WO2011096966A1 - Use of methylsulfonylmethane (msm) as a cooling agent - Google Patents

Use of methylsulfonylmethane (msm) as a cooling agent Download PDF

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Publication number
WO2011096966A1
WO2011096966A1 PCT/US2010/054828 US2010054828W WO2011096966A1 WO 2011096966 A1 WO2011096966 A1 WO 2011096966A1 US 2010054828 W US2010054828 W US 2010054828W WO 2011096966 A1 WO2011096966 A1 WO 2011096966A1
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msm
product
composition
temperature
embodiments
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PCT/US2010/054828
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French (fr)
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Anthony L. Keller
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Biogenic Innovations, Llc
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Priority to US61/301,112 priority
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Publication of WO2011096966A1 publication Critical patent/WO2011096966A1/en

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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08Materials not undergoing a change of physical state when used
    • C09K5/10Liquid materials
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/202Aliphatic compounds
    • A23L27/2022Aliphatic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463Organic compounds; Microorganisms; Enzymes
    • A23L3/3535Organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/36Freezing; Subsequent thawing; Cooling
    • A23L3/37Freezing; Subsequent thawing; Cooling with addition of or treatment with chemicals
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A23B - A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L7/00Cereal-derived products; Malt products; Preparation or treatment thereof
    • A23L7/10Cereal-derived products
    • A23L7/104Fermentation of farinaceous cereal or cereal material; Addition of enzymes or microorganisms

Abstract

Embodiments of the invention relate generally to compositions of methylsulfonylmethane (MSM) and a product, wherein the composition has altered warming or thawing characteristics. MSM is also combined with products in certain embodiments to facilitate reductions in temperature of products, to retard the warming of a product or to generate a product resistant to warming.

Description

USE OF METHYLSULFONYLMETHANE (MSM) AS A COOLING AGENT

CROSS REFERENCE TO RELATED APPLICATION

This application claims the benefit of co-pending U.S. Provisional

Application No. 61/301,112, filed February 3, 2010, which is incorporated herein its entirety.

FIELD

This disclosure relates generally to the use of methylsulfonylmethane (MSM) to facilitate temperature-modulation of products and maintenance of products at reduced temperatures.

BACKGROUND

Methylsulfonylmethane (MSM; (CH3)2S02), also known as dimethyl sulfone, is an organosulfur compound that is a metabolite of DMSO and certain sulfur-containing amino acids. MSM has been marketed primarily as a dietary supplement.

Numerous products require a reduction in temperature or maintenance at a reduced temperature during their production, storage, transportation and/or use. A common example is that water must be cooled in order to form ice, which may later be used to cool other products or materials that are present in a warmer environment. Another example is ice cream or other food products, which must be maintained at freezing temperatures during storage or transportation. Precise temperature control is also important in many applications. In other applications, rate of change of temperature, e.g. , the ability to cool a product quickly, is desirable. Example applications include systems for air conditioning, freezing, rapid freezing, refrigerating, manufacturing, storing, and transporting. Such applications may be in commercial, industrial, residential, and/or automotive settings, among others.

SUMMARY

Described herein is the unexpected discovery that combining MSM with a product results in a composition that, once frozen, requires more time to thaw or warm than a composition that does not comprise MSM. Thus, certain products that have been cooled will stay cool longer following exposure to a higher (e.g., elevated) temperature environment if the product comprises MSM than if the product does not comprise MSM. Additionally, certain products that have been frozen require more time to thaw following exposure to an environment with a temperature above the freezing point of the product if the product comprises MSM than if the product does not comprise added MSM. Further described herein is the unexpected discovery that addition of MSM to a product reduces the temperature of the product.

Thus, there is provided herein a method of generating a composition resistant to warming, comprising selecting a product to be cooled and combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition, thereby generating a composition resistant to warming. In some embodiments, the product to be cooled is an edible product.

Also provided herein is a method of retarding warming of a composition, comprising selecting a product to be cooled; combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition; and exposing the composition to an environment with a temperature greater than that of the composition for a period of time, wherein the time required for the composition to warm to the temperature of the environment is greater than the time required for a control product without MSM subject to the same conditions to warm to the temperature of the environment, thereby retarding warming of a composition. In some embodiments, the product to be cooled is an edible product.

Also provided herein is a method for cooling a composition, comprising: selecting a product to be cooled; and combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to cool the composition, thereby cooling the composition. In some embodiments, the product to be cooled is an edible product.

It will be further understood that the compositions and methods of reducing the temperature, retarding the warming or thawing, of a product, or methods of generating a product resistant to thawing, as disclosed herein, are useful beyond the specific circumstances that are described in detail herein. For instance such compositions and methods are expected to be useful for any number of conditions where cooling of a product, or maintain a product at a cool temperature is involved. BRIEF DESCRIPTION OF THE FIGURES

Fig. 1 illustrates that MSM increases the time required to thaw frozen tap water. The indicated amounts of MSM were combined with 500 mL of tap water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The solution with 50 g MSM never completely dissolved. The volume of thawed solution was measured for each MSM/tap water concentration at 72, 128, 188, 269, 435 and 565 minutes after removal from the freezer.

Fig. 2 illustrates that MSM increases the time required to thaw frozen tap water and maintains thawed tap water at a reduced temperature. The indicated amounts of MSM were combined with 500 mL of tap water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The solution with 50 g MSM never completely dissolved. The volume of thawed solution was measured for each MSM/tap water concentration at 140, 330 and 450 minutes after removal from the freezer (upper panel). Additionally, the temperature of the solution was measured at 195, 325 and 445 minutes after removal from the freezer using a laser radiation thermometer (lower panel).

Fig. 3 illustrates that MSM increases the time required to thaw frozen artificial sea water and maintains thawed artificial sea water at a reduced temperature. The indicated amounts of MSM were combined with 500 mL of artificial sea water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The solution with 50 g MSM never completely dissolved. The volume of thawed solution was measured for each MSM/artificial sea water concentration at 155, 340 and 490 minutes after removal from the freezer (upper panel). Additionally, the temperature of the solution was measured at 185, 335 and 485 minutes after removal from the freezer using a laser radiation thermometer. DETAILED DESCRIPTION

/. Terms

The following explanations of terms and methods are provided to better describe the present disclosure and to guide those of ordinary skill in the art in the practice of the present disclosure. The singular forms "a," "an," and "the" refer to one or more than one, unless the context clearly dictates otherwise. For example, the term "comprising a product" includes single or plural products and is considered equivalent to the phrase "comprising at least one product." The term "or" refers to a single element of stated alternative elements or a combination of two or more elements, unless the context clearly indicates otherwise. As used herein,

"comprises" means "includes." Thus, "comprising A or B," means "including A, B, or A and B," without excluding additional elements.

Unless explained otherwise, all technical and scientific terms used herein have the same meaning as commonly understood to one of ordinary skill in the art to which this disclosure belongs. It is further to be understood that all molecular weight or molecular mass values, given for molecules, are approximate, and are provided for description. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present disclosure, suitable methods and materials are described below. The materials, methods, and examples are illustrative only and not intended to be limiting. For example, conventional methods well known in the art to which a disclosed invention pertains are described in various general and more specific references, including, for example, Loudon, Organic Chemistry, Fourth Edition, New York: Oxford

University Press, 2002, pp. 360-361, 1084-1085; Smith and March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Fifth Edition, Wiley-Interscience, 2001; or Vogel, A Textbook of Practical Organic Chemistry, Including Qualitative Organic Analysis, Fourth Edition, New York: Longman, 1978. In case of conflict, the present specification, including explanations of terms, will control.

Administration: To provide or give a subject a compound, such as MSM, by any effective route. Exemplary routes of administration include, but are not limited to, injection (such as subcutaneous, intramuscular, intradermal, intraperitoneal, and intravenous), oral, sublingual, rectal, transdermal (such as topical), intranasal, vaginal and inhalation routes. A particular type of

administration is topical.

Combining: The mixing together of two or more substances. "Combining a product and MSM" includes the mixing together of a product and MSM to form a composition of the product and MSM. Combining a product and MSM can be done by any method known to those of skill in the art, including dissolving or mixing. MSM may be compounded, admixed, incorporated into, or deposited or sprayed on top of a product. Combining a product and MSM includes methods of combining MSM with a finished product as well as methods of combining MSM with an unfinished product during the manufacture of the product. Thus, combining a product and MSM includes combining the ingredients required for manufacturing a product with MSM, and then making the product, thereby combining the product and MSM.

Composition: A combination of two or more substances or compounds. The combination of substances may result in a liquid, a viscous solution, a gel, a semisolid, or a solid. MSM may be combined with a different substance or substances to form a composition. For example, in one embodiment, MSM is combined with water to form a composition. Compositions including MSM may contain from about 0.01% to about 99.9% MSM. Compositions including MSM may contain about 0.01% or less MSM. In some embodiments, a composition contains about 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20% MSM.

Contacting: Placement of two or more substances in direct physical association, including in solid, liquid and gas forms or substances. Contacting includes contact between one molecule and another molecule. Contacting can occur in vitro or in vivo.

Control: Samples believed to be normal (e.g., representative activity or function in the absence of the variable being tested) as well as laboratory values, even though possibly arbitrarily set, keeping in mind that such values can vary from laboratory to laboratory. A control group is practically identical to the treatment group, except for the single variable of interest whose effect is being tested, which is only applied to the treatment group.

Decrease or Reduce: A reduction in the quality, amount, or strength of something, including reducing the temperature of a product, compound or composition.

Dimethyl sulfoxide (DMSO): Dimethyl sulfoxide (DMSO), also known as methylsulfinylmethane or methyl sulfoxide, is an organosulfur compound with the formula

Figure imgf000007_0001
This colorless liquid is a polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, so that one may taste it soon after it comes into contact with the skin.

DMSO is well known as a nutritional supplement and as a pharmaceutical agent. One of skill in the relevant art will be familiar with these uses. Various grades of DMSO are available commercially (for example, product No. 472301 from Sigma- Aldrich, Corp., St. Louis, MO) and one of skill in the art will be familiar with a source of DMSO.

Effective amount of MSM: A quantity of MSM or a composition comprising MSM sufficient to achieve a desired effect on a product or another composition, or on a subject, being contacted with the MSM. An effective amount of MSM can be delivered in a single dose, or in several doses, during the course of various time intervals, for example daily or at other intervals. However, the effective amount MSM will be influenced by the MSM or composition comprising MSM applied, the method of application, the product or other composition, or subject, being contacted with the MSM or composition comprising MSM, and other factors that will be recognized by one of ordinary skill in the relevant field.

Environment: The area surrounding a product or composition, including the characteristics of that area, such as the temperature of the area.

Exposing: To subject something to an action, influence, or condition. For example, to subject a product, composition or compound to a particular environment.

Increase: To increase the quality, amount, or strength of something, including increasing the temperature of a product, compound or composition. Freezing point: The temperature at which a substance or composition transitions between liquid and solid state. A freezing temperature for a particular product or composition is a temperature at or below the freezing point for that product or composition.

Heat transfer fluid: A fluid that contacts a first device, substance, or object and transfers heat produced by the first device (substance or object) to other device(s) (or substance(s) or object(s)) that use or dissipate the heat. Heat transfer fluids include coolants and refrigerants. A composition containing MSM and water is an example of a heat transfer fluid. In some embodiments, a heat transfer fluid contains MSM, water and glycol.

Methylsulfonylmethane (MSM): An organosulfur compound with the formula (CH3)2S02. MSM is also known as DMS02, dimethyl sulfone, methyl sulfone and sulfonylbismethane. MSM has largely been marketed and sold as a dietary supplement.

MSM is structurally related to dimethyl sulfoxide (DMSO), but the behavior of these two is different. DMSO is a highly polar solvent and an excellent ligand, with water-like dissolving properties whereas MSM is less polar and less reactive. MSM i MSO. MSM has the following chemical structure:

Figure imgf000008_0001

Pharmaceutical composition: A chemical compound or composition capable of inducing a desired therapeutic or prophylactic effect when properly administered to a subject. A pharmaceutical composition can include a therapeutic agent, a diagnostic agent or a pharmaceutical agent. A therapeutic or

pharmaceutical agent is one that alone or together with an additional compound induces the desired effect (such as inducing a therapeutic or prophylactic effect when administered to a subject).

Product: Any substance or any combination of substances. The substance or substances may include liquid, a viscous solution, a gel, a semi-solid, or a solid. Non- limiting examples include edible products such as various foods and beverages, including frozen foods and beverages. Other examples include various industrial products. More examples include coolants, refrigerants, cryogenics, ice cream, fruit puree, water, water to be used in making ice and firefighting foam. A product can also be a combination of ingredients, such as a combination of ingredients required for manufacturing an edible or industrial product, or a product with a medical application. A product to be cooled is a product that will be exposed to an environment with a temperature below that of the product. A product to be frozen is a product that will be exposed to an environment with a temperature below the freezing point of the product.

Retarding: Slowing or extending the time required for something to occur. For example, retarding thawing of a product refers to extending the time required to thaw the product. Retarding warming of a product refers to extending the time required to warm a product. A product or composition with retarded warming characteristics is a composition or product that, when exposed to an environment with a greater temperature than that of the product or composition, will require more time to warm to the temperature of the environment than an equivalent product or composition that lacks retarded warming characteristics. For example, a composition comprising a combination of a product and an amount of MSM sufficient to yield a composition with retarded warming characteristics will require more time to warm to the temperature of an environment with a temperature greater than that of the composition than a composition that does not comprise an amount of MSM sufficient to yield a composition with retarded warming characteristics.

Shelf-life: The period of time a product may be stored before it becomes unfit for its intended purpose or before it becomes decreased in quality. Shelf-life varies depending on the product and the storage conditions. In some embodiments, shelf life may be extended by adding MSM to an edible product.

Subject: Living multi-cellular vertebrate organisms, a category that includes human and non-human mammals.

Under conditions sufficient for: A phrase used to describe any

environment or set of conditions that permits the desired activity or outcome. //. Overview of Several Embodiments

Described herein is a method for generating a composition resistant to warming, a method for retarding warming of a composition and a method of cooling a composition. Also described are certain compositions that comprise MSM.

Thus there is provided herein a method of generating a composition resistant to warming, comprising selecting a product to be cooled and combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition, thereby generating a composition resistant to warming. In some embodiments, the product to be cooled is an edible product. In some embodiments, selecting a product to be cooled comprises selecting a product to be frozen.

Also provided herein is a method of retarding warming of a composition, comprising selecting a product to be cooled; combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition; and exposing the composition to an environment with a temperature greater than that of the composition for a period of time, wherein the time required for the composition to warm to the temperature of the environment is greater than the time required for a control product without MSM subject to the same conditions to warm to the temperature of the environment, thereby retarding warming of a composition. In some embodiments, the product to be cooled is an edible product.

In some embodiments, a method of retarding warming of a composition comprises freezing the composition and exposing the composition to an environment with a temperature higher than that of the composition for a period of time comprises exposing the composition to an environment with a temperature above the freezing point of the composition. In some embodiments, , a method of retarding warming of a composition comprises wherein the time required for the composition to warm to the temperature of the environment is about 50% greater than the time required for the control product without MSM subject to the same conditions to warm to the temperature of the environment.

Also provided herein is a method for cooling a composition, comprising: selecting a product to be cooled; and combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to cool the composition, thereby cooling the composition. In some embodiments, the product to be cooled is an edible product. In some embodiments, a method for cooling a composition comprises wherein the product is a mixture of two or more ingredients and wherein the MSM reduces the temperature of the mixture to a lower temperature than the temperature of a combination of the same amount of MSM and each ingredient alone.

In some embodiments, the product to be cooled is an edible product. In some embodiments the product comprises a beverage, a frozen desert, fruit puree or water to be used in making ice. In some embodiments, the product comprises ice cream, yogurt, gelato, sorbet, or sherbert.

In various embodiments described herein, the product is used for a medical application. In some embodiments, the composition is incorporated into one or more of a water bath, a muscle wrap, or a cold pack.

In various embodiments described herein, the product is a heat transfer fluid.

In some embodiments, the product comprises water and glycol.

In some embodiments, the product is a liquid, a viscous solution, a gel, a semi-solid, or a solid.

In some embodiments, the composition has a longer shelf life compared to the product.

In some embodiments, the amount of MSM is ranges from about 0.2% to about 4% of the composition. In some embodiments, the amount of MSM is about 0.6% of the composition.

Some embodiments comprise a frozen dessert product with retarded warming characteristics, comprising the ingredients required to manufacture the frozen dessert product and about 0.2% to about 4% MSM. In some embodiments, the frozen dessert comprises ice cream yogurt, gelato, sorbet, or sherbert.

Some embodiments comprise a heat transfer fluid with retarded warming characteristics, comprising the components of the coolant, refrigerant or cryogenic and about 0.2% to about 4% MSM. Some embodiments comprise a product for medical applications with retarded warming characteristics, comprising the components of the product for medical application and about 0.2% to about 4% MSM. III MSM

MSM is an organosulfur compound with the formula (CH3)2S02. MSM is structurally related to dimethyl sulfoxide (DMSO), but the behavior of these two is different. DMSO is a highly polar solvent and an excellent ligand, with water-like dissolving properties whereas MSM is less polar and less reactive. MSM is well known as a nutritional supplement and as a pharmaceutical agent (see, e.g., Jacob and Appleton, MSM; the definitive guide: A comprehensive review of the science and therapeutics of Methylsulfonylmethane, Topanga, CA: Freedom Press, 2003). MSM is also known to be useful for the treatment of osteoarthritis (Kim et al. , Osteoarthritis Cartilage, 14:286-94, 2006) and hay fever (Barrager et al. , J. Altern. Complement. Med., 8: 167-74, 2002). One of skill in the relevant art will be familiar with these uses. Various grades of MSM are available commercially (for example, OptiMSM® MSM sold by Bergstrom Nutrition, Corp., Vancouver, WA); one of skill in the art will be familiar with a source of MSM. MSM is highly water soluble. At room temperature {e.g. , 70°F), aqueous solutions of 20% MSM can be prepared easily. Aqueous solutions of higher MSM concentrations are possible at temperatures higher that room temperature.

MSM used according to any of the embodiments provided herein may be isolated, purified or processed. MSM that has been granted a Generally Recognized As Safe (GRAS) designation is used for several embodiments described herein. In some embodiments, MSM is provided in a solid form. For example, MSM can be in the form of granules, powder, flakes, or prill. In several embodiments, MSM is provided in a solution. In some embodiments, MSM is used in combination with dimethyl sulfoxide (DMSO) and/or other related compounds. One of skill in the art will understand how to combine MSM with a product. For example, MSM can be dissolved in water-based products.

Disclosed herein are a variety of products with which MSM may be combined. One of skill in the art will recognize suitable products for combining with MSM. For example, such products include liquids, viscous solutions, gels, semi-solids, and solids. Non-limiting examples include edible products such as various foods and beverages, including frozen foods and beverages. Other examples include various industrial products. More examples include coolants, refrigerants, cryogenics, ice cream, fruit puree, water, water to be used in making ice and firefighting foam. More examples will be apparent to one of skill in the art, and are disclosed herein.

In certain embodiments, the product or composition may be a viscous solution, a gel, a semi-solid, or a solid. MSM may be compounded, admixed, incorporated into, or deposited on top of the product. In certain embodiments, combining MSM with a product comprises adding MSM to a product and mixing MSM into the product. In certain other embodiments, combining MSM with a product comprises spraying MSM onto the product. Any method of combining known in the art or yet to be devised may be used.

In several embodiments, the product is a liquid in which an amount of MSM is dissolved. In some embodiments, the liquid comprises additional dissolved solids. In some embodiments the product is a water-based liquid.

It will be understood by the skilled artisan that MSM may be combined with a finished product, or with an unfinished product. For example, MSM may be combined with a fruit puree, or MSM may be combined with the ingredients used for manufacturing a fruit puree. When the composition of fruit puree ingredients and MSM is used to manufacture fruit puree, a composition of fruit puree and MSM is generated. Other examples are described herein, including compositions of MSM and ice cream, etc. For example, MSM may be combined with the ingredients required to make ice cream, thereby making a composition comprising MSM and ice cream ingredients. When the composition of ice cream ingredients and MSM is used to manufacture ice cream, a composition of ice cream and MSM is generated. Alternatively, MSM can be combined with the ingredients used for manufacturing other frozen desserts or food products as described herein.

In several embodiments, a composition comprising MSM and a product or the ingredients required to make a product comprises at least about 0.01% to about 15% MSM (by weight). In some embodiments, a composition comprising MSM and a product or the ingredients required to make a product comprises MSM (by weight) in a range from about 0.01% to 0.1%, from about 0.1% to about 1%, from about 1% to about 5%, from about 6% to about 10%, from about 11% to about 15%, from about 2% to about 7% or from about 8% to about 15%. In some embodiments, a composition comprising MSM and a product or the ingredients required to make a product comprises at least about 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15% MSM (by weight).

In certain embodiments, MSM is in an amount of about 2 grams. In other embodiments, MSM is provided in an amount of about 10 grams. In certain embodiments MSM is provided in a range from about 3-5 g, 6-9 g, 2-4 g, 4-6 g, 6-8 g, or 8-10 g. These ranges are based on a product with a mass of about 500g;

however, in those embodiments where the mass of the product increases or decreases, MSM is added in similar proportions. In some embodiments, an initial amount of MSM is combined with a product, and then supplemented one or more additional times to maintain or increase the cooling effect.

IV. Methods for Altering Thawing or Warming of a Composition

Disclosed herein are methods of retarding warming of a composition, including methods of retarding thawing of a composition. Also disclosed herein are methods of generating a composition resistant to warming and methods of reducing the temperature (e.g. , cooling) a composition. The methods disclosed herein include combining MSM with a product or composition.

In several embodiments, the addition of MSM to a product yields a composition that is maintained at a reduced temperature for an increased period of time as compared to the product without MSM. For example, addition of MSM to a product can retard thawing or warming of the composition comprising the product and MSM, thereby maintaining the composition at a reduced temperature as compared to a product that does not comprise MSM. In certain embodiments, a composition comprising MSM, if frozen, remains frozen for a longer period of time.

Some embodiments include a method for retarding warming of a product or composition. Such embodiments are based on the novel discovery disclosed herein that a composition comprising a product and MSM that is cooled to a reduced temperature and then exposed to an environment with a temperature greater than the reduced temperature, requires more time to warm to the temperature of the environment than a composition that does not comprise MSM. Such methods comprise selecting a product to be cooled, and combining the product and an amount of MSM to form a composition, wherein the amount of MSM is sufficient to yield a composition with retarded warming characteristics, and exposing the composition to an environment with a temperature greater than that of the composition for a period of time, wherein the time required for the composition to warm to the temperature of the environment is greater than the time required for a control product without MSM subject to the same conditions to warm to the temperature of the environment, thereby retarding warming of a composition. In some embodiments, the MSM containing composition is exposed to a first environment with a temperature lower than that of the MSM containing composition for a period of time, followed by exposure of the composition to a second environment with a temperature greater than that of the first environment. In such embodiments, the composition comprising MSM will require more time to warm to the temperature of the second environment that a composition that does not comprise MSM.

For example, in one embodiment, methods for retarding warming of a product include combining water and an amount of MSM to form a composition, wherein the amount of MSM is sufficient to yield a composition having retarded warming characteristics, and exposing the water/MSM composition to an environment with a temperature greater than the temperature of composition. In this embodiment, the water/MSM composition requires more time to warm to the environment than water without MSM requires when exposed to the same conditions. In other embodiments, methods for retarding warming of a product include combining water and an amount of MSM to form a composition with a first temperature, wherein the amount of MSM is sufficient to yield a composition having retarded warming characteristics, and exposing the water/MSM composition to a first environment with a temperature lower that the first temperature, followed by exposing the water/MSM composition to a second environment with a temperature greater than the temperature of the first environment. In this embodiment, the water/MSM composition requires more time to warm to the temperature of the second environment than water without MSM requires when exposed to the same conditions. In other embodiments, the product comprises a food product, an industrial product or a product for use in a medical application, among others. The amount of MSM combined with the product varies depending on the product and on the method of combination. One of skill in the art will understand how much MSM to combine with a particular product.

In some embodiments of a method for retarding warming of a composition, the method includes retarding thawing of a composition. Such embodiments are based on the novel discovery disclosed herein that a composition comprising MSM, once frozen, requires more time to thaw than a composition that does not comprise MSM. Such methods comprise selecting a product to be cooled, and combining the product and an amount of MSM to form a composition, wherein the amount of MSM is sufficient to yield a composition with retarded warming characteristics, and exposing the composition to an environment with a temperature lower than the freeing point of the composition for a period of time sufficient to freeze the composition followed by exposing the composition to a second environment with a temperature greater than the freezing point of the composition. In such

embodiments, the composition will require more time to thaw than a composition that does not comprise an amount of MSM sufficient to yield a composition with retarded warming characteristics. Methods of exposing a composition to a temperature below the freezing point of the composition are familiar to the skilled artisan.

For example, in one embodiment, such methods include combining water and an amount of MSM sufficient to yield a water/MSM composition with retarded warming characteristics, freezing the water/MSM composition, and placing the composition at room temperature. In this embodiment, the water/MSM composition requires more time to thaw than water without MSM treated under the same conditions. In other embodiments, the product to be cooled comprises a food product, an industrial product or a product for use in a medical application, among others. The amount of MSM combined with the product to be cooled varies depending on the product to be cooled and on the method of combination. One of skill in the art will understand how much MSM to combine with a particular product to be cooled.

In some embodiments of a method for retarding warming of a composition, the ingredients required for manufacturing a product to be cooled and an amount of MSM sufficient to yield a composition with retarded warming characteristic are combined to yield a composition of ingredients and MSM, which is used to manufacture a composition comprising the product to be cooled and MSM. One of skill in the relevant art will understand the ingredients required to manufacture a product to be cooled and methods of combining these ingredients with an amount of MSM sufficient to yield a composition having retarded warming characteristics. Non- limiting examples of such products include frozen edible products such as ice cream, frozen yogurt, gelato, sorbet, popsicles, milkshakes, sherbet, frozen fruit, and other frozen desserts.

In another embodiment, a method of generating a composition resistant to warming is provided. In this embodiment, a product to be cooled is selected and combined with an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to yield a composition with retarded warming characteristics. If exposed to an environment with a temperature greater than that of the composition, such a composition requires more time to warm to the temperature of the environment than a control product without MSM subject to the same conditions.

In some embodiments of a method of generating a composition resistant to warming, the composition is resistant to thawing. In these embodiments, if the composition is frozen, and then exposed to an environment with a temperature greater than the freezing point of the composition, such a composition requires more time to thaw than a control product without MSM subject to the same conditions. Methods of freezing a composition are familiar to the skilled artisan. Non- limiting examples of such products include frozen edible products such as ice cream, frozen yogurt, gelato, sorbet, popsicles, milkshakes, sherbet, frozen fruit, and other frozen desserts. Other examples will be familiar to the skilled artisan and are described herein.

In some embodiments of generating a product resistant to warming, including methods of generating a product resistant to thawing, combining a product to be cooled and an amount of MSM comprises combining the ingredients required to manufacture the product to be cooled and an amount of MSM to yield a composition, and the composition is used to manufacture a composition resistant to warming, wherein the amount of MSM is sufficient to yield a composition with retarded warming characteristics.

In certain embodiments, compositions of a product to be cooled and an amount of MSM sufficient to yield a composition with retarded warming characteristics that are frozen remain frozen up to about 50% longer than products without MSM. In certain other embodiments, such products remain frozen from about 20% to about 40% longer, from about 10% to 19% longer, or from about 5%- 30% longer, including about 5%-10%, 10%- 15%, 15%-20%, 20%-25%, 25%-30%, 30%-40%, 40%-50% longer, or more (and overlapping ranges thereof). In further embodiments, MSM permits products to remain at a desired temperature longer (e.g. , 10%-100% longer, or 2- 10 fold longer) than products without MSM.

In other embodiments, compositions of a product to be cooled and an amount of MSM sufficient to yield a composition with retarded warming characteristics, if cooled, remain cool for a longer period that a product that does not contain MSM. In certain embodiments, such compositions that are cooled remain cool up to about 50% longer than products without MSM. In other embodiments, such compositions remain cool from about 20% to about 40% longer, from about 10% to 19% longer, or from about 5%-30% longer, including about 5%- 10%, 10%- 15%, 15%-20%, 20%-25%, 25%-30%, 30%-40%, 40%-50% longer, or more (and overlapping ranges thereof). In further embodiments, MSM permits compositions to remain at a desired temperature longer (e.g. , 10%- 100% longer, or 2-10 fold longer) than products without MSM.

Methods comprising selecting a product to be cooled will be apparent to the skilled artisan. For example, such a method may comprise identifying a product that will be exposed to an environment with a temperature below that of the product, and selecting such a product, thereby selecting a product to be cooled. In some embodiments, selecting a product to be cooled comprises selecting a product to be frozen. Such embodiments comprise identifying a product that will be exposed to an environment with a temperature below that of the freezing point of the product for a period of time sufficient to freeze the product, and selecting such a product, thereby selecting a product to be frozen.

V. Methods of Cooling a Composition

A method for reducing (e.g., cooling) the temperature of a product or composition is disclosed herein. The method comprises selecting a product to be cooled and combining an amount of MSM with the product to yield a composition, wherein the amount of MSM is sufficient to cool the composition. An amount of MSM sufficient to cool the composition reduces the temperature of the product or composition when in combination with the product.

In certain embodiments, the method of reducing the temperature of a product or composition includes a method of freezing a product or composition. The method comprises the steps of providing a product that is to be frozen; combining an effective amount of MSM with the product to yield a combination comprising the MSM and the product; and lowering the temperature of the combination comprising the MSM and the product to freeze the product. In these embodiments, MSM reduces the temperature of the product to below the freezing point of the product when in combination with the product.

When combined with MSM in certain embodiments, MSM can reduce the temperature of the product by an amount ranging from about 1% to about 30%, relative to the starting temperature of the product. In certain embodiments, the temperature reduction (relative to the initial temperature) is at least about 20%, while in some embodiments the reduction is at least about 10%. In still other embodiments, the temperature reduction ranges from about 1% to about 9%, including reductions of 2, 3, 4, 5, 6, 7, and/or 8%. In some embodiments, the addition of MSM reduces the temperature of a product by at least 1-5°C, 5-10°C, 10- 15°C, 15-20°C, 20-25°C, 25-30°C, 30-35°C, or more, and overlapping ranges thereof.

In certain embodiments, the product to be cooled is a mixture of two or more ingredients. In several of these embodiments, MSM reduces the temperature of the mixture to a lower temperature than the temperature of a combination of a same amount of MSM and each ingredient alone. For example, MSM may be combined with a mixture of water and glycol. In certain embodiments, MSM can cause the mixture to have a lower temperature when in combination than the temperature of the same amount of MSM combined with water without MSM or the same amount of MSM combined with glycol without MSM. In one embodiment, a glycol solution comprising MSM is colder than the same solution without MSM. In one embodiment utilizing glycol, a frozen glycol solution comprising MSM is achievable and further, in some embodiments, melts at a different rate than a comparable solution without MSM. The addition of ethylene glycol to water causes the freezing point of the latter to decrease. Thus, any damage that would be caused by the water freezing (e.g. , in a radiator or manufacturing process) is reduced or avoided by using a mixture of water and ethylene glycol as a coolant. Such a mixture may also have a boiling point that is higher than the boiling point of water, thereby reducing the risk of boiling-over in hot weather. In several embodiments of the invention, MSM is used to increase the effectiveness of, reduce the amount of, or entirely replace ethylene glycol.

In several embodiments, MSM acts as a surface cooling agent. Surfaces include, but are not limited to, surfaces on medical diagnostic equipment, medical bedding or coverings, household surfaces and the surface of a subject (e.g. , skin). In some embodiments, MSM is sprayed onto the surface. In other embodiments, MSM is injected under the surface. In several embodiments, a product to be cooled is partially or fully submerged or dipped into an MSM solution. In some

embodiments, at least a portion of a subject is submerged, dipped into, or otherwise contacted with MSM for, e.g. , treating burns or injuries or affecting body temperature on the surface of the subject.

In certain embodiments, a composition comprising a product to be cooled and MSM is subjected to freezing temperatures in order to freeze the composition. Thus, in some embodiments, combining a product to be cooled and an amount of MSM yields a composition, wherein the amount of MSM is sufficient to cool the composition, and wherein the elapsed time required to freeze the composition is reduced as compared to a control product not in combination with MSM subject to equivalent conditions.

In certain embodiments, when exposed to reduced temperature, certain compositions comprising a product to be cooled with an amount of MSM sufficient to cool the composition can be subjected to a lower temperature and maintain desirable characteristics as compared to a control product without added MSM. For example, in some embodiments a product comprising a dissolved solute with added MSM may be subjected to a lower temperature prior to precipitation of the solute as compared to that product with the dissolved solute and no MSM.

VI. Foods and Beverages

MSM is a natural substance, safe to ingest, and does not add caloric value. Thus in several embodiments MSM is combined with an edible food product or beverage in order to alter the cooling, thawing, or temperature characteristics thereof. In certain embodiments, MSM is a multifunctional compound that provides additional benefits, such as improvements in skin and other aesthetic benefits, cardiovascular health, neurological health, immunity, vision, etc.

In some embodiments, MSM is combined with a product that contains water, fat, oil, protein, carbohydrate or combinations thereof. One of skill in the art will understand how to make such combinations.

In several embodiments, MSM is combined with a dairy product. In some embodiments MSM is combined with ice cream, frozen yogurt, gelato, sorbet, popsicles, milkshakes, sherbet, frozen fruit, and other frozen desserts. In some embodiments, MSM is combined with foods to be frozen, such as frozen vegetables, pasta, and meats. Use of MSM, according to some embodiments, increases the shelf-life of frozen foods by maintaining the foods at a constant temperature, retarding the thawing or warming of frozen foods when they are exposed to an environment with a temperature greater than the freezing point of the frozen food, retarding the warming of the frozen food as described herein and/or lowering the temperature of the foods.

For example, in some embodiments, MSM is combined with a food product that is refrigerated. In such embodiments, if the refrigerated food product is exposed to a temperature above the refrigerated temperature, then the food product combined with MSM will remain at a lower temperature for a longer period of time compared to the equivalent food product without MSM. In some embodiments, MSM facilitates the freezing of frozen foods. In some embodiments, MSM reduces the amount of energy required to maintain the frozen foods in a frozen state during shipping and storage at a point of sale. In some embodiments, MSM increases the time that frozen foods remains frozen after removal from a freezer.

In several embodiments of the invention, a freeze-thaw damage resistant composition comprising MSM is provided. In some embodiments, by maintaining a more stable temperature, the number or range of freeze-thaw cycles is eliminated or reduced. In several embodiments, MSM is used to limit cell damage by quick cooling foods and/or by maintaining a stable temperature. Accordingly, in some embodiments, MSM improves the flavor, texture, appearance, density, and/or nutritional content of an edible product. In some embodiments, MSM reduces undesired crystallization and/or alters the size of the crystals. In some embodiments, MSM reduces or delays the development of freezer burn.

In several embodiments of the invention, combining MSM with a product to be cooled is used to facilitate the production of frozen foods. For example, in one embodiment, MSM is combined with ice cream or the ingredients required to make ice cream, thus decreasing the time needed to manufacture ice cream in commercial, professional and at-home ice cream machines. By decreasing the time to manufacture ice cream (or other frozen product), MSM is advantageous because it not only increases production capacity, but it also decreases exposure time of the frozen food to the environment, which may in turn improve texture, consistency, stability, appearance, flavor, etc. According to several embodiments, the use of MSM decreases the rate of desiccation or drying-out. In some embodiments, rapid cooling is achieved and results in higher moisture retention of an edible (or non- edible) product, thereby enhancing texture, consistency, stability, appearance, flavor, etc. In one embodiment, the use of MSM may be particularly well-suited for IQF (Individually Quick Frozen) technology or flash freezing. In several embodiments, MSM is used to facilitate the production of frozen foods by aiding in the cooling of the actual edible product, the packaging of the product, and/or the equipment used to manufacture, cool or store the product. In some embodiments, MSM is used to facilitate the freeze drying of a product. In addition to frozen foods, MSM is also combined with a product that is a refrigerated food in several embodiments. In some embodiments, MSM provides a benefit in the manufacturing process of dairy products such ice cream, milk, yogurt, butter, or cheese. Certain steps in the manufacturing, packaging, or shipping of these products require sustained reductions in temperature (in some cases, such as ice cream, to the freezing point). Thus, in certain embodiments, MSM combined with a dairy product reduces the amount of time for the dairy product to reach a desired reduced temperature, which may reduce the energy costs for the process of temperature reduction. In other embodiments, the addition of MSM increases the rate of temperature decrease, thus reducing the time in which harmful or unwanted bacteria could colonize the refrigerated product.

In yet other embodiments, the addition of MSM reduces the amount of energy required to maintain a product to be cooled at a reduced temperature, such as during shipping or at a refrigerated point of sale. In still other embodiments, when refrigeration systems are unavailable or not properly functioning, the combination of MSM and certain foods and/or beverages increases the time to spoilage as compared to foods/beverages without MSM. In such embodiments, MSM retards the thawing or warming of the food product to be cooled.

In certain embodiments, MSM is combined directly to a non-dairy beverage. MSM may be combined with beverages including, but not limited to, water, fruit juices, vegetable juice, soy milk, energy drinks, coffee (e.g. iced coffee), sports drinks, functional beverages (i. e. nutrient fortified water), alcoholic or non-alcoholic beverages, alcoholic or non-alcoholic mixers, sodas, diet beverages, teas and iced teas. In other embodiments, MSM is combined with water that is used to make ice, which is then combined with a beverage. In still other embodiments, MSM is combined with any other beverage class listed above that can be fully or partially frozen, and is used to make a frozen cube or slurry that is later combined with a liquid beverage (of the same or different type), and results in a chilled beverage. In other embodiments, the resulting product is fully or partially frozen. For example, in several embodiments, MSM is combined with fruit or yogurt, which is then frozen, resulting in frozen fruit or yogurt (e.g. , a popsicle) in a shorter period of time as compared to fruit or yogurt without MSM. In still other embodiments, MSM is combined with a fruit and/or vegetable puree, which is then frozen, resulting in a frozen fruit/vegetable smoothie in a shorter period of time as compared to purees without MSM. As described above, in such embodiments, the popsicles and/or smoothies would also remain frozen/cold for longer periods of time when they are exposed to an environment with a temperature greater than their freezing point as compared to those not having MSM.

In several embodiments, MSM is used in IQF applications, such as those for freezing and storing seafood and other frozen foods. Blast freezing is used in conjunction with MSM according to one embodiment. For example, MSM combined with an ingredient will freeze more quickly according to one embodiment, thereby increasing the efficiency of the blast freezing process (e.g. , by reducing blast freezing time or intensity). In several embodiments, MSM is beneficial for ice cream, yogurt, milk, frozen yogurt, cream, dairy, pizza, cakes, containers, bars, gallons, popsicles, sherbet, fruits, berries, vegetables, cheese production and preservation, beer and wine processing, pasteurization processes, and ice production In one embodiment, MSM serves as a cryoprotectant during the freezing and/or thawing process of edible products. In several embodiments, MSM is used in ice-packs or other cooling devices used for keeping foods and beverages at cold temperatures.

In some embodiments a frozen dessert product with retarded warming characteristics is provided. The product comprises the ingredients required to manufacture the frozen dessert product and an amount of MSM sufficient to yield a product with retarded warming characteristics, for example, about 0.2% to about 4% MSM. In some embodiments, the ingredients and MSM are used to manufacture a frozen dessert product. Non-limiting examples of such products include ice cream yogurt, gelato, sorbet, or sherbert, which comprise an amount of MSM as described herein.

VII. Medical Applications

In several embodiments, MSM is combined with a product for medical applications, wherein the product for medical applications is a product to be cooled. For example, a combination of MSM and a product for medical applications can be administered to a subject for medical purposes. In some embodiments, the combination is applied topically to a subject. In certain embodiments, a therapeutic benefit is gained directly from the reduced temperature of the product in combination with MSM, or the reduced temperature of the combination. For example, in some embodiments, MSM is combined with a product and the combination is topically applied to a subject to provide a benefit to a subject suffering from contact injuries, broken bones, sprained joints, bruises, spinal injuries, nerve damage, cold therapy, heat stroke, burns, fevers, elevated temperature, or heat exhaustion.

Non-limiting examples of products for medical applications are water baths, muscle wraps, cold packs, ice vests, cooling headbands, wristbands or other clothing, mattress or sleep pads, and other activatable cooling media. In some embodiments, MSM is packaged separately and then combined directly with a product, as with a water bath for example. In such embodiments, combining MSM with the product results in cooling of the product. In other embodiments, MSM is packaged with the product, but maintained in a divided or separate chamber that a user activates to combine the MSM with the product (e.g. , a "smack-pack"). In such embodiments, activation of the separate chamber by the user combines the product with MSM, resulting in cooling of the product. Additionally, in such embodiments, addition of MSM to the product for medical application results in a product resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the product, as compared to a control medical product not having MSM.

MSM is used for cold therapy, or cryotherapy, in several embodiments to decrease the flow of fluid into damaged tissues and/or block the release of inflammatory compounds. In some embodiments, MSM is used to cool areas in order to provide an anesthetic or numbing effect.

In certain embodiments, a liquid, gel, or other such media is already placed inside a muscle wrap or cold pack prior to use. In these embodiments, MSM is placed in an inner packet within the muscle wrap or cold pack to separate the MSM from the liquid. When the muscle wrap or cold pack is ready to be used, the inner packet is broken so that MSM combines with the liquid, causing a decrease in the temperature of the liquid media. In other embodiments, the pack further comprises a second component, such as ammonium-nitrate, that, when combined with the MSM and liquid media absorbs heat and functions synergistically with the MSM to yield a greater reduction in temperature of the liquid. In certain embodiments, MSM is used to replace the ammonium-nitrate in a cold pack. Additionally, in such embodiments, addition of MSM to the product for medical application results in a product resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the product, as compared to a control medical product not having MSM.

Advantageously, several embodiments of the present invention do not interfere with the use of medical aids or medicines and are used in connection with other medical aids and medicines to elicit a greater therapeutic benefit than either alone. For example, several embodiments as described herein are used in connection with DMSO (or other compounds related to MSM) to, for example, reduce inflammation.

Several embodiments are used for dental applications. In certain such embodiments, administration of the composition is oral. In some embodiments, MSM is combined with a liquid mouthwash rinse for home use in order to cool oral tissues, thereby alleviating minor oral pain. In some embodiments, MSM is provided as a rinse aid in a dentist's, orthodontist's or oral surgeon's office to provide cooling effects to a pre-existing rinse or irrigation liquid. In some embodiments, the liquid rinse or irrigation liquid is mixed with MSM and used prior to a procedure. In other embodiments, it is used during or after a procedure. Several embodiments comprise a small, orally applied cold pack, similar to that as described above for injuries, for use before, during or after dental procedures. MSM can act as (or increases the effectiveness of) dental anesthetics in some embodiments by acting as a cold numbing agent. Additionally, in such embodiments, addition of MSM to the product for medical application results in a product resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the product, as compared to a control medical product not having MSM. Other embodiments in the medical field include the use of MSM to reduce the temperature of intravenously delivered drugs or liquids. For example, certain medical conditions may benefit from the delivery of normal saline, or other fluids, at a reduced temperature. For example, reduced temperature delivery of fluids may provide an improved outcome in cardiac arrest patients who are treated with induced hypothermia to reduce cardiac tissue damage. In other embodiments, MSM is combined with, or provided in conjunction with chemotherapeutic agents, a side effect of which is a hot and/or tingling sensation at the delivery site. Additionally, in such embodiments, combination of MSM with a product for medical application results in a product resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the product, as compared to a control medical product not having MSM.

In the biomedical research arena, MSM is used in certain embodiments to rapidly cool or freeze tissue biopsy samples, cell culture cells, isolated cells (such as stem cells), or to preserve harvested organs. In certain embodiments, MSM is combined with a freezing media, which is then used to perfuse or wash the tissue/cells to be cooled. In other embodiments, MSM is deposited on the surface of the tissue/cells to be cooled, and the reduction in temperature is induced

subsequently. In several embodiments, MSM is used to preserve organs or to preserve/freeze/thaw organs, tissue, and cells (such as stem cells). In one embodiment, MSM increases the pluripotency or multipotency of stem cells. In several embodiments, MSM is used to limit biological cell damage by quick cooling and/or by maintaining a stable temperature. Accordingly, in some embodiments, MSM preserves the structural and/or functional integrity of cells and other tissue sample. In some embodiments, MSM reduces or prevents undesired intracellular and/or extracellular ice formation.

In several embodiments, MSM is used in cryogenic, cryobiology and cryonic applications. In one embodiment, MSM is used to facilitate cryopreservation of organisms, tissue and other organic materials. In one embodiment, MSM is used to cool cells or tissues to low sub-zero temperatures to reduce or stop one or more biochemical reactions. In one embodiment, MSM serves as a cryoprotectant during the freezing and/or thawing process. In some embodiments a product for medical applications with retarded warming characteristics is provided. The product comprises the ingredients required to manufacture the product for medical applications and an amount of MSM sufficient to yield a product with retarded warming characteristics, for example, about 0.2% to about 4% MSM. In some embodiments, the ingredients and MSM are used to manufacture a product for medical applications. Non-limiting examples of such products include a water bath, a muscle wrap, or a cold pack, that comprise an amount of MSM as described herein. VIII. Industrial Products or Compositions and Applications

Certain embodiments may be used for an industrial application, e.g. , in air conditioners, refrigerators, liquefied gases, and automobiles. In certain

embodiments, a composition comprising MSM is used as a heat transfer fluid, such as a coolant, a refrigerant, or a cryogenic replacement. In other embodiments, MSM is used with a heat transfer fluid, such as a coolant, a refrigerant, or a cryogenic to increase the cooling effect of the heat transfer fluid. Additionally, in certain embodiments, combination of MSM with a heat transfer fluid such as a coolant, a refrigerant, or a cryogenic, results in a composition resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the composition, as compared to a control product without MSM.

In certain embodiments, MSM is combined with a water and glycol mixture. In several of these embodiments, MSM causes the mixture to have a lower temperature when in combination than the temperature of the same amount of MSM combined with water without MSM or the same amount of MSM combined with glycol without MSM. In certain embodiments, addition of MSM to a water and glycol mixture results in a composition that is resistant to warming. In certain embodiments, addition of MSM to a water and glycol mixture, results in a composition resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the product, as compared to a control product without MSM. In certain embodiments, MSM is combined with a refrigerant, e.g. , a type of coolant which undergoes a phase change between a liquid and gas. In certain other embodiments, MSM is combined with a cryogenic, e.g. , a liquefied gas such as liquid nitrogen, used for specialized freezing and chilling applications. In some embodiments, a composition comprising MSM and a cryogenic is used in the production of liquefied gas production and cryogenic fuel production. In certain embodiments, addition of MSM to a refrigerant results in a composition resistant to thawing and that remains frozen/cold for longer periods of time when it is exposed to an environment with a temperature greater than the composition, as compared to a control product without MSM.

Because MSM is not a contaminant to the environment, other advantageous embodiments include the use of MSM in firefighting foam. Firefighting foam cools the fire and surrounding surfaces. By combining MSM with the firefighting foam, MSM reduces the temperature of the foam and keeps the foam at a cool temperature longer. As a result, in certain embodiments, a composition comprising MSM and firefighting foam is more effective at cooling the fire and surrounding surfaces than firefighting foam without MSM.

Other embodiments include the use of MSM in the production of artificial snow. Artificial snow is commonly made by cooling water to near its freezing point. A droplet generator, e.g. , a high pressure nozzle and compressed air, atomizes the cooled water into droplets. Prior to reaching the ground, the water freezes. If the water does not freeze, the resultant snow will be excessively wet and will become icy. Thus in certain embodiments, MSM is combined with the water prior to or during ejection from the nozzle to help the water freeze quickly, resulting in higher quality and a greater quantity of artificial snow. MSM may also be used to help create nucleation sites for the ice crystals to form. In addition, certain embodiments keep the artificial snow frozen for a longer time than artificial snow made without MSM.

Several embodiments include the use of MSM in ice rinks. The surface quality of ice in ice rinks is important for ice skaters and hockey players. In certain embodiments, ice rinks comprise a concrete slab, under which are pipes filled with coolants to keep the concrete slab cold, which in turn keep the ice cold. As discussed above, certain embodiments can be used as a coolant or to increase the effectiveness of a coolant within these pipes. Certain embodiments can also be used to form the layers of ice on top of the concrete slab in the ice rink. In still other embodiments, MSM is combined with the water used in an ice resurfacer to provide a quick freezing, and thus smoother and higher quality, ice surface. Certain embodiments keep the ice frozen for a longer time than ice made without MSM.

Certain other embodiments are used for ice sculptures. A sculptor must complete an ice sculpture prior to the ice melting. In certain embodiments, MSM combined with water to make the ice for an ice sculpture provides the sculptor with more time in creating his or her masterpiece. As discussed above, an additional benefit of MSM combined with water that is frozen is that the resultant ice remains frozen for a longer period of time, thus allowing ice sculptures to remain solid for longer times.

In other embodiments, MSM is effective in reducing the temperature of a product or material in fields including but not limited to super cooling (of materials or reactions), temperature regulation of magnets used in magnetic resonance imaging, control of reaction rates in chemistry, particularly polymer chemistry, atomic research, biological cell storage (MSM incorporation into liquid nitrogen or oxygen), specialized automobile coolant (summertime or heavy-duty vehicle auto- coolant for use in desert areas, police/fire equipment, military vehicles), postmortem applications (cooled saline/fixative for improved perfusion in pathology labs and better cadaver preservation).

In several embodiments, MSM is effective in reducing the temperature of a product or material in cryoelectronic and cryotronic applications. In one embodiment, MSM facilitates superconductivity or other conduction/resistance at low temperatures. In one embodiment, the electrical resistivity of a metallic conductor decreases as the temperature is lowered with the use of MSM. In a superconductor, resistance may be dropped abruptly to zero or near- zero when the material is cooled below its critical temperature with the use of MSM.

In some embodiments a heat transfer fluid with retarded warming characteristics is provided. The product comprises the ingredients required to manufacture the heat transfer fluid and an amount of MSM sufficient to yield a product with retarded warming characteristics, for example, about 0.2% to about 4% MSM. In some embodiments, the ingredients and MSM are used to manufacture a heat transfer fluid. Non-limiting examples of such products include a coolant, refrigerant or cryogenic, that comprise an amount of MSM as described herein.

With respect to the embodiments disclosed herein, unless otherwise specified, any method of combining known in the art or yet to be devised may be used. Also, any method of lowering a temperature known in the art or yet to be devised may be used.

EXAMPLES

Specific embodiments will be described with reference to the following non- limiting examples which should be regarded in an illustrative rather than a restrictive

Example 1. MSM increases the time required to thaw frozen tap water.

This example describes an experiment testing the thawing rate of various concentrations of MSM/tap water solutions. 0-50 grams of MSM was combined with 500 mL of tap water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The volume of thawed solution was measured for each MSM/tap water concentration at numerous time points. The results show that, at certain concentrations, tap water with MSM stayed frozen longer when compared with tap water without MSM. In particular, MSM in an amount from about 1 to about 20 g mixed with tap water results in a solution that, once frozen, remains frozen longer than tap water without MSM.

Methods

A Mettler Toledo Analytical Balance was used to weigh out various amounts of ActivMSM™ MSM (Bergstrom Nutrition, Vancouver, WA), as indicated in Table 1. Sixteen 20 ounce plastic drink bottles were labeled according to the mass of MSM to be added. Using a 1 L measuring cup, fifteen bottles were filled with approximately 500 mL of cold (approximately 54.1 °F) while one bottle was filled with 500 mL of hot (approximately 107.3 °F) tap water. After the labeled bottles were filled with a corresponding amount of MSM, they were capped and shaken to dissolve the MSM. The 50g of MSM did not completely dissolve. The bottles were then placed into the lower drawer of a drawer type freezer set at 23 °F (-5°C).

Over 24 hours later, the bottles were removed from the freezer and placed on a countertop (the first removal). The caps were twisted loose to reduce pressure in the bottles and to allow for expansion. With the exception of four bottles, all other bottles were frozen solid. For the four bottles not frozen solid, qualitative notes were made regarding the amount of ice present. After observation, the bottles were placed back into the freezer. Twenty-four hours later, the bottles were removed from the freezer again (the second removal). After 72 minutes, the bottles were uncapped and any liquid present was poured into a graduated cylinder, measured, and returned to the bottle. The same protocol was used to measure volume of liquid at three later time points (128, 188 and 269 minutes after removal from the freezer). Two additional measurements were made (435 and 565 minutes following removal from the freezer), after the bottles were transported for two hours at approximately 52°F. Again, the temperature and the volume of liquid present were measured and recorded. At the last time point, the sizes of any remaining ice cubes were ranked from 0 (no ice) to 6 (4" x 1" ice cube).

Table 1. Effect of MSM concentration on the thawing time of a frozen

MSM/tap water solution placed at room temperature.

Amt. of Temp. Temp. Check Melt Day 6 (mL)

MSM Day O Day O Day 1 T=72' T=128' T=188' T=269' T=435' T=565' Cube

2:43p 3: 10p 9 am (12:37p) (l :32p) (2:32p) (3:54p) (6:40p) (8:50p) size

De F mL mL mL mL mL mL 0-6

58.2 58.5 58 131 208 310 401 504 0 ig 56.3 58.3 20 98 167 263 348 482 5

2g 55.9 57.8 18 87 158 257 343 490 6

3g 55.5 57.3 18 78 148 254 344 490 6

4g 54.6 56.9 *3/4 22 83 154 257 366 504 5

5g 64.1 63.9 19 76 144 249 344 500 5

6g 56.9 59.7 20 80 150 261 356 510 5

7g 55 57.7 *l/2 19 79 146 249 350 494 4

8g 63.6 64.9 14 74 153 267 360 505 4

9g 62.9 60.8 *l/2 16 75 146 253 374 499 3

10g 58.1 57.7 *3/4 18 82 151 264 371 499 2

13g 55.4 57 21 84 153 264 361 506 3

15g 54.5 56.3 13 80 151 261 378 502 2 Amt. of Temp. Temp. Check Melt Day 6 (mL)

MSM Day O Day O Day 1 T=72' T=128' T=188' T=269' T=435' T=565' Cube

2:43p 3: 10p 9 am (12:37p) (l :32p) (2:32p) (3:54p) (6:40p) (8:50p) size

20g 53.3 55 17 90 161 274 381 508 1

50g 51 53.6 62 150 234 358 462 535 0

50g (H) 91.8 79.4 78 160 245 370 466 508 0

Results:

Results of this experiment are shown in Table 1 and Figure 1. At the first removal, all the bottles, except four, were frozen solid. Qualitative observations regarding the amount of ice present in the four bottles that were not completely frozen is shown in Table 1 (see column labeled "Check Day 1; 9 am" in Table 1).

Some liquid was present in all four of these bottles, and bubbles were seen moving among the ice with the sides of the bottles being squeezable.

At the second removal, all the bottles were frozen solid. Room temperature was measured at 71.2°F. 72 minutes after removal, the bottles were uncapped and any liquid present was poured into a graduated cylinder, measured, and returned to the bottle. The same protocol was used to measure the temperature and volume of liquid at 128, 188, 269, 435 and 565 minutes after removal from the freezer (see Table 1). Room temperature measurements were 71.5°F, 71.8°F, and 71.2°F for the 128, 188, and 269 minute time points, respectively. Ambient surrounding

temperature was 64°F at the 435 and 565 minute time points. As shown in Table 1, the size of any ice remaining at the 565 minute time point was ranked from 0 (no ice) to 6 (4" x 1" ice cube). All solutions containing MSM, except the 50g solutions, showed less thawing over the recorded timeframe than a solution containing tap water without MSM.

Overall, these results show that, when placed at room temperature, a frozen MSM/tap water solution stayed frozen longer than frozen tap water without MSM. In particular, MSM in an amount from about 2 to about 20 g mixed with 500 mL tap water (0.2% to 4% MSM by weight) results in a solution that, once frozen, remains frozen longer than tap water without MSM. Example 2. MSM increases the time required to thaw frozen tap water and maintains thawed tap water at a reduced temperature.

This example describes an experiment testing the thawing rate and the temperature of thawed MSM/tap water solutions. 0-50 grams of MSM was combined with 500 mL of tap water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The volume of thawed solution, as well as the temperature of thawed solution, was measured for each MSM/tap water concentration at numerous time points. In Example 2, a laser radiation thermometer was used to obtain temperature readings throughout the time the samples were incubated at room temperature. The results show that, when placed at room temperature, a frozen MSM/tap water solution stayed frozen longer, and remained at a lower temperature, than frozen tap water without MSM.

Methods:

The same procedure used in Example 1 was followed for weighing, adding

MSM to the bottles filled with tap water, and measuring the volume of thawed solution after the bottles had been frozen and placed at room temperature.

Additionally, a Raytek MiniTemp Laser Radiation thermometer was used for obtaining temperature readings during the thawing process. Melt volume was measured at 140, 330 and 450 minutes following removal from the freezer.

Temperature was measured at 195, 325 ad 445 minutes following removal from the freezer.

Table 2. Effect of MSM concentration on the thawing time and temperature of a frozen MSM/tap water solution placed at room temperature.

Figure imgf000034_0001
Figure imgf000035_0001

Results:

Results are shown in Table 2 and Figure 2. After six days in the same freezer, the bottles were removed from the freezer for analysis. All bottles were frozen solid. Room temperature when the bottles were removed from the freezer was measured at 62.3 °F (16.8 °C). At the measurement time points, room temperature was measured consistently at 64.9 °F (18.3 °C).

As shown in Table 2 and Figure 2, MSM in a range from about 2 g/500mL to about 10 g/500mL resulted in lower temperature measurements at the first time point (195 minutes after removal from the freezer). At the second time point (325 minutes after removal from the freezer), MSM in a range from about 2 g/500mL to about 9 g/500mL resulted in lower maintained temperatures. At the final time point (445 minutes after removal from the freezer), temperatures were variable across the range of MSM added; however, the majority of temperature readings for samples having between 2 g/500mL and 7 g/500mL were less than those taken for tap water without MSM.

Additionally, the results show that a MSM/tap water solution remained frozen longer compared to tap water without MSM, particularly in a range of 2-9 g of MSM/500 mL of tap water. Similar to Example 1, all solutions containing MSM, except the 50g solutions, showed less thawing over the recorded timeframe than a solution containing tap water without MSM. Overall, these results show that, when placed at room temperature, a frozen MSM/tap water solution stayed frozen longer and remained at a lower temperature than frozen tap water without MSM. In particular, MSM in an amount from about 2 to about 20 g mixed with tap water (0.2% to 4% MSM by weight) results in a solution that, once frozen, remains frozen longer than tap water without MSM.

Example 3. MSM increases the time required to thaw frozen artificial sea water and maintains thawed artificial sea water at a reduced temperature.

This example describes an experiment testing the thawing rate and the temperature of thawed MSM/artificial sea water solutions. 0-50 grams of MSM was combined with 500 mL of artificial sea water, the solutions were frozen, and then placed at room temperature and allowed to thaw. The volume of thawed solution, as well as the temperature of thawed solution, was measured for each MSM/artificial sea water solution at numerous time points. In this Example, a laser radiation thermometer was used to obtain temperature readings throughout the time the samples were incubated at room temperature. The results show that, when placed at room temperature, a frozen MSM/artificial sea water solution stayed frozen longer, and remained at a lower temperature, than frozen artificial sea water without MSM, particularly at concentrations of 2-7 g MSM/ 500 mL artificial sea water.

Methods:

The same procedure used in Example 2 was followed for weighing, adding MSM to the bottles filled with water, measuring the volume of thawed solution after the bottles had been frozen and placed at room temperature and measuring the temperature of the solutions during the thawing process. However, in this Example, artificial sea water was used in place of tap water and there was an additional freeze- thaw for which data was collected. Artificial sea water was prepared by adding 107.6 g of sodium chloride, 9.2 g magnesium chloride, 13.2 g of magnesium sulfate, 4.8 g of calcium chloride, and 2.6 g potassium chloride to 3862.4 mL of tap water. After measurements were made on a first freeze-thaw cycle, the bottles were placed back in the freezer, and a second round of measurements was made on a second freeze-thaw cycle. Table 3. Effect of MSM concentration on the thawing time and temperature of a frozen MSM/artificial sea water solution placed at room temperature.

Figure imgf000037_0001

Figure imgf000037_0002
Second Freeze Thaw Cycle

Amt. of Melt Volume (mL) Temp. (°F)

MSM

T=160' T=250' T=340' T=155' T=245' T=335'

10:25 l:20p l:25p 10:25a 11:50a l:20p

20g 150 *343 520 23.9 30.2 31.1

50g 159 *376 525 23.9 29.3 33.8

*These data points were taken an additional 25 minutes after the other samples at this time point.

Results:

Results are shown in Table 3 and Figure 3. After removal from the freezer, all the bottles were frozen solid. The results show that the addition of MSM to artificial salt water in an amount between 2 and 7 g per 500 mL maintains the temperature of the artificial sea water at a lower level at nearly all time points tested (see Table 3 and Figure 3). In particular, as the duration of time that the solution was incubated at room temperature increased the MSM-containing samples had consistently lower temperatures (see, for example T=335' for 2 and 3 g of MSM as compared to 0 g MSM). Additionally, the results show that a MSM/artificial sea water solution remained frozen longer compared to artificial sea water without MSM, particularly in a range of 1-7 g of MSM/500 mL of artificial sea water. However, with higher amounts of MSM, the melting characteristics of MSM- supplemented artificial sea water are more similar to those of artificial sea water without MSM. Similar results were obtained for the second freeze-thaw cycle (Table 3).

Overall, these results show that, when placed at room temperature, a frozen MSM/artificial sea water solution stayed frozen longer and remained at a lower temperature than frozen water without MSM. In particular, MSM in an amount from about 2 to about 7 g mixed with artificial sea water results in a solution that, once frozen, remains frozen longer than artificial sea water without MSM.

Example 4. MSM retards thawing of ice cream.

This example describes a representative method of generating an ice cream that is resistant to warming as well as a method of retarding the thawing of ice cream. In this example, MSM and the ingredients for making ice cream are provided. Ice cream is selected because it is a product that is susceptible to thawing, for example during transport. MSM is combined with the ice cream ingredients prior to the initial freezing of the ice cream. The MSM is provided at a

concentration of 1 % by weight of the final MSM/ice cream ingredient composition. The ingredients (including MSM) are mixed together and frozen according to standard methods for freezing ice cream, thereby generating an ice cream that is resistant to thawing. Additionally, the ice cream is placed at room temperature. The ice cream comprising MSM thaws at a reduced rate compared to a control ice cream that lacks MSM. The MSM-containing ice cream requires 30% more time to thaw compared to the control ice cream that lacks MSM. Thus, a method of retarding thawing of ice cream is provided.

In view of the many possible embodiments to which the principles of the disclosed invention may be applied, it should be recognized that the illustrated embodiments are only preferred examples of the invention and should not be taken as limiting the scope of the invention. Rather, the scope of the invention is defined by the following claims. We therefore claim as our invention all that comes within the scope and spirit of these claims.

Claims

We claim:
1. A method of generating a composition resistant to warming, comprising:
selecting a product to be cooled; and
combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition, thereby generating a composition resistant to warming.
2. A method of retarding warming of a composition, comprising:
selecting a product to be cooled;
combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to retard warming of the composition; and exposing the composition to an environment with a temperature greater than that of the composition for a period of time, wherein the time required for the composition to warm to the temperature of the environment is greater than the time required for a control product without MSM subject to the same conditions to warm to the temperature of the environment, thereby retarding warming of a composition.
3. A method for cooling a composition, comprising:
selecting a product to be cooled; and
combining the product and an amount of MSM to yield a composition, wherein the amount of MSM is sufficient to cool the composition, thereby cooling the composition.
4. The method of any one of claims 1, 2 or 3, wherein the product is an edible product.
5. The method of claim 4, wherein the product comprises a beverage, a frozen desert, fruit puree or water to be used in making ice.
6. The method of claim 5, wherein the product comprises ice cream, yogurt, gelato, sorbet, or sherbert.
7. The method of any one of claims 1, 2 or 3, wherein the product is used for a medical application.
8. The method of claim 7, wherein the composition is incorporated into one or more of a water bath, a muscle wrap, or a cold pack.
9. The method of any one of claims 1, 2 or 3, wherein the product is a heat transfer fluid.
10. The method of claim 9, wherein the product comprises water and glycol.
11. The method of claim 1, wherein selecting a product to be cooled comprises selecting a product to be frozen.
12. The method of claim 2, further comprising
freezing the composition; and
wherein exposing the composition to an environment with a temperature higher than that of the composition for a period of time comprises exposing the composition to an environment with a temperature above the freezing point of the composition.
13. The method of claim 2, wherein the time required for the composition to warm to the temperature of the environment is about 50% greater than the time required for the control product without MSM subject to the same conditions to warm to the temperature of the environment.
14. The method of claim 3, wherein the product is a mixture of two or more ingredients and wherein the MSM reduces the temperature of the mixture to a lower temperature than the temperature of a combination of the same amount of MSM and each ingredient alone.
15. The method of any one of the previous claims, wherein the composition has a longer shelf life compared to the product.
16. The method of any one of the previous claims, wherein the amount of
MSM is ranges from about 0.2% to about 4% of the composition.
17. The method of claim 16, wherein the amount of MSM is about 0.6% of the composition.
18. The method according to any one of the preceding claims, wherein the product is a liquid, a viscous solution, a gel, a semi-solid, or a solid.
19. A frozen dessert product with retarded warming characteristics, comprising the ingredients required to manufacture the frozen dessert product and about 0.2% to about 4% MSM.
20. The frozen dessert product of claim 19, wherein the product comprises ice cream yogurt, gelato, sorbet, or sherbert.
21. A heat transfer fluid with retarded warming characteristics, comprising the components of the coolant, refrigerant or cryogenic and about 0.2% to about 4% MSM.
22. A product for medical applications with retarded warming characteristics, comprising the components of the product for medical application and about 0.2% to about 4% MSM.
PCT/US2010/054828 2010-02-03 2010-10-29 Use of methylsulfonylmethane (msm) as a cooling agent WO2011096966A1 (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4477469A (en) * 1979-08-30 1984-10-16 Herschler R J Preparations containing methylsulfonylmethane and methods of use and purification
US4481354A (en) * 1982-12-20 1984-11-06 The Standard Oil Company Process and composition for lowering the reversible phase change temperature of nylon compositions
US4719028A (en) * 1985-11-19 1988-01-12 James Timothy W Thermal energy storage media
US20040029774A1 (en) * 2002-08-06 2004-02-12 Aly Gamay Composition and methods for the treatment of musculoskeletal disorders and collagen and elastin deficiencies

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4477469A (en) * 1979-08-30 1984-10-16 Herschler R J Preparations containing methylsulfonylmethane and methods of use and purification
US4481354A (en) * 1982-12-20 1984-11-06 The Standard Oil Company Process and composition for lowering the reversible phase change temperature of nylon compositions
US4719028A (en) * 1985-11-19 1988-01-12 James Timothy W Thermal energy storage media
US20040029774A1 (en) * 2002-08-06 2004-02-12 Aly Gamay Composition and methods for the treatment of musculoskeletal disorders and collagen and elastin deficiencies

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