US3876430A - Antistatic photographic material - Google Patents

Antistatic photographic material Download PDF

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Publication number
US3876430A
US3876430A US453893A US45389374A US3876430A US 3876430 A US3876430 A US 3876430A US 453893 A US453893 A US 453893A US 45389374 A US45389374 A US 45389374A US 3876430 A US3876430 A US 3876430A
Authority
US
United States
Prior art keywords
antistatic
photographic material
film
photographic
static
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
US453893A
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English (en)
Inventor
Nobuo Tsuji
Takayuki Inayama
Itsuki Toriya
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 US3876430A publication Critical patent/US3876430A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
    • G03C1/89—Macromolecular substances therefor
    • 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
    • G03C1/89—Macromolecular substances therefor
    • G03C1/895—Polyalkylene oxides

Definitions

  • Static charges tend to build up during the manufac ture and use of photographic films.
  • static charges are generated, for example, in the contact part between the photographic film and the roll, or by friction between the support surface and the emulsion layer during winding or unwinding the photographic film or by the peeling off of the emulsion layer from contact with a support.
  • Static charges are also generated when a motion picture camera or an automatic developing machine for X-ray films is used.
  • the antistatic agent can also be added to a photographic emulsion layer formed on the support or to a non-sensitive auxiliary layer (for example, a backing layer, anti-halation layer, interlayer, or protective layer).
  • a non-sensitive auxiliary layer for example, a backing layer, anti-halation layer, interlayer, or protective layer.
  • the anti-static agent can be coated on the film after development in order to prevent the adhesion of dirt and dust during the handling of the developed film.
  • antistatic agents do not exhibit satisfactory effects on photographic materials having an emulsion layer with high sensitivity, especially under low humidity conditions.
  • the antistatic effects frequently decrease with the passage of time, and also adhesion difficulties are frequently caused under high temperature high humidity conditions.
  • the antistatic agents sometimes adversely affect the photographic properties of photographic materials, and therefore have been difficult to apply to photographic materials. Accordingly, attempts have been made to employ various antistatic agents for photographic materials.
  • a and B each represent a straight chain or branched chain alkylene, xylylene or cyclohexylene group, and the straight chain or branched chain alkylene group may contain a double bond, triple bond or a (CH CH O) ,,CI-I- CHI group in the alkylene chain;
  • R R R and R each represent a lower alkyl group (e.g..
  • R and R and/or R and R each may be bonded to form a nitrogen-containing heterocyclic ring;
  • X is anion;
  • n is an integer of about 20 to 50; and
  • X is any anion which balances the charge of the positively charged nitrogen atom, and preferably is a halogen ion (e.g.. chlorine, bromine or iodine).
  • the intrinsic viscosities [1;] were measured in a 0.05 M NaCl aqueous solution at 24.7 i 002C using a modified Ostwald viscometer.
  • a suitable intrinsic viscosity range is from about 0.01 to 0.8, preferably 005 to 0.3.
  • the antistatic compound used in this invention does not adversely affect the photographic properties, such as sensitivity, gamma, or fog.
  • the compounds used in this invention can be synthe sized by reacting diamines of the formula (ll) A H (II) 5 a wherein R,, R R R and A are the same'as defined above, with bis-haloacetyl) glycolslof the formula (III) l yea c 0 B.
  • Examples of compounds of formula (III) include bis-(Chloroacetyl)-ethylene glycol, bis( chloroacetyl l ,4butanediol, bis-(chloroacetyl)-l ,3- propanediol, bis lchloroacetyh-l,IO-decanediol, bis- (chloroacetyl)-cyclohexanediol, bis- (chloroacetyl )xyleneglycol, bis-( chloroacetyl butenediol, bisichloroacetyl )butenediol, bis
  • the amount of the compound used in this invention varies according to the type of photographic material used, its form, the method of coating. etc.
  • the compound can be present in a layer of the photographic material. Generally, however, it is advisable to incorporate the compound in a surface layer in an amount of 0.01 to 1.0 g, especially 0.03 to 0.4 g, per square meter of the photographic film.
  • Suitable examples of photographic materials include black and white films, X-ray films, lithographic films, cine films, color papers, color films, etc.
  • the antistatic compound of this invention Prior to applying the antistatic compound of this invention to a photographic film, it is dissolved in water, an organic solvent such as methanol or acetone or a mixture of an organic solvent and water.
  • an organic solvent such as methanol or acetone or a mixture of an organic solvent and water.
  • a suitable concentration ranges from about 0.05 to 0.5% by weight with a suitable concentration being about 3 to by weight to the binder. Then. the resulting solution is sprayed or coated on the surface of the support or emulsion layer of the film, or the film is immersed in the solution and dried.
  • an antistatic layer can be formed by using the compound together with a binder such as gelatin, polyvinyl alcohol, cellulose acetate phthalate, cellulose acetate, polyvinyl acetate, polyvinyl chloride, polyvinylidene chloride, polyvinyl phthalate, polymethylmethacrylate, a co-polymer of styrene and maleic acid, cellulose acetate butyrate, cellulose ethylether phthalate, methyl cellulose, ethyl cellulose, polystyrene, cellulose nitrate, a polyurethane resin, a polyamide resin, a phenol resin, a urea resin, a melamine resin, etc.
  • a binder such as gelatin, polyvinyl alcohol, cellulose acetate phthalate, cellulose acetate, polyvinyl acetate, polyvinyl chloride, polyvinylidene chloride, polyvinyl phthalate, polymethylmethacryl
  • the antistatic layer can further contain various additives such as a hardening agent, e.g., formaldehyde, acrolein, chrom alum, etc., a slipping agent, e.g., sodium laurate, sodium stearate, etc., a matting agent, e.g., silica etc., or antihalation dye.
  • a hardening agent e.g., formaldehyde, acrolein, chrom alum, etc.
  • a slipping agent e.g., sodium laurate, sodium stearate, etc.
  • a matting agent e.g., silica etc.
  • antihalation dye e.g., sodium laurate, sodium stearate, etc.
  • the film support to which the present invention can be applied includes, for example, films of polyolefins such as polyethylene, polystyrene, a co-polymer of styrene and butadiene, cellulose esters such as cellulose triacetate, a polycarbonate, polyvinyl chloride, a polyamide, or polyesters such as polyethylene terephthalate, or baryta paper, synthetic paper-like sheets, or paper are coated with these substances on both sides.
  • polyolefins such as polyethylene, polystyrene, a co-polymer of styrene and butadiene
  • cellulose esters such as cellulose triacetate
  • a polycarbonate polyvinyl chloride
  • a polyamide polyamide
  • polyesters such as polyethylene terephthalate
  • baryta paper synthetic paper-like sheets, or paper are coated with these substances on both sides.
  • the surface resistivity was measured while a test piece was held by 10 cm long brass electrodes (using stainless steel at the parts contacting the test piece) with a distance of 0. 14 cm therebetween, using an insulation meter (Model MM-V-M, Takeda Riken K.K.) to
  • the static mark generating test was performed by placing an unexposed film on a rubber sheet with the antistatic agentcontaining side facing the rubber sheet. pressing them together by applying a rubber roller on top of the assembly, and then peeling off the film thereby generating static marks on the film.
  • the test was conducted at 23C at an RH of 30%.
  • test piece was conditioned under the above conditions for one day.
  • the sample was developed for 5 minutes at 20C using a developer solution of the following formulation.
  • EXAMPLE 1 An antistatic solution of the following formulation was coated on one surface of a polyethylene terephthalate film, and on the other surface, an emulsion for indirect roentgenography containing 9% of gelatin and 9% of silver halide was coated.
  • Antistatic Solution 1 Compound of This 0.010 g 0.017 g Invention Cellulose Triacetatc 0.34 g 0.34 g Solvent (a /8/8/2 1(15 g g mixture of ethylene chloride. methanol. tetrachloroethane. and phenol) The surface resistivity of the back surface of the processed film obtained and the state of static mark formation obtained are shown in Table 1 below.
  • EXAMPLE 2 An antistatic solution of the following formulation was coated on one surface of a cellulose triacetate film, and an indirect roentgenographic emulsion was coated on the other surface.
  • An antistatic photographic material comprising a support having thereon a photographic emulsion layer and a layer containing a compound expressed by the following formula R2 9 o l x ll I ⁇ cs c o B o .c cs
  • a and B each represent a straight chain or branched chain alkylene group, a xylylene group or a cyclohexylene group. in which the straight chain or branched chain alkylene group may contain a double bond. a triple bond or a (CH CH2 -,-CH- )CH group in the alkylene moiety: R,, R R and R each represent a lower alkyl group. or R and R and/or R and R may be combined together to form a nitrogencontaining heterocyclic ring; X is an anion; n is an integer of 20 to 50; and y is an integer of l to 20.
  • said layer is a surface layer and the amount of said compound is 0.01 to 1.0 g per square meter of the surface layer.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyamides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US453893A 1973-03-22 1974-03-22 Antistatic photographic material Expired - Lifetime US3876430A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP3283773A JPS5718175B2 (en)) 1973-03-22 1973-03-22

Publications (1)

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US3876430A true US3876430A (en) 1975-04-08

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US (1) US3876430A (en))
JP (1) JPS5718175B2 (en))
DE (1) DE2414005A1 (en))
GB (1) GB1410581A (en))

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118231A (en) * 1972-03-08 1978-10-03 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials containing antistatic agents

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH638362GA3 (en)) * 1977-06-10 1983-09-30
LU78153A1 (fr) * 1977-09-20 1979-05-25 Oreal Compositions cosmetiques a base de polymeres polyammonium quaternaires et procede de preparation
JP2684438B2 (ja) * 1990-07-20 1997-12-03 富士写真フイルム株式会社 帯電防止されたハロゲン化銀写真感光材料およびその製造法
US6066442A (en) 1995-10-23 2000-05-23 Konica Corporation Plastic film having an improved anti-static property
KR100526402B1 (ko) 2002-11-22 2005-11-08 주식회사 엘지화학 고리형 올레핀계 부가 중합체를 포함하는 네가티브Ｃ-플레이트(ｎｅｇａｔｉｖｅ Ｃ-ｐｌａｔｅ)형 광학이방성 필름 및 이의 제조방법
KR100618153B1 (ko) 2003-02-06 2006-08-29 주식회사 엘지화학 편광막의 보호필름, 편광판 및 이의 제조방법

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271148A (en) * 1962-07-19 1966-09-06 Eastman Kodak Co Mordanting of acid dyes
US3671468A (en) * 1969-09-04 1972-06-20 Chugai Pharmaceutical Co Ltd Polymers and process for preparing the same
US3794495A (en) * 1970-12-18 1974-02-26 Konishiroku Photo Ind Prevention of static in light-sensitive photographic materials using bisaminimide compounds
US3811887A (en) * 1970-12-18 1974-05-21 Konishiroku Photo Ind Photographic material comprising bisacylhydrazinium compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271148A (en) * 1962-07-19 1966-09-06 Eastman Kodak Co Mordanting of acid dyes
US3671468A (en) * 1969-09-04 1972-06-20 Chugai Pharmaceutical Co Ltd Polymers and process for preparing the same
US3794495A (en) * 1970-12-18 1974-02-26 Konishiroku Photo Ind Prevention of static in light-sensitive photographic materials using bisaminimide compounds
US3811887A (en) * 1970-12-18 1974-05-21 Konishiroku Photo Ind Photographic material comprising bisacylhydrazinium compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118231A (en) * 1972-03-08 1978-10-03 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic materials containing antistatic agents

Also Published As

Publication number Publication date
JPS49121523A (en)) 1974-11-20
JPS5718175B2 (en)) 1982-04-15
GB1410581A (en) 1975-10-22
DE2414005A1 (de) 1974-10-03

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