US2656273A - Photographic developers containing diamino-propanol tetracetic acid - Google Patents
Photographic developers containing diamino-propanol tetracetic acid Download PDFInfo
- Publication number
- US2656273A US2656273A US271284A US27128452A US2656273A US 2656273 A US2656273 A US 2656273A US 271284 A US271284 A US 271284A US 27128452 A US27128452 A US 27128452A US 2656273 A US2656273 A US 2656273A
- Authority
- US
- United States
- Prior art keywords
- developer
- tetracetic acid
- propanol
- diaminopropanol
- calcium
- 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.)
- Expired - Lifetime
Links
- MJPXFHUUIAIRSC-UHFFFAOYSA-N acetic acid;1,1-diaminopropan-1-ol Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CCC(N)(N)O MJPXFHUUIAIRSC-UHFFFAOYSA-N 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims description 9
- -1 SILVER HALIDE Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- CKJBFEQMHZICJP-UHFFFAOYSA-N acetic acid;1,3-diaminopropan-2-ol Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCC(O)CN CKJBFEQMHZICJP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 24
- 239000011575 calcium Substances 0.000 description 14
- 229910052791 calcium Inorganic materials 0.000 description 14
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 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 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229960001484 edetic acid Drugs 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- LSRUBRSFDNKORM-UHFFFAOYSA-N 1,1-diaminopropan-1-ol Chemical compound CCC(N)(N)O LSRUBRSFDNKORM-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000003352 sequestering agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229940001482 sodium sulfite Drugs 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CYXJEHCKVOQFOV-UHFFFAOYSA-N (4-amino-2-methylphenyl) hydrogen sulfate Chemical compound CC1=CC(N)=CC=C1OS(O)(=O)=O CYXJEHCKVOQFOV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229940094035 potassium bromide Drugs 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- CMHJKGDUDQZWBN-UHFFFAOYSA-N 2-(methylamino)-3-oxobutanoic acid Chemical compound CNC(C(C)=O)C(O)=O CMHJKGDUDQZWBN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 1
- 235000010261 calcium sulphite Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- ZDLBNXXKDMLZMF-UHFFFAOYSA-N cinitapride Chemical compound CCOC1=CC(N)=C([N+]([O-])=O)C=C1C(=O)NC1CCN(CC2CC=CCC2)CC1 ZDLBNXXKDMLZMF-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000004689 octahydrates Chemical class 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
- G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents
Definitions
- This invention relates to developers containing therein diaminopropanol' tetracetic acidas an on the quality of photographic'filinsprocessed therewith; The-prevention of these precipitates has previously received some attention; and" this difilculty 'ofthe presence of calcium in'developer solutions has been-iovercome to some extent by the use of compounds which hold the calcium inthe form'of-un-ionized complexes; Compounds which are especially characterized .bythis: property, such as.
- alkali hexametaphosphates and alkali tetraphosphates have: been used; in: developing solutions to reduce thetformatiomofj the calcium sulfite scum on :thefilms; and precipitation' of calcium *in the developer.
- these'ph'osphates stand. aqueousisolution. they gradually hydrolyze. to. the orthophosphates. which: notonly possess no; properties inhibiting calcium precipitation, butmay precipitate the calcium in the form of-calcium phosphate.
- orthophosphate is carried over: to the alum fixing bath, there is the possibility of the-precipitation of aluminum phosphate thereby.
- oxygen acids such as citric, tartaric, gluconic, etc.
- these acids have proved useful as calcium sequestering agents in photographicdeveloping solutions, but usually these acids'are so' weak that, in most instances, it is desirable to supplement their effect by also adding polyphosphates.
- amino polyacetic acids such as ethylenediamine tetracetic acid and" nitrolotri acetic acid in developing solutions, has previously been disclosed, but these compounds, although stable and effective, possess theundesirable property'of catalyzing oxidation of'the-developer by the air in the presence of traces 'of'iron'in the developer solution.
- a developer containing'0.5%' of'one of these materials, together .ewith 8 p; p. m. of iron and-.2 p. p. m. of'copper, will cause very rapid oxidation of the developer when air is bubbled'through the solutionfor 2 hours.
- One objectof our invention is: to provide a developer composition which contains: a. calcium" the formation of" calcium-containing sludges, scums, and scales in the developer-solution.
- a still further object of our, invention is to inhibit any local desensitization of the emulsion when immersed-in'the developer solution. Other objects of our invention will appear herein.
- the objects of our in-'- vention maybe accomplished by the addition of 1,3-diamino-2-propanol tetracetic acid to a developer composition in an amount constituting at least /2% of the solids in thecomposition.
- the diaminopropanol'. tetracetic acid may be added either to the developer composition in dry form or it may beincornoratedinthe aqueous solution of the developer. preferably prior to contacting the photographicmaterials with the developer solutions.
- the diaminopropanol tetracetic acid may be added to any of the. commonly employed developers, either those types'which contain borate salts, aszthe-alkaline material; or' those which contain a. carbonate,- as: the; alkaline material.
- Typical developers in which; diamino :p-ropanol tetracetic acid can be incorporated are the following:
- the diaminopropanol tetracetic: acid may be; employed: in; an amount of: at least: of the. total solidcontent, and preferablyzimasproportion of 2500. 10% therein-.:. It is; apparent;- thair. amount of: calcium see 3 questering agent which is needed will depend to a large extent upon the amount of calcium which will be present in the developing solution. This being the case, the proportion of diaminopropanol tetracetic acid which is employed will be within the judgment of the individual operator. The following example, however, illustrates a satisfactory relationship between the proportion of the diaminopropanol tetracetic acid and the-calcium which is present.
- Example 1 A developer containing monomethyl-p-aminophenol sulfate and hydroquinone developing agents and which was 0.5 molar with respect to sodium sulfite, and 0.07 molar with respect to sodium metaborate, and possessed a pH of about 9.8, was found to' precipitate densely with the addition of only 0.25 grams of calcium chloride per liter. However, it was found that when the following quantities of diaminopropanol tetracetic acid were added per liter, the amounts of calcium chloride designated could be added without any precipitation:
- Example 3 To illustrate the advantage of diaminopropanol tetracetic acid as regards promotion of oxidation of developer, 3 variations were employed as follows:
- Solutions 1 and 2 were found to remain relatively colorless and photographically active, while solution 3 was found to have oxidized to a deep brown color and was photographically inert.
- Example 4 Two grams per liter of diamino propanol tetracetic acid were added to a developer as spec-v out on this developer using the equivalent of 600 eight by ten inch sheets of photographic film per gallon of starting developer. 1.8 gallons of the replenisher were used to maintain the volume constant duringthe test. No appreciable precipitation occurred, and after a little deposit containing gelatin, silver, etc., had been filtered off, the remaining solution stayed clear and free of further deposit through the incubation and storage tests lasting 30 days. The film which had been processed in the solution was found to be free of any deposit thereon.
- Our invention is characterized by the sequestering of not only calcium, but magnesium or any other hard water cations which may be present in a developer solution.
- the diaminopropanol tetracetic acid in developer it was found that the average sequestering value thereof was 550 millimoles of calcium per mole of the diaminopropanol tetracetic acid, and theaction of this sequestering agent appeared to be substantially independent of the composition of the developer. Therefore, in order to obtain a complete sequestering eifect, it is desirable to use the diaminopropanol tetracetic acid in an amount at least corresponding to this value.
- Ezrample '5 A further illustration of the advantages of the diaminopropanol tetracetic acid over other amino sequestering agents was obtained by adding 5 p. p. m. of iron to the developer of Example 2, dividing this, and modifying the separate portions by adding 4 grams per liter of (a) diaminopropanol tetracetic acid (DPT) or (b) ethylenediamine tetracetic acid (EDT) together with sufficient sodium hydroxide to neutralize the acid. Oxidation was produced by rapidly bubbling finely dispersed air through the solutions. The developer containing the EDT discolored rapidly, being quite brown in 1 hour and dark in 2 hours and without developing activity.
- DPT diaminopropanol tetracetic acid
- EDT ethylenediamine tetracetic acid
- the developer containing the DPT discolored very little in 8 hours and lost no developing activity.
- Nitrolo triacetic acid and methylaminodiacetic acid have been found, like the ethylenediamine tetracetic acid, to also promote developer oxidation.
- the incorporation of the diamino propanol tetracetic acid in the developer may be accomplished by adding that material to emulsion compositions, and, as a result of treating those emulsions with developer solution, the diamino propanol tetracetic acid will be thereby introduced into the photographic developer composition.
- Another means by which the diaminopropanol tetracetic acid may be incorporated in the developer is 'byincorporating it in coatings which may have been applied to the photographic film in its preparation. Upon processing, the diaminopropanol tetracetic acid will be extracted from this coating or coatings by the developer solution.
- a photographic developer composition comprising a silver halide developing agent and 1,3-diamino-2-propanol tetracetic acid.
- An aqueous photographic developing solution comprising a solution of a silver halide developing agent and 1,3-amino-2-propanol tetracetic acid in water.
- a photographic developer in dry form comprising a silver halide developing agent and 1,3- diamino-z-propanol tetracetic acid.
- a photographic developing solution comprising an aqueous solution of a silver halide developing agent and 6-10 grams per liter of solution of 1,3-diamino-2-propano1 tetracetic acid.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1085004D FR1085004A (US20020095090A1-20020718-M00002.png) | 1952-02-12 | ||
| CA528734A CA528734A (en) | 1952-02-12 | Photographic developers containing diaminopropanol tetracetic acid | |
| US271284A US2656273A (en) | 1952-02-12 | 1952-02-12 | Photographic developers containing diamino-propanol tetracetic acid |
| GB3986/53A GB725573A (en) | 1952-02-12 | 1953-02-12 | Improvements in photographic development |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US271284A US2656273A (en) | 1952-02-12 | 1952-02-12 | Photographic developers containing diamino-propanol tetracetic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2656273A true US2656273A (en) | 1953-10-20 |
Family
ID=23034929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US271284A Expired - Lifetime US2656273A (en) | 1952-02-12 | 1952-02-12 | Photographic developers containing diamino-propanol tetracetic acid |
Country Status (4)
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759824A (en) * | 1954-05-18 | 1956-08-21 | Ralph B Atkinson | Method of photographic processing and developer therefor |
| US2860978A (en) * | 1954-04-01 | 1958-11-18 | Eastman Kodak Co | Photographic washing accelerators |
| US2875049A (en) * | 1956-11-05 | 1959-02-24 | Eastman Kodak Co | Stabilized photographic developers for color photography |
| US3186842A (en) * | 1957-10-25 | 1965-06-01 | Gevaert Photo Prod Nv | Diffusion transfer process for the manufacture of priniting plates |
| US3189454A (en) * | 1961-10-16 | 1965-06-15 | Eastman Kodak Co | Method of photographic development and fixing |
| US3260598A (en) * | 1961-05-29 | 1966-07-12 | Eastman Kodak Co | Photographic element-developer system |
| US3293035A (en) * | 1962-04-26 | 1966-12-20 | Gevaert Photo Prod Nv | Tanning development |
| US5399457A (en) * | 1993-10-15 | 1995-03-21 | Minnesota Mining And Manufacturing Company | Process for reducing sludge in diffusion transfer printing plates |
| EP0913330A1 (fr) | 1997-10-20 | 1999-05-06 | Cefma | Dispositif pour réaliser une découpe dans l'enveloppe d'un fardeau en défilement |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1472752C3 (de) * | 1965-05-03 | 1978-12-07 | Agfa-Gevaert Ag, 5090 Leverkusen | Entwicklerkonzentrat |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2168181A (en) * | 1936-06-25 | 1939-08-01 | Agfa Ansco Corp | Photographic treating bath |
| US2407645A (en) * | 1943-06-21 | 1946-09-17 | Martin Dennis Company | Aliphatic polycarboxylic amino acids and process of making them |
| US2544649A (en) * | 1949-01-14 | 1951-03-13 | Frederick C Bersworth | Caustic alkali composition of matter and its use as a polyvalent metal precipitationinhibitor |
-
0
- CA CA528734A patent/CA528734A/en not_active Expired
- FR FR1085004D patent/FR1085004A/fr not_active Expired
-
1952
- 1952-02-12 US US271284A patent/US2656273A/en not_active Expired - Lifetime
-
1953
- 1953-02-12 GB GB3986/53A patent/GB725573A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2168181A (en) * | 1936-06-25 | 1939-08-01 | Agfa Ansco Corp | Photographic treating bath |
| US2407645A (en) * | 1943-06-21 | 1946-09-17 | Martin Dennis Company | Aliphatic polycarboxylic amino acids and process of making them |
| US2544649A (en) * | 1949-01-14 | 1951-03-13 | Frederick C Bersworth | Caustic alkali composition of matter and its use as a polyvalent metal precipitationinhibitor |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2860978A (en) * | 1954-04-01 | 1958-11-18 | Eastman Kodak Co | Photographic washing accelerators |
| US2759824A (en) * | 1954-05-18 | 1956-08-21 | Ralph B Atkinson | Method of photographic processing and developer therefor |
| US2875049A (en) * | 1956-11-05 | 1959-02-24 | Eastman Kodak Co | Stabilized photographic developers for color photography |
| DE1056478B (de) * | 1956-11-05 | 1959-04-30 | Eastman Kodak Co | Verfahren zum Haltbarmachen farbphotographischer Farbentwickler-loesungen |
| US3186842A (en) * | 1957-10-25 | 1965-06-01 | Gevaert Photo Prod Nv | Diffusion transfer process for the manufacture of priniting plates |
| US3260598A (en) * | 1961-05-29 | 1966-07-12 | Eastman Kodak Co | Photographic element-developer system |
| US3189454A (en) * | 1961-10-16 | 1965-06-15 | Eastman Kodak Co | Method of photographic development and fixing |
| US3293035A (en) * | 1962-04-26 | 1966-12-20 | Gevaert Photo Prod Nv | Tanning development |
| US5399457A (en) * | 1993-10-15 | 1995-03-21 | Minnesota Mining And Manufacturing Company | Process for reducing sludge in diffusion transfer printing plates |
| EP0913330A1 (fr) | 1997-10-20 | 1999-05-06 | Cefma | Dispositif pour réaliser une découpe dans l'enveloppe d'un fardeau en défilement |
Also Published As
| Publication number | Publication date |
|---|---|
| GB725573A (en) | 1955-03-09 |
| FR1085004A (US20020095090A1-20020718-M00002.png) | 1955-01-26 |
| CA528734A (en) | 1956-08-07 |
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