DE1282449B - Photosensitive layers - Google Patents
Photosensitive layersInfo
- Publication number
- DE1282449B DE1282449B DEH53745A DEH0053745A DE1282449B DE 1282449 B DE1282449 B DE 1282449B DE H53745 A DEH53745 A DE H53745A DE H0053745 A DEH0053745 A DE H0053745A DE 1282449 B DE1282449 B DE 1282449B
- Authority
- DE
- Germany
- Prior art keywords
- activator
- leuco
- photosensitive
- layer
- dimethylamino
- 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.)
- Pending
Links
- 239000012190 activator Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 7
- -1 Ri is H Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 claims description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 239000012964 benzotriazole Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 11
- 239000000975 dye Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 2
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- WZKXBGJNNCGHIC-UHFFFAOYSA-N Leucomalachite green Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=CC=C1 WZKXBGJNNCGHIC-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
- G03C1/732—Leuco dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES 40BTWW PATENTAMT Int. Cl.: FEDERAL REPUBLIC OF GERMANY GERMAN 40BTWW PATENT OFFICE Int. Cl .:
G03cG03c
Deutsche Kl.: 57 b-1/72 German class: 57 b -1/72
Nummer: 1282449Number: 1282449
Aktenzeichen: P 12 82 449.6-51 (H 53745)File number: P 12 82 449.6-51 (H 53745)
Anmeldetag: 10. September 1964Filing date: September 10, 1964
Auslegetag: 7. November 1968Open date: November 7, 1968
Die Erfindung betrifft lichtempfindliche Schichten mit einer Leukoverbindung der FormelnThe invention relates to light-sensitive layers containing a leuco compound of the formulas
RxRx
(D Lichtempfindliche Schichten (D Photosensitive layers
(H)(H)
(NI)(NI)
worin R gleich H, (Ci-C>)-Alkyl oder Aryl, Ri gleich H, Alkyl, Aryl oderwhere R is H, (Ci-C>) - alkyl or aryl, Ri is the same H, alkyl, aryl or
Anmelder:Applicant:
Horizons Incorporated, Cleveland, Ohio (V. St. A.)Horizons Incorporated, Cleveland, Ohio (V. St. A.)
Vertreter:Representative:
Dr. W. Schalk, Dipl.-Ing. P. Wirth, Dipl.-Ing. G. M. Dannenberg und Dr. V. Schmied-Kowarzik, Patentanwälte, 6000 Frankfurt, Große Eschenheimer Str.Dr. W. Schalk, Dipl.-Ing. P. Wirth, Dipl.-Ing. G. M. Dannenberg and Dr. V. Schmied-Kowarzik, patent attorneys, 6000 Frankfurt, Große Eschenheimer Str.
Als Erfinder benannt: Robert H. Sprague, Chagrin Falls, Ohio; John A. Stewart, Parma, Ohio; James M. Lewis, Cleveland, Ohio (V. St. A.)Named inventor: Robert H. Sprague, Chagrin Falls, Ohio; John A. Stewart, Parma, Ohio; James M. Lewis, Cleveland, Ohio (V. St. A.)
Beanspruchte Priorität: V. St. v. Amerika vom 17. September 1963 (309407)Claimed priority: V. St. v. America September 17, 1963 (309407)
Der Gegenstand der Erfindung geht von einer lichtempfindlichen Schicht mit einer Leukoverbindung 30 der FormelnThe subject of the invention is based on a photosensitive layer with a leuco compound 30 of the formulas
und Z gleich O, S, Se oder NH ist, einer farblosen, stickstoffhaltigen heterocyclischen Verbindung als Aktivator und gegebenenfalls einem Bindemittel.and Z is O, S, Se or NH, a colorless, nitrogen-containing heterocyclic compound as Activator and optionally a binder.
Es ist bekannt, zum Auskopieren lichtempfindliche Schichten mit mindestens einem Aktivator und einer oxydierbaren Leukobase zu verwenden. Es ist auch bereits vorgeschlagen worden, einen Triphenylmethanfarbstoff als Leukobase zu verwenden und die Lichtempfindlichkeit des photographischen Auf-Zeichnungsmaterials, insbesondere gegenüber ultraviolettem Licht durch Zusatz bestimmter Aldehyde, Ester und Ketone zu verbessern.It is known to copy out photosensitive layers with at least one activator and one to use oxidizable leuco base. A triphenylmethane dye has also been proposed to use as a leuco base and the photosensitivity of the photographic recording material, especially to improve against ultraviolet light by adding certain aldehydes, esters and ketones.
Nachteilig an den bereits bekannten oder vorgeschlagenen photographischen Aufzeichnungsmaterialien der genannten Art ist, daß diese noch keine zufriedenstellende Empfindlichkeit gegenüber sichtbarem und ultraviolettem Licht besitzen.Disadvantages of the already known or proposed photographic recording materials of the kind mentioned is that this still does not have a satisfactory sensitivity to visible and ultraviolet light.
Aufgabe der Erfindung ist, direkt auskopierende lichtempfindliche Schichten anzugeben, die eine verbesserte Empfindlichkeit gegenüber sichtbarem und ultraviolettem Licht besitzen.The object of the invention is to provide photosensitive layers which can be copied out directly and which have an improved Have sensitivity to visible and ultraviolet light.
\R (HD\ R (HD
10« 630/99210 «630/992
worin R gleich H, (Ci-C2)-Alkyl oder Aryl, Ri Die bevorzugten Leukoverbindungen der anderenwhere R is H, (Ci-C 2 ) -alkyl or aryl, Ri are the preferred leuco compounds of the others
gleich H, Alkyl, Aryl oder Klasse sind vorzugsweise in 3,6-Stellung substituiert.equal to H, alkyl, aryl or class are preferably substituted in the 3,6-position.
J^ Besonders bevorzugt werden folgende Leukover-J ^ The following Leukover-
/ bindungen:/ bindings:
■N 5■ N 5
\£ 3,6-Bis-(diäthylamino)-9-(p-dimethylammo-\ £ 3,6-bis (diethylamino) -9- (p-dimethylammo-
phenyl)-xanthen,phenyl) -xanthene,
und Z gleich O, S, Se oder NH ist, einer farblosen, 3,6-Bis-(diäthylamino)-9-(p-diäthylamino-and Z is O, S, Se or NH, a colorless, 3,6-bis- (diethylamino) -9- (p-diethylamino-
stickstoffhaltigen heterocyclischen Verbindung als phenyl)-xanthen odernitrogen-containing heterocyclic compound as phenyl) -xanthene or
Aktivator und gegebenenfalls einem Bindemittel aus io 3,6-Bis-(dimethylamino)-9-(p-dimethylamino-Activator and optionally a binder from io 3,6-bis (dimethylamino) -9- (p-dimethylamino-
und ist dadurch gekennzeichnet, daß sie als Aktivator phenyl)-thioxanthen.
ein Triazol oder ein heterocyclisches Ketimid mitand is characterized in that it is phenyl) thioxanthene as an activator.
a triazole or a heterocyclic ketimide with
5 oder 6 Ringatomen enthält. Gemäß einer weiteren Ausgestaltung der Erfindung Die in den erfindungsgemäßen lichtempfindlichen enthält die lichtempfindliche Schicht als Leuko-Contains 5 or 6 ring atoms. According to a further embodiment of the invention In the photosensitive according to the invention contains the photosensitive layer as a leuco
Schichten als Aktivatoren anwesenden farblosen 15 verbindung 3,6-Bis-(dimethylamino)-9-(p-dimethyl-Layers as activators present colorless 15 compound 3,6-bis- (dimethylamino) -9- (p-dimethyl-
Triazole oder heterocyclischen Ketimide mit 5 oder aminophenyl)-xanthen.Triazoles or heterocyclic ketimides with 5 or aminophenyl) -xanthene.
6 Ringatomen können in zwei tautomeren Formen Die Herstellung von photographischen Aufzeichvorliegen, nämlich als nungsmaterialien mit der erfindungsgemäßen licht-6 ring atoms can exist in two tautomeric forms The production of photographic records, namely as voltage materials with the inventive light
/\ empfindlichen Schicht kann in an sich bekannter/ \ sensitive layer can be known in per se
* / \ 20 Weise vorgenommen werden, vorzugsweise wird eine* / \ 20 way, preferably one will be
hetero- CH2 dünne Schicht mit den lichtempfindlichen Verbin-hetero- CH 2 thin layer with the light-sensitive compounds
cyclischer | düngen auf einen inerten Schichtträger aufgebracht,cyclic | fertilize applied to an inert substrate,
Ring C = NH wobei ein Schichtträger aus einem filmbildendenRing C = NH where a support made of a film-forming
\ / - Kunststoff, der gegebenenfalls durchsichtig ist, sehr\ / - Plastic, which may be transparent, very much
\v/ 25 gut geeignet ist.\ v / 25 works well.
oder als Als Bindemittel kann jedes zur Herstellung vonor as a binder can be any for the production of
y\ photographischen Aufzeichnungsmaterialien übliche y \ photographic recording materials usual
/ \ Bindemittel verwendet werden. Gemäß einer Aus-/ \ Binders are used. According to an
hetero- CH gestaltung der Erfindung enthält die lichtempfindlichehetero- CH design of the invention includes the photosensitive
cyclischer || 3° Schicht als Bindemittel Cellulose oder ein Cellulose-cyclic || 3rd layer as a binder cellulose or a cellulose
Ring % C-NH2 derivat.Ring % C-NH 2 derivative.
Um die Lichtempfindlichkeit von erfindungsgemäßen lichtempfindlichen Schichten zu untersuchen, wurde folgendes Verfahren verwendet: Es Die wirksame Form der Aktivatoren scheint die 35 wurde eine Mischung von je 2 ecm Aceton und einer Struktur mit der Imidgruppe zu sein, jedoch ist 10%igen Polystyrollösung in Benzol hergestellt, der Wirkungsmechanismus noch nicht bekannt. Hierin wurden 3,6-Bis-(dimethylamino)-9-(p-dime-In order to investigate the photosensitivity of photosensitive layers according to the invention, The following procedure was used: It seems that the effective form of the activators was a mixture of 2 ecm acetone and one Structure with the imide group, however, 10% polystyrene solution is made in benzene, the mechanism of action not yet known. Here 3,6-bis (dimethylamino) -9- (p-dim-
AIs Aktivatoren werden folgende Verbindungen thylaminophenyl)-xanthen in gleicher Menge wie besonders bevorzugt: der verwendete Aktivator, wie er in Tabelle I auf-As activators, the following compounds are thylaminophenyl) -xanthene in the same amount as particularly preferred: the activator used, as shown in Table I
40 geführt ist, gelöst. Die erhaltene Beschichtungsflüssigkeit wurde auf einen Schichtträger aus einem40 is performed, solved. The obtained coating liquid was coated on a support made of a
t? ς rhi tv. τ* · 1 Die Belichtung des so hergestellten lichtempfind-t? ς rhi tv. τ * 1 The exposure of the photosensitive
ß. z^nioroenzinazoi 4J Hchen Materials .^11nJ6 entweder mit einer Reflektor-ß. z ^ nioroenzinazoi 4J Hchen Materials . ^ 11n J 6 either with a reflector-
Gemäß einer Ausgestaltung der Erfindung enthält Photolampe durch einen Stufenkeil vorgenommen,According to one embodiment of the invention, the photolamp is made by a step wedge,
die lichtempfindliche Schicht als Aktivator Benz- und zwar 5 Minuten lang mit der 30 cm vom licht-the light-sensitive layer as an activator Benz- for 5 minutes with the 30 cm from the light-
triazol oder Isoxazolonimid. empfindlichen Aufzeichnungsmaterial entferntentriazole or isoxazolonimide. removed sensitive recording material
In der erfindungsgemäßen lichtempfindlichen Lampe oder in einem Sensitometer unter VerwendungIn the photosensitive lamp according to the invention or in a sensitometer using
Schicht sind auch farbbildende Leukoverbindungen 50 eines geeigneten Tageslichtfilters,Layer are also color-forming leuco compounds 50 of a suitable daylight filter,
enthalten, und zwar entweder Leukotriarylmethan- Zur Fixierung des hergestellten Farbbildes wurden,contain, namely either leukotriaryl methane.
farbstoffe oder Leukoverbindungen, die sich von um ein beständiges, praktisch verwertbares Bilddyes or leuco compounds that differ from a stable, practically usable image
Leukoxanthenen, Leukothioxanthenen und Leuko- herzustellen, zwei an sich bekannte Verfahren ver-Leukoxanthenen, Leukothioxanthenen and Leuko- to produce, two known processes
acridinen ableiten und sich von Leukotriarylmethan- wendet. Bei einem Verfahren wurde das belichteteacridines and turns from leukotriaryl methane. In one process the was exposed
farbstoffen durch die Anwesenheit von einem oder 55 Aufzeichnungsmaterial zwei- oder mehrmals mitdyes due to the presence of one or more recording material two or more times
mehreren Brücken-Heteroatomen unterscheiden. einer Mischung aus 1 Teil Aceton und 4 Teilendifferentiate between several bridge heteroatoms. a mixture of 1 part acetone and 4 parts
Als Leukotriarylmethanfarbstoffe werden Vorzugs- Petroläther gespült. Bei dem anderen VerfahrenPreferred petroleum ethers are rinsed as leukotriarylmethane dyes. The other method
weise folgende oder ähnliche Verbindungen ver- wurde das belichtete Aufzeichnungsmaterial 4Mi-wise the following or similar compounds, the exposed recording material was 4Mi-
wendet: nuten lang in einem Konvektionsofen auf 125°C turns: take a long groove in a convection oven at 125 ° C
60 erwärmt.60 heated.
Leukokristallviolett, Nach der Fixierung wurde das photographische Leuco crystal violet, after fixation became photographic
LeukoopalbUu, Aufzeichnungsmaterial nochmals 4 Minuten lang LeukoopalbUu, recording material for another 4 minutes
Leukomalachitgrün, , mit einer Photolampe ohne Nachdunkeln total Leuco malachite green, total with a photo lamp without darkening
LeukorosaöiUa oder belichtet. Die Auswertung der belichteten, licht- LeukorosaöiUa or exposed. The evaluation of the exposed, light-
Leuko-p-rosanilln, 65 empfindlichen Aufzeichnungsmaterialien wurde da- Leuko-p-rosanilln, 65 sensitive recording materials was
P»p'.p"-TrtoetiiyHeukoopalblau, durch vorgenommen, daß die Dichte und die AnzahlP »p'.p" -TrtoetiiyHeukoopalblau, made by that the density and the number
p.p^-Trichlor-leukoopalblau, der· in dem entstandenen Bild sichtbaren Stufen nachp.p ^ -Trichlor-leukoopalblau, according to the steps visible in the resulting picture
p.p'-Bii-tetrftraethyl-diaminodiphenylmethan. der Fixierung abgelesen wurde.p.p'-bi-tetraethyl-diaminodiphenylmethane. the fixation was read.
5 65 6
Die bei den Belichtungen erzielten Ergebnisse sind in der nachfolgenden Tabelle aufgeführt.The results obtained with the exposures are shown in the table below.
Schichtträger + SchleierLayer support + veil
baren Stufenavailable levels
Ähnliche Ergebnisse wurden auch unter Verwendung von Leukokristall violett als Leuko verbindung und von 5-Chlorbenztriazol als Aktivator erhalten. Ersetzt man das 5-Chlorbenztriazol durch 3-Naphthylisooxazolonimid, so wird ein blaues Bild vergleichbarer Dichte erhalten.Similar results were also obtained using leuco crystal violet as the leuco compound and obtained from 5-chlorobenzotriazole as an activator. If the 5-chlorobenzotriazole is replaced by 3-naphthylisooxazolonimide, thus a blue image of comparable density is obtained.
Der photochemische Mechanismus bei der Belichtung der lichtempfindlichen Schicht ist noch nicht völlig geklärt. Man hat Grund zur Annahme, daß das erhaltene Bild aus einem Farbstoff gebildet wird, der ein Oxydationsprodukt der eingesetzten Leukobase ist. Der aktive Bestandteil der lichtempfindlichen Schicht scheint eine geringe Menge is eines Oxydationsproduktes der Leukobase zu sein, das sich mit dem Sauerstoff der Atmosphäre gebildet hat.The photochemical mechanism in the exposure of the photosensitive layer is still not fully clarified. There is reason to believe that the image obtained is composed of a dye which is an oxidation product of the leuco base used. The active component of the photosensitive The layer appears to be a small amount of an oxidation product of the leuco base, that formed with the oxygen in the atmosphere.
Durch die Erfindung wird erreicht, daß bei einem direkt auskopierenden, photographischen Aufzeichnungsmaterial eine verbesserte Lichtempfindlichkeit erhalten wird und beständige, praktisch verwertbare Bilder herzustellen sind.The invention achieves that in the case of a photographic recording material which is to be copied out directly improved photosensitivity is obtained and stable, practicable Images are to be produced.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US309407A US3284205A (en) | 1963-09-17 | 1963-09-17 | Benzotriazole and heterocyclic ketimide activators for leuco compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1282449B true DE1282449B (en) | 1968-11-07 |
Family
ID=23198109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH53745A Pending DE1282449B (en) | 1963-09-17 | 1964-09-10 | Photosensitive layers |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3284205A (en) |
| BE (1) | BE653197A (en) |
| DE (1) | DE1282449B (en) |
| GB (1) | GB1030887A (en) |
| NL (1) | NL6410585A (en) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364030A (en) * | 1964-04-29 | 1968-01-16 | Du Pont | Leuco dye-diacylazino light-sensitive dye former compositions |
| US3359109A (en) * | 1964-04-29 | 1967-12-19 | Du Pont | Leuco dye-n, n. o-triacylhydroxylamine light-sensitive dye former compositions |
| US3360370A (en) * | 1964-04-29 | 1967-12-26 | Du Pont | Leuco dye-aromatic bitriazole lightsensitive dye former compositions |
| US3395018A (en) * | 1964-04-29 | 1968-07-30 | Du Pont | Light-sensitive color-forming composition |
| US3390997A (en) * | 1964-04-29 | 1968-07-02 | Du Pont | Photosensitive composition comprising a triphenylemethane derivative and a nitrogen-containing photo-oxidant |
| US3390994A (en) * | 1966-02-17 | 1968-07-02 | Du Pont | Photodeactivatable light-sensitive color-forming composition |
| US4425424A (en) | 1982-04-08 | 1984-01-10 | Eastman Kodak Company | Dye-forming compositions |
| DE3717037A1 (en) * | 1987-05-21 | 1988-12-08 | Basf Ag | PHOTOPOLYMERIZABLE RECORDING MATERIALS, PHOTORESIS LAYERS AND FLAT PRINTING PLATES BASED ON THESE RECORDING MATERIALS |
| DE3717038A1 (en) * | 1987-05-21 | 1988-12-08 | Basf Ag | PHOTOPOLYMERIZABLE RECORDING MATERIALS, PHOTORESIS LAYERS AND FLAT PRINTING PLATES BASED ON THESE RECORDING MATERIALS |
| US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
| US5721287A (en) * | 1993-08-05 | 1998-02-24 | Kimberly-Clark Worldwide, Inc. | Method of mutating a colorant by irradiation |
| US5700850A (en) * | 1993-08-05 | 1997-12-23 | Kimberly-Clark Worldwide | Colorant compositions and colorant stabilizers |
| 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 |
| US5733693A (en) * | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
| US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
| CA2120838A1 (en) * | 1993-08-05 | 1995-02-06 | Ronald Sinclair Nohr | Solid colored composition mutable by ultraviolet radiation |
| US5643356A (en) * | 1993-08-05 | 1997-07-01 | Kimberly-Clark Corporation | Ink for ink jet printers |
| US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
| US5773182A (en) * | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
| US5865471A (en) * | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
| WO1997001605A1 (en) | 1995-06-28 | 1997-01-16 | Kimberly-Clark Worldwide, Inc. | Novel colorants and colorant modifiers |
| US5739175A (en) * | 1995-06-05 | 1998-04-14 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer |
| US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
| US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition 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 |
| US5798015A (en) * | 1995-06-05 | 1998-08-25 | Kimberly-Clark Worldwide, Inc. | Method of laminating a structure with adhesive containing a photoreactor composition |
| US5747550A (en) * | 1995-06-05 | 1998-05-05 | Kimberly-Clark Worldwide, Inc. | Method of generating a reactive species and polymerizing an unsaturated polymerizable material |
| US5811199A (en) * | 1995-06-05 | 1998-09-22 | Kimberly-Clark Worldwide, Inc. | Adhesive compositions containing a photoreactor composition |
| US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable 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 |
| AU6378696A (en) | 1995-06-05 | 1996-12-24 | Kimberly-Clark Worldwide, Inc. | Novel pre-dyes |
| US5855655A (en) | 1996-03-29 | 1999-01-05 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| KR19980701718A (en) | 1995-11-28 | 1998-06-25 | 바바라 에이취. 폴 | Improved Color Stabilizer |
| US6099628A (en) | 1996-03-29 | 2000-08-08 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US5782963A (en) | 1996-03-29 | 1998-07-21 | Kimberly-Clark Worldwide, Inc. | Colorant stabilizers |
| US5891229A (en) | 1996-03-29 | 1999-04-06 | 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 |
| EP1000090A1 (en) | 1998-06-03 | 2000-05-17 | Kimberly-Clark Worldwide, Inc. | Novel photoinitiators and applications therefor |
| KR100591999B1 (en) | 1998-06-03 | 2006-06-22 | 킴벌리-클라크 월드와이드, 인크. | Neo-nanoplasm and inkjet printing inks manufactured by microemulsion technology |
| BR9912003A (en) | 1998-07-20 | 2001-04-10 | Kimberly Clark Co | Enhanced inkjet ink compositions |
| ES2263291T3 (en) | 1998-09-28 | 2006-12-01 | Kimberly-Clark Worldwide, Inc. | CHEATS THAT INCLUDE QUINOID GROUPS AS PHOTOINIATORS. |
| EP1144512B1 (en) | 1999-01-19 | 2003-04-23 | Kimberly-Clark Worldwide, Inc. | Novel 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 |
| KR100772772B1 (en) | 2000-06-19 | 2007-11-01 | 킴벌리-클라크 월드와이드, 인크. | Novel Photoinitiators and Their Uses |
| WO2010067078A2 (en) * | 2008-12-10 | 2010-06-17 | Wista Laboratories Ltd. | 3,6-disubstituted xanthylium salts as medicaments |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2895892A (en) * | 1954-08-10 | 1959-07-21 | Chalkley Lyman | Photochemical process |
| US2927025A (en) * | 1956-10-23 | 1960-03-01 | Ibm | Photosensitive materials and recording media |
| US2981622A (en) * | 1959-07-13 | 1961-04-25 | Chalkley Lyman | Photographic process |
-
1963
- 1963-09-17 US US309407A patent/US3284205A/en not_active Expired - Lifetime
-
1964
- 1964-09-01 GB GB35784/64A patent/GB1030887A/en not_active Expired
- 1964-09-10 DE DEH53745A patent/DE1282449B/en active Pending
- 1964-09-11 NL NL6410585A patent/NL6410585A/xx unknown
- 1964-09-17 BE BE653197D patent/BE653197A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1030887A (en) | 1966-05-25 |
| US3284205A (en) | 1966-11-08 |
| BE653197A (en) | 1965-01-18 |
| NL6410585A (en) | 1965-03-18 |
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