JP7214738B2 - 硬化性組成物 - Google Patents
硬化性組成物 Download PDFInfo
- Publication number
- JP7214738B2 JP7214738B2 JP2020536244A JP2020536244A JP7214738B2 JP 7214738 B2 JP7214738 B2 JP 7214738B2 JP 2020536244 A JP2020536244 A JP 2020536244A JP 2020536244 A JP2020536244 A JP 2020536244A JP 7214738 B2 JP7214738 B2 JP 7214738B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- ethylenically unsaturated
- curable composition
- acrylate
- polymerizable
- 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 description 256
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 188
- 150000001875 compounds Chemical class 0.000 claims description 180
- -1 methyleneoxymethylene Chemical group 0.000 claims description 75
- 125000000623 heterocyclic group Chemical group 0.000 claims description 69
- 229910052751 metal Inorganic materials 0.000 claims description 65
- 239000002184 metal Substances 0.000 claims description 62
- 150000004696 coordination complex Chemical class 0.000 claims description 58
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 50
- 238000001723 curing Methods 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 29
- 230000005855 radiation Effects 0.000 claims description 25
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 21
- 150000002118 epoxides Chemical class 0.000 claims description 21
- 229910052725 zinc Inorganic materials 0.000 claims description 20
- 239000004609 Impact Modifier Substances 0.000 claims description 18
- 229920001400 block copolymer Polymers 0.000 claims description 18
- 150000002921 oxetanes Chemical class 0.000 claims description 17
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 150000007942 carboxylates Chemical class 0.000 claims description 14
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 150000002596 lactones Chemical class 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 238000010146 3D printing Methods 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 238000001029 thermal curing Methods 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 10
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052775 Thulium Inorganic materials 0.000 claims description 7
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 229910052735 hafnium Inorganic materials 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 229910052726 zirconium Inorganic materials 0.000 claims description 7
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052684 Cerium Inorganic materials 0.000 claims description 6
- 229910052691 Erbium Inorganic materials 0.000 claims description 6
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 6
- 229910052779 Neodymium Inorganic materials 0.000 claims description 6
- 229910052772 Samarium Inorganic materials 0.000 claims description 6
- 229910052771 Terbium Inorganic materials 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 229910052733 gallium Inorganic materials 0.000 claims description 6
- 229910052746 lanthanum Inorganic materials 0.000 claims description 6
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052689 Holmium Inorganic materials 0.000 claims description 5
- 229910052765 Lutetium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 4
- 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
- 150000002736 metal compounds Chemical class 0.000 claims description 4
- 238000007639 printing Methods 0.000 claims description 4
- HSPRVWPULGKMRC-UHFFFAOYSA-N 57526-50-8 Chemical compound C12CCCC2C2CC(CO)C1C2 HSPRVWPULGKMRC-UHFFFAOYSA-N 0.000 claims description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 239000011258 core-shell material Substances 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 3
- 238000003847 radiation curing Methods 0.000 claims description 3
- CGRJJOYCFCCGPX-UHFFFAOYSA-N 3-ethyloxetane Chemical compound CCC1COC1 CGRJJOYCFCCGPX-UHFFFAOYSA-N 0.000 claims description 2
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 25
- 125000000524 functional group Chemical group 0.000 description 24
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 239000004593 Epoxy Substances 0.000 description 20
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 239000011701 zinc Substances 0.000 description 19
- 239000000178 monomer Substances 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 150000001735 carboxylic acids Chemical class 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000004721 Polyphenylene oxide Substances 0.000 description 11
- 125000002843 carboxylic acid group Chemical group 0.000 description 11
- 229920000570 polyether Polymers 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000008064 anhydrides Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000011575 calcium Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical group 0.000 description 8
- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 7
- 239000011248 coating agent Substances 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
- 229920001169 thermoplastic Polymers 0.000 description 7
- 239000004416 thermosoftening plastic Substances 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 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 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
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 239000012952 cationic photoinitiator Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 150000004292 cyclic ethers Chemical class 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
- 229940117969 neopentyl glycol Drugs 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- 239000010936 titanium Substances 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002131 composite material Substances 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
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
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- 230000008569 process Effects 0.000 description 4
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- 230000009257 reactivity Effects 0.000 description 4
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
- 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 3
- HIGURUTWFKYJCH-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC1(COCC2OC2)CCCCC1 HIGURUTWFKYJCH-UHFFFAOYSA-N 0.000 description 3
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical group 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
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 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 3
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
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- 125000003566 oxetanyl group Chemical group 0.000 description 3
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
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- 241000894007 species Species 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- 125000000349 (Z)-3-carboxyprop-2-enoyl group Chemical group O=C([*])/C([H])=C([H])\C(O[H])=O 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
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- 125000005842 heteroatom Chemical group 0.000 description 1
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- 239000004611 light stabiliser Substances 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical group C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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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 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
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- LOFJKBAHPJENQS-UHFFFAOYSA-N tris(oxomethylidene)chromium Chemical compound O=C=[Cr](=C=O)=C=O LOFJKBAHPJENQS-UHFFFAOYSA-N 0.000 description 1
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- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0037—Production of three-dimensional images
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
- B29C64/10—Processes of additive manufacturing
- B29C64/106—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material
- B29C64/124—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- 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
- C09D7/65—Additives macromolecular
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2033/00—Use of polymers of unsaturated acids or derivatives thereof as moulding material
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- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2063/00—Use of EP, i.e. epoxy resins or derivatives thereof, as moulding material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2105/00—Condition, form or state of moulded material or of the material to be shaped
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Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Mechanical Engineering (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、
c) エポキシ含有化合物以外の少なくとも1種の重合性複素環部分含有化合物、
d) 任意選択的に、少なくとも1種の光開始剤、及び
e) 任意選択的に、少なくとも1種の衝撃改質剤。
a) 5~70重量%(又は5~20重量%又は7~15重量%)の少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 15~60重量%(又は20~50重量%又は25~45重量%)の、重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、
c) 20~60重量%(又は35~60重量%又は50~60重量%)の、エポキシ含有化合物以外の少なくとも1種の重合性の複素環部分含有化合物、
d)0~5重量%(又は0.1~5重量%又は1~4.5重量%)の少なくとも1種の光開始剤、及び
e) 0~20重量%(例えば、0.5~15重量%)の少なくとも1種の衝撃改質剤
を含み得、各成分の重量%は、硬化性組成物の総重量に基づく。
本発明の硬化性組成物は、少なくとも1種の重合性のエチレン性不飽和金属錯体を含む。2種以上の重合性のエチレン性不飽和金属錯体が硬化性組成物中に存在してもよい。本明細書中で使用される場合、「重合性」という用語は、付加重合において共有結合によって結合することが可能な物質を意味する。重合性のエチレン性不飽和金属錯体は、エチレン性不飽和の1つ、2つ、3つ又はそれ以上の部位(すなわち、2つ以上のエチレン性不飽和官能基)を含むことができる。
M(OC(=O)CR1=CH2)x(O-C(=O)-R2-C(=O)-O-R3-O-C(=O)CR4=CH2)y(I)
式中、Mは価数nの、水素(H)以外の元素(例えばZn、Ti、Ca、Mg、Al、Zr、Hf、Ga、Cr、La、Ce、Nd、Sm、Gd、Tb、Dy、Ho、Er、Tm、Yb及び/又はLu)であり、n=x+y、y=少なくとも1の整数、R1及びR4は同一であるか、又は異なり、H又はCH3であり、R2及びR3は同一であるか、又は異なり、各々が2個以上の炭素原子を含む二価の有機部分である。
HO-C(=O)-R2-C(=O)-O-R3-O-C(=O)CR4=CH2)y(II)
R1-CH=C(R2)C(=O)-X1-X2-X3-C(=O)-CH2-C(=O)-R3(III)
式中、R1は水素又はハロゲンであり、R2は水素、ハロゲン、C1~C6アルキルチオ基又はC1~C6アルキル基であり、R3はC1~C6アルキル基であり、X1及びX3は独立してO、S、又は式-N(R4)-の基であり、式中、R4はC1~C6アルキル基であり、X2はC2~C12アルキレン基又はC3~C12シクロアルキレン基である。アルキル基とアルキレン基は直鎖状(線状)でも分枝状でもよい。
上記エチレン性不飽和金属錯体との併用に適した重合性のエチレン性不飽和化合物としては、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に関与し得る炭素-炭素二重結合であって、炭素-炭素二重結合の少なくとも1つの炭素が第2の分子中の原子、特に炭素原子に共有結合するようになる炭素-炭素二重結合を含有する化合物が挙げられる。そのような反応は、エチレン性不飽和化合物が重合マトリックス又はポリマー鎖の一部となる重合又は硬化をもたらし得る。本発明の種々の実施形態において、追加のエチレン不飽和化合物(複数可)は、分子あたり1つ、2つ、3つ、4つ、5つ、又はそれ以上の炭素二重結合を含んでいてもよい。異なる数の炭素-炭素二重結合を含有する複数のエチレン性不飽和化合物の組み合わせを、本発明の硬化性組成物において利用することができる。炭素-炭素二重結合は、α,β-不飽和カルボニル部分、例えばアクリレート官能基若しくはメタクリレート官能基のようなα,β-不飽和エステル部分、又はアクリルアミド官能基若しくはメタクリルアミド官能基のようなα,β-不飽和アミド部分の一部として存在し得る。炭素-炭素二重結合はまた、ビニル基-CH=CH2(アリル基、-CH2-CH=CH2等)の形態で追加のエチレン性不飽和化合物中に存在してもよい。追加のエチレン性不飽和化合物には、炭素-炭素二重結合を含む2つ以上の異なる種類の官能基が存在していてもよい。例えばエチレン性不飽和化合物は、ビニル基(アリル基を含む)、アクリレート基、メタクリレート基、アクリルアミド基、メタクリルアミド基及びそれらの組み合わせからなる群から選択される2つ以上の官能基を含むことができる。
i) イソボルニル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、4-tert-ブチルシクロヘキシル(メタ)アクリレート及びそれらのアルコキシル化類似体等の環状単官能性(メタ)アクリレートモノマー、
ii) イソデシル(メタ)アクリレート、エトキシエトキシエチル(メタ)アクリレート、ポリエチレンモノ(メタ)アクリレート、ネオペンチルグリコール(メタ)アクリレート及びそのアルコキシル化類似体、並びに1モル、2モル、3モル又はそれ以上のカプロラクトンをヒドロキシエチル(メタ)アクリレートのようなヒドロキシアルキル(メタ)アクリレートに添加することによって調製されるカプロラクトン系(メタ)アクリレート(「ヒドロキシアルキル(メタ)アクリレートのカプロラクトン付加物」)、
iii) トリシクロデカンジメタノールジ(メタ)アクリレート、シクロヘキサンジメタノールジ(メタ)アクリレート及びそれらのアルコキシル化類似体のような環状二官能性(メタ)アクリレートモノマー、
iv) ポリエチレンジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート及びそのアルコキシル化類似体のような直鎖二官能性(メタ)アクリレートモノマー、及び
v) トリアリルイソシアヌレートトリ(メタ)アクリレート、トリメチロールトリ(メタ)アクリレート及びそのアルコキシル化類似体のような三官能性(メタ)アクリレートモノマー。
本発明の硬化性組成物は、1種以上の重合性の複素環部分含有化合物を含む。このような化合物は、化合物中に存在する1つ以上の複素環部分(複素環官能基)の反応(典型的には開環反応又は重合を含む)による硬化性組成物の硬化に関与することができる。複素環部分(単数又は複数)は、酸素原子等の少なくとも1個のヘテロ原子を含有する環構造等の、そのような反応が可能であることが当技術分野で公知の部分のいずれであってもよい。典型的には、複素環は3~6員環である。適切な複素環部分は、例えば、エポキシ基(複素環が2個の炭素原子及び1個の酸素原子を含む)、オキセタン基(複素環が3個の炭素原子及び1個の酸素原子を含む)、環状カーボネート基(複素環が、例えば3個の炭素原子及びカルボニル基の一部でもある炭素原子の両側に2個の酸素原子を含む)及びラクトン基(複素環基が、例えば、3~5個の炭素原子及びカルボニル基の一部でもある炭素原子に隣接する1個の酸素原子を含む)を含む。したがって、硬化性組成物は、エポキシド、オキセタン、環状カーボネート、ラクチド及びラクトンからなる群から選択される少なくとも1種の重合性複素環部分含有化合物を含み得る。本発明の一実施形態によれば、1種類の重合性複素環部分含有化合物のみが存在する。他の実施形態では、2つ以上の種類の重合性複素環部分含有化合物が存在する。複素環部分含有化合物は、2つ以上の異なる種類の重合性複素環を含むことができる。例えば、複素環部分含有化合物は、1つ以上のオキセタン環及び1つ以上のエポキシ環を含み得る(3-[(オキシラニルメトキシ)メチル]オキセタンは、このような化合物の例である)。
本発明の特定の実施形態では、本明細書に記載される硬化性組成物は、少なくとも1種の光開始剤を含み、放射エネルギーで硬化可能である。例えば光開始剤(複数可)は、α-ヒドロキシケトン、フェニルグリオキシレート、ベンジルジメチルケタール、α-アミノケトン、モノアシルホスフィン、ビスアシルホスフィン、ホスフィンオキシド及びそれらの組み合わせ(α-ヒドロキシルケトン及びアシルホスフィンオキシドのブレンド等)からなる群から選択することができる。特定の実施形態において、少なくとも1種の光開始剤は、1-ヒドロキシ-シクロヘキシル-フェニル-ケトン及び/又は2-ヒドロキシ-2-メチル-1-フェニル-1-プロパノンであることができる。他の実施形態では、少なくとも1種の光開始剤は、ホスフィンオキシド、特にビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキシド、(2,4,6-トリメチルベンゾイル)フェニルエトキシホスフィンオキシド、トリス(2,4,6-トリメチルベンゾイル)ホスフィンオキシド及びそれらの液体混合物であるか、又はそれらを含む。
本発明の特定の実施形態によれば、硬化性組成物は、1種以上の衝撃改質剤を含むことができる。ポリマー技術分野で知られた種類の衝撃改質剤のいずれかを使用することができるが、ブロックコポリマーである衝撃改質剤の添加が特に有利である。硬化性組成物は、例えば、1種以上の熱可塑性アクリルブロックコポリマーを含むことができる。このブロックコポリマーはコア-シェル構造を有することができる。第1の実施形態によれば、マトリックスは、一般式(A)nBを有する少なくとも1つの熱可塑性アクリルブロックコポリマーで構成され、式中、nは1以上の整数であり、Aは50℃を超える、好ましくは80℃を超えるTgを有するアクリル若しくはメタクリルホモ若しくはコポリマー又はポリスチレン、又はアクリル/スチレン若しくはメタクリル/スチレンコポリマーである。Tg(ガラス転移温度)は、規格ISO11357-2に従って、2回目の加熱パス後に、示差走査熱量計(DSC)を用いて測定する。加熱及び冷却速度は20℃/分である。
有利なことに、本発明の硬化性組成物は、無溶媒、すなわち、いかなる非反応性揮発性物質も含まないように配合され得る。
本明細書に記載される本発明の硬化性組成物は、フリーラジカル重合又は他の種類の重合(例えば、カチオン重合)によって硬化される組成物であることができる。本発明の硬化性組成物の最終使用用途には、インク、コーティング、接着剤、3D印刷樹脂、成形樹脂、シーラント、複合体等が含まれるが、これらに限定されない。
a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、
c) 少なくとも1種の重合性の複素環部分含有化合物(例えば、1種以上のエポキシド、オキセタン、環状カーボネート、ラクチド及び/又はラクトン)、
d) 任意選択的に、少なくとも1種の光開始剤、及び
e) 任意選択的に、少なくとも1種の衝撃改質剤
を含むことができる。
a) 5~70%、好ましくは5~20%、最も好ましくは7~15重量%の少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 10~60%、好ましくは10~40%、最も好ましくは15~30重量%の、重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、
c) 20~60%、好ましくは35~60%、最も好ましくは45~55重量%の少なくとも1種の重合性の複素環部分含有化合物(例えば1種以上のエポキシド、オキセタン、環状カーボネート、ラクチド及び/又はラクトン)、
d) 0~5重量%(例えば0.05~5重量%)の少なくとも1種の光開始剤、及び
e) 0~20重量%(例えば0.5~15重量%)の少なくとも1種の衝撃改質剤
を含むことができ、各成分の重量%は、硬化性組成物の総重量に基づく。
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工程、
b) 第1の層を少なくとも部分的に硬化させて、第1の硬化層を提供する工程、
c) 硬化性組成物の第2の層を第1の硬化層上にコーティングする工程、
d) 第2の層を少なくとも部分的に硬化させて、第1の硬化層に接着した第2の硬化層を提供する工程、及び
e) 三次元物品を作るために所望の回数工程c)及びd)を繰り返す工程。
a) 本発明に従い、液体形態である硬化性組成物の第1の層を表面上にコーティングする工程、
b) 第1の層を化学線に像様に露光して、第1の露光された画像形成された断面を形成し、放射は、露光された領域中の層の少なくとも部分的な硬化(例えば硬化性組成物中に最初に存在する重合性のエチレン性不飽和官能基の転化率%によって測定して、少なくとも50%の硬化)を引き起こすのに十分な強度及び持続時間のものである工程、
c) あらかじめ露光された画像形成された断面上に硬化性組成物の追加の層をコーティングする工程、
d) 追加の層を化学線に像様に露光して、追加の画像形成された断面を形成し、放射は、露光領域における追加の層の少なくとも部分的な硬化(例えば硬化性組成物中に最初に存在する重合性エチレン性不飽和官能基の転化率%によって測定して、少なくとも50%の硬化)を引き起こし、かつ以前に露光された画像形成された断面への追加の層の接着を引き起こすのに十分な強度及び持続時間のものである工程、
e) 三次元物品を作るために所望の回数、工程c)及びd)を繰り返す工程。
a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、及び
c) エポキシ含有化合物以外の少なくとも1種の重合性の複素環部分含有化合物
a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、及び
c) 少なくとも1種の重合性の複素環部分含有化合物。
a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、及び
c) 少なくとも1種の重合性の複素環部分含有化合物。
TA Instruments Q2000 Dynamic Mechanical Analyzerを用いて、0.1%歪、5℃/分の温度傾斜及び-150~200℃の間で1Hzの変形周波数で動的機械分析を行った。表示される温度窓がより小さい試料は、表示される窓の外側で正確に測定するには柔らかすぎるようになった。硬化性組成物を、所望の形状の物品を製造するために、100ft/分でコンベヤー上のランプ下(例えば、Heraeus Noblelightから市販されているマイクロ波動力付き中圧水銀蒸気ランプ)を通過させることにより、又は3D印刷機を使用することによって型の中で光重合した。物品をイソプロパノールで湿らせた布で拭き取って、残った未硬化樹脂を除去して綺麗にした。熱硬化した(「焼成した」)試料を、特に指定のない限り、125℃で16時間マッフル炉又は循環空気オーブンに入れた。
以下の成分を混合して硬化性組成物を調製した。
カルボン酸亜鉛混合物 41.18g
グリシジルメタクリレート 13.92g
エポキシノボラック樹脂 29.47g
アクリルオキシエチルジ(カプロラクトン)
(SR495B、Sartomer) 14.57g
Irgacure(R)2022光開始剤 0.85g
以下の硬化性組成物は、以下の成分を混合して調製した。
カルボン酸亜鉛混合物(CN2430、Sartomer) 37.94g
グリシジルメタクリレート 2.11g
アクリロキシエチルジ(カプロラクトン) 4.04g
プロピレンカーボネート 27.20g
トリシクロデカンジメタノールジアクリレート
(SR833S、Sartomer) 28.0g
Irgacure(R)2022光開始剤 0.80g
従来のアクリル-エポキシ「ハイブリッド」樹脂は、カチオン性光開始剤の使用を必要とし、該開始剤の活性は、配合物が硬化される際にウレタン結合の存在によって大幅に阻害される。本発明によるカルボン酸亜鉛錯体の使用は、ウレタン含有材料の存在下でアクリル-エポキシ相互貫入ネットワークの形成を可能にする。
カルボン酸亜鉛混合物(CN2430、Sartomer) 10.0g
SR531 20.0g
CN9004 15.0g
CN983 5.0g
ビスフェノールAジグリシジルエーテル、(DER331、Dow) 4.0g
3-エチル-3-ヒドロキシメチルオキセタン
(OXT-101、Sanyo Chemical) 3.0g
シクロヘキサンジメタノールジグリシジルエーテル
(Erisys(R)GE-22、エメラルド性能材料) 35.0g
Irgacure(R)2022光開始剤 0.80g
Claims (20)
- a) 少なくとも1種の重合性のエチレン性不飽和金属錯体、
b) 重合性のエチレン性不飽和金属錯体以外の少なくとも1種の重合性のエチレン性不飽和化合物、及び
c) エチレン性不飽和を含まない少なくとも1種の重合性の複素環部分含有化合物
から構成される硬化性組成物であって、
前記少なくとも1種の重合性のエチレン性不飽和金属錯体が、
(A)金属化合物と、(i)α-βエチレン性不飽和ヒドロキシル官能化化合物、及び(ii)多価カルボン酸又はカルボン酸無水物を含む反応性混合物の反応生成物である、(B)酸官能性化合物とを反応させて調製した少なくとも1種の重合性のエチレン性不飽和金属カルボン酸塩、又は
エチレン性不飽和ベータ-ジケトネート配位子から構成される少なくとも1種の重合性のエチレン性不飽和金属錯体
を含む、
硬化性組成物。 - 前記少なくとも1種の重合性のエチレン性不飽和金属錯体が、少なくとも1つの(メタ)アクリレート基から構成される少なくとも1種の重合性のエチレン性不飽和金属錯体を含む、請求項1に記載の硬化性組成物。
- 前記少なくとも1種の重合性のエチレン性不飽和金属錯体が、Zn、Ti、Ca、Mg、Al、Zr、Hf、Ga、Cr、La、Ce、Nd、Sm、Gd、Tb、Dy、Ho、Er、Tm、Yb及びLuからなる群から選択される金属を含む少なくとも1種の重合性のエチレン性不飽和金属錯体を含む、請求項1に記載の硬化性組成物。
- 前記少なくとも1種の重合性の複素環部分含有化合物c)が、オキセタン、環状カーボネート、ラクチド及びラクトンからなる群から選択される少なくとも1種の重合性の複素環部分含有化合物を含むか、又は前記硬化性組成物が、a)オキセタン、環状カーボネート、ラクチド及びラクトンからなる群から選択される少なくとも1種の重合性の複素環部分含有化合物、及びb)少なくとも1種のエポキシドから構成される、請求項1~3のいずれか一項に記載の硬化性組成物。
- 前記少なくとも1種の重合性の複素環部分含有化合物c)が、カプロラクトン、プロピレンカーボネート、3-エチル-3-ヒドロキシメチルオキセタン、3,3’-[1,4-フェニレンビス(メチレンオキシメチレン)]ビス[3-エチルオキセタン]、3-エチル-3-[(2-エチルヘキシル)オキシ]メチル]オキセタン、エチレンカーボネート、グリセロールカーボネート、ラクチド及びバレロラクトンからなる群から選択される少なくとも1種の重合性の複素環部分含有化合物を含む、請求項1~4のいずれか一項に記載の硬化性組成物。
- 重合性のエチレン性不飽和金属錯体以外の前記少なくとも1種の重合性のエチレン性不飽和化合物b)が、少なくとも1種の(メタ)アクリレート官能化化合物を含む、請求項1~5のいずれか一項に記載の硬化性組成物。
- 重合性のエチレン性不飽和金属錯体以外の前記少なくとも1種の重合性のエチレン性不飽和化合物b)が、少なくとも1種の(メタ)アクリレート及びヒドロキシ官能化化合物を含む、請求項1~6のいずれか一項に記載の硬化性組成物。
- 重合性のエチレン性不飽和金属錯体以外の前記少なくとも1種の重合性のエチレン性不飽和化合物b)が、少なくとも1種の(メタ)アクリレート及びエポキシ官能化化合物を含む、請求項1~7のいずれか一項に記載の硬化性組成物。
- 重合性のエチレン性不飽和金属錯体以外の前記少なくとも1種の重合性のエチレン性不飽和化合物b)が、ヒドロキシアルキル(メタ)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、環状トリメチロールプロパンホルマールアクリレート、トリシクロデカンメタノール(メタ)アクリレート、トリス((メタ)アクリロキシエチル)イソシアヌレート、グリセロールカーボネート(メタ)アクリレート及び脂肪族ポリウレタンアクリレートのカプロラクトン付加物からなる群から選択される少なくとも1種の化合物を含む、請求項1~8のいずれか一項に記載の硬化性組成物。
- 少なくとも1種の光開始剤をさらに含む、請求項1~9のいずれか一項に記載の硬化性組成物。
- コア-シェル衝撃改質剤及びブロックコポリマー衝撃改質剤からなる群から選択される少なくとも1種の衝撃改質剤をさらに含む、請求項1~10のいずれか一項に記載の硬化性組成物。
- 25℃で1000(mPa・s)以下の粘度を有する、請求項1~11のいずれか一項に記載の硬化性組成物。
- 請求項1~12のいずれか一項に記載の硬化性組成物を調製するのに有用な2成分系であって、a)から構成される第1の成分と、b)及びc)から構成される第2の成分とを含む、2成分系。
- 請求項1~12のいずれか一項に記載の硬化性組成物を硬化させて得られる硬化組成物。
- 請求項1~12のいずれか一項に記載の硬化性組成物を放射線に曝露させて部分硬化組成物を得ること、及び該部分硬化組成物を加熱して硬化組成物を得ることを含む、硬化組成物の製造方法。
- 請求項1~12のいずれか一項に記載の硬化性組成物を用いて物品を三次元的に印刷することを含む、物品を製造する方法。
- 前記物品が、放射線硬化及び熱硬化の両方を用いて硬化される、請求項16に記載の方法。
- 前記少なくとも1種の重合性の複素環部分含有化合物が、エポキシド、オキセタン、環状カーボネート、ラクチド及びラクトンからなる群から選択される少なくとも1種の重合性の複素環部分含有化合物を含む、請求項16又は17に記載の方法。
- 3D印刷手法を用いた三次元物品の製造における、請求項1~12のいずれか一項に記載の硬化性組成物、又は請求項13に記載の2成分系の使用。
- 請求項1~12のいずれか一項に記載の硬化性組成物の硬化、又は請求項19の使用の結果として得られる3D印刷物品。
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WO2019167948A1 (ja) * | 2018-03-02 | 2019-09-06 | 株式会社日本触媒 | インクジェット3dプリンター用光硬化性サポート材用組成物、インク、カートリッジ、サポート材の製造方法ならびに光造形物の製造方法 |
EP3962411A4 (en) | 2019-05-03 | 2023-01-25 | Johnson & Johnson Surgical Vision, Inc. | HIGHLY REACTIVE COMPOSITIONS WITH HIGH ABBE NUMBER |
US11708440B2 (en) | 2019-05-03 | 2023-07-25 | Johnson & Johnson Surgical Vision, Inc. | High refractive index, high Abbe compositions |
EP4237882A1 (en) | 2020-10-29 | 2023-09-06 | Johnson & Johnson Surgical Vision, Inc. | Compositions with high refractive index and abbe number |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008509398A (ja) | 2004-08-04 | 2008-03-27 | バイオトローブ, インコーポレイテッド | ディスペンサーアレイのロケーションを登録するための方法およびシステム |
JP2014024900A (ja) | 2012-07-25 | 2014-02-06 | Nippon Zeon Co Ltd | 感圧接着剤組成物、感圧接着性シート状成形体、これらの製造方法、及び表示装置 |
Family Cites Families (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3459790A (en) | 1965-12-20 | 1969-08-05 | Eastman Kodak Co | Polymerizable acrylic acid esters containing active methylene groups |
US3835003A (en) | 1968-08-20 | 1974-09-10 | American Can Co | Photopolymerization of oxetanes |
US3899382A (en) | 1973-03-08 | 1975-08-12 | Hideaki Matsuda | Anaerobic bonding agent |
US4215195A (en) | 1978-12-20 | 1980-07-29 | Eastman Kodak Company | Polymers of amide compounds useful in photographic materials |
US4503140A (en) * | 1982-05-18 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiation-sensitive compositions of polymers containing a π-metal carbonyl complex of conjugated polyolefin |
JPS6298304A (ja) * | 1985-10-25 | 1987-05-07 | Hitachi Ltd | プラスチツク光フアイバ− |
JPS62288618A (ja) * | 1986-06-09 | 1987-12-15 | Hitachi Ltd | 透明樹脂 |
WO1993023794A1 (en) * | 1992-05-21 | 1993-11-25 | Minnesota Mining And Manufacturing Company | Organometallic monomers and polymers with improved adhesion |
US5750590A (en) | 1995-02-22 | 1998-05-12 | Heraeus Kulzer Gmbh | Polymerizable material |
JP3161583B2 (ja) | 1995-07-21 | 2001-04-25 | 東亞合成株式会社 | 活性エネルギー線硬化型組成物 |
US5872297A (en) | 1995-08-24 | 1999-02-16 | S. C. Johnson Commercial Markets, Inc. | Ethylenically-unsaturated 1,3-diketoamide functional compounds |
DE69601455T2 (de) | 1995-11-22 | 1999-07-08 | Akzo Nobel Nv | Feuchtigkeitshärtende Beschichtungszusammensetzung |
JP3765896B2 (ja) | 1996-12-13 | 2006-04-12 | Jsr株式会社 | 光学的立体造形用光硬化性樹脂組成物 |
FR2758557B1 (fr) | 1997-01-21 | 1999-11-12 | Toagosei Co Ltd | Compose ayant un groupe oxetanyle, son procede de preparation et composition de durcissement |
US6287748B1 (en) | 1998-07-10 | 2001-09-11 | Dsm N.V. | Solid imaging compositions for preparing polyethylene-like articles |
US6399672B1 (en) * | 1999-06-02 | 2002-06-04 | Sartomer Technologies Co., Inc. | Oil soluble metal-containing compounds, compositions and methods |
EP1069120B1 (en) | 1999-07-15 | 2003-08-13 | Toagosei Co., Ltd. | Naphthalene derivative, binaphthalene derivative and biphenyl derivative and cationically curable compound |
US6811937B2 (en) * | 2001-06-21 | 2004-11-02 | Dsm Desotech, Inc. | Radiation-curable resin composition and rapid prototyping process using the same |
WO2003093901A1 (en) | 2002-05-03 | 2003-11-13 | Dsm Ip Assets B.V. | Radiation curable resin composition and rapid prototyping process using the same |
US6989225B2 (en) | 2002-07-18 | 2006-01-24 | 3D Systems, Inc. | Stereolithographic resins with high temperature and high impact resistance |
US6833231B2 (en) | 2002-07-31 | 2004-12-21 | 3D Systems, Inc. | Toughened stereolithographic resin compositions |
US20040137368A1 (en) | 2003-01-13 | 2004-07-15 | 3D Systems, Inc. | Stereolithographic resins containing selected oxetane compounds |
KR20050109555A (ko) | 2003-03-13 | 2005-11-21 | 사토머 테크놀로지 컴퍼니, 인코포레이티드 | 가역적 가교 수지 조성물 및 방법 |
US20050040562A1 (en) | 2003-08-19 | 2005-02-24 | 3D Systems Inc. | Nanoparticle-filled stereolithographic resins |
US20080103226A1 (en) | 2006-10-31 | 2008-05-01 | Dsm Ip Assets B.V. | Photo-curable resin composition |
EP2118169B2 (en) * | 2007-03-14 | 2021-03-17 | 3D Systems, Inc. | Curable composition |
WO2008115057A1 (en) | 2007-03-20 | 2008-09-25 | Dsm Ip Assets B.V. | Stereolithography resin compositions and three-dimensional objects made therefrom |
US8324319B2 (en) | 2007-11-20 | 2012-12-04 | Sridhar Laxmisha M | Redox-induced cationically polymerizable compositions with low cure temperature |
EP2215525B1 (en) * | 2007-11-27 | 2018-01-10 | 3D Systems Incorporated | Photocurable resin composition for producing three dimensional articles having high clarity |
US8809447B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
US9861452B2 (en) * | 2013-08-09 | 2018-01-09 | Dsm Ip Assets B.V. | Low-viscosity liquid radiation curable dental aligner mold resin compositions for additive manufacturing |
US10501572B2 (en) | 2015-12-22 | 2019-12-10 | Carbon, Inc. | Cyclic ester dual cure resins for additive manufacturing |
-
2018
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Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008509398A (ja) | 2004-08-04 | 2008-03-27 | バイオトローブ, インコーポレイテッド | ディスペンサーアレイのロケーションを登録するための方法およびシステム |
JP2014024900A (ja) | 2012-07-25 | 2014-02-06 | Nippon Zeon Co Ltd | 感圧接着剤組成物、感圧接着性シート状成形体、これらの製造方法、及び表示装置 |
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