US3756828A - Es photographic light sensitive material having good antistatic properti - Google Patents

Es photographic light sensitive material having good antistatic properti Download PDF

Info

Publication number
US3756828A
US3756828A US00232941A US3756828DA US3756828A US 3756828 A US3756828 A US 3756828A US 00232941 A US00232941 A US 00232941A US 3756828D A US3756828D A US 3756828DA US 3756828 A US3756828 A US 3756828A
Authority
US
United States
Prior art keywords
photographic
compound
film
photographic light
sensitive 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
Application number
US00232941A
Other languages
English (en)
Inventor
M Yoneyama
N Yamamoto
K Endo
Machi M Ashigara
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.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
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.)
Filing date
Publication date
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3756828A publication Critical patent/US3756828A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/38—Dispersants; Agents facilitating spreading
    • 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
    • G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings

Definitions

  • the present invention relates to a silver halide photographic light-sensitive material having good antistatic properties.
  • a photographic light-sensitive material is generally prepared by coating one or more light-sensitive photographic emulsion layers and subsidiary layers to the surface of a film of a poly-alpha-olefin such as polyethylene or polystyrene, a cellulose organic acid ester such as cellulose triacetate, or a polyester such as polyethylene terephthalate; the surface of a baryta-coated paper; or the surface of a sheet prepared by coating both surfaces of a paper with such a polymer as described above. Therefore, such photographic light-sensitive materials have considerable electrical insulation. Consequently it frequently happens that when the surface of the photographic light-sensitive material is rubbed against each other or rubbed by the surface of a foreign material during the manufacturing or the use of the material, electrostatic charges accumulate on the photographic material.
  • the accumulated electrostatic charges give rise to various disadvantages. For instance, when the accumulated electrostatic charges on a photographic light-sensitive film are discharged before development, the light-sensitive emulsion layer of the photographic film is exposed to the discharged light and spot-like or dendroid stains are formed on the photographic emulsion layer on development. Such stains are generally called static marks and the occurrence of the static marks reduces greatly or sometimes results in a complete loss of the commercial value of the photographic film. Because the presence of static marks cannot be confirmed before development, it is a quite troublesome problem.
  • the electrostatic charges accumulated on a film support or on the material during coating cause the ducing a secondary difficulty such as an unevenness in coating on application of the photographic emulsions.
  • these electrostatic charges are formed when a photographic film or paper is brought into contact with and rubbed by rollers or when the back surface of a photographic film or paper is brought into contact with and then separated from the surface of the photographic emulsion layer thereof during the rolling or unrolling step of the photographic film or paper.
  • these electrostatic charges are also formed when the back surface of a photographic film is brought into contact with the emulsion layer thereof and then separated therefrom as in rolling or unrolling of the photographic material which under high humidity conditions results in the adhesion of the photographic material to each other, when the surfaces of a photographic cine-film are rubbed by mechanical parts, when the back surface of the cine-film is brought into contact with the emulsion layer thereof and separated therefrom at the photographing or unrolling stage of the cinefilm, or when an X-ray photographic film is rubbed by mechanical parts or is separated from a fiourescent sensitizing paper in an automatic photographing machine. Furthermore, electrostatic charges are formed on photographic light-sensitive films or papers when they are brought into contact with packing materials.
  • An object of this invention is, therefore, to provide a photographic light-sensitive material on which the formation of static charges has been markedly reduced without resulting in adverse influences on the photographic properties thereof.
  • the aliphatic saturated or unsaturated branched or straight chain group R in the above general formula usually is an alkyl or alkenyl group having from about 6 to about 20 carbon atoms. Suitable such examples are hexyl, octyl, tertoctyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, hexadecenyl octadecyl and eicosyl.
  • Examples of the residual group represented by Y in the above formula include the residual groups of an alkanediol such as ethylene glycol, propylene glycol, butylene glycol and the like; polyethylene glycol; 1,4-dicyclohexane dimethanol; an alkanetriol such as glycerol, 1,2,3-butanetriol, 1,2,6- hexanetriol, etc.; a trimethylol alkane such as trimethylol propane; a multihydric alcohol such as sorbite, sorbitol, sorbitane, 2,2,6,6-tetramethylol cyclohexanol, pentaerythritol, saccharose, rafiinose, and the like.
  • an alkanediol such as ethylene glycol, propylene glycol, butylene glycol and the like
  • polyethylene glycol 1,4-dicyclohexane dimethanol
  • an alkanetriol such as glycerol,
  • a characteristic fact is that when the compound of the above-described formula is one in which Y is a residue containing no hydroxyl group, e.g., containing an ethyl group, such a compound has no antistatic effect, while the compounds of this invention in which Y is a residue containing a hydroxyl group show quite excellent antistatic effects.
  • Suitable alkali metals for M are sodium and potassium.
  • the term quaternary ammonium group is intended to cover both NH, and substituted ammonium groups having one or more substituents for example, short chain alkyl or hydroxy-alkyl groups such as methyl, ethyl and hydroxyethyl. Specific examples are (CH NH+ and (CH CH OH) NH+.
  • the difliculties caused by static marks during the production of photographic light-sensitive materials or during use of them can be eliminated.
  • a compound of this invention in a photographic light-sensitive film, the formation of electrostatic charges in placing the film in a cassette (magazine) or in mounting the magazine in a camera is very effectively prevented even under low humidity conditions.
  • the antistatic property of the film is not reduced with the passage of time.
  • the compound of this invention has the advantage that it provides a high electric conductivity to photographic films and papers and causes no difficulties in adhesion even at high temperatures.
  • the compound of this invention can be easily dissolved in such solvents as water and methanol and by adding it to photographic emulsion layers of a photographic lightsensitive film or paper or by applying it to the surface of a support for a photographic light-sensitive film or paper, the occurrence of electrostatic charges can be effectively prevented without giving rise to adverse effects on photographic properties such as sensitivity, gamma, and fog as well as properties such as the viscosity, the coagulation temperature, and the pH of photographic emulsions.
  • the amount of the compound can be varied according to the kind and shape of the photographic film or paper or the manner of applying the photographic emulsion to a support. However, it is preferred that the compound used in this invention be present in a photographic lightsensitive film or paper in an amount of from about 0.01 to about 2.0 g., preferably from about 0.04 to about 0.4 g. per square meter of the film or paper.
  • the compound used in this invention may be incorporated in any gelatincontaining layers of a photographic light-sensitive material, such as silver halide emulsion layer, a protective layer, an anti-halation layer, an undercoat, a backing layer, and the like, but is preferably incorporated in a surface layer of the light-sensitive material.
  • the compound of this invention can be effectively applied to the surface of a film support such as a cellulose triacetate film, a polyethylene terephthalate film, and the like, the surface of a paper, and the surface of a sheet prepared by coating a paper with a polymer such as polyethylene.
  • a film support such as a cellulose triacetate film, a polyethylene terephthalate film, and the like
  • the surface of a paper and the surface of a sheet prepared by coating a paper with a polymer such as polyethylene.
  • the compound of this invention when incorporated in the photographic layer of a photographic light-sensitive material, it can be incorporated into the emulsion to be used for the layer as a solution in water, in an organic solvent, or in a mixture thereof, it can be sprayed or applied onto the surface of the photographic layer, or the photographic light-sensitive material having photographic emulsion layers already prepared thereon can be immersed in a solution of the compound and dried.
  • a solution of the compound in water, an organic solvent such as methanol, or a mixture thereof can be sprayed or applied onto the back surface of the support or the film base may be immersed in a solution of the compound and dried.
  • the compound of this invention may be used together with a binder such as gelatin, polyvinyl alcohol, cellulose acetate phthalate, cellulose acetate, or other various polymers.
  • the compound of this invention can be used to prevent the formation of static charges on films or other shaped articles of polymers such as cellulose esters, polyesters, polystyrenes, polycarbonates, polyethylenes, polypropylenes, and other vinylic resins. Furthermore, it has been found that the compound used in this invention is also excellent as a wetting improving agent necessary for applying photographic coating compositions to a support at high speed.
  • the antistatic properties of the compound of this invention were evaluated in the following examples using a method in which a film strip containing the compound, adjusted to a relative humidity (RH) of 20 to 65%, was rolled by a gum roller and the amount of electrostatic charges formed were measured using a Faraday box.
  • This method comprised placing an unexposed photographic light-sensitive film containing the compound on a rubber sheet, pressing the film onto the rubber sheet using a gum 6 roller, and thereafter separating the film from the rubber sheet to form static marks. A measurement of the surface specific resistance was also made.
  • Example 1 An X-ray photographic light-sensitive material (Specimen No. 10) prepared by coating continuously an undercoated cellulose triacetate support with a high-sensitive emulsion for X-ray photograph containing 6% gelatin and 6% silver iodobromide and an aqueous solution of gelatin containing no antistatic agent as the surface protective layer and dried was immersed in a 1% aqueous solution of one compound of this invention (Compounds 1, 2, 6, 8, l0, 11, or 15 described above) for 30 seconds and dried to provide Specimens No. 1, No. 2, No. 3, No. 4, No. 5, No. 6 and No. 7, respectively.
  • a compound of this invention Compounds 1, 2, 6, 8, l0, 11, or 15 described above
  • Specimen No. 10 described above was treated in a manner as above with a 1% aqueous solution of saponin or alpha-sulfopalmitic acid methyl ester which is similar to the compound of this invention to provide comparison specimens (Specimen No. 8 and Specimen No. 9, respectively).
  • each of the specimens thus prepared was adjusted to a relative humidity of 40% and then passed into a Faraday gauge through a space between the two gum rollers, wherein the amount of the static charges formed was measured using a vacuum voltmeter.
  • each of the photographic film samples prepared above was placed on a white rubber sheet and after rolling the surface of the white rubber plate with a roller to provide a definite friction under the conditions of 23 C. and 40% relative humidity, the white rubber plate was separated from the film.
  • Each of the photographic film samples was then developed in a developing solution having the following composition for 4 minutes at 20 C. and then the amount of static marks thus formed was measured, whereby the antistatic properties of the compound were evaluated.
  • Example 2 A high-sensitive silver halide emulsion for negative use containing 6% gelatin and 12% silver iodobromide was mixed with a 4% aqueous solution of saponin as a wetting agent in an amount of S m1./kg. of the emulsion and the mixture was applied to an undercoated cellulose triacetate film support.
  • a coating composition for the surface protective layer prepared by adding 70 ml. of a 5% aqueous solution of a compound of this invention (Compound 1 shown above) to 1 kg. of an aqueous 7% solution of gelatin was applied to the silver halide emulsion layer thus formed. After setting by cooling, the sample was dried.
  • a comparison sample of photographic film was prepared by applying a surface protective gelatin layer using 100 ml. of a 4% aqueous solution of saponin or 70 ml. of a 5% aqueous solution of alpha-sulfopalmitic acid methyl ester in the same manner as described above.
  • the antistatic faculty and the amount of static charges formed for each of the photographic films were measured using the methods described in Example 1.
  • Example 3 1 g. of a compound (Compound 11 as shown above) of this invention was added to 90 ml. of distilled water and the solution was added to a solution prepared by dissolving 2 g. of cellulose acetate phthalate and 2 g. of triethanol amine in 600 ml. of methanol.
  • the solution thus prepared was applied to the back surface of a cellulose triacetate film and then a negative silver halide emulsion, containing 7% gelatin and 7% silver iodobromide, for cine-film was applied to the opposite surface of the film.
  • the surface specific resistance of the back surface of the photographic light-sensitive film thus prepared at a relative humidity of 30% was 5 10 ohms, which was much lower than the surface specific resistance (8X10 ohms) of the back surface of a control photographic film of the same composition but having no backing layer containing the compound of this invention.
  • Example 4 0.2 g. of chrome alum and 0.4 g. of saponin were added 2 kg. of an aqueous 2% gelatin solution and the solution obtained was divided into two parts. 30 ml. of
  • a 5% aqueous solution of a compound of this invention (Compound 1) was added to one of them, while ml. of a 5% aqueous solution of saccharose monolauric acid ester, a known antistatic agent, was added to the other part.
  • Each of these two solutions was applied as a protective layer to a high-sensitive emulsion layer, containing 6% gelatin and 6% silver iodobromide, for X-ray photography formed on a polyethylene terephthalate film support and then dried.
  • a high-sensitive negative photographic emulsion containing 7% gelatin and 8% silver iodobromide, was applied to the opposite surface of the film and then a mixture of 1 kg. of aqueous 2% gelatin solution and 100 ml. of 5% aqueous solution of the compound of this invention (Compound 10) was further applied to the emulsion layer as a protective layer. After drying the layers, the amount of static marks under a relative humidity of 30% was measured and the antistatic properties were determined from the amount of the static marks in the same manner as disclosed in Example 1. The results are shown in the following table.
  • Example 6 4% aqueous solution of saponin was added to a highsensitive silver halide emulsion for negative film use containing 7% gelatin and 8% silver iodobromide and the mixture was applied to an undercoated cellulose triacetate film support. After the layer was set, a mixture of 1 kg. of an aqueous 2% gelatin solution and 70 ml. of a 5% aqueous solution of a compound of this invention (Compound 1) was applied to the emulsion layer and, after the layer was set, was dried.
  • Compound 1 1 kg. of an aqueous 2% gelatin solution and 70 ml. of a 5% aqueous solution of a compound of this invention
  • the photographic film was placed under a condition of 2 0% relative humidity and then the film was passed through a high speed camera. Thereafter, the formation of static marks was measured. The results obtained are shown in the following table.
  • a color photographic film for negative film use prepared by applying continuously to a support a color photographic high sensitive emulsion containing a color coupler and an aqueous gelatin solution containing no antistatic agent as the surface protective layer of the following composition, a support of a cellulose triacetate film base having coated thereon in order from the support a red-sensitive silver iodobromide emulsion layer containing N-n-dodecyl-1-hydroxy-4-chloro-2-naphthamide as a cyan coupler, a gelatin intermediate layer, a green-sensitive silver iodobromide emulsion layer, containing 1-phenyl-3- dodecylamino-S-pyrazolone as a magenta coupler, a yellow filter layer containing colloidal silver, a blue-sensitive silver iodobromide emulsion layer containing 4-dodecyl benzoyl-2-methoxy-acetanilide as a yellow coupler and
  • each of the samples was adjusted to a relative humidity of 40% and the amount of the static marks formed was measured in the same manner as described in Example 1. From the amount of static marks, the antistatic properties were evaluated. Ihe results obtained are shown in the following table.
  • a photographic light-sensitive material having antistatic characteristics comprising a support containing thereon at least one silver halide photographic emulsion layer, and at least one subsidiary layer wherein at least one of the layers comprising said photographic light-sensitive material contains an ester deriavtive of an alphasulfofatty acid represented by the general formula attoly to... 1
  • R represents a saturated or unsaturated, branched or straight chain aliphatic group having more than 6 carbon atoms
  • M represents a hydrogen atom, an alkali metal atom, or a quaternary ammonium group
  • Y represents a residual group containing from 2 to 18 carbon atoms and having at least one hydroxyl group
  • n represents an integer of from 1 to 7.
  • said residual group is a residual group derived from a multihydric alcohol selected from the group consisting of ethylene glycol, polyethylene glycol, 1,4-dicyclohexane dimethanol, glycerol, 1,2,4-butanetriol, 1,2,6-hexanetriol, trimethylol propane, sorbitol, sorbitan, 2,2,6,6-tetrarnethylol cyclohexanol, pentaerythritol, saccharose, and raflinose.
  • a multihydric alcohol selected from the group consisting of ethylene glycol, polyethylene glycol, 1,4-dicyclohexane dimethanol, glycerol, 1,2,4-butanetriol, 1,2,6-hexanetriol, trimethylol propane, sorbitol, sorbitan, 2,2,6,6-tetrarnethylol cyclohexanol, pentaerythritol, saccharose, and r

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US00232941A 1971-03-11 1972-03-08 Es photographic light sensitive material having good antistatic properti Expired - Lifetime US3756828A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP46013315A JPS5040663B1 (enrdf_load_stackoverflow) 1971-03-11 1971-03-11

Publications (1)

Publication Number Publication Date
US3756828A true US3756828A (en) 1973-09-04

Family

ID=11829723

Family Applications (1)

Application Number Title Priority Date Filing Date
US00232941A Expired - Lifetime US3756828A (en) 1971-03-11 1972-03-08 Es photographic light sensitive material having good antistatic properti

Country Status (6)

Country Link
US (1) US3756828A (enrdf_load_stackoverflow)
JP (1) JPS5040663B1 (enrdf_load_stackoverflow)
CA (1) CA977597A (enrdf_load_stackoverflow)
DE (1) DE2211813A1 (enrdf_load_stackoverflow)
FR (1) FR2128802B1 (enrdf_load_stackoverflow)
GB (1) GB1381005A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3887377A (en) * 1972-07-22 1975-06-03 Fuji Photo Film Co Ltd Antistatic photographic light-sensitive materials
US4001023A (en) * 1972-05-26 1977-01-04 Agfa-Gevaert N.V. Adhesion of hydrophilic layers on polyester film
US4216290A (en) * 1974-05-22 1980-08-05 Agfa-Gevaert N.V. Coating of viscous aqueous gelatin compositions on a continuous web support
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing
US20210403421A1 (en) * 2017-02-10 2021-12-30 Lawrence Livermore National Security, Llc Biodegradable surfactants and related compositions, methods and systems

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001023A (en) * 1972-05-26 1977-01-04 Agfa-Gevaert N.V. Adhesion of hydrophilic layers on polyester film
US3887377A (en) * 1972-07-22 1975-06-03 Fuji Photo Film Co Ltd Antistatic photographic light-sensitive materials
US4216290A (en) * 1974-05-22 1980-08-05 Agfa-Gevaert N.V. Coating of viscous aqueous gelatin compositions on a continuous web support
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
US7250202B1 (en) 1998-06-18 2007-07-31 Ilford Imaging Ch Gmbh Recording sheets for ink jet printing
US6071688A (en) * 1998-07-29 2000-06-06 Eastman Kodak Company Providing additives to a coating composition by vaporization
US20210403421A1 (en) * 2017-02-10 2021-12-30 Lawrence Livermore National Security, Llc Biodegradable surfactants and related compositions, methods and systems

Also Published As

Publication number Publication date
JPS5040663B1 (enrdf_load_stackoverflow) 1975-12-25
FR2128802A1 (enrdf_load_stackoverflow) 1972-10-20
GB1381005A (en) 1975-01-22
FR2128802B1 (enrdf_load_stackoverflow) 1977-04-01
CA977597A (en) 1975-11-11
DE2211813A1 (de) 1972-09-28

Similar Documents

Publication Publication Date Title
US4975363A (en) Light-sensitive silver halide photographic materials
US4675278A (en) Silver halide photographic light-sensitive materials
US3502473A (en) Photographic elements containing a synthetic surface active material and inert particles
US4229524A (en) Photographic light sensitive material with antistatic property
US4050940A (en) Process for the preparation of a photographic material
US2197809A (en) Photographic process and emulsion utilizing cation-active surface active agents
US2976148A (en) Antistatic backing layers for photographic film
US3415649A (en) Process for the production of light-sensitive material containing coating aids
US3843368A (en) Silver halide photographic light-sensitive element
US3532501A (en) Water-soluble acid esters of polyoxyalkylenated pentaerythritol in silver halide emulsions
US3756828A (en) Es photographic light sensitive material having good antistatic properti
EP0127820B1 (en) Antistatic photographic base, method for preparing it and photographic element comprising said base
US4623614A (en) Silver halide photographic light-sensitive materials
US3850641A (en) Antistatic light-sensitive photographic material
US3811889A (en) Light-sensitive photographic material with antistatic layer
US4914018A (en) Antistatic photographic base and light-sensitive element
US4847186A (en) Silver halide photographic light-sensitive materials
US3938999A (en) Antistatic photographic sensitive materials
US3704128A (en) N-ylide compounds as antistatic agents in photography
US3876430A (en) Antistatic photographic material
US3775128A (en) Silver halide emulsion containing a triazine as antifoggant
US3033680A (en) Plasticized gelating compositions
US2577127A (en) Photographic element with colloid layer containing color former and nonionic wettingagent
US4042399A (en) Photographic element with improved slip
US3264108A (en) Antistatic photographic film