US3833403A - Process for subbing photographic polyester films - Google Patents

Process for subbing photographic polyester films Download PDF

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Publication number
US3833403A
US3833403A US00363051A US36305173A US3833403A US 3833403 A US3833403 A US 3833403A US 00363051 A US00363051 A US 00363051A US 36305173 A US36305173 A US 36305173A US 3833403 A US3833403 A US 3833403A
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US
United States
Prior art keywords
subbing
film
photographic
polyester film
composition
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
US00363051A
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English (en)
Inventor
M Kogure
Y Muroi
H Ohta
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.)
Konica Minolta Inc
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Konica Minolta Inc
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Filing date
Publication date
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Publication of US3833403A publication Critical patent/US3833403A/en
Assigned to KONICA CORPORATION reassignment KONICA CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: KONISAIROKU PHOTO INDUSTRY CO., LTD.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/91Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
    • G03C1/915Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means using mechanical or physical means therefor, e.g. corona
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/91Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/151Matting or other surface reflectivity altering material

Definitions

  • This invention relates to a process for subbing a photographic polyester film in order to have strong adhesion of a photographic gelatinous composition to the polyester film.
  • the invention pertains to a process for subbing a photographic polyester film in order to firmly adhere to the polyester film a photographic gelatinous composition, e.g., a gelatinsilver halide emulsion, a gelatinous composition containing an antihalation agent, or a gelatin backing composition, which comprises subjecting at least one side of the polyester film to electron bombardment, and
  • a photographic gelatinous composition e.g., a gelatinsilver halide emulsion, a gelatinous composition containing an antihalation agent, or a gelatin backing composition
  • An object of the present invention is to provide a process for subbing a polyester film in which no swelling or solubilizing agent for polyester is substantially used.
  • Another object of the invention is to provide a process for subbing a photographic polyester film without injuring the polyester film in flatness, which process makes it possible to firmly adhere a photographic gelatinous composition to the polyester film and does not give any detrimental influence to the photographic properties of said photographic gelatinous composition.
  • a process for subbing a polyester film which comprises subjecting at least one side of the polyester film to electron bombardment so that the contact angle thereof with water becomes less than 58, and then applying to the treated surface of the polyester film a subbing composition containing (a) a copolymer latex of a diolefin with other polymerizable ethylenically unsaturated monomer and (b) a compound having two or more of groups selected from ethyleneimino and methylsulfonyloxy groups. If any one of the conditions required in the said subbing proscribed later.
  • the polyester film used in the present invention is composed of an aliphatic diol and an aromatic dicarboxylic acid, and a typical example thereof is a polyethylene terephthalate film.
  • the copolymer latex used in the present invention is composed of a diolefin and other polymerizable ethylenically unsaturated monomer.
  • the diolefin include butadiene, 2-chloroprene, isoprene, neoprene and 2,3-methylbutadiene
  • examples of the said other polymerizable ethylenically unsaturated monomer include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, butyl acrylate, butyl methacrylate, chloroethyl acrylate, chloroethyl methacrylate, hydroxyethyl acrylate, hydroxyethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-ethylhexyl acrylate, glycidy
  • N,N-dialkyl acrylamides the alkyl includes, for example, methyl, ethyl, propyl, butyl and amyl, and the two alkyls may be same or different
  • copolymer lattice can be easily obtained as commercially available products.
  • Typical examples of the obtainable copolymer lattice are Hycar 2570x5, Hycar 1551, Hycar 1561, Hycar 1571, Hycar 1562, Hycar 1577, Nipol 4850, Nipol LX-l l0, Hycar LX-204, Hycar LX-303, Hycar LX-407, Hycar LX- 411, Hycar LX-4l5, Hycar LX-4l6, Hycar 2507 and Hycar 2518 produced by Nippon Geon Co.; Croslene SA-20, Croslene NA-lO, Croslene NS-16, Croslene 2M-30, Croslene NA-ll, Croslene SA-22, Croslene SA-23, Croslene SA-24, Croslene 2M-33, Croslene 2M-33A, Croslene 2M-36, Croslene 2M-38 and Croslene SK-SO produced by Takeda Chemical Industries, Ltd.; Dow
  • Binder LF-3 produced by Dainichi Seikako Co.
  • NK Binder SM-200R produced by Nakamura Kagaku Co.
  • Corporex No. 1001 and Corporex No. 1031 produced by Mitsubishi Gas Kagaku Co.
  • Wool Cement 3C and Wool Cement No. CS produced by Kyoritsu Kagaku Sangyo Co.
  • Bortex GV produced by Meisei Kagaku Co., and all of these are effectively usable.
  • the copolymer latex used in the present invention is preferably one'which contains 25 to 75 percent by weight of a diolefin and about to 30 percent by weight of a polymerizable ethylenically unsaturated monomer containing at least one reactive active or readily reactive) functional group having at the terminals at least one of hydroxyl, formyl, carboxyl, amido, alkoxy, isocyanato and ethyleneimino groups.
  • Typical examples of the compound having two or more groups selected from ethyleneimino and methylsulfonyl groups are as follows:
  • n is an integer of 1 to NCONH- CH1 CH, NHC ON (3).-- CH; CH,
  • n is an integer ol 1 to 10
  • n is an integer of 2 to 6
  • n is an integer of 2 to 200
  • the above-mentioned compound which is the aforesaid component (b), is used in an amount within the range from 0.01 to 100 percent, preferably from about 0.1 to 30 percent, by weight based on the weight of the aforesaid copolymer latex.
  • the compound as the component (b) is dissolved in water or an organic solvent or in a mixture of the two, and then added to the aforesaid copolymer latex to prepare a subbing composition.
  • the subbing composition is in the form of an aqueous dispersion, in general, but may alternatively be used, depending on the kind of drying means employed, in the form of a dispersion in a mixed solvent comprising water and methanol, ethanol, acetone or the like organic solvent lower in boiling point than water.
  • the organic solvent is used in 0.1 to 10 times the amount of waters
  • the subbing composition is applied by such means as coating and drying onto the surface of polyester film whose contact angle with water has brought to less than 58 according to electron bombardment.
  • the electron bombardment is carried out by use of such corona discharge apparatus or the like that electrons are discharged at a high speed between at least a pair of electrodes in the presence of a gas or under pressure.
  • the electron bombardment should be conducted to such an extent that the contact angle of polyester film with water becomes less than 58. If the contact angle is more than the said value, no satisfac-' tory subbing effect can be attained, as is clear from the working examples described later.
  • a polyester film is subjected to electron bombardment so that the contact angle thereof with water becomes less than 58", and then a subbing composition containing the aforesaid component (a) (copolymer latex) and the aforesaid component (b) (exemplified compound) is applied according to such means as, for example, coating and drying to the treated side of the polyester film, whereby the subbed polyester film surface becomes highly adherent to a photographic gelatinous composition and sufficiently maintains the excellent adhesion even under severe conditions.
  • the subbing composition according to the present invention does not give any detrimental influence to the photographic properties of photographic gelatinous composition and, moreover, does not require the use of swelling or dissolving for polyester to make it possible to overcome various problems derived from the use of said agents.
  • the subbing composition used in the present invention may contain various photographic additives in addition to the aforesaid components (a) and (b).
  • the subbing composition may be incorporated with such a hardener used to enhance the water resistance of photographic gelatinous composition as, for example, formaldehyde, mucochloric acid, acrolein, glyoxal, divinyl sulfone, vinyl sulfone, dichlorotriazine, hexahydrol ,3,5-triacryloyl-s-triazine, dihydroxybenzene, methylenebis acrylamide, dicarboxylic acid dinitrophenyl ester, dicarboxylic acid dichloromethyl ester, carbodiimide derivative, Woodwards reagent or chromium chloride.
  • a hardener used to enhance the water resistance of photographic gelatinous composition as, for example, formaldehyde, mucochloric acid, acrolein, glyoxal
  • the subbing composition may be incorporated with a surface active agent, e.g., natural saponin or anionic or nonionic synthetic surface active agent, in order to disperse the copolymer latex, and with a matting agent, e.g., colloidal silica, titanium oxide, zinc oxide, aluminum oxide polymethyl methacrylate or polystyrene beads, or starch powder.
  • a surface active agent e.g., natural saponin or anionic or nonionic synthetic surface active agent
  • a matting agent e.g., colloidal silica, titanium oxide, zinc oxide, aluminum oxide polymethyl methacrylate or polystyrene beads, or starch powder.
  • the subbing composition may be incorporated with dye or pigment for antihalation or for coloration of film base.
  • a subbing composition comprising 6 g. of Polylac SL-204 (produced by Mitsui Toatsu Co.), 0.18 g. of hexamethylenebis ethyleneimino ureide (the exemplified compound (1), wherein n
  • Dry film adhesion test invention The photographic emulsion layer surface of each sample was scratched with a razor so as to form squares. Subsequently, a cellophane adhesive tape was applied under finger pressure onto the said surface and then quickly stripped off therefrom, and the residual ratio of the photographic emulsion layer on the film base to the adhesion surface area of the tape was repre sented by percentage.
  • Wet film adhesion test invention The photographic emulsion layer surface of each sample was scratched with a razor so as to form squares. Subsequently, a cellophane adhesive tape was applied under finger pressure onto the said surface and then quickly stripped off therefrom, and the residual ratio of the photographic emulsion layer on the film base to the adhesion surface area of the tape was repre sented by percentage.
  • the photographic emul emulsion layer surface of each sample was scratched with the sharp tip of a gimlet so as to form squares and then rubbed, and the residual ratio of the photographic emulsion layer on the film base was represented by per centage.
  • a biaxially stretched polyethylene terephthalate film was pre-treated with a methanol solution containing p-chlorophenol, dried at 80 C. for 2 minutes, and then equally divided into two.
  • One film was coated with the above-mentioned subbing composition, and the other film was coated with the same composition as above, except that the trimethylenedimethane sulfonate was not contained.
  • These films were individually coated onto the subbed surfaces with the same roentgen emulsion as above, and then dried to prepare samples.
  • Example 3 Biaxially stretched polyethylene terephthalate films which had been subjected to corona discharge treatment under the same conditions as in the case of the sample (1) prepared in Example 1, were individually coated onto the surfaces with each of such subbing compositions as shown in Table 3, dried at C. for 1 minute, further coated with an antihalation backing gelatin layer containing an absorption dye, and then dried to prepare samples. These samples were subjected to the same sub layer adhesion tests as in Example l to obtain the results as set forth in Table 3.
  • Example 4 A biaxially stretched polyethylene terephthalate film, which had-been subjected to corona discharge treat- .ment under the same conditions as in the case of the Table 3 Sample Subbing composition (made I ccv Dry film Wet film No. by addition of water) adhesion adhesion (I0) Hycur 2570X5 (7 g.)
  • a process for subbing a photographic polyester 1.
  • a process for subbing photographic polyester film bing composition containing (a) a copolymer latex of as claimed incl aim l, wherein said compound (b) is a diolefin with other polymerizable ethylenically unsatthat whi h at lea t ne methylsulfonyloxy group in adurated monomer and (b) a compound having two or dition to one or more groups selected from more groups selected from ethylenermino and methylthyl i in and methylsulfonyloxy groups. sulfonyloxy groups.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Laminated Bodies (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
US00363051A 1972-05-30 1973-05-23 Process for subbing photographic polyester films Expired - Lifetime US3833403A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP47052978A JPS5232568B2 (es) 1972-05-30 1972-05-30

Publications (1)

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US3833403A true US3833403A (en) 1974-09-03

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ID=12929974

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Application Number Title Priority Date Filing Date
US00363051A Expired - Lifetime US3833403A (en) 1972-05-30 1973-05-23 Process for subbing photographic polyester films

Country Status (6)

Country Link
US (1) US3833403A (es)
JP (1) JPS5232568B2 (es)
BR (1) BR7303937D0 (es)
DE (1) DE2327302C3 (es)
GB (1) GB1401703A (es)
SU (1) SU576074A3 (es)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4168172A (en) * 1977-11-24 1979-09-18 Fuji Photo Film Co., Ltd. Method for subbing polyester films
US4197129A (en) * 1973-03-05 1980-04-08 Konishiroku Photo Industry Co., Ltd. Plastic support having improved adhesivness to material to be bonded thereto
US4429039A (en) 1975-03-31 1984-01-31 Fuji Photo Film Co., Ltd. Photographic element
US4440847A (en) * 1982-08-20 1984-04-03 Am International, Inc. Diazo material with waterborne drafting subbing composition of acrylic resin and aziridine and process of using
US5425980A (en) * 1994-02-22 1995-06-20 Eastman Kodak Company Use of glow discharge treatment to promote adhesion of aqueous coats to substrate
EP0736801A2 (en) * 1995-04-03 1996-10-09 Eastman Kodak Company Molecular grafting to energetically treated polyesters to promote adhesion of gelatin-containing layers
US5618659A (en) * 1995-03-01 1997-04-08 Eastman Kodak Company Photographic element containing a nitrogen glow-discharge treated polyester substrate

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5922217B2 (ja) * 1973-08-10 1984-05-25 富士写真フイルム株式会社 ポリエステルフイルムの下塗法
JPS57486B2 (es) * 1973-08-21 1982-01-06
JPS57487B2 (es) * 1974-08-31 1982-01-06
JPS5858656B2 (ja) * 1975-04-09 1983-12-26 富士写真フイルム株式会社 シヤシンザイリヨウ
GB1540067A (en) * 1975-09-26 1979-02-07 Bexford Ltd Coated film bases
JPS541612A (en) * 1977-04-27 1979-01-08 Du Pont Undercoat composition
US4220471A (en) * 1977-10-13 1980-09-02 Mitsubishi Paper Mills, Ltd. Photographic polypropylene coated paper support with corona discharge treatment and polymeric subbing layer
JPS5464572A (en) * 1977-11-02 1979-05-24 Mitsubishi Paper Mills Ltd Method of providing hydrophilic material to hydropholic surface
JPS5565949A (en) * 1978-11-13 1980-05-17 Fuji Photo Film Co Ltd Subbing method for photographic material
DE3060639D1 (en) * 1979-02-16 1982-08-26 Eastman Kodak Co Coating composition containing a polyaniline salt semiconductor, a method of preparing said composition and an element with a conductive layer formed from said composition
US5968646A (en) * 1996-01-19 1999-10-19 Eastman Kodak Company Molecular grafting of hardener/gelatin blends to energetically treated polyesters to promote adhesion of layers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2964404A (en) * 1957-07-26 1960-12-13 Eastman Kodak Co Hardening of gelating with aziridinylsulfonyl compounds
US3216825A (en) * 1961-02-23 1965-11-09 Eastman Kodak Co Photographic film element comprising butadiene polymeric coatings on polyethylene and other polymeric hydrocarbons
US3220842A (en) * 1961-09-01 1965-11-30 Eastman Kodak Co Electrically prepared subbing for photo-stencil film on polyethylene terephthalate support

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE633988A (es) * 1962-06-25
DE1298717B (de) * 1965-09-09 1969-07-03 Fuji Photo Film Co Ltd Aufbringen einer Unterschicht auf Polyesterfolien
FR1517367A (fr) * 1966-03-31 1968-03-15 Fuji Photo Film Co Ltd Traitement sous-jacent pour films photographiques
US3549406A (en) * 1968-04-26 1970-12-22 Eastman Kodak Co Process of coating polymer surfaces activated by corona discharge
JPS4843122B1 (es) * 1969-11-20 1973-12-17

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2964404A (en) * 1957-07-26 1960-12-13 Eastman Kodak Co Hardening of gelating with aziridinylsulfonyl compounds
US3216825A (en) * 1961-02-23 1965-11-09 Eastman Kodak Co Photographic film element comprising butadiene polymeric coatings on polyethylene and other polymeric hydrocarbons
US3220842A (en) * 1961-09-01 1965-11-30 Eastman Kodak Co Electrically prepared subbing for photo-stencil film on polyethylene terephthalate support

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4197129A (en) * 1973-03-05 1980-04-08 Konishiroku Photo Industry Co., Ltd. Plastic support having improved adhesivness to material to be bonded thereto
US4429039A (en) 1975-03-31 1984-01-31 Fuji Photo Film Co., Ltd. Photographic element
US4168172A (en) * 1977-11-24 1979-09-18 Fuji Photo Film Co., Ltd. Method for subbing polyester films
US4440847A (en) * 1982-08-20 1984-04-03 Am International, Inc. Diazo material with waterborne drafting subbing composition of acrylic resin and aziridine and process of using
US5425980A (en) * 1994-02-22 1995-06-20 Eastman Kodak Company Use of glow discharge treatment to promote adhesion of aqueous coats to substrate
US5538841A (en) * 1994-02-22 1996-07-23 Eastman Kodak Company Use of glow discharge treatment to promote adhesion of aqueous coatings to substrate
US5576164A (en) * 1994-02-22 1996-11-19 Eastman Kodak Company Photographic element having a polyester substrate with an oxygen modified surface region
US5582921A (en) * 1994-02-22 1996-12-10 Eastman Kodak Company Use of glow discharge treatment to promote adhesion of aqueous coatings to substrate
US5618659A (en) * 1995-03-01 1997-04-08 Eastman Kodak Company Photographic element containing a nitrogen glow-discharge treated polyester substrate
EP0736801A2 (en) * 1995-04-03 1996-10-09 Eastman Kodak Company Molecular grafting to energetically treated polyesters to promote adhesion of gelatin-containing layers
EP0736801A3 (en) * 1995-04-03 1997-02-26 Eastman Kodak Co Molecular grafting on polyesters pretreated with an energy source to promote the adhesion of layers containing gelatin
US5700577A (en) * 1995-04-03 1997-12-23 Eastman Kodak Company Molecular grafting to energetically treated polyesters to promote adhesion of gelatin-containing layers

Also Published As

Publication number Publication date
DE2327302A1 (de) 1973-12-13
SU576074A3 (ru) 1977-10-05
DE2327302B2 (de) 1980-12-04
DE2327302C3 (de) 1981-09-03
JPS5232568B2 (es) 1977-08-23
GB1401703A (en) 1975-07-30
JPS4911118A (es) 1974-01-31
BR7303937D0 (pt) 1974-08-15

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Legal Events

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AS Assignment

Owner name: KONICA CORPORATION, JAPAN

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302

Effective date: 19871021