US3715324A - Insoluble polymeric diazonium salt chromogen - Google Patents

Insoluble polymeric diazonium salt chromogen Download PDF

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US3715324A
US3715324A US00190393A US3715324DA US3715324A US 3715324 A US3715324 A US 3715324A US 00190393 A US00190393 A US 00190393A US 3715324D A US3715324D A US 3715324DA US 3715324 A US3715324 A US 3715324A
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chromogen
acid groups
groups
carboxylic acid
resin
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M Krall
B Hynes
G Krall
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3703Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/34Derivatives of acids of phosphorus
    • C11D1/345Phosphates or phosphites
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0057Oven-cleaning compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02Inorganic compounds ; Elemental compounds
    • C11D3/04Water-soluble compounds
    • C11D3/06Phosphates, including polyphosphates
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/30Amines; Substituted amines ; Quaternized amines

Definitions

  • the composition comprises an aqueous or substantially aqueous mixture of sodium hydroxide, a dimethyl polysiloxane, tetrasodium pyrophosphate, a polyethylene oxide mono and/or dihydrogen phosphate ester, a nonyl phenol polyethylene glycol ether and triethanol amine.
  • This invention relates to cleaning compositions. More precisely, the invention disclosed herein relates to a cleaning composition especially useful for removing accumulated grease or carbon from equipment such as stoves, grilles and related cooking equipment.
  • composition of the present invention comprises a mixture of essential ingredients which include sodium hydroxide, a dimethyl polysiloxane, tetrasodium pyrophosphate, a polyethylene oxide dihydrogen or monohydrogen phosphate ester, or mixture thereof, a nonyl phenol polyethylene glycol ether and tetraethanol amine.
  • the ingredients are dispersed in a suitable solvent medium preferably an aqueous or partially aqueous solvent medium.
  • the composition can be applied directly to the area of the equipment having grease and/or carbon accumulated thereon preferably While the equipment is at a temperature above about 200 F.
  • the composition can be applied directly to the surface of a grille heated at about 300 F. or higher.
  • elfervescence occurs and normally, all or substantially all of the grease and carbon is rapidly removed by way of the effervescent action.
  • a small amount of water can be applied dropwise to the area to re-establish the effervescent action. This operation can be continued until even the most resistant accumulation of grease and/or carbon is completely removed from the grille. After the effervescent action diminishes, the surface of the grille is then rinsed thoroughly and is ready for reuse.
  • compositions of the present invention will be apparent to those skilled in the art. Chief among these is that rubbing is not normally required and the removal of the accumulated grease and carbon from the surface is remarkably rapid. Moreover, there is another surprisingly unexpected advantage to be derived from the practice of the present invention. For example, as those skilled in the art know, food tends to stick to freshly cleaned grilles. This is especially true with such food as eggs, pancakes and others which could be mentioned. However, such sticking is rarely encountered with grilles cleaned by compositions of the present invention. This advantage is believed to be due to the presence of the linear dimethyl polysiloxane in the composition.
  • the above described active ingredients are dissolved or otherwise dispersed in a suitable inert medium which preferably is an aqueous or partially aqueous solvent medium.
  • a suitable inert medium which preferably is an aqueous or partially aqueous solvent medium.
  • the amount of water normally employed is sufficient to provide a composition wherein water represents from about to about 95but preferably between about to about 88percent by weight of the combined water and active ingredients.
  • EXAMPLE Mix 42.75 pounds of commercial grade NaOH (97% flake) in 900 pounds of water. While stirring, slowly add 4 pounds of a 10% by weight silicone antifoam emulsion.
  • the silicone involved in such antifoam emulsions are linear, food grade dimethyl polysiloxanes. Additional details relating to suitable silicone antifoam emulsions employed in the present invention can be found in Bulletin 04-096 dated February 1967 and Bulletin 04-0-88 dated October 1966 both published by Chemical Products Division, Dow Corning Corporation, Midland, Mich. Additional details relating to suitable silicone antifoam emulsons can be found on pp. 42 and 43 of Chemical and Plastics Physical Properties, 1968 edition, published by Union Carbide Corporation.
  • Alkapent M-60 is a mixture of polyoxyethylene mono and dihydrogen phosphate esters and specifically is a (p-nonylphenyl) omega-hydroxypoly(oxyethylene) mixture of dihydrogen phosphate and monohydrogen phosphate esters where the poly (oxyethylene) content averages 6 moles. Thereafter, 30 pounds of a nonionic surface active agent such as Tergitol NPX are added to the mixture.
  • Tergitol N PX is a nonionic, nonyl phenol polyethylene glycol ether having a hydrophile value (number of moles of ethylene oxide) of 10.5. Additional helpful details relating to Tergitol NPX can be found on page 22 of Chemical and Plastics Physical Properties, 1968 edition, published by Union Carbide Corporation. Nonionic surface active agents having characteristics of the type described therein are useful in the practice of the present invention. For example, on page 22 there are listed five specific nonyl phenol polyethylene glycol ethers wherein the hydrophobe is nonylphenol and wherein the number of moles of ethylene oxide, e.g., hydrophile, ranges from 4 in the case of NP-14 to 20 in the case of NP-40.
  • the final ingredient add 48 pounds of commercial grade triethanol amine.
  • the final aqueous mixture can then be packaged in squeeze bottles, aerosol cans or other suitable containers whereby the composition can be conveniently added directly to the surface of grilles, stoves or like utensils having grease and/ or carbon accumulated thereon.
  • a cleaning composition wherein the active ingredients consist essentially of from about 10 to 40 percent by weight NaOH; from about 0.05 to about 0.5 percent by weight of a linear dimethyl polysiloxane; from about 1 to about 5 percent by weight of tetrasodium pyrophosphate; from about to about 40 percent by weight of an alpha-(p-nonyl phenyl)-omega-hydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters wherein the oxyethylene content averages 6 moles; from about 5 to about 30 percent by weight of a nonyl phenol polyethylene glycol ether having a hydrophile value between 4 to and from about 10 to about 40 percent by weight of triethanol amine.
  • the concentration of said tetrasodium pyrophosphate is from about 2 to about 4 percent by weight; the concentration of said alpha-(p-nonyl phenyl)-omega-hydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters is from about 20 to about 30 percent by weight, the concentration of said nonyl phenol polyethylene glycol ether is from about 10 to about 25 percent by weight and the concentration of said triethanol amine is from about 20 to about 35 percent by weight.
  • an aqueous cleaning composition wherein the active ingredients consist essentially of from about 10 to about 40 percent by weight NaOH; from about 0.05 to about 0.5 percent by weight of a linear dimethyl polysiloxane; from about 1 to about 5 percent by weight of tetrasodium pyrophosphate; from about 10 to about 40 percent by weight of an alpha-(p-nonyl phenyl)-omegahydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters wherein the oxyethylene content averages 6 moles; from about 5 to about 30 percent by weight of a nonyl phenol polyethylene glycol ether having a hydrophile value of 10.5 and from about 10 to about 40 percent by weight of triethanol amine, said active ingredients being dispersed in water which is present in a concentration between about 75 to about 95 percent by weight of the combined weight of water and said active ingredients.
  • a method for cleaning a surface which comprises the step of applying the composition of claim 5 to said surface while said surface is heated at a temperature above about 200 F.
  • a method for cleaning a surface which comprises the step of applying the composition of claim 6 to said surface while said surface is heated at a temperature above about 200 F.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

A novel insoluble polymeric diazonium salt chromogen consisting of a diazotized aromatic polyamine bound by an amide linkage to a cation exchange resin can be prepared by reacting a cation exchange resin containing carboxylic acid groups or salts of such carboxylic acid groups with a halogenating agent to convert some of the resin carboxylic acid groups or salts of such acid groups to acyl halide groups, reacting the resulting acyl halide groups with an aromatic polyamine to form a resin containing amide linkages and free aromatic amino groups, and then diazotizing the free aromatic amino groups. The resulting insoluble chromogen can be used to detect coupling compounds by forming colored reaction products with such coupling compounds. This chromogen can also be used to detect enzyme activity wherein the enzyme catalyzes a reaction with a suitable substrate to release a coupling compound which will form a colored reaction product with the insoluble chromogen.

Description

United States Patent US. Cl. 252-529 8 Claims ABSTRACT OF THE DISCLOSURE A novel cleaning composition useful for removing grease and/ or carbon from stoves, grilles, cooking utensils and the like. The composition comprises an aqueous or substantially aqueous mixture of sodium hydroxide, a dimethyl polysiloxane, tetrasodium pyrophosphate, a polyethylene oxide mono and/or dihydrogen phosphate ester, a nonyl phenol polyethylene glycol ether and triethanol amine.
CROSS REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of U .S. patent application Ser. No. 779,618 filed Nov. 27, 1968 now abandoned.
BACKGROUND OF THE INVENTION Part I.The field of the invention This invention relates to cleaning compositions. More precisely, the invention disclosed herein relates to a cleaning composition especially useful for removing accumulated grease or carbon from equipment such as stoves, grilles and related cooking equipment.
Part II.Description of the prior art The problem of removing accumulated grease and carbon from grilles or like utensils and from the exterior and interior of stoves is one which is long outstanding in the art. This is particularly true in commercial establishments where the grilles and stoves are continually used throughout the business hours. In such establishments, considerable time and eEort is expended in cleaning equipment of the type described. For example, the grilles normally employed must be cleaned at least daily. Presently, the celaning operation involves the use of detergents or soaps usually in combination with an abrasive material such as pumice or the like. Depending upon the size of the grille, the operation will oftentimes consume the better part of an hour or more. The cleaning of the exterior or interior of stoves is equally ineflicient and time consuming since the stove must oftentimes be cooled before the operation can commence. Accordingly, the grease becomes more resistant to the cleaning composition employed and excess time is consumed.
SUMMARY OF THE INVENTION In accordance with the practice of the present invention a novel cleaning composition is presented which is surprisingly eifective in rapidly removing accumulated grease and carbon from cooking equipment. The composition of the present invention comprises a mixture of essential ingredients which include sodium hydroxide, a dimethyl polysiloxane, tetrasodium pyrophosphate, a polyethylene oxide dihydrogen or monohydrogen phosphate ester, or mixture thereof, a nonyl phenol polyethylene glycol ether and tetraethanol amine. The ingredients are dispersed in a suitable solvent medium preferably an aqueous or partially aqueous solvent medium. The composition can be applied directly to the area of the equipment having grease and/or carbon accumulated thereon preferably While the equipment is at a temperature above about 200 F. For example, the composition can be applied directly to the surface of a grille heated at about 300 F. or higher. Upon application, elfervescence occurs and normally, all or substantially all of the grease and carbon is rapidly removed by way of the effervescent action. Should the grease in some areas not be removed by the initial effervescent action, a small amount of water can be applied dropwise to the area to re-establish the effervescent action. This operation can be continued until even the most resistant accumulation of grease and/or carbon is completely removed from the grille. After the effervescent action diminishes, the surface of the grille is then rinsed thoroughly and is ready for reuse.
Many advantages of the composition of the present invention will be apparent to those skilled in the art. Chief among these is that rubbing is not normally required and the removal of the accumulated grease and carbon from the surface is remarkably rapid. Moreover, there is another surprisingly unexpected advantage to be derived from the practice of the present invention. For example, as those skilled in the art know, food tends to stick to freshly cleaned grilles. This is especially true with such food as eggs, pancakes and others which could be mentioned. However, such sticking is rarely encountered with grilles cleaned by compositions of the present invention. This advantage is believed to be due to the presence of the linear dimethyl polysiloxane in the composition.
DESCRIAPTION OF THE PREFERRED EMBODIMENT The active ingredients of the compositions of the present invention and the percent by weight thereof with respect to the total weight of active ingredients are set forth below.
Percent by weight In accordance with the practice of the present invention, the above described active ingredients are dissolved or otherwise dispersed in a suitable inert medium which preferably is an aqueous or partially aqueous solvent medium. For example, the amount of water normally employed is sufficient to provide a composition wherein water represents from about to about 95but preferably between about to about 88percent by weight of the combined water and active ingredients.
The invention and manners of practicing same will be better understood by reference to the following example. It is to be understood that the example is illustrative in nature and in no way should it be construed so as to limit the invention beyond those limitations expressly set forth in the present specification or in the claims which appear hereinafter.
EXAMPLE Mix 42.75 pounds of commercial grade NaOH (97% flake) in 900 pounds of water. While stirring, slowly add 4 pounds of a 10% by weight silicone antifoam emulsion. The silicone involved in such antifoam emulsions are linear, food grade dimethyl polysiloxanes. Additional details relating to suitable silicone antifoam emulsions employed in the present invention can be found in Bulletin 04-096 dated February 1967 and Bulletin 04-0-88 dated October 1966 both published by Chemical Products Division, Dow Corning Corporation, Midland, Mich. Additional details relating to suitable silicone antifoam emulsons can be found on pp. 42 and 43 of Chemical and Plastics Physical Properties, 1968 edition, published by Union Carbide Corporation. After mixing the above ingredients, add 5.5 pounds of commercial grade tetrasodium pyrophosphate (hydrate) and then add 45 pounds of Alkapent M-60. Alkapent M-60 is a mixture of polyoxyethylene mono and dihydrogen phosphate esters and specifically is a (p-nonylphenyl) omega-hydroxypoly(oxyethylene) mixture of dihydrogen phosphate and monohydrogen phosphate esters where the poly (oxyethylene) content averages 6 moles. Thereafter, 30 pounds of a nonionic surface active agent such as Tergitol NPX are added to the mixture. Tergitol N PX is a nonionic, nonyl phenol polyethylene glycol ether having a hydrophile value (number of moles of ethylene oxide) of 10.5. Additional helpful details relating to Tergitol NPX can be found on page 22 of Chemical and Plastics Physical Properties, 1968 edition, published by Union Carbide Corporation. Nonionic surface active agents having characteristics of the type described therein are useful in the practice of the present invention. For example, on page 22 there are listed five specific nonyl phenol polyethylene glycol ethers wherein the hydrophobe is nonylphenol and wherein the number of moles of ethylene oxide, e.g., hydrophile, ranges from 4 in the case of NP-14 to 20 in the case of NP-40. As the final ingredient, add 48 pounds of commercial grade triethanol amine. The final aqueous mixture can then be packaged in squeeze bottles, aerosol cans or other suitable containers whereby the composition can be conveniently added directly to the surface of grilles, stoves or like utensils having grease and/ or carbon accumulated thereon.
Many modifications in incidental details of the above example offered for the purpose of illustrating the invention can be employed without departing from the spirit and scope of the invention defined in the appended claims.
Having described the invention as well as manners of practicing same and preferred embodiments thereof what is declared as new and desired to be secured by US. Letters iPatents as follows:
1. A cleaning composition wherein the active ingredients consist essentially of from about 10 to 40 percent by weight NaOH; from about 0.05 to about 0.5 percent by weight of a linear dimethyl polysiloxane; from about 1 to about 5 percent by weight of tetrasodium pyrophosphate; from about to about 40 percent by weight of an alpha-(p-nonyl phenyl)-omega-hydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters wherein the oxyethylene content averages 6 moles; from about 5 to about 30 percent by weight of a nonyl phenol polyethylene glycol ether having a hydrophile value between 4 to and from about 10 to about 40 percent by weight of triethanol amine.
2. A cleaning composition of claim 1 wherein said ingredients are dispersed in water which is present in a concentration between about 75 to about 95 percent by weight of the combined weight of water and said active ingredients.
3. A composition of claim 1 wherein the concentration of NaOH is from about 20 to about 30 percent by weight, the concentration of said dimethyl polysiloxane is from about 0.1 to about 0.4 percent by weight. The concentration of said tetrasodium pyrophosphate is from about 2 to about 4 percent by weight; the concentration of said alpha-(p-nonyl phenyl)-omega-hydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters is from about 20 to about 30 percent by weight, the concentration of said nonyl phenol polyethylene glycol ether is from about 10 to about 25 percent by weight and the concentration of said triethanol amine is from about 20 to about 35 percent by weight.
4. A cleaning composition of claim 3 wherein said ingredients are dispersed in water which is present in a concentration between about to about percent by weight of the combined weight of water and said active ingredients.
5. An aqueous cleaning composition wherein the active ingredients consist essentially of from about 10 to about 40 percent by weight NaOH; from about 0.05 to about 0.5 percent by weight of a linear dimethyl polysiloxane; from about 1 to about 5 percent by weight of tetrasodium pyrophosphate; from about 10 to about 40 percent by weight of an alpha-(p-nonyl phenyl)-omegahydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters wherein the oxyethylene content averages 6 moles; from about 5 to about 30 percent by weight of a nonyl phenol polyethylene glycol ether having a hydrophile value of 10.5 and from about 10 to about 40 percent by weight of triethanol amine, said active ingredients being dispersed in water which is present in a concentration between about 75 to about 95 percent by weight of the combined weight of water and said active ingredients.
6. A composition of claim 5 wherein the concentration of NaOH is from about 20 to about 30 percent by weight; the concentration of said dimethyl polysiloxane is from about 0.1 to about 0.4 percent by weight; the concentration of said tetrasodium pyrophosphate is from about 2 to about 4 percent by weight; the concentration of said alpha-(p-nonyl phenyl)-omega-hydroxy poly-(oxyethylene) mixture of mono-hydrogen and di-hydrogen phosphate esters is from about 20 to about 30 percent by weight; the concentration of said nonyl phenol polyethylene glycol ether is from about 10 to about 25 percent by weight and the concentration of said triethanol amine is from about 20 to about 35 percent by weight.
7. A method for cleaning a surface which comprises the step of applying the composition of claim 5 to said surface while said surface is heated at a temperature above about 200 F.
8. A method for cleaning a surface which comprises the step of applying the composition of claim 6 to said surface while said surface is heated at a temperature above about 200 F.
References Cited Oven cleaner digest LEON D. ROSDOL, Primary Examiner E. L. ROLLINS, Assistant Examiner US. Cl. X.R. 252-548

Claims (6)

1. An insoluble polymeric diazonium salt chromogen having a coupling power from 4.25 to about 350 milligrams of naphthol per gram of chromogen as measured by Method A or Method B of the above specification consisting essentially of an insoluble cation exchange polymeric resin having reactive groups selected from the class consisting of carboxylic acid groups, potassium salts of such acid groups, and sodium salts of such acid groups attached to the resin and wherein a sufficient amount of the reactive groups are each individually bonded through an acyl-amide linkage to the diazotized form of a carbocyclic aromatic diamine moiety derived from a compound selected from the class consisting of benzidine, o-tolidine, 0-dianisidine, phenylenediamine and 2-chloro-1,4-diaminobenzene to achieve such coupling power.
2. A chromogen according to claim 1 wherein the cation exchange resin contains carboxylic acid groups.
3. A chromogen according to claim 1 wherein the cation exchange resin contains sodium salts of carboxylic acid groups.
4. A chromogen according to claim 1 having a coupling power, as measured by Method A or Method B of the above specification, of from about 25 to about 45 milligrams of naphthol per gram of chromogen.
5. A chromogen according to claim 1 having a coupling power, as measured by Method A or Method B of the above specification, of from about 190 to about 350 milligrams of naphthol per gram of chromogen.
6. A process for the preparation of an insoluble polymeric diazonium salt chromogen according to claim 1 which comprises reacting An insoluble cation exchange resin having reactive groups selected from the class consisting of carboxylic acid groups, potassium salts of such acid groups, and sodium salts of such acid groups attached to the resin with a halogenating agent to form acyl halide groups containing from 0.2 to 2.37 milliequivalents of acyl halide per gram of resin, reacting the resulting acyl halide groups with a carbocyclic aromatic diamine selected from the class consisting of benzidine, o-tolidine, o-dianisidine, phenylenediamine, and 2-chloro-1,4-diaminobenzene to form a resin having a sufficient amount of the reactive groups attached thereto each individually bonded through an acyl-amide linkage to a carbocyclic aromatic diamine moiety derived from a compound selected from the class consisting of benzidine, o-tolidine, o-dianisidine, phenylenediamine, and 2-chloro-1,4-diaminobenzene, said moiety having a free amino group, to subsequently achieve a coupling power from 4.25 to about 350 milligrams of naphthol per gram of chromogen as measured by Method A or Method B of the above specification, and diazotizing the free amino group of each said moiety to produce the insoluble polymeric diazonium salt chromogen having the above coupling power.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4285840A (en) * 1977-08-29 1981-08-25 Sandoz Ltd. Detergent compositions
US4578208A (en) * 1983-05-07 1986-03-25 Henkel Kommanditgesellschaft Auf Aktien Compositions and processes for cleaning and passivating metals
US4617063A (en) * 1984-12-04 1986-10-14 Morris Brian V Cleaning silver
US4695396A (en) * 1985-02-07 1987-09-22 Henkel Kommanditgesellschaft Auf Aktien Two-component alkaline cleaning compositions and methods of preparing and using same
US4784798A (en) * 1985-08-28 1988-11-15 Henkel Kommanditgesellschaft Auf Aktien Demulsifying cleaning preparation having a prolonged surface-wetting effect
US4988391A (en) * 1983-09-08 1991-01-29 Bormann Georg Von Process, plant and/or apparatus for treating oil-contaminated debris or like materials
US4992212A (en) * 1988-10-18 1991-02-12 Lever Brothers Company, Division Of Conopco, Inc. Alkaline light duty liquid detergents that are non-staining to aluminum
US5968370A (en) * 1998-01-14 1999-10-19 Prowler Environmental Technology, Inc. Method of removing hydrocarbons from contaminated sludge

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274551A (en) * 1939-06-30 1942-02-24 Eastman Kodak Co Derivatives of resins and their preparation
US2906715A (en) * 1954-11-29 1959-09-29 Bayer Ag Sulphonamides of organic polymers
US3230087A (en) * 1959-02-26 1966-01-18 Azoplate Corp Light-sensitive polymeric diazonium and azidoacrylamido reproduction materials and process for making plates therefrom

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2274551A (en) * 1939-06-30 1942-02-24 Eastman Kodak Co Derivatives of resins and their preparation
US2906715A (en) * 1954-11-29 1959-09-29 Bayer Ag Sulphonamides of organic polymers
US3230087A (en) * 1959-02-26 1966-01-18 Azoplate Corp Light-sensitive polymeric diazonium and azidoacrylamido reproduction materials and process for making plates therefrom

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemisches Zentralblatt, Jarrg, 128, S 11715 (1957). *
Hackh s Chemical Dictionary, Fourth Edition, 1969, Page 16. *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4285840A (en) * 1977-08-29 1981-08-25 Sandoz Ltd. Detergent compositions
US4578208A (en) * 1983-05-07 1986-03-25 Henkel Kommanditgesellschaft Auf Aktien Compositions and processes for cleaning and passivating metals
US4988391A (en) * 1983-09-08 1991-01-29 Bormann Georg Von Process, plant and/or apparatus for treating oil-contaminated debris or like materials
US4617063A (en) * 1984-12-04 1986-10-14 Morris Brian V Cleaning silver
AU569019B2 (en) * 1984-12-04 1988-01-14 Morris, B.V. Cleaning silver or silver-plated articles
US4695396A (en) * 1985-02-07 1987-09-22 Henkel Kommanditgesellschaft Auf Aktien Two-component alkaline cleaning compositions and methods of preparing and using same
US4784798A (en) * 1985-08-28 1988-11-15 Henkel Kommanditgesellschaft Auf Aktien Demulsifying cleaning preparation having a prolonged surface-wetting effect
US4992212A (en) * 1988-10-18 1991-02-12 Lever Brothers Company, Division Of Conopco, Inc. Alkaline light duty liquid detergents that are non-staining to aluminum
US5968370A (en) * 1998-01-14 1999-10-19 Prowler Environmental Technology, Inc. Method of removing hydrocarbons from contaminated sludge

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