CN1017842B - Optical rcording medium nd optical recording method - Google Patents
Optical rcording medium nd optical recording methodInfo
- Publication number
- CN1017842B CN1017842B CN89101902A CN89101902A CN1017842B CN 1017842 B CN1017842 B CN 1017842B CN 89101902 A CN89101902 A CN 89101902A CN 89101902 A CN89101902 A CN 89101902A CN 1017842 B CN1017842 B CN 1017842B
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- photochromic compound
- optical recording
- light
- recording media
- stretched film
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Abstract
In accordance with the present invention, there are provided photo-recording media comprising photochromic compounds having been dispersed or dissolved in stretched films or nematic liquid crystals, the transition moment of light absorption of said photochromic compounds being orientated in a definite direction. In the photo-recording media as provided, an information recorded in the photochromic compounds can be read out without destroying the same.
Description
The present invention relates to the method for a kind of optical recording media and optical recording, more particularly, relate to a kind of stable and super-sensitive optical recording media that contains photochromic compound (hereinafter to be referred as photochromic compound), and the optical record method that uses said optical recording media.
Someone proposes a kind of optical recording media of photochromic compound variation of absorption spectra before and after light reaction that utilizes and is used as rewritable optical recording media.Yet, in the optical recording media of above-mentioned recommendation, in the time of reading the information that is write down as if need, just can carry out in the time of must making light drop in light absorbing this wavelength coverage of this photochromic compound energy.Therefore, the light that is used to read this record both had been used to read the information that is write down, and also was used to erase simultaneously the said information that is recorded.For this reason, so serious practical problems occurred, that is the reproduction of this information is actually the said information of having eliminated.Thereby during the information that is write down in reading photochromic compound, this information promptly has been eliminated, also sense information more just.
In this connection, Jap.P. L-O-P publication number 209186/1987 has disclosed a kind of optical memory material, it is said that the memory that this kind material can prevent to be recorded in the photochromic compound disappears.Said optical memory material is by the photochromic compound dissolving that a class can be changed its molecular structure after the rayed of different wave length or is dispersed in the solid matter of (Cholesteric) liquid crystal phase that has cholesterol and makes.Yet, this method relates to such problem, be that cholesteryl liquid crystal is a kind of medium that has dissolving or dispersed dyestuff within it, and the method for synthetic this kind material is very complicated, its reason is must have asymmetric carbon atoms in the molecule of said cholesteryl liquid crystal, and must can be by the optically-active disassemble.
The present invention is intended to solve above-mentioned this class problem, the object of the present invention is to provide a kind of not only stable but also super-sensitive optical recording media that contains photochromic compound, and this medium can write down, reads and rewrite required information easily and stably.Another purpose of the present invention provides a kind of optic recording method that utilizes this kind optical recording media.
Comprise a kind of photochromic compound based on optical recording media of the present invention, the latter is dispersed or dissolved in stretched film, nematic crystal or the smectic shape liquid crystal, and the transition of the light absorption of said photochromic compound is apart from (transition moment) the direction orientation to fix.
In this optical recording media, irradiation along with light, the structure of photochromic compound changes, information is credited in this compound thus, by not detecting the poor of the apparent rotation angle in irradiate light front and back by light absorbing light at said photochromic compound, can read the information that is write down again with wavelength coverage.
Brief Description Of Drawings
Fig. 1 is expression with ultraviolet light and visible light alternately during the irradiates light recording medium, and the curve map that rotation angle changes on plane of polarization, wherein said optical recording media comprise the stretched film that the photochromic compound of dispersed or dissolving is arranged in a kind of.
Fig. 2 is illustrated in ultraviolet light irradiation down, when the information in the optical recording media of being recorded in is read with visible light, and the curve map that rotation angle changes, wherein said optical recording media comprises a kind of nematic crystal, and dissolving or dispergated photochromic compound are arranged in it.
Fig. 3 is expression with ultraviolet light and visible light alternately during the irradiates light recording medium, the curve map that rotation angle changes, and wherein said optical recording media comprises a kind of nematic crystal, the photochromic compound that dissolving is arranged in it or disperse.
Below will and use optical recording media involved in the present invention and be somebody's turn to do The optic recording method of medium is elaborated.
According to the present invention, photochromic compound is used as optical recording media, and said photochromic compound is dispersed in the stretched film, or is dispersed in nematic crystal or the smectic shape liquid crystal, and the transistion moment of its light absorption is with fixing direction orientation. Usually, the transistion moment of all light absorption obviously can show optical activity near absorbing wavelength district and its with the compound of fixed-direction orientation. Therefore, when the transistion moment of using a kind of light absorption has been pressed the photochromic compound of fixed-direction orientation, then information can be credited in this compound, and the information that records can be changed, meanwhile, by shining compound with the light of absorbing wavelength in the light absorbing scope of compound energy, then can change its apparent anglec of rotation. And in this case, owing to can observe the apparent anglec of rotation according to the mode identical with the situation of the common anglec of rotation, even can not also be like this in the light absorbing wave-length coverage at photochromic compound, thereby the light in the photochromic compound of charging to information can not light absorbing this wave-length coverage with this compound (being used for reading) shines, and when detecting the variation of the anglec of rotation, can read the information that is recorded in this photochromic compound. If adopt above-mentioned this method, then can under the condition of not eliminating the information that records in the photochromic compound, read the information of charging in it.
As previously mentioned, be used for photochromic compound of the present invention, its molecule needn't all need have optical activity. Therefore, various photochromic compounds all can be used for the present invention, comprise spiro-pyrans (spiropyran), fulgide, thioindigo, azobenzene and their derivative etc.
The object lesson that can be used for this class photochromic compound of the present invention comprises following these listed compounds:
(1) 1,3,3-trimethyl indoline also (indolino)-6 '-nitro benzo spiro-pyrans;
(2) 1,3,3-trimethyl indoline also-6 '-nitro-8 '-methoxyl benzo spiro-pyrans;
(3) 1,3,3-trimethyl indoline also-6,8 '-dibromo benzo spiro-pyrans;
(4) 1,3,3-trimethyl indoline also-5 '-nitro-8 '-methoxyl benzo spiro-pyrans;
(5) benzothiazole quinoline and spiro-pyrans (benzothiazolino-spiropyran);
(6) 1,3,3-trimethyl spiral shell [indoline also-2, the 3-naphtho-(2,1-b), (1,4) oxazine];
(7) 1,3,3-trimethyl-5-chlorine spiral shell [indoline also-2, the 3-naphtho-) (2,1-b) (1,4) oxazine];
(8) 1-(octyl group)-3,3-dimethyl spiral shell [indoline also-2, the 3-naphtho-(2,1-b) (1,4) oxazine];
(9) 1-(myristyl) 3,3-dimethyl spiral shell [indoline also-2, the 3-naphtho-(2,1-b) (1,4) oxazine];
(10) 1,3,3-trimethyl spiral shell [indoline also-2,3-phenanthro--(9,10) (1,4) oxazine];
(11) 1,3,3-trimethyl-5-chlorine spiral shell [dichloro-indole also-2,3-phenanthro-(9,10) (1,4) oxazine];
(12) 1,3,3-trimethyl spiral shell [dichloro-indole also-2,3-(3,6) the disulfo naphtho-(2, and 1-b) (1,4) oxazine] disodium;
(13) 2-butylidene (diphenyl methylene) succinic anhydride;
(14) diphenyl methylene (isopropylidene) succinic anhydride;
(15) 2,5-dimethyl-3-furyl ethylidene (isopropylidene) succinic anhydride;
(16) 2,5-dimethyl-3-thiophenyl ethylidene (isopropylidene) succinic anhydride;
(17) thioindigo;
(18) all naphtho-thioindigos;
(19) azobenzene;
(20) 4-methoxyl azobenzene;
(21) 2-(2,4-dinitro benzyl) pyridine; With
(22) 4,4 ', 4 " three (N, N-dimethylaminophenyl) methyl chlorides.
In the present invention, more than cited photochromic compound be dispersed in stretched film, perhaps in nematic crystal or the smectic shape liquid crystal, thus, the transistion moment of the light absorption of said compound is carried out orientation with fixing direction.
The optical recording media that at first description is comprised stretched film contains dispergated photochromic compound in this stretched film.Be used for stretched film of the present invention because of its birefringence, this film itself has an apparent rotation angle, and the apparent rotation angle that absorption produced of photochromic compound can apparent rotation angle form be observed, this angle is added in the apparent rotation angle of stretched film self.
The polymkeric substance that is used for above-mentioned this class stretched film of the present invention's formation comprises amorphous polyolefin resin, polymethacrylate resin (as polymethylmethacrylate), polyacrylate resin (as polymethyl acrylate), polycarbonate resin, diallyl phthalate resin, vibrin, polyethersulfone, poly-ethyl ketone, methylpentene polymer, poly-aryl ester resin, (polyarylate resins), tygon, polyolefin (as polypropylene and polybutylene), polyphenylene sulphur, nylon, fluorine resin, Polyvinylchloride, polystyrene, polyacrylonitrile, Pioloform, polyvinyl acetal, polyurethane, polyethers, polyvinyl alcohol (PVA), polyvinyl acetate, polyvinylether, and cellulose derivative.
In above-mentioned these polymkeric substance, use following material comparatively suitable: i.e. polyolefin (as tygon and polypropylene), polyvinyl alcohol (PVA), polymethacrylate resin (as polymethylmethacrylate), vibrin, and amorphous polyolefin resin.
For above-mentioned photochromic compound is dispersed in the stretched film, and the transistion moment of light absorption that makes said photochromic compound thus specifically, can adopt following any method with fixing direction orientation:
(1) polymkeric substance and the photochromic compound that will constitute stretched film is dissolved in a certain solvent, with casting the solution casting that is produced become membranaceous, then the film that is generated stretched.
(2) prepare stretched film earlier, with the solution impregnation of prepared film, carry out drying then then with photochromic compound.
(3) will constitute the polymkeric substance of stretched film and photochromic compound and put together and knead, and resulting pug mill will be molded as membranaceous product, and then stretch.
Being used for stretched film of the present invention should be with single shaft to stretching, and the draw ratio of film (drawin ratio) can change along with the kind of film, but generally is preferably 1.2-10000 doubly, doubly is good with 1.2-100 wherein, especially with 2-50 doubly for better.
Below will be to containing nematic crystal or smectic optical recording media is done a description, and said liquid crystal contains dissolving or dispergated photochromic compound.The liquid crystal that is used for nematic of the present invention or smectic shape comprises following material: promptly p-alkyl-p '-alkoxy azoxybenzene, p-alkoxy benzal-p '-alkyl benzene amine, p-alkyl benzal-p '-cyanoaniline, p-alkoxy benzal-p '-cyanoaniline, phenol benzoate, p-alkyl-p '-cyanobiphenyl, to cyano group-cyclohexylbenzene, cyclohexyl-cyclohexane, to the cyano-phenyl pyrimidine, and-4 '-alkyl biphenyl yl carboxylic acid [4-(4-alkyl-cyclohexyl) benzene] ester:
4-alkylbenzoic acid [4-cyano group benzene] ester:
4-alkyl-4 '-alkoxy methyl biphenyl:
The 4-(4-alkyl-cyclohexyl)-1-cyclohexene nitrile:
4-alkyl-cyclohexyl-1-carboxylic acid [4-alkoxy methyl benzene] ester:
4-alkyl-cyclohexyl-1-carboxylic acid [4-(5-alkoxy amyl group) benzene] ester:
The 4-(4-alkyl-cyclohexyl)-4 '-alkoxy methyl biphenyl:
4-(4-alkoxy methyl phenyl) cyclohexyl-1-carboxylic acid [4-cyano group benzene] ester:
And 4-(4-alkoxy methyl cyclohexyl)-4 '-(4-alkoxy methyl-cyclohexyl) biphenyl:
More than the carbon atom of cited alkyl (representing) or alkoxy (representing) with R ' with R for number is preferably 1-15, be good with 3-9 carbon atom especially wherein.
For photochromic compound is dissolved in the liquid crystal of nematic or smectic shape, make the transistion moment orientation of the light absorption of said photochromic compound whereby, need photochromic compound to be dissolved or be dispersed in the nematic crystal, then the nematic crystal that contains dissolving or dispersed photochromic compound that is produced is injected liquid crystal groove (cell).
The above-mentioned amount that is dispersed or dissolved in the photochromic compound in the stretched film is preferably 1 * 10
-4-100 parts (weight in the stretching, extension film is benchmark for 100 parts, down together) is wherein especially with 1 * 10
-3-50 parts is good; And dissolving or the photochromic compound that is dispersed in nematic crystal or the smectic shape liquid crystal are preferably 1 * 10
-4-100 parts (with nematic crystal or smectic weight is benchmark for 100 parts, down together) is wherein especially with 1 * 10
-3-50 parts is good.
Yet, in the present invention, also the lattice-site (sits) that can impel the photochromic compound molecular orientation can be introduced in the above-mentioned photochromic compound, if the molecule of this photochromic compound constitutes with this molecule, then can make the transistion moment of the light absorption of the photochromic compound after introducing thus reach orientation highly.
In the present invention, information is charged to or re-writed in the above-mentioned optical recording media and can be undertaken by following mode.That is with required position in the irradiate light optical recording media in the absorbing wavelength scope of photochromic compound (A).By above-mentioned irradiation, in the position of irradiate light, photochromic reactions has taken place, and photochromic compound (A) reversibly is transformed into (B) states different on the structure.In contrast be above-mentioned variation then not to take place without the position of said irradiate light.Like this, (A) and (B) two states can be charged to information in the said medium thus by arranging corresponding to the information in the optical recording media.If desire rewrites the information that once was credited in the optical recording media, the Zone Full that irradiate light in the absorbing wavelength scope of then available (B) is desired to be rewritten, existing all photochromic compounds in should the zone can be transformed into (A) state thus, and erase the information of record for the first time, after this new information can be credited to said zone.
In the present invention, reading of the information that is recorded can be undertaken by following mode, even the information of also charging in the above described manner or re-writing is arranged by (A) and order (B).Owing to (A) each have its different mutually respective absorption spectrum, and their apparent rotation angle is also inequality, thereby the variation of rotation angle can be used as readout mode (readont mode) with (B).In addition, because apparent rotation angle also can be observed by the same manner of common rotation angle, even in the not light absorbing wavelength coverage of photochromic compound also is like this, thereby according to the present invention, at (A) and (B) reading in the neither light absorbing wavelength coverage becomes possibility, and the difference under the situation about changing with absorptivity then is used as sense code.If reading at (A) or (B) of information record carried out in any absorbing wavelength scope, the irradiation of the light that then said record will be used to read and eliminating.Yet in invention, because the variation of rotation angle is used as sense code, thereby the information of charging in the photochromic compound can be read under situation about will not eliminate.
The present invention is described in further detail hereinafter with reference to embodiment, but the present invention is limited to these examples absolutely not.
Example 1
2.5 gram polyvinyl alcohol (PVA) (a kind of product that is used for spectrophotometry, Wako Junyaku K.K. produce) are added in 27.5 milliliters the distilled water, and this potpourri is stirred several hrs down at 60 ℃.Adding 10 ml concns in the polyvinyl alcohol (PVA) pasty liquid that is produced is 10
-41,3 of M, 3-trimethyl indoline also-6 '-nitro benzo spiro-pyrans (hereinafter to be referred as spiro-pyrans), and this mixed liquor is stirred to evenly.After stirring end,, till the bubble collapse that produces because of stirring, then it is poured in the porcelain dish this solution left standstill.The porcelain dish of waiting therefrom takes out film after at room temperature placing about 1 week, is cut to suitable size, then under heating film is stretched to 1.4 times.
By alternately above-mentioned film (thickness of film is 500 microns) being shone with ultraviolet ray (300-400 millimicron) and visible light (400 millimicrons to long wave), make it to carry out photochromic reactions, this reversible variation shown in Figure 1 has taken place in rotation angle with on the plane of polarization before and after polarimeter (plarimeter) assaying reaction thus.Said determination is to carry out in 589.3 millimicrons wavelength coverage, does not in fact observe the absorption of spiro-pyrans under this wavelength.The above results shows that in optical recording media, the information that is credited to can be rewritten, and the information of charging to or rewriteeing can be read under situation about not eliminating.
Example 2
Repeat the test of example 1, at room temperature be immersed in the structural formula I but will add the polyvinyl alcohol film (thickness of film is 300 microns) that makes behind 10 milliliters of ethanol
In the ethanolic solution of shown furyl fulgide, soak 20 minutes approximately after, its taking-up is dry in the air at air and its in succession, under heating, be stretched to 2.4 times then.After this by the same quadrat method described in the example 1, with ultraviolet ray and radiation of visible light, and mensuration furyl fulgide reacts the rotation angle on the plane of polarization of front and back.The result shows that when the shadow of fulgide was transformed into its chromoplast, rotation angle changed+0.5 ° in the time of 650 millimicrons, even also changes 0.05 ° in the time of 700 millimicrons.The absorption edge of fulgide chromoplast shows thus along near 600 millimicrons, reads even also can carry out non-destructive in this photochromic compound system.
Example 3
Under agitation, be 10 with 10 ml concns
-4The acetone soln of the furyl fulgide of M is added in the solution of being made up of 5.5 gram polymethylmethacrylates and 30 milliliters of acetone, and it is left standstill, and till the bubble collapse that is produced by stirring, then it is poured in the porcelain dish.At room temperature, porcelain dish was placed for 1 week in the darkroom.Therefrom take out formed film then, be cut to suitable size after, be stretched to 16 times (thickness is 100 microns).By the same quadrat method described in example 1 and the example 2, with ultraviolet ray and radiation of visible light, and the rotation angle on the plane of polarization before and after the reaction of mensuration furyl fulgide.The result shows, the ring closure of furyl fulgide during along with usefulness ultraviolet ray irradiation, rotation angle on the plane of polarization reduces 0.06 °, and when opening with the ring of furyl fulgide under the radiation of visible light, the rotation angle that reduces on the plane of polarization is returned to original size again.
Example 4
Polyethylene film (thickness is 100 microns) after stretching had an appointment to soak in 80 ℃ the toluene solution of furyl fulgide (seeing the structural formula I) take out after 2 hours, at air drying.By example 1 described same quadrat method, with ultraviolet light and radiation of visible light, and mensuration furyl fulgide reacts the rotation angle on the plane of polarization of front and back then.The result shows, is transformed into the structural change of chromoplast along with the ultraviolet ray irradiation time from shadow, and the rotation angle on the plane of polarization increases 0.02 °, and when using radiation of visible light, the rotation angle of increase is returned to original size again.This variation detects more than 10 times by the repetition aforesaid operations and confirms.
Example 5
At room temperature, with the structural formula I
6 milligrams of shown furyl fulgide are dissolved in 0.3 milliliter the nematic crystal (ZLI1132, Merck company produce), then solution are injected a parallel alignment-type liquid crystal groove, form optical recording media.This optical recording media is remained on 35 ℃, and with the rayed of furyl fulgide absorbing wavelength, to measure the variation of rotation angle opening width (dispersion).Gained the results are shown in Fig. 2.
When the used by optical recording medium ultraviolet ray (300-400 millimicron) of present embodiment was shone, the furyl fulgide was transformed into the ring closo from the ring open type, and photochromic reactions has taken place thus, and the opening width of rotation angle changes simultaneously.
Opening in a wide wavelength coverage of rotation angle takes place, even wavelength available is read greater than 600 millimicrons light (under the rayed of this wavelength, not observing the absorption of furyl fulgide).
Then with visible light (400 millimicrons to long wave) irradiation furyl fulgide, so the opening width of rotation angle is returned to original state.And on the one hand with 600 millimicrons light (under this wavelength, in fact do not observe the absorption of the ring open type and the ring closo of furyl fulgide) the irradiates light recording medium observes the variation of rotation angle, said on the other hand used by optical recording medium ultraviolet ray and visible light (400 millimeters to long wave) alternately shine, and observe the reversible variation of this rotation angle shown in Figure 3 thus.The above shows that according to optical record method of the present invention, information can be rewritten, and can carry out nondestructive reading.In addition, by heating up, liquid crystal is converted to isotropic phase, so the optical activity of liquid crystal loses.This shows that in optical recording media the orientation of photochromic compound is the key factor that manifests optical activity.
Example 6
Photochromic compound used in the example 5 is dissolved in the following structural formula II
In the shown ferroelectric liquid crystals, making it concentration is 0.01 mole (concentration in above-mentioned liquid crystal is 1 mole), then formed solution is injected the parallel alignment type liquid crystal groove, to form optical recording media.
Carry out rayed by method same in the example 5, the result shows, during with the ultraviolet ray irradiation, the rotation angle at 600 millimicrons of places changes+0.2 °, and when use radiation of visible light, and rotation angle returns back to that it was big or small originally.In addition, under heating up, liquid crystal is converted to the isotropy type, loses optical activity thereupon.
Claims (6)
1, a kind of optical recording media, it contains a kind of stretched film that is dispersed or dissolved in, and perhaps the transistion moment (transition moment) of the light absorption of the said photochromic compound of photochromic compound (hereinafter to be referred as photochromic compound) in nematic crystal or the smectic shape liquid crystal is carried out orientation with fixing direction.
2, optical recording media according to claim 1 is characterized in that said stretched film is a kind of film of uniaxial tension.
3, optical recording media according to claim 1 is characterized in that said stretched film is made of polyolefin, polyvinyl alcohol (PVA), polymethacrylate, polyester or amorphous polyolefin resin.
4, a kind of optical record method, it comprises
(1) use the interior irradiate light of this absorbing wavelength scope that can make photochromic compound change its structure to contain the optical recording media of photochromic compound, write down thus or rewrite information, wherein said photochromic compound is dispersed or dissolved in stretched film or nematic crystal or the smectic shape liquid crystal, and the transistion moment of the light absorption of this photochromic compound is with the fixed-direction orientation;
(2) light is read in the interior light conduct of this wavelength coverage that does not absorb with described photochromic compound, comes the irradiates light recording medium, detects the variation of the apparent rotation angle of rayed front and back thus, and with nondestructive mode sense information.
5, optical record method according to claim 4 is characterized in that said stretched film is the film after the uniaxial tension.
6, optical record method according to claim 4 is characterized in that said stretched film is to be made of polyolefin, polyvinyl alcohol (PVA), polymethylmethacrylate, polyester or amorphous polyolefin resin.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP994/1989 | 1988-01-06 | ||
| JP75366/1988 | 1988-03-28 | ||
| JP75366/88 | 1988-03-28 | ||
| JP75367/1988 | 1988-03-28 | ||
| JP63075366A JP2772345B2 (en) | 1988-03-28 | 1988-03-28 | Optical recording method |
| JP75367/88 | 1988-03-28 | ||
| JP64000994A JPH02181746A (en) | 1989-01-06 | 1989-01-06 | Optical recording medium |
| JP994/89 | 1989-01-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1038895A CN1038895A (en) | 1990-01-17 |
| CN1017842B true CN1017842B (en) | 1992-08-12 |
Family
ID=26334138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89101902A Expired CN1017842B (en) | 1988-03-28 | 1989-03-28 | Optical rcording medium nd optical recording method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1017842B (en) |
-
1989
- 1989-03-28 CN CN89101902A patent/CN1017842B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CN1038895A (en) | 1990-01-17 |
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