KR20140143088A - 상 변화 잉크용 비결정성 물질로서의 타르타르산 에스테르 및 시트르산 에스테르의 혼합물 - Google Patents
상 변화 잉크용 비결정성 물질로서의 타르타르산 에스테르 및 시트르산 에스테르의 혼합물 Download PDFInfo
- Publication number
- KR20140143088A KR20140143088A KR1020140059627A KR20140059627A KR20140143088A KR 20140143088 A KR20140143088 A KR 20140143088A KR 1020140059627 A KR1020140059627 A KR 1020140059627A KR 20140059627 A KR20140059627 A KR 20140059627A KR 20140143088 A KR20140143088 A KR 20140143088A
- Authority
- KR
- South Korea
- Prior art keywords
- ink
- tartaric acid
- citrate
- tartrate
- acid ester
- 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.)
- Ceased
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 52
- 239000000463 material Substances 0.000 title claims abstract description 43
- 230000008859 change Effects 0.000 title claims abstract description 42
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims description 24
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 title claims description 18
- 239000011975 tartaric acid Substances 0.000 title claims description 10
- 235000002906 tartaric acid Nutrition 0.000 title claims description 10
- 239000000976 ink Substances 0.000 title abstract description 126
- 150000002148 esters Chemical class 0.000 title description 6
- -1 citric acid ester Chemical class 0.000 claims abstract description 25
- 150000003899 tartaric acid esters Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 230000009477 glass transition Effects 0.000 claims description 10
- 229960001367 tartaric acid Drugs 0.000 claims description 9
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 8
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 4
- 239000001358 L(+)-tartaric acid Substances 0.000 claims description 4
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims description 4
- 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 4
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims description 4
- RTVKVYSZXNOXND-UHFFFAOYSA-N 1,1,3-tricyclopentyl-2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound C1CCC(C1)C(C(=O)O)C(C(=O)O)(C(C2CCCC2)(C3CCCC3)C(=O)O)O RTVKVYSZXNOXND-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- LCKIPSGLXMCAOF-HZPDHXFCSA-N dibenzyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound 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 3
- 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 3
- 229940048879 dl tartaric acid Drugs 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- VYLZSGQQVHTICN-UHFFFAOYSA-N tribenzyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C=1C=CC=CC=1COC(=O)CC(C(=O)OCC=1C=CC=CC=1)(O)CC(=O)OCC1=CC=CC=C1 VYLZSGQQVHTICN-UHFFFAOYSA-N 0.000 claims description 3
- CBKMOPGKNJBDFA-UHFFFAOYSA-N tricyclohexyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C1CCCCC1OC(=O)CC(C(=O)OC1CCCCC1)(O)CC(=O)OC1CCCCC1 CBKMOPGKNJBDFA-UHFFFAOYSA-N 0.000 claims description 3
- CFOWTNWLYYUUPZ-UHFFFAOYSA-N tris(1-methyl-4-propan-2-ylcyclohexyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound C(CC(O)(C(=O)OC1(CCC(CC1)C(C)C)C)CC(=O)OC1(CCC(CC1)C(C)C)C)(=O)OC1(CCC(CC1)C(C)C)C CFOWTNWLYYUUPZ-UHFFFAOYSA-N 0.000 claims description 3
- IMVBWAVSRXXOSN-UHFFFAOYSA-N tris(2-phenoxyethyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound OC(CC(=O)OCCOc1ccccc1)(CC(=O)OCCOc1ccccc1)C(=O)OCCOc1ccccc1 IMVBWAVSRXXOSN-UHFFFAOYSA-N 0.000 claims description 3
- HCNCFXGRIKTYQI-UHFFFAOYSA-N tris(2-phenylethyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound OC(CC(=O)OCCc1ccccc1)(CC(=O)OCCc1ccccc1)C(=O)OCCc1ccccc1 HCNCFXGRIKTYQI-UHFFFAOYSA-N 0.000 claims description 3
- HMVQLAHNCQKGGH-UHFFFAOYSA-N tris(3-phenylpropyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound OC(CC(=O)OCCCc1ccccc1)(CC(=O)OCCCc1ccccc1)C(=O)OCCCc1ccccc1 HMVQLAHNCQKGGH-UHFFFAOYSA-N 0.000 claims description 3
- ALFZETQIEXOIBP-UHFFFAOYSA-N tris(4-tert-butylcyclohexyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)(C)C1CCC(CC1)OC(=O)CC(O)(CC(=O)OC1CCC(CC1)C(C)(C)C)C(=O)OC1CCC(CC1)C(C)(C)C ALFZETQIEXOIBP-UHFFFAOYSA-N 0.000 claims description 3
- UEGYLOJHKXCEOT-MHUBRMLGSA-N bis(4-tert-butylcyclohexyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)[C@H](O)[C@@H](O)C(=O)OC1CCC(C(C)(C)C)CC1 UEGYLOJHKXCEOT-MHUBRMLGSA-N 0.000 claims description 2
- YRLYXFBOMQAATC-QZTJIDSGSA-N bis[(4-methoxyphenyl)methyl] (2r,3r)-2,3-dihydroxybutanedioate Chemical compound C1=CC(OC)=CC=C1COC(=O)[C@H](O)[C@@H](O)C(=O)OCC1=CC=C(OC)C=C1 YRLYXFBOMQAATC-QZTJIDSGSA-N 0.000 claims description 2
- HZBOQOXQPRQKTF-HZPDHXFCSA-N bis(4-methylphenyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1OC(=O)[C@H](O)[C@@H](O)C(=O)OC1=CC=C(C)C=C1 HZBOQOXQPRQKTF-HZPDHXFCSA-N 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 1
- 239000000049 pigment Substances 0.000 description 21
- 238000007639 printing Methods 0.000 description 18
- 239000003086 colorant Substances 0.000 description 16
- 238000007641 inkjet printing Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000012943 hotmelt Substances 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002178 crystalline material Substances 0.000 description 5
- VSSBWJOYPQVXKX-UHFFFAOYSA-N dioctadecyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCCCCCCCCCC)C=C1 VSSBWJOYPQVXKX-UHFFFAOYSA-N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000992 solvent dye Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- MYMKXVFDVQUQLG-UHFFFAOYSA-N 1,3,7,9-tetratert-butyl-11-fluoro-5-methyl-5h-benzo[d][1,3,2]benzodioxaphosphocine Chemical compound CC1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP(F)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C MYMKXVFDVQUQLG-UHFFFAOYSA-N 0.000 description 2
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 2
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 2
- OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 description 2
- LUWJPTVQOMUZLW-UHFFFAOYSA-N Luxol fast blue MBS Chemical compound [Cu++].Cc1ccccc1N\C(N)=N\c1ccccc1C.Cc1ccccc1N\C(N)=N\c1ccccc1C.OS(=O)(=O)c1cccc2c3nc(nc4nc([n-]c5[n-]c(nc6nc(n3)c3ccccc63)c3c(cccc53)S(O)(=O)=O)c3ccccc43)c12 LUWJPTVQOMUZLW-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- UGWZNTNLSUTFKX-WOJBJXKFSA-N bis(3-phenylpropyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound O=C([C@H](O)[C@@H](O)C(=O)OCCCC=1C=CC=CC=1)OCCCC1=CC=CC=C1 UGWZNTNLSUTFKX-WOJBJXKFSA-N 0.000 description 2
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- XOCUHWXGSSSCTJ-UHFFFAOYSA-N chembl3145171 Chemical compound O=C1C(N=NC=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 XOCUHWXGSSSCTJ-UHFFFAOYSA-N 0.000 description 2
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- 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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- DLDDIHRRFIDSOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(4-methoxyphenyl)methyl]phenol Chemical compound C1=CC(OC)=CC=C1CC1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DLDDIHRRFIDSOW-UHFFFAOYSA-N 0.000 description 1
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- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
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- 239000004234 Yellow 2G Substances 0.000 description 1
- OCKWAZCWKSMKNC-UHFFFAOYSA-N [3-octadecanoyloxy-2,2-bis(octadecanoyloxymethyl)propyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC OCKWAZCWKSMKNC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- WRAZZSHIESLGRR-QZTJIDSGSA-N bis(2-phenoxyethyl) (2r,3r)-2,3-dihydroxybutanedioate Chemical compound O=C([C@H](O)[C@@H](O)C(=O)OCCOC=1C=CC=CC=1)OCCOC1=CC=CC=C1 WRAZZSHIESLGRR-QZTJIDSGSA-N 0.000 description 1
- NNFHDLRXMNWDSO-QZTJIDSGSA-N bis[(4-methylphenyl)methyl] (2r,3r)-2,3-dihydroxybutanedioate Chemical compound C1=CC(C)=CC=C1COC(=O)[C@H](O)[C@@H](O)C(=O)OCC1=CC=C(C)C=C1 NNFHDLRXMNWDSO-QZTJIDSGSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- JBTHDAVBDKKSRW-UHFFFAOYSA-N chembl1552233 Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JBTHDAVBDKKSRW-UHFFFAOYSA-N 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000000982 direct dye Chemical class 0.000 description 1
- FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
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- 239000006025 fining agent Substances 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZNOGFZNFAYMXDC-UHFFFAOYSA-N hydroxyphosphanyloxyphosphinous acid 1,2,3,5-tetrakis(2,4-ditert-butylphenyl)-4-phenylbenzene Chemical compound OPOPO.CC(C)(C)C1=CC(C(C)(C)C)=CC=C1C(C(=C1C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)C=2C=CC=CC=2)=CC(C=2C(=CC(=CC=2)C(C)(C)C)C(C)(C)C)=C1C1=CC=C(C(C)(C)C)C=C1C(C)(C)C ZNOGFZNFAYMXDC-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000002122 magnetic nanoparticle Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WNWZKKBGFYKSGA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-2-[[2,5-dimethoxy-4-(phenylsulfamoyl)phenyl]diazenyl]-3-oxobutanamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C(N=NC=2C(=CC(=C(OC)C=2)S(=O)(=O)NC=2C=CC=CC=2)OC)C(C)=O)=C1OC WNWZKKBGFYKSGA-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000988 sulfur dye Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 239000000984 vat dye Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
Images
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
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/909,975 US9090791B2 (en) | 2013-06-04 | 2013-06-04 | Mixtures of ester of tartaric acid and ester of citric acid as amorphous materials for phase change inks |
| US13/909,975 | 2013-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140143088A true KR20140143088A (ko) | 2014-12-15 |
Family
ID=51899666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020140059627A Ceased KR20140143088A (ko) | 2013-06-04 | 2014-05-19 | 상 변화 잉크용 비결정성 물질로서의 타르타르산 에스테르 및 시트르산 에스테르의 혼합물 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9090791B2 (enExample) |
| JP (1) | JP6280442B2 (enExample) |
| KR (1) | KR20140143088A (enExample) |
| DE (1) | DE102014210120A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022239991A1 (ko) * | 2021-05-11 | 2022-11-17 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| WO2022239992A1 (ko) * | 2021-05-11 | 2022-11-17 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| KR20220153489A (ko) * | 2021-05-11 | 2022-11-18 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| WO2024053992A1 (ko) * | 2022-09-06 | 2024-03-14 | 삼성디스플레이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3677651B1 (en) * | 2019-01-04 | 2021-10-27 | Canon Production Printing Holding B.V. | Radiation-curable inkjet ink composition |
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|---|---|---|---|---|
| US4490731A (en) | 1982-11-22 | 1984-12-25 | Hewlett-Packard Company | Ink dispenser with "frozen" solid ink |
| US4889560A (en) | 1988-08-03 | 1989-12-26 | Tektronix, Inc. | Phase change ink composition and phase change ink produced therefrom |
| US4889761A (en) | 1988-08-25 | 1989-12-26 | Tektronix, Inc. | Substrates having a light-transmissive phase change ink printed thereon and methods for producing same |
| US5195430A (en) | 1989-05-24 | 1993-03-23 | Tektronix, Inc. | Dual roller apparatus for pressure fixing sheet material |
| US5231135A (en) | 1989-09-05 | 1993-07-27 | Milliken Research Corporation | Lightfast colored polymeric coatings and process for making same |
| US5221335A (en) | 1990-05-23 | 1993-06-22 | Coates Electrographics Limited | Stabilized pigmented hot melt ink containing nitrogen-modified acrylate polymer as dispersion-stabilizer agent |
| US5372852A (en) | 1992-11-25 | 1994-12-13 | Tektronix, Inc. | Indirect printing process for applying selective phase change ink compositions to substrates |
| US5621022A (en) | 1992-11-25 | 1997-04-15 | Tektronix, Inc. | Use of polymeric dyes in hot melt ink jet inks |
| US6221137B1 (en) | 1999-06-18 | 2001-04-24 | Xerox Corporation | Metal phthalocyanine colorants for phase change inks |
| US6726755B2 (en) | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
| US6476219B1 (en) | 2002-02-08 | 2002-11-05 | Xerox Corporation | Methods for preparing phthalocyanine compositions |
| US6472523B1 (en) | 2002-02-08 | 2002-10-29 | Xerox Corporation | Phthalocyanine compositions |
| US6590082B1 (en) | 2002-06-27 | 2003-07-08 | Xerox Corporation | Azo pyridone colorants |
| US6755902B2 (en) | 2002-06-27 | 2004-06-29 | Xerox Corporation | Phase change inks containing azo pyridone colorants |
| US6663703B1 (en) | 2002-06-27 | 2003-12-16 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6576748B1 (en) | 2002-06-27 | 2003-06-10 | Xerox Corporation | Method for making dimeric azo pyridone colorants |
| US6646111B1 (en) | 2002-06-27 | 2003-11-11 | Xerox Corporation | Dimeric azo pyridone colorants |
| US6673139B1 (en) | 2002-06-27 | 2004-01-06 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6713614B2 (en) | 2002-06-27 | 2004-03-30 | Xerox Corporation | Dimeric azo pyridone colorants |
| US6576747B1 (en) | 2002-06-27 | 2003-06-10 | Xerox Corporation | Processes for preparing dianthranilate compounds and diazopyridone colorants |
| US6696552B2 (en) | 2002-06-27 | 2004-02-24 | Xerox Corporation | Process for preparing substituted pyridone compounds |
| US7053227B2 (en) | 2002-09-27 | 2006-05-30 | Xerox Corporation | Methods for making colorant compounds |
| US6958406B2 (en) | 2002-09-27 | 2005-10-25 | Xerox Corporation | Colorant compounds |
| US6821327B2 (en) | 2002-09-27 | 2004-11-23 | Xerox Corporation | Phase change inks |
| US7186762B2 (en) | 2003-11-25 | 2007-03-06 | Xerox Corporation | Processes for preparing phase change inks |
| US7381831B1 (en) | 2007-04-04 | 2008-06-03 | Xerox Corporation | Colorant compounds |
| US7427323B1 (en) | 2007-06-07 | 2008-09-23 | Xerox Corporation | Quinacridone nanoscale pigment particles |
| US8293444B2 (en) * | 2009-06-24 | 2012-10-23 | Xerox Corporation | Purified polyester resins for toner performance improvement |
| US7973186B1 (en) | 2009-12-18 | 2011-07-05 | Xerox Corporation | Low molecular weight pigment dispersants for phase change ink |
| US8506040B2 (en) * | 2011-04-27 | 2013-08-13 | Xerox Corporation | Solid ink compositions comprising crystalline-amorphous mixtures |
| US8506694B2 (en) * | 2011-04-27 | 2013-08-13 | Xerox Corporation | Phase separation ink |
-
2013
- 2013-06-04 US US13/909,975 patent/US9090791B2/en active Active
-
2014
- 2014-05-19 KR KR1020140059627A patent/KR20140143088A/ko not_active Ceased
- 2014-05-20 JP JP2014104732A patent/JP6280442B2/ja not_active Expired - Fee Related
- 2014-05-27 DE DE201410210120 patent/DE102014210120A1/de not_active Ceased
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022239991A1 (ko) * | 2021-05-11 | 2022-11-17 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| WO2022239992A1 (ko) * | 2021-05-11 | 2022-11-17 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| KR20220153489A (ko) * | 2021-05-11 | 2022-11-18 | 삼성에스디아이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
| TWI819588B (zh) * | 2021-05-11 | 2023-10-21 | 南韓商三星Ｓｄｉ股份有限公司 | 油墨組成物、使用此組成物的層、以及包含此組成物的電泳裝置和顯示裝置 |
| WO2024053992A1 (ko) * | 2022-09-06 | 2024-03-14 | 삼성디스플레이 주식회사 | 잉크 조성물, 이를 이용한 막, 이를 포함하는 전기영동 장치 및 디스플레이 장치 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20140352576A1 (en) | 2014-12-04 |
| DE102014210120A1 (de) | 2014-12-04 |
| JP6280442B2 (ja) | 2018-02-14 |
| JP2014234517A (ja) | 2014-12-15 |
| US9090791B2 (en) | 2015-07-28 |
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