JP6157321B2 - オリゴマー性ロジンエステルを含有する相変化インク - Google Patents
オリゴマー性ロジンエステルを含有する相変化インク Download PDFInfo
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- JP6157321B2 JP6157321B2 JP2013231777A JP2013231777A JP6157321B2 JP 6157321 B2 JP6157321 B2 JP 6157321B2 JP 2013231777 A JP2013231777 A JP 2013231777A JP 2013231777 A JP2013231777 A JP 2013231777A JP 6157321 B2 JP6157321 B2 JP 6157321B2
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- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 title claims description 42
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 title claims description 37
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 title claims description 37
- 230000008859 change Effects 0.000 title claims description 29
- 150000002148 esters Chemical class 0.000 title claims description 19
- -1 cinnamic acid diester Chemical class 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000002947 alkylene group Chemical group 0.000 claims description 51
- 125000000732 arylene group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 43
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 239000003086 colorant Substances 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000005690 diesters Chemical class 0.000 claims description 6
- 235000002906 tartaric acid Nutrition 0.000 claims description 6
- 239000011975 tartaric acid Substances 0.000 claims description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- XBGRWNKCSCFCAA-UHDJGPCESA-N OCC1CCC(CO)O1.OC(=O)\C=C\C1=CC=CC=C1 Chemical compound OCC1CCC(CO)O1.OC(=O)\C=C\C1=CC=CC=C1 XBGRWNKCSCFCAA-UHDJGPCESA-N 0.000 claims description 2
- IOMZCYWFJSCYQN-UHDJGPCESA-N [2-(hydroxymethyl)furan-3-yl]methanol;(e)-3-phenylprop-2-enoic acid Chemical compound OCC=1C=COC=1CO.OC(=O)\C=C\C1=CC=CC=C1 IOMZCYWFJSCYQN-UHDJGPCESA-N 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- LCKIPSGLXMCAOF-HZPDHXFCSA-N dibenzyl (2r,3r)-2,3-dihydroxybutanedioate Chemical group O=C([C@H](O)[C@@H](O)C(=O)OCC=1C=CC=CC=1)OCC1=CC=CC=C1 LCKIPSGLXMCAOF-HZPDHXFCSA-N 0.000 claims description 2
- UXHUJQMSTNOTRT-ZIAGYGMSSA-N dicyclohexyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound O=C([C@H](O)[C@@H](O)C(=O)OC1CCCCC1)OC1CCCCC1 UXHUJQMSTNOTRT-ZIAGYGMSSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
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- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 229940114081 cinnamate Drugs 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 239000000976 ink Substances 0.000 description 132
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 66
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 33
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 33
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 33
- 229910052796 boron Inorganic materials 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 229910052760 oxygen Inorganic materials 0.000 description 33
- 239000001301 oxygen Substances 0.000 description 33
- 229910052698 phosphorus Inorganic materials 0.000 description 33
- 239000011574 phosphorus Chemical group 0.000 description 33
- 239000011593 sulfur Chemical group 0.000 description 33
- 229910052717 sulfur Inorganic materials 0.000 description 33
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 32
- 239000010703 silicon Chemical group 0.000 description 32
- 229910052710 silicon Inorganic materials 0.000 description 32
- 125000004122 cyclic group Chemical group 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229920006395 saturated elastomer Polymers 0.000 description 24
- 125000001424 substituent group Chemical group 0.000 description 18
- 239000000463 material Substances 0.000 description 17
- 125000003710 aryl alkyl group Chemical group 0.000 description 15
- 229920002601 oligoester Polymers 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000002877 alkyl aryl group Chemical group 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 125000002843 carboxylic acid group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 125000004018 acid anhydride group Chemical group 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003172 aldehyde group Chemical group 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 150000007942 carboxylates Chemical group 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 6
- 125000000468 ketone group Chemical group 0.000 description 6
- 125000002560 nitrile group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 125000005496 phosphonium group Chemical group 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 6
- 125000001174 sulfone group Chemical group 0.000 description 6
- 125000000542 sulfonic acid group Chemical group 0.000 description 6
- 125000003375 sulfoxide group Chemical group 0.000 description 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 6
- 125000000101 thioether group Chemical group 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- 125000005628 tolylene group Chemical group 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 5
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 5
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- MHVJRKBZMUDEEV-UHFFFAOYSA-N (-)-ent-pimara-8(14),15-dien-19-oic acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)C=C1CC2 MHVJRKBZMUDEEV-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical class CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
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- 229910021641 deionized water Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 235000011078 sorbitan tristearate Nutrition 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
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- MXYATHGRPJZBNA-UHFFFAOYSA-N 4-epi-isopimaric acid Natural products C1CCC(C(O)=O)(C)C2C1(C)C1CCC(C=C)(C)CC1=CC2 MXYATHGRPJZBNA-UHFFFAOYSA-N 0.000 description 2
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- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 description 2
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- MXYATHGRPJZBNA-KRFUXDQASA-N isopimaric acid Chemical compound [C@H]1([C@](CCC2)(C)C(O)=O)[C@@]2(C)[C@H]2CC[C@@](C=C)(C)CC2=CC1 MXYATHGRPJZBNA-KRFUXDQASA-N 0.000 description 2
- DJWFNQUDPJTSAD-UHFFFAOYSA-N n-octadecyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC DJWFNQUDPJTSAD-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 229940081141 hexadecanamide Drugs 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
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- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
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- 239000005445 natural material Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- YZVSLDRKXBZOMY-KNOXWWKRSA-N sandaracopimaric acid Natural products CC(=C)[C@]1(C)CCC[C@]2(C)[C@H]3CC[C@](C)(C=C)C=C3CC[C@@H]12 YZVSLDRKXBZOMY-KNOXWWKRSA-N 0.000 description 1
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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
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
-
- 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
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/680,271 US8778069B2 (en) | 2012-11-19 | 2012-11-19 | Phase change inks containing oligomeric rosin esters |
| US13/680,271 | 2012-11-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014101510A JP2014101510A (ja) | 2014-06-05 |
| JP2014101510A5 JP2014101510A5 (enExample) | 2016-12-22 |
| JP6157321B2 true JP6157321B2 (ja) | 2017-07-05 |
Family
ID=50726711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013231777A Expired - Fee Related JP6157321B2 (ja) | 2012-11-19 | 2013-11-08 | オリゴマー性ロジンエステルを含有する相変化インク |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US8778069B2 (enExample) |
| JP (1) | JP6157321B2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9120943B2 (en) * | 2013-10-15 | 2015-09-01 | Xerox Corporation | Bio-renewable phase change inks |
| JP7093150B2 (ja) * | 2018-12-06 | 2022-06-29 | 日本化薬株式会社 | 硬化性樹脂組成物及びその硬化物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5006170A (en) * | 1989-06-22 | 1991-04-09 | Xerox Corporation | Hot melt ink compositions |
| US5750604A (en) * | 1996-06-28 | 1998-05-12 | Tektronix, Inc. | Phase change ink formulation using a urethane isocyanate-derived resin |
| US5780528A (en) * | 1996-06-28 | 1998-07-14 | Tektronix, Inc. | Isocyanate-derived colored resins for use in phase change ink jet inks |
| US5919839A (en) * | 1996-06-28 | 1999-07-06 | Tektronix, Inc. | Phase change ink formulation using an isocyanate-derived wax and a clear ink carrier base |
| NL1012549C2 (nl) * | 1999-07-09 | 2001-01-10 | Ocu Technologies B V | Inktsamenstelling voor een smeltbare inkt en een werkwijze voor het bedrukken van een substraat met een dergelijke inktsamenstelling. |
| US20030101902A1 (en) * | 2001-12-04 | 2003-06-05 | Ann Reitnauer | Hot melt inks |
| US20080098929A1 (en) * | 2006-10-26 | 2008-05-01 | Xerox Corporation | Phase change inks |
| US20080098930A1 (en) * | 2006-11-01 | 2008-05-01 | Xerox Corporation | Colorant dispersant |
| US9499709B2 (en) * | 2010-03-01 | 2016-11-22 | Xerox Corporation | Oligomeric rosin esters for use in inks |
| US8968452B2 (en) * | 2011-04-27 | 2015-03-03 | Xerox Corporation | Phase change inks containing crystalline trans-cinnamic diesters and amorphous isosorbide oligomers |
| US8465579B2 (en) * | 2011-04-27 | 2013-06-18 | Xerox Corporation | Solid ink compositions comprising crystalline esters of tartaric acid |
| KR101318708B1 (ko) * | 2010-12-15 | 2013-10-16 | 에스케이이노베이션 주식회사 | 폴리프로필렌카보네이트를 이용한 로토그라비아 핫멜트 잉크 조성물 |
| US8906150B2 (en) * | 2011-04-27 | 2014-12-09 | Xerox Corporation | Phase change inks containing crystalline trans-cinnamic diesters and polyterpene resins |
-
2012
- 2012-11-19 US US13/680,271 patent/US8778069B2/en not_active Expired - Fee Related
-
2013
- 2013-11-08 JP JP2013231777A patent/JP6157321B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20140137767A1 (en) | 2014-05-22 |
| JP2014101510A (ja) | 2014-06-05 |
| US8778069B2 (en) | 2014-07-15 |
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