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

Definitions

• the present invention relates to light sensitive diazo type materials containing m,m-dioxydiphenols as coupling components and, particularly to diazotype intermediates of high opacity containing such coupling components.
• a diazotype layer in order to be satisfactory as an intermediate material, a diazotype layer must meet rigid and diverse specifications.
• the intermediate foil should have the fastest possible printing speed consistent with good opacity, and form a dye having both good actinic opacity and good visual opacity, since visual examination of the, intermediate is frequently necessary.
• the layer must exhibit satisfactory stability, both in the packageand in the developed foil. Both the packaged and developed foil must show good stability against yellowing, especially yellowing which occurs on exposure of a developed foil to ultraviolet radiation since such yellowing increases the opacity of the material.
• the dye formed should be free from a tendency to migrate or to ofiset when in contact with other materials. Heretofore, it has not been possible to combine all of these properties to a satisfactory degree in any commercial product.
• resorcinol One of the most widely used azo dye coupling components in diazo intermediate products is resorcinol. When freshly coated in high concentration, resorcinol yields a dye having good actinic opacity. However, as the coated material ages, difiusion and redistribution of thecomponents takes place so that in place of the monoazo coupling originally predominant, bis-coupling becomes important. Resorcinol is thus very sensitive to the diazo/ coupler ratio. Consequently, as the material ages, the visual opacity increases as the result of bis-dye formation while a marked falling oil in actinic opacity occurs at the same time.
• coupling components which provide layers of good stability having good actinic opacity of which m-hydroxyphenylurea and dimethyl aminomethyl-2,5-xylenol are examples. These materials, however, suffer from restricted solubility, are prone to offset under certain circumstances, and yield layers which fail to develop the dye images rapidly and completely on exposure to ammonia. In addition, their visual opacity is poor.
• Light sensitive diazotype materials containing m;m'- dioxydiphenols as coupling components and, more par ticularly, those intermediate materials of high opacitycontaining such couplers constitute the purposes and objects of the present invention.
• polyfunctional resorcinol etherscontemplated herein may be depicted by the following general formula:
• V Isopropyl alcohol ........a ..mls
• A is alkylene such kylenearylenealkylene, i.e., methylenephenylenemethyl ene, ethylenephenyleneethylene and the like; isoalkylidcne such as isopropylidene and the like;
• X and Y are hydro gen, alkyl such as methyl, ethyl, butyl, amyl, hexyl and the like; sulfo, halogen such as chlorine and bromine;
• n 1 when p is 0 and p +1 when p is a whole number, i.e., 2 when p is .l. V
• m,m'-ethylenedioxydiphenol was made by'a modi as ethylene, trimethylene, tetramethylene, pentamethylene, methyltrimethylene; al-
• this composition yielded a yellow ish-brown image with good visual density, opacity to ultraviolet light, dye stability, and developability.
• this composition When coated on cellulose acetate foil base, dried, irradiated withfactinic light'under a positive; original, and exposed to ammonia vapors, this composition yielded a yellowish-brown image, with excellent stability and good visual density. The printingspeed and ultraviolet opacity of this material were outstanding.
• Example V The procedure is the same as in Example I excepting that the coupling component used is m,m-trirnethylenedioxydiphenol of the following formula:
• This compound may be prepared as follows: m-Nitrophenol was reacted with 1,4-dibromobutane to give 3,3- -dinitrotetramethylenedioxydibenzene, M. 7 -7 C., which was reduced in isopropyl alcohol over palladium on carbon to the amine, M. 128-30 C. 'Diazotization and hydrolysis with dilute sulfuric acid were completed as in Example V and the desired compound was obtained as Example,
• This compound may be prepared 'as follows: 1,5-divbromopentane and m-nitrophenol were condensed to 3,3- dinitropentamethylenedioxydibenzene, M. 94-6 C. This was reduced in ethyl alcohol over palladium on carbon to the amine, M. 1'l9-2l C. Diazotization and hydrolysis with-dilute sulfuric acid; gave-the desired compound as colorless ,needles, M.
• Example IX The procedure is the same as in Example HI excepting that the coupling component is 6,6-dimethyl-3,3- trimethylenedioxydiphenol of the formula:
• OH OH CH CHI OCHICBICHIO This compound may be prepared as follows: B-nitro- 4-methylphenol was prepared from 3-nitro-4-methylaniline by diazotization and hydrolysis (Harvey and Roberson, J. Chem. Soc. 1938, 97-401). This was reacted with trimethylene bromide and alkali to yield 4,4'-dimethyl-3,3'-dinitrotrimethylenedioxydibenzene, M. 106- 9 C. Reduction in ethanol over palladium on carbon went smoothly to give the amino derivative, M. 129-30 C. Diazotization and hydrolysis by the usual method gave the desired compound, M. 139-41 C.
• Example X The procedure is the same as in Example III excepting that the coupling component is m,rn'-(p-phenylenedimethylenedioxy) cliphenol of the formula:
• This compound may be prepared as follows: m-Nitrophenol and p-phenylenedimethylene bromide were reacted to give 3,3-dinitro-p-phenylenedimethylenedioxydibenzene, M. 193-6" C.
• the amino compound, prepared by reduction in ethanol over palladium on carbon was diazotized and hydrolyzed to the desired compound, M. 724 C.
• Example XI The procedure is the same as in Example II excepting that the coupling component is 6,6-dihexyl-3,3'-isopropylidenedioxydiphenol of the formula:
• Example XIII The procedure is the same as in Example 11 excepting that the coupling component employed is 4,4',6,6'-tetramethyl-3,3'-trimethylenedioxydiphenol of the formula:
• Light sensitive diazotype materials comprising a base sensitized with a light sensitive diazonium compound, and as the coupling component, the compound of the following formula:
• V zonium salt (amylase) comprising a translucent base sensitized with a light sensir 1 7 r 8 tive diazonitlm compound, and as the eonplingcomlight-sensitive compound'isa p-4-morpholinylbenzene diaponent, a compound of theiollowin'g formula: V zonium salt. V .1 V
• PATENTS 1 Y are selected from the class consisting of hydrogen, 6 6 7 Great fi n r f 9 alkyl, sulfo and halogen; p is selected fi'om'the class con- 7 1 I 'sisting of 0 and a' whole number; and n ris l when p is 7 OTHER 0"and p+1 when p is 'a whole number.. 1 Chem. Abstracts, 47; 4369g ,(1953).

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

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Citations (3)

• 0
  • NL NL97385D patent/NL97385C/xx active
  • BE BE564689D patent/BE564689A/xx unknown
  • DE DENDAT1068556D patent/DE1068556B/de active Pending
  • NL NL225064D patent/NL225064A/xx unknown
• 1957
  • 1957-02-19 US US641023A patent/US2940852A/en not_active Expired - Lifetime
• 1958
  • 1958-01-29 GB GB2993/58A patent/GB840945A/en not_active Expired
  • 1958-02-19 CH CH5602558A patent/CH375988A/de unknown

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