EP0479029B1 - Silver halide photographic element and process for preparing a dispersion of discrete particles of water insoluble polymeric matting agent in aqueous compositions - Google Patents
Silver halide photographic element and process for preparing a dispersion of discrete particles of water insoluble polymeric matting agent in aqueous compositions Download PDFInfo
- Publication number
- EP0479029B1 EP0479029B1 EP91115719A EP91115719A EP0479029B1 EP 0479029 B1 EP0479029 B1 EP 0479029B1 EP 91115719 A EP91115719 A EP 91115719A EP 91115719 A EP91115719 A EP 91115719A EP 0479029 B1 EP0479029 B1 EP 0479029B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- silver halide
- compound
- dispersion
- matting agent
- 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
- -1 Silver halide Chemical class 0.000 title claims description 67
- 239000006224 matting agent Substances 0.000 title claims description 47
- 239000006185 dispersion Substances 0.000 title claims description 40
- 229910052709 silver Inorganic materials 0.000 title claims description 34
- 239000004332 silver Substances 0.000 title claims description 34
- 239000002245 particle Substances 0.000 title claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000010410 layer Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 239000000839 emulsion Substances 0.000 claims description 29
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 28
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 25
- 235000021286 stilbenes Nutrition 0.000 claims description 25
- 239000000084 colloidal system Substances 0.000 claims description 24
- 108010010803 Gelatin Proteins 0.000 claims description 22
- 229920000159 gelatin Polymers 0.000 claims description 22
- 235000019322 gelatine Nutrition 0.000 claims description 22
- 235000011852 gelatine desserts Nutrition 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 20
- 239000008273 gelatin Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 17
- 239000011241 protective layer Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 229910006069 SO3H Inorganic materials 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 102000009027 Albumins Human genes 0.000 claims description 4
- 108010088751 Albumins Proteins 0.000 claims description 4
- 229920002307 Dextran Polymers 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 229920000615 alginic acid Polymers 0.000 claims description 4
- 235000010443 alginic acid Nutrition 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920001480 hydrophilic copolymer Polymers 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 238000012545 processing Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- 238000011160 research Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000002344 surface layer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002216 antistatic agent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZFXPBTZXYNIAJW-UHFFFAOYSA-N 4-[2-(2-phenylethenyl)phenyl]triazine Polymers C=1C=CC=CC=1C=CC1=CC=CC=C1C1=CC=NN=N1 ZFXPBTZXYNIAJW-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000002601 radiography Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229960001755 resorcinol Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- UTDSSTFBUGDVAI-LURJTMIESA-N (2s)-1-prop-2-enoylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)C=C UTDSSTFBUGDVAI-LURJTMIESA-N 0.000 description 1
- FQOWJGGXNSRNJS-YFKPBYRVSA-N (2s)-2-(2-methylprop-2-enoylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C(C)=C FQOWJGGXNSRNJS-YFKPBYRVSA-N 0.000 description 1
- PPRBGMXQDAMDAB-BYPYZUCNSA-N (2s)-2-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C=C PPRBGMXQDAMDAB-BYPYZUCNSA-N 0.000 description 1
- SIADNYSYTSORRE-UHFFFAOYSA-N (4-chlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(Cl)C=C1 SIADNYSYTSORRE-UHFFFAOYSA-N 0.000 description 1
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 description 1
- BEWIWYDBTBVVIA-PLNGDYQASA-N (z)-4-(butylamino)-4-oxobut-2-enoic acid Chemical compound CCCCNC(=O)\C=C/C(O)=O BEWIWYDBTBVVIA-PLNGDYQASA-N 0.000 description 1
- HBQGCOWNLUOCBU-ARJAWSKDSA-N (z)-4-(ethylamino)-4-oxobut-2-enoic acid Chemical compound CCNC(=O)\C=C/C(O)=O HBQGCOWNLUOCBU-ARJAWSKDSA-N 0.000 description 1
- GPTNZCCQHNGXMS-SREVYHEPSA-N (z)-4-oxo-4-phenoxybut-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OC1=CC=CC=C1 GPTNZCCQHNGXMS-SREVYHEPSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- GXZPMXGRNUXGHN-UHFFFAOYSA-N 1-ethenoxy-2-methoxyethane Chemical compound COCCOC=C GXZPMXGRNUXGHN-UHFFFAOYSA-N 0.000 description 1
- IBTLFDCPAJLATQ-UHFFFAOYSA-N 1-prop-2-enoxybutane Chemical compound CCCCOCC=C IBTLFDCPAJLATQ-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- BOURDYMMTZXVRY-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)acetic acid Chemical compound CC(=C)C(=O)NCC(O)=O BOURDYMMTZXVRY-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- KBUHBJRHAZPSNI-UHFFFAOYSA-N 3-(butylcarbamoyl)but-3-enoic acid Chemical compound CCCCNC(=O)C(=C)CC(O)=O KBUHBJRHAZPSNI-UHFFFAOYSA-N 0.000 description 1
- SYIHZNJRLWJZAS-UHFFFAOYSA-N 3-(ethylcarbamoyl)but-3-enoic acid Chemical compound CCNC(=O)C(=C)CC(O)=O SYIHZNJRLWJZAS-UHFFFAOYSA-N 0.000 description 1
- JBTDFRNUVWFUGL-UHFFFAOYSA-N 3-aminopropyl carbamimidothioate;dihydrobromide Chemical compound Br.Br.NCCCSC(N)=N JBTDFRNUVWFUGL-UHFFFAOYSA-N 0.000 description 1
- BLRZZXLJCJKJII-UHFFFAOYSA-N 3-carbamoylbut-3-enoic acid Chemical compound NC(=O)C(=C)CC(O)=O BLRZZXLJCJKJII-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- VVAAYFMMXYRORI-UHFFFAOYSA-N 4-butoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCCCOC(=O)CC(=C)C(O)=O VVAAYFMMXYRORI-UHFFFAOYSA-N 0.000 description 1
- RTTAGBVNSDJDTE-UHFFFAOYSA-N 4-ethoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCOC(=O)CC(=C)C(O)=O RTTAGBVNSDJDTE-UHFFFAOYSA-N 0.000 description 1
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 1
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 1
- RYHAZBFRQQCSOJ-UHFFFAOYSA-N 5-methoxypent-1-en-3-one Chemical compound COCCC(=O)C=C RYHAZBFRQQCSOJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229940090898 Desensitizer Drugs 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- LZCXCXDOGAEFQX-UHFFFAOYSA-N N-Acryloylglycine Chemical compound OC(=O)CNC(=O)C=C LZCXCXDOGAEFQX-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Polymers 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 230000002742 anti-folding effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 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
- 239000000298 carbocyanine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- HOSFCSQXJQXSIQ-ZPZFBZIMSA-L disodium;5-[(4,6-dianilino-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4,6-dianilino-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].C=1C=C(\C=C\C=2C(=CC(NC=3N=C(NC=4C=CC=CC=4)N=C(NC=4C=CC=CC=4)N=3)=CC=2)S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=1NC(N=C(NC=1C=CC=CC=1)N=1)=NC=1NC1=CC=CC=C1 HOSFCSQXJQXSIQ-ZPZFBZIMSA-L 0.000 description 1
- YUZILKLGVPUFOT-YHPRVSEPSA-L disodium;5-[(6-anilino-4-oxo-1h-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(6-anilino-4-oxo-1h-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].C=1C=C(\C=C\C=2C(=CC(NC=3NC(NC=4C=CC=CC=4)=NC(=O)N=3)=CC=2)S([O-])(=O)=O)C(S(=O)(=O)[O-])=CC=1NC(N1)=NC(=O)N=C1NC1=CC=CC=C1 YUZILKLGVPUFOT-YHPRVSEPSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- BGVWGPMAGMJLBU-UHFFFAOYSA-N ethenyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC=C)=CC=CC2=C1 BGVWGPMAGMJLBU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000314 lubricant Substances 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
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/95—Photosensitive materials characterised by the base or auxiliary layers rendered opaque or writable, e.g. with inert particulate additives
Definitions
- the present invention relates to a silver halide photographic light-sensitive element having incorporated in a hydrophilic colloid layer thereof discrete particles of a water-insoluble polymeric matting agent and to a process for preparing a dispersion of discrete particles of said polymeric matting agent in aqueous compositions.
- water-insoluble matting agents have been used in top or back hydrophilic colloid layers of silver halide light-sensitive materials to prevent adhesion when materials are stored in rolls, cartridges or cassettes in conditions of relatively high humidity and temperature, to prevent electrostatic charges by reducing the area of contact of the photographic material, to prevent the formation of Newton's rings during printing and enlargement, or to decrease the occurrence of scratches during storage or packing of the photographic material.
- matting agents insoluble in neutral or acidic solutions and soluble in alkaline medium have been described in the art.
- alkali-soluble matting agents consisting of methacrylic acid - methylmethacrylate copolymers have been described in US Pat. Nos. 2,391,181, 2,992,101, 3,767,448 and 4,142,894, and in British Pat. No. 878,520, and copolymers of styrene and ⁇ , ⁇ -ethylenically unsaturated carboxy containing monomers have been described in British Pat. No. 1,055,713.
- Such matting agents can be incorporated in the photographic layers in the form of discrete particles by dispersing a solution of the matting agent in a water-immiscible organic solvent in an aqueous gelatin solution, eliminating the organic solvent, and then introducing the obtained dispersion into the coating composition of the photographic layer.
- Organic solvents or combinations thereof have been studied with the copolymers of methacrylic acid and methylmethacrylate, the basic solvent being butanol and mixtures thereof with other solvents. Since butanol is a solvent with low volatility it must be removed by cooling the dispersion and washing with deionized water.
- Alkali-soluble matting agents consisting of methacrylic acid - ethylmethacrylate copolymers containing from 20 to 50 % by weight of methacrylic acid have been described in US Pat. No. 4,447,525. These copolymers dissolve in high concentrations in highly volatile organic solvent such as ethylacetate, a solvent which can be easily removed by evaporation from the dispersion of the polymer in aqueous gelatin.
- the matting agents are characterized by the number average particle sizes (APS) of their discrete particles and in the patents there are teachings on how to control the APS in the process of synthesis thereof.
- APS number average particle sizes
- PSD particle size distribution
- Another characteristic of matting agents is their particle size distribution (PSD), in one aspect this is the measurement of the proportion of the larger size discrete particles present in the dispersion.
- PSD particle size distribution
- the presence of huge particles having a dimension which exceeds 10 ⁇ m in diameter may cause undesirable side effects such as disturbance of coating uniformity of the photographic material and disturbance of distinct layer relationships of a plurality of superposed layers of the photographic material.
- EP Appl. No. 370,405 discloses matting agents having a PSD not exceeding 10 ⁇ m which do not give rise to the above undesirable side effects. In spite of this, when the polymeric matting agent dispersion is mixed with aqueous gelatin, agglomeration of the beads can take place.
- the formation of aggregates in coating solutions may effectively form larger size particle groupings which cause undesirable side-effects such as a disturbance of coating uniformity, a formation of a haze in the processed light sensitive elements, an impairment of the transparency of the image formed, and a deterioration of the graininess of the image.
- US Patent No. 4,142,894 discloses a copolymer of methyl methacrylate and methacrylic acid with a molar ratio of 6:4 to 9:1 which does not form aggregates in coating solution even when the copolymer particles are used in a large quantity.
- GB Patent No. 1,496,534 discloses a silver halide photographic material having a surface layer containing at least one organic fluoro-compound and at least one carboxy compound containing a hydrophobic group, said material suffering less aggregation of matting agent in coating solution. These solutions are, from one way, referred to a selected and preferred matting agent, and from another way, difficult to realize. It is, therefore, strongly desired to develop an improved mixing process of polymeric matting agent dispersions with hydrophilic colloid to avoid said undesirable effects.
- DE 1,955,898 discloses a photographic material including resorcin in a silver halide emulsion layer and a poly-N-vinyl lactam or polyvinyl lactone in the emulsion layer or in a protective surface layer.
- the surface coating includes silica particles and a polycarboxylic sulfonic acid (such as a sulfonated stilbene compound) to reduce the milkiness produced by the presence in the photographic material of resorcin and polyvinyl lactam or polyvinyl lactone.
- the present invention relates to a process for providing a matt surface on a photographic element, which element comprises a support base, one or more light sensitive silver halide emulsion layers coated on said support base and at least one outer non-light sensitive protective layer, said process comprising:
- the present invention relates to a silver halide photographic element comprising a support base, one or more light-sensitive silver halide emulsion layers and at least one outer non-light sensitive protective layer comprising discrete particle of a polymeric matting agent and a stilbene polysulfonate compound.
- the present invention relates to a process for providing a matt surface on a photographic element, which element comprises a support base, one or more light sensitive silver halide emulsion layers coated on said support base and at least one outer non- light sensitive protective layer coated on said layers or the back side of said support base, said process comprising:
- Polymeric matting agents useful in the present invention can be compounds derived from the polymerization through ethylenically unsaturated groups of (a) repeating units derived from an ethylenic unsaturated monomer having carboxyl groups thereon and/or (b) repeating units derived from ethylenic unsaturated monomers capable of forming hydrophobic homopolymers.
- Examples of ethylenic unsaturated monomers having carboxyl groups thereon from which can derive the repeating units (a) of the polymeric matting agent include acrylic acid, methacrylic acid, maleic acid (including monosubstituted maleates such as monomethyl maleate, monoethyl maleate and monophenyl maleate), itaconic acid (including monosubstituted itaconate such as monomethyl itaconate, monoethyl itaconate and monobutyl itaconate), fumaric acid (including monosubstituted fumarate such as monomethyl fumarate and monoethyl fumarate), crotonic acid, citraconic acid, N-(meth)-acryloylamino acids such as N-acryloylglycine, N-methacryloylglycine, N-acryloylalanine, N-methacryloylalanine and N-acryloylproline, vinylbenzoic acid, maleic acid monoamide, N-al
- ethylenic unsaturated monomers from which can derive the repeating units (b) of the polymeric matting agent include acrylic acid esters such as methyl acrylate, ethyl acrylate, n-butyl acrylate and phenyl acrylate, methacrylic acid esters such as methyl methacrylate, ethyl methacrylate, isopropyl methacrylate and p-chlorophenyl methacrylate, styrenes such as styrene, methylstyrene, ⁇ -methylstyrene, chloromethylstyrene and bromostyrene, vinyl esters such as vinyl benzoate, vinylphenyl acetate and vinyl naphthoate, vinyl ethers such as allyl butyl ether, methoxyethyl vinyl ether and phenyl vinyl ether, olefins such as ethylene, propylene, 1-butene and 1-pentene, uns
- methacrylic acid is particularly preferable as the ethylenic unsaturated monomers having carboxyl groups thereon from which derive the repeating units (a) above and methacrylic acid esters such as methyl methacrylate and ethyl methacrylate are particularly preferable as ethylenic unsaturated monomers from which derive the repeating units (b) above.
- the preferred polymeric matting agent for use in the process of the present invention may be represented by the following formula: wherein m + n is equal to 100 (approximately 100 as endcapping groups may be present) and each of m and n represents respectively the percentage by weight of said repeating units (a) and (b) of said polymeric matting agent and R represents methyl or ethyl.
- the polymeric matting agent useful in the process of the present invention can be represented by the following formula: wherein p is an integer of from 1,000 to 10,000, preferably from 3,000 to 7,000 and R represents methyl or ethyl.
- Said polymers can be prepared from the polymerization through ethylenically unsaturated groups of the monomers described above, using any conventional polymerization mechanism, preferably free radical polymerization.
- the free radical polymerization is carried out by heating a reaction mass at a proper temperature (which usually does not exceed 100°C and preferably is between 50°C and 100°C) in a proper solvent (usually ethanol or methanol).
- the reaction mass contains the monomer (or a mixture of the two monomers) in a proper concentration with respect to the solvent (usually at a concentration that does not exceed 40% by weight of the monomer [or a mixture of the two monomers] with respect to the solvent, preferably between 15% to 30%) in the presence of a polymerization catalyst (for example of the free radical type, such as benzoyl peroxide or cumene hydroperoxide, or of the azoic type, such as ⁇ , ⁇ -azobisisobutyronitrile).
- a polymerization catalyst for example of the free radical type, such as benzoyl peroxide or cumene hydroperoxide, or of the azoic type, such as ⁇ , ⁇ -azobisisobutyronitrile.
- the present invention is not limited to processes and elements involving the specific examples of polymeric matting agents described above, the use of said examples representing a particular embodiment only. Any polymeric matting agents known in the photographic art can be used in combination with said polysulfonate stilbene compounds to reduce particle aggregation in coating solutions. Other examples of said polymeric matting agents can be found in Research Disclbsure, December 1989, Item 308119, Section XVI.
- a dispersion in water of the polymer described above is provided before the mixing step with an aqueous hydrophilic colloid solution.
- Any method known in the art can be used to provide the dispersion.
- the polymeric matting agent may be dissolved in a water insoluble organic solvent and then the obtained solution dispersed in water.
- the polymeric matting agent dispersion can be obtained directly from the polymerization under agitation of the monomer in water and/or an organic solvent, which is a solvent for the monomer(s) but not for the polymer.
- the organic solvent is eliminated from the dispersion by washing the dispersion with pure water or by heating, as known in the art.
- Useful organic solvents to prepare the above described dispersion include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,1-dichloromethane, 1,2-dichloroethane and 1,1, 1-trichloroethane, aliphatic esters such as ethyl acetate, butyl acetate and isopropyl acetate, aromatic hydrocarbons such as benzene, toluene and xylene, aliphatic hydrocarbons such as pentane and n-hexane, aliphatic ketones such as methyl ethyl ketone and methyl isobutyl ketone, higher aliphatic alcohols such as n-butanol and isobutanol.
- halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,1-dichloromethane, 1,2-dichloroethane and
- Said organic solvents have a boiling point which is preferably less than 150°C, and more preferably less than 100°C.
- the solvents also may have a solubility in water at 20°C which is preferably less than 20 grams per liter, and more preferably less than 10 grams per liter.
- the dispersion is then mixed with an aqueous hydrophilic colloid solution.
- the hydrophilic colloid is preferably gelatin, but also gelatin derivatives and any of the many other polymeric compounds known in the photographic art, such as albumin, polyvinyl alcohol, alginates, cellulose hydrolized esters, hydrophilic polyvinyl polymers, dextrans, polyacrylamides, acrylamide and alkylacrylate hydrophilic copolymers, can also be used, alone or in combination with gelatin.
- said mixing step is performed in the presence of a stilbene polysulfonate compound (i.e., a compound having a nucleus consisting of two sulfonated benzene rings joined by an ethylene group, said benzene rings being optionally substituted with organic substituents).
- a stilbene polysulfonate compound i.e., a compound having a nucleus consisting of two sulfonated benzene rings joined by an ethylene group, said benzene rings being optionally substituted with organic substituents.
- Said stilbene polysulfonate compound is preferably represented by the following formula (I): wherein X is SO 3 H or SO 3 M, in which M is an alkaline or alkaline earth metal, Y is represented by the following formula:
- Said stilbene polysulfonate compound is preferably represented by the following formula (II): wherein X, R 1 , R 2 and n are the same described in formula (I) above.
- stilbene polysulfonate compounds useful in the process of the present invention are listed below, but these are not the sole examples that can be used in the present invention.
- Other useful stilbene polysulfonate compounds are disclosed, for example, in US Pat. Nos. 2,875,058, 2,933,390, 2,945,762, 2,961,318 and in Research Disclosure, Item 17804, February 1979 and Item 308119, December 1989, Section V.
- said stilbene compounds have been previously employed in the textile field, paper field and photographic field as whitening agents, brighteners and/or supersensitizers in combination with carbocyanine derivatives.
- 251,282 discloses the use of a stilbene polysulfonate compound as deaggregant of carbocyanine dyes to obtain the proper absorption wavelength (other deaggregants are suggested and reference about dye aggregation, a different problem as compared with polymeric matting agent aggregation, is shown in Herz, Photographic Science and Engineering, 18 , pp. 323-335, May/June 1974). These references do not disclose said stilbene polysulfonate compounds as deaggregants for polymeric matting agents in photographic layers.
- Such stilbene polysulfonate compounds are sold under various trade names such as Leucophor B, Calcofluor White MR, Tinopal (SP, SFP, STP, MSP, WR, BV277, 2B, GS, NG), Blancofor SC, Hiltamine (BSP, N, 6T6).
- the stilbene polysulfonate compounds above can be present in an amount of from 0.05 to 5% by weight, preferably from 0.1 to 1%, of the total weight of the resulting hydrophilic colloid dispersion.
- said stilbene polysulfonate compound is dissolved in the hydrophilic colloid solution and then to that resulting solution is added the polymeric matting agent aqueous dispersion.
- the polymeric matting agents above become dispersed in the aqueous solution of the hydrophilic colloid in the form of finely divided particles with fewer than 1% of any particle aggregates having more than three particles. Preferably, there are substantially no aggregates of more than three particles.
- Said dispersions are then introduced into the coating composition of the outer light-insensitive layer of a silver halide light sensitive element.
- Said outer layer may be a surface protective layer coated on the silver halide emulsion layers, or a backing protective layer coated on the support base on the side opposite to that containing the light-sensitive layers, or may be both of them. It is more preferred to incorporate said dispersion into the surface protective layer.
- the present invention relates to a silver halide photographic element comprising a support base, one or more light-sensitive silver halide emulsion layers and at least one outer non-light sensitive protective layer coated on said layers or the back side of said support base, said at least one outer protective layer comprising discrete particles of a polymeric matting agent and a stilbene polysulfonate compound represented by the formula (I) above.
- said stilbene polysulfonate compound is represented by the formula (II) above.
- stilbene compounds useful in the photographic element of the present invention are the same listed above.
- the dispersion of polymeric matting agent in hydrophilic colloid solution containing the stilbene polysulfonate compounds is present in an outer layer of the photographic element of the present invention.
- the matting agents are preferably incorporated in a quantity of 50 to 600 mg., and more preferably from about 150 to about 400 mg. per square meter of the surface layer.
- the binding agent of such layer preferably is gelatin, but treated gelatins like the so-called acid or basic gelatins, the gelatins treated with enzymes, gelatin derivatives and modified gelatins, albumin, polyvinyl alcohol, alginates, cellulose hydrolized esters, hydrophilic polyvinyl polymers, dextrans, polyacrylamides, acrylamide and alkylacrylate hydrophilic copolymers, can also be used, alone or in combination with gelatin.
- additives such as those known in the art, including, but not limited to, hardeners, plasticizers, surfactants, antistatic agents, polymeric latexes, anti-calcium and antispot agents can be incorporated into said surface layer.
- the light-sensitive silver halide photographic elements of this invention may be any photographic color element such as color negative films, color reversal films, color papers, as well as any black-and-white photographic element such as X-ray light-sensitive elements, black-and-white photographic printing papers, black-and-white negative films.
- the photographic element of the present invention may be a color photographic element which comprises a plurality of hydrophilic (i.e., permeable to the water photographic processing solutions) emulsion layers containing silver halides dispersed in gelatin, associated with auxiliary hydrophilic gelatin layers, interlayers, antihalo layers, backing layers, said plurality of layers being coated onto a hydrophobic support base.
- hydrophilic i.e., permeable to the water photographic processing solutions
- emulsion layers containing silver halides dispersed in gelatin, associated with auxiliary hydrophilic gelatin layers, interlayers, antihalo layers, backing layers, said plurality of layers being coated onto a hydrophobic support base.
- Such silver halide emulsions are sensitive or sensitized to the blue and associated with non-diffusing yellow-forming couplers (upon color development with p-phenylene diamine after exposure), or are sensitized to the green and associated with non-diffusing magenta (blue red) forming couplers, or sensitized to the red and associated with non-diffusing cyan (blue-green) forming couplers.
- the photographic element can contain silver halide emulsions, chemical sensitizers, spectral sensitizers and desensitizers, optical brighteners, antifoggants and stabilizers, couplers, acutance dyes, hydrophilic colloids and gelatin substituents, coating aids, hardeners, plasticizers and antistatic agents, as known to the man skilled in the art and can be prepared by following known coating techniques applied to known support bases, as described in Research Disclosure, December 1978, 17643 and December 1989, 308119.
- the photographic elements of this invention after exposure, are processed to form a visible image upon association of the silver halide with an alkaline water medium in the presence of a developing agent contained in the medium or in the elements themselves, as known in the art.
- the processing comprises at least a color developing bath and, optionally, a pre-hardening bath, a neutralizing bath, a first (black and white) developing bath.
- the photographic element of the present invention may be an X-ray photographic element which comprises a polymeric base of the type commonly used in radiography, for instance a polyester base, and in particular a polyethylene terephthalate base.
- a silver halide emulsion layer in a hydrophilic colloid On at least one surface, preferably on both surfaces of the base there is coated a silver halide emulsion layer in a hydrophilic colloid.
- the emulsions coated on the two surfaces may also be different and comprise emulsions commonly used in photographic elements, such as silver chloride, silver iodide, silver chloro-bromide, silver chloro-bromo-iodide, silver bromide and silver bromo-iodide emulsions, the silver bromo-iodide emulsions being particularly useful for the X-ray elements.
- the silver halide crystals may have different shapes, for instance cubic, octahedral, spherical, tabular shapes, and may have epitaxial growth.
- the emulsions are coated on the base at a total silver coverage comprised in the range from 2 to 7 or 3 to 6 grams per square meter.
- the silver halide binding material used is a water-permeable hydrophilic colloid, which is preferably gelatin, but other hydrophilic colloids, such as gelatin derivatives, albumin, polyvinyl alcohol, alginates, cellulose hydrolized esters, hydrophilic polyvinyl polymers, dextrans, polyacrylamides, acrylamide hydrophilic copolymers and alkylacrylates can also be used alone or in combination with gelatin.
- the photographic elements of this invention in the light-sensitive silver halide emulsion layers or in other layers, can include additional addenda of a conventional nature, such as stabilizers, antifoggants, brighteners, absorbing materials, hardeners, coating aids, plasticizers, lubricants, matting agents, antikinking agents, antistatic agents, as described in Research Disclosure, Item 17643, December 1978 and in Research Disclosure, Item 18431, August 1979.
- additional addenda of a conventional nature such as stabilizers, antifoggants, brighteners, absorbing materials, hardeners, coating aids, plasticizers, lubricants, matting agents, antikinking agents, antistatic agents, as described in Research Disclosure, Item 17643, December 1978 and in Research Disclosure, Item 18431, August 1979.
- Preferred radiographic elements are of the type described in BE Patent 757,815 and in US Patent 3,705,858, i.e. elements wherein at least one light-sensitive silver halide emulsion layer is coated on both surfaces of a transparent support, the total silver coverage per surface unit for both layers being lower than about 6 g/m 2 , preferably lower than 5 g/m 2 .
- Such supports are preferably polyester film supports, such as polyethylene terephthalate films.
- said supports for use in medical radiography are blue tinted.
- Preferred blue tinting dyes are anthraquinone dyes, such as those described in US Patents 3,488,195; 3,849,139; 3,918,976; 3,933,502; 3,948,664 and in UK Patents 1,250,983 and 1,372,668.
- the exposed radiographic elements can be processed by any of the conventional processing techniques. Such processing techniques are illustrated for example in Research Disclosure, Item 17643, cited above. Roller transport processing is particularly preferred, as illustrated in US Patents 3,025,779; 3,515,556; 3,545,971 and 3,647,459 and in UK Patent 1,269,268. Hardening development can be undertaken, as illustrated in US Patent 3,232,761.
- a set of seven dispersions using some surface active coating aids and/or dispersing agents was prepared as follows.
- An aqueous solution of surfactant or dispersing agents of table 1 was added to 24 ml of a 10% aqueous solution of gelatin at 45°C with stirring.
- Compound A is a polysulfonated triazinyl stilbene compound, within the general formulas I and II above, and sold by Ciba-Geigy AG under TinopalTM SFP tradename.
- TritonTM is a tradename of polyethoxylated alkyl phenols sold by Rohm and Haas Co.
- TamolTM is a tradename of soluble salts of polymeric carboxylic acids
- TergitolTM is a tradename of sodium salts of alkanol sulfates sold by Union Carbide Co. Chemical Division
- TegobetaineTM is a tradename of betaine derivatives sold by Th. Goldschmidt AG
- a set of twenty dispersions using some surface active coating aids and/or dispersing agents was prepared, following the same procedure of example 1. All dispersions were tested as in example 1.
- table 3 the adjuvants added for each dispersion, and the results obtained according the procedure of example 1, are summarized.
- AGGREGATES of Table 3 means clusters of more than three particles.
- Compounds A,B,C,D are polysulfonated triazinyl stilbene compounds, included within the general formulas I and II above, respectively sold by Ciba-Geigy AG under TinopalTM SFP, SFP, 2B, STP, CH3517 tradenames.
- BrijTM is a tradename of polyoxyethylene alkyl ether nonionic surfactants sold by Atlas Chemical Ind.
- MaprofixTM is a tradename of sodium salts of alkyl sulfates sold by Onix Chemical Company
- NiaproofTM is a tradename of sodium salts of alkanol sulfates sold by Niacet Co.
- HostapurTM is a tradename of alkyl sulfonates sold by Hoechst AG.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Colloid Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2164890 | 1990-10-05 | ||
IT02164890A IT1253002B (it) | 1990-10-05 | 1990-10-05 | Elemento fotografico agli alogenuri d'argento e procedimento per preparare una dispersione in composizioni acquose di particelle discrete di un agente mattante polimerico insolubile in acqua |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0479029A1 EP0479029A1 (en) | 1992-04-08 |
EP0479029B1 true EP0479029B1 (en) | 1997-12-17 |
Family
ID=11184822
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91115719A Expired - Lifetime EP0479029B1 (en) | 1990-10-05 | 1991-09-17 | Silver halide photographic element and process for preparing a dispersion of discrete particles of water insoluble polymeric matting agent in aqueous compositions |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0479029B1 (ja) |
JP (1) | JP3054246B2 (ja) |
DE (1) | DE69128448T2 (ja) |
IT (1) | IT1253002B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7173778B2 (en) | 2004-05-07 | 2007-02-06 | 3M Innovative Properties Company | Stain repellent optical hard coating |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7101618B2 (en) | 2004-05-07 | 2006-09-05 | 3M Innovative Properties Company | Article comprising fluorochemical surface layer |
US20060216524A1 (en) | 2005-03-23 | 2006-09-28 | 3M Innovative Properties Company | Perfluoropolyether urethane additives having (meth)acryl groups and hard coats |
US8728623B2 (en) | 2007-08-31 | 2014-05-20 | 3M Innovative Properties Company | Hardcoats having low surface energy and low lint attraction |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH330158A (de) * | 1954-07-31 | 1958-05-31 | Typon Ag | Verfahren zur Herstellung von photographischem Material mit aufgerauhter, praktisch nichtmattierter Oberfläche |
GB1274302A (en) * | 1969-03-17 | 1972-05-17 | Agfa Gevaert | Photographic silver halide materials containing silica particles |
JPS537231A (en) * | 1976-07-08 | 1978-01-23 | Fuji Photo Film Co Ltd | Image formation |
-
1990
- 1990-10-05 IT IT02164890A patent/IT1253002B/it active IP Right Grant
-
1991
- 1991-09-17 EP EP91115719A patent/EP0479029B1/en not_active Expired - Lifetime
- 1991-09-17 DE DE69128448T patent/DE69128448T2/de not_active Expired - Fee Related
- 1991-10-03 JP JP3256414A patent/JP3054246B2/ja not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7173778B2 (en) | 2004-05-07 | 2007-02-06 | 3M Innovative Properties Company | Stain repellent optical hard coating |
Also Published As
Publication number | Publication date |
---|---|
IT1253002B (it) | 1995-07-10 |
IT9021648A1 (it) | 1992-04-05 |
EP0479029A1 (en) | 1992-04-08 |
JPH04248549A (ja) | 1992-09-04 |
DE69128448T2 (de) | 1998-07-16 |
DE69128448D1 (de) | 1998-01-29 |
JP3054246B2 (ja) | 2000-06-19 |
IT9021648A0 (it) | 1990-10-05 |
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