US3853559A - Photographic material utilizing an aromatic hydroxy compound and a 2-nitro-phenyl-aldehyde - Google Patents
Photographic material utilizing an aromatic hydroxy compound and a 2-nitro-phenyl-aldehyde Download PDFInfo
- Publication number
- US3853559A US3853559A US00390149A US39014973A US3853559A US 3853559 A US3853559 A US 3853559A US 00390149 A US00390149 A US 00390149A US 39014973 A US39014973 A US 39014973A US 3853559 A US3853559 A US 3853559A
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- US
- United States
- Prior art keywords
- light
- composition
- aldehyde
- aromatic hydroxy
- material according
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Definitions
- ABSTRACT Photo-sensitive material useful in wash-off imagery comprises a tannable hydrophilic colloid and a lightsensitive tanning agent precursor which is a mixture of an aromatic hydroxy compound and a 2'-nitr0-phenylaldehyde.
- the present invention relates to compositions useful in the so-called wash-off process of forming photographic images.
- this general procedure has been utilized to prepare images by the exposure to a light pattern a material in which such exposure effects a change in the physical properties of the material, particularly a change in the solubility or susceptibility of the matter to swelling or tackifying when in contact with a developing fluid.
- Subsequent removal of the more soluble form of the matter from an exposed coated layer through the use of the developing fluid results in an image defining the original exposure pattern.
- compositions useful in the wash off process were the bichromated colloids which tanned upon exposure to light substantially rich in'ultra-violet radiation.
- such natural colloids as glue, gelatin, and albumin
- synthetic hydrophilic polymers as polyvinyl alcohol and carboxymethyl cellulose were used to a great extent to prepar copies of line originals, engineering drawings, and the like.
- a group of wash-off imaging materials which have more recently found acceptance in the field are based for the most part on silver halide components which are dispersed in a substantially unhardened layer of tannable hydrophilic colloid.
- These materials utilize basic sil ver halide development chemistry in the formation of tanned colloid images in light-exposed areas; that is, the redox reaction resulting from the application of aromatic hydroxy developer compounds effects reduction to form a silver image and yields quinone-type oxidation products which tan the colloid at the development sites.
- these materials have been technologically successful, the growing scarcity of silver upon which these imaging compositions are wholly dependent presents a substantial limitation upon their continued employment.
- the present invention provides a process for the for mation of images by means of the tanning of hydrophilic colloid materials and utilizes the quinone oxidation products of aromatic hydroxy compounds to effect such tanning.
- this invention employs no precious metals such as silver, rather a light-sensitive 2'-nitro-phenyl-aldehyde is utilized in the imaging material.
- These aldehyde compounds which apparently yield the corresponding nitro acids through photolysis, enter into a light-initiated redox reaction as a result of which aromatic hydroxy compounds present in the composition yield colloidtanning quinone oxidation products.
- the resulting decrease in the solubility of the colloid matrix of a coated composition at the light-exposed reaction sites thus renders the matter readily developable by a simple water wash removal of unexposed composition to yield replica of the imagewise light exposure.
- the imaging materials of the present invention are generally in the form of a layer coated upon a suitable support such as paper, film, metal, glass, and the like.
- the layer of light-sensitive composition is prepared through the use of any of the commonly-employed provics of which the photographic arts are wholly aware and which may be selected in accordance with the preferences of the practitioner.
- the coatable composition of the present materials essentially comprises a matrix of a tannable hydrophilic colloid which serves as the binding medium of the composition and throughout which are distributed the aromatic hydroxy and light-sensitive 2'-nitro-phenylaldehyde tanning agent precursor compounds.
- These basic components may be readily formed into a fluid coating composition through the use of suitable solvent vehicles. Water preferably comprises a major proportion of such in view of the hydrophilic character of the colloid matrix. Additional water soluble or water compatible fluids or solvents of an organic nature may be included in the composition to assist in the solution or dispersion of the remaining components.
- the tannable hydrophilic colloids employed in the compositions of the present invention include those natural and synthetic compounds which have previously been used in the general class of was'h-off materials.
- colloids are gelatin, casein, glue, starch, albumin, polyvinyl alcohol, saponified cellulose acetate, carboxymethyl cellulose, and the like.
- composition matrix generally comprises the tannable colloid
- additional polymeric materials may be included to vary the physical properties according to the ultimate utilization of the material and the final image.
- various polymerizable components such as vinyl monomers and bifunctional cross-linking agents which have been found to increase the toughness and durability of tanned colloid imagesformed in the instant processes.
- a vinyl monomer such as acrylamide, and N-N'- methylenebisacrylamide as a cross-linking agent yields a composition which will provide particularly durable wash-off images after light exposure and development processing.
- the aromatic hydroxy compound components of the tanning agent precursor utilized in the present invention may be selected from any of those compounds which are identified with the usual development of silver halide photographic materials. As with such prior utilization, these compounds may be employed singularly or in combination to effect the desired rate of tanning development depending upon the remaining components of the light-sensitive layers.
- Useful such compounds for this purpose include hydroquinone, chlorohydroquinone, catechol, pyrogalllol, 4-methoxy-1- naphthol, sodium salicylate, phloroglucinol, gallic acid, p-methylaminophenol, and the like.
- the amount of this component is a coated imaging composition may generally range from 5 to about 15 percent by weight.
- the light-sensitive component of the tanning agent precursor combination may be one or more of the group of light-sensitive 2'mitro-phenyl-aldehydes such as o-nitro-benzaldehyde, 2,4-dinitrobenzaldehyde, 2,6- dinitrobenzaldehyde, o-nitrocinnamaldehyde.
- This component of the precursor combination may be employed in the ratio range of about 1 to 2 weight parts visual contrast of the image.
- the light-sensitive material l n (inert, high bloom) 20 gm. may be pre-dyed or pigmented to effect a desired de- Methanol 40 f b t th f I d th b Acetone 20 ml. gree o contrast e ween e ma image an e 0 Nitmbenzaldehyde 05 gm strate support. It should be recognized that the addition grllill rohlydroqilinone 0.4 gm.
- Example 1 a lightly-colored mm i composition devoid of contrasting pigments may be EXAMPLE 3 used in which event the resulting wash-off image can be visually intensified between application of dye solu- In the manner described Example gi g matetions or pigmented coloring matter which is specific to was Prepared from the following composltlon: the image or the substrate.
- the gelatin was swelled and dissolved in the water, and the catechol was then dissolved in the solution.
- the aldehyde compound dissolved in a mixture of the methanol and acetone was then added to complete the coating composition.
- the coated side of the resulting imaging material was exposed through an opaque stencil for about three minutes to the light of a bank ofG.E. F8T5 BLB lamps, rich in ultra-violet radiation, separated by about 15 mm. and set at a distance of about 20 mm. from the imaging material.
- the coating was washed with water at about 3035C. to yield a relief image of hardened composition in the exposed areas.
- the frontside exposure of wash-off materials is relegated to the formation of line and half-tone images, since adhesion of tanned image to base sheet is ensured by prolonged exposure.
- the materials of the present invention are nonetheless useful in continuous tone processing where they also enjoy the more rapid activity associated with that practice of exposing the imaging compositions through the substantially transparent base sheet. Exposure of material by this latter method can be employed to derive an indication of the relative photographic speed of wash-off compositions.
- the present materials exhibit a significant rate of response which may yet be in effect improved by strengthening the resulting image through incorporation of polymerizable monomeric compositions.
- EXAMPLE 16 Coated material was prepared according to the formulation of Example 5 and was imagewise exposed to the bank of lamps as in Example 1, but through the base sheet support, for a period of 30 seconds. Development treatment according to Example 1 resulted in a good relief image.
- Example 16 A 20-second exposure and treatment of the resulting coating under the conditions otherwise described in Example 16 resulted in a similar durable image.
- the coated material likewise provided a good resist image when exposed in a conventional white-print machine at a speed of about 1.5 meters per minute.
- Imaging material comprising a support and a coating thereon of a composition
- a composition comprising:
- Material according to claim 2 wherein said arosition comprises 55 to 90 parts by weight of said colloid, 5 to 15 parts by weight of said aromatic hydroxy compound, and 5 to 30 parts by weight of said lightsensitive aldehyde.
- a photo-imaging process comprising:
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00390149A US3853559A (en) | 1973-08-20 | 1973-08-20 | Photographic material utilizing an aromatic hydroxy compound and a 2-nitro-phenyl-aldehyde |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00390149A US3853559A (en) | 1973-08-20 | 1973-08-20 | Photographic material utilizing an aromatic hydroxy compound and a 2-nitro-phenyl-aldehyde |
Publications (1)
Publication Number | Publication Date |
---|---|
US3853559A true US3853559A (en) | 1974-12-10 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00390149A Expired - Lifetime US3853559A (en) | 1973-08-20 | 1973-08-20 | Photographic material utilizing an aromatic hydroxy compound and a 2-nitro-phenyl-aldehyde |
Country Status (1)
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US (1) | US3853559A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070003862A1 (en) * | 2005-06-16 | 2007-01-04 | Fujitsu Limited | Resist composition, method of forming resist pattern, semiconductor device and method of manufacturing thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3368900A (en) * | 1964-06-03 | 1968-02-13 | Du Pont | Polymerizable compositions and elements |
-
1973
- 1973-08-20 US US00390149A patent/US3853559A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3368900A (en) * | 1964-06-03 | 1968-02-13 | Du Pont | Polymerizable compositions and elements |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070003862A1 (en) * | 2005-06-16 | 2007-01-04 | Fujitsu Limited | Resist composition, method of forming resist pattern, semiconductor device and method of manufacturing thereof |
US7452657B2 (en) * | 2005-06-16 | 2008-11-18 | Fujitsu Limited | Resist composition, method of forming resist pattern, semiconductor device and method of manufacturing thereof |
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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 |