WO2005061636A1 - Solubility additive for ink compositions - Google Patents
Solubility additive for ink compositions Download PDFInfo
- Publication number
- WO2005061636A1 WO2005061636A1 PCT/US2004/020282 US2004020282W WO2005061636A1 WO 2005061636 A1 WO2005061636 A1 WO 2005061636A1 US 2004020282 W US2004020282 W US 2004020282W WO 2005061636 A1 WO2005061636 A1 WO 2005061636A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dye
- additive
- ink composition
- amino acid
- solvent
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 78
- 239000000654 additive Substances 0.000 title claims abstract description 59
- 230000000996 additive effect Effects 0.000 title claims abstract description 57
- 239000000975 dye Substances 0.000 claims abstract description 98
- 150000001413 amino acids Chemical class 0.000 claims abstract description 33
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 239000006184 cosolvent Substances 0.000 claims description 7
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 6
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 6
- 229960003237 betaine Drugs 0.000 claims description 5
- 238000007641 inkjet printing Methods 0.000 claims description 5
- 239000000980 acid dye Substances 0.000 claims description 4
- 229960002449 glycine Drugs 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- 229940000635 beta-alanine Drugs 0.000 claims description 3
- 229960003646 lysine Drugs 0.000 claims description 3
- 229960003080 taurine Drugs 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- -1 vulcan orange Chemical compound 0.000 description 19
- 239000000976 ink Substances 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 239000000049 pigment Substances 0.000 description 7
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- LMULDSDQRQVZMW-UHFFFAOYSA-N N-(5-chloro-2,4-dimethoxyphenyl)-4-[[5-(diethylsulfamoyl)-2-methoxyphenyl]diazenyl]-3-hydroxynaphthalene-2-carboxamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(N=NC=2C3=CC=CC=C3C=C(C=2O)C(=O)NC=2C(=CC(OC)=C(Cl)C=2)OC)=C1 LMULDSDQRQVZMW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- AOADSHDCARXSGL-ZMIIQOOPSA-M alkali blue 4B Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N.[Na+] AOADSHDCARXSGL-ZMIIQOOPSA-M 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 108700003601 dimethylglycine Proteins 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- PYUYQYBDJFMFTH-WMMMYUQOSA-N naphthol red Chemical compound CCOC1=CC=CC=C1NC(=O)C(C1=O)=CC2=CC=CC=C2\C1=N\NC1=CC=C(C(N)=O)C=C1 PYUYQYBDJFMFTH-WMMMYUQOSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- TUZVXWAXUWFKLT-UHFFFAOYSA-N 2-(14-methylpentadecyl)oxirane Chemical compound CC(C)CCCCCCCCCCCCCC1CO1 TUZVXWAXUWFKLT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- IPHYGCMVLYWKLM-UHFFFAOYSA-N 2-octadec-9-enoxyethanol;phosphoric acid Chemical compound OP(O)(O)=O.CCCCCCCCC=CCCCCCCCCOCCO IPHYGCMVLYWKLM-UHFFFAOYSA-N 0.000 description 1
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 1
- DWDURZSYQTXVIN-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]aniline Chemical compound C1=CC(=NC)C=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 DWDURZSYQTXVIN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VVAVKBBTPWYADW-UHFFFAOYSA-L Biebrich scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=CC=CC2=C1N=NC(C(=C1)S([O-])(=O)=O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 VVAVKBBTPWYADW-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 241000692870 Inachis io Species 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- GRPFBMKYXAYEJM-UHFFFAOYSA-M [4-[(2-chlorophenyl)-[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C(=CC=CC=1)Cl)=C1C=CC(=[N+](C)C)C=C1 GRPFBMKYXAYEJM-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- VOMZUJSUTZAURW-TXEARYQUSA-N alkali Blue G Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC2=CC=CC=C2S(O)(=O)=O)=C(\C=C2)/C=C/C\2=N\C2=CC=CC=C2)=CC=C1N VOMZUJSUTZAURW-TXEARYQUSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- HBHZKFOUIUMKHV-UHFFFAOYSA-N chembl1982121 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HBHZKFOUIUMKHV-UHFFFAOYSA-N 0.000 description 1
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- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
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- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- XDBZPHDFHYZHNG-UHFFFAOYSA-L disodium 3-[(5-chloro-2-phenoxyphenyl)diazenyl]-4-hydroxy-5-[(4-methylphenyl)sulfonylamino]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1S(=O)(=O)NC(C1=C2O)=CC(S([O-])(=O)=O)=CC1=CC(S([O-])(=O)=O)=C2N=NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 XDBZPHDFHYZHNG-UHFFFAOYSA-L 0.000 description 1
- LHRXTFDXJQAGAV-UHFFFAOYSA-L disodium 3-hydroxy-4-(naphthalen-1-yldiazenyl)naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(cc2cc(ccc2c1N=Nc1cccc2ccccc12)S([O-])(=O)=O)S([O-])(=O)=O LHRXTFDXJQAGAV-UHFFFAOYSA-L 0.000 description 1
- UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 description 1
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
- SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 229910001254 electrum Inorganic materials 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010940 green gold Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 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
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- VUTDNNGELGZRNP-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine oxide;dihydrate Chemical compound O.O.CCCCCCCCCCCCCC[N+](C)(C)[O-] VUTDNNGELGZRNP-UHFFFAOYSA-N 0.000 description 1
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 1
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- WOTPFVNWMLFMFW-ISLYRVAYSA-N para red Chemical class OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=C(N(=O)=O)C=C1 WOTPFVNWMLFMFW-ISLYRVAYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 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
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
Definitions
- the ink-jet printing process involves the ejection of fine droplets of an ink composition onto a print medium such as paper in response to electric signals generated by a controller, such as a microprocessor.
- the fine droplets are typically emitted by a printing head that passes over the print medium without contacting the print medium.
- the printing head in some embodiments, may include an orifice plate that has very small nozzles through which the ink droplets are ejected.
- the nozzles can be, for instance, less than 50 microns in diameter.
- the nozzles are in fluid communication with the ink composition. Ink drop ejection is currently achieved either thermally or piezoelectrically. In thermal ink-jet printing, each nozzle is associated with a resistor element.
- Each resistor element is in turn connected to a microprocessor, whose signals direct one or more resistor elements to heat up rapidly. This causes a rapid expansion of ink that forces a drop of ink through the associated nozzle onto the print medium.
- piezoelectric ink-jet printing ink droplets are ejected due to the vibrations of piezoelectric crystals stimulated by electrical signals generated by a microprocessor.
- Many ink-jet ink compositions contain a dye dissolved in a solvent.
- the dye is typically anionic.
- sulfonated dyes are widely used in ink-jet applications. Of particular advantage, these dyes may be dissolved or dispersed in an aqueous-based system.
- Dye aggregation may be especially prominent when using higher molecular weight dyes, such as those having molecular weights approaching 1 ,000 g/mol.
- Dye aggregation can also occur if the dye composition contains background salts and other impurities which may be left over fragments from commercial dye synthesis.
- the formation of dye aggregates can cause the dye to coalesce and form much larger clusters which lead to nozzle fouling. Once nozzle fouling occurs, the precision of the ink-jet printer becomes compromised. In fact, clogging of the nozzle can lead to the complete breakdown of the printer.
- the present invention is directed to an improved stabilized ink composition.
- the ink composition may be, for instance, designed for use with an ink-jet printer.
- the ink composition includes a dye, a solvent for the dye, and an additive comprising an amino acid or a derivative of an amino acid.
- the amino acid additive has been found to prevent the dye from coalescing in the solvent and fouling up a printer in which the dye composition is used.
- the additive has a polarity greater than the polarity of the solvent.
- the amino acid additive can increase the solubility of the dye in the solvent.
- the amino acid additive may be a zwitterion. Examples of particular amino acids that may be used in the present invention include glycine, lysine, taurine, beta-alanine, betaine, or mixtures thereof.
- the additive may comprise a sulfonic acid analog of an amino acid.
- the amino acid additive may have a dipole moment of greater than about 4 debye, such as greater than about 10 debye.
- the solvent contained within the dye composition is water.
- the dye may be a sulfonated dye or an acid dye.
- the dye composition may also contain various other ingredients, such as an organic cosolvent and/or a surfactant.
- the additive may be contained in the dye composition in an amount sufficient to prevent the dye from coagulating.
- the additive may be present in the dye composition at a mole fraction of greater than about 0.001 , such as greater than about 0.004.
- the additive may be present in the composition at a mole fraction of from about 0.004 to about 0.04, such as from about 0.01 to about 0.02.
- the above dye composition is printed onto a substrate using an ink-jet printer.
- the ink-jet printer may, for instance, include a print head that emits small droplets of the dye composition that are directed onto the substrate.
- the ink-jet printer may deposit the droplets onto the substrate without the print head contacting the substrate.
- the present invention include these and other modifications and variations as come within the scope and spirit of the invention.
- the dye within the formulation may have a tendency to form aggregates which may ultimately cause the dye to coalesce.
- Dye aggregation and coalescing is a particular problem when the dye formulation contains dyes having a high molecular weight. Once coalescing of the dye occurs, problems may be experienced in printing the dye formulations onto a substrate. For instance, should dye aggregates cause coalescing, the dye formulation may easily foul a printer, especially ink-jet printers.
- the present invention is generally directed to an additive for incorporation into a dye composition which tends to inhibit molecular aggregation of dyes and therefore leads to higher dye solubility.
- the additive is a material that forms a zwitterion in the dye composition and is more polar than the solvent into which the dye is dispersed.
- the additive of the present invention comprises an amino acid or a derivative of an amino acid, such as an amino acid analog.
- the additive of the present invention may be used in any suitable ink composition.
- the ink composition contains an ink or dye, a solvent for the dye, and various other ingredients.
- Suitable dyes that may be used with the additive of the present invention include, for instance, acid dyes, and sulfonated dyes including direct dyes.
- the dyes may be formulated to be used in an aqueous-based composition or in a nonaqueous-based composition.
- aqueous dyes that may be used in the present invention include Direct Black 19, Direct Blue 86, Direct Blue 199, Direct Yellow 132, Acid Yellow 132, Direct Red 9, Direct Red 32, Acid Yellow 23, Acid Blue 185, Acid Blue 9, Acid Red 17, Acid Red 52, Acid Red 249, and Reactive Red 180.
- dyes which may be used include Pigment Yellow 138, Pigment Red 122, Pigment Blue 15:3, toluidine red, Permanent Carmine FB, Fast Yellow AAA, Disazo Orange PMP, Lake Red C, Brilliant Carmine 6B, phthalocyanine blue, quinacridone red, dioxane violet, victoria pure blue, alkali blue toner, Furnace Yellow 10G, Disazo Yellow AAMX, Disazo Yellow AAOT, Disazo Yellow AAOA, yellow iron oxide, Disazo Yellow HR, ortho-nitroaniline orange, dinitroaniline orange, vulcan orange, toluidine red, chlorinated para red, brilliant fast scarlet, Naphthol Red 23, pyrazon red, Barium Red 2B, Calcium Red 2B, Strontium Red 2B, Manganese Red 2B, barium lithol red, Pigment Scarlet 3B Lake, Lake, Lake
- each of the above described dyes may be used in an aqueous-based composition.
- the dyes may be incorporated into a nonaqueous-based composition in which the solvent is an organic compound.
- the composition can also include an organic cosolvent and one or more surfactants.
- an organic acid may also be contained in the composition.
- the organic cosolvents that may be used in the composition are water- soluble.
- Exemplary water-soluble organic cosolvents include aliphatic alcohols, aromatic alcohols, diols, triols, amides, ketones, polyketones or ketoalcohols, nitrogen-containing heterocyclic ketones, ethers, glycol ethers, poly(glycol) ethers, alkylene glycols, polyalkylene glycols, thioglycols containing alkylene groups, lower alkyl ethers of polyhydric alcohols and lactams.
- Particular examples of organic cosolvents include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, and tert-butyl alcohol.
- Amides that may be used include dimethylformamide and dimethylacetamide.
- Ethers that may be used include tetrahydrofuran and dioxane, while particular glycols include ethylene glycol, propylene glycol, butylene glycol, triethylene glycol, 1 , 2, 6,-hexanetriol, thiodiglycol, hexylene glycol, and diethylene glycol.
- Lower alkyl ethers of polyhydric alcohols include glycerine, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, N-methyl-2-pyrrolidone, 2-pyrrolidone, and 1 , 3-dimethyl-2- imidazolidinone.
- Surfactants that may be used in the dye composition include anionic surfactants, cationic surfactants, amphoteric surfactants, non-ionic surfactants, and the like.
- anionic surfactants alkylsulfate, polyoxyethylene alkyl ether sulfate, including diphenyl sulfonate derivatives like, but not limited to, sodium hexadecyl diphenyloxide disulfonate, and ethoxylated oleoalcohol phosphate esters and the like can be used.
- As the cationic surfactants alkyltrimethylammonium chloride, dialkyldimethylammonium chloride, protonated POE amines and the like can be used.
- high-molecular weight surfactants high-molecular weight polyurethane, polyester and the like can be used.
- high-molecular weight polymers polymers having functional groups which have affinity toward pigments e.g. carbonyl group or/and amino group, can be used.
- Non-ionic surfactants include alkyl polyethylene oxides (POEs); alkyl phenyl POEs including polyoxyethylene alkylphenyl ethers; ethylene oxide/propylene oxide block copolymers; acetylenic POEs; POE esters; POE alkyl ethers; POE diesters; POE amines; POE amides; and dimethicone copolyols.
- non-ionic surfactants include polyoxyethylene sorbitan fatty acid ester, polyoxypropylene glycols, and polyoxypropylene alkyl ethers.
- U.S. Pat. No. 5,106,416 discusses many of the surfactants listed above in greater detail.
- Amphoteric surfactants such as substituted amine oxides or members of the octyl dimethyl glycine family of octylamine choloroacetic adducts may be used.
- Other amphoteric surfactants include alkyldimethyl aminoacetic acid betaine, alkyldimethyl amine oxide, alkylcarboxymethylhydroxyethyl imidazolium betaine and the like.
- surfactants that may be employed in the practice of this invention include secondary alcohol ethoxylates, SURFYNOLTM CT-11 , Octyl dimethyl glycine, sodium hexadecyl diphenyloxide disulfonate, oleyl triethoxy mono diphosphate, isohexadecyl ethylene oxide 20 (available from the ICI Group as ARLASOLVETM 200), and amine oxides such as N,N-dimethyl-N-dodecyl amine oxide, N,N-dimethyl-N-tetradecyl amine oxide, N,N-dimethyl-N-hexadecyl amine oxide, N,N-dimethyl-N-octadecyl amine oxide, N,N-dimethyl-N-(Z-9-octadecenyl)- N-amine oxide.
- secondary alcohol ethoxylates such as N,N-dimethyl-N-dodecyl
- the ink composition can contain the dye in an amount up to about 15% by weight, such as from about 0.2 to about 10% by weight.
- the organic cosolvent may be present in an amount up to about 50% by weight, such as from about 5% to about 30% by weight.
- One or more surfactants may be present in an amount up to about 40% by weight, such as from about 0.1 % by weight to about 15% by weight.
- organic acids may be present in an amount of around 5 to 10% by weight.
- the remainder of the ink composition comprises water and possibly other ingredients in minor amounts.
- the ink composition further contains an additive that serves to stabilize the composition and prevents the dye contained within the composition from coalescing.
- the additive in accordance with the present invention may be a zwitterion, possessing both a positive and negative charge simultaneously on opposite ends of the molecule.
- the present inventor has discovered that by using an additive having a greater polarity than the solvent contained in the dye composition, the additive serves to improve the solubility of the dye and prevent the dye from coalescing.
- the additive of the present invention may have a dipole moment of greater than about 4 debye, such as greater than about 6 debye.
- the dipole moment of the additive may be greater than about 10 debye, such as greater than about 12 debye, and even greater than about 15 debye.
- the dipole moment of water is less than 2 debye.
- the additive has a greater dipole moment than water.
- the additive may be added to the solvent while the dielectric constant of the liquid is measured. If the dielectric constant rises after addition of the additive, then the additive may be deemed to have a greater polarity.
- the additive may increase the dielectric constant of the liquid by at least 20%, by at least 50%, by at least 75%, or even by greater than 100%.
- the additive is an organic zwitterion, such as an amino acid or a derivative of an amino acid.
- a derivative of an amino acid may include, for instance, a sulfonic or phosphonic acid analog of an amino acid.
- Amino acid additives used in the present invention generally have a lower molecular weight.
- the amino acid additive may have a molecular weight of less than about 500, such as less than about 200 (based on standard atomic weights).
- the amino acid additive for many applications, also has relatively small or no side chains on the molecule.
- the side chains may have less than about 6 carbon atoms. In one particular embodiment, for instance, the side chains have less carbon atoms than the backbone of the molecule.
- Particular examples of amino acid additives that may be used in the present invention include glycine, lysine, taurine (which is an analog), beta-alanine, and betaine.
- the zwitterion additive of the present invention improves the solubility of dyes in a dye composition
- the additive becomes closely associated with the dye.
- dyes typically bear an electrical charge which results in the formation of an electrical double layer surrounding individual molecules or aggregates of the dye. These regions of high electrical field tend to strongly acquire and accumulate higher polarity species present in the solvent space.
- a zwitterion in accordance with the present invention such as an amino acid, is believed to have a strong tendency to preferentially accumulate in the electrical double layer region of the dye due to its much higher dipole moment than the solvent.
- the zwitterion additive When present in large concentrations in the immediate vicinity of the dye, the zwitterion additive is believed to confer substantial osmotic activity to the electrical double layer region causing the dye to be surrounded by solvent molecules, such as water.
- the amount the zwitterion additive is added to the dye composition depends upon the particular dye formulation and the desired results. In many embodiments, for instance, the additive should be present in the dye composition at a mole fraction of greater than about 0.001 , such as greater than about 0.004. For instance, the additive may be present in the dye composition at a mole fraction of from about 0.004 to less than about 0.1. For example, the additive may be present in the dye composition at a mole fraction of from about 0.004 to about 0.04, such as from about 0.01 to about 0.02.
- Dye compositions made in accordance with the present invention can be used in any suitable application.
- the dye compositions may be fed to any suitable printer and transferred onto a substrate.
- the dye composition may be fed through a non-impact printer, such as an ink-jet printer.
- Ink-jet printers typically include an ink-jet print head that has a plurality of orifices. A dye composition made according to the present invention may be expelled from one or more of these orifices thus exiting the print head of the ink-jet printer.
- Drops of the dye composition then travel a throw distance between the print head and the substrate, such as a paper.
- the orifices of the print head may be aligned in a single row or may be formed having various patterns.
- the composition may be expelled from these orifices either simultaneously or through selected orifices at any given time.
- any suitable ink-jet printing device can be used for applying dye compositions according to the present invention.
- ink-jet printers that may be used with the dye composition include, for instance, thermal ink-jet printers, piezoelectric printers, and valve jet printers.
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 Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020067011722A KR101155736B1 (en) | 2003-12-15 | 2004-06-23 | Solubility additive for ink compositions |
EP04756025A EP1694784A1 (en) | 2003-12-15 | 2004-06-23 | Solubility additive for ink compositions |
CN200480037311XA CN1894349B (en) | 2003-12-15 | 2004-06-23 | Solubility additive for ink compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/736,456 | 2003-12-15 | ||
US10/736,456 US7041160B2 (en) | 2003-12-15 | 2003-12-15 | Solubility additive for ink compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005061636A1 true WO2005061636A1 (en) | 2005-07-07 |
Family
ID=34653918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/020282 WO2005061636A1 (en) | 2003-12-15 | 2004-06-23 | Solubility additive for ink compositions |
Country Status (6)
Country | Link |
---|---|
US (1) | US7041160B2 (en) |
EP (1) | EP1694784A1 (en) |
KR (1) | KR101155736B1 (en) |
CN (1) | CN1894349B (en) |
TW (1) | TWI265960B (en) |
WO (1) | WO2005061636A1 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7066989B2 (en) * | 2003-01-08 | 2006-06-27 | Fuji Photo Film Co., Ltd. | Inkjet ink, production method of inkjet ink, inkjet ink set and inkjet recording method |
US7674328B2 (en) * | 2003-03-25 | 2010-03-09 | Hewlett-Packard Development Company, L.P. | Dye-based ink |
US7387666B2 (en) * | 2003-06-24 | 2008-06-17 | Hewlett-Packard Development Company, L.P. | Black ink-jet inks |
US8575417B2 (en) | 2007-02-23 | 2013-11-05 | The Procter And Gamble Company | Printed formed film web and method for making |
US8142876B2 (en) | 2007-02-23 | 2012-03-27 | The Procter & Gamble Company | Printed nonwoven web and method for making |
US7736688B2 (en) * | 2007-02-23 | 2010-06-15 | Procter & Gamble | Printed web and method for making |
JP4941784B2 (en) * | 2008-10-24 | 2012-05-30 | ブラザー工業株式会社 | Water-based ink for ink jet recording, ink cartridge, and ink jet recording apparatus |
JP4941785B2 (en) * | 2008-10-24 | 2012-05-30 | ブラザー工業株式会社 | Water-based ink for ink jet recording, ink cartridge, and ink jet recording apparatus |
KR101106328B1 (en) * | 2010-01-26 | 2012-01-18 | 에스비리모티브 주식회사 | Case for a secondary battery and method of manufacturing the same |
KR101282051B1 (en) | 2010-12-21 | 2013-07-04 | 한국과학기술원 | Fluorescent Dye-Siloxane Hybrid Resin |
JP6629041B2 (en) * | 2015-10-27 | 2020-01-15 | 株式会社パイロットコーポレーション | Water-based ballpoint pen ink composition and water-based ballpoint pen using the same |
WO2018080630A1 (en) * | 2016-10-25 | 2018-05-03 | Hewlett-Packard Development Company, L.P. | Dispersion and jettable composition containing metal oxide nanoparticles |
US11421123B2 (en) * | 2016-10-25 | 2022-08-23 | Hewlett-Packard Development Company, L.P. | Dispersion and jettable composition containing cesium tungsten oxide nanoparticles and a zwitterionic stabilizer |
US11384248B2 (en) * | 2017-03-23 | 2022-07-12 | Hewlett-Packard Development Company, L.P. | Infrared absorbing nanoparticle(s) |
Citations (3)
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JPS56135568A (en) * | 1980-03-28 | 1981-10-23 | Fujitsu Ltd | Ink for ink jet printer |
EP0659852A1 (en) * | 1993-12-20 | 1995-06-28 | Mitsubishi Chemical Corporation | Aqueous ink for ink-jet recording |
US6306204B1 (en) * | 1999-11-24 | 2001-10-23 | Xerox Corporation | Ink jet ink compositions and printing processes |
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CA1183491A (en) * | 1980-12-04 | 1985-03-05 | Eric W. Oldendorf | Technique of forming a riffled pad by coiling and securing a flexible strip |
US5106416A (en) | 1991-08-28 | 1992-04-21 | Hewlett-Packard Company | Bleed alleviation using zwitterionic surfactants and cationic dyes |
JPH08302253A (en) * | 1995-05-10 | 1996-11-19 | Asahi Glass Co Ltd | Ink for ink jet recording |
US5891232A (en) * | 1997-10-28 | 1999-04-06 | Hewlett-Packard Company | Smearfastness and fast drying times in inks containing macromolecular chromophores |
US6444019B1 (en) * | 1998-11-06 | 2002-09-03 | Videojet Technologies Inc. | Ink jet ink composition |
JP2001139854A (en) * | 1999-11-17 | 2001-05-22 | Konica Corp | Ink jet recording liquid and recording method for ink jet recording |
JP4155486B2 (en) | 2000-09-01 | 2008-09-24 | 株式会社リコー | Method for producing pigment dispersion |
US6572690B2 (en) | 2001-03-05 | 2003-06-03 | Hewlett-Packard Development Company, L.P. | Use of mixtures of organic acids to adjust properties of ink-jet inks |
US7066989B2 (en) * | 2003-01-08 | 2006-06-27 | Fuji Photo Film Co., Ltd. | Inkjet ink, production method of inkjet ink, inkjet ink set and inkjet recording method |
US7387666B2 (en) * | 2003-06-24 | 2008-06-17 | Hewlett-Packard Development Company, L.P. | Black ink-jet inks |
-
2003
- 2003-12-15 US US10/736,456 patent/US7041160B2/en not_active Expired - Lifetime
-
2004
- 2004-06-23 CN CN200480037311XA patent/CN1894349B/en not_active Expired - Fee Related
- 2004-06-23 WO PCT/US2004/020282 patent/WO2005061636A1/en not_active Application Discontinuation
- 2004-06-23 KR KR1020067011722A patent/KR101155736B1/en active IP Right Grant
- 2004-06-23 EP EP04756025A patent/EP1694784A1/en not_active Withdrawn
- 2004-12-01 TW TW093137089A patent/TWI265960B/en not_active IP Right Cessation
Patent Citations (3)
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JPS56135568A (en) * | 1980-03-28 | 1981-10-23 | Fujitsu Ltd | Ink for ink jet printer |
EP0659852A1 (en) * | 1993-12-20 | 1995-06-28 | Mitsubishi Chemical Corporation | Aqueous ink for ink-jet recording |
US6306204B1 (en) * | 1999-11-24 | 2001-10-23 | Xerox Corporation | Ink jet ink compositions and printing processes |
Non-Patent Citations (1)
Title |
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DATABASE WPI Section Ch Week 198149, Derwent World Patents Index; Class E23, AN 1981-89906D, XP002295223 * |
Also Published As
Publication number | Publication date |
---|---|
US20050126434A1 (en) | 2005-06-16 |
TWI265960B (en) | 2006-11-11 |
CN1894349A (en) | 2007-01-10 |
KR101155736B1 (en) | 2012-06-12 |
US7041160B2 (en) | 2006-05-09 |
CN1894349B (en) | 2010-12-22 |
KR20060135663A (en) | 2006-12-29 |
TW200535197A (en) | 2005-11-01 |
EP1694784A1 (en) | 2006-08-30 |
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