US3428456A - Antistatic photographic materials - Google Patents
Antistatic photographic materials Download PDFInfo
- Publication number
- US3428456A US3428456A US460819A US3428456DA US3428456A US 3428456 A US3428456 A US 3428456A US 460819 A US460819 A US 460819A US 3428456D A US3428456D A US 3428456DA US 3428456 A US3428456 A US 3428456A
- Authority
- US
- United States
- Prior art keywords
- antistatic
- carbon atoms
- alkyl
- photographic
- layers
- 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
- 239000000463 material Substances 0.000 title description 8
- -1 silver halide Chemical class 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 239000002216 antistatic agent Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 9
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 8
- 238000005266 casting Methods 0.000 description 7
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- OEZJOJOZIIEYJG-UHFFFAOYSA-N CCN(CC)P(O)(O)=O.Cl.Cl Chemical compound CCN(CC)P(O)(O)=O.Cl.Cl OEZJOJOZIIEYJG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000007600 charging Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007786 electrostatic charging Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SLGGJMDAZSEJNG-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;terephthalic acid Chemical compound OCCOCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 SLGGJMDAZSEJNG-UHFFFAOYSA-N 0.000 description 1
- PWFDYZBEJMWUPR-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-1-(4-nonylphenoxy)ethanol Chemical compound C(CCCCCCCC)C1=CC=C(OC(COCCOCCOCCOCCOCCOCCOCCOCCOCCO)O)C=C1 PWFDYZBEJMWUPR-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YUPUMTKNEQZQFR-UHFFFAOYSA-N CN(C1=CC=CC=C1)P(O)(O)=O.Cl.Cl Chemical compound CN(C1=CC=CC=C1)P(O)(O)=O.Cl.Cl YUPUMTKNEQZQFR-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000287531 Psittacidae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000012899 de-mixing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011346 highly viscous material Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000009828 non-uniform distribution Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
- G03C1/856—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2408—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyalkyl compounds
Definitions
- antistatic agents to, silver halide emulsion layers and/or auxiliary layers, such as protective or backing layers, of photographic materials in order to avoid electrostatic charging.
- a certain antistatic effect can be produced by means of the inorganic salts which already are present in the emulsions, such as sodium chloride, potassium bromide or sodium nitrate, all of which have a high electrical conductivity and are thus able to dissipate locally occurring electric charges.
- the protective action obtained with these salts generally is insufficient. More effective substances are required to impart a lowest possible charging capacity to the film as well as -a high conductivity.
- the further object is to provide photographic materials with at least one light-sensitive silver halide emulsion layer which have improved antistatic properties.
- Sluitable compounds include .those of the following formu a:
- R and R represent hydrogen, alkyl, preferably having up to 12 carbon atoms, cycolalkyl, such as cyclohexyl, aryl, preferably a phenyl or a naphthyl, phenyl alkyl such as benzyl or phenyl ethyl or R :and R together can stand for the ring members, preferably methylene groups, necessary to complete a 5 or 6-membered heterocyclic ring,
- R" represents alkyl, preferably with 12 to 20 carbon atoms, aryl, preferably a radial of the benzene series, more particular phenyl, which can be substituted with alkyl or olefinically unsaturated alkyl, preferably having between 1 and 20 carbon atoms, halogen, such as chloride and bromide, alkoxy groups having up to 12 carbon atoms and the like, which is substituted by an alkyl or alkylene radical with 1 to 12 carbon atoms,
- A represents alkylene radicals with 2 to 4 carbon atoms, advantageously ethylene radicals, which can be partially replaced by propylene and/or butylene radicals,
- n an integer from 1 to 40, advantageously 1 to
- the antistatic effect of the compounds of the present invention is unexpected because similar amido phosphoric acid esters with glycols or polyalkylene glycols with terminal 'hydroxy groups do not act as antistatic agents.
- preferred compounds are etherified at the end of the alkylene glycol chain with a substituent containing a long-chained alkyl group having between 12 and 20 carbon atoms and with polyalkylene glycol chains containing between 6 and 12 alkylene glycol units.
- the present antistatic agents are added to the photographic layers, more especially the protective layers for silver halide emulsion layers, advantageously in quantities from 1 to 25 percent by weight, calculated on the dry weight of binding agent of the layers, which binding agent is preferably gelatine.
- glycol ethers of the following general formula wherein R" and A have the above meaning are reacted according to common practice with an amidophosphoric acid dihalide or lower aliphatic ester in a molar ratio of about 2:1 in the presence of bases, such as pyridine.
- amidophosphoric acid diahalides used for the aforesaid reaction can be substituted in the amide group by alkyl radicals, advantageously those with 1 to 6 carbon atoms, by aryl radicals, particularly phenyl radicals, which in their turn can be substituted by alkyl groups, alkoxy groups, phenoxy groups, halogen atoms or other substituents, or by aralkyl groups, such as benzyl.
- the nitrogen atom of the amide group can form part of a heterocyclic ring, e.g. piperidine or morpholine.
- amidophosphoric acid dihalides or esters are those of the following formulae:
- the electrostatic charging in volts per cm. (v./cm.) is determined by means of the rotating field strength measuring instrument according to Schwenkhagen and the electric surface resistivity in ohms is determined with the Schneiden instrument.
- Example 2 A protective layer containing 12 g. of gelatine per litre of casting solution was cast in a thickness of 1 mu onto gelatino-silver halide emulsion layer of a photographic material.
- the protective layer solution ready for casting had 3 g. per litre of the compounds mentioned above added thereto and the casting was carried out in the same way. The following measurement results were obtained, using the test methods described above:
- R and R taken alone each represent hydrogen, alkyl, cycloalkyl, phenyl, naphthyl and phenylalkyl; R and R together represent the ring members necessary to complete a heterocyclic ring having 5 to 6 ring members;
- R" stands for a member of the group consisting of alkyl and aryl;
- A represents alkylene radicals having between 2 to 4 carbon atoms and it stands for an integer from 1 to 40.
- a light-sensitive photographic element containing at least one light-sensitive silver halide gelatin emulsion layer said photographic element having at least one layer containing an effective amount of an antistatic agent comprising a diester of amido-phosphoric acid having the formula wherein R and R when taken alone stand for hydrogen, alkyl having up to 12 carbon atoms, cycloalkyl, phenyl, naphthyL benzyl or phenyl ethyl,
- R and R together stand for the atoms necessary to complete a 5 or 6 membered ring
- R" stands for alkyl having from 12 to carbon atoms, phenyl or substituted products thereof wherein the substituents are saturated or unsaturated alkyl having up to 20 carbon atoms, halogen or alkoxy having up 0 12 carbon atoms,
- A stands for alkylene having from 2 to 4 carbon atoms and n stands for an integer from 1 to 40,
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA0046356 | 1964-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3428456A true US3428456A (en) | 1969-02-18 |
Family
ID=6935220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US460819A Expired - Lifetime US3428456A (en) | 1964-06-19 | 1965-06-02 | Antistatic photographic materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3428456A (de) |
| BE (1) | BE665615A (de) |
| CH (1) | CH450158A (de) |
| DE (1) | DE1447580A1 (de) |
| FR (1) | FR1437268A (de) |
| GB (1) | GB1113807A (de) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655387A (en) * | 1970-09-15 | 1972-04-11 | Eastman Kodak Co | Antistatic photographic compositions |
| US4272616A (en) * | 1978-06-07 | 1981-06-09 | Fuji Photo Film Co., Ltd. | Photographic radiation-sensitive materials having improved antistatic property |
| US4416830A (en) * | 1979-08-30 | 1983-11-22 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Polyether phosphoric acids or esters |
| US5174923A (en) * | 1989-02-03 | 1992-12-29 | Eastman Kodak Company | Cyclic phosphazene and salt antistatic composition |
| EP0638842A1 (de) * | 1993-07-27 | 1995-02-15 | Minnesota Mining And Manufacturing Company | Härten gelatinehaltiger Schichten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971897A (en) * | 1989-02-03 | 1990-11-20 | Eastman Kodak Company | Photographic silver halide element containing cyclic phosphazene and salt antistatic composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3264108A (en) * | 1963-03-19 | 1966-08-02 | Gen Aniline & Film Corp | Antistatic photographic film |
-
1964
- 1964-06-19 DE DE19641447580 patent/DE1447580A1/de active Pending
-
1965
- 1965-06-02 US US460819A patent/US3428456A/en not_active Expired - Lifetime
- 1965-06-03 CH CH780665A patent/CH450158A/de unknown
- 1965-06-10 GB GB24599/65A patent/GB1113807A/en not_active Expired
- 1965-06-18 FR FR21510A patent/FR1437268A/fr not_active Expired
- 1965-06-18 BE BE665615D patent/BE665615A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3264108A (en) * | 1963-03-19 | 1966-08-02 | Gen Aniline & Film Corp | Antistatic photographic film |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655387A (en) * | 1970-09-15 | 1972-04-11 | Eastman Kodak Co | Antistatic photographic compositions |
| US4272616A (en) * | 1978-06-07 | 1981-06-09 | Fuji Photo Film Co., Ltd. | Photographic radiation-sensitive materials having improved antistatic property |
| US4416830A (en) * | 1979-08-30 | 1983-11-22 | Gesellschaft Fur Biotechnologische Forschung Mbh (Gbf) | Polyether phosphoric acids or esters |
| US5174923A (en) * | 1989-02-03 | 1992-12-29 | Eastman Kodak Company | Cyclic phosphazene and salt antistatic composition |
| EP0638842A1 (de) * | 1993-07-27 | 1995-02-15 | Minnesota Mining And Manufacturing Company | Härten gelatinehaltiger Schichten |
| US5470699A (en) * | 1993-07-27 | 1995-11-28 | Minnesota Mining And Manufacturing Company | Hardening of gelatin-containing layers |
Also Published As
| Publication number | Publication date |
|---|---|
| BE665615A (de) | 1965-12-20 |
| CH450158A (de) | 1968-01-15 |
| FR1437268A (fr) | 1966-04-29 |
| DE1447580A1 (de) | 1968-12-19 |
| GB1113807A (en) | 1968-05-15 |
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