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US2940852A - m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity - Google Patents

m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity Download PDF

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US2940852A
US2940852A US641023A US64102357A US2940852A US 2940852 A US2940852 A US 2940852A US 641023 A US641023 A US 641023A US 64102357 A US64102357 A US 64102357A US 2940852 A US2940852 A US 2940852A
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opacity
diazotype
compound
coupling components
coupling
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Jr Clifford E Herrick
Chester E Slimowicz
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to DENDAT1068556D priority Critical patent/DE1068556B/de
Priority to NL97385D priority patent/NL97385C/xx
Priority to NL225064D priority patent/NL225064A/xx
Priority to BE564689D priority patent/BE564689A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US641023A priority patent/US2940852A/en
Priority to GB2993/58A priority patent/GB840945A/en
Priority to CH5602558A priority patent/CH375988A/en
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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
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/58—Coupling substances therefor

Definitions

  • the present invention relates to light sensitive diazo type materials containing m,m-dioxydiphenols as coupling components and, particularly to diazotype intermediates of high opacity containing such coupling components.
  • a diazotype layer in order to be satisfactory as an intermediate material, a diazotype layer must meet rigid and diverse specifications.
  • the intermediate foil should have the fastest possible printing speed consistent with good opacity, and form a dye having both good actinic opacity and good visual opacity, since visual examination of the, intermediate is frequently necessary.
  • the layer must exhibit satisfactory stability, both in the packageand in the developed foil. Both the packaged and developed foil must show good stability against yellowing, especially yellowing which occurs on exposure of a developed foil to ultraviolet radiation since such yellowing increases the opacity of the material.
  • the dye formed should be free from a tendency to migrate or to ofiset when in contact with other materials. Heretofore, it has not been possible to combine all of these properties to a satisfactory degree in any commercial product.
  • resorcinol One of the most widely used azo dye coupling components in diazo intermediate products is resorcinol. When freshly coated in high concentration, resorcinol yields a dye having good actinic opacity. However, as the coated material ages, difiusion and redistribution of thecomponents takes place so that in place of the monoazo coupling originally predominant, bis-coupling becomes important. Resorcinol is thus very sensitive to the diazo/ coupler ratio. Consequently, as the material ages, the visual opacity increases as the result of bis-dye formation while a marked falling oil in actinic opacity occurs at the same time.
  • coupling components which provide layers of good stability having good actinic opacity of which m-hydroxyphenylurea and dimethyl aminomethyl-2,5-xylenol are examples. These materials, however, suffer from restricted solubility, are prone to offset under certain circumstances, and yield layers which fail to develop the dye images rapidly and completely on exposure to ammonia. In addition, their visual opacity is poor.
  • Light sensitive diazotype materials containing m;m'- dioxydiphenols as coupling components and, more par ticularly, those intermediate materials of high opacitycontaining such couplers constitute the purposes and objects of the present invention.
  • polyfunctional resorcinol etherscontemplated herein may be depicted by the following general formula:
  • V Isopropyl alcohol ........a ..mls
  • A is alkylene such kylenearylenealkylene, i.e., methylenephenylenemethyl ene, ethylenephenyleneethylene and the like; isoalkylidcne such as isopropylidene and the like;
  • X and Y are hydro gen, alkyl such as methyl, ethyl, butyl, amyl, hexyl and the like; sulfo, halogen such as chlorine and bromine;
  • n 1 when p is 0 and p +1 when p is a whole number, i.e., 2 when p is .l. V
  • m,m'-ethylenedioxydiphenol was made by'a modi as ethylene, trimethylene, tetramethylene, pentamethylene, methyltrimethylene; al-
  • this composition yielded a yellow ish-brown image with good visual density, opacity to ultraviolet light, dye stability, and developability.
  • this composition When coated on cellulose acetate foil base, dried, irradiated withfactinic light'under a positive; original, and exposed to ammonia vapors, this composition yielded a yellowish-brown image, with excellent stability and good visual density. The printingspeed and ultraviolet opacity of this material were outstanding.
  • Example V The procedure is the same as in Example I excepting that the coupling component used is m,m-trirnethylenedioxydiphenol of the following formula:
  • This compound may be prepared as follows: m-Nitrophenol was reacted with 1,4-dibromobutane to give 3,3- -dinitrotetramethylenedioxydibenzene, M. 7 -7 C., which was reduced in isopropyl alcohol over palladium on carbon to the amine, M. 128-30 C. 'Diazotization and hydrolysis with dilute sulfuric acid were completed as in Example V and the desired compound was obtained as Example,
  • This compound may be prepared 'as follows: 1,5-divbromopentane and m-nitrophenol were condensed to 3,3- dinitropentamethylenedioxydibenzene, M. 94-6 C. This was reduced in ethyl alcohol over palladium on carbon to the amine, M. 1'l9-2l C. Diazotization and hydrolysis with-dilute sulfuric acid; gave-the desired compound as colorless ,needles, M.
  • Example IX The procedure is the same as in Example HI excepting that the coupling component is 6,6-dimethyl-3,3- trimethylenedioxydiphenol of the formula:
  • OH OH CH CHI OCHICBICHIO This compound may be prepared as follows: B-nitro- 4-methylphenol was prepared from 3-nitro-4-methylaniline by diazotization and hydrolysis (Harvey and Roberson, J. Chem. Soc. 1938, 97-401). This was reacted with trimethylene bromide and alkali to yield 4,4'-dimethyl-3,3'-dinitrotrimethylenedioxydibenzene, M. 106- 9 C. Reduction in ethanol over palladium on carbon went smoothly to give the amino derivative, M. 129-30 C. Diazotization and hydrolysis by the usual method gave the desired compound, M. 139-41 C.
  • Example X The procedure is the same as in Example III excepting that the coupling component is m,rn'-(p-phenylenedimethylenedioxy) cliphenol of the formula:
  • This compound may be prepared as follows: m-Nitrophenol and p-phenylenedimethylene bromide were reacted to give 3,3-dinitro-p-phenylenedimethylenedioxydibenzene, M. 193-6" C.
  • the amino compound, prepared by reduction in ethanol over palladium on carbon was diazotized and hydrolyzed to the desired compound, M. 724 C.
  • Example XI The procedure is the same as in Example II excepting that the coupling component is 6,6-dihexyl-3,3'-isopropylidenedioxydiphenol of the formula:
  • Example XIII The procedure is the same as in Example 11 excepting that the coupling component employed is 4,4',6,6'-tetramethyl-3,3'-trimethylenedioxydiphenol of the formula:
  • Light sensitive diazotype materials comprising a base sensitized with a light sensitive diazonium compound, and as the coupling component, the compound of the following formula:
  • V zonium salt (amylase) comprising a translucent base sensitized with a light sensir 1 7 r 8 tive diazonitlm compound, and as the eonplingcomlight-sensitive compound'isa p-4-morpholinylbenzene diaponent, a compound of theiollowin'g formula: V zonium salt. V .1 V
  • PATENTS 1 Y are selected from the class consisting of hydrogen, 6 6 7 Great fi n r f 9 alkyl, sulfo and halogen; p is selected fi'om'the class con- 7 1 I 'sisting of 0 and a' whole number; and n ris l when p is 7 OTHER 0"and p+1 when p is 'a whole number.. 1 Chem. Abstracts, 47; 4369g ,(1953).

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

Description

Patented June 14, 1960 m,m-DIGXYDIPENOLS AS COUPLING COMPO- NENTS IN DIAZOTYPE INTERMEDIA'IES OF HIGH OPACITY Clifiord E. Herrick, Jr., Cheuango Forks, and Chester E. Slimowicz, Vestal, N.Y., assignors to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. Filed Feb. 19, 1957, Ser. No. 641,023
7 Claims. (Cl. 96-91) The present invention relates to light sensitive diazo type materials containing m,m-dioxydiphenols as coupling components and, particularly to diazotype intermediates of high opacity containing such coupling components.
One of the most widely used techniques in the diazotype reproduction art involves the use of the so-called intermediate or transition print. Thus, in place of making a large number of copies from a-frail or valuable original, it is customary to make a single copy on an intermediate diazotype paper or foil. This intermediate diapositive is then used as the photo master for the production of additional prints.
There are many advantages in the use of an intermediate master. Wear and tear on a frail original are avoided. Owing to the high contrast of the diazotype process, some improvement in image density can usually be realized in the intermediate print, especially if the original itself be dirty or-old. Furthermore, the speed at which copies can be made is substantially-greater than when the original itself is used as a photo master, a fact attributable to the higher transparency of the foil base compared to the original base.
A variety of useful techniques using intermediate foil masters have been evolved, such as overlay printing, partial eradication of the original image, etc. Consequently, the production of a satisfactory intermediate material is a very basic and important part of diazotype technology.
in order to be satisfactory as an intermediate material, a diazotype layer must meet rigid and diverse specifications. The intermediate foil should have the fastest possible printing speed consistent with good opacity, and form a dye having both good actinic opacity and good visual opacity, since visual examination of the, intermediate is frequently necessary. The layer must exhibit satisfactory stability, both in the packageand in the developed foil. Both the packaged and developed foil must show good stability against yellowing, especially yellowing which occurs on exposure of a developed foil to ultraviolet radiation since such yellowing increases the opacity of the material. The dye formed should be free from a tendency to migrate or to ofiset when in contact with other materials. Heretofore, it has not been possible to combine all of these properties to a satisfactory degree in any commercial product.
One of the most widely used azo dye coupling components in diazo intermediate products is resorcinol. When freshly coated in high concentration, resorcinol yields a dye having good actinic opacity. However, as the coated material ages, difiusion and redistribution of thecomponents takes place so that in place of the monoazo coupling originally predominant, bis-coupling becomes important. Resorcinol is thus very sensitive to the diazo/ coupler ratio. Consequently, as the material ages, the visual opacity increases as the result of bis-dye formation while a marked falling oil in actinic opacity occurs at the same time. In addition, with the diazos most suitable for the production of high actinic opacity, resorcinol is too active a coupler especially at the higher coupler concentration which leads predominantly to mono-azo coupling and such layers cannot be satisfactorily stabilized against precoupling.
On the other hand, coupling components are known which provide layers of good stability having good actinic opacity of which m-hydroxyphenylurea and dimethyl aminomethyl-2,5-xylenol are examples. These materials, however, suffer from restricted solubility, are prone to offset under certain circumstances, and yield layers which fail to develop the dye images rapidly and completely on exposure to ammonia. In addition, their visual opacity is poor.
Among the host of materials studied as coupling components for diazotype intermediates, the 2,6-dialkyloxyand-dialkyl phenols as well as the resorcinol monoethers disclosed in US. Patent 2,516,931 have been found excellent in many respects in that they yield layers'having good stability towards precoupling, have good actininc opacity and better than average visual opacity. These materials, however, are often liquids or semi-solids and frequently have an offensive and penetrating medicinal odor. These properties have precluded their use incommercial materials.
We have now found that certain polyiunctionalderivatives of the resorcinol monoether class, i.e., m',rn-'dioirydiphenols, are especially well adapted for use a's couplers in intermediate materials. These couplers possess an unusual combination of satisfactory; visual and high actinic opacity and freedom from objectiorlable odor. EA further advantage of the high actinic opacity afi'o'rdd by this class of derivatives is that it permits the use of shading couplers for the purpose of enhancing even further the visual opacity without seriously compromising the actinic opacity requirements. Such a-course isnot practical with couplers which yield intermediate prints 'pos sessing 'm'dicore or at best only acceptableactinic-opacity. The materials have excellent solubility in SOlV!lIS." They fdrm layers free-from color shift-on-agingand 'yield dyes which are less prone to migrate than'the dyes-formed by the simple monoethers. -An especially suiprisingdiscovery 5 is the fact that while these 'polyfiinctional derivatives are readily stabilized against preco'upling, they ammoniadevelop readily and completely. In fact, their precoupling activity is so low that it is possible to combine themsatisfactorily with a class of diazo compounds, namely, the p-4-moipholinylbenzenediazo complexes which heretofore were unusable owing to their great coupling activity, to produce foils of outstandingly high printing speed and whose dye images possess outstanding actinic opacity. The result is a foil which sets a new standard owing to its high printing speed and actinic opacity and above average visual density in the diazotype art.
Light sensitive diazotype materials containing m;m'- dioxydiphenols as coupling components and, more par ticularly, those intermediate materials of high opacitycontaining such couplers constitute the purposes and objects of the present invention.
The polyfunctional resorcinol etherscontemplated herein may be depicted by the following general formula:
-' (allryleno),P
, Etamplell. 7
.Water A j m lled.
V Isopropyl alcohol ........a ..mls
. Formic acid m .1 Citric acid p gun 3. 'sulfosalicylic acid gms-.. Aluminum sulfate -gms- 3 m,m'-Ethylenedioxydiphenol "gins... 2 p-4-morpholinylbenzenediazonium chloride: zinc chloride complex a 1- gms in which A is alkylene such kylenearylenealkylene, i.e., methylenephenylenemethyl ene, ethylenephenyleneethylene and the like; isoalkylidcne such as isopropylidene and the like; X and Y are hydro gen, alkyl such as methyl, ethyl, butyl, amyl, hexyl and the like; sulfo, halogen such as chlorine and bromine; p
'is or a whole number; and n is 1 when p is 0 and p +1 when p is a whole number, i.e., 2 when p is .l. V
The following examples will serve to illustrate the invention'but it is to be understood that the invention is not restricted thereto.
. 7 Example I Methanol mls 57 Acetone rrils 4O Methyl Cellosolve acetate n mls 3 Sulfosalicylic acid gms 1 Thiourea gins .4 Zinc chloride gms .6 m,m-'Ethylenedioxydiphenol gms e 1.5 4-ethylamino-3-methylbenzenediazonium V chloride: zinc chloride complex -gms.. 1.9
; Whenthis solution was coated on a starch-filled 'cloth base which had beensurface-coated with a polyvinyl ace- .tate or on plastic-coated cloth or cellulose acetate foil base, dried, exposed to actinic light under a positive original, and treated with ammonia vapors, a yellowishbrown'positivecopy was obtained having good visual.
density and excellent actinic opacity.
A The m,m'-ethylenedioxydiphenol was made by'a modi as ethylene, trimethylene, tetramethylene, pentamethylene, methyltrimethylene; al-
fication of the method of Kohn and Wilhelm (Monat a shefte, 43, 545- (1923)), from resorcinol, ethylene bro-' nick, and aqueous sodium; hydroxide.
' when this composition was coated on precoated glasscloth base, dried, irradiated with actinic. light under a positive original, and exposed to ammonia vapors, it gave a yellowish-brown positive copy with excellent opacity to ultraviolet light, fade resistance, and stability. 7
posed to actinic light under a positive original, and treated with ammoniavapors, this composition yielded a yellow ish-brown image with good visual density, opacity to ultraviolet light, dye stability, and developability.
colorless needles, M. 105-8 C.
Examples IV V Methyl Cellosolve ;m1s 60 Methyl Cellosolve acetatemls l0 Sulfosalicylic acid gms 2 Phosphoric acid mls .3 Citric acid gms .5 'Formic acid 1 mls 20 m,m'-Ethylenedioxydiphenol '.I 3.2 p-4-morpholinylbenzenediazonium chloride; zinc chloride complex e gms 2.5
When coated on cellulose acetate foil base, dried, irradiated withfactinic light'under a positive; original, and exposed to ammonia vapors, this composition yielded a yellowish-brown image, with excellent stability and good visual density. The printingspeed and ultraviolet opacity of this material were outstanding.
Example V The procedure is the same as in Example I excepting that the coupling component used is m,m-trirnethylenedioxydiphenol of the following formula:
OH 0H 7 t V O0 CHsCHsCHsOO V 'This compound may be prepared by the method of -Kohn and Wilhelm (Monatshefte 43, 545-5 (1923)). A
more convenient laboratory method, however, is the 1'39 action of m-nitrophenol with trimethylcne bromide and alkali to give 3,3 -dinitro-trimethylenedioxydibenzene, M.
121-3 0., which was reduced catalytically in ethanol over palladium on carbon to yield m,m'-ethylenedioxydianiline, M. 15-1-3 C. Diazotization and hydrolysis with dilutesulfuric acid gave a product identical with the "compound prepared by Kohn and Wilhelm (l.c.).
V V E xample lfl V t The procedure is the same as in Examplell excepting that the coupling componentused enedioxydiphenol of the following formula:
p on 1 on oomcmcmomo' This compound may be prepared as follows: m-Nitrophenol was reacted with 1,4-dibromobutane to give 3,3- -dinitrotetramethylenedioxydibenzene, M. 7 -7 C., which was reduced in isopropyl alcohol over palladium on carbon to the amine, M. 128-30 C. 'Diazotization and hydrolysis with dilute sulfuric acid were completed as in Example V and the desired compound was obtained as Example,
The procedure is the same as in Example 111 excepting that the coupling component is m,m'-pent amethylenedioxydiphenol of the following formula:
OH OH o omomomomonio This compound may be prepared 'as follows: 1,5-divbromopentane and m-nitrophenol were condensed to 3,3- dinitropentamethylenedioxydibenzene, M. 94-6 C. This was reduced in ethyl alcohol over palladium on carbon to the amine, M. 1'l9-2l C. Diazotization and hydrolysis with-dilute sulfuric acid; gave-the desired compound as colorless ,needles, M. -l10 l C; After recrystallizais m,m'-tetramethyltion from benzene, the product melted at 110.542 C., and analyzed asfollows; C 70,98, H 6.94; calculated 070.86, H 6.94.
' Exampl ha w sdt re s e amc a n i a ple I e c p g t he' np ins cmnpasm. mplcy i m'- -m. y
im fl v ne i x i eacl Qft e i ll ns u Example IX The procedure is the same as in Example HI excepting that the coupling component is 6,6-dimethyl-3,3- trimethylenedioxydiphenol of the formula:
OH OH CH CHI OCHICBICHIO This compound may be prepared as follows: B-nitro- 4-methylphenol was prepared from 3-nitro-4-methylaniline by diazotization and hydrolysis (Harvey and Roberson, J. Chem. Soc. 1938, 97-401). This was reacted with trimethylene bromide and alkali to yield 4,4'-dimethyl-3,3'-dinitrotrimethylenedioxydibenzene, M. 106- 9 C. Reduction in ethanol over palladium on carbon went smoothly to give the amino derivative, M. 129-30 C. Diazotization and hydrolysis by the usual method gave the desired compound, M. 139-41 C.
Example X The procedure is the same as in Example III excepting that the coupling component is m,rn'-(p-phenylenedimethylenedioxy) cliphenol of the formula:
on m CHGOHMQ This compound may be prepared as follows: m-Nitrophenol and p-phenylenedimethylene bromide were reacted to give 3,3-dinitro-p-phenylenedimethylenedioxydibenzene, M. 193-6" C. The amino compound, prepared by reduction in ethanol over palladium on carbon was diazotized and hydrolyzed to the desired compound, M. 724 C.
Example XI The procedure is the same as in Example II excepting that the coupling component is 6,6-dihexyl-3,3'-isopropylidenedioxydiphenol of the formula:
'Ihis was prepared 4-hexylresorcinol, acetone, and hydrogen chloride by the method of Uoto and Makida (Jap. Pat. 289 (Jan. 30, 1951); Chem. Abstn, 47, 4369g (195 3) Ergmple XII Theprocedure is the same as in Example I excepting that thecouplin'g component employed isr'rnm'cthylenedioxydiphenolformaldehyde polymer of the formula:
Example XIII The procedure is the same as in Example 11 excepting that the coupling component employed is 4,4',6,6'-tetramethyl-3,3'-trimethylenedioxydiphenol of the formula:
OH OH OCHzCH CHrO This compound may be prepared as follows: 2,4-dimethyl-S-nitrophenol was obtained as indicated by Robertson and Robinson, J. Chem. Soc., 2201 (1927), and reacted with trimethylenebromide and alkali to give 5,5- dinitro 2,2,4,4' tetramethyltrimethylenedioxydibenzene, M. l7l-4 C. This reduced smoothly over palladium on carbon to the diamine, M. 112-15 C. Diazotization and hydrolysis with dilute sulfuric acid gave the desired compound, M. l42.5-4.5 C.
Modifications of the invention will occur to persons skilled in the art and We, therefore, do not intend to be limited in the patent granted except as necessitated by the appended claims.
We claim:
1. Light sensitive diazotype materials comprising a base sensitized with a light sensitive diazonium compound, and as the coupling component, the compound of the following formula:
(amylase) comprising a translucent base sensitized with a light sensir 1 7 r 8 tive diazonitlm compound, and as the eonplingcomlight-sensitive compound'isa p-4-morpholinylbenzene diaponent, a compound of theiollowin'g formula: V zonium salt. V .1 V
a n r r r v 1 5. The article as defined in claim 2whe'rein'thecou- 1 pling component is m,m'.-trimethy1enedioxydibhenol.
5 6 The article as defined in claim 2 wherein the coupling component is m,m '-tetrainethylenediokydiphenol.
' 7. The article asdefined'in claim' 2 wherein'th'ecoue pling component is m,m'-pentamethylenedioxydiphenol.
n o p 10 7 References Citedin the file of patent UNITED STATES PATENTS I 2,536,989 Von Glahn etal Jan. 2, 1951 ,wherein A is selected'from the class consisting of alkyl- 2,650,925 s Sept. 1, 1953 ene, alkylene-arylene-alkylene and isoalkylidene; X and I I FOREIGN PATENTS 1 Y are selected from the class consisting of hydrogen, 6 6 7 Great fi n r f 9 alkyl, sulfo and halogen; p is selected fi'om'the class con- 7 1 I 'sisting of 0 and a' whole number; and n ris l when p is 7 OTHER 0"and p+1 when p is 'a whole number.. 1 Chem. Abstracts, 47; 4369g ,(1953).
3. The article as defined, claim 2 wherein the couvll/Icmatslnefte, 43, 545 to (1923); I pling component is m,m,'-ethylenedioxydiphenol. Saunders, The Aromatic Diazo, 2nd ed., 1949, pub. by 4; The article as defined in claim 2 whereintthe cou- Edward Arnold & C0,, London, pages 197-200 and pling component is m,m'-ethylenedioxydiphenol and the 217-219. v I

Claims (1)

1. LIGHT SENSITIVE DIAZOTYPE MATERIALS COMPRISING A BASE SENSITIZED WITH A LIGHT SENSITIVE DIAZONIUM COMPOUND, AND AS THE COUPLING COMPONENT, THE COMPOUND OF THE FOLLOWING FORMULA:
US641023A 1957-02-19 1957-02-19 m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity Expired - Lifetime US2940852A (en)

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NL97385D NL97385C (en) 1957-02-19
NL225064D NL225064A (en) 1957-02-19
BE564689D BE564689A (en) 1957-02-19
US641023A US2940852A (en) 1957-02-19 1957-02-19 m, m'-dioxydiphenols as coupling components in diazotype intermediates of high opacity
GB2993/58A GB840945A (en) 1957-02-19 1958-01-29 úÝ, úÝ-dioxydiphenols as coupling components in diazotype materials
CH5602558A CH375988A (en) 1957-02-19 1958-02-19 Photosensitive diazotype material

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US3086861A (en) * 1960-07-01 1963-04-23 Gen Aniline & Film Corp Printing plates comprising ink receptive azo dye surfaces
US3113025A (en) * 1960-03-02 1963-12-03 Gen Aniline & Film Corp Diazotype materials for the production of black images
US3149972A (en) * 1960-08-16 1964-09-22 Gen Aniline & Film Corp Diazo and resinous coupler printing plates for photomechanical reproduction
US3183093A (en) * 1959-12-09 1965-05-11 Keuffel & Esser Co Light sensitive diazotype material containing dibenzyl alkylamine coupling agents
US3186845A (en) * 1961-11-11 1965-06-01 Keuffel & Esser Co Two-component diazotype material
US3300534A (en) * 1961-01-04 1967-01-24 Sun Oil Co Process for preparing phenolic compounds
US3499763A (en) * 1967-05-01 1970-03-10 Ibm Bis phenols as high opacity diazotype couplers
US3716364A (en) * 1970-09-02 1973-02-13 Addressograph Multigraph Diazotype materials
US3769018A (en) * 1970-05-13 1973-10-30 Oce Van Der Grinten Nv Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers
US4115590A (en) * 1964-02-26 1978-09-19 Ethyl Corporation Binuclear phenols for reducing plasma lipid levels
US4220805A (en) * 1978-09-18 1980-09-02 General Electric Company Linear dimers of bisphenols and method for making
US5569568A (en) * 1994-12-16 1996-10-29 Eastman Kodak Company Method for using a laser ablative recording element with low red or green absorption as a reprographic photomask
US9243007B2 (en) 2011-03-30 2016-01-26 Asahi Kasei Chemicals Corporation Organopolysiloxane, method for producing the same, and curable resin composition containing the organopolysiloxane

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JPS61104887A (en) * 1984-10-27 1986-05-23 Kanzaki Paper Mfg Co Ltd Thermal recording material

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GB626391A (en) * 1946-05-08 1949-07-14 Gen Aniline & Film Corp Photographic diazotype compositions containing n-acylamino phenol couplers
US2536989A (en) * 1948-01-20 1951-01-02 Gen Aniline & Film Corp Diazotype layers containing resorcinol derivatives
US2650925A (en) * 1948-05-03 1953-09-01 Laaketehdas Orion Oy N, n'-piperazine dicarbamate of 2, 4-di-hydroxyphenylthiol

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US2536989A (en) * 1948-01-20 1951-01-02 Gen Aniline & Film Corp Diazotype layers containing resorcinol derivatives
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Cited By (13)

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US3183093A (en) * 1959-12-09 1965-05-11 Keuffel & Esser Co Light sensitive diazotype material containing dibenzyl alkylamine coupling agents
US3113025A (en) * 1960-03-02 1963-12-03 Gen Aniline & Film Corp Diazotype materials for the production of black images
US3086861A (en) * 1960-07-01 1963-04-23 Gen Aniline & Film Corp Printing plates comprising ink receptive azo dye surfaces
US3149972A (en) * 1960-08-16 1964-09-22 Gen Aniline & Film Corp Diazo and resinous coupler printing plates for photomechanical reproduction
US3300534A (en) * 1961-01-04 1967-01-24 Sun Oil Co Process for preparing phenolic compounds
US3186845A (en) * 1961-11-11 1965-06-01 Keuffel & Esser Co Two-component diazotype material
US4115590A (en) * 1964-02-26 1978-09-19 Ethyl Corporation Binuclear phenols for reducing plasma lipid levels
US3499763A (en) * 1967-05-01 1970-03-10 Ibm Bis phenols as high opacity diazotype couplers
US3769018A (en) * 1970-05-13 1973-10-30 Oce Van Der Grinten Nv Diazotype materials containing resorcinol mono(aryloxy or arylthio)alkyl ethers
US3716364A (en) * 1970-09-02 1973-02-13 Addressograph Multigraph Diazotype materials
US4220805A (en) * 1978-09-18 1980-09-02 General Electric Company Linear dimers of bisphenols and method for making
US5569568A (en) * 1994-12-16 1996-10-29 Eastman Kodak Company Method for using a laser ablative recording element with low red or green absorption as a reprographic photomask
US9243007B2 (en) 2011-03-30 2016-01-26 Asahi Kasei Chemicals Corporation Organopolysiloxane, method for producing the same, and curable resin composition containing the organopolysiloxane

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NL97385C (en)
GB840945A (en) 1960-07-13
DE1068556B (en) 1959-11-05
BE564689A (en)
NL225064A (en)
CH375988A (en) 1964-03-15

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