US3025163A - Photographic element having polycarbonate sub-layer - Google Patents

Photographic element having polycarbonate sub-layer Download PDF

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Publication number
US3025163A
US3025163A US722464A US72246458A US3025163A US 3025163 A US3025163 A US 3025163A US 722464 A US722464 A US 722464A US 72246458 A US72246458 A US 72246458A US 3025163 A US3025163 A US 3025163A
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layer
dihydroxy
polycarbonate
film
vinyl
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Ossenbrunner Armin
Klockgether Helfried
Kruck Peter
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Agfa Gevaert NV
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Agfa AG
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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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/91—Photosensitive materials characterised by the base or auxiliary layers characterised by subbing layers or subbing means
    • G03C1/93—Macromolecular substances therefor

Definitions

  • the present invention relates to photographic film supports having improved anchoring layers for water permeable colloid layers, and more particularly to cellulose film supports having polycarbonate sublayers.
  • thermoplastic polycarbonates of high molecular weight especially those derived from di-(monohydroxyaryl) alkanes,'are very suitable for improving the resistance to breakage without showing the disadvantages of the other processes.
  • X is selected from thegroup consisting of monovalent cycloaliphatic and aromatic hydrocarbon fying the bonding layer that the maintenance of an adequate bonding effect is coupled with improved resist-
  • R R and R standing for the same or for different radicals.
  • - Preferred polycarbonates are such in which R"s are hydrogen atoms and Rs are aliphatic or cycloaliphatic hydrocarbon residues of the kind mentioned above, whereby the two R's may be the same or different members of action is very quickly produced.
  • the emulsion When subjected to mechanical stress, the emulsion lifts from the film material and it floats off in the photographic baths.
  • intermediate layers the polarity of whichconforms better to the gelatine than the acetyl cellulose, so that they can be provided with a gelatine anchoring layer without the; gelatine being firmly incorporated into the, surface of. the intermediate layer.
  • the intermediate layer can be so applied that the fracture of the emulsion layer is taken up at the boundary surface between the intermediate layer and support.
  • nitrocellulose lacquer intermediate layers has been proposed, it being known that these can be coated without additives with weakly acting solvents containing gelatine.
  • nitrocellulose is however not desirable owing to the fact that it is readily inflammable.
  • each R represents a hydrogen atom or the same or a different member of the groups mentioned above and each R represents a member of the group consisting of the methyl, the ethyl, the propyl, the isopr'opyl, the n-butyl, the tert. butyl, the isobutyl, the tert. amyl, thecyc'lopentyl, the cyclohexyl, and the phenyl being hydrogen.
  • each R is the same or Under these polycarbonates typical representatives are for instance the poly-(2,2-(4,4-dihydroxy-diphenylen)- propane-carbonate), the poly (2,2 (4,4-dihydroxy-diphenylen)-butane-carbonate), the poly-(2,2-(4,4'-dihydroxydiphenylen)-pentane-carbonate), the poly-(1,1-(4, 4'-dihydroxydiphenylen)-cyclohexane-carbonate), and the mixed poly (2,2 (4,4'-dihydroxy-diphenylen)-propaneand (4,4-dihydroxy-diphenylen)methane-carbonate).
  • Aliphatic dihydroxy compounds such as: ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, thiodiglycol, ethylene dithiodiglyeol, the di-, and polyglycols produced from propyleneoxide-l,2, o, m, or p-xylylene glycol, propanediol-1,3, butanediol-1,3, butanediol-l,4, 2-methylpropanediol-L3, pentanediol-l,5, 2-ethylpropanediol-l,3, hexanediol-1,6, octanediol-1,8, l-ethylhexane diol-l,3, and decanediol-l,l0, cycloaliphatic dihydroxy compounds such as cyclohexanediol-l,4, cyclohexanediol-1,2, 2,2-(
  • the aryl residues can be the same or different.
  • the aryl residues can furthermore carry hydrogen atoms or substituents which are incapable of taking part in the reaction to polycarbonates, e.g. the halogens and alkyl groups such as ethyl, methyl, propyl or tertiary butyl.
  • dihydroxydiaryl sulphones of the specified type the following may be mentioned:
  • dihydroxy compounds which may be used in admixture with the dihydroxydiaryl sulphones if desired, there may be mentioned the following: ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, the corresponding thioglycols, di- 01' poly-glycols obtained from propylene oxide-1,2, propanediol-l,2, propanediol-l,3, butanediol-1,3, butanediol-1,4, 2-methylpropanediol-1,3, pentanediol-l,5, 2-ethylpropanediol-l,3, hexanediol-l,6, octanediol-1,8, 2-ethylhexanediol-l,3 and decanediol-l,l0; cyclohexanediol-l,4, cyclohexanediol-l,
  • Di-monohydroxyarylalkanes as disclosed in copending application Serial No. 577,362, filed April 4, 1956, and in British specification No. 772,627, such as di-(p-hydroxyphenyl)-methane, 2,2- di-(p-hydroxyphenyl)-propane, 1,1-di-(p-hydroxyphenyl)- cyclohexane, l,1-di-(p-hydroxy-m-methylphenyl) cyclohexane, 2,2 di (o-hydroxy-p-tert.-butylphenyl) -propane and 3,4-di-(p-hydroxy-phenyl)-hexane and 1,1-di-(p-hydroxy-phenyl) 1 phenyl-ethane, furthermore methane derivatives which carry besides two hydroxylaryl groups, a further alkyl residue with at least two, and a second alkyl residue with one or more carbon atoms, e.g.
  • 2,2-di- (p-hydroxyphenyl) -butane 2,2 di (p-hydroxyphenyD- pentane, 3,3-di-(p-hydroxyphenyl)-pentane, 2,2-d1-(p-hydroxyphenyl)-2-methylbutane, 2,2-di-(p-hydroxy-phenyl)- hexane, 2,2-di-(p-hydroxyphenyl)-4-methylpentane, 2,2- di (p hydroxyphcnyl)-heptane, 4,4-(p-hydroxyphenyl)- heptane and 2,2-di-(p-hydroxyphenyl)tridecane.
  • the polyesters may be produced it, for example, bischloro-carbonates of dihydroxy diaryl sulphones or mixture thereof with the aforementioned dihydroxy com pounds, "are condensed with dihydroxy diaryl sulphones, or mixtures thereof with other dihydroxy compounds. These condensations are suitably brought about in the presence of inert solvents and acid-binding agents such as tertiary amines as described for analogous processes in British specification No. 772,627.
  • a further method of carrying out the process consists in passing phosgene either into an aqueous alkali solution or suspension of the dihydroxy diaryl sulphone, optionally in the presence of other dihydroxy compounds and inert solvents, or into a solution or suspension of these materials in an inert solvent optionally in the pres ence of acid-binding agents such as tertiary amines also as described for analogous processes in British specification No. 772,627. According to both methods of carrying out the process it is an advantage to accelerate the polycondensation by adding to the reaction mixture quaternary ammonium compounds in the form of their free bases or as salts.
  • the polycarbonates by inter-esterifying dihydroxy diaryl sulphones, optionally mixed with the aforementioned dihydroxy compounds and suitably in the presence of acidic or basic catalysts, with dialkyl or diaryl carbonates.
  • the basic catalysts preferably used are suitably neutralized in the course of, or at the end of, the polycondensation by adding base-binding substances are especially suitable since an excess thereof can be removed by evaporation or sublimation from the melt.
  • the aryl radicals may further carry substituents which are incapable of reacting during the conversion into the poly-carbonates such as halogen, or alkyl groups such as the methyl-, ethyl-, propylor the tert. butyl group.
  • Suitable dihydroxy-diaryl ethers or -thioethers are, for example:
  • the further dihydroxy compound which may be used in combination with the said ethers and thioethers may be the same as those disclosed above in connection with the production of polycarbonates derived from diaryl sulfones.
  • the polycarbonates produced from the above ethers and thioethers or mixtures of said compounds with further dihydroxy compounds may be produced by the same methods as the polycarbonates derived from diarylsulphones and mixtures of said sulphones with further dihydro compounds.
  • aromatic dihydroxy compounds derived from mixtures of aliphatic and/or cycloaliphatic dihydroxy compounds with aromatic dihydroxy compounds other than the above dihydroxy diarylalkanes, dihydroxydiarylsulfones, and dihydroxydiarylethers and -thioethers there may be used the following aromatic dihydroxy compounds:
  • ethylene glycol diethylene glycol, triethylene glycol, polyethylene glycol, thiodiglycol, ethylene dithiodiglycol, propane diol-1,2, propanediol-l,3, butanediol-1,3, butanediol-1,4, 2-methylpropanediol-1,3, pentanediol-1,5, 2-ethylpropanediol-1,3, hexanediol-1,6, octanediol-1,8, 2-ethylhexanediol-l,3, decanediol-1,l0, cyclohexanediol-1,4, cyclohexanediol-1,2- 0-, mor p-xylylene glycol, 2,2'-(4,4- dihydroxydichlorohexyl)-prop
  • polycarbonates derived from the disclosed sulphones, ethers and thioethers may be represented by way of example by the following formula:
  • R stands for one of the following bivalent radicals: SOFQ G G G O the phenyl radicals of which may be substituted and n stands for a whole number preferably greater than 10.
  • the mixed polycarbonates may contain the following units:
  • the polycarbonates may also be produced by the processes indicated in the following patents: British Patent 772,627; French Patents 1,149,261; 1,152,155; 1,152,156; 1,152,157; 1,152,158; Belgian Patents 546,375; 555,894.
  • the application of the polycarbonate intermediate layer to the organic cellulose ester film takes place from specific solvent mixtures, since otherwise adequate bonding to the support is not-produced.
  • Nonsolvents are preferably in quantities of 60 to 40 parts by weight and the solvent in quantities of 40 to 60 parts by weight.
  • the polycarbonates can be used alone, but can be admixed with other plastics, provided the various components are compatible with one another.
  • plastics are: nitrocellulose (nitrogen content 11.7- 12.3%), ethyl cellulose (ethoxyl content 48.049.5%) and co-polymers of ethylene and vinyl acetate or vinylpropionate preferably such containing 30 to 50 percent by weight of vinylester. It is possible in many cases to produce additional effects therewith.
  • intermediate layers are preferably provided with a further anchoring or bonding layer varying from about 0.05 to 2 microns in thickness.
  • additional layers may be produced from a mixture of (1) Gelatine and copolymers containing hydroxyl groups, preferably a partially saponified copolymer of vinyl chloride and vinyl acetate, or
  • the intermediate polycarbonate layer must have a certain minimum thickness, since otherwise the preparation penetrates in spite of the slight attacking action, and this results in poor bonding and also in lower resistance to breakage.
  • the aforementioned additional layer of gelatine and a polymer containing hydroxyl groups preferably consists essentially of gelatine and a partially hydrolysed copolymer of 40 to 60 parts by weight of vinyl chloride and 60 to 40 parts by weight of an organic vinyl ester, such as vinylacetate, vinylpropionate, vinylbutyrate, vinyl benzoate, this copolymer advantageously containing from 45 to 70% by Weight of vinyl chloride, 530% by weight of vinyl hydroxide and 10 to 40% by weight of organic vinyl ester.
  • the proportion of gelatine with respect to the copolymer can fluctuate within Wide limits; it is however advantageous to use a ratio of 2:3 parts by weight of gelatine to 3:2 parts of copolymer.
  • the aforementioned mixed acetals can be obtained bya conventional process, for example by heating the components for several hours in methanolic solution with sulphuric acid as catalyst.
  • aldehydes with water-solubilizing groups are aromatic aldehydes which are substituted in the aromatic nucleus by carboxyl, sulphonic acid or hydroxy groups, for example benzaldehyde-Z-sulphonic acid, benzaldehyde-2,2-disulphonic acid and p-hy- -droxy benzaldehyde.
  • the acid groups may be neutralized with bases capable of yielding water-soluble salts such as alkali metals (sodium, potassium, lithium) ammonia, amines such as primary, secondary and tertiary methyl-, ethyl-, propylamines, cyclohexylamine, morpholine, piperidine.
  • bases capable of yielding water-soluble salts such as alkali metals (sodium, potassium, lithium) ammonia, amines such as primary, secondary and tertiary methyl-, ethyl-, propylamines, cyclohexylamine, morpholine, piperidine.
  • the mixed acetals are preferably dissolved in a proportion of 0.75 to 1.25% in a mixture of methanol and one or more other organic solvents, for example acetone, tetrahydrofurane or dioxane.
  • a partially saponified copolymer of vinyl chloride and an organic vinyl ester for example vinyl acetate, vinyl propionate or vinyl butyrate, for example a paritially saponified copolymer of vinyl chloride and vinyl acetate.
  • organic vinyl ester for example vinyl acetate, vinyl propionate or vinyl butyrate
  • a paritially saponified copolymer of vinyl chloride and vinyl acetate are produced by known methods by saponification in methanol solution with sulphuric acid as catalyst, merely the organic ester groups being partially saponified.
  • Suitable saponified copolymers contain approximately 45- 70% by weight of vinyl chloride, 30% by weight of vinyl hydroxide and -40% by weight of vinyl acetate or another organic vinyl ester such as vinyl propionate, vinyl butyrate or vinyl benzoate.
  • Copolymers of vinyl chloride and e s-unsaturated carboxylic acids or partially saponified copolymers of vinyl chloride and esters of the aforementioned acids can alternatively be used.
  • the coating is advantageously produced by one of the conventional dipping processes.
  • Example 1 An acetyl cellulose film (61.0% acetic acid) is treated with the following base or substrate solution by the dipping process:
  • the film is thereafter provided with a gelatino silver halide emulsion layer having a thickness of 8 to 18 microns.
  • the resistance to breaking is good; the bonding effect is adequate. It is true that the emulsion breaks at low relative air humidities, but the breakage is not transferred to the support.
  • the layer is dried at 90-1 10 C. and subbed with the following solution:
  • the film support After being dried, the film support is cast with a gelatino silver halide emulsion. It has the same properties as in Example 1.
  • Example 3 A film support of acetyl cellulose (57% combined acetic acid) has applied thereto an intermediate layer consisting of the following solution:
  • the film support cast with photographic emulsion has the properties indicated in Example 1.
  • Example 4 An acetyl cellulose film support has applied thereto an intermediate layer from the following solution:
  • the film support cast with a gelatino silver halide emulsion has the properties indicated in Example 1.
  • the aforementioned combinations may not only be used for treating cellulose acetate films but also film supports of other organic cellulose esters such as cellulose acetate-butyrate, cellulose acetate-propionate.
  • the film supports usually have a thickness varying between about 60 to 200 microns, preferably 80 to 120 microns.
  • FIGURE is an enlarged cross-sectional view of one type of structure according to the present invention.
  • 1 represents a support of an organic cellulose ester
  • 2 represents an intermediate polycarbonate layer
  • 3 represents a subbing layer, such as one composed of a mixture of gelatine and a polymer containing hydroxyl groups or of a mixed acetal produced from polyvinylalcohol and aldehydes having acid groups and such being free of acid groups
  • 4 represents a water-permeable colloid layer, such as a gelatine silver halide emulsion layer.
  • a photographic element comprising a support composed of an acetyl cellulose ester; an intermediate layer comprising a high molecular weight linear thermoplastic polycarbonate coated on said support, said polycarbonate consisting essentially of recurring units of the formula:
  • OAOMHF a subbing layer coated on said polycarbonate layer and comprising a film-forming agent selected from the group consisting of (l) a mixed acetal of polyvinyl alcohol with an aldehyde devoid of water-solubilizing groups as well as an aldehyde containing a group selected from the class consisting of carboxylic and sulfonic acid groups and their water-soluble salts, and (2) a combination of gelatine with a partially hydrolyzed copolymer of vinyl chloride with a vinyl ester of a carboxylic acid; said subbing layer being coated with a gelatine-silver halide emulsion layer.
  • a film-forming agent selected from the group consisting of (l) a mixed acetal of polyvinyl alcohol with an aldehyde devoid of water-solubilizing groups as well as an aldehyde containing a group selected from the class consisting of carboxylic and sulfonic acid groups and their water-soluble salts
  • a photographic element comprising a support composed of an acetyl cellulose ester; an intermediate layer comprising a high molecular weight linear thermoplastic polycarbonate coated on said support, said polycarbonate consisting essentially of recurring units of the formula:
  • a hydrophobic film comprising a cellulose acetate support 60-200 microns thick, an adjacent break-resistant layer l-lO microns thick of a film-forming resinous theri16 5iasa polycarbonate ring units of the formula:
  • R R R R wherein X is selected from the group consisting of S, O,
  • R and R are selected from the groups consisting of H, branched and unbranched monovalent aliphatic hydrocarbons containing up to 10 carbon atoms, monovalent cycloaliphatic hydrocarbons, monovalent araliphatic hydrocarbons containing up to 4 carbon atoms as side chains, phenyl and furyl, Z represents the carbon and hydrogen atoms which complete a cycloaliphatic ring, and R is a member selected from the group consisting of hydrogen, monovalent branched and unbranched aliphatic hydrocarbon radicals of up to 5 carbon atoms, monovalent cycloaliphatic hydrocarbon, and monovalent aromatic hydrocarbon radicals; and a gelatine-silver halide emulsion bonded to said break-resistant layer through a subbing layer of a mixed acetal of polyvinyl alcohol with (I) an aromatic aldehyde containing a water-solubilizing group and (II) an aldehyde free of water-solubilizing groups, 50
  • subbing layer also contains a minor proportion of a partially saponified copolymer of vinyl chloride and a vinyl ester of a carboxylic acid, said copolymer being 45 to 70% by weight vinyl chloride, 5 to 30% by weight vinyl hydroxide, and 10 to 40% by weight said vinyl ester.
  • R R R R R R R having a molecular weight of about 40,000 -80,000 and consisting essentially 0t recurwherein R is a member selected from the group consisting of ethyl and methyl.

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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)
  • Laminated Bodies (AREA)
  • Paper (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Printing Plates And Materials Therefor (AREA)
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US722464A 1957-03-29 1958-03-19 Photographic element having polycarbonate sub-layer Expired - Lifetime US3025163A (en)

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DEA26849A DE1055949B (de) 1957-03-29 1957-03-29 Verfahren zur Vorbehandlung von Filmunterlagen fuer den Auftrag von hydrophilen Kolloidschichten

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BE (1) BE566227A (me)
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236678A (en) * 1960-08-29 1966-02-22 Gen Aniline & Film Corp Subbing layer for polycarbonate filmbase
US3316118A (en) * 1963-11-29 1967-04-25 Gen Aniline & Film Corp Mixed resin adhesive composition for securing hydrophobic calcium tungstate stale salt laver to hydrophilic base
US3506445A (en) * 1964-12-09 1970-04-14 Bexford Ltd Synthetic film materials

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1236935B (de) * 1961-10-17 1967-03-16 Agfa Ag Transparente photographische Verstaerkerfolien
IT1170997B (it) * 1981-05-26 1987-06-03 Minnesota Mining & Mfg Miglioramento nel sottostratare supporti di polietilentereftalato e pellicole fotografiche comprendenti detti supporti migliorati
GB8429729D0 (en) * 1984-11-24 1985-01-03 Wiggins Teape Group Ltd Base paper
US5290672A (en) * 1984-11-24 1994-03-01 The Wiggins Teape Group Limited Base paper for photographic prints

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2698241A (en) * 1952-06-07 1954-12-28 Du Pont Photographic elements and process of preparing the same
US2698240A (en) * 1950-03-22 1954-12-28 Du Pont Photographic films and their preparation
US2799666A (en) * 1956-01-26 1957-07-16 Eastman Kodak Co Linear polycarbonates from bis (hydroxyethoxy) aromatic compounds
US2874046A (en) * 1955-06-25 1959-02-17 Agfa Ag Process for the retreatment of foils consisting of highly polymeric substances for the application of hydrophilic colloids

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2698240A (en) * 1950-03-22 1954-12-28 Du Pont Photographic films and their preparation
US2698241A (en) * 1952-06-07 1954-12-28 Du Pont Photographic elements and process of preparing the same
US2874046A (en) * 1955-06-25 1959-02-17 Agfa Ag Process for the retreatment of foils consisting of highly polymeric substances for the application of hydrophilic colloids
US2799666A (en) * 1956-01-26 1957-07-16 Eastman Kodak Co Linear polycarbonates from bis (hydroxyethoxy) aromatic compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236678A (en) * 1960-08-29 1966-02-22 Gen Aniline & Film Corp Subbing layer for polycarbonate filmbase
US3316118A (en) * 1963-11-29 1967-04-25 Gen Aniline & Film Corp Mixed resin adhesive composition for securing hydrophobic calcium tungstate stale salt laver to hydrophilic base
US3506445A (en) * 1964-12-09 1970-04-14 Bexford Ltd Synthetic film materials

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GB862205A (en) 1961-03-01
DE1055949B (de) 1959-04-23
CH368378A (de) 1963-03-31
BE566227A (me)
FR1204417A (fr) 1960-01-26

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