US3258338A - Photographic material containing softening agent - Google Patents
Photographic material containing softening agent Download PDFInfo
- Publication number
- US3258338A US3258338A US162272A US16227261A US3258338A US 3258338 A US3258338 A US 3258338A US 162272 A US162272 A US 162272A US 16227261 A US16227261 A US 16227261A US 3258338 A US3258338 A US 3258338A
- Authority
- US
- United States
- Prior art keywords
- compound
- gelatin
- softening agent
- mol
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000463 material Substances 0.000 title claims description 31
- 239000004902 Softening Agent Substances 0.000 title description 37
- 150000001875 compounds Chemical class 0.000 claims description 40
- 108010010803 Gelatin Proteins 0.000 claims description 37
- 229920000159 gelatin Polymers 0.000 claims description 37
- 239000008273 gelatin Substances 0.000 claims description 37
- 235000019322 gelatine Nutrition 0.000 claims description 37
- 235000011852 gelatine desserts Nutrition 0.000 claims description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- -1 silver halide Chemical class 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
- 229910052709 silver Inorganic materials 0.000 description 10
- 239000004332 silver Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 9
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 9
- 239000007859 condensation product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 125000001117 oleyl 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])=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])[H] 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 150000003016 phosphoric acids Chemical class 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940126543 compound 14 Drugs 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 229940126142 compound 16 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229960000776 sodium tetradecyl sulfate Drugs 0.000 description 2
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OWTQQPNDSWCHOV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO OWTQQPNDSWCHOV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000120 polyethyl acrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/31—Plasticisers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/38—Dispersants; Agents facilitating spreading
-
- 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
- G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
-
- 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
- Y10S430/14—Dimensionally stable material
Definitions
- This invention relates to a process for improving the physical properties of a photographic material and more particularly to an improved process for softening gelatin containing layers of such a photographic material.
- gelatin photographic materials it is important to incorporate softening agents to the gelatin for rendering the gelatin layers made therefrom better resistant to treatments at a low relative humidity. Indeed, gelatin layers or gelatin containing layers without softening agents are very brittle at low degree of relative humidity.
- gelatin polyalcohols such as glycerol, lactic acid, substituted phenols monoglycerides of fatty acids or amides such as formanilide as a softening agent.
- water-soluble long-chained aliphatic amines containing an amide function As compounds improving the elasticity and the flexibility of gelatino silver halide emulsion layers, water-soluble long-chained aliphatic amines containing an amide function, metal soaps of sulfonated caster oil which are insoluble in the photographic processing baths, poly(methXy alcohols) and aqueous dispersions of poly(ethyl acrylate) are also added.
- glycerol or other polyalcohols are strongly hygroscopic and thus injure the photographic and physical properties of the layers at rather high relative humidity.
- Softening agents for articles made of proteinaceous material are not numerous since the compatibility of the softening agents with the proteinaceous material is mostly insufiicient.
- softening agents for gelatin used for photographic purposes, there has moreover to be paid attention to their possible influence on the photographic properties of the materials to be manufactured. In some cases the transparency of the material should not be injured by the addition of softening agents.
- the phosphonic acid compounds and phosphoric acid compounds used according to the invention correspond to the following general formula:
- R and R represents an alkyl radical or an R (O-alkylene) radical, preferably an radial,
- R represents a hydroxyl group, an alkyl radical, an
- alkoxy radical or an R -(Oalkylene) -O-- radical preferably an R -(O-CH CH ),,O radical, wherein R represents an alkyl radical, an alkaryl radical or an acyl radical,
- n an integer of from 1 to 50.
- the phosphonic and phosphoric acid compounds used according to this invention can easily be prepared from the corresponding acid chlorides or acid anhydrides by reaction with higher as well as with lower alcohols, with monoalkylene glycol alkylethers or with polyoxyalkylene glycol monoalkyl ethers.
- COMPOUND l.TRIETHYL ORTHOPHOSPHORIC ACID ESTER This compound is marketed as Triethyl Phosphate by Albright & Wilson, Ltd., London.
- COMPOUND 3.-TRIETHY'L PHOSPHONIC ACID ESTER This compound is marketed as Diethyl ethyl phosphonate by Virginia-Carolina Chemical Corporation, Richmond, Va., U.S.A.
- COMPOUND 7.-TRI(DIETHYLENE GLYCOL MONOETHYL ETHER) PHOSPHATE In a three-necked flask of 3 liter, fitted with a stirrer, a thermometer, a condenser, a dropping funnel and the necessary calcium chloride tubes, the following mixture is stirred and cooled till 0 C.:
- the formed mixture consisting of two layers is first heated for 30 min., then cooled and finally extracted with ether for 8 hours.
- the obtained ether-extract is dried over anhydrous sodium sudfate and after drying the ether is distilled.
- the residue is then kept for 2 hours on a water bath in the reduced pressure formed by a water-jet pump in order to eliminate the remained traces of pyridine, if still present.
- a mixture consisting of g. of tridecycloxy pentadecaethylene glycol, 4 g. of pyridine, 25 g. of phosphorus oxychloride and 50 cm. of benzene is refluxed for 1 hr. After cooling, the formed pyridine hydrochloride is filtered oif and hydrochloric gas is led through the benzene solution. After filtration, the benzene solution is stirred and boiled with 10 0111. of water and then evaporated to dryness.
- COMPOUND 12 The softening agent with the following composition:
- COMPOUND 15 The softening agent with the following composition A mixture consisting of 20 g. of the condensation product of 15 mol of ethylene oxide, 1 mol of nonyl phenyl, 0.8 g. of dry phosphorous pentoxide and cm. of anhydrous ether is refluxed for 2 hr. Thereupon the ether is distilled.
- COMPOUND 16 The softening agent with the following composition COMPOUND 17
- the softening agents can be used in various compositions of matter. They are especially suited for being incorporated in gelatin containing layers which form part of a photographic material.
- the phosphonic and phosphoric acid compounds according to the invention can favorably be applied in a photographic silver halide emulsion layer or in another gelatin containing layer of a light sensitive photographic material such as an antihalation layer or other backing layer or supercoat on the emulsion layer as well as in gelatin containing layers of an image-receiving material for the manufacture of' images according to the silver complex diffusion transfer process described in US. patent specification 2,352,014.
- These softening agents can also favorably be used in the gelatin layer of the socalled blank film described in French patent specification 1,265,552.
- These layers may comprise compounds such as colour couplers, chemical or optical sensitizers, anti-fogging agents, optical brightening agents, wetting agents, development accelerators and matting agents, and can be cast upon paper, glass plates or films e.g. of cellulose esters, polyesters, polystyrene, etc.
- the softening agents according to this invention have also a good antistatic effect. This eifect is strongly pronounced when the softening agent is incorporated into a layer which is in the outer side of the photographic material such as a backing layer.
- softening agents according to the present invention are equally well suited for being applied in lightsensitive silver halide emulsion layers.
- Softening agents with a molecular weight of more than 1500 and having more than 20 oxyalkylene groups in their structure when applied in the light-sensitive silver halide emulsion layer in an amount as small as possible in order to obtain a practically usable softening effect give already rise to formation of fog.
- Such softening agents can be used in another layer than the silver halide emulsion layer of a photographic material.
- the amount of softening agent which can be used de pends on the desired improvement of the flexibility of the layers wherein they are incorporated.
- these compounds are used in an amount of 10% to 30% based on the weight of dry proteinaceous material.
- the phosphonic and phosphoric acid compounds ac cording to this invention are preferably added before coating the gelatin solution.
- some of these compounds with no more than alkylene oxide groups are preferably emulsified in the gelatin solution by means of emulsifying agents.
- the most suitable emulsifying agents are the anionactive wetting agents such as sodium salts of alkylsulfonic acids e.g. sodium tetradecylsulfate and the sodium salt of the condensation product of oleic acid and methyltaurine of the formula
- anionactive wetting agents such as sodium salts of alkylsulfonic acids e.g. sodium tetradecylsulfate and the sodium salt of the condensation product of oleic acid and methyltaurine of the formula
- Example 1 The equal parts of a aqueous solution of gelatin at pH 7 to 8, of the compounds identified in the following table, based on the weight of the dry gelatin, are added. After thoroughly mixing the gelatin solutions are applied onto glass-plates which are treated previously in such a way that after drying, the gelatin layers can easily be stripped off.
- the gelatin layers with a thickness of about 150 m are stripped off and cut into strips with a width of 15 mm. Thereupon the number of folds until breaking are determined with a M.I.T. fold tester at relative humidity and 20 C.
- Example 2 160 cm? of a 10% alcoholic solution of compound 8 are added to 1 kg. of a light-sensitive silver halide emulsion comprising g. of gelatin. This emulsion is cast onto a cellulose triacetate support and dried.
- the number of folds until breaking of the emulsion strips determined at 30% relative humidity and 20 C. with a M.I.T. fold tester amounts to 20.
- a similar emulsion strip without softening breaks at the fourth fold.
- Example 3 LAYER A To 1 liter of a 8% aqueous solution of gelatin containing an anti-halation dyestuif, cm. of a 10% alcoholic solution of the softening agent described as compound 8 in Example 1 are added. The solution is applied onto a cellulose triacetate support and dried.
- LAYER B To 1 liter of a 8% aqueous solution of gelatin containing manganese dioxide, 150 cm. of a 10% alcoholic solution of the softening agent described as compound 8 in Example 1 are added. The solution is applied onto a cellulose triacetate support and dried.
- Photographic material comprising a support and at least one gelatin layer containing a compound of the formula:
- each of R and R represents an alkyl radical or a R (O-alkylene) radical
- R represents a hydroxyl group, an alkyl radical, an
- alkoxy radical or a R (O-alkylene),,O-- radical wherein R represents an alkyl radical, an alkaryl radical or an acyl radical, and n represents an integer of from 1 to 50,
- said compound being present in a quantity of at least 3% by weight of the gelatin.
- Photographic material according to claim 1 comprising at least one gelatino silver halide emulsion layer and at least one other gelatin layer free of silver halide emulsion, and wherein each of said gelatino emulsion layer and said other gelatin layer contain a compound corresponding to the formula of claim 1 in an amount equal to at least 3% by weight of the gelatin therein.
- the photographic material of claim 1 wherein said layer contains a compound of the formula 0-(0 HzO H2O)4 lauryl O PO-(CH2C HzO-)4 lauryl 7.
- R and R each represents an R (O-alkylene) radical or an R CO(O-alkylene) radical R represents a hydroxyl group
- R represents a hydrocarbon radical
- n represents a positive number from 1 to 50.
- Sheet metal according to claim 8 wherein said compound is present in an amount equal to at least 3% by weight of the gelatin in said layer.
- Sheet material according to claim 10 wherein the 14.
- the sheet material of Claim 8 wherein said layer contains a mixture of of a compound of the formula 15.
- the sheet material of claim 8, wherein said layer contains a compound of the formula References Cited by the Examiner UNITED STATES PATENTS 2,887,381 5/1959 Levy 9694 2,940,854 6/1960 Gray 9694 2,950,980 8/1960 Hirsch 106125 2,958,605 11/1960 Leineretal 106125 3,058,941 10/1962 Birum 106 OTHER REFERENCES Buttrey, D. N., Plasticizers, London, Cleaver-Hume Press Ltd., 1957, pp. 35, 36.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Spectroscopy & Molecular Physics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE40382 | 1960-12-29 | ||
| BE40757 | 1961-06-26 | ||
| DEG32594A DE1146362B (de) | 1960-12-29 | 1961-06-27 | Verfahren zum Verbessern der physikalischen Eigenschaften eines photographischen Materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3258338A true US3258338A (en) | 1966-06-28 |
Family
ID=27158410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US162272A Expired - Lifetime US3258338A (en) | 1960-12-29 | 1961-12-26 | Photographic material containing softening agent |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3258338A (ru) |
| BE (2) | BE598619A (ru) |
| GB (1) | GB1009187A (ru) |
| NL (1) | NL272967A (ru) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3332777A (en) * | 1963-01-04 | 1967-07-25 | Ciba Ltd | Silver halide emulsion preparation using phosphoric acid esters as flocculants |
| US3364044A (en) * | 1962-08-20 | 1968-01-16 | Agfa Ag | Gelatine compositions containing pentaerythritol esters of phosphoric acids |
| US3380826A (en) * | 1964-07-23 | 1968-04-30 | Sylvania Electric Prod | Fabrication of image display screens |
| US3443951A (en) * | 1964-07-02 | 1969-05-13 | Agfa Gevaert Nv | Photographic light-sensitive materials containing phosphoric acid ester of aliphatic polyols |
| US3547650A (en) * | 1967-11-13 | 1970-12-15 | Du Pont | Silver halide emulsion comprising a gelatin - polyvinyl compound dispersion |
| US3607289A (en) * | 1965-03-17 | 1971-09-21 | Agfa Gevaert Ag | Gelatin emulsions having improved properties |
| US3655387A (en) * | 1970-09-15 | 1972-04-11 | Eastman Kodak Co | Antistatic photographic compositions |
| US4211836A (en) * | 1978-01-23 | 1980-07-08 | Fuji Photo Film Co., Ltd. | Method for dispersing oil-soluble photographic additives |
| FR2494861A1 (fr) * | 1980-11-26 | 1982-05-28 | Wolfen Filmfab Veb | Procede pour l'incorporation d'additifs photographiques hydrophobes, dans des milieux acqueux |
| US4353979A (en) * | 1979-07-25 | 1982-10-12 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019896B1 (de) * | 1979-06-01 | 1985-10-02 | American Hoechst Corporation | Farbprüffolie |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2887381A (en) * | 1957-07-29 | 1959-05-19 | Levy Marilyn | Sensitized photographic substances |
| US2940854A (en) * | 1956-08-16 | 1960-06-14 | Eastman Kodak Co | Gelatin silver halide emulsion plasticized with dicarboxylic acid esters |
| US2950980A (en) * | 1958-09-10 | 1960-08-30 | Hirsch Arthur | Adhesive compositions |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
| US3058941A (en) * | 1959-12-14 | 1962-10-16 | Monsanto Chemicals | Compositions comprising an organic polymer and an organo phosphorus compound |
-
0
- NL NL272967D patent/NL272967A/xx unknown
- BE BE605378D patent/BE605378A/xx unknown
- BE BE598619D patent/BE598619A/xx unknown
-
1961
- 1961-12-26 US US162272A patent/US3258338A/en not_active Expired - Lifetime
- 1961-12-29 GB GB46787/61A patent/GB1009187A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2940854A (en) * | 1956-08-16 | 1960-06-14 | Eastman Kodak Co | Gelatin silver halide emulsion plasticized with dicarboxylic acid esters |
| US2887381A (en) * | 1957-07-29 | 1959-05-19 | Levy Marilyn | Sensitized photographic substances |
| US2958605A (en) * | 1958-07-22 | 1960-11-01 | Union Carbide Corp | Adhesive compositions |
| US2950980A (en) * | 1958-09-10 | 1960-08-30 | Hirsch Arthur | Adhesive compositions |
| US3058941A (en) * | 1959-12-14 | 1962-10-16 | Monsanto Chemicals | Compositions comprising an organic polymer and an organo phosphorus compound |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364044A (en) * | 1962-08-20 | 1968-01-16 | Agfa Ag | Gelatine compositions containing pentaerythritol esters of phosphoric acids |
| US3332777A (en) * | 1963-01-04 | 1967-07-25 | Ciba Ltd | Silver halide emulsion preparation using phosphoric acid esters as flocculants |
| US3443951A (en) * | 1964-07-02 | 1969-05-13 | Agfa Gevaert Nv | Photographic light-sensitive materials containing phosphoric acid ester of aliphatic polyols |
| US3380826A (en) * | 1964-07-23 | 1968-04-30 | Sylvania Electric Prod | Fabrication of image display screens |
| US3607289A (en) * | 1965-03-17 | 1971-09-21 | Agfa Gevaert Ag | Gelatin emulsions having improved properties |
| US3547650A (en) * | 1967-11-13 | 1970-12-15 | Du Pont | Silver halide emulsion comprising a gelatin - polyvinyl compound dispersion |
| US3655387A (en) * | 1970-09-15 | 1972-04-11 | Eastman Kodak Co | Antistatic photographic compositions |
| US4211836A (en) * | 1978-01-23 | 1980-07-08 | Fuji Photo Film Co., Ltd. | Method for dispersing oil-soluble photographic additives |
| US4353979A (en) * | 1979-07-25 | 1982-10-12 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic materials |
| FR2494861A1 (fr) * | 1980-11-26 | 1982-05-28 | Wolfen Filmfab Veb | Procede pour l'incorporation d'additifs photographiques hydrophobes, dans des milieux acqueux |
Also Published As
| Publication number | Publication date |
|---|---|
| BE605378A (ru) | |
| BE598619A (ru) | |
| GB1009187A (en) | 1965-11-10 |
| NL272967A (ru) |
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