US3199982A - Diazotype reproduction material - Google Patents
Diazotype reproduction material Download PDFInfo
- Publication number
- US3199982A US3199982A US266332A US26633263A US3199982A US 3199982 A US3199982 A US 3199982A US 266332 A US266332 A US 266332A US 26633263 A US26633263 A US 26633263A US 3199982 A US3199982 A US 3199982A
- Authority
- US
- United States
- Prior art keywords
- heat
- support
- diazotype
- agent
- diazo
- 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
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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
- G03C1/60—Compositions containing diazo compounds as photosensitive substances with macromolecular additives
Definitions
- FIG. 2 DIAZOTYPE REPRODUCTION MATERIAL Filed March 19, 1963 HEAT- DEVELOPAB LE TWO-COMPONENT PHOTOSENSITIVE DIAZOTYPE
- FIG. 2 SUPPORT I I HEAT- DEVELOPABLE TWO- COMPONENT PHOTOSENSITIVE DIAZOTYPE REPRODUCTION MATERIAL IO TWO-COMPONENT PHOTOSENSITIVE DIAZOTYPE LAYER 23 PRECOAT LAYER 22
- FIG. 2
- FIG 3 HEAT-ACTIVATABLE DEVELOPING AGENT 32 SUPPORT 3
- This invention relates to diazotype reproduction materials and methods for their production and use, and refers more particularly to two-component photosensitive diazotype reproduction materials which are developable by means of heat,'and to the methods and means for accomplishing the heat development of said materials Photosensitive diazotype materials are well known andhave many advantages over other means of reproduction when consider-ing the combined basis of quality and cost. The photosensitive diazotype materials, however, possess some inherent disadvantages depending upon their type.
- the dry diazo materials utilize gaseous ammonia to raise the pH of the coating after exposure to allow coupling of the diazo compound and coupler which are coated on the same support.
- gaseous ammonia which is obnoxious and dangerous to handle
- the semirwet system of diazo development utilizes a photosensitive material which comprises a base sheet and a coating of photosensitive diazo compound coated on the base sheet. After exposure under a master to actinic light, the sheet coated with the diazo compound is passed through a chemical bath which contains an alkali and a coupler to develop the image by dye formation.
- a liquid is required in the development step. The liquid affects the paper base and requires drying.
- the old systems used melting wax layers and the like inheat sensitive and not necessarily light sensitive materials.
- ammonium bicarbonate and'the like, which decompose freely at temperatures slightly above room temperature with the release of free gaseous ammonia and water vapor.
- the solid carbonates were. heated in juxtaposition to the exposed two-component diazotype paper to fully utilize thereleased gaseous ammonia on the exposed surface.
- This known material had the great disadvantage of very poor shelf life'which severely limited its practical use.
- Another known material incorporated urea with a photosensitive diazoic.
- Urea in a separate stratum was tried in another material.
- Developing sheets impregnated with a composition containing one compound or a combination of compounds which liberated the vapor of an alkali or a coupler were also tried.
- Another material incorporated a carboxamide such as formamide,- acetamide, urea, and methyl-urea as a humectant but not as a source of alkali ammonia.
- Another material was a multilayer diazotype material comprising a support, a layer containing. a diazo compound, a; fusible barrier layer which melted below the decomposition temperature of the diazo compound, and alayer containing a coupler, all coated on one side of a support.
- the diazotype material was placed, in contact with a master and subjected to infrared radiation. Imagewise generation and transfer of heat from the master to the multilayer diazotype material melted the fusible barrier. layer and permitted the diazo compound and coupler to form an azo dye.
- Another object is to provide a photosensitive heat-.
- Another object is to provide a photosensitive twocomponent heat-developable diazotype'reproduction material whichis heat-developable and which is stable to further application of heat.
- Another object of the present invention is to provide a photosensitive heat-developable diazotype material which is inexpensive and which gives'good quality diazo reproduction.
- the base necessary for the development is produced on the diazotype material at the time of development by thermally induced chemical or physical conversion of a base-releasing compound. The application of heat causes this compound to release the base necessary for the couplingreaction at the time of development.
- organic nitrogen compounds are suitable sources of base for heat-developable diazo mate-rials. These compounds can be incorporated in a sensitizing layer, in a precoat layer, or in a developing sheetdepending upon solubility and compatibility.
- the compounds ot the present invention are induced by elevated temperatures to release a base which increases the alkalinity of "the system and permits coupling to take place, thereby developing the latent image.
- organic nitrogen compounds suitable for use in the present invention are those cor-responding to the following general formula and. salts thereof: a i
- RINHR2 wherein R [and R are members selected from the groups from the following speciconsisting of: group A where R is a member selected from the group consisting of alkyl, hydroxyalkyl, ethoxycarbonyl alkyl, carboxyalkyl, carboxy carbamoyl alkyl, guanyl, arylguanyl, aminoguanyl, diallylamino-triazinyl, arylamino triazinyl, thiazoly-l, andpyridyl, and. R is a member selected from the group consisting of hydrogen, alkyl, and guanyl; and group B WHIBH'RL and R are members of the same heterocyclic ring.
- guanidine (as the bicarbonate salt), phenyi 'guanidine (as the carbonate salt); phenyl biguanide, vN; N-diallylmelamine, 2,4-diamino6 phenyl-s triazine, '2-am'inothiazole, and '2-aminopyridine.
- R and R are members of the same heterocyclic ring. .
- This group includes imid-azole, benzimidazole, and piperazine (as the hexahydrate).
- FIGURE 1 is a sectional v-iewof a heat-developable two-component photosensitive .diazotype reproduction material 10 comprising a support :11 and a heat-developable two-corrip0nent photosensitive diazotype layer 12 coated on said support;
- FIGURE 2 is a sectional view of a heat-developable two-component photosensitive diazotype' reproduction material 20 comprising a support 21, aprecoat. layer 22 coated on said support, and a two-component photosensitive diazotype layer 23 coated over said precorat layer on said support; and
- FIGURE. 3 is asectional view of a developing sheet 36 comprising a support 31 and "a heat-activatab'le developing agent 3'2 impregnated in said-support.
- the developing sheet is in contact with a two component'photosensitive diazotypereproduction material 40 comprising a support 41 and atwo-com ponent photosensitvie diazotype layer 42' coated on said support;
- One method of the present invention for thepreparation of a heatdeveloping reproduction material is to treat a support material with a solution of heat-activatable developing agent. After drying, the same support is coated on the same side or on the opposite side with a sensitizing solution comprising diazonium compound and couple-r.
- the coating is dried; In this method the heatactivatable developing agent is in the first or precoat layer.
- the sensitized support is exposed through a master to actinic radiations and is then developed by heat in the range between the activation temperature of the developing agent. and the scorching temperature of the support material.
- the heat-activated libenation of developing agent then causes the image to develop.
- the preparationand. .use-ot 'heat-developable tWo-component p'hotosensitive diaz-otype reproduction material precoated with heat-tactivatable developing agent of the present invention is illustrated in Example 5.
- the heat-activatalble developing agent is incorporated into the sensitizing with the photosensitive solution comprising diazonium compound and coupler.
- the solution is applied to a supportand then dried.
- the sensitized support is exposed through a master to actinic radiations and after exposure, heat is applied to the support.
- the temperature is preferably in range between the activation temperature. .of the developing agent and the scorching temperature of the support material.
- a developing sheet is prepared by impregnating a support with a solution of -il1eat-activ.atable developing agent in a suitable solvent. The solvent is then removed by drying.
- the developingshee-t is used to develop an exposed two-component photosensitive diazotype. reproduction material by placing it in face-to-fiace contact with the exposed sensitized surface of the diazotypc material and subjecting the assembly to heat in the range between the activation temperature of theqdeveloping agent and the scorching temperature of the diazotype support. This activates the developing agentand permits coupling to occur on the sensitized surface of the diazotype material.
- the preparation and use of a developing sheet utilizing the heat-activatahle developing agentof the present invention is illustnalted in Example 1. 1
- the developing temperature range is determined by two factors: first, the activation temperature of'the heatactivatable developing agent; and second, the scorching temperature of the diazotype support material.
- the activation tempenature is that degree of heat necessary to release or liberate the developing agent in the amount required for development of a two-component photosensitive diazotypereproduction material.
- the scorching temperature is that degree'of heat which darkens the background of a developed diazotype'print or which causes undesirable physical degradation 'of'the diazotype support material.. V p
- the prepared developing sheet was used to heat-develop ing sheet was used to heat-develop a diazotype reproduction material by placing it in contact with the sensitized sunface of the reproduction materialthat had been exposed to actinic-radiations through .a master; heating the developing sheet for a few seconds at C. while in contact with thesensitized surfacerof the reproduction material to release the base and thus eifect coupl ing, .and' dinally, sepa-ratingthe developing sheet from the diazo type reproduction material.
- a colored dye image- was formed on the diazotype reproduction material.
- Tetradecylamine, hexladecylamine, ootadecylamine, 2- amino thiazole, Z-aminopy-ridine, and benzim'idazole were used in place of the dodecylamine to produce the same result.
- Example 2N-methyl glucamine was :used from a 10% aqueous solution to prepare a developing sheet as in Example, 1. Used in the same manner to heat-develop a diazotype reproduction material, the same results were obtained.
- Example 3 N-methyl 'glucamine was used as a sen- G.
- Water 150 Tartaric acid A
- Trichloroacetic acid 7 1,3,6-naphthalenetrisulfonic acid, sodium salt 6 N-methyl glucamine 5 p-Dimethylamino benzene diazonium chloride,
- zinc chloride salt 4 2,3-dihydroxy-naphthalene-G-sulfonic acid
- Imidazole n-butylamine hydrochloride, L-glutamine, glycine ethyl ester hydrochloride, phenyl biguanide, aminoguanidine sulfate, guanidine acetate, and phenyl guanidine carbonate were used in place of N-methyl glucamine.
- Aminoguanidine bicarbonate was used in. half quantities. All produced a blue image with the exception of aminoguanidine sulfate which produced a red-violet image.
- Example 4.-N,N-diallyl melamine was used in a precoat layer coated from the following solution:
- zinc chloride salt 4 2,3-dihydroxynaphthalene-6-sulfonic acid
- Example 5 -2,4-diamino-6-phenyl-s-triazine was used from a saturated solution in dioxane to prepare a precoat layer on a support. This was then sensitized as in Example 4 to produce substantially the same results when heat-developed.
- Example 6 The sensitizing solution of Example 3 was prepared with 3 g. of benzimidazole in place of 5 g. of N-methyl glucamine. After a support was sensitized and heat-developed as in Example 3, a blue image corresponding to the master image was produced.
- Example 7 A mixture of the following composition was used to prepare a developing sheet:
- Example 8 A sensitizing solution was prepared according to the formula in Example 3 using 15 g. alpha-alanine in placeof the 5 g. N-methyl glucamine. The solution was coatedon a support and heat-developed to produce a blue dye image corresponding to the master image.
- a heat-developable diazo-type'material which comprises:
- R and R are members selected from one of the groups consisting of:
- a diazo sheet to imagewise actinic radiation
- said sheet comprising a support resistant to the scorching effects of heat at the conditions of thermal development, and a photosensitive diazonium compound, a coupler therefor, and a heat-activatable developing agent coated on said support, said agent having the general formula:
- R and R are members selected from one of the groups consisting of:
- R is a member selected from the group consisting of alkyl, thiazolyl, pyridyl, guanyl, and triazinyl, and R is selected from the group consisting of hydrogen, methyl, and guanyl; and group B Where R and R are members of the same heterocyclic ring; and
- a material in accordance with claim 4 in said 'agent is 2,4-diamino-6-phenyl-s-triazine.
- a method in accordance with claim said agent is n-butylarnine hydrochloride.
- a method in accordance with calim said agent is N-methyl glucamine.
- a method in accordance with claim said agent is phenyl biguanide.
- agent is guanidine acetate.
- a method in accordance with claim said agent is imidazole.
- agent is.N,N-diallyl melamine.
- a method in accordance with claim said agent is 2,4-diamino-6-phenyl-s triazine.
Description
Claims (2)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US266230A US3255007A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction materials |
US266332A US3199982A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction material |
DE19641447737 DE1447737A1 (en) | 1963-03-19 | 1964-03-14 | Heat-developable reproduction material for diazotype |
BE645321D BE645321A (en) | 1963-03-19 | 1964-03-17 | |
NL6402881A NL6402881A (en) | 1963-03-19 | 1964-03-18 | |
GB11670/64A GB1064974A (en) | 1963-03-19 | 1964-03-19 | Improvements in and relating to diazotype reproduction |
FR967920A FR1396590A (en) | 1963-03-19 | 1964-03-19 | Reproductive material capable of being thermally developed, intended for diazotype |
AT242364A AT277751B (en) | 1963-03-19 | 1964-03-19 | Heat developable diazotype material |
GB50143/66A GB1064975A (en) | 1963-03-19 | 1964-03-19 | Improvements in and relating to diazotype reproduction |
US482655A US3469981A (en) | 1963-03-19 | 1965-07-12 | Diazotype reproduction materials |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US266230A US3255007A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction materials |
US266332A US3199982A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction material |
Publications (1)
Publication Number | Publication Date |
---|---|
US3199982A true US3199982A (en) | 1965-08-10 |
Family
ID=26951714
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US266332A Expired - Lifetime US3199982A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction material |
US266230A Expired - Lifetime US3255007A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction materials |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US266230A Expired - Lifetime US3255007A (en) | 1963-03-19 | 1963-03-19 | Diazotype reproduction materials |
Country Status (6)
Country | Link |
---|---|
US (2) | US3199982A (en) |
AT (1) | AT277751B (en) |
BE (1) | BE645321A (en) |
DE (1) | DE1447737A1 (en) |
GB (2) | GB1064974A (en) |
NL (1) | NL6402881A (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3312551A (en) * | 1962-07-25 | 1967-04-04 | Keuffel & Esser Co | Heat and light sensitive diazo sulfonate and azo coupler coated sheet |
US3380830A (en) * | 1963-09-24 | 1968-04-30 | Bauchet & Cie | Heat developable diazo photocopying sheet |
US3389995A (en) * | 1964-09-15 | 1968-06-25 | Gen Aniline & Film Corp | Two-component heat developable diazotypes containing amidine compounds |
US3446620A (en) * | 1965-03-18 | 1969-05-27 | Addressograph Multigraph | Process for developing diazotype materials |
US3458314A (en) * | 1963-09-25 | 1969-07-29 | Keuffel & Esser Co | Process and device for developing a two-component diazotype material |
US3480433A (en) * | 1967-03-22 | 1969-11-25 | Eastman Kodak Co | Thermally activatable diazotype compositions |
US3493374A (en) * | 1965-07-01 | 1970-02-03 | Grinten Chem L V D | Heat-developable diazotype material |
US3520691A (en) * | 1966-03-19 | 1970-07-14 | Keuffel & Esser Co | Heat-developable diazotype material |
US3642483A (en) * | 1966-11-07 | 1972-02-15 | Ricoh Kk | Thermally developable diazotype copying materials |
US3910794A (en) * | 1972-04-20 | 1975-10-07 | Cellophane Sa | Imidazole couplers for two component diazotype systems |
US3918974A (en) * | 1970-05-01 | 1975-11-11 | Mita Industrial Co Ltd | Process for the diazo-type multicolor reproduction |
US3985562A (en) * | 1973-05-18 | 1976-10-12 | Agfa-Gevaert N.V. | Diazo recording process and material |
US4155762A (en) * | 1975-06-03 | 1979-05-22 | Ricoh Co., Ltd. | Liquid developer for binary diazo copying materials |
US4168171A (en) * | 1977-08-05 | 1979-09-18 | Minnesota Mining And Manufacturing Company | Light-sensitive thermal developable diazotype sheets with imidazoles |
US4230789A (en) * | 1978-03-13 | 1980-10-28 | Minnesota Mining And Manufacturing Company | Thermal diazotype sheets |
US4554236A (en) * | 1982-03-18 | 1985-11-19 | American Hoechst Corporation | Amino acid stabilizers for water soluble diazonium compound condensation products |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1447736A1 (en) * | 1964-02-29 | 1969-01-09 | Kalle Ag | Heat developable two-part diazotype copier material and process for making the same |
DE1303130B (en) * | 1964-03-10 | Van der Gnnten N V Venlo (Nieder lande) | Diazotype material to be developed with warmth | |
US3367776A (en) * | 1964-04-17 | 1968-02-06 | Addressograph Multigraph | Heat sensitive diazotype materials |
US3386826A (en) * | 1964-05-08 | 1968-06-04 | Ibm | Process for producing improved diazotype elements |
US3406072A (en) * | 1964-12-21 | 1968-10-15 | Gaf Corp | One-component diazotypes |
DE1572048C3 (en) * | 1965-09-10 | 1978-10-26 | Hoechst Ag, 6000 Frankfurt | Heat developable diazotype material |
US3512978A (en) * | 1966-03-21 | 1970-05-19 | Keuffel & Esser Co | Diazosulfonate composition,copying material,and method of use |
US3420405A (en) * | 1966-08-04 | 1969-01-07 | Us Plywood Champ Papers Inc | Package for copy sheets |
US3981730A (en) * | 1973-04-18 | 1976-09-21 | Mita Industrial Company, Ltd. | Diazo-type multicolor reproduction process |
JPS5744141A (en) * | 1980-08-29 | 1982-03-12 | Ricoh Co Ltd | Heat development type diazo copying material |
US4419432A (en) * | 1982-09-22 | 1983-12-06 | Keuffel & Esser Company | Diazotype composition stabilization |
JPS61104887A (en) * | 1984-10-27 | 1986-05-23 | Kanzaki Paper Mfg Co Ltd | Thermal recording material |
CN109127055B (en) * | 2018-08-20 | 2020-07-03 | 江苏广都建设有限公司 | Small-size flour mill that building engineering used |
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US1807761A (en) * | 1928-07-30 | 1931-06-02 | of wiesbaden-biebrich | |
US2459521A (en) * | 1944-10-14 | 1949-01-18 | Rca Corp | Electrolytic recording |
US2545423A (en) * | 1949-02-10 | 1951-03-13 | Gen Aniline & Film Corp | Diazotypes containing a guanide base in a gelatin layer to prevent dye diffusion |
US2593911A (en) * | 1948-12-31 | 1952-04-22 | Gen Aniline & Film Corp | Diazotypes containing a condensation product of dicyandiamide with formaldehyde and a salt of ammonia or an aromatic amine |
US2618555A (en) * | 1949-04-09 | 1952-11-18 | Kalle & Co Ag | Process for positive diazotype and negative metal reduction images and light-sensitive material therefor |
US2668111A (en) * | 1952-03-05 | 1954-02-02 | Certain Teed Prod Corp | Paper making processes |
US2732299A (en) * | 1952-07-22 | 1956-01-24 | Light sensitive | |
US2774669A (en) * | 1953-04-13 | 1956-12-18 | Dick Co Ab | Diazotype reproduction process |
US2822296A (en) * | 1951-11-01 | 1958-02-04 | Armour & Co | Rodent repellent material containing dodecylamine acetate |
GB816601A (en) * | 1954-07-09 | 1959-07-15 | Arnold Tanenbaum | Improvements in or relating to diazotype processes |
FR1249913A (en) * | 1959-11-23 | 1961-01-06 | Bauchet & Cie Ets | Heat-developable diazotype product |
US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
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CA519408A (en) * | 1955-12-13 | J. Schwoegler Edward | Corrosion inhibiting compositions | |
CA564915A (en) * | 1958-10-21 | S. Schwartz Robert | Dry electric facsimile paper | |
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US2358871A (en) * | 1940-05-20 | 1944-09-26 | Du Pont | Textile treatment |
NL150528B (en) * | 1949-05-14 | Hollandse Signaalapparaten Bv | PROCEDURE FOR MANUFACTURE OF TWISTLESS OR ALMOST TWISTLESS YARN AND THE YARN OBTAINED BY USING THIS PROCESS. | |
US2653091A (en) * | 1950-01-31 | 1953-09-22 | Rca Corp | Photographic diazotype composition and heat development thereof |
US2727820A (en) * | 1952-04-29 | 1955-12-20 | Gen Aniline & Film Corp | Light-sensitive diazotype layers containing carboxamides |
US2683088A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Soft bibulous sheet |
US2786807A (en) * | 1953-04-23 | 1957-03-26 | Faximile Inc | Dry electrical recording medium |
-
1963
- 1963-03-19 US US266332A patent/US3199982A/en not_active Expired - Lifetime
- 1963-03-19 US US266230A patent/US3255007A/en not_active Expired - Lifetime
-
1964
- 1964-03-14 DE DE19641447737 patent/DE1447737A1/en active Pending
- 1964-03-17 BE BE645321D patent/BE645321A/xx unknown
- 1964-03-18 NL NL6402881A patent/NL6402881A/xx unknown
- 1964-03-19 GB GB11670/64A patent/GB1064974A/en not_active Expired
- 1964-03-19 AT AT242364A patent/AT277751B/en not_active IP Right Cessation
- 1964-03-19 GB GB50143/66A patent/GB1064975A/en not_active Expired
Patent Citations (12)
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US1807761A (en) * | 1928-07-30 | 1931-06-02 | of wiesbaden-biebrich | |
US2459521A (en) * | 1944-10-14 | 1949-01-18 | Rca Corp | Electrolytic recording |
US2593911A (en) * | 1948-12-31 | 1952-04-22 | Gen Aniline & Film Corp | Diazotypes containing a condensation product of dicyandiamide with formaldehyde and a salt of ammonia or an aromatic amine |
US2545423A (en) * | 1949-02-10 | 1951-03-13 | Gen Aniline & Film Corp | Diazotypes containing a guanide base in a gelatin layer to prevent dye diffusion |
US2618555A (en) * | 1949-04-09 | 1952-11-18 | Kalle & Co Ag | Process for positive diazotype and negative metal reduction images and light-sensitive material therefor |
US2822296A (en) * | 1951-11-01 | 1958-02-04 | Armour & Co | Rodent repellent material containing dodecylamine acetate |
US2668111A (en) * | 1952-03-05 | 1954-02-02 | Certain Teed Prod Corp | Paper making processes |
US2732299A (en) * | 1952-07-22 | 1956-01-24 | Light sensitive | |
US2774669A (en) * | 1953-04-13 | 1956-12-18 | Dick Co Ab | Diazotype reproduction process |
GB816601A (en) * | 1954-07-09 | 1959-07-15 | Arnold Tanenbaum | Improvements in or relating to diazotype processes |
US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
FR1249913A (en) * | 1959-11-23 | 1961-01-06 | Bauchet & Cie Ets | Heat-developable diazotype product |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3312551A (en) * | 1962-07-25 | 1967-04-04 | Keuffel & Esser Co | Heat and light sensitive diazo sulfonate and azo coupler coated sheet |
US3380830A (en) * | 1963-09-24 | 1968-04-30 | Bauchet & Cie | Heat developable diazo photocopying sheet |
US3458314A (en) * | 1963-09-25 | 1969-07-29 | Keuffel & Esser Co | Process and device for developing a two-component diazotype material |
US3389995A (en) * | 1964-09-15 | 1968-06-25 | Gen Aniline & Film Corp | Two-component heat developable diazotypes containing amidine compounds |
US3446620A (en) * | 1965-03-18 | 1969-05-27 | Addressograph Multigraph | Process for developing diazotype materials |
US3493374A (en) * | 1965-07-01 | 1970-02-03 | Grinten Chem L V D | Heat-developable diazotype material |
US3520691A (en) * | 1966-03-19 | 1970-07-14 | Keuffel & Esser Co | Heat-developable diazotype material |
US3642483A (en) * | 1966-11-07 | 1972-02-15 | Ricoh Kk | Thermally developable diazotype copying materials |
US3480433A (en) * | 1967-03-22 | 1969-11-25 | Eastman Kodak Co | Thermally activatable diazotype compositions |
US3918974A (en) * | 1970-05-01 | 1975-11-11 | Mita Industrial Co Ltd | Process for the diazo-type multicolor reproduction |
US3910794A (en) * | 1972-04-20 | 1975-10-07 | Cellophane Sa | Imidazole couplers for two component diazotype systems |
US3985562A (en) * | 1973-05-18 | 1976-10-12 | Agfa-Gevaert N.V. | Diazo recording process and material |
US4155762A (en) * | 1975-06-03 | 1979-05-22 | Ricoh Co., Ltd. | Liquid developer for binary diazo copying materials |
US4168171A (en) * | 1977-08-05 | 1979-09-18 | Minnesota Mining And Manufacturing Company | Light-sensitive thermal developable diazotype sheets with imidazoles |
US4230789A (en) * | 1978-03-13 | 1980-10-28 | Minnesota Mining And Manufacturing Company | Thermal diazotype sheets |
US4554236A (en) * | 1982-03-18 | 1985-11-19 | American Hoechst Corporation | Amino acid stabilizers for water soluble diazonium compound condensation products |
Also Published As
Publication number | Publication date |
---|---|
AT277751B (en) | 1970-01-12 |
GB1064975A (en) | 1967-04-12 |
US3255007A (en) | 1966-06-07 |
DE1447737A1 (en) | 1969-01-09 |
NL6402881A (en) | 1964-09-21 |
GB1064974A (en) | 1967-04-12 |
BE645321A (en) | 1964-09-17 |
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