WO2010091807A1 - Photopolymerzusammensetzungen als verdruckbare formulierungen - Google Patents
Photopolymerzusammensetzungen als verdruckbare formulierungen Download PDFInfo
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- WO2010091807A1 WO2010091807A1 PCT/EP2010/000618 EP2010000618W WO2010091807A1 WO 2010091807 A1 WO2010091807 A1 WO 2010091807A1 EP 2010000618 W EP2010000618 W EP 2010000618W WO 2010091807 A1 WO2010091807 A1 WO 2010091807A1
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- Prior art keywords
- printing
- weight
- component
- acrylate
- isocyanate
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- 239000000203 mixture Substances 0.000 title claims description 74
- 229920000642 polymer Polymers 0.000 title abstract description 5
- 238000009472 formulation Methods 0.000 title description 19
- 238000007639 printing Methods 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 45
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000000007 visual effect Effects 0.000 claims abstract description 6
- -1 polyethylene terephthalate Polymers 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000004814 polyurethane Substances 0.000 claims description 26
- 229920002635 polyurethane Polymers 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 14
- 229920001228 polyisocyanate Polymers 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 8
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 5
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004698 Polyethylene Substances 0.000 claims description 5
- 150000003673 urethanes Chemical class 0.000 claims description 5
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 4
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 4
- 238000000862 absorption spectrum Methods 0.000 claims description 4
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical class CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
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- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 2
- 239000000020 Nitrocellulose Substances 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920001153 Polydicyclopentadiene Polymers 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 230000003595 spectral effect Effects 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 6
- 229920005862 polyol Polymers 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 19
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 18
- 239000010410 layer Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 11
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
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- 238000007650 screen-printing Methods 0.000 description 7
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 6
- ZOMLUNRKXJYKPD-UHFFFAOYSA-N 1,3,3-trimethyl-2-[2-(2-methylindol-3-ylidene)ethylidene]indole;hydrochloride Chemical compound [Cl-].C1=CC=C2C(C)(C)C(/C=C/C=3C4=CC=CC=C4NC=3C)=[N+](C)C2=C1 ZOMLUNRKXJYKPD-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- JVICFMRAVNKDOE-UHFFFAOYSA-M ethyl violet Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 JVICFMRAVNKDOE-UHFFFAOYSA-M 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 4
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- 150000003254 radicals Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 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
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000007945 N-acyl ureas Chemical class 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- FGPCETMNRYMFJR-UHFFFAOYSA-L [7,7-dimethyloctanoyloxy(dimethyl)stannyl] 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)O[Sn](C)(C)OC(=O)CCCCCC(C)(C)C FGPCETMNRYMFJR-UHFFFAOYSA-L 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 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 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 239000002981 blocking agent Substances 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- SQHOAFZGYFNDQX-UHFFFAOYSA-N ethyl-[7-(ethylamino)-2,8-dimethylphenothiazin-3-ylidene]azanium;chloride Chemical compound [Cl-].S1C2=CC(=[NH+]CC)C(C)=CC2=NC2=C1C=C(NCC)C(C)=C2 SQHOAFZGYFNDQX-UHFFFAOYSA-N 0.000 description 3
- 238000007646 gravure printing Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 3
- 229960000907 methylthioninium chloride Drugs 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 239000005060 rubber Substances 0.000 description 3
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- 239000004416 thermosoftening plastic Substances 0.000 description 3
- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-UHFFFAOYSA-N 0.000 description 3
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- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 2
- RHNNQENFSNOGAM-UHFFFAOYSA-N 1,8-diisocyanato-4-(isocyanatomethyl)octane Chemical compound O=C=NCCCCC(CN=C=O)CCCN=C=O RHNNQENFSNOGAM-UHFFFAOYSA-N 0.000 description 2
- PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 2
- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
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- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
- 108010076830 Thionins Proteins 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
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- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 2
- 238000013500 data storage Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
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- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 2
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
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- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- ADAUKUOAOMLVSN-UHFFFAOYSA-N gallocyanin Chemical compound [Cl-].OC(=O)C1=CC(O)=C(O)C2=[O+]C3=CC(N(C)C)=CC=C3N=C21 ADAUKUOAOMLVSN-UHFFFAOYSA-N 0.000 description 2
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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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
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- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
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- 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
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
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Landscapes
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Holo Graphy (AREA)
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- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
Claims
Priority Applications (7)
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CN2010800075012A CN102317336A (zh) | 2009-02-12 | 2010-02-02 | 作为可印刷配制剂的光聚合物组合物 |
RU2011137188/04A RU2011137188A (ru) | 2009-02-12 | 2010-02-02 | Фотополимерные композиции в качестве пригодных для печатания композиций |
EP10702444.0A EP2396359B1 (de) | 2009-02-12 | 2010-02-02 | Photopolymerzusammensetzungen als verdruckbare formulierungen |
SG2011049608A SG173436A1 (en) | 2009-02-12 | 2010-02-02 | Photo polymer compositions as printable formulations |
US13/201,004 US8715889B2 (en) | 2009-02-12 | 2010-02-02 | Photopolymer compositions as printable formulations |
CA2751911A CA2751911A1 (en) | 2009-02-12 | 2010-02-02 | Photo polymer compositions as printable formulations |
JP2011549467A JP5684733B2 (ja) | 2009-02-12 | 2010-02-02 | 印刷可能配合物としての感光性ポリマー組成物 |
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EP09001949A EP2218742A1 (de) | 2009-02-12 | 2009-02-12 | Photopolymerzusammensetzungen als verdruckbare Formulierungen |
EP09001949.8 | 2009-02-12 |
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US (1) | US8715889B2 (de) |
EP (2) | EP2218742A1 (de) |
JP (1) | JP5684733B2 (de) |
KR (1) | KR20110123242A (de) |
CN (1) | CN102317336A (de) |
CA (1) | CA2751911A1 (de) |
RU (1) | RU2011137188A (de) |
SG (1) | SG173436A1 (de) |
TW (1) | TW201035146A (de) |
WO (1) | WO2010091807A1 (de) |
Cited By (1)
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US20140009827A1 (en) * | 2011-03-04 | 2014-01-09 | Infitec Gmbh | Eye-glasses for viewing stereoscopic images or a perspective sub-image of same |
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EP2342249B1 (de) * | 2008-10-01 | 2017-10-25 | Covestro Deutschland AG | Prepolymerbasierte polyurethanformulierungen zur herstellung holografischer medien |
EP2342254B1 (de) * | 2008-10-01 | 2017-09-27 | Covestro Deutschland AG | Medien für volumenholographische aufzeichnung basierend auf sich selbstentwickelndem polymer |
EP2218743A1 (de) * | 2009-02-12 | 2010-08-18 | Bayer MaterialScience AG | Prepolymerbasierte Polyurethanformulierungen zur Herstellung holographischer Filme |
EP2218744A1 (de) * | 2009-02-12 | 2010-08-18 | Bayer MaterialScience AG | Methode zur Herstellung von holografischen Photopolymeren auf Polymerfolien |
KR101747467B1 (ko) * | 2009-11-03 | 2017-06-14 | 코베스트로 도이칠란드 아게 | 굴절률이 높고 이중 결합 밀도가 감소된 우레탄 아크릴레이트 |
ES2446344T3 (es) * | 2009-11-03 | 2014-03-07 | Bayer Intellectual Property Gmbh | Procedimiento para la producción de una película holográfica |
PL2317511T3 (pl) * | 2009-11-03 | 2012-08-31 | Bayer Materialscience Ag | Formulacje fotopolimerowe z nastawialnym mechanicznym modułem Guv |
US8889322B2 (en) * | 2009-11-03 | 2014-11-18 | Bayer Materialscience Ag | Photopolymer formulation having different writing comonomers |
CN104704407A (zh) | 2012-08-13 | 2015-06-10 | 拜耳材料科技股份有限公司 | 带有退耦元件的光引导板 |
JP6197020B2 (ja) * | 2015-12-17 | 2017-09-13 | 三井化学株式会社 | 光硬化性樹脂組成物、表示素子シール剤、液晶シール剤及び液晶表示パネルとその製造方法 |
EP3461636B1 (de) * | 2017-09-29 | 2021-05-19 | Wayray AG | Laminiertes holographisches display und herstellung davon |
KR102166846B1 (ko) * | 2017-12-11 | 2020-10-16 | 주식회사 엘지화학 | 포토폴리머 조성물 |
US11267913B2 (en) | 2018-02-14 | 2022-03-08 | Mighty Buildings, Inc. | 3D printed material, structure and method for making the same |
US11718580B2 (en) | 2019-05-08 | 2023-08-08 | Meta Platforms Technologies, Llc | Fluorene derivatized monomers and polymers for volume Bragg gratings |
WO2021011357A1 (en) | 2019-07-12 | 2021-01-21 | 3D Systems, Inc. | Build materials for 3d printing |
US11780819B2 (en) | 2019-11-27 | 2023-10-10 | Meta Platforms Technologies, Llc | Aromatic substituted alkane-core monomers and polymers thereof for volume Bragg gratings |
US20210155585A1 (en) * | 2019-11-27 | 2021-05-27 | Facebook Technologies, Llc | Anthraquinone derivatized monomers and polymers for volume bragg gratings |
US11879024B1 (en) | 2020-07-14 | 2024-01-23 | Meta Platforms Technologies, Llc | Soft mold formulations for surface relief grating fabrication with imprinting lithography |
CN113912809B (zh) * | 2021-12-02 | 2023-05-30 | 黄山中泽新材料有限公司 | 一种新型凹版印刷蓝色油墨用聚氨酯连接料及其制备方法 |
WO2024085619A1 (ko) * | 2022-10-18 | 2024-04-25 | 주식회사 엘지화학 | 홀로그램 기록 매체, 포토폴리머층 형성용 조성물, 및 광학 소자 |
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DE102004015983A1 (de) * | 2004-04-01 | 2005-10-20 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyetherallophanaten unter Verwendung von Zink-Verbindungen als Katalysatoren |
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IL200995A0 (en) | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Polyether-based polyurethane formulations for the production of holographic media |
EP2342254B1 (de) | 2008-10-01 | 2017-09-27 | Covestro Deutschland AG | Medien für volumenholographische aufzeichnung basierend auf sich selbstentwickelndem polymer |
IL200997A0 (en) * | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Special polyether-based polyurethane formulations for the production of holographic media |
IL200996A0 (en) * | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Photopolymer formulations having a low crosslinking density |
EP2342249B1 (de) | 2008-10-01 | 2017-10-25 | Covestro Deutschland AG | Prepolymerbasierte polyurethanformulierungen zur herstellung holografischer medien |
IL200722A0 (en) | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Photopolymer compositions for optical elements and visual displays |
EP2218744A1 (de) * | 2009-02-12 | 2010-08-18 | Bayer MaterialScience AG | Methode zur Herstellung von holografischen Photopolymeren auf Polymerfolien |
EP2218743A1 (de) * | 2009-02-12 | 2010-08-18 | Bayer MaterialScience AG | Prepolymerbasierte Polyurethanformulierungen zur Herstellung holographischer Filme |
PL2317511T3 (pl) * | 2009-11-03 | 2012-08-31 | Bayer Materialscience Ag | Formulacje fotopolimerowe z nastawialnym mechanicznym modułem Guv |
TWI506011B (zh) * | 2009-11-03 | 2015-11-01 | Bayer Materialscience Ag | 在光聚合物調配物中作為添加劑之氟胺基甲酸酯 |
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2009
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- 2010-02-02 JP JP2011549467A patent/JP5684733B2/ja active Active
- 2010-02-02 WO PCT/EP2010/000618 patent/WO2010091807A1/de active Application Filing
- 2010-02-02 SG SG2011049608A patent/SG173436A1/en unknown
- 2010-02-02 EP EP10702444.0A patent/EP2396359B1/de active Active
- 2010-02-02 CA CA2751911A patent/CA2751911A1/en not_active Abandoned
- 2010-02-02 RU RU2011137188/04A patent/RU2011137188A/ru unknown
- 2010-02-02 KR KR1020117018681A patent/KR20110123242A/ko not_active Application Discontinuation
- 2010-02-02 CN CN2010800075012A patent/CN102317336A/zh active Pending
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140009827A1 (en) * | 2011-03-04 | 2014-01-09 | Infitec Gmbh | Eye-glasses for viewing stereoscopic images or a perspective sub-image of same |
US9703108B2 (en) * | 2011-03-04 | 2017-07-11 | Infitec Gmbh | Eye-glasses for viewing stereoscopic images or a perspective sub-image of same |
Also Published As
Publication number | Publication date |
---|---|
CA2751911A1 (en) | 2010-08-19 |
EP2396359A1 (de) | 2011-12-21 |
JP2012517514A (ja) | 2012-08-02 |
US20110311906A1 (en) | 2011-12-22 |
EP2218742A1 (de) | 2010-08-18 |
RU2011137188A (ru) | 2013-03-20 |
US8715889B2 (en) | 2014-05-06 |
CN102317336A (zh) | 2012-01-11 |
TW201035146A (en) | 2010-10-01 |
JP5684733B2 (ja) | 2015-03-18 |
SG173436A1 (en) | 2011-09-29 |
KR20110123242A (ko) | 2011-11-14 |
EP2396359B1 (de) | 2017-09-27 |
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