CA1154963A - USE OF.alpha.,.alpha.'-BIS(DIALKYLAMINOBENZYLIDENE) KETONE DYES IN OPTICAL RECORDING ELEMENTS - Google Patents
USE OF.alpha.,.alpha.'-BIS(DIALKYLAMINOBENZYLIDENE) KETONE DYES IN OPTICAL RECORDING ELEMENTSInfo
- Publication number
- CA1154963A CA1154963A CA000369312A CA369312A CA1154963A CA 1154963 A CA1154963 A CA 1154963A CA 000369312 A CA000369312 A CA 000369312A CA 369312 A CA369312 A CA 369312A CA 1154963 A CA1154963 A CA 1154963A
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- CA
- Canada
- Prior art keywords
- dye
- bis
- binder
- support
- recording element
- 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
-
- 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
-
- 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
-
- 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
- G11B7/2531—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 glass
-
- 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
- G11B7/2535—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 polyesters, e.g. PET, PETG or PEN
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
-i-THE USE OF .alpha.,.alpha.'-BIS(DIALKYLAMINOBENZYLIDENE) KETONE DYES IN OPTICAL RECORDING ELEMENTS
Abstract of the Disclosure Dyes conforming to the structure:
Abstract of the Disclosure Dyes conforming to the structure:
Description
9~;~
THE USE OF ~,Q'-BIS(DIALKYLAMINOBENZYLIDENE) KETOlæ DYES IN OPTICAL RECORDING E-LEMENTS
Field of the Inventlon The present lnventlon re~htes to the use o~ cer taln ketone dye comp~sltl~ns ln op~lcal rec~rdlng element~.
T~e ke~ne d~es ~ave a high ex~inctlon coerrlcient ~t 4BB
nm, have good sclubllity ln organlc solvents ~nd are eom~
patible with common blnders. Thus, in one aspect, the pr~-ent lnventlcn relates to optical recordlng element~ ~hlch have a layer comprlsln~ an amorphous materlal lncl~lng a binder and the descrlbed dye.
Descri~tlon ~elative to the Prior Art Elements for reeording information by thermally altering the physical structure of ~ material ~re known.
1~ One such element comprises a layer of a pl~stic material ~olvent coated on a support. The plastic material can be thermally deformed by a writing beam (usually a laser beam) so that some of the plastic material is di~placed in the area illuminated by the beam. This deformation pattern retains its shape after the laser beam is "removed". The resulting deformation pattern can be read by pro~c~ing the pattern onto a viewing soreen.
More recently~ elements and means ha~e been pro-vided for rapidly recording large amounts ~ ~lg~tal lnror-: 25 matlon ln a small area. These elements pro~de a me~hod ~r recording vldeo ln~ormation whlch can be read b~ck with a hlgh s~gnal-to-nolse ratio (SNR). These elements employ a thln recording layer o~ a certaln metall~c ~r ~rg~nic ~ste-rial which ls vacuum-depo~lted on a ~upport. ~ecor~lng accomplished by a beam o~ ~lgh-energy density r~lat~on, such as a laser beam. Typically, the laser beam i8 rOCU8ed onto the surf~ce o~ the re~r~lng layer o~ the el~ment. The recording layer ls su~h that lt absorbs ener~y ~r3m the laser beam so that small portion~ o~ the layer burn, e~apo-rate or are otherwl8e ai~placed rrom t~e~e portion~. Thl8~echnlque is u~ually referre~ to as "ablative re~ lng~.
Normally9 there ls ~ont~nuou~ ~otion bet~een the l~er ~nd the l~yer ~o that~ as ~he la~er 1~ pul~ed ~r ~odul~ted~
dlscreke pits or holes o~ ~arying ~læe~ are create~ ~n the . . . -~L~S~9~i3 layer. The sizes and spacing of these holes constitute the encoded information. One element of this type is commonly referred to in the art as a "video disc".
Video discs of the ablative type can be read back using a laser beam similar to the one used to record the element. In conventional ablative video discs, the reading beam must also be significantly absorbed by the recording layer. A continuous reading beam is focused on the record-ing layer and the difference in optical density betwee~
pitted and unpitted areas is detectecl by a photodetector.
It will be readily apparent that the recordiny layer must absorb significantly less energy rom the reading beam than it absorbs from the writing beam if physical damage to the recording is to be avoided. This is usually accomplished by using a reading beam of m~lch lesser power than the writing beam.
It has recently been discovered that, if the deformations which are formed in the recording layer are of a certain type, the information represented by these deformations can be read using a reading beam which is not absorbed by the recording layer. By using a recording layer of amorphous material having an extremely high ab-sorbencyl it has been found that deformations having sharp-ly defined ridges can be formed. It is theorized that the ability to read with a laser which is not absorbed by the recording layer is the result of light scatterin~ or phase shift from the sharply defined ridges. For whatever reason, it is now possible to use a higher-power laser read beam which in turn provides a comparatively high signal-to-noise ratio output. The recording element and method for reading are described in copending, commonly assigned application Serial No. 318,158 filed December 18, 1~78, by Thomas and Wrobe~.
; ~ In the method of Thomas and Wrobel described in the preceding paragraph~ it is desirable to pro~ide a ~;~ recording layer which has'an absorption factor at the record-ing wavelength which is as high as possible. It was deter-mined that an absorption factor in excess of 20 was nec-essary to produce the deformations which were readable by a .
5 ~ ~ 3 read beam whlch was not absorbed by the recordlng layer.
I`he absorption ractor ls de~ined as the product cr ~he welght fractionor dye included in the dye-blnder composltlon and the molar extlnction coe~riclent o~ dye ~t the wave-length o~ the recording beam (E~), dlvlded by the molecularwelght o~ the dye (MW). The absorption ractor is reclted ln terms o~ unlts of liter per gram-centlmeter. Thus, the maxlmum absorptlon ~actor Or a partlcular dye-binder amor-phous recording composltlon ls li.mited by both the extinc-tion coefficient and the compatability o~ the dye wlth theblnder. One high-energy density radiation source ls an argon-laser which emits at about 488 nm. When recordlng usln6 this laser, lt ls desirable that the dye whlch ls ~n the amorphous compositlon have an extremely hlgh extinction coe~icient at this wavelength. Furthermore, it ls desira-ble that the dye be compatlble with the binder ln hlgh concentratlons. While the materlals dlsclosed ln the Thomas and Wrobel application clted ln the previous paragraph pro~ide ror absorption factors hlgh enough to permit the necessary types Or deformations to be formed, materlals whlch provide still higher absorption ractors have been sought.
Su~ary of the Inventior, Dyes have been discovered whose properties make them particularly use~ul ln Yldeo dlsc recordlng elements.
These dyes have extremely high extlnction coe~iclents at 488 nm and have excellent solubillty in common organlc solvents. These dyes are compatible ln hlgh concentration wlth binders which are useful ln video disc recording layers and can be used in these layers to provlde ex~remely high absorptlon factors.
The dyes are (4-dlalkylamlnobenzylldene) ~etones.
More specl~ically, the dyes conrorm to khe ~tructure:
O
H ~ H
(5~)~N~ .t ~ NtR)e (CH~) n , ~ , 1 ~'- " ';
~ji4~3163 wherein n is an lnteger rrom 0-5 and each R is independently selected ~rom the group consisting ~ stralght- and branched-chain alkyl groups Or ~bout 1-6 carbon atoms ~u~h as methyl, ethyl, isopropyl, t-butyl and the li~e. (Both 5 the acetone-derived c~pounds and the cyclopr~panone-derlved compounds are lntended to be lncluded when n ~ o.) In one aspect Or the present in~entlon, there ls provided a recordlng element comprlsing a ~upport havlng coated thereon a layer Or amorp~lous compositlon comprlslng a binder and a dye, wherein:
said amorphous material has an absorptlon ~actor Or ~t least 20 at 488 nm and sai~ dye is a (4-dialkylaminobenzylldene) ketone as described abcve.
1~ In another aspect, there is provlded a mekhod Or maklng the descrlbed recordlng element.
In another aspect Or the present inventlon, there is provided an in~ormatlon record comprlsing a support having coated thereon khe amorphous dye blnder composition described above and havlng ~ormed thereln a plurallty Or de~ormatlons. These de~ormatlons have a size smaller than 1.5 microns and comprlse a depresslon surr~unded by a sharply de~lned ridge. These derormatlons are such that they are detectable using a beam Or hlgh-energy density radlation which is not absorbed by the amorphous composl-tlon.
Detailed Descri2tion o~ the Inventlon Vseful dyes accordlng to the present inventlon conform to the structure:
O .~
H ~ H
~~ ~C-0~ =C-I~~
3 (R) N I~ N(R)æ
(Ctlæ) n mese dyes have exttnctlon coe~rlclents ~hlch are very high at 488 nm3 typl¢ally havlng a molar extinctlon coer~iclent at this wa~elength whlch exceeds ~bout 65,000. In addltionJ
, ~ . , ~S~63 the dyes are compatible at relatively high concentratlons wlth c~mmon binders which make them userul in video disc appllcati~ns. These dyes are soluble ln c~mmon ~ol-vents such as cyclohexanone, acekone~ benzene, xyl~ne ~nd the like.
Each R ln the ~tructura~ formula above ls alkyl ~8 described. ~r the purp~ses Or 1;he lnventlon, ~yes ha~lng substi~uted alkyl groups such as, ~or example, halogen-substltuted alkyl, e.g., chloromethyl, bromoethyl and ~he like, are considered to be equlvalent. Further~ the ben-zylidene gr~up can be substituted with groups other than the alkylamino group ln other posl~lons so long as ~hese sub-stituents do not adversely afrect the chromophore. The cycllc ketone ring, when present, can be slmllarly ~ubstl-tuted. ~se~ul substltuents include, ~or example 9 halogenand lower alkyl. However; dyes n~t havlng these ~ubstltu-ents are pre~erred because these substltuents add to the molecular welght and thererore decrease the value ~r ~/MW.
The dyes described above can be made by reactlng acetone or a cyclic ketone such as cyclopentan~ne wlth ~
dialkylaminobenzaldehyde. The ~tarting materials ~or maklng the dyes useful in the precent inventlon are well-known ln the art. The dyes are made by condensing the aldehyde and the ketone in an alkallne solutlon compr~slng an organlc
THE USE OF ~,Q'-BIS(DIALKYLAMINOBENZYLIDENE) KETOlæ DYES IN OPTICAL RECORDING E-LEMENTS
Field of the Inventlon The present lnventlon re~htes to the use o~ cer taln ketone dye comp~sltl~ns ln op~lcal rec~rdlng element~.
T~e ke~ne d~es ~ave a high ex~inctlon coerrlcient ~t 4BB
nm, have good sclubllity ln organlc solvents ~nd are eom~
patible with common blnders. Thus, in one aspect, the pr~-ent lnventlcn relates to optical recordlng element~ ~hlch have a layer comprlsln~ an amorphous materlal lncl~lng a binder and the descrlbed dye.
Descri~tlon ~elative to the Prior Art Elements for reeording information by thermally altering the physical structure of ~ material ~re known.
1~ One such element comprises a layer of a pl~stic material ~olvent coated on a support. The plastic material can be thermally deformed by a writing beam (usually a laser beam) so that some of the plastic material is di~placed in the area illuminated by the beam. This deformation pattern retains its shape after the laser beam is "removed". The resulting deformation pattern can be read by pro~c~ing the pattern onto a viewing soreen.
More recently~ elements and means ha~e been pro-vided for rapidly recording large amounts ~ ~lg~tal lnror-: 25 matlon ln a small area. These elements pro~de a me~hod ~r recording vldeo ln~ormation whlch can be read b~ck with a hlgh s~gnal-to-nolse ratio (SNR). These elements employ a thln recording layer o~ a certaln metall~c ~r ~rg~nic ~ste-rial which ls vacuum-depo~lted on a ~upport. ~ecor~lng accomplished by a beam o~ ~lgh-energy density r~lat~on, such as a laser beam. Typically, the laser beam i8 rOCU8ed onto the surf~ce o~ the re~r~lng layer o~ the el~ment. The recording layer ls su~h that lt absorbs ener~y ~r3m the laser beam so that small portion~ o~ the layer burn, e~apo-rate or are otherwl8e ai~placed rrom t~e~e portion~. Thl8~echnlque is u~ually referre~ to as "ablative re~ lng~.
Normally9 there ls ~ont~nuou~ ~otion bet~een the l~er ~nd the l~yer ~o that~ as ~he la~er 1~ pul~ed ~r ~odul~ted~
dlscreke pits or holes o~ ~arying ~læe~ are create~ ~n the . . . -~L~S~9~i3 layer. The sizes and spacing of these holes constitute the encoded information. One element of this type is commonly referred to in the art as a "video disc".
Video discs of the ablative type can be read back using a laser beam similar to the one used to record the element. In conventional ablative video discs, the reading beam must also be significantly absorbed by the recording layer. A continuous reading beam is focused on the record-ing layer and the difference in optical density betwee~
pitted and unpitted areas is detectecl by a photodetector.
It will be readily apparent that the recordiny layer must absorb significantly less energy rom the reading beam than it absorbs from the writing beam if physical damage to the recording is to be avoided. This is usually accomplished by using a reading beam of m~lch lesser power than the writing beam.
It has recently been discovered that, if the deformations which are formed in the recording layer are of a certain type, the information represented by these deformations can be read using a reading beam which is not absorbed by the recording layer. By using a recording layer of amorphous material having an extremely high ab-sorbencyl it has been found that deformations having sharp-ly defined ridges can be formed. It is theorized that the ability to read with a laser which is not absorbed by the recording layer is the result of light scatterin~ or phase shift from the sharply defined ridges. For whatever reason, it is now possible to use a higher-power laser read beam which in turn provides a comparatively high signal-to-noise ratio output. The recording element and method for reading are described in copending, commonly assigned application Serial No. 318,158 filed December 18, 1~78, by Thomas and Wrobe~.
; ~ In the method of Thomas and Wrobel described in the preceding paragraph~ it is desirable to pro~ide a ~;~ recording layer which has'an absorption factor at the record-ing wavelength which is as high as possible. It was deter-mined that an absorption factor in excess of 20 was nec-essary to produce the deformations which were readable by a .
5 ~ ~ 3 read beam whlch was not absorbed by the recordlng layer.
I`he absorption ractor ls de~ined as the product cr ~he welght fractionor dye included in the dye-blnder composltlon and the molar extlnction coe~riclent o~ dye ~t the wave-length o~ the recording beam (E~), dlvlded by the molecularwelght o~ the dye (MW). The absorption ractor is reclted ln terms o~ unlts of liter per gram-centlmeter. Thus, the maxlmum absorptlon ~actor Or a partlcular dye-binder amor-phous recording composltlon ls li.mited by both the extinc-tion coefficient and the compatability o~ the dye wlth theblnder. One high-energy density radiation source ls an argon-laser which emits at about 488 nm. When recordlng usln6 this laser, lt ls desirable that the dye whlch ls ~n the amorphous compositlon have an extremely hlgh extinction coe~icient at this wavelength. Furthermore, it ls desira-ble that the dye be compatlble with the binder ln hlgh concentratlons. While the materlals dlsclosed ln the Thomas and Wrobel application clted ln the previous paragraph pro~ide ror absorption factors hlgh enough to permit the necessary types Or deformations to be formed, materlals whlch provide still higher absorption ractors have been sought.
Su~ary of the Inventior, Dyes have been discovered whose properties make them particularly use~ul ln Yldeo dlsc recordlng elements.
These dyes have extremely high extlnction coe~iclents at 488 nm and have excellent solubillty in common organlc solvents. These dyes are compatible ln hlgh concentration wlth binders which are useful ln video disc recording layers and can be used in these layers to provlde ex~remely high absorptlon factors.
The dyes are (4-dlalkylamlnobenzylldene) ~etones.
More specl~ically, the dyes conrorm to khe ~tructure:
O
H ~ H
(5~)~N~ .t ~ NtR)e (CH~) n , ~ , 1 ~'- " ';
~ji4~3163 wherein n is an lnteger rrom 0-5 and each R is independently selected ~rom the group consisting ~ stralght- and branched-chain alkyl groups Or ~bout 1-6 carbon atoms ~u~h as methyl, ethyl, isopropyl, t-butyl and the li~e. (Both 5 the acetone-derived c~pounds and the cyclopr~panone-derlved compounds are lntended to be lncluded when n ~ o.) In one aspect Or the present in~entlon, there ls provided a recordlng element comprlsing a ~upport havlng coated thereon a layer Or amorp~lous compositlon comprlslng a binder and a dye, wherein:
said amorphous material has an absorptlon ~actor Or ~t least 20 at 488 nm and sai~ dye is a (4-dialkylaminobenzylldene) ketone as described abcve.
1~ In another aspect, there is provlded a mekhod Or maklng the descrlbed recordlng element.
In another aspect Or the present inventlon, there is provided an in~ormatlon record comprlsing a support having coated thereon khe amorphous dye blnder composition described above and havlng ~ormed thereln a plurallty Or de~ormatlons. These de~ormatlons have a size smaller than 1.5 microns and comprlse a depresslon surr~unded by a sharply de~lned ridge. These derormatlons are such that they are detectable using a beam Or hlgh-energy density radlation which is not absorbed by the amorphous composl-tlon.
Detailed Descri2tion o~ the Inventlon Vseful dyes accordlng to the present inventlon conform to the structure:
O .~
H ~ H
~~ ~C-0~ =C-I~~
3 (R) N I~ N(R)æ
(Ctlæ) n mese dyes have exttnctlon coe~rlclents ~hlch are very high at 488 nm3 typl¢ally havlng a molar extinctlon coer~iclent at this wa~elength whlch exceeds ~bout 65,000. In addltionJ
, ~ . , ~S~63 the dyes are compatible at relatively high concentratlons wlth c~mmon binders which make them userul in video disc appllcati~ns. These dyes are soluble ln c~mmon ~ol-vents such as cyclohexanone, acekone~ benzene, xyl~ne ~nd the like.
Each R ln the ~tructura~ formula above ls alkyl ~8 described. ~r the purp~ses Or 1;he lnventlon, ~yes ha~lng substi~uted alkyl groups such as, ~or example, halogen-substltuted alkyl, e.g., chloromethyl, bromoethyl and ~he like, are considered to be equlvalent. Further~ the ben-zylidene gr~up can be substituted with groups other than the alkylamino group ln other posl~lons so long as ~hese sub-stituents do not adversely afrect the chromophore. The cycllc ketone ring, when present, can be slmllarly ~ubstl-tuted. ~se~ul substltuents include, ~or example 9 halogenand lower alkyl. However; dyes n~t havlng these ~ubstltu-ents are pre~erred because these substltuents add to the molecular welght and thererore decrease the value ~r ~/MW.
The dyes described above can be made by reactlng acetone or a cyclic ketone such as cyclopentan~ne wlth ~
dialkylaminobenzaldehyde. The ~tarting materials ~or maklng the dyes useful in the precent inventlon are well-known ln the art. The dyes are made by condensing the aldehyde and the ketone in an alkallne solutlon compr~slng an organlc
2~ solvent. The s~lutl~n can be made alkallne by the additlon o~ sultable base such as potass~um hydroxide, sodium hydrox-ide and the llke. Use~ul organlc solvents lnclude methanol and ethanol. The reaction solutlon can be heated under rerlux to produce the desired pr~duct.
Illustrative ~yes which have been ~ade by this method include: _ 2,~-bis(4-diethylamlnobenzylidene)cycl~pent2none 2J6-bis(4--diethylamin~enzylldene~cyclohexarJone l~3-bls(4~diethylamin~ben ylidene)acet~ne
Illustrative ~yes which have been ~ade by this method include: _ 2,~-bis(4-diethylamlnobenzylidene)cycl~pent2none 2J6-bis(4--diethylamin~enzylldene~cyclohexarJone l~3-bls(4~diethylamin~ben ylidene)acet~ne
3~ Other userul dyes lnclude:
,~
' ' ;3 2,3-bis(4-dimethylaminobenzylidene)cyclopropanone 2,5-bisCLi (N-t-butyl-N-~ethylamino)benzylidene]-cyclopentanone The described dyes are compatible with binders which are useful in making laser recording element~. By "compatible" is meant that the dye can be mixed with the binder in sufficient concentration to provide the required absorption factor, e.g., greater than 20, without crystal-lizing after a layer of the dye and binder is coated and dried. Typically, the described dyes are compatible in dye-binder compositions comprising at least 50 percent dye by weight~ although higher concentrations and therefore higher absorption factors are possible. Because of the high extinction coefficient of the present dyes at 488 nm and their excellent compatibility with common binders, these dyes can be included in the composition over a ver-y wide range of concentration while maintaining the absorption ~actor in excess of 20. This facilitates the optimization of the element.
Useful binders include any film-forming material which is capable of being deformed upon exposure to high-energy density radiation such as a laser beam. Useful binders include cellulose acetate butyrate, polystyrenes, polysulfonamides~ polycarbonates, cellulose nitrate, poly-;~ 25 (ethyl methacrylate), poly(vinyl butyral) and the like.
Combinations o~ binders can also be used. Cellulose nitrate is the preferred binder.
A useful laser recording element comprises a support having coated thereon a layer of the dye included in the binder. Depending upon the desired mode of reading the element 3 the support can either be reflective or transpar-ent. In the case of a reflective support, both sides of the support can be reflective and a recording layer can be provided on both sides. The support can be any of a wide variety of materials i~ncluding glass, a self-supporting ~ polymer film such as poly(ethylene terephthalate) or cel-; lulose acetate, or metal. The support must have a rela-::
~:
. - .. ..
:
. .
~S~5~63 tively high melting point in order to a~oid deformation of the support during recording. The support is deslrably very smooth to minimize noise and dropouts. In certain preferred embodiments, the support is coated with a smoothing layer prior to the coating of the reflective surface and the described dye-binder composition.
The composition which is used as a smoothing layer is preferably a low-viscosity, polymerizable fluid which can be coated on the surface of the support. Following coating, polymerization of the fluid produces a microsmooth surface on the support. The support can be made reflective by vacuum metalization of the smooth surface. In pre~erred embodiments, the polymerizable fluid comprises photopoly~
merizable monomers. Preferably, the monomers or mixtures of monomers are a low-viscosity fluid in the absence of a solvent. Useful polymerizable fluid compositions are described in US Patents 4,0~2,173 and 4,171,979.
The recording layer comprising the described dye and binder can be coated by many of a wide variety of meth-ods. Most conveniently, the dye and binder are coated froma common solvent or, alternatively, from a mixture of misci-ble solvents. The dye-binder composition can be coated by spray coating, air knife coating, whirl coating or by any other suitable method. The thickness of the recording layer according to the present invention is not critical; however, best results are obtained when the thickness of the layer is ; between about 0.1 and about 10 microns.
The described recording compositions are capable of producing depressions or holes surrounded by sharply defined ridges. This type of deformation can be read back using a read beam which is not significantly absorbed by the recording layer. By "sharply defined ridge" is meant that the ridge and hole/depression have noticeable boundaries and that, as measured in the plane of the undeformed outer ~urface of the layer, the width of the ridge is less than or equal to the breadth of the hole depression. These dimen-sions can be measured from an electron micrograph.
The thickness, absorption factor and index of refraction of the recording compositions of the present .
' ' "~' . :
. , , ~54~6~
invention can be optimized by a method which is described in copending, commonly assigned application Serial No. 369,597 entitled PHYSICALLY OPTIMIZED OPI'ICAI. DISC STRUCTURE, METHOD
AND APPARATUS by Howe and Wrobel.
The following examples are presented.
Preparation 1: Preparation of 2,5-bis(4-diethylaminobenzyli-dene~cyclopentanone About 100 g of ~-diethylaminobenzaldehyde were dissolved in a solution of 80 g of potassium hydroxide in 1000 mL of methanol. About 26 g of cyclopentanone were added with stirring and the reaction mixture was heated under reflux on a steam bath for 3 hr. After chilling in the freezer, a solid precipitate was collected, washed with alcohol and recrystallized from a mixture of alcohol and acetonitrile. The title compound was confirmed by lts NMR
spectrum. This dye has an ~488/MW of 188.
Example 1: Video recording element This example is similar to Example II of the Howe and Wrobel application cited above.
A 110-mm-diameter circular glass substrate was whirl-coated with a surface-smoothing composition by flood-ing the glass substrate with the smoothing composition at low rpm (about 80-100 rpm) and then leveling the coating by advancing the speed to about 500 rpm. The surface-smoothing composition comprised:
pentaerythritol tetraacrylate 20 g a low-viscosity urethane-acrylate mono- 20 y mer (UV-curable Topcoat 874~C-2002~, Fuller O'Brien Corp) 2 ethoxyethanol 60 g a coumarin sensitizer composition 3 g surfactant 3 drops :; , The coated and dried surface-smoothing composition was cured by irradiatihg with a 3000-watt pulsed xenon arc lamp at 18 in for 4 min.
The thus smoothed surface of the substrate was then coated with a 500-~-thick reflecting layer of aluminum by vapor deposition.
\~
' ,, , ~1~4~;3 A recording layer was whirl-coated on the reflect-ing layer by flooding the reflecting layer with the dye-binder composition at low rpm and then leveling the coating at about 1300 rpm. The dye-binder cornposition was formed by dissolving 1 æ o~ cellulose nitrate and 1 g of the dye prepared in Preparation 1 in 60 g o~ cyclohexanone. After drying, the disc was ready to use.
Tracks were recorded in the recording layer of the disc using an argon-ion laser-light beam (488 nm) focused with a numerical aperture NAg = 0.525 while the disc was rotating at 1800 rpm. (The term "NAg" represents the numerical aperture of the focused gaussian beam of light measured to its e irradiance diameter.) The recorded tracks were then read back with a similarly focused helium-neon laser-light beam (633 nm) having a power of about 1 mW
on the disc surface. ~or an incident write power of about 10 mW, the SNR on readout was about 50. In comparison, a recording layer which was the same as that of this example, except that the dye was 3,3'-carbonylbis(7-diethylamino-coumarin), required an incident write power of about 15 mWto produce a recording which could be read back with an SNR
of 50.
Although the invention has been described in considerable detail with particular reference to certain preferred embodiments thereof, variations and modifications can be effected within the spirit and scope of the inven-tion.
..
~S~g6~
.. . . _ The ~4-~ialkylaminobenzyl~dene) ketone6 of thi 8 inventlon have the ~tructure:
H ~ H
C~ ~C~
(R) 2 N~ N (R) 2 wherein Rl i~ (CH2)n or CH2-l-CH2; wherein ~H3 n is ~n integer from 0-5 and e~ch R i~ independently eelected from the group con~i~ting of ~traightand br~nched-chAin ~lkyl groups of sbout 1-6 car~on atoms such as methyl, ethyl, i~o-propyl, ~obutyl and ~he llke. (Both the acetone-derived com-pound~ ~nd the cyclopropanone-derived compound~ are intended :~ o be included when n ~ o.) A u6eful dye formed within the sbove ~tructure i~
~ 3,5-b~6(4-diethyl~miDobenzyl~dene~ methyl-4-piperidorle.
:~ 20 : An ex~mple of the prepar~tion ~nd use of the above dye ln fi video recording element ~ presented below:
Psepar~t~o~ 2: Preparat~on o~ 3~5-bls(4~diethylam~nobenzy-lidene)-l-met~yl-4~p~peritone ethyl~4-piperidvne (2 .25g) and 7 ~ lg o ~: : p~d~ethylamino-benzaldehyde were ~dded to a solut~on of 4g : pot~lum bydroxide in 50 ml methanol. The reaction ml~ture was heate~ at refllex 3 1/2 hours and ~llowed to st~nd ~ room emper~ture overnight. The product wa~ collected ~nd ~- recrystallized fr~m 700 ml ~cetoni~rile. The W ~pectr~ of the isolated product w~ confii~tent with the ~eructure of the titled compound.
~ ~ 5~ ~ 6 EXAMPLE
A video recording element W~lB prep~red as ln Example 1 with ~he dye o~ prep~r~t~on 2. the solvent was ~ mixture of 30g of chlorobenzene ~nd 30g of cyclohexanone, instead of 60g of cyclohex~none. At ~ recordlng l~ser power of between 18 to 20m W, the SNR was 55db.
: s-~
~'~
,~
' ' ;3 2,3-bis(4-dimethylaminobenzylidene)cyclopropanone 2,5-bisCLi (N-t-butyl-N-~ethylamino)benzylidene]-cyclopentanone The described dyes are compatible with binders which are useful in making laser recording element~. By "compatible" is meant that the dye can be mixed with the binder in sufficient concentration to provide the required absorption factor, e.g., greater than 20, without crystal-lizing after a layer of the dye and binder is coated and dried. Typically, the described dyes are compatible in dye-binder compositions comprising at least 50 percent dye by weight~ although higher concentrations and therefore higher absorption factors are possible. Because of the high extinction coefficient of the present dyes at 488 nm and their excellent compatibility with common binders, these dyes can be included in the composition over a ver-y wide range of concentration while maintaining the absorption ~actor in excess of 20. This facilitates the optimization of the element.
Useful binders include any film-forming material which is capable of being deformed upon exposure to high-energy density radiation such as a laser beam. Useful binders include cellulose acetate butyrate, polystyrenes, polysulfonamides~ polycarbonates, cellulose nitrate, poly-;~ 25 (ethyl methacrylate), poly(vinyl butyral) and the like.
Combinations o~ binders can also be used. Cellulose nitrate is the preferred binder.
A useful laser recording element comprises a support having coated thereon a layer of the dye included in the binder. Depending upon the desired mode of reading the element 3 the support can either be reflective or transpar-ent. In the case of a reflective support, both sides of the support can be reflective and a recording layer can be provided on both sides. The support can be any of a wide variety of materials i~ncluding glass, a self-supporting ~ polymer film such as poly(ethylene terephthalate) or cel-; lulose acetate, or metal. The support must have a rela-::
~:
. - .. ..
:
. .
~S~5~63 tively high melting point in order to a~oid deformation of the support during recording. The support is deslrably very smooth to minimize noise and dropouts. In certain preferred embodiments, the support is coated with a smoothing layer prior to the coating of the reflective surface and the described dye-binder composition.
The composition which is used as a smoothing layer is preferably a low-viscosity, polymerizable fluid which can be coated on the surface of the support. Following coating, polymerization of the fluid produces a microsmooth surface on the support. The support can be made reflective by vacuum metalization of the smooth surface. In pre~erred embodiments, the polymerizable fluid comprises photopoly~
merizable monomers. Preferably, the monomers or mixtures of monomers are a low-viscosity fluid in the absence of a solvent. Useful polymerizable fluid compositions are described in US Patents 4,0~2,173 and 4,171,979.
The recording layer comprising the described dye and binder can be coated by many of a wide variety of meth-ods. Most conveniently, the dye and binder are coated froma common solvent or, alternatively, from a mixture of misci-ble solvents. The dye-binder composition can be coated by spray coating, air knife coating, whirl coating or by any other suitable method. The thickness of the recording layer according to the present invention is not critical; however, best results are obtained when the thickness of the layer is ; between about 0.1 and about 10 microns.
The described recording compositions are capable of producing depressions or holes surrounded by sharply defined ridges. This type of deformation can be read back using a read beam which is not significantly absorbed by the recording layer. By "sharply defined ridge" is meant that the ridge and hole/depression have noticeable boundaries and that, as measured in the plane of the undeformed outer ~urface of the layer, the width of the ridge is less than or equal to the breadth of the hole depression. These dimen-sions can be measured from an electron micrograph.
The thickness, absorption factor and index of refraction of the recording compositions of the present .
' ' "~' . :
. , , ~54~6~
invention can be optimized by a method which is described in copending, commonly assigned application Serial No. 369,597 entitled PHYSICALLY OPTIMIZED OPI'ICAI. DISC STRUCTURE, METHOD
AND APPARATUS by Howe and Wrobel.
The following examples are presented.
Preparation 1: Preparation of 2,5-bis(4-diethylaminobenzyli-dene~cyclopentanone About 100 g of ~-diethylaminobenzaldehyde were dissolved in a solution of 80 g of potassium hydroxide in 1000 mL of methanol. About 26 g of cyclopentanone were added with stirring and the reaction mixture was heated under reflux on a steam bath for 3 hr. After chilling in the freezer, a solid precipitate was collected, washed with alcohol and recrystallized from a mixture of alcohol and acetonitrile. The title compound was confirmed by lts NMR
spectrum. This dye has an ~488/MW of 188.
Example 1: Video recording element This example is similar to Example II of the Howe and Wrobel application cited above.
A 110-mm-diameter circular glass substrate was whirl-coated with a surface-smoothing composition by flood-ing the glass substrate with the smoothing composition at low rpm (about 80-100 rpm) and then leveling the coating by advancing the speed to about 500 rpm. The surface-smoothing composition comprised:
pentaerythritol tetraacrylate 20 g a low-viscosity urethane-acrylate mono- 20 y mer (UV-curable Topcoat 874~C-2002~, Fuller O'Brien Corp) 2 ethoxyethanol 60 g a coumarin sensitizer composition 3 g surfactant 3 drops :; , The coated and dried surface-smoothing composition was cured by irradiatihg with a 3000-watt pulsed xenon arc lamp at 18 in for 4 min.
The thus smoothed surface of the substrate was then coated with a 500-~-thick reflecting layer of aluminum by vapor deposition.
\~
' ,, , ~1~4~;3 A recording layer was whirl-coated on the reflect-ing layer by flooding the reflecting layer with the dye-binder composition at low rpm and then leveling the coating at about 1300 rpm. The dye-binder cornposition was formed by dissolving 1 æ o~ cellulose nitrate and 1 g of the dye prepared in Preparation 1 in 60 g o~ cyclohexanone. After drying, the disc was ready to use.
Tracks were recorded in the recording layer of the disc using an argon-ion laser-light beam (488 nm) focused with a numerical aperture NAg = 0.525 while the disc was rotating at 1800 rpm. (The term "NAg" represents the numerical aperture of the focused gaussian beam of light measured to its e irradiance diameter.) The recorded tracks were then read back with a similarly focused helium-neon laser-light beam (633 nm) having a power of about 1 mW
on the disc surface. ~or an incident write power of about 10 mW, the SNR on readout was about 50. In comparison, a recording layer which was the same as that of this example, except that the dye was 3,3'-carbonylbis(7-diethylamino-coumarin), required an incident write power of about 15 mWto produce a recording which could be read back with an SNR
of 50.
Although the invention has been described in considerable detail with particular reference to certain preferred embodiments thereof, variations and modifications can be effected within the spirit and scope of the inven-tion.
..
~S~g6~
.. . . _ The ~4-~ialkylaminobenzyl~dene) ketone6 of thi 8 inventlon have the ~tructure:
H ~ H
C~ ~C~
(R) 2 N~ N (R) 2 wherein Rl i~ (CH2)n or CH2-l-CH2; wherein ~H3 n is ~n integer from 0-5 and e~ch R i~ independently eelected from the group con~i~ting of ~traightand br~nched-chAin ~lkyl groups of sbout 1-6 car~on atoms such as methyl, ethyl, i~o-propyl, ~obutyl and ~he llke. (Both the acetone-derived com-pound~ ~nd the cyclopropanone-derived compound~ are intended :~ o be included when n ~ o.) A u6eful dye formed within the sbove ~tructure i~
~ 3,5-b~6(4-diethyl~miDobenzyl~dene~ methyl-4-piperidorle.
:~ 20 : An ex~mple of the prepar~tion ~nd use of the above dye ln fi video recording element ~ presented below:
Psepar~t~o~ 2: Preparat~on o~ 3~5-bls(4~diethylam~nobenzy-lidene)-l-met~yl-4~p~peritone ethyl~4-piperidvne (2 .25g) and 7 ~ lg o ~: : p~d~ethylamino-benzaldehyde were ~dded to a solut~on of 4g : pot~lum bydroxide in 50 ml methanol. The reaction ml~ture was heate~ at refllex 3 1/2 hours and ~llowed to st~nd ~ room emper~ture overnight. The product wa~ collected ~nd ~- recrystallized fr~m 700 ml ~cetoni~rile. The W ~pectr~ of the isolated product w~ confii~tent with the ~eructure of the titled compound.
~ ~ 5~ ~ 6 EXAMPLE
A video recording element W~lB prep~red as ln Example 1 with ~he dye o~ prep~r~t~on 2. the solvent was ~ mixture of 30g of chlorobenzene ~nd 30g of cyclohexanone, instead of 60g of cyclohex~none. At ~ recordlng l~ser power of between 18 to 20m W, the SNR was 55db.
: s-~
~'~
Claims (12)
1. A recording element comprising a support having coated thereon a layer of an amorphous composition comprising a binder and a dye, wherein:
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0-5 and each R is independentl7y selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0-5 and each R is independentl7y selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
2. The recording element according to Claim 1 wherein said support is reflecting.
3. The recording element according to Claim 1 wherein said binder is cellulose nitrate.
4. The recording element according to Claim 2 wherein said dye is selected from the group consisting of:
2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone and 1,3-bis(4-diethylaminobenzylidene)acetone.
2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone and 1,3-bis(4-diethylaminobenzylidene)acetone.
5. An information record comprising a support having coated thereon a layer comprising an amorphous compoeitlon comprising a binder and a dye, wherein:
said amorphous composition has an absorption factor of at leagt 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0-5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
said layer having formed therein a plurality of deformations having a size smaller than 1.5 microns, said deformations comprising a depression surrounded by a sharply defined ridge and are detectable using a beam of high-energy density radiation which is not absorbed by the amorphous composition.
said amorphous composition has an absorption factor of at leagt 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0-5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
said layer having formed therein a plurality of deformations having a size smaller than 1.5 microns, said deformations comprising a depression surrounded by a sharply defined ridge and are detectable using a beam of high-energy density radiation which is not absorbed by the amorphous composition.
6. The information record according to claim 5 wherein said support is reflecting.
7. The information record according to claim 5 wherein said binder is cellulose nitrate.
8. The information record according to Claim 7 wherein said dye is selected from the group consisting of:
2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylldene)cyclohexanone and 1,3-bis(4-diethylamlnobenzylidene)acetone.
2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylldene)cyclohexanone and 1,3-bis(4-diethylamlnobenzylidene)acetone.
9. A method of making a recording element com-prising the steps of coating a support with an amorphous composition comprising a binder and a dye and drying said composition wherein:
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0 to 5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein n is an integer from 0 to 5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms.
10. A method of providing a high absorption factor in a recording element, said method comprising the steps of forming a recording composition by combining a binder and a dye, wherein said dye conforms to the structure:
wherein n is an integer from 0-5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms; and coating said composition on support to form said recording element.
CLAIMS SUPPORTED BY SUPPLEMENTARY DISCLOSURE
wherein n is an integer from 0-5 and each R is independently selected from the group consisting of straight- and branched-chain alkyl groups of about 1-6 carbon atoms; and coating said composition on support to form said recording element.
CLAIMS SUPPORTED BY SUPPLEMENTARY DISCLOSURE
11. A recording element comprising a support having coated theroen a layer of an amouphous composition comprising a binder and a dye, wherein:
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein ;
n is and integer from 0-5 and each R is independently selected from the group consisting of straigt and branched-chain alkyl groups of about 1-6 carbon atoms.
said amorphous composition has an absorption factor of at least 20 at 488 nm and said dye conforms to the structure:
wherein ;
n is and integer from 0-5 and each R is independently selected from the group consisting of straigt and branched-chain alkyl groups of about 1-6 carbon atoms.
12. The recording element according to Claim 11 wherein said support is 3,5-bis(4-diethylaminobenzyli-dene)-1-methyl-4-piperidone.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12438280A | 1980-02-25 | 1980-02-25 | |
| US124,382 | 1980-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1154963A true CA1154963A (en) | 1983-10-11 |
Family
ID=22414531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000369312A Expired CA1154963A (en) | 1980-02-25 | 1981-01-26 | USE OF.alpha.,.alpha.'-BIS(DIALKYLAMINOBENZYLIDENE) KETONE DYES IN OPTICAL RECORDING ELEMENTS |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS56135557A (en) |
| BE (1) | BE887677A (en) |
| CA (1) | CA1154963A (en) |
| DE (1) | DE3106878A1 (en) |
| FR (1) | FR2476546A1 (en) |
| GB (1) | GB2070977B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57211145A (en) * | 1981-06-23 | 1982-12-24 | Japan Synthetic Rubber Co Ltd | Photoresist composition |
| JPS60500329A (en) * | 1982-12-31 | 1985-03-14 | ミネソタ マイニング アンド マニユフアクチユアリング コンパニ− | Recording medium for optical data storage |
| WO1984002795A1 (en) * | 1982-12-31 | 1984-07-19 | Minnesota Mining & Mfg | Recording medium for optical data storage |
| US4499165A (en) * | 1983-03-09 | 1985-02-12 | Eastman Kodak Company | Amorphous compositions of dyes and binder-mixtures in optical recording elements and information recorded elements |
| US8119041B2 (en) | 2001-09-05 | 2012-02-21 | Fujifilm Corporation | Non-resonant two-photon absorption induction method and process for emitting light thereby |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2133515B2 (en) * | 1970-07-09 | 1976-08-12 | E.I. du Pont de Nemours and Co., Wilmington, Del. (V.StA.) | LIGHT-SENSITIVE MIXTURE |
| WO1979000404A1 (en) * | 1977-12-19 | 1979-07-12 | Eastman Kodak Co | Medium for recording by thermal deformation |
-
1981
- 1981-01-26 CA CA000369312A patent/CA1154963A/en not_active Expired
- 1981-02-24 DE DE19813106878 patent/DE3106878A1/en active Granted
- 1981-02-24 GB GB8105725A patent/GB2070977B/en not_active Expired
- 1981-02-24 FR FR8103586A patent/FR2476546A1/en active Granted
- 1981-02-25 BE BE0/203921A patent/BE887677A/en not_active IP Right Cessation
- 1981-02-25 JP JP2669481A patent/JPS56135557A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BE887677A (en) | 1981-08-25 |
| DE3106878A1 (en) | 1982-01-07 |
| JPS56135557A (en) | 1981-10-23 |
| FR2476546B1 (en) | 1983-06-17 |
| GB2070977B (en) | 1983-09-21 |
| FR2476546A1 (en) | 1981-08-28 |
| GB2070977A (en) | 1981-09-16 |
| DE3106878C2 (en) | 1987-07-09 |
| JPH0155120B2 (en) | 1989-11-22 |
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