US3754919A - Photographic layers which contain uvabsorbers - Google Patents

Photographic layers which contain uvabsorbers Download PDF

Info

Publication number: US3754919A
Authority: US; United States
Prior art keywords: absorbent; compounds; compound; layers; contain
Prior art date: 1968-12-06
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

Application number

US00210611A

Other languages

English (en)

Inventor

J Sobel

F Nittel

W Himmelmann

W Pelz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Agfa Gevaert AG

Original Assignee

Agfa Gevaert AG

Priority date (The priority date 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 date listed.)

1968-12-06

Filing date

1971-12-21

Publication date

1973-08-28

1971-12-21 Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG

1973-08-28 Application granted granted Critical

1973-08-28 Publication of US3754919A publication Critical patent/US3754919A/en

1990-08-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 54
239000002250 absorbent Substances 0.000 claims abstract description 34
239000000463 material Substances 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 10
238000009835 boiling Methods 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 abstract description 5
239000011253 protective coating Substances 0.000 abstract description 3
125000005605 benzo group Chemical group 0.000 abstract description 2
239000010410 layer Substances 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 12
230000002745 absorbent Effects 0.000 description 8
238000001556 precipitation Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
238000005266 casting Methods 0.000 description 6
239000011241 protective layer Substances 0.000 description 6
108010010803 Gelatin Proteins 0.000 description 5
239000006096 absorbing agent Substances 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000000975 dye Substances 0.000 description 5
229920000159 gelatin Polymers 0.000 description 5
239000008273 gelatin Substances 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
238000012545 processing Methods 0.000 description 3
-1 silver halide Chemical class 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
230000008033 biological extinction Effects 0.000 description 2
238000004061 bleaching Methods 0.000 description 2
238000012937 correction Methods 0.000 description 2
230000001627 detrimental effect Effects 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000001397 quillaja saponaria molina bark Substances 0.000 description 2
229930182490 saponin Natural products 0.000 description 2
150000007949 saponins Chemical class 0.000 description 2
229910052709 silver Inorganic materials 0.000 description 2
239000004332 silver Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
238000004383 yellowing Methods 0.000 description 2
LVPFIQLQEJUWCB-UHFFFAOYSA-N 2,2-diethyl-3-hexyl-3-sulfobutanedioic acid Chemical compound CCCCCCC(C(O)=O)(S(O)(=O)=O)C(CC)(CC)C(O)=O LVPFIQLQEJUWCB-UHFFFAOYSA-N 0.000 description 1
YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
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 1
239000004904 UV filter Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical class C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- 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
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
- 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

the light stability of color photographic images is improved by overcoating the image carrying layer with a UV-protective coating which contains a UV-absorbing abandoned.
UV-absorbing layer contains as UV-absorbent a [52] US Cl 96/84 R 96/74 252/300 -phenolbenzo-triazole, the benzo ring of which is [51] hit Cl .IIIIIIIIIIIIIIIIIII dose 1/84 substituted with at least 1 alkoxy p.
the invention relates to photographic layers which contain UV-absorbent compounds.
UV-absorbent compounds which absorb light in the UV-region of the spectrum and are, therefore, suitable for the production of UV-filters and UV- protective coatings. Such coatings are used in photographic material for increasing the light fastness of colour images.
the UV-absorbent compounds should be incorporated in a separate protective layer in as high a concentration as possible in order to achieve the great est possible effect. Generally, it is not possible to use the UV-absorbent compounds homogeneously or heterogeneously distributed with the image dyes in one layer, because the absorbent compounds and the dyes are very frequently found to interact with each other so that bleaching of the image is increased.
the UV- absorbent compounds should be colourless and should have a high coefficient of extinction in the UV-region and should be as stable as possible.
the UVabsorbent compounds can be used in many different ways, e.g. in water insoluble binders. In this case, the finished colour image is coated with such a solution in a separate working step. This procedure, however, is only economical for images of large shapes and sizes and is, therefore, not generally applicable. Incorporation of water soluble and water insoluble UV- absorbent compounds in a diffusion fast manner in a protective layer has also been described. In this case, the chemical and physical properties of the UV- absorbent compound must meet certain requirements, e.g. it must be possible for the absorbent compound to be used in a highly concentrated form in layers of a thickness of l to 2 pm without precipitating from the protective layer in the form of crystals or an oil. The UV absorbent compound must, of course, be inert towards photographic processing baths and must not undergo yellowing on exposure to light.
Aromatic azines have, inter alia, been particularly recommended as UV- absorbent compounds, but these generally have a high melting point so that they are difiicult to use because of their tendency to crystallise.
Derivatives of this type which can easily be incorporated in photographic layers, which are described in German Patent No, 1,182,066, are slightly yellowish so that they are detrimental the white color images. The reason for this is that a slight absorption of light from the visible region of the spectrum occurs.
R and R are hydrogen, alkyl or alkoxy groups with up to l8 C-atoms, preferably with up to four C-atoms, in particular branched alkyl or alkoxy groups, but at least one of the substituents R and R is an alkoxy group;
R stands for hydrogen or alkyl with up to five carbon atoms in particular methyl.
Particular utility is exhibited by the following compounds:
the UV-absorbent compounds are particularly readily soluble in those particular solvents which are used as so-called oil forming agents in the production of photographic materials.
the solution can easily be emulsified in the casting solutions for the layers.
UV-absorbent compounds to be used according to the invention may also be used in combination with other UV-absorbent compounds particularly with those of the 2-hydroxyphenyl-benzotriazole series.
the UV-absorbent compounds do not deleteriously influence the photographic properties of adjacent layers and in particular the color coupling reaction of dissolved dye derivatives is not reduced. Many of the known UV-absorbent compounds even of the benztriazole series are detrimental in this respect. The molar extinction coefficient is exceptionally high, so that the quantity of UV-absorbent compound used can be kept compartively low.
the UV-absorbent compounds are preferably emulsified in the casting solutions for the particular layer in the form of their solutions in high boiling solvents, by using a suitable dispersing apparatus.
the proportions in which the UV-absorbent compounds are mixed with the solvents may vary between 1:1 and 1:0.1.
Low boiling auxiliary solvents such as ethyl acetate, methylene chloride, alcohols and mixtures of these solvents may be used. After dispersion, the low boiling solvents are removed in thin layer evaporators under vacuum.
Suitable water insoluble, high boiling compounds are, for example, dibutyl phthalate. tricresyl phosphate and particularly higher fatty acids, and preferably branched fatty acids having about 10 to 20 C-atoms.
the UV-absorbent compounds may be added directly to the silver halide emulsions which contain color couplers or to a gelatin-containing solution of the protective layer.
gelatin layers which contain the UV-absorbent compound may be arranged in any position in the various layers of the photographic material, but are preferably positioned above the layers which contain the image dye.
the UV-absorbent compounds are particularly suitable as the topmost layer for photographic multilayered materials of the usual arrangement.
the concentration of the UV-absorbent compounds in the layers may vary within wide limits. An addition of 10 to 50 percent by weight, based on the binder in the layer, has proved to be sufficient.
the concentration is so chosen that on exposure to
the improvement in fastness is determined by exposing both images at the same color density to the same degree of bleaching.
the ratio of lux hours required gives a measure of the improvement factor.
the improvement factor depends not only on the concentration of the UV-absorbent compound but also on the thickness of the protective layer.
the layers which contain the UV-absorbent compound are completely transparent in the dry state and 10 practically color-less. They are stable against the photographic processing baths, e.g. a colorforming development bath. No yellowing can be detected after prolonged exposure to light.
EXAMPLE 1 A solution of 30 g of compound I, 3 g of bis-(2- ethyl)-hexyl-sulfosuccinate and g of a mixture of highly branched aliphatic carboxylic acids having 15 to 19 C-atoms and 30 g of ethanol and 30 g of methylene 20 chloride are emulsified at 50C with 1 liter of a 10 percent gelatin solution which contains 50 ml of a 10 percent saponin solution as wetting agent.
a mixing siren is used as the emulsifying apparatus.
the dissolved UV-absorbent compound is introduced 5 near to the motor of the mixing siren through a tube.
the above mixture is applied onto a processed multilayer colorphotographic material bearing a color-image in true colors (layer thickness 3 #m).
the light fastness of the color photographic images is greater by a factor of 10 than that found when testing the protective layer which contains no UV-absorbent compound.
a commercial multi-layered color photographic material is coated with the above casting solution as described in Example 1.
the light fastness of the finished image is greater by a factor of about 10 than that of an untreated photographic material.
EXAMPLE 3 The same procedure is used as described in Example 1 but in the casting solution for the layer which contains the UV-absorbent compound, the mixture of branched fatty acids is replaced by an equal quantity of dibutyl phthalate.
EXAMPLE 4 The exceptionally high compatability. with conventional binding agents for photographic UV-absorbing layers in the presence of oil formers in opposition to chemically similar known compounds such as described in U.S. Pat. No. 3,253,921 is shown in the following example:
Test l Into 1 liter ofa 10 percent aqueous gelatin so- 3 ,754,9 1 9 6 lution which contains 2 ml of a 50 percent aqueous Dead multilayer color photographic material in the solution of phenol is emulsified at a temperature of manner described in Example 1. Compounds of the in- 55C during a time of 5 minutes, a solution of 100 vention do not crystallize in the layer.
the protective g of a compound 7 5 g of the bis-(2-ethyl)-hexyl action of the UV-absorbing layers containing comester of sulfosuccinic acid in 200 g of ethyl acetate. 5 pounds of the present invention is considerably higher After emulsification it is stirred for 5 minutes and the than the protective action of layers containing the ethyl acetate evaporized. above prior art compound,
Test 2 The test is performed in the same manner What is claimed is:
a photographic material comprising at least one contained ddi i ll 100 g f tri l h hate, layer containing a silver halide emulsion and incorpo- Test 3: The test is performed in the same manner as rated in a layer of said photographic material a UV- test I with the exception that the ethyl acetate soluabsorbing compound of the following formula:
l jfi Test 4 The test is performed in the same manner as test 2 with the exception that the ethyl acetate solution contained 400 g of the solvent and with the comparison compound of test 3 instead of compound 7. in which The above samples were stored at 40C and in the re- R, and R are, independently of each other, branched frigerator and the behaviour of the emulsions with repropoxy or butoxy groups; spect to the precipitation of the UV-absorbing agents R is hydrogen or an alkyl group having up to five C- is observed Results are shown in the following table. atoms.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)

US00210611A 1968-12-06 1971-12-21 Photographic layers which contain uvabsorbers Expired - Lifetime US3754919A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19681813161 DE1813161A1 (de)	1968-12-06	1968-12-06	Photographische Schichten mit einem Gehalt an ultraviolettes Licht absorbierenden Verbindungen

Publications (1)

Publication Number	Publication Date
US3754919A true US3754919A (en)	1973-08-28

Family

ID=5715495

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US00210611A Expired - Lifetime US3754919A (en)	1968-12-06	1971-12-21	Photographic layers which contain uvabsorbers

Country Status (5)

Country	Link
US (1)	US3754919A (de)
CH (1)	CH524160A (de)
DE (1)	DE1813161A1 (de)
FR (1)	FR2025551A1 (de)
GB (1)	GB1256025A (de)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3936305A (en) *	1973-12-03	1976-02-03	Mitsubishi Paper Mills, Ltd.	Color photographic photosensitive material containing ultraviolet ray-absorbing compound
US4080208A (en) *	1975-01-13	1978-03-21	Addressograph Multigraph Corporation	Photosensitive diazomicrofilm adapted to be readable but nonreproducible upon processing
US4126460A (en) *	1975-08-28	1978-11-21	Fuji Photo Film Co., Ltd.	Light sensitive printing plate comprising a matted overlayer
EP1571181A2 (de)	2004-02-24	2005-09-07	Fuji Photo Film Co., Ltd.	Anorganische feine Teilchen enthaltende Dispersion, Verfahren zu ihrer Herstellung, und Bildaufzeichnungsmaterial
EP1612054A1 (de)	2004-07-02	2006-01-04	Fuji Photo Film Co., Ltd.	Tintenstrahlaufzeichnungsmaterial.
EP1764796A2 (de)	2005-09-07	2007-03-21	FUJIFILM Corporation	Optisches Aufzeichnungsmedium und Herstellungsverfahren dafür
EP1768119A2 (de)	2005-08-25	2007-03-28	FUJIFILM Corporation	Optisches Informationsaufzeichnungsmedium, optisches Informationsaufzeichnungsverfahren und optisches Informationswiedergabeverfahren
EP1974948A2 (de)	2007-03-29	2008-10-01	FUJIFILM Corporation	Bildgebendes Verfahren mit einem wärmeempfindlichen Übertragungssystem
EP1974941A1 (de)	2007-03-29	2008-10-01	FUJIFILM Corporation	Bildgebendes Verfahren mit einem wärmeempfindlichen Übertragungssystem
EP1980409A2 (de)	2007-03-29	2008-10-15	FUJIFILM Corporation	Wärmeempfindliche Übertragungsfolie zur Verwendung in wärmeempfindlichen Übertragungssystemen und Bilderzeugungsverfahren mit wärmeempfindlichem Übertragungssystem
EP1985457A2 (de)	2007-04-25	2008-10-29	FUJIFILM Corporation	Kartonzylinder für ein hitzeempfindliches Übertragungsbildaufnahmeblatt, gerolltes hitzeempfindliches Übertragungsbildaufnahmeblatt zur Formung einer Rollenform und Bilderzeugungsverfahren
EP2020304A1 (de)	2007-08-03	2009-02-04	FUJIFILM Corporation	Tintenstrahlaufzeichnungsmedium
EP2055496A2 (de)	2007-11-01	2009-05-06	Fujifilm Corporation	Tintenstrahlaufzeichnungsmaterial
WO2010013582A1 (ja)	2008-07-30	2010-02-04	富士フイルム株式会社	インクジェット記録方法
WO2010013529A1 (ja)	2008-07-30	2010-02-04	富士フイルム株式会社	インクジェット記録方法
WO2010090213A1 (ja)	2009-02-04	2010-08-12	富士フイルム株式会社	熱分布表示体及び熱分布確認方法
WO2012015076A1 (en)	2010-07-29	2012-02-02	Fujifilm Corporation	Polymerizable composition
EP2436740A1 (de)	2003-09-29	2012-04-04	Fujifilm Corporation	Tinte für Tintenstrahldruck, Tintensatz für Tintenstrahldruck, Tintenstrahlaufzeichnungsmaterial und Herstellungsverfahren für Tintenstrahlaufzeichnungsmaterial und Tintenstrahlaufzeichnungsverfahren
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
WO2014124052A1 (en)	2013-02-06	2014-08-14	Fujifilm Hunt Chemicals, Inc.	Chemical coating for a laser-markable material

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0095920B1 (de) *	1982-06-01	1986-11-26	Konica Corporation	Farbphotographisches lichtempfindliches Material
JPS58209735A (ja) *	1982-06-01	1983-12-06	Konishiroku Photo Ind Co Ltd	カラ−写真感光材料
DE8235915U1 (de) *	1982-12-21	1983-04-14	Siemens AG, 1000 Berlin und 8000 München	Koaxialsteckvorrichtung
US4727158A (en) *	1985-09-03	1988-02-23	Ciba-Geigy Corporation	5-Higher alkyl substituted-2H-benzotriazoles
EP2615699B1 (de) *	2012-01-11	2017-03-22	Spinner GmbH	HF-Verbinder

1968
- 1968-12-06 DE DE19681813161 patent/DE1813161A1/de active Pending
1969
- 1969-11-25 CH CH1751669A patent/CH524160A/de not_active IP Right Cessation
- 1969-12-04 GB GB59188/69A patent/GB1256025A/en not_active Expired
- 1969-12-05 FR FR6942163A patent/FR2025551A1/fr not_active Withdrawn
1971
- 1971-12-21 US US00210611A patent/US3754919A/en not_active Expired - Lifetime

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3936305A (en) *	1973-12-03	1976-02-03	Mitsubishi Paper Mills, Ltd.	Color photographic photosensitive material containing ultraviolet ray-absorbing compound
US4080208A (en) *	1975-01-13	1978-03-21	Addressograph Multigraph Corporation	Photosensitive diazomicrofilm adapted to be readable but nonreproducible upon processing
US4126460A (en) *	1975-08-28	1978-11-21	Fuji Photo Film Co., Ltd.	Light sensitive printing plate comprising a matted overlayer
EP2436740A1 (de)	2003-09-29	2012-04-04	Fujifilm Corporation	Tinte für Tintenstrahldruck, Tintensatz für Tintenstrahldruck, Tintenstrahlaufzeichnungsmaterial und Herstellungsverfahren für Tintenstrahlaufzeichnungsmaterial und Tintenstrahlaufzeichnungsverfahren
EP2130876A1 (de)	2004-02-24	2009-12-09	FUJIFILM Corporation	Anorganische Feinpartikeldispersion, Herstellungsverfahren und Bildaufzeichnungsmaterial
EP1571181A2 (de)	2004-02-24	2005-09-07	Fuji Photo Film Co., Ltd.	Anorganische feine Teilchen enthaltende Dispersion, Verfahren zu ihrer Herstellung, und Bildaufzeichnungsmaterial
EP1612054A1 (de)	2004-07-02	2006-01-04	Fuji Photo Film Co., Ltd.	Tintenstrahlaufzeichnungsmaterial.
EP1768119A2 (de)	2005-08-25	2007-03-28	FUJIFILM Corporation	Optisches Informationsaufzeichnungsmedium, optisches Informationsaufzeichnungsverfahren und optisches Informationswiedergabeverfahren
EP1764796A2 (de)	2005-09-07	2007-03-21	FUJIFILM Corporation	Optisches Aufzeichnungsmedium und Herstellungsverfahren dafür
EP1974948A2 (de)	2007-03-29	2008-10-01	FUJIFILM Corporation	Bildgebendes Verfahren mit einem wärmeempfindlichen Übertragungssystem
EP1974941A1 (de)	2007-03-29	2008-10-01	FUJIFILM Corporation	Bildgebendes Verfahren mit einem wärmeempfindlichen Übertragungssystem
EP1980409A2 (de)	2007-03-29	2008-10-15	FUJIFILM Corporation	Wärmeempfindliche Übertragungsfolie zur Verwendung in wärmeempfindlichen Übertragungssystemen und Bilderzeugungsverfahren mit wärmeempfindlichem Übertragungssystem
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Also Published As

Publication number	Publication date
GB1256025A (en)	1971-12-08
DE1813161A1 (de)	1970-06-25
CH524160A (de)	1972-06-15
FR2025551A1 (de)	1970-09-11

Publication	Publication Date	Title
US3754919A (en)	1973-08-28	Photographic layers which contain uvabsorbers
US3707375A (en)	1972-12-26	Color photographic light sensitive materials having improved light fastness
US3843371A (en)	1974-10-22	Photographic material stabilised against the deleterious effects of ultraviolet radiation
US4383863A (en)	1983-05-17	2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
US3738837A (en)	1973-06-12	Light sensitive color photographic material
US3533794A (en)	1970-10-13	Color photographic light-sensitive material containing ultraviolet absorbing agents
US3936305A (en)	1976-02-03	Color photographic photosensitive material containing ultraviolet ray-absorbing compound
US3705805A (en)	1972-12-12	Photographic layers containing compounds which absorb ultraviolet light
DE2853866A1 (de)	1979-06-21	Verfahren zur stabilisierung organischer substratmaterialien einschliesslich photographischer farbstoffbilder gegenueber licht und stabilisiertes, photographisches material
JPH0352616B2 (de)	1991-08-12
JPS6127733B2 (de)	1986-06-26
DE2849346A1 (de)	1979-05-17	Verfahren zum stabilisieren organischer substrate einschliesslich photographischer farbbilder gegen licht
EP0011051A2 (de)	1980-05-14	Farbphotographisches Aufzeichnungsmaterial, Verfahren zu seiner Stabilisierung und Herstellung photographischer Farbbilder
US3794493A (en)	1974-02-26	Photographic layers which contain uv-absorbers
DE2034064B2 (de)	1978-07-20	Farbfotografisches Aufzeichenmaterial
US3785827A (en)	1974-01-15	Photographic material stabilised against ultraviolet radiation
US4576908A (en)	1986-03-18	Ultraviolet absorber in photographic elements
DE1695504A1 (de)	1972-03-02	Ultraviolette Strahlung absorbierende optische Aufheller
DE2528638A1 (de)	1976-01-15	Pivalylacetanilide und diese verbindungen enthaltendes photographisches aufzeichnungsmaterial
DE69713984T2 (de)	2003-02-06	UV-Absorber auf Basis von Benzotriazolen sowie photographische Elemente, die diese enthalten
DE2128296C3 (de)	1975-06-19	Spektral sensibilisierte photographische Silberhalogenidemulsion
US2395776A (en)	1946-02-26	Color photography
US3687671A (en)	1972-08-29	Photographic layers containing compounds which absorb ultraviolet light
DE1597539A1 (de)	1970-08-13	Verwendung von Pentamethinoxonolfarbstoffe enthaltenden Dispersionen zur Herstellung von Lichthofschutzschichten in photographischen Materialien
DE3730319C2 (de)	1996-05-09	Fotografisches Aufzeichnungsmaterial