EP0919862B1 - Photothermographic imaging element containing an antihalation dye - Google Patents
Photothermographic imaging element containing an antihalation dye Download PDFInfo
- Publication number
- EP0919862B1 EP0919862B1 EP98203843A EP98203843A EP0919862B1 EP 0919862 B1 EP0919862 B1 EP 0919862B1 EP 98203843 A EP98203843 A EP 98203843A EP 98203843 A EP98203843 A EP 98203843A EP 0919862 B1 EP0919862 B1 EP 0919862B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- photothermographic
- layer
- dye
- substituted
- photothermographic element
- 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
Links
- 238000003384 imaging method Methods 0.000 title claims description 26
- 239000000975 dye Substances 0.000 claims description 53
- 239000011230 binding agent Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 108010010803 Gelatin Proteins 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229920000159 gelatin Polymers 0.000 claims description 7
- 239000008273 gelatin Substances 0.000 claims description 7
- 235000019322 gelatine Nutrition 0.000 claims description 7
- 235000011852 gelatine desserts Nutrition 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 230000002209 hydrophobic effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- -1 silver halide Chemical class 0.000 description 77
- 239000010410 layer Substances 0.000 description 50
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 25
- 229910052709 silver Inorganic materials 0.000 description 24
- 239000004332 silver Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 16
- 239000003638 chemical reducing agent Substances 0.000 description 15
- 239000007800 oxidant agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- 238000012545 processing Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011241 protective layer Substances 0.000 description 11
- 239000003381 stabilizer Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 10
- 238000011160 research Methods 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 229920002451 polyvinyl alcohol Polymers 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- AQRYNYUOKMNDDV-UHFFFAOYSA-M silver behenate Chemical compound [Ag+].CCCCCCCCCCCCCCCCCCCCCC([O-])=O AQRYNYUOKMNDDV-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 230000001235 sensitizing effect Effects 0.000 description 4
- 150000003378 silver Chemical class 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- LOTMIRVNJTVTSU-UHFFFAOYSA-N 4-tert-butylbenzene-1,2-dicarbonitrile Chemical compound CC(C)(C)C1=CC=C(C#N)C(C#N)=C1 LOTMIRVNJTVTSU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000001007 phthalocyanine dye Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000003017 thermal stabilizer Substances 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- MOXDGMSQFFMNHA-UHFFFAOYSA-N 2-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1O MOXDGMSQFFMNHA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011066 ex-situ storage Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- JHKKTXXMAQLGJB-UHFFFAOYSA-N 2-(methylamino)phenol Chemical class CNC1=CC=CC=C1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 description 1
- NREKJIIPVVKRNO-UHFFFAOYSA-N 2-(tribromomethylsulfonyl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(S(=O)(=O)C(Br)(Br)Br)=NC2=C1 NREKJIIPVVKRNO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- PZTWFIMBPRYBOD-UHFFFAOYSA-N 2-acetylphthalazin-1-one Chemical compound C1=CC=C2C(=O)N(C(=O)C)N=CC2=C1 PZTWFIMBPRYBOD-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WLSZSLYALIHGPS-UHFFFAOYSA-N 2-bromo-2-(4-methylphenyl)sulfonylacetamide Chemical compound CC1=CC=C(S(=O)(=O)C(Br)C(N)=O)C=C1 WLSZSLYALIHGPS-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- KTWCUGUUDHJVIH-UHFFFAOYSA-N 2-hydroxybenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(O)C2=O)=O)=C3C2=CC=CC3=C1 KTWCUGUUDHJVIH-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- DFZVZKUDBIJAHK-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid silver Chemical compound [Ag].OC(C(=O)O)CCCCCCCCCCCCCCCC DFZVZKUDBIJAHK-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- LCMFKNJVGBDDNM-UHFFFAOYSA-N 2-phenyl-4,6-bis(tribromomethyl)-1,3,5-triazine Chemical compound BrC(Br)(Br)C1=NC(C(Br)(Br)Br)=NC(C=2C=CC=CC=2)=N1 LCMFKNJVGBDDNM-UHFFFAOYSA-N 0.000 description 1
- PHCOGQWRHWLVKP-UHFFFAOYSA-N 2-sulfoprop-2-enoic acid Chemical class OC(=O)C(=C)S(O)(=O)=O PHCOGQWRHWLVKP-UHFFFAOYSA-N 0.000 description 1
- IBWXIFXUDGADCV-UHFFFAOYSA-N 2h-benzotriazole;silver Chemical compound [Ag].C1=CC=C2NN=NC2=C1 IBWXIFXUDGADCV-UHFFFAOYSA-N 0.000 description 1
- UJBDWOYYHFGTGA-UHFFFAOYSA-N 3,4-dihydropyrrole-2-thione Chemical compound S=C1CCC=N1 UJBDWOYYHFGTGA-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- DSVIHYOAKPVFEH-UHFFFAOYSA-N 4-(hydroxymethyl)-4-methyl-1-phenylpyrazolidin-3-one Chemical compound N1C(=O)C(C)(CO)CN1C1=CC=CC=C1 DSVIHYOAKPVFEH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical class NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- SQARMCGNIUBXAJ-UHFFFAOYSA-N n-(2-hydroxyphenyl)benzenesulfonamide Chemical compound OC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 SQARMCGNIUBXAJ-UHFFFAOYSA-N 0.000 description 1
- GQORONPQIJQFDJ-UHFFFAOYSA-N n-(3,5-dibromo-4-hydroxyphenyl)benzenesulfonamide Chemical compound C1=C(Br)C(O)=C(Br)C=C1NS(=O)(=O)C1=CC=CC=C1 GQORONPQIJQFDJ-UHFFFAOYSA-N 0.000 description 1
- KFPBEVFQCXRYIR-UHFFFAOYSA-N n-(3,5-dichloro-4-hydroxyphenyl)benzenesulfonamide Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1NS(=O)(=O)C1=CC=CC=C1 KFPBEVFQCXRYIR-UHFFFAOYSA-N 0.000 description 1
- WHZPMLXZOSFAKY-UHFFFAOYSA-N n-(4-hydroxyphenyl)benzenesulfonamide Chemical compound C1=CC(O)=CC=C1NS(=O)(=O)C1=CC=CC=C1 WHZPMLXZOSFAKY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002557 polyglycidol polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical compound O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- YRSQDSCQMOUOKO-KVVVOXFISA-M silver;(z)-octadec-9-enoate Chemical compound [Ag+].CCCCCCCC\C=C/CCCCCCCC([O-])=O YRSQDSCQMOUOKO-KVVVOXFISA-M 0.000 description 1
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 1
- OIZSSBDNMBMYFL-UHFFFAOYSA-M silver;decanoate Chemical compound [Ag+].CCCCCCCCCC([O-])=O OIZSSBDNMBMYFL-UHFFFAOYSA-M 0.000 description 1
- MNMYRUHURLPFQW-UHFFFAOYSA-M silver;dodecanoate Chemical compound [Ag+].CCCCCCCCCCCC([O-])=O MNMYRUHURLPFQW-UHFFFAOYSA-M 0.000 description 1
- LTYHQUJGIQUHMS-UHFFFAOYSA-M silver;hexadecanoate Chemical compound [Ag+].CCCCCCCCCCCCCCCC([O-])=O LTYHQUJGIQUHMS-UHFFFAOYSA-M 0.000 description 1
- ORYURPRSXLUCSS-UHFFFAOYSA-M silver;octadecanoate Chemical compound [Ag+].CCCCCCCCCCCCCCCCCC([O-])=O ORYURPRSXLUCSS-UHFFFAOYSA-M 0.000 description 1
- OHGHHPYRRURLHR-UHFFFAOYSA-M silver;tetradecanoate Chemical compound [Ag+].CCCCCCCCCCCCCC([O-])=O OHGHHPYRRURLHR-UHFFFAOYSA-M 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- USFMMZYROHDWPJ-UHFFFAOYSA-N trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium Chemical compound CC(=C)C(=O)OCC[N+](C)(C)C USFMMZYROHDWPJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/49872—Aspects relating to non-photosensitive layers, e.g. intermediate protective layers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/7614—Cover layers; Backing layers; Base or auxiliary layers characterised by means for lubricating, for rendering anti-abrasive or for preventing adhesion
- G03C2001/7628—Back layer
Definitions
- This invention relates to a photothermographic imaging element suited for use with a red or near-infrared laser. More specifically, this invention relates to a photothermographic imaging element comprising an antihalation dye.
- photosensitive emulsion layers or other layers of silver halide light-sensitive materials colored layers that absorb light of specific wavelengths in order to provide filtration of unwanted wavelengths of light, absorb scattered light within a layer, or provide halation protection.
- These coloring layers can be located above the photosensitive layer, within the photosensitive layer, between the photosensitive layer and the support or on the opposite side of the support. When the colored layer is located in the latter three areas as described above, it is able to prevent unwanted back reflection of the light, thus providing halation protection to the photosensitive material.
- Antihalation is particularly important when a film is exposed using a laser because of the high intensity of light emitted by the laser necessitating high levels of dye to be used in order to provide adequate absorption of light. This can lead to undesirable coloration of the photographic element, particularly with regard to a photothermographic system where wet processing steps are unavailable to provide washout of the filtration dye.
- the problem to be solved by this invention is to provides a photothermographic element containing a dye that is useful for absorbing laser light in the red and near-infrared regions (i.e. in a wavelength range of 660 to 800 nm), that has very little extraneous absorption in unwanted areas of the visible spectrum, that is stable with time and that functions as an antihalation dye.
- This invention comprises a photothermographic imaging element comprising a support, a photothermographic imaging layer and at least one non-imaging layer positioned above the imaging layer, between the imaging layer and the support or on the side of the support opposite the imaging layer, wherein the non-imaging layer contains a dye of structure I: wherein
- a particular advantage of the dyes utilized in the preparation of a photothermographic element in accordance with the invention is the solubility of the dyes which allows coating of the antihalation element in a variety of polymeric binders. Another advantage is the excellent absorption of these dyes at the desired wavelengths as evidenced by their state-of-the-art properties as antihalation dyes in a photothermographic element. Another advantage is the stability of these dyes with time, both under hydrolytic and photolytic conditions.
- the dyes utilized in the photothermographic element of this invention is a dye of structure I: wherein
- M is preferably a multi-valent metal atom selected from the group consisting of: Mg, Ca, Sr, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, B, Al, Sn, Pb, Mo, Pd and Pt. Particularly preferred are Mg, Ni, Zn, and Cu.
- Alkyl and alkoxy groups preferably contain 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
- Alkyl groups include, for example, methyl, ethyl, propyl, isopropyl, butyl sec. butyl, tert. butyl, heptyl or decyl.
- Alkoxy groups include, for example, methoxy, ethoxy, propoxy, or tert. butoxy.
- Aryl and aryloxy groups preferably contain 6 to 12 carbon atoms, more preferably 5 to 8 carbon atoms.
- Aryl groups that can be used include, for example, phenyl, tolyl, naphthyl, 2,4-dimethylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 4-ethoxyphenyl, or 4-isopropoxyphenyl.
- Aryloxy groups include, for example, phenoxy, substituted phenoxy such as 2-methylphenoxy, 4-methylphenoxy, 2-ethylphenoxy, 4-ethylphenoxy, 4-eumylphenoxy, 4-isopropylphenoxy, 4-tert-butyl-phenoxy, 2-chlorophenoxy, or 4,-chlorophenoxy.
- Aromatic ring structures include, for example phenyl, 1,2-naphthyl, 2,3-naphthyl, or phenanthryl.
- Heteroaromatic rings include, for example, pyridine, pyrazine, pyridazine and pyrimidine.
- substituent groups refers to a substituted or unsubstituted alkyl
- benzene group refers to a substituted or unsubstituted benzene (with up to six substituents).
- substituent groups usable on molecules herein include any groups, whether substituted or unsubstituted, which do not destroy properties necessary for the photothermographic utility.
- substituents on any of the mentioned groups can include known substituents, such as: halogen, for example, chloro, fluoro, bromo, iodo; alkoxy, particularly those "lower alkyl" (that is, with 1 to 6 carbon atoms, for example, methoxy, ethoxy; substituted or unsubstituted alkyl, particularly lower alkyl (for example, methyl, trifluoromethyl); thioalkyl (for example, methylthio or ethylthio), particularly either of those with 1 to 6 carbon atoms; substituted and unsubstituted aryl, particularly those having from 6 to 20 carbon atoms (for example, phenyl); and substituted or unsubstituted heteroaryl, particularly those having a 5 or 6-membered ring containing 1 to 3 heteroatoms selected from N, O, or S (for example, pyridyl, thienyl, furyl, pyrrolyl); acid or acid or
- Alkyl substituents may specifically include "lower alkyl” (that is, having 1-6 carbon atoms), for example, methyl, or ethyl. Further, with regard to any alkyl group or alkylene group, it will be understood that these can be branched or unbranched and include ring structures.
- Dyes of structure I are known and some are commercially available.
- the dyes can be made by the methods outlined in The Phthalocyanines, Vol. I and II, Moser, F.H. and Thomas, A.L., CRC Press, Boca Raton, Florida, 1983 or by the method of Wöhrle, D.; Schnurpfeil, G.; Knothe, G. Dyes and Pigments 1992, 18 , 91.
- Illustrative dyes for use in the photothermographic element of this invention are represented, but not limited to, the examples shown in Table 1 (the peak absorption ( ⁇ max) of the dyes dissolved in acetone (or toluene) is also given in Table 1):
- the photothermographic element of this invention typically comprises a support, a photothermographic layer, a backing layer, an overcoat layer and various interlayers, such as, subbing layers, and filter layers.
- the dye is incorporated into a backing layer (e.g. a pelloid layer) or a layer between the support and the photothermographic layer.
- the layers of a photothermographic element are generally prepared from a solution containing a binder and other components to give the layer the desired properties in an appropriate solvent.
- an antihalation dye is dissolved in a solvent together with a binder for incorporation into the desired layer of the photothermographic element.
- the binder can be a hydrophobic binder preferably polymethyl methacrylate, polystyrene, polyvinyl butyral, or cellulose acetate butyrate.
- Preferred solvents for use with a hydrophobic binder are aromatic solvents, such as, toluene or xylene, ketone solvents, such as, methyl ethyl ketone, and methyl isobutyl ketone, tetrahydrofuran, ethyl acetate, chlorinated solvents such as dichloromethane.
- the solvent can contain water, if desired.
- the binder is a hydrophilic binder, preferably gelatin.
- the hydrophilic binder is generally dissolved in an aqueous medium for incorporation into the desired layer of the photothermographic element.
- the dye is preferably used in an amount of 10 to 10,000 ppm (parts per million), more preferably 10 to 1,000 ppm, based on the amount of binder in the layer.
- Typical photothermographic elements of this invention comprise at least one photothermographic layer containing in reactive association in a binder, preferably a binder comprising hydroxyl groups, (a) photographic silver halide prepared in situ and/or ex situ, (b) an image-forming combination comprising (i) an organic silver salt oxidizing agent, preferably a silver salt of a long chain fatty acid, such as silver behenate, with (ii) a reducing agent for the organic silver salt oxidizing agent, preferably a phenolic reducing agent, and (c) an optional toning agent.
- References describing such imaging elements include, for example, U.S. Patents 3,457,075; 4,459,350; 4,264,725 and 4,741,992 and Research Disclosure, June 1978, Item No. 17029.
- the latent image silver from the silver halide acts as a catalyst for the described image-forming combination upon processing.
- a preferred concentration of photographic silver halide is within the range of 0.01 to 10 moles of photographic silver halide per mole of silver behenate in the photothermographic material.
- Other photosensitive silver salts are useful in combination with the photographic silver halide if desired.
- Preferred photographic silver halides are silver chloride, silver bromide, silver bromochloride, silver bromoiodide, silver chlorobromoiodide, and mixtures of these silver halides. Very fine grain photographic silver halide is especially useful.
- the photographic silver halide can be prepared by any of the known procedures in the photographic art.
- Such procedures for forming photographic silver halides and forms of photographic silver halides are described in, for example, Research Disclosure , December 1978, Item No. 17029 and Research Disclosure , June 1978, Item No. 17643.
- Tabular grain photosensitive silver halide is also useful, as described in, for example, U.S. Patent No. 4,435,499.
- the photographic silver halide can be unwashed or washed, chemically sensitized, protected against the formation of fog, and stabilized against the loss of sensitivity during keeping as described in the above Research Disclosure publications.
- the silver halides can be prepared in situ as described in, for example, U.S. Patent No. 4,457,075, or prepared ex situ by methods known in the photographic art.
- the photothermographic element typically comprises an oxidation-reduction image forming combination that contains an organic silver salt oxidizing agent, preferably a silver salt of a long chain fatty acid.
- organic silver salts are resistant to darkening upon illumination.
- Preferred organic silver salt oxidizing agents are silver salts of long chain fatty acids containing 10 to 30 carbon atoms. Examples of useful organic silver salt oxidizing agents are silver behenate, silver stearate, silver oleate, silver laurate, silver hydroxystearate, silver caprate, silver myristate, and silver palmitate. Combinations of organic silver salt oxidizing agents are also useful. Examples of useful organic silver salt oxidizing agents that are not organic silver salts of fatty acids are silver benzoate and silver benzotriazole.
- the optimum concentration of organic silver salt oxidizing agent in the photothermographic element will vary depending upon the desired image, particular organic silver salt oxidizing agent, particular reducing agent and particular photothermographic element.
- a preferred concentration of organic silver salt oxidizing agent is within the range of 0.1 to 100 moles of organic silver salt oxidizing agent per mole of silver halide in the element.
- the total concentration of organic silver salt oxidizing agents is preferably within the described concentration range.
- reducing agents are useful in the photothermographic element.
- useful reducing agents in the image-forming combination include substituted phenols and naphthols, such as bis-beta-naphthols; polyhydroxybenzenes, such as hydroquinones, pyrogallols and catechols; aminophenols, such as 2,4-diaminophenols and methylaminophenols; ascorbic acid reducing agents, such as ascorbic acid, ascorbic acid ketals and other ascorbic acid derivatives; hydroxylamine reducing agents; 3-pyrazolidone reducing agents, such as 1-phenyl-3-pyrazolidone and 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone; and sulfonamidophenols and other organic reducing agents known to be useful in photothermographic elements, such as described in U.S. Patent 3,933,508, U.S. Patent 3,801,321 and Research Disclosure , June 1978, Item No. 17029. Combinations of organic acids and
- Preferred organic reducing agents in the photothermographic element are sulfonamidophenol reducing agents, such as described in U.S. Patent 3,801,321.
- useful sulfonamidophenol reducing agents are 2,6-dichloro-4-benzene- sulfonamidophenol; benzenesulfonamidophenol; and 2,6-dibromo-4-benzenesulfonamidophenol, and combinations thereof.
- An optimum concentration of organic reducing agent in the photothermographic element varies depending upon such factors as the particular photothermographic element, desired image, processing conditions, the particular organic silver salt and the particular oxidizing agent.
- the photothermographic element preferably comprises a toning agent, also known as an activator-toner or toner-accelerator.
- a toning agent also known as an activator-toner or toner-accelerator.
- Combinations of toning agents are also useful in the photothermographic element. Examples of useful toning agents and toning agent combinations are described in, for example, Research Disclosure , June 1978, Item No. 17029 and U.S. Patent No. 4,123,282.
- useful toning agents include, for example, phthalimide, N-hydroxyphthalimide, N-potassium-phthalimide, succinimide, N-hydroxy-1,8-naphthalimide, phthalazine, 1-(2H)-phthalazinone and 2-acetylphthalazinone.
- Post-processing image stabilizers and latent image keeping stabilizers are useful in the photothermographic element. Any of the stabilizers known in the photothermographic art are useful for the described photothermographic element. Illustrative examples of useful stabilizers include photolytically active stabilizers and stabilizer precursors as described in, for example, U.S. Patent 4,459,350. Other examples of useful stabilizers include azole thioethers and blocked azolinethione stabilizer precursors and carbamoyl stabilizer precursors, such as described in U.S. Patent 3,877,940.
- the photothermographic elements as described preferably contain various colloids and polymers alone or in combination as vehicles and binders and in various layers.
- Useful materials are hydrophilic or hydrophobic. They are transparent or translucent and include both naturally occurring substances, such as gelatin, gelatin derivatives, cellulose derivatives, polysaccharides, such as dextran, or gum arabic; and synthetic polymeric substances, such as water-soluble polyvinyl compounds like poly(vinylpyrrolidone) and acrylamide polymers.
- Other synthetic polymeric compounds that are useful include dispersed vinyl compounds such as in latex form and particularly those that increase dimensional stability of photographic elements.
- Effective polymers include water insoluble polymers of acrylates, such as alkylacrylates and methacrylates, acrylic acid, sulfoacrylates, and those that have cross-linking sites.
- Preferred high molecular weight materials and resins include poly(vinyl butyral), cellulose acetate butyrate, poly(methylmethacrylate), poly(vinylpyrrolidone), ethyl cellulose, polystyrene, poly(vinylchloride), chlorinated rubbers, polyisobutylene, butadiene-styrene copolymers, copolymers of vinyl chloride and vinyl acetate, copolymers of vinylidene chloride and vinyl acetate, poly(vinyl alcohol) and polycarbonates.
- Photothermographic elements can contain addenda that are known to aid in formation of a useful image.
- the photothermographic element can contain development modifiers that function as speed increasing compounds, sensitizing dyes, hardeners, antistatic agents, plasticizers and lubricants, coating aids, brighteners, other absorbing and filter dyes, such as described in Research Disclosure , December 1978, Item No. 17643 and Research Disclosure , June 1978, Item No. 17029.
- the photothermographic element can comprise a variety of supports.
- useful supports are poly(vinylacetal) film, polystyrene film, poly(ethyleneterephthalate) film, poly(ethylene naphthalate) film, polycarbonate film, and related films and resinous materials, as well as paper, glass, metal, and other supports that withstand the thermal processing temperatures.
- the layers of the photothermographic element are coated on a support by coating procedures known in the photographic art, including dip coating, air knife coating, curtain coating or extrusion coating using hoppers. If desired, two or more layers are coated simultaneously.
- Spectral sensitizing dyes are useful in the photothermographic element to confer added sensitivity to the element.
- Useful sensitizing dyes are described in, for example, Research Disclosure , June 1978, Item No. 17029 and Research Disclosure , December 1978, Item No. 17643.
- a photothermographic element as described preferably comprises a thermal stabilizer to help stabilize the photothermographic element prior to exposure and processing.
- a thermal stabilizer provides improved stability of the photothermographic element during storage.
- Preferred thermal stabilizers are 2-bromo-2-arylsulfonylacetamides, such as 2-bromo-2-p-tolysulfonylacetamide; 2-(tribromomethyl sulfonyl)benzothiazole; and 6-substituted-2,4-bis(tribromomethyl)-s-triazines, such as 6-methyl or 6-phenyl-2,4-bis(tribromomethyl)-s-triazine.
- a photothermographic element typically has a transparent protective layer comprising a film forming binder, preferable a hydrophilic film forming binder.
- binders include, for example, crosslinked polyvinyl alcohol, gelatin, or poly(silicic acid). Particularly preferred are binders comprising poly(silicic acid) alone or in combination with a water-soluble hydroxyl-containing monomer or polymer as described in the US Patent No. 4,828,971.
- the term "protective layer” is used in this application to mean a transparent, image insensitive layer that can be an overcoat layer, that is a layer that overlies the image sensitive layer(s), or a backing layer, that is a layer that is on the opposite side of the support from the image sensitive layer(s).
- the imaging element can contain an adhesive interlayer between the protective layer and the underlying layer(s).
- the protective layer is not necessarily the outermost layer of the imaging element.
- the protective layer can contain an electrically conductive layer having a surface resistivity of less than 5 x 10 11 ohms/square.
- electrically conductive overcoat layers are described in US Patent No. 5,547,821.
- a photothermographic imaging element generally includes at least one transparent protective layer containing matte particles.
- Either organic or inorganic matte particles can be used.
- organic matte particles are often in the form of beads, of polymers such as polymeric esters of acrylic and methacrylic acid, e.g., poly(methylmethacrylate), styrene polymers and copolymers.
- inorganic matte particles are of glass, silicon dioxide, titanium dioxide, magnesium oxide, aluminum oxide, barium sulfate, and calcium carbonate. Matte particles and the way they are used are further described in U.S. Patent Nos. 3,411,907, 3,754,924, 4,855,219, 5,279,934, 5,288,598, 5,378,577, 5,750,328 and 5,563,226.
- the protective layer should be transparent and should not adversely affect sensitometric characteristics of the photothermographic element such as minimum density, maximum density and photographic speed.
- Useful protective layers include those comprised of poly(silicic acid) and a water-soluble hydroxyl containing monomer or polymer that is compatible with poly(silicic acid) as described in U.S. Patent 4,741,992 and 4,828,971. A combination of poly(silicic acid) and poly(vinyl alcohol) is particularly useful.
- Other useful protective layers include those formed from polymethylmethacrylate, acrylamide polymers, cellulose acetate, crosslinked polyvinyl alcohol, terpolymers of acrylonitrile, vinylidene chloride, and 2-(methacryloyloxy)ethyl-trimethylammonium methosulfate, crosslinked gelatin, polyesters and polyurethanes.
- the photothermographic elements are exposed by means of various forms of energy, including those to which the photographic silver halides are sensitive, e.g., include ultraviolet, visible and infrared regions of the electromagnetic spectrum as well as electron beam and beta radiation, gamma ray, x-ray, alpha particle, neutron radiation and other forms of corpuscular wave-like radiant energy in either non-coherent (random phase) or coherent (in phase) forms produced by lasers. Exposures are monochromatic, orthochromatic, or panchromatic depending upon the spectral sensitization of the photographic silver halide. Imagewise exposure is preferably for a time and intensity sufficient to produce a developable latent image in the photothermographic element.
- the resulting latent image is developed merely by overall heating the element to thermal processing temperature.
- This overall heating merely involves heating the photothermographic element to a temperature within the range of 90°C. to 180°C. until a developed image is formed, such as within 0.5 to 60 seconds.
- a preferred thermal processing temperature is within the range of 100°C. to 140°C.
- Heating means known in the photothermographic imaging arts are useful for providing the desired processing temperature for the exposed photothermographic element.
- the heating means is, for example, a simple hot plate, iron, roller, heated drum, microwave heating means, or heated air.
- Thermal processing is preferably carried out under ambient conditions of pressure and humidity. Conditions outside of normal atmospheric pressure and humidity are useful.
- the components of the photothermographic element can be in any location in the element that provides the desired image. If desired, one or more of the components can be in one or more layers of the element. For example, in some cases, it is desirable to include certain percentages of the reducing agent, toner, stabilizer and/or other addenda in the overcoat layer over the photothermographic imaging layer of the element. This, in some cases, reduces migration of certain addenda in the layers of the element.
- the components of the imaging combination be "in association" with each other in order to produce the desired image.
- association herein means that in the photothermographic element the photographic silver halide and the image forming combination are in a location with respect to each other that enables the desired processing and forms a useful image.
- the other examples of the present invention can be made in an analogous fashion, from the appropriately substituted phthalonitrile and a multi-valent metal salt.
- emulsion Component Grams Silver Behenate dispersion (contains 26.4% by weight silver behenate in 8.5% by weight methyl ethyl ketone (MEK) / toluene (80:20) solution of polyvinylbutyral (ButvarTM B-76 available from Monsanto Co., USA) 877.8 Silver bromide (silver bromide emulsion contains 45.9 g Ag in 9% by weight MEK solution of Butvar B-76) containing sodium Iodide (NaI) (0.1% by weight) 127.1 Sensitizing dye (0.17% by weight solution in MEK / 2-ethoxy ethanol (90:10)) 64.4 Succinimide (toner) 3.5 phthalimide (toner) 14.0 SF-96 (10% by weight SF-96 in MEK.
- SF-96TM a silicone available from General Electric Co., U.S.A.
- Palmitic acid (10% by weight in 10.5% by weight MEK solution of Butvar B-76) 30.6 N (4-hydroxyphenyl)benzenesulfonamide (12% by weight in 10.5% by weight MEK solution of Butvar B-76) 350.0 Butvar B-76 (10.5% by weight in MEK / Toluene 65:35) 105.2
- the resulting photothermographic solution silver halide composition was coated at a wet laydown of 68.6 grams/m 2 on a blue (0.16 overall visual density) poly-(ethyleneterephthalate) film support, containing 250 ppm of dye C-1.
- composition (B) Component Grams Distilled Water 226.4 Polyvinyl Alcohol (PVA) (6.2% by weight in distilled water) (binder) 443.0 Tetraethyl Orthosilicate (35.4% by weight in methanol / water (53:47)) (hardener) 251.6 p-Toluene Sulfonic Acid (1N solution in distilled water) 3.1 para-isononylphenoxy polyglycidol, Olin 10GTM available from Olin Corp., USA (10% by weight in distilled water) 10.0 Silica (1.5 micron) (matting agent) 3.0
- the resulting overcoat formulation (B) was coated at a wet laydown of 40.4 grams/m 2 . The coating was permitted to dry.
- An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation: Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight in Acetone) (Antihalation dye) 12.5 Butvar B-76 (6.0% by weight in MEK / Toluene (80:20)) (binder) 191.4 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3 The resulting composition was coated at a wet laydown of 50.8 grams/m 2 on a poly(ethyleneterephthalate) film support. The coating was permitted to dry and was then overcoated with the same overcoat composition (B) in Example 1. The resulting pelloid overcoat formulation was coated at a wet laydown of 40.4 grams/m 2 . The coating was permitted to dry.
- An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation: Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight 17.5 Butvar B-76 (6.2% by weight in MEK / Toluene80:20) (binder) 186.4 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3
- the resulting composition was coated at a wet laydown of 50.8 grams/m 2 on a poly(ethyleneterephthalate) film support.
- the coating was permitted to dry and was then overcoated with the same overcoat composition (B) in Example 1.
- the resulting pelloid overcoat formulation was coated at a wet laydown of 40.4 grams/m 2 . The coating was permitted to dry.
- An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation: Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight in acetone) (Antihalation dye) 21.2 Butvar B-76 (6.3% by weight in MEK / Toluene 80:20) (binder) 182.7 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3 The resulting composition was coated at a wet laydown of 50.8 grams/m 2 on a poly(ethyleneterephthalate) film support. The coating was permitted to dry and was then overcoated with the same overcoat composition (B) in Example 1. The resulting pelloid overcoat formulation was coated at a wet laydown of 40.4 grams/m 2 . The coating was permitted to dry.
- the dyes of the invention may also be coated as solid particle dispersions in a hydrophilic layer.
- Ingredient Amount Dye 4 1.0 g 0.437% aqueous TX 200 23.0 g 1.8 mm Zirbeads 60 cc
- the dye and TX 200 (octylphenoxyethylene oxide sulfonate, commercially available from Rohm and Haas) solution were combined in a clean, dry 120 cc amber bottle and the pH was recorded. The pH was adjusted to ⁇ 5 if needed, and the Zirbeads (zirconia beads)were then added, the bottle was sealed and milled on a SWECO vibratory mill for 5 days. Filter off Zirbeads to provide a dye slurry used in the next step.
- TX 200 octylphenoxyethylene oxide sulfonate, commercially available from Rohm and Haas
- the gel was melted at a temperature of 45°C or greater, the Olin 10G was added to this, followed by the dye slurry, and finally water in the amounts shown in the table.
- the final pH of the melt was recorded, and they were chill set for future coatings.
- the hardener solution was added to the melt just prior to coating.
- This solid particle dispersion (SPD) may be coated on the backside of the support as a pelloid layer, between the support and the emulsion, between the support and an interlayer, or between a polymeric underlayer and the emulsion.
- Ingredient Amount Dye slurry 13.18 g gelatin (G9461, 12.5%) 18.0 g Olin 10G 1.35 g water 51.21 g hardener solution 1.25 g in 5 g water 6.25 g
- the examples were exposed using a 683 nm 30 mw laser and processed at 123°C for 5 sec to produce a developed silver image.
- the developed silver image had a maximum density of 3.5 with a relative Log E speed of 1.00 measured at a density of 1.0 above D min .
- the SMPTE patterns from the exposed and developed examples were visually evaluated on a light box and graded according to their sharpness and overall appearance:
- the examples of the present invention provide sharp images without increasing the visual density significantly.
Description
- This invention relates to a photothermographic imaging element suited for use with a red or near-infrared laser. More specifically, this invention relates to a photothermographic imaging element comprising an antihalation dye.
- There is often desired for photosensitive emulsion layers or other layers of silver halide light-sensitive materials, colored layers that absorb light of specific wavelengths in order to provide filtration of unwanted wavelengths of light, absorb scattered light within a layer, or provide halation protection. These coloring layers can be located above the photosensitive layer, within the photosensitive layer, between the photosensitive layer and the support or on the opposite side of the support. When the colored layer is located in the latter three areas as described above, it is able to prevent unwanted back reflection of the light, thus providing halation protection to the photosensitive material.
- Antihalation is particularly important when a film is exposed using a laser because of the high intensity of light emitted by the laser necessitating high levels of dye to be used in order to provide adequate absorption of light. This can lead to undesirable coloration of the photographic element, particularly with regard to a photothermographic system where wet processing steps are unavailable to provide washout of the filtration dye.
- The problem to be solved by this invention is to provides a photothermographic element containing a dye that is useful for absorbing laser light in the red and near-infrared regions (i.e. in a wavelength range of 660 to 800 nm), that has very little extraneous absorption in unwanted areas of the visible spectrum, that is stable with time and that functions as an antihalation dye.
- This invention comprises a photothermographic imaging element comprising a support, a photothermographic imaging layer and at least one non-imaging layer positioned above the imaging layer, between the imaging layer and the support or on the side of the support opposite the imaging layer, wherein the non-imaging layer contains a dye of structure I: wherein
- M is a multi-valent metal atom;
- R1, R4, R5, R8, R9, R12,R13, R16 independently represent a hydrogen atom, or a substituted or unsubstituted, branched or unbranched alkyl group;
- R2, R3, R6, R7, R10, R11, R14, R15 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted, branched or unbranched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group; or one or more of the adjacent pairs R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15 and R15 and R16 taken together may represent the atoms necessary to form a substituted or unsubstituted aromatic or heteroaromatic ring and wherein the dye has a peak absorption between 660 and 800 nm.
-
- A particular advantage of the dyes utilized in the preparation of a photothermographic element in accordance with the invention is the solubility of the dyes which allows coating of the antihalation element in a variety of polymeric binders. Another advantage is the excellent absorption of these dyes at the desired wavelengths as evidenced by their state-of-the-art properties as antihalation dyes in a photothermographic element. Another advantage is the stability of these dyes with time, both under hydrolytic and photolytic conditions.
-
- M is a multi-valent metal atom;
- R1, R4, R5, R8, R9, R12,R13, R16 independently represent a hydrogen atom, or a substituted or unsubstituted, branched or unbranched alkyl group;
- R2, R3, R6, R7, R10, R11, R14, R15 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted, branched or unbranched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group; or one or more of the adjacent pairs R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15 and R15 and R16 taken together may represent the atoms necessary to form a substituted or unsubstituted aromatic or heteroaromatic ring, and wherein the dye has a peak absorption between 660 and 800 nm.
-
- M is preferably a multi-valent metal atom selected from the group consisting of: Mg, Ca, Sr, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, B, Al, Sn, Pb, Mo, Pd and Pt. Particularly preferred are Mg, Ni, Zn, and Cu.
- Alkyl and alkoxy groups preferably contain 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Alkyl groups include, for example, methyl, ethyl, propyl, isopropyl, butyl sec. butyl, tert. butyl, heptyl or decyl. Alkoxy groups include, for example, methoxy, ethoxy, propoxy, or tert. butoxy. Aryl and aryloxy groups preferably contain 6 to 12 carbon atoms, more preferably 5 to 8 carbon atoms. Aryl groups that can be used include, for example, phenyl, tolyl, naphthyl, 2,4-dimethylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 4-ethoxyphenyl, or 4-isopropoxyphenyl. Aryloxy groups, include, for example, phenoxy, substituted phenoxy such as 2-methylphenoxy, 4-methylphenoxy, 2-ethylphenoxy, 4-ethylphenoxy, 4-eumylphenoxy, 4-isopropylphenoxy, 4-tert-butyl-phenoxy, 2-chlorophenoxy, or 4,-chlorophenoxy.
- Aromatic ring structures include, for example phenyl, 1,2-naphthyl, 2,3-naphthyl, or phenanthryl. Heteroaromatic rings include, for example, pyridine, pyrazine, pyridazine and pyrimidine.
- When reference in this application is made to a particular moiety it is to be understood that the moiety may itself be unsubstituted or substituted with one or more substituents (up to the maximum possible number). For example, "alkyl group" refers to a substituted or unsubstituted alkyl, while "benzene group" refers to a substituted or unsubstituted benzene (with up to six substituents). Generally, unless otherwise specifically stated, substituent groups usable on molecules herein include any groups, whether substituted or unsubstituted, which do not destroy properties necessary for the photothermographic utility. Examples of substituents on any of the mentioned groups can include known substituents, such as: halogen, for example, chloro, fluoro, bromo, iodo; alkoxy, particularly those "lower alkyl" (that is, with 1 to 6 carbon atoms, for example, methoxy, ethoxy; substituted or unsubstituted alkyl, particularly lower alkyl (for example, methyl, trifluoromethyl); thioalkyl (for example, methylthio or ethylthio), particularly either of those with 1 to 6 carbon atoms; substituted and unsubstituted aryl, particularly those having from 6 to 20 carbon atoms (for example, phenyl); and substituted or unsubstituted heteroaryl, particularly those having a 5 or 6-membered ring containing 1 to 3 heteroatoms selected from N, O, or S (for example, pyridyl, thienyl, furyl, pyrrolyl); acid or acid salt groups such as any of those described below; and others known in the art. Alkyl substituents may specifically include "lower alkyl" (that is, having 1-6 carbon atoms), for example, methyl, or ethyl. Further, with regard to any alkyl group or alkylene group, it will be understood that these can be branched or unbranched and include ring structures.
- Dyes of structure I are known and some are commercially available. The dyes can be made by the methods outlined in The Phthalocyanines, Vol. I and II, Moser, F.H. and Thomas, A.L., CRC Press, Boca Raton, Florida, 1983 or by the method of Wöhrle, D.; Schnurpfeil, G.; Knothe, G. Dyes and Pigments 1992, 18, 91.
-
- The photothermographic element of this invention typically comprises a support, a photothermographic layer, a backing layer, an overcoat layer and various interlayers, such as, subbing layers, and filter layers. In preferred embodiments of the invention, the dye is incorporated into a backing layer (e.g. a pelloid layer) or a layer between the support and the photothermographic layer.
- The layers of a photothermographic element are generally prepared from a solution containing a binder and other components to give the layer the desired properties in an appropriate solvent. In accordance with this invention, an antihalation dye is dissolved in a solvent together with a binder for incorporation into the desired layer of the photothermographic element. The binder can be a hydrophobic binder preferably polymethyl methacrylate, polystyrene, polyvinyl butyral, or cellulose acetate butyrate. Preferred solvents for use with a hydrophobic binder are aromatic solvents, such as, toluene or xylene, ketone solvents, such as, methyl ethyl ketone, and methyl isobutyl ketone, tetrahydrofuran, ethyl acetate, chlorinated solvents such as dichloromethane. The solvent can contain water, if desired. In other embodiments of the invention the binder is a hydrophilic binder, preferably gelatin. The hydrophilic binder is generally dissolved in an aqueous medium for incorporation into the desired layer of the photothermographic element.
- The dye is preferably used in an amount of 10 to 10,000 ppm (parts per million), more preferably 10 to 1,000 ppm, based on the amount of binder in the layer.
- Typical photothermographic elements of this invention comprise at least one photothermographic layer containing in reactive association in a binder, preferably a binder comprising hydroxyl groups, (a) photographic silver halide prepared in situ and/or ex situ, (b) an image-forming combination comprising (i) an organic silver salt oxidizing agent, preferably a silver salt of a long chain fatty acid, such as silver behenate, with (ii) a reducing agent for the organic silver salt oxidizing agent, preferably a phenolic reducing agent, and (c) an optional toning agent. References describing such imaging elements include, for example, U.S. Patents 3,457,075; 4,459,350; 4,264,725 and 4,741,992 and Research Disclosure, June 1978, Item No. 17029.
- In the photothermographic material it is believed that the latent image silver from the silver halide acts as a catalyst for the described image-forming combination upon processing. A preferred concentration of photographic silver halide is within the range of 0.01 to 10 moles of photographic silver halide per mole of silver behenate in the photothermographic material. Other photosensitive silver salts are useful in combination with the photographic silver halide if desired. Preferred photographic silver halides are silver chloride, silver bromide, silver bromochloride, silver bromoiodide, silver chlorobromoiodide, and mixtures of these silver halides. Very fine grain photographic silver halide is especially useful. The photographic silver halide can be prepared by any of the known procedures in the photographic art. Such procedures for forming photographic silver halides and forms of photographic silver halides are described in, for example, Research Disclosure, December 1978, Item No. 17029 and Research Disclosure, June 1978, Item No. 17643. Tabular grain photosensitive silver halide is also useful, as described in, for example, U.S. Patent No. 4,435,499. The photographic silver halide can be unwashed or washed, chemically sensitized, protected against the formation of fog, and stabilized against the loss of sensitivity during keeping as described in the above Research Disclosure publications. The silver halides can be prepared in situ as described in, for example, U.S. Patent No. 4,457,075, or prepared ex situ by methods known in the photographic art.
- The photothermographic element typically comprises an oxidation-reduction image forming combination that contains an organic silver salt oxidizing agent, preferably a silver salt of a long chain fatty acid. Such organic silver salts are resistant to darkening upon illumination. Preferred organic silver salt oxidizing agents are silver salts of long chain fatty acids containing 10 to 30 carbon atoms. Examples of useful organic silver salt oxidizing agents are silver behenate, silver stearate, silver oleate, silver laurate, silver hydroxystearate, silver caprate, silver myristate, and silver palmitate. Combinations of organic silver salt oxidizing agents are also useful. Examples of useful organic silver salt oxidizing agents that are not organic silver salts of fatty acids are silver benzoate and silver benzotriazole.
- The optimum concentration of organic silver salt oxidizing agent in the photothermographic element will vary depending upon the desired image, particular organic silver salt oxidizing agent, particular reducing agent and particular photothermographic element. A preferred concentration of organic silver salt oxidizing agent is within the range of 0.1 to 100 moles of organic silver salt oxidizing agent per mole of silver halide in the element. When combinations of organic silver salt oxidizing agents are present, the total concentration of organic silver salt oxidizing agents is preferably within the described concentration range.
- A variety of reducing agents are useful in the photothermographic element. Examples of useful reducing agents in the image-forming combination include substituted phenols and naphthols, such as bis-beta-naphthols; polyhydroxybenzenes, such as hydroquinones, pyrogallols and catechols; aminophenols, such as 2,4-diaminophenols and methylaminophenols; ascorbic acid reducing agents, such as ascorbic acid, ascorbic acid ketals and other ascorbic acid derivatives; hydroxylamine reducing agents; 3-pyrazolidone reducing agents, such as 1-phenyl-3-pyrazolidone and 4-methyl-4-hydroxymethyl-1-phenyl-3-pyrazolidone; and sulfonamidophenols and other organic reducing agents known to be useful in photothermographic elements, such as described in U.S. Patent 3,933,508, U.S. Patent 3,801,321 and Research Disclosure, June 1978, Item No. 17029. Combinations of organic reducing agents are also useful in the photothermographic element.
- Preferred organic reducing agents in the photothermographic element are sulfonamidophenol reducing agents, such as described in U.S. Patent 3,801,321. Examples of useful sulfonamidophenol reducing agents are 2,6-dichloro-4-benzene- sulfonamidophenol; benzenesulfonamidophenol; and 2,6-dibromo-4-benzenesulfonamidophenol, and combinations thereof.
- An optimum concentration of organic reducing agent in the photothermographic element varies depending upon such factors as the particular photothermographic element, desired image, processing conditions, the particular organic silver salt and the particular oxidizing agent.
- The photothermographic element preferably comprises a toning agent, also known as an activator-toner or toner-accelerator. Combinations of toning agents are also useful in the photothermographic element. Examples of useful toning agents and toning agent combinations are described in, for example, Research Disclosure, June 1978, Item No. 17029 and U.S. Patent No. 4,123,282. Examples of useful toning agents include, for example, phthalimide, N-hydroxyphthalimide, N-potassium-phthalimide, succinimide, N-hydroxy-1,8-naphthalimide, phthalazine, 1-(2H)-phthalazinone and 2-acetylphthalazinone.
- Post-processing image stabilizers and latent image keeping stabilizers are useful in the photothermographic element. Any of the stabilizers known in the photothermographic art are useful for the described photothermographic element. Illustrative examples of useful stabilizers include photolytically active stabilizers and stabilizer precursors as described in, for example, U.S. Patent 4,459,350. Other examples of useful stabilizers include azole thioethers and blocked azolinethione stabilizer precursors and carbamoyl stabilizer precursors, such as described in U.S. Patent 3,877,940.
- The photothermographic elements as described preferably contain various colloids and polymers alone or in combination as vehicles and binders and in various layers. Useful materials are hydrophilic or hydrophobic. They are transparent or translucent and include both naturally occurring substances, such as gelatin, gelatin derivatives, cellulose derivatives, polysaccharides, such as dextran, or gum arabic; and synthetic polymeric substances, such as water-soluble polyvinyl compounds like poly(vinylpyrrolidone) and acrylamide polymers. Other synthetic polymeric compounds that are useful include dispersed vinyl compounds such as in latex form and particularly those that increase dimensional stability of photographic elements. Effective polymers include water insoluble polymers of acrylates, such as alkylacrylates and methacrylates, acrylic acid, sulfoacrylates, and those that have cross-linking sites. Preferred high molecular weight materials and resins include poly(vinyl butyral), cellulose acetate butyrate, poly(methylmethacrylate), poly(vinylpyrrolidone), ethyl cellulose, polystyrene, poly(vinylchloride), chlorinated rubbers, polyisobutylene, butadiene-styrene copolymers, copolymers of vinyl chloride and vinyl acetate, copolymers of vinylidene chloride and vinyl acetate, poly(vinyl alcohol) and polycarbonates.
- Photothermographic elements can contain addenda that are known to aid in formation of a useful image. The photothermographic element can contain development modifiers that function as speed increasing compounds, sensitizing dyes, hardeners, antistatic agents, plasticizers and lubricants, coating aids, brighteners, other absorbing and filter dyes, such as described in Research Disclosure, December 1978, Item No. 17643 and Research Disclosure, June 1978, Item No. 17029.
- The photothermographic element can comprise a variety of supports. Examples of useful supports are poly(vinylacetal) film, polystyrene film, poly(ethyleneterephthalate) film, poly(ethylene naphthalate) film, polycarbonate film, and related films and resinous materials, as well as paper, glass, metal, and other supports that withstand the thermal processing temperatures.
- The layers of the photothermographic element are coated on a support by coating procedures known in the photographic art, including dip coating, air knife coating, curtain coating or extrusion coating using hoppers. If desired, two or more layers are coated simultaneously.
- Spectral sensitizing dyes are useful in the photothermographic element to confer added sensitivity to the element. Useful sensitizing dyes are described in, for example, Research Disclosure, June 1978, Item No. 17029 and Research Disclosure, December 1978, Item No. 17643.
- A photothermographic element as described preferably comprises a thermal stabilizer to help stabilize the photothermographic element prior to exposure and processing. Such a thermal stabilizer provides improved stability of the photothermographic element during storage. Preferred thermal stabilizers are 2-bromo-2-arylsulfonylacetamides, such as 2-bromo-2-p-tolysulfonylacetamide; 2-(tribromomethyl sulfonyl)benzothiazole; and 6-substituted-2,4-bis(tribromomethyl)-s-triazines, such as 6-methyl or 6-phenyl-2,4-bis(tribromomethyl)-s-triazine.
- A photothermographic element typically has a transparent protective layer comprising a film forming binder, preferable a hydrophilic film forming binder. Such binders include, for example, crosslinked polyvinyl alcohol, gelatin, or poly(silicic acid). Particularly preferred are binders comprising poly(silicic acid) alone or in combination with a water-soluble hydroxyl-containing monomer or polymer as described in the US Patent No. 4,828,971.
- The term "protective layer" is used in this application to mean a transparent, image insensitive layer that can be an overcoat layer, that is a layer that overlies the image sensitive layer(s), or a backing layer, that is a layer that is on the opposite side of the support from the image sensitive layer(s). The imaging element can contain an adhesive interlayer between the protective layer and the underlying layer(s). The protective layer is not necessarily the outermost layer of the imaging element.
- The protective layer can contain an electrically conductive layer having a surface resistivity of less than 5 x 1011 ohms/square. Such electrically conductive overcoat layers are described in US Patent No. 5,547,821.
- A photothermographic imaging element generally includes at least one transparent protective layer containing matte particles. Either organic or inorganic matte particles can be used. Examples of organic matte particles are often in the form of beads, of polymers such as polymeric esters of acrylic and methacrylic acid, e.g., poly(methylmethacrylate), styrene polymers and copolymers. Examples of inorganic matte particles are of glass, silicon dioxide, titanium dioxide, magnesium oxide, aluminum oxide, barium sulfate, and calcium carbonate. Matte particles and the way they are used are further described in U.S. Patent Nos. 3,411,907, 3,754,924, 4,855,219, 5,279,934, 5,288,598, 5,378,577, 5,750,328 and 5,563,226.
- A wide variety of materials can be used to prepare the protective layer that is compatible with the requirements of photothermographic elements. The protective layer should be transparent and should not adversely affect sensitometric characteristics of the photothermographic element such as minimum density, maximum density and photographic speed. Useful protective layers include those comprised of poly(silicic acid) and a water-soluble hydroxyl containing monomer or polymer that is compatible with poly(silicic acid) as described in U.S. Patent 4,741,992 and 4,828,971. A combination of poly(silicic acid) and poly(vinyl alcohol) is particularly useful. Other useful protective layers include those formed from polymethylmethacrylate, acrylamide polymers, cellulose acetate, crosslinked polyvinyl alcohol, terpolymers of acrylonitrile, vinylidene chloride, and 2-(methacryloyloxy)ethyl-trimethylammonium methosulfate, crosslinked gelatin, polyesters and polyurethanes.
- Particularly preferred protective layers are described in above-mentioned U.S. Patent Nos. 5,310,640 and 5,547,821
- The photothermographic elements are exposed by means of various forms of energy, including those to which the photographic silver halides are sensitive, e.g., include ultraviolet, visible and infrared regions of the electromagnetic spectrum as well as electron beam and beta radiation, gamma ray, x-ray, alpha particle, neutron radiation and other forms of corpuscular wave-like radiant energy in either non-coherent (random phase) or coherent (in phase) forms produced by lasers. Exposures are monochromatic, orthochromatic, or panchromatic depending upon the spectral sensitization of the photographic silver halide. Imagewise exposure is preferably for a time and intensity sufficient to produce a developable latent image in the photothermographic element.
- After imagewise exposure of the photothermographic element, the resulting latent image is developed merely by overall heating the element to thermal processing temperature. This overall heating merely involves heating the photothermographic element to a temperature within the range of 90°C. to 180°C. until a developed image is formed, such as within 0.5 to 60 seconds. By increasing or decreasing the thermal processing temperature a shorter or longer time of processing is useful. A preferred thermal processing temperature is within the range of 100°C. to 140°C.
- Heating means known in the photothermographic imaging arts are useful for providing the desired processing temperature for the exposed photothermographic element. The heating means is, for example, a simple hot plate, iron, roller, heated drum, microwave heating means, or heated air.
- Thermal processing is preferably carried out under ambient conditions of pressure and humidity. Conditions outside of normal atmospheric pressure and humidity are useful.
- The components of the photothermographic element can be in any location in the element that provides the desired image. If desired, one or more of the components can be in one or more layers of the element. For example, in some cases, it is desirable to include certain percentages of the reducing agent, toner, stabilizer and/or other addenda in the overcoat layer over the photothermographic imaging layer of the element. This, in some cases, reduces migration of certain addenda in the layers of the element.
- It is necessary that the components of the imaging combination be "in association" with each other in order to produce the desired image. The term "in association" herein means that in the photothermographic element the photographic silver halide and the image forming combination are in a location with respect to each other that enables the desired processing and forms a useful image.
- The following examples illustrate the preparation of dyes of structure I and their evaluation in photothermographic elements.
- A mixture of 25 parts of 4-tert-butylphthalonitrile, and 3.1 parts of magnesium chloride in 220 parts of n-pentanol was treated with 22.7 parts of 1,8-diazabicyclo[5.4.0]undec-7-ene, and subsequently heated to reflux for 18 h. The mixture was cooled, poured into 2500 parts of a 4:1 methanol/water mixture, stirred for 1 h, and then the dark precipitate was filtered and washed well with 1000 parts of methanol. Drying under vacuum provided 21.5 parts of dye 4 suitable for use in the present invention, λmax- 672 nm (acetone), ε = 26.9 x 104.
- A mixture of 3 parts of 4-tert-butylphthalonitrile, and 0.7 parts of zinc chloride in 25 parts of n-pentanol was treated with 2.5 parts of 1,8-diazabicyclo[5.4.0]undec-7-ene, and heated to reflux for 18 h. After cooling, the mixture was poured into 250 parts of a 4:1 methanol/water mixture, and stirred for 1 h. The dark precipitate was filtered, washed with an additional 150 parts of methanol, and dried under vacuum to provide 2.9 parts of dye 6, λmax-671 nm (acetone), ε = 28.8 x 104.
- A mixture of 5 parts of 4-tert-butylphthalonitrile, and 0.9 parts of copper(II) chloride was treated with 4.5 parts of 1,8-diazabicyclo[5.4.0]undec-7-ene, and heated to reflux for 18 h. After cooling, the mixture was poured into 250 parts of a 4:1 methanol/water mixture, and stirred for 1 h. The dark precipitate was 521 filtered, washed with an additional 150 parts of methanol, and dried under vacuum to provide 4.5 parts of dye 2, λmax-677 nm (toluene), ε = 25.8 x 104.
- The other examples of the present invention can be made in an analogous fashion, from the appropriately substituted phthalonitrile and a multi-valent metal salt.
- The following components were mixed to form an emulsion (A):
Component Grams Silver Behenate dispersion (contains 26.4% by weight silver behenate in 8.5% by weight methyl ethyl ketone (MEK) / toluene (80:20) solution of polyvinylbutyral (Butvar™ B-76 available from Monsanto Co., USA) 877.8 Silver bromide (silver bromide emulsion contains 45.9 g Ag in 9% by weight MEK solution of Butvar B-76) containing sodium Iodide (NaI) (0.1% by weight) 127.1 Sensitizing dye (0.17% by weight solution in MEK / 2-ethoxy ethanol (90:10)) 64.4 Succinimide (toner) 3.5 phthalimide (toner) 14.0 SF-96 (10% by weight SF-96 in MEK. SF-96™ a silicone available from General Electric Co., U.S.A.) 1.6 2-Bromo-2-[(4-methylphenyl)sulfonyl] acetamide 2.6 Naphthyl triazine (print-up stabilizer) 0.6 Palmitic acid (10% by weight in 10.5% by weight MEK solution of Butvar B-76) 30.6 N (4-hydroxyphenyl)benzenesulfonamide (12% by weight in 10.5% by weight MEK solution of Butvar B-76) 350.0 Butvar B-76 (10.5% by weight in MEK / Toluene 65:35) 105.2 Component Grams Distilled Water 226.4 Polyvinyl Alcohol (PVA) (6.2% by weight in distilled water) (binder) 443.0 Tetraethyl Orthosilicate (35.4% by weight in methanol / water (53:47)) (hardener) 251.6 p-Toluene Sulfonic Acid (1N solution in distilled water) 3.1 para-isononylphenoxy polyglycidol, Olin 10G™ available from Olin Corp., USA (10% by weight in distilled water) 10.0 Silica (1.5 micron) (matting agent) 3.0 - An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation:
Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight in Acetone) (Antihalation dye) 12.5 Butvar B-76 (6.0% by weight in MEK / Toluene (80:20)) (binder) 191.4 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3 - An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation:
Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight 17.5 Butvar B-76 (6.2% by weight in MEK / Toluene80:20) (binder) 186.4 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3 - An emulsion (A) was prepared as described in Example 4, coated on clear support, except that on the pelloid side of the film an Antihalation dye was coated with the following formulation:
Component Grams Phthalocyanine Dye #4 (Table 1) (2.3% by weight in acetone) (Antihalation dye) 21.2 Butvar B-76 (6.3% by weight in MEK / Toluene 80:20) (binder) 182.7 SF-96 (10% by weight SF-96 in MEK.) (surfactant) 0.3 - The dyes of the invention may also be coated as solid particle dispersions in a hydrophilic layer.
Ingredient Amount Dye 4 1.0 g 0.437% aqueous TX 200 23.0 g 1.8 mm Zirbeads 60 cc - The dye and TX 200 (octylphenoxyethylene oxide sulfonate, commercially available from Rohm and Haas) solution were combined in a clean, dry 120 cc amber bottle and the pH was recorded. The pH was adjusted to <5 if needed, and the Zirbeads (zirconia beads)were then added, the bottle was sealed and milled on a SWECO vibratory mill for 5 days. Filter off Zirbeads to provide a dye slurry used in the next step.
- The gel was melted at a temperature of 45°C or greater, the Olin 10G was added to this, followed by the dye slurry, and finally water in the amounts shown in the table. The final pH of the melt was recorded, and they were chill set for future coatings. The hardener solution was added to the melt just prior to coating. This solid particle dispersion (SPD) may be coated on the backside of the support as a pelloid layer, between the support and the emulsion, between the support and an interlayer, or between a polymeric underlayer and the emulsion.
Ingredient Amount Dye slurry 13.18 g gelatin (G9461, 12.5%) 18.0 g Olin 10G 1.35 g water 51.21 g hardener solution 1.25 g in 5 g water 6.25 g - The examples were exposed using a 683 nm 30 mw laser and processed at 123°C for 5 sec to produce a developed silver image. The developed silver image had a maximum density of 3.5 with a relative Log E speed of 1.00 measured at a density of 1.0 above Dmin.
- The SMPTE patterns from the exposed and developed examples were visually evaluated on a light box and graded according to their sharpness and overall appearance:
- 1- unacceptable- heavy flaring, blurred edges, text unreadable
- 2- marginally acceptable- edges sharp, text blurred
- 3- acceptable- sharp edges, sharp high contrast text. The results are tabulated in Table 2.
-
- As can be readily seen, the examples of the present invention provide sharp images without increasing the visual density significantly.
Example | Visual density (Dmin) | Density @ peak | SMPTE resolution | Remarks |
4 | 0.24 | 0.26 | 1 | comparative |
5 | 0.15 | 1.0 | 2 | invention |
6 | 0.17 | 1.4 | 3 | invention |
7 | 0.20 | 1.7 | 3 | invention |
Claims (9)
- A photothermographic imaging element comprising a support bearing an photothermographic imaging layer and at least one non-imaging layer positioned above the imaging layer, between the imaging layer and the support or on the side of the support opposite the imaging layer, wherein the non-imaging layer contains a dye of structure I: whereinM is a multi-valent metal atom;R1, R4, R5, R8, R9, R12,R13, R16 independently represent a hydrogen atom, or a substituted or unsubstituted, branched or unbranched alkyl group;R2, R3, R6, R7, R10, R11, R14, R15 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted, branched or unbranched alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group; or one or more of the adjacent pairs R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R7 and R8, R8 and R9, R9 and R10, R10 and R11, R11 and R12, R13 and R14, R14 and R15 and R15 and R16 taken together may represent the atoms necessary to form a substituted or unsubstituted aromatic or heteroaromatic ring, and wherein the dye has a peak absorption between 660 and 800 nm.
- A photothermographic element according to claim 1, wherein the non-imaging layer containing the dye of structure (I) is a pelloid layer on the side of the support opposite the photothermographic layer.
- A photothermographic element according to claim 1, wherein the non-imaging layer containing the dye of structure (I) is an antihalation layer positioned between the support and the photothermographic layer.
- A photothermographic element according to claim 1, wherein at least one of R2 or R3 is a tertiary alkyl.
- A photothermographic element according to claim 1, M is Mg, Ni, Zn, or Cu.
- A photothermographic element according to claim 1, wherein the layer containing the dye comprises a hydrophobic binder.
- A photothermographic element according to claim 1, wherein the layer containing the dye comprises a hydrophilic binder.
- A photothermographic element according to claim 7, wherein the hydrophilic binder is gelatin.
- A photothermographic element according to claim 1, wherein the photothermographic element comprises at least two dyes of structure (I).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US97931797A | 1997-11-26 | 1997-11-26 | |
US979317 | 1997-11-26 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0919862A1 EP0919862A1 (en) | 1999-06-02 |
EP0919862B1 true EP0919862B1 (en) | 2003-10-15 |
Family
ID=25526841
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98203843A Expired - Lifetime EP0919862B1 (en) | 1997-11-26 | 1998-11-14 | Photothermographic imaging element containing an antihalation dye |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0919862B1 (en) |
JP (1) | JPH11242306A (en) |
DE (1) | DE69818948T2 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6287755B1 (en) * | 1998-04-20 | 2001-09-11 | Konica Corporation | Thermally developable photosensitive material |
JP3922953B2 (en) * | 2002-03-29 | 2007-05-30 | 富士フイルム株式会社 | Photothermographic material |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5223382A (en) * | 1991-12-02 | 1993-06-29 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4258129A (en) * | 1974-10-31 | 1981-03-24 | Fuji Photo Film Co., Ltd. | Thermally developable light sensitive material using trivalent and tetravalent cerium compounds |
DE69327875D1 (en) * | 1993-11-29 | 2000-03-23 | Imation Corp | Silver halide photographic material with reduced fog and staining |
EP0889355B1 (en) * | 1997-07-04 | 2004-05-19 | Agfa-Gevaert | (Photo) thermographic material with a blue background |
-
1998
- 1998-11-14 EP EP98203843A patent/EP0919862B1/en not_active Expired - Lifetime
- 1998-11-14 DE DE69818948T patent/DE69818948T2/en not_active Expired - Lifetime
- 1998-11-25 JP JP10333956A patent/JPH11242306A/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5223382A (en) * | 1991-12-02 | 1993-06-29 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
Also Published As
Publication number | Publication date |
---|---|
EP0919862A1 (en) | 1999-06-02 |
DE69818948D1 (en) | 2003-11-20 |
DE69818948T2 (en) | 2004-07-29 |
JPH11242306A (en) | 1999-09-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2648152B2 (en) | Protective layer for heat treatable elements | |
EP0334656B1 (en) | Thermally processable element comprising a backing layer | |
EP0969313B1 (en) | Photothermographic element having desired color | |
EP1102120B1 (en) | Thermally processable imaging element | |
US4886739A (en) | Thermally processable imaging element and process | |
US4459350A (en) | Photothermographic material and processing comprising a substituted triazine | |
EP0613046B1 (en) | Thermally processable imaging element comprising a barrier layer | |
EP0613045B1 (en) | Method for the manufacture of a thermally processable imaging element | |
JP2002311535A (en) | Thermally developable material and image forming method using the same | |
EP0919864B1 (en) | Support containing an antihalation dye for use in photothermographic elements | |
EP0919862B1 (en) | Photothermographic imaging element containing an antihalation dye | |
EP0742477B1 (en) | Spectrally sensitized photothermographic elements | |
US4857439A (en) | Photothermographic element and process | |
US5508162A (en) | Photothermographic elements containing a combination of spectral sensitizers | |
US5891610A (en) | Thermally processable imaging element with improved adhesion of the overcoat layer | |
US5714311A (en) | Thermally processable imaging element comprising aryliodonium compounds | |
EP0962813B1 (en) | Thermally processable imaging element | |
EP0919863B1 (en) | Thermally processable imaging element having improved physical properties |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): DE FR GB |
|
AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
|
17P | Request for examination filed |
Effective date: 19991102 |
|
AKX | Designation fees paid |
Free format text: DE FR GB |
|
17Q | First examination report despatched |
Effective date: 20020802 |
|
GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): DE FR GB |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20031024 Year of fee payment: 6 |
|
REF | Corresponds to: |
Ref document number: 69818948 Country of ref document: DE Date of ref document: 20031120 Kind code of ref document: P |
|
ET | Fr: translation filed | ||
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20041004 Year of fee payment: 7 |
|
26N | No opposition filed |
Effective date: 20040716 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20050729 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20051114 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20051130 Year of fee payment: 8 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF THE APPLICANT RENOUNCES Effective date: 20060316 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20051114 |