US2756253A - Aroyl resorcinol compounds - Google Patents

Aroyl resorcinol compounds Download PDF

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US2756253A
US2756253A US408576A US40857654A US2756253A US 2756253 A US2756253 A US 2756253A US 408576 A US408576 A US 408576A US 40857654 A US40857654 A US 40857654A US 2756253 A US2756253 A US 2756253A
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photographic
compounds
ultraviolet
compound
aroyl
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US408576A
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Loria Anthony
George W Sawdey
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Eastman Kodak Co
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Eastman Kodak Co
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155—Organic compounds therefor

Definitions

  • This invention relates to new products and new photographic elements protected against the harmful effects of ultraviolet radiation.
  • R represents an alkyl (e. g. methyl, ethyl, propyl, isopropyl, n-butyl, n-amyl, n-hexyl, n-dodecyl, etc.)
  • R1 represents an organic group selected from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of sulfo (including alkali metal salts thereof, e. g. sodium, potassium, etc.), and carboxyl' (including alkali metal salts thereof, e. g. sodium, potassium, etc.), e. g. 0-, m-, and p-sulfophenyl, o-, m-, and p-carboxyphenyl, 3,5-dicarboxyphenoxymethyl, etc.
  • sulfo including alkali metal salts thereof, e. g. sodium, potassium, etc.
  • carboxyl' including alkali metal salts thereof, e. g. sodium, potassium, etc.
  • the ultraviolet absorbing compounds can be incorporated in the photographic element in a variety of ways, depending on the ultimate use of the photographic element and the degree of protection desired.
  • the ultraviolet absorbing compound can be dissolved or dispersed in a solvent medium together with a colloidal binder, such as gelatin, cellulose esters (e. g. cellulose acetate, etc.), synthetic resins (e. g. polyvinyl acetals, hydrolyzed polyvinyl acetate, etc.), etc., and the resulting mixture coated over the light-sensitive layer of'the photographic element.
  • a colloidal binder such as gelatin, cellulose esters (e. g. cellulose acetate, etc.), synthetic resins (e. g. polyvinyl acetals, hydrolyzed polyvinyl acetate, etc.), etc.
  • the ultraviolet filter layer need not be an outer layer, but this layer can be placed over one of the layers subject to the harmful effects of ultraviolet radiation.
  • the ultraviolet filter layer can be placed between the blue and green sensitive layers, alternatively, the ultraviolet filter layer can be placed between the green and the red sensitive layers.
  • the material useful in absorbing the ultraviolet radiation can be incorporated directly in the light-sensitive emulsion instead of, or in addition to, being present in another layer.
  • the amount of ultraviolet absorbing compound used can be varied, depending upon the efiect desired and the use to which the material is to be put.
  • the support of the photographic element can be transparent, such as a cellulose ester support, or the support can be opaque, such as a paper support.
  • Other supports, such as glass, metal, etc., can be employed, if desired.
  • Typical compounds selected from those represented by Formula I which can be used in practicing our invention comprise those represented by the following formulas:
  • R has the values given above.
  • the reduction can advantageously be effected with hydrogen using Raney nickel catalyst.
  • Intermediates IV can advantageously be obtained by the Hoesch synthesis (by reaction of the resorcinol compound with l-cyano-3-nitrobenzene). See Organic Reactions, vol. 5, pp. 387-412.
  • the sulfo compounds can advantageously be obtained in the form of the sulfonic acid chloride, which undergoes hydrolysis in the presence of the water present in the bathing or coating solutions.
  • the 3,S-dicarboxyphenoxymethyl (R1) compounds are first obtained in the form of their alkyl esters (e. g. methyl, ethyl, etc.), which can be easily hydrolyzed in aqueous alkali (e. g. sodium hydroxide, sodium carbonate, etc.) to the salts of the respective carboxylic acids.
  • alkyl esters e. g. methyl, ethyl, etc.
  • aqueous alkali e. g. sodium hydroxide, sodium carbonate, etc.
  • Example 1 4-n-hexylresorcinol was prepared according to the method of Desai et al.Proc. Indian Acad. Sci, vol. 13A, pages l77-83 (Chemical Abstracts, vol. 36, page 90). The 4-n-hexylresorcinol was then condensed by the Hoesch reaction with l-cyano-3-nitrobenzene, according to directions given by Yamashita (Bull. of the Chem. Soc.
  • the dimethyl ester thus obtained was suspended in alcoholic alkali and shaken at room temperature for several minutes. Spontaneous hydrolysis of the dirnethyl ester occurred, yielding the sodium salt of the desired acid.
  • This sodium salt can be used directly, or the reaction medium brought to a neutral pH.
  • the a-(3,5-dicarbomethoxyphenoxy)acetyl chloride used in the above example was prepared by condensing S-hydroxyisophthalic acid dirnethyl ester with the sodium salt of chloroacetic acid in the presence of sodium methoxide.
  • the sodium salt of the resulting substituted phenoxy acetic acid was treated with phosphorous pentachloride (in ligroin) to yield the desired acid chloride.
  • the S-hydroxyisophthalic acid dimethyl ester was obtained by treating 5-hydroxyisophthalic acid with sulf onylchloby treatment with methanol;
  • Example 2 ;- -4- ⁇ 3-[-(3,5-dicarb0xyphenoxy)acetamide] benzoyl ⁇ -6-n-d0decylresorcinol (sodium salt) -ONa .-ONa
  • Example 3.4-[3-(3-sulfobenzamide)benzoyl1-6-nhexylresorcinol (sodium salt) l 0111301.) NH-dQ A OxNB This compound was prepared in the same manner as that of Example 1 above, except that 3-chlorosulfonylbenzoyl chloride was substituted for the a-(3,5-dicarbomethoxyphenoxy)acetyl chloride. The resulting chlorosulfonyl chloride product was crystallized twice from benzene, yielding a pale yellow material melting at 150- 151 C. On analysis, the following results were obtained.
  • Example 4 Application to photographic element 1 g. of the chlorosulfonyl compound obtained in EX- ample 3, having a melting point of ISO-151 C., was dissolved in a mixture of 6 ml. of ethyl alcohol and ml. of aqueous sodium hydroxide, containing 10% by weight of the sodium hydroxide. This solution was added to 89 ml. of water and the pH of the solution adjusted to 7.0 by the addition of citric acid.
  • Processed film or paper strips were then bathed in the above solution for 10 minutes, and thereafter rinsed and dried. Measurement of the density of the film or paper strips indicated that an appreciable density to ultraviolet light had been acquired. Exposure of the films or strips to the deleterious effects of daylight caused no detectable deterioration of the photographic images present in the processed film or paper strips.
  • photographic elements containing a photographic silver halide emulsion layer can be treated with other ultraviolet absorbing compounds embraced by Formula I above.
  • R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from 1 to 12, and R1 represents a phenoxymethyl radical, said radical being substituted by a member selected from the group consisting of a carboxyl radical and an alkali metal salt of said carboxyl radical.
  • R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from from 1 to 12, and R1 represents a phenyl radical, said radical being substituted by a member selected from the group consisting of a sulfo radical and an alkali metal salt of said sulfo radical.
  • R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from 1 to 12.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

2,756,253 Ice Hatented July 24, 1955 2,756,253 AROYL RESORCINOL COMPOUNDS Anthony Loria and George W. Sawdey, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Original application October 31, 1952, Se-
rial No. 317,904, now Patent No. 2,719,086, dated September 27, 1955. Divided and this application February 5, 1954, Serial No. 408,576
8 Claims. (Cl. 260-507) This invention relates to new products and new photographic elements protected against the harmful effects of ultraviolet radiation.
It is known that certain materials such as cellulosic films and photographic layers, are adversely affected by ultraviolet radiation when such materials are exposed to daylight. In the case of photographic layers, the ultraviolet radiation sometimes causes undesired exposure of the layer, or layers, since photographic silver halide emulsions are sensitive to blue, violet and ultraviolet regions of the spectrum, in addition to any. other sensitivity which may be given them, and in the exposure of such material, it is frequently desirable to prevent the action of ultraviolet light on the sensitive emulsion. This is especially true in the case of photographic materials designed for use in color photography where the film has been sensitized to the longer wavelength regions where it is desirable to record only the rays of the visible spectrum.
Color photographs on multilayer photographic material, particularly where the dye images are formed in sensitive emulsion layers by color development, are susceptible to fading and discoloration by the action of ultraviolet radiation to which the photographs are subjected during viewing. It is also known that the residual couplers contained in the emulsion layers after formation of the picture images in certain processes are attacked by ultraviolet radiation and form a stain which is undesirable in the finished photograph. The action of ultraviolet radiation on finished color photographs is particularly noticeable in positive prints on paper or other opaque supports, since this type of print is frequently viewed in daylight where there is a high content of ultraviolet radiation. This dye fading and yellowing appears to be caused primarily by those wavelengths of light which lie close to the visual region of the spectrum, i. e. 360-400 millimicrons. We have now found that certain new ultravioletab sorbing compounds can be used to overcome the aforementioned difliculties, without attendant harmful action by the ultraviolet absorbing compound itself.
It is, therefore, an object of our invention to provide new. compounds and photographic elements protected against the harmfui efiects of ultraviolet radiation. A further object is to provide photographic color materials which have been protected against the harmful effects of ultraviolet radiation. Other objects will become apparent from a consideration of the following description.
The new ultraviolet absorbing compounds which we propose to employ in our invention are advantageously represented by the following general formula:
I. OH
whereinR represents an alkyl (e. g. methyl, ethyl, propyl, isopropyl, n-butyl, n-amyl, n-hexyl, n-dodecyl, etc.)
group or an alkoxyl (e. g. methoxyl, ethoxyl, etc.) group, and R1 represents an organic group selected from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of sulfo (including alkali metal salts thereof, e. g. sodium, potassium, etc.), and carboxyl' (including alkali metal salts thereof, e. g. sodium, potassium, etc.), e. g. 0-, m-, and p-sulfophenyl, o-, m-, and p-carboxyphenyl, 3,5-dicarboxyphenoxymethyl, etc. These ultraviolet absorbing compounds can be incorporated in the photographic element in a variety of ways, depending on the ultimate use of the photographic element and the degree of protection desired. Advantageously, the ultraviolet absorbing compound can be dissolved or dispersed in a solvent medium together with a colloidal binder, such as gelatin, cellulose esters (e. g. cellulose acetate, etc.), synthetic resins (e. g. polyvinyl acetals, hydrolyzed polyvinyl acetate, etc.), etc., and the resulting mixture coated over the light-sensitive layer of'the photographic element. Where the photographic element is a material intended for use in color photography, the ultraviolet filter layer need not be an outer layer, but this layer can be placed over one of the layers subject to the harmful effects of ultraviolet radiation. For example, in a multilayer material comprising three difierentially sensitized layers, the red sensitive layer being adjacent to the support, the green sensitive layer being superposed on the red sensitive layer, and the blue sensitive layer being outermost with respect to the other light-sensitive layers, the ultraviolet filter layer can be placed between the blue and green sensitive layers, alternatively, the ultraviolet filter layer can be placed between the green and the red sensitive layers. If desired, the material useful in absorbing the ultraviolet radiation can be incorporated directly in the light-sensitive emulsion instead of, or in addition to, being present in another layer. The amount of ultraviolet absorbing compound used can be varied, depending upon the efiect desired and the use to which the material is to be put.
The support of the photographic element can be transparent, such as a cellulose ester support, or the support can be opaque, such as a paper support. Other supports, such as glass, metal, etc., can be employed, if desired.
Typical compounds selected from those represented by Formula I which can be used in practicing our invention comprise those represented by the following formulas:
0.11 4- 3- (3-su1fobenzamido benzoyl] 6-11-hexy1resorcinol 4-{3- [a- (3,5-dicarboxyphenoxy) acetamido] benzoy1}-6-nhexylresorcinol 3. O
0 3H 4- [3- (3-snlfobenzamido) benzoyl] 6-methy1res orcinol J-H ll 4-{3-[01- (3,5-dicarboxyphenoxy) acetamido]benz0yl}-6-ndo'decylresorcinol no o- 0-011 I I 436E130!) un-c-omoQ 4-{a-[ (3-carboxyphenoxy) acetamido] benzoyl}-6-n-hexylresorcinol NHo l mu
4-[3- (3-sulfobenzamido)benzoyl] -6-ethoxyresorcinol s. on
The compounds represented by Formula I above can advantageously be prepared by condensing together a compound selected from those represented by the following general formula:
u R IHa with a compound selected from those of the following general formula:
IV. OH
wherein R has the values given above. The reduction can advantageously be effected with hydrogen using Raney nickel catalyst. Intermediates IV can advantageously be obtained by the Hoesch synthesis (by reaction of the resorcinol compound with l-cyano-3-nitrobenzene). See Organic Reactions, vol. 5, pp. 387-412.
The sulfo compounds can advantageously be obtained in the form of the sulfonic acid chloride, which undergoes hydrolysis in the presence of the water present in the bathing or coating solutions. In like manner, the 3,S-dicarboxyphenoxymethyl (R1) compounds are first obtained in the form of their alkyl esters (e. g. methyl, ethyl, etc.), which can be easily hydrolyzed in aqueous alkali (e. g. sodium hydroxide, sodium carbonate, etc.) to the salts of the respective carboxylic acids.
The following examples will serve to illustrate the manner whereby the new compounds represented by mula. sen, e p pared.
Example 1 .-4{3 [a- (3,5 -dicarb0xyphenoxy acetamid o] benzoyl}-6-n-hexylresorcinol (sodium salt) 4-n-hexylresorcinol was prepared according to the method of Desai et al.Proc. Indian Acad. Sci, vol. 13A, pages l77-83 (Chemical Abstracts, vol. 36, page 90). The 4-n-hexylresorcinol was then condensed by the Hoesch reaction with l-cyano-3-nitrobenzene, according to directions given by Yamashita (Bull. of the Chem. Soc.
of Japan, No. 7, vol. 3, page 180). The substituted benzophenone thus produced had the following formula and melted at 95-96 C.
0 HQ L aHiam) NO:
The above compound was then catalytically reduced in the presence of Raney nickel under a hydrogen pressure of 42 pounds to produce the corresponding amino derivative. This amino derivative was crystallized from a mixture of benzene-heptane (2: 1) and it had a melting point of 68-70 C.
4.2 g. of the above amine (0.0134 mole) melting at 6870 C. were dissolved in 25 ml. of acetonitrile and treated with a solution of 3.84 g. (0.0134 mole) of a-(3,5-dicarbomethoxyphenoxy) acetyl chloride in 25 ml. of acetonitrile. There was a rise of 10 (C.) on mixing the solutions and a copious quantity of hydrochloric acid gas was evolved. The resulting solution was then heated at 65 C. for 10 minutes and allowed to stand for one hour. The solution was then filtered and cooled to 5-10 C. The dimethyl ester of the desired product precipitated, and it was filtered and recrystallized from fresh acetonitrile. There were thus obtained 4.8 g. of white plates melting at l46148 C. On analysis, the following results were obtained:
The dimethyl ester thus obtained was suspended in alcoholic alkali and shaken at room temperature for several minutes. Spontaneous hydrolysis of the dirnethyl ester occurred, yielding the sodium salt of the desired acid. This sodium salt can be used directly, or the reaction medium brought to a neutral pH.
The a-(3,5-dicarbomethoxyphenoxy)acetyl chloride used in the above example was prepared by condensing S-hydroxyisophthalic acid dirnethyl ester with the sodium salt of chloroacetic acid in the presence of sodium methoxide. The sodium salt of the resulting substituted phenoxy acetic acid was treated with phosphorous pentachloride (in ligroin) to yield the desired acid chloride. The S-hydroxyisophthalic acid dimethyl ester was obtained by treating 5-hydroxyisophthalic acid with sulf onylchloby treatment with methanol;
Example 2;- -4-{3-[-(3,5-dicarb0xyphenoxy)acetamide] benzoyl}-6-n-d0decylresorcinol (sodium salt) -ONa .-ONa
HO- l- Calculated for CarHfiNOa Found Percent 68 The dimethyl ester was spontaneously hydrolyzed to the sodium salt of the desired acid by suspending the dimethyl ester in an alcoholic alkali solution. The sodium salt of the acid was thus obtained.
Example 3.4-[3-(3-sulfobenzamide)benzoyl1-6-nhexylresorcinol (sodium salt) l 0111301.) NH-dQ A OxNB This compound was prepared in the same manner as that of Example 1 above, except that 3-chlorosulfonylbenzoyl chloride was substituted for the a-(3,5-dicarbomethoxyphenoxy)acetyl chloride. The resulting chlorosulfonyl chloride product was crystallized twice from benzene, yielding a pale yellow material melting at 150- 151 C. On analysis, the following results were obtained.
Calculated tor CMHMCINOQS Found Percent Percent O) m n The chlorosulfonyl compound thus produced was suspended in an alcoholic alkali solution, thus yielding the desired sodium salt.
Example 4.Application to photographic element 1 g. of the chlorosulfonyl compound obtained in EX- ample 3, having a melting point of ISO-151 C., was dissolved in a mixture of 6 ml. of ethyl alcohol and ml. of aqueous sodium hydroxide, containing 10% by weight of the sodium hydroxide. This solution was added to 89 ml. of water and the pH of the solution adjusted to 7.0 by the addition of citric acid.
Processed film or paper strips were then bathed in the above solution for 10 minutes, and thereafter rinsed and dried. Measurement of the density of the film or paper strips indicated that an appreciable density to ultraviolet light had been acquired. Exposure of the films or strips to the deleterious effects of daylight caused no detectable deterioration of the photographic images present in the processed film or paper strips.
In a manner similar to that illustrated in Example 4, photographic elements containing a photographic silver halide emulsion layer can be treated with other ultraviolet absorbing compounds embraced by Formula I above.
This application is a division of our application Serial No. 317,904, filed October 31, 1952, now U. S. Patent 2,719,086, issued September 27, 1955.
What we claim as our invention and desire secured by Letters Patent of the United States is:
l. A compound selected from those represented by the following general formula:
EDGE-Q.
wherein R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from 1 to 12, and R1 represents a phenoxymethyl radical, said radical being substituted by a member selected from the group consisting of a carboxyl radical and an alkali metal salt of said carboxyl radical.
3. A compound selected from those represented by the following general formula:
O -Q- -Q I it 1 TH Rl wherein R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from from 1 to 12, and R1 represents a phenyl radical, said radical being substituted by a member selected from the group consisting of a sulfo radical and an alkali metal salt of said sulfo radical.
4. A compound selected from those represented by the following general formula:
O i: 1 m
wherein R represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from 1 to 12.
5. A compound selected from those represented by the following general formula:
0 -QNa ONa , 7' wherein represents an alkyl group of the formula CmH2m+1 wherein m represents a positive integer of from 9 ,2-
6, The compound represented by the following formula:
- 8. The compound represented by the following formula:
S OzNa References Cited in the file of this patent UNITED STATES PATENTS Misslin et a1, Jan. 14, 1941

Claims (1)

1. A COMPOUND SELECTED FROM THOSE REPRESENTED BY THE FOLLOWING GENERAL FORMULA:
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057921A (en) * 1959-06-11 1962-10-09 American Cyanamid Co Aminohydroxybenzophenones and triazine derivatives thereof
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228398A (en) * 1937-02-10 1941-01-14 Soc Of Chemical Ind Condensation products and process of making the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2228398A (en) * 1937-02-10 1941-01-14 Soc Of Chemical Ind Condensation products and process of making the same

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057921A (en) * 1959-06-11 1962-10-09 American Cyanamid Co Aminohydroxybenzophenones and triazine derivatives thereof
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives

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