JPH037097B2 - - Google Patents

Info

Publication number: JPH037097B2
Authority: JP; Japan
Prior art keywords: group; color; fluorine; short chain; color former
Prior art date: 1980-04-09
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

JP56053769A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56161542A (en

Inventor

Kareru Uan Puke Rafuaeru

Jakobu Monbaryuu Maruseru

Jozefu Uandoaru Jan

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.)

Agfa Gevaert NV

Original Assignee

Agfa Gevaert NV

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.)

1980-04-09

Filing date

1981-04-08

Publication date

1991-01-31

1981-04-08 Application filed by Agfa Gevaert NV filed Critical Agfa Gevaert NV

1981-12-11 Publication of JPS56161542A publication Critical patent/JPS56161542A/ja

1991-01-31 Publication of JPH037097B2 publication Critical patent/JPH037097B2/ja

Status Granted legal-status Critical Current

Links

-1 carbonylmethoxy group Chemical group 0.000 claims description 53
239000000839 emulsion Substances 0.000 claims description 43
229910052709 silver Inorganic materials 0.000 claims description 31
239000004332 silver Substances 0.000 claims description 31
239000000463 material Substances 0.000 claims description 28
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 19
239000011737 fluorine Substances 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 10
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 9
239000003086 colorant Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
239000000084 colloidal system Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000011593 sulfur Chemical group 0.000 claims description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
150000001555 benzenes Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
125000002723 alicyclic group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
150000001491 aromatic compounds Chemical class 0.000 claims description 2
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical class 0.000 claims description 2
125000004149 thio group Chemical group *S* 0.000 claims description 2
MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims 1
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
239000010410 layer Substances 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
150000001875 compounds Chemical class 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
230000000515 cyanogenic effect Effects 0.000 description 9
238000011161 development Methods 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000007259 addition reaction Methods 0.000 description 8
239000000975 dye Substances 0.000 description 8
239000004816 latex Substances 0.000 description 8
229920000126 latex Polymers 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
108010010803 Gelatin Proteins 0.000 description 7
239000002253 acid Substances 0.000 description 7
229920000159 gelatin Polymers 0.000 description 7
239000008273 gelatin Substances 0.000 description 7
235000019322 gelatine Nutrition 0.000 description 7
235000011852 gelatine desserts Nutrition 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
LAEATGZANNLZNQ-UHFFFAOYSA-N 4-(2-chloro-1,1,2-trifluoroethyl)sulfonylbenzoyl chloride Chemical compound FC(Cl)C(F)(F)S(=O)(=O)C1=CC=C(C(Cl)=O)C=C1 LAEATGZANNLZNQ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
229940125851 compound 27 Drugs 0.000 description 4
239000005457 ice water Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 3
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 3
LGDRIAAANGFYJK-UHFFFAOYSA-N 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoyl chloride Chemical compound FC(F)(F)C(F)C(F)(F)OC1=CC=C(C(Cl)=O)C=C1 LGDRIAAANGFYJK-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000003999 initiator Substances 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
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 2
FOBJABJCODOMEO-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanamide Chemical group NC(=O)C(F)(F)C(F)(F)C(F)(F)F FOBJABJCODOMEO-UHFFFAOYSA-N 0.000 description 2
JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
229910021612 Silver iodide Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
MPLZNPZPPXERDA-UHFFFAOYSA-N [4-(diethylamino)-2-methylphenyl]azanium;chloride Chemical compound [Cl-].CC[NH+](CC)C1=CC=C(N)C(C)=C1 MPLZNPZPPXERDA-UHFFFAOYSA-N 0.000 description 2
IFVYHJRLWCUVBB-UHFFFAOYSA-N allyl thiocyanate Chemical compound C=CCSC#N IFVYHJRLWCUVBB-UHFFFAOYSA-N 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
230000002860 competitive effect Effects 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000005012 migration Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
229940045105 silver iodide Drugs 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
239000004071 soot Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YXDMSFJDVHXFCV-UHFFFAOYSA-N 1,1,2,2-tetramethylcyclopentane Chemical group CC1(C)CCCC1(C)C YXDMSFJDVHXFCV-UHFFFAOYSA-N 0.000 description 1
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
IBWZJGRIWSCQHS-UHFFFAOYSA-N 1-(2-chloro-1,1,2-trifluoroethyl)sulfanyl-4-methylbenzene Chemical compound CC1=CC=C(SC(F)(F)C(F)Cl)C=C1 IBWZJGRIWSCQHS-UHFFFAOYSA-N 0.000 description 1
XAWXNFATQVEAGE-UHFFFAOYSA-N 1-(2-chloro-1,1,2-trifluoroethyl)sulfonyl-4-methylbenzene Chemical compound CC1=CC=C(S(=O)(=O)C(F)(F)C(F)Cl)C=C1 XAWXNFATQVEAGE-UHFFFAOYSA-N 0.000 description 1
GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
WFELVFKXQJYPSL-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(Cl)=O WFELVFKXQJYPSL-UHFFFAOYSA-N 0.000 description 1
ODPJQZNJZWLTJH-UHFFFAOYSA-N 2,3-dihydrotriazolo[4,5-d]pyrimidin-5-one Chemical class O=C1N=CC2=NNNC2=N1 ODPJQZNJZWLTJH-UHFFFAOYSA-N 0.000 description 1
LRKLDHJJKJBSIP-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]hexanoyl chloride Chemical compound CCCCC(C(Cl)=O)OC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC LRKLDHJJKJBSIP-UHFFFAOYSA-N 0.000 description 1
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
CITRBORWAIVSJU-UHFFFAOYSA-N 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)(F)C(F)C(F)(F)F)C=C1 CITRBORWAIVSJU-UHFFFAOYSA-N 0.000 description 1
UFHFSNVXOOEKOJ-UHFFFAOYSA-N 4-(2-chloro-1,1,2-trifluoroethyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=C(S(=O)(=O)C(F)(F)C(F)Cl)C=C1 UFHFSNVXOOEKOJ-UHFFFAOYSA-N 0.000 description 1
WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002494 Zein Polymers 0.000 description 1
SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
238000012644 addition polymerization Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
229960001748 allylthiourea Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001246 colloidal dispersion Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
230000001808 coupling effect Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000010556 emulsion polymerization method Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
150000002731 mercury compounds Chemical class 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
150000002736 metal compounds Chemical class 0.000 description 1
VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
SCMMLUUUPBPHMB-UHFFFAOYSA-N methyl 4-(1,1,2,3,3,3-hexafluoropropoxy)benzoate Chemical compound COC(=O)C1=CC=C(OC(F)(F)C(F)C(F)(F)F)C=C1 SCMMLUUUPBPHMB-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000001421 myristyl 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])[H] 0.000 description 1
VAVZHSBOROHMQD-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=CC(O)=C1 VAVZHSBOROHMQD-UHFFFAOYSA-N 0.000 description 1
UKNCFCOXZUVDGW-UHFFFAOYSA-N n-(4-amino-2-hydroxyphenyl)-4-(2-chloro-1,1,2-trifluoroethoxy)benzamide Chemical compound OC1=CC(N)=CC=C1NC(=O)C1=CC=C(OC(F)(F)C(F)Cl)C=C1 UKNCFCOXZUVDGW-UHFFFAOYSA-N 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000004010 onium ions Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000123 paper Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
150000003284 rhodium compounds Chemical class 0.000 description 1
230000005070 ripening Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003378 silver Chemical class 0.000 description 1
ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
FYOWZTWVYZOZSI-UHFFFAOYSA-N thiourea dioxide Chemical compound NC(=N)S(O)=O FYOWZTWVYZOZSI-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1
239000005019 zein Substances 0.000 description 1
229940093612 zein Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- 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
- G03C7/346—Phenolic couplers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Silver Salt Photography Or Processing Solution Therefor (AREA)

JP5376981A 1980-04-09 1981-04-08 Photographic material containing novel cyan formable coloring agent Granted JPS56161542A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8011693		1980-04-09

Publications (2)

Publication Number	Publication Date
JPS56161542A JPS56161542A (en)	1981-12-11
JPH037097B2 true JPH037097B2 (2)	1991-01-31

Family

ID=10512674

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5376981A Granted JPS56161542A (en)	1980-04-09	1981-04-08	Photographic material containing novel cyan formable coloring agent

Country Status (4)

Country	Link
US (1)	US4342825A (2)
EP (1)	EP0037602B1 (2)
JP (1)	JPS56161542A (2)
DE (1)	DE3164072D1 (2)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60209735A (ja) *	1984-04-03	1985-10-22	Konishiroku Photo Ind Co Ltd	ハロゲン化銀カラ−写真感光材料
US7279522B2 (en) *	2001-09-05	2007-10-09	3M Innovative Properties Company	Fluoropolymer dispersions containing no or little low molecular weight fluorinated surfactant
US6521395B1 (en) *	2002-01-30	2003-02-18	Eastman Kodak Company	Infrared couplers for incorporating and recovering metadata
US20080015304A1 (en) *	2006-07-13	2008-01-17	Klaus Hintzer	Aqueous emulsion polymerization process for producing fluoropolymers
GB0514398D0 (en)	2005-07-15	2005-08-17	3M Innovative Properties Co	Aqueous emulsion polymerization of fluorinated monomers using a fluorinated surfactant
US7671112B2 (en)	2005-07-15	2010-03-02	3M Innovative Properties Company	Method of making fluoropolymer dispersion
GB0525978D0 (en)	2005-12-21	2006-02-01	3M Innovative Properties Co	Fluorinated Surfactants For Making Fluoropolymers
GB0523853D0 (en) *	2005-11-24	2006-01-04	3M Innovative Properties Co	Fluorinated surfactants for use in making a fluoropolymer
US7754795B2 (en)	2006-05-25	2010-07-13	3M Innovative Properties Company	Coating composition
US8119750B2 (en) *	2006-07-13	2012-02-21	3M Innovative Properties Company	Explosion taming surfactants for the production of perfluoropolymers

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2895826A (en) *	1956-10-08	1959-07-21	Eastman Kodak Co	Photographic color couplers containing fluoroalkylcarbonamido groups
US3758308A (en) *	1971-02-18	1973-09-11	Eastman Kodak Co	Silver halide emulsion containing para fluoro phenols
US3880661A (en) *	1971-12-29	1975-04-29	Eastman Kodak Co	Silver halide emulsion containing acylamidophenol photographic couplers
JPS532728B2 (2) *	1974-01-25	1978-01-31
JPS5412220B2 (2) *	1974-04-12	1979-05-21
US4124396A (en) *	1977-03-03	1978-11-07	Eastman Kodak Company	2,5-Dicarbonylaminophenol dye-forming couplers
JPS5938577B2 (ja) *	1979-05-07	1984-09-18	コニカ株式会社	シアン色素画像の形成方法

1981
- 1981-03-16 EP EP81200293A patent/EP0037602B1/en not_active Expired
- 1981-03-16 DE DE8181200293T patent/DE3164072D1/de not_active Expired
- 1981-03-25 US US06/247,404 patent/US4342825A/en not_active Expired - Lifetime
- 1981-04-08 JP JP5376981A patent/JPS56161542A/ja active Granted

Also Published As

Publication number	Publication date
EP0037602B1 (en)	1984-06-13
EP0037602A1 (en)	1981-10-14
US4342825A (en)	1982-08-03
DE3164072D1 (en)	1984-07-19
JPS56161542A (en)	1981-12-11

Publication	Publication Date	Title
JPH0549975B2 (2)	1993-07-27
JPH0374375B2 (2)	1991-11-26
US4430422A (en)	1984-02-07	Method of dispersing photographic adjuvants in a hydrophilic colloid composition
JPH037097B2 (2)	1991-01-31
JPS5937497B2 (ja)	1984-09-10	カラ−写真材料の汚染防止剤
JPS5941183B2 (ja)	1984-10-05	感光材料
JPS5814668B2 (ja)	1983-03-22	シヤシンヨウゲンゾウヤク
JPS6326377B2 (2)	1988-05-30
JPH0257295B2 (2)	1990-12-04
JPH0332773B2 (2)	1991-05-14
EP0416684B1 (en)	1997-01-29	Photographic yellow couplers, method for their preparation and intermediates therefor
EP0037597B1 (en)	1984-06-13	Novel cyan-forming couplers and photographic elements containing such couplers
EP0001650B1 (en)	1982-07-28	Acylacetanilide compounds and their use as yellow forming colour couplers for silver halide photography
EP0269766B1 (en)	1991-02-06	Colour photographic element
EP0348133A2 (en)	1989-12-27	Novel pyrazolone photographic colour couplers and photographic elements contaning them
JPS6355543A (ja)	1988-03-10	発汗現象及びスタチツクマ−ク発生を防止したハロゲン化銀写真感光材料
JPH0248097B2 (ja)	1990-10-24	Karaashashinkankozairyo
JPS6037459B2 (ja)	1985-08-26	写真用シアンカプラ−
JPH0251492B2 (2)	1990-11-07
US3619196A (en)	1971-11-09	Light-sensitive color-photographic emulsions
JPS63241538A (ja)	1988-10-06	ハロゲン化銀写真感光材料
JPS6327703B2 (2)	1988-06-03
US4458011A (en)	1984-07-03	Ballasted compounds and photographic elements containing such compounds
JPH0583897B2 (2)	1993-11-30
JPS6410061B2 (2)	1989-02-21