CA1061158A - Light sensitive layer containing o-naphthoquinone diazide, resin and aminoalkoxysilane - Google Patents
Light sensitive layer containing o-naphthoquinone diazide, resin and aminoalkoxysilaneInfo
- Publication number
- CA1061158A CA1061158A CA234,234A CA234234A CA1061158A CA 1061158 A CA1061158 A CA 1061158A CA 234234 A CA234234 A CA 234234A CA 1061158 A CA1061158 A CA 1061158A
- Authority
- CA
- Canada
- Prior art keywords
- printing plate
- amino
- resin
- plate according
- alkoxy silane
- 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
Links
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
- G03F7/075—Silicon-containing compounds
- G03F7/0751—Silicon-containing compounds used as adhesion-promoting additives or as means to improve adhesion
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Printing Plates And Materials Therefor (AREA)
Abstract
Abstract of the Disclosure This invention relates to an improvement in a presensitized print-ing plate having, on an electrolytically oxidized surface of an aluminum support, a light-sensitive copying layer containing an o-naphthoquinone diazide compound and at least one resin selected from the group con-sisting of a novolak and a resol, the improvement comprising the inclusion in said copying layer of an amino alkoxy silane compound of the formula
Description
PRINTING PLATE PRESENSITIZED WITH AN
O-NAPHTHOQUINONE-DIAZIDE COMPOUND
This invention relates to a printing plate presensitized by means of an o-naphthoquinone diaæide compound, which plate contains a novo-lak or a resol resin in its copying layer and includes an aluminum support with an electrolyticalLy oxidized coated surface, the printing plate exhibiting an improved adhesion of the copying layer to the oxi-dized surface of the support.
Printing plates of the above-described type sensitized by means of o-quinone diazide compounds are known. The adheslon of their resin-containing copying layers to the electrolyticaLly oxidlzed aluminum sur-faces is good. Nevertheless, an improvement of the adhesion is s1:ill desirable, because pnnting forms prepated from such printing plates yield longer runs. It already has been proposed to further improve the adhesion between the copying layer and the support in printing plates of this type by a further treatment of the electrolytically oxidized aluminum surfaces, but this means that an additional process step is requLred for the preparation of the printing plate, which increases the cost of the plate and renders it more difficult to control the manufacturing process.
- It is the object of the present invention to provide a presensitiz-ed printing plate of the above-described type in which the adhesion of the copying layer to the oxidized aluminum surface is improved in a simpler manner. In the presensitized printing plate according to the presentinvention, the copying layer contains an amino alkoxy silane compound of the following formula R - (CH ) - Si - (OR')
O-NAPHTHOQUINONE-DIAZIDE COMPOUND
This invention relates to a printing plate presensitized by means of an o-naphthoquinone diaæide compound, which plate contains a novo-lak or a resol resin in its copying layer and includes an aluminum support with an electrolyticalLy oxidized coated surface, the printing plate exhibiting an improved adhesion of the copying layer to the oxi-dized surface of the support.
Printing plates of the above-described type sensitized by means of o-quinone diazide compounds are known. The adheslon of their resin-containing copying layers to the electrolyticaLly oxidlzed aluminum sur-faces is good. Nevertheless, an improvement of the adhesion is s1:ill desirable, because pnnting forms prepated from such printing plates yield longer runs. It already has been proposed to further improve the adhesion between the copying layer and the support in printing plates of this type by a further treatment of the electrolytically oxidized aluminum surfaces, but this means that an additional process step is requLred for the preparation of the printing plate, which increases the cost of the plate and renders it more difficult to control the manufacturing process.
- It is the object of the present invention to provide a presensitiz-ed printing plate of the above-described type in which the adhesion of the copying layer to the oxidized aluminum surface is improved in a simpler manner. In the presensitized printing plate according to the presentinvention, the copying layer contains an amino alkoxy silane compound of the following formula R - (CH ) - Si - (OR')
2 n I m .~
?~ 8 wherein R is an amino group or an aminoalkyl amino group with 1 to 4 carbon atoms, R' is an alkyl group with 1 to 4 carbon atoms, and R" is either the methyl group or R-(CH2), and wherein m is 2 or 3, n isl, 2, or3, and p is either 0 or 1, and m and p, taken together, being 3, - 10 by which the adhesion of the copying layer to the oxidized surface of the support is improved.
Examples of suitable amino alkoxy silane compounds which may be present in the copying layer to improve the adhesion between the copying layer and the support are the following compounds:
!~ aminomethyl triethoxy silane NH2-CH2-Si- (OC2H~)3 ,13-aminoethyl triethoxy silane NH2-(CH2)2-Si-(OC2H5)3 ~-aminopropyl triethoxy silane NH2-(CH2)3-Si-(oc2H5)3 ~-aminopropyl trimethoxy silane N H2 ~ (CH2) 3 -Si- (OCH3) 3 N-(~-aminoethyl)-~-aminopropyl trimethoxy silane NH2 CH2-CH2-NH-(CH2)3-Si-(ocH ) The amino alkoxy silane compound contained in the copying layer is a bi-fun tional compound. Probably, it combines on the one hand with the oxidized surface of the support and on the other hand with the novolak or resol, thus improving the adhesion between the copying layer and the aluminum surface, It is assumed that at least part of the amino alkoxy silane compound improving the adhesion of the copying layer to the surface of the support is attached to the novolak or resol and to the surface of the support. The proportion of amino alkoxy silane compound in the copying layer is very small. It ranges from 0. 3 to 5 per cent by weight, preferably from 0 . 8 to 1. 5 per cent by weight, based on the weight of the total quantity of resin contained in the copying layer.
The total ~uantity of resin is composed entirely or substantially entirely of novolak or resol or of a mixture of novolak and resol. Other resins, if any, are present in minor quantities only, i.e. not more than 10 per cent by weight, calculated on the total quantity of resin present.
Epoxy resin, pplyvinyl ether, polyvin~l acetate, and polyvinyl acetal I
are examplary of resins of which only minor quantities may be present~
The printing plates prepared in accordance with the present in-vention have the advantage that from the printing forms obtained there-from, longer runs may be obtained until they are worn off than from simi-lar printing plates containing no amino alkoxy silane compound In the copying layer. Printing plates containing a dye in the copying layer, in order that the developed printing image of the printing form obtained is more visible, have still another advantage, viz. if corrections should become necessary, the corrected areas of the printing forms obtained from the printing plates according to the invention have the same appear-ance as other background areas, whereas in the case of printing forms made from similar printing plates containing no amino alkoxy silane compound in the copying layer, the corrected areas differ from the re-maining background areas~ so that the entire image assumes a mottled appearance which impedes visual fault control of the printing form. As compared with other known printing plates of the same type, in which the improved adhesion is produced by an addLtlonal process step, the prlnting plates according to the invention have the advantage that thelr manufas~ture is slmpler and can be con-trolled more easlly.
The following examples wlll further lllustrate the lnvention:
Example 1 An eleGtro-chemlcally roughened and anodlzed surface of an - ~ aluminum foll with an oxide layer welghing about 3 grams pe~ square meter was whirler-coated wlth a light-sensltlve layer of the following composition. - The quantities stated are ln per cent by welght, -6.6% of a novolak ("Alnovol PN 429"), 1.1% of the cumyl phenol ester of naphtl4oquinone-` - (1, 2) -dlazide- (2) -sulfonic acid- (4), ~. . .
0.6% of 2, 2'-bis~naphthoquinone-(1, 2)-dlazide-(2)-sulfonyloxy-(5) }dinaphthyl-(l, 1') methane, 0,08% of crystal vlolet, 0,24% of 1, 2-naphthoqulnone-diazide-(2)-sulfo chloride~
0.066% of y-aminopropyl trlethoxy silane, and 91.314% of a solvent mixture of 80 per cent by weight ; ~ ~ 20 of glycol monomethyl ether and 20 per cent by weight of butyl acetate, The coated plate was dried at 120C.
For the preparatlon of an offset prlnting form, the resultlng printing plate was exposed, developed wlth an alkallne developer, and then corrected. The plate was then used for prlntlng in an offset ma-chlne ("Multillth 1850"), As cornpared with a prlntlng form obtained from a slmilar prlntlng plate whlch contained no amlno alkoxy silane compound, the length of the run was increased by at least 40%, viz.
159, 000 coples as compared wlth 111, 000 coples.
ale~narl~
Example 2 A light-sensltlve offset printlng plate was produced as descrlbed ln Example 1, using the following formulation:
6.3% of novolak ("Alnovol PN 430"), 1.48% of the condensation product of 2, 3, 4-trihydroxy-~. !
benzophenone and naphthoqulnone-(l, 2)-dlazlde-~: (2~-sulfochlorlde-(5), Q, 7% of 2, 2 ' -bis ~ naphthoquinone- (1, 2~ -dlazlde- (2) -sulfonyloxy-(5) ~dlnaphthyl-(1, 1')-methane, - 10 0.3% of a resol resin ("Phenodur PR 897"), ~t ~ ~
~; ~ 0.2% of 1, 2-naphtho~uinone diazlde-(2)-sulfochlorlde, 0.066% of N-(~-amlnoethyl)-7-aminopropyl-trimethoxy-silane, ., 0.084% of me-thyl violet, and 90, 8 7% of the solvent mlxture used ln Example 1 .
, ~ A prlnting form was prepared ln the usual manner and used for prirltlng in an offset machine of the type "Heidelberger offset rll,achine KOR" . ~ prlnting form containlng no amino alkoxy silane ylelded a run of 170, 000 copies, whereas a plate containing such an a~ditlon yielded a run of 260, 000 prints, which corresponds ~o an increase of more than 50 per cent.
Example 3 A light-sensltlve prlnting plate was prepared as descrlbed in Example 1, using the following formulation:
6.3% of novolak (as ln Example 1), 0.~% of an epoxy resin ("Epikote 1001", a product of Deutsche Shell Chemle CmbH.), 0,3% of a resol resln (as in Example 2), r~dema~ ~ 5 _ 1O48% of the condensation product of 2,3,4~-trihydroxy-benzophenone and naphthoquinone-(1,2)-diazide- (2) -sulfonic acid- (5), 0 . 7% of 2, 2' ~bis-[naphthoquinone-(l, 2)-diazide-(2)-sulEonyl-oxy- (5)~ -dinaphthyl- (1 ,1 ' ) -methane, 0.2% of 1,2-naphthoquinone-diazide-(2)-sulfochloride-(4), 0 . 088% of methyl violet, O.066% of N-(,B-aminoethyl)-~-aminopropyl-trimethoxy silane, and 90.466Yo of the solvent mixture used in Example 1.
The printing form obtained from the resulting printing plate was used :Eor printing on a "Heidelberger GTO" offset machine.
The run obtainable was increased by rou~hly 25%, viz. 225,000 copies as compared with 178,000 copies. ~ I
The surface of an aluminum foil was first silicated in an alkaline solution by an electro-chemical process and then anodized, and the re-sulting plate was then coated, as described in Example 1, wLth a light-sensitlve layer of the following composition:
6.6% of novolak (as in Example l), 1.1% of the condensation product of 2,3,4-trihydroxy-benzophenone and naphthoquinone- (1, 2~-diazide-(2)-sulfonic acid-(5)r 0.55% of 2,2' bis-~naphthoquinone-(1,2~-diazide-(2)-sulfonyl~oxy- (5)~ -dinaphthyl- (1 ,1 ' ) -methane, 0 . 078% of crystal violet, O . 24% of 1, 2-naphthoquinone-diazide-(2)-sulfochloride, O . 049% of N - (,B-aminoethyl)- ~-aminopropyl-tri-methoxy silane, and 91.383% of the solvent mixture used in Example 1.
The resulting printing form yielded a run which was increased by 45%, i . e ., 1 46, 000 copies a s compared with 98, 000 copies .
It will be obvious to those skilled in the art that many modifi-,~ , cations may be made within the scope of the present invention withoutdeparting from the spirit thereof, and the invention includes all such modification s .
?~ 8 wherein R is an amino group or an aminoalkyl amino group with 1 to 4 carbon atoms, R' is an alkyl group with 1 to 4 carbon atoms, and R" is either the methyl group or R-(CH2), and wherein m is 2 or 3, n isl, 2, or3, and p is either 0 or 1, and m and p, taken together, being 3, - 10 by which the adhesion of the copying layer to the oxidized surface of the support is improved.
Examples of suitable amino alkoxy silane compounds which may be present in the copying layer to improve the adhesion between the copying layer and the support are the following compounds:
!~ aminomethyl triethoxy silane NH2-CH2-Si- (OC2H~)3 ,13-aminoethyl triethoxy silane NH2-(CH2)2-Si-(OC2H5)3 ~-aminopropyl triethoxy silane NH2-(CH2)3-Si-(oc2H5)3 ~-aminopropyl trimethoxy silane N H2 ~ (CH2) 3 -Si- (OCH3) 3 N-(~-aminoethyl)-~-aminopropyl trimethoxy silane NH2 CH2-CH2-NH-(CH2)3-Si-(ocH ) The amino alkoxy silane compound contained in the copying layer is a bi-fun tional compound. Probably, it combines on the one hand with the oxidized surface of the support and on the other hand with the novolak or resol, thus improving the adhesion between the copying layer and the aluminum surface, It is assumed that at least part of the amino alkoxy silane compound improving the adhesion of the copying layer to the surface of the support is attached to the novolak or resol and to the surface of the support. The proportion of amino alkoxy silane compound in the copying layer is very small. It ranges from 0. 3 to 5 per cent by weight, preferably from 0 . 8 to 1. 5 per cent by weight, based on the weight of the total quantity of resin contained in the copying layer.
The total ~uantity of resin is composed entirely or substantially entirely of novolak or resol or of a mixture of novolak and resol. Other resins, if any, are present in minor quantities only, i.e. not more than 10 per cent by weight, calculated on the total quantity of resin present.
Epoxy resin, pplyvinyl ether, polyvin~l acetate, and polyvinyl acetal I
are examplary of resins of which only minor quantities may be present~
The printing plates prepared in accordance with the present in-vention have the advantage that from the printing forms obtained there-from, longer runs may be obtained until they are worn off than from simi-lar printing plates containing no amino alkoxy silane compound In the copying layer. Printing plates containing a dye in the copying layer, in order that the developed printing image of the printing form obtained is more visible, have still another advantage, viz. if corrections should become necessary, the corrected areas of the printing forms obtained from the printing plates according to the invention have the same appear-ance as other background areas, whereas in the case of printing forms made from similar printing plates containing no amino alkoxy silane compound in the copying layer, the corrected areas differ from the re-maining background areas~ so that the entire image assumes a mottled appearance which impedes visual fault control of the printing form. As compared with other known printing plates of the same type, in which the improved adhesion is produced by an addLtlonal process step, the prlnting plates according to the invention have the advantage that thelr manufas~ture is slmpler and can be con-trolled more easlly.
The following examples wlll further lllustrate the lnvention:
Example 1 An eleGtro-chemlcally roughened and anodlzed surface of an - ~ aluminum foll with an oxide layer welghing about 3 grams pe~ square meter was whirler-coated wlth a light-sensltlve layer of the following composition. - The quantities stated are ln per cent by welght, -6.6% of a novolak ("Alnovol PN 429"), 1.1% of the cumyl phenol ester of naphtl4oquinone-` - (1, 2) -dlazide- (2) -sulfonic acid- (4), ~. . .
0.6% of 2, 2'-bis~naphthoquinone-(1, 2)-dlazide-(2)-sulfonyloxy-(5) }dinaphthyl-(l, 1') methane, 0,08% of crystal vlolet, 0,24% of 1, 2-naphthoqulnone-diazide-(2)-sulfo chloride~
0.066% of y-aminopropyl trlethoxy silane, and 91.314% of a solvent mixture of 80 per cent by weight ; ~ ~ 20 of glycol monomethyl ether and 20 per cent by weight of butyl acetate, The coated plate was dried at 120C.
For the preparatlon of an offset prlnting form, the resultlng printing plate was exposed, developed wlth an alkallne developer, and then corrected. The plate was then used for prlntlng in an offset ma-chlne ("Multillth 1850"), As cornpared with a prlntlng form obtained from a slmilar prlntlng plate whlch contained no amlno alkoxy silane compound, the length of the run was increased by at least 40%, viz.
159, 000 coples as compared wlth 111, 000 coples.
ale~narl~
Example 2 A light-sensltlve offset printlng plate was produced as descrlbed ln Example 1, using the following formulation:
6.3% of novolak ("Alnovol PN 430"), 1.48% of the condensation product of 2, 3, 4-trihydroxy-~. !
benzophenone and naphthoqulnone-(l, 2)-dlazlde-~: (2~-sulfochlorlde-(5), Q, 7% of 2, 2 ' -bis ~ naphthoquinone- (1, 2~ -dlazlde- (2) -sulfonyloxy-(5) ~dlnaphthyl-(1, 1')-methane, - 10 0.3% of a resol resin ("Phenodur PR 897"), ~t ~ ~
~; ~ 0.2% of 1, 2-naphtho~uinone diazlde-(2)-sulfochlorlde, 0.066% of N-(~-amlnoethyl)-7-aminopropyl-trimethoxy-silane, ., 0.084% of me-thyl violet, and 90, 8 7% of the solvent mlxture used ln Example 1 .
, ~ A prlnting form was prepared ln the usual manner and used for prirltlng in an offset machine of the type "Heidelberger offset rll,achine KOR" . ~ prlnting form containlng no amino alkoxy silane ylelded a run of 170, 000 copies, whereas a plate containing such an a~ditlon yielded a run of 260, 000 prints, which corresponds ~o an increase of more than 50 per cent.
Example 3 A light-sensltlve prlnting plate was prepared as descrlbed in Example 1, using the following formulation:
6.3% of novolak (as ln Example 1), 0.~% of an epoxy resin ("Epikote 1001", a product of Deutsche Shell Chemle CmbH.), 0,3% of a resol resln (as in Example 2), r~dema~ ~ 5 _ 1O48% of the condensation product of 2,3,4~-trihydroxy-benzophenone and naphthoquinone-(1,2)-diazide- (2) -sulfonic acid- (5), 0 . 7% of 2, 2' ~bis-[naphthoquinone-(l, 2)-diazide-(2)-sulEonyl-oxy- (5)~ -dinaphthyl- (1 ,1 ' ) -methane, 0.2% of 1,2-naphthoquinone-diazide-(2)-sulfochloride-(4), 0 . 088% of methyl violet, O.066% of N-(,B-aminoethyl)-~-aminopropyl-trimethoxy silane, and 90.466Yo of the solvent mixture used in Example 1.
The printing form obtained from the resulting printing plate was used :Eor printing on a "Heidelberger GTO" offset machine.
The run obtainable was increased by rou~hly 25%, viz. 225,000 copies as compared with 178,000 copies. ~ I
The surface of an aluminum foil was first silicated in an alkaline solution by an electro-chemical process and then anodized, and the re-sulting plate was then coated, as described in Example 1, wLth a light-sensitlve layer of the following composition:
6.6% of novolak (as in Example l), 1.1% of the condensation product of 2,3,4-trihydroxy-benzophenone and naphthoquinone- (1, 2~-diazide-(2)-sulfonic acid-(5)r 0.55% of 2,2' bis-~naphthoquinone-(1,2~-diazide-(2)-sulfonyl~oxy- (5)~ -dinaphthyl- (1 ,1 ' ) -methane, 0 . 078% of crystal violet, O . 24% of 1, 2-naphthoquinone-diazide-(2)-sulfochloride, O . 049% of N - (,B-aminoethyl)- ~-aminopropyl-tri-methoxy silane, and 91.383% of the solvent mixture used in Example 1.
The resulting printing form yielded a run which was increased by 45%, i . e ., 1 46, 000 copies a s compared with 98, 000 copies .
It will be obvious to those skilled in the art that many modifi-,~ , cations may be made within the scope of the present invention withoutdeparting from the spirit thereof, and the invention includes all such modification s .
Claims (9)
1. In a presensitized printing plate having, on an electrolytically oxidized surface of an aluminum support, a light-sensitive copying layer containing an o-naphthoquinone diazide compound and at least one resin selected from the group consisting of a novolak and a resol, the improvement comprising the inclusion in said copying layer of an amino alkoxy silane compound of the formula wherein R is an amino group or an amino alkyl-amino group with 1 to 4 carton atoms, R' is an alkyl group with 1 to 4 carbon atoms, and R" is either the methyl group or R-(CH2)n, and wherein m is 2 or 3 , n is 1, 2, or 3, and p is 0 or 1, and m and p, taken together, being 3, whereby the adhesion of the copying layer to the oxidized surface of the support is increased.
2. A presensitized printing plate according to claim 1 in which the copying layer contains about 2 to 9 parts by weight of resin per part by weight of o-naphthoquinone diazide compound and at least about 90 per cent by weight of the resin is a novolak or a resol resin, or a mixture thereof.
3. A presensitized printing plate according to claim 2 in which the copying layer contains about 0.3 to 5 per cent by weight of the amino alkoxy silane compound, calculated on the total quantity of resin con-tained in the layer.
4. A presensitized printing plate according to claim 2 in which the copying layer contains about 0.8 to 1.5 per cent by weight of the amino alkoxy silane compound, calculated on the total quantity of resin con-tained in the layer.
5. A presensitized printing plate according to claim 1 in which the amino alkoxy silane compound is .gamma.-aminopropyl triethoxy silane.
6. A presensitized printing plate according to claim 1 in which the amino alkoxy silane compound is N-(.beta.-aminoethyl)-.gamma.-aminopropyl-trimethoxy silane.
7. A presensitized printing plate according to claim 1 in which the amino alkoxy silane compound is aminomethyl triethoxy silane.
8. A presensitized printing plate according to claim 1 in which the amino alkoxy silane compound is .gamma.-aminoethyl triethoxy silane.
9. A presensitized printing plate according to claim 1 in which the amino alkoxy silane compound is .gamma.-aminopropyl trimethoxy silane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2441315A DE2441315A1 (en) | 1974-08-29 | 1974-08-29 | PRESSURE PLATE PRESENSITIZED WITH O-NAPHTHOQUINONDIAZIDE COMPOUND |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061158A true CA1061158A (en) | 1979-08-28 |
Family
ID=5924350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA234,234A Expired CA1061158A (en) | 1974-08-29 | 1975-08-27 | Light sensitive layer containing o-naphthoquinone diazide, resin and aminoalkoxysilane |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5152002A (en) |
| BE (1) | BE832775A (en) |
| BR (1) | BR7505522A (en) |
| CA (1) | CA1061158A (en) |
| DE (1) | DE2441315A1 (en) |
| DK (1) | DK387175A (en) |
| FR (1) | FR2283461A1 (en) |
| GB (1) | GB1514552A (en) |
| IE (1) | IE41520B1 (en) |
| IT (1) | IT1041533B (en) |
| LU (1) | LU73261A1 (en) |
| NL (1) | NL7510061A (en) |
| SE (1) | SE405049B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2034911B (en) * | 1978-10-26 | 1983-02-09 | Toray Industries | Dry planographic printing plate |
| FR2478641A1 (en) * | 1980-03-24 | 1981-09-25 | Rhone Poulenc Ind | Sulphonyl oxy-di:oxa-1,4-oxo-aza-tri:alkoxy-silyl hydrocarbyl benzene - useful photosensitisers in photoresist compsns. |
| US4400100A (en) * | 1981-03-02 | 1983-08-23 | International Business Machines Corp. | Four layered ribbon for electrothermal printing |
| DE3473359D1 (en) * | 1983-06-29 | 1988-09-15 | Fuji Photo Film Co Ltd | PHOTOSOLUBILIZABLE COMPOSITION |
| JPH04161957A (en) * | 1990-10-24 | 1992-06-05 | Nippon Paint Co Ltd | Photopolymerizative compound and sensitive planography print plate |
| JP2003119344A (en) | 2001-10-12 | 2003-04-23 | Shin Etsu Chem Co Ltd | Hybrid compound, resist material and method of forming pattern |
| JP5407563B2 (en) * | 2008-07-04 | 2014-02-05 | Ｊｓｒ株式会社 | Positive radiation sensitive resin composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS494851B1 (en) * | 1968-04-26 | 1974-02-04 | ||
| US3615538A (en) * | 1968-08-02 | 1971-10-26 | Printing Dev Inc | Photosensitive printing plates |
| JPS5119982B2 (en) * | 1972-01-26 | 1976-06-22 | ||
| FR2193864B1 (en) * | 1972-07-31 | 1974-12-27 | Rhone Poulenc Sa |
-
1974
- 1974-08-29 DE DE2441315A patent/DE2441315A1/en not_active Ceased
-
1975
- 1975-08-26 BE BE159492A patent/BE832775A/en not_active IP Right Cessation
- 1975-08-26 NL NL7510061A patent/NL7510061A/en not_active Application Discontinuation
- 1975-08-27 LU LU73261A patent/LU73261A1/xx unknown
- 1975-08-27 SE SE7509509A patent/SE405049B/en unknown
- 1975-08-27 CA CA234,234A patent/CA1061158A/en not_active Expired
- 1975-08-27 IT IT51079/75A patent/IT1041533B/en active
- 1975-08-27 GB GB35340/75A patent/GB1514552A/en not_active Expired
- 1975-08-27 IE IE1872/75A patent/IE41520B1/en unknown
- 1975-08-28 FR FR7526479A patent/FR2283461A1/en active Granted
- 1975-08-28 JP JP50104489A patent/JPS5152002A/en active Pending
- 1975-08-28 BR BR7505522*D patent/BR7505522A/en unknown
- 1975-08-28 DK DK387175A patent/DK387175A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE405049B (en) | 1978-11-13 |
| GB1514552A (en) | 1978-06-14 |
| IE41520L (en) | 1976-02-29 |
| DK387175A (en) | 1976-03-01 |
| DE2441315A1 (en) | 1976-03-11 |
| BE832775A (en) | 1976-02-26 |
| IT1041533B (en) | 1980-01-10 |
| JPS5152002A (en) | 1976-05-08 |
| LU73261A1 (en) | 1977-04-15 |
| IE41520B1 (en) | 1980-01-16 |
| NL7510061A (en) | 1976-03-02 |
| FR2283461B1 (en) | 1978-04-07 |
| FR2283461A1 (en) | 1976-03-26 |
| BR7505522A (en) | 1976-08-03 |
| SE7509509L (en) | 1976-03-01 |
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