US3788850A - Surface-active compounds for use as coating aids for film-forming coating compositions - Google Patents
Surface-active compounds for use as coating aids for film-forming coating compositions Download PDFInfo
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- US3788850A US3788850A US00150196A US3788850DA US3788850A US 3788850 A US3788850 A US 3788850A US 00150196 A US00150196 A US 00150196A US 3788850D A US3788850D A US 3788850DA US 3788850 A US3788850 A US 3788850A
- Authority
- US
- United States
- Prior art keywords
- coating
- stands
- coating compositions
- layer
- coating aids
- Prior art date
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- Expired - Lifetime
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- 239000008199 coating composition Substances 0.000 title abstract description 24
- 150000001875 compounds Chemical class 0.000 title abstract description 22
- 238000000576 coating method Methods 0.000 title description 48
- 239000011248 coating agent Substances 0.000 title description 47
- 239000000084 colloidal system Substances 0.000 abstract description 31
- 239000000463 material Substances 0.000 abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 10
- -1 SILVER HALIDE Chemical class 0.000 abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 230000002209 hydrophobic effect Effects 0.000 abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 5
- 150000001340 alkali metals Chemical class 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 229910052709 silver Inorganic materials 0.000 abstract description 5
- 239000004332 silver Substances 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 108010010803 Gelatin Proteins 0.000 description 19
- 229920000159 gelatin Polymers 0.000 description 19
- 239000008273 gelatin Substances 0.000 description 19
- 235000019322 gelatine Nutrition 0.000 description 19
- 235000011852 gelatine desserts Nutrition 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- SOQJHZSJZSNCBD-UHFFFAOYSA-N 14-methylpentadecyl hydrogen sulfate Chemical compound CC(C)CCCCCCCCCCCCCOS(=O)(=O)O SOQJHZSJZSNCBD-UHFFFAOYSA-N 0.000 description 6
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- CFSSWEQYBLCBLH-UHFFFAOYSA-N iso-hexadecyl alcohol Natural products CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WWKJSUQDMGKSIF-UHFFFAOYSA-N 16-methylheptadecyl hydrogen sulfate Chemical compound CC(C)CCCCCCCCCCCCCCCOS(O)(=O)=O WWKJSUQDMGKSIF-UHFFFAOYSA-N 0.000 description 3
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910021612 Silver iodide Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012612 commercial material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940045105 silver iodide Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 2
- 239000004440 Isodecyl alcohol Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000004435 Oxo alcohol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KBAYQFWFCOOCIC-GNVSMLMZSA-N [(1s,4ar,4bs,7s,8ar,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methanol Chemical compound OC[C@@]1(C)CCC[C@]2(C)[C@H]3CC[C@H](C(C)C)C[C@H]3CC[C@H]21 KBAYQFWFCOOCIC-GNVSMLMZSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 229920001477 hydrophilic polymer Polymers 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- SYXUBXTYGFJFEH-UHFFFAOYSA-N oat triterpenoid saponin Chemical compound CNC1=CC=CC=C1C(=O)OC1C(C=O)(C)CC2C3(C(O3)CC3C4(CCC5C(C)(CO)C(OC6C(C(O)C(OC7C(C(O)C(O)C(CO)O7)O)CO6)OC6C(C(O)C(O)C(CO)O6)O)CCC53C)C)C4(C)CC(O)C2(C)C1 SYXUBXTYGFJFEH-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920002494 Zein Polymers 0.000 description 1
- 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 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003831 antifriction material Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- WZEMSIKSCALWJZ-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO.CCO WZEMSIKSCALWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 229920001480 hydrophilic copolymer Polymers 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric 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
- G03C1/38—Dispersants; Agents facilitating spreading
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Definitions
- n 1 or m stands for 1 to 30 in which case n is 0 or 1,
- M stands for hydrogen, an alkali metal atom, ammonium or organic ammonium
- R stands for a branched-chain aliphatic group of 8 to 20 carbon atoms, which has at least 2 points of branching are described.
- the coating compositions are particularly useful in the formation of photographic silver halide materials and the layers coated therefrom do not exhibit hydrophobic areas leading to repellency spots or comets.
- This invention relates to surface active compounds suitable for use as coating aids for film-forming coating compositions comprising a hydrophilic colloid, and to hydrophilic colloid compositions comprising said coating aids.
- colloid compositions ready for coating are entirely hydrophilic to obtain a uniform layer therewith comprising no hydrophobic inclusions that may lead to repellency spots or comets in the said layer.
- the entire surface of a layer formed from such colloid compositions should be hydrophilic so that it can be rewet readily either by the processing solutions if said layer is the top layer of a photographic material to be processed, or by the coating composition, that will be applied to said layer for forming a next layer.
- air-bubbles are more easily carried along by a hydrophobic surface than by a hydrophilic surface, which air-bubbles will manifest themselves as small undeveloped areas in the processed material; moreover, when the material comprises hydrophobic inclusions so that its surface is not entirely hydrophilic but shows hydrophobic areas, water will not uniformly wet the said surface in that it is repelled on the hydrophobic, areas and form drops thereon. After processing such materials cannot be dried uniformly. They show a poor retouchability when it is desired to retouch such like materials.
- the maximum speed of the moving layer to be overcoated, at which no repellency occurs can be increased, when and to the extent that the surface to be overcoated is more hydrophilic; local hydrophobic areas at the surface of the "Ice layer to be overcoated can give rise to the formation of so-called repellency spots or comets in the said next layer.
- Saponin is conventionally used as coating aid for coating compositions comprising hydrophilic colloids. Though this product excells by its favorable anticomet action, it may vary markedly from batch to batch and is much more expensive than synthetic coating aids.
- a number of synthetic surface active agents have been proposed for use as coating aids to facilitate the coating of compositions comprising hydrophilic colloids more particularly gelatin layers. Most of these coating aids do improve some properties of the layer. However, they also adversely affect other desired properties. For instance, hydrophilic colloid layers comprising coating aids, which pervent the formation of comets in the said layers, may have an inadequate rewettability, which causes difficulties in the processing of photographic elements or it may be diffiicult to overcoat such layers when in wet state which is quite undesirable especially in simultaneous multilayer appilcations. In order to overcome these disadvantages it has been proposed to use mixtures of coating aids having different properties.
- 1111 stands for 0 in which case n is 1 or m stands for l to 30 in which case n is 0 to 1,
- M stands for hydrogen, an alkali metal atom such as lithium, sodium, potassium, ammonium or organic ammonium, e.g. diethanol ammonium, triethanol ammonium, triethyl ammonium and morpholinium,
- coating aids for use in coating compositions comprising a hydrophilic film-forming colloid such as gelatin. These coating aids are very easily to prepare and inexpensive.
- coating aids of this nature are the sulphates derived from alicyclic alcohols such as hydroabietyl alcohol and from the widely known branchedchain primary oxo-alcohols having at least 10 carbon atoms and at least 2 points of branching such as isodecyl alcohol, isotridecyl alcohol, isohexadecyl alcohol and isooctadecyl alcohol.
- Isodecyl alcohol is a commercial material prepared from C -olefins (tripropylene) by means of the oxo-synthesis (cf. H.
- Isotridecyl alcohol is a commercial material prepared from C olefins (triisobutylene, tetrapropylene or di(2-methyl-1- pentene)) by means of the oxo-reaction and is a mixture of primary branched-chain C -alcohols.
- Isohexadecyl alcohol and isooctadecyl alcohol are commercial materials prepared by aldol-condensation of C or C -aldehydes formed by oxo-synthesis; isohexadecyl alcohol is a mixture of branched-chain primary C -alcohols mainly consisting of alcohols as represented by the formula:
- alkali such as potassium hydroxide
- composition and properties of branched-chain oxo-alcohols which can be usde to form the coating aids of the invention or which can be used to synthesize Guerbet alcohols for use in the preparation of coating aids of the invention can be found in Fortschr. Chem. Forsch. Bd. 11/1, pp. 121-134.
- PREPARATION 1 Sodium isooctadecyl sulphate To a suspension of 28 :g. of sulphur trioxide in 200 ml. of anhydrous dichloroethane and 50 ml. of anhydrous dioxan a solution of 81 g. of isootadecyl alcohol (commercially available e.g. from Farbwerke Hoechst AG, Frankfurt (M), Hdchst, Germany) in 200 ml. of anhydrous dichloroethane was added dropwise at 5 C. The solution was kept overnight at room temperature. Subsequently, it was neutralized whilst stirring vigorously with a solution of 24 g. of sodium carbonate in 200 ml. of water.
- isooctadecyl sulphate To a suspension of 28 :g. of sulphur trioxide in 200 ml. of anhydrous dichloroethane and 50 ml. of anhydrous diox
- Coating aids according to the present invention promote the uniformity of coating and markedly reduce the tendency to form repellency spots.
- Coating compositions containing the coating aids of use according to the invention can be applied to dry surfaces as well as to wet surfaces and form layers that can be overco'ated easily in wet as well as in dry state, the said layers being either light-sensitive layers or not.
- Light-sensitive hydrophilic colloid materials comprising these coating aids also show improve wettability by photographic processing liquids.
- blends of two or more coating aids according to the present invention may sometimes be advisable to use blends of two or more coating aids according to the present invention. Indeed, it is observed frequently that one coating aid according to the invention performs best in one respect e.g. as regards its anticomet properties, whereas another is definitely superior in a different effect e.g. promoting uniformity of coating. These blends provide the major effects required and can often show characteristics superior to either coating aid alone. These effects may also result with blends of the coating aids of use according to the present invention with known coating aids such as saponine and other synthetic coating aids.
- the coating aids of the present invention has also favorable properties for dispersing or emulsifying substances in hydrophilic colloid compositions, which as a result of the presence of said coating aids also show improved coating characteristics.
- they are suitable as dispersing agent or emulsifying agent for substances that are to be incorporated into layers comprising a hydrophilic colloid and that would give rise to the formation of repellency spots in said layers when no compounds according to the invention were present.
- the coating aids according to the present invention are mainly intended for use in coating compositions comprising gelatin as hydrophilic colloid, they can also be used as coating aid for coating compositions comprising other hydrophilic colloidal materials or mixtures of them, e.g. hydrophilic natural colloids, modified hydrophilic natural colloids or synthetic hydrophilic polymers. More particularly these colloids may be selected of such film-forming natural or modified natural hydrophilic colloids as e.g. glue, casein, zein, hydroxyethyl cellulose, carboxymethyl cellulose, methyl cellulose, carboxymethyl hydroxyethyl cellulose, gum, arabic, sodium alginate and hydrophilic derivatives of such colloids.
- hydrophilic colloids e.g. glue, casein, zein, hydroxyethyl cellulose, carboxymethyl cellulose, methyl cellulose, carboxymethyl hydroxyethyl cellulose, gum, arabic, sodium alginate and hydrophilic derivatives of such colloids.
- polyvinyl alcohol poly-N-vinyl pyrrolidone
- polyvinyl amine polyethylene oxide
- polystyrene sulphonic acid polyacrylic acid
- hydrophilic copolymers and derivatives of such polymers e.g. to UK. Patent Specification 1,139,891 filed J an. 5, 1965 by Gevaert-Agfa NV. and to French Patent Specification 1,507,874 filed Jan. 10, 1967 by Gevaert- Agfa N.V., which relate i.a. to heatand/or pressuresensitive materials comprising a recording layer mainly consisting of a dispersion of hydrophobic thermoplastic polymer particles in a hydrophilic colloid binder.
- coating aids according to the present invention improve the coating characteristics of coating compositions already at a concentration as low as 0.01% by weight relative to the weight of dry colloid. Larger concentrations, however, can also be used but generally the concentration is not higher than 5% by weight based on the weight of dry colloid.
- the coating aids according to the invention are particularly suitable for use in a coating composition
- a coating composition comprising gelatin as hydrophilic colloid, either as an aqueous solution of gelatin or as a photographic emulsion, which ordinarily is composed of an aqueous solution of gelatin containing as the light-sensitive material therein, a silver halide such as silver bromide, silver chloride, silver iodide. or mixtures thereof or another light-sensitive substance.
- the emulsion may contain other added substances such as sensitizing dyes, hardeners, stabilizers, pH-adjusting compounds, color couplers, antifogging agents, development accelerators, thickening agents, developing agents, softening agents, or the like.
- the coating aids of the invention are useful in gelatin photographic emulsions, not only those, which are non-optically sensitized, but also in orthochromatic and panchromatic emulsions.
- This also includes gelatin emulsions intended for color photography such as those containing color forming couplers and finegrain emulsions of the Lippmann-type.
- the coating aids of use according to the present invention and their mixtures with other coating aids are also very useful in various other types of coating compositions in which gelatin is an important constituent, for example, in gelatin coating compositions to be applied as antihalation layer to the back or front of the base in a photographic material, as protective layer, as filter layer, as intermediate layer, as anticurling layer etc., which layers can also contain all kinds of other ingredients such as filling agents, hardening agents, antistatic agents, antifriction agents, or in any type of gelatin layer, which is coated from a composition comprising an aqueous solution of gelatin.
- the coating compositions in accordance with our invention may be coated on a transparent support e.g. of glass, cellulose esters, polyethylene terephthalate, or on a non- EXAMPLE 1
- a transparent support e.g. of glass, cellulose esters, polyethylene terephthalate, or on a non- EXAMPLE 1
- a series of two aqueous gelatin solutions comprising per kg. 50 g. of gelatin were prepared.
- gelatin solution Repellency spots per sq. m. (A) 18 (AH-l0 ml. of a 5% aqueous solution of the compound of preparation 3 We claim:
- a coating composition comprising a hydrophilic colloid and at least one surface active compound corresponding to the formula:
- n stands for 0 in which case n is 1 or m: stands for 1 to 30 in which case n is 0 or 1,
- M stands for hydrogen, an alkali metal atom, ammonium or organic ammonium
- R stands for a branched-chain aliphatic group of 8 to 20 carbon atoms, which has at least 2 points of branching.
- M stands for hydrogen, an alkali metal atom, ammonium or organic ammonium
- R stands for a branched-chain aliphatic group of 8 to 20 carbon atoms, which has at least 2 point of branchmg.
- the coating composition of claim 1 wherein the surface active compound is an isooctadecylsulfate.
- a photographic element according to claim 5 wherein the compound of the designated formula is an isooctadecylsulfate.
- a photographic element according to claim 5 wherein the compound of the designated formula is an isohexadecylsulfate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Colloid Chemistry (AREA)
- Paints Or Removers (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2704970 | 1970-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3788850A true US3788850A (en) | 1974-01-29 |
Family
ID=10253336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00150196A Expired - Lifetime US3788850A (en) | 1970-06-04 | 1971-06-04 | Surface-active compounds for use as coating aids for film-forming coating compositions |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3788850A (enrdf_load_stackoverflow) |
| BE (1) | BE767904A (enrdf_load_stackoverflow) |
| CH (1) | CH578890A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2127033A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2099746A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1345533A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4916054A (en) * | 1987-03-20 | 1990-04-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic element containing a coating aid |
| JPH0610728B2 (ja) | 1986-05-28 | 1994-02-09 | コニカ株式会社 | 新規な界面活性剤を含有するハロゲン化銀写真感光材料 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3918252A1 (de) * | 1989-06-05 | 1990-12-13 | Henkel Kgaa | Fettalkylsulfate und fettalkyl-polyalkylenglycolethersulfate, verfahren zu ihrer herstellung und ihre verwendung |
-
1971
- 1971-04-26 GB GB2704970A patent/GB1345533A/en not_active Expired
- 1971-05-27 FR FR7119680A patent/FR2099746A5/fr not_active Expired
- 1971-05-28 CH CH777471A patent/CH578890A5/xx not_active IP Right Cessation
- 1971-06-01 BE BE767904A patent/BE767904A/xx unknown
- 1971-06-01 DE DE19712127033 patent/DE2127033A1/de active Pending
- 1971-06-04 US US00150196A patent/US3788850A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0610728B2 (ja) | 1986-05-28 | 1994-02-09 | コニカ株式会社 | 新規な界面活性剤を含有するハロゲン化銀写真感光材料 |
| US4916054A (en) * | 1987-03-20 | 1990-04-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic element containing a coating aid |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2127033A1 (de) | 1971-12-16 |
| BE767904A (fr) | 1971-12-01 |
| CH578890A5 (enrdf_load_stackoverflow) | 1976-08-31 |
| GB1345533A (en) | 1974-01-30 |
| FR2099746A5 (enrdf_load_stackoverflow) | 1972-03-17 |
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