GB2094015A - Non-silver, positive-working, radiation-sensitive composition - Google Patents
Non-silver, positive-working, radiation-sensitive composition Download PDFInfo
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- GB2094015A GB2094015A GB8204901A GB8204901A GB2094015A GB 2094015 A GB2094015 A GB 2094015A GB 8204901 A GB8204901 A GB 8204901A GB 8204901 A GB8204901 A GB 8204901A GB 2094015 A GB2094015 A GB 2094015A
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- United Kingdom
- Prior art keywords
- radiation
- composition
- sensitive
- composition according
- positive
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- 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
- G03F7/022—Quinonediazides
- G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Anon-silver, positive-working, essentially alkali-insoluble, radiation-sensitive composition, which becomes alkali-soluble on exposure to radiation, comprises a non-silver, positive-acting, essentially alkali-insoluble radiation-sensitive component, a radiation absorbing component and an essentially alkali-soluble polymeric binder. A radiation-sensitive element comprises a transparent substrate coated with the radiation-sensitive composition. A duplicating film is prepared by exposing the composition through the substrate and then image-wise exposing the composition through a mask in front of the composition followed by treatment with an alkaline developer to remove those areas of the composition subjected to both exposures.
Description
SPECIFICATION
Non-silver, positive-working, radiationsensitive composition
This invention relates to positive-working, radiation-sensitive compositions that are free of silver and to elements formed by coating such compositions, and to duplicating films prepared from such elements. Compositions of this general type that are free of silver are often termed non-silver containing compositions.
In the graphic arts field a lithographic printing plate is produced by imagewise-exposure of a presenitised plate, comprising a substrate overcoated with a positive- or negative-working radiationsensitive composition, to radiation followed by development. The imagewise-exposure is effected by passing radiation through a mask, comprising a transparent film having thereon areas transparent or opaque to the impressed radiation, to the presensitised plates.
In the case of a negative plate that has been exposed to light through a negative transparency, the light-sensitive material, commonly a diazo compound, is caused to harden and thereby become insoluble in a desensitising solution applied to the plates after light exposure for the purpose of removing that part of the light-sensitive coating which, because it was protected from the light of the negative, was not light-hardened. The light-hardened surface of a negative plate will be the oleophilic surface compatible with the greasy ink and is called the "image area", the surface from which the nonhardened light-sensitive material has been removed by a desensitiser will be, or can be converted to, a hydrophilic surface having little affinity for the greasy ink and is called the "non-image" area.
A positive plate is generally one upon which the non-image area is the portion of the light-sensitive diazo compound exposed to light while the unexposed portion is either oleophilic or adapted to be converted by chemical reaction to a hardened oleophilic ink-receptive image area.
It is known to use duplicating masks comprising transparent substrates, a first surface of which was overcoated with silver containing compositions which were image-wise exposed to radiation and then developed whereby the coatings in the unexposed areas were removed permitting transmission of radiation while the exposed areas became opaque precluding transmission of radiation upon imagewise exposure of a presensitised plate through the mask.
While the masks prepared in this manner are of excellent quality they are very expensive due to the high cost of silver. Thus, there has been considerable research directed to producing duplicating films which are not based in silver content.
A non-silver containing element for production of
masking films, as described in Japanese Patent 76-69627, comprises a double layered coating on a transparent substrate, one layer of which in contact with the substrate comprises a component opaque to the radiation and the other layer overlying said opaque layer comprises a radiation-sensitive component. After development there remains transparent areas of the original elements which were not exposed and from which the soluble photosensitive and opaque layers have been removed and the exposed areas comprising substrate coated with the opaque layer and overcoated with the transparent, light-hardened layer. However, these coatings are generally thick whereby the resolution of the resultant film is decreased.Japanese Patent 76-135691 described another non-silver containing element comprising a double layered coating wherein the radiation-opaque layer comprises a vacuum deposited metal which must be etched in order to permit, after exposure and development of the exposed radiation-sensitive layer, passage of radiation during exposure of the pre-sensitised lithographic plate.
These elements require long exposure times and the etching process releases metal ions which create disposaiprnblems. In the process described in U.S.
Patent 4,149,888 the photo-sensitive element comprises a transparent radiation-sensitive element and an ammonia activated coupling agent. According to that invention the element is imagewise exposed and developed after which the transparent image is rendered opaque by exposure to ammonia fumes whereby the unexposed transparent radiationsensitive component is caused to couple with the coupling agent to form a radiation-opaque product.
That process, and therefore the photosensitive element, has the disadvantage of handling and disposal of noxious fumes. Yet another non-silver containing element is the peel apart system described in Japanese Patent 79-104902 which is based on a decrease in adhesive strength at photosensitive componentsubstrate interfaces upon imagewise exposure to radiation. Those systems have the disadvantage of poor resolution.
A composition according to the invention is free of silver and is a positive-working, radiation-sensitive composition and is alkali insoluble but is rendered alkali soluble upon exposure to the radiation and comprises at least one positive-working, radiationsensitive, essentially alkali-insoluble component, at least one radiation absorbing component and at least one alkali soluble polymeric binder.
By the invention it is possible to provide a low cost substitute for silver-containing composition and which may be used to prepare radiation-sensitive elements that are convertible into duplicating masks for the production of lithographic printing plates. By the invention it is possible to overcome the disadvantages of the previously known non-silver containing elements and yet it is possible to provide masks of quality similar to the quality of the more expensive silver-containing masks.
Suitable positive-acting radiation-sensitive components for use in the invention include the diazo oxides such as the water-insoluble esters and amides of naphthoquinone diazide sulphonic or carboxylic acids as described, e.g. in U.S. Patent 3,969,118 and Light Sensitive Systems by J. Kosar (John Wiley & Sons, Inc., N.Y. 1965, pp 336ff); and acrylic polymers (such as polymethacrylates and polyacrylates), and mixtures thereof.
Preferred positive-acting, water-insoluble, radiation-sensitive components comprise esters formed bythe reaction of diazo - 1,2 - naphthoquinone sulphonylhalides, wherein the diazo group is in the 1 - or 2-position and the halide is in the 4- or 5-position, with condensation polymers formed by reaction of mono- or poly-hydroxyaryl compounds with ketones or aldehydes.
The above hydroxyaryl compounds include phenol, naphthol, resorchinol, phloroglucinol and pyrogallol, and mixtures thereof.
The aldehydes and ketones useable in preparation of the esters include formaldehyde, benzaldehyde and acetone, and mixtures thereof.
A preferred positive-acting, radiation-sensitive component comprises the ester formed by reaction of 2 - diazo - 1,2 - naphthoquinone - 5 - sulphonyl chloride with a polymer formed by condensation of a cresol with formaldehyde (such as Alnoval PN 430 manufactured byAmerican Hoechst Corp, Alnoval being a trade mark).
The radiation absorbing components which may be used include triazines, triazoles and diarylketones, and mixtures thereof.
The triazoles which may be used according to the invention include benzotriazoles of the Formula I
wherein R' is an aryl group which is substituted with at least one hydroxy, alkoxy, aryloxy, aralkoxy group wherein the alkoxy, aryloxy and aralkoxy groups may be further substituted with at least one group selected from hydroxy, halo, nitro, substituted- or unsubstituted-amino and which aryl group may be further substituted with one or more groups selected from alkyl, aryl, aralkyl which may be unsubstituted or substituted with at least one group selected from hydroxy, halo, nitro, substituted or unsubstituted amino;;
R2, R3, R4 and R5 are the same or different and are selected from the group comprising hydrogen, alkyl aryl, aralkyl, alkoxy, aralkoxy, aryloxy, nitro, halo, substituted amino wherein said alkyl, aryl, arakyl, alkoxy, aralkoxy and aryloxy groups may be substituted or unsubstituted.
or R2 and R3, R3 and R4 and/or R4 and R5 together form alkylene, alkenylene or fused ring structures.
Any alkyl moieties in the compounds of Formula 1 may contain, for instance, 1 to 8 carbon atoms.
The diarylketones that may be used include compounds of the Formula II
wherein Ar1 and Ar2 may be the same or different and are selected from the group consisting of R1, as defined above,
wherein each group R2 is as defined above and two or more of the group R2 may form an alkylene, alkenylene or fused ring structure, and q is an integerfrom 1 to 7.
Preferably the radiation absorbing component is selected from the group consisting of Michler's ketone, or a compound of Formula I, wherein R2, R3,
R4 and R5 are each hydrogen and R' is
wherein t-Bu is t-butyl. Such compounds are available commercially as Tinuvin P and Tinuvin 328, respectively. Tinuvin is a trade mark. Mixtures of such compounds are very useful.
Most preferably the radiation absorbing component is a compound of the Formula I wherein R', R2,
R3, R4, and Rs are defined above or mixtures thereof.
The polymeric binders which may be used in preparing the composition of the invention include the alkali-soluble products of the condensation of monoor poly-hydroxyaryl compounds with ketones or aldehydes as described above.
The radiation-sensitive composition may comprise about 10 to about 40% radiation-sensitive component, about4to about 10% radiation absorbing component and about 30 to about 85% alkalisoluble polymeric binder, all percentages being based on total composition weight.
More preferably, the radiation-sensitive composition comprises about 15 to about 35% radiationsensitive component, about 5 to about 10% radiation-absorbing component and about 40 to about 60% polymeric binder, all percentages being based on the total weight of the composition.
Additionally, if desired, the radiation-sensitive composition may contain one or more additives, normally selected from thermal polymerisation inhibitors, scratch resistant polymers, dyes to indicate contrast and/or print-out, radiation sensitivity enhancers, contrast enhancers, and print-out enhancers.
Thus the radiation-sensitive composition may also contain about 1.0 to about 2.0% thermal polymerisation inhibitors, about 0.5 to about 10.0% scratch resistant polymers, about 1.0 to about 5.0% radiation sensitivity enhancers, about 1.0 to about 10.0% dyes to indicate print-out and/or contrast and about 1.0 to about 5.0% of compounds to aid in print-out, percentages being based on total solids content.
A positive-working, radiation-sensitive element according to the invention is free of silver and comprises a substrate that is transparent to the radiation and that carries on a face a layer of the described positive-working radiation-sensitive composition.
The substrates which may be used in accordance with the instant invention are polyesters, exemplified by poly(ethylene terephthalate) (e.g. Mylar manufactured by DuPont); polycarbonates, (e.g.
Lexan manufactured by General Electric Co.), glass plates; quartz plates; polyolefins (such as poly(methylpentene) and transparent polypropylene); transparent polyamides (e.g. nylons, such as
Trogamid T manufactured by Dynamit Nobel) and transparent silicones. Mylar, Lexan, and Trogamid are trade marks.
In practice the coating may be applied to the substrate by methods known to the art including spray coating, dip coating, electrostatic coating, melt coat
ing, roller coating, and reverse roller coating.
If necessary, the coating composition may first be dissolved in a solvent and after coating the substrate the solvent may be removed by methods known to the art.
Solvents for use in preparation of the coating solutions may be exemplified by polar organic solvents,
halogenated alkanes, alcohols, ketones and ethers, and mixtures thereof.
Illustrative of the polar organic compounds are dimethylformamide (DMF), dimethylacetamide, dimethylsulphoxide, acetonitrile, and 1 - methyl - 2 pyrrolidone, and mixtures thereof.
The halogenated alkanes may be illustrated by methylene chloride, ethylene dichloride and perchloroethylene, and mixtures thereof.
Examples of alcohols useful in accordance with this invention are methanol, ethanol, isopropanol and amyl alcohols, and mixtures thereof.
The ketones useful in accordance with this invention may be illustrated by methyl ethyl ketone (MEK) and methyl isobutyl ketone, and mixture thereof.
The ethers include 2-methoxyethanol, e.g. methyl cellosolve, Cellosolve being a trade mark.
A preferred solvent comprises a mixture of 10 to 20% DMF, O to 20% MEK, 20 to 50% methylene chloride, 0 to 15% methanol and 20 to 50% methyl
Cellosolve, most preferably 11.9% MEK, 11.9% DMF, 33.3% methyl Cellosolve, 33.3% methylene chloride and 9.5% methanol.
A negative or, preferably, a positive duplicating film may be prepared from the described radiationsensitive element by exposing the element to radiation through the transparent substrate and thereby rendering the composition alkali soluble to a predetermined depth from the said coated face of the substrate, then imagewise exposing the element to radiation through a mask that is in front of or in contact with the surface of the layer that is distant from the said face and thereby rendering the exposed areas alkali soluble, and then removing the imagewise exposed areas by treating the exposed element with an alkali developer.
Thus those areas that were exposed through both the transparent support and the mask are removed while the areas that were not imagewise exposed through the mask provide opaque areas for preparing printing plates.
The portion of the radiation-sensitive composition which is rendered alkali-soiuble, in the first step, is a volume elementwhose dimensions are the surface area of the substrate face and the depth of penetration of the radiation into the composition. The depth of penetration is a function of the concentration of radiation-absorbing component in the composition.
Thus, as the concentration increases the thickness of the coating may be decreased and as the concentration decreases it is necessary to increase the coating thickness.
The duplicating films may be prepared by exposure of the radiation-sensitive elements to various types of radiation, as known in the art, including UV, visible light, IR, electron beam and lasers.
The exposed elements may be developed by treatment with alkaline developers, as known in the art, including aqueous sodium silicate and phosphates.
The following examples illustrate but do not limit the invention.
Example 1
A mixture comprising, a phenol-formaldehyde resin 8.4 g 2-diazo-1 ,2-naphthoquinone4- sulphonylchloride 1.475 g the reaction product of a cresolformaldehyde resin and 2-diazo-1,2naphthoquinone-5-sulphonyl chloride 4.425 g
Tinuvin P 0.437 g
Tinuvin 328 0.437 g and Orasil Red B 3.500 g was dissolved in a 105 ml of a solvent comprising 11.9% MEK, 11.9% DMF, 33.3% methyl Cellosolve, 33.3% methylene chloride, and 9.5% methanol, all of the solvent percentages being in parts by volume based on total volume.
Orasil is a trade mark.
The above solution was applied by meniscus coating to a sheet of Mylar and dried. The resulting element was
I. exposed in a Berkey Ascor 5KW exposure to an
Addalux 1406-04 diazo bulb through the transparent substrate for about 18 seconds and then through a mask in front of the composition for about 15 seconds followed by,
II. development with an about 5% by a weight aqueous sodium silicate composition to yield a mask which would prevent undesirable transmission of the radiation through the opaque areas up to exposures, in the above unit, for about 4 minutes and above, and can be used repeatedly without detrimental effects to the opacity of the mask.
Example 2
A mixture comprising, a phenol-formaldehyde resin 10.58 g 2-diazo-l ,2-naphthoquinone-5-sulphonic acid, alkyl ester 3.97 g the product of the reaction of 2-diazo-1,2 naphthoquinone-5-sulphonyl chloride with the product of the reaction of pyrogallol with acetone 3.97 g
Orasil Red B 4.41 g contrast enhancer 0.37 g
Tinuvin P 0.39 g
Tinuvin 328 0.39 g was dissolved in 105 ml of the solvent of Example 1.
The above composition was used as indicated in
Example 1 and similar results were obtained.
Claims (17)
1. A composition that is free of silver and that is a positive-working, radiation-sensitive, composition and that is alkali insoluble but is rendered alkali soluble upon exposure to radiation and that comprises at least one positive-working, radiation-sensitive, essentially alkali insoluble component, at least one radiation-absorbing component and at least one alkali soluble polymeric binder.
2. A composition according to claim1 in which the radiation-sensitive component is a water insoluble ester or amide of a naphthoquinone diazide sulphonic or carboxylic acid.
3. A composition according to claim 2 in which the radiation-sensitive component is an ester of a diazo - 1,2, - naphthoquinone sulphonyl halide wherein the diazo group is in the 1 or 2 position and the halide is in the 4 or 5 position.
4. A composition according to claim 2 or claim 3 in which the ester is an ester formed with a condensation polymerformed bythe reaction of a mono- or poly-hydroxy aryl compound with a ketone or aldehyde.
5. A composition according to claim 4 in which the ester is formed with a cresol formaldehyde resin.
6. A composition according to any preceding claim in which the radiation-absorbing componding is a triazine, triazole or diarylketone.
7. A composition according to claim 6 in which the radiation-absorbing component comprises a compound of the formula
wherein t-Bu is t-butyl, or a mixture thereof.
8. A composition according to any preceding claim in which the polymeric binder is a condensation product of a mono- or polyhydroxy aryl compound with a ketone or aldehyde.
9. A composition according to claim 8 in which the binder is a phenol formaldehyde resin.
10. A composition according to claim 1 comprising the reaction product of 2 - diazo - 1,2 - naphthoquinone - 5 - sulphonyl chloride with a cresol formaldehyde resin, a radiation-absorbing component
comprising a mixture of the compounds defined in
claim 7, and a phenol formaldehyde resin as alkali
soluble polymeric binder.
11. A composition according to any preceding
claim also including a contrast enhancer and a
radiation-sensitive enhancer.
12. Acomposition according to any preceding claim containing from 10 to 40% of the radiationsensitive component, 4 to 10% of the radiationabsorbing component and 30 to 85% alkali soluble polymeric binder, all percentages being by weight based on the weight of total composition.
13. An element that is free of silver and that is a positive-working, radiation-sensitive element and that comprises a substrate that is transparent to the radiation and that carries on a face a layer of a composition according to any preceding claim.
14. A process for preparing a duplicating film which comprises exposing an element according to claim 13 through the transparent substrate to radiation and thereby rending the composition alkali soluble to a predetermined depth from the face, imagewise exposing the element to radiation through a mask in front of or in contact with the surface of the layer that is distant from the face and thereby rendering the exposed areas alkali soluble, and then removing the imagewise exposed areas by treating the exposed element with an alkali developer.
15. A process according to claim 14 in which exposure and development results in formation of a positive duplicating film.
16. A duplicating film made by a process according to claim 14 or claim 15.
17. A process of making a lithographic printing plate by imagewise exposure of a plate carrying a radiation sensitive composition through a mask according to claim 16.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23640081A | 1981-02-20 | 1981-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2094015A true GB2094015A (en) | 1982-09-08 |
Family
ID=22889334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8204901A Withdrawn GB2094015A (en) | 1981-02-20 | 1982-02-19 | Non-silver, positive-working, radiation-sensitive composition |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS57155534A (en) |
| AU (1) | AU8021782A (en) |
| DE (1) | DE3206108A1 (en) |
| FR (1) | FR2500645A1 (en) |
| GB (1) | GB2094015A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0334233A2 (en) * | 1988-03-23 | 1989-09-27 | Hitachi Chemical Co., Ltd. | Photosensitive resin composition and pattern formation using the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2614847B2 (en) * | 1986-06-16 | 1997-05-28 | 東京応化工業 株式会社 | Positive photosensitive composition |
| JPH01133045A (en) * | 1987-11-17 | 1989-05-25 | Mitsubishi Electric Corp | Resist pattern forming method |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1052699A (en) * | 1963-12-03 | |||
| FR1530266A (en) * | 1966-07-08 | 1968-06-21 | Kalle Ag | Method and equipment for duplicating silver films |
| GB1204917A (en) * | 1967-11-14 | 1970-09-09 | Howson Algraphy Ltd | Photographic printing plates |
| CA933791A (en) * | 1969-06-13 | 1973-09-18 | Broyde Barret | Additives to positive photoresists which increase the sensitivity thereof |
| US3984250A (en) * | 1970-02-12 | 1976-10-05 | Eastman Kodak Company | Light-sensitive diazoketone and azide compositions and photographic elements |
| BE789951A (en) * | 1971-10-14 | 1973-04-11 | Hoechst Co American | METHOD FOR PRODUCING IMAGES BY MEANS OF A PHOTOSENSITIVE LAYER |
| DE2331377C2 (en) * | 1973-06-20 | 1982-10-14 | Hoechst Ag, 6000 Frankfurt | Photosensitive copying material |
| JPS5619619B2 (en) * | 1973-07-27 | 1981-05-08 | ||
| DE2541982A1 (en) * | 1975-09-20 | 1977-03-24 | Ibm Deutschland | PROCESS FOR Awareness Raising A POSITIVE WORKING PHOTORESIST AND PHOTORESIS MATERIAL |
| DE3071134D1 (en) * | 1979-06-01 | 1985-11-07 | Hoechst Co American | Colour testing foil |
| JPS566236A (en) * | 1979-06-28 | 1981-01-22 | Fuji Photo Film Co Ltd | Photosensitive material and pattern forming method using it |
| JPS5666844A (en) * | 1979-11-05 | 1981-06-05 | Kaneo Yamamoto | Manufacture of diazo photosensitive paper preventing ground discoloration of copy |
-
1982
- 1982-02-05 AU AU80217/82A patent/AU8021782A/en not_active Abandoned
- 1982-02-17 JP JP2522082A patent/JPS57155534A/en active Pending
- 1982-02-19 GB GB8204901A patent/GB2094015A/en not_active Withdrawn
- 1982-02-19 FR FR8202822A patent/FR2500645A1/en not_active Withdrawn
- 1982-02-19 DE DE19823206108 patent/DE3206108A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0334233A2 (en) * | 1988-03-23 | 1989-09-27 | Hitachi Chemical Co., Ltd. | Photosensitive resin composition and pattern formation using the same |
| EP0334233A3 (en) * | 1988-03-23 | 1991-04-03 | Hitachi Chemical Co., Ltd. | Photosensitive resin composition and pattern formation using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2500645A1 (en) | 1982-08-27 |
| AU8021782A (en) | 1982-08-26 |
| DE3206108A1 (en) | 1982-11-04 |
| JPS57155534A (en) | 1982-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |