US3165409A - Derivatives of certain highly branched chain acids as coating aids - Google Patents
Derivatives of certain highly branched chain acids as coating aids Download PDFInfo
- Publication number
- US3165409A US3165409A US171560A US17156062A US3165409A US 3165409 A US3165409 A US 3165409A US 171560 A US171560 A US 171560A US 17156062 A US17156062 A US 17156062A US 3165409 A US3165409 A US 3165409A
- Authority
- US
- United States
- Prior art keywords
- coating
- gelatin
- aid
- coating aids
- sodium salt
- 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
- 238000000576 coating method Methods 0.000 title claims description 61
- 239000011248 coating agent Substances 0.000 title claims description 58
- 239000002253 acid Substances 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title description 2
- 239000000839 emulsion Substances 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 108010010803 Gelatin Proteins 0.000 description 26
- 229920000159 gelatin Polymers 0.000 description 26
- 239000008273 gelatin Substances 0.000 description 26
- 235000019322 gelatine Nutrition 0.000 description 26
- 235000011852 gelatine desserts Nutrition 0.000 description 26
- 239000000203 mixture Substances 0.000 description 15
- 159000000000 sodium salts Chemical class 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000008199 coating composition Substances 0.000 description 7
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- -1 taurine compound Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- MKWKNSIESPFAQN-UHFFFAOYSA-N N-cyclohexyl-2-aminoethanesulfonic acid Chemical compound OS(=O)(=O)CCNC1CCCCC1 MKWKNSIESPFAQN-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 101100189913 Caenorhabditis elegans pept-1 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CAVXVRQDZKMZDB-UHFFFAOYSA-N sodium;2-[dodecanoyl(methyl)amino]ethanesulfonic acid Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CCS(O)(=O)=O CAVXVRQDZKMZDB-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003746 surface roughness Effects 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
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/38—Dispersants; Agents facilitating spreading
Definitions
- aqueous gelatin coating compositions particularly gelatin-silver halide photographic emulsions
- a coating aid to facilitate the application of the layer to the support.
- This application of gelatin composition can be either as a single layer or in multilayers such as by simultaneous application.
- the presence of coating aid reduces defects such as repellencies, pencil line streaks, and the like in the coating when dry. In such coating operations, however, the coating aids used often fail to induce adequate rewettability of the layer which usually exhibits surface slickness.
- this surface slickness or slipperiness is especially undesirable in certain photo graphic products because of difficulties in handling and possible telescoping of the film wound in the form of rolls.
- a mixture of two surfactants as the coating aid to impart both desired surface roughness and rewettability of the dry coating.
- the mixing of coating aids sometimes bothersome but in addition some of the surfactants proposed for that purpose are naturally occurring materials and may vary in quality or contain impurities undesirable for photographicuse.
- n is an integer 1 or 2
- Q is a bond or R is alkyl of 1 to4 carbon atoms or cycloalkyl
- M is a substituent such as Na, K, Li, NH or alkylammonium to give a water soluble salt.
- the branched alkyl substituent attached to the benzene ring have 8-16 carbon atoms although included within our invention are the coating aids'in which two alkyl substituents may be on the benzene ring, the sum of the carbons of these alkyls being 8-16 carbon atoms.
- some of the compounds which have been considered most convenient to use are alkaryl compounds in which the sum of the alkyl substituents of the alkaryl has 8, 10, 12, 15 or the like carbon atoms either one or two alkyls being attached to'the benzene ring.
- the nitrogen of the taurine compound has as a substituent thereon alkyl of 14 carbon atoms such as methyl, ethyl or cycloalkyl i.e. cyclohexyl.
- Some coating aids for use in gelatin coating compositions in accordance with our invention are:
- Example 1 354 parts (0.359 mole) of a 23.8% aqueous solution' of the sodium salt of N-cyclohexyltaurine was evaporated in vacuo on a steam bath to /s /2 the original volume so as to remove any cyclohexylamine which might be present. The mass was then diluted withwater to 354 parts and 200 parts of acetone were added. Added simultaneously to the stirred solution at 60 C. while emulsion layer and a clear gelatin overcoating were apaids was used so as to give both good developer spread and resistance to slipping. The following results were obtained:
- Example4 In a coating run similar to that described in Example 3 except that N-pentadecylphenoxyacetyl-N-methyltaurine,
- Example 5 In a coating run similar to that described in Example 3 in which N-p-t.-octylpheiioxyacetylglycyl N-methyltau l R L rine, sodium salt (OPGMT), was used as the coating aid; Coating Aidv 325 ifi the following results were obtained: v (25 ft.) Streaks R 1 7 L n rol 12 Med Coating Aid len e ies Mottle tiidir ial T 0 (25it.
- a compositionof matter comprising gelatin cone.
- R is branched alkyl, (R) totals 8 to 16 carbon atoms, n is an integer of 1 to 2, Q is selected from the group consisting of a bond and C--HNCH2 I; R is selected from the group consisting of alkyls of 1 to 4 carbon atoms and cycloalkyl, and M is a substituent selected from the group consisting of Na, K, Li, NH, and alkylammonium. 2.
- a composition of matter comprising gelatin containing coating aid corresponding to the following formula:
- R is branched alkyl of 8 to 16 carbon atoms and R is selected from the group consisting of alkyls of 1 to 4 carbon atoms and cycloalkyl.
- M is a substituent selected from the group consisting of Na, K, Li, NH, and alkylammonium.
- composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-ptert.-octylphenoXyacetyl-N-cyclohexyltaurine.
- composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-ptert.-octylphenoxyacetyl-N-methyltaurine.
- composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N- pentadecylphenoxyacetyl-N-methyltaurine.
- composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-p- .tert.-octylphenoxyacetylglycyl-N-methyltaurine.
- composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-2,4- di (tert.amyl) phenoxyacetyl-N-cyclohexyltaurine.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
United States Patent Ofifice 3,165,409 Patented Jan. 12, 1965 3,165,409 DERIVATIVES OF CERTAIN HIGHLY BRANCHED CHAIN ACIDS AS COATING AIDS William J. Knox, Jr., Rochester, N.Y., and Robert E. Sticker, Lawrence, Kama, assignors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey N Drawing. Filed Feb. 7, 1962, Ser. No. 171,560 11 Claims. (Cl. 9694) This invention relates to coating aids for gelatin coating solutions particularly for photographic purposes which are certain alkaryloxyalkanoyl.taurine salts.
In the application of aqueous gelatin coating compositions, particularly gelatin-silver halide photographic emulsions, to a support such as film base or paper, it is desirable that there be present therein a coating aid to facilitate the application of the layer to the support. This application of gelatin composition can be either as a single layer or in multilayers such as by simultaneous application. The presence of coating aid reduces defects such as repellencies, pencil line streaks, and the like in the coating when dry. In such coating operations, however, the coating aids used often fail to induce adequate rewettability of the layer which usually exhibits surface slickness. In many cases, this surface slickness or slipperiness is especially undesirable in certain photo graphic products because of difficulties in handling and possible telescoping of the film wound in the form of rolls. Often it has been necessary to use a mixture of two surfactants as the coating aid to impart both desired surface roughness and rewettability of the dry coating. Not onlyis the mixing of coating aids sometimes bothersome but in addition some of the surfactants proposed for that purpose are naturally occurring materials and may vary in quality or contain impurities undesirable for photographicuse.
One object of our invention is to provide gelatin coating compositions from which layers having both adequate rewettability after drying-and sufiicient roughness of surface to facilitate handling may be obtained. Another object of our invention is to provide gelatin coating compositions from which coatings having few if any repellencies, pencil line streaks or other undesirable defects may be obtained. A further object of our invention is to provide coating aids comprising certain synthetically prepared taurines. Other objects of our invention will appear herein.
We have found that taurines which have alkaryloxyalkanoyl substituents show good properties when incorporated in photographic emulsions or other gelatin coating compositions as coating aids. The resulting compositions have provided coatings having good handling characteristics. Coating aids which we have found to be particularly useful in gelatin compositions are those having the formula:
8 to 16 carbon atoms, n is an integer 1 or 2, Q is a bond or R is alkyl of 1 to4 carbon atoms or cycloalkyl, and
M is a substituent such as Na, K, Li, NH or alkylammonium to give a water soluble salt.
We have found that when these compounds are incorporated in small amounts in gelatin coating compositions those compositions exhibit good coating properties. This has been found to be true both in coating operations in which a single-layer has been applied to a support or in multiple coating'operations such as described in US. 2,761,991 of T. A. Russell. It was found that any amount of coating aid present in the gelatin composition was effective in giving better coatings but that it is especially convenient to operate within the range of 05-15%, based on the weight of the gelatin, of coating aid in the composition and preferably within therange of 110%. In the coating aids in accordance with our invention it is preferred that the branched alkyl substituent attached to the benzene ring have 8-16 carbon atoms although included within our invention are the coating aids'in which two alkyl substituents may be on the benzene ring, the sum of the carbons of these alkyls being 8-16 carbon atoms. For instance, some of the compounds which have been considered most convenient to use are alkaryl compounds in which the sum of the alkyl substituents of the alkaryl has 8, 10, 12, 15 or the like carbon atoms either one or two alkyls being attached to'the benzene ring. The nitrogen of the taurine compound has as a substituent thereon alkyl of 14 carbon atoms such as methyl, ethyl or cycloalkyl i.e. cyclohexyl.
Some coating aids for use in gelatin coating compositions in accordance with our invention are:
Nasalt of N-p-t.-octylphenoxyacetyl-N-cyclohexyltaurine Na salt of N-p-t.-octylphenoxyacetyl-N-methyltaurine Na salt of N -p-t.-octylphenoxyacetylglycyl-N-methyltau- -r1ne Na salt of N-(branched)nonylphenoxyacetyl-N-methyltaurine i 4 Na salt of N-(branched)nonylphenoxyacetyl-N-cyclohexyltaurine Na salt of N-(branched)dodecylphenoxyacetyl-N-methyl-' taurine Na salt of N-(branched)dodecylphenoxyacetyl-N-cyclohexyltaurine Na salt of N-(branched)dodecylphenoxyacetyl-N-ethyltaurine The following examples illustrate the preparation of coating aids ofthe type referred to and their use in preparing film products.
Example 1 354 parts (0.359 mole) of a 23.8% aqueous solution' of the sodium salt of N-cyclohexyltaurine was evaporated in vacuo on a steam bath to /s /2 the original volume so as to remove any cyclohexylamine which might be present. The mass was then diluted withwater to 354 parts and 200 parts of acetone were added. Added simultaneously to the stirred solution at 60 C. while emulsion layer and a clear gelatin overcoating were apaids was used so as to give both good developer spread and resistance to slipping. The following results were obtained:
two ethereal extracts were combined, dried oversodium sulfate, and filtered. The ether was mostly evaporated off at room temperature; further evaporationwas then carried out at 80 C. for several days, followed by evaporation in vacuoat 55 C." The light tan'product thus ,5 surfaqtantconcentration Dr 1 O f f 1 GI 06 0 e e 81101 obta ned, N p.- t. octylphenoxyacetyl N cyclohexyl- V gg g Friction 7 2 m taurine, sodium salt, was useful as a coating aid in aque-: Wet Emui, wot Overcoat, ous gelatin compositions. g
Exampl 2 V 0.13 0.5 g. gone 0.25 0.5 one 1690 arts 4.2 moles of a 40% solution in water of 5 8,55 7 n 0 5 N the sodium salt of N-methyltaurine' Was evaporated 111' standard St 17 7 9 vacuo on a steam bath to approximately /2 the original volume thereby removing any methylamine present. The masswas diluted to 1690 parts with Water and was further 15 diluted with 6000 parts of 1:2 acetonezwater. 1185 parts moles) of p c y p y y chloride and 168 carrying a clear gelatin overcoat andthe area which devel0ps Parts 25% sdium t added if); iri tiv iy n iiififsio l ioififiiiii zt tin g iififii fii multaneously to the thestllfred solutlon at 600 "Whlle wet. A developer spread of 4.0 em. or more is desirable. maintaining a PH The t having been Si(ifi fiifiigaiffiifi ieiiiii iil r iiififiTfifi completed, the reactlon'mass was surfed for one 110111 at gelatin overcoat against the uncoated side of a similar sheet. renlwing .aceto-ne and a The iii}? iiiii fiiis f 231 551? c ofii'i s iiiiiiiifiglioiiiii fitfi tlon s shghfly turbldbut cleared p dllutlon to Difficulties occur in stacking coated sheets if the coefficient concentration and coolingto room temperature. The vffliction'is lessihwl flb011t0-25- material, N-p-t.-octylphenoxyacetyl-N-methyltaurine, so- E l 7 dium salt, was found to impart good coating properties to gelatin coating compositions in which it is incorporated as will be indicated below.
NOTE-I11 the above tables repellencies are the number of dull and uncoated spotsin the area referred to.
1 Developer spread is determined as follows One cc. of developer solution is delivered-i a. standard manner to a surface of photographically sensitized paper In a coating experiment similar tothat described in the preceding example, N-p-t.-octylphenoxyacetyl N cyclohexyltaurine, sodium salt (OPCT), was used as the coat- Example 3 0 ing aid. The following results were obtained:
In a coating experiment in which a single coating of an aqueous solution of gelatin was applied to cellulose ace- Surfactant Cmmentmim fggg of Repenencies tate film base .N-p-t.-octylphenoxyacetyl-N-methyltaurine, Wet W et Overcoat 3111. Friction (7.5'sq. ft.) sodium salt (OPT), was used as the coating aid at aconym, m i centration of 0.22 gram per pound of gelatin solution. I V g t The following results were obtained as compared with-a g- 8-2 3g 8- V control in which no coating aid was used: 0Z5 015 16:60 f 02627 None Repellencies Standard Standard 8.04. 0.715 None Coating aid: (25 ft.)
Control 13 40 j a p 8 OPT 2.
Example4 In a coating run similar to that described in Example 3 except that N-pentadecylphenoxyacetyl-N-methyltaurine,
ample 3, N-p-t.-octylphe ioxyacetyl-N cyclohexyltaurine,
following results were obtained:
sodium salt (PPT), was used as a coating aid, the follow- Repel- Longiing results (as compared with a control in WhlCh no coat- Coating Aid I lencies Meme tudmal ing aid was used) were obtained: a a streaks.
. RQPQL Longi Control 12 S1 Med. Coating Aid leiicies Mottle tudinal OPCT 0 M S1" (25 it.) Streaks S1 81' Example 9 6 3 s1 S1. In a coating experiment similar to that described 111'- the preceding example, N-2,4-di(t -amyl)phenoxyacetyl- N-cyclohexyltaurine, sodium salt (ACT), was used as the coating aid. The following results Wereobtained:
7 Example 5 In a coating run similar to that described in Example 3 in which N-p-t.-octylpheiioxyacetylglycyl N-methyltau l R L rine, sodium salt (OPGMT), was used as the coating aid; Coating Aidv 325 ifi the following results were obtained: v (25 ft.) Streaks R 1 7 L n rol 12 Med Coating Aid len e ies Mottle tiidir ial T 0 (25it. Streaks V g t i V The occurrence of pencil line streaks is a persistent de- SFfiri:::::::::::::::::I:: 3 sii 'i'r'ciII El: fact wallngs achieved by the Simultaneous l r t fi e of two gelatin layers to a filmbase or paper. The ability Example 6 of a coating aid to reduce the incidence of pencil line In a coating experiment in which both a photographic sion containing the coating aid has a spread of about 5 cm. when coated in a standard manner on a soap-cleaned, plied to paper by a multiple hopper coating technique as horizontal surface of a highly polished stainless steel described in US. Patent No. 2,76l,99l-using N'-p-t.- 0ctylplate. i phenoxyacetyl-N-methyltaurine, sodium salt (OPT), com- We claim:
pared to a standard in which a mixture of two coating ,75
In a coating experimentsimilarto, that described in Exsodium salt (OPCT), was used as thecoating aid. The
streaks is indicated when 1 ml. of a photographic emul-= 1. A compositionof matter comprising gelatin cone.
' )n In which R is branched alkyl, (R) totals 8 to 16 carbon atoms, n is an integer of 1 to 2, Q is selected from the group consisting of a bond and C--HNCH2 I; R is selected from the group consisting of alkyls of 1 to 4 carbon atoms and cycloalkyl, and M is a substituent selected from the group consisting of Na, K, Li, NH, and alkylammonium. 2. A composition of matter comprising gelatin containing coating aid corresponding to the following formula:
In which R is branched alkyl of 8 to 16 carbon atoms and R is selected from the group consisting of alkyls of 1 to 4 carbon atoms and cycloalkyl. 4. A gelatin-silver halide photographic emulsion containing a coating aid corresponding to the following for- (Rh it 6 In which R is branched alkyl, (R) n totals 8 to 16 carbon atoms, n is an integer of 1 to 2, Q is selected from the group consisting of a bond and R is selected from the group consisting of alkyls of 1 to 4 carbon atoms and cycloalkyl,
and M is a substituent selected from the group consisting of Na, K, Li, NH, and alkylammonium.
5. A composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-ptert.-octylphenoXyacetyl-N-cyclohexyltaurine.
6. A gelatin-silver halide photographic emulsion containing therein as a coating aid the sodium salt of N-ptert.-octylphenoxyacetyl-N-cyclohexyltaurine.
7. A composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-ptert.-octylphenoxyacetyl-N-methyltaurine.
8. A gelatin-silver halide photographic emulsion containing therein as a coating aid the sodium salt of N-ptert.-octylphenoxyacetyl-N-methyltaurine.
9. A composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N- pentadecylphenoxyacetyl-N-methyltaurine.
10. A composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-p- .tert.-octylphenoxyacetylglycyl-N-methyltaurine.
, 11. A composition of matter comprising gelatin containing therein as a coating aid the sodium salt of N-2,4- di (tert.amyl) phenoxyacetyl-N-cyclohexyltaurine.
References Cited in the file of this patent UNITED STATES PATENTS 2,739,891 Knox et al Mar. 27, 1956 2,823,123 Knox et al. Feb. 11, 1958 2,899,327 Christopher et a1 Aug. 11, 1959 2,933,406 Salzberg et a1 Apr. 16, 1960 3,003,877 McLaughlin et al Oct. 10, 1961 3,026,202 Knox et al. Mar. 20, 1962 3,038,804 Knox et al. June 12, 1962 3,042,522 Ben-Ezra et al. July 3, 1962 3,068,101 Knox et al. Dec. 11, 1962
Claims (1)
- 4. A GELATIN-SILVER HALIDE PHOTOGRAPHIC EMULSION CONTAINING A COATING AID CORRESPONDING TO THE FOLLOWING FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US171560A US3165409A (en) | 1962-02-07 | 1962-02-07 | Derivatives of certain highly branched chain acids as coating aids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US171560A US3165409A (en) | 1962-02-07 | 1962-02-07 | Derivatives of certain highly branched chain acids as coating aids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3165409A true US3165409A (en) | 1965-01-12 |
Family
ID=22624207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US171560A Expired - Lifetime US3165409A (en) | 1962-02-07 | 1962-02-07 | Derivatives of certain highly branched chain acids as coating aids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3165409A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778268A (en) * | 1969-05-28 | 1973-12-11 | Konishiroku Photo Ind | Light-sensitive silver halide photographic material |
| US6339054B1 (en) | 1999-04-20 | 2002-01-15 | Ecolab, Inc. | Composition and method for road-film removal |
| US6350725B1 (en) | 1999-04-20 | 2002-02-26 | Ecolab, Inc. | Composition and method for road-film removal |
| US6551974B1 (en) | 1999-04-20 | 2003-04-22 | Ecolab Inc. | Polish compositions for gloss enhancement, and method |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2739891A (en) * | 1953-07-17 | 1956-03-27 | Eastman Kodak Co | Method of preparing photographic products |
| US2823123A (en) * | 1955-12-29 | 1958-02-11 | Eastman Kodak Co | Coating out of gelatin layers |
| US2899327A (en) * | 1959-08-11 | Glue setting accelerators | ||
| US2933406A (en) * | 1957-09-11 | 1960-04-19 | Borden Co | Protein and nonionic agent compositions |
| US3003877A (en) * | 1957-06-27 | 1961-10-10 | Eastman Kodak Co | Spot prevention in photographic emulsions and colloid layers |
| US3026202A (en) * | 1958-08-07 | 1962-03-20 | Eastman Kodak Co | Gelatin coating compositions |
| US3038804A (en) * | 1956-07-30 | 1962-06-12 | Eastman Kodak Co | Coating aids for gelatin compositions |
| US3042522A (en) * | 1958-06-13 | 1962-07-03 | Gen Aniline & Film Corp | Photographic film and a composition for improving the slippage characteristics thereof |
| US3068101A (en) * | 1960-03-07 | 1962-12-11 | Eastman Kodak Co | Coating aid for gelatin and gelatinous silver halide emulsions |
-
1962
- 1962-02-07 US US171560A patent/US3165409A/en not_active Expired - Lifetime
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899327A (en) * | 1959-08-11 | Glue setting accelerators | ||
| US2739891A (en) * | 1953-07-17 | 1956-03-27 | Eastman Kodak Co | Method of preparing photographic products |
| US2823123A (en) * | 1955-12-29 | 1958-02-11 | Eastman Kodak Co | Coating out of gelatin layers |
| US3038804A (en) * | 1956-07-30 | 1962-06-12 | Eastman Kodak Co | Coating aids for gelatin compositions |
| US3003877A (en) * | 1957-06-27 | 1961-10-10 | Eastman Kodak Co | Spot prevention in photographic emulsions and colloid layers |
| US2933406A (en) * | 1957-09-11 | 1960-04-19 | Borden Co | Protein and nonionic agent compositions |
| US3042522A (en) * | 1958-06-13 | 1962-07-03 | Gen Aniline & Film Corp | Photographic film and a composition for improving the slippage characteristics thereof |
| US3026202A (en) * | 1958-08-07 | 1962-03-20 | Eastman Kodak Co | Gelatin coating compositions |
| US3068101A (en) * | 1960-03-07 | 1962-12-11 | Eastman Kodak Co | Coating aid for gelatin and gelatinous silver halide emulsions |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778268A (en) * | 1969-05-28 | 1973-12-11 | Konishiroku Photo Ind | Light-sensitive silver halide photographic material |
| US6339054B1 (en) | 1999-04-20 | 2002-01-15 | Ecolab, Inc. | Composition and method for road-film removal |
| US6350725B1 (en) | 1999-04-20 | 2002-02-26 | Ecolab, Inc. | Composition and method for road-film removal |
| US6551974B1 (en) | 1999-04-20 | 2003-04-22 | Ecolab Inc. | Polish compositions for gloss enhancement, and method |
| US6602350B2 (en) | 1999-04-20 | 2003-08-05 | Ecolab Inc. | Composition and method for road-film removal |
| US6864220B2 (en) | 1999-04-20 | 2005-03-08 | Ecolab Inc. | Composition and method for road-film removal |
| US20050199272A1 (en) * | 1999-04-20 | 2005-09-15 | Ecolab Inc. | Composition and method for road-film removal |
| US7223722B2 (en) | 1999-04-20 | 2007-05-29 | Ecolab Inc. | Polish compositions for gloss enhancement, and method |
| US7482315B2 (en) | 1999-04-20 | 2009-01-27 | Ecolab Inc. | Composition and method for road-film removal |
| US20090188533A1 (en) * | 1999-04-20 | 2009-07-30 | Ecolab Inc. | Composition and method for road-film removal |
| US7951245B2 (en) | 1999-04-20 | 2011-05-31 | Ecolab Usa Inc. | Composition and method for road-film removal |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3754924A (en) | Photographic silver halide element with an antistatic outer layer comprising a fluorinated surfactant and a polymethacrylate matting agent | |
| US2240472A (en) | Photographic gelatin layer containing a di-(polyalkylene glycoxy) alkane | |
| US3775126A (en) | Light-sensitive element comprising a coating layer containing a mixture of a cationic perfluorinated alkyl and an alkylphenoxypoly(propylene oxide) | |
| US2639234A (en) | Antistatic photographic film | |
| US3165409A (en) | Derivatives of certain highly branched chain acids as coating aids | |
| US3850640A (en) | Coating quality and reducing static simultaneously | |
| US3026202A (en) | Gelatin coating compositions | |
| US3220844A (en) | Photographic products | |
| JPH01161338A (en) | Silver halide photographic sensitive material | |
| US2739891A (en) | Method of preparing photographic products | |
| US2240476A (en) | Photographic gelatin layer containing an ester of sulphosuccinic acid | |
| US3295979A (en) | Friction reducing coatings for photographic elements | |
| US3769022A (en) | Photosensitive silver halide emulsions comprising coating aids | |
| US3507660A (en) | Photographic materials containing long-chain alkyl sucrose urethane | |
| US2897081A (en) | Antifogging agent and bactericide for photographic emulsions | |
| US2633423A (en) | Antiabrasion coatings for gelatino silver halide emulsion layers consisting of resins obtained by condensing 5-substituted hydantions with formaldehyde | |
| US2940854A (en) | Gelatin silver halide emulsion plasticized with dicarboxylic acid esters | |
| US3062649A (en) | Photographic film with antistatic layer | |
| US2240471A (en) | Photographic gelatin layer containing a n-acylated amino acid | |
| US2992108A (en) | Gelatin coating compositions | |
| US2358056A (en) | Manufacture of paper for photographic purposes | |
| US3515556A (en) | Photographic developing process utilizing hemlock tannin polymer | |
| US3684512A (en) | Photographic monobaths | |
| US2649374A (en) | Antistatic photographic film | |
| US2240470A (en) | Photographic gelatin layer containing a monoester of sorbitol |