US3346386A - Polycondensation products of phosphoric acid amides with aliphatic polyethers as developer adjuvants - Google Patents
Polycondensation products of phosphoric acid amides with aliphatic polyethers as developer adjuvants Download PDFInfo
- Publication number
- US3346386A US3346386A US329364A US32936463A US3346386A US 3346386 A US3346386 A US 3346386A US 329364 A US329364 A US 329364A US 32936463 A US32936463 A US 32936463A US 3346386 A US3346386 A US 3346386A
- Authority
- US
- United States
- Prior art keywords
- phosphoric acid
- developer
- compound
- adjuvants
- silver halide
- 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
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- 229920000570 polyether Polymers 0.000 title claims description 11
- 150000003012 phosphoric acid amides Chemical class 0.000 title claims description 10
- 125000001931 aliphatic group Chemical group 0.000 title description 5
- 238000006068 polycondensation reaction Methods 0.000 title description 3
- 239000002671 adjuvant Substances 0.000 title description 2
- -1 SILVER HALIDE Chemical class 0.000 claims description 16
- 239000000839 emulsion Substances 0.000 claims description 14
- 229910052709 silver Inorganic materials 0.000 claims description 13
- 239000004332 silver Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 22
- 238000011161 development Methods 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- GLZWNFNQMJAZGY-UHFFFAOYSA-N octaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCO GLZWNFNQMJAZGY-UHFFFAOYSA-N 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 229960004838 phosphoric acid Drugs 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- 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 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
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- DETXZQGDWUJKMO-UHFFFAOYSA-N alpha-hydroxymethanesulfonic acid Natural products OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- 238000011156 evaluation Methods 0.000 description 1
- DXRFSTNITSDOKK-UHFFFAOYSA-N formaldehyde;sulfurous acid Chemical class O=C.OS(O)=O DXRFSTNITSDOKK-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WAVRVGRGJKDBQY-UHFFFAOYSA-N n-diethoxyphosphorylpropan-1-amine Chemical compound CCCNP(=O)(OCC)OCC WAVRVGRGJKDBQY-UHFFFAOYSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 239000004297 potassium metabisulphite Substances 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-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
- 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
- G03C5/3056—Macromolecular additives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
- C08G65/3356—Polymers modified by chemical after-treatment with organic compounds containing phosphorus having nitrogen in addition to phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
-
- 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
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/15—Lithographic emulsion
Definitions
- the invention relates, to a process for the production of photographic images, the development of the exposed photographic material being carried out in the presence of polycondensation products of phosphoric acid amide derivatives with aliphatic polyethers.
- Phototechnical films of the co called lithoor line-type are increasingly being used in the reprography, in particular photo production of screened photographic prints.
- Lithoor line films. are such films which can be developed in developer c0mpositions containing formaldehyde bisulfite compounds to very high 'y-values and thus to sharp screened dots.
- the term 'y is to be understood the tangent of the angle between the straight-line portion of the characteristic curve (or H and D curve) of the leg E axis.
- a further object is to provide compounds which simultaneously effect the development in such a manner that the period of time during which that high *y-value is obtained can be extended so that the development is more convenient and simpler.
- R represents an alkyl group preferably with up to 5 carbon atoms or an aryl, preferably phenyl or alkyl phenyl, or aralkyl, such as benzyl group
- R can have the same meaning as R or can represent a hydrogen atom
- X represents halogen atoms such as bromine or preferably chlorine, or alkoxy groups, preferably short-chain groups having up to 5 carbon atoms such as methoxy and ethoxy
- R and R can be together the methylene groups to form a heterocyclic rin in particular a piperidine or pyrrolidine ring.
- polyethers are polyethylenglycols which contain at least 3, preferably 410 CH CH .O- units.
- polyether are advantageously reacted with, 1 mol Qf theamido phosphoric acid compound.
- lithe development or litho developer we intend a development process which yields images with very steep gradation of at least 3 by the use of a developer which contains a formaldehyde-bisulfite compound.
- Suitable for the process according to the invention are all silver halide emulsions which show a sufiiciently high gradation effect with developers which contain formaldehyde.
- the silver salts in such least 50 mol percent of according sions, the
- ernnl-t silver halide of which contains at least 65 mol percent of silver chloride and 35 mol percent or less silver in the emulsion. It is advantageous to use from 10 to 100' mg. per mol of silver halide.
- the compounds are added to the developer solutions or to the emulsions, advantageously in quantities of 30 to 300 mg./ liter of the emulsion-casting solution.
- the final dried silver halide emulsion layer with such addition accordingly contains between 0.5 and 10 mgrof the compound per squarc meter.
- the ry-value in the development is shifted from about 6 to 8 to 15; Moreover, the period of development time during which the steepest gradation or screen dot sharpness is produced is raised from about 1 minute to 3 to 4 minutes.
- An additional advantage is that a developer containing formaldehyde is much less dependent'upon temperature when it has such an additive. Whereas a developer *without this additive reacts with a considerable development acceleration and thus a pronounced shortening of the development time when the temperature is raised by 1 to 2, good results are obtained with a developer temperature between 15 and 40 when phosphoric acid amide esters are added. Because of the longer processing period, the advantages described above lead to much more reliable Working.
- the compounds according to the invention can be'added to the developer composition in an amount of 0.01 to 10 grams per liter of the aqueous composition.
- the phosphoric acid amide esters according to the invention are prepared by conventional esterification methods; the degree of condensation of the ester can be influenced as required by variations in the reaction time and in the reaction temperature. The higher the temperature, the higher is the. degree of condensation of the phosphoric acid amide esters, in particular the integer'Z" of the polyether ester formula can be influenced by varying the temperature. Thus, compounds were obtained in which Z had a value of about 100, 300, 800 or 1000. The degree' of condensation can further. be influenced, in particular the integer ,Z referred to hereinbefore, by varying the proportion of the starting compounds for theconden'sation.
- COMPOUND II 41.2 g. of nonaethylene glycol, 31.2 g. of pyridine and 19g. of N,N-diethyl phosphoric acid amidedichloride are reacted and worked up in the manner described above.
- COMPOUND IV 41.4 g. of nonaethylene glycol, 31.2 'g. of pyridine and 22.4 g. of N-methyl-N-phenyl phosphoric acid amidedichloride are reacted in a manner analogous to Compound 'I. There are formed 50 g. of'a brown-coloured semi-solid substance, which is diluted with water and decolourised with activated carbon.
- ethylene glycol in the presence of'reesterification catalysts, such as sodium or sodium'alcoholate, for several hours at 100 to 120 C.
- the ethyl alcohol that is liberated is constantly distilled 01? in vacuo and the residue can be used I for the purpose of the present invention.
- Example 1 A'gelatino-silver halide emulsion with 15 mol percent of AgBr and of AgCl is washed, ripened to the maximum sensitivity and, after adding 4-hydroxy-6-methyl- 1,3,3a,7-tetrazaindol or other stabilisers and a Wetting agent, cast onto a suitable film support; 7
- film strips are prepared with the use of the same emulsions, 80 mg. of octaethylene glycol or 80 mg. of the Made up with water to 1 litre.
- Example 2 Film strips of the emulsion described in'Example 1 are exposed behind a grey stepped wedge and are developed in the developer referred to above for periods from 1 to 6 minutes (Experiment A). The same film specimens, after addition of mg. of the Compound I (Experiment B) and 100 mg. of the phosphorous acid glycol ester according to Example 1 of Belgian Patent 609,497 (Experiment C), are developed in the same developer. 1
- Example 3 An emulsion as in Example 1 is given the usual additives (wetting agents, stabilisers and hardeners) and is divided into three portions and cast as follows onto a film support:
- reaction products has the following formula:
- R1 R2 Z wherein R and R have the meaning defined in claim 1, m can be 0 and an integer from 3 to 10; n is an integer from 3 to 10 and Z is an integer from 1 to 1000.
- reaction product has the following formula 1
- An aqueous composition containing a silver halide photographic developer and from 0.01 to 10 grams per liter of a compound of the following formula:
- m can be 0 and an integer from 3 to 10; n is an integer from 3 to 10 and Z is an integer from 1 to 1000.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA41899A DE1200682B (de) | 1962-12-17 | 1962-12-17 | Verfahren zur Herstellung photographischer Bilder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3346386A true US3346386A (en) | 1967-10-10 |
Family
ID=6932802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US329364A Expired - Lifetime US3346386A (en) | 1962-12-17 | 1963-12-10 | Polycondensation products of phosphoric acid amides with aliphatic polyethers as developer adjuvants |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3346386A (en)) |
| BE (1) | BE641382A (en)) |
| CH (1) | CH450914A (en)) |
| DE (1) | DE1200682B (en)) |
| GB (1) | GB1057948A (en)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471048A (en) * | 1981-07-10 | 1984-09-11 | Ciba Geigy Ag | Photographic material |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3156718A (en) * | 1960-04-16 | 1964-11-10 | Bayer Ag | Process for preparing thiophosphoric, thiophosphonic, and thiophosphinic acid esters |
| US3157685A (en) * | 1962-03-06 | 1964-11-17 | Stauffer Chemical Co | Partial esters of phosphoric acid and a method of preparing them |
| US3158483A (en) * | 1957-03-08 | 1964-11-24 | Eastman Kodak Co | Photographic developers containing polyalkylene glycols |
| US3162534A (en) * | 1962-05-14 | 1964-12-22 | Powers Chemco Inc | Photographic developer |
-
1962
- 1962-12-17 DE DEA41899A patent/DE1200682B/de active Pending
-
1963
- 1963-12-10 US US329364A patent/US3346386A/en not_active Expired - Lifetime
- 1963-12-13 GB GB49357/63A patent/GB1057948A/en not_active Expired
- 1963-12-13 CH CH1527963A patent/CH450914A/de unknown
- 1963-12-17 BE BE641382A patent/BE641382A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158483A (en) * | 1957-03-08 | 1964-11-24 | Eastman Kodak Co | Photographic developers containing polyalkylene glycols |
| US3156718A (en) * | 1960-04-16 | 1964-11-10 | Bayer Ag | Process for preparing thiophosphoric, thiophosphonic, and thiophosphinic acid esters |
| US3157685A (en) * | 1962-03-06 | 1964-11-17 | Stauffer Chemical Co | Partial esters of phosphoric acid and a method of preparing them |
| US3162534A (en) * | 1962-05-14 | 1964-12-22 | Powers Chemco Inc | Photographic developer |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4471048A (en) * | 1981-07-10 | 1984-09-11 | Ciba Geigy Ag | Photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1200682B (de) | 1965-09-09 |
| GB1057948A (en) | 1967-02-08 |
| BE641382A (en)) | 1964-06-17 |
| CH450914A (de) | 1968-05-15 |
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