JP2020521837A - 硬化性組成物及びその使用 - Google Patents
硬化性組成物及びその使用 Download PDFInfo
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- JP2020521837A JP2020521837A JP2019564457A JP2019564457A JP2020521837A JP 2020521837 A JP2020521837 A JP 2020521837A JP 2019564457 A JP2019564457 A JP 2019564457A JP 2019564457 A JP2019564457 A JP 2019564457A JP 2020521837 A JP2020521837 A JP 2020521837A
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- Prior art keywords
- meth
- group
- curable composition
- acrylate
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 179
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 147
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 claims abstract description 23
- -1 alkheteroaryl groups Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 230000005855 radiation Effects 0.000 claims description 31
- 229920005862 polyol Polymers 0.000 claims description 28
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 238000000576 coating method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 16
- 125000000962 organic group Chemical group 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 150000002148 esters Chemical group 0.000 claims description 12
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 238000010146 3D printing Methods 0.000 claims description 9
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 8
- 230000001070 adhesive effect Effects 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 238000010894 electron beam technology Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000000465 moulding Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 6
- 239000000565 sealant Substances 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- BQHDXNZNSPVVKB-UHFFFAOYSA-N diethyl 2-methylidenepropanedioate Chemical compound CCOC(=O)C(=C)C(=O)OCC BQHDXNZNSPVVKB-UHFFFAOYSA-N 0.000 claims description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004831 Hot glue Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000012939 laminating adhesive Substances 0.000 claims description 3
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical group [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 3
- 239000013307 optical fiber Substances 0.000 claims description 3
- 229920001692 polycarbonate urethane Polymers 0.000 claims description 3
- GTELLNMUWNJXMQ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO GTELLNMUWNJXMQ-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- 238000001723 curing Methods 0.000 description 28
- 238000009472 formulation Methods 0.000 description 26
- 150000003077 polyols Chemical class 0.000 description 22
- 239000000758 substrate Substances 0.000 description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 239000000178 monomer Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 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 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 125000001475 halogen functional group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 229920005906 polyester polyol Polymers 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 7
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 7
- 239000000976 ink Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 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 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 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 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 4
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 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 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZMDDERVSCYEKPQ-UHFFFAOYSA-N Ethyl (mesitylcarbonyl)phenylphosphinate Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C ZMDDERVSCYEKPQ-UHFFFAOYSA-N 0.000 description 2
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- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
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- 239000002585 base Substances 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
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- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003568 thioethers Chemical group 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- PJCBRWRFLHBSNH-UHFFFAOYSA-N (2,5-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C=CC=CC=2)=C1 PJCBRWRFLHBSNH-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
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- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 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
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl 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])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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- LOFJKBAHPJENQS-UHFFFAOYSA-N tris(oxomethylidene)chromium Chemical compound O=C=[Cr](=C=O)=C=O LOFJKBAHPJENQS-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
a)構造RaRbC=CHRc(式中、Ra及びRbは、互いに同じか又は異なり、−C(=O)XRd、−CH2C(=O)XRe、及び−C(=O)Rfから選択され、ただし、Ra及びRbは、両方ともが−CH2C(=O)XReではなく;各Xは、独立してO又はNRiであり、各Riは、H又は有機基から独立して選択され、Rcは、H又はC1若しくはC2のアルキルであり、各Rd及びReは、H、アルカリ金属若しくは有機基から独立して選択され;各Rfは有機基であり;又は、Rd、Re若しくはRfのうちの2つが、それらが結合している原子と一緒になって環を形成する)を有する少なくとも1つのコモノマーと;
b)少なくとも1つの(メタ)アクリレート官能化化合物と
を含む、硬化性組成物が提供される。
本発明の硬化性組成物は、反応性炭素−炭素二重結合(すなわちエチレン性不飽和部位)を含む化合物として一般に特徴付けられ得る(少なくとも1つの)1つ以上のコモノマーa)を含み、炭素−炭素二重結合に関与する炭素原子の1つは、2つのC=O(カルボニル)含有基で置換され、炭素−炭素二重結合のそのような炭素原子は、2つのC=O含有基のそれぞれのC=O部分の炭素原子に直接結合しているか、又は2つのC=O含有基の一方のC=O部分の炭素原子に直接結合し、他方のC=O含有基のC=O部分の炭素原子に中間的−CH2−基を介して間接的に結合している(C=C−CH2−C(=O)−部分を生成する)。炭素−炭素二重結合に関与する他の炭素原子は、非置換(末端メチレン基、C=CH2をもたらす)であるか、又はC1又はC2アルキル基で置換されている(アルケン基C=CHCH3若しくはC=CCH2CH3をもたらす)。
又は、
R及びR’は、それらが結合している原子と一緒になって、C1−C15アルキル、ハロ−(C1−C15アルキル)、C3−C12シクロアルキル、ハロ−(C3−C12シクロアルキル)、ヘテロシクリル、ヘテロシクリル−(C1−C15アルキル)、アリール、アリール−(C1−C15アルキル)、ヘテロアリール、C1−C15アルコキシ、C1−C15アルキルチオ、ハロ、ヒドロキシル、ニトロ、アジド、シアノ、アシルオキシ、カルボキシ、又はエステルで任意選択的に置換されていてもよい5〜7員複素環を形成する)を有するコモノマーa)として硬化性組成物中に存在する。
R=R’=エチル;
R=イソプロピル、R’=メチル;
R=フェニル、R’=メチル;
R=R’=フェニル;
R=R’=n−プロピル;
R=2−チオフェン、R’=トリフルオロメチル;
R=t−ブチル;R’=トリフルオロメチル;
R=n−ヘキシル、R’=トリフルオロメチル;
R=R’=イソプロピル;
R=メチル、R’=ブロモメチル;
R=2−フラニル、R’=トリフルオロメチル;
R=n−プロピル、R’=トリフルオロメチル;
R=エチル、R’=トリフルオロメチル;
R=メチル、R’=ジクロロメチル;
R=フェニル、R’=ジフルオロメチル;
R=R’=クロロメチル;
R=メチル、R’=ジフルオロメチル;
R=メチル、R’=クロロジフルオロメチル;
R=メチル、R’=ジクロロメチル;
R=4−クロロフェニル、R’=ジフルオロメチル;
R=メチル、R’=クロロメチル;
R=2,4−ジクロロフェニル、R’=トリフルオロメチル;
R=2,4−ジメトキシフェニル、R’=メチル;
R=R’=イソボルニル;
R=R’=シクロヘキシル;
R=エチル、R’=イソボルニル;
R=エチル、R’=シクロヘキシル;及び
R=4−メトキシフェニル、R’=メチル。
又は、
R1及びR2は、それらが結合している原子と一緒になって、C1−C15アルキル、ハロ−(C1−C15アルキル)、C3−C12シクロアルキル、ハロ−(C3−C12シクロアルキル)、ヘテロシクリル、ヘテロシクリル−(C1−C15アルキル)、アリール、アリール−(C1−C15アルキル)、ヘテロアリール、C1−C15アルコキシ、C1−C15アルキルチオ、ハロ、ヒドロキシル、ニトロ、アジド、シアノ、アシルオキシ、カルボキシ、又はエステルで任意選択的に置換されていてもよい5〜7員複素環を形成する)を有する1つ以上のメチレンベータ−ジケトンモノマーを含む。
R1=R2=エチル;
R1=イソプロピル、R2=メチル;
R1=フェニル、R2=メチル;
R1=R2=フェニル;
R1=R2=n−プロピル;
R1=2−チオフェン、R2=トリフルオロメチル;
R1=t−ブチル;R2=トリフルオロメチル;
R1=n−ヘキシル、R2=トリフルオロメチル;
R1=R2=イソプロピル;
R1=メチル、R2=ブロモメチル;
R1=2−フラニル、R2=トリフルオロメチル;
R1=n−プロピル、R2=トリフルオロメチル;
R1=エチル、R2=トリフルオロメチル;
R1=メチル、R2=ジクロロメチル;
R1=フェニル、R2=ジフルオロメチル;
R1=R2=クロロメチル;
R1=メチル、R2=ジフルオロメチル;
R1=メチル、R2=クロロジフルオロメチル;
R1=メチル、R2=ジクロロメチル;
R1=4−クロロフェニル、R2=ジフルオロメチル;
R1=メチル、R2=クロロメチル;
R1=2,4−ジクロロフェニル、R2=トリフルオロメチル;
R1=2,4−ジメトキシフェニル、R2=メチル;
R1=R2=イソボルニル;
R1=R2=シクロヘキシル;
R1=エチル、R2=イソボルニル;
R1=エチル、R2=シクロヘキシル;及び
R1=4−メトキシフェニル、R2=メチル。
Rd=エチル、Rf=フェニル;
Rd=エチル、Rf=n−プロピル;
Rd=エチル、Rf=メチル;
Rd=Rf=メチル;
Rd=エチル、Rf=イソプロピル;
Rd=Rf=エチル;
Rd=Rf=シクロヘキシル;
Rd=Rf=イソボルニル;
Rd=イソボルニル、Rf=エチル;
Rd=シクロヘキシル、Rf=エチル;
Rd=エチル、Rf=ベンジル;
Rd=エチル、Rf=クロロメチル;
Rd=エチル、Rf=チオフェン;
Rd=エチル、Rf=フラニル;
Rd=メチル、Rf=クロロメチル;
Rd=シクロペンチルメチル、Rf=フェニル;
Rd=エチル、Rf=ジフルオロメチル;
Rd=テトラヒドロフラニルメチル、Rf=フェニル;
Rd=エチル、Rf=1−ブロモ−エチル;
Rd=エチル、Rf=シクロヘキシル;
Rd=イソプロピル、Rf=クロロメチル;
Rd=エチル、Rf=シクロペンチル;
Rd=2−メトキシエチル、Rf=メチル;
Rd=−CH2CH2OC(=O)CH3、Rf=メチル;
Rd=フラニルメチル、Rf=メチル;及び
Rd=ベンジル、Rf=メチル;
本発明の硬化性組成物は、少なくとも1つの(メタ)アクリレート官能化化合物b)を含むことをさらに特徴とする。(メタ)アクリレート官能化化合物b)は、分子あたり1つ以上の(メタ)アクリレート官能基を有する有機化合物として説明され得る。本明細書で使用される場合、「(メタ)アクリレート」という用語は、アクリレート官能基及びメタクリレート官能基の両方を指す。本発明における使用に適した(メタ)アクリレート官能化化合物は、一般に、エステル基に対してアルファの少なくとも1つの炭素−炭素二重結合、特にフリーラジカル反応又はアニオン反応、特に紫外線放射又は電子ビーム放射によって開始される反応に関与し得る炭素−炭素二重結合を含むエチレン性不飽和化合物(少なくとも1つのα,β−不飽和エステル部分を含む化合物)として説明され得る。そのような反応は、重合又は硬化をもたらすことができ、それにより(メタ)アクリレート官能化化合物が重合マトリックス又はポリマー鎖の一部になる。本発明の様々な実施形態において、(メタ)アクリレート官能化化合物は、分子あたり1つ、2つ、3つ、4つ、5つ、又はそれ以上の(メタ)アクリレート官能基を含んでもよい。異なる数の(メタ)アクリレート基を含む複数の(メタ)アクリレート官能化化合物の組み合わせが、本発明の硬化性組成物において利用され得る。
硬化性組成物を紫外線等の光を使用して硬化させる場合、一般に、c)1つ以上の光開始剤を含むように組成物を配合することが望ましい。しかしながら、電子ビーム又は化学的硬化が使用される場合、硬化性組成物はいかなる光開始剤も含む必要はない。
本発明の硬化性組成物は、c)の代わりに、又は上記成分a)、b)及びc)に加えて、1つ以上の添加剤を任意選択的に含有してもよい。そのような添加剤は、これらに限定されないが、酸化防止剤、紫外線吸収剤、光安定剤、消泡剤、流動剤又はレベリング剤、着色剤、顔料、分散剤(湿潤剤)、スリップ添加剤、充填剤、チキソトロープ剤、艶消し剤、フリーラジカル重合性官能基を含まないアクリル樹脂等の熱可塑性物質、ワックス、又はコーティング、シーラント、接着剤、成形若しくはインク技術で従来利用されている添加剤のいずれかを含む他の様々な添加剤を含む。
本発明の硬化性組成物は、他の可能な用途の中でも、インク(食品包装用を含むグラフィックアート用途)、成形樹脂、3D印刷樹脂、コーティング(例えば光ファイバコーティング)、シーラント及び接着剤(例えばUV硬化性ラミネート接着剤、UV硬化性ホットメルト接着剤)として有用である。
a)本発明による硬化性組成物の第1の層を表面にコーティングするステップと;
b)第1の層を硬化させて、硬化した第1の層を提供するステップと;
c)硬化性組成物の第2の層を硬化した第1の層にコーティングするステップと;
d)第2の層を硬化させて、硬化した第1の層に接着した硬化した第2の層を提供するステップと;
e)ステップc)及びd)を必要な回数繰り返して、三次元物品を構築するステップと
を含む。
a)本発明による液体形態の硬化性組成物の第1の層を表面にコーティングするステップと;
b)第1の層を化学線に画像通りに曝露して、第1の曝露された画像化断面を形成するステップであって、放射は、曝露領域における層の少なくとも部分的な硬化(例えば、少なくとも80%又は少なくとも90%の硬化)をもたらすのに十分な強度及び持続時間の放射であるステップと;
c)硬化性組成物の追加の層を、以前に曝露された画像化断面にコーティングするステップと;
d)追加の層を化学線に画像通りに曝露して、追加の画像化断面を形成するステップであって、放射は、曝露領域における追加の層の少なくとも部分的な硬化(例えば、少なくとも80%又は少なくとも90%の硬化)をもたらし、以前に曝露された画像化断面への追加の層の接着をもたらすのに十分な強度及び持続時間の放射であるステップと;
e)ステップc)及びd)を必要な回数繰り返して、三次元物品を構築するステップと
を含む方法を提供する。
b)少なくとも1つの(メタ)アクリレート官能化化合物と
を含む、それらから本質的になる、又はそれらからなる硬化性組成物。
又は、
R1及びR2は、それらが結合している原子と一緒になって、C1−C15アルキル、ハロ−(C1−C15アルキル)、C3−C12シクロアルキル、ハロ−(C3−C12シクロアルキル)、ヘテロシクリル、ヘテロシクリル−(C1−C15アルキル)、アリール、アリール−(C1−C15アルキル)、ヘテロアリール、C1−C15アルコキシ、C1−C15アルキルチオ、ハロ、ヒドロキシル、ニトロ、アジド、シアノ、アシルオキシ、カルボキシ、又はエステルで任意選択的に置換されていてもよい5〜7員複素環を形成する)を有する1つ以上のメチレンベータ−ジケトンモノマーを含む、態様1〜3の硬化性組成物。
a)態様1〜17のいずれかによる硬化性組成物の第1の層を表面にコーティングするステップと;
b)第1の層を硬化させて、硬化した第1の層を提供するステップと;
c)硬化性組成物の第2の層を硬化した第1の層にコーティングするステップと;
d)第2の層を硬化させて、硬化した第1の層に接着した硬化した第2の層を提供するステップと;
e)ステップc)及びd)を必要な回数繰り返して、三次元物品を構築するステップと
を含む方法。
Claims (26)
- a)構造RaRbC=CHRc(式中、Ra及びRbは、互いに同じか又は異なり、−C(=O)XRd、−CH2C(=O)XRe、及び−C(=O)Rfから選択され、ただし、Ra及びRbは、両方ともが−CH2C(=O)XReではなく;各Xは、独立してO又はNRiであり、各Riは、H又は有機基から独立して選択され、Rcは、H又はC1若しくはC2のアルキルであり、各Rd及びReは、H、アルカリ金属若しくは有機基から独立して選択され;各Rfは有機基であり;又は、Rd、Re若しくはRfのうちの2つが、それらが結合している原子と一緒になって環を形成する)を有する少なくとも1つのコモノマーと;
b)少なくとも1つの(メタ)アクリレート官能化化合物と
を含む、硬化性組成物。 - 各Rd、Re、Rf及びRgが、置換又は非置換であってもよい、アルキル基、アルケニル基、シクロアルキル基、ヘテロシクリル基、アルキルヘテロシクリル基、アリール基、アラルキル基、アルカリール基、ヘテロアリール基、アルクヘテロアリール基、オキシアルキレン基又はポリオキシアルキレン基から独立して選択される、請求項1に記載の硬化性組成物。
- 1,1−ジエステル−1−アルケン、1,1−ジケト−1−アルケン、1−エステル−1−ケト−1−アルケン及びイタコネートからなる群から選択される少なくとも1つのコモノマーa)を含む、請求項1又は2に記載の硬化性組成物。
- Ra及びRbが両方とも−C(=O)ORdであり、RcがHである少なくとも1つのコモノマーa)を含む、請求項1〜3のいずれかに記載の硬化性組成物。
- Ra及びRbが両方とも−C(=O)Rfであり、RcがHである少なくとも1つのコモノマーa)を含む、請求項1〜3のいずれかに記載の硬化性組成物。
- Raが−C(=O)ORdであり、Rbが−C(=O)Rfであり、RcがHである少なくとも1つのコモノマーa)を含む、請求項1〜3のいずれかに記載の硬化性組成物。
- Raが−C(=O)ORdであり、Rbが−CH2C(=O)OReであり、RcがHである少なくとも1つのコモノマーa)を含む、請求項1又は2に記載の硬化性組成物。
- コモノマーa)として少なくとも1つのメチレンマロネートを含む、請求項1〜3のいずれかに記載の硬化性組成物。
- R及びR’が同じであり、C1−C15アルキル及びC5−C12シクロアルキルからなる群から選択される、請求項9に記載の硬化性組成物。
- 前記少なくとも1つのコモノマーa)が、ジシクロヘキシルメチレンマロネート、ジイソボルニルメチレンマロネート、エチルイソボルニルメチレンマロネート、ジヘキシルメチレンマロネート及びジエチルメチレンマロネートからなる群から選択される少なくとも1つのメチレンマロネートを含む、請求項1〜3及び8〜10のいずれかに記載の硬化性組成物。
- 構造(II)
又は、
R1及びR2は、それらが結合している原子と一緒になって、C1−C15アルキル、ハロ−(C1−C15アルキル)、C3−C12シクロアルキル、ハロ−(C3−C12シクロアルキル)、ヘテロシクリル、ヘテロシクリル−(C1−C15アルキル)、アリール、アリール−(C1−C15アルキル)、ヘテロアリール、C1−C15アルコキシ、C1−C15アルキルチオ、ハロ、ヒドロキシル、ニトロ、アジド、シアノ、アシルオキシ、カルボキシ、又はエステルで任意選択的に置換されていてもよい5〜7員複素環を形成する)を有する1つ以上のメチレンベータ−ジケトンモノマーを含む、請求項1〜3のいずれかに記載の硬化性組成物。 - 前記少なくとも1つの(メタ)アクリレート官能化化合物b)が、脂肪族モノアルコール(非アルコキシル化)の(メタ)アクリレートエステル、アルコキシル化脂肪族モノアルコールの(メタ)アクリレートエステル、脂肪族ポリオール(非アルコキシル化)の(メタ)アクリレートエステル、アルコキシル化脂肪族ポリオールの(メタ)アクリレートエステル、芳香族アルコール(非アルコキシル化)の(メタ)アクリレートエステル、アルコキシル化芳香族アルコールの(メタ)アクリレートエステル、エポキシ(メタ)アクリレート、ポリエーテル(メタ)アクリレート、ウレタン(メタ)アクリレート、ポリエステル(メタ)アクリレート、及びそれらのアミン及びスルフィド変性誘導体、並びにそれらの組み合わせからなる群から選択される少なくとも1つの(メタ)アクリレート官能化化合物を含む、請求項1〜12のいずれかに記載の硬化性組成物。
- 少なくとも1つの(メタ)アクリレート官能化化合物b)が、イソボルニル(メタ)アクリレート、エトキシル化トリメチロールプロパントリアクリレート、トリシクロデカンジメタノールジアクリレート、ポリエーテル脂肪族ウレタンアクリレート及びポリカーボネートウレタンアクリレートからなる群から選択される少なくとも1つの(メタ)アクリレート官能化化合物を含む、請求項1〜13のいずれかに記載の硬化性組成物。
- コモノマーa)及び(メタ)アクリレート官能化化合物b)の総重量を基準として、合計で約1重量%〜約99重量%のコモノマーa)、及び合計で約1重量%〜約99重量%の(メタ)アクリレート官能化化合物b)を含む、請求項1〜14のいずれかに記載の硬化性組成物。
- コモノマーa)及び(メタ)アクリレート官能化化合物b)の総重量を基準として、合計で約10重量%〜約90重量%のコモノマーa)、及び合計で約10重量%〜約90重量%の(メタ)アクリレート官能化化合物b)を含む、請求項1〜15のいずれかに記載の硬化性組成物。
- c)少なくとも1つの光開始剤をさらに含む、請求項1〜16のいずれかに記載の硬化性組成物。
- 請求項1〜17のいずれかに記載の硬化性組成物を硬化させることにより得られる硬化組成物。
- 請求項1〜17のいずれかに記載の硬化性組成物を硬化させることを含む、硬化組成物を作製する方法。
- 硬化性組成物が、放射線に曝露される、請求項19に記載の方法。
- 硬化性組成物が、紫外線放射又は電子ビーム放射に曝露される、請求項19又は20に記載の方法。
- 三次元物品を作製する方法であって、
a)請求項1〜17のいずれかに記載の硬化性組成物の第1の層を表面にコーティングするステップと;
b)前記第1の層を硬化させて、硬化した第1の層を提供するステップと;
c)前記硬化性組成物の第2の層を前記硬化した第1の層にコーティングするステップと;
d)前記第2の層を硬化させて、前記硬化した第1の層に接着した硬化した第2の層を提供するステップと;
e)ステップc)及びd)を必要な回数繰り返して、前記三次元物品を構築するステップと
を含む方法。 - 硬化させるステップが、硬化性組成物の層を放射線に曝露することにより実行される、請求項22に記載の方法。
- 光ファイバコーティング等のコーティング、UV硬化ラミネート接着剤若しくはUV硬化性ホットメルト接着剤等の接着剤、シーラント、インク、3D印刷樹脂又は成形樹脂における、請求項1〜17のいずれかに記載の硬化性組成物の使用。
- 3D物品の作製における、請求項1〜17のいずれかに記載の硬化性組成物の使用。
- 請求項1〜17のいずれかに記載の硬化性組成物の使用により得られる3D物品。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023149445A1 (ja) * | 2022-02-07 | 2023-08-10 | ナミックス株式会社 | 液状重合性組成物及びそれを用いる硬化性樹脂組成物 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
WO2020050932A1 (en) * | 2018-09-04 | 2020-03-12 | Applied Materials, Inc. | Formulations for advanced polishing pads |
TR201906545A2 (tr) * | 2019-05-02 | 2020-09-21 | Bahcesehir Ueniversitesi | Ultravi̇yole (uv) işin etki̇si̇ i̇le hizla kürleşebi̇lme özelli̇ği̇ne sahi̇p poli̇meri̇k malzeme üreti̇mi̇ |
US11932571B2 (en) | 2019-05-24 | 2024-03-19 | Covestro (Netherland) B.V. | Radiation curable compositions for coating optical fiber with enhanced high-speed processability |
EP3990254A1 (en) * | 2019-06-26 | 2022-05-04 | Henkel IP & Holding GmbH | Curable compositions |
EP4038151A1 (en) | 2019-10-01 | 2022-08-10 | 3D Systems, Inc. | Optically active build materials for 3d printing |
EP3838592A1 (en) * | 2019-12-17 | 2021-06-23 | Evonik Operations GmbH | Composition comprising polyesters for additive manufacturing |
WO2021150844A1 (en) | 2020-01-24 | 2021-07-29 | Sirrus, Inc. | Compositions containing 1,1-disubstituted activated alkenes useful in additive manufacturing and articles formed therefrom |
WO2021183340A1 (en) | 2020-03-10 | 2021-09-16 | Sirrus, Inc. | Radiation cured copolymers of dicarbonyl substituted-l-alkenes and electron rich comonomers |
FR3116824B1 (fr) * | 2020-12-01 | 2023-11-03 | Bostik Sa | Composition adhésive bicomposante à base de monomère itaconate |
EP4151410A1 (en) | 2021-09-17 | 2023-03-22 | Arkema France | Photosensitive composition |
CN114316250B (zh) * | 2021-12-30 | 2024-06-18 | 深圳飞扬骏研新材料股份有限公司 | 一种聚醚族仲胺酯树脂及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2330033A (en) * | 1939-11-16 | 1943-09-21 | Gen Electric | Method of preparing methylene malonic esters |
JPS6462363A (en) * | 1985-04-12 | 1989-03-08 | Ensain Bitsukufuoode Ind Inc | Paint and optical article and optical fiber using the same |
JPH1087566A (ja) * | 1996-09-09 | 1998-04-07 | Nof Corp | ヒドロキシアルキルフェノン誘導体及びその重合体並びに光重合開始剤 |
JP2000327724A (ja) * | 1999-05-25 | 2000-11-28 | Toagosei Co Ltd | 活性エネルギー線硬化型組成物 |
WO2017009184A1 (en) * | 2015-07-10 | 2017-01-19 | Arkema France | Curable compositions comprising mono-functional acrylates |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2313501A (en) | 1939-08-15 | 1943-03-09 | Eastman Kodak Co | Process for preparing methylene dialkyl malonates |
FR1115001A (fr) * | 1954-11-20 | 1956-04-18 | Cie Francaise Des Plastiques I | Procédé d'obtention de copolymères méthacryliques en émulsion |
DE1569968B1 (de) | 1960-10-19 | 1969-11-06 | Eastman Kodak Co | Verwendung von hochgereinigten monomeren Estern der Methylenmalonsaeure als autopolymerisierbare Klebstoffe |
US3221745A (en) | 1962-09-12 | 1965-12-07 | Eastman Kodak Co | Method of bonding body tissue together using methylenemalonic acid esters |
US3557185A (en) | 1967-03-06 | 1971-01-19 | Toa Gosei Chem Ind | Stabilized alpha-cyanoacrylate adhesive compositions |
DE2042610C3 (de) | 1970-08-27 | 1979-03-15 | Wacker-Chemie Gmbh, 8000 Muenchen | Verfahren zur Herstellung von Methylenmalonester |
US3975422A (en) | 1972-11-21 | 1976-08-17 | Johnson & Johnson | Preparation of bis (2-cyanoacrylate)monomers |
US4049698A (en) | 1976-08-05 | 1977-09-20 | Eastman Kodak Company | Process for producing methylene malonic esters |
US4160864A (en) | 1976-09-07 | 1979-07-10 | Eastman Kodak Company | Adhesive compositions comprising methyl allyl methylenemalonate |
US4056543A (en) | 1976-09-07 | 1977-11-01 | Eastman Kodak Company | Process of preparing substituted acrylates |
FR2684681B1 (fr) * | 1985-04-12 | 1998-07-31 | Ensign Bickford Ind Inc | Compositions de revetement, procede de revetement, et article en verre revetu. |
FR2611705B1 (fr) | 1987-03-05 | 1989-07-13 | Union Pharma Scient Appl | Procede de preparation de monesters ou diesters de l'acide endoethano-9, 10 dihydro-9, 10 anthracene bicarboxylique-11, 11, nouveaux monesters ou diesters ainsi prepares et utilisation de ceux-ci pour la preparation de methylenemalonates symetriques ou asymetriques |
CN1154129A (zh) * | 1994-06-28 | 1997-07-09 | 三点医药有限公司 | pH调节的生物相容性单体和聚合物组合物 |
US5550172A (en) | 1995-02-07 | 1996-08-27 | Ethicon, Inc. | Utilization of biocompatible adhesive/sealant materials for securing surgical devices |
DE19508049C2 (de) | 1995-02-23 | 1997-02-06 | Schering Ag | Verwendung von Methylenmalondiesterderivaten zur Herstellung von gasenthaltenden Mikropartikeln |
FR2755136B1 (fr) | 1996-10-25 | 1999-01-22 | Virsol | Procede de preparation de nanoparticules de methylidene malonate, nanoparticules contenant eventuellement une ou plusieurs molecules biologiquement actives et compositions pharmaceutiques les contenant |
US6353268B1 (en) | 1997-08-22 | 2002-03-05 | Micron Technology, Inc. | Semiconductor die attachment method and apparatus |
FR2774096B1 (fr) | 1998-01-29 | 2000-04-07 | Virsol | Nouveaux copolymeres tensioactifs a base de methylidene malonate |
FR2778100B1 (fr) | 1998-04-29 | 2001-05-04 | Virsol | Nouvelles microspheres a base de poly(methylidene malonate), leur procede de preparation et compositions pharmaceutiques les contenant |
US6512023B1 (en) | 1998-06-18 | 2003-01-28 | Closure Medical Corporation | Stabilized monomer adhesive compositions |
FR2789314B1 (fr) * | 1999-02-09 | 2001-04-27 | Virsol | Materiau de suture de plaies a base de methylidene malonate |
US6245933B1 (en) | 1999-11-19 | 2001-06-12 | Closure Medical Corporation | Transesterification method for making cyanoacrylates |
FR2812551B1 (fr) | 2000-08-07 | 2003-03-28 | Virsol | Forme pharmaceutique comprenant un materiau support a base de methylidene malonate et un facteur de regulation cellulaire |
CA2513410A1 (en) * | 2003-01-22 | 2004-08-19 | Kaneka Corporation | Polymer and curable compositions improved in storage stability |
SG189937A1 (en) * | 2010-10-20 | 2013-06-28 | Bioformix Inc | Synthesis of methylene malonates using rapid recovery in the presence of a heat transfer agent |
JP6267643B2 (ja) | 2011-10-19 | 2018-01-24 | シラス・インコーポレイテッド | 多官能性モノマー、多官能性モノマーを製造する方法、これらから形成された重合性組成物および製品 |
EP2831125B1 (en) | 2012-03-30 | 2016-10-05 | Sirrus, Inc. | Methods for activating polymerizable compositions, polymerizable systems, and products formed thereby |
WO2013149173A1 (en) * | 2012-03-30 | 2013-10-03 | Bioformix Inc. | Ink and coating formulations and polymerizable systems for producing the same |
EP2943462B1 (en) | 2013-01-11 | 2018-06-27 | Sirrus, Inc. | Method to obtain methylene malonate via bis(hydroxymethyl) malonate pathway |
EP3161084B1 (en) * | 2014-06-24 | 2020-02-26 | 3M Innovative Properties Company | Adhesive precursor composition, two-part adhesive kit, and method of making an adhesive composition |
CN105294914B (zh) * | 2014-07-18 | 2017-11-21 | 大金工业株式会社 | 含氟共聚物和溶剂型涂料用组合物 |
DE102015105993A1 (de) * | 2015-04-20 | 2016-10-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Mittel zur Erzeugung eines Druckbildes und Verwendung hiervon als Druckfarbe insbesondere zum 3D-Druck |
US9567475B1 (en) * | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
CN110891979A (zh) | 2017-07-14 | 2020-03-17 | 赛鲁斯股份有限公司 | 亚甲基丙二酸酯的uv固化工艺 |
-
2018
- 2018-05-23 CA CA3064314A patent/CA3064314A1/en active Pending
- 2018-05-23 JP JP2019564457A patent/JP2020521837A/ja active Pending
- 2018-05-23 KR KR1020197037855A patent/KR102571880B1/ko active IP Right Grant
- 2018-05-23 EP EP18727757.9A patent/EP3630857A1/en active Pending
- 2018-05-23 WO PCT/EP2018/063465 patent/WO2018219729A1/en active Application Filing
- 2018-05-23 CN CN201880036549.2A patent/CN110709436B/zh active Active
- 2018-05-23 US US16/617,085 patent/US11591425B2/en active Active
- 2018-05-29 TW TW107118317A patent/TWI675075B/zh active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2330033A (en) * | 1939-11-16 | 1943-09-21 | Gen Electric | Method of preparing methylene malonic esters |
JPS6462363A (en) * | 1985-04-12 | 1989-03-08 | Ensain Bitsukufuoode Ind Inc | Paint and optical article and optical fiber using the same |
JPH1087566A (ja) * | 1996-09-09 | 1998-04-07 | Nof Corp | ヒドロキシアルキルフェノン誘導体及びその重合体並びに光重合開始剤 |
JP2000327724A (ja) * | 1999-05-25 | 2000-11-28 | Toagosei Co Ltd | 活性エネルギー線硬化型組成物 |
WO2017009184A1 (en) * | 2015-07-10 | 2017-01-19 | Arkema France | Curable compositions comprising mono-functional acrylates |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023149445A1 (ja) * | 2022-02-07 | 2023-08-10 | ナミックス株式会社 | 液状重合性組成物及びそれを用いる硬化性樹脂組成物 |
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US20200277423A1 (en) | 2020-09-03 |
CN110709436B (zh) | 2022-06-28 |
WO2018219729A1 (en) | 2018-12-06 |
KR20200015581A (ko) | 2020-02-12 |
CN110709436A (zh) | 2020-01-17 |
CA3064314A1 (en) | 2018-12-06 |
TWI675075B (zh) | 2019-10-21 |
KR102571880B1 (ko) | 2023-08-28 |
EP3630857A1 (en) | 2020-04-08 |
TW201903065A (zh) | 2019-01-16 |
US11591425B2 (en) | 2023-02-28 |
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