US3418469A - Diazo reproduction - Google Patents
Diazo reproduction Download PDFInfo
- Publication number
- US3418469A US3418469A US445704A US44570465A US3418469A US 3418469 A US3418469 A US 3418469A US 445704 A US445704 A US 445704A US 44570465 A US44570465 A US 44570465A US 3418469 A US3418469 A US 3418469A
- Authority
- US
- United States
- Prior art keywords
- diazo
- layer
- particles
- reproduction
- discrete
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 25
- 239000000463 material Substances 0.000 description 28
- 239000002245 particle Substances 0.000 description 24
- 230000033458 reproduction Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 229920001169 thermoplastic Polymers 0.000 description 12
- 239000012530 fluid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000004416 thermosoftening plastic Substances 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 150000008049 diazo compounds Chemical class 0.000 description 7
- -1 DIAZO Chemical class 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- IIUJCQYKTGNRHH-UHFFFAOYSA-N 2,4-dihydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1O IIUJCQYKTGNRHH-UHFFFAOYSA-N 0.000 description 1
- HRWJUSVKPYSOSI-UHFFFAOYSA-N 2,5-diethoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OCC)=CC(N2CCOCC2)=C1OCC HRWJUSVKPYSOSI-UHFFFAOYSA-N 0.000 description 1
- MADGGJXZXKOPDW-UHFFFAOYSA-N 2,5-dimethoxy-4-morpholin-4-ylbenzenediazonium Chemical compound C1=C([N+]#N)C(OC)=CC(N2CCOCC2)=C1OC MADGGJXZXKOPDW-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- NUTRHYYFCDEALP-UHFFFAOYSA-N 4-bromo-3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=C(Br)C(O)=C1 NUTRHYYFCDEALP-UHFFFAOYSA-N 0.000 description 1
- XJNHUSFVTDWFFU-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-2,4-diene-2,6-diol Chemical compound OC1=CC=CC2(O)SC12 XJNHUSFVTDWFFU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 238000007687 exposure technique Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
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
Definitions
- a method for image formation on diazotype material includes the use of developable diazotype composition having an outer coating of a layer of discrete solid particles of a thermoplastic polymeric material which is ordinarily permeable to diazotype developing fluids, but when heated will form a coalesced impermeable film.
- a developer fluid such as ammonia vapors or an alkaline solution of azo dye coupler
- the present invention relates to diazo reproduction and refers more particularly to materials and methods for making diazo reproductions.
- diazo materials are exposed to actinic radiation through a transparent or translucent original, thereby destroying the light-sensitive diazo compound in the exposed areas.
- the undecomposed diazo compound is then combined with a coupling component in the presence of an alkali to form a dye. It is not presently possible to copy two-sided printed materials or graphic information on opaque bases by this procedure, nor is it possible to make a reversal copy by this procedure.
- one object of the present invention is to provide materials and methods for making diazo reproductions, which overcome the disadvantages of the prior art.
- Another object is to provide materials and methods for copying opaque and two-sided originals.
- Another object is to provide materials and methods for making direct and reversal copies.
- Another object is to provide methods for making diazo reproductions by the reflex technique.
- Another object is to provide methods for making diazo transparencies without ultraviolet radiation.
- Another object is to provide methods for making diazo intermediates from originals having printed matter on both sides.
- the objects of the present invention may be realized by impressing an image on a diazo material overcoated with a layer of discrete coalesceable thermoplastic particles, by means of infrared radiation or ultraviolet radiation, and developing the image by means of ammonia vapors or a liquid developer.
- the diazo material may be of the dry-developing variety or the semi-moist variety. In the dry-developing type, the diazo compound and the coupler are on the same support. In the semi-moist type, only the diazo compound is on the support; the coupler is in the aqueous developer.
- the discrete coalesceable thermoplastic particles may also be coated together with the diazo compound.
- the diazo material preferably comprises a diazo layer on a support which is substantially vapor and liquid-impervious. Paper may be used but plastic films are better.
- a conventional dry-developing diazo material was overcoated with 3,418,469 Patented Dec. 24, 1968 a discontinuous layer of discrete coalesceable thermoplastic latex particles which coalesce above a given temperature.
- the uniform, discontinuous layer was substantially transparent except for a slight haze which was barely visible.
- the discontinuous layer was permeable to vapors and liquids.
- the resulting sheet was used in a normal manner by contact exposure to ultraviolet radiation which decomposed the diazo compound in the light-struck areas and by development in ammonia vapors to produce a positive reproduction of good quality.
- thermographic methods coupled with retention of the original conventional methods.
- Thermal imaging may take place in a thermographic copying machine using an original with infrared-absorbing graphics.
- the thermal exposure coalesces the latex particles in the image areas so that the particles adhere to each other and to the support in these areas.
- the coalesced particles thus form a vapor barrier or mask that prevents development in heated areas while the uncoalesced particles permit coupling in the uu heated areas.
- Development with ammonia produces a reversal copy of the original.
- Subsequent uniform exposure to ultraviolet radiation stabilizes the image.
- Exposure in the thermoprinting machine may be either by front-printing or back-printing.
- the former permits copying two-sided or opaque originals.
- Thermographic and photographic exposure techniques may be combined in any sequence to obtain composite copies of two or more originals.
- the film substrate prevents ammonia permeation through the support to the underlying diazo layer, but paper and cloth substrates were still suitable for producing excellent reproductions.
- a barrier coating of ammonia-impermeable polymer may be used.
- a semi-moist diazo material was also used.
- the sensitized layer was overcoated with the latex and used for photographic or thermographic copying to give positives, negatives, or combinations of both.
- Development in the semi-moist developer proceeds normally for the ultra-violet-exposed copy, since the uncoalesced particles permit penetration of the developer into the sensitized layer.
- Another example of this invention employs a developing sheet which releases alkali vapors upon heating.
- the alkali-releasing temperature is below the particle-coalescing temperature to prevent serious image degradation.
- the diazo material was placed in intimate contact with the alkali-releasing sheet with the particle layer in contact with the alkali-releasing sheet.
- the composite was then passed through a heating machine which heats the paper to the alkali-releasing temperature.
- an infrared-absorbing layer on the alkali sheet permits development by infrared radiation in a thermographic machine.
- Suitable supports for the diazo layer were paper, film, cloth and similar bases. Where the support is transparent, the reproduction may be used as a transparency for projection purposes or as an intermediate for further reproduction.
- photosensitive diazo compounds were 4-diethyl-amino-benzene diazonium borofluoride; 2,5-dimethoxy-4-morpholino-benzene diazonium borofluoride; 2,5 diethoxy-4-morpholino-benzene-diazonium borofluoride; 4 ethylbenzylamino benzene diazonium chloride; and mixtures thereof.
- Other photosensitive diazonium compounds may be used.
- Couplers were 2,4-dihydroxy-benzamide; 1-methyl-3-hydroxy-4-acetylamido-benzene; 3-hydroxy-2- naphthoic acid ethanolamide hydrochloride; diresorcinol sulfide; 4 bromo 3,5 dihydroxy benzoic acid amide; resorcinol; (2 hydroxy 4 methyl)-beta-pheny1-glutaric acid; 3-hydroxy-2-naphtholic acid ethylene-diamine amide hydrochloride; and mixtures thereof.
- Other couplers may also be used.
- Some suitable latexes were Rhoplex B-85 acrylic resin latex, Vinac WR- polyvinyl acetate emulsion, poly- EM non-ionic polyethylene emulsion, emulsion M polystyrene emulsion, Poly-EM11 anionic polyethylene emulsion.
- the latexes were diluted to 1 to 10 percent by volume for coating purposes.
- the particles were discrete when coated but were coalesced by the application of heat.
- the layer of discrete particles is permeable to ammonia and to aqueous developer, but the coalesced particles are impervious to ammonia and to aqueous developer.
- diazo material may be used as the starting material. It is coated with the layer of discrete coalesceable thermoplastic particles in a thin and transparent layer. In fact, the layer is barely discernible except as a slight haze on transparent supports.
- a diazo reproduction material consisting essentially of:
- a substantially fluid-impermeable support a layer of light-sensitive diazotype composition coated on said support, said composition comprising a light-sensitive diazonium compound capable of forming a dye with azo coupler compound;
- a diazo reproduction material consisting essentially of:
- a substantially fluid-impermeable support a layer of light-sensitive diazotype composition coated on said support, said composition comprising a light-sensitive diazonium compound and an azo coupler compound capable of forming a dye with said diazonium compound;
- a diazo reproduction material according to claim 1 wherein said permeable layer consists essentially of discrete, coalesceable, thermoplastic particles of polyvinyl acetate.
- a method of image reproduction comprising:
- a developer fluid capable of promoting the formation of an azo dye in said diazotype composition, whereby said developer fluid penetrates the permeable areas of said polymer particle layer and effects dye formation in those portions of said diazotype composition immediately underlying said permeable areas.
- said developer fluid comprises an alkaline solution of an azo coupler compound.
- a method of image reproduction according to claim 7 including a further fixing step, after the application of developer, comprising exposing said material to ultraviolet radiation.
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)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US445704A US3418469A (en) | 1965-04-05 | 1965-04-05 | Diazo reproduction |
DE19661572076 DE1572076A1 (de) | 1965-04-05 | 1966-04-02 | Diazotypieverfahren und Diazotypiematerial |
BE678993D BE678993A (en)) | 1965-04-05 | 1966-04-04 | |
AT320066A AT277752B (de) | 1965-04-05 | 1966-04-04 | Diazotypiematerial |
SE04502/66A SE326102B (en)) | 1965-04-05 | 1966-04-04 | |
FR56426A FR1473770A (fr) | 1965-04-05 | 1966-04-05 | Procédé et matériel pour la diazotypie |
NL6604532A NL6604532A (en)) | 1965-04-05 | 1966-04-05 | |
GB15108/66A GB1134943A (en) | 1965-04-05 | 1966-04-05 | Improvements in and relating to diazo-type reproduction |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US445704A US3418469A (en) | 1965-04-05 | 1965-04-05 | Diazo reproduction |
Publications (1)
Publication Number | Publication Date |
---|---|
US3418469A true US3418469A (en) | 1968-12-24 |
Family
ID=23769896
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US445704A Expired - Lifetime US3418469A (en) | 1965-04-05 | 1965-04-05 | Diazo reproduction |
Country Status (7)
Country | Link |
---|---|
US (1) | US3418469A (en)) |
AT (1) | AT277752B (en)) |
BE (1) | BE678993A (en)) |
DE (1) | DE1572076A1 (en)) |
GB (1) | GB1134943A (en)) |
NL (1) | NL6604532A (en)) |
SE (1) | SE326102B (en)) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3514597A (en) * | 1966-04-05 | 1970-05-26 | Agfa Gevaert Nv | Thermographic recording processes and materials |
US4650738A (en) * | 1984-10-22 | 1987-03-17 | American Hoechst Corporation | Negative working diazo color proofing method |
US4659642A (en) * | 1984-10-22 | 1987-04-21 | American Hoechst Corporation | Positive working naphthoquinone diazide color proofing transfer process |
US5124227A (en) * | 1990-03-15 | 1992-06-23 | Graphics Technology International Inc. | Protective overcoats for diazo type layers |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US2691587A (en) * | 1949-07-20 | 1954-10-12 | Rca Corp | Developing of diazotype images |
US2732299A (en) * | 1952-07-22 | 1956-01-24 | Light sensitive | |
US3027256A (en) * | 1957-11-22 | 1962-03-27 | Dietzgen Co Eugene | Production of light-sensitive diazotype materials |
US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
FR1336307A (fr) * | 1962-07-19 | 1963-08-30 | Bauchet & Cie Ets | Produit diazotype photosensible développable par la chaleur et son procédé de préparation |
FR1377477A (fr) * | 1963-09-24 | 1964-11-06 | Bauchet & Cie Ets | Procédé de fabrication d'un article à surface photosensible diazotype thermodéveloppable et article réalisé par application de ce procédé |
US3272629A (en) * | 1962-01-25 | 1966-09-13 | Nashua Corp | Photosensitive diazotype materials |
US3284201A (en) * | 1961-12-21 | 1966-11-08 | Grinten Chem L V D | Three layered light-sensitive diazotype material |
-
1965
- 1965-04-05 US US445704A patent/US3418469A/en not_active Expired - Lifetime
-
1966
- 1966-04-02 DE DE19661572076 patent/DE1572076A1/de active Pending
- 1966-04-04 SE SE04502/66A patent/SE326102B/xx unknown
- 1966-04-04 AT AT320066A patent/AT277752B/de not_active IP Right Cessation
- 1966-04-04 BE BE678993D patent/BE678993A/xx unknown
- 1966-04-05 GB GB15108/66A patent/GB1134943A/en not_active Expired
- 1966-04-05 NL NL6604532A patent/NL6604532A/xx unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2691587A (en) * | 1949-07-20 | 1954-10-12 | Rca Corp | Developing of diazotype 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 |
US2732299A (en) * | 1952-07-22 | 1956-01-24 | Light sensitive | |
US3027256A (en) * | 1957-11-22 | 1962-03-27 | Dietzgen Co Eugene | Production of light-sensitive diazotype materials |
US3046128A (en) * | 1958-07-03 | 1962-07-24 | Dietzgen Co Eugene | Thermally developable diazotype photoprinting material and production thereof |
US3284201A (en) * | 1961-12-21 | 1966-11-08 | Grinten Chem L V D | Three layered light-sensitive diazotype material |
US3272629A (en) * | 1962-01-25 | 1966-09-13 | Nashua Corp | Photosensitive diazotype materials |
FR1336307A (fr) * | 1962-07-19 | 1963-08-30 | Bauchet & Cie Ets | Produit diazotype photosensible développable par la chaleur et son procédé de préparation |
FR1377477A (fr) * | 1963-09-24 | 1964-11-06 | Bauchet & Cie Ets | Procédé de fabrication d'un article à surface photosensible diazotype thermodéveloppable et article réalisé par application de ce procédé |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3514597A (en) * | 1966-04-05 | 1970-05-26 | Agfa Gevaert Nv | Thermographic recording processes and materials |
US4650738A (en) * | 1984-10-22 | 1987-03-17 | American Hoechst Corporation | Negative working diazo color proofing method |
US4659642A (en) * | 1984-10-22 | 1987-04-21 | American Hoechst Corporation | Positive working naphthoquinone diazide color proofing transfer process |
US5124227A (en) * | 1990-03-15 | 1992-06-23 | Graphics Technology International Inc. | Protective overcoats for diazo type layers |
Also Published As
Publication number | Publication date |
---|---|
GB1134943A (en) | 1968-11-27 |
DE1572076A1 (de) | 1970-02-12 |
NL6604532A (en)) | 1966-10-06 |
SE326102B (en)) | 1970-07-13 |
AT277752B (de) | 1970-01-12 |
BE678993A (en)) | 1966-09-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: SECURITY NATIONAL BANK, A NATIONAL BANKING ASSOCIA Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHASE MANHATTAN BANK, N.A. THE; A NATIONAL BANKING Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHEMICAL BANK, A BANKING INSTITUTION OF NY. Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CONTINENTAL ILLINOIS NATIONAL BANK & TRUST CO., OF Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: BANK OF CALIFORNIA N.A. THE; A NATIONAL BANKING AS Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 Owner name: CHEMICAL BANK, A BANKING INSTITUTION OF, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:KEUFFEL & ESSER COMPANY A.N.J. CORP;REEL/FRAME:003969/0808 Effective date: 19820323 |