US3272635A - Compositions containing leuco xanthene dyes and suitable activators - Google Patents
Compositions containing leuco xanthene dyes and suitable activators Download PDFInfo
- Publication number
- US3272635A US3272635A US273569A US27356963A US3272635A US 3272635 A US3272635 A US 3272635A US 273569 A US273569 A US 273569A US 27356963 A US27356963 A US 27356963A US 3272635 A US3272635 A US 3272635A
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- leuco
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
- G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
- G03C1/732—Leuco dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S204/00—Chemistry: electrical and wave energy
- Y10S204/901—Effecting a color change by wave energy
Definitions
- This invention relates to non-silver photosensitive compositions which print-out an image directly upon exposure to a suitable dosage of visible light, and to the use to such compositions as thin films in photographic processes. More particularly this invention relates to photosensitive compositions comprising at least one colorless leuco compound which when intimately admixed with one or more colorless activator compounds, yields a mixture which when exposed to visible light prints out a visible image directly, at speeds which are of practical significance, and to the processing of such compositions to yield a permanent useful image.
- the leuco compounds which may be utilized in accordance with the present invention comprise two recognized classes of dye forming colorless compounds which are generally similar to the leuco triarylrnethane dyes except that they are characterized by the presence of one or more bridging hetero atoms and therefore are compounds which maybe represented by the general formulas wherein each R is selected from the group consisting of H, lower alkyl and aryl and may be the same or different and R is selected from the group consisting of H, alkyl and aryl, including particularly and and wherein Z represents a member selected from the group consisting of 0, 8, Se and NH.
- Carboxylic acids represented by the general formula wherein R is selected from the group consisting of H, alkyl, aralkyl, aryl, and
- R being selected from the group consisting of H, alkyl, aralkyl and aryl;
- Cyclic keto compounds represented by the general formula where Q represent-s the non-metallic atoms necessary to complete a tfiveor siX-rnembered heterocyclic ring and wherein the -ke-to oxygen is attached to a ring carbon in said ring.
- a mixture is prepared consisting of equal parts by volume of acetone and a 10% solution of polystyrene in benzene, 2 cc. of each being used in most instances. Then the indicated weights of the leuco compound and of the activator were dissolved in the mixture.
- the resulting composition formed from originally colorless materials had a cloudy or hazy appearance or a faint pinkish color in most instances.
- the composition was coated by means of a Bird applicator on SOOHD Mylar in a coating having an 0.0015 inch wet thickness and the coating was permitted to dry in air. Thereafter the composition was exposed either to a photoilood lamp through a step tablet or on an Eastman Kodak sensitometer with a suitable filter.
- the resulting image was fixed by a solvent wash or by exposure to heat. Thereafter the density of the image was read and the LES. was computed as described below.
- the polystyrene was omitted from the compositions and instead a mixture of benzene and acetone was used as the solvent for the indicated amounts of the leuco compound and the activator.
- the solution was poured onto filter paper and the photosensitive material was then exposed through an Eastman No. 2 Step Tablet to one General Electric Refiector Photoflood lamp for 30 seconds at a distance of 12 inches from the lamp to the sensitive material.
- the densities of the resulting step wedge were read on an Eastman No. 1 color densitometer through the green filter.
- L.E.S. (abbreviation for light exposure speed) refers to a speed rating system developed at the Wright Air Development Division of Air Research and Development Command (USAF), and is defined as the reciprocal of the exposure in meter candle seconds which is required to produce a double diffuse reflection density of 0.2 density units above base plus fog.
- USF Wright Air Development Division of Air Research and Development Command
- compositions consisting of the indicated weight of 3,6- bis-(dimethylamino) -9 (p-dimethylaminophenyl)xanthene (hereinafter identified as D-l79), and the indicated Weight of the specified activator dissolved in a mixture of acetone and 2 cc. of a 10% solution of polystyrene in benzene coated 0.0015-inch wet thickness on Mylar and air-dried were exposed using an Eastman No. 101 sensitometer for the indicated time with the light converted by the use of 8. 78AA Eastman filter to equal mean noonday light or to one General Electric No. 2 Reflector Photofiood lamp (RFL2), at a distance of 12 inches.
- RTL2 General Electric No. 2 Reflector Photofiood lamp
- Step Tablet was used to print a step tablet.
- the exposed material was stabilized by two or more successive rinses in a mixture of 1 part acetone and 4 parts petroleum ether, or by being maintained at 125 C. in a convectiontype oven for four (4) minutes.
- the stabilized material was reexposed for 5 minutes to the RFLZ with no darkening.
- the densities in the resulting step wedge were read with an Eastman No. 1 color densitometer using the green filter, the results for the photoflood exposures are reported in Table I and the densitometer exposures in Table II.
- the real active ingredient in the mixture is that very minute amount of an oxidized product which results when the leuco base is exposed to oxygen e.g. in the ordinary atmosphere.
- each of the activators listed above, or mixtures of the same bring about oxidation of the leuco compound upon exposure to a suitable dose of visible light and as a result form a direct visible print-out image in the light struck areas.
- the relative proportions of the leuco dye bases and the activators for the same may be varied considerably from the weight proportions given by way of illustration in the examples and are preferably within the range between 10 to 1 and l to 10 parts by weight.
- compositions of the present invention would be stored in cool dark relatively dry surroundings.
- composition which prints out a visible image directly as a result of exposure to visible light
- said composition comprising an initimate mixture consisting essentially of (1) at least one leuco compound selected from the group consisting of leuco compounds represented by one of the following general formulas wherein each R is selected from the group consisting of H, lower alkyl and aryl and not all of the Rs need be the same and wherein R is selected from the group consisting of H, lower alkyl and aryl and Z is selected from O, S, Se and -NH:
- R is selected from the group consisting of H, alkyl, aralkyl, aryl and II "C I Rb R being selected from the group consisting of H, alkyl, aralkyl and aryl; and A is selected from the group consisting of alkyl, alkaryl and aryl and (c) cyclic keto compounds represented by the general formula 1 wherein Q represents the non-metallic atoms necessary to complete a heter-ocyclic ring with at least 5 and not more than 6 atoms in the ring and wherein the keto oxygen is attached to a ring carbon atom is said ring;
- composition of claim 1 wherein the leuco compound is a xanthene.
- composition of claim 2 wherein the leuco compound is a 3,6 bis(dialkylamino) 9 (p dialkylaminophenyl)xant-hene.
- a dry film consisting of the composition of claim 1 dispersed in a thin layer on an inert support.
Description
United States Patent COMPOSITIONS CONTAINTNG LEUCO XAN- THENE DYES AND SUHTABLE ATHVATORS Robert H. Sprague, Chagrin Falls, John A. Stewart,
Parma, and James M. Lewis, Cleveland, Ohio, assignors to Horizons Incorporated, Cleveland, Ohio, a corporation of New Jersey No Drawing. Filed Apr. 17, 1963, Ser. No. 273,569
7 Claims. (Cl. 96-90) This invention relates to non-silver photosensitive compositions which print-out an image directly upon exposure to a suitable dosage of visible light, and to the use to such compositions as thin films in photographic processes. More particularly this invention relates to photosensitive compositions comprising at least one colorless leuco compound which when intimately admixed with one or more colorless activator compounds, yields a mixture which when exposed to visible light prints out a visible image directly, at speeds which are of practical significance, and to the processing of such compositions to yield a permanent useful image.
(1) THE LEUCO COMPOUNDS The leuco compounds which may be utilized in accordance with the present invention comprise two recognized classes of dye forming colorless compounds which are generally similar to the leuco triarylrnethane dyes except that they are characterized by the presence of one or more bridging hetero atoms and therefore are compounds which maybe represented by the general formulas wherein each R is selected from the group consisting of H, lower alkyl and aryl and may be the same or different and R is selected from the group consisting of H, alkyl and aryl, including particularly and and wherein Z represents a member selected from the group consisting of 0, 8, Se and NH.
As indicated, the preferred leuco compounds of this class are substituted in the 3,=6-positions and include 3,6 bis dimethylamino -9-(p-dirnethylaminophenyl xanthene 3,6-bis( diethylamino -9- (p-dimethylaminophenyl xanthene 3,272,635 Patented Sept. 13, 1966 3,6 bis (diethylamino -9-(p-diethylaminophenyl) xanthene 3, 6 bis dimethylamino) -9- (p-dimethylarninophenyl thioxanthene (2) THE ACTIVATORS A diverse group of colorless C:O containing organic compounds have been found to be useful in the present invention. These compounds may be grouped as follows:
1) Carboxylic acids represented by the general formula wherein R is selected from the group consisting of H, alkyl, aralkyl, aryl, and
R being selected from the group consisting of H, alkyl, aralkyl and aryl;
(3) Cyclic keto compounds represented by the general formula where Q represent-s the non-metallic atoms necessary to complete a tfiveor siX-rnembered heterocyclic ring and wherein the -ke-to oxygen is attached to a ring carbon in said ring.
(3) EVALUATION PROCEDURE The data reported in the tables which ifollow is the result of tests establishing the effect of visible light on mixtures of various activator compounds with the indicated leuco bases. In general one of three procedures was followed.
In the first two, a mixture is prepared consisting of equal parts by volume of acetone and a 10% solution of polystyrene in benzene, 2 cc. of each being used in most instances. Then the indicated weights of the leuco compound and of the activator were dissolved in the mixture. The resulting composition formed from originally colorless materials had a cloudy or hazy appearance or a faint pinkish color in most instances. The composition was coated by means of a Bird applicator on SOOHD Mylar in a coating having an 0.0015 inch wet thickness and the coating was permitted to dry in air. Thereafter the composition was exposed either to a photoilood lamp through a step tablet or on an Eastman Kodak sensitometer with a suitable filter.
the use of a 78AA filter, to equal mean noon-day light.
The resulting image was fixed by a solvent wash or by exposure to heat. Thereafter the density of the image was read and the LES. was computed as described below.
-In a third procedure, the polystyrene was omitted from the compositions and instead a mixture of benzene and acetone was used as the solvent for the indicated amounts of the leuco compound and the activator. The solution was poured onto filter paper and the photosensitive material was then exposed through an Eastman No. 2 Step Tablet to one General Electric Refiector Photoflood lamp for 30 seconds at a distance of 12 inches from the lamp to the sensitive material. The densities of the resulting step wedge were read on an Eastman No. 1 color densitometer through the green filter.
L.E.S. (abbreviation for light exposure speed) refers to a speed rating system developed at the Wright Air Development Division of Air Research and Development Command (USAF), and is defined as the reciprocal of the exposure in meter candle seconds which is required to produce a double diffuse reflection density of 0.2 density units above base plus fog. As in the more conventional ASA system used to rate silver halide films, the higher the LES number the faster the film is.
Compositions consisting of the indicated weight of 3,6- bis-(dimethylamino) -9 (p-dimethylaminophenyl)xanthene (hereinafter identified as D-l79), and the indicated Weight of the specified activator dissolved in a mixture of acetone and 2 cc. of a 10% solution of polystyrene in benzene coated 0.0015-inch wet thickness on Mylar and air-dried were exposed using an Eastman No. 101 sensitometer for the indicated time with the light converted by the use of 8. 78AA Eastman filter to equal mean noonday light or to one General Electric No. 2 Reflector Photofiood lamp (RFL2), at a distance of 12 inches. An Eastman Kodak No. 2 Step Tablet was used to print a step tablet. The exposed material was stabilized by two or more successive rinses in a mixture of 1 part acetone and 4 parts petroleum ether, or by being maintained at 125 C. in a convectiontype oven for four (4) minutes. The stabilized material was reexposed for 5 minutes to the RFLZ with no darkening. The densities in the resulting step wedge were read with an Eastman No. 1 color densitometer using the green filter, the results for the photoflood exposures are reported in Table I and the densitometer exposures in Table II.
Table I Densities, RFLZ Weight, Type 01 Exp. No. 01 No. Activators Used With D-179 mg. Fixing Min. Steps Gross Base Net Fog i ffffi jjr" 1111;311:1311: "i 5 19 Q36 2 .1 Ia-Naphthoie Aci 5 21 1.57 0.25 1.32 D-179 5 21 2. 57 0. as 2. 24 3 g Acld I 5 21 2.12 0. 25 1,37
5 21 2.02 0.23 1.79 5 18 1.85 0.34 1.51 -179 5 21 1. 45 0. 25 1, 20 7 lg f egl f f fff f 5 21 2. oo 0.15 1,85 8 2,4-Diehlorophenoxyaeetic Aeid, 5 21 2. 60 0. 29 2. 31 9 {is tt fffi'iit ffffith'itfiiit? 5 21 w w {g q q s 2 21 a. 00 0. 21 2, 79 11 igfi t ro e 5 8 0.48 0.23 0.20
D 1'%8fX f iT i?:::: 5 11 M4 13 {(113 ,$Tr1ehloroacetan1hde 5 11 L [L28 L02 14 l-Aeeto-Z-naphthol 5 21 1.77 0.78 0.99 15 lg-1Z9. t Ta 5 21 1.31 0. 30 1.01 gg e e 5 12 0.87 0.28 0,59 {152 i? 5 12 1,61 0. 20 1, 4 {g gtgg f- 5 10 1.19 0.32 .187 18 Acetoacet-2,5-dichlor0-N-benzoyla1ilide f"-1 5 6 0.77 0.48 0.29 19 1I 3c e1t7gaeet- 2,5-d1chloro-N-(m-nltro enz0y)an11de 5 9 0'60 016 0. 44 23223it???lfiii ffiifififtifl itz:: 5 18 0.18 2.18 21 {hjioii ltg-Benzoyl Aeeto-4,3,3-dichl0robenzidide- 5 12 L16 0' 44 0' 72 D 1 5 17 1. 77 0.24 1. 53 t i liz g t y t t i g 2g 0. 35 90 25. rhenifiimimw 0.13 1. as 9 5 11 2.20 0.17 2. 03 26.-. 3-M Ll l-ll ll 11-57911Rfiiiffffifi? 5 14 27 1,3-Diphenyl-5-pyrazolone. 5 1 r 28 Benzothiazolone 1 0 50 D 17g 5 12 2. 32 0. 1. 87
FIXING Two distinct methods of fixing or stabilizing the colored image produced have been described. In the one the exposed material is subjected to two or more second rinses with a suitable solvent and in the other the exposed material is subjected to mild heat (125) for about 4 minutes. The method of stabilization selected in any specific instance will depend to some extent upon the materials being used and it is to be noted that many of the slower compositions may be preferable to some of the faster compositions because some of the latter are less susceptible to heat or dry fixing than some of the former.
While not wishing to be bound by any specific theory as to the manner in which the exposure to visible light to an initimate mixture comprising two or more originally colorless compounds produced a colored image, it is believed that the final colored image which forms in the light struck areas is always the dye which forms as a result of oxidation of the leuco base. Furthermore it appears that when the photosensitive mixture is prepared, on
mixing the compounds which are colorless, a weakly tinted mixture is formed.
It is also considered possible that the real active ingredient in the mixture is that very minute amount of an oxidized product which results when the leuco base is exposed to oxygen e.g. in the ordinary atmosphere.
Whatever the true mechanism each of the activators listed above, or mixtures of the same, bring about oxidation of the leuco compound upon exposure to a suitable dose of visible light and as a result form a direct visible print-out image in the light struck areas.
PROPORTIONS The relative proportions of the leuco dye bases and the activators for the same may be varied considerably from the weight proportions given by way of illustration in the examples and are preferably within the range between 10 to 1 and l to 10 parts by weight.
As with other photosensitive compositions if not used at the time they are prepared the compositions of the present invention would be stored in cool dark relatively dry surroundings.
Having now described the invention in accordance with the patent statutes it is not intended that it be limited except as may be required by the appended claims.
We claim:
1. A composition which prints out a visible image directly as a result of exposure to visible light said composition comprising an initimate mixture consisting essentially of (1) at least one leuco compound selected from the group consisting of leuco compounds represented by one of the following general formulas wherein each R is selected from the group consisting of H, lower alkyl and aryl and not all of the Rs need be the same and wherein R is selected from the group consisting of H, lower alkyl and aryl and Z is selected from O, S, Se and -NH:
R\ Z /R R R 1';
and wherein each R has the same meaning as indicated above and Z represents a member selected from the .group consisting of O, S, Se and -NH', and (2) at least one colorless non-toxic C=O containing organic compound selected from the group consisting of (a) carboxylic acids represented by the general formula RCOOH wherein R is selected from the group consisting of aryl and alkaryl (b) acyclic keto compounds represented by the general formula wherein R" is selected from the group consisting of aryl,
I NH-aryl and i i" C H:C Nary1 wherein R is selected from the group consisting of H, alkyl, aralkyl, aryl and II "C I Rb R being selected from the group consisting of H, alkyl, aralkyl and aryl; and A is selected from the group consisting of alkyl, alkaryl and aryl and (c) cyclic keto compounds represented by the general formula 1 wherein Q represents the non-metallic atoms necessary to complete a heter-ocyclic ring with at least 5 and not more than 6 atoms in the ring and wherein the keto oxygen is attached to a ring carbon atom is said ring;
said compounds being present in the mixture in proportions ranging between 1:10 and 10:1 relative to each other,
by weight.
2. The composition of claim 1 wherein the leuco compound is a xanthene.
3. The composition of claim 2 wherein the leuco compound is a 3,6 bis(dialkylamino) 9 (p dialkylaminophenyl)xant-hene.
4. A dry film consisting of the composition of claim 1 dispersed in a thin layer on an inert support.
5. The film of claim 4 wherein the support is a film forming plastic.
6. The film of claim 4 wherein the mixture is supported by a cellulose compound selected from the group consisting of cellulose and film forming cellulose derivatives.
7. The film of claim 4 wherein the support is transparent.
References Cited by the Examiner UNITED STATES PATENTS NORMAN G. TORCHIN, Primary Examiner.
10 D. D. PRICE, Assistant Examiner.
Claims (1)
1. A COMPOSITION WHICH PRINTS OUT A VISIBLE IMAGE DIRECTLY AS A RESULT OF EXPOSURE TO VISIBLE LIGHT SAID COMPOSITION COMPRISING AN INTIMATE MIXTURE CONSISTING ESSENTIALLY OF (1) AT LEAST ONE LEUCO COMPOUND SELECTED FROM THE GROUP CONSISTING OF LEUCO COMPOUNDS REPRESENTED BY ONE OF THE FOLLOWING GENERAL FORMULAS
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US273569A US3272635A (en) | 1963-04-17 | 1963-04-17 | Compositions containing leuco xanthene dyes and suitable activators |
| GB11956/64A GB1058316A (en) | 1963-04-17 | 1964-03-20 | Print out compositions |
| NL6403246A NL6403246A (en) | 1963-04-17 | 1964-03-26 | |
| FR970762A FR1395130A (en) | 1963-04-17 | 1964-04-13 | Activated photographic compositions |
| DEH52379A DE1283091B (en) | 1963-04-17 | 1964-04-16 | Photosensitive layer |
| BE646720D BE646720A (en) | 1963-04-17 | 1964-04-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US273569A US3272635A (en) | 1963-04-17 | 1963-04-17 | Compositions containing leuco xanthene dyes and suitable activators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3272635A true US3272635A (en) | 1966-09-13 |
Family
ID=23044485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US273569A Expired - Lifetime US3272635A (en) | 1963-04-17 | 1963-04-17 | Compositions containing leuco xanthene dyes and suitable activators |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3272635A (en) |
| BE (1) | BE646720A (en) |
| DE (1) | DE1283091B (en) |
| GB (1) | GB1058316A (en) |
| NL (1) | NL6403246A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445232A (en) * | 1965-10-21 | 1969-05-20 | Horizons Research Inc | Photography |
| US3769023A (en) * | 1971-05-07 | 1973-10-30 | Horizons Inc | Light sensitive reproduction and electron beam sensitive material |
| US4049457A (en) * | 1975-03-20 | 1977-09-20 | Bard Laboratories, Inc. | Photosensitive composition of polynitrate ester, aromatic amines and organic esters |
| US5834157A (en) * | 1995-12-23 | 1998-11-10 | Agfa-Gevaert Ag | 2-acylamino-9-arylacridines, process for their preparation and photosensitive mixtures containing them |
| JP2007522245A (en) * | 2004-02-12 | 2007-08-09 | ザ リサーチ ファウンデーション オブ ステイト ユニヴァーシティ オブ ニューヨーク | Pharmaceutical complex |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441561A (en) * | 1943-07-23 | 1948-05-18 | Chalkley Lyman | Photochemical preparation of stable dyes |
| US2895892A (en) * | 1954-08-10 | 1959-07-21 | Chalkley Lyman | Photochemical process |
| US2981622A (en) * | 1959-07-13 | 1961-04-25 | Chalkley Lyman | Photographic process |
| US3121632A (en) * | 1961-08-30 | 1964-02-18 | Horizons Inc | Photographic process and composition including leuco triphenylmethane dyes |
-
1963
- 1963-04-17 US US273569A patent/US3272635A/en not_active Expired - Lifetime
-
1964
- 1964-03-20 GB GB11956/64A patent/GB1058316A/en not_active Expired
- 1964-03-26 NL NL6403246A patent/NL6403246A/xx unknown
- 1964-04-16 DE DEH52379A patent/DE1283091B/en active Pending
- 1964-04-17 BE BE646720D patent/BE646720A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441561A (en) * | 1943-07-23 | 1948-05-18 | Chalkley Lyman | Photochemical preparation of stable dyes |
| US2895892A (en) * | 1954-08-10 | 1959-07-21 | Chalkley Lyman | Photochemical process |
| US2981622A (en) * | 1959-07-13 | 1961-04-25 | Chalkley Lyman | Photographic process |
| US3121632A (en) * | 1961-08-30 | 1964-02-18 | Horizons Inc | Photographic process and composition including leuco triphenylmethane dyes |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445232A (en) * | 1965-10-21 | 1969-05-20 | Horizons Research Inc | Photography |
| US3769023A (en) * | 1971-05-07 | 1973-10-30 | Horizons Inc | Light sensitive reproduction and electron beam sensitive material |
| US4049457A (en) * | 1975-03-20 | 1977-09-20 | Bard Laboratories, Inc. | Photosensitive composition of polynitrate ester, aromatic amines and organic esters |
| US5834157A (en) * | 1995-12-23 | 1998-11-10 | Agfa-Gevaert Ag | 2-acylamino-9-arylacridines, process for their preparation and photosensitive mixtures containing them |
| JP2007522245A (en) * | 2004-02-12 | 2007-08-09 | ザ リサーチ ファウンデーション オブ ステイト ユニヴァーシティ オブ ニューヨーク | Pharmaceutical complex |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1283091B (en) | 1968-11-14 |
| BE646720A (en) | 1964-08-17 |
| GB1058316A (en) | 1967-02-08 |
| NL6403246A (en) | 1964-10-19 |
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