WO1994020579A1 - A hot melt ink composition - Google Patents
A hot melt ink composition Download PDFInfo
- Publication number
- WO1994020579A1 WO1994020579A1 PCT/GB1994/000404 GB9400404W WO9420579A1 WO 1994020579 A1 WO1994020579 A1 WO 1994020579A1 GB 9400404 W GB9400404 W GB 9400404W WO 9420579 A1 WO9420579 A1 WO 9420579A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hot melt
- ink composition
- melt ink
- composition
- concentration
- Prior art date
Links
- 239000012943 hotmelt Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims description 119
- 238000007641 inkjet printing Methods 0.000 claims abstract description 21
- 239000003792 electrolyte Substances 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 14
- 239000000049 pigment Substances 0.000 claims description 13
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical group [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 12
- 229940116357 potassium thiocyanate Drugs 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- -1 ester derivatives of 12- hydroxydodecanoic acid Chemical class 0.000 claims description 11
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 229920000554 ionomer Polymers 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- 238000007639 printing Methods 0.000 claims description 7
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- OZSKVMIBRHDIET-UHFFFAOYSA-N 12-hydroxy-n-(2-hydroxyethyl)octadecanamide Chemical group CCCCCCC(O)CCCCCCCCCCC(=O)NCCO OZSKVMIBRHDIET-UHFFFAOYSA-N 0.000 claims description 5
- VYWRBUBXZALATG-UHFFFAOYSA-N 2-hydroxyoctadecanamide Chemical class CCCCCCCCCCCCCCCCC(O)C(N)=O VYWRBUBXZALATG-UHFFFAOYSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 5
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 claims description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- CKFGINPQOCXMAZ-UHFFFAOYSA-N methanediol Chemical compound OCO CKFGINPQOCXMAZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940037312 stearamide Drugs 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- ZOAIGCHJWKDIPJ-UHFFFAOYSA-M caesium acetate Chemical compound [Cs+].CC([O-])=O ZOAIGCHJWKDIPJ-UHFFFAOYSA-M 0.000 claims description 2
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 239000011874 heated mixture Substances 0.000 claims 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims 1
- 239000000976 ink Substances 0.000 description 121
- 239000000126 substance Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 7
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 235000019241 carbon black Nutrition 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 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
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000992 solvent dye Substances 0.000 description 3
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 229920001079 Thiokol (polymer) Polymers 0.000 description 2
- MNCUCCJMXIWMJJ-OWOJBTEDSA-N [(e)-2-thiocyanatoethenyl] thiocyanate Chemical compound N#CS\C=C\SC#N MNCUCCJMXIWMJJ-OWOJBTEDSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 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 2
- 235000012756 tartrazine Nutrition 0.000 description 2
- 239000004149 tartrazine Substances 0.000 description 2
- HDDLVZWGOPWKFW-UHFFFAOYSA-N trimethyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound COC(=O)CC(O)(C(=O)OC)CC(=O)OC HDDLVZWGOPWKFW-UHFFFAOYSA-N 0.000 description 2
- DKBXPLYSDKSFEQ-UHFFFAOYSA-L turquoise gll Chemical compound [Na+].[Na+].[Cu+2].N1=C(N=C2[N-]3)[C]4C(S(=O)(=O)[O-])=CC=CC4=C1N=C([N-]1)C4=CC=CC(S([O-])(=O)=O)=C4C1=NC(C=1C4=CC=CC=1)=NC4=NC3=C1[C]2C=CC=C1 DKBXPLYSDKSFEQ-UHFFFAOYSA-L 0.000 description 2
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 2
- SMKKEOQDQNCTGL-ZETCQYMHSA-N (2s)-2-[(2-nitrophenoxy)methyl]oxirane Chemical compound [O-][N+](=O)C1=CC=CC=C1OC[C@H]1OC1 SMKKEOQDQNCTGL-ZETCQYMHSA-N 0.000 description 1
- WNDULEJVCPEASN-UHFFFAOYSA-N (4-anilinonaphthalen-1-yl)-bis[4-(dimethylamino)phenyl]methanol Chemical compound C1=CC(N(C)C)=CC=C1C(O)(C=1C2=CC=CC=C2C(NC=2C=CC=CC=2)=CC=1)C1=CC=C(N(C)C)C=C1 WNDULEJVCPEASN-UHFFFAOYSA-N 0.000 description 1
- GAXDEROCNMZYCS-QXMHVHEDSA-N (z)-n,n-dimethyloctadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)C GAXDEROCNMZYCS-QXMHVHEDSA-N 0.000 description 1
- RAADJDWNEAXLBL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene Chemical compound C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 RAADJDWNEAXLBL-UHFFFAOYSA-N 0.000 description 1
- OCQDPIXQTSYZJL-UHFFFAOYSA-N 1,4-bis(butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NCCCC)=CC=C2NCCCC OCQDPIXQTSYZJL-UHFFFAOYSA-N 0.000 description 1
- QOSTVEDABRQTSU-UHFFFAOYSA-N 1,4-bis(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC)=CC=C2NC QOSTVEDABRQTSU-UHFFFAOYSA-N 0.000 description 1
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-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
- 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 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
- CZNYJWQJSGRKRA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]aniline Chemical compound NC1=CC=CC=C1C1=NN=C(C=2C=CC(Cl)=CC=2)O1 CZNYJWQJSGRKRA-UHFFFAOYSA-N 0.000 description 1
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- YCUVUDODLRLVIC-UHFFFAOYSA-N Sudan black B Chemical compound C1=CC(=C23)NC(C)(C)NC2=CC=CC3=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 YCUVUDODLRLVIC-UHFFFAOYSA-N 0.000 description 1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 239000013036 UV Light Stabilizer Substances 0.000 description 1
- MINJAOUGXYRTEI-UHFFFAOYSA-N [3-benzoyloxy-2,2-bis(benzoyloxymethyl)propyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC(COC(=O)C=1C=CC=CC=1)(COC(=O)C=1C=CC=CC=1)COC(=O)C1=CC=CC=C1 MINJAOUGXYRTEI-UHFFFAOYSA-N 0.000 description 1
- OASXQMASFWOQMH-UHFFFAOYSA-N [Ba].C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 Chemical compound [Ba].C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 OASXQMASFWOQMH-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N aconitic acid Chemical compound OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OGOBUJSXNMFAEE-UHFFFAOYSA-N azanium;3,6-di(nonyl)naphthalene-1-sulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC(CCCCCCCCC)=CC2=CC(CCCCCCCCC)=CC=C21 OGOBUJSXNMFAEE-UHFFFAOYSA-N 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
- 229920005601 base polymer Polymers 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 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
- ALLOLPOYFRLCCX-UHFFFAOYSA-N chembl1986529 Chemical compound COC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ALLOLPOYFRLCCX-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
- 229920001577 copolymer Polymers 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
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- UKHVLWKBNNSRRR-ODZAUARKSA-M dowicil 200 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C\C=C/Cl)C3 UKHVLWKBNNSRRR-ODZAUARKSA-M 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005686 electrostatic field Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- PASCYLAFGHJSHW-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methyl]-3-(methylamino)propanoate Chemical compound CCOC(=O)C(CNC)CC1=CC=C(OC)C=C1 PASCYLAFGHJSHW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- WTIFIAZWCCBCGE-UUOKFMHZSA-N guanosine 2'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OP(O)(O)=O WTIFIAZWCCBCGE-UUOKFMHZSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 235000010187 litholrubine BK Nutrition 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OKRNLSUTBJUVKA-UHFFFAOYSA-N n,n,n',n'-Tetrakis(2-hydroxyethyl)adipamide Chemical compound OCCN(CCO)C(=O)CCCCC(=O)N(CCO)CCO OKRNLSUTBJUVKA-UHFFFAOYSA-N 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
- UQJQVUOTMVCFHX-UHFFFAOYSA-L nabam Chemical compound [Na+].[Na+].[S-]C(=S)NCCNC([S-])=S UQJQVUOTMVCFHX-UHFFFAOYSA-L 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 235000012752 quinoline yellow Nutrition 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229940099373 sudan iii Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960000943 tartrazine Drugs 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood 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
Definitions
- This invention relates to the field of continuous ink-jet printing
- ink is emitted in a continuous stream
- the inks used for continuous ink-jet printing are liquid at
- Liquid inks present various difficulties: for example, they respond differently depending upon the type of printing media used.
- the print quality usually depends on the type of paper used, which also has an effect on the drying time and on waterfastness. Although water-borne inks have been widely used, they exhibit poor
- humectant such as diethylene glycol
- Liquid inks without curable additives typically are not useful on non-porous surfaces, such and metal, glass, or plastic, because they are too prone to smearing. Furthermore, liquid inks are very sensitive to temperature changes which influence the ink viscosity and interfacial tension, which, in turn, influence the ink interaction with the medium.
- a hot melt ink This ink is normally solid at room temperature. When the ink is heated, it melts to form a low viscosity fluid which can be ejected as droplets.
- Hot melt ink was originally used by Berry et al. (U.S. Patent No. 3,653,932) in electrostatically controlled continuous ink-jet printing.
- the ink was comprised of a waxy component which is solid at room temperature.
- the term "hot melt ink” defines an ink that is in a solid
- Hot melt inks normally comprise vehicles, such as natural waxes, resins and/or long chain fatty acids, esters, or alcohols which melt when
- the ink is heated to jetting temperatures.
- heated droplets Upon jetting, heated droplets
- This print may be slightly raised
- low molecular weight waxes and polymers typically present in hot melt inks have low polarity and show very poor solvating ability towards ionic polar material used as electrolytes in continuous ink-jet printing.
- electrolyte ions must dissociate in the ink composition, thereby allowing ionic separation upon application of an external electric field.
- inks can also be used in continuous ink-jet printing.
- compositions is too high for electrical charging in continuous ink jet
- resistivity control agents such as inorganic salts, water-soluble amines,
- the present invention overcomes the problems associated with
- liquid state has a conductivity of greater than about 100
- hot melt inks for continuous ink-jet printing that have good
- ⁇ may be applied at acceptable temperatures, such as from about 75° C to about 175° C, preferably from about 90° C to about 140° C, and most preferably at about 115° C.
- the hot melt inks of the present invention may also comprise, and
- a viscosity reducing agent preferably do comprise, in addition to the two components mentioned above, a viscosity reducing agent, and a hardening agent.
- a flexibiiizing agent may also be used to reduce ink brittleness.
- compositions melt in the ranges discussed above, and have a viscosity
- ink compositions preferably from about 5 centipoises to about 15 centipoises.
- Said ink compositions also have a conductivity from about 100 microsiemens/cm
- microsiemens/cm preferably from about 500
- microsiemens/cm to about 2000 microsiemens/cm, and most preferably
- the electrolyte used in the hot melt ink compositions according to the present invention is an inorganic salt.
- the lithium salt of trifluoromethanesulphonic acid, as well as cesium acetate and cesium iodide are also suitable.
- the electrolyte should be readily soluble and dissociate well in the specific electrolyte solvating and dissociating compound chosen.
- the electrolyte should also be thermally stable in the temperature range of about 75°C to about 175° C and be non-toxic.
- the electrolyte can be present in the ink composition in an amount from about 0.1% to about 5% by weight of the composition.
- the ink composition should contain from about 0.5% to about 3% of electrolyte by weight of the composition.
- the electrolyte solvating and dissociating compound used in the hot melt ink compositions according to the present invention can be chosen from the group consisting of alkanolamides and polyethylene
- the alkanolamide to be used in the ink compositions of the present invention should be chosen on the basis of the conductivity, viscosity, volatility and melting
- Alkanolamides useful in the formulation of the hot melt ink compositions according to the present invention can also be obtained from Witco Company under the trade mark "Witcamide”.
- bis- monoethanolamides and bis-diethanolamides of dibasic fatty acids may also be utilized in the present invention.
- One such useful compound has
- Polyethylene glycol can also be used as the electrolyte-solvating and dissociating compound of the hot melt ink compositions according to the present invention.
- Polyethylene glycol having a molecular weight having a molecular weight
- Low molecular weight polyethylene glycol (below 1 ,000 MW)
- polyethylene (above 10,000 MW) glycol becomes brittle.
- polyethylene glycol having a molecular weight in the range of about
- 1000 to 2000 is preferred, because it results in an ink having good adhesion and minimal smearing.
- Viscosity reducing agents may also be employed in the hot melt
- a viscosity reducing agent allows the viscosity of the ink composition to be adjusted to a desired value.
- Suitable viscosity reducing agents for use in ink compositions of the present invention include stearamide, stearyl monoethanolamide stearate, and ethylene glycol distearate (EGDS).
- the viscosity reducing agent should be present in an amount of from about 0 to about 50 % by weight of the ink composition.
- composition depends on the viscosity desired by the user, and the
- a hardening agent may also be used in the hot melt ink
- compositions of the present invention to obtain ink having a desired
- Useful hardening agents include
- ricinoleamides hydroxystearamides, hydrogenated castor oil, EGDS, esters of methylene glycol, esters of propylene glycol, esters of ethylene
- glycol esters of glycol, stearyl esters of 12-hydroxystearic acid, and
- hydroxy acids such as 12-hydroxydodecanoic acid and derivatives
- Ricinoleamides and hydroxystearamides are preferably employed as the hardening agent, with N(2-hydroxyethyl)-12-hydroxystearamide
- Suitable hydroxystearamides include those sold under
- a viscosity reducing agent need be employed in the hot melt ink composition of the present invention, one or both are preferably employed. Most preferably, both a viscosity reducing agent and a hardening agent should be used.
- the electrolyte should be present in an amount from about 0.5 to 3.0 % by weight of the ink composition, and the
- a flexibilizing agent may also be used in the hot melt ink
- compositions of the present invention to reduce ink brittleness.
- flexibilizing agents include ethylene vinyl acetate copolymers,
- polyamides polyamides, amide waxes, and ionomers.
- Useful ionomers may be
- Carboxyl-containing ionomers can be obtained by direct
- copolymer is generally available as the free acid, which can be neutralized to the degree desired with metal hydroxides, acetates, and similar salts.
- ionomers typically contain a certain number of inorganic salt groups attached to a polymer chain, such as from about 1 up to 15 mol % ionic groups pendants to a base polymer, such as hydrocarbon, oxygen, or nitrogen-containing hydrocarbon, or perfluorinated polymer
- An ionomer can be defined as a polymer composed of a
- Ionic hydrocarbon polymers for elastomers or plastics are
- the flexibilizing agent should be present in an amount of from
- the image forming material can be
- a visual image on the substrate such as a colourant
- the amount of image forming agent is not critical. Typically the amount of image forming agent will be from about 0.1 to about 10 percent, based upon the weight of the jet ink composition, preferably
- the colourant may be either a dye, or a pigment.
- exemplary dyes include the following list: solvent yellow 162, 79, 81 , solvent orange
- Suitable dyes for use in the hot melt ink compositions of the present invention also include Pontamine; Food Black 2; Carodirect
- D&C Red #28 (Acid Red 92), available from Pylam; Direct Brill Pink B
- solvent dyes and within the class of solvent dyes, spirit soluble dyes are preferred because of their high
- suitable spirit solvent dyes include Neozapon Red 492 (BASF), Orasol Red G (Ciba-Geigy),
- Supra Yellow GD 167 Cartasol Brilliant Yellow 4GF (Sandoz), Pergasol Yellow CGP (Ciba-Geigy), Orasol Black RL (Ciba-Geigy), Orasol Black
- pigment yellows 1 , 3, 12, 13, 14, 16, 17, 73, 74, 81 , 83, 97, 98, 106, 113, and 114 pigment reds 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 37, 38, 48:1, 48:2, 48:3, 48:4, 57:1, 57:2, 57:3, 88, 122, 146, and 147
- pigment blacks 1 20, carbon black, acetylene black, bone black, lamp black, graphite, and the like.
- Examples of other suitable pigments include Violet Toner VT-8015 (Paul Uhlich), Normandy Magenta RD-2400 (Paul Uhlich), Paliogen Violet 5100 (BASF), Paliogen Violet 5890 (BASF), Permanent Violet VT2645 (Paul Uhlich), Heliogen Green L8730 (BASF), Argyle Green
- Thermoplast NSD PS PA Ugine Kuhlmann of Canada
- RD-8192 (Paul Uhlich), Oracet Pink RF (Ciba-Geigy), Paliogen Red 3871 K (BASF), Paliogen Red 3340 (BASF), Lithol Fast Scarlet L4300
- the hot melt ink composition of the present invention may contain
- Suitable corrosion inhibitors include from 0.5% to 5% of an
- the sulphonate compound may be selected from the group consisting of
- the hot melt ink composition of the present invention may also be used as a hot melt ink composition of the present invention.
- additives which may be any substance that can enhance the ink with regard to (i) improved solubility of other components, (ii) improved print quality, (iii) improved adhesion of the ink to the media, and/or (iv) control of wetting characteristics, which may, among other
- the ink may contain a biocide.
- Suitable biocides include sorbic acid, 1-(3-chloroallyl)-3,5,7-triaza-1-azoniaadamantane chloride, commercially available as Dowicil 200 (Dow Chemical Company, Midland, Mich.), vinylenebis-thiocyanate, commercially
- surfactants may be present in the hot melt ink composition of the
- plasticizers such as pentaerythritol tetrabenzoate, commercially available
- citrate commercially available as Citroflex 1 , (Monoflex Chemical Company, Greensboro, N.C.), N,N-dimethyl oleamide,
- Halcomid M-18-OL (C. P. Hall Company, Chicago, III.), and the like, may be present.
- Antioxidants and/or UV light stabilizer can also be used either in combination, or separately, in concentrations of about 0.01 by weight up to about 5% by weight.
- Useful antioxidants include hindered phenols
- hindered amines such as Tinuvin 770, 765, and 622, and
- the hot melt ink compositions of the present invention will exhibit the following characteristics, at their temperature of application: (1) a
- the operating temperatures of the inks according to the present invention are generally from about 90°C to about 140° C, with a temperature of 115°C being preferred. Higher temperatures are acceptable, although they may reduce the lifetime of the heater and printhead in which the inks are used. Generally, the operating temperature of the inks is selected to obtain suitable ink viscosity while avoiding extensive fuming or smoking.
- the viscosity of the jet ink composition at the operating temperature of the ink is generally from about 1 to about 50 centipoises, preferably from about 2 to about 20 centipoises, and most preferably from about 5 to about 15 centipoises.
- the viscosity of a given ink formulation can be adjusted depending on the specific type and amount
- the ink composition should, of course, be thermally stable in its molten state so that it does not undergo decomposition to yield either gaseous products, or form solid deposits in the heater system.
- composition should enable printed images with sufficient flexibility to
- Hot melt ink compositions of the present invention are generally
- melting point which generally is from about 80° to about 130° C.
- the molten mixture may be subjected to grinding in an attritor or ball mill apparatus to effect dispersion of the pigment in the binder.
- Printed images may be generated with the hot melt inks of the
- a substrate such as paper or transparency material.
- compositions of the hot melt inks according to the present invention are provided.
- substrates e.g., paper, metal, wood, plastics or glass without the need to form any special surface layer on the substrate.
- substrates e.g., paper, metal, wood, plastics or glass without the need to form any special surface layer on the substrate.
- plastic substrate causes enhanced adhesion of the ink composition due
- hot melt ink compositions penetrate into the substrates as they cool.
- hot melt ink compositions according to the present invention are further illustrated by the following non-limiting examples.
- This composition had a viscosity at 115°C of 13.8 centipoises and a conductivity at 115°C of 508 microsiemens/cm.
- This composition had a viscosity at 115°C of 16.2 centipoises and a conductivity at 115°C of 441 microsiemens/cm.
- This composition had a viscosity at 115°C of 11.6 centipoises and a conductivity at 115°C of 799 microsiemens/cm.
- This composition had a viscosity at 115°C of 10.3 centipoises and a conductivity at 115°C of 769 microsiemens/cm.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU61460/94A AU6146094A (en) | 1993-03-11 | 1994-03-02 | A hot melt ink composition |
EP94908407A EP0738301A1 (en) | 1993-03-11 | 1994-03-02 | A hot melt ink composition |
JP6519710A JPH08507322A (en) | 1993-03-11 | 1994-03-02 | Hot melt ink composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/029,892 US5286288A (en) | 1993-03-11 | 1993-03-11 | Hot melt inks for continuous jet printing |
US08/029,892 | 1993-03-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994020579A1 true WO1994020579A1 (en) | 1994-09-15 |
Family
ID=21851433
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1994/000404 WO1994020579A1 (en) | 1993-03-11 | 1994-03-02 | A hot melt ink composition |
Country Status (5)
Country | Link |
---|---|
US (1) | US5286288A (en) |
EP (1) | EP0738301A1 (en) |
JP (1) | JPH08507322A (en) |
AU (1) | AU6146094A (en) |
WO (1) | WO1994020579A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5800600A (en) * | 1994-07-14 | 1998-09-01 | Tonejet Corporation Pty Ltd | Solid ink jet ink |
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US5902841A (en) * | 1992-11-25 | 1999-05-11 | Tektronix, Inc. | Use of hydroxy-functional fatty amides in hot melt ink jet inks |
JPH06306319A (en) * | 1993-04-26 | 1994-11-01 | Brother Ind Ltd | Hot-melt ink for ink-jet printer |
US5514209A (en) * | 1993-05-04 | 1996-05-07 | Markem Corporation | Hot melt jet ink composition |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5973025A (en) * | 1994-04-12 | 1999-10-26 | Sri International | Aqueous ink compositions containing a binder of a neutralized acidic resin |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US5685754A (en) | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
AU682975B2 (en) * | 1994-07-14 | 1997-10-23 | Tonejet Limited | Solid ink jet ink |
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- 1994-03-02 JP JP6519710A patent/JPH08507322A/en active Pending
- 1994-03-02 EP EP94908407A patent/EP0738301A1/en not_active Ceased
- 1994-03-02 WO PCT/GB1994/000404 patent/WO1994020579A1/en not_active Application Discontinuation
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5800600A (en) * | 1994-07-14 | 1998-09-01 | Tonejet Corporation Pty Ltd | Solid ink jet ink |
Also Published As
Publication number | Publication date |
---|---|
AU6146094A (en) | 1994-09-26 |
JPH08507322A (en) | 1996-08-06 |
US5286288A (en) | 1994-02-15 |
EP0738301A1 (en) | 1996-10-23 |
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