JP6316428B2 - N−ビニルオキサゾリジノンを含有するインクジェット印刷インキ - Google Patents
N−ビニルオキサゾリジノンを含有するインクジェット印刷インキ Download PDFInfo
- Publication number
- JP6316428B2 JP6316428B2 JP2016533884A JP2016533884A JP6316428B2 JP 6316428 B2 JP6316428 B2 JP 6316428B2 JP 2016533884 A JP2016533884 A JP 2016533884A JP 2016533884 A JP2016533884 A JP 2016533884A JP 6316428 B2 JP6316428 B2 JP 6316428B2
- Authority
- JP
- Japan
- Prior art keywords
- radiation curable
- curable composition
- meth
- vinyloxazolidinone
- acryloyl
- 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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- 238000007641 inkjet printing Methods 0.000 title claims description 28
- VUEZBQJWLDBIDE-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidin-2-one Chemical compound C=CN1CCOC1=O VUEZBQJWLDBIDE-UHFFFAOYSA-N 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims description 63
- 230000005855 radiation Effects 0.000 claims description 60
- -1 acryloyl compounds Chemical class 0.000 claims description 31
- 238000007639 printing Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000758 substrate Substances 0.000 claims description 17
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000000962 organic group Chemical group 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000012462 polypropylene substrate Substances 0.000 claims 1
- 239000000976 ink Substances 0.000 description 34
- 239000000178 monomer Substances 0.000 description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001155 polypropylene Polymers 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Chemical group 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000003847 radiation curing Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229920001567 vinyl ester resin Chemical group 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000005686 electrostatic field Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HXFNRRNDWNSKFM-UHFFFAOYSA-N 3-ethenyl-5-methyl-1,3-oxazolidin-2-one Chemical compound CC1CN(C=C)C(=O)O1 HXFNRRNDWNSKFM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 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 1
- 0 *C(*)(C(*)(O1)I)N(C=C)C1=O Chemical compound *C(*)(C(*)(O1)I)N(C=C)C1=O 0.000 description 1
- QOVCUELHTLHMEN-UHFFFAOYSA-N 1-butyl-4-ethenylbenzene Chemical compound CCCCC1=CC=C(C=C)C=C1 QOVCUELHTLHMEN-UHFFFAOYSA-N 0.000 description 1
- DMADTXMQLFQQII-UHFFFAOYSA-N 1-decyl-4-ethenylbenzene Chemical compound CCCCCCCCCCC1=CC=C(C=C)C=C1 DMADTXMQLFQQII-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- CUTWSDAQYCQTGD-UHFFFAOYSA-N 2-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)C(C)OC(=O)C=C CUTWSDAQYCQTGD-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
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- 238000005886 esterification reaction Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- YJSSCAJSFIGKSN-UHFFFAOYSA-N hex-1-en-2-ylbenzene Chemical compound CCCCC(=C)C1=CC=CC=C1 YJSSCAJSFIGKSN-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Description
本発明は、インクジェット印刷用の印刷インキとしての放射線硬化性組成物の使用に関し、その際、前記放射線硬化性組成物は、式I
R1〜R4は、互いに独立して、水素原子であるかまたは10個以下の炭素原子を有する有機基である]
のN−ビニルオキサゾリジノンを含有する。
R1〜R4は、互いに独立して、水素原子であるかまたは10個以下の炭素原子を有する有機基である]
のN−ビニルオキサゾリジノンを含有する。
R1〜R4の全てが水素原子である化合物(略してNVO)であるか、または、
R1がC1〜C4アルキル基、特にメチル基であってかつR2〜R4の全てが水素原子である化合物(N−ビニル−5−メチルオキサゾリジノン、略してNVMO)であるか、または、
R1およびR2が水素原子であってかつR3およびR4がC1〜C4アルキル基、特にメチル基である化合物を挙げることができる。
本明細書におけるモノマーとは、1つの重合性エチレン性不飽和基を有する化合物であると定義される。モノマーは、好ましくは、300g/モル未満、特に200g/モル未満の分子量を有する。これは特に反応性希釈剤として作用する。可能なモノマーは、例えば、C1〜C20−アルキル(メタ)アクリレート、20個までの炭素原子を含むカルボン酸のビニルエステル、20個までの炭素原子を含むビニル芳香族化合物、エチレン性不飽和ニトリル、1〜10個の炭素原子を含むアルコールのビニルエーテルから選択される。
本明細書におけるオリゴマーとは、2〜10個の重合性エチレン性不飽和基を有する化合物であると定義される。平均で1.5〜6個、特に2〜5個の重合性基を有する化合物が好ましい。
上記モノマーおよび/またはオリゴマーに加えて、前記放射線硬化性組成物は、すでに高い分子量を有しているポリマーを含有することができる。そのようなポリマーは、3000超、特に5000超の分子量Mwを有することができる(標準物質としてポリスチレンを用いかつ溶離液としてテトラヒドロフランを用いたゲル浸透クロマトグラフィーにより測定)。
実施例1
N−ビニルオキサゾリジノンとして、式I[式中、R1〜R4は水素原子である]の化合物(略してNVO)と、R1がメチル基であってかつR2〜R4の全てが水素原子である化合物(N−ビニル−5−メチルオキサゾリジノン、略してNVMO)とを使用した。
得られた塗膜の密着性を調べるために、“Crystal”Scotch粘着テープを使用した。この粘着テープを露光済みのコーティングに付け、剥離し、このコーティングがこの粘着テープと共に剥離されたか否かを調べた。層を作製するためのベルト速度は、それぞれ15m/分、3×15m/分であった。層の厚さは、それぞれ6μm、12μmであった。
前記印刷インキの組成および密着性試験の結果の組成を第1表に示す。
Claims (12)
- 請求項1に記載の放射線硬化性組成物の使用であって、式I中のR1〜R4の少なくとも2つが水素原子であり、かつ残りのR1〜R4の全てが10個以下の炭素原子を有する有機基である、前記使用。
- 請求項1または2に記載の放射線硬化性組成物の使用であって、式IのN−ビニルオキサゾリジノンが、
R1〜R4の全てが水素原子である化合物であるか、または、
R1がC1〜C4アルキル基であってかつR2〜R4の全てが水素原子である化合物であるか、または、
R1およびR2が水素原子であってかつR3およびR4がC1〜C4アルキル基である化合物である、前記使用。 - 請求項1から3までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物が前記N−ビニルオキサゾリジノンを0.5〜80質量%の量で含有する、前記使用。
- 請求項1から4までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物がさらに、少なくとも1つの(メタ)アクリロイル基を有する化合物(以後、略して(メタ)アクリロイル化合物と呼ぶ)を含有する、前記使用。
- 請求項1から5までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物が2〜5個の(メタ)アクリロイル基を有する(メタ)アクリロイル化合物を含有する、前記使用。
- 請求項1から6までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物の全ての放射線硬化性化合物の少なくとも70質量%が(メタ)アクリロイル化合物およびN−ビニルオキサゾリジノンである、前記使用。
- 請求項1から7までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物が10質量%未満の水または有機溶媒を含有する、前記使用。
- 請求項1から8までのいずれか1項に記載の放射線硬化性組成物の使用であって、前記放射線硬化性組成物が少なくとも1種の光開始剤を含有する、前記使用。
- 請求項1から9までのいずれか1項に記載の放射線硬化性組成物を印刷インキとして使用する、インクジェット印刷法。
- 請求項10に記載のインクジェット印刷法であって、前記放射線硬化性組成物を基材に印刷し、次いで放射線により硬化させる、前記方法。
- 請求項10または11に記載のインクジェット印刷法であって、ポリプロピレン基材に印刷する、前記方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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EP13180035 | 2013-08-12 | ||
EP13180035.1 | 2013-08-12 | ||
PCT/EP2014/066767 WO2015022228A1 (en) | 2013-08-12 | 2014-08-05 | Ink-jet printing ink comprising n-vinyloxazolidinone |
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JP2016529360A JP2016529360A (ja) | 2016-09-23 |
JP6316428B2 true JP6316428B2 (ja) | 2018-04-25 |
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JP2016533884A Active JP6316428B2 (ja) | 2013-08-12 | 2014-08-05 | N−ビニルオキサゾリジノンを含有するインクジェット印刷インキ |
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US (1) | US9447295B2 (ja) |
EP (1) | EP3033399B1 (ja) |
JP (1) | JP6316428B2 (ja) |
CN (2) | CN105431497A (ja) |
ES (1) | ES2655486T3 (ja) |
HU (1) | HUE035653T2 (ja) |
PL (1) | PL3033399T3 (ja) |
WO (1) | WO2015022228A1 (ja) |
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RU2761204C2 (ru) | 2017-02-10 | 2021-12-06 | Басф Се | Мономеры на основе акрилата для применения в качестве реакционноспособных разбавителей в составах для печати |
WO2018146259A1 (en) | 2017-02-10 | 2018-08-16 | Basf Se | Acrylate-based monomers for use as reactive diluents in printing formulations |
GB2573472A (en) * | 2017-02-13 | 2019-11-06 | Fujifilm Speciality Ink Systems Ltd | Printing method and ink |
WO2018146494A1 (en) * | 2017-02-13 | 2018-08-16 | Fujifilm Speciality Ink Systems Limited | Printing method and ink |
WO2019077364A1 (en) * | 2017-10-20 | 2019-04-25 | Fujifilm Speciality Ink Systems Limited | PRINTING INK |
GB201805694D0 (en) * | 2018-04-05 | 2018-05-23 | Fujifilm Speciality Ink Systems Ltd | Printing ink |
GB201807963D0 (en) | 2018-05-16 | 2018-07-04 | Fujifilm Speciality Ink Systems Ltd | Printing ink |
JP7532381B2 (ja) * | 2018-09-24 | 2024-08-13 | ビーエーエスエフ ソシエタス・ヨーロピア | 3d印刷において使用するためのuv硬化性組成物 |
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EP4339248A1 (en) | 2022-09-19 | 2024-03-20 | Agfa Nv | Pigmented free radical curable inkjet inks |
GB202304514D0 (en) | 2023-03-28 | 2023-05-10 | Fujifilm Speciality Ink Systems Ltd | Printing ink |
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US2818362A (en) * | 1954-05-18 | 1957-12-31 | American Cyanamid Co | N-vinyl-2-oxazolidone and polymerization products thereof and method of making |
US4113895A (en) * | 1976-11-19 | 1978-09-12 | American Can Company | Method for producing multilayered coated substrate |
JPS57109813A (en) * | 1980-12-27 | 1982-07-08 | Toagosei Chem Ind Co Ltd | Curing composition |
US4831153A (en) | 1983-06-27 | 1989-05-16 | The Dow Chemical Company | Preparation of N-vinyl-2-oxazolidinone |
US4639472A (en) * | 1984-12-17 | 1987-01-27 | The Dow Chemical Company | N-vinyl-2-oxazolidinones as reactive diluents in actinic radiation curable coatings |
US4774309A (en) * | 1985-07-09 | 1988-09-27 | The Dow Chemical Company | N-vinyl-2-oxazolidinones as reactive diluents in actinic radiation curable coatings |
DE3704098A1 (de) | 1987-02-11 | 1988-08-25 | Basf Ag | Strahlungshaertbare acrylate |
JPH04314769A (ja) * | 1991-04-11 | 1992-11-05 | Citizen Watch Co Ltd | 記録液 |
GB2264118B (en) | 1992-02-07 | 1996-01-10 | Sericol Ltd | Radiation-curable compositions |
JP3086531B2 (ja) * | 1992-03-13 | 2000-09-11 | シチズン時計株式会社 | 記録液 |
EP1205815B1 (en) * | 2000-11-10 | 2009-12-23 | Samsung Electronics Co., Ltd. | Liquid inks comprising surface-treated colorant particles and manufacturing method thereof |
CN1442456A (zh) * | 2002-01-08 | 2003-09-17 | 三星电子株式会社 | 包括稳定有机溶胶的液体油墨 |
JP2007154031A (ja) * | 2005-12-05 | 2007-06-21 | Fujifilm Corp | インク組成物 |
EP2358832A1 (de) | 2008-11-21 | 2011-08-24 | Basf Se | Druckfarbe, enthaltend n-vinylcaprolactam und weitere n-vinylamidmonomere |
CN102348696B (zh) * | 2009-03-13 | 2015-06-17 | 太阳化学有限公司 | 可用于可能量固化的组合物中的环状氨基甲酸酯化合物 |
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2014
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- 2014-08-05 WO PCT/EP2014/066767 patent/WO2015022228A1/en active Application Filing
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- 2014-08-05 ES ES14747646.9T patent/ES2655486T3/es active Active
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- 2014-08-05 US US14/910,965 patent/US9447295B2/en active Active
- 2014-08-05 JP JP2016533884A patent/JP6316428B2/ja active Active
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CN105431497A (zh) | 2016-03-23 |
EP3033399A1 (en) | 2016-06-22 |
PL3033399T3 (pl) | 2018-03-30 |
JP2016529360A (ja) | 2016-09-23 |
ES2655486T3 (es) | 2018-02-20 |
WO2015022228A1 (en) | 2015-02-19 |
CN110256902A (zh) | 2019-09-20 |
US9447295B2 (en) | 2016-09-20 |
EP3033399B1 (en) | 2017-10-11 |
US20160193852A1 (en) | 2016-07-07 |
HUE035653T2 (en) | 2018-05-28 |
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