US3282693A - Photographic printout methods and materials utilizing organic azide compounds and coupler compounds therefor - Google Patents

Photographic printout methods and materials utilizing organic azide compounds and coupler compounds therefor Download PDF

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US3282693A
US3282693A US227561A US22756162A US3282693A US 3282693 A US3282693 A US 3282693A US 227561 A US227561 A US 227561A US 22756162 A US22756162 A US 22756162A US 3282693 A US3282693 A US 3282693A
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group
light
sensitive
class consisting
print
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John J Sagura
James A Van Allan
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to DEE20480A priority Critical patent/DE1258265B/de
Priority to FR851233A priority patent/FR1280220A/fr
Priority to GB3998/61A priority patent/GB978092A/en
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Priority to US227561A priority patent/US3282693A/en
Priority to DEP1269A priority patent/DE1269478B/de
Priority to GB38383/63A priority patent/GB1066965A/en
Priority to FR949188A priority patent/FR84410E/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
    • G03C1/695—Compositions containing azides as the photosensitive substances

Definitions

  • This invention relates to photographic reproduction methods and materials and particularly to photographic print-out system comprising certain organic azides in combination with certain nitrogen containing heterocyclic compounds hereinafter referred to as 'heterocyclic couplers.
  • organic azido compounds useful in the present invention have the general formulae:
  • Ar represents an aryl group (e.g. phenyl, a-naph thyl, B-naphthyl, and aryl gnoups substituted with any of the nucleophilic and electnophilic groups, for example, 4-methoxyphenyl, 3-ethylphenyl, 2-propylphenyl, 2- chlorophenyl, 3-fluorophenyl, 4-nitrophenyl, Z-hydroxyphenyl, 3-hydroxyphenyl, Z-aminophenyl, 4-phenoxyphenyl, 4-phenylthiophenyl, 4-azidophenylthio-4-phenyl, 7-Stilb8ZO16, 9-acridine, 2-methoxy-7-chloro-9-acridine, ahydroxy-Bmaphthyl, fl-hydroxy oz naphthyl, etc.); Q represents a group selected from the class consisting of the oxygen atom, the sulfur atom, the
  • methyl, ethyl, propyl, butyl, etc. an aryl group (e.g. phenyl -4-methylphenyl, 3-ethylphenyl, 2-methoxyphenyl, 4-ethoxyphenyl, 4-nitrophenyl, Z-nitrophenyl, etc.), a substituted sulfonyl group (e.g.
  • methylsulfonyl phenethylsu-lfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, phenylsulfonyl, p-tolylsulfonyl, m-tolylsulfonyl, etc), an alhoyl group (eg actyl, trichloroacetyl, trifluoroacetyl, propionyl, 'butryl, etc.), an anoyl group (e.g. benzoyl, naphthoyl, etc), a carbalkoxy group (e.g.
  • R represents .a group selected from the class consisting of the azido grouup, and an alkyl group (e.g. methyl, ethyl, propyl, etc.)
  • R represents a group selected from the class consisting of the azido group, an alkyl group (e.g. methyl, ethyl, propyl, etc.), an amino group (e.g. amino, N-phenylamino, N-methylamino, N propylamino, etc.)
  • R represents a member selected from the class consisting of the hydrogen atom, and an alkyl group (e.g. methyl, ethyl, phenethyl, propyl, etc.).
  • Azide e.g. methyl, ethyl, propyl, etc.
  • an aryl group e.g. phenyl, tolyl, naphthyl, etc.
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl group (e.g. methyl, ethyl, phenethyl, 2-hydroxyethyl, propyl, butyl, etc.), an alkoxy group (e.g. methoxy, ethoxy, propoxy, butoxy, phenethoxy, etc.), an aryl group (e.g.
  • aryl group e.g. phenyl, tolyl, etc.
  • the nitro group e.g. a halogen atom (e.g. chlorine, bromine, fluorine, etc.), the hydroxy group, the oxygen atom, etc. and the non-metallic atoms such that when the R and R groups are taken together with adjacent carbon atoms in the benzene ring (to which they are attached) they form a fused carbocyclic ring (e.g. phenyl) or a fused heterocyclic ring;
  • W represents a group selected from the class consisting of the sulfur atom, the selenium atom, the oxygen atom, the
  • R represents an alkyl group (e.g. methyl, ethyl, etc.);
  • X represents an acid anion (e.g. chloride, bromide, iodide, chlorate, p-toluenesulfonate, thiocyanate, etc.);
  • R represents a group selected from the class consisting of the hydrogen atom, an alkyl group (e.g.
  • n represents an integer of COUPLER Name
  • Phenothiazine 3-nitrophenothiazine. l-methoxyphenothiazine. l-hydroxyphenothiazine. 3-isopropoxyphenothiazinev 3,G-dimethylphenothiazine.
  • Dihydrobenzothiazine S-methylphenothiazine. Benzo[a]phenothiazine. 9-methoxybenzo[a]phenothiazine. Benzo[b]phenothiazine. 6,1l-dioxobenzo[b]phen0thiazine.
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl group 1,6-dimethoxybenz0[b]phen0thiazine.
  • Benzo[c]phenothiazine Dibenzo[a,j]phenothiazine.
  • Benzo[a]phenoselenazine Benzo[c]phenothiazine.
  • the azides represented by the second and third formulae above i.e., th'e aroyl azides and their vinylogs, are generally less active than the other azides for the purpose of the present invention unless a third substance,
  • Specific salts which have been found to be useful include ammonium chloride itself and the hydrochlorid'es of, for example, 4-aminodiphenylamine, 3,3'-dimethoxybenzidine, Z-aminobenzothiazole, 1,1'-diphenylhydrazine, poly(aminostyrene), diethylamine, guanidine, 2-aminobiphenyl, p-toluidine, and phenothiazine among others.
  • hydrochlorid'es of, for example, 4-aminodiphenylamine, 3,3'-dimethoxybenzidine, Z-aminobenzothiazole, 1,1'-diphenylhydrazine, poly(aminostyrene), diethylamine, guanidine, 2-aminobiphenyl, p-toluidine, and phenothiazine among others.
  • the light-sensitive elements of the present invention may be prepared 'by conventional coating procedures.
  • the azides and heterocyclic couplers are dissolved or dispersed in a natural or synthetic polymer in a suitable solvent and coated on a suitable photographic support by means of a plate Whirler or other device capable of producing a thin, uniform coating of the light-sensitive composition.
  • the vehicle in which the light-sensitive composition is coated may be any of the natural or synthetic high polymers ordinarily used for photographic layers, such as gelatin, casein, polystyrene, vinyl resins including poly(vinyl alcohol), poly(vinyl b utal) 'etc., cellulose derivatives, or mixtures of these polymers.
  • the support for the light-sensitive layer may be a plate, sheet or strip of any of the commonly used materials, such as paper, cellulose derivatives, .glass, synth'etic high polymers and the like. Any of the solvents commonly employed in the art for coating high polymer layers may be used with advantage, an excellent solvent for this purpose being Z-butanone.
  • solvents such as cyclohexanone, cellosolve, benzene, methyl ethyl ketone, ethylene chloride, toluene, methyl isobutyl ketone, cellosolve acetate, etc. which have higher boiling points than the basic solvent used, such as acetone in the preparation of the coating composition.
  • solvents such as cyclohexanone, cellosolve, benzene, methyl ethyl ketone, ethylene chloride, toluene, methyl isobutyl ketone, cellosolve acetate, etc.
  • solvents such as cyclohexanone, cellosolve, benzene, methyl ethyl ketone, ethylene chloride, toluene, methyl isobutyl ketone, cellosolve acetate, etc.
  • solvents such as cyclohexanone, cellosolve, benzene, methyl ethyl
  • the invention also includes, in another embodiment, the provision of light-sensitve elements in which the light-sensitive composition is inconporated in the base layer thus eliminating one of the two coating operations usually required.
  • This may be accomplished by dissolving the aztide, the heterocyclic coupler, and a high polymer such as cellulose triacetate in a suitable organic solvent such as a mixture of methylene chloride and methanoland coating the resulting composition on a glass plate or other suitable surface.
  • the coating When the coating has dried sufliciently it is stripped from the glass plate to produce a self-supporting film containing the light sen-sitive azide-heterocyclic couple-r composition.
  • any of the high polymers, natural or synthetic, such as those mentioned :above, that can be cast into clear flexible films, can be used in place of cellulose triacetate to make self-supporting light sensitive elements.
  • the light-sensitive 'elements of the invention whether of the type in which the azide-heterocyclic coupler composition is coated in a colloid layer on a separate support or of the type in which the base itself contains the light sensitive composition, produce a colored print-out image on an uncolored background when exposed through .a pattern to a suitable source of .actinic light.
  • the lightsensitive layer becomes colored where it is exposed to light and thus a positive print-out imag'e will be obtained when the exposure is made through a negative or a negative image when the exposure is made through a positive.
  • Any suitable suorce of actinic light may be employed for the exposure including an lamps, mercury lamps, photofiood lamps and sun lamps.
  • Example I A coating solution consisting of 50 grams of a 10% dope of Vinylite VYLF in 2-butanone, 1.0 gram or 2- tazido-1phenylcarbamylbenzimidazole land 0.3 gram of benzo[b]
  • Vinylite VYLF is a copolymer of vinyl chloride and vinyl acetate, -88% vinyl chloride, molecular weight 6,000.
  • Example 2 Twenty grams of 2-az-ido-l-carbobutoxymethylcarbamylbenzimidazole and 1.0 gram of benzo[b]phenoxazine were dissolved :in 600 grams of a 10% dope of cellulose acetate propionate polymer in Z-butanone. This solution was coated onto a paper support and exposed as in Example 1 to produce a blue-black image.
  • Example 3 A coating solution was prepared by dissolving 0.3 gram of 2-azido 1 car-bobu-toxymethylcarbamylbenzimidazole and 0.1 gram of aoridan in 25 grams of 10% Vinylite VYLF in Z-butanone. This coating When exposed to a source of ultraviolet radiation produced a purple printout image.
  • Example 4 A coating solution was prepared by dissolving 0.3 gram of 2-rnethoxy-6-chloro-9-azidoacridine and 0.2 gram of ph'enothiazine in 25 grams of 10% Vinylite VYLF in 2- butanone. When this composition was coated on a photographic support and exposed to a .source of ultraviolet radiation, a red-brown print-out image was obtained.
  • Example 5 A coating composition was prepared by dissolving 14 grams of Z-azidobenzoxaz-ole, 1.8 grams of benzo[a]- phenot-hiazine and 0.5 gram of 4-quinolizone in 150 grams of a vinyl dope in 105 grams of Z-butanone.
  • the vinyl dope was composed of 40% Vinylite VYLF (described above) and 60% Vinylite VYHH, the latter being a copolymer of vinyl chloride and a vinyl acetate containing 8588% of vinyl chloride and having a molecular weight of 10,000.
  • This composition was coated onto a conventional cellulose acetate photographic support and dried to produce a light-sensitive photographic element having a concentration of about 3 grams of solids per square foot. When exposed to an ultraviolet-rich light source through a photographic negative a positive print-out image was obtained. This image was stabilized by heating the photographic element to a temperature of about -100" C. for a short period of time.
  • Example 6 A solution of 0.4 gram of Z-azidobenzoxazole and 0.25 gram of phenothiazine in 25 grams of a benzene dope containing 1% by weight of crepe rubber and 5% by Weight ofi polystyrene was Whirl-coated onto a paper support and allowed to dry. The resulting coating was ex.- posed for 30 seconds to a s-unlamp at 'a distance of 10 inches through a negative pattern to produce a blue-on- 7 white positive image. This print was stabilized by heating at 100-430 C. for 20 seconds.
  • Example 8 To 40 ml. of a 10% solution of Viny-lite VYLF in 2- b uta-n-one was added 0.176 gram of 2,4-diazid-o-6-methylpyrimidine and 0.4 gram of phenothiazin-e and the mixture was shaken to effect solution. The resulting solution was coated on paper by means of a plate whirler and the plate whirled until dry. The coated side of the paper plate was exposed through a negative pattern for 30 seconds to a sun-lamp at a distance of 10 inches to produce a sepi'aon-white positive print. This print was stabilized by heating 100130 C. for 20 seconds.
  • Example 9 To 50 ml. of a 10% solution of Vinylite VYLF in 2- butanone was added 0.1 gram of 2,4,6-triazido-sym-triazine, 0.3 gram of phenothiazine and 5 drops of dimethyl sulfoxide. The resulting mixture was shaken to effect solution and then coated on a paper support as in Example 8. The dry paper plate was exposed through a negative pattern for 30 seconds to a sunlamp at 10 inches to produce a sepia-on-wh-ite positive print.
  • Example 10 A coating solution was prepared by dissolving 0.1 gram of 5-azid-otetrazole[-a]phthalazine and 0.2 gram of phenothiazine in 100 ml. of a 10% Vinylite VYLF-2-butan0ne solution. This solution was coated on a paper support by means of a plate whirler and whirled until dry. The resulting light-sensitive plate was exposed through a negative pattern for 1 minute to a sunlamp at a distance of 10 inches to produce a vi-oleton-white positive print.
  • Example 11 A 10% Vinyli-te VYLF solution in Z-butanone containing 0.1 gram of phenoth-i'azine and 0.13 gram of 4,4- diazidodiphenyl sulfide was coated on paper by means of a plate whirler. The dry plate was exposed through a negative to a sun-lamp at 10 inches for 1 minute to obtain a violet-on-white positive image.
  • Example 12 A 5% by weight solution of polyvinylbutal in methanol was saturated with Z-aminobiphenyl hydrochloride. Equivalent amounts of phenothiazine and 'benz-oyl azide were added. The resulting solution was coated on :paper by means of a plate whirler and the plate whirled until dry. The dry plate was exposed through a negative to a sunlamp at a distance of 10 inches for 1 minute to obtain a red-violet positive print-out image. The plate was then stabilized by washing with warm water for five minutes.
  • Example 13 A 5% by weight solution of polyvinylbutal in methanol was saturated with aniline hydrochloride. Equivalent amounts of 2,4,G-triazido-sym-triazine and phenqthiazine were added. The resulting solution was coated on paper by means of a plate whirler and the plate whirled until 8 dry. The dry plate was exposed through a negative to a sunlamp at a distance of 10 inches for 1 minute to obtain a blue print-out image of good quality. This procedure was repeated employing a number of other salts of basic ammonia derivaties in place of the aniline hydrochloride. Table I below lists the salts and the color of the print-out images obtained in each case.
  • the color of the image formed in the embodiments of the invention in which the lightsensitive composition contains an aroyl azide or a vinylog of such an azide, a heterocyclic coupler, and a salt of a basic derivative of ammonia is dependent upon the pH of the stabilized coating.
  • the dye base in this system is apparently red in color while its salts are blue.
  • the color of the print-out image is, therefore, determined by the relative amounts of dye base and dye salt present and thus may range from blue through violet or red-violet as shown in Table I above.
  • Example 14 A light-sensitive element comprising a composite support and light sensitive layer was prepared by dissolving 5 grams of 1-phenylcarbamido-2-azidobenzimidazole, 1 gram of benz[a]phenothiazine and 20 grams of cellulose triacetate in 162 grams of methylene chloride and 18 grams of methanol and coating the resulting dope on a glass plate to a thickness of 0.035 inch. The coating was dried for 6 hours at room temperature. The film was then stripped from the glass plate and exposed for two minutes to a sunlamp through a step-wedge negative. The visible image was intensified by heating several minutes at 65 C. A maximum density (Dmax) of 3.3 and a minimum density (Dmin) of 0.22 were obtained in the print-out image.
  • Dmax maximum density
  • Dmin minimum density
  • Example 15 To 25 grams of a 10% dope of cellulose acetate propionate in 2-butanone were added 0.5 gram of the azide compound and 0.2 gram of the heterocyclic coupler. After solution was complete, the dope was used to make a coating on paper stock at a coverage of approximately 2 grams per square foot. The dope coating was exposed through a negative to a source of ultraviolet light to effect the print-out. Occasionally, the light-sensitive compounds were incompletely soluble in Z-butanone; in such cases they were dissolved in a benzene or ethylene chloride dope of polystyrene or a methanolic dope of polyvinyl butal and then coated in the usual manner. The images formed are described below.
  • the ratio of the reactants can be varied considerably although it is generally preferred to employ approximately stoichiometric amounts of the azides and heterocyclic couplers. Any ratio of azide to heterocyclic coupler which will produce a print-out image of the desired contrast may be employed; however, the ratio required for this purpose depends upon the contrast desired, the intensity of color of the compound produced, the color of the background and the particular azide and heterocyclic coupler combination employed.
  • Mixtures of two or more azide compounds with one or more heterocyclic couplers, or mixtures of one azide compound with two or more heterocyclic couplers are used to advantage in our print-out system.
  • neutral-toned print-out images are desirable in portrait proofing applications.
  • Neutral-toned print-out images are proucked by using two color image-forming systems which produce colors that combine to form a neutral image.
  • the two color-forming systems should preferably have the same or nearly the same photographic speeds so that the neutral tones will be produced at all levels of image densities.
  • Various variations from neutral tones are produced by either varying the ratios of the two color-forming systems from the neutral tone producing combination, or by using other mixtures of color-forming systems. Representative systems are illustrated by the following examples.
  • Example 18 To 25 grams of a 10% solution of vinylite resin (decribed in Example 5) in Z-butanone was added 0.5 gram of 2-azido-1-phenylcarbamylbenzimidazole, 0.2 gram of phenothiazine and 0.2 gram of benzo[c]phenothiazine. This dope was coated by means of a plate-whirler onto a baryta-coated paper stock, dried and exposed to an ultraviolet light source through a continuous tone negative. The resulting print-out color when compared to that obtained from a similar formulation which lacked benzo[c] phenothiazine, exhibited a hue shift toward the green. This composition gave more pleasing prints with certain subjects, such as landscapes and marine scenes.
  • Example 20 To 60 grams of a 10% solution of polystyrene in ethylene chloride was added 1.5 gram of 2-azido-1-phenylzinc, and 0.1 gram of phenothiazine. Coatings made from this formulation yielded a blue print-out image which was less saturated than that obtained when the benzofbjphenoxazine was omitted. This combination affords a better rendition of certain subjects, such as snow scenes and architectural subjects.
  • certain of the light-sensitive compositions of the presetnt invention are also afiected by heat and this property can be used to advantage.
  • certain of the azides can be inactivated, or removed from the coating by thermal diffusion by heating at temperatures of about 75150 C. for periods ranging from about 10 to 30 seconds or more. This makes it,
  • heat may also be employed to intensify the print-out image obtained by exposure to light.
  • the composition described in Example 14 which contains l-phenylcarbamido-2-azidobenzimidazole and benz[a]phenothiazinc is an example of such a composition.
  • the print-out images can be stabilized advantageously by treating them with certain solvents which are capable of differentially extracting the residual light-sensitive azide from the photographic layer while leaving the major part of the print-out dye image and not attacking the vehicles.
  • Solvents useful for this purpose at room temperature include methanol, ethanol, butyl acetate, a 4:1 mixture of isopropanol and acetone. Trichloroethylene is used to advantage at elevated temperatures for removing residual azide compound.
  • a light-sensitive photographic element of claim 1 in which the said light sensitive organic azide and the said coupler compound are incorporated together with the said organic colloid binder in a self-supporting layer.
  • the organic colloid binder is an organic high polymer selected from the class consisting of gelatin; casein; rubber; cellulose acetate; a copolymer of cellulose acetate and cellulose propionate; polystyrene; poly(vinyl alcohol); poly- (vinyl butal); and copolymers of vinyl chloride and vinyl acetate;
  • the organic azide has Formula IV
  • the coupler has Formula IX.
  • a light-sensitive photographic element comprising a photographic support coated with a light-sensitive composition comprising:
  • At least one organic high polymer selected from the class consisting of gelatin; casein; rubber; cellulose acetate; a copolymer of cellulose acetate and cellulose propionate; polystyrene; poly(vinyl alcohol); poly(vinyl 'butal); and copolymers of vinyl chloride and vinyl acetate;
  • a light-sensitive photographic element comprising a photographic support coated with a light-sensitive composition comprising:
  • (l) at least one organic high polymer selected from the class consisting of gelatin; casein; rubber; cellulose acetate; a copolymer of cellulose acetate and cellulose propionate; polystyrene; poly(vinyl alcohol); poly(vinyl butal); and copolymers of vinyl chloride and vinyl acetate;
  • a light-sensitive photographic element comprising a photographic support coated with a light-sensitive com- 45 position comprising:
  • At least one organic high polymer selected from the class consisting of gelatin; casein; rubber; cellulose acetate; a copolymer of cellulose acetate and cellulose propionate; polystyrene; poly(vinyl alcohol); poly(vinyl butal); and copolymers of vinyl chloride and vinyl acetate; (2) 2-azido-1-carboisobutoxymethylcarbamylbenzimidazole; and (3) benzo[b]phenox-azine.
  • a light-sensitive photographic element comprising a photographic support coated with a light-sensitive composition comprising:
  • (l) at least one organic high polymer selected from the class consisting of gelatin; casein; rubber; cellulose acetate; a copolymer of cellulose acetate and cellulose propionate; polystyrene; poly(vinyl alcohol); poly(vinyl butal); and copolymers of vinyl chloride and vinyl acetate;
  • Ar represents an aryl group
  • Q represents a group selected from the class consisting of the oxygen atom, the sulfur atom, the selenium atom, and a NR group
  • R represents a group selected from the class consisting of the hydrogen atom, an alkyl group, an aryl group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxy group, an aroyl group, a carbalkoxy group, and a carbamyl group
  • R and R each represents a group selected from the class consisting of the hydrogen atom, an alkyl group, an alkoxy group, an aryl group, the nitro group, a halogen
  • a light-sensitive photographic element of claim 7 containing additionally 2-azido-l-phenylcarbamylbenzimidazole and phenothiazine in the light-sensitive composition.
  • a light-sensitive photographic element of claim 8 containing additionally 2-azido-l-phenylcarbamylbenzimd azole in the light-sensitive composition.
  • a light-sensitive photographic element of claim 9 containing additionally phenothiazine in the light-sensitive composition.
  • a light-sensitive photo-graphic element of claim 10 containing additionally 2-azido-IphenyIcarbamylbenzimidazole in the light-sensitive composition.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
US227561A 1960-02-05 1962-10-01 Photographic printout methods and materials utilizing organic azide compounds and coupler compounds therefor Expired - Lifetime US3282693A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DEE20480A DE1258265B (de) 1960-02-05 1961-01-21 Lichtempfindliche photographische Schicht
FR851233A FR1280220A (fr) 1960-02-05 1961-01-31 Nouveau produit photographique donnant des images directement visibles, et images obtenues sur ledit produit
GB3998/61A GB978092A (en) 1960-02-05 1961-02-02 Photographic printing paper
US227561A US3282693A (en) 1960-02-05 1962-10-01 Photographic printout methods and materials utilizing organic azide compounds and coupler compounds therefor
DEP1269A DE1269478B (de) 1960-02-05 1963-09-07 Lichtempfindliche Schicht
GB38383/63A GB1066965A (en) 1960-02-05 1963-09-30 Photographic print-out materials
FR949188A FR84410E (fr) 1960-02-05 1963-10-01 Nouveau produit photographique donnant des images directement visibles, et images obtenues sur ledit produit

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US688860A 1960-02-05 1960-02-05
US227561A US3282693A (en) 1960-02-05 1962-10-01 Photographic printout methods and materials utilizing organic azide compounds and coupler compounds therefor

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Cited By (25)

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US3411905A (en) * 1965-06-14 1968-11-19 Eastman Kodak Co Photographic masking process
US3519424A (en) * 1966-02-25 1970-07-07 Eastman Kodak Co Photosensitive compounds and elements
US3532500A (en) * 1967-07-25 1970-10-06 Eastman Kodak Co Light sensitive vesicular composition comprising an azido-s-triazine compound
US3617278A (en) * 1967-03-31 1971-11-02 Eastman Kodak Co Azide sensitizers and photographic elements
US3660093A (en) * 1968-07-08 1972-05-02 Agfa Gevaert Ag Dry azido thermal diffusion copying process
US3716367A (en) * 1971-05-26 1973-02-13 American Cyanamid Co N-succinimide additives for azide imaging systems
US3767409A (en) * 1971-08-02 1973-10-23 Eastman Kodak Co Photographic triorganophosphine-azide dye forming composition and article
US3779762A (en) * 1971-05-26 1973-12-18 American Cyanamid Co N-succinimide additives for azide imaging systems
US3844793A (en) * 1970-10-19 1974-10-29 American Cyanamid Co Photosensitive azido material
US3856531A (en) * 1971-08-02 1974-12-24 Eastman Kodak Co Photographic compositions and processes
US3923522A (en) * 1973-07-18 1975-12-02 Oji Paper Co Photosensitive composition
US3933497A (en) * 1972-12-08 1976-01-20 American Cyanamid Company Photosensitive azido processes
US3964911A (en) * 1972-12-22 1976-06-22 La Cellophane Photographic reproduction processes using diazonium salts and substituted spiro[benzopyrane]
US4139390A (en) * 1977-02-10 1979-02-13 Eastman Kodak Company Presensitized printing plate having a print-out image
US4271251A (en) * 1978-10-19 1981-06-02 Fuji Photo Film Co., Ltd. Photosensitive compositions
US4556625A (en) * 1982-07-09 1985-12-03 Armstrong World Industries, Inc. Development of a colored image on a cellulosic material with monosulfonyl azides
US4622284A (en) * 1984-03-01 1986-11-11 Digital Recording Corporation Process of using metal azide recording media with laser
US4695531A (en) * 1985-07-25 1987-09-22 Minnesota Mining And Manufacturing Company Light-sensitive elements for radiographic use in the formation of an X-ray image
US4886735A (en) * 1987-05-21 1989-12-12 Basf Aktiengesellschaft Photopolymerizable recording materials and photoresist layers and lithographic printing plates based thereon
EP0779536A1 (fr) 1995-12-04 1997-06-18 Konica Corporation Produit d'enregistrement sensible à la lumière et à la chaleur et procédé d'enregistrement l'utilisant
EP2100731A2 (fr) 2008-03-11 2009-09-16 Fujifilm Corporation Précurseur de plaque d'impression lithographique et procédé d'impression lithographique
EP2541322A1 (fr) 2008-10-15 2013-01-02 International Paper Company Composition, procédé de préparation et procédé d'application et d'exposition pour papier d'imagerie lumineuse
US8586279B2 (en) 2008-10-15 2013-11-19 International Paper Company Imaging particulates, paper and process, and imaging of paper using dual wavelength light
WO2022181288A1 (fr) 2021-02-26 2022-09-01 富士フイルム株式会社 Élément sensible aux rayonnements uv et kit sensible aux rayonnements uv
WO2022202362A1 (fr) 2021-03-22 2022-09-29 富士フイルム株式会社 Outil de test et méthode de test

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US2062650A (en) * 1935-01-23 1936-12-01 West End Chemical Company Production of noncrystalline borax
US2844465A (en) * 1954-03-17 1958-07-22 Chalkley Lyman Photographic process
US3061435A (en) * 1954-04-03 1962-10-30 Azoplate Corp Lithographic printing plates and azido compositions therefor
US3099559A (en) * 1959-08-31 1963-07-30 Gen Aniline & Film Corp Silver-free color reproduction process and composition therefor

Cited By (28)

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US3411905A (en) * 1965-06-14 1968-11-19 Eastman Kodak Co Photographic masking process
US3519424A (en) * 1966-02-25 1970-07-07 Eastman Kodak Co Photosensitive compounds and elements
US3617278A (en) * 1967-03-31 1971-11-02 Eastman Kodak Co Azide sensitizers and photographic elements
US3532500A (en) * 1967-07-25 1970-10-06 Eastman Kodak Co Light sensitive vesicular composition comprising an azido-s-triazine compound
US3660093A (en) * 1968-07-08 1972-05-02 Agfa Gevaert Ag Dry azido thermal diffusion copying process
US3844793A (en) * 1970-10-19 1974-10-29 American Cyanamid Co Photosensitive azido material
US3716367A (en) * 1971-05-26 1973-02-13 American Cyanamid Co N-succinimide additives for azide imaging systems
US3779762A (en) * 1971-05-26 1973-12-18 American Cyanamid Co N-succinimide additives for azide imaging systems
US3767409A (en) * 1971-08-02 1973-10-23 Eastman Kodak Co Photographic triorganophosphine-azide dye forming composition and article
US3856531A (en) * 1971-08-02 1974-12-24 Eastman Kodak Co Photographic compositions and processes
US3933497A (en) * 1972-12-08 1976-01-20 American Cyanamid Company Photosensitive azido processes
US3964911A (en) * 1972-12-22 1976-06-22 La Cellophane Photographic reproduction processes using diazonium salts and substituted spiro[benzopyrane]
US3923522A (en) * 1973-07-18 1975-12-02 Oji Paper Co Photosensitive composition
US4139390A (en) * 1977-02-10 1979-02-13 Eastman Kodak Company Presensitized printing plate having a print-out image
US4271251A (en) * 1978-10-19 1981-06-02 Fuji Photo Film Co., Ltd. Photosensitive compositions
US4556625A (en) * 1982-07-09 1985-12-03 Armstrong World Industries, Inc. Development of a colored image on a cellulosic material with monosulfonyl azides
US4622284A (en) * 1984-03-01 1986-11-11 Digital Recording Corporation Process of using metal azide recording media with laser
US4695531A (en) * 1985-07-25 1987-09-22 Minnesota Mining And Manufacturing Company Light-sensitive elements for radiographic use in the formation of an X-ray image
US4886735A (en) * 1987-05-21 1989-12-12 Basf Aktiengesellschaft Photopolymerizable recording materials and photoresist layers and lithographic printing plates based thereon
EP0779536A1 (fr) 1995-12-04 1997-06-18 Konica Corporation Produit d'enregistrement sensible à la lumière et à la chaleur et procédé d'enregistrement l'utilisant
EP2100731A2 (fr) 2008-03-11 2009-09-16 Fujifilm Corporation Précurseur de plaque d'impression lithographique et procédé d'impression lithographique
EP2541322A1 (fr) 2008-10-15 2013-01-02 International Paper Company Composition, procédé de préparation et procédé d'application et d'exposition pour papier d'imagerie lumineuse
US8586279B2 (en) 2008-10-15 2013-11-19 International Paper Company Imaging particulates, paper and process, and imaging of paper using dual wavelength light
US8586280B2 (en) 2008-10-15 2013-11-19 International Paper Company Composition, process of preparation and method of application and exposure for light imaging paper
US8980523B2 (en) 2008-10-15 2015-03-17 International Paper Company Imaging particulates, paper and process, and imaging of paper using dual wavelength light
EP2899592A1 (fr) 2008-10-15 2015-07-29 International Paper Company Substrat revêtu d'une composition particulaire pour imagerie utilisant une lumière à longueur d'onde double et procédé pour la production de cette composition
WO2022181288A1 (fr) 2021-02-26 2022-09-01 富士フイルム株式会社 Élément sensible aux rayonnements uv et kit sensible aux rayonnements uv
WO2022202362A1 (fr) 2021-03-22 2022-09-29 富士フイルム株式会社 Outil de test et méthode de test

Also Published As

Publication number Publication date
FR1280220A (fr) 1961-12-29
GB978092A (en) 1964-12-16
FR84410E (fr) 1965-02-05
DE1269478B (de) 1968-05-30
DE1258265B (de) 1968-01-04
GB1066965A (en) 1967-04-26

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