EP0093924A2 - Matériel d'enregistrement photographique - Google Patents
Matériel d'enregistrement photographique Download PDFInfo
- Publication number
- EP0093924A2 EP0093924A2 EP83103982A EP83103982A EP0093924A2 EP 0093924 A2 EP0093924 A2 EP 0093924A2 EP 83103982 A EP83103982 A EP 83103982A EP 83103982 A EP83103982 A EP 83103982A EP 0093924 A2 EP0093924 A2 EP 0093924A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- recording material
- radical
- material according
- photographic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 27
- 229920000126 latex Polymers 0.000 claims abstract description 81
- 239000004816 latex Substances 0.000 claims abstract description 44
- 108010010803 Gelatin Proteins 0.000 claims abstract description 22
- 229920000159 gelatin Polymers 0.000 claims abstract description 22
- 239000008273 gelatin Substances 0.000 claims abstract description 22
- 235000019322 gelatine Nutrition 0.000 claims abstract description 22
- 235000011852 gelatine desserts Nutrition 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 4
- 239000013543 active substance Substances 0.000 claims abstract description 3
- -1 silver halide Chemical class 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000000975 dye Substances 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 238000010525 oxidative degradation reaction Methods 0.000 claims description 2
- OYMXAJVFLHYOEE-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)prop-1-ene-1-sulfonic acid Chemical compound CC(C)=C(S(O)(=O)=O)NC(=O)C=C OYMXAJVFLHYOEE-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims 1
- 230000000536 complexating effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000011230 binding agent Substances 0.000 abstract description 14
- 229920006037 cross link polymer Polymers 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 238000005554 pickling Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 0 *C[C@](CC(*)=CC1C2CC2)C1N(C(C1)=O)N=C1NC(C1C=*CCC1)=O Chemical compound *C[C@](CC(*)=CC1C2CC2)C1N(C(C1)=O)N=C1NC(C1C=*CCC1)=O 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 description 2
- PWQANAQVNKODIO-UHFFFAOYSA-N 4-(2-carboxyprop-1-enyl)-2,4,6-trimethylhepta-2,5-dienedioic acid Chemical compound OC(=O)C(C)=CC(C)(C=C(C)C(O)=O)C=C(C)C(O)=O PWQANAQVNKODIO-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
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- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 2
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- YQCFXPARMSSRRK-UHFFFAOYSA-N n-[6-(prop-2-enoylamino)hexyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCNC(=O)C=C YQCFXPARMSSRRK-UHFFFAOYSA-N 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
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- 238000005691 oxidative coupling reaction Methods 0.000 description 2
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
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- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- AAXGLZUUHYACNA-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) prop-2-enoate Chemical compound COC(=O)COC(=O)C=C AAXGLZUUHYACNA-UHFFFAOYSA-N 0.000 description 1
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- MMIOSYPJSGTWEM-UHFFFAOYSA-N 2-(2-ethenylphenyl)acetic acid Chemical class OC(=O)CC1=CC=CC=C1C=C MMIOSYPJSGTWEM-UHFFFAOYSA-N 0.000 description 1
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
- MLFIYYDKLNZLAO-UHFFFAOYSA-N 2-aminoethane-1,1-diol Chemical compound NCC(O)O MLFIYYDKLNZLAO-UHFFFAOYSA-N 0.000 description 1
- ZULYWHOJRVBUJU-UHFFFAOYSA-N 2-aminoethylurea Chemical compound NCCNC(N)=O ZULYWHOJRVBUJU-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical class C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 description 1
- GROXSGRIVDMIEN-UHFFFAOYSA-N 2-methyl-n-prop-2-enylprop-2-enamide Chemical compound CC(=C)C(=O)NCC=C GROXSGRIVDMIEN-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 1
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 1
- RPNFCOCPQNDGPX-UHFFFAOYSA-N 4-methylhepta-2,5-dienedioic acid Chemical compound CC(C=CC(=O)O)C=CC(=O)O RPNFCOCPQNDGPX-UHFFFAOYSA-N 0.000 description 1
- WNEUWSYZWIROPS-UHFFFAOYSA-N 4-methylnona-2,7-dienedioic acid Chemical compound OC(=O)C=CC(C)CCC=CC(O)=O WNEUWSYZWIROPS-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- WXFIHSTVGBYMEE-UHFFFAOYSA-N 5-(2-carboxyethenyl)nona-2,7-dienedioic acid Chemical compound C(C=CC(=O)O)C(CC=CC(=O)O)C=CC(=O)O WXFIHSTVGBYMEE-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-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
- 239000004471 Glycine Substances 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 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 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- JBSVNYYKRNVOME-UHFFFAOYSA-N [2,2,2-trichloro-1-(2-methylprop-2-enoyloxy)ethyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(Cl)(Cl)Cl)OC(=O)C(C)=C JBSVNYYKRNVOME-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000005399 allylmethacrylate group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- OIPQUBBCOVJSNS-UHFFFAOYSA-L bromo(iodo)silver Chemical compound Br[Ag]I OIPQUBBCOVJSNS-UHFFFAOYSA-L 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 150000003940 butylamines Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- WJMQFZCWOFLFCI-UHFFFAOYSA-N cyanomethyl prop-2-enoate Chemical compound C=CC(=O)OCC#N WJMQFZCWOFLFCI-UHFFFAOYSA-N 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- JSERQGNBTYSHLP-UHFFFAOYSA-N deca-2,8-dienedioic acid Chemical compound OC(=O)C=CCCCCC=CC(O)=O JSERQGNBTYSHLP-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 125000006366 methylene oxy carbonyl group Chemical group [H]C([H])([*:1])OC([*:2])=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- HLEWRNFSHDSFFF-UHFFFAOYSA-N octa-2,6-dienedioic acid Chemical compound OC(=O)C=CCCC=CC(O)=O HLEWRNFSHDSFFF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001047 purple dye Substances 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005406 washing Methods 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/142—Dye mordant
Definitions
- the invention relates to a photographic recording material which contains crosslinked polymer latices in photographic light-sensitive and non-light-sensitive layers.
- Gelatin is generally used as a binder for photographic layers because of its advantageous properties as a protective colloid, as a dispersant and because of its chemical properties. Gelatin also has disadvantages as a photographic binder. So e.g. inadequate dimensional stability under changing climatic conditions, i.e. at different temperatures and humidity levels that are inherent in the layers formed from it.
- a disadvantage of these polymers is that they increase the viscosity of the coating solutions when mixed with gelatin, especially when the crosslinking agents required for layer hardening are added to the coating solutions. With the dwell times of the casting solutions that occur during the coating process, this leads to an increase in viscosity which makes a defined layer application per unit area impossible. Furthermore, linear high molecular weight polyacrylamides in aqueous solutions are so viscous that processing such solutions is associated with considerable difficulties.
- the object of the invention is to provide crosslinked polymer latices which are not susceptible to hydrolysis, which do not impair the sensitometric properties of color photographic materials and which are compatible with the customary binders and which can be prepared in a simple manner.
- the crosslinked polymer latices of the invention can always be used in an advantageous manner when it is necessary to use a synthetic binder and to avoid the disadvantages of a sharp increase in viscosity which is generally associated therewith. They are also suitable for introducing residues of photographically active agents in the form of substituents into a photographic layer.
- the structural unit characterized by the general formula represents the polymerized form of a low molecular weight carboxylic acid amide.
- Suitable monomeric carboxylic acid derivatives are those which are copolymerizable with the monomers M and V described below, e.g. Methacrylic acid, acrylic acid, crotonic acid, maleic acid or (vinylphenyl) acetic acid derivatives.
- R 2 and R 3 represent hydrogen, alkyl, aralkyl, aryl or a radical which has the function of a photographic building block, for example a color coupler, a UV absorber, a white coupler, a dye, a developer, a dye-releasing or releasing compound , an optical brightener, a metal ion donor, an antifoggant, a toner or a compound reactive with formalin.
- a color coupler for example a color coupler, a UV absorber, a white coupler, a dye, a developer, a dye-releasing or releasing compound , an optical brightener, a metal ion donor, an antifoggant, a toner or a compound reactive with formalin.
- R 2 or R 3 will generally be a radical with one of the functions mentioned. In principle, however, it is also possible for R 2 and R 3 together to represent such a radical.
- R 2 or R3 represents a color coupler residue which is capable of undergoing oxidative coupling with an oxidized p-phenylenediamine compound.
- oxidative coupling With oxidative coupling, the formation of a dye by reaction of the oxidized form, for example a phenylenediamine, with a nucleophile is closed understand.
- the precursor of a nucleophile for example a color coupler, becomes a nucleophile under development conditions, ie under alkaline conditions.
- R 2 or R 3 are color-coupling compounds which are contained as structural elements in conventional color couplers.
- the following color-coupling residues are mentioned as examples:
- R 2 or R 3 can also represent other residues of agents effective in the photographic layer, the following examples being mentioned:
- examples are those which are capable of fixing diffusing anionic dyes.
- a process that is of interest for example, for color diffusion processes or for determining filter dyes.
- Compounds which contain imidazolinium, pyridiium or tetraalkylammonium groups are particularly suitable for this purpose, examples of which are the above compounds C 9 , C 10 and C 12 .
- the polymer latices of the invention can advantageously also contain residues bonded to the nitrogen atom via an alkylene group, which stabilize the photographic material against UV light and / or oxidative degradation, as R 2 and R 3 .
- alkylene group which stabilize the photographic material against UV light and / or oxidative degradation
- R 2 and R 3 examples of such radicals are those denoted by C 1 to C 5 .
- radicals C 6 and C 7 are examples of radicals which complex metal ions and which, for example, enable metal complex dyes to be formed in photographic layers. Such residues preferably contain aminocarboxylic acid groups.
- V is the radical formed from a monomer which can be polymerized by addition polymerization and has at least two ethylenically unsaturated groups, the monomer corresponding to the following formula
- Particularly advantageous monomers for the formation of the units V are trivinylcyclohexane, divinylbenzene, tetraallyloxyethane, 1,4-butylene dimethacrylate. Two or more of the monomers mentioned can also be used side by side to form units V of the polymers according to the invention.
- a wide variety of monoethylenically unsaturated monomers copolymerizable with the customary monomers can be used for the units M.
- Monomers with conjugated ethylenically unsaturated bonds are also suitable for this purpose.
- Typical suitable monomers N are: ethylene, propylene, 1-butene, 4-methylpentene-1, styrene, ⁇ -methylstyrene, monoethylenically unsaturated esters of aliphatic acids, for example vinyl acetate, isopropenyl acetate, allyl acetate and the like; Esters of ethylenically unsaturated mono- and dicarboxylic acids, for example methyl methacrylate, ethyl acrylate, glycidyl acrylate, glycidyl methacrylate, butyl acrylate, cyanomethyl (meth) acrylate, nitrophenyl (meth) acrylate, carbomethoxymethyl (me
- Water-soluble monomers such as e.g. Acrylic acid, methacrylic acid, itaconic acid, maleic acid, acrylamido-2-methylpropanesulfonic acid, sulfoethyl methacrylate, N-vinyl pyrrolidone, vinyl pyridine or dimethylaminoethyl methacrylate.
- the grouping M can be formed not only from a single monomer, but also from various of the monomers mentioned.
- the latices according to the invention can be produced in various ways. According to a preferred production process, crosslinked polymer latices are used, which are converted into the polymeric amides in polymer-analogous reactions. Suitable starting compounds are e.g. Crosslinked (meth) acrylic ester latices which react with amines to form the polymeric amides according to the invention.
- the starting latices can be polymerized in a known manner by emulsion copolymerization of monomeric Esters with polyfunctional monomers, such as described in DE-OS 26 52 464, are prepared.
- monomeric esters which have a sufficient reactivity for the following stage to be performed in the aminolysis'.
- monomeric esters which are suitable for producing the crosslinked starting latices are (meth) acrylic acid methyl ester, cyanomethyl (meth) acrylate, nitrophenyl (meth) acrylate, carbomethoxymethyl (meth) acrylate, carboethoxymethyl (meth) acrylate or chloromethyl (meth) acrylate.
- Another production possibility is to start from crosslinked (meth) acrylic acid latices, as described in DE-OS 26 52 464. In this case it is necessary to activate the carboxylic acid groups before the reaction with the amines. opportunities for activating the carboxylic acid groups are known and are described, for example, in Houben-Weyl, volume 15/1 (1974), p. 28.
- the acid groups can also be activated by conversion into the acid halide or anhydride form.
- the reagents known from low molecular weight chemistry are suitable for this, such as thionyl chloride, phosphorus pentachloride, phosphorus trichloride or acetic anhydride.
- the crosslinked reactive starting latices are then reacted with amines to form the polymer latices according to the invention.
- the latices used as starting compounds can be present as aqueous dispersions. In those cases where the reactive starting latices can react with water, the starting latices are used as dispersions which contain organic, preferably polar, organic solvents as dispersants. It is often also expedient to use mixtures of water and organic solvent as dispersants.
- reaction conditions such as reaction time, temperature and the use of catalysts depend on the starting latex used.
- the reaction conditions can be chosen as they are known from the analogous reactions of linear uncrosslinked polymers or from low molecular weight chemistry. Descriptions of these possibilities can be found in Houben-Weyl, Volume 14/2 (1963), p. 738, Makromol. Chem., Rapid Connun. 1, 655 (1980), European Polymer Journal 15, 167 (1979), J. Polym. Sci. Chem. Ed. 12, 2453 (1974), J. Polym. Sci. Chem. Ed. 16, 1435 (1978), J. Polym. Sci.
- Suitable amines are ammonia or alkylamines, for example methylamine, dimethylamine, ethylamine, pro pylamine, or butylamine, arylamines, for example aniline, 4-methylaniline or optionally substituted aminophenols, aralkylamines, for example optionally substituted butylamines, aminocarboxylic acids, for example lysine or glycine, alkylenediamines, for example diaminoethane, diaminohexane or N, N'-dimethylaminopropylenediamine, hydroxyethanolamine, for example aminoethanolamine , Alkoxyalkylamines, for example methoxyethylamine, aminopyridines, for example 4-aminomethylpyridine or aminoalkylimidazoles, for example N-3-aminopropylimidazole, aminoureas, for example aminoethylurea, secondary cyclic amines in which R 2 and R
- the particles of the latices of the invention generally have diameters from 20 nm to 1 ⁇ m and preferably 30 to 300 nm.
- the latices are coated with the binders customary in photographic materials such as e.g. Gelatin, polyvinyl alcohol, carboxymethyl cellulose or hydroxyethyl cellulose are compatible and form transparent layers when mixed.
- the latices can be cleaned by the processes known to the person skilled in the art, for example by flakes or redispers yaw, by dialysis, by ultrafiltration or by mixing with gelatin, pasta and water.
- the latices can be stabilized by wetting agents. Often, however, stabilization by adding wetting agents is not necessary, especially if the latices contain ionic groups such as carboxyl or sulfonyl groups or quaternary ammonium groups.
- the latices are generally used as aqueous dispersions. If the preparation is carried out in a non-aqueous medium, the solvent is removed by known methods, e.g. by distillation, dialysis, ultrafiltration or by flaking and redispersing.
- the latices are generally mixed with natural or synthetic binders such as gelatin or other hydrophilic macromolecular substances.
- the amount of latex added is usually 20 to 85% by weight, preferably 50 to 85% by weight, based on the total amount of the binder used.
- the latices according to the invention are preferably used in a mixture with gelatin as a binder.
- the latices of the invention can advantageously be used in a wide variety of photographic materials, both in photosensitive and non-photosensitive layers of such materials.
- non-photosensitive Layers may be called receiving layers as used in diffusion transfer materials, further photographic auxiliary layers which are used in connection with light-sensitive layers.
- the latices can be used as a binder or for modifying the binder. They are also suitable as Ba - sis for polymer couplers or other polymeric excipients for use in a variety of radiation-sensitive materials, such as lithographic plates, photoresist materials and electrophotographic electrostatographic and radiographic materials.
- a mixture of 200 g of water, 2.5 g of a 30% by weight solution of the wetting agent as described for starting latex A, 29.4 g of carbomethoxymethyl acrylate and 1.2 g of divinylbenzene was heated to 75 ° C. under nitrogen. After stirring for 10 minutes, a solution of 0.3 g of potassium peroxodisulfate in 10 g of water and a solution of 0.3 g of sodium metabisulfite in 10 g of water were simultaneously added dropwise within one hour. After stirring for a further 3 hours at 75 ° C., the latex obtained was filtered. The solids content was 11.5% by weight.
- Latex 1 As described under Latex 1, the starting latices A to E were reacted with various amines. The reaction conditions and the degree of conversion are given in Table 1 below.
- the latices 3, 4, 9, 10 and 12 can be used as binder additives.
- the latices 1, 2, 5, 6, 7, 8, 11 and 13 are suitable for fixing metal ions such as Cu ++ , Zn ++ , Ni ++ while the latices 1, 2, 6, 8, 11 and 13 after quaternization with alkylating agents such as benzyl chloride, dimethyl sulfate, epichlorohydrin or chloroethanol, can also be used as mordants.
- a usgangslatex A (8.6 wt .-% aqueous dispersion) was mixed with 20 mol% (based on the Ester Disability Laboratory), KOH and stirred at 30 ° C. After 1 hour the pH of the latex had dropped to 7.5. It was then reacted with 2,4-dichloro-3-methyl-6- (5-aminopentylcarbonamido) phenol in water / acetonitrile as described for latex 2. After dialysis, a cross-linked latex with carboxylate and color coupling groups was obtained. The degree of conversion is 38% by weight, based on the color-coupling groups.
- the latex was then flocked by adding a cyclohexane / acetone mixture, the polymer was filtered off, washed and redispersed in water.
- the latex obtained contains the coupler residue R A. The conversion is determined by determining the acid number and is 55%.
- a 10 wt .-% aqueous binder solution consisting of a mixture of gelatin and linear high molecular weight polyacrylamide in a weight ratio of 10: 1 and 100 ml of a 0.2 wt .-% solution of the below.
- Hardening agent A in water was poured onto a cellulose triacetate base provided with an adhesive layer using a conventional cascade casting machine and dried.
- the curing agent A used has the formula
- the material was stored for 7 days at 30 ° C and 50% relative humidity.
- the wet scratch resistance (NKF) and the swelling factor (QF) were then measured.
- a metal tip of a defined size is passed over the wet layer and loaded with increasing weight.
- the wet scratch resistance is indicated by the weight at which the tip leaves a visible scratch mark on the layer.
- a high weight corresponds to a high wet scratch resistance.
- the swelling is after 10 minutes of treatment of a test strip in distilled water at 22 ° C gra measured vimetrically. It is characterized by the swelling factor:
- the example was repeated using the latices 6 and 12 according to the invention instead of polyacrylamide.
- the changes (in%) of swelling factor ( ⁇ QF) and wet scratch resistance ( ⁇ NKF) were determined using the following formulas:
- the layer properties are significantly improved by the compounds according to the invention compared to linear polymers.
- the resulting mordant samples were soaked for 2 minutes and placed in an aqueous dye solution of 0.05 g of the compound immersed in 100 ml of phosphate buffer (pH 13.5), 1, 2, 3 and 5 minutes.
- a strong coloring of the pickling layers was obtained after just 1 minute.
- the advantageous pickling ability of the pickling layers is shown by the fact that the dye cannot be removed even by washing for several hours.
- the example was made using a cyan dye of the formula and a purple dye of the formula repeated. These samples, too, can be washed for several hours without being discolored.
- the latices of the invention are compared to graft polymers on acrylamide as described in US Pat. No. 3,026,293.
- the viscosities of latex 11 according to the invention and of the copolymer mixture specified in Example 1 of US Pat. No. 3,026,293 were compared.
- the run-out times of the polymer dispersions set at 10% by weight from a DIN cup (4 mm nozzle) were used as a measure of the viscosity.
- the example shows the more favorable viscosity behavior of the latex of the invention compared to the polymer of US Pat. No. 3,026,293, which is composed of similar monomers.
- the latex 16 was admixed with a silver halide gelatin emulsion which was sensitized to red according to the color coupler introduced.
- the silver halide gelatin emulsion used consisted of 75 g of silver bromide iodide (iodide content 3 mol%) and 72 g of gelatin, based on 1 kg of emulsion.
- the emulsion thus prepared was applied to a cellulose triacetate layer support provided with an adhesive layer and dried.
- the sample was exposed using a sensitometer and then processed in the manner described below. Relative sensitivity and color yield were determined.
- a material was used which, instead of the latex according to the invention, contained 16 2,4-dichloro-3-methyl-6- (tridecylcarbonamido) phenol dissolved in tricresyl phosphate in the form of an emulsion.
- the relative sensitivity was determined using a sensitometer.
- the smaller number means higher sensitivity (3 units correspond to a DIN).
- the example shows that with the latexes containing color couplers according to the invention, higher sensitivities and color yields are obtained.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3217020 | 1982-05-06 | ||
DE19823217020 DE3217020A1 (de) | 1982-05-06 | 1982-05-06 | Photographisches aufzeichnungsmaterial |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0093924A2 true EP0093924A2 (fr) | 1983-11-16 |
EP0093924A3 EP0093924A3 (en) | 1985-01-09 |
EP0093924B1 EP0093924B1 (fr) | 1987-05-27 |
Family
ID=6162923
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83103982A Expired EP0093924B1 (fr) | 1982-05-06 | 1983-04-23 | Matériel d'enregistrement photographique |
Country Status (5)
Country | Link |
---|---|
US (1) | US4513080A (fr) |
EP (1) | EP0093924B1 (fr) |
JP (1) | JPS58214146A (fr) |
CA (1) | CA1248392A (fr) |
DE (2) | DE3217020A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0185793A1 (fr) * | 1984-12-24 | 1986-07-02 | Agfa-Gevaert N.V. | Latex d'un copolymère et matériaux photographiques à base d'halogénures d'argent contenant un tel latex |
EP0224951A1 (fr) * | 1985-11-26 | 1987-06-10 | Agfa-Gevaert N.V. | Elément récepteur d'image comprenant des agents anti-altération de couleurs |
EP0274764A1 (fr) * | 1987-01-16 | 1988-07-20 | Agfa-Gevaert N.V. | Mordants polymères pour colorants acides |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0666029B2 (ja) * | 1984-03-09 | 1994-08-24 | 富士写真フイルム株式会社 | 写真感光材料 |
JPS6169061A (ja) * | 1984-09-12 | 1986-04-09 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
EP0219101B1 (fr) * | 1985-10-16 | 1992-12-30 | Konica Corporation | Matériau photographique à l'halogénure d'argent |
JPS62178233A (ja) * | 1986-01-31 | 1987-08-05 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPS63257751A (ja) * | 1987-04-15 | 1988-10-25 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPH07122747B2 (ja) * | 1987-09-11 | 1995-12-25 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
IT1232339B (it) * | 1989-09-25 | 1992-01-28 | Minnesota Mining & Mfg | Elementi fotografici multistrato aventi una migliorata qualita' di stesa. |
JPH0466934A (ja) * | 1990-07-04 | 1992-03-03 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
GB9203350D0 (en) * | 1992-02-17 | 1992-04-01 | Ici Plc | Polymeric film |
US5384235A (en) * | 1992-07-01 | 1995-01-24 | Eastman Kodak Company | Photographic elements incorporating polymeric ultraviolet absorbers |
US5858633A (en) * | 1994-12-21 | 1999-01-12 | Eastman Kodak Company | Photographic elements containing 3-alkyl group substituted 2-hydroxyphenylbenzotriazole UV absorbing polymers |
US5766834A (en) * | 1996-05-17 | 1998-06-16 | Eastman Kodak Company | Photographic element containing ultraviolet absorbing polymer |
US6136496A (en) * | 1998-02-08 | 2000-10-24 | Agfa-Gevaert, N.V. | Imaging element for making an improved printing plate according to the silver salt diffusion transfer process |
DE69806019D1 (de) * | 1998-11-23 | 2002-07-18 | Agfa Gevaert Nv | Verfahren zur Herstellung eines Bildelements, das zur Herstellung einer Druckplatte nach dem Silbersalz-Diffusionsübertragungsverfahren verwendet werden kann |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2355313A1 (fr) * | 1976-06-15 | 1978-01-13 | Agfa Gevaert | Copulants polymeres pour la photographie aux halogenures d'argent |
DE2846044A1 (de) * | 1977-10-24 | 1979-04-26 | Konishiroku Photo Ind | Fotografisches element |
US4193796A (en) * | 1978-12-20 | 1980-03-18 | Eastman Kodak Company | Polymers for use in image receiving elements for metallizable dyes in image transfer film units |
GB2029593A (en) * | 1978-08-31 | 1980-03-19 | Fuji Photo Film Co Ltd | Photographic material containing a polymer mordant |
US4234671A (en) * | 1978-03-20 | 1980-11-18 | Konishiroku Photo Industry Co., Ltd. | Color diffusion transfer dye mordant |
GB2064800A (en) * | 1979-11-05 | 1981-06-17 | Fuji Photo Film Co Ltd | Photographic material |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1101409A (en) * | 1965-06-01 | 1968-01-31 | Fuji Photo Film Co Ltd | Improvements in and relating to photographic light sensitive materials |
US3615624A (en) * | 1968-01-29 | 1971-10-26 | Eastman Kodak Co | Peptizers for silver halide emulsions useful in photography |
US3591387A (en) * | 1969-04-02 | 1971-07-06 | Eastman Kodak Co | Silver halide emulsions comprising polymeric acrylamides as sensitizing additives |
US3852073A (en) * | 1970-12-31 | 1974-12-03 | Polaroid Corp | Silver halide emulsions comprising polymeric peptizers |
GB1381263A (en) * | 1971-01-11 | 1975-01-22 | Agfa Gevaert | Polymeric mordanting agents for anionic compounds |
US3816129A (en) * | 1973-01-02 | 1974-06-11 | Polaroid Corp | Synthetic silver halide emulsion binder |
DE2304319A1 (de) * | 1973-01-30 | 1974-08-08 | Agfa Gevaert Ag | Polymere verbindungen und ihre verwendung in photographischen farbmaterialien |
DE2541754C2 (de) * | 1975-09-19 | 1986-01-09 | Agfa-Gevaert Ag, 5090 Leverkusen | Photographische Silberhalogenidemulsion |
US4145221A (en) * | 1977-11-08 | 1979-03-20 | Gaf Corporation | Synthetic polymer latices in photographic silver halide emulsions containing multivalent metal salts |
EP0027284B1 (fr) * | 1979-10-15 | 1983-09-14 | Agfa-Gevaert N.V. | Latex à base de copolymères et matériaux photographiques aux halogénures d'argent contenant ce latex |
US4288523A (en) * | 1980-03-14 | 1981-09-08 | Polaroid Corporation | Diffusion control layers in diffusion transfer photographic products |
JPS6022340B2 (ja) * | 1980-04-07 | 1985-06-01 | 富士写真フイルム株式会社 | 写真感光材料 |
JPS5719735A (en) * | 1980-07-10 | 1982-02-02 | Fuji Photo Film Co Ltd | Photographic sensitive material |
JPS5794752A (en) * | 1980-12-05 | 1982-06-12 | Fuji Photo Film Co Ltd | Color photographic sensitive silver halide material |
-
1982
- 1982-05-06 DE DE19823217020 patent/DE3217020A1/de not_active Withdrawn
-
1983
- 1983-04-23 EP EP83103982A patent/EP0093924B1/fr not_active Expired
- 1983-04-23 DE DE8383103982T patent/DE3371819D1/de not_active Expired
- 1983-05-04 CA CA000427420A patent/CA1248392A/fr not_active Expired
- 1983-05-04 JP JP58077666A patent/JPS58214146A/ja active Pending
-
1984
- 1984-09-10 US US06/648,616 patent/US4513080A/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2355313A1 (fr) * | 1976-06-15 | 1978-01-13 | Agfa Gevaert | Copulants polymeres pour la photographie aux halogenures d'argent |
DE2846044A1 (de) * | 1977-10-24 | 1979-04-26 | Konishiroku Photo Ind | Fotografisches element |
US4234671A (en) * | 1978-03-20 | 1980-11-18 | Konishiroku Photo Industry Co., Ltd. | Color diffusion transfer dye mordant |
GB2029593A (en) * | 1978-08-31 | 1980-03-19 | Fuji Photo Film Co Ltd | Photographic material containing a polymer mordant |
US4193796A (en) * | 1978-12-20 | 1980-03-18 | Eastman Kodak Company | Polymers for use in image receiving elements for metallizable dyes in image transfer film units |
GB2064800A (en) * | 1979-11-05 | 1981-06-17 | Fuji Photo Film Co Ltd | Photographic material |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0185793A1 (fr) * | 1984-12-24 | 1986-07-02 | Agfa-Gevaert N.V. | Latex d'un copolymère et matériaux photographiques à base d'halogénures d'argent contenant un tel latex |
EP0224951A1 (fr) * | 1985-11-26 | 1987-06-10 | Agfa-Gevaert N.V. | Elément récepteur d'image comprenant des agents anti-altération de couleurs |
EP0274764A1 (fr) * | 1987-01-16 | 1988-07-20 | Agfa-Gevaert N.V. | Mordants polymères pour colorants acides |
Also Published As
Publication number | Publication date |
---|---|
EP0093924A3 (en) | 1985-01-09 |
EP0093924B1 (fr) | 1987-05-27 |
JPS58214146A (ja) | 1983-12-13 |
US4513080A (en) | 1985-04-23 |
CA1248392A (fr) | 1989-01-10 |
DE3371819D1 (en) | 1987-07-02 |
DE3217020A1 (de) | 1983-11-10 |
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