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Sommaire du brevet 2267497 

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Disponibilité de l'Abrégé et des Revendications

L'apparition de différences dans le texte et l'image des Revendications et de l'Abrégé dépend du moment auquel le document est publié. Les textes des Revendications et de l'Abrégé sont affichés :

  • lorsque la demande peut être examinée par le public;
  • lorsque le brevet est émis (délivrance).
(12) Brevet: (11) CA 2267497
(54) Titre français: COMPOSITIONS COMESTIBLES BASSES CALORIES D'UN EXCIPIENT ET D'UN INGREDIENT ACTIF ET LEURS PROCEDES DE PREPARATION
(54) Titre anglais: EDIBLE, LOW CALORIE COMPOSITIONS OF A CARRIER AND AN ACTIVE INGREDIENT AND METHODS FOR PREPARATION THEREOF
Statut: Périmé et au-delà du délai pour l’annulation
Données bibliographiques
(51) Classification internationale des brevets (CIB):
  • A61K 9/14 (2006.01)
  • A61K 9/00 (2006.01)
  • A61K 9/20 (2006.01)
(72) Inventeurs :
  • TURK, RICHARD S. (Etats-Unis d'Amérique)
  • DULEBOHN, JOEL I. (Etats-Unis d'Amérique)
  • STITLEY, JAMES W., JR. (Etats-Unis d'Amérique)
(73) Titulaires :
  • NATURA, INC.
(71) Demandeurs :
  • NATURA, INC. (Etats-Unis d'Amérique)
(74) Agent: LAVERY, DE BILLY, LLP
(74) Co-agent:
(45) Délivré: 2004-05-25
(86) Date de dépôt PCT: 1996-10-04
(87) Mise à la disponibilité du public: 1998-04-09
Requête d'examen: 1999-04-01
Licence disponible: S.O.
Cédé au domaine public: S.O.
(25) Langue des documents déposés: Anglais

Traité de coopération en matière de brevets (PCT): Oui
(86) Numéro de la demande PCT: PCT/US1996/015972
(87) Numéro de publication internationale PCT: WO 1998014173
(85) Entrée nationale: 1999-04-01

(30) Données de priorité de la demande: S.O.

Abrégés

Abrégé français

Des compositions comestibles basses calories contiennent, en plus d'un ingrédient actif, tel que des agents aromatisants, et des agents édulcorants, des agents thérapeutiques, des agents cosmétiques et des agents luminescents, un excipient se présentant sous forme de gel ou de verre, lequel est le produit de réaction amorphe d'un acide aminé de base, d'un acide carboxylique, d'une source d'ions métalliques et d'eau. L'invention concerne également des procédés de production desdites compositions.


Abrégé anglais


Edible, low calorie compositions contain, in addition to an active ingredient,
such as flavoring agents, sweetening agents, therapeutic
agents, cosmetic agents and luminescent agents, a gel or glass carrier which
is the amorphous reaction product of a basic amino acid, a
carboxylic acid, a source of metallic ions and water. Methods of making the
compositions are disclosed.

Revendications

Note : Les revendications sont présentées dans la langue officielle dans laquelle elles ont été soumises.


CLAIMS
1. A composition comprising a carrier and an active
ingredient, said carrier comprising the amorphous reaction
product of a basic amino acid, a carboxylic acid, a metallic
ion selected from the group consisting of magnesium, sodium,
calcium, potassium and zinc ions, and water, said amorphous
reaction product being selected from the group consisting of a
gel or glass.
2. A composition of claim 1 in which the amorphous reaction
product is a gel.
3. A composition of claim 1 in which the amorphous product
is a glass.
4. A composition of claim 1 in which the active ingredient
is oil soluble.
5. A composition of claim 4 in which the active ingredient
is a flavoring agent.
6. A composition of claim 1 in which the active ingredient
is a therapeutic agent.
7. A composition of claim 1 in which the active ingredient
is an artificial sweetener.
8. A composition of claim 3 in which the glass is ground
into particles.
9. A sugar substitute comprising a carrier which is the
amorphous reaction product of a basic amino acid, a carboxylic
acid, a metallic ion source selected from the group consisting
of magnesium, sodium, calcium, potassium and zinc ions, and
water in combination with an artificial sweetener, the ratio
of the basic amino acid to the carboxylic acid to the metallic
ion source to the water being in the range of from 1/2 mole

amino acid: 1 mole carboxylic acid: 1/2 mole metallic ion
source: 2 moles water to 2 moles amino acid: 1 mole carboxylic
acid: 2 moles metallic ion source: 10 moles water.
10. A sugar substitute of claim 9 in which the amorphous
reaction product is a glass.
11. A sugar substitute of claim 10 in which the glass is
ground into particles.
12. A sugar substitute of claim 9 in which the amorphous
reaction product is a gel.
13. A sugar substitute of claim 9 in which the artificial
sweetener is sodium saccharin.
14. A sugar substitute of claim 9 in which the artificial
sweetener is acesulfame K.
15. A sugar substitute of claim 9 in which the artificial
sweetener is aspartame.
16. A method of preparing a gel containing an active
ingredient, said method comprising dissolving a basic amino
acid in water, adding to the thus formed solution a mono- or
di-carboxylic acid, a metallic ion source selected from the
group consisting of magnesium, sodium, calcium, potassium and
zinc ions, and an active ingredient and reacting the mixture
to form a gel, wherein the ratio of the basic amino acid to
the carboxylic acid to the metallic ion source to the water
being in the range of from 1/2 mole amino acid: 1/2 mole metallic
ion source: 1 mole carboxylic acid: 2 moles water to 2 moles
amino acid: 1 mole carboxylic acid: 2 moles metallic ion
source: 10 moles water.
17. A gel prepared by the method of claim 16.

18. A method of preparing a gel containing an active
ingredient, said method comprises first dissolving a basic
amino acid in water, adding a mono-, di or tri-carboxylic acid
and a metallic ion source selected from the group consisting
of magnesium, sodium, calcium, potassium and zinc ions to the
thus formed solution, reacting the mixture to form a gel and
then adding an active ingredient to the gel, wherein the
ratio of the basic amino acid to the carboxylic acid to the
metallic ion source to the water being in the range of from 1/2
mole amino acid: 1 mole carboxylic acid: 1/2 mole metallic ion
source: 2 moles water to 2 moles amino acid: 1 mole carboxylic
acid: 2 moles metallic ion source: 10 moles water.
19. A gel prepared by the method of claim 18.
20. A glass prepared by dehydrating a gel made by the method
of claim 16.
21. A glass prepared by dehydrating a gel made by the method
of claim 18.
22. A composition comprising a carrier and an active
ingredient, said carrier comprising the amorphous reaction
product of
a basic amino acid selected from the group consisting of
lysine, ornithine, diaminopimelic acid, glycine, .beta.-alanine, 4-
aminobutyric acid, 5-aminovaleric acid, 6-aminocaproic acid,
and 7-aminoheptanoic acid;
a carboxylic acid selected from the group consisting of
mono-, di-, and tri-carboxylic acids;
a metallic ion selected from the group consisting of
magnesium, sodium, calcium, potassium and zinc ions; and
water, said amorphous reaction product being selected
from the group consisting of a gel or glass.

23. The composition of claim 22 wherein the carboxylic
acid is selected from the group consisting of acetic, citric,
malic, succinic, tartaric, and fumaric acid.

Description

Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.


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EDIBLE, LOW CALORIE COMPOSITIONS OF A CARRIER AND
AN ACTIVE INGREDIENT AND METHODS FOR PREPARATION THEREOF
Field of the Invention
The present invention generally relates to compositions of
carriers and active ingredients. More particularly, it relates
to edible, low calorie compositions of carriers and an active
ingredient, such as a flavoring agent.
Background of the Invention
Many active ingredients, such as flavoring agents and
artificial sweeteners, because of their intensity or potency
must be combined with carriers or bulking agents to obtain
compositions having the desired concentration of the active
ingredient for its intended use.
Currently available compositions of carriers and active
ingredients have limitations. For example, it has not been
possible to combine artificial sweeteners with known carriers to
produce low calorie artificial sweetener compositions that
possess all the desired organoleptic and physical properties of
sugar. As a result, it has not been possible to make certain
bakery products, such as low calorie cookies resembling crisp
sugar cookies, or low calorie candies.
The replacement of sugar in foods is as difficult in
practice as the replacement of fats. Bulking agents are added
with the removal of fat or sugar, consequently replacing the
total solids content in the food. Several types of bulking
agents are used; maltodextrins, polyols and polydextroses.
Maltodextrins are non-sweet nutritive polymers of glucose. They
can be used as carriers of artificial sweeteners and to build
soluble solids. They are added with other agents to inhibit
sugar crystallization, control freezing point and increase
viscosity of the food. They are fully caloric, (4 kcal/gm),
ingredients. Polyols are bulking agents which include sorbitol,
maltitol, xylitol, and lactitol. The general factors in using
polyols are their caloric content, Taxation potential,
solubility, relative sweetness and stability. The average
acceptable caloric value of polyols is 2.4 kcal/g. They are

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generally produced commercially by hydrogenation of sugars
(glucose to sorbitol, fructose to mannitol, xylose to xylitol,
lactose to lactitol) using metal catalysts.
Polydextroses are polymers of dextrose with a caloric
content of about 1 kcal/g. Improvements in processing have
produced cleaner tasting products. In various applications,
polydextrose can also function as a humectant and a low calorie
solids builder. They are used in baked goods, baking mixes,
chewing gums, frostings, dressings, frozen dairy desserts,
gelatins, fillings, hard and soft candies and puddings.
In baking, sucrose contributes to the flavor and tenderness
of the baked item and controls the viscosity of the batter.
Sugar also helps to limit the amount of free water which during
baking determines the starch gelatinization temperature and the
egg protein denaturation temperature. These temperatures are
important to the final quality of the product. Flour provides
starch which must gelatinize during baking by absorbing water
resulting in increasing the viscosity and eventually solidifies
as a gel when cooled. Polydextrose has been used up to about
30% for replacement of dextrose in cakes.
The state diagram of the system sucrose-water can be used
to discuss structure-function relations in food systems. Plots
of percent weight of sucrose in water versus glass and melting
transition points of solid and solutions in the high sugar
solids region (>60%) are relevant to low moisture food systems
such as cookie, cracker and candy manufacture. The glass
forming versus crystallizing behavior of sucrose represents a
critical functional attribute of sugar in foods. The sucrose
concentration in the food increases at baking temperatures until
baking is complete and the food begins to cool. During cooling
the food goes through a rubbery phase. At this point the food
temperature lies within the glass transition temperature of the
sucrose solution and the point of supersaturation of sugar in
water. During cooling this sucrose can either be recrystallized
or remain in the amorphous state.
In cookies, the sucrose (added in the recipe) and final
water content are important. For example a cookie made with
only 42 parts sucrose instead of 60 parts and baked to 4.5%

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moisture is a deformable rubber at room temperature as opposed
to a desirable crisp glass. Also since room temperature is well
above the glass transition temperature, diffusion processes are
accelerated and degradation of the texture occurs.
S Amorphous sugars in food are very stable below the glass
transition temperature since physical processes occurring in the
glass state are very slow. Physical changes in the amorphous
state which are diffusion dependent include crystallization,
stickiness, and collapse (time dependent loss of structure) and
volatilization of flavors. Chemical changes in the amorphous
state which are diffusion dependent include oxidation and off-
flavor development.
There is a need for novel edible, low calorie compositions
of carriers and active ingredients which do not have the
limitations of the currently available compositions.
Summary of the Invention
It is an object of the present invention to disclose novel
edible, low calorie compositions of carriers and active
ingredient ( s ) .
It also is an object to disclose methods of preparing such
novel compositions.
The novel compositions of the present invention are gels
and glasses, which contain an active ingredient and a carrier
which is the amorphous reaction product of a basic amino acid,
a carboxylic acid, a metallic oxide or salt and water.
The term "gel" as used herein means aqueous compositions
having high viscosity and rubber-like properties similar to
concentrated sugar solutions, such as KARO° syrup. The term
"gel" is not intended to denote any polymerization or
crosslinking of the components of the aqueous composition.
The novel gel compositions of the present invention may be
prepared by either adding the active ingredient to the carrier
ingredients and forming a gel, or by forming a gel from the
carrier ingredients and adding the active ingredient to the gel.
Novel glass compositions of the present invention can be
prepared by dehydrating gel compositions containing active
ingredient (s) . If a granular composition is desired, the glass

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can be ground and sieved. Alternatively, a granular composition
can be obtained by dehydrating a gel carrier to form a glass,
grinding the glass to the desired size particles and blending
the ground glass particles with the active ingredient to obtain
a uniform, granular composition.
Preferred Embodiments of the Invention
In an especially preferred embodiment of the invention, a
gel composition is prepared by dissolving an amino acid, lysine
monohydrate, in water at about 60°C to about 95°C to form a
concentrated solution, and adding to the solution a carboxylic
acid, citric acid, a metallic oxide, magnesium oxide, and an
active ingredient, an artificial sweetener, sodium saccharin.
Upon standing at ambient temperature the gel composition forms
immediately to within about 30 seconds.
The gel compositions at 65%-85o solids content show high
viscosity (500 to 10,000 centipoise) behavior similar to
concentrated sugar syrups and there is no problem with
recrystallization as with sugar and other sugar substitutes. At
even higher solids concentrations the gel compositions have the
properties of a toffee or chewy candy without crystallization.
In another preferred embodiment, a glass composition is
prepared by dehydrating a gel composition of the present
invention by heating it in a microwave and then cooling it to
form the glass. If desired, the glass can be ground to the
desired particle size.
Representative of the basic amino acids which can be used
to make the carriers of the present invention are the free base,
salts and hydrates of lysine, ornithine, diaminopimelic acid,
and amino acids of the formula: NH2(CHZ)nCOOH in which n is 1 to
6, such as glycine, ~i-alanine, 4-aminobutyric acid, 5-
aminovaleric acid, 6-aminocaproic acid and 7-aminoheptanoic
acid. Some of these amino acids are available as food or
pharmaceutical grade ingredients.
Representative of the carboxylic acids that can be used to
make the carriers of the present invention are mono-, di-, and
tri-carboxylic acids, such as acetic, citric, malic, succinic,
tartaric, and fumaric acid.

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The preferred metal oxide for use in preparing the carriers
of the present invention is magnesium oxide, which is commonly
used in foods. Other non-toxic metal oxides, such as zinc oxide
and calcium oxide, or metal hydroxides, such as the hydroxides
of magnesium, calcium, sodium, and potassium also can be used.
In addition, soluble salts and carbonates of magnesium and
calcium can also be used.
For the gel carrier the ratio of the basic amino acid to
the carboxylic acid to the metallic ion source to the water is
usually from 1/2 mole amino acid . 1 mole carboxylic acid . 1/2
mole metallic ion source . 2 moles water to 2 moles amino
acid . 1 mole carboxylic acid . 2 moles metallic ion source . 10
moles water. In the preferred method of preparing the gel
carrier, the amino acid is first dissolved in the water and the
other ingredients are added to the amino acid solution to obtain
a reaction mixture having a pH of about 5 to about 9. The
ingredients are allowed to react at temperatures of from about
50°C to about 95°C. The reaction mixture usually forms a gel
within about 30 seconds.
The glass carrier is readily prepared from a viscous gel by
dehydrating it under microwave radiation at a setting of 50~
power to 100% power for about 0.5 minutes to about 15 minutes or
by conventional oven drying methods at temperatures of about
120°C to about 180°C for about 10 minutes to about 60 minutes.
The advantage of microwave drying is the rapid release of water
and the development of the glass structure in the microwave.
The active ingredients that can be used with the carriers
to form the compositions of the present invention include
without limitation, flavoring agents, colors, cosmetic agents,
luminescents and therapeutic agents. The only limitation on the
active ingredient is that it is not adversely affected by the
. ingredients of the carrier.
A wide variety of therapeutic agents can be used as the
active ingredient(s). Certain of the therapeutic agents also
have fluorescent and phosphorescent properties including
salicylic acid, p-amino benzoic acid, folic acid, vitamin A,
fluorescein, riboflavin and pH indicators. The fluorescent and
phosphorescent properties can be used in food products and the

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like to determine the viable life of the products and whether
they have been exposed to adverse conditions.
Many flavorings are esters, acids and aldehydes which are
potentially compatible with the components of the amino acid gel
and glass. These flavorings or artificial flavors can be
incorporated with artificial sweeteners to give a sugar candy,
syrup or gum. One potential application is the introduction of
flavor packets for coffee and tea products. A line of gummy
bear-like products of different flavors for novelty uses is
possible (e. g. edible gummy labels like glue or a glue
stick/flavor) .
A wide variety of flavoring agents can be used in the
compositions of the present convention. Many flavorings are
water insoluble or only slightly soluble in water. These
flavorings such as cherry, mint, cinnamon, and orange are
usually dissolved in a vegetable oil carrier. The oil can be
added to the viscous gel of the present invention and uniformly
suspended as small droplets of oil in the aqueous gel. When the
gel carrier is dried these oil droplets become entrapped or
encapsulated in the glass carrier. This entrapment can be seen
under a light microscope as small oil globules immobilized in a
clear glass.
The glass carrier provides a stable environment for the
flavoring or fragrance and provides a means of controlled
release. The advantage of the use of these carriers is that
diffusion of volatile components from the oil droplet and
through the glass carrier is extremely slow. However, full
flavor or fragrance is released when the glass carrier is
dissolved by mouth saliva or if the material is heated
substantially above its glass transition temperature (130°C).
Most flavorings also are susceptible to oxidation and
entrapment is used to increase the shelf life. Prior art
methods use spray drying of the flavor with polymeric gums which
entrap the flavor. The method of the present invention differs
from existing methods of entrapment since the flavoring is
encased in the glass carrier. The carrier compositions
containing flavoring agents can be used in cake mixes, beverage
powders, gelatin desserts, candies, and the like.

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Several classes of flavors with different organoleptic
properties and typical flavoring agents are listed below:
Flavoring Chemical Name
Balsamic
Anise methyl p-anisate
Balsam cinnamyl alcohol
Caramel acetanisole
Chocolate maltol, 2 methyl butyraldehyde
Cinnamon cinnamaldehyde
Honey allyl phenylacetate
Sweet ethyl vanillin
Vanilla vanillin
Citrus
Lemon citral dimethyl acetal
Lime undecyl alcohol
Orange decyl acetate
Coffee
Coffee methyl cyclopentenolone
Fatty
Butter 2,3 pentanedione
Cheese butyric acid
Creamy tributyrin
Floral
Blossom neryl acetate
Carnation 5-phenyl 1-pentanol
Gardenia geranyl tiglate
Hyacinth p-tolyl phenylacetate
Jasmin benzyl acetate
Lilac terpineol
Rose butyl phenylacetate
Fruity
Apple isoamyl hexanoate
Apricot allyl butrate
Banana allyl heptanoate
Cherry benzyl acetate
Coconut decalactone
Grape isobutyl isobuyrate
Melon 2,6 dimethyl 5-heptenal
Peach decalactone
Pear ethyl decanoate
Pineapple hexyl butyrate
Plum 2-hexenal
Raspberry butyl valerate
Strawberry ethyl isobutyrate

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Flavoring Chemical Name
Minty
Minty dl-menthol
Nutty
Almond benzaldehyde
Hazelnut 2,3 diethylpyrazine
Peanut 2-methoxy 3 methylpyrazine
Walnut 2,3 dimethylpyrazine
Smoky
Smoky guaiacol
Woody cuminaldehyde
The practice of the present invention is further
illustrated by the examples.
Example 1
Preparation of Gel and Glass
A gel was prepared by dissolving 175 gm of lysine
monohydrate in 105 gm water at 60°C-95°C. To this solution was
added 43 gm MgO, 205 gm of citric acid (anhydrous). The gel
that formed after about 10 seconds was microwaved at 100 % power
(1400 watts/2450 megahertz) for 7 to 10 minutes and then cooled
in a freezer to room temperature (20°C) to form a glass. The
glass was ground and sieved to give various particle sizes
similar to table sugar. The following mixture of mesh sizes
was prepared: 24 Mesh (33%), 32 Mesh (410), 42 Mesh (17%) and
60 Mesh (6%) .
The glass contained 29 gm (1 ounce), 11.7 gms by weight
protein, 0% carbohydrate, 0% fat, no cholesterol and no sodium.
The mineral content was 1300 mg magnesium and 480 mg calcium.
The calorie content was 71.6 kilocalories or 2.46 kcal/gm.
Example 2
Preparation of Gel and Glass
The procedure of Example 1 was followed except that the
amount of magnesium oxide in the formulation was reduced. The
gel was formed by dissolving 132 gm of lysine monohydrate in

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150 gm water at 60°C-95°C. To this solution were added 21.6 gm
Mg0 and 6.72 gm Ca0 and 147 gm of citric acid (monohydrate) .
The resulting gel was microwaved at 1000 power (1400 watts/2450
megahertz) for 7-10 minutes and then cooled to 20°C in a
freezer to form a glass. Because calcium citrate is only
slightly soluble in water the ratio and amount of Ca0/Mg0
should be controlled to produce a clear gel and glass. Typical
ratios range from 0 to 0.33.
Example 3
Preparation of Sugar Substitute
About 250 gms of the ground glass carrier of Example 1 was
mixed with 6.3 gm of aspartame to form a granular, sugar-like,
artificial sweetener. The carrier-aspartame composition was
used to replace 250 g of sugar in the following recipe for
sugar cookies.
5008 flour
2508 sugar or sugar replacer
225g shortening
25g nonfat dry milk
5g salt
4g sodium bicarbonate
5g baking powder
85g water
The batter was baked at 350°F for ten minutes. The batter
and cookies had the same color and appearance of control
sugar cookies made using sugar. The amount of citrus flavor
of the cookies depended on the amount of anhydrous citric
acid used. Cookies made with the ground glass carrier of
Example 1, which was made with anhydrous citric acid, had a
lemon taste. Similar cookies made with a ground glass
carrier, which was made with an equal amount of citric acid
monohydrate in place of the anhydrous citric acid, did not
have a lemon or citrus flavor.

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Example 4
Preparation of Sugar Substitutes
Artificial sweeteners that can be used with the carriers
of the present invention to replace sugar besides aspartame,
include acesulfame K, and sodium saccharin.
Artificial sweetener compositions may be prepared as
follows:
To 240 gm of the ground glass mixtures from Examples 1
and 2 are added the following amounts of the artificial
IO sweeteners: 1.2 gm of acesulfame or 0.4 gm of sodium
saccharin. The ground glass and artificial sweetener
mixtures had a tart/sweet taste using the ground glass of
Example 1 or a sweet taste using the ground glass mixture of
Example 2.
Example 5
Alternative Method of Preparing Sugar Substitute
A gel was prepared by dissolving 100 gm of lysine
monohydrate in 100 gm water at 60°C-95°C. To this solution
was added 24 gm Mg0 and 115 gm of citric acid (anhydrous) and
1.195 gm acesulfame K. The gel which formed after 10 seconds
was microwaved at 100% power (1400 watts/2450 megahertz) for
7 to 10 minutes and then cooled in a freezer to 20°C to form
a glass. The glass was ground and sieved to give various
particle sizes similar to table sugar. The following mixture
of mesh sizes was prepared: 24 Mesh (33%), 32 Mesh (41%), 42
Mesh (17%) and 60 Mesh (6%). The material had the
organoleptic and physical properties of crystalline table
sugar.
Example 6
Preparation of Sugar Substitute with Calcium Oxide
A gel was formed by dissolving 110 gm of lysine
monohydrate in 100 gm water at 60°C-95°C. To this solution
was added 18 gm Mg0 and 5.6 gm Ca0 and 122.5 gm of citric
acid (monohydrate) and 1.243 gm acesulfame K. The gel that
formed after 20 seconds was microwaved at 100% power (1400
watts/2450 megahertz) for 7 to 10 minutes and then cooled to

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20°C in a freezer to form a glass. The material when ground
as described in Example 5 had the desired properties of
crystalline sugar and a clean sweet taste without a sour
aftertaste.
Additional sugar substitutes were made using 6.402 gms
of encapsulated aspartame (NutrasweetTM) or 2.502 gms of
powdered aspartame in place of the acesulfame K.
Example 7
Preparation of Sugar Substitute with Malic Acid
A clear gel was made by adding 50 gm of lysine
monohydrate and 50 gm of lysine monohydrochloride to 100 gm
of water at 60°C-95°C. To this solution were added 20 gm Mg0
and 82 gm of malic acid and 60 ml of sodium saccharin. The
slightly yellow gel which formed immediately was microwaved
at 100 power (1400 watts/2450 megahertz) for 5 to 7 minutes
and cooled to 20°C. The resulting glass which was ground as
described in Example 5 had the sweet taste and the texture of
crystalline sugar.
The pH of the glass can be reduced by increasing the
ratio of the lysine HC1/lysine HOH from 1.0 to 2.5. Flavor
changes from neutral/sweet to sour/sweet are obtained if the
ratio is increased and other ingredients are kept constant.
The glasses of Examples 1-2 and 4-7 possess a blue
fluorescence and a blue green phosphorescence lasting up to
20 seconds when excited by longwave W light. As a result
these glasses can be used to impart fluorescence or
phosphorescence to the products to which they are added.
Example 8
Preparation of Hard Candy
A hard candy was prepared without the use of sugar by
heating 100 gm of water (60°C-90°C) and dissolving in it 110
gm lysine monohydrate. To this solution was added 18 gm MgO,
5.6 gm Ca0 and 122.5 gm of citric acid monohydrate. A clear
gel formed after 10 seconds. The gel was cooled to just
above room temperature and artificial sweetener (1.24 gm
acesulfame K), food coloring (20 drops red) and flavoring (40
drops artificial cherry) were added. Equal portions of the

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gel were dehydrated by microwaving at 100% power (1400
watts/2450 megahertz) for 7 to 10 minutes or oven drying at
120°C for 30 minutes.
The resulting glasses were brittle like sugar and had
the taste and texture of a hard candy made from sugar.
Example 9
Preparation of Hard Candy
The procedure of Example 8 was repeated reducing the
relative amounts of magnesium oxide and calcium oxide by the
addition of sodium hydroxide. To the lysine solution were
added, in order, 6.1 gm NaOH, 12.5 gm MgO, 3.0 gm Ca0 and
122.5 gm of citric acid monohydrate to form a clear gel. The
gel was cooled to just above room temperature and artificial
sweetener (1.24 gm acesulfame K), food coloring (20 drops
red) and flavoring (40 drops artificial cherry) are added.
The gel was dehydrated by microwaving at 100% power (1400
watts/2450 megahertz) for 7 to 10 minutes or by oven drying
at 120°C for 45 minutes to obtain a glass which had the taste
and texture of a hard candy.
Example 10
Preparation of Taffy-like Product
A gel was prepared from 100 ml water, 110 gm lysine
monohydrate, 18 gm MgO, 5.6 gm CaO, and 122.5 gm citric acid
monohydrate(65% solids by weight). The mixture was evaporated
to between 78 to 81o solids by weight after which flavoring
and artificial sweetener 0.4 gms (sodium saccharin) were
added. The candy was soft and chewy with a texture of taffy.
Example 11
Preparation of Glass with PABA
A glass was prepared from 10 grams of lysine monohydrate
dissolved in 6 gm water, 2.45 gm MgO, and 7.45 gm of succinic
acid. Para aminobenzoic acid (PABA) was added at 0.01%-0.16%
by weight of the total dry ingredients. The clear gel which
formed was dried in a microwave at 1000 power (1400
watts/2450 megahertz) for 60 seconds and cooled to 20°C to
form a glass. The phosphorescence of the material was

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observed to have different colors under short and long
wavelength UV light. At 365 nm the phosphorescence was
blue/green lasting up to 25 seconds and was similar to that
observed without the PABA. Under shortwave UV (254 nm) the
phosphorescence was intensely blue/white lasting up to 20
seconds. Without PABA the shortwave phosphorescence was
substantially reduced in intensity and was less blue and more
green in color. The fluorescence of the solid glass was
substantially brighter than the gel at both wavelengths of
excitation.
Example 12
Preparation of Glasses with Chromophores
Compositions containing salicylic acid (ortho
hydroxybenzoic acid, benzoic acid, and vanillin
(3-methoxysalicylaldehyde)) was prepared by the method of
Example 11 but with chromophores in place of the PABA. The
following table shows the phosphorescence observed after
excitation with W light at 254 nm or 365 nm:
Color/Intensity Color/Intensity
Compound (254 nm) (365 nm)
Salicylate blue++ blue++
Benzoic green- blue/green-
vanillin blue/white++ blue/green-
PABA blue/white++ blue/green-
(- indicates no change from control ++ indicates intense
color observed)
Example 13
Preparation of Gels and Glasses with Other Amino Acids
Clear gel and glasses were prepared from other amino
acids having a linear carbon chain separating the amino and
carboxyl group. The following amino acids and (weights) were
used as substitutes for lysine monohydrate in Example 11

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above: glycine (4.6 gm), a-alanine (5.4 gm), 4-aminobutyric
acid [GABA] (6.3 gm), 6-aminocaproic acid (7.9 gm). The
presence of 0.0086 gm vanillic acid (0.060) produced a
green/blue phosphorescence. Without the vanillic acid there
was no phosphorescence.
Example 14
Preparation of Glass with Fluorescein
The method of Example 11 was repeated except that the
PABA was replaced by adding 0.009 gm of fluorescein (sodium
salt). The solid fluorescein salt did not fluoresce unless
dissolved in a solvent. The dried glass showed a brilliant
yellow/white fluorescence. The solid glass was placed in
pure ethanol and it was observed that no fluorescein was
dissolved from the glass over several months.
Example 15
Preparation of Glass with vitamin A
The method of Example 11 was repeated but 10 gm lysine
and 10 ml water were used to dissolve 4 gm ZnO, 8.3 gm malic
acid, and 0.01 gm of Vitamin A acetate. The yellow gel was
microwaved to give a solid glass having Vitamin A activity
and giving blue fluorescence (with longwave UV excitation)
and green phosphorescence.
Example 16
Preparation of Glass with Vitamin E
The method of Example 15 was repeated but 0.036 gm of
Vitamin E was used instead of Vitamin A acetate.
Example 17
Preparation of Glass with Folic Acid
The method of Example 15 was repeated but 0.02 gm folic
acid was used in place of Vitamin A acetate.

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Example 18
Preparation of Glass with Glycine
Differences in phosphorescence were observed by
substituting glycine for lysine. With Vitamin A acetate blue
- 5 phosphorescence was observed if lysine was used but no
phosphorescence was observed with glycine. Either 10 gm
lysine or 4.7 gm glycine and 10 ml of water dissolve 2.45 gm
MgO, 7.4 gm succinic acid and 0.02 gm Vitamin A acetate which
is dried in a microwave.
Example 19
Preparation of Glass with pH Sensitive Active Ingredient
Compounds which are sensitive to pH can be incorporated
in the glass. 0.01 gms of bromophenol blue or bromocresol
purple were dissolved in the lysine or glycine glass of
Example 18. A red fluorescence was observed with the dry
glasses. The red fluorescence corresponds to the emission
observed with these dyes dissolved in ethanol. Excitation at
260 nm gives fluorescence at 585 nm for these dyes.
The products prepared as described in the Examples are
low in calories. The calories supplied by the amino acid
portion of the gel or glass can be treated as calories
supplied by protein. In humans the protein fraction breaks
down to C02, H20 and urea. The amount of protein breakdown
can normally be measured by analysis of the urine and feces
as well as measurement of respiratory gas exchange. The
average metabolic energy (1 Cal = 1 kilocalorie) derived from
protein is 4.1 Cal/g, from carbohydrate, 4.1 Cal/g, and from
lipid, 9.3 Cal/g. Since carbohydrate and lipid are not
components of this food they are not included in the
calculation. Normally however, the foodstuff containing the
gel or glass may also contain carbohydrate, fat and other
protein components and an alternative (indirect) approach is
needed to calculate calories.
It also can be assumed that the organic acid portion is
fully digested and the acids are fully metabolized to CO2 and
H20. It is reasonable to use heat of combustion data for
these compounds. The inorganic components and water do not

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contribute calories to the diet. However, the calcium and
magnesium in the material may act to prevent absorption of
the components into the gut (laxative effect) and reduce the
calorie intake.
It will be apparent to those skilled in the art that a
wide variety of active ingredients may be incorporated into
the compositions of the present invention without departing
from the spirit and scope of the invention. Therefore, it is
intended that the invention only be limited by the scope of
the claims.

Dessin représentatif

Désolé, le dessin représentatif concernant le document de brevet no 2267497 est introuvable.

États administratifs

2024-08-01 : Dans le cadre de la transition vers les Brevets de nouvelle génération (BNG), la base de données sur les brevets canadiens (BDBC) contient désormais un Historique d'événement plus détaillé, qui reproduit le Journal des événements de notre nouvelle solution interne.

Veuillez noter que les événements débutant par « Inactive : » se réfèrent à des événements qui ne sont plus utilisés dans notre nouvelle solution interne.

Pour une meilleure compréhension de l'état de la demande ou brevet qui figure sur cette page, la rubrique Mise en garde , et les descriptions de Brevet , Historique d'événement , Taxes périodiques et Historique des paiements devraient être consultées.

Historique d'événement

Description Date
Inactive : CIB expirée 2016-01-01
Inactive : CIB expirée 2016-01-01
Inactive : CIB de MCD 2006-03-12
Inactive : CIB de MCD 2006-03-12
Inactive : CIB de MCD 2006-03-12
Inactive : CIB de MCD 2006-03-12
Le délai pour l'annulation est expiré 2005-10-04
Lettre envoyée 2004-10-04
Accordé par délivrance 2004-05-25
Inactive : Page couverture publiée 2004-05-24
Lettre envoyée 2004-03-15
Préoctroi 2004-03-01
Inactive : Taxe finale reçue 2004-03-01
Taxe finale payée et demande rétablie 2004-02-25
Réputée abandonnée - omission de répondre à un avis sur les taxes pour le maintien en état 2003-10-06
Un avis d'acceptation est envoyé 2003-09-05
Lettre envoyée 2003-09-05
Un avis d'acceptation est envoyé 2003-09-05
Lettre envoyée 2003-08-27
Inactive : Approuvée aux fins d'acceptation (AFA) 2003-08-13
Inactive : Correspondance - Transfert 2003-06-30
Inactive : Lettre officielle 2003-06-20
Lettre envoyée 2003-06-03
Inactive : Transfert individuel 2003-04-16
Modification reçue - modification volontaire 2003-03-19
Modification reçue - modification volontaire 2003-01-21
Inactive : Dem. de l'examinateur par.30(2) Règles 2002-07-26
Modification reçue - modification volontaire 2002-01-11
Inactive : Dem. de l'examinateur par.30(2) Règles 2001-07-12
Inactive : Lettre officielle 2001-02-27
Lettre envoyée 2001-02-26
Lettre envoyée 2001-02-26
Lettre envoyée 2001-02-26
Lettre envoyée 2001-02-26
Inactive : Correspondance - Formalités 2001-02-22
Inactive : Renseign. sur l'état - Complets dès date d'ent. journ. 2001-01-17
Inactive : Rétablissement - Transfert 2001-01-15
Exigences de rétablissement - réputé conforme pour tous les motifs d'abandon 2001-01-15
Inactive : Abandon. - Aucune rép. à lettre officielle 2000-12-08
Inactive : Renseignement demandé pour transfert 2000-09-08
Inactive : Lettre officielle 2000-09-05
Inactive : Supprimer l'abandon 2000-08-11
Inactive : Abandon. - Aucune rép. à lettre officielle 2000-07-04
Inactive : Correspondance - Formalités 2000-06-30
Inactive : Transfert individuel 2000-06-30
Inactive : Page couverture publiée 1999-05-27
Inactive : Lettre de courtoisie - Preuve 1999-05-11
Inactive : CIB attribuée 1999-05-04
Inactive : Acc. récept. de l'entrée phase nat. - RE 1999-05-04
Inactive : CIB en 1re position 1999-05-04
Demande reçue - PCT 1999-05-03
Toutes les exigences pour l'examen - jugée conforme 1999-04-01
Exigences pour une requête d'examen - jugée conforme 1999-04-01
Demande publiée (accessible au public) 1998-04-09

Historique d'abandonnement

Date d'abandonnement Raison Date de rétablissement
2003-10-06

Taxes périodiques

Le dernier paiement a été reçu le 2004-02-25

Avis : Si le paiement en totalité n'a pas été reçu au plus tard à la date indiquée, une taxe supplémentaire peut être imposée, soit une des taxes suivantes :

  • taxe de rétablissement ;
  • taxe pour paiement en souffrance ; ou
  • taxe additionnelle pour le renversement d'une péremption réputée.

Veuillez vous référer à la page web des taxes sur les brevets de l'OPIC pour voir tous les montants actuels des taxes.

Historique des taxes

Type de taxes Anniversaire Échéance Date payée
Taxe nationale de base - générale 1999-04-01
Requête d'examen - générale 1999-04-01
TM (demande, 2e anniv.) - générale 02 1998-10-05 1999-04-01
TM (demande, 3e anniv.) - générale 03 1999-10-04 1999-07-22
Enregistrement d'un document 2000-06-30
TM (demande, 4e anniv.) - générale 04 2000-10-04 2000-08-22
Rétablissement 2001-01-15
Enregistrement d'un document 2001-01-15
TM (demande, 5e anniv.) - générale 05 2001-10-04 2001-08-27
TM (demande, 6e anniv.) - générale 06 2002-10-04 2002-09-26
Enregistrement d'un document 2003-04-16
Rétablissement 2004-02-25
TM (demande, 7e anniv.) - générale 07 2003-10-06 2004-02-25
2004-02-25
Taxe finale - générale 2004-03-01
Titulaires au dossier

Les titulaires actuels et antérieures au dossier sont affichés en ordre alphabétique.

Titulaires actuels au dossier
NATURA, INC.
Titulaires antérieures au dossier
JAMES W., JR. STITLEY
JOEL I. DULEBOHN
RICHARD S. TURK
Les propriétaires antérieurs qui ne figurent pas dans la liste des « Propriétaires au dossier » apparaîtront dans d'autres documents au dossier.
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Description du
Document 
Date
(aaaa-mm-jj) 
Nombre de pages   Taille de l'image (Ko) 
Revendications 2003-01-21 4 136
Revendications 2003-03-18 4 113
Abrégé 1999-04-01 1 36
Description 1999-04-01 16 751
Revendications 1999-04-01 2 68
Page couverture 1999-05-21 1 34
Revendications 2002-01-11 3 98
Description 2002-01-11 16 749
Page couverture 2004-04-22 1 30
Avis d'entree dans la phase nationale 1999-05-04 1 202
Demande de preuve ou de transfert manquant 2000-04-04 1 109
Courtoisie - Lettre d'abandon (lettre du bureau) 2001-01-15 1 171
Avis de retablissement 2001-02-26 1 173
Courtoisie - Certificat d'enregistrement (document(s) connexe(s)) 2001-02-26 1 113
Courtoisie - Certificat d'enregistrement (document(s) connexe(s)) 2001-02-26 1 113
Courtoisie - Certificat d'enregistrement (document(s) connexe(s)) 2001-02-26 1 113
Avis du commissaire - Demande jugée acceptable 2003-09-05 1 160
Courtoisie - Certificat d'enregistrement (document(s) connexe(s)) 2003-08-27 1 106
Courtoisie - Lettre d'abandon (taxe de maintien en état) 2003-12-01 1 177
Avis de retablissement 2004-03-15 1 166
Avis concernant la taxe de maintien 2004-11-29 1 173
PCT 1999-04-01 7 265
Correspondance 1999-05-10 1 33
Correspondance 2000-06-30 6 399
Correspondance 2000-09-05 1 8
Correspondance 2000-09-07 1 13
Correspondance 2001-01-15 3 81
Correspondance 2001-02-22 1 34
Correspondance 2001-02-23 1 13
Correspondance 2003-06-20 1 21
Taxes 2001-08-27 1 42
Taxes 2000-08-22 1 40
Taxes 2002-09-26 1 40
Taxes 1999-07-22 1 46
Correspondance 2004-03-01 1 29
Taxes 2004-02-25 1 41