US3698907A - Light-sensitive silver halide color-photographic material - Google Patents
Light-sensitive silver halide color-photographic material Download PDFInfo
- Publication number
- US3698907A US3698907A US101141A US3698907DA US3698907A US 3698907 A US3698907 A US 3698907A US 101141 A US101141 A US 101141A US 3698907D A US3698907D A US 3698907DA US 3698907 A US3698907 A US 3698907A
- Authority
- US
- United States
- Prior art keywords
- absorber
- light
- silver halide
- exemplified
- photographic material
- 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
- 239000000463 material Substances 0.000 title abstract description 21
- 229910052709 silver Inorganic materials 0.000 title abstract description 20
- 239000004332 silver Substances 0.000 title abstract description 20
- -1 silver halide Chemical class 0.000 title abstract description 20
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 abstract description 12
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 abstract description 12
- 239000006097 ultraviolet radiation absorber Substances 0.000 abstract description 2
- 239000006096 absorbing agent Substances 0.000 description 55
- 239000002904 solvent Substances 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000839 emulsion Substances 0.000 description 24
- 239000010410 layer Substances 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 18
- 239000000523 sample Substances 0.000 description 14
- 108010010803 Gelatin Proteins 0.000 description 12
- 229920000159 gelatin Polymers 0.000 description 12
- 239000008273 gelatin Substances 0.000 description 12
- 235000019322 gelatine Nutrition 0.000 description 12
- 235000011852 gelatine desserts Nutrition 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 238000005562 fading Methods 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229960002380 dibutyl phthalate Drugs 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 3
- 229910001864 baryta Inorganic materials 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XTMNKERQBBIEOT-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O XTMNKERQBBIEOT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- XBGIYLMKMCTDEB-UHFFFAOYSA-N (2-chloro-3,4-diphenylphenyl) dihydrogen phosphate Chemical compound C=1C=CC=CC=1C1=C(Cl)C(OP(O)(=O)O)=CC=C1C1=CC=CC=C1 XBGIYLMKMCTDEB-UHFFFAOYSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- WNCMAOMHAVGIAT-UHFFFAOYSA-N (4-tert-butyl-2,3-diphenylphenyl) dihydrogen phosphate Chemical compound C=1C=CC=CC=1C=1C(C(C)(C)C)=CC=C(OP(O)(O)=O)C=1C1=CC=CC=C1 WNCMAOMHAVGIAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 description 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- UCVPKAZCQPRWAY-UHFFFAOYSA-N dibenzyl benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 UCVPKAZCQPRWAY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 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
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- LORSVOJSXMHDHF-UHFFFAOYSA-N tris(4-tert-butylphenyl) phosphate Chemical compound C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C=CC(=CC=1)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1 LORSVOJSXMHDHF-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
Definitions
- UV-absorber to be used for such purpose as mentioned above should be colorless or substantially colorless, in general, and be inert to other photographic additives and various treating liquids, and are required to be excellent in UV-absorbing property and stable to UV-light.
- those of the hydroxybenzotriazole type have been known as excellent UV-absorbers.
- the hydroxybenzotriazole type UV-absorbers display their excellent UV-absorbing properties when dispersed according to the solvent dispersion method into the layers constituting light-sensitive color-photographic materials.
- the solvent dispersion method is effective for finely and uniformly dispersing a non-diffusing aromatic compound in non-crystalline form into a hydrophilic binder, and is carried out in such a manner that a non-diffusing aromatic compound is added to an organic solvent comprising a difiicultly watersoluble high boiling solvent or a mixture thereof with a low boiling solvent and then dispersed in a hydrophilic binder.
- the hydroxybenzotriazole type UV-absorber has excellent solubility for the abovementioned organic solvent. For this reason, there has been adopted such a procedure that an oleophilic group of a relatively long chain is introduced into the hydroxybenzotriazole type UV-absorber to enhance the solubility thereof for said organic solvent. Due to introduction of 3,698,907 Patented Oct. 17, 1972 the oleophilic group, however, the UV-absorber is increased in molecular weight, but does not change in fundamental structure for UV-absorption.
- the UV-absorber cannot display the same UV-absorbing effect as attained before introduction of the oleophilic group, unless the amount of the UV-absorber is increased. If the amount of the UV-absorber is increased, however, there are brought about coloration, staining and the like drawbacks.
- R R R R and R are individually a hydrogen or a halogen atom, or an alkyl, cycloalkyl, alkoxy, aryl, carbalkoxy or alkylsulfonic group, is used in combination with a compound of the general Formula II,
- R and R are individually hydrogen, alkyl, alkoxy or acyl group; X is -C() or COO--; and n is 1 or 2, the UV-absorber shows prominent solubility for an organic solvent comprising a diflicultly watermiscible high boiling solvent or a mixture thereof with a low boiling solvent.
- groups R R and R in the above-mentioned general Formula I may be less in number of carbon atoms, so that when incorporated with the above-mentioned hydroxybenzotriazole type UV-absorber, a lightsensitive silver halide photographic material can be prevented from deterioration in photographic properties due to increase in amount of UV-absorber or organic solvent, can retain the UV-absorber stably and can give a colored dye image which has been improved in light fastness.
- each of the groups R R and R has 6 or less carbon atoms and the sum of the carbon atoms of R R and R is 8 or less.
- a hydroxybenzotriazole type UV-absorber containing substituents having such a small number of carbon atoms can also be dissolved quite successfully in the organic solvent used in the solvent dispersion method due to the presence of a compound of the general Formula II.
- Table 1 set forth below shows the results obtained by comparing the amount, necessary for dissolving 1 g. of a UV-absorber of the general Formula I, of a solvent comprising dibutyl phthalate alone with that of a solvent comprising a 1:1 mixture of dibutyl phthalate and a compound of the general Formula II, and the results obtained by measuring the time required for each of the resulting solution to deposit the UV-absorber when stored at C.
- Table 2 shows the results obtained by measuring the variation in time required for deposition of UV- fear of deposition of the UV-absorber or no such fear as coloration or staining due to increase in amount of the absorber when each of the solvents set forth in Table 1 UV-absorber; and there is no such fear'that the resulting was used in excess of the required amount.
- the hydroxybenzotriazole type UV-absorber of the general Formula I when used in the solvent dispersion method in combination with the compound of the general Formula II, there can be attained such advantages that not only the amount of the organic solvent used but also the amount of the UV-absorber can be decreased; the UV-absorber can be stably dispersed without any fear of deposition, so that even during the prepara tion and storage of a light-sensitive silver halide colorphotographic material incorporated therewith, there is no inhibited from penetration of various photographic treating liquids due to increase in amount of the organic solvent used.
- hydroxybenzotriazole type UV- absorbers of the general Formula I are as follows:
- a light-sensitive silver halide color-photographic material incorporated with said compounds may be prepared by dissolving a mixture of the compounds of the Formula I and II in suitable proportions in a difficultly water-riscible high boiling solvent, if necessary in admixture with a low boiling solvent as an auxiliary solvent, dispersing the resulting solution into an aqueous gelatin solution by use of a suitable surface active agent, adding the thus formed dispersion to an aqueous gelatin solution for forming a silver halide photographic emulsion layer or other layer, and then subjecting the resulting mixture to ordinary process for preparing a light-sensitive silver halide color-photographic material.
- a low boiling solvent has been used as the auxiliary solvent, it may be removed by the water-washing treatment carried out after cooling, setting and finely dividing the dispersion, by the heating of the dispersion or by the drying treatment carried out during preparation of the photographic material.
- the silver halide photographic emulsion to he employed in the above case may be any of silver chloride, silver bromide and silver iodobromide emulsions. These emulsions may have been subjected to gold, sulfur or the like chemical sensitization and to color sensitization, and may have been incorporated with stabilizers, vehicles, hardeners, couplers, anti-stain agents, brightening agents and antioxidants.
- the amount of the UV-absorber of the general Formula I is adequately 1 to mg. per 100 cm. of the area to be coated, and the amount of the compound of the general Formula II is desirably 0.1 to 2 parts per part of the UV-absorber. Further, the amount of the organic solvent necessary to dissolve said compounds is preferably substantially equal to that of the compound of the general Formula II.
- the organic solvent used in the solvent dispersion method may be any of the conventional solvents.
- Typical examples of the difiicultly water-miscible high boiling solvent include di-n-butyl phthalate, benzyl phthalate, triphenyl phosphate, tri-o-cresyl phosphate, diphenyl-monop-t-butylphenyl phosphate, monophe'nyl-di-p-t-bu-tylphenyl phosphate, diphenyl-mono-o-chlorophenyl phosphate and tri-p-t-butyl phenyl phosphate.
- Typical examples of the low boiling solvent include methyl acetate, ethyl acetate, propyl acetate, n-butyl acetate, ethyl propionate, carbon tetrachloride, chloroform, methanol, ethanol, dimethylformamide, dioxane and methyl Cellosolve acetate.
- Light-sensitive silver halide color-photographic materials of the present invention which are prepared in the above manner have such excellent characteristics as mentioned previously and, when subjected to ordinary color development, can give colored dye images which have been markedly improved in light fastness.
- EXAMPLE 1 A green-sensitive gelatinous silver chlorobromide emulsion containing a magenta coupler was coated on a photographic baryta paper and then dried to form a light-sensitive emulsion layer.
- samples (1) to (6) were prepared. (Provided that the sample (1) contained only the gelatin solution, and the sample (2) contained only the UV-absorber.)
- Trio-eresy1 phosphate 0.5 cc. Exempllfied UV-absorder 3..-. 1 g. 4 - ⁇ Exemplified compound 12.-... 0.5 g. 89 0.03 0.06 Do.
- Tri-o-cresyl phosphate 0.5 cc.
- Tri-o-cresyl phosphate 0.5 cc.
- This gelatin dispersion ner as in Example 1 the exemplified UV-absorber (5) of was coated on the aforesaid green-sensitive emulsion laythe Formula I and each of the exemplified compounds (6), er so that the amount of the UV-absorber became 0.5 mg. 13), (18) and (26) of the Formula II. Subsequently, per 100 cmfi, and then dried to form an interlayer. the emulsion was coated on a photographic baryta pa- On this interlayer was further coated a blue-sensitive per so that the amount of the UV-absorber (5) besilver chlorobromide emulsion containing a yellow coucame 8.2 mg.
- sample (13) was a so-called blank sample which had only a gelatin inter- TABLE 5 Fade-O-meter exposure Green density lowerltng Strain density ra o Amount (D/DoXlOO), Before After State of Sample number Content of emulsion added percent test test surface 7 gon-adlliigltignfi.g -.fi ns 15 0. 04 0. l4 Unchanged.
- Tri-o-cresyl phosphate 0.5 cc.
- Trl-o-oresyl phosphate 0.5 cc.
- Trl-o-cresyl phosphate 0.5 cc.
- Trl-ocresyl phosphate 0.5 cc.
- Exempllfied UV-absorber 1 1 g. 16
- a light-sensitive silver halide color-photographic material characterized by having a layer incorporated with a dispersion, in an organic solvent comprising a diflicultly water-miscible high boiling solvent or a mixture thereof with a low boiling solvent, of at least one UUV-absorber of the general Formula I wherein R R R R and R are individually a hydrogen or halogen atom or an alkyl, cycloalkyl, alkoxy, aryl, carbalkoxy or alkylsulfonic group, and at least one compound of the general Formula II alkoxy, or acyl group; X is CO or -C00-: and n is 1 or 2.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44105148A JPS4830493B1 (enrdf_load_stackoverflow) | 1969-12-29 | 1969-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3698907A true US3698907A (en) | 1972-10-17 |
Family
ID=14399627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US101141A Expired - Lifetime US3698907A (en) | 1969-12-29 | 1970-12-23 | Light-sensitive silver halide color-photographic material |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3698907A (enrdf_load_stackoverflow) |
| JP (1) | JPS4830493B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2063861A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1336300A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923519A (en) * | 1972-01-03 | 1975-12-02 | Polaroid Corp | U.V. light absorbers in supports of integral diffusion transfer film units |
| US4009038A (en) * | 1974-05-23 | 1977-02-22 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| US4148648A (en) * | 1977-02-16 | 1979-04-10 | Polaroid Corporation | Diffusion transfer elements comprising U V light absorbers |
| US4456681A (en) * | 1982-05-28 | 1984-06-26 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials |
| US4518686A (en) * | 1982-06-05 | 1985-05-21 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material containing UV filter compounds |
| US4540656A (en) * | 1982-06-01 | 1985-09-10 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material |
| US4865957A (en) * | 1985-10-17 | 1989-09-12 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material comprising a combination of cyan couplers and UV absorbers |
| US5455152A (en) * | 1994-09-27 | 1995-10-03 | Eastman Kodak Company | Benzotriazole based UV absorbing monomers and photographic elements containing polymers formed from them |
| US5538842A (en) * | 1993-07-02 | 1996-07-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| USRE37693E1 (en) * | 1982-06-05 | 2002-05-07 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material containing UV filter compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547584A (en) * | 1983-12-29 | 1985-10-15 | General Foods Corporation | 3-Hydroxy-4-methoxyphenyl benzoates |
-
1969
- 1969-12-29 JP JP44105148A patent/JPS4830493B1/ja active Pending
-
1970
- 1970-12-23 US US101141A patent/US3698907A/en not_active Expired - Lifetime
- 1970-12-24 DE DE19702063861 patent/DE2063861A1/de active Pending
- 1970-12-29 GB GB6163770A patent/GB1336300A/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923519A (en) * | 1972-01-03 | 1975-12-02 | Polaroid Corp | U.V. light absorbers in supports of integral diffusion transfer film units |
| US4009038A (en) * | 1974-05-23 | 1977-02-22 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| US4148648A (en) * | 1977-02-16 | 1979-04-10 | Polaroid Corporation | Diffusion transfer elements comprising U V light absorbers |
| US4456681A (en) * | 1982-05-28 | 1984-06-26 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials |
| US4540656A (en) * | 1982-06-01 | 1985-09-10 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material |
| US4518686A (en) * | 1982-06-05 | 1985-05-21 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material containing UV filter compounds |
| USRE37693E1 (en) * | 1982-06-05 | 2002-05-07 | Konishiroku Photo Industry Co., Ltd. | Color photographic light-sensitive material containing UV filter compounds |
| US4865957A (en) * | 1985-10-17 | 1989-09-12 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material comprising a combination of cyan couplers and UV absorbers |
| US5538842A (en) * | 1993-07-02 | 1996-07-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US5455152A (en) * | 1994-09-27 | 1995-10-03 | Eastman Kodak Company | Benzotriazole based UV absorbing monomers and photographic elements containing polymers formed from them |
| US5554759A (en) * | 1994-09-27 | 1996-09-10 | Eastman Kodak Company | Benzotriazole based uv absorbing monomers and photographic elements containg polymers formed them |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2063861A1 (de) | 1971-07-01 |
| GB1336300A (en) | 1973-11-07 |
| JPS4830493B1 (enrdf_load_stackoverflow) | 1973-09-20 |
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