ES2605472T3 - Compuesto de carbamato cíclico útil en composiciones curables con energía - Google Patents
Compuesto de carbamato cíclico útil en composiciones curables con energía Download PDFInfo
- Publication number
- ES2605472T3 ES2605472T3 ES10708581.3T ES10708581T ES2605472T3 ES 2605472 T3 ES2605472 T3 ES 2605472T3 ES 10708581 T ES10708581 T ES 10708581T ES 2605472 T3 ES2605472 T3 ES 2605472T3
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- Spain
- Prior art keywords
- carbamate
- compound
- acrylate
- group
- dical
- Prior art date
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- -1 Cyclic carbamate compound Chemical class 0.000 title claims abstract description 63
- 239000000203 mixture Substances 0.000 title claims description 115
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 75
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 33
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 27
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims abstract description 20
- 229920000570 polyether Chemical group 0.000 claims abstract description 20
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 16
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 14
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 72
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 45
- 238000001723 curing Methods 0.000 claims description 34
- 125000001931 aliphatic group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 230000005855 radiation Effects 0.000 claims description 21
- 125000000524 functional group Chemical group 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 238000003776 cleavage reaction Methods 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 230000007017 scission Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- JJFFNQSUUAIWHB-UHFFFAOYSA-N carbamic acid;prop-2-enoic acid Chemical compound NC(O)=O.OC(=O)C=C JJFFNQSUUAIWHB-UHFFFAOYSA-N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical group NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 claims description 4
- 229940123973 Oxygen scavenger Drugs 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims description 3
- VPJXQGSRWJZDOB-UHFFFAOYSA-O 2-carbamoyloxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(N)=O VPJXQGSRWJZDOB-UHFFFAOYSA-O 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- DJPWEXJHYGPFIU-UHFFFAOYSA-N hexadecyl carbamate Chemical compound CCCCCCCCCCCCCCCCOC(N)=O DJPWEXJHYGPFIU-UHFFFAOYSA-N 0.000 claims 1
- 238000006845 Michael addition reaction Methods 0.000 abstract description 4
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical group CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002966 varnish Substances 0.000 description 31
- 238000009472 formulation Methods 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000976 ink Substances 0.000 description 19
- 239000000463 material Substances 0.000 description 16
- 239000000178 monomer Substances 0.000 description 13
- 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
- 239000000047 product Substances 0.000 description 11
- 238000010894 electron beam technology Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- 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
- 238000006356 dehydrogenation reaction Methods 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 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 description 6
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000284 extract Substances 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
- 238000002360 preparation method Methods 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 150000003335 secondary amines Chemical group 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 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 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 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
- 238000000605 extraction Methods 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
- 210000003813 thumb Anatomy 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 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
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000012949 free radical photoinitiator Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000013067 intermediate product 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
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- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 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
- 239000004925 Acrylic resin Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 229920001451 polypropylene glycol Chemical group 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene 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 group 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
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- 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
- 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
- OILBZAPVLYOYQO-UHFFFAOYSA-N 2-[4-[2-[4-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 OILBZAPVLYOYQO-UHFFFAOYSA-N 0.000 description 1
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- GOXNUYXRIQJIEF-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1,3-oxazolidin-2-one Chemical class OCCN1CCOC1=O GOXNUYXRIQJIEF-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000012546 transfer Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15993009P | 2009-03-13 | 2009-03-13 | |
| US159930P | 2009-03-13 | ||
| PCT/GB2010/000441 WO2010103281A1 (en) | 2009-03-13 | 2010-03-11 | Cyclic carbamate compounds useful in energy-curable compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2605472T3 true ES2605472T3 (es) | 2017-03-14 |
Family
ID=42225085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10708581.3T Active ES2605472T3 (es) | 2009-03-13 | 2010-03-11 | Compuesto de carbamato cíclico útil en composiciones curables con energía |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9428471B2 (enExample) |
| EP (1) | EP2406239B1 (enExample) |
| JP (1) | JP5731413B2 (enExample) |
| KR (1) | KR20110136850A (enExample) |
| CN (1) | CN102348696B (enExample) |
| CA (1) | CA2754712A1 (enExample) |
| ES (1) | ES2605472T3 (enExample) |
| WO (1) | WO2010103281A1 (enExample) |
| ZA (1) | ZA201106470B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3033399T3 (pl) * | 2013-08-12 | 2018-03-30 | Basf Se | Farba drukarska do druku strumieniowego zawierająca n-winyloksazolidynon |
| US10320881B2 (en) * | 2014-12-09 | 2019-06-11 | Cronus Cyber Technologies Ltd. | Operating system fingerprint detection |
| CN109562596B (zh) * | 2016-08-10 | 2022-02-01 | 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 |
| US12187907B2 (en) | 2020-07-31 | 2025-01-07 | Sun Chemical Corporation | Self-initiated energy curable ink compositions |
| EP4211195A1 (en) | 2020-09-10 | 2023-07-19 | Sun Chemical Corporation | Led energy curable ink compositions |
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 |
| NZ274966A (en) * | 1993-11-22 | 1998-01-26 | Upjohn Co | Substituted-hydroxyacetyl piperazine phenyl oxazolidinone derivatives, use in pharmaceutical compositions |
| EP1272567A2 (en) | 2000-04-03 | 2003-01-08 | 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 KR KR1020117023944A patent/KR20110136850A/ko not_active Withdrawn
- 2010-03-11 JP JP2011553514A patent/JP5731413B2/ja not_active Expired - Fee Related
- 2010-03-11 WO PCT/GB2010/000441 patent/WO2010103281A1/en not_active Ceased
- 2010-03-11 CA CA2754712A patent/CA2754712A1/en not_active Abandoned
- 2010-03-11 EP EP10708581.3A patent/EP2406239B1/en active Active
- 2010-03-11 CN CN201080011808.XA patent/CN102348696B/zh active Active
- 2010-03-11 US US13/256,115 patent/US9428471B2/en active Active
- 2010-03-11 ES ES10708581.3T patent/ES2605472T3/es active Active
-
2011
- 2011-09-05 ZA ZA2011/06470A patent/ZA201106470B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010103281A1 (en) | 2010-09-16 |
| JP2012520277A (ja) | 2012-09-06 |
| KR20110136850A (ko) | 2011-12-21 |
| US9428471B2 (en) | 2016-08-30 |
| EP2406239A1 (en) | 2012-01-18 |
| US20120015159A1 (en) | 2012-01-19 |
| CA2754712A1 (en) | 2010-09-16 |
| CN102348696B (zh) | 2015-06-17 |
| CN102348696A (zh) | 2012-02-08 |
| JP5731413B2 (ja) | 2015-06-10 |
| ZA201106470B (en) | 2012-05-30 |
| EP2406239B1 (en) | 2016-09-14 |
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