US2536989A - Diazotype layers containing resorcinol derivatives - Google Patents

Diazotype layers containing resorcinol derivatives Download PDF

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Publication number
US2536989A
US2536989A US3326A US332648A US2536989A US 2536989 A US2536989 A US 2536989A US 3326 A US3326 A US 3326A US 332648 A US332648 A US 332648A US 2536989 A US2536989 A US 2536989A
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US
United States
Prior art keywords
resorcinol
diazotype
transition
light
copies
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 - Lifetime
Application number
US3326A
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English (en)
Inventor
Glahn William H Von
Lester N Stanley
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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
Priority to NL72166D priority Critical patent/NL72166C/xx
Priority to NL646405009A priority patent/NL144426B/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US3326A priority patent/US2536989A/en
Priority to GB522/49A priority patent/GB656364A/en
Priority to DEP31451A priority patent/DE864657C/de
Priority to CH283457D priority patent/CH283457A/fr
Application granted granted Critical
Publication of US2536989A publication Critical patent/US2536989A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C1/58—Coupling substances therefor

Definitions

  • the efliciency of the process involving the production of a transition or intermediate print depends upon the opacity of the azo dye image produced upon such intermediate or such transition print to ultraviolet light and upon the transparency of the background portions thereof. It depends also upon the visual densi y of the image produced on the intermediate or transition print, since images of poor visual density, such as yellow on a white or transparent background, while having the desired degree of opacity to ultraviolet light, nevertheless, have the disadvantage of rendering difficult the detection of flaws in the intermediate image, and it is often necessary to make a contrasting print from the transition print before such flaws can be detected.
  • Prints of a deep color having a good visual density can be obtained from diazotypes including such azo components as phloroglucinol, but despite the density of the color constituting the image, its actinic opacity or photographic densityis insufiicient to reproduce the image satisfactorily in diazotype copies made therefrom.
  • the azo coupling component used for the production of such images on prints which are to be used as intermediate or transition copies must be such as to produce, upon coupling with the diazc compound employed, a yellow to brown azo dye which will sufiiciently absorb ultraviolet light to prevent decomposition by light of the diazo compound in the areas to be reproduced from the intermediate 9; transition copies,
  • Coupling components such as resorcinol have been employed heretofore in diazotype transition.
  • colorations produced with res-l orcinol are in many cases not fast to light, and tend to fade over a period of time, particularly when exposed to prolonged or repeated actinic radiation used in making final copies from the transition prints. Furthermore, colorations thus produced often tend to offset; for example, they rub off when the transition copy is passed over hot rollers in the printing machine.
  • a new class of azo coupling components can be employed in a light sensitive layer together with a suitable light sensitive diazo compound, or as a developer for a one-component diazotype layer, to form an image in a sepia color of high actinic opacity and good visual density, while at the same time avoiding the difiiculties mentioned above which are encountered by similar use of resorcinol.
  • the class of compounds employed as azo coupling components in accordance with this invention are carbonic ester derivatives of resorcinol which can be prepared by reacting resorcinol with phosgene in the presence of a suitable HCl acceptor or reaction medium, such as pyridine, dimethyl aniline, quinoline or other tertiary nitrogen bases.
  • a suitable HCl acceptor or reaction medium such as pyridine, dimethyl aniline, quinoline or other tertiary nitrogen bases.
  • n. isan integer of the series of 0,,1,,2, 3 Allof the. compositions or mixtures formed by the aforesaid. reaction can be used as coupling. components. in. diazotype compositions and processes in accordance with this invention.
  • the. product obtained possesses a high degree of stability against premature coupling, under the usual conditions of temperature. and humidity to which it is subjected during prolonged storage, as well as under accelerated; aging. tests which simulate the effect of. prolonged storage.
  • transition. prints having a colorl'ess background of. excellent actinic transparency l rom two-component diazotype materials which include the resorcinol: derivatives of this invention as coupling components, even after prolonged storage such as may be required for commercial. distribution of the material.
  • the image produced with materials of this invention has equal or better covering power and: opacity toultraviolet light, superior f'ast'nes's to; light and; washing, better visual density, and reatly Improved: resistance: to: ofisetting; as cont-r pared with transition prints produced with resorcinol.
  • the transition prints produced in accordance with the invention are therefore highly advantageous for the production of large numbers oflcopies.
  • a transparent. base such asstransparentized paper, a film of transparent plastic material such as regenerated cellulose or an organic derivative of cellulose- (cellulose ethers and esters such as ethyl cellulose. or cellulose acetate) can be used.
  • the base is: coated or impregnated with a sensitizing composition in any manner known to the art, particularly by applying thereto a solution containing the light sensitive diazo compound together with the other ingredients ordinarily used in diazotype sensitizing compositions such as metal salts, stabilizers, anti-oxidants, humectants and the like.
  • the solvent medium employed is preferably compounded to penetrate or impregmate the base material and ordinarily contains asubst'antial proportion of water to insure solution of the sensitizing components therein.
  • a carbonic ester derivative of resorcinol' of the type described above is incorporated in the sensitizing composition, or can be applied separately (e. g., by apply-- ing it in a separate solution or by rubbing it in powdered form on the surface of the carrier);
  • diazo components we prefer to use those which are derived from p-diamines of the benzene series, particularly those in which at least one of the hydrogens of one of the amino groups is substituted by such groups as alkyl, alkoxyalkyl, aryl, aralkyl, alkylol', cycloaliphatic and' heterocyclic groups.
  • diazo components have also been found suitable,. such as diazoanhydrides of amino naphthols. These. diazo compounds can be used in: the. form of.
  • amines from which suitable light sensitive dia'zo cone pounds are derived include p-amino-N'--(-2'-hy'- droxyethyl)QT-methyl-amino-benzene, p-aminm diphenylamine, monoethylamino-2'-(or -&'-) methyl 4 arninobenzene, 1 N"- ethyl- N:'-- (2:"-.
  • the lightsensitive layers can be sensitized byany of the various methods employed in": diazotype processes.
  • the carbonicv ester'de rivatives of resorcinol' described above can be ap:-.-- plied to the transparent or'semi-transparent base: or carrier in a coating solution, together with a; stabilized diazo compoundi or the aforesaid" coupling components can be robbed on the surface to'be sensitized in powdered form. before or. after application of the. diazo compound.
  • the sensitive layer is formed by applying the.
  • Example 2 Transparentized paper was coated with a solution made up with water to a volume of 100 cc., containing the following ingredients:
  • sorcinol instead :oftheeaforesaid carbonic; est r: derivativeeoi :resorcinoh .Eiuperior---resultswere obtained similar to;those oirExample' 1;
  • Exampled Transparentized paper wascoated with a solu-" tion; made up to a'volume of 100' ccrwith water; containing the following ingredients:
  • an aqueous alkaline solution such as a solution of an alkali metal carbonate or tertiary phosphate (e. g., a 5-20% aqueous sodium carbonate solution) can be applied in a wet or semi-wet development step to the sensitized materials after they have been exposed to light under an original to be reproduced.
  • the prints prepared in this manner have clear sharply defined images accurately reproducing the original; whereas, when resorcinol is used instead of the carbonic ester derivatives of the invention, the images tend to become blurred 7 by reason of the comparatively water-sensitive nature of the coloration produced.
  • One-component diazotype transition print material can be made in the same manner as disclosed in the examples, except that the carbonic ester derivatives of resorcinol are omitted in preparing the sensitizing compositions, and are included instead in an aqueous alkaline developing solution which is applied to the prints after exposure to light in accordance with a predetermined original design or pattern.
  • Such solutions contain for example alkaline reacting salts such as alkali metal carbonates or tertiary phosphates, and the carbonic ester derivative of resorcinol, the latter being employ-ed, for example, in a concentration of l to 10%.
  • the alkaline salts e.
  • g., sodium carbonate can be used, for example, in a concentration of to 2G%.
  • sharp images are thus obtained, which are superior in this respect to prints similarly obtained by use of resorcinol as the developer.
  • the prints obtained in wet development of oneor two-component layers in accordance with the invention have the same advantages as described in the examples.
  • films e. g., of regenerated cellulose or of organic derivatives of cellulose, such as cellulose acetate or ethyl cellulose, can be used as the carrier and sensitized with compositions similar to those in the examples.
  • Ordinary paper or other opac ue carriers can be used where transparency is not desired in the copies produced.
  • the step which comprises reacting the residual light sensitive diazo compound contained in a light sensitive diazotype layer after exposure thereof to light in a pre-determined pattern, with a carbonic ester which is a reaction product of 1 mol of phosgene with 1 to 2 mols of resorcinol in the presence of an alkaline reagent.
  • the improvement which comprises developing the image thereby formed by reaction of the residual diazo compound with a carbonic ester which is a reaction product of 1 mol of phosgene with 1- to 2 mols of resorcinol in the presence of an alkaline reagent.
  • a light sensitive diazotype layer on a suitable base containing a light sensitive diazo compound and a carbonic ester which is a reaction product of 1 mol of phosgene with 1 to 2 mols of resorcinol.
  • Diazotype photoprinting material for transition copies comprising a transparent carrier having thereon a light sensitive layer comprising a light sensitive diazo compound and a carbonic ester which is a reaction product of 1 mol of phosgene with l to 2 mols of resorcinol.
  • Diazotype photoprinting material comprising a carrier having thereon a light sensitive layer containing a diazotized p-diamine of the benzene series and a carbonic ester which is a reaction product of 1 mol of phosgene with l to 2 mols o1 resorcinol.
  • Diazotype photoprinting material for transition copies comprising a transparent carrier having thereon a light sensitive layer containing a diazo compound of l-mono-ethylamfno-2-methyle-aminobenzene, and a carbonic ester which is a reaction product of 1 mol of phosgene with l to 2 mols of resorcinol.
  • Diazotype photoprinting material for transition copies comprising a transparent carrier having thereon a light sensitive layer containing a diazo compound of l-N,N-diethylamino--aminobenzene and a carbonic ester which is a reaction roduct of 1 mol oi phosgene with 1 to 2 mols of resorcinol.
  • Diazotype photoprinting material for transition copies comprising a transparent carrier having thereon a light sensitive layer containing a diazo compound of N 2 hydroxyethyl) N methylamino-p-aminobenzene and a carbonic ester which is a reaction product of 1 mol of phosgene with l to 2 mols of resorcinol.

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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)
  • Paper (AREA)
US3326A 1948-01-20 1948-01-20 Diazotype layers containing resorcinol derivatives Expired - Lifetime US2536989A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL72166D NL72166C (en(2012)) 1948-01-20
NL646405009A NL144426B (nl) 1948-01-20 Elektrische schakelinrichting, omvattende een in willekeurige richtingen dwars op zijn lengteas verzwenkbare, staafvormige bedieningshefboom.
US3326A US2536989A (en) 1948-01-20 1948-01-20 Diazotype layers containing resorcinol derivatives
GB522/49A GB656364A (en) 1948-01-20 1949-01-07 Diazotype photo-printing layers containing resorcinol derivatives
DEP31451A DE864657C (de) 1948-01-20 1949-01-12 Material fuer die Herstellung von Diazotypien
CH283457D CH283457A (fr) 1948-01-20 1949-01-19 Procédé de préparation de copies diazotypes.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3326A US2536989A (en) 1948-01-20 1948-01-20 Diazotype layers containing resorcinol derivatives

Publications (1)

Publication Number Publication Date
US2536989A true US2536989A (en) 1951-01-02

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US3326A Expired - Lifetime US2536989A (en) 1948-01-20 1948-01-20 Diazotype layers containing resorcinol derivatives

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US (1) US2536989A (en(2012))
CH (1) CH283457A (en(2012))
DE (1) DE864657C (en(2012))
GB (1) GB656364A (en(2012))
NL (2) NL144426B (en(2012))

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2940852A (en) * 1957-02-19 1960-06-14 Gen Aniline & Film Corp m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity
US3022171A (en) * 1956-07-26 1962-02-20 Agfa Ag Photographic filter and antihalation layers
US3028365A (en) * 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3148172A (en) * 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US3153008A (en) * 1955-07-05 1964-10-13 Gen Electric Aromatic carbonate resins and preparation thereof
US3157622A (en) * 1961-01-03 1964-11-17 Gen Electric Resinous compositions
US3269986A (en) * 1956-10-04 1966-08-30 Gen Electric Linear resinous polycarbonates of dihydroxy polysulfones
US3769018A (en) * 1970-05-13 1973-10-30 Oce Van Der Grinten Nv Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA6706181B (en(2012)) * 1966-10-18

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR836144A (fr) * 1935-03-21 1939-01-11 Kodak Pathe Perfectionnements aux procédés de photographie en couleurs et en particulier aux révélateurs chromogènes
US2246425A (en) * 1938-06-18 1941-06-17 Kalle & Co Ag Production of diazotype reflex copies
US2334495A (en) * 1939-07-22 1943-11-16 Ilford Ltd Color photography
US2437868A (en) * 1946-06-22 1948-03-16 Gen Aniline & Film Corp Diazotype layers containing resorcinol monoesters

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR836144A (fr) * 1935-03-21 1939-01-11 Kodak Pathe Perfectionnements aux procédés de photographie en couleurs et en particulier aux révélateurs chromogènes
US2246425A (en) * 1938-06-18 1941-06-17 Kalle & Co Ag Production of diazotype reflex copies
US2334495A (en) * 1939-07-22 1943-11-16 Ilford Ltd Color photography
US2437868A (en) * 1946-06-22 1948-03-16 Gen Aniline & Film Corp Diazotype layers containing resorcinol monoesters

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028365A (en) * 1953-10-16 1962-04-03 Bayer Ag Thermoplastic aromatic polycarbonates and their manufacture
US3153008A (en) * 1955-07-05 1964-10-13 Gen Electric Aromatic carbonate resins and preparation thereof
US3148172A (en) * 1956-07-19 1964-09-08 Gen Electric Polycarbonates of dihydroxyaryl ethers
US3022171A (en) * 1956-07-26 1962-02-20 Agfa Ag Photographic filter and antihalation layers
US3269986A (en) * 1956-10-04 1966-08-30 Gen Electric Linear resinous polycarbonates of dihydroxy polysulfones
US2940852A (en) * 1957-02-19 1960-06-14 Gen Aniline & Film Corp m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity
US3157622A (en) * 1961-01-03 1964-11-17 Gen Electric Resinous compositions
US3769018A (en) * 1970-05-13 1973-10-30 Oce Van Der Grinten Nv Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers

Also Published As

Publication number Publication date
DE864657C (de) 1953-01-26
CH283457A (fr) 1952-06-15
NL144426B (nl)
NL72166C (en(2012))
GB656364A (en) 1951-08-22

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