EP1340621B1 - Recording materials - Google Patents
Recording materials Download PDFInfo
- Publication number
- EP1340621B1 EP1340621B1 EP03003513A EP03003513A EP1340621B1 EP 1340621 B1 EP1340621 B1 EP 1340621B1 EP 03003513 A EP03003513 A EP 03003513A EP 03003513 A EP03003513 A EP 03003513A EP 1340621 B1 EP1340621 B1 EP 1340621B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- ink
- recording
- recording material
- paper
- cellulose
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000463 material Substances 0.000 title claims abstract description 44
- -1 triazolopyrimidine compound Chemical class 0.000 claims abstract description 37
- 229920000159 gelatin Polymers 0.000 claims abstract description 28
- 235000019322 gelatine Nutrition 0.000 claims abstract description 28
- 239000000758 substrate Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229920002678 cellulose Polymers 0.000 claims abstract description 13
- 239000001913 cellulose Substances 0.000 claims abstract description 13
- 239000001828 Gelatine Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 230000004888 barrier function Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 5
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 5
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 5
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 claims description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
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- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- IGWTYANIFQDPDR-UHFFFAOYSA-N CC(C)Sc1nc2nc(C)cc(O)n2n1 Chemical compound CC(C)Sc1nc2nc(C)cc(O)n2n1 IGWTYANIFQDPDR-UHFFFAOYSA-N 0.000 claims description 2
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- UHPJWJRERDJHOJ-UHFFFAOYSA-N ethene;naphthalene-1-carboxylic acid Chemical compound C=C.C1=CC=C2C(C(=O)O)=CC=CC2=C1 UHPJWJRERDJHOJ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004417 polycarbonate Substances 0.000 claims description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
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- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 claims description 2
- 125000001174 sulfone group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 108010010803 Gelatin Proteins 0.000 abstract 2
- 239000008273 gelatin Substances 0.000 abstract 2
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- INVVMIXYILXINW-UHFFFAOYSA-N 5-methyl-1h-[1,2,4]triazolo[1,5-a]pyrimidin-7-one Chemical compound CC1=CC(=O)N2NC=NC2=N1 INVVMIXYILXINW-UHFFFAOYSA-N 0.000 abstract 1
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- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
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- 238000011068 loading method Methods 0.000 description 6
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- 239000000049 pigment Substances 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 5
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- 230000008569 process Effects 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
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- 239000004816 latex Substances 0.000 description 3
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- 239000004014 plasticizer Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 229910001593 boehmite Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical compound O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 description 1
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- SJHHXGGXZKPIDE-UHFFFAOYSA-N 2-[1-(dimethylcarbamoyl)pyridin-1-ium-4-yl]ethanesulfonate Chemical compound CN(C)C(=O)[N+]1=CC=C(CCS([O-])(=O)=O)C=C1 SJHHXGGXZKPIDE-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
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- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
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- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 1
- DMYFWUKYJRKQMJ-UHFFFAOYSA-L [Al+2].[O-]C([O-])=O Chemical compound [Al+2].[O-]C([O-])=O DMYFWUKYJRKQMJ-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 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 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- 150000001455 metallic ions Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M2205/00—Printing methods or features related to printing methods; Location or type of the layers
- B41M2205/38—Intermediate layers; Layers between substrate and imaging layer
-
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/502—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording characterised by structural details, e.g. multilayer materials
- B41M5/506—Intermediate layers
-
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5227—Macromolecular coatings characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants
-
- 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
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5236—Macromolecular coatings characterised by the use of natural gums, of proteins, e.g. gelatins, or of macromolecular carbohydrates, e.g. cellulose
Definitions
- the present invention relates to a recording material for recording using the ink jet printing process.
- Ink jet recording is a non-impact printing method wherein droplets of a recording fluid, the ink, are formed by forcing the fluid through a tiny nozzle (or a series of nozzles) under computer control and deposited on a recording material such as paper or transparent film.
- a recording material such as paper or transparent film.
- thermal drop-on-demand printers piezo drop-on-demand printers
- continuous ink jet printers continuous ink jet printers.
- Ink jet recording has been intensively developed in recent years, and has found broad application as output for personal computers in the office and the home because of its low noise characteristic, capability of high speed printing, and facility of multi-colour printing.
- Ink jet printing techniques particularly those using mainly aqueous inks, have undergone rapid development both in respect of reliability and the image quality that the printing apparatus can achieve, and in respect of the cost price of the printing apparatus. Consequently, increasingly severe requirements are being set for the recording materials.
- the recording produced by means of an ink jet processes is required to have, for example, good water and smear resistance, high resolution, high colour density, sufficient ink gradation, and good light fastness.
- the polymeric binder may, for example, be gelatine; a cellulose derivative such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, ethyl hydroxypropyl cellulose, or carboxymethylhydroxyethyl cellulose; a vinyl polymer such as poly (vinyl alcohol) or poly (vinyl pymolidone); or a mixture of such binders.
- the recording layer also comprises a cationogenic substance in order to bind the dyes from the inks, together with other functional additives such as an absorbent pigment or a surfactant.
- a cationogenic substance for use in such recording layers are well known, and include, for example, polyvalent metallic ions, quaternary ammonium salts, polyamines and salts thereof, polymeric ammonium compounds, and basic latexes.
- United States Patent 5,457,486 discloses a recording sheet which comprises (a) a base sheet; (b) a material selected from the group consisting of tetrazolium compounds, indolinium compounds, imidazolinium compounds, and mixtures thereof; (c) an optional pigment; and (d) an optional binder; similarly United States Patent 5,441,795 discloses ink jet recording sheets containing pyridinium or piperazinium compounds.
- Such recording materials may provide prints and images of good quality, and are suitable for their intended purposes.
- a need remains for improved recording sheets which exhibit good image quality when printed with aqueous inks, particularly when printing a multi-colour image in which very dark or dense tints are to be reproduced.
- the ink Due to the greater quantity of ink laid down, the ink can be slow to absorb into the surface of the recording sheet as this absorption depends on swelling of the polymer layer. Further, this slow absorption is becoming more of a problem as printers develop and printing speeds increase, and can lead to visible print deficiencies such as coalescence caused by drops mixing on the print surface before the ink is absorbed.
- United States Patent 5,657,064 discloses ink jet recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, or indazole compounds; United States Patent 5,659,348 discloses recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, or pyrazine compounds; United States Patent 5,729,266 discloses recording sheets containing oxazole, isoxazole, oxazolidinone, oxazoline salt, morpholine, thiazole, thiazolidine, thiadiazole, and phenothiazine compounds; however these inventions particularly relate to improving the drying performance of recording sheets, and especially to reducing the curl of sheets dried with microwave radiation and not to improving the rate of absorption of the in
- Japanese Patent Application 2000-094,829 discloses ink jet recording sheets containing triazolopyrimidines of formula I, wherein Z is hydrogen or CH 2 SH. However this invention particularly relates to improving the light fastness of printed recording sheets and not to improving the rate of absorption of the ink.
- a recording material suitable for ink jet recording comprising a sheet like substrate and arranged on at least one side of the substrate at least one ink-receptive recording layer comprising:
- the supporting substrate for the recording materials of the invention may be any of those known for use in printing and imaging media.
- Suitable substrates include, for example paper, high wet-strength paper, tracing paper, heavyweight paper, fine art paper, card, board, coated paper such as resin coated, polyethylene coated, and barrier layer coated paper, synthetic papers, canvas, cloth, fabric, metals such as aluminium, and polymeric substrates such as filled plastics, opaque plastics, or transparent materials, for example cellulose acetates, poly(ethylene), poly(propylene), poly (vinyl chloride), poly (ethylene terephthalate) and poly (ethylene naphthalate), polycarbonate, polysulphone, polyether sulphone, poly (arylene sulphone), poly(arylene ether ketone sulphone), cellophane, polyvinyl fluoride, polyimide, and the like.
- the supporting substrate is polyethylene coated paper or barrier layer coated paper.
- barrier layer coated paper is meant a paper coated with a water repellent resin barrier layer provided in the form of a latex comprising fine particles of a film-forming polymer suspended in an aqueous carrier.
- the latex is allowed to form a film during the coating and drying process.
- the barrier layer may comprise almost any film-forming latex polymer.
- the polymer of the barrier layer may preferably have a glass transition point of at least 40° C, more preferably approximately 50° C - 100° C.
- the polymer of the barrier layer may optionally contain other additives as are known in the art, such as for example, UV absorbers, light stabilisers such as hindered amines, optical brightening agents, or tinting agents.
- the barrier layer may additionally contain a proportion of an inorganic filler and other additives to improve the operation of the coating process, for example polymeric thickeners, lubricating agents, dispersants, and adhesion promoters.
- the gelatine for the ink-receptive layer of the recording materials of the invention may be any gelatine known for use in imaging materials, for example skin or bone gelatine, treated gelatine such as deionised gelatine, modified gelatine such as phthalated gelatine or phenylcarbamoylated gelatine, or a cationically modified gelatine.
- treated gelatine such as deionised gelatine, modified gelatine such as phthalated gelatine or phenylcarbamoylated gelatine, or a cationically modified gelatine.
- a particularly suitable gelatine is a deionised ossein gelatine of high isoelectric point
- triazolopyrimidine compounds are s -triazolo[1,5- a ]pyrimidine compounds commonly referred to as tetra-aza indene compounds and having the general structure I .
- substituents W, X and Y which may be the same or different, are individually R, OR, SR, SOR, SO 2 R, NRR', NR(COR'), CO 2 R, CONRR', SO 2 NRR', NRSO 2 R', CN, NO 2 , halogen, sulphonic acid, or phosphonic acid, wherein the groups R and R' are independently hydrogen, branched or unbranched C 1 - C 20 substituted or unsubstituted, saturated or unsaturated hydrocarbon, e.g., alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, alkylaryl, or arylalkyl; the substituent Z is R, OR, SR, SOR, SO 2 R, NRR', NR(COR'), CO 2 R, CONRR', SO 2 NRR', NRSO 2 R', CN, NO 2 , halogen,
- Tetra-aza indene compounds are known compounds or may be prepared by known methods, and in particular by the condensation of an appropriate aminotriazole with a suitable ⁇ -dicarbonyl compound.
- An especially preferred class of tetra-aza indene compounds according to formula I are those wherein the group Y is a hydroxy group.
- Another suitable compound is 4-hydroxy-2,6-dimethyl-1,3,3a,7-tetra-aza indene having the structure: which is hereinafter referred to as compound 2 .
- Another suitable compound is 4-hydroxy-2-methylthio-6-methyl-1,3,3a,7-tetra-aza indene having the structure: which is hereinafter referred to as compound 3 .
- Another suitable compound is 4-hydroxy-2-isopropylthio-6-methyl-1,3,3a,7-tetra-aza indene having the structure: which is hereinafter referred to as compound 6 .
- Certain tetra-aza indene compounds may form salts and that this invention also includes relevant salts of such compounds.
- An ionisable group is one which is capable of forming an anionic group or a cationic group in the medium of use. Suitable ionisable groups include salt forming substituents such as sulphonic acid, carboxylic acid, phosphonic acid, and basic nitrogen containing groups. Further, hydroxy groups located as substituents W or Y of the formula I are frequently sufficiently acidic to enable salt formation and therefore salts of such compounds, including the hereinbefore described compounds 2, 3, and 6, may be used in the invention.
- Suitable binders include poly (vinyl alcohol) and copolymers and derivatives thereof; carbohydrates such as tragacanth gum, sodium alginate, or water-soluble starch derivatives; water-accepting cellulose derivatives such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, or carboxymethylhydroxyethyl cellulose; polyalkylene oxides such as polyethylene oxide and polypropylene oxide or derivatives thereof; water-accepting acrylate, methacrylate, or maleate polymers and copolymers and derivatives thereof; poly (vinyl pyrrolidone) and copolymers and derivatives thereof; casein; and mixtures of such binders.
- Preferred additional binders include cellulose derivatives such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, methyl hydroxye
- the ink-receptive recording layer of the recording materials of the present invention may comprise additional components as known in the art for use in recording materials.
- the ink receptive layer or layers may comprise one or more absorbent filler or pigment.
- Suitable absorbent fillers or pigments for the ink-receptive recording layer or layers include for example clay, kaolin, talc, silica, calcium carbonate, diatomaceous earth, barium sulphate, titanium dioxide, aluminium oxide, zinc oxide, boehmite, starch, synthetic organic pigments, a blend of calcium fluoride and silica, zinc oxide, blends of zinc sulphide with barium sulphate, satin white, and the like, as well as mixtures of two or more of the above fillers.
- Preferred fillers include porous synthetic amorphous silica, porous boehmite, porous synthetic alumina, and precipitated calcium carbonate. Fillers may be present in any effective amount, and if present, typically are present in amounts of from about 1 to about 60 percent by weight of the coating composition.
- the ink-receptive recording layer of the recording materials of the present invention may additionally comprise one or more cationogenic substance.
- Suitable cationogenic substances for the ink-receptive recording layer include quaternary ammonium polymers such as poly (dimethyl diallyl ammonium chloride); quaternary phosphonium polymers; basic polymers such as polyethyleneimine, polyvinylamine and copolymers and derivatives thereof; polymers and copolymers comprising basic monomers such as vinyl pyridine, vinyl imidazole, and amine containing (meth)acrylates; salts and quaternised reaction products from such basic polymers; reaction products of a low molecular weight polyfunctional amine with a compound polyfunctional to amino groups such as epichlorohydrin; cationically modified poly (vinyl alcohols); or a polyvalent metallic cation.
- the cationogenic substances best known for this purpose are polymeric quaternary ammonium compounds.
- the ink-receptive layer or layers may advantageously also comprise further auxiliary agents as are known in the art, for example surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- auxiliary agents for example surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- the recording material of the invention may comprise two or more ink-receptive layers, any or all of which may comprise the inventive combination of gelatine and a triazolopyrimidine compound as hereinbefore described.
- the inventive combination is provided in the upper layer or layers of an ink-receptive system comprising two or more layers according to this aspect of the invention.
- the lower layer or layers may be any ink receiving system as is known in the art.
- the binder in the lower ink-receptive layer or layers of a recording material according to this aspect of the invention comprises gelatine.
- any of the ink-receptive layers may advantageously also comprise further auxiliary agents as hereinbefore described, for example additional binders, cationogenic substances, fillers or pigments, surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- additional binders for example additional binders, cationogenic substances, fillers or pigments, surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- the coated amount of the ink-receptive layer or layers may be determined by the printing apparatus, the quantity of ink to be printed, the substrate, and the components used.
- the total dry coating weight of the ink-receptive layer or layers may be up to about 50 gm -2 , preferably from about 2 gm -2 to about 10 gm -2 , most preferably from about 5 gm -2 to about 10 gm -2 .
- One of the advantages of the recording materials of the present invention comprising a triazolopyrimidine compound as a coalescence-reducing additive is that good image quality may be achieved with a low coating weight of the ink-receptive layer or layers.
- the ratio of the dry coating weight of the gelatine and cellulose derivative of the preferred embodiments is not particularly limited and may vary between about 1:0.1 and about 1:5.
- the triazolopyrimidine compound may be present in any effective amount in the coated ink-receptive recording layer. Typically, the triazolopyrimidine compound is present in an amount of from about 0.001 to about 4 gm -2 of the substrate surface to which it is applied, and preferably from about 0.01 to about 0.5 gm -2 , although the amount can be outside these ranges depending on the application and compound used.
- One of the advantages of the preferred tetra-aza indene compounds of the invention is that significant image quality improvements may be realised from the incorporation of only a small quantity of the tetra-aza indene compound as a coalescence-reducing additive.
- the tetra-aza indene compound may be provided to the coating formulation by any convenient means, such as a solution in a suitable solvent or as a dispersion in a suitable carrier.
- the compound is provided as an aqueous solution. Therefore preferable compounds include those possessing a water solubilising group such as an ionisable substituent
- the preferred compounds 2, 3, and 6 of the invention may be dissolved in aqueous base, such as sodium or potassium carbonate, and provided to the coating formulation as a solution of the salt.
- the preferred compounds may be dissolved in the coating formulation at a suitable pH.
- the tetra-aza indene compounds may also be provided as a dispersion of the solid.
- the ink-receptive layer or layers may conveniently be produced as aqueous formulations and coated on to the substrate by any suitable coating means, such as a slide bead coater, a curtain coater, a rod coater, a gravure coater, a blade coater, an air knife coater, or a bar coater.
- suitable coating means such as a slide bead coater, a curtain coater, a rod coater, a gravure coater, a blade coater, an air knife coater, or a bar coater.
- the surface of the support may be treated in order to improve the adhesion of the bottom layer to the support prior to applying the coating layer to the support. Suitable treatments include buffing, corona discharge, or the application of an undercoating or subbing layer to the surface of the support. Such subbing layers are known in the art.
- the back surface of the material may be left uncoated or may have a coating for lay-flat or for write on properties. Additionally, lubricants to promote paper transport in the printing apparatus may be added to the back layer. Alternatively, the ink-receptive layer or layers may be provided on both sides of the substrate.
- an ink jet recording method comprising the steps of ejecting droplets of an ink composition comprising at least a colorant and a carrier liquid onto the recording medium of the present invention to deposit the ink droplets onto the recording medium in an imagewise pattern, thereby generating images on the recording sheet.
- the ink is an aqueous ink, that is to say an ink in which the carrier liquid is predominantly water, but may also comprise one or more water soluble organic cosolvent such as a polyhydric alcohol.
- the ink also comprises one or more surfactants.
- the materials of the invention are suitable for use with inks comprising dyes or pigments as colorants, but are most suitable for use with dyed inks.
- inks are well known in the art.
- the materials of the invention are suitable for use with any type of ink jet printer, for instance a thermal drop-on-demand printer, a piezo drop-on-demand printer, or a continuous ink jet printer.
- the printer may be a desk top ink jet printer or a wide format ink jet printer.
- the printing apparatus is a desk top drop-on-demand ink jet printer.
- the recording materials disclosed herein have been referred to primarily as being useful for aqueous ink jet printers, they may also be used in any other printing or imaging process, such as printing with pen plotters, handwriting with ink pens, and with conventional printing processes such as flexographic printing and the like, provided that the ink employed to form the image is compatible with the ink-receptive layer of the recording sheet.
- a comparison recording material was prepared as follows:
- Coating formulation A was prepared using the components given in Table 1.
- Table 1 Component % by weight Deionised water 79.4 Deionised ossein gelatine 11.98 Optical brightener 4.47 Toning agent 0.2 4% sodium hydroxide solution 3.19 Glycerol 0.16 Surfactant A 50% solution 0.6 Total 100
- Surfactant A was Olin 10G commercially available from Olin Chemicals. Glycerol was present as a plasticiser.
- the toning agent was an 0.25% dispersion of a combination of C.I. Pigment Blue 15:1 and C.LPigment Violet 23.
- the optical brightener was a 3.33% solution of a diaminostilbene optical brightener.
- Coating formulation B was prepared using the components given in Table 2.
- Table 2 Component % by weight Deionised water 84.07 Deionised ossein gelatine 11.98 4% sodium hydroxide solution 3.19 Glycerol 0.16 Surfactant A 50% solution 0.6 Total 100
- Coating formulation C was prepared using the components given in Table 3.
- Table 3 Component % by weight Deionised water 91.64 20% Phenol 0.75 Deionised ossein gelatine 2.69 Methyl hydroxypropyl cellulose 2.69 4% sodium hydroxide solution 0.92
- Surfactant C 1.2
- Surfactant B 0.08 Total 100
- Surfactant B was a 5% solution of a fluorinated surfactant commercially available under the trade name Lodyne S-107 from Ciba.
- Surfactant C was a 3% solution of an alkyl phenol ethoxylate surfactant commercially available under the trade name Triton X-100 from Union Carbide Chemicals and Plastics Company Inc.
- the comparison recording material was prepared by simultaneously coating four layers onto a barrier coated plain paper base of total substance 160 gm -2 according to the details given in table 4. The two upper layers were coated separately for ease of coating but comprise the same components.
- Table 4 Layer Formulation Dry Coating Weight First coating layer A 1.71 gm -2 Second coating layer B 1.69 gm -2 Third coating layer C 1.53 gm -2 Fourth coating layer C 1.53 gm -2 Total dry coat weight: 6.46 gm -2
- Formulations for recording materials according to the invention were then prepared by adding tetra-aza indene compounds to samples of the coating formulation C using the compounds and quantities shown in table 5 to provide the formulations D - H for the invention.
- Formulation C has a pH of approximately 9 and the compounds dissolve to provide a solution of the salt of the tetra-aza indene compound.
- Table 5 Formulation Compound added Quantity D Compound 2 0.5 % E Compound 2 1.0 % F Compound 3 0.5 % G Compound 3 1.0 % H Compound 6 0.5 %
- the coated samples were printed using dyed inks and a Epson 870 ink jet printer with a test pattern comprising patches of cyan, magenta, yellow, and black inks at an ink loading of 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%, and blue, green, and red patches made by printing the coloured inks in combination at the same loadings to give a maximum ink loading of 200% (i.e. a 100% blue patch by printing 100% cyan + 100% magenta inks and so on, and similarly with the green patches made by printing cyan + yellow inks, and the red patches by printing magenta + yellow inks).
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- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Photoreceptors In Electrophotography (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Ink Jet (AREA)
Abstract
Description
- The present invention relates to a recording material for recording using the ink jet printing process.
- Ink jet recording is a non-impact printing method wherein droplets of a recording fluid, the ink, are formed by forcing the fluid through a tiny nozzle (or a series of nozzles) under computer control and deposited on a recording material such as paper or transparent film. There are several classes of ink jet printer, for instance thermal drop-on-demand printers, piezo drop-on-demand printers, and continuous ink jet printers. Ink jet recording has been intensively developed in recent years, and has found broad application as output for personal computers in the office and the home because of its low noise characteristic, capability of high speed printing, and facility of multi-colour printing. Ink jet printing techniques, particularly those using mainly aqueous inks, have undergone rapid development both in respect of reliability and the image quality that the printing apparatus can achieve, and in respect of the cost price of the printing apparatus. Consequently, increasingly severe requirements are being set for the recording materials. The recording produced by means of an ink jet processes is required to have, for example, good water and smear resistance, high resolution, high colour density, sufficient ink gradation, and good light fastness.
- One type of recording material commonly used for the ink jet printing process is described as a swelling polymer system, and comprises one or more ink-receptive recording layer formed of one or more water-accepting polymeric binders arranged on a suitable substrate. The polymeric binder may, for example, be gelatine; a cellulose derivative such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, ethyl hydroxypropyl cellulose, or carboxymethylhydroxyethyl cellulose; a vinyl polymer such as poly (vinyl alcohol) or poly (vinyl pymolidone); or a mixture of such binders.
- Optionally, the recording layer also comprises a cationogenic substance in order to bind the dyes from the inks, together with other functional additives such as an absorbent pigment or a surfactant. Suitable cationogenic substances for use in such recording layers are well known, and include, for example, polyvalent metallic ions, quaternary ammonium salts, polyamines and salts thereof, polymeric ammonium compounds, and basic latexes.
- Further,
United States Patent 5,457,486 discloses a recording sheet which comprises (a) a base sheet; (b) a material selected from the group consisting of tetrazolium compounds, indolinium compounds, imidazolinium compounds, and mixtures thereof; (c) an optional pigment; and (d) an optional binder; similarlyUnited States Patent 5,441,795 discloses ink jet recording sheets containing pyridinium or piperazinium compounds. - Such recording materials may provide prints and images of good quality, and are suitable for their intended purposes. However, a need remains for improved recording sheets which exhibit good image quality when printed with aqueous inks, particularly when printing a multi-colour image in which very dark or dense tints are to be reproduced. Due to the greater quantity of ink laid down, the ink can be slow to absorb into the surface of the recording sheet as this absorption depends on swelling of the polymer layer. Further, this slow absorption is becoming more of a problem as printers develop and printing speeds increase, and can lead to visible print deficiencies such as coalescence caused by drops mixing on the print surface before the ink is absorbed.
-
United States Patent 5,657,064 discloses ink jet recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, or indazole compounds;United States Patent 5,659,348 discloses recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, or pyrazine compounds;United States Patent 5,729,266 discloses recording sheets containing oxazole, isoxazole, oxazolidinone, oxazoline salt, morpholine, thiazole, thiazolidine, thiadiazole, and phenothiazine compounds; however these inventions particularly relate to improving the drying performance of recording sheets, and especially to reducing the curl of sheets dried with microwave radiation and not to improving the rate of absorption of the ink. -
discloses ink jet recording sheets containing triazolopyrimidines of formula I, wherein Z is hydrogen or CH2SH. However this invention particularly relates to improving the light fastness of printed recording sheets and not to improving the rate of absorption of the ink.Japanese Patent Application 2000-094,829 - Thus there is still a requirement for an improved image receiving material which is rapid to dry without coalescence when printed with heavy ink loads and which provides good quality dense images. We have developed such a material.
- According to this invention there is provided a recording material suitable for ink jet recording comprising a sheet like substrate and arranged on at least one side of the substrate at least one ink-receptive recording layer comprising:
- gelatine; and
- at least one triazolopyrimidine compound or a salt thereof.
- The supporting substrate for the recording materials of the invention may be any of those known for use in printing and imaging media. Suitable substrates include, for example paper, high wet-strength paper, tracing paper, heavyweight paper, fine art paper, card, board, coated paper such as resin coated, polyethylene coated, and barrier layer coated paper, synthetic papers, canvas, cloth, fabric, metals such as aluminium, and polymeric substrates such as filled plastics, opaque plastics, or transparent materials, for example cellulose acetates, poly(ethylene), poly(propylene), poly (vinyl chloride), poly (ethylene terephthalate) and poly (ethylene naphthalate), polycarbonate, polysulphone, polyether sulphone, poly (arylene sulphone), poly(arylene ether ketone sulphone), cellophane, polyvinyl fluoride, polyimide, and the like. Preferably the supporting substrate is polyethylene coated paper or barrier layer coated paper.
- By barrier layer coated paper is meant a paper coated with a water repellent resin barrier layer provided in the form of a latex comprising fine particles of a film-forming polymer suspended in an aqueous carrier. The latex is allowed to form a film during the coating and drying process. The barrier layer may comprise almost any film-forming latex polymer. The polymer of the barrier layer may preferably have a glass transition point of at least 40° C, more preferably approximately 50° C - 100° C. The polymer of the barrier layer may optionally contain other additives as are known in the art, such as for example, UV absorbers, light stabilisers such as hindered amines, optical brightening agents, or tinting agents. The barrier layer may additionally contain a proportion of an inorganic filler and other additives to improve the operation of the coating process, for example polymeric thickeners, lubricating agents, dispersants, and adhesion promoters.
- The gelatine for the ink-receptive layer of the recording materials of the invention may be any gelatine known for use in imaging materials, for example skin or bone gelatine, treated gelatine such as deionised gelatine, modified gelatine such as phthalated gelatine or phenylcarbamoylated gelatine, or a cationically modified gelatine. A particularly suitable gelatine is a deionised ossein gelatine of high isoelectric point
- Various permutations of the triazolopyrimidine ring system are known, but especially suitable triazolopyrimidine compounds are s-triazolo[1,5-a]pyrimidine compounds commonly referred to as tetra-aza indene compounds and having the general structure I.
wherein
the substituents W, X and Y, which may be the same or different, are individually R, OR, SR, SOR, SO2R, NRR', NR(COR'), CO2R, CONRR', SO2NRR', NRSO2R', CN, NO2, halogen, sulphonic acid, or phosphonic acid, wherein the groups R and R' are independently hydrogen, branched or unbranched C1 - C20 substituted or unsubstituted, saturated or unsaturated hydrocarbon, e.g., alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, alkylaryl, or arylalkyl;
the substituent Z is R, OR, SR, SOR, SO2R, NRR', NR(COR'), CO2R, CONRR', SO2NRR', NRSO2R', CN, NO2, halogen, sulphonic acid, or phosphonic acid, wherein the groups R and R' are independently, branched or unbranched C1 - C20 unsubstituted, saturated or unsaturated hydrocarbon, e.g., alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, alkylaryl, or arylalkyl;
or wherein two or more of the groups W, X, Y, R, and R', may be combined to form a ring system or systems. Preferred substituents W, X and Y include in particular hydrogen, methyl, ethyl, and hydroxy groups. Preferred substituents Z include in particular methyl, ethyl, and hydroxy groups. - Tetra-aza indene compounds are known compounds or may be prepared by known methods, and in particular by the condensation of an appropriate aminotriazole with a suitable β-dicarbonyl compound.
- An especially preferred class of tetra-aza indene compounds according to formula I are those wherein the group Y is a hydroxy group.
-
-
-
- It is to be understood that many tetra-aza indene compounds are potentially tautomeric and that this invention also includes all relevant tautomers of such compounds. In particular, compounds of formula I wherein one of the groups W, X, Y, or Z is a hydroxy group or an NHR group, including the hereinbefore described compounds 2, 3, and 6, may exist as tautomers.
- It is further to be understood that certain tetra-aza indene compounds, particularly those having an ionisable group as a substituent group, may form salts and that this invention also includes relevant salts of such compounds. An ionisable group is one which is capable of forming an anionic group or a cationic group in the medium of use. Suitable ionisable groups include salt forming substituents such as sulphonic acid, carboxylic acid, phosphonic acid, and basic nitrogen containing groups. Further, hydroxy groups located as substituents W or Y of the formula I are frequently sufficiently acidic to enable salt formation and therefore salts of such compounds, including the hereinbefore described compounds 2, 3, and 6, may be used in the invention.
- There may also be present in the ink-receptive layer or layers additional water receptive polymeric binders compatible with the gelatine. Suitable binders include poly (vinyl alcohol) and copolymers and derivatives thereof; carbohydrates such as tragacanth gum, sodium alginate, or water-soluble starch derivatives; water-accepting cellulose derivatives such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, or carboxymethylhydroxyethyl cellulose; polyalkylene oxides such as polyethylene oxide and polypropylene oxide or derivatives thereof; water-accepting acrylate, methacrylate, or maleate polymers and copolymers and derivatives thereof; poly (vinyl pyrrolidone) and copolymers and derivatives thereof; casein; and mixtures of such binders. Preferred additional binders include cellulose derivatives such as hydroxyethyl cellulose, methyl hydroxypropyl cellulose, carboxymethyl cellulose, methyl hydroxyethyl cellulose, or carboxymethylhydroxyethyl cellulose.
- Therefore according to one especially preferred embodiment of the invention there is provided a recording material suitable for ink jet recording comprising a sheet like substrate and arranged on at least one side of the substrate at least one ink-receptive recording layer comprising:
- gelatine;
- a cellulose derivative; and
- at least one triazolopyrimidine compound or a salt thereof;
- Further, the ink-receptive recording layer of the recording materials of the present invention may comprise additional components as known in the art for use in recording materials. For instance the ink receptive layer or layers may comprise one or more absorbent filler or pigment. Suitable absorbent fillers or pigments for the ink-receptive recording layer or layers include for example clay, kaolin, talc, silica, calcium carbonate, diatomaceous earth, barium sulphate, titanium dioxide, aluminium oxide, zinc oxide, boehmite, starch, synthetic organic pigments, a blend of calcium fluoride and silica, zinc oxide, blends of zinc sulphide with barium sulphate, satin white, and the like, as well as mixtures of two or more of the above fillers. Preferred fillers include porous synthetic amorphous silica, porous boehmite, porous synthetic alumina, and precipitated calcium carbonate. Fillers may be present in any effective amount, and if present, typically are present in amounts of from about 1 to about 60 percent by weight of the coating composition.
- Further, the ink-receptive recording layer of the recording materials of the present invention may additionally comprise one or more cationogenic substance. Suitable cationogenic substances for the ink-receptive recording layer include quaternary ammonium polymers such as poly (dimethyl diallyl ammonium chloride); quaternary phosphonium polymers; basic polymers such as polyethyleneimine, polyvinylamine and copolymers and derivatives thereof; polymers and copolymers comprising basic monomers such as vinyl pyridine, vinyl imidazole, and amine containing (meth)acrylates; salts and quaternised reaction products from such basic polymers; reaction products of a low molecular weight polyfunctional amine with a compound polyfunctional to amino groups such as epichlorohydrin; cationically modified poly (vinyl alcohols); or a polyvalent metallic cation. The cationogenic substances best known for this purpose are polymeric quaternary ammonium compounds.
- In addition to the components already mentioned, it is to be understood that the ink-receptive layer or layers may advantageously also comprise further auxiliary agents as are known in the art, for example surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- Furthermore there may also be present additional layers in the recording materials of this aspect of the invention. Specifically, the recording material of the invention may comprise two or more ink-receptive layers, any or all of which may comprise the inventive combination of gelatine and a triazolopyrimidine compound as hereinbefore described.
- Preferably, the inventive combination is provided in the upper layer or layers of an ink-receptive system comprising two or more layers according to this aspect of the invention. The lower layer or layers may be any ink receiving system as is known in the art.
- According to a particularly preferred embodiment of the invention there is provided a recording material suitable for ink jet recording comprising in the following order:
- 1) a sheet like substrate;
- 2) at least one lower ink-receptive recording layer; and
- 3) at least one upper ink-receptive recording layer comprising in combination:
- gelatine;
- a cellulose derivative; and
- at least one triazolopyrimidine compound or a salt thereof;
- Preferably, the binder in the lower ink-receptive layer or layers of a recording material according to this aspect of the invention comprises gelatine.
- In addition to the components already mentioned, it is to be understood that any of the ink-receptive layers may advantageously also comprise further auxiliary agents as hereinbefore described, for example additional binders, cationogenic substances, fillers or pigments, surfactants, plasticisers, lubricants, latexes, cross linking agents, antistatic agents, fungicides, dispersants, antifoams, toning agents, ultraviolet absorbers, and optical brighteners.
- The coated amount of the ink-receptive layer or layers may be determined by the printing apparatus, the quantity of ink to be printed, the substrate, and the components used. The total dry coating weight of the ink-receptive layer or layers may be up to about 50 gm-2, preferably from about 2 gm-2 to about 10 gm-2, most preferably from about 5 gm-2 to about 10 gm-2. One of the advantages of the recording materials of the present invention comprising a triazolopyrimidine compound as a coalescence-reducing additive is that good image quality may be achieved with a low coating weight of the ink-receptive layer or layers.
- The ratio of the dry coating weight of the gelatine and cellulose derivative of the preferred embodiments is not particularly limited and may vary between about 1:0.1 and about 1:5.
- The triazolopyrimidine compound may be present in any effective amount in the coated ink-receptive recording layer. Typically, the triazolopyrimidine compound is present in an amount of from about 0.001 to about 4 gm-2 of the substrate surface to which it is applied, and preferably from about 0.01 to about 0.5 gm-2, although the amount can be outside these ranges depending on the application and compound used. One of the advantages of the preferred tetra-aza indene compounds of the invention is that significant image quality improvements may be realised from the incorporation of only a small quantity of the tetra-aza indene compound as a coalescence-reducing additive.
- The tetra-aza indene compound may be provided to the coating formulation by any convenient means, such as a solution in a suitable solvent or as a dispersion in a suitable carrier. Preferably the compound is provided as an aqueous solution. Therefore preferable compounds include those possessing a water solubilising group such as an ionisable substituent The preferred compounds 2, 3, and 6 of the invention may be dissolved in aqueous base, such as sodium or potassium carbonate, and provided to the coating formulation as a solution of the salt. Alternatively the preferred compounds may be dissolved in the coating formulation at a suitable pH. Alternatively the tetra-aza indene compounds may also be provided as a dispersion of the solid.
- Another advantage of the invention is that the ink-receptive layer or layers may conveniently be produced as aqueous formulations and coated on to the substrate by any suitable coating means, such as a slide bead coater, a curtain coater, a rod coater, a gravure coater, a blade coater, an air knife coater, or a bar coater. Some of these methods allow for simultaneous coatings of two or more layers, which is preferred from a manufacturing economic perspective.
- If desired, the surface of the support may be treated in order to improve the adhesion of the bottom layer to the support prior to applying the coating layer to the support. Suitable treatments include buffing, corona discharge, or the application of an undercoating or subbing layer to the surface of the support. Such subbing layers are known in the art.
- The back surface of the material may be left uncoated or may have a coating for lay-flat or for write on properties. Additionally, lubricants to promote paper transport in the printing apparatus may be added to the back layer. Alternatively, the ink-receptive layer or layers may be provided on both sides of the substrate.
- According to another aspect of the present invention, there is provided an ink jet recording method comprising the steps of ejecting droplets of an ink composition comprising at least a colorant and a carrier liquid onto the recording medium of the present invention to deposit the ink droplets onto the recording medium in an imagewise pattern, thereby generating images on the recording sheet. Preferably the ink is an aqueous ink, that is to say an ink in which the carrier liquid is predominantly water, but may also comprise one or more water soluble organic cosolvent such as a polyhydric alcohol. Frequently the ink also comprises one or more surfactants. The materials of the invention are suitable for use with inks comprising dyes or pigments as colorants, but are most suitable for use with dyed inks. Such inks are well known in the art. The materials of the invention are suitable for use with any type of ink jet printer, for instance a thermal drop-on-demand printer, a piezo drop-on-demand printer, or a continuous ink jet printer. The printer may be a desk top ink jet printer or a wide format ink jet printer. In a particularly preferred embodiment, the printing apparatus is a desk top drop-on-demand ink jet printer.
- Although the recording materials disclosed herein have been referred to primarily as being useful for aqueous ink jet printers, they may also be used in any other printing or imaging process, such as printing with pen plotters, handwriting with ink pens, and with conventional printing processes such as flexographic printing and the like, provided that the ink employed to form the image is compatible with the ink-receptive layer of the recording sheet.
- The following example will serve to illustrate the invention.
- A comparison recording material was prepared as follows:
- Coating formulation A was prepared using the components given in Table 1.
Table 1 Component % by weight Deionised water 79.4 Deionised ossein gelatine 11.98 Optical brightener 4.47 Toning agent 0.2 4% sodium hydroxide solution 3.19 Glycerol 0.16 Surfactant A 50% solution 0.6 Total 100 - Surfactant A was Olin 10G commercially available from Olin Chemicals. Glycerol was present as a plasticiser. The toning agent was an 0.25% dispersion of a combination of C.I. Pigment Blue 15:1 and C.LPigment Violet 23. The optical brightener was a 3.33% solution of a diaminostilbene optical brightener.
- Coating formulation B was prepared using the components given in Table 2.
Table 2 Component % by weight Deionised water 84.07 Deionised ossein gelatine 11.98 4% sodium hydroxide solution 3.19 Glycerol 0.16 Surfactant A 50% solution 0.6 Total 100 - 1.9 g of a 1% solution of 1-(N,N-dimethylcarbamoyl)4-(2-sulphoethyl) pyridinium inner salt cross linking agent was added to this formulation before coating as a hardener.
- Coating formulation C was prepared using the components given in Table 3.
Table 3 Component % by weight Deionised water 91.64 20% Phenol 0.75 Deionised ossein gelatine 2.69 Methyl hydroxypropyl cellulose 2.69 4% sodium hydroxide solution 0.92 Surfactant C 1.2 Surfactant B 0.08 Total 100 - Surfactant B was a 5% solution of a fluorinated surfactant commercially available under the trade name Lodyne S-107 from Ciba. Surfactant C was a 3% solution of an alkyl phenol ethoxylate surfactant commercially available under the trade name Triton X-100 from Union Carbide Chemicals and Plastics Company Inc.
- The comparison recording material was prepared by simultaneously coating four layers onto a barrier coated plain paper base of total substance 160 gm-2 according to the details given in table 4. The two upper layers were coated separately for ease of coating but comprise the same components.
Table 4 Layer Formulation Dry Coating Weight First coating layer A 1.71 gm-2 Second coating layer B 1.69 gm-2 Third coating layer C 1.53 gm-2 Fourth coating layer C 1.53 gm-2 Total dry coat weight: 6.46 gm-2 - Formulations for recording materials according to the invention were then prepared by adding tetra-aza indene compounds to samples of the coating formulation C using the compounds and quantities shown in table 5 to provide the formulations D - H for the invention. Formulation C has a pH of approximately 9 and the compounds dissolve to provide a solution of the salt of the tetra-aza indene compound.
Table 5 Formulation Compound added Quantity D Compound 2 0.5 % E Compound 2 1.0 % F Compound 3 0.5 % G Compound 3 1.0 % H Compound 6 0.5 % - Recording materials wherein the upper ink-receptive layer comprises a combination of gelatine, a cellulose derivative, and a triazolopyrimidine compound according to a preferred embodiment of the present invention were then coated according to the coating assembly shown in table 4 except that formulation C for the upper two layers was replaced by tetra-aza indene compound to the formulations for the two upper layers gives a total coating weight for the tetra-aza indene compound of 0.14 gm-2, an addition of 0.5% gives a coating weight of 0.28 gm-2, and an addition of 1% gives a coating weight of 0.56 gm-2.
- The coated samples were printed using dyed inks and a Epson 870 ink jet printer with a test pattern comprising patches of cyan, magenta, yellow, and black inks at an ink loading of 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, and 100%, and blue, green, and red patches made by printing the coloured inks in combination at the same loadings to give a maximum ink loading of 200% (i.e. a 100% blue patch by printing 100% cyan + 100% magenta inks and so on, and similarly with the green patches made by printing cyan + yellow inks, and the red patches by printing magenta + yellow inks). It is expected that coalescence will start to appear when the ink is not absorbed sufficiently rapidly at the higher ink loadings. With each colour, the density of the patch at which coalescence was first observed is given in table 6.
Table 6 Sample Formulation Ink loading for coalescence Blue Green Red Black Yellow Magenta Cyan Comparison C 40% 50% 50% 40% - 70% 70% Invention D 50% 60% - 60% - - - Invention E - - - - - - - Invention F - - - - - - - Invention G - - - - - - - Invention H - - - - - - - - In the above table the symbol - means that coalescence was not observed even at the highest ink loading. It is seen that the comparison sample showed significant coalescence at moderate to high ink loads, that the inventive sample containing formulation D comprising the lowest level of compound 2 in the two upper layers showed a significant improvement, and that none of the other inventive samples showed any coalescence at all in this test. This shows the usefulness of the inventive materials.
Claims (9)
- A recording material suitable for ink jet recording comprising a sheet like substrate and arranged on at least one side of the substrate at least one ink-receptive recording layer, characterised in that the recording layer comprises:a. gelatinewherein
andthe substituents W, X and Y, which may be the same or different, are individually R, OR, SR, SOR, SO2R, NRR', NR(COR'), CO2R, CONRR', SO2NRR', NRSO2R', CN, NO2, halogen, sulphonic acid, or phosphonic acid, wherein the groups R and R' are independently hydrogen, branched or unbranched C1 - C20 substituted or unsubstituted, saturated or unsaturated hydrocarbon, e.g., alkyl, alkenyl, alkynyl, cycloalkyl, cycloakenyl, aryl, heteroaryl, alkylaryl, or arylalkyl;the substituent Z is R, OR, SR, SOR, SO2R, NRR', NR(COR'), CO2R, CONRR', SO2NRR', NRSO2R', CN, NO2, halogen, sulphonic acid, or phosphonic acid, wherein the groups R and R' are independently, branched or unbranched C1 - C20 unsubstituted, saturated or unsaturated hydrocarbon, e.g., alkyl, alkenyl alkynyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, alkylaryl, or arylalkyl;or wherein two or more of the substituents or groups W, X, Y, R, and R', may be combined to form a ring system or systems. - A recording material suitable for ink jet recording according to claim 1, characterised in that the recording layer comprises:a cellulose derivative.
- A recording material suitable for ink jet recording according to claim 2 comprising in the following order:1) said sheet like substrate;2) at least one lower ink-receptive recording layer; and3) said at least one ink-receptive recording layer.
- A recording material according to either of claims 2 or 3 wherein the cellulose derivative is selected from hydroxyethyl cellulose, methylhydroxypropyl cellulose, carboxymethyl cellulose, carboxymethylhydroxyethyl cellulose, methylhydroxyethyl cellulose, and mixtures thereof.
- A recording material according to any of claims 1 - 4 wherein the substrate is selected from paper, high wet-strength paper, tracing paper, heavyweight paper, fine art paper, card, board, resin coated paper, polyethylene coated paper, barrier layer coated paper, synthetic paper, canvas, cloth, fabric, cellulose acetates, poly(ethylene), poly(propylene), poly (vinyl chloride), poly (ethylene terephthalate) poly (ethylene naphthalate), polycarbonate, polysulphone, polyether sulphone, poly (arylene sulphone), poly(arylene ether ketone sulphone), cellophane, polyvinyl fluoride, and polyimide.
- A recording material according to claim 5 wherein the substrate is a coated paper selected from resin coated paper, polyethylene coated paper, and barrier layer coated paper.
- A recording material according to any of claims 1-3 whereinthe substituent Y of the triazolopyrimidine compound of formula I is hydroxy;the substituents or groups X, W, Z, R, and R' are as defined in claim 1
andwherein two or more of the substituents or groups W, X, R, and R' may be combined to form a ring system or systems. - A recording material according to claim 7 wherein the triazolopyrimidine compound is 4-hydroxy-2-isopropylthio-6-methyl-1,3,3a,7-tetra-aza indene.
- An ink jet recording method comprising the steps of ejecting droplets of an aqueous ink composition comprising at least a colorant and a carrier liquid onto a recording material according to any of claims 1 - 8 to deposit the ink droplets onto the recording material in an imagewise pattern, thereby generating images on the recording material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0204699 | 2002-02-28 | ||
| GB0204699A GB2385809A (en) | 2002-02-28 | 2002-02-28 | Ink-jet recording material |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP1340621A2 EP1340621A2 (en) | 2003-09-03 |
| EP1340621A3 EP1340621A3 (en) | 2006-03-15 |
| EP1340621B1 true EP1340621B1 (en) | 2008-02-13 |
Family
ID=9931967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03003513A Expired - Lifetime EP1340621B1 (en) | 2002-02-28 | 2003-02-15 | Recording materials |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1340621B1 (en) |
| AT (1) | ATE385904T1 (en) |
| DE (1) | DE60319023D1 (en) |
| GB (1) | GB2385809A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795245B2 (en) | 2005-05-20 | 2010-09-14 | Atlantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| WO2013147836A1 (en) * | 2012-03-30 | 2013-10-03 | Hewlett-Packard Development Company, L.P. | Recording material |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006011797A1 (en) | 2004-07-30 | 2006-02-02 | Fuji Photo Film B.V. | Recording media |
| EP1878829A1 (en) * | 2006-07-12 | 2008-01-16 | Papierfabriken Cham-Tenero AG | Coated base paper |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5234491B2 (en) * | 1973-10-25 | 1977-09-03 | ||
| GB1500278A (en) * | 1975-07-24 | 1978-02-08 | Kodak Ltd | Photographic silver halide emulsions |
| US4578285A (en) * | 1983-03-16 | 1986-03-25 | Polaroid Corporation | Ink jet printing substrate |
| JPH0687124B2 (en) * | 1987-02-26 | 1994-11-02 | アグフアーゲヴエルト・アクチエンゲゼルシヤフト | Photo recording material |
| JP2990681B2 (en) * | 1992-08-12 | 1999-12-13 | 富士写真フイルム株式会社 | Magnetic recording media |
| US5441795A (en) | 1993-03-19 | 1995-08-15 | Xerox Corporation | Recording sheets containing pyridinium compounds |
| US6846525B2 (en) * | 1993-03-19 | 2005-01-25 | Xerox Corporation | Recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, and pyrazine compounds |
| US6180238B1 (en) | 1993-03-19 | 2001-01-30 | Xerox Corporation | Recording sheets containing oxazole, isooxazole, oxazolidinone, oxazoline salt, morpholine, thiazole, thiazolidine, thiadiazole, and phenothiazine compounds |
| US5457486A (en) | 1993-03-19 | 1995-10-10 | Xerox Corporation | Recording sheets containing tetrazolium indolinium, and imidazolinium compounds |
| US6482503B1 (en) | 1993-03-19 | 2002-11-19 | Xerox Corporation | Recording sheets containing pyrrole, pyrrolidine, pyridine, piperidine, homopiperidine, quinoline, isoquinoline, quinuclidine, indole, and indazole compounds |
| JP3758378B2 (en) * | 1998-09-25 | 2006-03-22 | コニカミノルタホールディングス株式会社 | Inkjet recording paper |
-
2002
- 2002-02-28 GB GB0204699A patent/GB2385809A/en not_active Withdrawn
-
2003
- 2003-02-15 AT AT03003513T patent/ATE385904T1/en not_active IP Right Cessation
- 2003-02-15 DE DE60319023T patent/DE60319023D1/en not_active Expired - Lifetime
- 2003-02-15 EP EP03003513A patent/EP1340621B1/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7795245B2 (en) | 2005-05-20 | 2010-09-14 | Atlantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| US8835441B2 (en) | 2005-05-20 | 2014-09-16 | Amgen Inc. | Heterobicyclic metalloprotease inhibitors |
| WO2013147836A1 (en) * | 2012-03-30 | 2013-10-03 | Hewlett-Packard Development Company, L.P. | Recording material |
| CN104093570A (en) * | 2012-03-30 | 2014-10-08 | 惠普发展公司,有限责任合伙企业 | Recording material |
| CN104093570B (en) * | 2012-03-30 | 2016-01-27 | 惠普发展公司,有限责任合伙企业 | Recording materials |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1340621A2 (en) | 2003-09-03 |
| EP1340621A3 (en) | 2006-03-15 |
| ATE385904T1 (en) | 2008-03-15 |
| DE60319023D1 (en) | 2008-03-27 |
| GB0204699D0 (en) | 2002-04-17 |
| GB2385809A (en) | 2003-09-03 |
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