DE1226878B - Photosensitive diazo layer - Google Patents
Photosensitive diazo layerInfo
- Publication number
- DE1226878B DE1226878B DEK42354A DEK0042354A DE1226878B DE 1226878 B DE1226878 B DE 1226878B DE K42354 A DEK42354 A DE K42354A DE K0042354 A DEK0042354 A DE K0042354A DE 1226878 B DE1226878 B DE 1226878B
- Authority
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- Germany
- Prior art keywords
- methyl
- parts
- phenol
- piperazino
- dimethyl
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B06—GENERATING OR TRANSMITTING MECHANICAL VIBRATIONS IN GENERAL
- B06B—METHODS OR APPARATUS FOR GENERATING OR TRANSMITTING MECHANICAL VIBRATIONS OF INFRASONIC, SONIC, OR ULTRASONIC FREQUENCY, e.g. FOR PERFORMING MECHANICAL WORK IN GENERAL
- B06B1/00—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency
- B06B1/10—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency making use of mechanical energy
- B06B1/16—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency making use of mechanical energy operating with systems involving rotary unbalanced masses
- B06B1/167—Orbital vibrators having masses being driven by planetary gearings, rotating cranks or the like
- B06B1/168—Rotary pendulum vibrators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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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
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. CL:Int. CL:
G 03 cG 03 c
Deutsche Kl.: 57 b -12/05 German class: 57 b -12/05
Nummer: 1226 878Number: 1226 878
Aktenzeichen: K 42354IX a/57 bFile number: K 42354IX a / 57 b
Anmeldetag: 9. Dezember 1960Filing date: December 9, 1960
Auslegetag: 13. Oktober 1966Opening day: October 13, 1966
Die Erfindung betrifft eine lichtempfindliche Diazoschicht, in der sich mindestens eine Diazoverbindung und mindestens eine Kupplungskomponente befindet und die für die Herstellung von Zwischenoriginalen verwendbar ist.The invention relates to a photosensitive diazo layer in which there is at least one diazo compound and at least one coupling component is located and that for the production of intermediate originals is usable.
Es ist bekannt, daß man in der Diazotypie mit HiKe von lichtempfindlichen Schichten, die bei der Entwicklung gelbe bis grünlichgelbe Farbstoffe geben, Zwischenoriginale erhält, die sich sehr gut zum Weiterkopieren ζ. B. auf Diazotypie-Kopierschichten eignen. Beispiele für die Zusammensetzung derartiger lichtempfindlicher Schichten sind in der deutschen Patentschrift 697 744 angegeben, in der auch verschiedene Oxyverbindungen als Azokomponenten aufgeführt sind.It is known that in the diazotype with HiKe of light-sensitive layers that are used during development give yellow to greenish-yellow dyes, receive intermediate originals, which are very good for copying ζ. B. suitable on diazotype copy layers. Examples of the composition of such photosensitive ones Layers are given in German Patent 697 744, in which various Oxy compounds are listed as azo components.
Es ist ferner bekannt, als Azokomponenten für den genannten Zweck Hydroxy-dialkyl-morpholinomethylbenzole zu verwenden.It is also known, as azo components for the stated purpose, hydroxydialkylmorpholinomethylbenzenes to use.
Mit diesen bekannten lichtempfindlichen Diazoschichten erhält man jedoch Zwischenoriginale von nur durchschnittlicher Abdeckkraft. Die mit diesen Schichten erhältlichen Bilder ziehen auf den Schichtunterlagen außerdem nur schlecht auf und weisen auch eine nur mäßige Wasserfestigkeit auf. Aufgabe der Erfindung ist es, lichtempfindliche Diazoschichten für Zwischenoriginale zu schaffen, die auf dem Trägermaterial gut aufziehen und mit denen man Bilder von hoher Abdeckkraft erhält, die zudem eine verbesserte Wasserfestigkeit aufweisen. Gegenstand der Erfindung ist eine lichtempfindliche Diazoschicht der vorstehend genannten Art, mit welcher diese Verbesserungen erzielt werden. Sie enthält als Kupplungskomponenten mindestens eine Verbindung der FormelWith these known photosensitive diazo layers, however, intermediate originals of only average covering power. The images available with these layers pull on the layer base in addition, only poorly and also have only moderate water resistance. task The invention is to provide photosensitive diazo layers for intermediate originals which are on the support material open well and with which you get pictures of high covering power, which also improves Have water resistance. The invention relates to a photosensitive diazo layer of the above named way with which these improvements are achieved. It contains as coupling components at least one compound of the formula
Lichtempfindliche DiazoschichtPhotosensitive diazo layer
OHOH
worin R1 und R2 für gleiche oder verschiedene Alkylgruppen mit gerader oder verzweigter Kohlenstoff kette und R3 für eine Alkylgruppe, Hydroxyalkylgruppe, Aralkylgruppe, Arylgruppe, Carboxylgruppe oder Carbonsäureestergruppe stehen und die Kohlenstoffatome des Piperazinrings durch gleiche oder verschiedene Alkylreste mit gerader oder verzweigter Kohlenstoffkette substituiert sein können, wobei samtliehe Alkylgruppen in gerader Kohlenstoffkette nicht mehr als 5 Kohlenstoffatome aufweisen.where R 1 and R 2 represent identical or different alkyl groups with straight or branched carbon chain and R 3 represent an alkyl group, hydroxyalkyl group, aralkyl group, aryl group, carboxyl group or carboxylic acid ester group and the carbon atoms of the piperazine ring are substituted by identical or different alkyl radicals with straight or branched carbon chain can be, all of the alkyl groups in a straight carbon chain having no more than 5 carbon atoms.
Anmelder:Applicant:
Kalle Aktiengesellschaft,Kalle Aktiengesellschaft,
Wiesbaden-Biebrich, Rheingaustr. 190-196Wiesbaden-Biebrich, Rheingaustr. 190-196
Als Erfinder benannt:Named as inventor:
Dr. Heinz Schlesinger, WiesbadenDr. Heinz Schlesinger, Wiesbaden
Die erfindungsgemäß als Azokomponenten in Diazotypie-Kopierschichten zu verwendenden substituierten Dialkylphenole können beispielsweise nach dem Verfahren der Mannich-Kondensation durch Umsetzung von Dialkylphenolen mit äquimolekularen Mengen Formaldehyd und substituierten Piperazinen hergestellt werden.According to the invention as azo components in diazotype copying layers Substituted dialkylphenols to be used can, for example, according to the process the Mannich condensation by reacting dialkylphenols with equimolecular amounts Formaldehyde and substituted piperazines are produced.
Für die genannte Umsetzung geeignete Hydroxydialkylbenzole sind beispielsweise 2,5-Dimethylphenol, 2,3-Dimethylphenol, 3,5-Dimethylphenol, 2,6-Dimethylphenol, 3-Methyl-5-äthylphenol, 2-Methyl-5-isopropylphenol, 5-Methyl-2-isopropylphenol, 3-Methyl-6-äthylphenol. Hydroxydialkylbenzenes suitable for the reaction mentioned are, for example, 2,5-dimethylphenol, 2,3-dimethylphenol, 3,5-dimethylphenol, 2,6-dimethylphenol, 3-methyl-5-ethylphenol, 2-methyl-5-isopropylphenol, 5-methyl-2-isopropylphenol, 3-methyl-6-ethylphenol.
Als N-substituierte Piperazine für diese Reaktion werden z. B. genannt N-Methyl-piperazin, N-Hydroxyäthyl-piperazin,
N-Äthyl-piperazin, N-Benzyl-piperazin, N-Phenyl-piperazin, Piperazin-1-carbonsäureester.
Diese N-substituierten Piperazine können außerdem noch am Kohlenstoff substituiert sein, beispielsweise
l-Phenyl-2-methyl-piperazin, l-Phenyl-2-äthylpiperazin,
l-Phenyl-3-äthyl-piperazin.
.: Im folgenden wird an einem Beispiel die Herstellung einer Azokomponenten beschrieben, wie sie erfindungsgemäß
in lichtempfindlichen Diazoschichten verwendet werden soll. Dabei ist, wie auch in den weiter unten
folgenden Beispielen, als Einheit für 1 Volumteil 1 ml einzusetzen, wenn als Einheit für 1 Gewichtsteil 1 g
genommen wird.As N-substituted piperazines for this reaction, for. B. called N-methyl-piperazine, N-hydroxyethyl-piperazine, N-ethyl-piperazine, N-benzyl-piperazine, N-phenyl-piperazine, piperazine-1-carboxylic acid ester. These N-substituted piperazines can also be substituted on the carbon, for example 1-phenyl-2-methyl-piperazine, 1-phenyl-2-ethylpiperazine, 1-phenyl-3-ethyl-piperazine.
.: In the following, the production of an azo component is described using an example as it is to be used according to the invention in light-sensitive diazo layers. As in the examples below, 1 ml is to be used as the unit for 1 part by volume if 1 g is taken as the unit for 1 part by weight.
/In 150 Volumteilen werden 98 Gewichtsteile 2,5-Dimethylphenol gelöst, 85 Volumteile 30%iger Formaldehyd zugesetzt und unter Rühren und Kühlen eine Lösung von 130 Gewichtsteilen N-Phenyl-piperazin in 70 Volumteilen Methanol zugetropft. Nach 5stündigem Rühren wird über Nacht stehengelassen, wobei das abgeschiedene Öl kristallisiert. Der Kristallbrei wird mit 100 Volumteilen Methanol verrieben und abgesaugt. Das Rohprodukt liefert beim Umkristallisieren aus 1500 Volumteilen Essigsäureäthylester 74 Gewichtsteile reines 2,5-Dimethyl-4-[4'-phenyl-piperazino-(l')-methyl]-phenol vom Schmelzpunkt 184 bis 185 0C. Als Nebenprodukt kristallisiert aus der Essig-/ 98 parts by volume of 2,5-dimethylphenol are dissolved in 150 parts by volume, 85 parts by volume of 30% formaldehyde are added and a solution of 130 parts by weight of N-phenylpiperazine in 70 parts by volume of methanol is added dropwise with stirring and cooling. After stirring for 5 hours, the mixture is left to stand overnight, during which the oil which has separated out crystallizes. The crystal pulp is triturated with 100 parts by volume of methanol and filtered off with suction. When recrystallized from 1500 parts by volume of ethyl acetate, the crude product gives 74 parts by weight of pure 2,5-dimethyl-4- [4'-phenyl-piperazino- (l ') -methyl] -phenol with a melting point of 184 to 185 ° C. The by-product crystallizes from the Vinegar-
609 670/372609 670/372
säureäthylester-Mutterlauge beim Einengen unreines 2,5- Dimethyl - 6 - [4' - phenyl - piperazine - (1') - ntöthyl] phenol aus, das nach Umkristallisieren aus Äthanol bei 133 bis 134° C schmilzt. Die Konstitution der vorstehend beschriebenen beiden Isomeren kann durch katalytische Hydrierung mittels Kupfer-Chromoxyd-Katalysator bei etwa 130 at und 165° C bewiesen werden. Dabei liefert das Kondensationsprodukt vom Schmelzpunkt 184 bis 185°C das 2,4,5-Trimethylphenol (Schmelzpunkt171 bis 720C) und dasjenige vom Schmelzpunkt 133 bis 134° C das 2,3,6-Trimethylphenol (Schmelzpunkt' 63 bis 64° C).ethyl ester mother liquor on concentration of impure 2,5-dimethyl-6 - [4 '- phenyl - piperazine - (1') - ntoethyl] phenol, which melts at 133 to 134 ° C after recrystallization from ethanol. The constitution of the two isomers described above can be proven by catalytic hydrogenation using a copper-chromium oxide catalyst at about 130 at and 165 ° C. In this case, the condensation product gives a melting point 184 to 185 ° C 2,4,5-trimethylphenol (mp 1 71-72 0 C) and that of a melting point of 133-134 ° C 2,3,6-trimethylphenol (melting point '63 to 64 ° C).
In analoger Weise, gegebenenfalls unter geringfügigen .Abänderungen, wie Art und Menge des Lösungsmittels, angepaßt an die Löslichkeit der Reaktionspartner, kann man auch die anderen erfindungsgemäßen Verbindungen herstellen, die sowohl als freie Basen als auch in Form ihrer Salze isoliert und verwendet werden können.In an analogous manner, possibly with minor Modifications such as the type and amount of the Solvent, adapted to the solubility of the reactants, one can also use the other solvents according to the invention Prepare compounds that are isolated and used both as free bases and in the form of their salts can be.
Als weitere erfindungsgemäße Verbindungen werden genannt:Further compounds according to the invention are mentioned:
2,6-Dimethyl-4-[4'-phenyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 114° C). 3,5-Dimethyl-'2-[4'-methyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 99 bis 100° C). 2,5-Dimethyl-4-[4'-methyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 174 bis 1750C). 2,3-Dimethyl-6-[4'-phenyl-piperazino-(l')-methyl]* phenol (Schmelzpunkt 142 bis 143° C). . -2,6-Dimethyl-4- [4'-phenyl-piperazino- (1 ') -methyl] -phenol (melting point 114 ° C). 3,5-Dimethyl-'2- [4'-methyl-piperazino- (1 ') -methyl] -phenol (melting point 99 to 100 ° C). 2,5-dimethyl-4- [4'-methyl-piperazino- (1 ') -methyl] -phenol (melting point 174 to 175 ° C.). 2,3-Dimethyl-6- [4'-phenyl-piperazino- (1 ') -methyl] * phenol (melting point 142 to 143 ° C). . -
2,5-Dimethyl-4-[4'-i6-hydroxyäthyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 136 bis 137° C). 2,5-Dimethyl-4-[4'-benzyl-piperazino-(l')-methyl]-phenol-chlorhydrat (Schmelzpunkt 2370C unter Zersetzung).2,5-dimethyl-4- [4'- i 6-hydroxyethyl-piperazino- (l ') -methyl] -phenol (melting point 136 to 137 ° C). 2,5-dimethyl-4- [4'-benzyl-piperazino (l ') - methyl] -phenol hydrochloride (melting point 237 0 C with decomposition).
3-Methyl-6-isopropyl-4-[4'-methyl-piperazino- = (1 ')-methyl]-phenol-chlorhydrat (Schmelzpunkt 213 bis 214° C unter Zersetzung). -3-Methyl-6-isopropyl-4- [4'-methyl-piperazino- = (1 ') -methyl] -phenol-chlorohydrate (melting point 213 to 214 ° C with decomposition). -
3-Methyl-5-äthyl-2-[4'-phenyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 118d C).3-methyl-5-ethyl-2- [4'-phenyl-piperazino- (l ') -methyl] -phenol (melting point 118 ° C.).
2,6-Dimethyl-4-[4'-benzyl-piperazino-(l')-methyl]-phenol (Schmelzpunkt 151 bis 152°C). 3,5-Dimethyl-2-[4'-carbäthoxy-piperazino-(l')-methyl]-phenol (Schmelzpunkt 92° C). 2,5-Dimethyl-4-[4'-äthyl-piperazino-(l')-methyl]-phenol-chlorhydrat (Schmelzpunkt 217 bis 218°C unter Zersetzung).2,6-Dimethyl-4- [4'-benzyl-piperazino- (1 ') -methyl] -phenol (melting point 151-152 ° C). 3,5-Dimethyl-2- [4'-carbethoxy-piperazino- (1 ') -methyl] -phenol (melting point 92 ° C). 2,5-Dimethyl-4- [4'-ethyl-piperazino- (l ') -methyl] -phenol-chlorohydrate (melting point 217 to 218 ° C with decomposition).
2,6-Dimethyl-4-[4'-/8-hydroxyäthyl-piperazino-
: (l')-methyl]-phenol (Schmelzpunkt 136 bis 137° C).
2,6-Dimethyl-4-[3'-methyl-4'-phenyl-piperazino-(iO-methylj-phenol-chlörhydrat
(Schmelzpunkt 181 bis 182° C unter Zersetzung). 2,6-Dimethyl-4-[4'-carbäthoxy-piperazino-(l')-methyl]-phenol
(Schmelzpunkt 114 bis 115° C). 2,5-Dimethyl-4-[4'-carbäthoxy-piperazino- ■
(l>methyl]-phenol (Schmelzpunkt 101 bis 102° C). SjS-Dimethyl^-^'-carbpropoxy-piperazino-(l')-methyl]-phenol
(Schmelzpunkt 74° C). ■' 2,6-Dimethyl-4-[4'-carbpropoxy-piperazino-(l')-methyl]-phenolsulfat
(Schmelzpunkt 201 bis 202° C unter Zersetzung).
■ ! 2,5-Dimethyl-4-[4'-carbpropoxy-piperazino- :'2,6-dimethyl-4- [4'- / 8-hydroxyethyl-piperazino-: (l ') -methyl] -phenol (melting point 136 to 137 ° C). 2,6-Dimethyl-4- [3'-methyl-4'-phenyl-piperazino- (iO-methyl-phenol-chlorohydrate (melting point 181 to 182 ° C with decomposition). 2,6-Dimethyl-4- [4 '-carbethoxy-piperazino- (l') -methyl] -phenol (melting point 114 to 115 ° C). 2,5-dimethyl-4- [4'-carbethoxy-piperazino- ■ (l> methyl] -phenol (melting point 101 to 102 ° C) SjS-Dimethyl ^ - ^ '- carbpropoxy-piperazino- (1') - methyl] -phenol (melting point 74 ° C) ■ '2,6-Dimethyl-4- [4'-carbpropoxy piperazino (l ') methyl] phenol sulfate (melting point 201 to 202 ° C with decomposition).
■ ! 2,5-dimethyl-4- [4'-carbpropoxy-piperazino- : '
(l')-methyl]-phenolsulfat (Schmelzpunkt 181 bis - ■ - 183 ° C unter Zersetzung).(l ') - methyl] phenol sulfate (melting point 181 to - ■ - 183 ° C with decomposition).
2,6-Dimethyl-4-[4'-tolyl-piperazinö-(l')-methyl]-phenol (Schmelzpunkt 123 bis 124° C). 3,5-Dimethyl-2-[4'-tolyl-piperäzino-(l')-methyl]-. phenol (Schmelzpunkt 149 bis 1500C). °2,6-Dimethyl-4- [4'-tolyl-piperazinö- (l ') -methyl] -phenol (melting point 123-124 ° C). 3,5-dimethyl-2- [4'-tolyl-piperazino- (1 ') -methyl] -. phenol (melting point 149 to 150 ° C.). °
Die erfiüdungsgemäß zu verwendenden Azokompoinenten kuppeln mit allen in- der Diazotypie üblicherweise verwendeten Diazoverbindungen. Durch Kupplung mit bestimmten Diazoverbindungen, besonders mit p-Aminodiazobenzolverbindungen, entstehen gelbe bis grünlichgelbe Farbstoffe von einem so günstigen Absorptionsvermögen, daß sie eine hervorragende Abdeckkraft aufweisen, die sie für das Herstellen von Zwischenoriginalen ausgezeichnet brauchbar macht.The azo components to be used according to the invention couple with all diazo compounds commonly used in the diazotype. By coupling with certain diazo compounds, especially p-aminodiazobenzene compounds, yellow ones are produced to greenish yellow dyes of such a favorable absorption capacity that they have an excellent covering power have, which makes them excellently useful for the production of intermediate originals.
Die lichtempfindlichen -Diazoschichten ziehen infolge der starken Hydrotropie der darin enthaltenen Azokomponenten sehr gut auf das übliche Schichtträgermaterial, z. B. auf Transparentpapier, auf. Außerdem besitzen die mit den Schichten erhaltenen Kupplungsprodukte eine gesteigerte Wasserfestigkeit. Sie erzeugen ferner sehr kontrastreiche Linien mit starker Abdeckkraft. Infolgedessen werden auch Vorlagen mit schwäch gezeichneten dünnen -Linien vermittels der Diazoschichten noch deutlich •"wiedergegeben. Es hat sich ferner gezeigt, daß sich die erfindungsgemäßen Azokomponenten auch sehr .gut als Mischkomponenten mit anderen Azokomponenten zur Erzeugung von braunen und schwärzen Farbtönen eignen.The light-sensitive diazo layers pull as a result the strong hydrotropy of the azo components it contains very well on the usual layer support material, z. B. on tracing paper. In addition, those obtained with the layers have Coupling products have increased water resistance. They also produce very high-contrast lines with strong covering power. As a result, templates with weakly drawn, thin lines are also used of the diazo layers are still clearly shown. It has also been shown that the invention Azo components also very good as mixed components with other azo components Generation of brown and black color tones are suitable.
Eine . Acetylcellulosefolie wird "mit einer Lösung folgender Zusammensetzung gestrichen: 45 Volunv teile Methylglykol, 45 Volumteile Methyläthylketon, 10 Volumteile Wasser, 1,5 Gewichtsteile Zitronen? säure, 1,6 Gewichtsteüe Borsäure, 0,6 Gewichtsteile Sulfosalicylsäure, 4,5 Gewichtsteüe 3,5-Dimethyl-2 - [4' - methyl - piperazino -(I')- methyl] - phenol und 4,0 Gewichtsteüe der Diazoverbindung aus 1-Amino-3-methyl-4-N-äthylaminobenzol in Form des Flüoborates. Nach dem Trocknen belichtet man mit Hilfe einer 12-Ampere-Bogenlampe unter einer Vorlage und entwickelt in üblicher Weise mit Ammoniakgas. ;One . Acetyl cellulose sheet is "with a solution." The following composition is deleted: 45 parts by volume of methyl glycol, 45 parts by volume of methyl ethyl ketone, 10 parts by volume of water, 1.5 parts by weight of lemons? acid, 1.6 parts by weight boric acid, 0.6 parts by weight Sulfosalicylic acid, 4.5 parts by weight of 3,5-dimethyl-2 - [4 '- methyl - piperazino - (I') - methyl] - phenol and 4.0 parts by weight of the diazo compound from 1-amino-3-methyl-4-N-ethylaminobenzene in the form of the Flüoborates. After drying, it is exposed with the aid a 12 amp arc lamp under a template and developed in the usual way with ammonia gas. ;
Die erhaltenen Pausen weisen einen gelben Farbton auf und sind als Zwischenoriginale geeignet.The pauses obtained have a yellow hue and are suitable as intermediate originals.
Eine Lösung von 4,5 Gewichtsteüen 2,6-Dimethyl-4-[4' - carbäthoxy-piperazino - (l')-methyl] -phenol, 1 Vot lumteü konzentrierter reiner Salzsäure, 6 Gewichtsteüen Zitronensäure, 3 Gewichtsteüen Borsäure, 2 Gewichtsteüen Aluminiumsulfat und 4 Gewichtsteüen der Diazoverbindung aus l-Amino-4-morphoHnobenzol in Form des Zinkchlofiddoppelsalzes in 100 Volumteüen Wasser werden in üblicher Weise auf transparentes Papier gestrichen und getrocknet. Nach der Belichtung unter einer Vorlage mit Hufe einer 12-Ampere-Kohlenbogenlampe entwickelt man mit Ammoniakgas. Die Pausen, die einen gelben Farbton aufweisen, können zur Herstellung weiterer Kopien als Zwischenoriginale benutzt werden.A solution of 4.5 parts by weight of 2,6-dimethyl-4- [4 '- carbäthoxy-piperazino - (l') - methyl] -phenol, 1 vote lumen of concentrated pure hydrochloric acid, 6 parts by weight of citric acid, 3 parts by weight of boric acid, 2 parts by weight Aluminum sulfate and 4 parts by weight of the diazo compound from l-amino-4-morphoHnobenzene in The form of the zinc chloride double salt in 100 parts by volume of water becomes transparent in the usual way Paper coated and dried. After exposure, under a template with a 12 ampere charcoal arc lamp is developed with ammonia gas. The breaks, which have a yellow hue, can can be used as intermediate originals to produce further copies.
Man verfährt wie im Beispiel 1 und ersetzt 4,5 Ge? wichtsteüe 3,5;-Dimethyl-2- [4'-methyl- piperazino* (l')-methyl]-phenbl durch 4 Gewichtsteüe 2,5-Dime-. thyl-4-[4'-äthyl-piperazino-(l')-methyl]-phenol-chlor-.. hydrat. Die erhaltenen Pausen besitzen eine gute Weiterkopierfähigkeit.·Proceed as in Example 1 and replace 4.5 Ge? weight 3,5; -Dimethyl-2- [4'-methylpiperazino * (l ') - methyl] -phenbl by 4 parts by weight of 2,5-dimen-. ethyl-4- [4'-ethyl-piperazino- (l ') -methyl] -phenol-chloro- .. hydrate. The pauses obtained are easy to copy further.
- " ... . B eis ρ i el 4,- ".... As far as ρ i el 4,
Die Streichlösung hat die gleiche Zusammensetzung, wie im Beispiel 2, nur ersetzt man die dort angegebene.;The spreadable solution has the same composition, as in example 2, only you replace the one given there .;
Kupplungskomponente durch 4,2 Gewichtsteile 2,5-Dimethyl-4-[4'-phenyl-piperazino-(l')-methyl]-phenol. Coupling component with 4.2 parts by weight of 2,5-dimethyl-4- [4'-phenyl-piperazino- (1 ') -methyl] -phenol.
Auf ein opakes Papier streicht man eine Lösung folgender Zusammensetzung: 6 Gewichtsteile Zitronensäure, 3 Gewichtsteile Borsäure, 4,5 Gewichtsteile Thioharnstoff, 15 Volumteile Isopropylalkohol, 2 Gewichtsteile 2,5-Dimethyl-4- [4'-methyl-piperazino-(l')-methyl]-phenol, 0,6 Gewichtsteile 2-Hydroxynaphthalin-3,6-disulf osäure (Natriumsalz), 2 Gewichtsteile der Diazoverbindungen aus l-Amino-4-morpholinobenzol in Form des Zinkchloriddoppelsalzes in 85 Volumteilen Wasser.A solution of the following composition is spread on an opaque paper: 6 parts by weight of citric acid, 3 parts by weight boric acid, 4.5 parts by weight thiourea, 15 parts by volume isopropyl alcohol, 2 parts by weight 2,5-dimethyl-4- [4'-methyl-piperazino- (l ') -methyl] -phenol, 0.6 parts by weight of 2-hydroxynaphthalene-3,6-disulfonic acid (sodium salt), 2 parts by weight of the diazo compounds from l-amino-4-morpholinobenzene in the form of the zinc chloride double salt in 85 parts by volume Water.
Nach dem Trocknen wird in üblicher Weise unter einer 12-Ampere-Bogenlampe belichtet und mit Ammoniakgas entwickelt. Die erhaltenen Pausen weisen einen hellen Braunton auf. Verwendet man zum Beschichten ein transparentes Papier, so lassen sich die erhaltenen Pausen als Zwischenoriginale verwenden, zoAfter drying, exposure is carried out in the usual way under a 12-ampere arc lamp and with ammonia gas developed. The breaks obtained have a light brown tone. Used for coating a transparent paper, the pauses obtained can be used as intermediate originals, zo
Die Lösung von 3 Gewichtsteilen 2,6-Dimethyl-4-[4'-tolyl-piperazino-(l')-methyl]-phenol, 3 Gewichtsteilen Zitronensäure, 2 Gewichtsteilen Thioharnstoff, 1 Gewichtsteil Borsäure und 4 Gewichtsteilen des Zinkchlorid-Doppelsalzes der Diazoverbindung aus l-Amino-3-methyl-4-N-äthyl-aminobenzol in einem Gemisch aus 50 Volumteüen Isopropylalkohol und 40 Volumteüen Wasser wird auf ein mit einer Acetylcellulose-Lackschicht versehenes transparentes Papier aufgestrichen. Die Schicht wird nach dem Trocknen in üblicher Weise unter einer Vorlage belichtet und mit Ammoniakgas entwickelt. Man erhält ein Bild der Vorlage in gelben Farbtönen, das gute Abdeckkraft besitzt.The solution of 3 parts by weight of 2,6-dimethyl-4- [4'-tolyl-piperazino- (l ') - methyl] -phenol, 3 parts by weight of citric acid, 2 parts by weight of thiourea, 1 part by weight of boric acid and 4 parts by weight of the Zinc chloride double salt of the diazo compound from l-amino-3-methyl-4-N-ethyl-aminobenzene in one Mixture of 50 parts by volume of isopropyl alcohol and 40 parts by volume of water is applied to a layer of acetyl cellulose lacquer coated transparent paper. The layer will dry in Usually exposed under an original and developed with ammonia gas. You get a picture of the Template in yellow tones that has good covering power.
Claims (1)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL272342D NL272342A (en) | 1960-12-09 | ||
| BE611215D BE611215A (en) | 1960-12-09 | ||
| DEK42354A DE1226878B (en) | 1960-12-09 | 1960-12-09 | Photosensitive diazo layer |
| CH1346361A CH409627A (en) | 1960-12-09 | 1961-11-20 | Two-component diazotype layer |
| US156117A US3139341A (en) | 1960-12-09 | 1961-11-30 | Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound |
| GB43009/61A GB955886A (en) | 1960-12-09 | 1961-12-01 | Material having a two-component diazotype coating |
| FR881383A FR1312138A (en) | 1960-12-09 | 1961-12-08 | Two-component diazotype layers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK42354A DE1226878B (en) | 1960-12-09 | 1960-12-09 | Photosensitive diazo layer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1226878B true DE1226878B (en) | 1966-10-13 |
Family
ID=7222720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK42354A Pending DE1226878B (en) | 1960-12-09 | 1960-12-09 | Photosensitive diazo layer |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3139341A (en) |
| BE (1) | BE611215A (en) |
| CH (1) | CH409627A (en) |
| DE (1) | DE1226878B (en) |
| FR (1) | FR1312138A (en) |
| GB (1) | GB955886A (en) |
| NL (1) | NL272342A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3404005A (en) * | 1963-10-01 | 1968-10-01 | Ind Dyestuff Company | Diazo light-sensitive composition and element |
| GB1244434A (en) * | 1968-05-15 | 1971-09-02 | Ricoh Kk | Improvements in and relating to photosensitive materials |
| US3976491A (en) * | 1974-11-26 | 1976-08-24 | Scott Paper Company | Diazo compositions and diazotype materials prepared from same |
| US4108664A (en) * | 1976-11-01 | 1978-08-22 | Gaf Corporation | Light-sensitive negative-working film containing a diazo oxide sensitizer and a p-toluenesulfonyl halide or a 2,4-dihalo-S-triazine |
| US8624064B2 (en) * | 2007-12-19 | 2014-01-07 | Dow Corning Toray Company, Ltd. | 4-hydroxyphenylalkylamine derivative |
| CN102633749A (en) * | 2012-03-22 | 2012-08-15 | 浙江大学 | Preparation method of 1-(4-(2-methoxy ethyoxyl) phenyl) piperazine hydrochloride |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882271A (en) * | 1959-04-14 | Xcixcxh | ||
| US2767186A (en) * | 1956-10-16 | Quaternary ammonium salts of substi- | ||
| US2415786A (en) * | 1944-01-06 | 1947-02-11 | Burroughs Wellcome Co | Unsymmetrically substituted piperazines |
| US2467358A (en) * | 1946-06-15 | 1949-04-12 | Gen Aniline & Film Corp | Preparation of diazo prints utilizing resorcinol carbonamides as coupling components |
| US2537106A (en) * | 1946-10-18 | 1951-01-09 | Gen Aniline & Film Corp | Poly-acetoacetyl derivatives of polyamines as azo components in diazotype photoprinting material |
| NO98358A (en) * | 1958-01-18 | |||
| DE1086124B (en) * | 1958-06-14 | 1960-07-28 | Kalle Ag | Diazotype copying layers for the production of intermediate originals |
-
0
- NL NL272342D patent/NL272342A/xx unknown
- BE BE611215D patent/BE611215A/xx unknown
-
1960
- 1960-12-09 DE DEK42354A patent/DE1226878B/en active Pending
-
1961
- 1961-11-20 CH CH1346361A patent/CH409627A/en unknown
- 1961-11-30 US US156117A patent/US3139341A/en not_active Expired - Lifetime
- 1961-12-01 GB GB43009/61A patent/GB955886A/en not_active Expired
- 1961-12-08 FR FR881383A patent/FR1312138A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE611215A (en) | |
| GB955886A (en) | 1964-04-22 |
| NL272342A (en) | |
| US3139341A (en) | 1964-06-30 |
| FR1312138A (en) | 1962-12-14 |
| CH409627A (en) | 1966-03-15 |
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