EP0014982A2 - Matériel diazotypique à deux composants - Google Patents

Matériel diazotypique à deux composants Download PDF

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Publication number
EP0014982A2
EP0014982A2 EP80100807A EP80100807A EP0014982A2 EP 0014982 A2 EP0014982 A2 EP 0014982A2 EP 80100807 A EP80100807 A EP 80100807A EP 80100807 A EP80100807 A EP 80100807A EP 0014982 A2 EP0014982 A2 EP 0014982A2
Authority
EP
European Patent Office
Prior art keywords
hydroxy
diazonium salt
material according
naphthalene
sulfonic acid
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.)
Granted
Application number
EP80100807A
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German (de)
English (en)
Other versions
EP0014982B1 (fr
EP0014982A3 (en
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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Application filed by Hoechst AG filed Critical Hoechst AG
Priority to AT80100807T priority Critical patent/ATE1398T1/de
Publication of EP0014982A2 publication Critical patent/EP0014982A2/fr
Publication of EP0014982A3 publication Critical patent/EP0014982A3/de
Application granted granted Critical
Publication of EP0014982B1 publication Critical patent/EP0014982B1/fr
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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, comprising at least one photosensitive diazonium salt and a coupler.
  • a two-component diazotype material consisting of a support and a photosensitive layer applied thereon, comprising 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-hydroxy-naphthalene derivatives, e.g. B. 2-hydroxy-naphthalene-3-carboxamides, which are used in combination with p-aminobenzene diazonium salts for blue and, in combination with other couplers, for black settings.
  • 1-hydroxy-naphthalene-3,8-sulfonic acid amides are also known as blue couplers, for which, however, either no technical details are given or those that are not specific Let suitability conclude. They are characterized as lightfast, slowly coupling with pale blue or, in combination with a special p-amino-benzene diazonium salt (blue salt), with a beautiful blue color and as strongly basic.
  • p-aminobenzene diazonium salts also have some serious disadvantages.
  • the dyes With a pH shift, e.g. B. by acidic vapors, the dyes lose their contrast and turn, similar to pH indicator dyes, to burgundy to light yellow tones.
  • light-sensitive p-amino Benzene diazonium salts also limit thermal stability, 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 little reddish blue coupler, the coupling speed of which is similar to that of the yellow and brown couplers added.
  • DE-AS 20 00 819 describes 1-hydroxy-naphthalene-3-sulfonic acid-8-sulfonic acid amide derivatives as blue couplers, preferably in combination with p-aminobenzene diazonium salts. In combination with p-mercaptobenzene diazonium salts, these also form reddish, violet dyes which are neither useful for blue nor for black settings.
  • DE-AS 12 29 844 1-Bydroxy-naphthalin-8-sulfonamides, which may be further substituted, are known as alkali donors in diazotype materials.
  • 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-mercaptobenzene 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.
  • a 2,5-dialkoxy-4-arylmercaptobenzene diazonium salt in particular 2,5-diethoxy-4-p-tolylmercaptobenzene diazonium salt, is preferably used as the benzene diazonium salt.
  • R 1 and R 2 are preferably alkyl or alkenyl, aryl, aralkyl or cycloalkyl having up to 10 carbon atoms, which are substituted by alkyl or alkoxyl up to 4 carbon atoms, by carboxyl, by acyl having up to 3 carbon atoms, by pbenoxy, 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.
  • naphthosultone-3-sulfochloride reacts Room temperature with excess aniline quantitatively to naphthosultone-3-sulfonic acid anilide, and this in turn reacts quickly and quantitatively at room temperature with methylamine to 1-hydroxy-naphthalene-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 radicals also have a certain influence on the coupling rate and the color.
  • the 1-hydroxy-naphthalene-3,8-di (alkyl, aralkyl, alkenyl or cycloalkyl) sulfonamides couple somewhat faster and are more reddish than the 1-hydroxy-naphthalene-3-arylsulfonamido-8-alkylsulfonamides.
  • the 1-hydroxy-naphthalene-3,8-di (N-arylsulfonamides) are even more greenish. The latter are less resistant to light and tend to yellow slightly.
  • 1-Hydroxy-naphthalene-3-arylsulfonamido-8-alkylsulfonamides such as 1-hydroxy-naphthalene-3-p-tolylsulfonamido-8-h-butylsulfonamide are particularly suitable for black adjustments.
  • Amines which are suitable for the reaction are, in addition to ammonia, alkylamines, for. B. methylamine, ethylamine, n or iso propylamine, butylamine, 2-ethylhexylamine or decylamine, alkenylamines, e.g. B. allylamine, aralkylamines, e.g. B. benzylamine, phenethylamine, phenylbutylamine, cycloalkylamines, e.g. B.
  • cyclohexylamine, cyclooctylamine, 4-t-butylcyclohexylamine, and aniline derivatives which may be substituted by amine, alkyl, alkoxy or halogen, for.
  • aniline derivatives which may be substituted by amine, alkyl, alkoxy or halogen, for.
  • the aliphatic residues can also be without Disadvantage to be substituted.
  • inexpensive technical amines z. B.
  • 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, for. B. cellulose acetobutyrate is dispersed.
  • Simple phenol derivatives e.g. B. 2-hydroxydiphenyl, 2,2'-dihydroxydiphenyl, 2-hydroxyethoxyphenol, 2-hydroxybenzoic acid amide, 3,6-dimethylphenol as Mannich base or resorcylic acid with their derivatives, e.g. B. 2,4-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid amide, 2,4-dihydroxybenzoic acid ethanolamide or 2,4-dihydroxybenzoic acid ethyl ester into consideration.
  • each 100 ml of a solution are in the form of their double salts with zinc chloride solved.
  • the solutions are made on polyester film with a Wet weight of approx. 100 g / m 2 applied 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 after fresh (I) and after two, four and seven (II, III, IV) days in the forced storage test at 60 ° C (hot box) the development following the exposure under a template with ammonia measured.
  • the values included in the following table show that the density drop for the p-mercaptobenzene diazonium salts is very much lower 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 group with a sulfonic acid group reduces the amount of red in the dye even further.
  • Solutions a) to h) are coated in the first case immediately (A), in the second case after 6 hours (B) and in the third case after 24 hours (C) in each case a polyester film coated with cellulose acetopropionate.
  • a polyester film coated with cellulose acetopropionate already the fresh solutions a - e are considerably darker than the solutions f - h and accordingly the base of the break is darker from the beginning after imagewise exposure and development with the materials a - e.
  • Material a is basically blue, materials b - e blue-gray, and materials f - h light to light gray.
  • Transparent paper coated with cellulose acetobutyrate is coated with a solution of the following composition and dried:

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)
  • Prostheses (AREA)
  • Radiation-Therapy Devices (AREA)
  • Liquid Developers In Electrophotography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP80100807A 1979-02-26 1980-02-18 Matériel diazotypique à deux composants Expired EP0014982B1 (fr)

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 true EP0014982A2 (fr) 1980-09-03
EP0014982A3 EP0014982A3 (en) 1981-01-21
EP0014982B1 EP0014982B1 (fr) 1982-07-28

Family

ID=6063930

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80100807A Expired EP0014982B1 (fr) 1979-02-26 1980-02-18 Matériel diazotypique à deux composants

Country Status (8)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0161655A3 (en) * 1984-05-18 1987-05-27 Hoechst Aktiengesellschaft Light-sensitive composition and two-component diazotype material prepared therefrom

Families Citing this family (1)

* 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

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL51536C (fr) * 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 (fr) * 1957-02-04 1959-11-05
GB1052977A (fr) * 1963-09-14
GB1052978A (fr) * 1963-11-26
GB1217294A (en) * 1968-04-17 1970-12-31 Ricoh Kk Improvements in and relating to photosensitised materials
JPS4814255B1 (fr) * 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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0161655A3 (en) * 1984-05-18 1987-05-27 Hoechst Aktiengesellschaft Light-sensitive composition and two-component diazotype material prepared therefrom

Also Published As

Publication number Publication date
DE3060684D1 (de) 1982-09-16
ES8101784A1 (es) 1980-12-16
FI800532A7 (fi) 1980-08-27
EP0014982B1 (fr) 1982-07-28
JPS55129338A (en) 1980-10-07
ES488914A0 (es) 1980-12-16
JPS6239727B2 (fr) 1987-08-25
EP0014982A3 (en) 1981-01-21
FI68733B (fi) 1985-06-28
FI68733C (fi) 1985-10-10
US4273850A (en) 1981-06-16
DE2907446A1 (de) 1980-09-04
DK79980A (da) 1980-08-27
ATE1398T1 (de) 1982-08-15

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