JP6312560B2 - 非晶質尿素を含むインク - Google Patents
非晶質尿素を含むインク Download PDFInfo
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- JP6312560B2 JP6312560B2 JP2014170636A JP2014170636A JP6312560B2 JP 6312560 B2 JP6312560 B2 JP 6312560B2 JP 2014170636 A JP2014170636 A JP 2014170636A JP 2014170636 A JP2014170636 A JP 2014170636A JP 6312560 B2 JP6312560 B2 JP 6312560B2
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- amorphous
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- urea
- phase change
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 35
- 239000004202 carbamide Substances 0.000 title claims description 29
- 230000008859 change Effects 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000000976 ink Substances 0.000 description 123
- 239000012071 phase Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 32
- 239000011162 core material Substances 0.000 description 23
- 239000003086 colorant Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 16
- 239000000049 pigment Substances 0.000 description 15
- -1 small molecule amine Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000007639 printing Methods 0.000 description 8
- 239000002178 crystalline material Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005291 magnetic effect Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000399 optical microscopy Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000992 solvent dye Substances 0.000 description 3
- 238000003786 synthesis reaction 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
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CC(CCNC(*)=O)CC(C)(C)CNC(*)=O Chemical compound CC(CCNC(*)=O)CC(C)(C)CNC(*)=O 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)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 BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 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
- 238000005520 cutting process Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 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 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- DAVRGGJTJDTVQT-UHFFFAOYSA-N n-(2-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCC1=CC=CC=C1 DAVRGGJTJDTVQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- GUTWGLKCVAFMPJ-UHFFFAOYSA-N 1-(2,6-dibromo-4-methylanilino)-4-hydroxyanthracene-9,10-dione Chemical compound BrC1=CC(C)=CC(Br)=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O GUTWGLKCVAFMPJ-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- 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
- PINBPLCVZSKLTF-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC(C(F)(F)F)=CC=C1C(F)(F)F PINBPLCVZSKLTF-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- OEWRSPSSAUTKPO-UHFFFAOYSA-N 2,6-dibromo-3-fluorophenol Chemical compound OC1=C(Br)C=CC(F)=C1Br OEWRSPSSAUTKPO-UHFFFAOYSA-N 0.000 description 1
- BOJVIFKSTRCIRJ-UHFFFAOYSA-N 2,6-dichloro-4-fluorophenol Chemical compound OC1=C(Cl)C=C(F)C=C1Cl BOJVIFKSTRCIRJ-UHFFFAOYSA-N 0.000 description 1
- IIKSFQIOFHBWSO-UHFFFAOYSA-N 2,9-bis(2-phenylethyl)anthra(2,1,9-def:6,5,10-d'e'f')diisoquinoline-1,3,8,10(2h,9h)-tetrone Chemical compound O=C1C(C2=C34)=CC=C3C(C=35)=CC=C(C(N(CCC=6C=CC=CC=6)C6=O)=O)C5=C6C=CC=3C4=CC=C2C(=O)N1CCC1=CC=CC=C1 IIKSFQIOFHBWSO-UHFFFAOYSA-N 0.000 description 1
- RPTRFSADOICSSK-UHFFFAOYSA-N 2-(2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1F RPTRFSADOICSSK-UHFFFAOYSA-N 0.000 description 1
- YCAKYFIYUHHCKW-UHFFFAOYSA-N 2-(3,4-difluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C(F)=C1 YCAKYFIYUHHCKW-UHFFFAOYSA-N 0.000 description 1
- YEAUYVGUXSZCFI-UHFFFAOYSA-N 2-(3-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(F)=C1 YEAUYVGUXSZCFI-UHFFFAOYSA-N 0.000 description 1
- KNZIPRGWALMMQE-UHFFFAOYSA-N 2-[4-[2-[4-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCOC=2C=CC(=CC=2)C(C)(C)C=2C=CC(OCCOC(=O)CCC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)=CC=2)=C1 KNZIPRGWALMMQE-UHFFFAOYSA-N 0.000 description 1
- MEYRABVEYCFHHB-UHFFFAOYSA-N 2-bromo-4-fluorophenol Chemical compound OC1=CC=C(F)C=C1Br MEYRABVEYCFHHB-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- DZNJMLVCIZGWSC-UHFFFAOYSA-N 3',6'-bis(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N(CC)CC)C=C1OC1=CC(N(CC)CC)=CC=C21 DZNJMLVCIZGWSC-UHFFFAOYSA-N 0.000 description 1
- FJDLQLIRZFKEKJ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(N)=O)=CC(C(C)(C)C)=C1O FJDLQLIRZFKEKJ-UHFFFAOYSA-N 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 description 1
- YSCNMFDFYJUPEF-OWOJBTEDSA-N 4,4'-diisothiocyano-trans-stilbene-2,2'-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(N=C=S)=CC=C1\C=C\C1=CC=C(N=C=S)C=C1S(O)(=O)=O YSCNMFDFYJUPEF-OWOJBTEDSA-N 0.000 description 1
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 1
- XWLYWWDJKAPLDA-UHFFFAOYSA-N 4-(diethylaminomethyl)-2,5-dimethylphenol Chemical compound CCN(CC)CC1=CC(C)=C(O)C=C1C XWLYWWDJKAPLDA-UHFFFAOYSA-N 0.000 description 1
- ZLVFYUORUHNMBO-UHFFFAOYSA-N 4-bromo-2,6-dimethylphenol Chemical compound CC1=CC(Br)=CC(C)=C1O ZLVFYUORUHNMBO-UHFFFAOYSA-N 0.000 description 1
- CUTFAPGINUFNQM-UHFFFAOYSA-N 4-bromo-2-nitrophenol Chemical compound OC1=CC=C(Br)C=C1[N+]([O-])=O CUTFAPGINUFNQM-UHFFFAOYSA-N 0.000 description 1
- WMUWDPLTTLJNPE-UHFFFAOYSA-N 4-bromo-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Br WMUWDPLTTLJNPE-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- NXYYRSJPSPRDEO-UHFFFAOYSA-N 5-(diethylamino)-2-nitrosophenol Chemical compound CCN(CC)C1=CC=C(N=O)C(O)=C1 NXYYRSJPSPRDEO-UHFFFAOYSA-N 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- OQSSNGKVNWXYOE-UHFFFAOYSA-N N=C=O.N=C=O.CCC(C)CC(C)(C)C Chemical compound N=C=O.N=C=O.CCC(C)CC(C)(C)C OQSSNGKVNWXYOE-UHFFFAOYSA-N 0.000 description 1
- 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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 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
- 230000000903 blocking effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 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
- 239000003795 chemical substances by application Substances 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
- 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 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- IEEIDZAXDTVGGN-RMRYJAPISA-N cyclopenta-1,3-dien-1-yl(diphenyl)phosphane;(1s)-1-(2-diphenylphosphanylcyclopenta-1,3-dien-1-yl)-n,n-dimethylethanamine;iron(2+) Chemical compound [Fe+2].C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1[C@@H](N(C)C)C IEEIDZAXDTVGGN-RMRYJAPISA-N 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
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- 238000010017 direct printing Methods 0.000 description 1
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- FEMOFHMHEFIHKN-UHFFFAOYSA-N ethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FEMOFHMHEFIHKN-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000006025 fining agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000007774 longterm Effects 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000002122 magnetic nanoparticle Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 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
- 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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 239000004014 plasticizer Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 101150008563 spir gene Proteins 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 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
- C09D11/30—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
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Description
この実施例は、TMHDI系の分岐鎖状アルキルコアに基づく、非晶質ビス−尿素の調製および特徴決定を示す。
VESTANAT(登録商標)TMDIとして、Evonik Corporationから入手できる、2,2,4−トリメチルヘキサメチレンジイソシアネート、TMHDIを、分岐鎖状のアルキルコア材料として使用する。前記材料は、2,2,4および2,4,4の異性体の1:1の混合物として存在する。簡単にするために、前記2,2,4異性体のみを示す。TMHDIを、2当量の種々の小分子アミンと反応させ、以下のスキーム1に基づいて、ビス−尿素を製造した。
サンプル(1)−(5)の粘度および熱分析を測定した。図1および図2に、サンプル(1)についてのデータを示す。レオロジートレースは、非晶質の化合物と一致する。DSCは、2.48℃のTg(ガラス転移点)を示した。以下の表2に、サンプル(1)−(5)の前記非晶質ビス−尿素の特性をまとめる。
この実施例は、実施例1によるTMHDI系の分岐鎖状アルキルコアに基づく、非晶質ビス−尿素を包含するインクの調製および特徴決定を示す。
非晶質ビス−尿素のサンプル(1)−(5)を含む5つのインクを、結晶質材料としてのN−フェニルエチルベンズアミド(N−PEB)、および、TBCT媒体におけるシアン顔料分散液を使用して調製した。前記配合を、以下にまとめる。
インクのレオロジーを、5つ全てのインクについて測定し、一例を図3に示した。表3は、試験したインク配合が、吐出用の140℃において、適切な粘度(すなわち、約10cps)を有することを示す。
印刷の堅牢性を試験するために、インク1−3を、Xerox(登録商標)Digital Color Elite Gloss、120gsm(DCEG)コート紙上に、K−prooferグラビア印刷プレートを使用して印刷した。前記プレートは、低圧力での圧力ロールセットを備える。前記グラビアプレートの温度を、142℃に設定したが、実際のプレート温度は、約134℃であった。前記K−proofer装置(RK Print Coat Instrument Ltd., Litlington、Royston、Heris、SG8 0OZ、U.K.により製造)は、各種のインクを小規模でスクリーンし、種々の基材上での画像品質を評価するのに有用な印刷ツールである。前記インクにより、前記基材から容易に除去され得ない、堅牢な画像が取得された。適用された重さ528gの、垂直から約15°の角度で湾曲したチップを有する金属チップにより、おおよそ13mm/sの速度で、前記画像を横切って線を引いた場合、インクは、前記画像から、目視により除去されなかった。前記チップは、おおよそ12mmの曲率半径を有する、旋盤の先が丸くなった切断ビットに類似している。
3つの印刷されたインク(インク1−3)を、TROMを使用して、結晶化速度について試験した。試験を、印刷された基材上での凝固時間をまねるように開発した。速い印刷についての試験インクの適合性を評価するために、結晶質成分を含む固体インクの結晶化速度を測定するための定量法を開発した。TROM(時間分離光学顕微鏡法)は、種々の試験サンプル間での比較を可能にし、結果として、速く結晶化するインクの設計に関してなされる進行をモニターするための有用なツールである。
Claims (4)
- 結晶質成分と、
尿素成分とを含み、
前記尿素成分が、分岐鎖状のアルキルコアと尿素官能基とを含む、式IVの化合物及びIV’の化合物のうち少なくとも一方を含み、
式IV及び式IV’中、各Rが、C 1 からC 6 の分岐鎖状または直鎖状のアルキルから独立して選択され、前記分岐鎖状のアルキルコアの分岐度合いが、非晶質の前記尿素成分を提供するのに十分である、
相変化インク。 - 前記各Rが、それぞれ独立に、イソアミル、n−プロピル、tert−ペンチル、n−ブチル、及びsec−ブチルからなる群から選択される、請求項1に記載の相変化インク。
- 結晶質成分と、
非晶質成分とを含み、
前記非晶質成分が、式IVの化合物及びIV’の化合物のうち少なくとも一方を含み、
式IV及び式IV’中、各Rが、C 1 からC 6 の分岐鎖状または直鎖状のアルキルから独立して選択され、前記非晶質成分が、−15℃から30℃の範囲のガラス転移点を有する、
相変化インク。 - 前記各Rが、それぞれ独立に、イソアミル、n−プロピル、tert−ペンチル、n−ブチル、及びsec−ブチルからなる群から選択される、請求項3に記載の相変化インク。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/018,334 | 2013-09-04 | ||
| US14/018,334 US9074104B2 (en) | 2013-09-04 | 2013-09-04 | Inks comprising amorphous ureas |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015048480A JP2015048480A (ja) | 2015-03-16 |
| JP2015048480A5 JP2015048480A5 (ja) | 2017-09-28 |
| JP6312560B2 true JP6312560B2 (ja) | 2018-04-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014170636A Active JP6312560B2 (ja) | 2013-09-04 | 2014-08-25 | 非晶質尿素を含むインク |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9074104B2 (ja) |
| JP (1) | JP6312560B2 (ja) |
| KR (1) | KR102112370B1 (ja) |
| DE (1) | DE102014217360A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9422440B2 (en) * | 2013-12-06 | 2016-08-23 | Xerox Corporation | Bis-ureas as amorphous materials for phase-change ink |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231135A (en) | 1989-09-05 | 1993-07-27 | Milliken Research Corporation | Lightfast colored polymeric coatings and process for making same |
| 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 |
| 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 |
| US6726755B2 (en) | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
| US6576748B1 (en) | 2002-06-27 | 2003-06-10 | Xerox Corporation | Method for making dimeric azo pyridone colorants |
| US6673139B1 (en) * | 2002-06-27 | 2004-01-06 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6755902B2 (en) | 2002-06-27 | 2004-06-29 | Xerox Corporation | Phase change inks containing azo pyridone colorants |
| US6646111B1 (en) * | 2002-06-27 | 2003-11-11 | 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 |
| US6590082B1 (en) | 2002-06-27 | 2003-07-08 | Xerox Corporation | Azo pyridone colorants |
| US6663703B1 (en) | 2002-06-27 | 2003-12-16 | Xerox Corporation | Phase change inks containing dimeric azo pyridone colorants |
| US6713614B2 (en) | 2002-06-27 | 2004-03-30 | Xerox Corporation | Dimeric azo pyridone colorants |
| US6860928B2 (en) * | 2002-09-04 | 2005-03-01 | Xerox Corporation | Alkylated urea and triaminotriazine compounds and phase change inks containing same |
| US6958406B2 (en) | 2002-09-27 | 2005-10-25 | Xerox Corporation | Colorant compounds |
| US7053227B2 (en) * | 2002-09-27 | 2006-05-30 | Xerox Corporation | Methods for making colorant compounds |
| US6821327B2 (en) * | 2002-09-27 | 2004-11-23 | Xerox Corporation | Phase change inks |
| US7220300B2 (en) * | 2004-12-04 | 2007-05-22 | Xerox Corporation | Phase change inks containing bis(urea-urethane) compounds |
| US7153349B2 (en) * | 2004-12-04 | 2006-12-26 | Xerox Corporation | Phase change inks containing curable trans-1,2-cyclohexane bis(urea-urethane) compounds |
| US7144450B2 (en) * | 2004-12-04 | 2006-12-05 | Xerox Corporation | Phase change inks containing trans-1,2-cyclohexane bis(urea-urethane) compounds |
| US7381831B1 (en) | 2007-04-04 | 2008-06-03 | Xerox Corporation | Colorant compounds |
| US7811370B2 (en) * | 2007-04-24 | 2010-10-12 | Xerox Corporation | Phase change ink compositions |
| US7427323B1 (en) * | 2007-06-07 | 2008-09-23 | Xerox Corporation | Quinacridone nanoscale pigment particles |
| US8029861B2 (en) * | 2008-09-23 | 2011-10-04 | Xerox Corporation | Ink carriers containing low viscosity functionalized waxes, phase change inks including same, and methods for making same |
| US8506040B2 (en) * | 2011-04-27 | 2013-08-13 | Xerox Corporation | Solid ink compositions comprising crystalline-amorphous mixtures |
| US8906150B2 (en) * | 2011-04-27 | 2014-12-09 | Xerox Corporation | Phase change inks containing crystalline trans-cinnamic diesters and polyterpene resins |
| US8328924B2 (en) * | 2011-04-27 | 2012-12-11 | Xerox Corporation | Phase change inks and methods of making the same |
| US8500260B2 (en) | 2011-04-27 | 2013-08-06 | Xerox Corporation | Ink compositions incorporating substituted oxazoline compounds or substituted oxazoline derivatives |
-
2013
- 2013-09-04 US US14/018,334 patent/US9074104B2/en active Active
-
2014
- 2014-08-21 KR KR1020140108876A patent/KR102112370B1/ko not_active Expired - Fee Related
- 2014-08-25 JP JP2014170636A patent/JP6312560B2/ja active Active
- 2014-08-29 DE DE201410217360 patent/DE102014217360A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE102014217360A1 (de) | 2015-03-05 |
| JP2015048480A (ja) | 2015-03-16 |
| US9074104B2 (en) | 2015-07-07 |
| KR102112370B1 (ko) | 2020-05-19 |
| KR20150027695A (ko) | 2015-03-12 |
| US20150059615A1 (en) | 2015-03-05 |
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