US2793118A - One component diazotype material containing at least two light sensitive diazocompounds - Google Patents

One component diazotype material containing at least two light sensitive diazocompounds Download PDF

Info

Publication number
US2793118A
US2793118A US371022A US37102253A US2793118A US 2793118 A US2793118 A US 2793118A US 371022 A US371022 A US 371022A US 37102253 A US37102253 A US 37102253A US 2793118 A US2793118 A US 2793118A
Authority
US
United States
Prior art keywords
diazo
type
compound
rays
diazotype
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
US371022A
Other languages
English (en)
Inventor
Sanders Theodorus Pe Wilhelmus
Hutgens Karel Maria
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.)
Chemische Fabriek L Van der Grinten NV
Original Assignee
Grinten Chem L V D
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
Application filed by Grinten Chem L V D filed Critical Grinten Chem L V D
Application granted granted Critical
Publication of US2793118A publication Critical patent/US2793118A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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

Definitions

  • the diazotype material according to the invention is particularly valuable for copying from what are often called artistic tracings, for example of furniture or architectural subjects, drawn in lead-pencil and crayon.
  • artistic tracings for example of furniture or architectural subjects
  • diazotype material yielding pictures giving a good rendering of the lead-pencil and crayon lines of the said artistic tracings.
  • the materials may also be usefully applied to copying from continuous tone diapositives if the light sensitive layer is a diazo film layer.
  • the diiferent types of diazo compounds will hereinafter be described.
  • the semi-wet diazotype process has become of considerable importance for the development of one component diazotype material.
  • diazo compounds of the following structure are preferred:
  • R1 and R2 each represent an alkyl radical
  • X is an anion
  • Y a substituent.
  • Diazo compounds of this kind are preferred for various technical reasons, for example because the amino compounds from which they are prepared are stable and because these diazo com pounds have sufiicient coupling activity for development with buttered developing solutions of a slightly alkaline reaction. Any substituent Y in the position indicated makes this type of diazo compound, as far as the coupling activity is concerned, suitable for semi-wet development as previously defined, even substituents such as SOsH and COOH are suitable, though, in general, the latter have a tendency to decrease rather than to increase the coupling activity. (Of course, the azodyestuffs formed should not be too soluble as they would then have a tendency to bleed.)
  • Diazotypc materials containing these diazo compounds do not however yield good renderings of the said artistic tracings, the gradation produced being too steep if the diazo content is higher than 0.3 millimol per square metre, and if-as is normalthe decomposition product formed Patented May 21, 1957 from the diazo compound upon exposure does not yield an internal screen, which internal screen would prolong exposure.
  • the diazo content of normal diazotype materials is usually higher than 0.3 millimol per square meter, in order to obtain copies of sufiicient density of line.
  • Sunlight may be used for the purpose of diazotype printing, but nowadays a mercury vapour lamp (usually a high pressure mercury vapour lamp) is most frequently used.
  • the diazotype material according to the invention will produce better rendition of the said artistic tracings when the exposure is made in sunlight or when made in the light of a mercury vapour lamp. If not otherwise stated the use of a high pressure mercury vapour lamp will, in the following description, be supposed. When exposed in monochromatic light, the required effect is not produced. Likewise when the material is exposed to carbon arc-light, which formerly was frequently used, and still is used, for diazotype printing, there will be no appreciable effect.
  • One component diazotype material contains at least two different types (type i and ll) of light sensitive diazo compounds and has a total content of at least 0.3 millimol diazo compound per m9.
  • the novelty of this material consists in the following: it contains at least one diazo compound of type 1 of the following structure:
  • R1 and R2 each represent an alkyl radical
  • X is an anion
  • Y a substituent, which has, for rays of 4050 A., an epsilon value greater than 1.5)(10 and, for rays of 3650 A., an epsilon value lower than that for rays of 4050 A.; it contains at least one diazo compound of type II having, for rays of 3650 A., an epsilon value greater than 1.5 10 and, for rays of 4050 A., an epsilon value lower than for rays of 3650 A.; for rays of 4050 A.
  • the epsilon value of the diazo compound(s) of type 1 minus the epsilon value of the diazo compound(s) of type II is at least LOXIO; for rays of 3650 A.
  • the epsilon value of the diazo compound(s) of type II minus the epsilon value of the diazo compound(s) of type I is at least l.0 l0 the gamma value of the diazotype material containing the mixture of the diazo compounds of types I and II is less than that of material with the diazo compound(s) of type I or type ll, (whichever of these types has the lower gamma value), and the diazo compounds couple more rapidly than p-diazodiethylaniline.
  • total content of diazo compounds is to be understood the content of all the diazo compounds present in the diazotype material, i. e. the one or more diazo compounds of type I plus the one or more diazo compounds of type II, plus possibly other diazo compounds present in the diazo layer.
  • epsilon indicates the molar extinction coeificient, as measured in a layer of one centimetre thickness of an aqueous molar solution of the diazo compound.
  • the diazotype material according to the invention will yield a picture of softer gradation than a diazotype material with the same total" diazo content but made with only the softest working of these diazo compounds.
  • This is schematically illustrated by the graph of the drawing.
  • the ordinate of the graph indicates gamma values as derived from Example 1.
  • the points 1, 2, 3, 4 and 5 in the graph have been calculated from the series of gamma value determinations, carried out on stepwedge prints on five diazotype materials coated with the same diazo compounds of both the types I and II, but in varying ratios.
  • Point 1 indicates the gamma value, when only the diazo compound of type I has been used, point 5 the gamma value of the corresponding diazotype material, exclusively coated with the diazo compound of type II.
  • the points 2, 3 and 4 indicate the gamma values obtained with diazotype materials containing both the diazo compounds in three difierent ratios.
  • each ratio has a corresponding gamma value.
  • the desired gamma value for example the lowest of the gamma values for these mixtures, can be obtained.
  • the lowest gamma value is to be found very near to point 3. This lowest gamma value is not, however, always the most desirable. Which of the possible gamma values will give the most attractive results may depend on the nature of the tracing or diapositive to be reproduced.
  • the gamma value of the diazotype material containing the mixture of the diazo compounds of types I and II should be less than the gamma values of comparable diazotype materials respectively containing only one of the diazo compounds of said mixture, of either type I or II. So the mixture 4 does not enter into the scope of this invention, as its gamma value is the same as that of a material containing diazo compound l.
  • the rapidity of coupling in comparison with that of p-diazodiethylaniline can be determined in vitro by measuring the time in which a certain portion (e. g. of the diazo compound to be measured will have coupled in a given molar concentration (e. g.
  • phenylmethylpyrazolone in a given molar concentration (e. g. 1.0 millimolar) in a butter mixture of a given composition and having a given pH value, at a given temperature.
  • a two-component diazotype material containing two diazo compounds viz.: l-diazo-4-dimethylamino-2-carboxybenzene and l-diazo4-m0noethylamino-3-methylbenzene, and one or more azo-coupling components, which after exposure under the tracing and development in gaseous ammonia, gives a good rendering of lead-pencil and crayon lines, is known.
  • This diazotype material does not contain a mixture of diazo compounds used according to the invention and it is not suitable for the semi-wet development diazotype process, because the diazo compounds have insufficient coupling activity for this process.
  • R represents a cyclohexyl radical
  • X represents an anion
  • R is a cyclohexyl radical.
  • diazo compounds of type I are: 1-diazo-4-diethylamino-3-methylbenzene, l-diazo-4- N-methyl N-cyclohexyl amino-3-chlorobenzene, l-diazo- 4-diethylamino-3-chlorobenzene; some of type II are: ldiazo-4-cthylbenzylaminobenzene, l-diazo-4-monoethylamino-3-trifiuoromethylbcnzene, 1 diazo- 4 -monocyclohexyl-amino-3-chlorobenzene, l-diazo-4-mono(4'methylcyclohexyl) amino-B-chlorobenzene.
  • the invention is not limited to diazotype material, containing only one diazo compound of type I' plus one diazo compound of type II. As will appear from the examples, more than one of either of the two types may be used. Likewise it may be advantageous, for example for obtaining a special hue in the copies, to add to the diazo mixture one or more diazo compounds not belonging to either of the types I or II in small quantities which will not essentially interfere with the etfect which should be obtained according to the invention.
  • diazo compounds examples include: l-diazo-ZzS-diethoxy- 4 benzoylaminobenzene, l-diazo-Z:S-dibenzyloxyi-benzoylaminobenzene, l-diazo-2z5-dibutoxy-4 acetylaminobenzene, 1-diazo-2 5-diethoxy-4-ethylmercaptobenzene, ldiazo 2:5-diethoxy-4-(4-ethoxyphenyl)benzene, l-diazo- Z-diethylaminobenzene, l-diazo-4-phenylaminobenzene, 1- diazo-4- (4'-ethoxy-phenylamino -benzene.
  • the diazotype material according to the invention may as also illustrated in the examples, contain additional chemicals, such as are in general use in diazotype materials.
  • the diazo compoimds used should, of course, bleach out upon exposure, so as to yield a colourless or nearly colourless background.
  • the sensitizing preparations may be applied to the base or support in any of various ways well known to those skilled in the art, for example, by dipping, spraying, coating, or brushing. They may be applied in excess, the excess being subsequently removed, for example, by a doctor blade or roller or an air jet.
  • Example 1 In this example two diazo compounds, the one of type I and the other of type II, are used.
  • diazo compound type I has an epsilon value of approximately l.5 and diazo compound type II one of approximately 3.5 1O
  • diazo compound type I has an epsilon value of approximately 3.1)(10 and diazo compound type II one of approximately 0.2 10 Both the diazo compounds yield a clear background upon exposure to light.
  • a second sheet of the same strawpulp paper was prepared with a solution containing:
  • This paper surface also contained 0.90 millimol of the diazo compound per :11. (diazotype paper No. 5).
  • Sheets of the same strawpulp paper were prepared with mixtures of the two above solutions so that three further diazotype papers (Nos. 2, 3 and 4) were obtained, respectively having at their surfaces:
  • the five diazotype papers were exposed under a neutral stepwedge, after which they were developed by the ap plication of approximately 9 g. per 111. of the following developing solution:
  • Example 2 A sheet of paper of g. per mi, suitable for the diazotype process, was coated with a solution, which contained:
  • the paper surface contained: approximately 0.5 millimol diazo compound of type I and approximately 0.2 millimol diazo compound of type II per m).
  • the sheet was exposed (with slight under-exposure) under a tracing, drawn in lead-pencil and crayon on natural tracing paper, and developed by the application of a film of approximately 9 g. per m? of the following developing liquid:
  • Example 3 A sheet of woodpulp paper of 80 g. per in suitable for the diazotype process, was coated with a solution, which contained:
  • the application was made so that the treated paper surface contained: approximately 0.48 millimol diazo com pound of type I and approximately 0.17 millimol diazo compound of type II, all per mfi.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per in. of the following developing liquid:
  • 1-diazo-4-diethylamino-3-iodobenzenc was prepared by condensing 1:3-dinitro-4-chlorobenzene with diethylamine followed by partial reduction by means of sodium disulphide, recrystallisation of the 1-nitro-3-amino-4-diethylaminobenzene obtained thereby, diazotization of the amino compound and replacement of the diazo group by the iodo substituent according to the Sandmeyer-reaction, reduction of the 1-nitro-3-iodo-4-diethylaminobenzene and diazotization of the amino compound.
  • l-diazo-4- monoethylamin-3-chlorobenzene was obtained by the method used for making the diazo compounds of Example using monoethy
  • Example 4 A sheet of paper of 80 g. per m. suitable for the diazotype process, was coated with a solution, which contained:
  • the application was made so that the treated paper surface contained: approximately 0.5 millimol diazo compound of type I and approximately 0.2 millimol diazo compound of type II per [11.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m of the following developing liquid:
  • Example 5 A sheet of g. per mfl, suitable for the diazotype process, was coated with a solution, which contained:
  • the application was made by applying about 8.5 cc. of the solution per square meter of the sheet material, so as to produce a paper surface containing: approximately 0.43 millimol diazo compound of type I and approximately 0.17 millimol diazo compound of type II per m3.
  • the sheet was exposed with slight under-exposure in the light of a normal pressure mercury vapour lamp (Cooper Hewitt-lamp) under a tracing, drawn in leadpencil and crayon on natural tracing paper, and developed by the application of a film of approximately 9 g. per mi of the developing liquid described in Example 2.
  • a normal pressure mercury vapour lamp (Cooper Hewitt-lamp) under a tracing, drawn in leadpencil and crayon on natural tracing paper, and developed by the application of a film of approximately 9 g. per mi of the developing liquid described in Example 2.
  • Example 6 On a film of g. per in. of cclluloseacctatc with 50% combined acetic acid content there was cast, at a temperature of 30 C., 100 cc. per m? of the following colloidal solution:
  • the layer thus formed was dried in an air current at 50 C.
  • the application was made so that the sensitized layer contained: approximately 0.87 millimol diazo compound of type I and approximately 0.43 millimol diazo compound of type II per mi.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per 1n.'- of the developing liquid described in Example 3.
  • a dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype film containing, in a concentration equal to the total diazo content of the example, only the softer working of the diazo compounds.
  • the transparent copy may be used as a diapositive for projection purposes.
  • Example 7 A sheet of paper of 80 g. per m.'-', suitable for the diazotype process, was coated with a solution, which contained:
  • the application was made so that the treated paper surface contained: approximately 0.24 millimol of each diazo compound of type I and approximately 0.22 millimol diazo compound of type II per m.
  • Example 3 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m? of the developing liquid, described in Example 3.
  • a dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, the diazo compounds of type I only or one of these only or the diazo compound of type II only.
  • the three diazo compounds were manufactured in the same manner as those of Example I using respec tively di-normal-butylamine, N-methyl N-cyclohexyl amine and monobenzylamine.
  • Example 8 A sheet of paper of 80 g. per m? suitable for the diazotype process, was coated with a solution, which contained:
  • the treated paper surface contained: approximately 0.47 millimol diazo compound of type I plus approximately 0.11 millimol of each diazo compound of type 11, per m.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per in. of the following developing liquid:
  • a dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, the diazo compound of type I only or the diazo compounds of type II only or one of these only.
  • 1 diazo 4 monocyclohexylamino 3 trifluoromethylbenzene was obtained by condensing l-nitro-Ibtri fiuoromethyl-4-chl0robenzene with monocyclohexylamine, followed by reduction and diazotization.
  • Example 9 A sheet of paper of 80 g. per m suitable for the diazotype process, was coated with a solution, which contained:
  • the application was made so that the treated paper surface contained: approximately 0.42 millimol diazo compound of type 1, approximately 0.14 millimol diazo compound of type II and 0.1 millimol l-diazo-4-monophenylamino-benzene chloride per m3.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m. of the developing liquid as described in Example 3.
  • a dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, only the diazo compound of type I together with 1-diazo-4-monophenylarnino-benzene chloride or only the diazo compound of type II together with l-diazo4-monophenylamino-benzene chloride.
  • l-diazo- 4-monophenylamino-benzene is commercially available under the name of para-diazo-diphenylamine.
  • Example 10 Baryta-coated paper was provided on its baryta-coated side with a layer of 10 g. per in? of cellulose acetate with 50% combined acetic acid content. On the cellulose acetate side there was cast, at a temperature of 30 C., cc. per m? of the following colloidal solution:
  • the layer thus formed was dried in an air current at 50 C. Over the cellulose acetate layer of 50% combined acetic acid content there was thus formed a layer, approximately 3 microns thick, of cellulose acetate with 28% combined acetic acid content. This latter layer was sensitized by impregnating with the solution of Example 6 and drying.
  • the sensitized surface contained: approximately 0.87 millimol diazo comwas; i s
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g, per m? of the developing liquid described in Example 3.
  • a dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, only the softer working of the diazo compounds.
  • Example 11 A sheet of paper of 150 g. per m? was, by means of an adhesive, provided on both sides with a layer, approximately 10 microns thick, of cellulose acetate with 50% combined acetic acid content.
  • the sheet was superficially hydrolysed on both sides in the following way:
  • the application was made so that the sensitized surface contained: approximately 0.22 millimol diazo compound of type I and approximately 0.17 millimol diazo compound of type II per m.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m of the developing liquid described in Example 3. A red brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, only the softer working of the diazo compounds.
  • l-diazo-4-diisobutylamino-3-sulpho-benzene was prepared by condensing 1-nitro-3-sulpho-4-chlorobenzene with diisobutylamine, followed by reduction and diazotization.
  • Example 12 A sheet of paper of 80 g. per m. suitable for the diazotype process, was coated with a solution, which contained:
  • the treated paper surface contained: approximately 0.38 millimol diazo compound of type I and approximately 0.15 millimol diazo compound of type II per m.
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m? of the developing liquid described in Example 1. A dark, nearly black copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, only the softer working of the diazo compounds.
  • 1-diazo-4-ethylbenzylaminobenzene was prepared by nitrosation of N-ethyl-N-benzylaniline, reduction and diazotizanon.
  • Example 13 A sheet of paper of g. per m3, suitable for the diazotypo process, was coated with a solution, which contained:
  • the application was made so that the treated paper surface contained: approximately 0.40 millimol diazo compound of type I and approximately 0.16 millimol diazo compound of type II per m.”
  • Example 2 The sheet was exposed as in Example 2 and developed by the application of a film of approximately 9 g. per m of the developing liquid described in Example 1. A violet brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the exa1n ple, only the softer working of the diazo compounds.
  • 1-diazo-4-diethylamino-2-chlorobenzene was prepared by nitrosation of N-diethyl-m-chloroaniline, reduction and diazotization.
  • Example 14 A sheet of paper of g. per m1, provided on both sides with a layer of cellulose acetate having 50% c0mbined acetic acid content, was superficially hydrolysed on both sides in the same way as described in Example I I, dried, washed and sensitized on one side only with a solution containing:
  • the application was made so that the sensitized surface contained: 0.46 millimol diazo compound of type l and 0.19 millimol diazo compound of type II, per 111.
  • the sheet was exposed under a photographic diapositive and developed by the application of a film of approximately 9 g. per m. of the developing liquid of Example 4.
  • a violet copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing', in a concentration equal to the total diazo content of 1 the example, only the softer working of the diazo compounds.
  • Example 15 A sheet of paper of 80 g. per m3, suitable for the diazotype process, was coated with a solution, which contained:
  • the treated paper surface contained: approximately 0.5 millimol diazo compound of type I and approximately 0.2 millimol diazo compound of type II per mi.
  • Example 2 The sheet was exposed as in Example 2 and developed as in Example 3. A dark brown copy was obtained having softer gradation than would have been obtained, under otherwise comparable circumstances, with a diazotype paper containing, in a concentration equal to the total diazo content of the example, only the more soft-working of the two diazo compounds.
  • 1-diazo-4-ethylethanolamino-3-chlorobenzene was prepared in the same manner as the diazo compounds of Example 1, using N-ethyl-N- ethanolamine.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive diazo compound, hereinafter referred to as the type I compound, of the formula wherein R1 and R2 each represent an alkyl radical, X is an anion and Y a substituent replacing hydrogen, and at least one other light sensitive para amino benzene diazo compound, hereinafter referred to as the type II compound, said type I compound having for rays of 4050 A. an epsilon value greater than l.5 and for rays of 3650 A.
  • an epsilon value lower than for rays of 4050 A. said type II compound having for rays of 3650 A. an epsilon value greater than x10 and for rays of 4050 A. an epsilon value lower than for rays of 3650 A., the epsilon value of said type I compound for rays of 4050 A. exceeding that of said type 11 compound for rays of 4050 A. by at least 1.0)(10, the epsilon value of said type II compound for rays of 3650 A. exceeding that of said type I compound for rays of 3650 A.
  • the relative quantities of said type I compound and said type II compound being such that the gamma value of said diazotype material containing said mixture of diazo compounds is less than the gamma values of comparable diazotype materials respectively containing only said type I compound and only said type II compound as the lightsensitive constituent, said diazo compounds coupling more rapidly than para-diazo-diethylaniline and being incapable of forming an azo dyestufl with their own light decomposition products, the azo dyestuffs formed in the image parts of said material upon the development of such parts with a liquid containing at least one azo coupling 14 component, after an image-wise exposure of said material under polychromatic actinic light, being all of substantially the same color and being incapable of forming an azo dyestuff with their own light decomposition products.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive diazo compound, hereinafter referred to as the type I compound, of the formula wherein R1 and R: each represent an alkyl radical, X is an anion and Y a substituent replacing hydrogen, and at least one other light sensitive diazo compound, hereinafter referred to as the type II compound, of the formula IIIIX HN R wherein R is an alkyl radical, X an anion and Y a substituent replacing hydrogen, said type I compound having for rays of 4050 A.
  • the diazo compounds coupling more rapidly than para-diazodiethylaniline.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive diazo compound, hereinafter referred to as the type I compound, of the formula wherein R1 and R2 each represent an alkyl radical, X is an anion and Y a substituent replacing hydrogen, and at least one other light sensitive diazo compound hereinafter referred to as the type II compound, of the formula NsX wherein R is a cyclohexyl radical and X is an anion, said type I compound having for rays of 4050 A.
  • the gamma value of said diazotype material containing said mixture of diazo compounds being less than the gamma values of comparable diazotype materials respectively containing only said type I compound and only said type II compound as the lightsensitive constituent, said diazo compounds coupling more rapidly than para-diazo-diethylaniline.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive diazo compound, hereinafter referred to as the type I compound, of the formula (C: l): wherein X is an anion, and at least one other light sensitive diazo compound, hereinafter referred to as the type II compound, of the formula wherein R is a cyclohexyl radical and X is an anion, said type I compound having for rays of 4050 A. an epsilon value greater than 1.5)( and for rays of 3650 A.
  • an epsilon value lower than for rays of 4050 A. said type II compound having for rays 3650 A. an epsilon value greater than 1.5 l0* and for rays of 4050 A. an epsilon value lower than for rays of 3650 A., the epsilon value of said type I compound for rays of 4050 A. exceeding that of said type 11 compound for rays of 4050 A. by at least l.0 10 the epsilon value of said type II compound for rays of 3650 A. exceeding that of said type I compound for rays of 3650 A.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive l-diazo, 3-chloro, 4-diethyl amino benzene, hereinafter referred to as the type I compound, and at least l-diazo, 3-chloro, 4-cyclohexyl-amino benzene, hereinafter referred to as the type II compound, said type I compound having for rays of 4050 A. an epsilon value greater than 1.5)(10 and for rays of 3650 A.
  • an epsilon value lower than for rays of 4050 A. said type II compound having for rays of 3650 A. an epsilon value greater than 1.5)(10 and for rays of 4050 A. an epsilon value lower than for rays of 3650 A., the epsilon value of said type I compound for rays of 4050 A. exceeding that of said type II compound for rays of 4050 A. by at least 1.0 l0 the epsilon value of said type II compound for rays of 3650 A. exceeding that of said type I compound for rays of 3650 A.
  • a one component positive diazotype material suitable for development by the semi-wet development process comprising a sensitized sheet material containing per square meter at least 0.3 millimol of a mixture of light sensitive diazo compounds including at least one light sensitive l-diazo, 3-chloro, 4-diethyl amino benzene, hereinafter referred to as the type I compound, and at least one I-diazo, 3-chloro, 4-(methylcyclohexyl) amino benzene, hereinafter referred to as the type II compound, said type I compound having for rays of 4050 A. an epsilon value greater than 1.5)(10 and for rays of 3650 A.
  • an epsilon value lower than for rays of 4050 A. said type II compound having for rays of 3650 A. an epsilon value greater than 1.5 X 10 and for rays of 4050 A. an epsilon value lower than for rays of 3650 A., the epsilon value of said type I compound for rays of 4050 A. exceeding that of said type II compound for rays of 4050 A. by at least 1.0x 10 the epsilon value of said type II compound for rays of 3650 A. exceeding that of said type I compound for rays of 3650 A.
  • the gamma value of said diazotype material containing said mixture of diazo compounds being less than the gamma values of comparable diazotypc materials respectively containing only said type I compound and only said type II compound as the light-sensitive constituent, said diazo compounds coupling more rapidly than para-diazo-diethylaniline.

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)
US371022A 1952-08-13 1953-07-29 One component diazotype material containing at least two light sensitive diazocompounds Expired - Lifetime US2793118A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL171784 1952-08-13

Publications (1)

Publication Number Publication Date
US2793118A true US2793118A (en) 1957-05-21

Family

ID=19750576

Family Applications (1)

Application Number Title Priority Date Filing Date
US371022A Expired - Lifetime US2793118A (en) 1952-08-13 1953-07-29 One component diazotype material containing at least two light sensitive diazocompounds

Country Status (7)

Country Link
US (1) US2793118A (fr)
BE (1) BE521426A (fr)
CH (1) CH327756A (fr)
DE (1) DE1015679B (fr)
FR (1) FR1090494A (fr)
GB (1) GB726755A (fr)
NL (2) NL80603C (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2994610A (en) * 1956-09-26 1961-08-01 Agfa Ag Color radiography
US3121232A (en) * 1954-12-15 1964-02-11 United States Radium Corp Color radiographic film
US3238044A (en) * 1962-03-14 1966-03-01 Grinten Chem L V D One-component diazotype material
US3331690A (en) * 1964-06-08 1967-07-18 Ibm Development of diazotype papers without a coupler
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
US3382070A (en) * 1964-01-02 1968-05-07 Gen Aniline & Film Corp Black-line moist diazotype process
US3385705A (en) * 1963-10-09 1968-05-28 Philips Corp Photo-sensitive material having a shallow layer containing a benzenediazo sulfonic acid compound or salts thereof
US3484241A (en) * 1967-01-16 1969-12-16 Ibm Diazo type films with extended linear latitude
US3539347A (en) * 1967-03-08 1970-11-10 Keuffel & Esser Co Diazinium compounds and diazotype material therefrom
US3622326A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
US3849138A (en) * 1961-03-24 1974-11-19 Applied Photo Sciences Color photography
JPS5280118A (en) * 1975-12-26 1977-07-05 Mitsubishi Paper Mills Ltd Diazo photosensitive material for intermediates
JPS5297725A (en) * 1976-02-13 1977-08-16 Mitsubishi Paper Mills Ltd Diazo photosensitive material for intermediates
US4148646A (en) * 1977-06-13 1979-04-10 Trans World Technology Laboratories, Inc. Continuous tone diazotype process
US4224397A (en) * 1979-01-26 1980-09-23 Trans World Technology Laboratories Inc. (Twt Labs, Inc.) Continuous tone diazo material

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4581996A (en) * 1982-03-15 1986-04-15 American Hoechst Corporation Aluminum support useful for lithography
DE3307364A1 (de) * 1983-03-02 1984-09-06 Hoechst Ag, 6230 Frankfurt Zweikomponenten-diazontypiematerial

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1967371A (en) * 1931-03-28 1934-07-24 Kalle & Co Ag Process of preparing copies
US2532126A (en) * 1946-12-16 1950-11-28 Gen Aniline & Film Corp Diazotype photographic material
GB677772A (en) * 1946-07-23 1952-08-20 Philips Nv Improvements in or relating to the production of photographic images
US2659672A (en) * 1948-01-09 1953-11-17 Hall Harding Ltd Diazotype photoprinting materials

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1967371A (en) * 1931-03-28 1934-07-24 Kalle & Co Ag Process of preparing copies
GB677772A (en) * 1946-07-23 1952-08-20 Philips Nv Improvements in or relating to the production of photographic images
US2532126A (en) * 1946-12-16 1950-11-28 Gen Aniline & Film Corp Diazotype photographic material
US2659672A (en) * 1948-01-09 1953-11-17 Hall Harding Ltd Diazotype photoprinting materials

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121232A (en) * 1954-12-15 1964-02-11 United States Radium Corp Color radiographic film
US2994610A (en) * 1956-09-26 1961-08-01 Agfa Ag Color radiography
US3849138A (en) * 1961-03-24 1974-11-19 Applied Photo Sciences Color photography
US3238044A (en) * 1962-03-14 1966-03-01 Grinten Chem L V D One-component diazotype material
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
US3385705A (en) * 1963-10-09 1968-05-28 Philips Corp Photo-sensitive material having a shallow layer containing a benzenediazo sulfonic acid compound or salts thereof
US3382070A (en) * 1964-01-02 1968-05-07 Gen Aniline & Film Corp Black-line moist diazotype process
US3331690A (en) * 1964-06-08 1967-07-18 Ibm Development of diazotype papers without a coupler
US3484241A (en) * 1967-01-16 1969-12-16 Ibm Diazo type films with extended linear latitude
US3539347A (en) * 1967-03-08 1970-11-10 Keuffel & Esser Co Diazinium compounds and diazotype material therefrom
US3622326A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
JPS5280118A (en) * 1975-12-26 1977-07-05 Mitsubishi Paper Mills Ltd Diazo photosensitive material for intermediates
JPS573929B2 (fr) * 1975-12-26 1982-01-23
JPS5297725A (en) * 1976-02-13 1977-08-16 Mitsubishi Paper Mills Ltd Diazo photosensitive material for intermediates
JPS578459B2 (fr) * 1976-02-13 1982-02-16
US4148646A (en) * 1977-06-13 1979-04-10 Trans World Technology Laboratories, Inc. Continuous tone diazotype process
US4224397A (en) * 1979-01-26 1980-09-23 Trans World Technology Laboratories Inc. (Twt Labs, Inc.) Continuous tone diazo material

Also Published As

Publication number Publication date
DE1015679B (de) 1957-09-12
NL80603C (fr)
NL171784B (nl)
CH327756A (de) 1958-02-15
GB726755A (en) 1955-03-23
FR1090494A (fr) 1955-03-30
BE521426A (fr)

Similar Documents

Publication Publication Date Title
US2793118A (en) One component diazotype material containing at least two light sensitive diazocompounds
US3113025A (en) Diazotype materials for the production of black images
US3338713A (en) Diazotype material
US2792303A (en) Process for the production of diazotype copies
US2552354A (en) Diazotype layers containing diazos of n-(2-hydroxypropyl)-phenylenediamines
US1934011A (en) Light-sensitive layer
US3397058A (en) Diazotype material
US3169869A (en) Diazotype material
US2500099A (en) Diazo sulfonate light-sensitive element containing a diketone azo component
US3622326A (en) Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
US2532126A (en) Diazotype photographic material
US2542716A (en) Multicolor diazotype layers
US2494906A (en) Cyan component for diazotype color process
US2536398A (en) Pyrazolone diazotype couplers
US2672418A (en) Light-sensitive diazotype material
US2661291A (en) Antidiffusion diazotypes having tetrazo diphenyls as the light sensitive agent
US2516931A (en) Diazotype layers containing resorcinol mono-ethers
US3397985A (en) Light sensitive diazotype material and diazonium compounds therefor
US3081166A (en) Process for making positive diazotype copies by exposure to light of a mercury vaporlamp and light-sensitive material suited for this process
US3628954A (en) Diazo material and visible light development process therefore
US3416924A (en) Heat-developable diazotype material
US3367776A (en) Heat sensitive diazotype materials
US2632703A (en) Light sensitive diazotype materials containing tetrazo diphenyl compounds
US2542560A (en) Diazotypes on plastic surfaced carrier containing 5,5' diresorcinol
US2542566A (en) 2, 2', 4, 4'-tetrahydroxybiphenyl coupling component for diazotype layers