US3022171A - Photographic filter and antihalation layers - Google Patents

Photographic filter and antihalation layers Download PDF

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Publication number
US3022171A
US3022171A US672199A US67219957A US3022171A US 3022171 A US3022171 A US 3022171A US 672199 A US672199 A US 672199A US 67219957 A US67219957 A US 67219957A US 3022171 A US3022171 A US 3022171A
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Prior art keywords
dihydroxy
acid
diphenylene
antihalation
support
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US672199A
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Ossenbrunner Armin
Klockgether Helfried
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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
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/835—Macromolecular substances therefor, e.g. mordants
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups

Definitions

  • the present invention relates to light-absorbing photographic layers and more particularly to antihalation and filter layers for light sensitive photographic materials comprising silver halide emulsion layers.
  • the antihalation layer generally consists of an antihalation dye which is removed in the photographic processing baths, and a binding agent, generally gelatine or, because of their better mechanical properties, alkali-soluble plastics.
  • Copolymers of styrene and acrylic acid, vinyl isobutyl ether and maleic acid, vinyl butyl ether and maleic acid, and styrene and maleic acid according to US. patent specification No. 2,077,789;
  • antihalation layers can be produced which have excellent properties if high molecular alkali-soluble polycarbonic acid esters of aliphatic, cycloaliphatic, araliphatic and/or aromatic dihydroxy compounds containing acid groups, optionally in admixture with organic dihydroxy compounds Without acid groups are used as binding agents.
  • polycarbonic acid esters contain recurring units of the formula:
  • R stands for a bivalent organic radical containing as sole reactive group an acid group, such as at least one carboxylic and/or sulphonic acid group, whereby in part of these recurring units R may stand for a bivalent organic radical containing no acid groups or other reactive groups, said bivalent organic radical being derived from the aforementioned organic dihydroxy compounds by subtraction of the hydroxy groups.
  • R stands for a bivalent organic radical containing as sole reactive group an acid group, such as at least one carboxylic and/or sulphonic acid group
  • the alkali-soluble polycarbonic acid esters of high molecular weight which are to be used in accordance with the invention can be obtained by reacting aliphatic, cycloaliphatic, araliphatic or aromatic dihydroxy compounds containing acid groups, if desired admixed with cycloaliphatic, araliphatic or aromatic dihydroxy compounds without acid groups, with carbonic acid chlorides such as bis-halogen, carbonic acid esters of dihydroxy compounds or with phosgene, for example according to the prescription given in German application F13,040 (now German Patent 971,790) or Belgian Patent 532,543.
  • Such polycarbonates canthus contain the radicals of dihydroxy carboxylic acids such as tartaric acid, dihydroxy stearic acids, 2,5-dihydroxycyclohexane carboxylic acid, 4,4-dihydroxydicyclohexyl carboxylic acid-(2.2), 1,5-dihydroxy benzoic acid, 3,6-dihydroxybenzene-1,2-dicarboxy1ic acid, 4,4'-dihydroxydiphenyl-2,2-dicarboxylic acid and especially di-(monohydroxy aryl)alkanes containing carboxyl groups, such as 4,4'-dihydroxy-3,3'-dicarb0xy diphenylmethane and 4,4'-dihydroxy-3,3-dicarboxy-5,5'-dimethyl diphenyl methane, and also dihydroxysulphonic acids such as 1,4-dihydroxybenzene sulphonic acid-(2), 1,6-dihydroxynaphthalene sulphonic acid-(3) and 4,4'-d
  • Particularly suitable for the process of the invention are those polycarbonic acid esters, for the production of which 4,4-dihydroxy-3,3-dicarboxy diphenyl methane or 4,4-dihydroxy 3,3 dicarboxy 5,5 dimethyl diphenyl methane have been used.
  • aliphatic dihydroxy compounds ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, thiodiglycol, ethylene dithiodiglycol, the diand polyglycols produced from propyleneoxide-LZ, o, m, or p- Xylene glycol, propanedioll,3, butanediol-l,3, butanediol- 1,4, 2-methylpropanediol-l,3, pentanediol-l,5, Z-ethylpropanediol-L3, hexanediol-L6, octanediol-i,8, l-ethylhexanediol-1,3, and decanediol-1,l0,
  • aromatic dihydroxy compounds are the di-monohydroxy arylene sulphones and particularly the di-monohydroxy arylene alkanes, such as 4,4-di.- hydroxy-diphenylene sulphone, 2,2'-dihydroxydiphenylene sulphone, 3,3'-dihydroxydiphenylene sulphone, 4,4'-dihydroxy-Z,2,-dimethyl-diphenylene sulphone, 4,4'-dihydroxy- 3,3'-dimethyl-diphenylene sulphone, 2,2-dihydroxy-4,4'- dimethyl-diphenylene sulphone, 4,4-dihydroxy-2,2 '-diethyldiphenylene sulphone,
  • diphenylene) -propane (melting point 114 '0), 2,2- (5 ,5 'dihyd1'oxy-3-isopropyl-diphenylene) -butane, 1,1-(4,4-dihydroxy 3,37 dimethyl-diphenylene)-cyclohexane, 2,2- (4,4-dihydroxy-3,3 -dibuty1-diphenylene) propane, 2,2- (4,4-dihydroxy-3,3-diphenyl-diphenylene) -propane, 2,2-(4,4-dihydroxy-2,2-dimethyl-diphenylene)-propane, 1,1 (4,4-dihydroxy-3,3'-dimethyl-6,6-dibutyl-diphenylene)-'butane,
  • the 4,4'-dihydroxy-diphenylene alkanes are preferred, especially the 2,2-(4,4-dihydroxy-diphenylone-propane and the 1,1 (4,4 dihydroxy-diphenyiene)- cyclohexane.
  • the polycarbonates can be produced for example by introducing .phosgene into solutions, of dihydroxy compounds or of mixtures of the aforesaid dihydroxy compounds in organic bases, such as dimethylaniline, diethylaniline, trimethylamine, and pyridine, or in 'indifierent organic solvents, such as petrol, ligroin, cyclohexane, methylcyclohexane, benzene, toluene, xylene, chloroform, .methylenechloride, carbon tetrachloride, trichloroethylone, 'dichloroethane, methacetate, and ethylacetate, with addition of an acid-binding agent, e.g. tertiary amines.
  • organic bases such as dimethylaniline, diethylaniline, trimethylamine, and pyridine
  • 'indifierent organic solvents such as petrol, ligroin, cyclohexane
  • a process particularly suitable bonates consists in introducing phcsgene into the aqueous solution or suspension or salts, such as lithium, sodium, potassium, and calcium salts of the dihydroztyv compounds, preferably in the presence of an excess of a base, such as lithium, sodiunn potassium, and calcium hydroxide or carbonate.
  • a base such as lithium, sodiunn potassium, and calcium hydroxide or carbonate.
  • the conversion in the aqueous solution is promoted by the addition of solvents of the kind mentioned above which are inert to the reaction and capable of dissolving phosgene and eventually the produced polycarbonate.
  • reaction conditions should preferably be so that one mole of the phosgene reacts with one mole of the dihydroxy compounds. Suitable temperatures are from about 0 C. to C.
  • catalysts When using phosgene or bis-chlorocarbonic acid esters .as derivatives of the carbonic acid in producing polcarbonates catalysts also may be advantageous.
  • Such catalysts are for instance tertiary or quaternary organic bases or salts thereof, such as trimethylamine, triethyldimethylcycloamine, dimethylamline, diethylaniline,
  • hydrochlorides and tetramethylammoniumliydroxide, triethyloctadecylammoniumchloride, dimethyl benzylphenylammonium-chloride, trimethylcyclohexylammoniumbromide, and N-methylpyridiniurnchloride, in amounts from about 0.05 to about 5 percent by Weight.
  • tetramethylammoniumliydroxide triethyloctadecylammoniumchloride
  • dimethyl benzylphenylammonium-chloride trimethylcyclohexylammoniumbromide
  • N-methylpyridiniurnchloride in amounts from about 0.05 to about 5 percent by Weight.
  • surface active agents such as alkali metal salts of higher fatty acids or of sulphonic acids of higher aliphatic or of aromatic hydrocarbons and polyoxyethylated alcohols and phenols. Greater amounts of the alkali or alkaline earth metal for producing polycarquaternary ammonium bases mentioned above, too, act
  • reducing agents for example sodium or 1 aqueous alkalies such as sodium groups of the polycarbonates consisting of the chloro- 5 carbonic acid ester group and which terminate the chains, such as the phenols, for instance, phenol, tert. butylphenyl-, the cyclo-hexylphenyl-, and 2,2(4,4-dihdroxyphenylene-4'-methoxyphenylene) propane, aniline and methylaniline, it is possible to regulate the molecular weight of the polycarbonate-s in wide limits.
  • reducing agents for example sodium or 1 aqueous alkalies such as sodium groups of the polycarbonates consisting of the chloro- 5 carbonic acid ester group and which terminate the chains, such as the phenols, for instance, phenol, tert. butylphenyl-, the cyclo-hexylphenyl-, and 2,2(4,4-dihdroxyphenylene-4'-methoxyphenylene) propane, ani
  • the working up of the reaction mixture may be effected when operating in the presence of acid-binding agents and organic solvents such as methylene chloride or benzene, in such a manner that the reaction mixture is dissolved cold in dilute sodium hydroxide solution, the organic layer separated, the aqueous layer filtered oil and the polycarbonate precipitated from the filtrate by acidification, or that the organic solvent is distilled oil from the reaction mixture upon acidification with dilute hydrochloric acid and the polycarbonate filtered off.
  • acid-binding agents and organic solvents such as methylene chloride or benzene
  • the new polycarbonates are soluble in addition to a number of organic solvents such as acetone, tetrahydrofurane, dioxane, dimethyl formamide, mixture of methanol and benzene or ethanol and benzene, further in or potassium hydroxide or sodium carbonate solution.
  • organic solvents such as acetone, tetrahydrofurane, dioxane, dimethyl formamide, mixture of methanol and benzene or ethanol and benzene, further in or potassium hydroxide or sodium carbonate solution.
  • the antihalation layers produced from the aforementioned polycarbonates and antihalation dyestuffs known as such are distinguished by sufficient solubility in alkaline silver halide developing solutions even if these are Weakly alkaline and contain considerable amounts of salts, furthermore by a good resistance to abrasion and to transfer to emulsions layer disposed in contact with said antihalation layer.
  • the described antihalation layers may be produced on supports of cellulose ester's, such as cellulose acetate, cellulose acetobutyrate, nitrocellulose, polyesters of terephthalic acid and glycol, polyvinylchloride and copolymers of vinylchloride with maleic anhydride or maleic acid esters, polystyrene, and high molecular linear polycarbonates as disclosed for instance in Belgian Patent 532,543.
  • cellulose ester's such as cellulose acetate, cellulose acetobutyrate, nitrocellulose
  • polyesters of terephthalic acid and glycol polyesters of terephthalic acid and glycol
  • polyvinylchloride and copolymers of vinylchloride with maleic anhydride or maleic acid esters polystyrene
  • high molecular linear polycarbonates as disclosed for instance in Belgian Patent 532,543.
  • the polycarbonates of the present invention may be applied in admixture with other synthetic or natural resins containing alkali-solubilizing groups, such as copolymers of styrene and acrylic acids, vinylisobutylether and maleic acid, acrylonitrile, vinylbutylether and maleic half esters, celluloseacetatephthalate, polyyinylphthalate.
  • alkali-solubilizing groups such as copolymers of styrene and acrylic acids, vinylisobutylether and maleic acid, acrylonitrile, vinylbutylether and maleic half esters, celluloseacetatephthalate, polyyinylphthalate.
  • the present invention is illustrated by the accompanying drawing representing a cross-section in enlarged scale through a photographic material according to the present invention.
  • Example 1 8 g. of an antihalation dye, such as a dyestufi of the formula:
  • the layer dissolves satisfactorily on processing in the photographic baths and does not transfer to the emulsion layer under the conditions prevailing in practice, even with long storage.
  • the above polycarbonate is produced in the following manner:
  • Example 2 6 g. of an antihalation dye as for instance a dyestuff of the formula:
  • the filter residue After filtration of the residue, the filter residue is washed first with hydrochloric acid and subsequently with water until no further chlorine is detectable in the wash water.
  • the filter residue is dried at 80 C. under vacuo.
  • Further dyestuiis which may be used ior the production of the antihalation layers are for instance those disclosed in British specifications 694,681 and 760,739.
  • Example 3 12 g. of an antihalation dye according to U.S. patent specification No. 2,282,890, Example 2-,
  • the solution is applied to the back of a foil of a polyester of terephthalic acid-and. glycol having layers of silver halide emulsion on the front.
  • Example 4 halide emulsion layer is then applied to the front of the V support.
  • the properties of the antihalation layer conform to the requirements which have been stated.
  • the polycarbonate is obtained according to the process disclosed in Example 1, replacing the dihydroxy compound of'said example by an equimolecular amount of the dihydroxy compound disclosed in the preceding paragraph.
  • Example 5 I A solution of 4.7 g, of the dyestufi disclosed in Exarnple 2, 3 g. of a copolymer of an alkali-soluble copolymer of styrene and methacrylic acid according to U.S.
  • the polycarbonate is obtained according to the process disclosed in Example l,'replacing the dihydroxy com pound of said example by an equimolecular amount of the dihydroxy compound disclosed in the preceding paragraph.
  • a light-sensitive photographic material comprising a light transmitting support, a photographically lightsensitive silver halide gelatin layer coated on one side of said support and an alkali-soluble antihalation layer con taining a light absorbing antihalation dyestufi coated on the other side of said'support, said antihalation layer containing as a binding agent substantially a major proportion of a high molecular film-forming linear polycarbonic ester of at least one dihydroxy compound selected from the class consisting of aliphatic, cycloaliphatic, araliphatic and aromatic compounds having hydroxy groups selected from the class consisting of alcoholic and phenolic hydroxy groups, at least 30 molar percent of the dihydroxy compound units in the ester also containing from one to two acid groups selected from the class consisting of carboxyl and sulfonic acid groups to render the ester soluble in aqueous alkaline solutions.
  • the bonding material is a mixture of a polyvinyl phthalate bonding agent and a polycarbonate of both bis (4-hydroxy-3-carboxy-S-methyl phenyl) methane and 2,2-bis,(parahydr0xy phenyl) propane.
  • the bonding material is a mixture'of (I) a bonding copolymer of styrene with maleic acid and (II) a polycarbonate of both bis-(4-hydroxy-3-carboxy-5-methylphenyl) methane and 2,2-bis (parahydroxy phenyl) propane.
  • the bonding material is a mixture of (1) acopolymerof acrylonitrile, vinyl 'butyl ether, and maleic acid monoethyl ester and (II) a polycarbonate of 2,2'-dicarboxy-4,4'-dihydroxy-dicyclohexyl.

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  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US672199A 1956-07-26 1957-07-16 Photographic filter and antihalation layers Expired - Lifetime US3022171A (en)

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DEA25378A DE1035472B (de) 1956-07-26 1956-07-26 Verfahren zur Herstellung von Lichthofschutzschichten

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CH (1) CH357630A (en))
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FR (1) FR1179663A (en))
GB (1) GB817240A (en))
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3152098A (en) * 1960-08-31 1964-10-06 Union Carbide Corp Colored polycarbonate resin compositions
US3239582A (en) * 1958-05-21 1966-03-08 Dow Chemical Co Blend of polycarbonate resin and alkenylaromatic resin
US3258356A (en) * 1966-06-28 Coat of cured poly epoxide resin
US3262782A (en) * 1961-02-08 1966-07-26 Agfa Ag Matted antihalation layer for photographic materials
US3601017A (en) * 1968-11-23 1971-08-24 Philips Corp Method of suppressing interference fringes in photosensitive material

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1254016B (de) * 1960-09-03 1967-11-09 Adox Fotowerke Dr C Schleussne Verfahren zur Herstellung von Lichthofschutzschichten
BE610269A (en)) * 1960-11-16

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE532543A (en)) * 1953-10-16
DE372933C (de) * 1920-06-07 1923-04-03 Hoechst Ag Verfahren zur Darstellung von harzartigen Kondensationsprodukten aus Phenolen und Aldehyden
US1884035A (en) * 1932-02-20 1932-10-25 Eastman Kodak Co Photographic film with antihalation coating
US2455653A (en) * 1945-02-21 1948-12-07 Goodrich Co B F Di(alkenyl carbonato) aromatic compounds and polymers thereof
US2461485A (en) * 1945-06-21 1949-02-08 Gen Aniline & Film Corp Xanthylium dye salts as filter and antihalation dyes in photographic materials
US2462527A (en) * 1947-01-27 1949-02-22 Du Pont Photographic antihalation elements
US2536989A (en) * 1948-01-20 1951-01-02 Gen Aniline & Film Corp Diazotype layers containing resorcinol derivatives

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE372933C (de) * 1920-06-07 1923-04-03 Hoechst Ag Verfahren zur Darstellung von harzartigen Kondensationsprodukten aus Phenolen und Aldehyden
US1884035A (en) * 1932-02-20 1932-10-25 Eastman Kodak Co Photographic film with antihalation coating
US2455653A (en) * 1945-02-21 1948-12-07 Goodrich Co B F Di(alkenyl carbonato) aromatic compounds and polymers thereof
US2461485A (en) * 1945-06-21 1949-02-08 Gen Aniline & Film Corp Xanthylium dye salts as filter and antihalation dyes in photographic materials
US2462527A (en) * 1947-01-27 1949-02-22 Du Pont Photographic antihalation elements
US2536989A (en) * 1948-01-20 1951-01-02 Gen Aniline & Film Corp Diazotype layers containing resorcinol derivatives
BE532543A (en)) * 1953-10-16

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3258356A (en) * 1966-06-28 Coat of cured poly epoxide resin
US3239582A (en) * 1958-05-21 1966-03-08 Dow Chemical Co Blend of polycarbonate resin and alkenylaromatic resin
US3152098A (en) * 1960-08-31 1964-10-06 Union Carbide Corp Colored polycarbonate resin compositions
US3262782A (en) * 1961-02-08 1966-07-26 Agfa Ag Matted antihalation layer for photographic materials
US3601017A (en) * 1968-11-23 1971-08-24 Philips Corp Method of suppressing interference fringes in photosensitive material

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FR1179663A (fr) 1959-05-27
DE1035472B (de) 1958-07-31
NL105283C (en))
CH357630A (de) 1961-10-15
GB817240A (en) 1959-07-29
BE559529A (en))
NL219293A (en))

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