EP0014982B1 - Zweikomponenten-Diazotypiematerial - Google Patents

Zweikomponenten-Diazotypiematerial Download PDF

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Publication number
EP0014982B1
EP0014982B1 EP80100807A EP80100807A EP0014982B1 EP 0014982 B1 EP0014982 B1 EP 0014982B1 EP 80100807 A EP80100807 A EP 80100807A EP 80100807 A EP80100807 A EP 80100807A EP 0014982 B1 EP0014982 B1 EP 0014982B1
Authority
EP
European Patent Office
Prior art keywords
diazonium salt
hydroxynaphthalene
sulfonic acid
alkyl
light
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.)
Expired
Application number
EP80100807A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0014982A3 (en
EP0014982A2 (de
Inventor
Hans-Dieter Dr. Frommeld
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.)
Hoechst AG
Original Assignee
Hoechst AG
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
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6063930&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0014982(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT80100807T priority Critical patent/ATE1398T1/de
Publication of EP0014982A2 publication Critical patent/EP0014982A2/de
Publication of EP0014982A3 publication Critical patent/EP0014982A3/de
Application granted granted Critical
Publication of EP0014982B1 publication Critical patent/EP0014982B1/de
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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
    • G03C1/54—Diazonium salts or diazo anhydrides
    • 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 a two-component diazotype material, consisting of a support and a photosensitive layer, applied thereon, of at least one photosensitive diazonium salt and a coupler.
  • a two-component diazotype material consisting of a support and a photosensitive layer, applied thereon, of at least one photosensitive diazonium salt and a coupler.
  • Many compounds coupling to a blue dye have been described for use in two-component diazotype materials.
  • the main part relates to 2-hydroxynaphthalene derivatives, e.g. B. 2-hydroxynaphthalene-3-carboxamides, which are used in combination with p-aminobenzene diazonium salts for blue and, in combination with other couplers, for black settings.
  • 1-hydroxynaphthalene-3,8-sulfonamides are also known as blue couplers, for which either no technical information is given or those which are not specific Let suitability close. They are characterized as lightfast, slowly coupling with pale blue or, in combination with a special p-aminobenzene diazonium salt (blue salt), with a beautiful blue color and as strongly basic.
  • p-aminobenzene diazonium salts also have some serious disadvantages.
  • the dyes lose their contrast and, like pH indicator dyes, turn from wine red to light yellow tones.
  • the thermal stability is also limited, which leads to loss of contrast when storing unexposed material.
  • Blacks are achieved in the diazo type by mixing two or more couplers [Kosar, " Light-Sensitive Systems", Wiley & Sons, New York (1965), p. 303]. For this, it is usually necessary to use a blue coupler with little red tinge, the coupling speed of which is of a similar order of magnitude as that of the yellow and brown couplers added.
  • the invention thus relates to a two-component diazotype material, consisting of a support and a photosensitive layer applied thereon, which contains at least one benzene diazonium salt and at least one coupler as the photosensitive component, characterized by the combination of at least one 2,5-dialkoxy-4-mercapto - Benzene diazonium salt and at least one compound of the general formula wherein R 1 and R 2 are the same or different and are hydrogen, alkyl, alkenyl, aralkyl, aryl or cycloalkyl, which may be further substituted.
  • the benzene diazonium salt used is preferably a 2,5-dialkoxy-4-arylmercaptobenzene diazonium salt, in particular 2,5-diethoxy-4-p-tolylmer-captobenzene diazonium salt, which in the form of its tetrafluoborate, sulfate or chloride as double salt, e.g. with zinc chloride, is used.
  • R 1 and R 2 preferably denote alkyl or alkenyl, aryl, aralkyl or cycloalkyl each having up to 10 carbon atoms, which are alkyl or alkoxyl each having up to 4 carbon atoms, by carboxyl or by acyl each having up to 3 carbon atoms , can be substituted by phenoxy, by halogen, in particular chlorine or bromine, by hydroxyl or by optionally alkyl-substituted amine.
  • R 1 is an optionally substituted aryl and R 2 is an optionally substituted alkyl, alkenyl, aralkyl or cycloalkyl have proven particularly useful.
  • naphthosulfone-3-sulfochloride reacts quantitatively with excess aniline to give naphthosulfone-3-sulfonic acid anilide, and this in turn reacts quickly and quantitatively with methylamine at room temperature to 1-hydroxynaphthalene-3-sulfonic acid anilide-8-sulfonic acid methylamide.
  • the solubility in aqueous or organic solvents is strongly dependent on the type of radicals R 1 and R 2 .
  • the residues also have a certain influence on the coupling speed and the color.
  • the 1-hydroxynaphthalene-3,8-di (alkyl, aralkyl, alkenyl or cycloalkyl) sulfonamides couple somewhat faster and are reddish tinged than the 1-hydroxynaphthalene-3-arylsulfonamido-8-alkylsulfonamides.
  • the 1-hydroxynaphthalene-3,8-di (N-arylsulfonamides) are even more greenish. The latter are less resistant to light and tend to yellow slightly.
  • 1-Hydroxynaphthalene-3-arylsulfonamido-8-alkylsulfonamides such as 1-hydroxynaphthalene-3-p-tolylsulfonamido-8-n-butylsulfonamide are particularly suitable for black adjustments.
  • Amines which are suitable for the reaction are, in addition to ammonia, alkylamines, e.g. Methylamines, ethylamine, n- or isopropylamine, butylamine, 2-ethylhexylamine or decylamine, alkenylamines, e.g. Allylamine, aralkylamines, e.g. Benzylamine, phenethylamine, phenylbutylamine, cycloalkylamines, e.g.
  • alkylamines e.g. Methylamines, ethylamine, n- or isopropylamine, butylamine, 2-ethylhexylamine or decylamine
  • alkenylamines e.g. Allylamine
  • aralkylamines e.g. Benzylamine, phenethylamine, phenylbutylamine,
  • aniline derivatives which can be substituted by amine, alkyl, alkoxy or halogen, e.g. Toluidine, xylidine, difluoroaniline, tribromaniline, 4-morpholino-2,5-dimethoxyaniline or aminoacetophenone.
  • the aliphatic radicals can also be substituted without disadvantage.
  • Inexpensive technical amines are e.g.
  • Ethanolamine hydroxypropylamine, diethylaminoethylamine, morpholinopropylamine, pyrrolidinoethylamine, 4-amino (N-methylpyrrolidine), piperidinobutylamine, butoxypropylamine, phenoxyethylamine or aminopropionic acid.
  • the blueprint layer preferably in a lacquer layer of cellulose ester, e.g. Cellulose acetobutyrate is dispersed.
  • Simple phenol derivatives e.g. 2-hydroxydiphenyl, 2,2'-dihydroxydiphenyl, 2-hydroxyethoxyphenol, 2-hydroxybenzoic acid amide, 3,6-dimethylphenol as Mannich base or resorcyic acid with their derivatives, e.g. 2,4-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid amide, 2,4-dihydroxybenzoic acid ethanolamide or 2,4-dihydroxybenzoic acid ethyl ester.
  • each 100 ml of a solution are in the form of their double salts with zinc chloride solved.
  • the solutions are applied to polyester film with a wet weight of approx. 100 g / m 2 and dried.
  • the amount of diazo is dimensioned so that the contrast of the different patterns is approximately the same.
  • TD-205 with Wratten-106 filter
  • the density is aged in fresh (1) and 2.4 and 7 (ll, 111, IV) d in the forced storage test at 60 ° C (hot box) Material measured with ammonia after development following exposure under a template.
  • the values included in the following table show that the density drop for the p-mercaptobenzene diazonium salts is very much less than for the p-aminobenzene diazonium salts.
  • the compounds according to the invention produce neutral blue tones as desired. It is noteworthy that the replacement of a sulfonic acid amide by a sulfonic acid anilide grouping further reduces the red content in the dye.
  • Solutions a) to h) are used in the first case to coat immediately (A), in the second case after 6 h (B) and in the third case after 24 h (C) a polyester film coated with cellulose acetopropionate.
  • the fresh solutions a) to e) are considerably darker than the solutions f) to h) and accordingly the base of the break is darker from the start after the image-wise exposure and development of the materials a) to e).
  • the 1-hydroxynaphthalene-4.8 derivatives no longer give usable blueprints. The reason for the break is clearly dark.
  • the material a) is basically blue, the materials b) to e) blue-gray, and the materials f) to h) light to slightly gray.
  • Transparent paper coated with cellulose acetobutyrate is coated with a solution of the following composition and qretried:

Landscapes

  • 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)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Radiation-Therapy Devices (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Prostheses (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP80100807A 1979-02-26 1980-02-18 Zweikomponenten-Diazotypiematerial Expired EP0014982B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT80100807T ATE1398T1 (de) 1979-02-26 1980-02-18 Zweikomponenten-diazotypiematerial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792907446 DE2907446A1 (de) 1979-02-26 1979-02-26 Zweikomponenten-diazotypiematerial
DE2907446 1979-02-26

Publications (3)

Publication Number Publication Date
EP0014982A2 EP0014982A2 (de) 1980-09-03
EP0014982A3 EP0014982A3 (en) 1981-01-21
EP0014982B1 true EP0014982B1 (de) 1982-07-28

Family

ID=6063930

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80100807A Expired EP0014982B1 (de) 1979-02-26 1980-02-18 Zweikomponenten-Diazotypiematerial

Country Status (8)

Country Link
US (1) US4273850A (enrdf_load_stackoverflow)
EP (1) EP0014982B1 (enrdf_load_stackoverflow)
JP (1) JPS55129338A (enrdf_load_stackoverflow)
AT (1) ATE1398T1 (enrdf_load_stackoverflow)
DE (2) DE2907446A1 (enrdf_load_stackoverflow)
DK (1) DK79980A (enrdf_load_stackoverflow)
ES (1) ES488914A0 (enrdf_load_stackoverflow)
FI (1) FI68733C (enrdf_load_stackoverflow)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2903342A1 (de) * 1979-01-29 1980-07-31 Hoechst Ag Derivate des 2-hydroxy-naphthalins
DE3418469A1 (de) * 1984-05-18 1985-11-21 Hoechst Ag, 6230 Frankfurt Lichtempfindliches gemisch und hiermit hergestelltes zweikomponenten-diazotypiematerial

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL51536C (enrdf_load_stackoverflow) * 1939-06-08
US2537098A (en) * 1946-04-12 1951-01-09 Gen Aniline & Film Corp Sulfonamide azo coupling components used in diazo types
US2560137A (en) * 1948-12-21 1951-07-10 Gen Aniline & Film Corp Diazotype photoprinting material
DE1068555B (enrdf_load_stackoverflow) * 1957-02-04 1959-11-05
GB1052977A (enrdf_load_stackoverflow) * 1963-09-14
GB1052978A (enrdf_load_stackoverflow) * 1963-11-26
GB1217294A (en) * 1968-04-17 1970-12-31 Ricoh Kk Improvements in and relating to photosensitised materials
JPS4814255B1 (enrdf_load_stackoverflow) * 1968-06-01 1973-05-04
GB1278640A (en) * 1969-01-09 1972-06-21 Ricoh Kk Improvements in and relating to photosensitive materials
US3761263A (en) * 1971-11-03 1973-09-25 Eastman Kodak Co Diazotype compositions and photographic processes

Also Published As

Publication number Publication date
EP0014982A3 (en) 1981-01-21
JPS55129338A (en) 1980-10-07
EP0014982A2 (de) 1980-09-03
JPS6239727B2 (enrdf_load_stackoverflow) 1987-08-25
DE2907446A1 (de) 1980-09-04
DE3060684D1 (de) 1982-09-16
FI68733B (fi) 1985-06-28
DK79980A (da) 1980-08-27
ES8101784A1 (es) 1980-12-16
ES488914A0 (es) 1980-12-16
US4273850A (en) 1981-06-16
FI800532A7 (fi) 1980-08-27
FI68733C (fi) 1985-10-10
ATE1398T1 (de) 1982-08-15

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