US1821281A - Manufacture of diazo-types - Google Patents
Manufacture of diazo-types Download PDFInfo
- Publication number
- US1821281A US1821281A US196993A US19699327A US1821281A US 1821281 A US1821281 A US 1821281A US 196993 A US196993 A US 196993A US 19699327 A US19699327 A US 19699327A US 1821281 A US1821281 A US 1821281A
- Authority
- US
- United States
- Prior art keywords
- diazo
- reducing agent
- compound
- discoloration
- azo
- 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
Links
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
- G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives
Definitions
- This invention relates to the production of diazo-types in which layers containing dlazocompounds which are stable in the dark but are decomposed by light, are exposed to light through a transparent original and are then developed.
- the sensitive layer is spread on suitable carriers such as paper or the like.
- suitable carriers such as paper or the like.
- the papers or the. like thus obtained are suitable for lmaking reproductions of transparent images such as drawings, photographs and the like.
- the image obtained is positive when a ;transparent positive has been used.
- the development causes also the fixation of the image because a further action of light will notalter it.
- the first technical process for dlitaining gjpositive copies was that of Green, Cross & Bevan (German Patent 56,606 of September 3rd, 1890) who used the diazo derivativeof the dyestufi prim-uline as a sensitive substance and after exposure to light through a transparent-original developed in' a bath containing an azo-dyestufi component and generally an alkali. 1
- Diazotypecopies obtained from a sensitive layer containing diazonium compounds havingin para position to the diazo group a tertiary bound nitrogen atom will have the same disadvantage as other diazotypes of becoming yellow or brownish during storage.
- the invention is based on the observation that the discoloration of the background in all kinds of diazotype processes can be prevented even for extended periods if a reducing agent is added to the sensitive layer, or during or after development of the picture.
- Preferred reducing. agents are organic substances such as aldehydes, amino compounds, aliphatic amido-compounds, poly-oXy-com- 1 pounds or the like,.-and the reducing agents are preferably used together with very small quantities of the substances with catalytic action defined as anti-oxygenes by Moureu (Chemisch Monlblatt 1922 I 1317; Comptes Rendus 174 pages 258-26 i and following). I
- the reducing agents are added to the sensitivelayers together with the other constituents the additional advantage is obtained that the small discolouring effect due to the oxidation of the components of the layer which may occur during long storage of it in 4 the unexposed state is also prevented.
- reducing agents makes it possible to maintain the required white background and thereby improve the use of the abovenientioned diazonium-compounds containing in para-position to the diazo-group a tertiary nitrogen atom as a substituent, but it does not make it possible to use always.
- a developing process with alkali alone, except with freshly-made sensitive layers because this development requires a sensitive layer containing all ingredients necessary to forman azo-dyes-tuti' and the resistance to coupling of such layers is not improved sufficiently by the aforesaid reducing agent.
- dia-zocompounds which show no great resistance to coupling in practical admixture with 2120- dyestutf componentsand acids which are not injuriousto paper.
- diam-compounds One can advantageously use such diazo-compounds as, like the aforesaid d'iuzonium salts, contain a tertiary nitrogen atom as-a substituent in the para-position to the diazo-group and form with suitable azo-dyestufi' components. the desired dark tone on a completely white ground.
- a non-coupling compound which however in the development of the photoprint with an alkali is converted into a coupling com ponent.
- Such compounds may be obtained for instance by the action on a coupling component of an agent which inhibits the phenolfunction.
- hydrorylamine may. be cited.
- the agent may be added to the mixture of diazo-compound and azo-couplingv component with which the sensitive layer isproduced but it may also be caused to react previously with the azo-dyestufi component so as to form a derivatlve of this-component having no tend- .ency tocouple, which. d'erivative, however,
- ammonia vapour may be prepared intentionally moist.
- hydroxylamine which may be added, for example, in the form of hydroxylamine-hydrochloride, the latter forms compounds not only with the phloro-glucinol but also with azo-coupling components in general (phenols), to form compounds (probably 'oximes derived from the ketoform ofthe phenol in question) which do not have a tendency to couple, although by combined action of a diazo compound and an alkali they pass into compounds which do have this tendency.
- the print maybe developed with a pulverized alkaline substance strewn on the image. Care should be taken that sufficient moisture is present because in dry condition the development proceeds too slowly.
- a suitable alkaline substance for this purpose is sodium stannate.
- diazonium salts having impala-position to the diazogroup a tertiary nitrogen atom as a substitucnt and in which the benzene nucleus containing the diazo group has still one onmore other substituents.
- salts like barium chloride. If the development is carried out in a bath, for example abath containing an axe-coupling component, the salt may lie-added to the bath. In most cases however it is preferable to bring it together with the other components in the sensitive layer.
- the solution is brushed on paper and dried.
- the solution is painted on paper and dried.
- the paper is only permanent for a relatively,
- Example 5 A solution is made of:
- Example 6 The procedure is' as described in Example 3. The picture obtained, however, is not developed by ammonia vapour but by friction with pulverulent sodium stannate. In this case also there is produced a black picture on a white ground that does not yel low.
- Example 7 The procedure isa's described in Example 3, but a larger proportion of hydroxylamine hydrochloride is added and instead of 2 parts of oxalic acid there are 'used 3 parts of sodium acetate. The drying operation is performed particularly carefully at a low temperature. After exposure, the pic? ture is developed by heating it, for example with a'hot smoothing iron.
- the process of rendering the background of the diazo type prints substantially stable against discoloration which comprises including therein a substance comprising a reducing agent, and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration-of the components forming the back-ground of said prints. 4
- the process of rendering the background of the diazo type prints substantially stable against. discoloration which comprises including therein a reducing aliphatic compoundcapable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- e A 4 The process of rendering the back ground of the diazo type prints substantially stable against discoloration which comprises including therein areducingamino compound capable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- the process of rendering the background of the diazo type prints substantially stable against discoloration which comprises including therein an aldehyde capable of arresting under normal conditions the discoloration of the components forming the background of said prints.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light and a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of said print, exposing such layer, and contacting the exposed layer with a developer containing an azo dyestufi' component.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light, an azo dyestuflt' component and a, reducing agent capable of arrest ing under normal conditions the discoloration of the components forming the background of said prints, exposing such layer, and developing the exposed layer.
- the reducing agent is an amino comtermed antioxygene of Moureu which substance is capable of arrestingunder normal conditions the discoloration of the components forming the back-ground of said prints, exposing such layer, and developing the exposed layer.
- the process for making diazo type prints which comprises applyingjzo' a base a layer containing a diazo compound bleaching on exposure to light, a non-coupling compound decomposable into an azo dyestufi coinponentanda reducing agent capable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints, exposing such layer, and developing the exposed layer.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light, a non-coupling compound decomposable into an azo dyestufi' component, and asubstance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of said print, exposing such layer, and developing the exposed layer.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching-on exposure to light and a reducing agent capable of arresting under normal conditions the discoloration of the components forming the back-ground of said print, exposing such said prints.
- the process for making diazo type prints which comprisesapplying to a base a layer containing a dia'zo compound bleaching onexposure to light and a substance comprising a reducing agent and a catalyticallyactive material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the background of said prints, exposing such layer, and contacting the exposed layer with a developer containing an azo dyestutf component, and a substance comprising a reducing agent and a catalytically active material *termed antioxygene of Moureu which substance is capable of arresting under normal -conditions the discoloration of the components forming the back-ground of 'said prints.
- the process for making diazo type prints which. comprises applying'to a base a layer containing a diazo compound bleaching-on-exposure to light, an azo dyestuif component, and a reducing agent capable of arresting under normal conditions the discolorationof the components forming the background of said prints, exposing such layer, and contacting the exposed layer with a developer'containing a reducing agent capable of arresting under normal conditions the discloration of the components forming the back-ground ofsaid prints.
- the components forming the back-ground of veloper containing a reducing agent capable wherein the. reducing agent in both instances a compound decomposableinto an the components forming the back-ground of 20. .
- the process according to claim 19 wherein the reducing agent in both instances is an amino compound capable of arresting under normal conditions the discoloration of.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light, an azo dyestuiicomponent and a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the compo nents forming the back-ground of said prints, exposing such layer, and contacting the exposed layer with a developer containing a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the background of said prints;
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light,.a non-coupling compound decomposable into an azo dyestuit component and a reducing agent capable of arresting under normal conditions the discoloration of the components of the background of said prints, exposing such layer, and contactingthe exposed layer with a de- 10" of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- the process according to claim 22 is an amino compound capable of arresting under normal conditions the disgtoloration of the components of the back-ground of said prints.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching on exposure to light, a non-coupling azo dyestufi component'and a substancecomprising a reducing agent and a talytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of said prints, andcontacting the-exposed layer to a developer containing a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the background of said prints.
- the proce for makingdiazo type prints which comp ises applying to a base 130 a layer containing a diazo compound bleach-- ing on exposure to light, exposing such layer, and contacting the exposed layer with a de-. veloper containing an azo dyestufi' component and a reducing agent capable of arresting-under normal conditions the discoloration of the components forming the back ground ofsaid prints.
- the process according to claim wherein the reducing agent is an amino compound capable of arresting under normal conditions the discoloration of the components forming the back-ground of said 27.
- the process for making diazo type prints which comprises applying to a base a layer conta ning a diazo compound bleaching on exposure to light, exposing such layer, and contacting the exposed layer with a developer containing an azo dyestutf component and a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- the process for making diazo type prints which comprises applying; to a base .a layer containing a diazo compound bleachmg on exposnie to light, and an azo dyestufi com onent ex )osin such la er and contacting the exposed layer with a developer containing a reducing 'agent capable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- a layer containing a diazo compound bleaching on exposure to light, and an azo dyestufi' component exposing such layer, and contacting the exposed layer with a developer con-- taining a substance comprising a reducing agent and a catalytically active material termed antidxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of said prints.
- the process for making diazo type prints which comprises applying to a base a layer containing a diazo compound bleaching' on exposure to light and a non-coupling compound decomposable into an 2120 dyestuff component, exposing such layer, and contacting the exposed layer with a developer containing a reducing agent capable of arresting-under normal conditions I the discoloration of the components forming the back-ground of said prints.
- the'reducing agent is an amino compound capable of arresting under normal conditions the discoloration of the compo nents forming the back-ground of said prints.
- the process for making diazo type prints which comprises applying to a base 'a layer containing a diazo compound bleaching on exposure to light and a non-coupling compound decomposable into an azo dyestuii component, 51nd contacting the exposed layer with a developer containing a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the background of said prints.
- the salt is a salt of a strong base with a volatile acid which salt upon heating yields an alkaline material.
- the salt is a salt of a strong base with a. heat decomposable acid which salt upon heatingyiclds an alkaline material.
- the diazo group and a reducing agent capable of arresting under normal conditions :the discoloration of the components forming the back-ground of the finished print.
- a base hav ng a S8IlS1- tive layer thereon containing a diazo compound, an azo dyestuif,component,.and a substance comprising a reducing agent and a catalytically active material termed antioxygene of Moureu which substance is ca- .pable .of arresting under normal conditions and a reducing agent capable of arresting under normal conditions the discoloration of the components forming the back-ground of the finished print.
- tive layer thereon containing a diazo compound, a non-coupling compound decomposable into an azo dyestufi' component, a substance comprising a reducing agent and a- As a new product, a base having-a sensi- 515 catalytically active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of the finished print.
- a base having ii -r sensitive layer thereon containing a diazo compound bleaching on exposure. to light and containing in the para-position toxthe diazo group a tertiary nitrogen atom substituted in the benzene nucleus or not but not containing a substituent which can rev pound bleaching on exposure to light and containing in the para-position to the diazo group a.
- non-coupling compound decomposable into an azo dyestuil' component and a substance comprising a reducing agent and a catalyticallv active material termed antioxygene of Moureu which substance is capable of arresting under normal conditions the discoloration of the components forming the back-ground of the finished print.
- non-coupling compound is the reaction product of an azo dvestuff component and a substance inhib ting the phenol function of said are dyestufl component.
- non-coupling compound is the reaction product of an azo dyestuiit' compo- Dent and hydroxylamine.
- non-coupling compound is the reaction product of an azo dyestufi component and semicarbazide.
- non-coupling compound is the reaction product of an azo dyestuff component and a substance inhibiting the phenol function of said azo dyestuif component.
- non-coupling compound is the reaction product of an azo dyestutf component and hydroxylamine.
- non-coupling compound is the reaction product of an azo dyestutf component and semicarbazide.
- reducing agent is hydroxylout which can react with the diazo group and an azo dyestufi' component, substantially stable against premature coupling which comprises including therein a reducing agent other than an acid capable of arresting the coupling activity of the components of said layer.
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL1821281X | 1926-12-11 | ||
GB1184627A GB294972A (en) | 1927-05-03 | 1927-05-03 | Improvements in the manufacture of diazo-types |
Publications (1)
Publication Number | Publication Date |
---|---|
US1821281A true US1821281A (en) | 1931-09-01 |
Family
ID=26248567
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US196993A Expired - Lifetime US1821281A (en) | 1926-12-11 | 1927-06-06 | Manufacture of diazo-types |
Country Status (2)
Country | Link |
---|---|
US (1) | US1821281A (nl) |
BE (1) | BE343251A (nl) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487446A (en) * | 1945-12-08 | 1949-11-08 | Gen Aniline & Film Corp | Process for preventing stains on photographic color material during drying following exposure, bleaching, and fixing treatment |
US2597306A (en) * | 1949-10-05 | 1952-05-20 | Little Inc A | Printing process wherein an alkaline substance passing through stencil openings effects coupling of an azo dye in situ |
US2644756A (en) * | 1947-02-08 | 1953-07-07 | Polaroid Corp | Photographic process for forming a positive transfer image |
US2680062A (en) * | 1949-07-23 | 1954-06-01 | Keuffel & Esser Co | Process for the production of azo dyestuff images |
US2739061A (en) * | 1952-09-10 | 1956-03-20 | Grinten Chem L V D | Process for the production of diazotype copies |
US2741558A (en) * | 1952-03-11 | 1956-04-10 | Grinten Chem L V D | Process for the manufacture of diazotype copies |
US2773768A (en) * | 1951-03-20 | 1956-12-11 | Grinten Chem L V D | Light-sensitive diazotype material |
US3135607A (en) * | 1961-04-28 | 1964-06-02 | Nashua Corp | Heat development of diazo recording and copying papers which comprise a quaternary ammonium halide |
US3607271A (en) * | 1968-01-12 | 1971-09-21 | Oce Van Der Grinten Nv | Phloroglucinol developer for lingt-sensitive planographic plates |
US4090879A (en) * | 1976-11-15 | 1978-05-23 | Gaf Corporation | Developing solutions for 2-component diazo-type materials |
US4411979A (en) * | 1981-01-28 | 1983-10-25 | Ricoh Company, Ltd. | Diazo type thermosensitive recording material |
WO1988002878A1 (en) * | 1986-10-20 | 1988-04-21 | Macdermid, Incorporated | Image reversal system and process |
-
0
- BE BE343251D patent/BE343251A/xx unknown
-
1927
- 1927-06-06 US US196993A patent/US1821281A/en not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2487446A (en) * | 1945-12-08 | 1949-11-08 | Gen Aniline & Film Corp | Process for preventing stains on photographic color material during drying following exposure, bleaching, and fixing treatment |
US2644756A (en) * | 1947-02-08 | 1953-07-07 | Polaroid Corp | Photographic process for forming a positive transfer image |
US2680062A (en) * | 1949-07-23 | 1954-06-01 | Keuffel & Esser Co | Process for the production of azo dyestuff images |
US2597306A (en) * | 1949-10-05 | 1952-05-20 | Little Inc A | Printing process wherein an alkaline substance passing through stencil openings effects coupling of an azo dye in situ |
US2773768A (en) * | 1951-03-20 | 1956-12-11 | Grinten Chem L V D | Light-sensitive diazotype material |
US2741558A (en) * | 1952-03-11 | 1956-04-10 | Grinten Chem L V D | Process for the manufacture of diazotype copies |
US2739061A (en) * | 1952-09-10 | 1956-03-20 | Grinten Chem L V D | Process for the production of diazotype copies |
US3135607A (en) * | 1961-04-28 | 1964-06-02 | Nashua Corp | Heat development of diazo recording and copying papers which comprise a quaternary ammonium halide |
US3607271A (en) * | 1968-01-12 | 1971-09-21 | Oce Van Der Grinten Nv | Phloroglucinol developer for lingt-sensitive planographic plates |
US4090879A (en) * | 1976-11-15 | 1978-05-23 | Gaf Corporation | Developing solutions for 2-component diazo-type materials |
US4411979A (en) * | 1981-01-28 | 1983-10-25 | Ricoh Company, Ltd. | Diazo type thermosensitive recording material |
WO1988002878A1 (en) * | 1986-10-20 | 1988-04-21 | Macdermid, Incorporated | Image reversal system and process |
Also Published As
Publication number | Publication date |
---|---|
BE343251A (nl) |
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