US3847615A - Image-receiving material for color diffusion transfer process - Google Patents

Image-receiving material for color diffusion transfer process Download PDF

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Publication number
US3847615A
US3847615A US00338715A US33871573A US3847615A US 3847615 A US3847615 A US 3847615A US 00338715 A US00338715 A US 00338715A US 33871573 A US33871573 A US 33871573A US 3847615 A US3847615 A US 3847615A
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United States
Prior art keywords
image
polymer
receiving material
transfer process
diffusion transfer
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US00338715A
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English (en)
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T Miyazako
T Yoshida
S Sakaguchi
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • 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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/42—Structural details
    • G03C8/52—Bases or auxiliary layers; Substances therefor

Definitions

  • This invention relates to an image-receiving material for a color photographic diffusion transfer process, more specifically, it relates to an image-receiving material for a color photographic diffusion transfer process, which image-receiving material has an improved layer for controlling the neutralization rate.
  • a color former such as a dye developer or a diffusible coupler type developer has been incorporated in a negative light-sensitive layer together with a silver halide photographic emulsionand after exposing the negative light-sensitive emulsion layer, the negative layer is brought into contact with a positive layer with an alkali processing agent between them, whereby the silver halide photographic emulsion is developed and at the same time the above-mentioned color former is diffused into the alkali processing agent and then transferred into the positive layer.
  • a color former such as a dye developer or a diffusible coupler type developer
  • the color former an alkaline and water-insoluble material has been mainly employed, but this type of color former is subject to the fault that when the positive layer containing it is exposed to air after the transfer is finished the material is oxidized to be decolored or to form stains.
  • an acid poly mer layer for neutralization is placed between the image-receiving layer and the support of the positive layer. That is to say, by placing the acid polymer layer for neutralization between the two layers, the dye image transferred can be prevented from being oxidized and thus the occurence of decoloring and the formation of stains are prevented.
  • this polymer layer is called a neutralization rate-controlling layer in this specificationlbetween the dye'image-receiving layer and the acid polymer layer for neutralization.
  • One object of this invention is, therefore, to provide a polymer suitable for the neutralization ratecontrolling layer of an image-receiving layer.
  • the image-receiving material for a color diffusion transfer process of this invention fundamentally comprises a support having thereon an acid polymer layer for neutralization, a neutralization rate-controlling layer and an image-receiving layer capable of mordanting dyes.
  • Examples of the support used in this invention are baryta-coated papers; laminate papers coated with a resin such as polyethylene polypropylene, and polystyrene; sheets of a cellulose organic acid ester such as cellulose diacetate, cellulose triacetate, cellulose butyrate, cellulose propionate and cellulose acetate butyrate; sheets of an inorganic acid ester such as cellulose nitrate; sheets of a polyester such as polyethylene terephthalate; sheets of polyvinylacetals such as polyvinyl I formal, polyvinyl butyral, polyvinyl acetal and polyvinyl benzal; and sheets of a polyalkylene such as polystyrene, polypropylene, polyethylene and polyvinyl chloride; polycarbonate, etc.
  • a resin such as polyethylene polypropylene, and polystyrene
  • sheets of a cellulose organic acid ester such as cellulose diacetate, cellulose triacetate, cellulose butyrate,
  • the polymer for the acid polymer layer for neutralization of the image-receiving material of this invention there can be used any polymer having one or more Another object of this invention is to provide an image-receiving layer for a color photographic diffusion carboxyl groups, sulfo groups or a group which changes to a carboxyl group by hydrolysis, and which has a filmforming property, including homopolymers, copolymers or graft polymers of vinylbenzenesulfonic acid and like materials.
  • the acid polymer preferably has a molecular weight of from about 10,000 to about 100,000.
  • polymer for the acid polymer layer for neutralization examples include the monoethyl ester, the monopropyl ester, the monopentyl ester and the monohexyl ester of the l l copolymer of maleic anhydride and ethylene; the monoethyl ester, the monopropyl ester, the monopentyl ester, and the monohexyl ester of the l 1 copolymer of maleic anhydride and methyl vinyl ether; polyacrylic acid; polymethacrylic acid; copolymers of acrylic acid and methacrylic acid in various component ratios; and copolymers of acrylic acid or methacrylic acid and other vinylic monomers in various component ratios, e.g., for example, acrylic esters, methacrylic esters, vinylethers and the like, suitably containing at least 30 molar percent of acrylic acid or methacrylic acid, and preferably from about 50 molar percent to about molar percent of acrylic acid or methacryl
  • Such a polymer as mentioned above is usually dissolved in an alcohol such as methanol, ethanol, propa- 3 nol and butanol; a ketone such as acetone, methyl ethyl ketone and cyclohexanone; an ester such as ethyl acetate and butyl acetate; or a mixture of these solvents, and then applied on the support as a solution.
  • an alcohol such as methanol, ethanol, propa- 3 nol and butanol
  • a ketone such as acetone, methyl ethyl ketone and cyclohexanone
  • an ester such as ethyl acetate and butyl acetate
  • the thickness of the acid polymer layer thus formed cannot be defined generally since it is well varied according to the composition and the amount of the alkali processing agent used, but it is suitably -30 microns.
  • the polymer used in the neutralization ratecontrolling layer is an alkali permeable and water permeable polymer. Practically speaking, the polymer used in the neutralization rate-controlling layer is a homopolymer, copolymer or graft polymer of a monomethacrylic acid ester and/or a monoacrylic acid ester of a polyhydric alcohol.
  • polyhydric alcohol used so long as the resulting polymer is alkali and water permeable.
  • preferred polyhydric alcohols used in this invention which can be aliphatic or aromatic in nature, can be defined as compounds having at least two aliphatic hydroxy groups, preferably compounds having from 2 to 5 aliphatic hydroxy groups, and having from 2 to 12 carbon atoms.
  • diols such as polyethylene glycol, polyethylene oxide, polypropylene oxide, polybutylene oxide, polycyclohexene oxide, polystyrene oxide, p0-
  • hydroxypentyl acrylate 2,2-dimethyl-hydroxypropyl acrylate, diethylene glycol monoacrylate, trimethylolpropane monoacrylate, pentaerythritol monoacrylate and the like.
  • addition-polymerizable monomer can be used, with preferred monomers being those having a vinyl or vinylidene group.
  • amides or esters having 3-15 carbon atoms of acrylic acid or methacrylic acid, such as, acryl amide, methacrylamide, diacetoneacrylamide, acryloyl morpholine, alkyl acrylates and methacrylates such as methyl methacrylate, ethyl methacrylate, propyl acrylate, propyl methyacrylate, chloroethyl acrylate, chloroethyl methacrylate, butyl acrylate, pentyl methacrylate, hexyl acrylate and hexyl methacrylate, vinyl esters such as vinyl acetate, vinyl butyrate, vinyl propionate, vinyl benzoether; styrenes such styrene, chlorostyrene, methoxystyrene, methylstyrene,
  • the proportion of the monomethacrylic acid ester of the polyhydric alcohol or the monoacrylic acid ester of the polyhydric alcohol be more than 50 mole percent, particularly more than mole percent.
  • the molecular weight of the polymer used in the neutralization rate-controlling layer is usually more than 10,000, preferably from 50,000 to 600,000.
  • gelatin As components used to form a graft polymer with the above esters used in this invention, it is preferred to use gelatin, polyvinyl alcohol, polyacrylamide, carboxymethyl cellulose, starch, hydroxyethyl cellulose, etc.
  • the polymers used in the neutralization ratecontrolling layer can be prepared by any ordinary method such as a solution polymerization, a graft polymerization and the like. Practical examples of preparing the polymers are illustrated below.
  • Synthesis Example 1 200 g of 2-hydroxyethyl methacrylate was added to a mixed solvent of 550 ml of water and 550 ml of ethanol in a reaction vessel. After adding to the mixture 1 g of potassium persulfate and l g of sodium hydrogen sulfite, oxygen in the reaction vessel was purged with nitrogen gas and then the mixture was stirred for 4 hours at 60C. in the vessel.
  • the reaction product liquid was filtered and then poured in cold water of (10 times the amount the filtrate), whereby the purified polymer prepared by the reaction was precipitated.
  • the polymer was recovered and dried by means of a vacuum dryer.
  • the amount of the polymer was 160g and the molecular weight thereof was 350,000.
  • Synthesis Example 2 176 g of 2-hydroxyethyl methacrylate and 24 g of acrylamide were added to a mixed solvent of 550 ml of water and 550 ml of ethanol in areaction vessel. After further adding to the mixture 0.8 g of potassium persulfate and 0.8 g of sodium hydrogen sulfite, the vessel was purged with nitrogen gas and the mixture was stirred'for 3 hours at C. The reaction product wasplaced in a pouch of a dialysis film, and after conducting dialysis for 15-20 hours in running water the product was dried by means of a freeze dryer. The amount of the product was 197 g and the mean molecular weight thereof was 20,000.
  • Synthesis Example 3 300 g of 3hydroxypropyl methacrylate was added to a mixed solvent of 400 ml of water and 800 ml of ethanol in a reaction vessel, and after adding further to the mixture 1 g ofazobisisobutyronitrile the vessel was filled with nitrogen gas. The mixture was then stirred for 3.5 hours while maintaining the reaction system at a temperature of 70C. The reaction product liquid was filtered and poured in cold water times the amount thereof), whereby the polymer prepared by the reaction was precipitated. The polymer thus precipiated was recovered and dried by means of a vacuum dryer.
  • the amount of the polymer was 260 g and the mean molecular weight thereof was 570,000.
  • Synthesis Example 4 94 g of 2-hydroxyethyl acrylate was copolymerized with 106 g of 2-hydroxyethyl methacrylate in the same manner as in Synthesis Example 2. The amount of the copolymer thus prepared was 186 g and the mean molecular weight thereof was 230,000.
  • Synthesis Example 5 419 g of 2-hydroxyethyl methacrylate and 81 g of methyl-methacrylate were added to a mixed solvent of 500 ml of water and 1500 ml of methanol in a reaction vessel. After further adding to the mixture 1.5 g of henzoyl peroxide, the oxygen in the vessel was purged with nitrogen gas and then the mixture was stirred for 4.5 hours at 60C. The copolymer thus formed was purified and dried in the same manner as in Synthesis Example 3. The amount of the copolymer was 430 g and the mean molecular weight thereof was 480,000.
  • Synthesis Example 6 50 g of hydroxyethyl cellulose was added to a mixed solvent of 750 ml of water and 150 ml of ethanol and was dissolved therein at 60C. in a reaction vessel. After-purging the vessel with nitrogen gas, the temperature of the reaction system was raised to 75C and then,
  • reaction system was stirred for 4 hours at 75C.
  • the reaction product was placed in a pouch of a dialysis membrane, and after conducting dialysis for hours in running water the product was dried by means of a freeze dryer.
  • the amount of the polymer was 88 g.
  • the polymers for the neutralization rate-controlling layer used in this invention can be dissolved in various kinds of solvents and in particular it is preferred to dissolve the polymers in a solvent such as ethanol, me-
  • the polymer to be mixed with the neutralization rate-controlling polymers of this invention preferably has good miscibility. Accordingly, it is preferred to use a polymer which has a polarity similar to the neutralization rate-controlling polymer.
  • the mixing ratio may be selected as desired but the proportion of the other polymer is preferably about 50 percent or less.
  • the dry thickness of the neutralizationrate-controlling layer composed of the polymer or polymers of the dye image receiving unit used in this invention be 3-20 microns, but the thickness may be varied properly according to the end use contemplated.
  • an image-receiving material it is necessary to use a material which has a layer which is hydrophilic and which is capable of mordanting a diffusible dye. So, it is preferred to use a hydrophilic, basic and film-forming polymer or a hydrophilic and film-forming polymer containing a basic polymer.
  • a hydrophilic, basic and film-forming polymer or a hydrophilic and film-forming polymer containing a basic polymer As specific examples of the image-receiving layer in this invention, a mixture of polyvinyl alcohol and poly-4-vinyl pyridine as described in US Pat. No.
  • 3,148,061 is preferably used, but other materials such as a partially acetalated product of polyvinyl alcohol (degree of acetylation is no more than 20'percent) and trialkylammonium benzaldehyde quaternary salt, a copolymer of vinyl alcohol and N-vinylpyrrolidone (any copolymerization ratio can be used), a condensed acetalation product (from about 4 l to about 2 1 molar condensate) of polyvinyl alcohol and poly-N-vinylpyrrolidone, and a condensed acetalation product (from about 4 1 to about 2 1 molar condensate) of polyvinyl alcohol and 4- pyridine carboxy aldehyde can also be used for the image-receiving layer.
  • This testing is merely exemplary of materials which meet the above general criteria.
  • the image-receiving material of this invention may further have, if desired, an intermediate layer for improving the adhesion between the support and the polymer layer and between the polymer layers themselves.
  • an intermediate layer for improving the adhesion between the support and the polymer layer and between the polymer layers themselves.
  • materials used for the intermediate material are polyvinyl alcohol, gelatin, carboxymethyl cellulose, hydroxyethyl cellulose, polyvinyl pyrrolidone, polyvinyl acetal, etc.
  • the thickness of the intermediate layer is suitably from about lg. to about 10p..
  • the image-receiving material of this invention has various advantages, e.g., the density of the images formed is higher and thus images of a wide range of gradation can be reproduced.
  • the polymer for the neutralization rate-controlling layer of this invention can be used for the neutralization rate-controlling layer of image-receiving materials for various types of color diffusion transfer processes.
  • the polymer may be used for the neutralization rate-controlling layers in a system using dye developers as described in U.S. Pat. No. 2,983,606 and also in a system using coupler developers as described in U.S. Pat. No. 3,227,551.
  • Example 1 The color image-receiving material, the alkali processing agent and the negative light-sensitive film were prepared in the manner described below. After imagewise exposure of the negative light-sensitive film, the negative film was combined with the color imagereceiving material, and the alkali processing agent (20C) inserted therebetween so that the thickness of the layer of the alkali processing agent was about 200 microns, whereby the diffusion transfer processing was conducted. The period required for the diffusion transfer process was 2 minutes.
  • a white baryta-coated layer having a polyethylene coating thereon was coated with layers (a), (b), and (c) in that order.
  • the alkali processing agent was prepared by blending the following components:
  • a .cellulose triacetate film having a gelatin undercoat was coated with the following three layers as a monchromatic system. i
  • aqueous emulsion was applied to the support in a dry thickness of 1.5 microns.
  • a silver iodobromide emulsion (7 mole percent silver iodide) containing 3.5 X 10 mole of silver and 6.5 g of gelatin per 100 g of emulsion was applied to the dye developer layer in a dry thickness of 1.5 microns.
  • an image-receiving material was prepared as a comparison sample in the same way as above except that a 10 wt. percent aqueous solution of polyvinyl alcohol (polymerization degree 1,800, saponification degree 98 percent) was applied in a dry thickness of 8 microns in place of the homopolymer of 2- hydroxyethyl methacrylate as the neutralization ratecontrolling layer of the image-receiving material.
  • polyvinyl alcohol polymerization degree 1,800, saponification degree 98 percent
  • Example 2 An imagereceiving material was prepared in the same way as in Example 1 except that the copolymer prepared by copolymerizing 2-hydroxyethyl methacrylate and acrylamide in a mole ratio of 4 l by the procedure of Synthesis Example 2 was-used as the neutralization rate-controlling layer. When the diffusion transfer was conducted using the image-receiving material as in Example 1, almost the same results as in Example 1 were obtained.
  • Example 3 An image-receiving material was prepared in the same way as in Example 1 except that the homopolyin a mixed solvent of 10 ml of N-nv mer of 3-hydroxypropyl methacrylate prepared in Synthesis Example 3 was used as the neutralization ratecontrolling layer. In this case also, almost the same results as in Example 1 were obtained when the same diffusion transfer as in Example 1 was conducted.
  • Example 4 An image-receiving material was prepared in the same way as in Example 1 except that the copolymer of 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate prepared in Synthesis Example 4 was used for the neutralization rate-controlling layer. When the same diffusion transfer as in Example 1 was conducted using this image-receiving material, almost the same results as in Example 1 were obtained.
  • Example 5 An image-receiving material was prepared in the same way as in Example 1 except that the graft polymer prepared by polymerizing 2-hydroxyethyl methacrylate in a solution of hydroxyethyl cellulose as in Syntehis Example 6 was used for the neutralization ratecontrolling layer and the solution of the polymer just after the polymerization reaction was finished was applied as it was to the acid polymer layer in a thickness of 8 microns.
  • the same diffusion transfer process as Example 1 was conducted using this image-receiving material, almost the same results as in Example 1 were obtained.
  • An image-receiving material for a color diffusion transfer process which comprises a support having thereon, in sequence, an acid polymer layer, a neutralization rate-controlling layer, and an image receiving layer, said neutralization rate-controlling layer comprising at least one polymer selected from the homopolymer, the copolymer and the graft polymer of the monomethacrylic acid ester of a polyhydric alcohol or the monoacrylic acid ester of a polyhydric alcohol.
  • An image-receiving material for color diffusion transfer process which comprises a support having thereon, in sequence, an acid polymer layer, a neutralization rate-controlling layer and an image receiving layer, said image-receiving layer comprising a polymer containing poly-4-vinylpyridine and said neutralization rate-controlling layer comprising at least one polymer selected from the homopolymer, the copolymer and the graft polymer of the monomethacrylic acid ester of a polyhydric alcohol or the monoacrylic acid ester of a polyhydric alcohol.

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US00338715A 1972-03-07 1973-03-07 Image-receiving material for color diffusion transfer process Expired - Lifetime US3847615A (en)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4056394A (en) * 1976-04-14 1977-11-01 Eastman Kodak Company Timing layer for color transfer film units comprising copolymer with activation energy to penetration greater than 18 kcal/mole
US4061496A (en) * 1976-04-14 1977-12-06 Eastman Kodak Company Combination of two timing layers for photographic products
FR2366599A1 (fr) * 1976-04-14 1978-04-28 Eastman Kodak Co Produit composite pour la photographie en couleurs par diffusion transfert comprenant une couche barriere a activite temporaire
US4088493A (en) * 1974-11-26 1978-05-09 Agfa-Gevaert Aktiengesellschaft Diffusion retarding layers comprising polymers of dimethoxyethylene
US4123275A (en) * 1975-07-24 1978-10-31 Fuji Photo Film Co., Ltd. Color diffusion transfer photographic materials with vinyl copolymer neutralization rate controlling layer
US4178182A (en) * 1973-08-24 1979-12-11 Fuji Photo Film Co., Ltd Color diffusion-transfer photographic element
US4190447A (en) * 1978-01-09 1980-02-26 Eastman Kodak Company Cover sheets for integral imaging receiver elements
US4193795A (en) * 1977-10-06 1980-03-18 Eastman Kodak Company Photographic film units containing a polymeric mordant which covalently bonds with certain dyes
US4415647A (en) * 1982-09-29 1983-11-15 Eastman Kodak Company Polymeric vehicle for dye image-receiving layer containing a poly(vinylimidazole) mordant
US5506089A (en) * 1993-03-09 1996-04-09 The Chromaline Corporation Photosensitive resin composition
US5972557A (en) * 1997-06-10 1999-10-26 Fuji Photo Film Co., Ltd. Photographic elements having temporary barrier layer
FR2848556A1 (fr) * 2002-12-13 2004-06-18 Bio Merieux Procede de polymerisation radicalaire controlee

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6029103B2 (ja) * 1976-12-10 1985-07-09 富士写真フイルム株式会社 カラ−拡散転写法用写真要素
JPS6012625B2 (ja) * 1977-10-05 1985-04-02 富士写真フイルム株式会社 カルボン酸ポリマ−層を有する拡散転写写真感光材料
US4288523A (en) * 1980-03-14 1981-09-08 Polaroid Corporation Diffusion control layers in diffusion transfer photographic products
US4359517A (en) * 1981-04-30 1982-11-16 Polaroid Corporation Diffusion transfer products with two timing layers for production of transparencies

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3421893A (en) * 1967-05-26 1969-01-14 Polaroid Corp Acrylic polymer spacer layers for photographic elements

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3421893A (en) * 1967-05-26 1969-01-14 Polaroid Corp Acrylic polymer spacer layers for photographic elements

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4178182A (en) * 1973-08-24 1979-12-11 Fuji Photo Film Co., Ltd Color diffusion-transfer photographic element
US4088493A (en) * 1974-11-26 1978-05-09 Agfa-Gevaert Aktiengesellschaft Diffusion retarding layers comprising polymers of dimethoxyethylene
US4123275A (en) * 1975-07-24 1978-10-31 Fuji Photo Film Co., Ltd. Color diffusion transfer photographic materials with vinyl copolymer neutralization rate controlling layer
US4061496A (en) * 1976-04-14 1977-12-06 Eastman Kodak Company Combination of two timing layers for photographic products
FR2366599A1 (fr) * 1976-04-14 1978-04-28 Eastman Kodak Co Produit composite pour la photographie en couleurs par diffusion transfert comprenant une couche barriere a activite temporaire
US4056394A (en) * 1976-04-14 1977-11-01 Eastman Kodak Company Timing layer for color transfer film units comprising copolymer with activation energy to penetration greater than 18 kcal/mole
US4193795A (en) * 1977-10-06 1980-03-18 Eastman Kodak Company Photographic film units containing a polymeric mordant which covalently bonds with certain dyes
US4190447A (en) * 1978-01-09 1980-02-26 Eastman Kodak Company Cover sheets for integral imaging receiver elements
US4415647A (en) * 1982-09-29 1983-11-15 Eastman Kodak Company Polymeric vehicle for dye image-receiving layer containing a poly(vinylimidazole) mordant
US5506089A (en) * 1993-03-09 1996-04-09 The Chromaline Corporation Photosensitive resin composition
US6020436A (en) * 1993-03-09 2000-02-01 The Chromaline Corporation Photosensitive resin composition
US5972557A (en) * 1997-06-10 1999-10-26 Fuji Photo Film Co., Ltd. Photographic elements having temporary barrier layer
FR2848556A1 (fr) * 2002-12-13 2004-06-18 Bio Merieux Procede de polymerisation radicalaire controlee

Also Published As

Publication number Publication date
GB1396476A (en) 1975-06-04
DE2311207A1 (de) 1973-09-13
FR2175131B1 (enrdf_load_stackoverflow) 1976-11-05
FR2175131A1 (enrdf_load_stackoverflow) 1973-10-19
JPS5246496B2 (enrdf_load_stackoverflow) 1977-11-25
JPS4892022A (enrdf_load_stackoverflow) 1973-11-29

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