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US3650831A - Method of cleaning surfaces - Google Patents

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US3650831A
US3650831A US805797A US3650831DA US3650831A US 3650831 A US3650831 A US 3650831A US 805797 A US805797 A US 805797A US 3650831D A US3650831D A US 3650831DA US 3650831 A US3650831 A US 3650831A
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caustic
acid
color
foam
applying
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US805797A
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Eric Jungermann
Aaron B Herrick
Armando Carlo
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Dial Corp
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Armour Dial Inc
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/06—Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0057—Oven-cleaning compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments

Definitions

  • ABSTRACT A method of removing deposits of soil from surfaces, which comprises applying to said surfaces a caustic alkali including an acid-base color indicator, and applying an aqueous solution which is sufficiently acidic to substantially neutralize the caustic and visibly change the color of the caustic.
  • the method has particular efficacy for the cleaning of the interior surfaces of ovens and similar surfaces.
  • This invention relates to a method of cleaning deposits of soils from surfaces, for example, the interior surfaces of ovens and the like.
  • a widely used oven cleaner is the spread-on, sodium hydroxide or potassium hydroxide formulations that are messy to apply and must be handled with care as the highly caustic material is capable of injuring the user.
  • MOre recently, aerosol oven cleaners having a considerably lower concentration of alkali and containing a nonionic or ionic detergent with a solvent suchas water or alcohol have appeared. However, they are generally not as effective as the higher caustic content cleaners, although safer to use than the highly caustic formulas.
  • a method for removing deposits of soils from surfaces by applying to such surfaces a caustic, an acid-base color indicator, and thereafter applying an aqueous acidic solution to substantially neutralize the caustic, such as to a pH between about 4 and 10.5.
  • an aqueous acidic solution to substantially neutralize the caustic, such as to a pH between about 4 and 10.5.
  • the method comprises applying to such surfaces a caustic alkali foam containing an acid-base color indicator, and then applying sufficient aqueous acidic solution to the surface so as to substantially neutralize the caustic and to effect a change in color of the caustic.
  • the acid-base indicator may be included in the aqueous acidic solution or may be applied apart from either the caustic or the acid.
  • the caustic cleaner be in the form of a highly caustic alkali foam that is dispensed from an aerosol can.
  • the caustic foam is left on the surface long enough to do its job, generally about 20-30 minutes in the case of ovens.
  • the concentration of caustic used as percent.free hydroxyl may be from about 5 percent to about percent or more, preferably about 7-8 percent.
  • Any strong caustic alkali may be used, such as sodium hydroxide or potassium hydroxide or mixtures thereof. It may be in the form of a water solution, and it is preferable that a surfactant or combination of surfactants be employed to impart foaming characteristics.
  • the surfactant may be either anionic or nonionic, including but not restricted to anionic surfactants such as alkyl aryl sulfonates,.alcohol or fatty acid sulfonates or ether sulfates, alkyl amide or ester sulfonates, and fatty acid glycerol ester sulfates or ether sulfonates; and nonionic surfactants such as ethoxylated alcohols and alkylphenols, alkyanolamides, and block copolymers of ethylene and propyleneglycol.
  • anionic surfactants such as alkyl aryl sulfonates,.alcohol or fatty acid sulfonates or ether sulfates, alkyl amide or ester sulfonates, and fatty acid glycerol ester sulfates or ether sulfonates
  • nonionic surfactants such as ethoxylated alcohol
  • a suitable potassium or sodium soap may optionally be added and may consist of various combinations of tallow, cocoa, red oil, tall oil, stearic and oleic fatty acids.
  • a small amount of hexylene or propylene glycol may be added as a solubilizer; and various other ingredients may be added for their known effects such as sodium carboxy methyl cellulose or starch as thickening agents to aid foam adherence to the surface, and water soluble silicones as foam boosters and soil releaseagents.
  • An example of a preferred caustic foamcleaner to be dispensed from an aerosol container is:
  • Preferably 90-60 percent proportion of the above preferred cleaner is added, to an aerosol container along with 4-10 percent of a liquefied propellant for example fluorocarbons such as Freon 12 or Freon 114 or mixtures thereof or known hydrocarbon propellants.
  • a liquefied propellant for example fluorocarbons such as Freon 12 or Freon 114 or mixtures thereof or known hydrocarbon propellants.
  • the neutralizer should be sufiiciently acidic to reduce the alkalinity of the caustic to a relatively safe level.
  • Suitable active ingredients include any generally weak acid or acid salt, and the following are preferred: sodium dihydrogen phosphate, citric acid, hemi sodium phosphate, carbamide phosphoric acid, gluconic acid, ethylene diamine tetracetic acid, phosphoric acid, and any appropriate combinations thereof.
  • Other acids such as dilute mineral acids may be used but generally in low concentration or very dilute form.
  • the acid is preferably present in about 10 3 to l0"6 moles per liter hydrogen ion concentration; but this is widely variable since merely more of lower concentrations and less of higher concentrations will be used to substantially neutralize the caustic.
  • An example of a preferred neutralizer to be dispensed from an aerosol container is:
  • a defoamer to aid in the penetration of the acid or acid salt into the caustic foam.
  • incorporation of a soap in the first stage aids in defoaming by the neutralizer acting to convert the soap to a fatty acid.
  • Suitable acid-base indicators include any that effect a color or change or color at a pH of between about 4 and about 1 l and include but are not restricted to phenolphthalein, thymolphthalein, brilliant yellow, thymol blue, cresol purple, neutral red, phenol red, bromthymol blue, chlorphenol red, methyl red, bromcresol green, and alizarine yellow.
  • the acidbase indicator may be added to the first stage formulation, thereby visibly coloring the caustic foam i.e., phenolphthalein in about 0.2 percent by weight concentration will produce a red foam in the above described specific preferred caustic, thymolphthalein will produce blue, brilliant yellow will produce orange, and meta cresol purple will produce purple.
  • the second stage neutralizer would be sprayed on prior to wiping.
  • the neutralizer renders the caustic safe and the safe level is indicated by a change in color of the foam.
  • a caustic foam that includes phenolphthalein is sprayed on the surface to be cleaned a red color is developed.
  • Thymolphthalein indicator would also turn colorless, brilliant yellow indicator would become yellow and meta cresol purple would also become yellow. Bromthymol blue will change from blue to yellow and neutral red from light brown to red.
  • compositions of the present invention may be applied by brushing or daubing, they are preferably applied from two separate aerosol cans and/or spr'ay bottles.
  • the two-formulations may be applied via separate nozzles of a compartmentalized aerosol or via separable bottle aerosol nozzle and propellant combinations, and like means.
  • EXAMPLE I Exemplary caustic formulations were prepared as set forth in Table 1. Each of the formulations was added to an aerosol container, using about -96 percent of the formulation and about 4-l0 percent of a suitable propellant such as dichloro difluoromethane (Freon 12), tetrafluoro dichloro ethane (Freon 114), pentafluoro monochloro ethane (Freon 115), trifluoro trichloro ethane (Freon 113) cyclic hexafluoro dichloro butane (Freon C 316), octafluoropropane (Freon 218), cyclic octafluoro butane (Freon C 318), propane, butane, pentane, isobutane, hexane, eptane, octane, nonane and decane, or mixtures thereof.
  • a suitable propellant
  • a preferred acidic formulation was prepared as set forth hereinabove. It was packaged in a spray bottle and also in an aerosol can propelled with carbon dioxide, nitrogen, nitrous oxide or a combination of Freon 12, Freon l l and Freon l 14.
  • Table l The examples set forth in Table l were sprayed upon standard soiled panels.
  • the panels had vitreous porcelain surfaces and the soil resulted from deposits of general organic food constituents, including butter, that had been subjected to about 350F. heat for 30 minutes. All products formed good initial foams that were evaluated for stability and adhesion after a 20-minute period.
  • the panels were then sprayed with the neutralizing formulation until a change in color was observed. The foams then broke and the substantially neutralized residues were wiped off the panels with a cloth. No burns or skin irritation occurred. Where heavy spots of soil deposit remained, the panel was treated a second time. All soil was removed.
  • the method of removing deposits of calcined food soils from surfaces which comprises applying to said surfaces a highly caustic foam having about 5 percent or more of free hydroxyl and containing an amount of an acid-base indicator that will roduce a color change at a H of about 4 to about 11; and t en applying an aqueous acr no solution to substantially neutralize-the caustic foam to produce a change in color of said foam.
  • the method of removing deposits of soil from surfaces which comprises applying to said surfaces a caustic alkali having about 5 percent or more of free hydroxyl, said caustic containing an acid-base indicator that changes color at a pH weak acid solution of either citric acid or sodium hydrogen from surfaces which comprises applying to said surfaces an alkaline material containing a caustic alkali having about 5 percent or more of free hydroxyl and an acid-base indicator that produces a color change at a pH of about 4 to about 1 l; and then applying an aqueous solution which is sufficiently acidic to substantially neutralize the alkaline material and to change the color of the alkaline material.
  • said acid-base indicator is selected from the group consisting of phenolphthalein, thymolphthalein, brilliant yellow, meta cresol purple, thymol blue, neutral red, phenol red, methyl red, paranitro phenol and bromthymol blue.

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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 method of removing deposits of soil from surfaces, which comprises applying to said surfaces a caustic alkali including an acid-base color indicator, and applying an aqueous solution which is sufficiently acidic to substantially neutralize the caustic and visibly change the color of the caustic. The method has particular efficacy for the cleaning of the interior surfaces of ovens and similar surfaces.

Description

United States Patent Jungermann et al.
[451 Mar. 21, 1972 [54] METHOD OF CLEANING SURFACES [72] Inventors: Eric Jungermann, Chicago; Aaron B. Herrick, La Grange; Armando Carlo, Chicago, all of ill.
[73] Assignee: Armour-Dial, Inc., Chicago, Ill.
[22] Filed: Mar. 10, 1969 [21] Appl. No.: 805,797
[52] US. Cl ..134/27, 134/40, 252/156, 252/408 [51] Int. Cl ..B08b 3/08 [58] Field of Search 1 34/27, 28, 29, 22, 40; 252/408, 103, 156
[56] References Cited UNITED STATES PATENTS Phair ..252/408 X Sutton...
Primary Examiner-Joseph Scovronek Assistant ExaminerD. G. Millman Attorney-Carl C. Batz and Richard G. l-larrer [57] ABSTRACT A method of removing deposits of soil from surfaces, which comprises applying to said surfaces a caustic alkali including an acid-base color indicator, and applying an aqueous solution which is sufficiently acidic to substantially neutralize the caustic and visibly change the color of the caustic. The method has particular efficacy for the cleaning of the interior surfaces of ovens and similar surfaces.
5 Claims, No Drawings METHOD OF CLEANING SURFACES This invention relates to a method of cleaning deposits of soils from surfaces, for example, the interior surfaces of ovens and the like.
The cleaning of the interior surfaces of household cooking ovens is a difficult, tedious, and lengthy chore. A widely used oven cleaner is the spread-on, sodium hydroxide or potassium hydroxide formulations that are messy to apply and must be handled with care as the highly caustic material is capable of injuring the user. MOre recently, aerosol oven cleaners having a considerably lower concentration of alkali and containing a nonionic or ionic detergent with a solvent suchas water or alcohol have appeared. However, they are generally not as effective as the higher caustic content cleaners, although safer to use than the highly caustic formulas.
In accordance with the present invention a method is provided for removing deposits of soils from surfaces by applying to such surfaces a caustic, an acid-base color indicator, and thereafter applying an aqueous acidic solution to substantially neutralize the caustic, such as to a pH between about 4 and 10.5. When the caustic has been substantially neutralized, a color change takes place due to the presence of the acid-base color indicator thereby indicating to the user that the surface can be wiped clean without the need of rubber gloves or the worry of skin irritation. In a preferred embodiment, the method comprises applying to such surfaces a caustic alkali foam containing an acid-base color indicator, and then applying sufficient aqueous acidic solution to the surface so as to substantially neutralize the caustic and to effect a change in color of the caustic. In the alternative the acid-base indicator may be included in the aqueous acidic solution or may be applied apart from either the caustic or the acid.
We prefer that the caustic cleaner be in the form of a highly caustic alkali foam that is dispensed from an aerosol can. The caustic foam is left on the surface long enough to do its job, generally about 20-30 minutes in the case of ovens. The concentration of caustic used as percent.free hydroxyl may be from about 5 percent to about percent or more, preferably about 7-8 percent. Any strong caustic alkali may be used, such as sodium hydroxide or potassium hydroxide or mixtures thereof. It may be in the form of a water solution, and it is preferable that a surfactant or combination of surfactants be employed to impart foaming characteristics. The surfactant may be either anionic or nonionic, including but not restricted to anionic surfactants such as alkyl aryl sulfonates,.alcohol or fatty acid sulfonates or ether sulfates, alkyl amide or ester sulfonates, and fatty acid glycerol ester sulfates or ether sulfonates; and nonionic surfactants such as ethoxylated alcohols and alkylphenols, alkyanolamides, and block copolymers of ethylene and propyleneglycol. In addition a suitable potassium or sodium soap may optionally be added and may consist of various combinations of tallow, cocoa, red oil, tall oil, stearic and oleic fatty acids. A small amount of hexylene or propylene glycol may be added as a solubilizer; and various other ingredients may be added for their known effects such as sodium carboxy methyl cellulose or starch as thickening agents to aid foam adherence to the surface, and water soluble silicones as foam boosters and soil releaseagents. An example of a preferred caustic foamcleaner to be dispensed from an aerosol container is:
Ingredient 94 by weight 45% Potassium hydroxide l9.l7 Stearic acid 0.5 Oleic acid 4.8 Hexylene glycol 4.0 Acid-base indicator 0.2 Water 7l.4
Total 100.0%
Preferably 90-60 percent proportion of the above preferred cleaner is added, to an aerosol container along with 4-10 percent of a liquefied propellant for example fluorocarbons such as Freon 12 or Freon 114 or mixtures thereof or known hydrocarbon propellants.
The neutralizer should be sufiiciently acidic to reduce the alkalinity of the caustic to a relatively safe level. Suitable active ingredients include any generally weak acid or acid salt, and the following are preferred: sodium dihydrogen phosphate, citric acid, hemi sodium phosphate, carbamide phosphoric acid, gluconic acid, ethylene diamine tetracetic acid, phosphoric acid, and any appropriate combinations thereof. Other acids such as dilute mineral acids may be used but generally in low concentration or very dilute form. The acid is preferably present in about 10 3 to l0"6 moles per liter hydrogen ion concentration; but this is widely variable since merely more of lower concentrations and less of higher concentrations will be used to substantially neutralize the caustic. An example of a preferred neutralizer to be dispensed from an aerosol container is:
It is preferred to add a defoamer to aid in the penetration of the acid or acid salt into the caustic foam. In the alternative the incorporation of a soap in the first stage aids in defoaming by the neutralizer acting to convert the soap to a fatty acid.
Suitable acid-base indicators include any that effect a color or change or color at a pH of between about 4 and about 1 l and include but are not restricted to phenolphthalein, thymolphthalein, brilliant yellow, thymol blue, cresol purple, neutral red, phenol red, bromthymol blue, chlorphenol red, methyl red, bromcresol green, and alizarine yellow. The acidbase indicator may be added to the first stage formulation, thereby visibly coloring the caustic foam i.e., phenolphthalein in about 0.2 percent by weight concentration will produce a red foam in the above described specific preferred caustic, thymolphthalein will produce blue, brilliant yellow will produce orange, and meta cresol purple will produce purple. After the caustic has been applied and allowed sufficient time to work, the second stage neutralizer would be sprayed on prior to wiping. The neutralizer renders the caustic safe and the safe level is indicated by a change in color of the foam. Thus when a caustic foam that includes phenolphthalein is sprayed on the surface to be cleaned a red color is developed. When the neutralizer is applied the color disappears as the foam is substantially neutralized. Thymolphthalein indicator would also turn colorless, brilliant yellow indicator would become yellow and meta cresol purple would also become yellow. Bromthymol blue will change from blue to yellow and neutral red from light brown to red.
Although the compositions of the present invention may be applied by brushing or daubing, they are preferably applied from two separate aerosol cans and/or spr'ay bottles. As a further alternative the two-formulations may be applied via separate nozzles of a compartmentalized aerosol or via separable bottle aerosol nozzle and propellant combinations, and like means.
Thisinvention is still further illustrated by specific examples, which are not to be construed as composition limitations upon the scope thereof.
EXAMPLE I .Exemplary caustic formulations were prepared as set forth in Table 1. Each of the formulations was added to an aerosol container, using about -96 percent of the formulation and about 4-l0 percent of a suitable propellant such as dichloro difluoromethane (Freon 12), tetrafluoro dichloro ethane (Freon 114), pentafluoro monochloro ethane (Freon 115), trifluoro trichloro ethane (Freon 113) cyclic hexafluoro dichloro butane (Freon C 316), octafluoropropane (Freon 218), cyclic octafluoro butane (Freon C 318), propane, butane, pentane, isobutane, hexane, eptane, octane, nonane and decane, or mixtures thereof.
A preferred acidic formulation was prepared as set forth hereinabove. It was packaged in a spray bottle and also in an aerosol can propelled with carbon dioxide, nitrogen, nitrous oxide or a combination of Freon 12, Freon l l and Freon l 14.
The examples set forth in Table l were sprayed upon standard soiled panels. The panels had vitreous porcelain surfaces and the soil resulted from deposits of general organic food constituents, including butter, that had been subjected to about 350F. heat for 30 minutes. All products formed good initial foams that were evaluated for stability and adhesion after a 20-minute period. The panels were then sprayed with the neutralizing formulation until a change in color was observed. The foams then broke and the substantially neutralized residues were wiped off the panels with a cloth. No burns or skin irritation occurred. Where heavy spots of soil deposit remained, the panel was treated a second time. All soil was removed.
TABLE I 3. The method of removing deposits of calcined food soils from surfaces, which comprises applying to said surfaces a highly caustic foam having about 5 percent or more of free hydroxyl and containing an amount of an acid-base indicator that will roduce a color change at a H of about 4 to about 11; and t en applying an aqueous acr no solution to substantially neutralize-the caustic foam to produce a change in color of said foam.
43113 m e t hod of removing deposits of calcined food soils Example, percent by weight of ingredient Ingredient:
50% potassium hydroxide Surfactant (expressed as fatty acid). Ilexylono or propylene glycol. Water Thymolphthalein Phenolphthalein.. Brilliant yellow... Meta cresol purple. Para-nitro phenol...
Methyl red Phenol red Carboxymethyl cellulose 0.2
Total 100. 0 100. 0 100. 0 100. 0 100. 0 100.0 100.0
Color of caustic foam Blue Red Orange.-- Purple.... Yellow Yellow Red. Initial foam stability G d Good. G d Good..... Good. Good Good. Foam Stability, minutes Good. Good. Goo Poor Poor Good. Foam adhesion, 20 minutes..... Fair,...... Poor Poor Poor Poor.. Poor Poor. Neutralized color Colorless.. Colorless.. Yellow.. Colorless.. ed. Yellow. pH range of color. 9.3- 8.0- 7. 4- 7.0- 6. 2 8.0 Change l0.5....... 9.8 9.0 5.0 4.4.... 6.4. Soil removal Good... Good..... Good..... ood- Good..... G d-.... Good.
1 Color slightly unstable.
1 All foams were substantially neutralized by spraying ona% phosphate.
While this invention has been described with respect to specific embodiments of the method of removing deposits of soils from surfaces, such is by way of illustration and not in limitation; and it is to be understood that variations and modifications thereof obvious to those skilled the art may be made without departing from the spirit or scope of this inventron.
What is claimed is: g l
1. The method of removing deposits of soil from surfaces which comprises applying to said surfaces a caustic alkali having about 5 percent or more of free hydroxyl, said caustic containing an acid-base indicator that changes color at a pH weak acid solution of either citric acid or sodium hydrogen from surfaces which comprises applying to said surfaces an alkaline material containing a caustic alkali having about 5 percent or more of free hydroxyl and an acid-base indicator that produces a color change at a pH of about 4 to about 1 l; and then applying an aqueous solution which is sufficiently acidic to substantially neutralize the alkaline material and to change the color of the alkaline material.
5. The method of claim 4 in which said acid-base indicator is selected from the group consisting of phenolphthalein, thymolphthalein, brilliant yellow, meta cresol purple, thymol blue, neutral red, phenol red, methyl red, paranitro phenol and bromthymol blue.

Claims (4)

  1. 2. The method of removing deposits of soils from surfaces which comprises applying to said surfaces a caustic alkali having about 5 percent of more of free hydroxyl; applying an aqueous acidic solution containing an acid-base indicator that changes color at pH between about 4 and 11 to substantially neutralize the caustic.
  2. 3. The method of removing deposits of calcined food soils from surfaces, which comprises applying to said surfaces a highly caustic foam having about 5 percent or more of free hydroxyl and containing an amount of an acid-base indicator that will produce a cOlor change at a pH of about 4 to about 11; and then applying an aqueous acidic solution to substantially neutralize the caustic foam to produce a change in color of said foam.
  3. 4. The method of removing deposits of calcined food soils from surfaces which comprises applying to said surfaces an alkaline material containing a caustic alkali having about 5 percent or more of free hydroxyl and an acid-base indicator that produces a color change at a pH of about 4 to about 11; and then applying an aqueous solution which is sufficiently acidic to substantially neutralize the alkaline material and to change the color of the alkaline material.
  4. 5. The method of claim 4 in which said acid-base indicator is selected from the group consisting of phenolphthalein, thymolphthalein, brilliant yellow, meta cresol purple, thymol blue, neutral red, phenol red, methyl red, paranitro phenol and bromthymol blue.
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US4006091A (en) * 1975-03-14 1977-02-01 Amway Corporation Plastic bottle storable oven cleaner
US4390465A (en) * 1981-06-22 1983-06-28 Fremont Industries, Inc. Low temperature composition for plating pretreatment of ferrous metals
US4683008A (en) * 1985-07-12 1987-07-28 Sparkle Wash, Inc. Method for cleaning hard surfaces
US4965063A (en) * 1985-05-24 1990-10-23 Irene Casey Cleaner and disinfectant with dye
FR2673640A1 (en) * 1991-03-07 1992-09-11 Reckitt Colman New compositions for household use, processes for their preparation and their applications especially in the field of household maintenance
US5154917A (en) * 1990-09-11 1992-10-13 Beecham Inc. Color change mouthrinse
US5223245A (en) * 1990-09-11 1993-06-29 Beecham Inc. Color change mouthrinse
US5482654A (en) * 1994-11-09 1996-01-09 Warnaway Corporation Safety indicator system
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US5626685A (en) * 1985-10-18 1997-05-06 Spindler; William E. Method of removing a water insoluble surface coating from a surface
US5770222A (en) * 1989-12-22 1998-06-23 Imarx Pharmaceutical Corp. Therapeutic drug delivery systems
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US5842815A (en) * 1995-11-23 1998-12-01 Arthur Michael Rogers Howes Chemical treatment of treading surfaces
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US5922304A (en) * 1989-12-22 1999-07-13 Imarx Pharmaceutical Corp. Gaseous precursor filled microspheres as magnetic resonance imaging contrast agents
US5935553A (en) * 1989-12-22 1999-08-10 Imarx Pharmaceutical Corp. Methods of preparing gas-filled liposomes
US5985246A (en) * 1989-12-22 1999-11-16 Imarx Pharmaceutical Corp. Contrast agents for ultrasonic imaging and methods for preparing the same
US5997898A (en) * 1995-06-06 1999-12-07 Imarx Pharmaceutical Corp. Stabilized compositions of fluorinated amphiphiles for methods of therapeutic delivery
US6028066A (en) * 1997-05-06 2000-02-22 Imarx Pharmaceutical Corp. Prodrugs comprising fluorinated amphiphiles
US6033645A (en) * 1996-06-19 2000-03-07 Unger; Evan C. Methods for diagnostic imaging by regulating the administration rate of a contrast agent
US6071494A (en) * 1996-09-11 2000-06-06 Imarx Pharmaceutical Corp. Methods for diagnostic imaging using a contrast agent and a renal vasodilator
US6088613A (en) * 1989-12-22 2000-07-11 Imarx Pharmaceutical Corp. Method of magnetic resonance focused surgical and therapeutic ultrasound
US6117414A (en) * 1991-04-05 2000-09-12 Imarx Pharmaceutical Corp. Method of computed tomography using fluorinated gas-filled lipid microspheres as contract agents
US6120751A (en) * 1997-03-21 2000-09-19 Imarx Pharmaceutical Corp. Charged lipids and uses for the same
US6123923A (en) * 1997-12-18 2000-09-26 Imarx Pharmaceutical Corp. Optoacoustic contrast agents and methods for their use
US6139819A (en) * 1995-06-07 2000-10-31 Imarx Pharmaceutical Corp. Targeted contrast agents for diagnostic and therapeutic use
US6143276A (en) * 1997-03-21 2000-11-07 Imarx Pharmaceutical Corp. Methods for delivering bioactive agents to regions of elevated temperatures
US6146657A (en) * 1989-12-22 2000-11-14 Imarx Pharmaceutical Corp. Gas-filled lipid spheres for use in diagnostic and therapeutic applications
US6156292A (en) * 1991-09-17 2000-12-05 Sonus Pharmaceuticals, Inc. Gaseous ultrasound contrast media and method for selecting gases for use as ultrasound contrast media
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