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Sommaire du brevet 2306913 

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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) Demande de brevet: (11) CA 2306913
(54) Titre français: COMPOSITION A BASE D'EMULSIFIANT-LIPIDE
(54) Titre anglais: EMULSIFIER-LIPID COMPOSITION
Statut: Réputée abandonnée et au-delà du délai pour le rétablissement - en attente de la réponse à l’avis de communication rejetée
Données bibliographiques
(51) Classification internationale des brevets (CIB):
  • A21D 2/16 (2006.01)
  • A23D 9/013 (2006.01)
(72) Inventeurs :
  • ZIMMERMAN, STEPHEN PAUL (Etats-Unis d'Amérique)
  • REED, JADA DAWN (Etats-Unis d'Amérique)
  • SEIDEN, PAUL (Etats-Unis d'Amérique)
(73) Titulaires :
  • THE PROCTER & GAMBLE COMPANY
(71) Demandeurs :
  • THE PROCTER & GAMBLE COMPANY (Etats-Unis d'Amérique)
(74) Agent: DIMOCK STRATTON LLP
(74) Co-agent:
(45) Délivré:
(86) Date de dépôt PCT: 1998-10-16
(87) Mise à la disponibilité du public: 1999-04-29
Requête d'examen: 2000-04-12
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/US1998/021969
(87) Numéro de publication internationale PCT: WO 1999020111
(85) Entrée nationale: 2000-04-12

(30) Données de priorité de la demande:
Numéro de la demande Pays / territoire Date
60/062,849 (Etats-Unis d'Amérique) 1997-10-20

Abrégés

Abrégé français

L'invention concerne une composition à base d'émulsifiant-lipide comprenant un constituant monoglycéridique, un constituant ester polyglycérolique ainsi qu'un constituant de matière grasse. Le constituant monoglycéridique est choisi entre le mono-diglycéride, des monoglycérides distillés ou leurs mélanges, et il comprend environ 2,0 % à 50 % de la composition d'émulsifiant-lipide. Le constituant mono-diglycéridique ou monoglycéridique distillé préféré présente une concentration élevée (?60 %) de monoglycéride. Le constituant ester polyglycérolique comprend environ 0,5 % à environ 40 % de la composition d'émulsifiant-lipide. L'ester polyglycérolique comprend moins de 50 % de polyol libre. L'ester polyglycérolique comprend environ 2 à environ 10 unités glycérol par fraction de polyglycérol. Moins de 40 % des groupes hydroxyle des unités glycérol sont estérifiés avec de l'acide myristique, de l'acide palmitique, de l'acide stéarique ou des mélanges de ces acides. Le constituant de matière grasse peut être une matière grasse digestible ou une matière grasse non digestible et il constitue environ 20 % à environ 97,5 % de la composition d'émulsifiant-lipide. La matière grasse non digestible, si on l'utilise, présente de préférence des propriétés similaires à celles d'un triglycéride, par exemple, un polyester de polyol acide gras. Les compositions d'émulsifiant-lipide sont adaptées à une utilisation dans des compositions de pâte amidonée. La composition d'émulsifiant-lipide est particulièrement adaptée à une utilisation dans des pâtes à base d'amidon transformables en feuilles destinées à être frites dans une matière grasse non digestible, où elle sert à complexer l'amidon, à réguler la répartition d'eau et à lier l'eau.


Abrégé anglais


An emulsifier-lipid composition comprising a monoglyceride component, a
polyglycerol ester component and a fat component. The monoglyceride component
is selected from mono-diglyceride, distilled monoglycerides or mixture
thereof, and comprises about from about 2.0 % to about 50 % of the emulsifier-
lipid composition. The preferred mono-diglyceride or distilled monoglyceride
component has a high concentration (60 %) of monoglyceride. The polyglycerol
ester component comprises from about 0.5 % to about 40 % of the emulsifier-
lipid composition. The polyglycerol ester comprises less than 50 % free
polyol. The polyglycerol ester comprises from about 2 to about 10 glycerol
units per polyglycerol moiety. The glycerol units have less than 40 % of their
hydroxyl groups esterified with myristic acid, palmitic acid, stearic acid, or
mixtures of these acids. The fat component may be a digestible fat or non-
digestible fat and comprises from about 20 % to about 97.5 % of the emulsifier-
lipid composition. The non-digestible fat, if used, preferably has properties
similar to a triglyceride, for example, a polyol fatty acid polyester. The
emulsifier-lipid compositions are suitable for use in starched-based dough
compositions. The emulsifier-lipid compositions are particularly suitable for
use in starched-based sheetable doughs intended to be fried in non-digestible
fat, where it serves to complex starch, control water distribution and bind
water.

Revendications

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


16
What is claimed is:
1. An emulsifier-lipid composition characterized in that it comprises:
a) from 2.0% to 50% of a monoglyceride component comprising;
(i) from 30% to 98% monoglycerides having an iodine value in the range of
from 2 to 120;
(ii) less than 2% free glycerine;
(iii) the balance being diglycerides and triglycerides;
b) from 0.5% to 40% of a polyglycerol ester component comprising;
(i) less than 50% free polyol glycerine;
(ii) from 2 to 10 glycerol units per polyglycerol moiety wherein less than 40%
of their hydroxyl groups are esterified with myristic acid, palmitic acid,
stearic acid, or mixtures thereof; and
c) from 20% to 97.5% fat.
2. The emulsifier-lipid composition according to Claim 1 wherein the
polyglycerol ester
comprises less than 30% glycerine.
3. The emulsifier-lipid composition according to any one of the preceding
claims wherein the
monoglyceride component comprises from 10% to 40%, preferably 12% to 30% of
the
emulsifier-lipid composition.
4. The emulsifier-lipid composition of according to any one of the preceding
claims wherein
the polyglycerol ester component comprises from 1.0% to 35%, preferably 1.5%
to 30% of the
emulsifier-lipid composition.
5. The emulsifier-lipid composition according to any one of the preceding
claims wherein the
polyglycerol ester component has less than 5.0% cyclic polyglycerol esters and
less than 5.0%
diglycerides.
6. The emulsifier-lipid composition according to any one of the preceding
claims wherein the
monoglyceride component comprises from 70% to 90% monoglycerides.
7. The emulsifier-lipid composition according to any one of the preceding
claims wherein the
polyglycerol ester component has from 10% to 33% hydroxyl groups esterified.

17
8. The emulsifier-lipid composition according to any one of the preceding
claims
wherein the fat is a non-digestible fat.

Description

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


CA 02306913 2000-04-12
WO 9920111 PCT/US98121969
EMULSIFIER-LIPID COMPOSITION
TECHNICAL FIELD
The present invention relates to emulsifier-lipid compositions. More
specifically, the present
invention relates to emulsifier-lipid composition particularly useful in the
preparation of sheetable
Boughs, such as fabricated snacks, especially low-fat fabricated snacks.
BACKGROUND
Emulsifiers are commonly used in the preparation of Boughs which are further
processed by
sheeting, extruding, frying, baking and other food processing activities. The
composition and
functionality of the emulsifier has great impact on the process feasibility of
the dough and the texture of
the final product. In the process of sheeting, dough compositions are formed
into a sheet using various
sheeting processes or equipment such as a roll mill. The dough is subjected to
various stressful processes
(e.g., mixing, sheeting, milling, and extrusion). During the mixing, milling
and sheeting of the dough, the
starch cells swell and burst releasing amylose (i.e., free starch). The
amylose interacts with the water in
the dough to give a cohesive, elastic dough sheet. However, if too much
amylose is present in the dough
composition, the dough will become sticky and adhere to the sheeting and
cutting equipment. The
presence of large amounts of amylose in the dough composition will also result
in a rigid and stiff dough
that prevents the dough from being sheeted and from expanding during frying.
This results in an end food
product that is dense, hard and brittle.
Emulsifiers, in particular, mono-diglycerides are generally added at low
levels to the dough
compositions. The emulsifier helps prevent stickiness of the dough by
complexing a portion of the
amylose while allowing enough stiffrtess and adhesiveness in the dough to form
a cohesive and elastic
dough sheet.
Determining which patricular emulsifier to use in a particular dough
composition is extremely
difficult. The almost infinite number of chemical compositions available and
the physical surface-active
properties of the emulsifier generally preclude accurate predictions of
emulsifier behavior in the sheeted
dough. Further complicating the determination is the uncertainty of blending
the emulsifier with other
lipid systems such as other emulsifiers, trigiyceride, and non-digestible
fats.
Several references describe the use of emulsifiers in sheeted Boughs. U.S.
Patent No. 4,678,672 to
Dartey et al., issued July 7, 1987, discloses a reduced calorie cracker
comprising at least one emulsifier
having a hydrophilic/lipophilic balance (HLB) of 11 selected from sorbitan
monostearate, mono- and/or
diglycerides, polyoxyethylene sorbitan fatty acid esters, and sodium stearoyl-
2-lactylate. Dartey et al. also
discloses that lower HLB emulsifiers such as ethoxylated mono- and
diglyceride, polyglycerol esters and

CA 02306913 2000-04-12
WO 99/20111 PCTlUS9&!21969
2
diacetyl tartaric acid esters may be used in combination with emulsifiers
having an HLB of 11. This
reference however does not disclose the specific composition of the various
emulsifiers. Further the
emulsifier-lipid compositions do not contain a non-digestible fat.
Although those skilled in the art use various emulsifiers in sheeted doughs as
processing aids,
they are not apt to encounter problems in practice when making sheetable
doughs intended to be fried in
non-digestible fat. For example, it has been found that when monoglycerides or
mono-digiycerides having
certain compositions are combined with non-digestible fat and put into a
starch-based dough composition,
the dough becomes less elastic. The doughs tend to change shape easily,
especially dwing processing.
During frying, the Boughs may shrink. This results in a product that is dense
and hard. It has also been
found that when certain polyglycerol esters and non-digestible fats are
combined and used in a starch-
based dough formula, the dough composition is very elastic. The ability of the
dough to retain its original
shape after processing is increased. This results in a product that is
expanded and foamy.
Conventional processing techniques also do not address the problems of
combining emulsifiers
and non-digestible fat nor direct the processor as to which compositions,
among the infinite number of
compositions, are suitable for use in fabricated snacks fried in non-
digestible fat. For example, when
polyglycerol esters having certain chemical compositions and/or higher levels
of hydrophilic moieties are
combined with non-digestible fat, phase separation can occur.
It can be seen that known methods of emulsification do not address the problem
of providing an
emulsifier or an emulsifier-lipid composition that will provide a sheetable,
cohesive and extensible dough
suitable for frying in non-digestible fat without adverse textural
disadvantages.
Accordingly, it is the object of the present invention to provide emulsifier-
lipid compositions.
It is another object of the present invention to provide emulsifier-lipid
compositions suitable for
use in fabricated snacks, especially chips fried in non-digestible fat.
It is still aaother object of the invention to provide an emulsifier-lipid
composition comprising a
combination of components having specific compositions.
The emulsifier-lipid composition of the present invention is meant to reduce
the aforementioned
problems related to emulsifier use, dough rheology and textural disadvantages
in the finished product.
SUMMARY OF THE INVENTION
The present invention relates to a novel emulsifier-lipid composition
comprising at least three
components. This emulsifier-lipid composition comprises a specific blend of a
monoglyceride component
(which consists of mono-diglycerides and/or distilled monogiycerides), a
polyglycerol ester component,
and a fat component. The first component is a monoglyceride component which
comprises from about
2.0% to about 50% of the emulsifier-lipid composition. The monoglyceride
component has a high
concentration (>60%) of monoglyceride. The second component is a polyglycerol
ester component which

CA 02306913 2000-04-12
WO 99120111 PCT/US98/21969
3
comprises from about 0.5% to about 40% of the emulsifier-lipid composition.
The polyglycerol ester
comprises less than 50% free polyp!. The polygiycerol ester comprises from
about 2 to about 10 eivcerol
units per polyglycerol moiety. The glycerol units have less than 40% of their
hydroxyl groups esterified
with myristic acid, palmitic acid, stearic acid, or mixtures of these acids.
The third component is a fat
component which comprises from about 20% to about 97.5% of the emulsifier-
lipid composition. A non-
digestible fat, if used, for all or part of the fat component preferably has
properties similar to a
triglyceride, for example, a polyp! fatty acid polyester.
The emulsifier-lipid composition blend may be prepared by mixing together the
above
components in the specified amounts. It has been found that the emulsifier
blend of the present invention
provides significant improvements in crispness of fabricated snacks fried in
non-digestible fat. The
emulsifier improves the organoleptical properties of the snack and provides a
method for producing a
snack having a unique structure. The improved results are not achievable with
any of the individual
components alone or with two-component systems using the same or similar
emulsifier.
DETAILED DESCRIPTION
Definitions
The term "sheetable dough" as used herein is a dough capable of being placed
on a smooth
surface and rolled to the desired final thickness without tearing or forming
holes.
The term "monoglyceride" as used herein refers to fatty acids containing one
fatty acid chain
attached to the glycerol. The monoglyceride component described herein is
comprised of 30-98%
monoglycerols, less than 2% free glycerine, and diglycerides with a small
amount of free glycerine or free
fatty acids.
The term "mono-diglyceride" as used herein refers to a mixture of fatty acid
monoglycerides and
fatty acid diglycerides, triglycerides and free glycerine and free fatty acids
with a monoglyceride level
greater than 30%.
The term "distilled monoglyceride" as used herein refers to a fractionated
mixture of fatty acid
monoglycerides with a monoglyceride level greater than 60%.
The term "polyglycerol" as used herein refers to condensed glycerol molecules,
such as dimeric
glycerol (diglycerol), trimeric glycerol (triglycerol), etc. Commercial
polyglycerol products are normally
mixtures containing glyceml in varying amounts of polymerization from
monomer~ic glycerol up to
tetrameric or higher glycerol condensates.
The term "emulsifier" as used herein refers to a single emulsifier.
All percentages are by weight unless otherwise stated.
Emulsifier-lipid composition

CA 02306913 2000-04-12
WO 99120111 PCT/US95/21969
4
The emulsifier-Lipid composition comprises three functional components: a
monoglyceride
component, a polyglycerol ester component, and a fat component.
One component of the emulsifier system is a monoglyceride component. The
monoglyceride component is comprised of mono-diglycerides, distilled
monoglycerides or mixtures
thereof. The monoglyceride component of the emulsifier-lipid composition of
the present invention may
be a mixture of saturated and unsaturated glycerol esters of fatty acids
typically derived from
hydrogenated to non-hydrogenated vegetable oils such as soybean oil, corn oil,
olive oil, sunflower oil,
cottonseed oil, palm oil and like vegetable oils, and animal fats such as
tallow and lard. The
monoglyceride component comprises at least 30% monoglycerides. Preferably,
concentrated mono-
diglycerides (i.e, containing >30% monoglyceride) or distilled monoglycerides
are used. The more
concentrated mono-diglycerides or distilled monoglycerides comprise at least
about 60%, preferably from
at least about 70% to at least about 98%, more preferably from at least about
80% to at least about 95%,
and most preferably about 90% monoglyceride, with the balance being
diglycerides with small amounts of
triglyceride and free glycerine. Preferably the amount of free glycerine
present in the mono-diglyceride
component is less than about 2.0%. The amount of monoglyceride present in the
mono-diglyceride or
distilled monoglyceride can be determined using AOCS Cd 11-b-91 (95).
The mono-diglycerides or distilled monoglycerides useful in the present
invention have an iodine
value in the range of from about 2 to about 120, preferably from about 20 to
about 100, more preferably
from about 40 to about 80, and most preferably from about 50 to about 75. The
iodine value can be
determined using AOCS method Cd 1-25 (93).
Preferably the mono-digiycerides or distilled monogiyceride have a linolenic
fatty acid level of
less than 3.5%.
Specific mono-diglycerides or distilled monoglycerides within the scope of the
present invention
are commercially available. Monoglycerides suitable for use in the present
invention are sold under the
trade names of Dimodan~ available from Danisco, New Century, Kansas and DMG
70, available from
Archer Daniels Midland Company, Decattu, Illinois.
The monoglyceride component comprises from about 2.0% to about 50%, preferably
from about
5.0% to about 40%, more preferably from about 10% to about 30%, and most
preferably from about 12%
to about 25% of the total emulsifier-lipid composition.
The second component of the emulsifier-lipid composition is a polyglycerol
ester. Examples of
polyglycerol ester include decaglyceroi decaoleate, triglycerol monostearate,
octaglycerol monostearate,
and octaglycerol mono-palmitate. These materials are normally not obtained in
pure fonm, but are
generally the reaction products of an esterification between a preselected cut
of polyglycerols and desired
saturated fatty acids. The result is a distribution of poiyglycerol mono-ester
and higher-esters determined
by ratio of reactants and reaction conditions.

CA 02306913 2000-04-12
WO 99120111 PCT/US98/21969
The polyglycerol esters of the present invention are specifically tailored by
controlling the
hydrophilic-lipophilic balance (HLB) of the polyglycerol esters. This is done
by controlling the balance of
esterified to unesterified hydroxyl groups during the process of
esterfication. With an increasing number
of hydroxyl groups esterified, the polyglycerol ester becomes progressively
more lipophilic. This
hydrophilic-lipophilic balance of the polyglycerol ester is important in
preparing polyglycerol ester for use
in sheeted Boughs.
Unesterified polyglycerols, long chain polyglycerol monoesters, and diesters
and tri-esters of
diglycerols and triglycerols should be limited in the polyglycerol ester
component of the present invention.
Unreacted polyglycerol (i.e. unesterfied) retained in the finished esters have
little or no emulsifier
functiona!iry, but because of their more polar nature are less soluble in non-
digestible lipids leading to
phase separation and a non-homogenous emulsifier-lipid composition.
The smaller chained polyglyceroi monoesters are very functional components of
the polyglycerol
esters in the poiyglyceroi ester component of the emulsifier-lipid composition
and thus their concentration
should be relatively high compared to other ester moieties. The di- and
triesters of di- and triglycerols are
too lipophilic and may also have a deleterious effect on the finished snack
product. Saturated diglycerides
(e.g. dipalmitin, distearin) and the cylic diglycerol esters are deleterious
emulsifier components and
therefore their concentrations should be minimized in the polyglycerol esters.
Preferably the polyglycerol
esters of the present invention comprise less than 5% cylic diglycerol esters
and less than 5% diglycerides.
Polyglycerol esters can be purified through fractionation, molecular
distillation or solvent
crystallization. The fractionated polyglycerol esters are more functional and
can be used at Power
concentration.
The composition of the poiyglycerol ester can be determined by Supercritical
Fluid
Chromatography described in the Analytical Methods section herein below.
The polyglycerol esters suitable for use in the present invention comprise
less than 50%,
preferably from about 2.0% to about 40%, and more preferably from about 5.0%
to about 25% free
glycerine; from about 5.0% to about 60%, preferably from about 15% to about
50%, more preferably from
about 10% to about 45% and most preferably from about 25% to about 40%
monoester. The polyglycerol
ester of the present invention additionally has from about 2 to about 10
glycerol units per polyglycerol
moiety wherein the glycerol units have less than 40%, preferably from about
18% to about 33%, more
preferably from about 20% to about 30% of their hydroxyl groups esterified
with myristic acid, palmitic
acid, stearic acid or mixtures thereof.
The polyglycerol ester component comprises from about 0.5% to about 40%,
preferably from
about 1.0% to about 35%, more preferably from about 1.5% to about 30% and most
preferably 2.0% to
about 25% of the total emulsifier-lipid composition.
Polyglycerol esters suitable for use in the present invention are sold under
the trade name Lonza
Polyaldo~.

CA 02306913 2000-04-12
wo 99no>< >< >< PcTiUS9sn >< 969
6
The third component of the emulsifier-lipid composition of the present
invention is a fat. The
terms "fat" and "oil" are used interchangeably herein unless otherwise
specified. The terms "fat" or "oil"
refer to edible fatty substances in a general sense, including natural or
synthetic fats and oils consisting
essentially of triglycerides, such as, for example soybean oil, corn oil,
cottonseed oil, sunflower oil, palm
oil, coconut oil, canola oil, fish oil, lard and tallow, which may have been
partially or completely
hydrogenated as well as non-toxic fatty materials having properties similar to
triglycerides, herein referred
to as non-digestible fats, which materials may be partially or fully
indigestible. Reduced calorie fats and
edible non-digestible fats, oils or fat substitutes are also included in the
term.
The term "non-digestible fat" refers to those edible fatty materials that are
partially or totally
indigestible, e.g., polyol fatty acid polyesters, such as GLEAN~.
Particularly preferred are non-digestible fats such as those described in U.
S. Patent Nos. 3,600,186 to
Mattson et al., issued May 12, 1970; 4.005,195 to Jandacek, issued January 25,
1977; 4,005,196 to
Jandacek et al., issued January 25, 1977; 4,034,083 to Mattson, issued Juiy 5,
1977; and 4,241,054 to
Volpenhein et al., issued December 23, 1980, all of which are incorporated by
reference.
By "polyol" is meant a polyhydric alcohol containing at least 4, preferably
from 4 to 11 hydroxyl
groups. Polyols include sugars (i.e., monosaccharides, disaccharides, and
trisaccharides), sugar alcohois,
other sugar derivatives (i.e., alkyl glucosides), polyglycerols such as
diglycerol and triglycerol,
pentaerythritol, sugar ethers such as sorbitan and polyvinyl alcohols.
Specific examples of suitable sugars
are mannose, galactose, arabinose, xylose, ribose, apiose, rhamnose, psicose,
fructose, sorbose, tagatose,
ribulose, xylulose, and erthrulose. Oiigosaccharides suitable for use herein
include, for example, maltose,
kojibiose, nigerose, cellobiose, lactose, melibiose, gentiobiose, turanose,
rutinose, trehalose, sucrose and
raffmose. Polysaccharides suitable for use herein include, for example,
amylose, glycogen, cellulose,
chitin, inuiin, agarose, rylans, mannan and galactans. Although sugar alcohols
are not carbohydrates in a
strict sense, the naturally occurring sugar aicohols are so closely related to
the carbohydrates that they are
also preferred for use herein. Natural sugar alcohols which are suitable for
use herein are sorbitol,
mannitol, and gaiactitol. Particularly preferred classes of materials suitable
for use herein include the
monosaccharides, the disaccharides and sugar alcohols. Preferred unesterified
polyols include glucose,
fructose, glycerol, alkoxylated polyglycerols, sugar ethers, and linked
alkoxyiated glycerines as described
in U.S. Patent No. 5,516,544 to Sekula et al., issued June 14, 1996,
incorporated by reference. A
particularly preferred polyol is sucrose. Preferred alkoxylated glycerols are
described in the following
U.S. Patents, incorporated by reference herein; U.S. 5,273,772 to Cooper,
issued Dec. 28, 1993; U.S.
5,288,884 to Cooper, issued Feb. 22, 1994; U.S. 5,298,637 to Cooper, issued
March 29, 1994; U.S.
5,362,894 to Handwerker et al., issued Nov. 8, 1994; U.S. 5,374,446 to Ferenz
et al., issued Dec. 20, 1994;
U.S. 5,387,429 to Cooper, issued Feb. 7, 1995; U.S. 5,427,815 to Ferenz,
issued June 27, 1995; U.S.
5,466,843 to Cooper, issued Nov. 14, 1995; U.S. 5,516,544; U.S. 5,589,217 to
Mazurek, issued Dec. 31,
1996; and U.S. 5,597,605 to Mazurek, issued Jan. 28, 1997. More preferred
alkoxylated glycerines are

CA 02306913 2000-04-12
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7
linked alkoxylated glycerines and are described in the following patents,
previously incorporated herein,
5,374,446; 5,427,815; and 5,516,544. Especially preferred alkoxylated
glycerines are those described in
U.S. Patent Number 5,516,544, previously incorporated by reference.
By "polyol fatty acid polyester" is meant a polyol having at least 4 fatty
acid ester groups. Pofyol
fatty acid esters that contain 3 or less fatty acid ester groups are generally
digested in, and the products of
digestion are absorbed from, the intestinal tract much in the manner of
ordinary triglyceride fats or oils,
whereas those polyol fatty acid esters containing 4 or more fatty acid ester
groups are substantially non-
digestible and consequently non-absorbable by the human body. It is not
necessary that all of the hydroxyl
groups of the polyol be esterified, but it is preferable that disaccharide
molecules contain no more than 3
unesterified hydroxyl groups for the purpose of being non-digestible.
Typically, substantially all, e.~., at
least about 85%, of the hydroxyl groups of the polyol are esterified. In the
case of sucrose polyesters,
typically from about 7 to 8 of the hydroxyl groups of the polyol are
esterified.
The polyol fatty acid esters typically contain fatty acid radicals typically
having at least 4 carbon
atoms and up to 26 carbon atoms. These fatty acid radicals can be derived from
naturally occurring or
synthetic fatty acids. The fatty acid radicals can be saturated or
unsaturated, including positional or
geometric isomers, (e.g., cis- or traps- isomers) and can be the same for all
ester groups, or can be
mixtures of different fatty acids.
Liquid non-digestible oils can also be used in the practice of the present
invention. Liquid non-
digestible oils which have a complete melting point below about 37°C
include liquid polyol fatty acid
polyesters (see Jandacek; U.S. Patent 4,005,195; issued January 25, 1977);
liquid esters of tricarballylic
acids (see Hamm; U.S. Patent 4,508,746; issued April 2, 1985); liquid diesters
of dicarboxylic acids such
as derivatives of malonic and succinic acid (see Fulcher; U.S. Patent
4,582,927; issued April 15, 1986);
liquid triglycerides of alpha-branched chain carboxylic acids (see Whyte; U.S.
Patent 3,579,548; issued
May 18, 1971); liquid ethers and ether esters containing the neopentyl moiety
(see Minich; U.S. Patent
2,962,419; issued Nov. 29, 1960); liquid fatty polyethers of polyglycerol (See
Hunter et al; U.S. Patent
3,932,532; issued Jan. 13, 1976); liquid alkyl glycoside fatty acid polyesters
(see Meyer et al; U.S. Patent
4,840,815; issued June 20, 1989); liquid polyesters of two ether linked
hydroxypolycarboxylic acids (e.g.,
citric or isocitric acid) (see Huhn et al; U.S. Patent 4,888,195; issued
December 19, 1988); various liquid
esterfied alkoxylated polyols including liquid esters of epoxide-extended
polyols such as liquid esterified
propoxylated glycerins (see White et al; U.S. Patent 4,861,613; issued August
29, 1989; Cooper et al; U.S.
Patent 5,399,729; issued March 21, 1995: Mazurek; U.S. Patent 5,589,217;
issued December 31, 1996;
and Mazurek; U.S. Patent 5,597,605; issued January 28, 1997); liquid
esterified ethoxylated sugar and
sugar alcohol esters (see Ennis et al; U.S. Patent 5,077,073); liquid
esterified ethoxylated alkyl gtycosides
(see Ennis et al; U.S. Patent 5,059,443, issued October 22, 1991); liquid
esterified alkoxylated
polysaccharides (see Cooper; U.S. Patent 5,273,772; issued December 28, 1993);
liquid linked esterified
alkoxylated polyols (see Ferenz; U.S. Patent 5,427,815; issued June 27, 1995
and Ferenz et al; U.S. Patent

CA 02306913 2000-04-12
WO 99120111 PCT/U598/21969
8
5,374,446; issued December 20, 1994); liquid esterfied polyoxyalkylene block
copolymers (see Cooper:
U.S. Patent 5,308,634; issued May 3, 1994); liquid esterified polyethers
containing ring-opened oxoiane
units (see Cooper; U.S. Patent 5,389,392; issued February 14, 1995); liquid
alkoxylated polyglycerol
polyesters (see Harris; U.S. Patent 5,399,371; issued March 21, 1995); liquid
partially esterified
polysaccharides (see White; U.S. Patent 4,959,466; issued September 25, 1990);
as well as liquid
polydimethyl siloxanes (e.g., Fluid Silicones available from Dow Corning). All
of the foregoing patents
relating to the liquid nondigestible oil component are incorporated herein by
reference. Solid non-
digestible fats or other solid materials can be added to the liquid non-
digestible oils to prevent passive oil
loss. Particularly preferred non-digestible fat compositions include those
described in U.S. 5,490,995
issued to Corrigan, 1996, U.S. 5,480,667 issued to Corrigan et al, 1996, U.S.
5,451,416 issued to Johnston
et al, 1995 and U.S. 5,422,131 issued to Elsen et al, 1995. U.S. 5,419,925
issued to Seiden et al, 1995
describes mixtwes of reduced calorie triglycerides and poiyoi polyesters that
can be used herein but
provides more digestible fat than is typically preferred.
The preferred non-digestible fats are fatty materials having properties
similar to triglycerides such
as sucrose polyesters. OLEAN~, a preferred non-digestible fat, is made by The
Procter and Gamble
Company. These preferred non-digestible fats are described in Young; et al.,
U.S. Patent 5.085,884,
issued February 4, 1992, and U. S. Pat. 5,422,131, issued June 6, 1995 to
Elsen et al.
The fat component of the emulsifier-lipid composition of the present invention
comprises from
about 20% to about 97.5%, preferably from about 65% to about 90%, and more
preferably from about
70% to about 85% of the emulsifier-lipid composition.
The emusifier-lipid composition of the present invention has unique thermal
properties, onset of
crystallization and endothermic area that relate to the performance of the
emulsifier in dough systems.
Determination of the thermal properties using a DSC is well known in the art.
Briefly, the onset of
crystallization and endothermic area is determined by using a Differential
Scanning Calorimeter (DSC),
Perkin Elmer Model # 7 . The emulsifier-lipid composition is placed into a DSC
pan and crimped. The
sample is scanned at a rate of about 5°C/min. The temperature is raised
beyond the melting point of the
emulsifier-lipid blend (indicated by an exothermic peak and return to
baseline). After the melting, the
sample is then cooled at a rate of about -5°C/min. until a temperature
of 0°C is reached. The point at
which the endotherm begins to move away from the baseline is the onset of
crystallization. The
endothermic area is also used to determine how the emulsifier will perform in
Boughs. The endothermic
area between the dough making and onset of crystallization temperature is used
for this purpose.
The emulsifiers of the present invention preferably have an onset of
crystallization in the range of
from about t00°F (37.7°C) to about 135°F (57.2°C).
The onset of crystallization temperature and the
amount of crystallization that can occur relates to the ability of the
emulsifier or emulsifier blend to
disperse homogeneously throughout the dough and adequately disperse the water
present in dough
compositions. The endothertnic area (i.e., the area shown above typical dough
making sheet formation

CA 02306913 2000-04-12
WO 99/20111 PCT/US98I21969
9
temperature) is the measurement used to predict how the emulsifier will behave
during sheeting. The
snacks of the present invention have an endothermic area above 108°F
(42.4°C) of less than about 150
millijoules, preferably less than about 125 miilijoules, more preferably from
about 1 to about 80
millijouies, more preferably from about 2 to about 40 millijoules, and most
preferably from about 4 to
about 10 millijoules .
The droplet size of the emulsifier-lipid composition has been found to be an
indication of the type
of internal product structure and void size and area that will be present in
the finished product. Since this
void size is also related to the texture of the resulting fried snack, the
type and size of oil droplets formed
are important. The method for determining the oii droplet size is described
herein. The oil droplets of the
emulsifi:r-lipid composition of the present invention are small and uniform in
size. This enables the
emulsifier-lipid composition to disperse homogeneously throughout the dough
composition. When
dispersed in water, the emulsifier-lipid composition of the present invention
tends to aggregate in clusters
of several hundred droplets. At 100x magnification, the aggregate droplet size
is preferably less than 3.0
cm2, preferably less than l.Scm2, and more preferably between 0.01 to 0.05
cm2.
The emulsifier-lipid composition of the present invention is generally used in
farinaceous
fabricated snack such as potato chips, corn chips, tortilla chips, half
products, and extruded snacks at a
level of from about 0.5% to about 8.0 % based on the weight of the dough.
Preparation
The emulsifier-lipid composition of the present invention is prepared by melt-
blending and
mixing the components until a homogeneous liquid is obtained. Melt-blending
may be accomplished by
individually maintaining or raising the temperatures of the components to a
point above their respective
melting temperatures and then thoroughly blending, or by mixing the components
at room temperature and
raising the temperature of the mixture to at least the melting point of the
highest-to-melt component
followed by thorough blending to form a homogeneous liquid.
ANALYTICAL METHODS
SUPERCRITICAL FLUID CHROMATOGRAPHY
A sample of polyglycerol ester is first silylated to derivatize any unreacted
hydroxyl groups. The
silylated sample is then injected into the supercritical fluid chromatograph
(SFC). The esters are separated
by degree of esterification on a DB 1 capillary column and detected by a flame
ionization detector. The
distribution of esters is calculated by peak area.
Eouinment and Conditions
SFC: Lee scientific series 6000 supercritical fluid chromatograph or
equivalent;
SFC Conditions:

CA 02306913 2000-04-12
WO 99/20111 PCT/US98/21969
A) Capillary Column
DB1, 0.2 a film, 50 a ID, 10 m. l&W Scientific
B) Temperatures
Oven - 90°C
Detector - 400°C
C) Pressure Proeram
Pressure, Time 125; 375, 25; 375, 10; 0, 0
D) C02
SFC grade, Scott Specialty Gases
E) HvdroQen
Approximately 30 mL / minute
F) Air
Approximately 300-350 mL / minute
G) Auxiliary Gas (Nitrosen)
Approximately 25 mL / minute
H) Svrinae for SFC infection
50 ul Hamilton
I) Vials
2 or 4 dram Kimble Glass Fischer Scientific #03-340-1 C
J) Hot Plate
90°C
K) Filter
0.45 a Alltech Associates #2092
L) Disposable Svrin~e
3.0 mL Fisher Scientific #14-823-39
Reaeents
BSTFA (bis(Trimethylsilyl~trifluoroacetamide) Supelco, lnc. #3-3027; TMSI
(Trimethylsilylimidazole)
Supelco, Inc. #3-3068; Pyridine ACS Grade MCB #PX2020-O1
Analvzine Standard
The sample is melted completely and mixed well. A disposable piper is used to
weigh 80-100 mg of
sample into a four dram vial. The sample weight is recorded. 1 mL of Pyridine
and 1 mL of
TMSI/BSTFA solution (mixed 5:1) is added to the vial. The vial is capped and
heated on the hot plate at
90°C for 15 minutes. The sample is allowed to cool. A 0.45-micron
filter is placed on the end of a 3-cc

CA 02306913 2000-04-12
WO 99120111 PC'T/US98I21969
disposable syringe. The derivatized standard is poured into the disposable
syringe and filtered into a GC
vial. The sample is injected into the Supercritical Fluid Chromatograph.
Emulsion Droplet Size Method
1. Fifty (SO) grams of emulsifier composition are heated to a complete melt at
1 SS°F.
2. An equal amount of water, 50 grams, is added to the emulsifier pre-heated
to I 70°F.
3. The water and emulsifier blend are mixed using a stainless steel whisk,
mixing for 30 seconds, adding
water in 50 gram increments to the solution until the water is 5.5 times the
amount of emulsifier (275
grams); or all of the water and emulsifier are mixed using a lab scale shear
mixer (ex. ,lanke and
Kunkel SD-45 at a setting of 7) for 60 seconds until the two components are
thoroughly combined.
4. A sample of the emulsion is placed on a new, clean microscope slide with a
cover slip and evaluated
at a magnification of 100x using a Zeiss light microscope with polarized light
filters and photographic
attachments .
5. A picture of the emulsion is taken within 120 seconds of formation.
6. Droplet size is measured using a 2.6 cm X 2.6 cm grid with 0.2 cm line
increments for Polaroid
pictures sized 1 I .S cm X 8.9 cm. Any magnification of pictures will require
comparable
magnification of grid size.
The following examples are submitted for a better understanding of the
invention and are not
intended to limit the scope of the present invention. In the examples,
emulsifier-lipid compositions are
added at the level indicated to fabricated snack compositions.

CA 02306913 2000-04-12
12
EX.~IVIPLE 1
The following composition is used to make an emulsifier-lipid composition:
Ingredient Wt. %
Non-digestible fat 85.00
Polyglycerol ester (PGE) 2,?5
Distilled Monoglyceride 12.75
(DMG)
J
The PGE is a hexaglycerol monoester of palmitic and stearic acids available
from Lonza,
Fair Lawn, NJ as PoIyaldo with an HLB of about 10, a monoester level of about
28%, a
saponification value of 100~5 , a hydroxyl value of 415~30 and a free polyol
level less than 22%.
The DMG has a monoester level of > 90% and an iodine value between 60-70 and
is sold under the
tradename of Dimodan-OK, available from Danisco, New Century KS. The non-
digestible fat is
OLEAN~, available from The Procter & Gamble Company, Cincinnati, OH.
Chemical Comnositinn of Pnlvaivc-Prnl FctPrc
Components Percentage
Monoglycerol monopalmitate 1.7
Diglycerol monopalmitate 7,3
Triglycerol monopalmitate 8.8
Tetraglycerol monopalmitate 4.6
Pentaglycerol monopalmitate, Monoglycerol5.6
dipalmitate
Total Monopalmitate 28.0
Diesters 25.9
Triesters 16.6
Tetraesters 6.1
Pentaesters 2.4
Free Polyol 21.1
AMENDED SHEET

CA 02306913 2000-04-12
WO 9y/20111 PCT1US98/21969
i3
T'he physical properties of the emulsifier system are:
Property Value
Onset of Crystallization, C 48 (1 l8vF)
Area of Crystallization, mj 0.84
Complete Melt Point, C 67 (153vF)
Oil Droplet Agglomerate Size Range,0.01-0.33
cm cQ 100x
magnification
EXAMPLE 2
The following composition is used to make an emulsifier-lipid composition:
Ingredient art %
Non-digestible fat 85.00
Polyglycerol ester (PGE) 2.25
Distilled Monoglycerid(DMG)12.75
The PGE is predominantly diglycerol monopalmitate available from Lonza, Fair
Lawn, NJ with an
HLB of less than 10, a monoester level of about 43%, a saponification value of
124, a hydroxyl value of
402, and a free polyol level of about 17%. The DMG has a monoester level of _>
90% and an iodine value
between 60-70 and is sold under the tradename of Dimodan-OK, available from
Danisco, New Century,
KS. The non-digestible fat is GLEAN~, available from The Procter & Gamble
Company, Cincinnati, OH.

CA 02306913 2000-04-12
14
Chemical C'nmnncitinnc nfPnlval..~A~.,i c~.m-..
Components Percentage
Monoglycerol monopa 0.4
Diglycerol monopalmitate 25.7
Triglycerol monopalmitateg.g
Tetraglycerol monopalmitate3.9
Pentaglycerol monopalmitate,4.3
Monoelvcerol di almitate
Total Monopalmitate 43.1
Diesters 30.6
Triesters g.0
Tetraesters l , g
Pentaesters 0.0
Free Polyol 16.6
EXAMPLE 3
The following composition was used to make an emulsifier system:
In redient Wt %
Non-di estible fat 85.00
Pol 1 cerol ester PGE) 2.25
Distilled Mono 1 ceride (DMG)12.75
The PGE is predominantly diglycerol monopalmitate available from Lonza, Fair
Lawn, N1
with an HLB of less than 10, a monoester level of about 44%, a saponification
value of 133, a
hydroxyl value of 378, and a free polyol level of less than 13%. The DMG
available from Danisco
as Dimodan-OK has a monoester level of > 90% and an iodine value between 60-
70. The OLEAN is
available from The Procter & Gamble Company, Cincinnati, OH.
AMENDED SHEET

CA 02306913 2000-04-12
15
Chemical COmt)OSltlOn of Polvelvcerni Fcrrra
Components Percentage
Monoglycerol monopalmitate 0.3
Diglycerol monopalmitate 24.8
Triglycerol monopalmitate 11.3
Tetraglycerol monopalmitate 4.9
Pentaglycerol monopalinitate,2.8
Monoglycerol
di almitate
Total Monopalinitate 44.1
Diesters 31.8
Triesters 9.6
Tetraesters 1.6
Pentaesters 0.4
Free Polyol 12.~
s'~id~Ei~'~~~3 ~~~~'~'

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Historique d'événement

Description Date
Inactive : CIB expirée 2016-01-01
Demande non rétablie avant l'échéance 2004-07-26
Inactive : Morte - Aucune rép. dem. par.30(2) Règles 2004-07-26
Réputée abandonnée - omission de répondre à un avis sur les taxes pour le maintien en état 2003-10-16
Inactive : Abandon. - Aucune rép dem par.30(2) Règles 2003-07-24
Inactive : Dem. de l'examinateur par.30(2) Règles 2003-01-24
Lettre envoyée 2000-12-28
Inactive : Transfert individuel 2000-11-10
Inactive : Page couverture publiée 2000-06-22
Inactive : CIB en 1re position 2000-06-14
Inactive : Lettre de courtoisie - Preuve 2000-06-13
Inactive : Acc. récept. de l'entrée phase nat. - RE 2000-06-06
Demande reçue - PCT 2000-06-05
Toutes les exigences pour l'examen - jugée conforme 2000-04-12
Exigences pour une requête d'examen - jugée conforme 2000-04-12
Demande publiée (accessible au public) 1999-04-29

Historique d'abandonnement

Date d'abandonnement Raison Date de rétablissement
2003-10-16

Taxes périodiques

Le dernier paiement a été reçu le 2002-09-30

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Historique des taxes

Type de taxes Anniversaire Échéance Date payée
Taxe nationale de base - générale 2000-04-12
Requête d'examen - générale 2000-04-12
TM (demande, 2e anniv.) - générale 02 2000-10-16 2000-04-12
Enregistrement d'un document 2000-11-10
TM (demande, 3e anniv.) - générale 03 2001-10-16 2001-10-01
TM (demande, 4e anniv.) - générale 04 2002-10-16 2002-09-30
Titulaires au dossier

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

Titulaires actuels au dossier
THE PROCTER & GAMBLE COMPANY
Titulaires antérieures au dossier
JADA DAWN REED
PAUL SEIDEN
STEPHEN PAUL ZIMMERMAN
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Description du
Document 
Date
(aaaa-mm-jj) 
Nombre de pages   Taille de l'image (Ko) 
Description 2000-04-12 15 693
Abrégé 2000-04-12 1 65
Revendications 2000-04-12 2 39
Page couverture 2000-06-22 1 74
Avis d'entree dans la phase nationale 2000-06-06 1 201
Courtoisie - Certificat d'enregistrement (document(s) connexe(s)) 2000-12-28 1 113
Courtoisie - Lettre d'abandon (R30(2)) 2003-10-02 1 166
Courtoisie - Lettre d'abandon (taxe de maintien en état) 2003-12-11 1 177
Correspondance 2000-06-07 1 14
PCT 2000-04-12 13 470