WO1991014205A1 - Silver removal from photographic products - Google Patents
Silver removal from photographic products Download PDFInfo
- Publication number
- WO1991014205A1 WO1991014205A1 PCT/EP1991/000406 EP9100406W WO9114205A1 WO 1991014205 A1 WO1991014205 A1 WO 1991014205A1 EP 9100406 W EP9100406 W EP 9100406W WO 9114205 A1 WO9114205 A1 WO 9114205A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silver
- accelerator
- bleach
- fixing agent
- fix
- Prior art date
Links
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 37
- 239000004332 silver Substances 0.000 title claims abstract description 37
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000007844 bleaching agent Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 34
- 238000011084 recovery Methods 0.000 claims description 11
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 7
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 7
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 7
- 235000018417 cysteine Nutrition 0.000 claims description 7
- 229960003067 cystine Drugs 0.000 claims description 7
- 150000003573 thiols Chemical class 0.000 claims description 6
- 229960002433 cysteine Drugs 0.000 claims description 5
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 5
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 5
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 4
- 229940099500 cystamine Drugs 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229940035024 thioglycerol Drugs 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- -1 aliphatic thiol Chemical class 0.000 abstract description 3
- 238000010186 staining Methods 0.000 abstract description 3
- 230000007850 degeneration Effects 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 239000000463 material Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PURYCGFBBYVQEQ-UHFFFAOYSA-N 1-(dimethylamino)ethanethiol Chemical compound CC(S)N(C)C PURYCGFBBYVQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- KZTASAUPEDXWMQ-UHFFFAOYSA-N azane;iron(3+) Chemical compound N.[Fe+3] KZTASAUPEDXWMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001739 density measurement Methods 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- PGWMQVQLSMAHHO-UHFFFAOYSA-N sulfanylidenesilver Chemical compound [Ag]=S PGWMQVQLSMAHHO-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004846 x-ray emission Methods 0.000 description 1
Classifications
-
- 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/44—Regeneration; Replenishers
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/395—Regeneration of photographic processing agents other than developers; Replenishers therefor
- G03C5/3952—Chemical, mechanical or thermal methods, e.g. oxidation, precipitation, centrifugation
-
- 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/42—Bleach-fixing or agents therefor ; Desilvering processes
- G03C7/421—Additives other than bleaching or fixing agents
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Knives (AREA)
- Removal Of Insulation Or Armoring From Wires Or Cables (AREA)
Abstract
The invention resides in treating an image-wise exposed and colour developed photographic element with a bleaching agent and a fixing agent. The fixing agent comprises an aliphatic thiol as accelerator. The accelerator present in the fixing agent both stabilizes the fixing agent so that it can be used commercially and prevents staining resultant upon the degeneration of the thiol in the bleach fix bath. The invention also provides a means for efficient silver removal from the fixing bath thereby obviating a separate silver removal stage.
Description
SILVER REMOVAL FROM PHOTOGRAPHIC PRODUCTS
DESCRIPTION
The present invention relates to improvements in silver removal from photographic products, and particularly from developed photographic materials to enable successful silver removal during a bleach-fix step.
It is common to use a bleach step followed by a fix step, optionally with a washing step between to remove silver from images in negative photographic products. With print materials such as colour photographic paper the bleach can be combined with the fix to give a bleach-fix composition. However the silver removing power of this bleach-fix composition is insufficient to remove all silver from camera speed materials. This is believed to be caused by inhibiting materials absorbed onto the developed silver surface.
Thus one problem in the art is to remove the inhibiting absorbed materials from the developed silver surface, of the photographic product whether positive or negative.
Another problem lies with silver recovery. It is common to remove silver from used photographic reagents. This is usually effected as a separate step either chemically or electrolyticall . This recovery progress is more easily effected from the fix step rather than the bleach-fix step, and further it would be most desirable if silver recovery could be effected, in a large part at least, as a function of the silver removal process from the photographic material rather than as a separate removal process.
These problems have in part been addressed in US-A-3,893,858. In this disclosure an accelerator selected from certain aliphatic thiols is used to assist silver removal. These thiols may be selected from compounds containing a thio-group in combination with one or more solubilizing groups.
We have now found however that where the accelerators are used per se as a prebath prior to the bleach-fix step, their useful life is not long enough to be commercially worthwhile, whereas if the accelerator is added to the bleach-fix there is a tendancy for the accelerator to cause staining as a result of the accelerator reacting with itself in the bleach-fix on standing. For these reasons the use of accelerators has not been common in the art over the last few years.
We have now found that these stability problems may be addressed by adding the accelerator to the fixer which produces the bleach-fix. This has two effects; first it stabilizes the accelerator thereby to increase its active life, and second the stabilizing effect alleviates any subsequent staining problems. More importantly however silver removal may be effected at the fixer stage.
Accordingly the inclusion of the accelerator in the fixer has the effect of promoting product quality while allowing effective silver removal from the fixer stage thereby, with care, allowing the silver recovery
without the previously required separate silver recovery step.
In a preferred embodiment in accordance with the invention the silver recovery is effected by precipitation of a silver product as a result of an intereaction of the accelerator with a silver complexed species which can be readily recovered, by usual methods of solid/liquid separation such as filtration.
According therefore to a first aspect of the present invention there is provided a method for photographic processing in which an image-wise exposed and colour developed photographic element is contacted with a fixing agent, wherein said element is also contacted with an accelerator selected from a bleach accelerating amount of a thiol or a photographically effective salt thereof, said thiol being selected from monothiolglycerol, cystine, cystamine, cysteine, and aminoal ylenethiols of the formula:
wherein each of R 1 and R2 is individually H, CH3 or
C 2H5, and n is an integer having a value of 1 to 3; prior to contact with a bleach-fix agent to oxidize metallic silver and remove the same from the element;
characterised in that the accelerator is present as part of the fixing agent composition.
In a preferred form of the invention the fixing agent comprises a thiosulphate or chemically analogous compound and the bleach-fix bath contains a ferric amino polycarboxylic acid.
In a further aspect of the present invention there is provided a method for the recovery of silver from a photographic process in which an image-wise exposed and colour developed silver containing photographic
element is contacted with a fixing agent before contact with a bleach-fixing solution;
which recovery method comprises adding to the fixing agent an accelerator selected from monothioglycerol, cystine, cystamine, cysteine, and aminoalkylenethiols of the formula
in which R 1 and R2 is each H, CH3 or C2H5, and N is an integer having a value of 1 to 3;
thereby to cause the silver to precipitate as a silver salt thereby to substantially remove silver from the reaction medium prior to the bleach-fix stage.
Preferably the bleach-fixing agent is a thiosulphate and the silver is removed as a precipitate of silver sulphide or silver thiol. Preferred accelerating agents in accordance with the present invention are dimethylaminoe hane thiol, (DMAET) and its
thiouronium derivatives, thioglycerol, cysteine and cystine.
The invention will now be described, by way of illustration only, with reference to the following Example, and with reference to the accompanying drawings wherein:
Figure 1 shows a graph of the sensitometry of kodacolor VR100 film processed through a standard C-41 process. This is compared to the same film processed through the example process.
Figure 2 shows a graph of the sensitometry of Kodacolor VR200 film processed through a standard C-41 process. This is compared to the same film processed through the example process.
Figure 3 shows a graph of the sensitometry of Kodacolor VR400 film processed through a standard C-41 process. This is compared to the same film processed through the example process.
Figure 4 shows a graph of the sensitometry of Kodacolor VRIOOO film processed through a standard C-41 process. This is compared to the same film process through the example process.
These figures demonstrate that the process has little or no effect on the final sensitometry i.e. a film processed through the control process would be undistinguishable from an image point of view from one processed in a standard C-41 process.
EXAMPLE
A fix was prepared according to the following formula using commercially available materials:
Experimental Accelerating Fix.
ammonium thiosulphate 32Og ethylenediamine tetracetic acid(EDTA) 2g sodium metabisulphite 8g dimethylaminoethanthiol (DMAET) 5g water to 1 litre
The pH of this solution was adjusted to 6.5 by the addition of acetic acid.
A bleach-fix was prepared according to the following formula using commercially available materials:-
Experimental Bleach-fix.
1.56M ammonium iron(III) EDTA solution 75mls ammonium thiosulphate 60g sodium sulphite 8g water to 1 litre
The pH of this solution was adjusted to 6.0 by the addition of acetic acid.
A developer, bleach and fix were made up using Kodak C-41 20 litre kits according to the instructions enclosed in the kit boxes.
Strips of four Kodak colour negative films, VR100, VR200, VR400, VRIOOO were exposed to simulated daylight through a 0.2 log exposure sensitometric
wedge for 0.01 seconds. These strips were kept for 24 hours then processed through the following process:
Similar strips of exposed and aged film were processed in a standard C-41 process as described in the C-41 manual. The processed strips were measured using a Macbeth densitometer and compared. Figures 1-4 show the results for the four different films. The levels of residual silver in all strips Dmaxs were all less than could be detected with any confidence by X-ray Fluorescence Spectroscopy i.e. 25mg/sq.m.
The experiment was repeated with a number of other compounds in place of the DMAET in the experimental fix, all used at a concentration of 5g/l. Table 1 below shows the red, green and blue Dmax densities of
- li ¬ the four films processed in the experimental process with the different experimental fixes, using the experimental fixes, using the experimental bleach-fix for 2'00" in all cases.
- 12 -
Table 1
In those films that had been processed with an additive present in the fix, no sil could be. detected by infra-red density measurements.
Claims
1. A method for photographic processing in which an image-wise exposed and colour developed photographic element is contacted with a fixing agent, wherein said element is also contacted with an accelerator selected from a bleach accelerating amount of a thiol or a photographically effective salt thereof, said thiol being selected from monothiolglycerol, cystine, cystamine, cysteine, and an aminoal-ylenethiol of the formula
N - (CH2)n-SH
R2
wherein each of R 1 and R2 is individually H, CH3 or
C 2H5, and n is an integer having a value of 1 to 3; prior to contact with a bleach-fix agent to oxidize metallic silver and remove the same from the element; characterised in that the accelerator is present as part of the fixing agent composition.
2. A method according to claim 1 characterised in that the fixing agent contains a thiolsulphate and the bleach-fix agent contains a ferric amino polycarboxylic acid.
3. A method according to either of claims 1 or 2 characterised in that the accelerator is selected from
DMAET or its thiouronium derivative, thioglycerol cysteine or cystine.
4. A method according to either of claims 2 or 3 characterised in that the ratio by weight of accelerator to the thiosulphate in the fixer bath is 1 to 2:100.
5. A method for the recovery of silver from a photographic process in which an image-wise exposed and colour developed silver containing element is contacted with a fixing agent before contact with a bleach-fixing solution; which recovery method comprises adding to the fixing agent an accelerator selected from thioglycerol cystine, cystamine, cysteine, and an amnioalkylenethio of the formula:
RJ
wherein each of R1 and R2 is individually H, CH3 or
C 2H5, and n is an integer having a value of 1 to 3;
thereby to cause the silver to precipitate as a silver salt to substantially remove silver from the reaction medium prior to the bleach-fix stage.
6. A method according to claim 5 characterised in that the fixing agent contains a thiosulphate and the bleach-fix stage contains a ferric amino carboxylic acid.
7. A method according to either of claims 5 or 6 characterised in that the accelerator is selected from DMAET or its thiouronium derivative, thioglycerol cysteine or cystine.
8. A method according to either of claims 6 or 7, characterised in that the weight ratio of accelerator to the thiosulphate in the fixer bath is 1 to 2:100.
9. A method according to claim 1 and substantially as hereinbefore set forth with reference to, and/or as illustrated in. Figures 1 to 4 of the accompanying drawings.
10. A method for the recovery of silver substantially as hereinbefore set forth with reference to, and/or as illustrated in. Figures 1 to 4 of the accompanying drawings.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69102696T DE69102696T2 (en) | 1990-03-07 | 1991-03-05 | SILVER REMOVAL FROM PHOTOGRAPHIC PRODUCTS. |
| EP91904935A EP0518905B1 (en) | 1990-03-07 | 1991-03-05 | Silver removal from photographic products |
| JP91504601A JPH05506727A (en) | 1990-03-07 | 1991-03-05 | Silver removal from photographic products |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909005130A GB9005130D0 (en) | 1990-03-07 | 1990-03-07 | Silver removal from photographic products |
| GB9005130.1 | 1990-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1991014205A1 true WO1991014205A1 (en) | 1991-09-19 |
Family
ID=10672186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1991/000406 WO1991014205A1 (en) | 1990-03-07 | 1991-03-05 | Silver removal from photographic products |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0518905B1 (en) |
| JP (1) | JPH05506727A (en) |
| AT (1) | ATE108032T1 (en) |
| DE (1) | DE69102696T2 (en) |
| GB (1) | GB9005130D0 (en) |
| WO (1) | WO1991014205A1 (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1138842A (en) * | 1965-06-11 | 1969-01-01 | Agfa Gevaert Ag | Bleach-fixing for photographic silver images |
| GB1150466A (en) * | 1966-05-06 | 1969-04-30 | Fuji Photo Film Co Ltd | Improvements in Colour Photography Processes |
| GB1411985A (en) * | 1972-10-18 | 1975-10-29 | Ilford Ltd | Silver recovery process |
| US4293639A (en) * | 1979-05-09 | 1981-10-06 | Fuji Photo Film Co., Ltd. | Bleaching compositions for photographic processing |
| EP0173540A2 (en) * | 1984-08-20 | 1986-03-05 | Konica Corporation | Color image forming method |
| EP0213710A2 (en) * | 1985-07-18 | 1987-03-11 | Konica Corporation | Method of processing silver halide color photographic material |
-
1990
- 1990-03-07 GB GB909005130A patent/GB9005130D0/en active Pending
-
1991
- 1991-03-05 WO PCT/EP1991/000406 patent/WO1991014205A1/en active IP Right Grant
- 1991-03-05 AT AT91904935T patent/ATE108032T1/en not_active IP Right Cessation
- 1991-03-05 EP EP91904935A patent/EP0518905B1/en not_active Expired - Lifetime
- 1991-03-05 DE DE69102696T patent/DE69102696T2/en not_active Expired - Fee Related
- 1991-03-05 JP JP91504601A patent/JPH05506727A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1138842A (en) * | 1965-06-11 | 1969-01-01 | Agfa Gevaert Ag | Bleach-fixing for photographic silver images |
| GB1150466A (en) * | 1966-05-06 | 1969-04-30 | Fuji Photo Film Co Ltd | Improvements in Colour Photography Processes |
| GB1411985A (en) * | 1972-10-18 | 1975-10-29 | Ilford Ltd | Silver recovery process |
| US4293639A (en) * | 1979-05-09 | 1981-10-06 | Fuji Photo Film Co., Ltd. | Bleaching compositions for photographic processing |
| EP0173540A2 (en) * | 1984-08-20 | 1986-03-05 | Konica Corporation | Color image forming method |
| EP0213710A2 (en) * | 1985-07-18 | 1987-03-11 | Konica Corporation | Method of processing silver halide color photographic material |
Non-Patent Citations (2)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN vol. 001, no. 136 (E-062) 10 November 1977, & JP-A-52 073033 (FUJI SHASHIN FILM KK) 18 June 1977, see the whole document * |
| PATENT ABSTRACTS OF JAPAN vol. 11, no. 276 (P-613)(2723) 08 September 1987, & JP-A-62 075525 (KONISHIROKU PHOTO INDUSTRY CO LTD) 07 April 1987, see the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0518905B1 (en) | 1994-06-29 |
| GB9005130D0 (en) | 1990-05-02 |
| ATE108032T1 (en) | 1994-07-15 |
| DE69102696D1 (en) | 1994-08-04 |
| DE69102696T2 (en) | 1994-10-20 |
| EP0518905A1 (en) | 1992-12-23 |
| JPH05506727A (en) | 1993-09-30 |
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