US3692525A - Ultraviolet protection of photographic-materials - Google Patents
Ultraviolet protection of photographic-materials Download PDFInfo
- Publication number
- US3692525A US3692525A US143619A US3692525DA US3692525A US 3692525 A US3692525 A US 3692525A US 143619 A US143619 A US 143619A US 3692525D A US3692525D A US 3692525DA US 3692525 A US3692525 A US 3692525A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- phenyl
- ultraviolet
- photographic
- 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.)
- Expired - Lifetime
Links
- 230000006750 UV protection Effects 0.000 title description 3
- 239000000463 material Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 108010010803 Gelatin Proteins 0.000 abstract description 13
- 229920000159 gelatin Polymers 0.000 abstract description 13
- 239000008273 gelatin Substances 0.000 abstract description 13
- 235000019322 gelatine Nutrition 0.000 abstract description 13
- 235000011852 gelatine desserts Nutrition 0.000 abstract description 13
- 239000000839 emulsion Substances 0.000 abstract description 12
- 230000005855 radiation Effects 0.000 abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 238000005562 fading Methods 0.000 abstract 2
- -1 silver halide Chemical class 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 239000006096 absorbing agent Substances 0.000 description 10
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- YTZPUTADNGREHA-UHFFFAOYSA-N 2h-benzo[e]benzotriazole Chemical class C1=CC2=CC=CC=C2C2=NNN=C21 YTZPUTADNGREHA-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 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 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 239000012496 blank sample Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 238000001739 density measurement Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- KYMSAPXLDYKYEN-UHFFFAOYSA-N 4-phenyl-2H-benzo[e]benzotriazole Chemical class C1(=CC=CC=C1)C1=CC2=CC=CC=C2C=2NN=NC21 KYMSAPXLDYKYEN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UVKOJLKMODVQGC-UHFFFAOYSA-N OC1=C(C2=C(NN=N2)C2=CC=CC=C12)C1=CC=CC=C1 Chemical class OC1=C(C2=C(NN=N2)C2=CC=CC=C12)C1=CC=CC=C1 UVKOJLKMODVQGC-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 239000011230 binding agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/22—Naphthotriazoles
-
- 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
Definitions
- This invention relates to a photographic element, and the preparatory process therefor, containing a light-sensitive silver halide emulsion stabilized against the deleterious effects of ultraviolet radiation and, more particular- 1y, to said element stabilized by the incorporation therein of certain naphthotriazoles.
- UV absorbers Many and varied compounds have been used as ultraviolet absorbers. Criteria for acceptable absorbers include non-diifusibility, freedom from color, inertness, compatibility and, of course, good ultraviolet absorption and stability to ultraviolet. Such compounds have been used either incorporated into the silver halide emulsion layer or in a layer superior but contiguous thereto. Among the methods for accomplishing such incorporation is a solvent-dispersion technique in which the ultraviolet absorber compound is dissolved in an organic plasticizer which is, in turn, intimately blended into an aqueous gelatin solution. This procedure, however, has certain shortcomings, chief among which is a decrease in the light stability of the incorporated absorber compounds.
- R, R and R each preferably represents hydrogen or an alkyl of 1 to 20 carbon atoms, at least one of the groups R, R and R containing at least mism of less than 250 A. may also be present. These insaid groups being 3 to 24 and preferably being 4 to 16. Other non-chromophoric substituents with a bathochromism of less than 250A. may also be present. These include halogen, preferably chlorine, carboxy, carbalkoxy, cyan, sulfamyl (sulfonamide), carbanyl (carboxamido), etc.
- Substituted alkyls may also be used as, for example, hydroalkyl, haloalkyl, cyanalkyl, alkoxyalkyl and lactam methylene. Details as to specific substituents can be found in the co-pending application of Catino and Strobel, Ser. No. 504,206, filed Oct. 23, 1965, now abandoned, and in corresponding French Pat. 1,497,191 issued Aug. 28, 1967.
- the general method of preparation of these compounds involved the diazotizing and coupling of an orthoamino phenol to an amino naphthalene or the diazotizing and coupling of an o-nitronaphthylaminc to a substituted phenol in such a manner that the coupling is either ortho to the amino group of the naphtho ring or ortho to the hydroxy group of the phenol.
- compositions of this invention include: 2 (2-hydroxy-5-t-octylphenyl)naphtho(1,2-d)triazole,
- A represents a naphthalene ring bound by 2 adjacent carbon atoms to two nitrogen atoms of the triazole ring and B represents the phenyl radical containing a hydroxyl group ortho to the nitrogen atom of the triazole ring to which the phenyl radical is linked,.the col-. umns below list other substituents suitable for the compositions of this invention.
- famyl naphtho G-N ,N-dimethylsul- (2-hydroxy-3,5'-ditertiaryamyl)phenyliamyl naphtha.
- E-cyano naphtho (2'-hydroxy-3 ,5 -ditertiaryamyl)phenyl.
- fi-methoxy naphtho (2"hydroxy-3,5-ditertiaryamyl)aphenyl.
- the compounds are incorporated into the emulsion layer or into a layer contiguous therewith by the solvent dispersion procedure as discussed previously.
- a representative system uses high-boiling, water-immiscible organic plasticizers.
- the plasticizer system containing the ultraviolet absorber, and such additives as desired or required, is dispersed in an aqueous gelatin solution with the aid of an emulsifier to produce a finely divided, non-crystalline form of a non-diffusable ultraviolet absorber.
- the gelatin layers were prepared by adding 15 grams of the above absorber dispersion (containing 1.2 grams of the ultraviolet absorber) to 200 ml. of a 2.5% gelatin solution containing 5 ml. of saponin and applying this solution to aclear film support such that the dry coating thickness was 4 to 5 microns. These clear gelatin layers were processed through the solutions normally employed in color print work.
- Sections 1 x /2" were cut from the clear film and superposed on the unexposed color print paper which had been processed in the normal manner. These absorber hours in the Atlas Fade-Ometer and subjected to the ultraviolet radiation as heretofore explained. The yellow discoloration resulting from ultraviolet degradation of unused color former was again determined by reflection density measurements. In addition the loss in yellow dye covered strips were then exposed for ten hours in an Atlas 5 density was determined by similar yellow dye density Fade-Ometer to the radiation of a single enclosed violet measurements with correction made for the yellow stain carbon arc in which 20.3% of the emitted radiation is in developed. Results are tabulated below.
- Example 9 the sample containing the preferred compound of this invention [2-(2'-hydroxy-3',5-ditertiaryamylphenyl)naphthotriazole], there is a twofold decrease in the amount of yellow stain developed on exposure to ultraviolet radiation in comparison with those samples containing the absorber compounds of the prior art (Examples 11 and 12).
- the loss in yellow dye density in the aforesaid Example 9 is 1.5 to 2.7 times less than the corresponding loss in the samples compounded with the absorbers of the prior art. Since these EXAMPLES 8- 14 These examples illustrate the suitability of the ultraviolet absorber compounds of this invention when incorporated into one of the color forming layers of a multilayer color photographic element.
- Dispersions containing the ultraviolet absorber compound with a cyan color former were prepared following a procedure analogous to that described in Examples 1-7 above with both the ultraviolet absorber and the cyan color former dissolved in the solvents.
- the dispersion composition was constituted as listed below.
- Each dispersion was, in turn, admixed with red sensitized silver halide emulsions containing the necessary coating finals and this mixture was then coated over the yellow and magenta dye-forming layers on a paper support to form a multilayer color photographic element. After the element was given red, green and blue separation exposure and processed, it was then positioned for 10 results are measures of the intra-layer and extra-layer ultraviolet degradation effects respectively, they are indicative of the protective ability of the naphthotriazoles when either intimately admixed in the emulsion layer or applied as an exterior coating over the emulsion layer.
- a photographic element comprising a support having thereon at least one photographic silver halide emulsion layer and a superposed gelatin layer, at least one of said layers containing a hydrophobic compound having the formula:
- R, R and R each represents a member selected from the class consisting of hydrogen, halogen, alkyl groups having from 1 to 20 carbon atoms, hydroxyalkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkoxy, aryloxy, cyano, carbalkoxy, alkyl sulfonyl, sulfamyl, N-alkyl sulfamyl, N-phenyl sulfamyl, N-heterocyclic sulfamyLcarbamyl, N-alkyl carbamyl, N phenyl carbamyl, N heterocyclic canbamyl and lactam methylene groups, at least one of the groups R, R and R containing at least 3. carbon atoms.
- a photographic element as defined in claim 2 wherein the layer containing said compound is formed from a dispersion comprising a hydrophilic colloid binder material, a high-boiling, water immiscible organic plasticizer and said compound.
- v i I 4 A photographic element as defined in claim 1 wherein said superposed gelatin layer contains said compound;
- a photographic element as definedin claim 4 wherein the superposed gelatin layer containing said compound, is formed from a dispersion comprising gelatin, a high boiling water immiscible organic plasticizer and said compound.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67673167A | 1967-10-20 | 1967-10-20 | |
| US14361971A | 1971-05-14 | 1971-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3692525A true US3692525A (en) | 1972-09-19 |
Family
ID=26841252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US143619A Expired - Lifetime US3692525A (en) | 1967-10-20 | 1971-05-14 | Ultraviolet protection of photographic-materials |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3692525A (enExample) |
| BE (1) | BE722542A (enExample) |
| DE (1) | DE1803746A1 (enExample) |
| FR (1) | FR1588447A (enExample) |
| GB (1) | GB1239258A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968704A (en) * | 1988-08-13 | 1990-11-06 | Pfizer Inc. | Pyridine compounds which are useful as anti-arrhythmic agents |
| US5772920A (en) * | 1995-07-12 | 1998-06-30 | Clariant Finance (Bvi) Limited | U.V. absorber compositions |
| WO2013103139A1 (ja) | 2012-01-06 | 2013-07-11 | コニカミノルタアドバンストレイヤー株式会社 | フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置 |
-
1968
- 1968-10-11 GB GB1239258D patent/GB1239258A/en not_active Expired
- 1968-10-18 DE DE19681803746 patent/DE1803746A1/de active Pending
- 1968-10-18 FR FR1588447D patent/FR1588447A/fr not_active Expired
- 1968-10-18 BE BE722542D patent/BE722542A/xx unknown
-
1971
- 1971-05-14 US US143619A patent/US3692525A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968704A (en) * | 1988-08-13 | 1990-11-06 | Pfizer Inc. | Pyridine compounds which are useful as anti-arrhythmic agents |
| US5772920A (en) * | 1995-07-12 | 1998-06-30 | Clariant Finance (Bvi) Limited | U.V. absorber compositions |
| WO2013103139A1 (ja) | 2012-01-06 | 2013-07-11 | コニカミノルタアドバンストレイヤー株式会社 | フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1803746A1 (de) | 1969-07-10 |
| BE722542A (enExample) | 1969-04-01 |
| FR1588447A (enExample) | 1970-04-10 |
| GB1239258A (enExample) | 1971-07-14 |
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