EP0312707A1 - Colour former solutions, their preparation and use - Google Patents
Colour former solutions, their preparation and use Download PDFInfo
- Publication number
- EP0312707A1 EP0312707A1 EP88111115A EP88111115A EP0312707A1 EP 0312707 A1 EP0312707 A1 EP 0312707A1 EP 88111115 A EP88111115 A EP 88111115A EP 88111115 A EP88111115 A EP 88111115A EP 0312707 A1 EP0312707 A1 EP 0312707A1
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- EP
- European Patent Office
- Prior art keywords
- solutions
- color
- alkyl aromatic
- color formers
- preparation
- 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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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
Definitions
- the invention relates to solutions of color formers in alkyl aromatic hydrocarbons. Appropriate solutions with a color former content of 3 - 8% are used in the production of pressure-sensitive recording materials.
- the process is linked to the production of the color former, ie the production of the solutions is not possible for a company that purchases the finished, dry color former.
- the process is complex since at least residual water, but often also additional auxiliary solvents, have to be removed from the color former solution.
- the problem is solved by providing solutions of color formers according to claims 1 to 4 and by a process for their preparation according to claims 5 to 7.
- the solutions according to the invention are concentrates and are used for the production of pressure-sensitive recording materials.
- Alkyl aromatic hydrocarbons are aromatic compounds which contain alkyl groups with preferably 1-18 carbon atoms, such as alkyl biphenyls, in particular iso-propyl-biphenyl, tert-butylbiphenyl, dialkyl-biphenyl, in particular di-isopropylbiphenyl and di-tert-butyl-biphenyl, alkylbenzenes , hydrogenated and partially hydrogenated terphenyls, especially cyclohexyldiphenyl and alkylnaphthalenes such as mono-, di- and trialkylnaphthalenes with alkyl groups which can contain 1 to 4 carbon atoms.
- alkyl biphenyls in particular iso-propyl-biphenyl, tert-butylbiphenyl, dialkyl-biphenyl, in particular di-isopropylbiphenyl and di-tert-butyl-
- the preferred alkyl aromatic hydrocarbons are dialkylnaphthalenes, where the alkyl chains are the same or different and can each contain 1 to 4 carbon atoms. Examples include dimethyl, diethyl, diisopropyl, di-tert-butyl, methyl-ethyl, methyl-propyl, methyl-isopropyl, methyl-butyl, methyl-tert-butyl or isopropyl-tert. -butylnaphthalenes, the position of the alkyl groups on the naphthalene ring being arbitrary. Mixtures of different alkylnaphthalenes and mixtures of naphthalenes substituted at different positions (mixture of isomers) are preferred for technical and economic reasons.
- Color formers which can be used according to the invention are the color formers of the various groups which are usually used in pressure-sensitive recording materials, such as, for. B. 3,3-bis (aminophenyl) phthalide, 3,3-bis (indolyl) phthalide, 3-amino-fluorane, Spirodipyrans, chromenoindoles, phenoxazines, carbazolyl methanes, or triaryl methanes.
- These color formers can be contained individually or in a mixture with one or more, including the various groups, in the solutions according to the invention.
- the mixtures of color formers in particular play a major role in achieving targeted colors and tints.
- the dissolving process takes place at a temperature in the range from 65 to 160 ° C., preferably in the range from 80 to 120 ° C.
- Highly viscous solutions are obtained, from which no color formers crystallize, even when stored for several weeks or when cooled to temperatures down to -10 ° C.
- these highly concentrated solutions can be diluted to a concentration of 3 to 10% by mixing with appropriate amounts of alkyl aromatic hydrocarbons at room temperature, but preferably at a slightly elevated temperature up to about 50 ° C.
- These solutions are used as color former solutions, microencapsulated in pressure-sensitive carbonless papers.
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- Color Printing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
Description
Die Erfindung betrifft Lösungen von Farbbildnern in alkylaromatischen Kohlenwasserstoffen.
Entsprechende Lösungen mit einem Gehalt an Farbbildnern von 3 - 8 % werden bei der Herstellung von druckempfindlichen Aufzeichnungsmaterialien verwendet.The invention relates to solutions of color formers in alkyl aromatic hydrocarbons.
Appropriate solutions with a color former content of 3 - 8% are used in the production of pressure-sensitive recording materials.
Aus transport- und produktionstechnischen Gründen besteht ein Bedarf an entsprechenden Konzentraten mit möglichst hohem Gehalt an Farbbildnern. Dies scheiterte jedoch bislang daran, daß bei den meisten Farbbildnern die Löslichkeitsgrenze bei etwa 2 - 10 Gew.-% Farbbildnern erreicht ist.
Aus DE-A-36 05 552 ist ein Verfahren bekannt, hochkonzentrierte Lösungen von Farbbildnern auf Triphenylmethanbasis in verschiedenen unterschiedlichen Lösemitteln herzustellen, indem die Farbbildner nach ihrer Herstellung in wäßrigem Milieu in das wasserunlösliche Lösemittel eingebracht werden. Dabei lassen sich hochkonzentrierte Lösungen mit einem Gehalt von 10 - 50 Gew.-% bevorzugt 10 - 35 Gew.-% an Farbbildnern herstellen.
Die entsprechenden Lösungen sind einerseits auf Farbbildner auf Basis von Triphenylmethanderivaten und auf die Lösung von jeweils nur einem Farbbildner beschränkt. Andererseits ist das Verfahren an die Herstellung des Farbbildners gekoppelt, d. h., die Herstellung der Lösungen ist für ein Unternehmen, das die fertigen, trocknen Farbbildner bezieht, nicht möglich. Zudem ist das Verfahren aufwendig, da zumindest Restwasser, oft aber auch noch zusätzliche Hilfslösungsmittel aus der Farbbildnerlösung entfernt werden müssen.For transport and production reasons, there is a need for corresponding concentrates with the highest possible color former content. However, this has so far failed because most color formers have reached the solubility limit of about 2 to 10% by weight color formers.
From DE-A-36 05 552 a method is known for using highly concentrated solutions of color formers To produce triphenylmethane base in various different solvents by introducing the color formers into water-insoluble solvents after their preparation in an aqueous medium. Highly concentrated solutions with a content of 10-50% by weight, preferably 10-35% by weight, of color formers can be produced.
The corresponding solutions are limited on the one hand to color formers based on triphenylmethane derivatives and to the solution of only one color former. On the other hand, the process is linked to the production of the color former, ie the production of the solutions is not possible for a company that purchases the finished, dry color former. In addition, the process is complex since at least residual water, but often also additional auxiliary solvents, have to be removed from the color former solution.
Es ist daher Aufgabe der Erfindung, Lösungen von gegebenenfalls mehreren Farbbildnern in alkylaromatischen Kohlenwasserstoffen bereitzustellen, die auch mehr als 50 % Farbbildner enthalten können, die nicht auf nur eine Gruppe von Farbbildnern beschränkt sind und die in einfacher Weise auch mit trockenen, als Handelsware bezogenen, Farbbildnern hergestellt werden können, ohne daß weitere Hilfslösemittel oder Wasser zusätzlich verwendet und abgetrennt werden müssen.It is therefore an object of the invention to provide solutions of optionally a plurality of color formers in alkylaromatic hydrocarbons which may also contain more than 50% of color formers, which are not limited to only one group of color formers and which can also be obtained in a simple manner with dry, commercially available products, Color formers can be produced without additional auxiliary solvents or water having to be used and separated.
Die Lösung der Aufgabe erfolgt durch Bereitstellen von Lösungen von Farbbildnern gemäß der Ansprüche 1 bis 4 und durch ein Verfahren zu ihrer Herstellung gemäß der Ansprüche 5 bis 7. Die erfindungsgemäßen Lösungen sind Konzentrate und werden zur Herstellung von druckempfindlichen Aufzeichnungsmaterialien verwendet.The problem is solved by providing solutions of color formers according to claims 1 to 4 and by a process for their preparation according to claims 5 to 7. The solutions according to the invention are concentrates and are used for the production of pressure-sensitive recording materials.
Es ist bekannt, daß sich die meisten Stoffe umso besser in einem Lösemittel lösen, je höher dessen Temperatur ist. Beim Abkühlen dieser, bei höherer Temperatur hergestellten Lösungen, kristallisiert der gelöste Stoff aus, bis das jeweilige Lösungsgleichgewicht erreicht ist. Entsprechendes gilt auch für Lösungen von Farbbildnern in alkylaromatischen Kohlewasserstoffen: Stellt man z. B. 20 %ige Lösungen der Farbbildner her, indem diese bei 100 °C in alkylaromatischen Kohlenwasserstoffen gelöst werden, so bilden sich beim Abkühlen gesättigte Lösungen. Die über den Sättigungsgrad liegende Menge an eingebrachtem Farbbildner kristallisiert aus. Bei handelsüblichen Farbbildnern liegt der Sättigungsgrad in alkylaromatischen Kohlenwasserstoffen bei Raumtemperatur bei etwa 2 - 10 Gew.-%, bezogen auf die Lösung.
Überraschenderweise aber tritt dieser Effekt nicht mehr auf, wenn in den alkylaromatischen Kohlenwasserstoffen mehr als 40 Gew.-%, bezogen auf die Lösung, Farbbildner gelöst werden. Beim Abkühlen derartiger hochübersättigter Lösungen kristallisieren keine Farbbildner aus. Es verbleibt vielmehr eine homogene, hochviskose Lösung, die bei Raumtemperatur mehrere Wochen stabil bleibt. Die Lösung kann durch Hinzufügen entsprechenden weiteren Lösemittels auf einen Gehalt von 3 - 10 Gew.-% verdünnt werden. Sie kann somit als Konzentrat eines Farbbildners dienen.It is known that most substances dissolve in a solvent the better its temperature. When these solutions, which are produced at a higher temperature, cool down, the solute crystallizes out until the respective solution equilibrium is reached. The same applies to solutions of color formers in alkyl aromatic hydrocarbons. B. 20% solutions of the color formers ago by dissolving them at 100 ° C in alkyl aromatic hydrocarbons, so saturated solutions are formed on cooling. The amount of color former introduced, which is above the degree of saturation, crystallizes out. In the case of commercially available color formers, the degree of saturation in alkylaromatic hydrocarbons at room temperature is approximately 2-10% by weight, based on the solution.
Surprisingly, however, this effect no longer occurs if more than 40% by weight, based on the solution, of color formers are dissolved in the alkylaromatic hydrocarbons. When such highly supersaturated solutions cool, no color formers crystallize out. Rather, what remains is a homogeneous, highly viscous solution that remains stable for several weeks at room temperature. The solution can be diluted to a content of 3 to 10% by weight by adding appropriate further solvent. It can thus be used as a concentrate for a color former.
Alkylaromatische Kohlenwasserstoffe sind aromatische Verbindungen, die Alkylgruppen mit vorzugsweise 1 - 18 Kohlenstoffatomen enthalten, wie Alkylbiphenyle, insbesondere iso-Propyl-biphenyl, tert.-Butylbiphenyl, Dialkyl-biphenyl, insbesondere Di-isopropylbiphenyl und Di-tert.-butyl-biphenyl, Alkylbenzole, hydrierte und teilhydrierte Terphenyle, insbesondere Cyclohexyldiphenyl und Alkylnaphthaline wie Mono-, Di- und Trialkylnaphthaline mit Alkylgruppen die 1 bis 4 C-Atome enthalten können.
Die bevorzugten alkylaromatischen Kohlewasserstoffe sind Dialkylnaphthaline, wobei die Alkylketten gleich oder verschieden sind und jeweils 1 bis 4 C-Atome enthalten können.
Beispiele hierfür sind Dimethyl-, Diethyl-, Diisopropyl, Di-tert.-butyl-, Methyl-ethyl-, Methyl-propyl, Methyl-isopropyl-, Methyl-butyl-, Methyl-tert.-butyl- oder Isopropyl-tert.-butylnaphthaline, wobei die Position der Alkylgruppen am Naphthalinring beliebig ist. Aus technischen und wirtschaftlichen Gründen bevorzugt sind Gemische verschiedener Alkylnaphthaline sowie Gemische von an verschiedenen Stellen substituierten Naphthalinen (Isomerengemisch).Alkyl aromatic hydrocarbons are aromatic compounds which contain alkyl groups with preferably 1-18 carbon atoms, such as alkyl biphenyls, in particular iso-propyl-biphenyl, tert-butylbiphenyl, dialkyl-biphenyl, in particular di-isopropylbiphenyl and di-tert-butyl-biphenyl, alkylbenzenes , hydrogenated and partially hydrogenated terphenyls, especially cyclohexyldiphenyl and alkylnaphthalenes such as mono-, di- and trialkylnaphthalenes with alkyl groups which can contain 1 to 4 carbon atoms.
The preferred alkyl aromatic hydrocarbons are dialkylnaphthalenes, where the alkyl chains are the same or different and can each contain 1 to 4 carbon atoms.
Examples include dimethyl, diethyl, diisopropyl, di-tert-butyl, methyl-ethyl, methyl-propyl, methyl-isopropyl, methyl-butyl, methyl-tert-butyl or isopropyl-tert. -butylnaphthalenes, the position of the alkyl groups on the naphthalene ring being arbitrary. Mixtures of different alkylnaphthalenes and mixtures of naphthalenes substituted at different positions (mixture of isomers) are preferred for technical and economic reasons.
Erfindungsgemäß verwendbare Farbbildner sind die in druckempfindlichen Aufzeichnungsmaterialien üblicherweise eingesetzten Farbbildner der verschiedenen Gruppen wie z. B. 3,3-Bis-(aminophenyl)-phthalide, 3,3-Bis-(indolyl)-phthalide, 3-Amino-fluorane, Spirodipyrane, Chromenoindole, Phenoxazine, Carbazolyl-methane, oder Triarylmethane. Diese Farbbildner können einzeln oder im Gemisch mit einem oder mehreren, auch der verschiedenen Gruppen in den erfindungsgemäßen Lösungen enthalten sein. Gerade die Gemische von Farbbildnern spielen eine große Rolle, um gezielte Farben und Farbtönungen zu erzielen. Obwohl sich generell alle diese Farbbildner in allen erfindungsgemäßen alkylaromatischen Kohlenwasserstoffen lösen, sind nicht alle Farbbildner in ihrem Löseverhalten gleich. Es unterscheidet sich je nach Aromatizitätsgrad des Farbbildners. Da sich aber auch die alkylaromatischen Kohlenwasserstoffe in ihrem Aromatizitätsgrad unterscheiden, besteht für den Fachmann die Möglichkeit, die eingesetzten Farbbildner und Lösemittel entsprechend ihrem Aromatizitätsgrad aufeinander abzustimmen, d. h. er kann z. B. bei Verwendung von Farbbildnern mit einem Anteil an langkettigen aliphatischen Gruppen als alkylaromatische Kohlenwasserstoffe solche bevorzugt einsetzen, die einen Anteil an langkettigen aliphatischen Substituenten haben, um eine möglichst gute Löslichkeit zu erzielen. Hierzu kann es auch zweckmäßig sein, ein Gemisch verschiedener alkylaromatischer Kohlenwasserstoffe einzusetzen.
Die Herstellung von hochkonzentrierten Lösungen von Farbbildnern in alkylaromatischen Lösemitteln, die auch die beanspruchten Lösungen umfassen, aber nicht auf sie beschränkt sind, erfolgt dadurch, daß die Farbbildner in der gewünschten Konzentration, die im Bereich von 40 bis 75 % liegen kann, in an sich bekannter Weise bei erhöhter Temperatur, in den alkylaromatischen Kohlenwasserstoffen gelöst, und diese Lösungen auf Umgebungstemperatur abgekühlt werden. Dieser Lösevorgang erfolgt bei einer Temperatur im Bereich von 65 °C bis zur Siedetemperatur des Lösemittels. Ist allerdings der Zersetztungspunkt des Farbbildners niedriger als der Siedepunkt des Lösemittels so bildet die Zersetztungtemperatur den oberen Grenzwert. Im allgemeinen erfolgt der Lösevorgang bei einer Temperatur im Bereich von 65 - 160 °C, bevorzugt im Bereich von 80 - 120 °C.
Erhalten werden hochviskose Lösungen aus denen auch bei mehrwöchiger Lagerung sowie auch beim Abkühlen auf Temperaturen bis zu - 10 °C keine Farbbildner auskristallisieren. Andererseits können diese hochkonzentrierten Lösungen durch Vermischen mit entsprechenden Mengen an alkylaromatischen Kohlenwasserstoffen bei Raumtemperatur, bevorzugt aber bei leicht erhöhter Temperatur bis etwa 50 °C auf eine Konzentration von 3 - 10 % verdünnt werden. Diese Lösungen werden als Farbbildnerlösungen mikroverkapselt in druckempfindlichen Durchschreibepapieren eingesetzt.Color formers which can be used according to the invention are the color formers of the various groups which are usually used in pressure-sensitive recording materials, such as, for. B. 3,3-bis (aminophenyl) phthalide, 3,3-bis (indolyl) phthalide, 3-amino-fluorane, Spirodipyrans, chromenoindoles, phenoxazines, carbazolyl methanes, or triaryl methanes. These color formers can be contained individually or in a mixture with one or more, including the various groups, in the solutions according to the invention. The mixtures of color formers in particular play a major role in achieving targeted colors and tints. Although in general all of these color formers dissolve in all alkyl aromatic hydrocarbons according to the invention, not all color formers are identical in their dissolving behavior. It differs depending on the degree of aromaticity of the color former. However, since the alkyl aromatic hydrocarbons also differ in their degree of aromaticity, the person skilled in the art has the possibility of coordinating the color formers and solvents used with one another in accordance with their degree of aromaticity, ie he can e.g. B. when using color formers with a proportion of long-chain aliphatic groups as alkyl aromatic hydrocarbons preferably use those which have a proportion of long-chain aliphatic substituents in order to achieve the best possible solubility. For this purpose it can also be expedient to use a mixture of different alkyl aromatic hydrocarbons.
The preparation of highly concentrated solutions of color formers in alkyl aromatic solvents, which also include, but are not limited to, the claimed solutions, is carried out in that the color formers in themselves in the desired concentration, which can be in the range from 40 to 75% known manner at elevated temperature, in the alkyl aromatic Dissolved hydrocarbons, and these solutions are cooled to ambient temperature. This dissolving process takes place at a temperature in the range from 65 ° C. to the boiling point of the solvent. However, if the decomposition point of the color former is lower than the boiling point of the solvent, the decomposition temperature forms the upper limit. In general, the dissolving process takes place at a temperature in the range from 65 to 160 ° C., preferably in the range from 80 to 120 ° C.
Highly viscous solutions are obtained, from which no color formers crystallize, even when stored for several weeks or when cooled to temperatures down to -10 ° C. On the other hand, these highly concentrated solutions can be diluted to a concentration of 3 to 10% by mixing with appropriate amounts of alkyl aromatic hydrocarbons at room temperature, but preferably at a slightly elevated temperature up to about 50 ° C. These solutions are used as color former solutions, microencapsulated in pressure-sensitive carbonless papers.
40 g eines handelsüblichen Farbbildnergemisches für schwarze Durchschriften druckempfindlicher Durchschreibepapiere werden mit 60 g Dimethylnaphthalin (Isomerengemisch) angeteigt und unter Rühren auf 65 °C erwärmt. Dabei löst sich der Farbbildner im Dimethylnaphthalin zu einer klaren Lösung. Diese Lösung ist auch nach dem Abkühlen auf Raumtemperatur nach 2 Wochen noch stabil.40 g of a commercially available color former mixture for black copies of pressure-sensitive carbonless papers are pasted with 60 g of dimethylnaphthalene (isomer mixture) and heated to 65 ° C. with stirring. The color former dissolves in the Dimethylnaphthalene to a clear solution. This solution is still stable after 2 weeks after cooling to room temperature.
300 g Diisopropylnaphthalin (Isomerengemisch) werden auf 160 °C erhitzt. Unter Rühren werden 700 g eines Farbbildnergemisches entsprechend Beispiel 1 zugegeben und so lange gerührt, bis sich eine klare Lösung gebildet hat. Beim Abkühlen auf Raumtemperatur entsteht eine hochviskose, homogene Lösung in der auch nach 2 Wochen Lagerung keine Ausfällung zu erkennen ist.
Eine Probe der Lösung wird 2 d bei - 10 °C gelagert. Auch hier ist keine Ausfällung zu beobachten.
100 g der Lösung werden mit 900 g Diisopropylnaphthalin versetzt und unter Rühren auf 40 °C erwärmt. Es entsteht eine klare Lösung mit einem Gehalt an 7 % Farbbildner.300 g of diisopropylnaphthalene (mixture of isomers) are heated to 160 ° C. 700 g of a color former mixture corresponding to Example 1 are added with stirring and the mixture is stirred until a clear solution has formed. When cooling to room temperature, a highly viscous, homogeneous solution is formed in which no precipitation can be seen even after 2 weeks of storage.
A sample of the solution is stored for 2 d at -10 ° C. No precipitation can be observed here either.
100 g of the solution are mixed with 900 g of diisopropylnaphthalene and heated to 40 ° C. with stirring. A clear solution with a 7% color former content is formed.
30 g eines Farbbildnergemisches entsprechend aus Beispiel 1 werden bei 65 °C in Dimethylnaphthalin gelöst und danach auf Raumtemperatur abgekühlt. Nach einem d hat sich am Boden des Gefäßes ein Belag an auskristallisiertem Farbbildner abgesetzt.30 g of a color former mixture corresponding to Example 1 are dissolved in dimethylnaphthalene at 65 ° C. and then cooled to room temperature. After ad a deposit of crystallized color former has settled on the bottom of the vessel.
Claims (8)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT88111115T ATE70779T1 (en) | 1987-10-23 | 1988-07-12 | SOLUTIONS OF COLOR IMAGERS, THEIR PREPARATION AND USE. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873735976 DE3735976A1 (en) | 1987-10-23 | 1987-10-23 | SOLUTIONS OF COLORED IMAGES, THEIR PRODUCTION AND USE |
| DE3735976 | 1987-10-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0312707A1 true EP0312707A1 (en) | 1989-04-26 |
| EP0312707B1 EP0312707B1 (en) | 1991-12-27 |
Family
ID=6338971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88111115A Expired - Lifetime EP0312707B1 (en) | 1987-10-23 | 1988-07-12 | Colour former solutions, their preparation and use |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0312707B1 (en) |
| JP (1) | JP2540360B2 (en) |
| AT (1) | ATE70779T1 (en) |
| DE (2) | DE3735976A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0599448A2 (en) * | 1992-10-26 | 1994-06-01 | Koch Industries, Inc. | Solvant for use in carbonless paper, comprising diisopropylmethylnaphthalene, and products utilising same |
| EP0601690A1 (en) * | 1992-12-02 | 1994-06-15 | Koch Industries, Inc. | Solvent for use in carbonless paper, comprising diisopropylbiphenyl and triisopropylbiphenyl, and products utilising the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2075539A (en) * | 1980-04-16 | 1981-11-18 | Ciba Geigy Ag | Stable, Highly Concentrated Colour Former Solutions |
| EP0234394A2 (en) * | 1986-02-21 | 1987-09-02 | Bayer Ag | Highly concentrated stable solutions of dyes |
-
1987
- 1987-10-23 DE DE19873735976 patent/DE3735976A1/en not_active Withdrawn
-
1988
- 1988-07-12 AT AT88111115T patent/ATE70779T1/en active
- 1988-07-12 DE DE8888111115T patent/DE3867203D1/en not_active Expired - Fee Related
- 1988-07-12 EP EP88111115A patent/EP0312707B1/en not_active Expired - Lifetime
- 1988-10-24 JP JP63266303A patent/JP2540360B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2075539A (en) * | 1980-04-16 | 1981-11-18 | Ciba Geigy Ag | Stable, Highly Concentrated Colour Former Solutions |
| EP0234394A2 (en) * | 1986-02-21 | 1987-09-02 | Bayer Ag | Highly concentrated stable solutions of dyes |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0599448A2 (en) * | 1992-10-26 | 1994-06-01 | Koch Industries, Inc. | Solvant for use in carbonless paper, comprising diisopropylmethylnaphthalene, and products utilising same |
| EP0599448A3 (en) * | 1992-10-26 | 1995-03-29 | Koch Ind Inc | Solvant for use in carbonless paper, comprising diisopropylmethylnaphthalene, and products utilising same. |
| US5489332A (en) * | 1992-10-26 | 1996-02-06 | Koch Industries, Inc. | Carbonless paper solvent comprising diisopropylmethylnaphthalene and products utilizing same |
| EP0601690A1 (en) * | 1992-12-02 | 1994-06-15 | Koch Industries, Inc. | Solvent for use in carbonless paper, comprising diisopropylbiphenyl and triisopropylbiphenyl, and products utilising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3735976A1 (en) | 1989-05-03 |
| JPH01152164A (en) | 1989-06-14 |
| ATE70779T1 (en) | 1992-01-15 |
| JP2540360B2 (en) | 1996-10-02 |
| DE3867203D1 (en) | 1992-02-06 |
| EP0312707B1 (en) | 1991-12-27 |
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