CA1132979A - Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image - Google Patents

Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image

Info

Publication number: CA1132979A
Authority: CA; Canada
Prior art keywords: sulfonamido; hydroxy; compound; aryl; alkyl
Prior art date: 1979-05-01
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

Application number

CA326,712A

Other languages

English (en)

Inventor

Thomas E. Gompf

Claude F. Gerbal

Pierre D. Collet

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eastman Kodak Co

Original Assignee

Eastman Kodak Co

Priority date (The priority date 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 date listed.)

1979-05-01

Filing date

1979-05-01

Publication date

1982-10-05

1979-05-01 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1979-05-01 Priority to CA326,712A priority Critical patent/CA1132979A/fr

1982-10-05 Application granted granted Critical

1982-10-05 Publication of CA1132979A publication Critical patent/CA1132979A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 112
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 title claims abstract description 58
238000000034 method Methods 0.000 title claims abstract description 41
230000008569 process Effects 0.000 title claims abstract description 30
-1 sulfonamido compound Chemical class 0.000 claims abstract description 133
125000000217 alkyl group Chemical group 0.000 claims abstract description 65
238000012545 processing Methods 0.000 claims abstract description 63
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 55
125000003118 aryl group Chemical group 0.000 claims abstract description 49
230000000717 retained effect Effects 0.000 claims abstract description 26
239000000463 material Substances 0.000 claims abstract description 24
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 17
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 16
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 16
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims abstract description 16
238000009792 diffusion process Methods 0.000 claims abstract description 16
238000007254 oxidation reaction Methods 0.000 claims abstract description 12
230000003647 oxidation Effects 0.000 claims abstract description 10
238000012546 transfer Methods 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 77
229910052709 silver Inorganic materials 0.000 claims description 74
239000004332 silver Substances 0.000 claims description 74
239000000839 emulsion Substances 0.000 claims description 50
239000003795 chemical substances by application Substances 0.000 claims description 27
238000011161 development Methods 0.000 claims description 22
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 18
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
239000002243 precursor Substances 0.000 claims description 16
230000000875 corresponding effect Effects 0.000 claims description 15
230000006872 improvement Effects 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
238000004061 bleaching Methods 0.000 claims description 8
238000009826 distribution Methods 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
QBQNBOWKCYXJIZ-UHFFFAOYSA-N 5-[[4-[(3-chloro-4-hydroxyphenyl)diazenyl]phenyl]sulfonylamino]-N,N-didodecyl-2-hydroxy-3,4,6-trimethylbenzamide Chemical compound CC1=C(O)C(C(=O)N(CCCCCCCCCCCC)CCCCCCCCCCCC)=C(C)C(NS(=O)(=O)C=2C=CC(=CC=2)N=NC=2C=C(Cl)C(O)=CC=2)=C1C QBQNBOWKCYXJIZ-UHFFFAOYSA-N 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
230000003472 neutralizing effect Effects 0.000 claims 12
230000004888 barrier function Effects 0.000 claims 5
WAXDDKMKYJYFPM-UHFFFAOYSA-N [4-[[3-[[3-[4-[2,4-bis(2-methylbutan-2-yl)phenoxy]butylcarbamoyl]-4-hydroxy-2-methylnaphthalen-1-yl]sulfamoyl]phenyl]diazenyl]-5-(methanesulfonamido)naphthalen-1-yl] ethyl carbonate Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2C(OC(=O)OCC)=CC=C1N=NC(C=1)=CC=CC=1S(=O)(=O)NC(C1=CC=CC=C1C=1O)=C(C)C=1C(=O)NCCCCOC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC WAXDDKMKYJYFPM-UHFFFAOYSA-N 0.000 claims 4
HCXZXEPQLAUQMF-UHFFFAOYSA-N 7-[2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetyl]-4-[[4-[(3-chloro-4-hydroxyphenyl)diazenyl]phenyl]sulfonylamino]-1-hydroxy-3-phenyl-2-propyl-2H-naphthalene-1-carboxamide Chemical compound C12=CC=C(C(=O)COC=3C(=CC(=CC=3)C(C)(C)CC)C(C)(C)CC)C=C2C(C(N)=O)(O)C(CCC)C(C=2C=CC=CC=2)=C1NS(=O)(=O)C(C=C1)=CC=C1N=NC1=CC=C(O)C(Cl)=C1 HCXZXEPQLAUQMF-UHFFFAOYSA-N 0.000 claims 3
XHWHVLRDLDORDP-WCNVQLFYSA-N CCC(C)(C)C1=CC(C(C)(C)CC)=CC=C1OCCCCC1(NS(=O)(=O)C=2C=CC(=CC=2)\N=N\C=2C3=C(NS(C)(=O)=O)C=CC=C3C(O)=C(C=2)S(=O)(=O)NC(C)(C)C)C2=CC=CC=C2C(O)=C(C(N)=O)C1C Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC=C1OCCCCC1(NS(=O)(=O)C=2C=CC(=CC=2)\N=N\C=2C3=C(NS(C)(=O)=O)C=CC=C3C(O)=C(C=2)S(=O)(=O)NC(C)(C)C)C2=CC=CC=C2C(O)=C(C(N)=O)C1C XHWHVLRDLDORDP-WCNVQLFYSA-N 0.000 claims 3
238000007599 discharging Methods 0.000 claims 2
HLOBHXSSJVYSJT-UHFFFAOYSA-N 7-[2-[2,3-bis(2-methylbutan-2-yl)phenoxy]acetyl]-4-[[4-[(3-chloro-4-hydroxyphenyl)diazenyl]phenyl]sulfonylamino]-1-hydroxy-3-phenyl-2-propyl-2H-naphthalene-1-carboxamide Chemical compound OC1(C(C(=C(C2=CC=C(C=C12)C(COC1=C(C(=CC=C1)C(C)(C)CC)C(C)(C)CC)=O)NS(=O)(=O)C1=CC=C(C=C1)N=NC1=CC(=C(C=C1)O)Cl)C1=CC=CC=C1)CCC)C(=O)N HLOBHXSSJVYSJT-UHFFFAOYSA-N 0.000 claims 1
AZOTUWMZGUOCIV-UHFFFAOYSA-N N,N-didodecyl-2-hydroxy-5-[[3-[[4-hydroxy-8-(methanesulfonamido)naphthalen-1-yl]diazenyl]phenyl]sulfonylamino]-3,4,6-trimethylbenzamide Chemical compound CC1=C(C(C(=O)N(CCCCCCCCCCCC)CCCCCCCCCCCC)=C(C(=C1C)NS(=O)(=O)C1=CC(=CC=C1)N=NC1=CC=C(C2=CC=CC(=C12)NS(=O)(=O)C)O)C)O AZOTUWMZGUOCIV-UHFFFAOYSA-N 0.000 claims 1
SRIZMKPMLGYIKR-WCNVQLFYSA-N OC1(C=C(C(C2=CC=CC=C12)(CCCCOC1=C(C=C(C=C1)C(C)(C)CC)C(C)(C)CC)NS(=O)(=O)C1=CC=C(C=C1)/N=N/C1=CC(=C(C2=CC=CC(=C12)NS(=O)(=O)C)O)S(NC(C)(C)C)(=O)=O)C)C(=O)N Chemical compound OC1(C=C(C(C2=CC=CC=C12)(CCCCOC1=C(C=C(C=C1)C(C)(C)CC)C(C)(C)CC)NS(=O)(=O)C1=CC=C(C=C1)/N=N/C1=CC(=C(C2=CC=CC(=C12)NS(=O)(=O)C)O)S(NC(C)(C)C)(=O)=O)C)C(=O)N SRIZMKPMLGYIKR-WCNVQLFYSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 82
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
239000000975 dye Substances 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
239000010410 layer Substances 0.000 description 41
238000002360 preparation method Methods 0.000 description 38
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 37
239000000047 product Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000013078 crystal Substances 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000008273 gelatin Substances 0.000 description 23
229920000159 gelatin Polymers 0.000 description 23
239000002904 solvent Substances 0.000 description 23
108010010803 Gelatin Proteins 0.000 description 22
235000019322 gelatine Nutrition 0.000 description 22
235000011852 gelatine desserts Nutrition 0.000 description 22
229910052757 nitrogen Inorganic materials 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
230000018109 developmental process Effects 0.000 description 20
239000003208 petroleum Substances 0.000 description 19
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
239000004848 polyfunctional curative Substances 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
238000001816 cooling Methods 0.000 description 10
229940073584 methylene chloride Drugs 0.000 description 10
229920000139 polyethylene terephthalate Polymers 0.000 description 10
239000005020 polyethylene terephthalate Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000012670 alkaline solution Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
238000009835 boiling Methods 0.000 description 7
150000002148 esters Chemical group 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 7
150000002989 phenols Chemical class 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
239000007787 solid Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 5
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 5
230000001681 protective effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000012190 activator Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000007844 bleaching agent Substances 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
150000008049 diazo compounds Chemical class 0.000 description 3
239000012156 elution solvent Substances 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000002955 isolation Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
AIEKCSPWYXDSKK-UHFFFAOYSA-N 2-hydroxy-3,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(O)=C1C AIEKCSPWYXDSKK-UHFFFAOYSA-N 0.000 description 2
FJWJYHHBUMICTP-UHFFFAOYSA-N 4,4-dimethylpyrazolidin-3-one Chemical compound CC1(C)CNNC1=O FJWJYHHBUMICTP-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
PRIIBHRLIUIMMF-UHFFFAOYSA-N 5-amino-n,n-didodecyl-2-hydroxy-3,4,6-trimethylbenzamide Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)C(=O)C1=C(C)C(N)=C(C)C(C)=C1O PRIIBHRLIUIMMF-UHFFFAOYSA-N 0.000 description 2
VJQHQIRKHZXMQF-UHFFFAOYSA-N 7-nitro-3-phenylnaphthalen-1-ol Chemical compound C=1C2=CC=C([N+]([O-])=O)C=C2C(O)=CC=1C1=CC=CC=C1 VJQHQIRKHZXMQF-UHFFFAOYSA-N 0.000 description 2
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-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
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
NHCUYZJWKREOHS-UHFFFAOYSA-N [4-[(3-chlorosulfonylphenyl)diazenyl]-5-(methanesulfonamido)naphthalen-1-yl] ethyl carbonate Chemical compound C12=C(NS(C)(=O)=O)C=CC=C2C(OC(=O)OCC)=CC=C1N=NC1=CC=CC(S(Cl)(=O)=O)=C1 NHCUYZJWKREOHS-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
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WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
239000001048 orange dye Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000012466 permeate Substances 0.000 description 1
CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
UQOHKJVQMDNTBF-UHFFFAOYSA-N phenyl 2-hydroxy-3,4,6-trimethylbenzoate Chemical compound OC1=C(C)C(C)=CC(C)=C1C(=O)OC1=CC=CC=C1 UQOHKJVQMDNTBF-UHFFFAOYSA-N 0.000 description 1
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
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 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000001044 red dye Substances 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Silver Salt Photography Or Processing Solution Therefor (AREA)
Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

CA326,712A 1979-05-01 1979-05-01 Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image Expired CA1132979A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA326,712A CA1132979A (fr)	1979-05-01	1979-05-01	Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA326,712A CA1132979A (fr)	1979-05-01	1979-05-01	Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image

Publications (1)

Publication Number	Publication Date
CA1132979A true CA1132979A (fr)	1982-10-05

Family

ID=4114109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA326,712A Expired CA1132979A (fr)	1979-05-01	1979-05-01	Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image

Country Status (1)

Country	Link
CA (1)	CA1132979A (fr)

1979
- 1979-05-01 CA CA326,712A patent/CA1132979A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-10-05	MKEX	Expiry

Publication	Publication Date	Title
CA1249473A (fr)	1989-01-31	Colorants cyan a base de derive de substitution de 4-nitrophenylazo-1-naphtol, possedant une meilleure stabilite a la lumiere
US4108850A (en)	1978-08-22	Positive-working immobile photographic azo compounds
US4142891A (en)	1979-03-06	Photographic products and processes employing nondiffusible azo dye-releasing compounds
EP0009989B1 (fr)	1985-01-23	Matériau d'enregistrement photographique comprenant des composés bloqués, utilisables en photographie
US4263393A (en)	1981-04-21	Novel electron donor precursors and photographic element containing them
US4371604A (en)	1983-02-01	Photographic material suited for use in diffusion transfer photography
US4255510A (en)	1981-03-10	Development restrainer precursors for photographic elements
US4619884A (en)	1986-10-28	Photographic products employing nondiffusible N',N'-diaromatic carbocyclic--or diaromatic heterocyclic--sulfonohydrazide compounds capable of releasing photographically useful groups
EP0059269B1 (fr)	1985-05-22	Eléments photographiques contenant des colorants bloqués ou des composés bloqués libérant des colorants et procédés pour leur utilisation
EP0011567B1 (fr)	1983-02-09	Elément photographique comprenant un 2,5-disulfonamidophénol ballasté comme composé pour bloquer des agents oxydés de transfert d'électrons
US4204870A (en)	1980-05-27	Photographic products and processes employing novel nondiffusible heterocyclyazonaphthol dye-releasing compounds
CA1144921A (fr)	1983-04-19	Produits et procedes pour la photographie, utilisant de nouveaux composes non diffusibles, qui liberent des colorants azoiques
US4258120A (en)	1981-03-24	Substituted sulfonamido compounds, photosensitive elements, film units, and processes for retaining a photographic image with same
US4149892A (en)	1979-04-17	Color diffusion transfer photographic elements
US4420550A (en)	1983-12-13	Photographic products and processes employing novel nondiffusible magenta dye-releasing compounds and precursors thereof
US4419435A (en)	1983-12-06	Photographic products and processes employing 6-heterocyclylazo-3-pyridinol nondiffusible cyan dye-releasing compounds and precursors thereof
CA1132979A (fr)	1982-10-05	Composes sulfonamido substitues, et elements photosensibles, pellicules et procedes pour garder une image
US4471045A (en)	1984-09-11	4-Hydroxyalkyl-substituted 3-pyrazolidinone electron transfer agents
US4605697A (en)	1986-08-12	Substituted sulfonamido compounds, photosensitive elements, film units, and processes for retaining a photographic image with same
US4436799A (en)	1984-03-13	Photographic products and processes employing novel nondiffusible magenta dye-releasing compounds and precursors thereof
US4391896A (en)	1983-07-05	Mixture of nondiffusible redox dye-releasers for curve shape control
US4564577A (en)	1986-01-14	Naphthoquinone redox dye-releasers
US4463081A (en)	1984-07-31	4-Hydroxyalkyl-substituted 3-pyrazolidinone electron transfer agents
US4152153A (en)	1979-05-01	Sulfonamido dye releasing compounds in photographic elements
US4192678A (en)	1980-03-11	N-alkyl- or N-aryl-benzisoxazolone scavenger compounds