US3547646A - Light-sensitive imaging material containing hydrazones - Google Patents
Light-sensitive imaging material containing hydrazones Download PDFInfo
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- US3547646A US3547646A US691333A US3547646DA US3547646A US 3547646 A US3547646 A US 3547646A US 691333 A US691333 A US 691333A US 3547646D A US3547646D A US 3547646DA US 3547646 A US3547646 A US 3547646A
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- Prior art keywords
- light
- sensitive
- printing
- chloride
- sulfone
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- 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
- Such a sensitizing process is employed in order to broaden the effective wave length band response of a printing material and aims at the sensitization for a visible zone. Accordingly, the process may be effectively applied to the case where there is used a tungsten lamp which emits a large amount of visible light, but cannot display successful sensitizing effects in the case of a commercially available diazo copying machine in which ultraviolet light is utilized.
- the present invention is entirely different in object, structure and effect from such sensitizing process as mentioned above. That is, the present method uses a hydrazone compound, represented by the general formula shown later, in a free-radical type imaging material to increase the sensitivity of a light sensitive system within the light-sensitive wave length area inherent to the photo- 3,547,646 Patented Dec. 15, 1970 activator employed (ordinarily 350-420 mg).
- a hydrazone compound represented by the general formula shown later
- a free-radical type imaging material to increase the sensitivity of a light sensitive system within the light-sensitive wave length area inherent to the photo- 3,547,646 Patented Dec. 15, 1970 activator employed (ordinarily 350-420 mg).
- the light-sensitive wave length area of the printing material of the present invention is in the ultaviolet zone, as mentioned above, and the room lamps employed at the time of production and printing of the printing material may be covered with filters which can shield only ultraviolet light, whereby the operations can be safely effected in considerably bright rooms.
- the hydrazone compounds employed in the present method are colorless or slight yellow, and there is little danger that the backgrounds of printing materials are colored and stained or the qualities thereof are degraded.
- alkyl group or aryl group examples of these compounds are as follows.
- photoactivators to be used in the light-sensitive printing materials of the present invention ie. photoactivators capable of yielding free radicals by action of light, may be any of those which have been known heretofore. Typical examples of such photoactivators are as follows:
- Rx represents 1-5 substituents on the benzene ring which substituents are selected from the group consisting of nitro, halogen, alkyl, haloalkyl, acetyl, haloacetyl, alkaryl and alkoxy groups, and not all of these substituents are required to be same.
- substituents are selected from the group consisting of nitro, halogen, alkyl, haloalkyl, acetyl, haloacetyl, alkaryl and alkoxy groups, and not all of these substituents are required to be same.
- color modifiers there are those usable as the socalled negative-position type which originally are colorless substances but are convertible into a colored state by action of free radicals formed from the above-mentioned photoactivators, and those usable as the so-called positive-positive type which originally are colored substances but are changed in color or are decolored to colorless by action of the free radicals.
- various coloring matters are effectively used, including, for example, amine compounds such as diphenylamine, benzylamine, triphenylamine, N-hydroXyethyl-N-ethylaniline and p,p-methylenebis (N,N-diethylaniline); leuco bases of dyes such as leuco-malachite green, Michlers hydrol and Lcucomethylene Blue; and various dyes of the diphenylmethane, triphenylmethane, thiazine, oxazine, xanthene, anthraquinone, iminonphthoquinone and ammethine types.
- amine compounds such as diphenylamine, benzylamine, triphenylamine, N-hydroXyethyl-N-ethylaniline and p,p-methylenebis (N,N-diethylaniline)
- leuco bases of dyes such as leuco-malachi
- the method of the present invention is etfectively applied not only to printing materials in which have been used other known sensitizers, but also to printing materials incirporated with color tone improvers, extenders and binder resins which have heretofore been used in this kind of printing materials.
- FIG. 1 relates to unsensitized material.
- FIG. 2 relates to material sensitized according to prior art.
- FIGS. 3 and 4 relate to material sensitized according to the present invention.
- the present invention concerns means for sensitizing a light-sensitive printing material, characterized by adding to the light-sensitive system a hydrazone compound represented by the aforesaid general formula.
- the effective amount of said hydrazone compound to be added is at least 0.001 part by weight per part of the photoactivator, and favorable results can be obtained when tre hydrazone compound is added in substantially the same amount as that of the photoactivator.
- fixing and the like treatments may be effected in the same manner as in the case of the conventional printing materials.
- the characteristics of the present invention reside in that the hydrazone compound added to a lightsensitive system makes it possible to shorten the time of printing with ultraviolet light and to effect printing by use of a weak light source without coloring the background of the printing material.
- Tribromomethylphenyl sulfone-IO g. Diethanolaniline30 g.
- the thus obtained light-sensitive printing materials were individually attached with a photographic negative and were exposed for 3 seconds to an 800 w. high pressure mercury lamp at a distance of 5 cm., whereby the materials (c) and (d) gave deep blue positive images whereas the materials (a) and (b) gave mere light blue positive images.
- the light-sensitive printing materials bearing individual images obtained in the above were dipped for one minute in a fixing solution of the composition shown below, whereby copies entirely stable to light were obtained.
- the backgrounds of the copies using the materials (b) and (d) were colored to orange to injure the photographic qualities of the copies, whereas the background of the copy using the present material (c) was White Without being colored or stained.
- FIGS. 1 to 4 show, respectively, the sensitivity spectra of printing materials coated with the light-sensitive emulsions of the compositions (a) to (d) which were used in this example.
- FIG. 1 is the sensitivity spectrum of the unsensitized light-sensitive printing material.
- FIG. 2 is the sensitivity spectrum of the light-sensitive printing material sensitized according to a known sensitizing process. As is clear from the spectrum, the material was made light-sensitive over a broader wave length band. In contrast to this, the printing material in accordance with the present invention was increased only in the sensitivity of inherent light-sensitive wave length area, as seen in the spectrum of FIG. 3. However, the printing material using, in combination, a sensitizer according to the present invention and that employed in the known process was not only increased in the sensitivity of inherent light-sensitive Wave length area but was also broadened in the light-sensitive wave length band. Thus, it is not objectionable at all to use the sensitizers of the present invention in combination with known sensitizers.
- EXAMPLE 2 Under a red safety lamp, a light-sensitive composition shown below was applied onto a photographic baryta paper and was dried.
- Hexabromodimethyl sulfone g. Diphenylamine-30 g. Benzophenone-benzoylhydrazone(sensitizer IV)--5 g. Acetone-500 cc.
- the thus obtained light-sensitive printing material was attached to a photographic negative and was exposed for 3 seconds to an 800 w. high pressure mercury lamp at a distance of 5 cm., whereby a deep blue positive image With a white background was immediately obtained.
- the printing material bearing said image was dipped for one minute in a fixing solution of the following compositions to obtain a copy entirely stable to light.
- EXAMPLE 3 In the same manner as in Example 2, a light-sensitive composition shown below was applied onto a photographic baryta paper.
- the thus obtained light-sensitive printing material was exposed to a 500 w. xenon lamp so that the exposed surface came to have an illuminance of 10,000 luxes and was then subjected to fixing in the same manner as in Example 2, whereby the exposure time could be shortened to of the time required in the case of a conventional printing material.
- EXAMPLE 4 In the same manner as in Example 2, a light-sensitive composition shown below was applied onto a photographic baryta paper.
- EXAMPLE 5 In the same manner as in Example 2, a light-sensitive emulsion of the composition shown below was applied onto a photographic baryta paper.
- EXAMPLE 6 In the same manner as in Example 2, a light-sensitive emulsion of the composition shown below was applied onto a photographic baryta paper.
- the thus obtained light-sensitive printing material was exposed for 5 seconds to a 500 w. xenon lamp so that the exposed surface came to have an illuminance of 20,000 luxes to obtain a green positive image with a white background.
- a control material containing no sensitizer required 10 seconds in obtaining a positive image of the same intensity by exposure under the same conditions as above.
- EXAMPLE 7 In the same manner as in Example 2, a light-sensitive emulsion of the composition shown below was applied onto a photographic baryta paper.
- the thus obtained light-sensitive printing material was exposed for 10 seconds to a 500 w. xenon lamp so that the exposed surface came to have an illuminance of 20,000 luxes to obtain a bleached colorless (white) negative image with a greenish blue background.
- a control material containing no sensitizer required 20 seconds in obtaining a negative image of the same extent by exposure under the same conditions as above.
- Light-sensitive imaging material comprising:
- R is an aryl, or heterocyclic group
- R is hydrogen, or an alkyl or aryl group.
Description
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8226766 | 1966-12-16 |
Publications (1)
Publication Number | Publication Date |
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US3547646A true US3547646A (en) | 1970-12-15 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US691333A Expired - Lifetime US3547646A (en) | 1966-12-16 | 1967-12-18 | Light-sensitive imaging material containing hydrazones |
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Cited By (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3630656A (en) * | 1968-10-19 | 1971-12-28 | Bayer Ag | Process for the dyeing and printing of metal-containing polyolefin textile materials |
US3886211A (en) * | 1968-12-10 | 1975-05-27 | Ciba Geigy Corp | Carboxylic acid hydrazide derivatives |
US4150987A (en) * | 1977-10-17 | 1979-04-24 | International Business Machines Corporation | Hydrazone containing charge transport element and photoconductive process of using same |
US4233209A (en) * | 1978-11-15 | 1980-11-11 | Ciba-Geigy Corporation | Hindered phenol hydrazones and compositions stabilized therewith |
US4244604A (en) * | 1979-05-23 | 1981-01-13 | Minnesota Mining And Manufacturing Company | Image-offsetting |
US4262937A (en) * | 1979-05-23 | 1981-04-21 | Minnesota Mining And Manufacturing Company | Carbonless imaging system |
US4334015A (en) * | 1979-05-23 | 1982-06-08 | Minnesota Mining And Manufacturing Company | Imaging compositions |
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 |
US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
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 |
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US2892713A (en) * | 1954-07-08 | 1959-06-30 | Agfa Ag | Photographic color development employing pyrazoline compounds |
AT221721B (en) * | 1958-08-21 | 1962-06-12 | Sandoz Ag | Process for the preparation of new hydrazides |
GB921322A (en) * | 1960-05-23 | 1963-03-20 | Charles E Frosst & Company | Substituted hydrazide compounds |
-
1967
- 1967-12-18 US US691333A patent/US3547646A/en not_active Expired - Lifetime
Patent Citations (4)
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US2892714A (en) * | 1954-07-08 | 1959-06-30 | Agfa Ag | Photographic color development with pyrazoline developers |
US2892713A (en) * | 1954-07-08 | 1959-06-30 | Agfa Ag | Photographic color development employing pyrazoline compounds |
AT221721B (en) * | 1958-08-21 | 1962-06-12 | Sandoz Ag | Process for the preparation of new hydrazides |
GB921322A (en) * | 1960-05-23 | 1963-03-20 | Charles E Frosst & Company | Substituted hydrazide compounds |
Cited By (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3630656A (en) * | 1968-10-19 | 1971-12-28 | Bayer Ag | Process for the dyeing and printing of metal-containing polyolefin textile materials |
US3886211A (en) * | 1968-12-10 | 1975-05-27 | Ciba Geigy Corp | Carboxylic acid hydrazide derivatives |
US4150987A (en) * | 1977-10-17 | 1979-04-24 | International Business Machines Corporation | Hydrazone containing charge transport element and photoconductive process of using same |
US4233209A (en) * | 1978-11-15 | 1980-11-11 | Ciba-Geigy Corporation | Hindered phenol hydrazones and compositions stabilized therewith |
US4244604A (en) * | 1979-05-23 | 1981-01-13 | Minnesota Mining And Manufacturing Company | Image-offsetting |
US4262937A (en) * | 1979-05-23 | 1981-04-21 | Minnesota Mining And Manufacturing Company | Carbonless imaging system |
US4334015A (en) * | 1979-05-23 | 1982-06-08 | Minnesota Mining And Manufacturing Company | Imaging compositions |
US5683843A (en) * | 1993-08-05 | 1997-11-04 | Kimberly-Clark Corporation | Solid colored composition mutable by ultraviolet radiation |
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 |
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 |
US6120949A (en) | 1993-08-05 | 2000-09-19 | Kimberly-Clark Worldwide, Inc. | Photoerasable paint and method for using photoerasable paint |
US5858586A (en) | 1993-08-05 | 1999-01-12 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
US6066439A (en) | 1993-08-05 | 2000-05-23 | Kimberly-Clark Worldwide, Inc. | Instrument for photoerasable marking |
US5700850A (en) | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
US5643701A (en) * | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Electrophotgraphic process utilizing mutable colored composition |
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 |
US6054256A (en) | 1993-08-05 | 2000-04-25 | Kimberly-Clark Worldwide, Inc. | Method and apparatus for indicating ultraviolet light exposure |
US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
US6127073A (en) | 1993-08-05 | 2000-10-03 | Kimberly-Clark Worldwide, Inc. | Method for concealing information and document for securely communicating concealed information |
US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
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 |
US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
US6342305B1 (en) | 1993-09-10 | 2002-01-29 | Kimberly-Clark Corporation | Colorants and colorant modifiers |
US5709955A (en) | 1994-06-30 | 1998-01-20 | Kimberly-Clark Corporation | Adhesive composition curable upon exposure to radiation 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 |
US6090236A (en) | 1994-06-30 | 2000-07-18 | Kimberly-Clark Worldwide, Inc. | Photocuring, articles made by photocuring, and compositions for use in photocuring |
US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species 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 |
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 |
US5747550A (en) * | 1995-06-05 | 1998-05-05 | Kimberly-Clark Worldwide, Inc. | Method of generating a reactive species and polymerizing an unsaturated polymerizable material |
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 |
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 |
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 |
US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
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 |
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 |
US5891229A (en) | 1996-03-29 | 1999-04-06 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
US5782963A (en) | 1996-03-29 | 1998-07-21 | 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 |
US6277897B1 (en) | 1998-06-03 | 2001-08-21 | Kimberly-Clark Worldwide, Inc. | 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 |
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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