DE3704263A1 - IR methine dye - Google Patents
IR methine dyeInfo
- Publication number
- DE3704263A1 DE3704263A1 DE19873704263 DE3704263A DE3704263A1 DE 3704263 A1 DE3704263 A1 DE 3704263A1 DE 19873704263 DE19873704263 DE 19873704263 DE 3704263 A DE3704263 A DE 3704263A DE 3704263 A1 DE3704263 A1 DE 3704263A1
- Authority
- DE
- Germany
- Prior art keywords
- pentamethine
- dye
- formula
- optical recording
- production
- 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.)
- Withdrawn
Links
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
- G11B7/247—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes methine or polymethine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/252—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers
- G11B7/253—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates
- G11B7/2533—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of layers other than recording layers of substrates comprising resins
Abstract
Description
Zur Herstellung von optischen Aufzeichnungsmaterialien werden Pentamethinfarbstoffe der FormelFor the production of optical recording materials become pentamethine dyes of the formula
worin R Wasserstoff oder Alkyl bedeutet, verwendet, wie es z. B. in EP 023 736, JP 58 219 090, US-P 4 547 444 und DE-OS 3 413 940 beschrieben ist. Die Herstellung des Farbstoffes mit Anion = C10₄- und R = CH₃ ist aus Helv. Chim. Acta 28, 604, 611 (1945) und J. Am. Chem. Soc. 80, 3772 (1958) bekannt.where R is hydrogen or alkyl used, as z. B. is described in EP 023 736, JP 58 219 090, US-P 4 547 444 and DE-OS 3 413 940. The preparation of the dye with anion = C10₄ - and R = CH₃ is from Helv. Chim. Acta 28, 604, 611 (1945) and J. Am. Chem. Soc. 80, 3772 (1958).
Für die Herstellung solcher Aufzeichnungsmaterialien nach dem Spin-Coating-Verfahren oder durch Gießverfahren benötigt man Farbstoffe, die in den verwendeten Auf tragsmedien leicht löslich sind und nicht rekristalli sieren. Üblicherweise verwendete Lösungsmittel in sol chen Auftragsmedien sind chlorierte Kohlenwasserstoffe, wie Dichlormethan oder 1,2-Dichlor-ethan, und Ketone, wie Cyclohexanon oder Butanon.For the production of such recording materials according to the spin coating process or by casting process you need dyes that are used in the on media are easily soluble and not recrystallized sieren. Commonly used solvents in sol The application media are chlorinated hydrocarbons, such as dichloromethane or 1,2-dichloroethane, and ketones, such as cyclohexanone or butanone.
Diese Lösungsmittel greifen jedoch normalerweise ein aus Kunststoff gefertigtes Trägermaterial an, was nicht ge wünscht wird. Mit solchen Kunststoffen verträgliche Lösungsmittel sind Alkohole und Glykole, vorzugsweise Methanol und Butanol, in denen aber die Pentamethinfarb stoffe der Formel (I) häufig nur ungenügend löslich sind.However, these solvents usually intervene Plastic-made carrier material, which is not ge is desired. Compatible with such plastics Solvents are alcohols and glycols, preferably Methanol and butanol, but in which the pentamethine color Substances of the formula (I) are often only insoluble are.
Es war deshalb überraschend, daß ein Methansulfonat eines solchen Pentamethinfarbstoffes der FormelIt was therefore surprising that a methanesulfonate of such a pentamethine dye of the formula
in Alkoholen in hoher Konzentration löslich ist.is soluble in alcohol in high concentration.
Die vorliegende Erfindung betrifft demnach das Penta methin der Formel (II), ein Verfahren zu dessen Her stellung und dessen Verwendung in alkoholischer Lösung zur Herstellung von optischen Aufzeichnungsmaterialien. The present invention accordingly relates to the penta methine of formula (II), a process for the preparation thereof position and its use in alcoholic solution for the production of optical recording materials.
Die erfindungsgemäße Herstellung des Pentamethins der Formel (II) geschieht durch Kondensation von 1,1-Bis-(4- dimethylaminophenyl)-ethen mit ortho-Ameisensäureestern, vorzugsweise dem Methyl- und Ethylester, in Acetanhydrid unter Zusatz eines Äquivalentes Methansulfonsäure bei Temperaturen zwischen Raumtemperatur und dem Siedepunkt des Mediums, vorzugsweise bei 35-100°C. Der Pentamethin farbstoff der Formel (II) wird durch Verdünnen mit aromatischen Lösungsmitteln, vorzugsweise Toluol, Xylol, ausgefällt. Die Reaktionszeit beträgt je nach Temperatur 15 Minuten bis 10 Stunden.The inventive production of the pentamethine Formula (II) is done by condensation of 1,1-bis- (4- dimethylaminophenyl) ethene with ortho-formic acid esters, preferably the methyl and ethyl esters, in acetic anhydride with the addition of an equivalent of methanesulfonic acid Temperatures between room temperature and the boiling point of the medium, preferably at 35-100 ° C. The pentamethine dye of formula (II) is diluted with aromatic solvents, preferably toluene, xylene, failed. The reaction time depends on the temperature 15 minutes to 10 hours.
Die Löslichkeiten des Pentamethins der Formel (II) in
verschiedenen Alkoholen sind in der folgenden Tabelle
zusammengestellt:
AlkoholLöslichkeit von II in g/lThe solubilities of the pentamethine of the formula (II) in various alcohols are summarized in the following table:
Alcohol solubility of II in g / l
Ethanol<200 Methanol<200 Butanol/Methanol 2/1<200Ethanol <200 Methanol <200 Butanol / methanol 2/1 <200
Die Herstellung des optischen Aufzeichnungsmaterials erfolgt beispielsweise nach dem Spin-Coating-Verfahren durch Auftragen einer Lösung des Pentamethins der Formel (II) in beispielsweise Methanol, dem ein Binder zuge setzt sein kann, auf eine Trägerplatte, vorzugsweise eine Kunststoffplatte.The production of the optical recording material takes place, for example, according to the spin coating method by applying a solution of the pentamethine of the formula (II) in, for example, methanol to which a binder is added can be placed on a carrier plate, preferably a plastic plate.
26,6 g 1,1-Bis(4-dimethylaminophenyl)-ethen und 7,8 g
ortho-Ameisensäuretriethylester werden in 50 ml Acet
anhydrid vorgelegt. Dazu werden während 15 min 5,0 g
Methansulfonsäure getropft. Anschließend wird die blaue
Lösung 60 min bei 80°C gerührt. Bei dieser Temperatur
werden 150 ml Toluol hinzugefügt. Es fällt ein bronze
farbenes Kristallisat aus. Es wird 1/4 h unter Rückfluß
gerührt. Nach dem Abkühlen wird abgesaugt, mit Toluol
gewaschen und im Vakuum getrocknet:
28,9 g (90,3% d. Th.) Pentamethinfarbstoff der Formel
(II).
Schmelzbereich: 205 bis 210°C.26.6 g of 1,1-bis (4-dimethylaminophenyl) ethene and 7.8 g of ortho-formic acid triethyl ester are placed in 50 ml of acetic anhydride. For this purpose, 5.0 g of methanesulfonic acid are added dropwise over 15 minutes. The blue solution is then stirred at 80 ° C. for 60 min. At this temperature 150 ml of toluene are added. A bronze colored crystal precipitates. The mixture is stirred under reflux for 1/4 h. After cooling, the product is filtered off with suction, washed with toluene and dried in vacuo:
28.9 g (90.3% of theory) of pentamethine dye of the formula (II).
Melting range: 205 to 210 ° C.
Eine 5%ige Lösung des Pentamethins der Formel (II) in einem Gemisch aus Butanol/Methanol 2/1, die 2,5% eines Polymeren auf Basis Polyvinylacetat enthält, wird nach dem Spin-Coating-Verfahren auf eine Trägerplatte aus Polymethylmethacrylat aufgebracht, wobei sich eine Schicht von 0,8 µm bildet. Die Platte kann mit Hilfe eines Halbleiterlasers beschrieben und gelesen werden.A 5% solution of the pentamethine of formula (II) in a mixture of butanol / methanol 2/1, the 2.5% of a Contains polymers based on polyvinyl acetate spin coating on a carrier plate Polymethyl methacrylate applied, with one Layer of 0.8 microns forms. The plate can with the help a semiconductor laser can be written and read.
Claims (5)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873704263 DE3704263A1 (en) | 1987-02-12 | 1987-02-12 | IR methine dye |
| NL8800069A NL8800069A (en) | 1987-02-12 | 1988-01-12 | INFRARED METHIN DYE. |
| JP63024048A JPS63202665A (en) | 1987-02-12 | 1988-02-05 | Pentamethine dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873704263 DE3704263A1 (en) | 1987-02-12 | 1987-02-12 | IR methine dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3704263A1 true DE3704263A1 (en) | 1988-08-25 |
Family
ID=6320766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873704263 Withdrawn DE3704263A1 (en) | 1987-02-12 | 1987-02-12 | IR methine dye |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS63202665A (en) |
| DE (1) | DE3704263A1 (en) |
| NL (1) | NL8800069A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0403157A2 (en) * | 1989-06-12 | 1990-12-19 | Minnesota Mining And Manufacturing Company | Thermal dye bleach construction |
| EP0417555A1 (en) * | 1989-09-13 | 1991-03-20 | Bayer Ag | Pentamethine dyes and derivatives |
| EP0606710A2 (en) * | 1992-11-16 | 1994-07-20 | Minnesota Mining And Manufacturing Company | Photochemical generation of dyes |
-
1987
- 1987-02-12 DE DE19873704263 patent/DE3704263A1/en not_active Withdrawn
-
1988
- 1988-01-12 NL NL8800069A patent/NL8800069A/en not_active Application Discontinuation
- 1988-02-05 JP JP63024048A patent/JPS63202665A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0403157A2 (en) * | 1989-06-12 | 1990-12-19 | Minnesota Mining And Manufacturing Company | Thermal dye bleach construction |
| EP0403157A3 (en) * | 1989-06-12 | 1991-05-02 | Minnesota Mining And Manufacturing Company | Thermal dye bleach construction |
| EP0417555A1 (en) * | 1989-09-13 | 1991-03-20 | Bayer Ag | Pentamethine dyes and derivatives |
| US5138070A (en) * | 1989-09-13 | 1992-08-11 | Bayer Aktiengesellschaft | Pentamethine dyestuffs and derivatives |
| EP0606710A2 (en) * | 1992-11-16 | 1994-07-20 | Minnesota Mining And Manufacturing Company | Photochemical generation of dyes |
| EP0606710A3 (en) * | 1992-11-16 | 1994-09-07 | Minnesota Mining & Mfg | Photochemical generation of dyes. |
| US5389498A (en) * | 1992-11-16 | 1995-02-14 | Minnesota Mining And Manufacturing Company | Photochemical generation of dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8800069A (en) | 1988-09-01 |
| JPS63202665A (en) | 1988-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |