Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3165409 A
Publication typeGrant
Publication dateJan 12, 1965
Filing dateFeb 7, 1962
Priority dateFeb 7, 1962
Publication numberUS 3165409 A, US 3165409A, US-A-3165409, US3165409 A, US3165409A
InventorsKnox Jr William J, Sticker Robert E
Original AssigneeEastman Kodak Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Derivatives of certain highly branched chain acids as coating aids
US 3165409 A
Abstract  available in
Images(3)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

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

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2739891 *Jul 17, 1953Mar 27, 1956Eastman Kodak CoMethod of preparing photographic products
US2823123 *Dec 29, 1955Feb 11, 1958Eastman Kodak CoCoating out of gelatin layers
US2899327 *Dec 5, 1955Aug 11, 1959 Glue setting accelerators
US2933406 *Sep 11, 1957Apr 19, 1960Borden CoProtein and nonionic agent compositions
US3003877 *Jun 27, 1957Oct 10, 1961Eastman Kodak CoSpot prevention in photographic emulsions and colloid layers
US3026202 *Aug 7, 1958Mar 20, 1962Eastman Kodak CoGelatin coating compositions
US3038804 *Jul 30, 1956Jun 12, 1962Eastman Kodak CoCoating aids for gelatin compositions
US3042522 *Jun 13, 1958Jul 3, 1962Gen Aniline & Film CorpPhotographic film and a composition for improving the slippage characteristics thereof
US3068101 *Mar 7, 1960Dec 11, 1962Eastman Kodak CoCoating aid for gelatin and gelatinous silver halide emulsions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3778268 *Sep 11, 1972Dec 11, 1973Konishiroku Photo IndLight-sensitive silver halide photographic material
US6339054Dec 15, 1999Jan 15, 2002Ecolab, Inc.Composition and method for road-film removal
US6350725Apr 20, 1999Feb 26, 2002Ecolab, Inc.Composition and method for road-film removal
US6551974Jun 23, 2000Apr 22, 2003Ecolab Inc.Polish compositions for gloss enhancement, and method
US6602350Nov 30, 2001Aug 5, 2003Ecolab Inc.Composition and method for road-film removal
US6864220Nov 30, 2001Mar 8, 2005Ecolab Inc.Composition and method for road-film removal
US7223722Mar 14, 2003May 29, 2007Ecolab Inc.Polish compositions for gloss enhancement, and method
US7482315Mar 7, 2005Jan 27, 2009Ecolab Inc.Composition and method for road-film removal
US7951245Jan 26, 2009May 31, 2011Ecolab Usa Inc.Composition and method for road-film removal
US20050199272 *Mar 7, 2005Sep 15, 2005Ecolab Inc.Composition and method for road-film removal
US20090188533 *Jan 26, 2009Jul 30, 2009Ecolab Inc.Composition and method for road-film removal
Classifications
U.S. Classification430/635, 430/636, 106/154.3
International ClassificationG03C1/38
Cooperative ClassificationG03C1/38
European ClassificationG03C1/38