CA1067327A - Hardening photographic layers containing protein with a carbamoyl pyridinium compound - Google Patents
Hardening photographic layers containing protein with a carbamoyl pyridinium compoundInfo
- Publication number
- CA1067327A CA1067327A CA233,572A CA233572A CA1067327A CA 1067327 A CA1067327 A CA 1067327A CA 233572 A CA233572 A CA 233572A CA 1067327 A CA1067327 A CA 1067327A
- Authority
- CA
- Canada
- Prior art keywords
- hardener
- process according
- hardening
- layers
- solution
- 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
Links
- -1 carbamoyl pyridinium compound Chemical class 0.000 title claims abstract description 16
- 108090000623 proteins and genes Proteins 0.000 title claims abstract description 16
- 102000004169 proteins and genes Human genes 0.000 title claims abstract description 15
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 21
- 239000000243 solution Substances 0.000 claims description 26
- 239000001828 Gelatine Substances 0.000 claims description 22
- 229920000159 gelatin Polymers 0.000 claims description 22
- 235000019322 gelatine Nutrition 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000005266 casting Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
- 239000010410 layer Substances 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 40
- 239000000460 chlorine Substances 0.000 description 36
- 239000011734 sodium Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- 235000018102 proteins Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 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 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000009931 harmful effect Effects 0.000 description 3
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000000654 additive Substances 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
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 description 1
- RMFRFTSSEHRKKW-UHFFFAOYSA-N 1,2-bis(diisopropylphosphino)ethane Chemical compound CC(C)P(C(C)C)CCP(C(C)C)C(C)C RMFRFTSSEHRKKW-UHFFFAOYSA-N 0.000 description 1
- RGIIAYDCZSXHGL-UHFFFAOYSA-N 2-pyridin-4-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCC1=CC=NC=C1 RGIIAYDCZSXHGL-UHFFFAOYSA-N 0.000 description 1
- QBNQNDKOKMBUJW-UHFFFAOYSA-N 4,6-dichloro-2H-triazin-5-one Chemical compound ClC1=C(C(=NN=N1)Cl)O QBNQNDKOKMBUJW-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
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical class C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- SCNIGJIBVSZFTG-UHFFFAOYSA-N carbonyl dichloride;morpholine Chemical compound ClC(Cl)=O.C1COCCN1 SCNIGJIBVSZFTG-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical class NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 229960000943 tartrazine Drugs 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- 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
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/30—Hardeners
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Pyridine Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2439551A DE2439551C2 (de) | 1974-08-17 | 1974-08-17 | Verfahren zur Härtung photographischer Schichten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067327A true CA1067327A (en) | 1979-12-04 |
Family
ID=5923462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA233,572A Expired CA1067327A (en) | 1974-08-17 | 1975-08-15 | Hardening photographic layers containing protein with a carbamoyl pyridinium compound |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4063952A (en, 2012) |
| JP (1) | JPS5832699B2 (en, 2012) |
| BE (1) | BE829895A (en, 2012) |
| CA (1) | CA1067327A (en, 2012) |
| CH (1) | CH598618A5 (en, 2012) |
| DE (1) | DE2439551C2 (en, 2012) |
| FR (1) | FR2282125A1 (en, 2012) |
| GB (1) | GB1510834A (en, 2012) |
| IT (1) | IT1041222B (en, 2012) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2924035A1 (de) * | 1979-06-13 | 1981-01-08 | Agfa Gevaert Ag | Verfahren zur kettenverlaengerung von gelatine durch partielle haertung |
| DE3037912A1 (de) * | 1980-10-08 | 1982-05-27 | Agfa-Gevaert Ag, 5090 Leverkusen | Lichtempfindliches fotografisches silberhalogenid-aufzeichnungsmaterial |
| JPS60237445A (ja) * | 1984-05-10 | 1985-11-26 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPS61100743A (ja) * | 1984-10-24 | 1986-05-19 | Fuji Photo Film Co Ltd | ゼラチンの硬化方法 |
| JPS61128241A (ja) * | 1984-11-28 | 1986-06-16 | Fuji Photo Film Co Ltd | ゼラチンの硬化方法 |
| JPS61217377A (ja) * | 1985-03-08 | 1986-09-26 | 信越ポリマ−株式会社 | 電子部品収納トレ− |
| JPH0612408B2 (ja) * | 1986-05-09 | 1994-02-16 | 富士写真フイルム株式会社 | ゼラチンの硬化方法 |
| DE3626221A1 (de) * | 1986-08-02 | 1988-02-04 | Agfa Gevaert Ag | Farbfotografisches aufzeichnungsmaterial zur herstellung farbiger aufsichtsbilder |
| DE3629388A1 (de) * | 1986-08-29 | 1988-03-03 | Agfa Gevaert Ag | Verfahren zur haertung proteinartige bindemittel enthaltender schichten |
| DE3638638A1 (de) * | 1986-11-12 | 1988-05-19 | Agfa Gevaert Ag | Farbfotografisches aufzeichnungsmaterial |
| JPH0687124B2 (ja) * | 1987-02-26 | 1994-11-02 | アグフアーゲヴエルト・アクチエンゲゼルシヤフト | 写真記録材料 |
| DE3819082A1 (de) * | 1988-06-04 | 1989-12-14 | Agfa Gevaert Ag | Farbfotografisches silberhalogenidmaterial |
| DE3819469A1 (de) * | 1988-06-08 | 1989-12-14 | Agfa Gevaert Ag | Fotografisches aufzeichnungsmaterial |
| DE4119982C2 (de) * | 1991-06-18 | 1993-09-30 | Du Pont Deutschland | 1,3-Bis-carbamoylimidazoliumverbindungen und Verfahren zum Härten von Gelatine enthaltenden Schichten |
| US5601971A (en) * | 1991-06-18 | 1997-02-11 | Sterling Diagnsotic Imaging, Inc. | Hardening of hydrophilic colloids with imidazolium and triazine combinations |
| US5236822A (en) * | 1991-10-03 | 1993-08-17 | Eastman Kodak Company | Method and composition for hardening gelatin |
| US5547832A (en) * | 1992-07-07 | 1996-08-20 | Eastman Kodak Company | Method for hardening photographic materials |
| US5378842A (en) * | 1993-12-21 | 1995-01-03 | E. I. Du Pont De Nemours And Company | Imidazolium hardeners for proteinaceous materials |
| US5411856A (en) * | 1994-01-10 | 1995-05-02 | Eastman Kodak Company | Carbamyl-substituted bis(vinylsulfonyl) methane hardeners |
| EP0674227B1 (en) | 1994-03-22 | 1996-06-12 | Agfa-Gevaert N.V. | Imaging element and method for making a printing plate according to the silver salt diffusion transfer process |
| EP0692473A1 (en) * | 1994-07-12 | 1996-01-17 | Minnesota Mining And Manufacturing Company | Process for preparing carbamoyl pyridinium compounds |
| EP0698822B1 (en) | 1994-08-22 | 1999-03-17 | Agfa-Gevaert N.V. | Lithographic printing plate precursor with a flexible support and method for making a lithographic printing plate therewith |
| DE69423620T2 (de) * | 1994-10-31 | 2000-08-10 | Tulalip Consultoria Comercial Sociedade Unipessoal S.A., Funchal | Pyridiumcarbamoyl Härtemittel enthaltendes photographisches Silberhalogenidmaterial |
| EP0717312A1 (en) * | 1994-12-16 | 1996-06-19 | Minnesota Mining And Manufacturing Company | Hardened silver halide photographic elements |
| EP0722116A1 (en) * | 1995-01-12 | 1996-07-17 | Minnesota Mining And Manufacturing Company | Antistatic film bases and photographic elements comprising said antistatic film bases |
| EP0745901B1 (en) | 1995-05-31 | 1999-03-17 | Agfa-Gevaert N.V. | A concentrated dampening solution with an improved shelf life for printing with a lithographic printing plate obtained according to the silver salt diffusion transfer process |
| EP0754971A1 (en) | 1995-07-18 | 1997-01-22 | Agfa-Gevaert N.V. | Material for industrial radiography and development method thereof |
| DE19526468A1 (de) * | 1995-07-20 | 1997-01-23 | Agfa Gevaert Ag | Härtungsmittel für fotografische Materialien |
| EP0774693B1 (en) | 1995-11-16 | 2000-05-24 | Agfa-Gevaert N.V. | A method for making by phototypesetting a lithographic printing plate according to the silver salt diffusion transfer process |
| EP0779554A1 (en) | 1995-12-14 | 1997-06-18 | Agfa-Gevaert N.V. | A correcting liquid for a silver imaged lithographic printing plate |
| CA2193040A1 (en) | 1996-01-19 | 1997-07-20 | Jeremy M. Grace | Molecular grafting of carboxyl reactive hardeners to energetically treated polyesters to promote adhesion of layers |
| EP0790532B1 (en) | 1996-02-14 | 2000-07-05 | Agfa-Gevaert N.V. | A method for making a lithographic printing plate according to the silver salt diffusion transfer process |
| EP0791858B1 (en) | 1996-02-26 | 2000-10-11 | Agfa-Gevaert N.V. | A method for making by phototypesetting a lithographic printing plate according to the silver salt diffusion transfer process |
| US6500527B2 (en) * | 2001-02-01 | 2002-12-31 | 3M Innovative Properties Company | Image receptor sheet |
| US6468339B1 (en) | 2001-08-23 | 2002-10-22 | Eastman Kodak Company | Alumina filled gelatin |
| US6933024B2 (en) * | 2002-07-18 | 2005-08-23 | Hewlett-Packard Development Company, L.P. | Water soluble polymers as inkjet recording materials |
| JP2006508826A (ja) * | 2002-12-04 | 2006-03-16 | フジ フォト フィルム ビー．ブイ． | インクジェット記録媒体 |
| WO2004110774A1 (en) * | 2003-06-18 | 2004-12-23 | Fuji Photo Film B.V. | Ink-jet recording medium |
| JP2007502220A (ja) * | 2003-08-13 | 2007-02-08 | フジ フォト フィルム ビー．ブイ． | インクジェット記録媒体 |
| EP1677989B1 (en) * | 2003-10-03 | 2008-01-30 | FUJIFILM Manufacturing Europe B.V. | Recording medium |
| WO2005032837A1 (en) * | 2003-10-03 | 2005-04-14 | Fuji Photo Film B.V. | Recording medium |
| JP2011518782A (ja) | 2008-04-10 | 2011-06-30 | フジフィルム・マニュファクチュアリング・ヨーロッパ・ベスローテン・フエンノートシャップ | ヘパリン結合部位および／またはヘパラン硫酸結合部位を富化した組換えタンパク質 |
| WO2010001149A2 (en) * | 2008-07-04 | 2010-01-07 | Fujifilm Manufacturing Europe Bv | Coating method for medical devices |
| EP2344593A2 (en) * | 2008-10-02 | 2011-07-20 | Fujifilm Manufacturing Europe BV | Antimicrobial coating |
| GB0921460D0 (en) | 2009-12-08 | 2010-01-20 | Fujifilm Mfg Europe Bv | Anti-fibrotic hydrogel compositions |
| GB201014388D0 (en) | 2010-08-31 | 2010-10-13 | Fujifilm Mfg Europe Bv | Biocompatible compositions for tissue augmentation |
| GB201119182D0 (en) | 2011-11-07 | 2011-12-21 | Fujifilm Mfg Europe Bv | Porous tissue scaffolds |
| GB201119173D0 (en) | 2011-11-07 | 2011-12-21 | Fujifilm Mfg Europe Bv | Porous tissue scaffolds |
| EP3181358A1 (en) | 2015-12-15 | 2017-06-21 | Agfa Graphics NV | Processless lithographic printing plate |
| EP3322008A1 (en) | 2016-11-11 | 2018-05-16 | Oxis Energy Limited | Electrode for lithium sulphur cell |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1296513B (de) * | 1965-12-30 | 1969-05-29 | Adox Du Pont Fotowerke | Verfahren zum Haerten von gelatinehaltigen photographischen Schichten, insbesondere Halogensilberemulsionsschichten |
| US3645743A (en) * | 1968-08-27 | 1972-02-29 | Agfa Gevaert Ag | Process for hardening protein layers |
| BE754789A (nl) * | 1969-08-21 | 1971-02-15 | Agfa Gevaert Nv | Werkwijze voor het verharden van fotografische lagen |
| DE2225230C2 (de) * | 1972-05-24 | 1984-12-06 | Agfa-Gevaert Ag, 5090 Leverkusen | Verfahren zur Härtung photographischer Schichten |
| US3880665A (en) * | 1972-05-24 | 1975-04-29 | Agfa Gevaert Ag | Hardening with a heterocyclic carbamoyl ammonium compound of a photographic material containing a silver halide layer |
-
1974
- 1974-08-17 DE DE2439551A patent/DE2439551C2/de not_active Expired
-
1975
- 1975-06-05 BE BE1006717A patent/BE829895A/xx not_active IP Right Cessation
- 1975-08-12 IT IT50924/75A patent/IT1041222B/it active
- 1975-08-12 US US05/604,010 patent/US4063952A/en not_active Expired - Lifetime
- 1975-08-14 FR FR7525380A patent/FR2282125A1/fr active Granted
- 1975-08-15 CA CA233,572A patent/CA1067327A/en not_active Expired
- 1975-08-15 CH CH1068775A patent/CH598618A5/xx not_active IP Right Cessation
- 1975-08-15 GB GB34045/75A patent/GB1510834A/en not_active Expired
- 1975-08-15 JP JP50098664A patent/JPS5832699B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1510834A (en) | 1978-05-17 |
| JPS5159625A (en) | 1976-05-24 |
| IT1041222B (it) | 1980-01-10 |
| JPS5832699B2 (ja) | 1983-07-14 |
| FR2282125A1 (fr) | 1976-03-12 |
| FR2282125B1 (en, 2012) | 1978-10-27 |
| US4063952A (en) | 1977-12-20 |
| BE829895A (nl) | 1975-12-05 |
| DE2439551A1 (de) | 1976-02-26 |
| DE2439551C2 (de) | 1985-11-21 |
| CH598618A5 (en, 2012) | 1978-05-12 |
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