CA1099288A - Copulateurs a base de phenylsulfamoyle, substances qui en contiennent et elements photographiques pour trame sonore integrale - Google Patents

Copulateurs a base de phenylsulfamoyle, substances qui en contiennent et elements photographiques pour trame sonore integrale

Info

Publication number: CA1099288A
Authority: CA; Canada
Prior art keywords: coupler; dye; carbon atoms; ballast; solvent
Prior art date: 1978-07-27
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

CA312,037A

Other languages

English (en)

Inventor

Harland J. Osborn

Robert G. Cameron

Edward J. Walsh

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.)

1978-07-27

Filing date

1978-09-25

Publication date

1981-04-14

1978-09-25 Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co

1981-04-14 Application granted granted Critical

1981-04-14 Publication of CA1099288A publication Critical patent/CA1099288A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 34
-1 Phenylsulfamoyl Chemical group 0.000 title claims description 54
239000002904 solvent Substances 0.000 claims abstract description 84
238000010521 absorption reaction Methods 0.000 claims abstract description 33
238000001228 spectrum Methods 0.000 claims abstract description 26
239000002245 particle Substances 0.000 claims abstract description 25
230000015572 biosynthetic process Effects 0.000 claims abstract description 15
229910052709 silver Inorganic materials 0.000 claims description 60
239000004332 silver Substances 0.000 claims description 60
239000000839 emulsion Substances 0.000 claims description 38
125000004432 carbon atom Chemical group C* 0.000 claims description 36
125000000217 alkyl group Chemical group 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
239000000084 colloidal system Substances 0.000 claims description 14
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 8
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 7
230000002209 hydrophobic effect Effects 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
CWNSVVHTTQBGQB-UHFFFAOYSA-N N,N-Diethyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CC)CC CWNSVVHTTQBGQB-UHFFFAOYSA-N 0.000 claims description 5
230000006872 improvement Effects 0.000 claims description 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
229960002380 dibutyl phthalate Drugs 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229940000425 combination drug Drugs 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 3
239000000975 dye Substances 0.000 abstract description 87
238000005755 formation reaction Methods 0.000 abstract description 7
QGFHUZDBGWMHEN-UHFFFAOYSA-N 1-hydroxy-n-(3-sulfamoylphenyl)naphthalene-2-carboxamide Chemical group NS(=O)(=O)C1=CC=CC(NC(=O)C=2C(=C3C=CC=CC3=CC=2)O)=C1 QGFHUZDBGWMHEN-UHFFFAOYSA-N 0.000 abstract description 4
239000010410 layer Substances 0.000 description 77
229910001868 water Inorganic materials 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
230000009102 absorption Effects 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000000034 method Methods 0.000 description 17
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 16
239000007787 solid Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
239000000243 solution Substances 0.000 description 15
230000003595 spectral effect Effects 0.000 description 14
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
150000002828 nitro derivatives Chemical class 0.000 description 10
239000003921 oil Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
108010010803 Gelatin Proteins 0.000 description 9
239000008273 gelatin Substances 0.000 description 9
229920000159 gelatin Polymers 0.000 description 9
235000019322 gelatine Nutrition 0.000 description 9
235000011852 gelatine desserts Nutrition 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000008569 process Effects 0.000 description 8
238000012545 processing Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
238000000576 coating method Methods 0.000 description 7
238000011161 development Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000011248 coating agent Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000002356 single layer Substances 0.000 description 6
235000010265 sodium sulphite Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
230000004044 response Effects 0.000 description 5
238000012360 testing method Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
239000007844 bleaching agent Substances 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
230000035945 sensitivity Effects 0.000 description 4
GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 4
235000019982 sodium hexametaphosphate Nutrition 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
241001479434 Agfa Species 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfate Natural products OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
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 3
229940093499 ethyl acetate Drugs 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
239000011229 interlayer Substances 0.000 description 3
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
CSGQJHQYWJLPKY-UHFFFAOYSA-N CITRAZINIC ACID Chemical compound OC(=O)C=1C=C(O)NC(=O)C=1 CSGQJHQYWJLPKY-UHFFFAOYSA-N 0.000 description 2
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 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000008431 aliphatic amides Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
238000004061 bleaching Methods 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000013058 crude material Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008098 formaldehyde solution Substances 0.000 description 2
230000006870 function Effects 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
QHDYIMWKSCJTIM-UHFFFAOYSA-N phenyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)OC1=CC=CC=C1 QHDYIMWKSCJTIM-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 2
235000019252 potassium sulphite Nutrition 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
230000001235 sensitizing effect Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000007704 transition Effects 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 2
238000001429 visible spectrum Methods 0.000 description 2
JYHRLWMNMMXIHF-UHFFFAOYSA-N (tert-butylamino)boron Chemical compound [B]NC(C)(C)C JYHRLWMNMMXIHF-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
YDKAZDLKVFEUNI-UHFFFAOYSA-N 2-(2-ethylsulfanylethylsulfanyl)ethane-1,1-diol Chemical compound CCSCCSCC(O)O YDKAZDLKVFEUNI-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
UKJRKKQWBUZLPP-UHFFFAOYSA-N 3-methyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](C)=CSC2=C1 UKJRKKQWBUZLPP-UHFFFAOYSA-N 0.000 description 1
MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
WBQWCMNVBGTAAM-UHFFFAOYSA-N 4-[2,4-bis(2-methylbutan-2-yl)phenoxy]butanoyl chloride Chemical compound CCC(C)(C)C1=CC=C(OCCCC(Cl)=O)C(C(C)(C)CC)=C1 WBQWCMNVBGTAAM-UHFFFAOYSA-N 0.000 description 1
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
FNTZXIYFSZLXSW-UHFFFAOYSA-N COC(=O)C1=CC=CC=C1C(=O)OC.CCOC(=O)C1=CC=CC=C1C(=O)OCC.CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC.CCOC(=O)C1=CC=CC=C1C(=O)OCC.CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC FNTZXIYFSZLXSW-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000243251 Hydra Species 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910021538 borax Inorganic materials 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
239000006227 byproduct Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000002720 diazolyl group Chemical group 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000011152 fibreglass Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229940116335 lauramide Drugs 0.000 description 1
ILRSCQWREDREME-UHFFFAOYSA-N lauric acid amide propyl betaine Natural products CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000006224 matting agent Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000003607 modifier Substances 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
CIPHTOQKGSLCLV-UHFFFAOYSA-N n-phenylnaphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CC=C1 CIPHTOQKGSLCLV-UHFFFAOYSA-N 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920006289 polycarbonate film Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
150000003303 ruthenium Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
KICVIQZBYBXLQD-UHFFFAOYSA-M sodium;2,5-dihydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=C(O)C(S([O-])(=O)=O)=C1 KICVIQZBYBXLQD-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229910001428 transition metal ion Inorganic materials 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
229920003176 water-insoluble polymer Polymers 0.000 description 1
239000001043 yellow dye Substances 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers

Landscapes

Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)
Optical Record Carriers And Manufacture Thereof (AREA)
Heat Sensitive Colour Forming Recording (AREA)
Pyridine Compounds (AREA)

CA312,037A 1978-07-27 1978-09-25 Copulateurs a base de phenylsulfamoyle, substances qui en contiennent et elements photographiques pour trame sonore integrale Expired CA1099288A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US92874178A	1978-07-27	1978-07-27
US928,741		1978-07-27

Publications (1)

Publication Number	Publication Date
CA1099288A true CA1099288A (fr)	1981-04-14

Family

ID=25456673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA312,037A Expired CA1099288A (fr)	1978-07-27	1978-09-25	Copulateurs a base de phenylsulfamoyle, substances qui en contiennent et elements photographiques pour trame sonore integrale

Country Status (5)

Country	Link
JP (1)	JPS5941575B2 (fr)
CA (1)	CA1099288A (fr)
DE (1)	DE2930392A1 (fr)
FR (1)	FR2433777A1 (fr)
GB (1)	GB2027430B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62269958A (ja) *	1986-05-19	1987-11-24	Fuji Photo Film Co Ltd	ハロゲン化銀カラ−写真感光材料
DE3620167A1 (de) *	1986-06-14	1987-12-17	Bayer Ag	Verwendung einer chromhaltigen legierung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB909318A (en) *	1960-08-22	1962-10-31	Ferrania Spa	Improvements in the preparation of photographic colour images by colour development
GB1104729A (en) *	1965-10-13	1968-02-28	Agfa Gevaert Nv	Colour couplers for cyan
BE794284A (fr) *	1972-01-19	1973-07-19	Minnesota Mining & Mfg	Piste sonore sans argent pour photographie en couleur
JPS5796173A (en) *	1980-09-29	1982-06-15	Aruuma Shisutemusu Inc	Vertical load supporting frame

1978
- 1978-09-25 CA CA312,037A patent/CA1099288A/fr not_active Expired
1979
- 1979-07-26 GB GB7926025A patent/GB2027430B/en not_active Expired
- 1979-07-26 FR FR7919313A patent/FR2433777A1/fr active Granted
- 1979-07-26 DE DE19792930392 patent/DE2930392A1/de not_active Withdrawn
- 1979-07-27 JP JP54096010A patent/JPS5941575B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2930392A1 (de)	1980-02-14
JPS5941575B2 (ja)	1984-10-08
FR2433777A1 (fr)	1980-03-14
GB2027430A (en)	1980-02-20
JPS5521096A (en)	1980-02-14
FR2433777B1 (fr)	1985-03-15
GB2027430B (en)	1982-11-17

Legal Events

Date	Code	Title	Description
1998-04-14	MKEX	Expiry

Publication	Publication Date	Title
US4178183A (en)	1979-12-11	Thiazolyl coupler compositions and photographic elements suited to forming integral sound tracks
US5019492A (en)	1991-05-28	Photographic element and process comprising a blocked photographically useful compound
CA1251679A (fr)	1989-03-28	Blanchiment accru d'elements photographiques a l'halogenure d'argent et au colorant adsorbe
JPH0480375B2 (fr)	1992-12-18
EP0173302A2 (fr)	1986-03-05	Matériau photographique couleur à l'halogénure d'argent
US4522917A (en)	1985-06-11	Photographic silver halide light-sensitive material
US4250251A (en)	1981-02-10	Phenylsulfamoyl couplers, coupler compositions and photographic elements suited to forming integral sound tracks
US4678743A (en)	1987-07-07	Silver halide color photographic material
US4741994A (en)	1988-05-03	Silver halide color photographic material
US5242783A (en)	1993-09-07	Photographic material and process
US4040829A (en)	1977-08-09	Multilayer multicolor photographic materials
CA1099288A (fr)	1981-04-14	Copulateurs a base de phenylsulfamoyle, substances qui en contiennent et elements photographiques pour trame sonore integrale
US5612173A (en)	1997-03-18	One equivalent couplers and low PKA release dyes
US4233389A (en)	1980-11-11	Fluorinated 1-hydroxy-2-naphthamide coupler compositions and photographic elements suited to forming integral sound tracks
US5051343A (en)	1991-09-24	Photographic elements containing removable couplers
CA1099742A (fr)	1981-04-21	Copulateurs fluores a base de 1-hydroxy-2-naphtamide; substances qui en contiennent et elements photographiques servant a preparer des bandes sonores integrees
JPH0521219B2 (fr)	1993-03-23
EP0285176A2 (fr)	1988-10-05	Matériau photographique à l'halogénure d'argent
EP0492442B1 (fr)	1998-04-08	Eléments photographiques contenant un colorant filtre, éliminable
US5399469A (en)	1995-03-21	Spatially fixed absorber dyes in less sensitive layers
JP3247500B2 (ja)	2002-01-15	写真要素
GB2034061A (en)	1980-05-29	Silver halide colour photographic lightsensitive material
US5246820A (en)	1993-09-21	Carbamic acid solubilized smearing couplers
JPS62247363A (ja)	1987-10-28	ハロゲン化銀カラ−写真感光材料およびその処理方法
EP0250201A2 (fr)	1987-12-23	Elément photographique à l'halogénure d'argent et procédé