JPS5843729B2 - Halogen cover - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for preventing electrification of silver halide photographic materials.

When a silver halide photographic material is charged with static electricity during its manufacture or use, when it is discharged, it causes a problem called a static mark.

During production, silver halide photographic materials are subjected to friction and peeling from other substances during various processes such as winding, rewinding, coating, and transport during drying, resulting in electrical charge and electrical discharge. Then, the silver halide photographic light-sensitive material coated with the photosensitive layer is exposed to light, and when it is developed, a failure occurs due to uneven exposure called static marks.

Furthermore, when using manufactured silver halide photographic materials, especially under conditions of low humidity, static electricity may cause static marks, or dust may adhere, causing various problems. happens.

Various antistatic agents have been used in photographic films.

However, not only are few of these antistatic agents satisfactory especially at low humidity, but many of them do not exhibit sufficient effects unless used at high concentrations.

Many conventional antistatic agents, when used in large amounts, have a negative effect on the sensitivity, fog, and storage stability of silver halide photographic materials, or are accompanied by adhesion failure, bleeding phenomena, etc., so they are not necessarily satisfactory in practical terms. It wasn't something.

The object of the present invention is to provide an antistatic agent that does not have the above-mentioned drawbacks, and also to provide a method for satisfactorily preventing charging of a silver halogenide photographic light-sensitive material using the antistatic agent.

The present inventor has proposed that the above object can be achieved by using a product obtained by addition copolymerizing glycidol and ethylene oxide to a phenol aldehyde condensate (hereinafter referred to as the addition polymer of the present invention) as an antistatic agent. I found out.

That is, the antistatic agent is added to the constituent elements of the silver halide photographic material, such as the silver halide emulsion layer, the subbing layer,
Contained in at least one layer such as an intermediate layer, a filter layer, an anti-ration layer, a protective layer, a backing layer, or (d) on the outermost layer of a silver halide photographic light-sensitive material,
A desired antistatic effect can be imparted to the silver halide photographic material by coating or coating on a support.

Moreover, in this case, no adverse effect is exerted on the photographic performance of the silver halide photographic light-sensitive material, such as sensitivity, gradation, fog, and storage stability.

The phenolaldehyde condensate used as a raw material for obtaining the addition polymer of the present invention includes, for example, phenolaldehyde having a repeating structural unit as shown in the following general formula (I), with or without a substituent. Condensates are typically included.

General formula (I) (wherein R1 and R2 are hydrogen atom, halogen atom, carboxyl group, acyl group, alkoxycarbonyl group, alkyl group, substituted alkyl group, alkoxy group or phenyl group, R3 is hydrogen atom, methyl group or α -Represents a furyl group.

Examples of phenol-aldehyde condensates with or without such substituents include the following.

Phenol-formalin resin 4-methyl-phenol-formalin resin 2-t-7”
Chill-phenol-formalin resin 4-t-7” Chill-
Phenol-formalin resin 4-Octyl-phenol-formalin resin 4-nonyl-phenol-formalin resin 2,4-di-nonyl-phenol-formalin resin 4-)'Tethyl-phenol-formalin resin 4-Tetrate-phenol-formalin resin Resin 2-octadecyl-phenol-formalin resin 4-octadecyl-phenol-formalin resin 3-pentadecyl-7 enol-formalin resin 2,4-di-t-butyl-phenol-formalin resin 2-methyl-4-tetradecyl-phenol- Formalin resin 2-chloro-phenol-formalin resin 4-promorphphenol-formalin resin 3-nitro-phenol-
Formalin resin 4-Carboxy-phenol-formalin resin 2-Chlor-4-hydroxyethyl-phenol-formalin resin 2-Chlor-4-chloroethyl-phenol-formalin resin 2-Iodoethyl-4-methoxycarbonyl-phenol-formalin resin 4- Methoxy-phenol-formalin resin 4-Methylcarboxy-phenol-formalin resin 2-hydroxymethyl-3-methyl-phenol-formalin resin 4-nonyl-phenol/2,4-di-nonylphenol-formalin resin Phenol-acetaldehyde resin 4- Methyl-phenol-acetaldehyde resin 4-tert-butyl-phenol-acetaldehyde resin 2-octyl-phenol-acetaldehyde resin 4-nonyl-phenol-acetaldehyde resin 3-pentadecyl-phenol-acetaldehyde resin 2,4-cy t-7”Til -phenol-acetaldehyde resin 2-methyl-4-tetradecyl-phenol-acetaldehyde resin 4-chloro-phenol-acetaldehyde resin 2-promorphphenol-acetaldehyde resin 2-chloroethyl-4-chloro-phenol-acetaldehyde resin 2-yo)'methyl- 4-Methoxycarbonyl-phenol-acetaldehyde resin 2-methylcarboxyphenol-acetaldehyde resin 4-,/Nyl-phenol/2,4-dinonylphenol acetaldehyde resin 4-tetradecyl-phenol-acetaldehyde resin 2-octadecyl-phenol -Acetaldehyde resin 4-Octadecyl-phenol-acetaldehyde resin 4-Methoxy-phenol-acetaldehyde resin 4-tert-butyl-phenol-furfural resin 2,4-di-nonyl-phenol-furfural resin 4-Dodecyl-phenol-furfural resin 4 -Carboxy-phenol-furfural resin 2-chloro-4-hydroxyethyl-phenol-furfural resin 2-hydroxymethyl-3-methyl-phenol-furfural resin 4-/ni-7enol/2,4-di-nonylphenol-furfural resin These phenol-aldehyde resins are generally obtained by condensation reaction of phenols and aldehydes, but they can also be obtained by condensation reaction with phenols using acetylene instead of acetaldehyde as a raw material, such as phenol acetaldehyde resin. , it is possible to produce resins having the same repeating basic structural unit, and regardless of the production method, all of these resins can be effectively used as raw materials for addition copolymerization of glycidol and ethylene oxide in the present invention. be able to.

In addition, the phenol aldehyde condensate used as a raw material for obtaining the addition polymer of the present invention includes, for example, a phenol form having or not having a substituent having a repeating structural unit as shown in the following general formula (III). lJ
By treating the condensate with hydrogen halogenide, a product in which the remaining methylol group at the end of the condensate is converted into a halogenated methyl group is also included.

(In the formula, R1 and R2 represent a hydrogen atom, a halogen atom, a carboxyl group, an acyl group, an alkoxycarbonyl group, an alkyl group, a substituted alkyl group, an alkoxy group, or a phenyl group.

) Phenols with or without such substituents
Examples of products obtained by halogenating formalin condensates include the following.

Brominated - Phenol - Formalin Resin Brominated - 4 - Methyl - Phenol - Formalin Resin Chlorinated - 2 - t - 7 " Chill - Phenol - Formalin Resin Chlorinated - 4 - t - 7 " Chill - Phenol - Formalin Resin Brominated -4-octyl-phenol-formalin resin chlorination -4-cumyl-phenol-formalin resin bromination-4-/Nyl-phenol-formalin resin chlorination -2,4-di-nonyl-phenol-formalin resin chlorination- 4-tetradecyl-phenol-formalin resin brominated-2-octadecyl-phenol-formalin resin chlorinated-2,4-di-t-butyl-phenol-formalin resin brominated-2-methyl-4-tetradecyl-phenol-
Chlorinated Formalin Resin -2-Chlor-phenol-Formalin Resin Brominated-4-7'' Romophenol-Formalin Resin Chlorinated-2-Chlor-4-hydroxyethylphenol-Formalin Resin JJ-formed-4-methoxy-phenol- Formalin resin The addition polymer of the present invention is a product obtained by addition-copolymerizing glycidol and ethylene oxide to the above-mentioned phenolaldehyde condensate. and is introduced into the position of the hydroxyl group of the phenyl nucleus as a block copolymerized group as shown in the following general formula (III) or general formula (IV).

General formula (III) (In each formula, Xl, X2, yl, and y2 represent the degree of polymerization.

Further, addition polymers of the present invention include those in which glycidol and ethylene oxide are introduced as random copolymerized groups.

To produce the addition polymer of the present invention, one or a mixture of two or more of the above-mentioned phenol-aldehyde resins or halogenated phenol-formalin resins is dissolved in an organic solvent such as toluene, xylene, or dioxane. , in the presence of an alkaline catalyst such as potassium hydroxide, 13
While stirring at 0-140°C, glycidol was added dropwise over a period of about 5 hours to cause an addition polymerization reaction, and then 130-140°C
Ethylene oxide is blown into the reaction mixture with stirring at a temperature of 0.degree. C. to cause an addition polymerization reaction. After completion of the addition polymerization reaction, the reaction mixture is neutralized with glacial acetic acid, and then the organic solvent is removed under reduced pressure.

Furthermore, if the reaction is carried out by reversing the order of addition of glycidol and ethylene oxide, a copolymer with opposite blocks can be obtained.

The glycidol and ethylene oxide addition copolymer obtained in this way generally has a viscous or sock-like shape, and is free from water, methanol, ethanol,
Soluble in organic solvents such as acetone, dioxane, methylcellosolve, and dimethylformamide.

The amount of addition polymerization of glycidol and ethylene oxide is approximately 1 to 20 moles of glycidol and 5 moles of ethylene oxide per repeating basic structural unit of the product obtained by rogogenation treatment of phenol aldehyde condensate or phenol formalin condensate. About 100 mol is preferable.

If more than this amount is added, it is not preferable because it may cause problems such as fog to the silver halide photographic light-sensitive material.

Next, typical examples of the addition polymer of the present invention will be shown.

Exemplary Compound 1 Glycidol and ethylene oxide addition copolymer of 4-t-octyl-phenol formalin resin (Addition copolymerization of 5 moles of glycidol and 20 moles of ethylene oxide per basic structural unit of resin) Exemplary Compound 2 4-Butyl-phenol formalin resin glycidol and ethylene oxide addition copolymer (1 mol of glycidol, 8 mol of ethylene oxide per basic structural unit of resin)
Molar addition copolymerization) Exemplary compound 3 Glycidol and ethylene oxide addition copolymer of 4-nonyl-phenol formalin resin (3 moles of glycidol, 1 mole of ethylene oxide per basic structural unit of the resin)
5 mol addition copolymerization) Exemplary compound 4 Glycidol and ethylene oxide addition copolymer of 4-methyl-phenol formalin resin (5 mol glycidol, 1 ethylene oxide per basic structural unit of resin)
5 molar addition copolymerization) Exemplary compound 5 Glycidol and ethylene oxide addition copolymer of 4-nonyl-phenol/2,4-di-nonyl-phenol formalin resin (molar ratio 1/1) (glycidol per basic structural unit of resin) 20 moles, ethylene oxide 2
0 mol addition copolymerization) Exemplary compound 6 4-t-octyl-phenol formalin resin glycidol and ethylene oxide addition copolymer (Addition copolymerization of 3 mol glycidol and 10 mol ethylene oxide per basic structural unit of resin) Exemplary compound 7 2 - Glycidol and ethylene oxide addition copolymer of chloro-4-nonyl-phenol formalin resin (
Addition copolymerization of 5 moles of glycidol and 18 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 8 Addition copolymer of glycidol and ethylene oxide of brominated-4-t-butyl-phenol formalin resin (addition copolymerization of glycidol and ethylene oxide per basic structural unit of resin) 1 mol, ethylene oxide 7 mol addition copolymerization) Exemplary compound 9 4-Methoxy-phenol-formalin resin glycidol and ethylene oxide addition copolymer (addition copolymerization of 15 mol glycidol and 10 mol ethylene oxide per basic structural unit of resin) Compound 10 4-7 toxycarbonyl-phenol-furfuralide addition copolymer (addition copolymerization of 5 moles of glycidol and 10 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 11 Chlorinated-4-phenylphenol-formalin resin Addition copolymer of glycidol and ethylene oxide (addition copolymerization of 20 moles of fucidol and 5 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 12 4 - Addition copolymerization of glycidol and ethylene oxide of M7' syl-phenol-formalin resin Coalescence (addition copolymerization of 10 moles of glycidol and 3 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 13 Addition copolymer of glycidol and ethylene oxide of 4-cumyl-phenol-formalin resin (10 moles of glycidol per basic structural unit of resin) , addition copolymerization of 30 moles of ethylene oxide) Exemplary compound 14 Example of addition copolymerization of glycidol and ethylene oxide of 4-iso-propyl-phenol-formalin resin (addition copolymerization of 7 moles of glycidol and 10 moles of ethylene oxide per basic structural unit of the resin) Compound 15 Glycidol and ethylene oxide addition copolymer of 3-nitrophenol-formalin resin (addition copolymerization of 20 moles of glycidol and 50 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 16 Addition copolymer of 4-n-octyl-phenol-formalin resin Glycidol and ethylene oxide addition copolymer (addition copolymerization of 5 moles of glycidol and 10 moles of ethylene oxide per basic structural unit of resin) Exemplary compound 17 Glycidol and ethylene oxide addition copolymer of 4-t-butyl-phenol-formalin resin (resin g) Addition copolymerization of 5 moles of fucidol and 5 moles of ethylene oxide) Exemplary compound 18 Glycidol and ethylene oxide addition copolymer of 4-t-octyl-phenol formalin resin (110 moles of glycidol per basic structural unit of the resin) , addition copolymerization of 30 moles of ethylene oxide) The addition polymer of the present invention can be added to silver halide emulsion layers, subbing layers, intermediate layers, filter layers, antihalation layers, protective layers, or backing layers, which are the constituent elements of silver halide photographic materials. To incorporate it into a coating layer, etc., it can be directly added and dissolved in the coating solution used to form those layers, or it can be dissolved in water or an organic solvent such as methanol, ethanol, acetone, dioxane, methyl cellosolve, etc. alone or in a mixture. It may be added to the coating liquid.

In addition, when applying to the surface of a support or the outermost layer of a silver halide photographic light-sensitive material, a solution prepared using a similar solvent may be sprayed onto the surface, or the surface may be dipped in the solution and then dried. Bye.

When the addition polymer of the present invention is applied to a silver halide photographic light-sensitive material, the amount thereof varies depending on the type of addition polymer and the location where it is applied, but it is present in the range of 5X10' to IXIO-5 mol per square meter of the light-sensitive material. By this, an effective antistatic effect can be exhibited.

However, the amount to be used is not limited to this range, and the optimum amount for obtaining appropriate effects can be arbitrarily selected.

Various types of hydrophilic colloids, including gelatin, are used as binders for silver halide photographic materials to which the present invention is effectively applied.

In this case, gelatin includes not only gelatin but also derivative gelatin, and derivative gelatin includes, for example, a reaction product of gelatin and an acid anhydride as described in U.S. Pat. No. 2,614,928, and a reaction product of gelatin and isocyanate. or a reaction product of gelatin and a compound having an active halogen atom.

The acid anhydrides used in the reaction with gelatin include, for example, maleic anhydride, phthalic anhydride, benzoic anhydride, acetic anhydride, isatoic anhydride, succinic anhydride, etc., and the incyanate compounds include, for example, Phenyl isocyanate, p-bromophenyl incyanate, p
-chlorophenylisocyanate, p-) IJ isocyanate, p-nitrophenyl isocyanate, naphthylisocyanate, and the like.

Furthermore, examples of compounds having active halogen atoms include benzenesulfonyl chloride, p-methoxybenzenesulfonyl chloride, p-phenoxybenzenesulfonyl chloride, p-bromobenzenesulfonyl chloride, p-toluenesulfonyl chloride, m-nitrobenzenesulfonyl chloride, m- Sulfobenzoyl dichloride, naphthalene-β-sulfonyl chloride, p-chlorobenzenesulfonyl chloride, 3-
Nitro-4-aminobenzenesulfonyl chloride, 2
-carboxy-4-bromobenzenesulfonyl chloride, m-carboxybenzenesulfonyl chloride, 2
-amino-5-methylbenzenesulfonyl chloride,
Phthalyl chloride, p-nitrobenzoyl chloride, benzoyl chloride, ethyl chlorocarbonate,
Furoyl chloride and the like are included.

In addition to the above-mentioned derivative gelatin and ordinary photographic gelatin, colloidal albumin, agar, gum arabic, dextran, alginic acid, such as acetyl content, may be used as a hydrophilic colloid to prepare a silver halide photographic emulsion. Cellulose derivatives such as cellulose acetate hydrolyzed to 19-26%, polyacrylamide, imidized polyacrylamide, casein, vinyl alcohol polymers containing urethane carboxylic acid groups or cyanoacetyl groups such as vinyl alcohol-vinyl cyanoacetate copolymers. , polyvinyl alcohol, polyvinylpyrrolidone, hydrolyzed polyvinyl acetate, polymers obtained by polymerizing proteins or saturated acylated proteins with monomers having vinyl groups, polyvinylpyridine, polyvinylamine, polyaminoethyl methacrylate, polyethyleneimine, etc. These hydrophilic colloids can also be used to form constituent layers of light-sensitive materials other than emulsion layers, such as intermediate layers, protective layers, filter layers, backing layers, and the like.

Silver halide photographic materials to which the present invention can be applied include, for example, black and white photographic materials, color photographic materials,
Any type of false color photographic light-sensitive material may be used, including photographic light-sensitive materials used for various purposes such as general use, printing, X-ray use, radiation use, etc. Mechanically, negative type, positive type, Examples include all types of photographic materials such as diffusion transfer type materials.

The silver halide emulsions used in these silver halide photographic light-sensitive materials contain all types of halogens such as silver chloride, silver iodide, silver bromide, silver iodobromide, silver chlorobromide, and silver chloroiodobromide. Silver oxide can be used as a photosensitive component, and this emulsion can contain ruthenium, rhodium, palladium, iridium, platinum,
Noble metal sensitization using salts of noble metals such as gold, such as ammonium chloroparadate, potassium chloroparadite, potassium chloroparadite, potassium chlorooleate, etc., sulfur sensitization using sulfur compounds, and reduction enhancement using stannous salts, polyamines, etc. Various chemical sensitizations such as sensitization or sensitization using polyalkylene oxide compounds can be performed.

This emulsion can also be optically sensitized with cyanine dyes, merocyanine dyes, complex cyanine dyes, etc., and can also be optically sensitized with various couplers such as colorless couplers, colored couplers, development inhibitor releasing couplers, etc., as well as mercury compounds, triazoles, etc. stabilizers such as azaindene-based compounds, benzthiazolium-based compounds, zinc compounds, hardeners such as mucohalogenic acids, vinyl sulfone compounds, and co-existence of alkylacrylates or alkyl methacrylates with acrylic acid or methacrylic acid. Film property improvers consisting of water-dispersible fine particulate polymeric substances obtained by emulsion polymerization of polymers, styrene-maleic acid copolymers, styrene-maleic anhydride half-alkyl ester copolymers, etc., such as saponin, polyethylene glycol Coating aids such as lauryl ether, wetting agents such as compounds such as those described in U.S. Pat. , ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 2
・1,7,9-tetramethyl-5-decyne-4,7-diol 3,6-dimethyl-4-octyne-3,6-diol, propylene glycol, hexylene glycol, bentanediol, ■・4-cyclohexanediol , 1,4-cyclohexane dimetatool, ■・3-cyclohexanediol, 1,2-cyclohexane dimetatool, ■-methyl-3,4-cyclohexanediol,
Various other photographic additives such as 4-hydroxycyclohexane methanol, trimethylolethane, and trimethylolpropane may also be added.

The addition polymer of the present invention is an extremely good antistatic agent,
When used alone, it exhibits an excellent antistatic effect, but when used in combination with other antistatic agents, it also exhibits an excellent antistatic effect.

In particular, some conventional antistatic agents have extremely good antistatic properties, but they have the disadvantage of causing a bleeding phenomenon on the surface of the silver halide photographic material to which they are applied, making them difficult to use. By using such an antistatic agent in combination with the addition polymer of the present invention, the desired antistatic effect can be obtained in an amount within a range that does not cause the bleed phenomenon.

As described above, the addition polymer of the present invention has the advantage that, when used in combination, other antistatic agents, which have heretofore been considered difficult to use, can be effectively used.

For example, the most typical example of other desirable antistatic agents that can be used in combination with the addition polymer of the present invention is a compound represented by the following general formula (V).

General formula (V) (wherein R is an alkyl group having 1 to 20 carbon atoms, Zl and Z2 represent the degree of polymerization, and z and +z2 = 1 to 50.

) The N-polyoxyethylene acylamide represented by the general formula (V) has excellent antistatic property 1) Although it is JIJ,
It has the disadvantage that its antistatic performance is insufficient under very low relative humidity conditions, and when used in increased amounts, a bleed phenomenon occurs.

However, by using it in combination with the addition polymer of the present invention, it becomes possible to use it effectively without producing these disadvantages.

Examples of the compound represented by the general formula (V) include commercially available Amizet 5C1 Amizet 10C (both manufactured by Nikko Chemical Co., Ltd.).

By combining these compounds and the addition polymer of the present invention...
When applied to silver halide photographic materials, it exhibits excellent antistatic effects without any adverse effects on photographic properties such as photosensitivity and fog, storage stability, and physical properties.

As a support for the silver halide photographic material to which the present invention is applied, any support such as a film made of polyethylene terephthalate, polycarbonate, polystyrene, polypropylene, cellulose acetate, etc., baryta paper, polyethylene laminate paper, etc. can be used. can.

Next, the present invention will be illustrated by examples, but the embodiments of the present invention are not limited thereto.

Example 1 A silver iodobromide gelatin high-sensitivity emulsion containing 2.0 mol% of silver iodide was gold sensitized during the second ripening, and then an azaindene compound as a stabilizer, formalin as a hardening agent, and a coating aid were added. Saponin was added as an agent, and the mixture was coated on a polyethylene terephthalate film and dried.

Next, an aqueous gelatin solution containing formalin as a hardening agent and saponin as a coating aid was prepared, divided into 5 parts, and exemplified compounds (2) were added to each of the 4 parts as an antistatic agent.
), (3), (6) and (8) in 11 parts of solution 5? After addition, each of the five components was coated as a protective layer on the silver iodobromide emulsion layer and dried to prepare a sample.

These samples were incubated at 25°C and 20% relative temperature (RE) for 12
After adjusting the humidity for a period of time, the unexposed sample was rubbed with a rubber in a dark room under the same air-conditioning conditions, and then subjected to normal development processing, and the occurrence of static marks was observed.

As a result, the occurrence of static marks was extremely noticeable in the sample in which the exemplified compound as an antistatic agent was not added to the protective layer, but in the four samples in which each exemplified compound as an antistatic agent was added to the protective layer. No static marks were observed in any of the samples.

Note that no change in photographic properties was observed due to the addition of each exemplified compound.

Example 2 A silver iodobromide gelatin high-sensitivity emulsion containing 1.5 mol % of silver iodide was subjected to gold sensitization during the second ripening, and then the same stabilizers, hardeners, and coating aids as in Example 1 were added. The agent was processed, applied onto a polyethylene terephthalate film, and dried.

Next, an aqueous gelatin solution containing mucochloric acid as a hardening agent and saponin as a coating aid was coated thereon as a protective layer and dried.

The film thus obtained was divided into 8 parts, and exemplified compound 1) was added as an antistatic agent on each of the 7 protective layers.
(4), (5), (8), 00), (12) and (1
A solution prepared by dissolving 4) in methanol was applied and dried to deposit each exemplified compound in an amount of IOP per square meter to prepare samples.

These samples were treated in the same manner as in Example 1, and the occurrence of static marks was observed.

As a result, the generation of static marks was extremely noticeable in the samples to which the exemplified compounds as antistatic agents were not attached on the protective layer, but the occurrence of static marks was very noticeable in the samples to which the exemplified compounds as antistatic agents were attached. However, no static marks were observed.

Note that no change in photographic properties was observed due to the addition of each exemplified compound.

Example 3 A silver iodobromide gelatin high-sensitivity emulsion containing 1.5 mol % of silver iodide was gold sensitized during the second ripening and then coated with an azaindene compound as a stabilizer and glyoxal as a hardener. Saponin was added as an auxiliary agent, and the mixture was coated onto a polyethylene terephthalate film and dried.

Next, an aqueous gelatin solution containing formalin as a hardening agent and saponin as a coating aid is prepared, and this is divided to form an exemplified compound which is an addition polymer of the present invention and N-polymer as another antistatic agent. A mixture of oxyethylene acylamide and oxyethylene acylamide as shown in Table 1 below was added, coated on the silver iodobromide emulsion layer, dried, and used as a sample.

These samples were heated at 25°C and at relative humidity of 10%, 15%, and 2.
Set the humidity to 0%, 30%, and 40% and adjust the humidity for 12 hours each.
The film was rubbed with rubber in a dark room under the same air-conditioning conditions, subjected to normal development processing, and the occurrence of static marks was observed.

Claims (1)

[Claims] 1. A method for preventing static electricity on silver halide photographic materials, characterized by using a product obtained by addition copolymerizing glycidol and ethylene oxide to a phenolaldehyde condensate.