GB2208514A - New cyanine dyes for optical recording - Google Patents
New cyanine dyes for optical recording Download PDFInfo
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- GB2208514A GB2208514A GB8818387A GB8818387A GB2208514A GB 2208514 A GB2208514 A GB 2208514A GB 8818387 A GB8818387 A GB 8818387A GB 8818387 A GB8818387 A GB 8818387A GB 2208514 A GB2208514 A GB 2208514A
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- 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
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- Heat Sensitive Colour Forming Recording (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
r. c-! -- 2218 5 1.1 4 _ f - CYANINE COMPOUNDS The present invention
relates to novel cyanine compounds.
Prevalently used among inorganic recording mediums for semiconductor laser are those containing a predominant amount of tellurium for forming a recording layer. Tellurium-type materials, however, have the drawbacks of being toxic, low in corrosion resistance, expensive and unfit to densify. Research is under way to develop orgahic dyes which can replace the inorganic tellurium-type materials.
Given below are important characterisitics required of organic dyes useful as recording mediums:
(1) properties of markedly absorbing near infrared light at approximately 700 to 900 nm and undergoing fusion, sublimation, decomposition and like changes by exposure to the action of resulting heat energy; (2) desirable ability to cause the recording layer to reflect intensely the light for detection of signals in reproduction; (3) good solubility in a solvent in view Of need for formation of recording layer by wet coating method; (4) high stability in shape retention and excellent retention of recorded information and unlikelihood of 1 - 2 degradation due to irradiation of light in reproduction, resulting in retention of recorded inormation for 10 years or more.
While organic dyes are advantageous in being low in toxicity, high in corrosion resistance, inexpensive and fit to densify as compared with the foregoing inorganic materials, an organic dye remains to be developed which has the characterisitic described above in item (2) among the required characterisitics (1) to (4).
An object of the present invention is to provide a cyanine corr(pound suitable for use as a near infrared light-absorbable organic dye which is useful as a recording medium of optical disk for semiconductor laser.
Another object of the invention is to provide a cyanine compound having the characterisitics (1) to (4) which are required of near infrared lightabsorbable organic dyes useful as recording mediums of optical disk for semiconductor laser.
A further object of the invention is to provide a cyanine compound having a reflectivity as high as that of inorganic tellurium-type materials.
A still further object of the invention is to provide a cyanine compound having an outstanding solubility in a solvent.
Other features of the invention will become f 1 - 3 apparent from the following description.
The cyanine compound of the invention is a novel compound undisclosed in literature and represented by the f ormula (1) CH3 CH3 X CH3 "3 X 1: N+ =< I N ChCC-2CH N 1 z v R, wherein..
X is -NR2R3 group (wherein R2 and R3 are the same or different, and each represent hydrogen, lower alkyl or hydroxy-lower alkyl) or lower alkoxy, Y is hydrogen, -NR4R5 group (wherein R4 and R5 are the same or different, and each represent hydrogen, lower alkyl or hydroxy-lower alkyl), lower alkyl or lower alkoxy, R, is an optionally substituted lower alkyl, and Z is acidic residue, with the proviso that when Y is hydrogen, X is not lower alkoxy.
Japanese Unexamined Patent Publication No.85791/1984 discloses a compound (hereinafter referred to as "compound A") which is similar to the compound of the present invention and which is represented by the formula ( 1) CH3 CH3 CH3 CH3 CH3 1 OCH3 C_ CH=CO-3 CH C104 N+ N CH3 CH3 Howeve, the compound A, which has a poor solubility in a solvent and composes a dye layer which is low in optical reflectivity, is not suitable for use as a near infrared light-absorbable organic dye which is useful as a recordirfg medium of optical disk for semiconductor laser.
Shown below are specific examples of the groups represented by X, Y, Rll R2, R3, R4r R5 and Z.
Examples of the lower alkyl group are alkyl groups having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like.
Examples of the hydroxy-lower alkyl group are alkylgroups having 1 to 4 carbon atoms and substituted with one hydroxyl group such as hydroxy methyl, 1 hydroxyethyl, 2-hydroxyethyl, 3-hydroxypropyl, 4 hydroxybutyl, 2-hydroxy-2,2-dimethylethyl, 2-hydroxy-l methylethyl, 3-hydroxy-1-methylpropyl and the like.
Examples of the lower alkoxy group are alkoxy 1 ---5 - groups having 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy and the like.
Examples of the -NR2R3 group and the -NR4R5 group are amino, N,Ndimethylamino, N,N-diethylamino, Nethyl-N-(2-hydroxyethyl)amino, N,Nbis(hydroxymethyl)amino, N,N-bis(hydroxyethyl)amino, N-methyl-Nethylamino, N-methyl-N-n-propylamino, N-methyl-N-n-butylamino and the like.
Examples of the optionally substituted lower alkyl groups are not only the above-exemplified alkyl groups of 1 to 4 carbon atoms but alkyl groups of 1 to 4 carbon atoms which may optionally have at least one substituent selected from the group consisting of Cl_C4 alkoxy, hydroxyl, sulfo, carboxy, (Cl-C4 alkyl)amino, acetoxy and (Cl-C4 alkoxy)carbonyl, such as methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-hydroxyethyl, 2ethoxyethyl, 2-(n-butoxy)ethyl, n- butoxymethyl, -(CH2)n-So3Na (wherein n is an integer of 1 to 4), -(CH2)n- COONa (wherein n is an integer of 1 to 4), methylaminomethyl, dimethylaminomethyl, acetoxymethyl, methoxycarbonylmethyl and the like.
Examples of the group Z are halogen, alkyl sulfate residue, arylsulfonate residue, perchlorate residue, tetrafluoroborate residue, ary1carboxylic acid residue and the like. When Z is halogen, examples of Z_ are Cl-, Pr-, I-, F- and the like. When Z is alkyl sulfate residue, examples of z- are CH3S04-1 C2H5S04-, nC3H7S04-, n-C4H9S04- and the like. When Z is arylsulfonate residue, examples of Z- are F\_S03 1 CH3- a S03- and the like. Wne Z is perchlorate residue, examples of Z- are C104- and the like. When Z is tetrafluoroborate residue, examples of Z- are BF4- and the like. When Z is arylcarboxylic acid residue, examples of Z are r\-Coo- and the like.
Preferable of the compounds according to the invention arethose wherein X is lower alkoxy, Y is lower alkoxy, R, is lower alkyl or lower alkoxylower alkyl and Z is halogen or perchlorate residue. Preferred compounds further include those wherein Y is substituted at the 6- or 7-position of the indolenine ring, particularly 6position.
The compound of the formula (1) according to the invention can be prepared by various processes, for example, by the following process which can produce the compound with ease, hence desirable.
The compound of the invention can be prepared by subjecting an indolenium salt represented by the formula C113 CH3 N+ CH3 Z- 2 1 Y R1 wherein X, Y, R, and Z are as defined above and a conventional o-anilino- acrolein-anil hydrochloride represented by the formula F\\I-NH-CH=CH-CH=NJ/ HCl (3) This condensation reaction is conducted in the presence of a fatty acid salt in an anhydrous organic acid. Examples of useful fatty acid salts are sodium acetate, potassium acetate, calcium acetate, sodium propionate, potassium propionate and the like. The fatty acid salt is used in an amount of about 0.5 to about 3 moles, preferably about 1 to about 2 moles, per mole of the compound of the formula (2). Examples of useful anhydrous organic acids are acetic anhydride, propionic anhydride, butyric anhydride, y-butyrolactone and the like. The anhydrous organic acid is used in an amount of about 10 to about 100 moles, preferably about 20 to about 50 moles, per mole of the compound of the formula (2). The proportions of compounds of the formulas (2) and (3) are about 0.2 to about 1.5 moles, preferably about 0.4 to about 0.7 mole, of the latter per mole of the former. The reaction smoothly proceeds at a temperature of about 50 to about 1500C, preferably about 100 to about 1400C and is completed in about 10 to about 60 minutes.
The indolenium salts of the formula (2) include novel compounds undisclosed in literature, and can be prepared, for example, by the following process (in which the compounds (2a) and (2b) are indolenium salts).
0 0H3 X NH2 CH3-C-C-Br CH3 5) CH3 CH3 X 1 N11 C ['3 (4) (6) C 3 CH3 X Y 2 a CH3 C113 X 1,-- C 112) 1/ 1 K1 alkylating agent alkali ( 7) CH3 CH3 C[13 2 N+ H1 2 b H 12 (8) 9 - wherein:
Z1 is acidic residue other than perchlorate residue and tetrafluoroborate residue, Z2 is perchlorate residue or tetrafluoroborate residue, and X, Y and R, are as defined above.
The reaction between the conventional aniline derivative of the formula (4) and the conventional 3 bromo-3-methyl-2-butanone of the formula (5) is performed in the presence of an acid scavenger. Examples of useful acid scavengers are pyridine, triethylamine, tri-n propylamine,'tr-i-n-butylamine and like tertiary amines, sodium carbonate, potassium carbonate, calcium carbonate and like alkali metal salts of carbonic acids, sodium acetate, potassium acetate, calcium acetate and like is alkali metal salts of acetic acids and the like. The acid scavenger is used in an amount of about 0.3 to about 5 moles, preferably about 0.5 to about 1.5 moles, per mole of the compound of the formula (4). The proportions of compounds of the formulas (4) and (5) are about 0.3 mole to about 5 moles, preferably about 0.5 to about 1.5 moles, of the latter per mole of the former. The reaction is conducted at a temperature in the range of from room temperature to about 2000C, preferably from about 50 to about 1501C and is completed in several hours to about 25 hours, preferably about 5 to about 15 hours.
- 10 The compound of the formula (2a) can be prepared by causing an alkylating agent to act on the indolenine derivative of the formula (6). Examples of the alkylating agent which can be used are alkyl toluenesulfonates such as methyl toluenesulfonate, ethyl toluenesulfonate, npropyl toluenesulfonate, isopropyl toluenesulfonate, nbutyl toluenesulfonate and the like, halogenated alkyls such as ethyl bromide, n-propyl bromide, n- butyl bromide, ethyl iodide, n-propyl iodide, n-propyl chloride, n-butyl chloride and the like, dialkyl sulfates such as dimethyl sulfate, diethyl sulfate and the like, a mixture of acid and epoxy compound (e.g., a mixture of hydrochloric acid, sulfuric acid or like inorganic acid, acetic acid, propionic acid or like organic acid and ethylene oxide, propylene oxide or the like), etc. The alkylating agent is used in an amount of about 0.3 to about 5 moles, preferably about 0.5 to about 2 moles, per mole of the compound of the formula (6). The reaction is carried out in the absence or in the presence of a solvent. Useful solvents include, for example, toluene, xylene and like alkyl benzenes, noctane, n-decane, cyclohexane, decalin and like aliphatic hydrocarbons, benzene, naphthalin, tetralin and like aromatic hydrocarbons, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene and like halogenated hydrocarbons, etc. The reaction is conducted at a temperature in the range of from room temperature to about 2000C, preferably from about 50 to about 1500C and is completed in about 2 to about 30 hours, preferably about 3 to about 15 hours.
The compound of the formula (7) can be prepared by treating the compound (2a) with alkali in a suitable solvent such as water. The alkali to be used can be any of conventional alkalis such as sodium hydroxide, potassium hydroxide and the like. The amount of alkali used is about 1 to about 20 moles, preferably about 1 to about 5 moles', per mole of the compound (2a). The amount of the solvent used is about 2 to about 100 moles, preferably about 2 to about 20 moles, per mole of the compound (2a). The reaction is conducted at a temperature of 0 to about 1500C, preferably from 0 to about 1000C and is completed in dozens of minutes to about 10 hours, preferably about 1 to about 5 hours.
The compound (2b) can be prepared by causing the compound of the formula (7) to react with the compound of the formula (8) in the presence of a suitable solvent such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butanol, isobutyl alcohol, tert-butyl alcohol and like alcohols, benzene, toluene, xylene, n-octane, n-decane, cyclohexane, decalin, trichloroethane, tetrachloroethane, chlorobenzene, dichlorobenzene and like hydrocarbons, etc.
The proportions of compounds of the formulas (7) and (8) are about 0.3 to about 10 moles, preferably about 0.5 to about 3 moles, of the latter per mole of the former. The reaction is conducted at a temperature of 0 to about 700C and is completed in about 10 minutes to about 3 hours.
The compound of the invention thus obtained can be easily separated and purified, for example, by column chromatography, recrystailization and the like.
The compound of the formula (1) according to the invention has a high solubility in an organic solvent such as methanol,ethanol, diacetone alcohol or like alcohols, or dichloromethane, dichloroethane or like aliphatic halogenated hydrocarbons. The compound involves an absorption maximum at about 670 to about 750 nm and has a is high molar absorptivity. When used as a recording medium of optical disk for semiconductor laser, the compound of the invention shows a high reflectivity by the reading laser light (780 nm) for reproduction, hence valuable in use.
Given below are a reference example illustrating the preparation of compound of the formula (2) and preparation examples illustrating the preparation of compounds according to the invention.
Reference Example A mixture of 15.36 9 of 2,4-dimethoxyaniline, t 16.06 g of 3-bromo-3-methyl-2-butanone and 8.0 g of pyridine was reacted at a temperature of 50 to 550C for.5 hours. The reaction mixture was further reacted under reflux for 7 hours. After completion of the reaction, the reaction mixture was poured into 70 ml of water and the mixture was extracted with 30 ml of dichloromethane. The solvent was distilled off and the residue was subjected to vacuum distillation, giving 12.0 9 of 2,3,3-trimethyl-5,7dimethoxyindolenine having a boiling point of 125 to 1300C/2-3mmHg.
A nTixture of 10.96 g of 2,3,3-trimethyl-5,7dimethoxyindolenine obtained above, 11.00 9 of ethyl ptoluenesulfonate and 60 ml of toluene was reacted under reflux for 8 hours. The reaction mixture was subjected to extraction with 50 ml of water, giving lethyl-2,3,3trimethyl-5,7-dimethoxyindoleniumtoluenesulfonate.
To the extract was added 20 9 of 20% NaOH, and the mixture was reacted at 700C for 3 hours. The reaction mixture was submitted to extraction with 30 ml of toluene. The toluene was distilled off and the residue was subjected to vacuum distillation, giving 6.00 9 of 1ethyl-2-methylene-3,3dimethyl-5,7-dimethoxYindoline with a boiling point of 122 to 1290C/34mmHg.
A 2.87 g quantity of 70% HC104 was added to a mixture of 4.95 9 of 1ethyl-2-methylene-3,3-dimethyl-5,7- - 14 dimethoxyindoline and 60 ml of isopropanol at not higher than 200C. The mixture was stirred at room temperature for 1 hour and cooled to not higher than SOC. The deposited crystals were filtered off, washed with isopropanol and dried, giving 6.54 g of 1-ethyl-2,3,3trimethyl-5,7- dimethoxyindoleniumperchlorate with a melting point of 222.5 to 226.50C.
Preparation Example 1 To 60 ml of acetic anhydride were added 4.75 g of compound of the formula (2) (wherein X=N,N dimethylaminor, Y=hydrogen, Rl=methyl, Z_=C104_), 1.94 g of c-anilino-acrolein-anile hydrochloride and 2.5 g of potassium acetate. The mixture was refluxed for 10 minutes and poured into 350 ml of water. The deposited crystals were filtered off, washed with water and recrystallized from methanol, giving 3.44 g of compound of the formula (1) (wherein X=N,N-dimethylamino, Y=hydrogen, Rl=methyl, Z_==C104_). Shown below are the melting point, absorption maximum (Xmax) and molar absorptivity (c) of the compound.
Melting point: 219-2211C imax: 732 nm (diacetone alcohol) F- 2.30 X 105 cm-1 Preparation Example 2 A 3.80 9 quantity of compound of the formula (1) - 15 is (wherein X=N,N-dimethylamino, Y=hydrogen, Rl=ethyl, Z=C104_) was produced by repeating the same procedure as in Preparation Example 1 using 4.96 9 of compound of the formula (2) (wherein X=N,N-dimethylamino, Y=hydrogen, Rl=ethyl, Z-=:C104_).
Melting point: 195-2000C Imax: 728 nm (methanol) 2.34 X 105 cm-1 Preparation Example 3 A 4.21 9 quantity of compound of the formula (1) (wherein X=methoxy, Y=methoxy (7-position of the indolenine ring, the same hereinafter), Rl=ethyl, Z_= C104_) was produced by repeating the same procedure as in Preparation Example 1 using 5.22 g of compound of the formula (2) (wherein X=methoxy, Y=methoxy (7-position), Rl=ethyl, Z_=C104_).
Melting point: 250-2521C Imax: 693 nm (diacetone alcohol) F-: 1.84 X 105 cm-1 Preparation Example 4 The compound of the formula (1) (wherein X=ethoxy, Y=ethoxy (7-position), Rl=ethyl, Z_=C104_) was produced by repeating the same procedure as in Preparation Example 1 using the compound of the formula (2) (wherein X=ethoxy, Y=ethoxy (7-position), Ri=ethyl, Z_=C104_), - 16 xmax: 698 nm (dichloromethane) ú: 1.72 X 105 cm-1 Compounds were produced in Preparation Examples 5 to 22 by repeating the same procedure as in Preparation Example 1 using a suitable class of compound of the formula (2).
Preparation Example 5 Compound of the formula (1) (X=N,Ndimethylamino, Y=methyl (7-position), Rl=methyl, Z_=C104_) Imax: 737 nm (diacetone alcohol) 2.20 X 105 cm-1 Preparation Example 6 Compound of the formula (1) (X=N,Ndimethylamino, Y=methoxy (7-position), Rl=ethyl, Z_=Clxmax: 747 nm (diacetone alcohol) 2.28 X 105 cm-1 Preparation Example 7 F- Compound of the formula (1) (X=N,N-diethylamino, Y=hydrogen, Rl=ethyl, Z_=C2H5S04_) Imax: 735 nm (diacetone alcohol) F-: 2.10 X 105 cm-1 Preparation Example 8 Compound of the formula (1) (X=N-ethyl-N-(2 hydroxyethyl)amino, Y=hydrogen, Rl=ethyl, Z_=CH3-0-SO3_) 1 t 1 xmax: 735 nm (diacetone alcohol) 2.10 X 105 cml Preparation Example 9 Compound of the formula (1) (X=methoxy, Y=methoxy (6-position), Rl=methoxymethyl, Z_= F \\l-S03-) kmax: 702 nm (diacetone alcohol) F-: 1.60 X 105 cm-1 Preparation Example 10 Compound of the formula (1) (X=methoxy, Y=methyl (7-position), Rj=2-hydroxyethyl, Z_=C104) xmgx: 679 nm (diacetone alcohol) 1.84 X 105 cm-1 Preparation Example 11 Compound of the formula (1) (X=methoxy, Y=methyl is (7-position), Rj=2-methoxyethyl, Z_=C104_) xmax: 679 nm (diacetone alcohol) F-: 1.85 X 105 cm-1 Preparation Example 12 Compound of the formula (1) (X=methoxy, Y=methyl (6-position), Rl=n-propyl, Z_=1_) xmax: 683 nm (diacetone alcohol) 1.74 X 105 cm-1 Preparation Example 13 Compound of the formula (1) (X=ethoxy, Y=methyl (.7-position), Rl=ethyl, Z_=BF4) imax: 681 nm (dichloroethane) 1.75 X 105 cm-1 Preparation Example 14 Compound of the formula (1) (X=n-propoxy, Y=methyl (7-position), Rl=ethyl, Z-=C'04- Imax: 683 nm (diacetone alcohol) 1.63 X 105 cm-1 Preparation Example 15 Compound of the formula (1) (X=methoxy, Y=ethyl (7-position), Rl=ethyl, Z_=C104_) Ima7x: 681 nm (diacetone alcohol) 1.82 X 105 cm-1 Preparation Example 16 Compound of the formula (1) (X=methoxy, Y=isopropyl (7-position), Rl=methyl, Z_=I_) imax: 681 nm (diacetone alcohol) E 1.62 X 105 cm-1 Preparation Example 17 Compound of the formula (1) (X=methoxy, Y=methoxy (6-position), Rl=n-buthyl, Z_=I_) xmax: 703 nm (diacetone alcohol) E 1.62 X 105 cm-1 Preparation Example 18 Compound of the formula (1) (X=amino, Y=hydrogen, Rl=ethyl, Z_=C104_) 1 r 1 V 25 Imax: 730 nm (diacetone alcohol) E: 2.30 X 105 cm-1 Preparation Example 19 Compound of the formula (1) (X=N,N bis(hydroxymethyl)amino, Y=hydrogen, Rl=ethyl, Z_=C104_) Xmax: 734 nm (diacetone alcohol) E:: 2.13 X 105 cm-1 Preparation Example 20 Comoound of the formula (1) (X=methoxy, Y=methoxy (6-position), Rl=n- buthyl, Z=C104_) xma7x: 699 nm (dichloromethane) 1.61 X 105 cm-1.
Preparation Example 21 Compound of the formula (1) (X=methoxy, Y=methoxy (7-position), Rl=acetoxyethyl, Z_=C104_) Imax: 693 nm (diacetone alcohol) E:: 1.75 X 105 cm-1 Preparation Example 22 Compound of the formula (1) (X=methoxy, Y=methoxy (7-position), Rl=methoxyethyl, Z_=I_) xmax: 695 nm (diacetone alcohol) 1.80 X 105 cm-1 Reflection Test Each of cyanine dyes as shown below in Table 1 was dissolved in dichloromethane to a concentration of 20 1 - 20 g/l. The solution was applied to an acrylic plate by a spin coater at 1500 rpm to form a layer of 600 to 700 A thickness, which was then dried. optical reflection was measured by 780 nm laser beam from the other side of substrate. Table 1 below shows the results. Table 1 - Cyanine Dye - Optical Reflectivity(%) Dye of Prep. Ex. 1 40 Dye of Prep. Ex. 2 40 Dye of Prep. Ex. 3 42 Dye ofPrep. Ex. 7 40 Dye of Prep. Ex. 20 41 Dye of Prep. Ex. 22 41 Compound A 24 Test for Solubility in Solvent Each of cy4nine dyes as shown below in Table 2 was dissolved in methanol and the solubility was determined at room temperature with the results indicated below in Table 2.
11 Cyanine Dye Ex. 1 Ex. 2 Ex. 3 Ex. 7 Ex. 20 Ex. 22 Dye of Prep. Dye of Prep. Dye of Prep. Dye of Prep. Dye of Prep. Dye of Prep. Compound A 21 Table 2
Solubility (g/1) 20 30 30 Over 30 Over 30 Over 30 UP to 10 1
Claims (5)
- CLAIMS:(1) A cyanine compound represented by the formula 0H3 0H3 X CH3 CH3 X CH =C H) -2 C H =< 1. z N+ 'N Y R R 1 ( 1) wherein:X rs -NR2R 3 group (wherein R2 and R3 are the same or different, and each represent hydrogen, lower alkyl or hydroxylower alkyl) or lower alkoxy, Y is hydrogen, -NR4R5 group (wherein R4 and R5 are the same or different, and each represent hydrogen, lower alkyl or hydroxy-lower alkyl), lower alkyl or lower alkoxy, R, is an optionally substituted lower alkyl, and z is acidic residue, with the proviso that when Y is hydrogen, X is not lower alkoxy.
- 2. A compound according to claim 1 wherein Z is halogen or perchlorate residue.
- 3. A compound according to claim 2 wherein X and Y are both lower alkoxy.
- 4. A compound according to claim 3 wherein Y is substituted at the 6- or the 7-position of the indolenine i:1 - It - 2 3 - ring.
- 5. A compound according to claim 4 wherein R, is lower alkyl or lower alkoxy-lower alkyl.1 Published 1986 at 7-ne Patent Office, S-.ae Ho,-sE 66 7' 'F.:" Hc!bcrr.London WClR 4TP- Purther copies Tnay be obtained from The Patert Office Sales Branch. St Mary Cray. Orpington. Kent BR5 3RD. Printed by Multiplex techniques ltd. St Mary Cray. Kent. Con. 1;87.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19890887 | 1987-08-07 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8818387D0 GB8818387D0 (en) | 1988-09-07 |
| GB2208514A true GB2208514A (en) | 1989-04-05 |
| GB2208514B GB2208514B (en) | 1991-01-16 |
Family
ID=16398944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8818387A Expired - Fee Related GB2208514B (en) | 1987-08-07 | 1988-08-02 | Cyanine compounds |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3826697A1 (en) |
| FR (1) | FR2619119B1 (en) |
| GB (1) | GB2208514B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2235463A (en) * | 1989-08-23 | 1991-03-06 | Ilford Ltd | Novel photographic pentamethine cyanine dyes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE29918139U1 (en) | 1999-10-14 | 2000-05-25 | Hörgeräte Seifert GmbH, 81377 München | Otoplasty for behind-the-ear (BTE) hearing aids |
| US9631096B2 (en) | 2012-01-20 | 2017-04-25 | Cornell University | Dye compositions, methods of preparation, conjugates thereof, and methods of use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1863679A (en) * | 1932-06-21 | Polymethine dyestttees | ||
| US2131853A (en) * | 1932-09-14 | 1938-10-04 | Agfa Ansco Corp | Substituted hepta-and penta-methinecyanines |
| US3974147A (en) * | 1973-04-02 | 1976-08-10 | Minnesota Mining And Manufacturing Company | Reduced styryl dyes |
| JPH0613238B2 (en) * | 1982-11-08 | 1994-02-23 | 株式会社リコー | Optical information recording medium |
| DE3529061A1 (en) * | 1984-08-13 | 1986-02-13 | Ricoh Co., Ltd., Tokio/Tokyo | OPTICAL INFORMATION RECORDING MATERIAL |
| DE3479360D1 (en) * | 1984-09-11 | 1989-09-14 | Ricoh Kk | Optical information recording medium |
-
1988
- 1988-08-02 GB GB8818387A patent/GB2208514B/en not_active Expired - Fee Related
- 1988-08-05 DE DE19883826697 patent/DE3826697A1/en not_active Ceased
- 1988-08-05 FR FR8810607A patent/FR2619119B1/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2235463A (en) * | 1989-08-23 | 1991-03-06 | Ilford Ltd | Novel photographic pentamethine cyanine dyes |
| GB2235463B (en) * | 1989-08-23 | 1992-04-29 | Ilford Ltd | Photographic emulsions containing pentamethine cyanine dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2619119B1 (en) | 1992-03-20 |
| FR2619119A1 (en) | 1989-02-10 |
| GB8818387D0 (en) | 1988-09-07 |
| DE3826697A1 (en) | 1989-02-16 |
| GB2208514B (en) | 1991-01-16 |
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Effective date: 19980802 |