation curable coatings |
| US4933462A (en) | 1988-07-25 | 1990-06-12 | The Dow Chemical Company | Synthesis of 3-(2-hydroxyethyl)-2-oxazolidinones |
| GB9014299D0 (en) | 1990-06-27 | 1990-08-15 | Domino Printing Sciences Plc | Ink composition |
| US5358946A (en) * | 1992-05-29 | 1994-10-25 | The Du Pont Merck Pharmaceutical Company | Heterocycle-substituted amides, carbamates and ureas as agents for the treatment of atherosclerosis |
| CA2174107C (en) * | 1993-11-22 | 2005-04-12 | Steven J. Brickner | Esters of substituted-hydroxyacetyl piperazine phenyl oxazolidinones |
| US6965019B2 (en) | 2000-04-03 | 2005-11-15 | Sun Chemical Corporation | Mono-and bis-hydrazone pigments |
| TW200500360A (en) * | 2003-03-01 | 2005-01-01 | Astrazeneca Ab | Hydroxymethyl compounds |
| KR100854211B1 (ko) * | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| TWI389897B (zh) * | 2005-02-22 | 2013-03-21 | Chugai Pharmaceutical Co Ltd | 1- (2H) -isoquinolinone derivatives |
| TWI357902B (en) * | 2005-04-01 | 2012-02-11 | Lg Life Science Ltd | Dipeptidyl peptidase-iv inhibiting compounds, meth |
| CA2570090C (en) | 2006-12-06 | 2014-08-19 | Brightside Technologies Inc. | Representing and reconstructing high dynamic range images |
-
2010
- 2010-03-11 CN CN201080011808.XA patent/CN102348696B/zh active Active
- 2010-03-11 CA CA2754712A patent/CA2754712A1/en not_active Abandoned
- 2010-03-11 US US13/256,115 patent/US9428471B2/en active Active
- 2010-03-11 KR KR1020117023944A patent/KR20110136850A/ko not_active Withdrawn
- 2010-03-11 JP JP2011553514A patent/JP5731413B2/ja not_active Expired - Fee Related
- 2010-03-11 ES ES10708581.3T patent/ES2605472T3/es active Active
- 2010-03-11 EP EP10708581.3A patent/EP2406239B1/en active Active
- 2010-03-11 WO PCT/GB2010/000441 patent/WO2010103281A1/en not_active Ceased
-
2011
- 2011-09-05 ZA ZA2011/06470A patent/ZA201106470B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010103281A1 (en) | 2010-09-16 |
| JP5731413B2 (ja) | 2015-06-10 |
| EP2406239A1 (en) | 2012-01-18 |
| CA2754712A1 (en) | 2010-09-16 |
| US20120015159A1 (en) | 2012-01-19 |
| JP2012520277A (ja) | 2012-09-06 |
| ES2605472T3 (es) | 2017-03-14 |
| CN102348696B (zh) | 2015-06-17 |
| US9428471B2 (en) | 2016-08-30 |
| ZA201106470B (en) | 2012-05-30 |
| CN102348696A (zh) | 2012-02-08 |
| EP2406239B1 (en) | 2016-09-14 |
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