US3503744A - Photographic bleaching out of azomethine and azoaniline dyes - Google Patents
Photographic bleaching out of azomethine and azoaniline dyes Download PDFInfo
- Publication number
- US3503744A US3503744A US616503A US3503744DA US3503744A US 3503744 A US3503744 A US 3503744A US 616503 A US616503 A US 616503A US 3503744D A US3503744D A US 3503744DA US 3503744 A US3503744 A US 3503744A
- Authority
- US
- United States
- Prior art keywords
- light
- image
- color
- sensitive
- color modifier
- 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
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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/02—Direct bleach-out processes; Materials therefor; Preparing or processing such materials
-
- 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
- G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances
Definitions
- R is hydrogen, alkyl, amino, or substituted amino
- a keto-methylene group is a keto-methylene group, pyrazolone group, or a nucleus having an active hydrogen-containing coupler component.
- Imagewise exposure of the material to light provides a like distribution of reactive halogen free radicals which have a bleaching effect on the color modifier and results in image formation.
- the image may be fixed by heating acidic anhydrides incorporated in the material or by washing the material to remove at least one of the color modifier or organic halogen compounds.
- the present invention relates to making photocopies and particularly to providing a stable color modifier which may react with an initiator to produce a visible image in accordance with a light pattern and more particularly relates to a bleaching-out process where the light-struck portions of the light-sensitive materials are rendered colorless leaving the portions of the photosensitive material which have not been struck by light in their colored form.
- An object of the present invention is to provide a photocopy material and method whereby permanent copies can be made with actinic light.
- the present invention uses a compound of the following general formula:
- R and R individually mean alkyl or hydroxyalkyl; R means hydrogen, alkyl or amino group optionally substituted;
- the above compound which is used in the invention has found its application in color films and photographic papers and it is recognized as such a dye which is formed by color development of the color film or photographic paper with a color developer of the diethyl-p-phenylenediamine type after light exposure. Accordingly, the lightsensitive material of the present invention which uses the above-said dye does not suffer from color image fading which is encountered in the prior art.
- the light-fastness of the printing material of the invention is practically satisfactory. For instance, no fading is observed when the color image on the printing material is subjected to irradiation from a carbon arc lamp at a distance of 45 cm. at a temperature of 50 C. under a relative humidity of 45% for 8 hours in a fading-out tester.
- the colored image formed on the light-sensitive material of the invention is remarkably excellent in lightfastness.
- the compounds which are usable in the invention can be prepared with relative ease.
- the high molecular binder various compounds, for example, cellulose derivatives such as acetylcellulose, ethylcellulose, etc., polymeric vinyl compounds such as polyvinyl chloride, polyvinyl acetate, polyvinylidene chloride, polystyrene, etc., or synthetic rubbers such as styrene-maleic anhydride copolymer, cyclized rubber, butadiene-copolymer can be used.
- a solvent such solvent may be selected that can thoroughly dissolve the binder used.
- a solvent such as acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, dioxane, cyclohexanone, etc. and a mixed solvent such as acetone-methanol, acetonebenzene, etc. can be mentioned.
- a sensitizer can be ,added as an auxiliary component and the bleaching action can be elfected by the action of light having specific range of wave length, and so the colored image can be prepared by forming multi-layers of several kinds of color modifiers and then bleaching each of the layers by the action of light having specific wave length.
- a sensitizing dye used for photography such as cyanine, merocyanine, styryl or acridine dye can efiectively be used. Following dyes are the examples of the sensitizing dyes:
- 1%, based on the lightsensitive solution, of lead oxide, titanium dioxide, starch, etc. may be added.
- the fixing of the light-sensitive, printing materiahof this invention is effected by heating said material after it has been printed or by subjecting the material to the treatment with solvent.
- a heat-fixing agent might have been added previously, if necessary.
- anhydrous acids such as phthalic anhydride, maleic anhydride, succinic anhydride or organic acids such as ben-. zoic acid, phenylacetic acid, phenoxy-acetic acid, phthalaldehydic acid, palmitic acid, stearic acid, etc. are effective.
- These heat-fixing agents can be added to the binder solution together with the' photo-initiator and the color modifier.
- salts such as sodium metaborate, sodium carbonate, sodium salicylate, sodium oxalate, etc. are also eflective, but these salts cannot be added to the binder solution and so they are overcoated on the surface of the light-sensitive layer of the 1ightsensitive, printing material of this invention as an aqueous solution containing about 0.5% of the salts.
- the light-sensitive, printing material of this invention can be produced according to the known method by dissolving each of the aforementioned components in the binder solution and coating the resulting solution on a suitable supporting material.
- The' preferable quantitative ratio of each of the above components is roughly limited as follows:
- the supporting material although any of paper, plastic film base, glass plate and metal plate may be used, generally, a clear image of good resolving power and high density can be obtained, when a photographic paper or plastic-coated paper is used as the supporting material. Furthermore, when a photographic film base is used, a clear transparent image can be formed. In general, it is most preferable to coat the light-sensitive layer on the supporting material in such amount that the thickness of the light-sensitive layer may be' about 2-3,u.
- a clear image can be produced when the light-sensitive, printing material of this invention thus obtained is exposed through :an original thereby to eifect imagewise bleaching of a dye.
- the fixing of an image is effected by stabilizing the residual photo-initiator by heating the printed material or by removing the residual photo-initiator by treating with a suitable solvent.
- the above heating method may be carried out by means of heating rollers, hot plates, etc. having a surface temperature of about 80-150 C. for about 0.5-2 minutes.
- a solvent such solvent that does not dissolve the residual dye but dissolves olfthe photo-initiator, is selectively used.
- the treatingperiod of 1 5 minutes is suificient for fixing with a solvent and a stable image' can be obtained thereby.
- the mixed solvent comprising trichloro- 8 ethylene, ethyl acetate, and cyclohe'xane is suitable andefiective. I, p p
- Example 2 Being exposed analogouslyto the Example 1, a clear red image was formed.
- a stable image was prepared by treating said image with a heat roller having surface temperature of C. for 1 minute.
- EXAMPLE 4 10 g. of cellulose acetate were dissolved in 100 cc. of an acetone-benzene (50:50) mixture, and then the mixture of 0.2 g. of p-me'thoxybenzoyl-(p-diethylaminophenylimino)-acetanilide [Color Modifier (2) as above], 0.3 g. of 1-phenyl-3-methyl 4 (p-diethylaminophenylimino)-S-pyrazolone, 0.35 g. of 2-carboxyanilino-4-(pdiethylaminophenylimino) naphthoquinone and 10 g. of carbon tetrabromide was dissolved therein. This solution was printed on the baryta paper analogously to the Example 1 and was dried. 1 f
- the light-sensitive film thus formed in tri-pack was divided into four sections. Each of the four sections was exposed with a 500 W-refiective photoflood lamp at 10 cm. distance for 1 minute, the first section through Kodak Wratten filter #49 (blue filter), the second section through Kodak Wratten filter #61 (green filter), the third section through Kodak Wratten filter #29 (red filter) and the fourth section Without any filter, and dipped for 3 minutes in ethyl acetate-cyclohexane (1:1). Each of the sections was colored to a tint corresponding to that of the filter used, that is, the first section to blue, the second section to green, the third section to red and the fourth section to achromatic. These colors were entirely stable after being exposed again.
- a light-sensitive printing material containing a color modifier and an organic halogen-containing compound capable of producing free radicals upon exposure to light to react with said color modifier to produce a color change, said color modifier being an azoaniline or azomethine dye of the general formula:
- R and R are alkyl or hydroxyalkyl;
- R is hydrogen, alkyl, amino, or substituted amino;
- a keto-methylene group is a keto-methylene group, pyrazolone group, or a nucleus having an active hydrogen-containing coupler component.
- color modifier compound is selected from the group of compounds identified as Formulas 1 through 21 inclusive of the specification.
- a photo-sensitive element comprising a base sheet coated with the color modifier and initiator according to claim 1.
- a multi-color photo-sensitive element comprising a base sheet having a plurality of separate layers of the material according to claim 1 [with each layer including a different color modifier whereby light passing through a selected filter will affect only one color modifier compound in one layer and such layer can be fixed thereafter and whereby light passing through a selected different filter will affect a second and different color modifier in a second and different layer which can be fixed thereby producing a multi-c0lor image.
- the color modifier in the second layer is: twCyano-w-(pdiethylaminophenylimino) aceto (p-octadecenyl succinylamino) phenone; and
- the color modifier in the third layer is: 2-carboxystearylamino 4 (p-diethylaminophenylim no) naphth0- qumone.
- a method of making permanent color copies comprising:
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US61650367A | 1967-02-16 | 1967-02-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3503744A true US3503744A (en) | 1970-03-31 |
Family
ID=24469746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US616503A Expired - Lifetime US3503744A (en) | 1967-02-16 | 1967-02-16 | Photographic bleaching out of azomethine and azoaniline dyes |
Country Status (1)
Country | Link |
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US (1) | US3503744A (en) |
Cited By (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0016732A1 (en) * | 1979-03-26 | 1980-10-01 | Ciba-Geigy Ag | Process for producing photographic images, and suitable photographic material |
EP0651286A1 (en) * | 1993-10-28 | 1995-05-03 | Eastman Kodak Company | Photographic elements containing indoaniline dummy dyes |
US5616443A (en) * | 1993-08-05 | 1997-04-01 | Kimberly-Clark Corporation | Substrate having a mutable colored composition thereon |
US5643356A (en) * | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Ink for ink jet printers |
US5645964A (en) * | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5685754A (en) * | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US5739175A (en) * | 1995-06-05 | 1998-04-14 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer |
US5747550A (en) * | 1995-06-05 | 1998-05-05 | Kimberly-Clark Worldwide, Inc. | Method of generating a reactive species and polymerizing an unsaturated polymerizable material |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
US5798015A (en) * | 1995-06-05 | 1998-08-25 | Kimberly-Clark Worldwide, Inc. | Method of laminating a structure with adhesive containing a photoreactor composition |
US5811199A (en) * | 1995-06-05 | 1998-09-22 | Kimberly-Clark Worldwide, Inc. | Adhesive compositions containing a photoreactor composition |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US5849411A (en) * | 1995-06-05 | 1998-12-15 | Kimberly-Clark Worldwide, Inc. | Polymer film, nonwoven web and fibers containing a photoreactor composition |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3104973A (en) * | 1960-08-05 | 1963-09-24 | Horizons Inc | Photographic bleaching out of cyanine dyes |
-
1967
- 1967-02-16 US US616503A patent/US3503744A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3104973A (en) * | 1960-08-05 | 1963-09-24 | Horizons Inc | Photographic bleaching out of cyanine dyes |
Cited By (60)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0016732A1 (en) * | 1979-03-26 | 1980-10-01 | Ciba-Geigy Ag | Process for producing photographic images, and suitable photographic material |
US6066439A (en) | 1993-08-05 | 2000-05-23 | Kimberly-Clark Worldwide, Inc. | Instrument for photoerasable marking |
US5908495A (en) | 1993-08-05 | 1999-06-01 | Nohr; Ronald Sinclair | Ink for ink jet printers |
US5616443A (en) * | 1993-08-05 | 1997-04-01 | Kimberly-Clark Corporation | Substrate having a mutable colored composition thereon |
US5643701A (en) * | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Electrophotgraphic process utilizing mutable colored composition |
US5643356A (en) * | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Ink for ink jet printers |
US5645964A (en) * | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US5683843A (en) * | 1993-08-05 | 1997-11-04 | Kimberly-Clark Corporation | Solid colored composition mutable by ultraviolet radiation |
US5858586A (en) | 1993-08-05 | 1999-01-12 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US6054256A (en) | 1993-08-05 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Method and apparatus for indicating ultraviolet light exposure |
US5721287A (en) | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
US6060200A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms and methods |
US6060223A (en) | 1993-08-05 | 2000-05-09 | Kimberly-Clark Worldwide, Inc. | Plastic article for colored printing and method for printing on a colored plastic article |
US6120949A (en) | 1993-08-05 | 2000-09-19 | Kimberly-Clark Worldwide, Inc. | Photoerasable paint and method for using photoerasable paint |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6127073A (en) | 1993-08-05 | 2000-10-03 | Kimberly-Clark Worldwide, Inc. | Method for concealing information and document for securely communicating concealed information |
US6342305B1 (en) | 1993-09-10 | 2002-01-29 | Kimberly-Clark Corporation | Colorants and colorant modifiers |
EP0651286A1 (en) * | 1993-10-28 | 1995-05-03 | Eastman Kodak Company | Photographic elements containing indoaniline dummy dyes |
US5460930A (en) * | 1993-10-28 | 1995-10-24 | Eastman Kodak Company | Photographic elements containing indoaniline dummy dyes |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
US6090236A (en) | 1994-06-30 | 2000-07-18 | Kimberly-Clark Worldwide, Inc. | Photocuring, articles made by photocuring, and compositions for use in photocuring |
US5709955A (en) | 1994-06-30 | 1998-01-20 | Kimberly-Clark Corporation | Adhesive composition curable upon exposure to radiation and applications therefor |
US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
US5686503A (en) * | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and applications therefor |
US5685754A (en) * | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6235095B1 (en) | 1994-12-20 | 2001-05-22 | Ronald Sinclair Nohr | Ink for inkjet printers |
US5739175A (en) * | 1995-06-05 | 1998-04-14 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer |
US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
US5747550A (en) * | 1995-06-05 | 1998-05-05 | Kimberly-Clark Worldwide, Inc. | Method of generating a reactive species and polymerizing an unsaturated polymerizable material |
US6063551A (en) | 1995-06-05 | 2000-05-16 | Kimberly-Clark Worldwide, Inc. | Mutable dye composition and method of developing a color |
US5798015A (en) * | 1995-06-05 | 1998-08-25 | Kimberly-Clark Worldwide, Inc. | Method of laminating a structure with adhesive containing a photoreactor composition |
US5849411A (en) * | 1995-06-05 | 1998-12-15 | Kimberly-Clark Worldwide, Inc. | Polymer film, nonwoven web and fibers containing a photoreactor composition |
US5837429A (en) | 1995-06-05 | 1998-11-17 | Kimberly-Clark Worldwide | Pre-dyes, pre-dye compositions, and methods of developing a color |
US5811199A (en) * | 1995-06-05 | 1998-09-22 | Kimberly-Clark Worldwide, Inc. | Adhesive compositions containing a photoreactor composition |
US6033465A (en) | 1995-06-28 | 2000-03-07 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
US5885337A (en) | 1995-11-28 | 1999-03-23 | Nohr; Ronald Sinclair | Colorant stabilizers |
US6168655B1 (en) | 1995-11-28 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6168654B1 (en) | 1996-03-29 | 2001-01-02 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US6524379B2 (en) | 1997-08-15 | 2003-02-25 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6503559B1 (en) | 1998-06-03 | 2003-01-07 | Kimberly-Clark Worldwide, Inc. | Neonanoplasts and microemulsion technology for inks and ink jet printing |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6228157B1 (en) | 1998-07-20 | 2001-05-08 | Ronald S. Nohr | Ink jet ink compositions |
US6265458B1 (en) | 1998-09-28 | 2001-07-24 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368396B1 (en) | 1999-01-19 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Colorants, colorant stabilizers, ink compositions, and improved methods of making the same |
US6331056B1 (en) | 1999-02-25 | 2001-12-18 | Kimberly-Clark Worldwide, Inc. | Printing apparatus and applications therefor |
US6294698B1 (en) | 1999-04-16 | 2001-09-25 | Kimberly-Clark Worldwide, Inc. | Photoinitiators and applications therefor |
US6368395B1 (en) | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
US6486227B2 (en) | 2000-06-19 | 2002-11-26 | Kimberly-Clark Worldwide, Inc. | Zinc-complex photoinitiators and applications therefor |
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