US2875053A - Photographic elements containing polymeric esters as ultraviolet absorbing compounds - Google Patents

Photographic elements containing polymeric esters as ultraviolet absorbing compounds Download PDF

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Publication number
US2875053A
US2875053A US511168A US51116855A US2875053A US 2875053 A US2875053 A US 2875053A US 511168 A US511168 A US 511168A US 51116855 A US51116855 A US 51116855A US 2875053 A US2875053 A US 2875053A
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photographic
group
compounds
compound
ultraviolet absorbing
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Louis M Minsk
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to GB15197/56A priority patent/GB793292A/en
Priority to FR1156855D priority patent/FR1156855A/fr
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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
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/14—Esterification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • 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
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor

Definitions

  • Another object of my invention is to provide new compounds and methods of making these new compounds. Another object is to provide photographic elements protected against the harmful effects of ultraviolet radiation. A further object is to provide photographic color materials which have been protected against the harmful effects of ultraviolet radiation. Other objects will become apparent from a consideration of the following description and examples.
  • the polymeric ultraviolet absorbing compounds of my invention are represented by polymerized monoethylenically-unsaturated compounds having chemically attached thereto through an ester or an amide linkage a compound having its maximum absorption between 260- 400 m with no substantial absorption between 400- 700 III/4. Since the ultraviolet absorbing component is prepared, according to my invention, by .reaction with a polymerized monoethylenically-unsaturated compound containing reactive chemical groups, such as carboxylic anhydride or carboxylic halide (e. g., chloride, bromide,
  • reaction need not be complete in order to obtain the advantages of my invention. That is, not all of the reactive anhydride or carboxylic halide groups in the polymerized compounds need undergo reaction. However, it is generally advantageous to have at least 10 percent of such reactive groups combined with the ultraviolet absorbing component.
  • I provide the new ultraviolet absorbing compounds by reacting an ultraviolet absorbing compound containing a hydroxyalkyl (e. g., B-hydroxyethyl, B-hydroxypropyl, -hydroxypropl, etc.), an aminoalkyl (e g., aminoethyl, aminopropyl,etc.) or an aminoaryl e. g., aminophenyl, aminotolyl, etc.) group with a linear synthetic polymer containing carboxylic halide or carboxylic anhydride groups;
  • a hydroxyalkyl e. g., B-hydroxyethyl, B-hydroxypropyl, -hydroxypropl, etc.
  • an aminoalkyl e.g., aminoethyl, aminopropyl,etc.
  • aminoaryl e. g., aminophenyl, aminotolyl, etc.
  • alkylvinyl ethers e. g., ethylvinyl ether, etc.
  • acrylic acid a-methacrylic acid, etc.
  • corresponding polymers of maleyl and fumaryl halides e. g., chlorides, bromides, etc.
  • polyacrylyl halides e. g., polyacrylyl chloride, polymethacrylyl chloride, etc.
  • polyacrylic anhydrides e. g., polyacrylic anhydride, poly a-methacrylic anhydride, etc.
  • Useful interpolymers of maleic anhydride, substituted maleic anhydrides (e. g., citraconic anhydride, phenyl maleic anhydride, etc.); fumaryl halides, maleyl halides with vinyl compounds are 'described in Voss et a1. U. S. Patent 2,047,398, dated July 14, 1936.
  • Useful polymers of acrylic halides i. e.,.
  • acrylic halides and a-methacrylic halides are described in' Marck et al. U. S. Patent 1,984,417, dated December 18, 1934.
  • Such polymers include, for example, polyacrylyl chloride, polymethacrylyl chloride, as well as copolymers of these halides with a vinyl (or. vinylidene) compound, such as vinyl acetate, styrene, ethyl acrylate, acrylonitrile, etc,
  • the ultraviolet invention containing a hydroxyalkyl, aminoalkyl or aminoy group
  • absorbing components used in my which are reacted with the synthetic polymers listed above comprise a class of compounds having sub stantially no absorption of visible radiation, i. e., they are colorless, but having the property of absorbing substantial amounts of radiation shorter than 400 m
  • the hydroxyalkyl, aminoallryl or aminoaryl groups required in the ultravioletabsorbing component can be attached to the molecule through'a carbon linkage, or this group canbe attached through some other linkage such as an ether linkage '(e. g., ,B-hydroxyethoxy, etc.).
  • the ultravioletabsorbing components which can be reacted with the synthetic resins listed above are those represented by the following general formulas:
  • R and R each represents an alkyl group (e. g., methyl, ethyl, etc.) or an aryl group (e. g., phenyl, mand p-tolyl, 0-, mand p-methoxyphenyl, etc.), R and R each represents an aryl group (e. g., phenyl, o-, mand p-tolyl, etc.), R represents an aryl group (e. g.,
  • R represents an alkyl group (e. g., methyl, ethyl, etc.) or an aryl group (e. g., such as thoselisted above for R (provided that at least R or R contains a hydroxyalkyl radical), and R represents an aminoaryl group (e. g., o-, 'mand p-aminophenyl, etc.).
  • the intermediates represented by Formula I above can advantageously be prepared by condensing together a hydrazine compound selected from those represented by the following general formula: (VI) IIQNIITRI R2 he e R1 n R2 ha th a u given ab e with a phydr'oxyetho xybenaaldehyde selected from those represented by the following general formula: (V11) 0 i J-1r H O-OII2CH2-O
  • the condensations can advantageously be carried out in the presence of an acid condensing agent, such as glacial acetic acid, etc. While the reaction mixture can be heated, there is generally no advantage in doing so due to the exothermic nature of the reaction.
  • the intermediates represented by Formula II above can advantageously be prepared by heating together a compound selected from those represented by the following general formula:
  • this compound contained C, 69.5% and H, 5.8%, whereas the calculated values are C, 69.6% and H, 5.5%.
  • the compounds selected from those represented by Formula III above can advantageously be prepared according to the method described in Sawdey U. S. application Sei'. no. 419,239, filed March 2.9, 1954 (now U. S. Patent 2,739,888, issued March 27, 1956), i. e., by reacting a compound corresponding to that of Formula III above, except that a methylene group is present in the 5-position, with an aromatic aldehyde, such as P-B- hydroxyethoxybenzaldehyde.
  • the compounds of Formula IV above can advantageously be prepared by condensing a compound selected from those represented by Formula VI above with an aromatic aldehyde containing a primary amino group, such as p-aminobenzaldehyde.
  • the polymeric ultraviolet absorbing compounds of my invention comprising an amide of a compound represented by Formula V above can be prepared by first e0ndensing the compound of Formula IX with one of the polymerized monoethylenically-unsaturated' compounds of my invention, followed by condensation of this product with an aldehyde represented by Formula X above.
  • FIG. l of the accompanying drawing illustrates schematically 'a cross-sectional view of a sensitive photographic element having an ultraviolet filter layer contaim ing one of the compounds of my invention.
  • These intraviolet absorbing compounds can be incorporated in the photographic element in a variety of ways, depending on the ultimate use of the photographic element and the degree of protection desired.
  • the ultraviolet absorbing compound can be dissolved or dispersed in a solvent medium together with a colloidalbinder, such as gelatin, cellulose esters (e. g., cellulose acetate, etc.), synthetic resins (e.
  • the ultraviolet filter layer need not be an outer layer, but this layer can be placed over one of the layers subject to the harmful effects of ultraviolet radiation.
  • theultraviolet filter layer can be placed between the blue andgreen sensitive layers.
  • the ultraviolet filter layer can be placed between the green and the red sensitive layers.
  • the material useful in absorbing the ultraviolet radiation can be incorporated directly i n the light-sensitive emulsion instead of, or in"addition to, being present in another layer.
  • the amount of ultraviolet absorbing compound used can be varied, depending upon the effect desired and the use to whichthe materialis to be put.
  • the support ofv the photographic element can be transparent, such as a cellulose ester (cellulose acetate, etcl) support.
  • Other supports such 135 6? C. -Analysis.-N, found: 10.2 hydroxyethoxybenzaldehyde Reaction with "stirring ona steam bathfo r 2% hours. distilled water were then added and heating was con- .with ether in a Soxhlet apparatus.
  • styrene-maleic anhydride interpolymer [.In an all-glass outfit, equipped with a reflux condenser and calcium chloride tube and a mechanical stirrer, g. of styrene-maleic anhydrideinterpolymer were dispersed in 80 ml. of dry pyridine. To this dope were added g.
  • Thelight-colored product did not appear to be direct- "ly soluble in dilute ammonium or sodium hydroxide
  • Crystallization was again induced by addition of water to the boiling solution to incipient turbidity and chilling.
  • the product was filtered onto a Biichner funnel, washed with water on the funnel, and dried in a vacuum desiccator over calcium chloride under a constantly applied water pump vacuum. Seven and one-half g. of light buif crystals, which melted at 1323 C., were obtained.
  • Te'n .g. of acrylic anhydride and g. of 3-;8-aminoethyl-5-benzalthiazolidinedione-2,4 hydrochloride was re- In an all-glass outfit, equipped with a reflux condenser with calcium chloride tube and a mechanical stirrer, were placed 7 g. of polyacrylic 'anhydride, 9g. of 3-aminoethylthiazolidinedione-2,4, and -70 ml. of dry pyridine.
  • the reaction was heated on a steam bath for two hours, and 3.5 ml. of distilled water were added. After minutes of additional heating, the dope was cooled and poured into 3 liters of ether. The soft precipitate was extracted with fresh ether and redissolved on a steam bath in 90 ml. of acetone with sufiicient water added to effect solution. The dope was poured into 1 /2 liters of distilled water containing 10ml. 'of concentrated hydrochloric acid and the soft precipitate obtained was kneaded repeatedly with fresh l-liter portions of distilled water until free from acid. The'product-was dried in a vacuum desiccator over calcium chloride under a constantly applied water pump vacuum. The yield was 8 g.
  • Example E The m-;3-hydroxyethoxybenzaldehyde' used in Example E above was prepared according to the method described by Bernstein et al., ibid., using 'rn-'hydroxybenzaldehyde in place of p-hydroxybenzaldehyde. It had a boiling point of 143.8 C. at 0.4 mm.
  • Example 2 1.0 g. of the polymeric compoundobtained as described in Example F above was wetted with 1 cc. of acetone and 5 drops of 28% ammonium hydroxide. 20.0 cc. of water was added and solution was effected by gentle warming and tln's solution was :then added to 20 cc. of warm 10% aqueous gelatin solution.
  • Fig. 1 illustrates schematically a cross-sectional view of a photographic element containing -a .layer having incorporated therein a polymeric ultraviolet absorbing compound obtained according to my invention.
  • a support 10'of any suitable material, such as cellulose acetate, or paper, having thereon an emulsion layer 11 is coated with a filter layer 12 having incorporated therein a polymeric ultraviolet absorbing compound obtained according to my invention, such as is described in Example C above.
  • Fig. 1 of the drawing is merely representative of other structures which can be employed in my invention and that the element can have other layers, not shown, as additional lightsensitive layers, subbing layers, anti-halation layers, etc.
  • hydroxyalkyl as used herein, l mean.such a group as HOCH CH which might be attached directly 'to an aryl group, or HOCH CH O which contains theHOCH CH group and is attached to an aryl -groupthrough an oxygen atom (or other linkage, such as sulfur).
  • esterification or amide formation characteristic of my invention occurs at the alcoholic hydroxyl (and not at aphenolic hydroxyl) or primary amino group, respectively.
  • Esterification at a phenolic hydroxide' would affect the absorption characteristics of the compounds represented by Formulas I-III above,
  • a photographic element comprising a support, at least one photographic silver halide emulsion layer and incorporated in one of the layers of said photographic element an ester of a compound selected from the group consisting of those represented by the following three general formulas:
  • R and R each represents a member selected from the group consisting of an alkyl group and an aryl group
  • R,, R, and R each represents an aryl group
  • R represents a member selected from the group consisting of an alkyl group and an aryl group, provided that at least one of the groups selected from the group consisting of R and R contains a hydroxyalkyl radical containing from 2 to 3 carbon atoms, the hydroxyl group of the hydroxyalkyl group of said compound selected from the group consisting 10 a t a of (a), (b), and (0) having been esterified by a polymerized monoethylenically-unsaturated compound containing reactive groups selected from the group consisting of carboxylic' halide and carboxylic anhydride groups.
  • a photographic element comprising a support, at least one photographic gelatino-silver-halide emulsion layer, and incorporated in one of the layers of said photographic element an ester of a compound selected from those represented by the following general formula:
  • R and R each represents a member selected from the group consisting of an alkyl group containing from 1 to 2 carbon atoms and a monocyclic aryl group of the benzene series, said compound having been esterified by a polymerized monoethylenically-unsaturated compound containing a group selected from the group consisting of carboxylic halide and carboxylic anhydride groups.
  • a photographic element comprising a support, at least one photographic gelatino-silver-halide emulsion layer superposed on said support, and an outer gelatin layer containing an ester of a styrene-maleic anhydride interpolymer and p-;8-hydroxyethoxybenzaldehyde-ozmethyl-ot-phenylhydrazone.
  • a photographic element comprising a support, at least one photographic gelatino-silver-halide emulsion layer, and incorporated in one of the layers of said photographic element an ester of a compound selected from those represented by the following general formula:
  • R represents an aryl group, said compound having been esterified by a polymerized monoethylenically-unsaturated compound containing a group selected from the group consisting of carboxylic halide and carboxylic anhydride groups.
  • a photographic element comprising a support, at least one photographic gelatino-silver-halide emulsion layer, and incorporated in one of the layers of said photographic element an ester of a compound selected from those represented by the following general formula:
  • R represents a monocyclic aryl group of the benzene series, said compound having been esterified by a polymerized monoethylenically-unsaturated compound containing a group selected from the group consisting of carboxylic halide and carboxylic anhydride groups.
  • a photographic element comprising a support, at least one photographic gelatino silver-halide emulsion layer superposed on said support, and an outer gelatin :layer containing an ester of a styrene-ma'leic anhydride interpolymer and 2-hydroxy-4-B hydroxyethoxybenz0- phenone.
  • a photographic element comprising a support, at least one photographic gelatino-silver-halide emulsion layer, and incorporated in one of the layers of said photographic element an ester of a compound selected "from those represented by the following general formula:
  • a photographic element comprising a support, at least one photographic gelat'ino-silver-halide emulsion layer superposed on said support, and an outer gelatin layer containing an ester 'ofpolyacrylic anhydride and 3 ethyl 5 p 1(5 hydroxyethoxy'wenzal 2 phenylimino-4-thiazolidone.

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  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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US511168A 1955-05-26 1955-05-26 Photographic elements containing polymeric esters as ultraviolet absorbing compounds Expired - Lifetime US2875053A (en)

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BE547975D BE547975A (de) 1955-05-26
US511168A US2875053A (en) 1955-05-26 1955-05-26 Photographic elements containing polymeric esters as ultraviolet absorbing compounds
GB15197/56A GB793292A (en) 1955-05-26 1956-05-16 Photographic elements containing ultraviolet absorbing compounds
FR1156855D FR1156855A (fr) 1955-05-26 1956-05-26 Nouveau produit photographique protégé contre l'ultraviolet et nouveaux composés absorbants utiles pour sa préparation

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987503A (en) * 1957-01-04 1961-06-06 Eastman Kodak Co Polyesters light-stabilized with 4-thiazolidone derivatives
US3116675A (en) * 1959-06-08 1964-01-07 Thompson Ramo Wooldridge Inc Distinct and accurate symbol displays on photo products
US3142658A (en) * 1960-10-26 1964-07-28 Us Rubber Co Diolefin polymer rubber stabilized with bis
US3175905A (en) * 1960-10-08 1965-03-30 Azoplate Corp Light sensitive material
US3197504A (en) * 1961-02-16 1965-07-27 Du Pont Chlorobenzaldehyde hydrazones and their hydrazonium salts
US3215530A (en) * 1960-11-16 1965-11-02 Agfa Ag Color photographic element protected against fading and method of applying protective film thereto
US3330680A (en) * 1963-10-29 1967-07-11 Polaroid Corp Novel image-receiving elements
US3414650A (en) * 1964-07-08 1968-12-03 Gaf Corp Sunscreening methods
US3993658A (en) * 1972-11-20 1976-11-23 Sterling Drug Inc. Thiazolidinylidene-isoindolines
US4106941A (en) * 1974-07-17 1978-08-15 Eastman Kodak Company Photographic silver halide elements containing optical brightening water-soluble interpolymers
WO1981001059A1 (en) * 1979-10-12 1981-04-16 Minnesota Mining Mfg Gmbh Polymeric ultraviolet absorbers and photographic material including them
US4269925A (en) * 1979-10-29 1981-05-26 Polaroid Corporation Polymeric optical filter agents and photographic products and processes containing same
US4298676A (en) * 1979-10-29 1981-11-03 Polaroid Corporation Optical filter agents and photographic products and processes containing same
US4468494A (en) * 1979-10-29 1984-08-28 Polaroid Corporation Polymeric pH-sensitive optical filter agents having hydrazone moieties attached thereto
US20080160222A1 (en) * 2003-08-08 2008-07-03 Richard Harding Alignment Layer with Reactive Mesogens for Aligning Liquid Crystal Molecules

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3330656A (en) * 1963-08-14 1967-07-11 Polaroid Corp Novel photographic products and processes
GB1482921A (en) 1973-07-31 1977-08-17 Glaxo Lab Ltd Polymers
US4076913A (en) 1973-07-31 1978-02-28 Glaxo Laboratories Limited Solid or gel polymers containing a plurality of free hydrazone groups

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2357393A (en) * 1939-05-22 1944-09-05 Gen Aniline & Film Corp Process for the production of photographic color images
US2691579A (en) * 1952-10-31 1954-10-12 Eastman Kodak Co Ultraviolet absorbing layers
US2739888A (en) * 1954-03-29 1956-03-27 Eastman Kodak Co Photographic elements containing thiazolidine derivatives

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2357393A (en) * 1939-05-22 1944-09-05 Gen Aniline & Film Corp Process for the production of photographic color images
US2691579A (en) * 1952-10-31 1954-10-12 Eastman Kodak Co Ultraviolet absorbing layers
US2739888A (en) * 1954-03-29 1956-03-27 Eastman Kodak Co Photographic elements containing thiazolidine derivatives

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987503A (en) * 1957-01-04 1961-06-06 Eastman Kodak Co Polyesters light-stabilized with 4-thiazolidone derivatives
US3116675A (en) * 1959-06-08 1964-01-07 Thompson Ramo Wooldridge Inc Distinct and accurate symbol displays on photo products
US3175905A (en) * 1960-10-08 1965-03-30 Azoplate Corp Light sensitive material
US3142658A (en) * 1960-10-26 1964-07-28 Us Rubber Co Diolefin polymer rubber stabilized with bis
US3215530A (en) * 1960-11-16 1965-11-02 Agfa Ag Color photographic element protected against fading and method of applying protective film thereto
US3197504A (en) * 1961-02-16 1965-07-27 Du Pont Chlorobenzaldehyde hydrazones and their hydrazonium salts
US3330680A (en) * 1963-10-29 1967-07-11 Polaroid Corp Novel image-receiving elements
US3414650A (en) * 1964-07-08 1968-12-03 Gaf Corp Sunscreening methods
US3993658A (en) * 1972-11-20 1976-11-23 Sterling Drug Inc. Thiazolidinylidene-isoindolines
US4106941A (en) * 1974-07-17 1978-08-15 Eastman Kodak Company Photographic silver halide elements containing optical brightening water-soluble interpolymers
WO1981001059A1 (en) * 1979-10-12 1981-04-16 Minnesota Mining Mfg Gmbh Polymeric ultraviolet absorbers and photographic material including them
EP0027242A1 (de) * 1979-10-12 1981-04-22 Minnesota Mining And Manufacturing Company Polymere Ultraviolettabsorber, photographisches Material, das diese Absorber enthält, und Verfahren
US4269925A (en) * 1979-10-29 1981-05-26 Polaroid Corporation Polymeric optical filter agents and photographic products and processes containing same
US4298676A (en) * 1979-10-29 1981-11-03 Polaroid Corporation Optical filter agents and photographic products and processes containing same
US4468494A (en) * 1979-10-29 1984-08-28 Polaroid Corporation Polymeric pH-sensitive optical filter agents having hydrazone moieties attached thereto
US20080160222A1 (en) * 2003-08-08 2008-07-03 Richard Harding Alignment Layer with Reactive Mesogens for Aligning Liquid Crystal Molecules
US8409674B2 (en) * 2003-08-08 2013-04-02 Merck Patent Gmbh Alignment layer with reactive mesogens for aligning liquid crystal molecules
US8481130B2 (en) 2003-08-08 2013-07-09 Merck Patent Gmbh Alignment layer with reactive mesogens for aligning liquid crystal molecules

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BE547975A (de)
GB793292A (en) 1958-04-16

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