EP0708932A1 - Photographisches element mit verringerter restanfärbung - Google Patents
Photographisches element mit verringerter restanfärbungInfo
- Publication number
- EP0708932A1 EP0708932A1 EP94921905A EP94921905A EP0708932A1 EP 0708932 A1 EP0708932 A1 EP 0708932A1 EP 94921905 A EP94921905 A EP 94921905A EP 94921905 A EP94921905 A EP 94921905A EP 0708932 A1 EP0708932 A1 EP 0708932A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dispersion
- scavenger
- crystalline solid
- disulfonamidophenol
- carbon atoms
- 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.)
- Withdrawn
Links
- 239000006185 dispersion Substances 0.000 claims abstract description 135
- 239000002516 radical scavenger Substances 0.000 claims abstract description 47
- 239000007787 solid Substances 0.000 claims abstract description 32
- 239000002245 particle Substances 0.000 claims abstract description 31
- 239000002270 dispersing agent Substances 0.000 claims abstract description 14
- 238000003801 milling Methods 0.000 claims abstract description 12
- 239000012736 aqueous medium Substances 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- -1 silver halide Chemical class 0.000 claims description 39
- 239000000839 emulsion Substances 0.000 claims description 35
- 229910052709 silver Inorganic materials 0.000 claims description 33
- 239000004332 silver Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229920003169 water-soluble polymer Polymers 0.000 claims 1
- 239000010410 layer Substances 0.000 description 67
- 239000000975 dye Substances 0.000 description 50
- 239000011229 interlayer Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 229940125904 compound 1 Drugs 0.000 description 27
- 108010010803 Gelatin Proteins 0.000 description 20
- 239000008273 gelatin Substances 0.000 description 20
- 229920000159 gelatin Polymers 0.000 description 20
- 235000019322 gelatine Nutrition 0.000 description 20
- 235000011852 gelatine desserts Nutrition 0.000 description 20
- 239000000463 material Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000011161 development Methods 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 6
- 238000010186 staining Methods 0.000 description 6
- CWNSVVHTTQBGQB-UHFFFAOYSA-N N,N-Diethyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CC)CC CWNSVVHTTQBGQB-UHFFFAOYSA-N 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- ZTFYJIXFKGPCHV-UHFFFAOYSA-N 2-propan-2-ylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C(C)C)=CC=C21 ZTFYJIXFKGPCHV-UHFFFAOYSA-N 0.000 description 3
- 101100221809 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cpd-7 gene Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229940116335 lauramide Drugs 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N lauric acid amide propyl betaine Natural products CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 150000004986 phenylenediamines Chemical class 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- CJAOGUFAAWZWNI-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetramethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N(C)C)C=C1 CJAOGUFAAWZWNI-UHFFFAOYSA-N 0.000 description 1
- JHKKTXXMAQLGJB-UHFFFAOYSA-N 2-(methylamino)phenol Chemical compound CNC1=CC=CC=C1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical class C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 description 1
- FJWJYHHBUMICTP-UHFFFAOYSA-N 4,4-dimethylpyrazolidin-3-one Chemical compound CC1(C)CNNC1=O FJWJYHHBUMICTP-UHFFFAOYSA-N 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
- LGMWBTURBRPNCJ-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methoxybenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(OC)=C1 LGMWBTURBRPNCJ-UHFFFAOYSA-N 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229940090898 Desensitizer Drugs 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- NUAFPTFZCCVGLC-UHFFFAOYSA-N S(=O)(=O)(O)C(C(=O)O)CC(=O)O.C(C)C(CCCC)([Na])CC Chemical compound S(=O)(=O)(O)C(C(=O)O)CC(=O)O.C(C)C(CCCC)([Na])CC NUAFPTFZCCVGLC-UHFFFAOYSA-N 0.000 description 1
- DDSBWFLCPJEHLM-UHFFFAOYSA-N S(=O)(=O)(O)C(C(=O)O)CC(=O)O.CC(CCCC)([Na])C Chemical compound S(=O)(=O)(O)C(C(=O)O)CC(=O)O.CC(CCCC)([Na])C DDSBWFLCPJEHLM-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- HOLVRJRSWZOAJU-UHFFFAOYSA-N [Ag].ICl Chemical compound [Ag].ICl HOLVRJRSWZOAJU-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012992 electron transfer agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical class N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 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
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XZTJQQLJJCXOLP-UHFFFAOYSA-M sodium;decyl sulfate Chemical compound [Na+].CCCCCCCCCCOS([O-])(=O)=O XZTJQQLJJCXOLP-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
-
- 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/39212—Carbocyclic
- G03C7/39216—Carbocyclic with OH groups
Definitions
- This invention relates to a method of reducing dye stain in a photographic element and to a photographic element having reduced dye stain.
- scavengers for oxidized developing agents to photographic elements to allow the scavenger to interact with the oxidized developing agent and prevent unwanted reaction between oxidized developer and components of the photographic element.
- scavengers for oxidized developing agent known in the art are disulfonamidophenol derivatives disclosed in U.S. Patents Nos. 4,205,987 to Erikson et al, 4,447,523 to Ross et al and 4,952,474 to Tsukahara et al.
- One aspect of this invention comprises a photographic element comprising a support having thereon at least one silver halide emulsion layer, and a layer, which is the same or different from the silver halide layer, comprising crystalline solid particles consisting essentially of a disulfonamidophenol oxidized developer scavenger dispersed in an aqueous medium.
- Another aspect of the present invention comprises a process for preparing a crystalline solid particle dispersion of a disulfonamidophenol oxidized developer scavenger, comprising the steps of: (a) milling crystalline solid particles of the scavenger in an aqueous medium in the presence of a dispersing agent and in the substantial absence of an organic solvent to form a first dispersion; and
- a further aspect of this invention comprises a process of preparing a photographic element which comprises the steps of: (a) milling the crystalline solid of the scavenger in an aqueous medium in the presence of a dispersing agent and in the substantial absence of an organic solvent to form a first dispersion;
- This invention provides a method of reducing undesired dye stain in a photographic element when a disulfonamidophenol oxidized developer scavenger is used. This is achieved by the use of the scavenger in the form of a crystalline solid particle dispersion.
- disulfonamidophenol oxidized developer scavengers are used as conventional oil-in-water dispersions, and their use in the form of crystalline solid particle dispersions has not, up to now, been described or suggested.
- disulfonamidophenol oxidized developer scavengers useful in the practice of the present invention are well known and can be prepared by synthesis techniques known in the art.
- Preferred disulfonamidophenol scavengers have the formula:
- R and R! represents a substituted or unsubstituted alkyl or aryl group
- G is hydroxy or an alkali labile precursor thereof; each of R ⁇ and R3 is individually alkyl of 1 to 30 carbon atoms, aryl of 6 to 30 carbon atoms or heterocyclic of 5 to 30 carbon atoms containing one or more ring hetero atoms; and each of R ⁇ , R5 and R ⁇ is individually hydrogen, halogen, alkyl of 1 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms or aryloxy of 6 to 30 carbon atoms; each of Ar 1 and Ar 2 independently is an aryl group; and each of R 7 , R 8 , and R 9 independently is a monovalent group such as hydrogen, a halogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, an alkenyl group, an alkynyl group, a heterocyclic group, an alkoxy group, an alkylthio group, or an acylamino group, each of which may
- Particularly preferred disulfonamidophenol scavengers are compounds of the formula:
- the scavenger compounds should be crystalline solids and substantially water insoluble at coating conditions, which generally involve temperatures from 10 C to 50 C, and pH from 5.0 to 7.0.
- the crystalline solid particle dispersion can be formed by precipitating or reprecipitating the compound in the form of a dispersion in the presence of one or more dispersing agents, or by well known milling techniques. Reprecipitating techniques which involve dissolving the scavenger and precipitating by changing the solvent and/or pH in the presence of a dispersing agent are well known in the art. Reprecipitating techniques are described, for example, in US Application Serial No. 07/812,503 by Texter, et al, filed 12/20/91, and are herein incorporated by reference.
- Milling techniques are also well known in the art, and examples include ball milling, media milling, attritor milling, jet milling or colloid milling the scavenger in the presence of a dispersing agent.
- the dispersing agent is preferably an anionic, nonionic or zwitterionic surfactant, or a water soluble homopolymer or copolymer. Mixtures of two or more dispersing agents can be used in the practice of this invention.
- the total amount of dispersing agent can vary over a wide range, generally from about 1% to about 200%, preferably about 5% to about 100%, the percentages being by weight, based on the weight of the scavenger.
- Particularly preferred dispersing agents are an alkali metal salt of an alkarylene sulfonic acid, such as the sodium salt of dodecyl benzene sulfonic acid, the sodium salt of isopropylnaphthalene sulfonic acid or a mixture of monomers, dimers, trimers and tetramers of the sodium salt of isopropylnaphthalene sulfonic acid; an alkali metal salt of an alkyl sulfuric acid, such as sodium decyl sulfate or sodium dodecyl sulfate; or an alkali metal salt of an alkyl sulfosuccinate, such as sodium bis (2-ethylthexyl) succinic sulfonate, diethylpentyl sodium sulfosuccinate, dimethylpentyl sodium sulfosuccinate.
- an alkali metal salt of an alkarylene sulfonic acid such as the sodium
- milling media is used to prepare the dispersion
- the mill is charged with the media such as, for example, spheres of silica, sand, zirconium oxide, zirconium silicate, alumina, titania, glass, etc.
- the bead sizes typically range from 0.25 to 3.0 millimeters (mm) in diameter.
- the scavenger particles in the dispersion should have mean diameters from 0.01 to 10.0 micrometers ( ⁇ m) and preferably from 0.05 to 5.0 micrometers ( ⁇ m) .
- the use of solid particle dispersions in imaging are described, for example in, US Patent No. 4,006,025 to Swank et al and US Patent No.
- the scavenger compounds can be used in the ways and for the purposes that scavengers for oxidized developing agent are employed in the art. They can be incorporated in a silver halide emulsion layer of the photographic element or in a separate layer of the element. When incorporated in a separate layer, that layer is preferably an interlayer between silver halide emulsion layers although it can be an undercoat layer coated below all of the silver halide emulsion layers or an overcoat layer coated above all of the silver halide emulsion layers.
- the two silver halide layers preferably comprise a coupler that can react with oxidized developer such as a color developer to form or release a photographically useful group.
- oxidized developer such as a color developer
- photographically useful groups are known in the art and may be groups such as dyes, development modifiers such as development inhibitors, and the like.
- the amount of scavenger compound employed will depend upon the particular purpose for which the scavenger is to be used and the degree of scavenging desired. Typically useful results are obtained when the scavenger is employed in an amount of between about 5 and 1000 mg/sq. meter per layer.
- the vehicle for the crystalline solid particle dispersion can be essentially any photographic vehicle, such as gelatin and other hydrophilic colloids, or various synthetic polymers such as polyvinyl alcohol or acrylamide polymers.
- Photographic vehicles commonly employed in silver halide photographic elements are described in Research Disclosure. December 1978, Item No. 17643, Section IX, the disclosure of which is incorporated herein by reference.
- the photographic elements of the present invention can be simple black-and-white or monochrome elements comprising a support bearing a layer of the silver halide emulsion, or they can be multi-layer and/or multicolor elements. They can be designed for processing with separate solutions or for in-camera processing.
- Multicolor elements contain dye image forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
- the layers of the element, including the layers of the image-forming units, can be arranged in any desired order.
- the emulsion or emulsions can be disposed as one or more segmented layers, e.g., as by the use of microvessels or microcells, as described in U.S. Patent No. 4,362,806 to Whitmore.
- a preferred photographic element comprises a support bearing at least one blue-sensitive silver halide emulsion layer having associated therewith a yellow image dye-providing material, at least one green-sensitive silver halide emulsion layer having associated therewith a magenta image dye-providing material and at least one red- sensitive silver halide emulsion layer having associated therewith a cyan image dye-providing material, the element containing a scavenger of this invention.
- the scavenger is in an interlayer between silver halide emulsion layers sensitive to the same or different silver halide emulsion layers.
- the elements of the present invention can contain additional layers conventional in photographic elements, such as overcoat layers, spacer layers, filter layers, antihalation layers, pH lowering layers (sometimes referred to as acid layers and neutralizing layers), timing layers, opaque reflecting layer, opaque light-absorbing layers and the like.
- the support can be any suitable support used with photographic elements. Typical supports include polymeric films, paper (including polymer-coated paper) , glass and the like. Details regarding supports and other layers of the photographic elements of this invention are contained in Research Disclosure, December 1978, Item 17643, referred to above.
- the support can be coated with a magnetic recording layer as discussed in Research Disclosure 34390 of November 1992, the disclosure of which is incorporated herein by reference.
- the light-sensitive silver halide emulsions employed in the photographic elements of this invention can include coarse, regular or fine grain silver halide crystals or mixtures thereof and can be comprised of such silver halides as silver chloride, silver bromide, silver bromo-iodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide, and mixtures thereof.
- the emulsions can be negative working or direct positive emulsions. They can form latent images predominantly on the surface of the silver halide grains or in the interior of the silver halide grains. They can be chemically and spectrally sensitized in accordance with usual practices.
- the emulsions typically will be gelatin emulsions although other hydrophilic colloids can be used in accordance with usual practice. Details regarding the silver halide emulsions are contained in Research Disclosure. Item 17643, December 1978, and the references listed therein.
- the photographic silver halide emulsions can contain other addenda conventional in the photographic art. Useful addenda are described, for example, in Research Disclosure, December 1978, Item 17643.
- Useful addenda include spectral sensitizing dyes and desensitizers, antifoggants, masking couplers, DIR couplers, DIR compounds, anti-stain agents, image dye stabilizers, absorbing materials, coating aids, plasticizers and lubricants, and the like.
- the dye image-providing material employed in the photographic element can be incorporated in the silver halide emulsion layer or in a separate layer associated with the emulsion layer.
- the dye image-providing material can be any of a number known in the art, such as dye-forming couplers, bleachable dyes, dye developers and redox dye- releasers, and the particular one employed will depend on the nature of the element and the type of image desired.
- Dye image-providing materials employed with conventional color materials designed for processing with separate solutions are preferably dye-forming couplers; i.e., compounds which couple with oxidized developing agent to form a dye.
- Preferred couplers which form cyan dye images are phenols and naphthols.
- Preferred couplers which form magenta dye images are pyrazolones and pyrazolotriazoles.
- Preferred couplers which form yellow dye images are benzoylacetanilides and pivalylacetanilides.
- Dye image-providing materials useful in diffusion transfer film units contain a dye moiety and a monitoring moiety.
- the monitoring moiety in the presence of an alkaline processing solution and as a function of silver halide development, is responsible for a change in mobility of the dye moiety.
- These dye image-providing materials can be initially mobile and rendered immobile as a function of silver halide development, as described in U.S. Pat. No. 2,983,606. Alternatively, they can be initially immobile and rendered mobile, in the presence of an alkaline processing solution, as a function of silver halide development. This latter class of materials include redox dye-releasing compounds.
- the monitoring group is a carrier from which the dye is released as a direct function of silver halide development or as an inverse function of silver halide development.
- Compounds which release dye as a direct function of silver halide development are referred to as negative-working release compounds, while compounds which release dye as an inverse function of silver halide development are referred to as positive-working release compounds.
- the developing agents that can be used to develop the photographic elements of this invention, the oxidized form of which can be reduced by the scavengers of this invention, include hydroquinones, aminophenols, 3-pyrazolidones and phenylene diamines . Some of these developing agents, when used for certain applications, are referred to in the art as electron transfer agents.
- the particular developing agent employed will depend on the particular type of photographic element to be processed. For example, phenylene diamines are the developers of choice for use with color photographic elements containing dye-forming couplers, while 3-pyrazolidones are preferably used with image transfer materials containing redox dye releasers .
- Representative developing agents include: hydroquinone, N-methylaminophenol, l-phenyl-3- pyrazolidone, l-phenyl-4, 4-dimethyl-3-pyrazolidone, 1- phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone, N,N- diethyl-p-phenylenediamine, 3-methyl-N,N-diethyl-p- phenylenediamine, 3-methoxy-N,N-diethyl-p- phenylenediamine, N,N,N' ,N' -tetramethyl-p- phenylenediamine.
- Dispersion A of a photographically useful disulfonamidophenol oxidized developer scavenger, Compound 1, was prepared by placing 120 g of Compound 1 in a 1-gallon glass jar containing 664 g distilled water, 16.0 g of a 75% aqueous solution of diethylhexyl sodium sulfosuccinate, commercially available as Aerosol OT from American Cyanamid, and 2000 ml of 1.8 mm zirconium oxide beads. The jar was rolled at a speed of 103 ft/min for 7 days. The milled slurry was mixed with gelatin and water to yield a dispersion containing 6% Compound 1 and 9% gelatin.
- Dispersion B was prepared in the same manner as Dispersion A except it contained 8.0 g of a 75% aqueous solution of Aerosol OT, 60.0 g of a 10% aqueous solution of polyvinylpyrrolidone and 312.0 g distilled water.
- a conventional oil-in-water dispersion, Dispersion C, of compound 1 was prepared by dissolving 12.0 g of compound 1 in 6.0 g of N, N-diethyl lauramide and 24.0 g of ethyl acetate at 60C, then combining with an aqueous phase consisting of 16.0 g gelatin, 6.0 g of a 10% solution of a mixture of monomers, dimers, trimers and tetramers of the sodium salt of isopropylnaphthalene sulfonic acid, commercially available as Alkanol-XC from DuPont, and 136.0 g distilled water. The mixture was then passed through a colloid mill 5 times, followed by evaporation of the ethyl acetate using a rotary evaporator and replacement with distilled water to yield a dispersion having 6.0% compound 1 and 8.0% gelatin.
- Dispersion D was prepared the same as Dispersion C except N, N-di-n-butyl lauramide was substituted for N, N-diethyl lauramide.
- Dispersion E was prepared the same as Dispersion D except 12.0 g of N, N-di-n-butyl lauramide and 130.0 g of water were used.
- Dispersion F was prepared the same as Dispersion C except 1, 4-cyclohexylenedimethylene bis (2-ethylhexanoate) was substituted for N, N-diethyl lauramide.
- Dispersion G was prepared the same as Dispersion C except N, N-diethyl lauramide was omitted from the formulation, and 142.0 g of distilled water was used.
- a conventional oil-in-water dispersion, Dispersion H, of a photographically useful hydrazide oxidized developer scavenger, Compound 2 was prepared by dissolving 12.0 g of Compound 2 in 12.0 g of di-n- butylphthalate and 24.0 g of ethyl acetate at 60C, then combining with an aqueous phase consisting of 16.0 g gelatin, 6.0 g of a 10% solution of Alkanol-XC and 130.0 g distilled water. The mixture was then passed through a colloid mill 5 times, followed by evaporation of the ethyl acetate using a rotary evaporator and replacement with distilled water to yield a dispersion having 6.0% compound 2 and 8.0% gelatin.
- Dispersion I was prepared the same as Dispersion H except 3.0 g N, N-diethyl lauramide was substituted for 12.0 g di-n-butylphthalate, and 139.0 g distilled water was used.
- oxidized developer dispersions were evaluated as set forth below in color negative photographic material prepared, exposed and processed according to conventional procedures .
- Multilayer films were prepared, each comprising three color records separated by one or more interlayers, each of which contains a dispersion of oxidized developer scavenger.
- the purpose of the interlayer is to prevent oxidized developer generated in one of the color layers from affecting any chemical reactions in another color layer.
- the dye stain of concern is manifested by a spectral absorption at 640-660 nm. Therefore in evaluating the dispersions of this invention compared to conventional oil-in-water dispersions, the dispersions were incorporated into an interlayer positioned between green- and red-sensitive layers of a multilayer film structure.
- the multilayer film structure contained additional color sensitive layers and interlayers .
- the additional interlayers contained no oxidized developer scavenger, the oxidized developer scavenger being evaluated or a hydrazide oxidized developer scavenger (Cpd. 2) known to be non-staining at the relevant wavelength.
- EXAMPLE 1 the oxidized developer scavenger Compound 1 dispersed as a crystalline solid particle dispersion, Dispersion A, is compared to a conventional oil-in-water dispersion of Compound 1, Dispersion C.
- red-and green-sensitive layers are separated by an interlayer that contains the above dispersions as designated below.
- the photographic element used as a CONTROL in this example contained no oxidized developer scavenger and contained the following relevant layers and materials: FILM STRUCTURE I
- a COMPARISON film structure was prepared in the same manner as the CONTROL except that the interlayer contained 0.9688 g/square meter gelatin and 0.0431 g/square meter Compound 1 incorporated as Dispersion C, a conventional oil-in-water dispersion.
- a film of the INVENTION was prepared in the same manner as the control except that the interlayer contains 0.9688 g/square meter gelatin and 0.0431 g/square meter Compound 1 incorporated as Dispersion A, a crystalline solid particle dispersion.
- the photographic film elements prepared as above were tested for 645 nm dye aggregate as follows:
- the presence (1) of the staining species can be estimated qualitatively by visual examination of the spectrum of a film sample. Quantifying the amount of 645 nm peak is done by the following differencing procedure.
- the spectral density of the film element at 645 nm is recorded.
- the film element is then treated in a persulfate bath to remove the staining species.
- the 645 nm spectral density of the film element is again recorded, and the difference (2) between the two values is calculated.
- Table I demonstrate that the dye stain present with the conventional oil- in-water dispersion, Dispersion C, is not present with the crystalline solid particle dispersion of this invention, Dispersion A.
- the photographic film elements were tested for the ability of the interlayer formulation to prevent color contamination as follows:
- each interlayer formulation may be determined by the following method.
- the multilayer containing interlayers formulated with the control, comparison or invention dispersions was exposed to red or green light only.
- the exposed color record is the only layer that developed and was designated the
- EXAMPLE 2 the oxidized developer scavenger Compound 1 dispersed as crystalline solid particle dispersions, Dispersion A and Dispersion B, are compared to the conventional oil-in-water dispersion of Compound 1, Dispersion C.
- red- and green-sensitive layers are separated by an interlayer that contains the dispersions as described below.
- the photographic element used as a control in this example contains the following relevant layers and materials :
- AgBrl tabular grain emulsion 4.1%I, 0.80x0.09 ⁇ m, sensitized with dye cpds 3 & 4, 0.87 mmole/Ag mole, 0.6458 g/m 2 magenta dye forming coupler, cpd 5, 0.4090 g/m 2 magenta dye forming coupler, cpd 6, 0.0678 g/m 2 non color forming DIR coupler, cpd 7, 0.0086 g/m 2 magenta dye forming coupler, cpd 8, 0.0107 g/m 2 gelatin, 1.4316 g/m 2 INTERLAYER: oxidized developer scavenger (DISPERSION H) , 0.0861 g/m 2 gelatin, 0.9688 g/m 2
- the above film structure includes an interlayer which contains a non-staining hydrazide scavenger and is the CONTROL
- a COMPARISON film structure was prepared in the same manner as the CONTROL except that in the interlayer, Dispersion H containing Compound 2, was replaced with 0.0431 g/square meter Compound 1 incorporated as a conventional oil-in-water dispersion, Dispersion C.
- a second multilayer film of the invention, INVENTION 2-2 was prepared in the same manner as the CONTROL except that in the interlayer, Dispersion H containing Compound 2 was replaced with 0.0431 g/square meter Compound 1 incorporated as Dispersion B, a crystalline solid particle dispersion in accordance with this invention.
- the multilayer films prepared above were tested for 645 nm dye aggregate as set forth in Example 1 above. As reported in Table II, the crystalline solid particle dispersions of INVENTION 2-1 and INVENTION 2-2 retain less stain than the COMPARISON so that their performance is equal to or better than the nonstaining CONTROL and better than the COMPARISON.
- interlayers present in the multilayer film element contained a non-staining hydrazide scavenger which does not affect the results of the evaluation. These interlayers were not varied in Example 2.
- the oxidized developer scavenger Compound 1 dispersed as a crystalline solid particle dispersion, Dispersion B is compared to conventional oil-in-water dispersions of Compound 1, as Dispersion F, Dispersion G, Dispersion E and Dispersion D.
- Red- and green-sensitive layers are separated by an interlayer that contains the dispersions as described below.
- the photographic element used as COMPARISON 3-1 in this example contains the following layers and materials: FILM STRUCTURE III GREEN SENSITIVE LAYER: AgBrl tabular grain emulsion, 4.1% I,
- INTERLAYER oxidized developer scavenger (DISPERSION F) , 0.0431 g/m 2 gelatin, 0.9688 g/m 2
- a second multilayer comparative film COMPARISON 3-2 was prepared in the same manner as COMPARISON 3-1, except that in the interlayer, the conventional oil-in-water dispersion of Compound 1, Dispersion F, is replaced with 0.0431 g/square meter Compound 1 incorporated as a conventional oil-in-water dispersion, Dispersion G.
- COMPARISON 3-3 was prepared in the same manner as COMPARISON 3-1, except that in the interlayer, the conventional oil-in-water dispersion of Compound 1 Dispersion F is replaced with 0.0431 g/square meter Compound 1 incorporated as a conventional oil-in-water dispersion, Dispersion E.
- a fourth multilayer comparative film, COMPARISON 3-4 was prepared in the same manner as COMPARISON 3-1 except that in the interlayer, the conventional oil-in-water dispersion of Compound 1 Dispersion F is replaced with 0.0431 g/square meter Compound 1 incorporated as a conventional oil-in-water dispersion, Dispersion D.
- INVENTION was prepared in the same manner as COMPARISON 3-1 except that in the interlayer, the conventional oil-in-water dispersion of Compound 1, Dispersion F, is replaced with 0.0431 g/square meter Compound 1 incorporated as a crystalline solid particle dispersion in accordance with this invention Dispersion B.
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1994/005448 WO1995031753A1 (en) | 1994-05-16 | 1994-05-16 | Photographic element having reduced dye stain |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0708932A1 true EP0708932A1 (de) | 1996-05-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94921905A Withdrawn EP0708932A1 (de) | 1994-05-16 | 1994-05-16 | Photographisches element mit verringerter restanfärbung |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0708932A1 (de) |
| JP (1) | JPH09500984A (de) |
| WO (1) | WO1995031753A1 (de) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1193129A (en) * | 1982-06-18 | 1985-09-10 | Robert E. Ross | Photographic elements containing scavengers for oxidized developing agents |
| JPS6146950A (ja) * | 1984-08-10 | 1986-03-07 | Fuji Photo Film Co Ltd | 写真感光材料 |
| US5198517A (en) * | 1991-08-06 | 1993-03-30 | Eastman Kodak Company | Polymeric scavengers for oxidized developing agents and photographic elements containing the same |
| US5192646A (en) * | 1991-12-09 | 1993-03-09 | Eastman Kodak Company | Photographic elements having sulfoxide coupler solvents and addenda to reduce sensitizing dye stain |
| US5300394A (en) * | 1992-12-16 | 1994-04-05 | Eastman Kodak Company | Dispersions for imaging systems |
-
1994
- 1994-05-16 EP EP94921905A patent/EP0708932A1/de not_active Withdrawn
- 1994-05-16 JP JP7529597A patent/JPH09500984A/ja active Pending
- 1994-05-16 WO PCT/US1994/005448 patent/WO1995031753A1/en not_active Ceased
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| Title |
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| See references of WO9531753A1 * |
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| Publication number | Publication date |
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| WO1995031753A1 (en) | 1995-11-23 |
| JPH09500984A (ja) | 1997-01-28 |
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