US3375113A - Sensitizing planographic plates for photo-lithography - Google Patents
Sensitizing planographic plates for photo-lithography Download PDFInfo
- Publication number
- US3375113A US3375113A US225380A US22538062A US3375113A US 3375113 A US3375113 A US 3375113A US 225380 A US225380 A US 225380A US 22538062 A US22538062 A US 22538062A US 3375113 A US3375113 A US 3375113A
- Authority
- US
- United States
- Prior art keywords
- diazo compound
- photo
- plates
- sensitizing
- lithography
- 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
- 230000001235 sensitizing effect Effects 0.000 title description 4
- 238000000206 photolithography Methods 0.000 title description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- -1 Arom-atic Diazo Compounds Chemical class 0.000 description 1
- 101100367123 Caenorhabditis elegans sul-1 gene Proteins 0.000 description 1
- 241000252067 Megalops atlanticus Species 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/016—Diazonium salts or compounds
- G03F7/0166—Diazonium salts or compounds characterised by the non-macromolecular additives
Definitions
- This invention relates to the manufacture of photolithographic printing plates. It is more particularly concerned With an improved diazo wash solution for'treating the surface .of a planographic printing plate to make it photosensitive. k
- the present invention is based on the finding that photo-sensitive diazo compounds can be adequately stabilized without appreciably impairing their sensitivity by treatment with phosphoric acid.
- the photo-sensitivity of the diazo compounds treated with phosphoric acid is four or more times that of the sulfonated diazo compounds; yet plates prepared from the phosphonated compounds have been stored for over one and one half years without spoilage.
- the amount of phosphoric acid used to stabilize the diazo compounds is relatively high, in the range of 3.5 to 7.5 parts of weight per part of the diazo compound. This ratio is quite important. If lesser amounts are used, the stability imparted is insuflicient and the diazo compound ages poorly. If greater amounts are used, the ink receptivity of the developed surface is inadequate. The reason for this is not known with certainty. It is not clear at present what portion of the diazo compound is complexed, buffered, reacted with or the like to produce the stabilizing effect without adversely effecting sensitivity. Other mineral acids such as sulphuric and nitric are known to be less effective or deleterious at these concentrations.
- the diazo compound used in the practice of this invention is *diazotized para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal.
- An equal molar amount of formaldehyde is preferably used.
- the diazonium salt is preferably in water solution in a concentration in the range of 0.5 to 2 weight percent.
- the phosphoric acid is added by simple mixing to obtain the desired sensitizing wash solution.
- the wash solution can be applied to the hydrophilic surface of any suitable planographic printing plate, such as a clay-casein surface on a paper web that has been precoated with a barrier coating.
- a suitable planographic printing plate such as a clay-casein surface on a paper web that has been precoated with a barrier coating.
- Metal foils, plastic coated papers, plastic sheets, and the like can alse be used.
- the hydrophilic cellulosic type of coating described in US. 2,778,735 on any suitable base as described therein is preferred.
- the wash solution is applied in any convenient manner, e.g., roll coating, with an air knife, dip- Delaware 3,375,113 Patented Mar, 26, 9 8
- the negative was a halftone lithographic film negative (-150 lines/inch) with a Lithographic Technical Foundation sensitivity guide. The following results were obtained.
- the plates prepared with the diazo compound treated with 6.37 parts of phosphoric acid were compared to the plates prepared using the same diazo compound but sul- 1 It might be noted that the same type of planographic plates coated with the diazo compound unstabilized in any manner have a shelf life of less than a month.
- a presensitized printing plate comprising a base material having thereon a coating comprising 1) the double metal salt of the condensation product of a diazotized para-amino-diphenylamine and formaldehyde and (2) phosphoric acid.
- a photo-lithographic printing plate for use in planegraphic printing comprising a base sheet coated with a lithographic coating and sensitized with a diazo compound stabilized with in the range of 3.5 to 7.5 parts by weight of phosphoric acid per part by weight of said diazo compound, said diazo compound being diazotized para-amino-diphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal.
- a solution of a stabilized diazo compound for treating a planogra-phic printing plate to make it photo-sensitive comprising a water solution of diazotize-d para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal and in the range of 3.5 to 7.5 parts by weight thereon ofphosphoric acid per part by Weight of said diazo compound.
- a photo-sensitive planographic printing plate comprising a base having a planographic printing surface coated with in the range of 0.05 to 0.30 grams .per square meter of the evaporation product of a water solution of diazotized para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of zinc chloride, stabilized with in the range of 3.5 to 7.5 pants by weight of phosphoric acid per part by Weight of said diazo compound.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Printing Plates And Materials Therefor (AREA)
Description
3,375,113 SENSITIZING PL GRAPHIC PLATES FOR PHOTO-LITHOGRAPHY Towers Doggett, Westbrook, vMaine, assignor, by mesne assignments, to Scott Paper Company, County, Pa., a corporatio of Pennsylvania No Drawing. Filed'Sept. '21, 1962, Ser. No. 225,380
This invention relates to the manufacture of photolithographic printing plates. It is more particularly concerned With an improved diazo wash solution for'treating the surface .of a planographic printing plate to make it photosensitive. k
On difliculty with sensitizing photo-lithographic printing Plates With a P -sensit ve d ab co poun h b en that the diazo compound aged rapidly and within a few days became water insoluble and ink receptive. Various means have been used to make the diazo compounds more stable, such as sulfonation by means of sulphites as described in U.S. Patent 2,778,735. While the storage stability of plates sensitized by a sulfonate-d diazo compound is several months or more, the plates are not too sensitive to light and require considerable exposure. The ability of a sulfonated diazo compound to attract the oleaginous printing ink may be inadequate even after prolonged exposure to light. -It has usually been necessary to treat a developed plate with an oleophilic agent to improve the aflinity of the exposed diazo compound for the printing ink.
The present invention is based on the finding that photo-sensitive diazo compounds can be adequately stabilized without appreciably impairing their sensitivity by treatment with phosphoric acid. The photo-sensitivity of the diazo compounds treated with phosphoric acid is four or more times that of the sulfonated diazo compounds; yet plates prepared from the phosphonated compounds have been stored for over one and one half years without spoilage.
The amount of phosphoric acid used to stabilize the diazo compounds is relatively high, in the range of 3.5 to 7.5 parts of weight per part of the diazo compound. This ratio is quite important. If lesser amounts are used, the stability imparted is insuflicient and the diazo compound ages poorly. If greater amounts are used, the ink receptivity of the developed surface is inadequate. The reason for this is not known with certainty. It is not clear at present what portion of the diazo compound is complexed, buffered, reacted with or the like to produce the stabilizing effect without adversely effecting sensitivity. Other mineral acids such as sulphuric and nitric are known to be less effective or deleterious at these concentrations.
The diazo compound used in the practice of this invention is *diazotized para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal. An equal molar amount of formaldehyde is preferably used. The diazonium salt is preferably in water solution in a concentration in the range of 0.5 to 2 weight percent. The phosphoric acid is added by simple mixing to obtain the desired sensitizing wash solution.
The wash solution can be applied to the hydrophilic surface of any suitable planographic printing plate, such as a clay-casein surface on a paper web that has been precoated with a barrier coating. Metal foils, plastic coated papers, plastic sheets, and the like can alse be used. The hydrophilic cellulosic type of coating described in US. 2,778,735 on any suitable base as described therein is preferred. The wash solution is applied in any convenient manner, e.g., roll coating, with an air knife, dip- Delaware 3,375,113 Patented Mar, 26, 9 8
ping, spraying, and the like. In the range of 0:05 to 0.30 grams of the diazo compound (dry weight and excluding acid) per square meter of the surface will normally be used.
Example The ph o-sensiti mp u d used in thi ex mple wa d a otizs para-.am nod p s mins o d ns d i h n equa molar amount o f ldehyde an co ve t d o the doub e alt of zi c chl de- A 0 s w ig t p cen wa e solu ion of t is compo d wa m xed h an 8 percent solution of phosphoric acid in varying proportions. The solutions thus obtained were applied'by an air knife coater to a paper lithographic printing plate made as described in the example of UJS. 2,778,735, except that the phosphoric acid and diazo compound mixture was Insed in place vof the light sensitive coating of the patent. The amount of diazo compound applied was 0.15 grams/ per square meter. The plates were aged for four hours at 70 C. This is considered to be equal to about 6 months natural aging at room temperature. The aged plates were tested using a conventional offset lithographic press with Addressograph-Multigraph Company ML 36 ink and A-M Repelex diluted with water (1 part to 7 parts water).
The negative was a halftone lithographic film negative (-150 lines/inch) with a Lithographic Technical Foundation sensitivity guide. The following results were obtained.
Weight Ratio of Phos- Start-Up on phoric Acid (100%) to Press Printing Results Diazo Compound 0. Satisfactory. Unsatisfactory. 1.70 do Do. 2. 55 do Do. 8. 40 do D0. 4. 25 do Fairly satisfactory. 6. 10 do. Satisfactory. 6. 37 ..do Do. 8. 50 Do.
Plates treated with the 6.37 acid/diazo compound solution were stored for twenty months and then tested. The start-up, toning properties and fidelity of these plates were satisfactory.
The plates prepared with the diazo compound treated with 6.37 parts of phosphoric acid were compared to the plates prepared using the same diazo compound but sul- 1 It might be noted that the same type of planographic plates coated with the diazo compound unstabilized in any manner have a shelf life of less than a month.
Having thus described this invention, what is sought to be protected by Letters Patent is succinctly set forth in the following claims.
What is claimed is:
1. A presensitized printing plate comprising a base material having thereon a coating comprising 1) the double metal salt of the condensation product of a diazotized para-amino-diphenylamine and formaldehyde and (2) phosphoric acid.
2. A photo-lithographic printing plate for use in planegraphic printing comprising a base sheet coated with a lithographic coating and sensitized with a diazo compound stabilized with in the range of 3.5 to 7.5 parts by weight of phosphoric acid per part by weight of said diazo compound, said diazo compound being diazotized para-amino-diphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal.
3. A solution of a stabilized diazo compound for treating a planogra-phic printing plate to make it photo-sensitive comprising a water solution of diazotize-d para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of a divalent heavy metal and in the range of 3.5 to 7.5 parts by weight thereon ofphosphoric acid per part by Weight of said diazo compound.
4. A photo-sensitive planographic printing plate comprising a base having a planographic printing surface coated with in the range of 0.05 to 0.30 grams .per square meter of the evaporation product of a water solution of diazotized para-aminodiphenylamine condensed with formaldehyde and converted to the double salt of zinc chloride, stabilized with in the range of 3.5 to 7.5 pants by weight of phosphoric acid per part by Weight of said diazo compound.
References Cited UNITED STATES PATENTS 1,983,005 12/1934 Sakurai 9691 Zahn 96-91X May 260-191 Frost et a1. 9633 XR Neugebauer 96-33 XR Neugeb-auer et a1 9633 Brinnick et a1. .96-75 Seven et a1. 3633 XR FOREIGN PATENTS Great Britain.
OTHER REFERENCES 15 Saunders, K..H., The Arom-atic Diazo Compounds,"
2nd ed., Arnold and Co., London, 1949, pp. 76-80.
J. TRAVIS BROWN, Acting Primary Examiner.
NORMAN G. TO-RCHIN, Examiner. R. L. STONE, Assistant Examiner.
Claims (1)
1. A PRESENSITIZED PRINTING PLATE COMPRISING A BASE MATERIAL HAVING THEREON A COATING COMPRISING (1) THE DOUBLE METAL SALT OF THE CONDENSATION PRODUCT OF A DIAZOTIZED PARA-AMINO-DIPHENYLAMINE AND FORMALDEHYDE AND (2) PHOSPHORIC ACID.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US225380A US3375113A (en) | 1962-09-21 | 1962-09-21 | Sensitizing planographic plates for photo-lithography |
| GB36371/63A GB994605A (en) | 1962-09-21 | 1963-09-16 | Improvements relating to photo-lithographic printing plates and solutions for sensitizing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US225380A US3375113A (en) | 1962-09-21 | 1962-09-21 | Sensitizing planographic plates for photo-lithography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3375113A true US3375113A (en) | 1968-03-26 |
Family
ID=22844636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US225380A Expired - Lifetime US3375113A (en) | 1962-09-21 | 1962-09-21 | Sensitizing planographic plates for photo-lithography |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3375113A (en) |
| GB (1) | GB994605A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510307A (en) * | 1965-01-02 | 1970-05-05 | Kalle Ag | Process for the preparation of a printing plate presensitized with a diazonium salt |
| US5424165A (en) * | 1991-12-17 | 1995-06-13 | Fuji Photo Film Co., Ltd. | Diazo resin light-sensitive composition containing organic compound having at least 3 carboxyl groups |
| JP3477389B2 (en) | 1993-06-21 | 2003-12-10 | ヘレナ ラボラトリーズ コーポレーション | How to analyze a liquid sample |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1983005A (en) * | 1927-05-14 | 1934-12-04 | Zaiden Hojin Rikagaku Kenkyujo | Positive sensitized paper |
| US2100063A (en) * | 1931-12-09 | 1937-11-23 | Kaile & Co Ag | Process for the production of tanned pictures |
| US2266229A (en) * | 1941-12-16 | Ijnitfffc | ||
| GB640491A (en) * | 1947-04-02 | 1950-07-19 | Gen Aniline & Film Corp | Diazotype photoprinting material comprising amine salts of sulfonic acid containing azo coupling components |
| US2624673A (en) * | 1948-03-01 | 1953-01-06 | Warren S D Co | Photosensitive printing plate having a light-sensitive coating consisting of a nonprotein colloid, a phosphate, and a chromium compound |
| US2679498A (en) * | 1954-05-25 | Atent office | ||
| US2687958A (en) * | 1949-05-14 | 1954-08-31 | Azoplate Corp | Light-sensitive layers for the printing industry |
| US2739889A (en) * | 1950-12-08 | 1956-03-27 | Azoplate Corp | Process for fixing lithographic diazotype printing foils having been exposed to light |
| US2778735A (en) * | 1953-05-22 | 1957-01-22 | Warren S D Co | Photo-sensitive coated paper plate for photo-lithography |
-
1962
- 1962-09-21 US US225380A patent/US3375113A/en not_active Expired - Lifetime
-
1963
- 1963-09-16 GB GB36371/63A patent/GB994605A/en not_active Expired
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2266229A (en) * | 1941-12-16 | Ijnitfffc | ||
| US2679498A (en) * | 1954-05-25 | Atent office | ||
| US1983005A (en) * | 1927-05-14 | 1934-12-04 | Zaiden Hojin Rikagaku Kenkyujo | Positive sensitized paper |
| US2100063A (en) * | 1931-12-09 | 1937-11-23 | Kaile & Co Ag | Process for the production of tanned pictures |
| GB640491A (en) * | 1947-04-02 | 1950-07-19 | Gen Aniline & Film Corp | Diazotype photoprinting material comprising amine salts of sulfonic acid containing azo coupling components |
| US2624673A (en) * | 1948-03-01 | 1953-01-06 | Warren S D Co | Photosensitive printing plate having a light-sensitive coating consisting of a nonprotein colloid, a phosphate, and a chromium compound |
| US2687958A (en) * | 1949-05-14 | 1954-08-31 | Azoplate Corp | Light-sensitive layers for the printing industry |
| US2739889A (en) * | 1950-12-08 | 1956-03-27 | Azoplate Corp | Process for fixing lithographic diazotype printing foils having been exposed to light |
| US2778735A (en) * | 1953-05-22 | 1957-01-22 | Warren S D Co | Photo-sensitive coated paper plate for photo-lithography |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3510307A (en) * | 1965-01-02 | 1970-05-05 | Kalle Ag | Process for the preparation of a printing plate presensitized with a diazonium salt |
| US5424165A (en) * | 1991-12-17 | 1995-06-13 | Fuji Photo Film Co., Ltd. | Diazo resin light-sensitive composition containing organic compound having at least 3 carboxyl groups |
| JP3477389B2 (en) | 1993-06-21 | 2003-12-10 | ヘレナ ラボラトリーズ コーポレーション | How to analyze a liquid sample |
Also Published As
| Publication number | Publication date |
|---|---|
| GB994605A (en) | 1965-06-10 |
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