[go: up one dir, main page]

WO1986001505A1 - Compositions diazoiques jaune citron - Google Patents

Compositions diazoiques jaune citron Download PDF

Info

Publication number
WO1986001505A1
WO1986001505A1 PCT/US1984/001385 US8401385W WO8601505A1 WO 1986001505 A1 WO1986001505 A1 WO 1986001505A1 US 8401385 W US8401385 W US 8401385W WO 8601505 A1 WO8601505 A1 WO 8601505A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
methyl
hydrogen
ethyl
diazonium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1984/001385
Other languages
English (en)
Inventor
Robert C. Desjarlais
Edward W. Bennett
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
James River Graphics Inc
Original Assignee
James River Graphics Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by James River Graphics Inc filed Critical James River Graphics Inc
Priority to JP59503317A priority Critical patent/JPS62500099A/ja
Priority to PCT/US1984/001385 priority patent/WO1986001505A1/fr
Priority to EP19840903333 priority patent/EP0192638A1/fr
Publication of WO1986001505A1 publication Critical patent/WO1986001505A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/58—Coupling substances therefor
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio 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
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides

Definitions

  • the present invention relates to diazo photoreproduction, and more particularly, to coupling compounds and diazonium compounds for use in diazo photoreproduction.
  • one or more coupling components are included as ingredients of a sensitizing composition.
  • the sensitizing composition also includes a diazo sensitizer which decomposes when subjected to actinic radiation. Accordingly, after exposure, coupling between the coupling component or components and the diazo sensitizer can only occur in those areas where decomposition was not complete. Development is effected by subjecting the exposed composition to alkaline atmosphere, e.g., by bringing it into contact with ammonia vapors, to neutralize the acidic inhibitor with the concomitant formation of dyestuff in the nonexposed areas due to coupling of the residual diazo compound and the coupling components.
  • coupling components are typically described as being couplers of a given color, with the color being the color of the dye which is usually obtained when the particular coupler in question couples with a diazonium compound.
  • couplers such as monohydric phenols, catechols, catechol derivatives, resor ⁇ inols, resorcinol derivatives, diketones, acetoacetic acid derivatives, acetonitriles, cyanoacetamides and the like, usually result in yellow, orange, sepia, brown, red or maroon azo dyes.
  • couplers from such classes of materials are conveniently referred to as yellow, orange, sepia, brown, red, or maroon couplers.
  • couplers such as hydroxy naphthoic acid derivatives, dioxynaphthalene derivatives, pyronones, hydroxypyridones, and the like, usually result in blue or violet azo dyes, and thus are conveniently referred to as blue or violet couplers.
  • One group of highly useful coupling components are the yellow couplers, since the dyes obtained from these couplers usually have actinic absorption characteristics which permit their use as the sole coupler in a diazo composition which is employed to prepare diazotype "masters" or intermediates, and since couplers from this group can often be employed as shading components when used in conjunction with another coupler or couplers.
  • compounds containing active methylene groups compounds such as acetonitriles, derivatives of acetonitriles, and the like, have been employed as yellow couplers in diazo compositions, (c.f., for example, U.S.
  • This tendency to precouple prior to exposure and development has limited the use of these materials somewhat, since even a slight amount of precoupling can result in the formation of an azo dye in those areas of the diazotype material which are the background or "cleared" areas of the diazotype print.
  • active-methylene types of couplers also result, upon coupling, in dyes which have an undesirable reddish hue and/or which have a tendency to fade upon subsequent exposure to light.
  • the print obtained possess satisfactory contrast, density, dye brightness, background clarity, etc.
  • those areas of the light-sensitive material subjected to the actinic effects of the exposure radiation should be totally devoid of spurious discoloration.
  • the light-sensitive diazonium compound should, ideally, yield colorless products upon light-induced decomposition.
  • D min minimum density (or minimum density) (D min ) of prints made using such compounds to rapidly discolor to an objectionable pink color. Consequently, although the diazos described in the prior art provided high speeds of reproduction, a need continues to exist for high speed diazonium salts which possess thermal stability, good dye stability to acid and light, provide a background or minimum density (D min ) which is resistant to discoloration, and develop rapidly as well as allowing a wider range of azo dye colors, especially a more neutral blue color with B.O.N. arylamides, such as
  • one object of the present invention resides in the provision of light-sensitive diazonium compounds wherein the disadvantages discussed above are eliminated or at least mitigated to a substantial extent.
  • Another object of the present invention resides in the provision of diazo sensitizing compositions capable of providing image reproduction substantially devoid of background discoloration.
  • R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of hydrogen, a halogen atom, alkyl of about 1 to 6 carbon atoms, aralkyl of about 6 to 10 carbon atoms, aryl of about 6 to 10 carbon atoms, branched alkyl of about 1 to 6 carbon atoms, alkoxy of about 1 to 6 carbon atoms, and alkylthio, at least one of R 1 , R 2 , and R 3 being other than hydrogen or a halogen atom;
  • X is S, SO, or SO 2 ;
  • Y is hydrogen or a halogen atom.
  • the present invention also provides novel diazonium salts which possess excellent photo speed, and yet possess good thermal stability, develop rapidly, allow a wide range of azo dye colors and, importantly, provide exceptional resistance to discoloration in the Dmm. areas.
  • the decomposition products of the diazo compounds exhibit a resistance to discoloration upon exposure to UV light, and the azo dyes resulting from the diazos are resistant to changes in pH such as acidic conditions.
  • the diazonium salts of the present invention are of the following general formula:
  • R 1 is tertiary butyl or tertiary amyl, preferably in a position para to the oxygen of the phenoxy group;
  • Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkylthio, arylthio, alkylthio, halogen, allyl, allyloxy, allylthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, dialkyl carbonamido, and the like;
  • R 2 and R 3 are the same or different and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, betachloroalkyl, branched alkyl, or a structure wherein R 2 and R 3 may be linked together to form a heterocyclic structure, optionally including a sulfur atom, an oxygen atom, or a substituted trivalent nitrogen atom, e.g., morpholino, piperidino, thiomorpholino, piperazino, pyrrolidino; and
  • X is an anion
  • the lemon-yellow coupling components of the present invention are compounds of the general formula:
  • R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of hydrogen, a halogen atom, alkyl of about 1 to 6 carbon atoms, aralkyl of about 6 to 10 carbon atoms, aryl of about 6 to 10 carbon atoms, branched alkyl of about 1 to 6 carbon atoms, alkoxy of about 1 to 6 carbon atoms, and alkylthio, at least one of R 1 , R 2 and R 3 being other than hydrogen or a halogen atom;
  • X is S, SO, or SO 2 ; and
  • Y is hydrogen or a halogen atom.
  • Preferred compounds within this group are those in which R 1 and R 3 are selected from methyl, ethyl, isopropyl or a halogen atom and R 2 is hydrogen; and wherein R 1 and either R 2 and R 3 are hydrogen with the other of either R 2 or R 3 being selected from other than hydrogen or a halogen atom.
  • 2,2'-dihydroxy-3,3',6,6'-tetramethyl diphenyl sulfide i.e., R 2 and Y are hydrogen; R 1 and R 3 are methyl; X is S); 2,2'-dihydroxy-3,3'dimethyldiphenyl sulfide (i.e., R 1 , R 2 and Y are H; and R 3 is methyl); and 2,2'-dihydroxy-3,3'-diisopropyl6, 6'-dimethyldiphenyl sulfide (i.e., R 1 is methyl; R 2 is hydrogen; and R 3 is isopropyl).
  • Such compounds can be prepared by reacting an appropriately substituted phenol with sulfur dichloride in the presence of an inert solvent. Temperatures of from about 5°C to about 35°C are preferred, with temperatures of from about 5° to about 15°C being particularly preferred with the lower-boiling inert solvents.
  • the reaction may, if desired, be conducted under an atmosphere of a stream of dry, inert gas to facilitate the removal of the hydrogen chloride which is evolved.
  • the resulting compounds are easily recovered as crystalline solids having relatively high melting points.
  • the sulfoxide and sulfone derivatives of these sulfides are prepared by treating the sulfide with an appropriate amount of an oxidizing agent, such as hydrogen peroxide, chromic oxide, potassium permanganate, and the like.
  • an oxidizing agent such as hydrogen peroxide, chromic oxide, potassium permanganate, and the like.
  • Synthesis of the compounds of the present invention is facilitated by the use of starting phenols which are substituted by halogen in the position para to the hydroxy group.
  • the predominant reaction of a phenol with sulfur dichloride is para substitution.
  • 4-halogen substituted phenols are used to block the 4-position. This leaves the 2-position open for substitution. After this has been completed, if desired, the 4-position can be unblocked by reductive dehalogenation.
  • the light sensitive diazonium compounds which can be employed in preparing the light-sensitive diazo compositions of the present invention are any of the numerous light-sensitive diazonium compounds which are available in the prior art, and the particular lightsensitive diazonium compound which is employed is not critical in the practice of this invention.
  • Illustrative of such compounds are the stabilized salts or double salt complexes of diazonium derivatives of a phenylenediamine, for example, stabilized salts of diazonium derivatives of such compounds as N-methyl-pphenylenediamine, N-ethyl-p-phenylenediamine, Nhydroxyethyl-p-phenylenediamine, N-methyl-N-(betahydroxyethyl)-p-phenylenediamine, N-ethyl-N-(betahydroxyethyl)-p-phenylenediamine, N-butyl-N-(betahydroxyethyl)-p-phenylenediamine, N,N-di-(beta-hydroxyethyl)-p-phenylenediamine, N-benzyl-N-ethyl-pphenylenediamine, N-ethyl-2-methyl-4-aminoaniline, N,Ndimethyl
  • the nature of the salt used to stabilize or complex the diazonium derivative is not critical, and can be, for example, a zinc chloride double salt, a cadmium chloride double salt, a tin chloride double salt, a borofluoride salt, a sulfate salt, a hexafluorophosphate salt, and the like.
  • a particularly preferred class of diazonium compounds for use with the couplers disclosed herein are the diazonium compounds which comprise another aspect of the present invention.
  • the diazonium compounds are represented by the following formula:
  • R 1 is tertiary butyl or tertiary amyl, preferably in a position para to the oxygen of the phenoxy group;
  • Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkythio, arylthio, alkylthio, halogen, allyl, allyloxy, allyIthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, dialkyl carbonamido, and the like; R 2 and R 3 are the same or different and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, beta-chloroalkyl, branched alkyl, or a structure wherein R 2 and R 3 may be linked together to form a heterocyclic structure, optionally including a sulfur atom, an. oxygen atom, or a substituted
  • X is an anion
  • R 1 is t-butyl
  • R 2 and R 3 are both methyl or ethyl or combine to form a morpholino group
  • Y is hydrogen, a halogen, methyl, ethyl, methoxy, morpholino, a thioether, a phenoxy group, or a substituted phenoxy group.
  • the diazonium compounds of the present invention are characterized by a tertiary butyl phenoxy or tertiary amyl phenoxy group which is located meta to the diazonium group.
  • the replacement of the chloro group of the prior art by a tertiary butyl or amyl group results in a bathochromic shift of both the diazo compound and the resulting azo dyes.
  • improved dye color and photospeed are obtained as compared to the chloro substituted compound, without any sacrifice in thermal stability.
  • the nature of the group which is located para to the t-butyl or t-amyl phenoxy group is also important.
  • the nature of this group affects the photo speed. For example, it has been found that a phenoxy substituent provides a compound having a photo speed slower than that of a compound having a chloro substituent. At the same time, the color obtained is shifted depending on this latter group. In the example above, a chloro group gives violet colors with conventional blue couplers, while a phenoxy group gives a more neutral blue.
  • the group substituted para to the t-butyl or t-amyl phenoxy group affects the photo speed and dye color of the resulting compound according to its relative electron donating ability. It is preferred that it should be less electron donating than methoxy, such as thioether, a methyl group, an ethyl group, a halogen, a hydrogen, or a phenoxy.
  • methoxy such as thioether, a methyl group, an ethyl group, a halogen, a hydrogen, or a phenoxy.
  • the salt forming anions employed are any of those conventionally employed in derivatives of diazotized para-phenylene diamine.
  • Such anions include salt-forming anions such as sulfate, chloride, phosphate, tetrafluoborate, hexafluorophosphate and sulfonate, as well as preferred double salts of zinc chloride, cadmium chloride, and tin chloride.
  • Table I provides a list of substitutions made to prepare compounds falling within the above formula.
  • R 1 is tertiary butyl group located in the para position on the phenoxy ring.
  • the anion in each case is PF 6 .
  • Also provided in Table I are the waveleng 3 th absorbance ( ⁇ max ) and the extinction coefficient
  • the diazonium compounds of the present invention are particularly suited for two-component dry processes, wherein development is achieved by the utilization of ammonia gas.
  • a coupling compound is generally intimately mixed with the diazo sensitizer and stabilized against premature coupling.
  • Development is effected by coupling the diazo compound with the coupling compound by passing the material which has previously been exposed to light, through an alkaline gas, such as ammonia.
  • an alkaline gas such as ammonia.
  • Suitable coupling components which can be employed in conjunction with the diazonium salts in a two component diazo reproduction process include: 6 ,7-dihydroxynaphthalene-2-sulfonic acid sodium salt 2-(m-hydroxyphenoxy) ethanol 2, 3-dihydroxynaphthalene 1, 8-dihydroxynaphthalene phloroglucinol resorcinol octylresorcinol
  • Particularly preferred coupling components are betahydroxynaphthoic acid arylamides. Upon coupling with the diazos of the present invention, intense violet or blue dyes are produced.
  • Particularly preferred coupling components are the lemon yellow couplers disclosed herein. It should be understood that mixtures of light-sensitive diazonium compounds can be employed in the practice of the present invention without departing from the scope thereof, and that other couplers can be employed in conjunction with the yellow couplers hereinbefore described in preparing diazo compositions in accordance with the present invention without departing from the scope thereof.
  • black-line diazo compositions comprising one or more couplers from the particuuar class of lemon-yellow azo coupling components set forth above in full detail, along with one or more lightsensitive diazonium compounds and one or more BON blue azo coupling components such as 2-hydroxy-3-naphthoic acid, 2'-methoxyanilide, 2-hydroxy-3-naphthoic acid,
  • storage-stable i.e., are resistant to precoupling
  • color-shift with changes in pH i.e., are resistant to color-shift with changes in pH.
  • any of the acid stabilizers which are generally employed in the art may be present to prevent the precoupling of the diazonium salt and coupling component, including organic acids such as citric acid, tartaric acid, boric acid, 5-sulfosalicylic acid, acetic acid, as well as inorganic acids, such as sulfuric acid, perchloric acid, fluoboric acid, hexafluorophosphoric acid, and the like.
  • organic acids such as citric acid, tartaric acid, boric acid, 5-sulfosalicylic acid, acetic acid
  • inorganic acids such as sulfuric acid, perchloric acid, fluoboric acid, hexafluorophosphoric acid, and the like.
  • Other additives which are genrally included in the light sensitive diazo layer to prevent precoupling include acidic salts, such as zinc chloride, magnesium chloride, cadmium chloride, and the like.
  • additives generally employed in diazo-type photoreproduction can be employed in conjunction with the diazonium salt of the present invention.
  • substances which increase the developing speed such as glycerol, polyethylene glycol, and urea
  • surface improving substances such as finely divided silica (colloidal or non-colloidal), aluminum oxide, barium sulfate, rice starch, and the like
  • binders such as gelatin, gum arabic, cellulose ethers, starch derivatives, polyvinyl alcohol, dispersions of synthetic resins, such as dispersions of cationic, nonionic, and anionic polyvinyl acetate
  • substances intended to retard deterioration of the background of the copies such as thiourea, hindered phenolics, and the like.
  • the diazo compositions can be applied to any conventional support employed in diazo reproduction processes.
  • the diazo material may be applied to an opaque support such as white paper or opaque linen, or a transparent support such as tracing paper, tracing linen, cellulose ester foil, polyester foil, transparentized paper, and the like.
  • the diazonium salt composition can be applied directly to the surface of the support or may be present in a hydrophilic film layer which may or may not be attached to the support by means of one or more conventional sublayers.
  • novel diazonium salts of the present invention can be prepared by various routes well known to those skilled in the art.
  • 2-(4'-tert.butyl)phenoxy-5-chloro nitrobenzene can be produced by reacting 2,5-chloro-nitrobenzene with para-tert.butylphenol after which the resulting compound is converted to the corresponding amine.
  • the amino group is then alkylated and the resulting alkylated compound is subjected to nitration in acetic acid in the presence of acetic anhydride.
  • t-butyl or t-amyl group can be positioned at any location on the phenoxy ring, it is preferred that it be located in the para position.
  • the tertiary butyl group is particularly well suited as a donating group due to the lack of reactivity on the adjacent carbon atom during the nitration step just prior to reduction and diazotization.
  • the solution was then cooled and the solid nuggets which formed were filtered out.
  • the nuggets were then suspended in water, heated to liquify them while keeping the solution acidic by the addition of hydrochloric acid as necessary. After cooling, the solid lumps were filtered. These were dissolved in hot Isopar G (trademark of Exxon for a hydrocarbon fraction) and the excess water distilled out.
  • the product dissolved in hot Isopar G (trademark of Exxon for a hydrocarbon fraction) was decanted from a small amount of black tars clinging to the vessel. The decanted solution was cooled to room temperature and then to -5°C. The resulting crystals were filtered, washed with hexane and air dried, to recover 154g of product melting at 72-78°C (98% yield).
  • the mix was divided into 6 equal portions and to each was added yellow couplers of Table 1 in the amounts shown in Table 1.
  • the solutions were bead imbibition coated onto polyester films (containing a suitable bonding layer and an overcoat of cellulose acetate propionate of approximately .25 mils thickness).
  • the films were dried for 5 minutes at 70°C.
  • the films were processed in the ordinary manner (i.e., using a Kodak #2 photographic step tablet as a master, the films were exposed in a Scott 716TM microprinter equipped with a
  • Gallium doped mercury vapor lamp followed by development in a TecnifaxTM Model 6000 ammonia developer which had an ammonia feed rate of 1.3 ml./min. of 26° Baume ammonia introduced onto a hot plate whereby ammonia gas and water vapor are delivered to the film surface).
  • Compound IV is a yellow coupler of the present invention.
  • Compounds I-III and VI are representative compounds of the prior art for comparison purposes.
  • Compound V is a known compound but has not previously been suggested as a coupler.
  • the solution measured 1000 centipoise viscosity and was coated onto a 7 mil polyester film containing a suitable bonding layer using a #30 wire wound Mayer rod.
  • the film was dried for 3 minutes at 85°C in a convection oven.
  • the film was cut into rectangular pieces (105 x 148 mm) and processed in an Addressograph/Multigraph OP-50 R Bruning diazo microfiche duplicator at exposure setting 7.
  • these films were developed at 140°F (60°C), 160°F (71°C), and 180°F (82°C), respectively. The results are as follows:
  • step B To 89 .7 gm of the amine of step B was added 133 gm of trimethyl phosphate. The solution was heated to 180°C at which time the reaction became exothermic, raising the temperature to 210°C. The reaction was cooled and then 60 gm of granular potassium carbonate was added and the resulting solution refluxed for two hours. The solution was again cooled and 28.5 gm of sodium hydroxide dissolved in water was added. The solution was then heated to reflux for two hours. At this time the condenser was removed while heating was continued to allow the methanol to evaporate. After standing for 48 hours, the pH was basic and a solid mass formed. This was extracted with methylene chloride.
  • the resulting solids were filtered, washed with hexane and then recrystallized by dissolving in a minimum of acetone, adding ethyl acetate equal to the acetone, and then hexane.
  • the yield was 10.3 gm (50% yield) having a melting point of 117-118°C (decomposition).
  • the spectra showed a ⁇ max of 4010A, with an extinction coefficient of 23,278.
  • the resulting solution was coated onto cellulose propionate subbed polyethylene terephthalate and' dried in an oven at 70°C for five minutes.
  • the sensitized films were processed in the following well-known manner. Using a Kodak #2 photographic step tablet as a master, the films were exposed in a Scott 716 microprinter equipped with a gallium-doped mercury vapor lamp, followed by development in a Tecnifax Model 6000 ammonia developer which had an ammonia feed rate of 1.3 m./min. introduced onto a hot plate whereby ammonia gas and water vapor are delivered to the film surface.
  • the maximum density of the unexposed area was 2.55 while the minimum density was .04 in the exposed area, as measured with a MacBeth TR 524 densitometer with a visual filter. Density measurements reported in the remainder of the present application were also made by the same densitometer.
  • Methyl Ethyl Ketone 10 5 Sulfosalicylic Acid 2.18 2-hydroxy-3-naphoic acid-2' ethylanilide 2.91 The solution was divided into two equal parts. To one part (part A) was added 2.27 gm of 2-chloro-4-N,N-dimethyl amino-5-(4'chloro)phenoxy benzene diazonium hexafluorophosphate ( ⁇ max 3950 ⁇ ).
  • part B To the other part (part B) was added 2.38 gm of 2-chloro-4-N,N-dimethylamino-5(4'-tert.-butyl) phenoxy benzene diazonium hexafluorophosphate ( ⁇ m a x 4010 ⁇ ) .
  • the solutions were bead imbibition coated onto polyester films containing a suitable bonding layer and covered with an overcoat of a layer of cellulose acetate propionate of approximately .25 mils thickness. The films were dried for 5 minutes at 70°C.
  • the sensitized films were processed in the following ordinary manner.
  • the solution was divided into two equal parts. To one part (part A) was added 0.48 gm of 2-chloro-4-N,Ndimethyl-amino-5-(4'-chloro) phenoxy benzene diazonium tetrafluoborate. To the other part (part B) was added 0.50 gm of 2-chloro-4-N,N-dimethyl-amino-5- (4'-tert.-butyl) phenoxy benzene diazonium tetrafluoroborate. The solutions were coated onto a polyester film containing a suitable bonding layer using a #28 wire wound Mayer rod, then dried 5 minutes at 70°C in a convection oven. The other side of the polyester film was coated with a silica dispersed into a suitable polymer matrix and dried. The films were each cut to proper size and processed as in Example VI to yield prints of A and B:
  • Wingstay L (trademark of Goodyear Tire .40 and Rubber Co.) Thiourea .12
  • the solution was divided into two equal parts, part A and part B.
  • part A was added 1.0 gm of 2-chloro-4-N,Ndimethylamino-5-(4'-tert.-butyl) phenoxy benzene diazonium tetrafluoroborate.
  • part B was added .9 gm of 2chloro-4-N,N-dimethyl amino-5-(4'methyl) phenoxy benzene diazonium tetrafluoroborate.
  • the resulting solutions were bead imbibition coated onto clear polyester films, dried, and processed as in Example VII.
  • the resulting print obtained from film coated from part A was a more neutral black color than that from part B.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Une composition diazoïque photosensible comprend au moins un composé diazoïque photosensible ayant la formule (I) et au moins un élément diazoïque de copulation ayant la formule (II).
PCT/US1984/001385 1984-08-30 1984-08-30 Compositions diazoiques jaune citron Ceased WO1986001505A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP59503317A JPS62500099A (ja) 1984-08-30 1984-08-30 レモン−イエロ−ジアゾ組成物
PCT/US1984/001385 WO1986001505A1 (fr) 1984-08-30 1984-08-30 Compositions diazoiques jaune citron
EP19840903333 EP0192638A1 (fr) 1984-08-30 1984-08-30 Compositions diazoiques jaune citron

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1984/001385 WO1986001505A1 (fr) 1984-08-30 1984-08-30 Compositions diazoiques jaune citron

Publications (1)

Publication Number Publication Date
WO1986001505A1 true WO1986001505A1 (fr) 1986-03-13

Family

ID=22182245

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1984/001385 Ceased WO1986001505A1 (fr) 1984-08-30 1984-08-30 Compositions diazoiques jaune citron

Country Status (3)

Country Link
EP (1) EP0192638A1 (fr)
JP (1) JPS62500099A (fr)
WO (1) WO1986001505A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2342099A (en) * 1942-04-10 1944-02-22 American Cyanamid Co Preparation of barium salts of alkyl phenol sulphides
US3619191A (en) * 1967-09-13 1971-11-09 Tecnifax Corp The Diazo-type materials
US3634090A (en) * 1968-09-03 1972-01-11 Keuffel & Esser Co Light sensitive one-component diazotype material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2342099A (en) * 1942-04-10 1944-02-22 American Cyanamid Co Preparation of barium salts of alkyl phenol sulphides
US3619191A (en) * 1967-09-13 1971-11-09 Tecnifax Corp The Diazo-type materials
US3634090A (en) * 1968-09-03 1972-01-11 Keuffel & Esser Co Light sensitive one-component diazotype material

Also Published As

Publication number Publication date
JPS62500099A (ja) 1987-01-16
EP0192638A1 (fr) 1986-09-03

Similar Documents

Publication Publication Date Title
US2245628A (en) Reflex copying process
US3248220A (en) Two-component diazotype material
US3113025A (en) Diazotype materials for the production of black images
US3764321A (en) Photographic dry copying process with a neutrostyryl dye
US2694009A (en) Diazo-n-sulfonate light-sensitive material
US4492749A (en) Diazotype materials with 2-hydroxy-naphthalene having sulfonamide substituent as coupler
US3397058A (en) Diazotype material
US3462271A (en) Diazotype material
US3619191A (en) Diazo-type materials
US4590263A (en) High speed diazonium salts useful in diazo type photoreproduction
US2946684A (en) Diazotype copying processes
US3615578A (en) Light-sensitive diazo compounds and light-sensitive material containing them
US3281245A (en) Diazotype material
WO1986001505A1 (fr) Compositions diazoiques jaune citron
US3679413A (en) Photographic process which produces neutral dye image in diazotype material
US3585033A (en) Diazotype composition employing 3'-substituted 2-hydroxy-3-naphthanilides as couplers
US2411811A (en) Light-sensitive materials
US3694247A (en) Heat-sensitive copying material
US3331869A (en) Halogenated phloroglucinol carboxylic acid
US3442650A (en) Diazonium compounds and diazotype materials containing them
US3976491A (en) Diazo compositions and diazotype materials prepared from same
US4642383A (en) Fast coupling lemon-yellow phenolic couplers
US2542849A (en) Diazotypes containing pyronones
US3442652A (en) Diazonium compounds and diazotype material
US3615487A (en) Method for the production of diazo-type intermediate originals

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): JP

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BE DE FR GB NL

WWE Wipo information: entry into national phase

Ref document number: 1984903333

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1984903333

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1984903333

Country of ref document: EP