US2659672A - Diazotype photoprinting materials - Google Patents

Diazotype photoprinting materials Download PDF

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Publication number
US2659672A
US2659672A US66579A US6657948A US2659672A US 2659672 A US2659672 A US 2659672A US 66579 A US66579 A US 66579A US 6657948 A US6657948 A US 6657948A US 2659672 A US2659672 A US 2659672A
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United States
Prior art keywords
diazo
light
coupling
component
coupling component
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Expired - Lifetime
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US66579A
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English (en)
Inventor
Leuch Werner Paul
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Hall Harding Ltd
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Hall Harding Ltd
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    • 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

Definitions

  • the present invention relates the production of light-sensitive layers by means of diazo compounds capable of producing prints in two "or more contrasting colours and in particular in "primarycolours red, yellow or blue, or in comv plementary colours such as red and green or orange and blue or yellow and violet from one D floriginal depending on the composition of the f light-sensitive layer.
  • drawings produced by this process may be drawings exe-
  • the drawings can be of a kind where one ink transmits no light at all and the other a definite proportion only of the total quantity of light transmitted during a given exposure time. makes it possible to obtain two complementary This colours or two desired primary colours out of a possible of three, or three colours simultaneproduce photographic prints in two or more contrasting colours from monochromatic photographic transparencies of different degrees of density.
  • the principle on which the present invention operates is that two or more diazo compounds are used at least one of which (B) is incapable of forming a, dyestufi with the coupling components (C) present in the light sensitive layer (in the case of layers developed by the ammonia 5 gas method) or in the developer (in-the case of moist or semi-dry development), but is capable of coupling with its own decomposition product I (D) produced during exposure to light, and that at least one other diazo compound (A) is used which is capable of coupling with the coupling as such a manner that suflicient difference in printing out speeds results between at least two of the diazo compounds used.
  • This quantity may, according to they wave length sensitivity of the respective diazo compounds, have to be varied to suit the spectral composition of ,the light used for exposure.
  • diazo compounds (B) which are not capable under the usual conditions of development of forming a dye'stufi with the coupling component already present in the unexposed light-sensitive layer or applied subsequently with the developer
  • members of the class of diazo anhydrides or diazo oxides, particularly those of the naphthalene series have been found to be specially advantageous. These generally are compounds which bleach out in a neutral or acid medium, and are incapable of forming dyestuffs with coupling components of medium coupling velocity such for example as 2.3-hydroxynaphthalene-G-sulphonic acid, or the amide of 2.4-resorcylic acid.
  • the other diazo compounds (A) which are ca-' pable of coupling with the coupling component (C) may be any of the diazo compounds generally used in the production of diazotype prints aetacv'a quently, and dye results on development. with such an arrangement it is therefore possible that in those portions of a drawing which transmit no light at all, only diazo component A can form a dyestufi; in this case blue with coupling component C, while diazo B, not having been affected by light, remains incapable of forming a'dye.
  • the coupling components to be used according to this invention are chosen to give the desired colours with the diazo compounds used and in general are compounds of moderate coupling energy so that they do not couple with diazo compound denoted as (B) under the conditions used. Coupling components of high coupling energy such as phloroglucinol are therefore generally not suitable.
  • a large variety of coupling components are, however, suitable, examples of such being the 6-mono-sulphonic acids of 2.3- and 3.8-dihydroxyn-aphthalenes, the amide of 2.4- resorcylic acid, resorcinolpropyl ether, m-hydroxyphenyl urea and the monoglycol ether of pyrocatechol.
  • diazo component A is capable of forming a blue dyestufi with coupling component C under given conditions.
  • Diazo component B however is incapable of forming a dyestuff with coupling component C under the same conditions.
  • diazo component B forms, during exposure to light, a coupling component D with which it is capable of forming a red dyestufi in those portions of the copy where not all the diazo component has been destroyed by the light. Where this decomposititon of B with consequent formation of coupling component D is about 50% of the total of B in the layer the red dye is most intense.
  • the two diazo compounds A and B either must possess diiferent sensitiveness to the light of a given light source or must be mixed in such proportions in the sensitizing solution, that one diazo component prints out faster than the other.
  • the proportions have to be arranged so that for instance there is still a considerable amount of diazo component B left in some of those portions where A has already been completely destroyed by the action of light.
  • conselayer of the described type can best be studied by exposing it under a grey wedge photometer used for sensitometry. with a definite wedge constant.
  • ponent E which possesses approximately the this can for instance be achieved by adding yet another coupling com-' same coupling energy as coupling component C and which produces a yellow dye with diazo component A and, of course, no colour with diazo component B.
  • the image is composed chiefly of green and'red dyes.
  • a suitable light-sensitive layer of the type described contains also stabilisers which ensure good keeping qualities of the material before printing and ingredients which counteract the yellowing of the copy after it has been made.
  • the anti-yellowing agents can be incorporated in the developer, but the light-sensitive layer and developer must be compounded in such a manner 'that'no excess alkali is left on the paper after completed development, if good stability of the prints is desired.
  • EXAMPLE 1 (Solution 1 ,for blue) In 150 cc. water dissolve 12 gr. tartaric acid 10 gr. thiourea 5.1 gr. zinc chloride double salt of l-N-ethyl-hydroxy-ethylamino benzene-i-diazonium chloride (Diazo compound A) 4.5 gr. 2.3 dihydroxynaphthalene 6 sulphonic acid (Coupling component C) 1o gr. zinc chloride 3 cc. diethylene glycol or glycerine (Solution 2 for red) 150 cc. water 12 gr. tartaric acid 10 gr. thiourea 6 gr. zinc chloride 3 cc. diethylene glycol 3.6 gr.
  • Diazo compound A 4.5 gr. 2.3 dihydroxynaphthalene 6 sulphonic acid
  • Coupling component C 1o gr. zinc chloride 3 cc. diethylene glycol or glycerine
  • EXAMPLE 2 In this example the diazo compound designated as diazo compound A in Example 1 is replaced by a mixture of 3 grams of the zinc chloride double salt of 3-chloro l diethyl amino benzene-4- oliazonium choride and 4 grams of the zinc chloride double salt oi t-diethylamino-l-toluene-3- diazonium chloride.
  • the light tones are reproduced in red, the medium tones chiefly in yellow and the darker tones in stance, in an original ink drawing, alterations.
  • the present. process enables the dark lines of the original, drawing to be reproduced in alight colour and. the lighter lines of the drawing to be reproduced.
  • EXAMPIE 3 A solution is prepared from 100 cc. of water in which are dissolved 6 gr. tartaric acid gr. thiourea 5 gr. zinc chloride 2 cc. polyglycol 3 gr. sodium salt of the diazoanhydride 01' 1- amino-2-naphthol-3.6 disulphonic acid 8 gr. zinc chloride double salt of 4-diethylaminol-diazonium chloride 1 gr. monoglycolether o1 pyrocatechol This solution when coated on paper and exposed and developed in the manner described in Example 1 gives a print in which the pencil lines of the drawing are shown in violet-blue, whereas the darker ink lines 01' the drawing are shown in bright yellow.
  • the diazo anhydride used in this example is replaced by the diazo anhydride used in Example 1 then the pencil lines of the original drawing are reproduced in brilliant red and the ink lines of the gas method) or in the developer (in the case of moist or semi-dry development) but is capable of coupling with its own decomposition product;
  • a light-sensitive layer for the production of a multi-colored' diazotype photographic print which contains a coupling component, C, and two diazo compounds at least one, B, of which is a .member of the group consisting of diazo anhydrides and diazo oxides which diazo compound is incapable of forming a dyestufi with said coupling component C but iscapable of coupling with the decomposition product, D, produced from B by the action of light and another one, A. of which is capable of coupling with said coupling component C, the relative quantities of the said diazo compounds A and B being such that there is a substantial diflerence in their printing out speeds.
  • a light-sensitive layer according to claim 1 in which the diazo compounds present in the light-sensitive layer are the zinc chloride double salt of 1-N-ethyl-hydroxy-ethylamino-benzene- 4-diazonium chloride and the sodium salt of the diazo anhydride 0: 1-amino-2-naphtho1-4-sulphonic acid and in which the coupling component is 2,8-dihydroxynaphthalene-6-sulphonic acid.
  • a light-sensitive layer for the production of a multi-colored diazotype photographic print which contains a coupling component, C, and at least two diazo compounds one, B, of which is a member of the group consisting of diazo anhydrides and diazo oxides which diazo compound is incapable of forming a dyestufl with said coupling component C but is capable of coupling with the decomposition product, D, producedtrom B by the action 01' light.
  • the light-sensitive layer being further characterized in that the diazo compounds present therein are the zinc chloride double salt of 1- N ethyl hydroxy ethylamino benzene 4- diazonium chloride and the sodium salt or the diazo anhydride or 2-amino-1-naphthol-5-sulphonic acid and in that the coupling component is 2.3-dihydroxynaphthalene-s-sulphonic acid.
  • a process for the production of a multicolored diazotype print by coating at least two light-sensitive diazo compounds on a support and exposing the coated material behind a transparent design to the action of actinic light and then developing the print by coupling the diazo compounds with coupling components characterized in that the light-sensitive layer contains a coupling component, C, in that one, B, or the diazo compounds is a member of the group consisting of diazoanhydrides and diazo oxides which diazo compound is incapable of forming a dyestuif with coupling component C but is capable of coupling with the decomposition product, D, produced from said diazo compound 3 by the action of light thereon, in that a second one, A, of the diazo compounds is capable of coupling with said coupling component C, the relative quantities of A and B being such that, under the conditions of exposure to the light source employed, there is a substantial diiference in their printing out speeds, and in that after exposure to light the print is developed by treatment with an alkaline substance.

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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)
US66579A 1948-01-09 1948-12-21 Diazotype photoprinting materials Expired - Lifetime US2659672A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB277685X 1948-01-09
GB221248X 1948-12-22

Publications (1)

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US2659672A true US2659672A (en) 1953-11-17

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Country Status (5)

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US (1) US2659672A (de)
CH (1) CH277685A (de)
DE (1) DE825203C (de)
FR (1) FR978378A (de)
GB (1) GB644493A (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741558A (en) * 1952-03-11 1956-04-10 Grinten Chem L V D Process for the manufacture of diazotype copies
US2793118A (en) * 1952-08-13 1957-05-21 Grinten Chem L V D One component diazotype material containing at least two light sensitive diazocompounds
US3052542A (en) * 1958-07-24 1962-09-04 Gen Aniline & Film Corp Intermediate master for use in the diazotype process and a process for producing same
US3309200A (en) * 1963-06-03 1967-03-14 Itek Corp Data reproduction process
US3353984A (en) * 1963-04-18 1967-11-21 Landau Raphael Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method
US3515554A (en) * 1966-07-25 1970-06-02 Philips Corp Diazo type paper and new high speed diazo reproduction process
US4292394A (en) * 1978-11-13 1981-09-29 E. I. Du Pont De Nemours And Company Process for preparing multicolor toned images on a single photosensitive layer
FR2558274A1 (fr) * 1984-01-17 1985-07-19 Chemistry Technology Sa Procede de production d'images positives sur un support a partir d'un cliche transparent positif utilisant une surface sensible diazoique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE565736A (de) * 1957-03-16

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1444469A (en) * 1917-05-31 1923-02-06 Firm Of Kalle & Co Ag Manufacture of light copy paper
US1760780A (en) * 1927-09-06 1930-05-27 Kalle & Co Ag Light-sensitive layers and process of preparing them
US1934011A (en) * 1931-01-16 1933-11-07 Kalle & Co Ag Light-sensitive layer
US1936957A (en) * 1927-09-19 1933-11-28 Kalle & Co Ag Light-sensitive layer
US2037542A (en) * 1933-02-18 1936-04-14 Kalle & Co Ag Light sensitive materials containing light sensitive diazo compounds
US2298444A (en) * 1940-10-15 1942-10-13 Eastman Kodak Co Light sensitive diazotype material
US2350843A (en) * 1943-08-05 1944-06-06 Eastman Kodak Co Diazotype photographic material

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1444469A (en) * 1917-05-31 1923-02-06 Firm Of Kalle & Co Ag Manufacture of light copy paper
US1760780A (en) * 1927-09-06 1930-05-27 Kalle & Co Ag Light-sensitive layers and process of preparing them
US1936957A (en) * 1927-09-19 1933-11-28 Kalle & Co Ag Light-sensitive layer
US1934011A (en) * 1931-01-16 1933-11-07 Kalle & Co Ag Light-sensitive layer
US2037542A (en) * 1933-02-18 1936-04-14 Kalle & Co Ag Light sensitive materials containing light sensitive diazo compounds
US2298444A (en) * 1940-10-15 1942-10-13 Eastman Kodak Co Light sensitive diazotype material
US2350843A (en) * 1943-08-05 1944-06-06 Eastman Kodak Co Diazotype photographic material

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741558A (en) * 1952-03-11 1956-04-10 Grinten Chem L V D Process for the manufacture of diazotype copies
US2793118A (en) * 1952-08-13 1957-05-21 Grinten Chem L V D One component diazotype material containing at least two light sensitive diazocompounds
US3052542A (en) * 1958-07-24 1962-09-04 Gen Aniline & Film Corp Intermediate master for use in the diazotype process and a process for producing same
US3353984A (en) * 1963-04-18 1967-11-21 Landau Raphael Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method
US3309200A (en) * 1963-06-03 1967-03-14 Itek Corp Data reproduction process
US3515554A (en) * 1966-07-25 1970-06-02 Philips Corp Diazo type paper and new high speed diazo reproduction process
US4292394A (en) * 1978-11-13 1981-09-29 E. I. Du Pont De Nemours And Company Process for preparing multicolor toned images on a single photosensitive layer
FR2558274A1 (fr) * 1984-01-17 1985-07-19 Chemistry Technology Sa Procede de production d'images positives sur un support a partir d'un cliche transparent positif utilisant une surface sensible diazoique

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Publication number Publication date
FR978378A (fr) 1951-04-12
GB644493A (en) 1950-10-11
CH277685A (de) 1951-09-15
DE825203C (de) 1951-12-17

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