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Patent 1117358 Summary

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(12) Patent: (11) CA 1117358
(21) Application Number: 1117358
(54) English Title: EMULSIFIERS FOR BAKED GOODS
(54) French Title: EMULSIFIANTS POUR ALIMENTS CUITS
Status: Term Expired - Post Grant
Bibliographic Data
(51) International Patent Classification (IPC):
  • A21D 2/16 (2006.01)
(72) Inventors :
  • BUCK, DAN F. (United States of America)
  • SUGGS, JAMES L. (United States of America)
(73) Owners :
  • EASTMAN KODAK COMPANY
(71) Applicants :
  • EASTMAN KODAK COMPANY (United States of America)
(74) Agent: GOWLING WLG (CANADA) LLP
(74) Associate agent:
(45) Issued: 1982-02-02
(22) Filed Date: 1978-04-07
Availability of licence: N/A
Dedicated to the Public: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
802,091 (United States of America) 1977-05-31

Abstracts

English Abstract


EMULSIFIERS FOR BAKED GOODS
Abstract of the Disclosure
Disclosed are emulsifiers for baked goods prepared by melt
blending and powdering (1) a fatty acid monoglyceride and (2) at least
one compound selected from succinylated monoglyceride, diacetyl tartaric
acid esters of monoglyceride, ethoxylated monoglyceride, polyoxyethylene
sorbitan monostearate, and sodium and calcium stearoyl-2-lactylate.
Such emulsifiers may be added directly to dough from which the bakery
products are made without the use of inert carriers. Physical char-
acteristics of the bread, such as strength and softness, are enhanced.
- 1 -


Claims

Note: Claims are shown in the official language in which they were submitted.


We claim:
1. A water-dispersible powder adapted to be
incorporated into bread dough without the necessity of a
dispersing aid and which is adapted to enhance certain physical
properties of bread produced from said dough, the individual
particles of said powder consisting essentially of a
homogeneous blend of (1) about 25% to about 75% by weight of at
least one fatty acid monoglyceride in which the fatty acid
radical contains from 12 to 22 carbon atoms, and (2) about 75%
to about 25% by weight of diacetyl tartaric acid esters of
monoglyceride.
2. A water-dispersible powder adapted to be
incorporated into bread dough without the necessity of a
dispersing aid and which is adapted to enhance certain physical
properties of bread produced from said dough, said powder being
prepared by
(a) heating (1) about 25% to about 75% by weight of
at least one fatty acid monoglyceride in which
the fatty acid radical contains from 12 to 22
carbon atoms at least to its melting temperature,
and (2) about 75% to about 25% of diacetyl
tartaric acid esters of monoglyceride,
(b) forming a powder from said homogeneous blend, and
(c) cooling said powder to thereby solidity said
powder.
3. A water-dispersible powder adapted to be
14

incorporated into bread dough without the necessity of a
dispersing aid and which is adapted to enhance certain physical
properties of bread produced from said dough, said powder being
prepared by
(a) melt blending a mixture
(1) about 25% to about 75% by weight of at least
one fatty acid monoglyceride in which the
fatty acid radical contains from 12 to 22
carbon atoms and
(2) about 75% to about 25% of diacetyl tartaric
acid esters of monoglyceride,
thereby to form a molten homogeneous blend,
(b) forming beads of material from said homogeneous
blend of a size generally between about 150 and
about 300 microns, and
(c) cooling said beads of material to thereby
solidity said beads.
4. Method of preparing a water-dispersible powder
adapted to be incorporated into bread dough without the
necessity of a dispersing aid and which is adapted to enhance
certain physical properties of bread produced from said dough,
said method comprising the steps of
(a) heating (1) about 25% to about 75% by weight of
at least one fatty acid monoglyceride in which
the fatty acid radical contains from 12 to 22

carbon atoms at least to its melting temperature,
and (2) about 75% to about 25% of diacetyl
tartaric acid esters of monoglyceride,
(b) forming a powder from said homogeneous blend of a
particle size between about 150 and about 300
microns, and
(c) cooling said powder to thereby solidify said
powder.
5. Method of preparing a water-dispersible powder
adapted to be incorporated into bread dough without the
necessity of a dispersing aid and which is adapted to enhance
certain physical properties of bread produced from said dough,
said method comprising the steps of
(a) melt blending a mixture of
(1) about 25% to about 75% by weight of at least
one fatty acid monoglyceride in which the
fatty acid radical contains from 12 to 22
carbon atoms and
(2) about 75% to about 25% of diacetyl tartaric
acid esters of monoglyceride,
thereby to form a molten homogeneous blend,
(b) forming beads of material from said homogeneous
blend of a size generally between about 150 and
about 300 microns, and
(c) cooling said beads of material to thereby
solidify said beads.
16

Description

Note: Descriptions are shown in the official language in which they were submitted.


3~
. :
This invention relates generally to bakery products, and
more specifically this invention relates to dry powdered emul-
sifiers, useful in the dough from which bakery products are made,
- to enhance physlcal characteristics such as dough strength and
crumb softness.
Combination dough strengtheners and crumb softeners are
widely used in the baking industry. Such products of which we
are aware, however, depend on the addition of an inert diluent
or carrier for dispersibility in sponges and doughs. For exam-
ple, distilled monoglycerides are widely used as crumb softeners
in the baking industry. Compounds such as succinylated mono-
glycerides are used as strengtheners. Distilled monoglycerides,
however, must be combined with inert carriers such as water,
fat, flour, starch, milk solids, etc., to be dispersible in
sponges and doughs. The use of such inert carriers is undesir-
able for several obvious reasons. Handling of the potent, con-
centrated emulsifier is preferred to the dilu-ted emulsifier.
~lso, flavor is often affected by carriers.
Patents of interest in this field include U.S. Patent No.
3,370,9S8 which deals with succinylated monoglyceride and its
use in combination with other food emulsifiers in the presence
of fats or oils used in baking. This patent suggests slurrying
the succinylated monoglyceride in water in the presence of a
coemulsifier. U.S. Patents No. 3,379,535 and 3,592,660 deal
~- with conditioners for bread dough comprising monoglycerides and
water. U.S. Patent No. 3,851,066 relates to pro-tein enriched
bakery products containing emulsifiers such as ethoxylated
monoglycerides, ethoxylated esters of sorbitol, sorbitan and
isosorbides; salts of fatty acid-lactylic acid derivatives,
succinylated monoglycerides and ethoxylated fatty alcohols.
This patent states that the blend is usually, although not neces-
sarily, a plastic mass which is easily dispersed in dough or in
-2-
. .

the shortening. U.S. Patent No. 3,494,771 relates to adding to
emulsifiers a dispersion consisting essentially of (1) a con-
jointly solidified mixture of propylene glycol monostearate and
a monoglyceride, (2) stearyl lactylic acid, and (3) water. This
patent discloses that the components may be melted together to
form a molten blend and then spray chilling the molten blend to
form a beadlet product. Another patent of interest is U.S. Patent
~o. 2,938,027 which relates to esters of acetyl tartaric and citric
acids. Other patents exemplifying the state of the art include
~.S. Patent Nos. 3,843,817; 3,388,999; 2,208,857; 3,914,452;
3,145,107; 3,145,108 and 3,145,109.
It is an object of this invention to provide powdered
emulsifiers prepared by melt blending certain dough strengtheners
and crumb softeners which powder is readily dispersible in bakery
dough or sponge.
It is another object of this invention to provide dry
emulsifier powders which improve dough conditioning, retard the
.,
rate of crumb firming, and enhance the physical appearance of
~` finished bakery goods.
It is still another object of this invention to provide
dry powdered emulsifiers comprising a homogeneous mixture of a
strengthener and a softener which is dispersible in dough without
~- the use of dispersing aids.
`~ Other objects will appear hereinafter.
Thus, in accordance with the present teachings, a water-
dispersible powder which is adapted to be incorporated into bread
dough without the necessity of a dispersing aid and which is
' adapted to enhance certain physical proper-ties of bread produced -~
from such dough, the individual particles of the powder consist
essentially of a homogeneous blend of (1) about 25% to about 75%
by weight of at least one fatty acid monoglyceride in which the
fatty acid radical contains from 12 to 22 carbon atoms, and (2)
'
~ -3-

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about 'i5~ to about 25% by weight of dlacetyl tartaric acid
esters of monoglyceride.
The present invention also provides a water-dispersible
~ powder which is adapted to be incorporated into bread dough
: without the necessity of a dispersing aid and which is adapted
to enhance certain physical properties of bread produced from
said dough, the powder being prepared by
(a~ heating (1) about 25% to about 75% by weight of at least
one fatty acid monoglyceride in which the fatty acid
- 10 radical contains from 12 to 22 carbon atoms at least to
its melting temperature, and (2~ about 75% to about
25% of diacetyl tartaric acid esters of monoglyceride at
;.
~`. .
,`
.
.~ 30
`:
. -3a-

3~3
least to the melting temperature to form a homcgeneous moleen
mass,
(b) forming a powder from the homogeneous molten mass of a particle
~ize generally between aboutl50 and about 300 microns, and
(c) cooling the powder to thereby solidify the powder.
The emulsifier is particularly useful in breads and buns, but
is also very useful in other bakery products such as pizza, cookies and
doughnut 8 .
The preferred blends comprise distilled monoglyceride and
succinylated monoglyceride; distilled monoglyceride and diacetyl tartaric
acid esters of monoglyceride; or ternary blends of distilled mono-
glycerides, succinylated monoglycerides, and diacetyl ~artaric acid
esters of monoglyceride. In the ternary blend, the proportions indicated
above still apply, and the succinylated monoglyceride and diacetyl
tartaric acid esters of monoglyceride may suitably be present in
approximately equal amounts.
'~onoglycerides" comprise 9 cl~ss of monoestess of mixed mono-
esters and die~ters of glycerine and fatty acids. Typically, monoglyceride
compositions ~uitable for use in accorda~ce with the invention are those
having an iodine value within the range of 1 to about 70. These mono-
glycerides are usually prepared by conventional methods of glycerolysis
of edible fa~s and oilE; that is, by reacting glycerine with a fatty acid,
glyceride, or other fatty acid ester or by directly esterifying glycerine
with a fatty acid having from about 12 to about 22 carbon atomæ. Typical
of such glycerides are glyceryl monooleate, glyceryl monostearate, and
~; glyceryl monopalmitace. Monoglycerides prepared by conventional means
from hydrogenated palm oil or hydrogenated vegetable oil, ~uch as
Myverol* 18-04 and Myverol* 18-06 di~tilled monoglyceride~ (products ~f
Eastman Chemical Products, Inc.), respectively, are preferred.
"Succinylated monoglycerides" are succinyl half-esters formed ~-
by reacting one mol of succinic acid with one ~ol of the above-described
monoglyceride6. These material~ ~re usually prepared by reacting succinic
. ':
*Trademarks
-- 4 --

3~
anhydride with a monoacylated glyceride as further described in U.S.
Patent 3,293,272.
Diacetyl tartaric acid esters of monoglyceride are well known
in the art. For example, see U.S. Patent No. 2,236,516. Certain of
these esters are in widespread commercial use. They are prepared, as
described in this patent, by reaction, for instance, of a higher fatty
acid mono- and/or di-glyceride with diacetyl tartaric acid anhydride or
acetyl citric acid anhydride.
Diacetyl tartaric acid esters of monoglycerides are available
commercially, for example, as Myvatem* dispersing agent, marketed by
Eastman Chemical Products, Inc.
"Ethoxylated monoglycerides" are reaction products of the
above-described monoglycerides with ethylene oxide. Typically, these
condensation products contain from 10 to 95 weight percent of ethylene
oxide based on 100 parts by weight of ethoxylated monoglyceride. More
commonly, these additives will contain from 25 to 80 weight percent of
ethylene oxide and 15 to 25 moles of ethylene oxide per mol of mono-
glyceride Procedures for making these materials are further described
~` in U.S. Patent 3,433,645.
Polyoxyethylene sorbitan monostearate is an ethoxylated fatty
` acid ester of sorbitan. Polyoxyethylene derivatives of the sorbitan
.:.
; fatty acid esters may be prepared by reacting sorbitan with ethylene
oxide prior to esterification, or by preparing a partial sorbitan fatty
~` acid ester first and thereafter reacting the fatty acid ester with
ethylene oxide. The preparation of polyoxyethylene fatty acid esters of
sorbitan is further described in U.S. Patent 2,380,166. This compound
is available commercially under the trademark Polysorbate 60, a product
~ ;:
marketed by Imperial Chemical Industries Limited.
~` Surprisingly, it has been found that when powders are made from
melt blends of these materials, the powders comprising a strengthener and
a softener can be dispersed in sponge or brew easily without the aid of a
dispersing aid. h~hen the powders are prepared separately and mixed,
*Tr adema rk
- 5 -
' ~

3~
however, such difficulty is encountered that dispersing aids are
required. Indications are that powders prepaxed from melt blends
have unexpected properties. For example, melting points of
powders made from melt blends are not predictable from the melting
points of the components as indicated in the table below.
Melting Point, C.
SMG Succinylated Monoglyceride (SMG) 57
; MYVEROL 18-04 Distilled Monoglyceride (18-04) 62
MYVEROL 18-06 Distilled Monoglyceride (18-06) 64
Ethoxylated Monoglyceride (EMG) 28
MYVATEM diacetyl tartaric acid ester of 30
monoglyceride
Polyoxyethylene sorbitan monostearate At 25C.-Yellow Oily Li~uid
Sodium stearoyl-2-lactylate 41
SMG/18-04 (2:1) 49
90~ SMG/18-0~ (2:1) 48
10% MYVATEM
,! SMG/18-04 (1:1) 53
; SMG/18-04 (1:3) 55
EMG/18-06 (1:3) 58
; MYVATEM/18-04 (1:3) 57
Polyoxyethylene sorbitan monostearate/18-04 (1:3) 58
Sodium stearoyl-2-lactylate/18-04 (3:1) 47
The homogeneous powder according to this invention is
prepared by melt blending the monoglyceride with the other
selected ingredient or ingredients until a homogeneous mass is
obtained and then forming a powder from the mass. Melt blending
may be accomplished by individually maintaining or raising the
temperatures of the compounds to a point above their respective
melting temperatures so each is a molten mass and then thoroughly
.~ .
- - blending, or by mixing the ingredients at room temperature and
then raising the temperature of the mixture at least to the
melting point of the highest-to-melt ingredient followed by
thoroughly blending to form a homogeneous mass. Preferably, melt
blending is accomplished at a temperature of between about 80C.
and 120~C~ Powdering may be accomplished by conYentional means
such as, for example, spray chilling, freezing and pulverizing,
or by any other means known in the art. Laboratory experiments
-6-

3~
indicate that the quality o~ product produced on small scale
. by powdering in a blender using dry ice is quite satisfactory.
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Such powdering is accomplished by first heating a mixture of the selected
ingredients until a molten or liquified mass is formed, and then rapidly
stirring until the mass is homogenized. For example, 100 grams of
molten ml~ture in a 250 ml. beaker may be stirred until the mixture is
~ found to be homogenized. Tne mixture may then be poured out and cooled
'.
until solidified, typically for about 24 hours at room temperature. The
-` solid may then be powdered in a high speed stirring device such as a
Waring* Blendor using dry ice. The dry ice is subsequently evaporated ;
and the powder residue sieved to an approximate size of 50-300 microns.
The powder is white, free flowing, and is readily incorporated into a
baking sponge or brew.
The powder produced as described above is found to be especially
;: :
useful in the production of bread. The powder may be added to either
the "sponge" or the "brew". The powder is preferably added in amounts
, of between about 3 oz. and about 12 oz. per lOO lbs. of flour.
The sponge-dough method of bread production involves the mixing
of part of the ingredients to form a sponge which is then fermented for
~; approximately four hours. The sponge is then mixed with the remaining
ingredients until the desired gluten structure is obtained. After the
second mixing period and a suitable rest period, the dough is divided
*, for further processing. The sponge-dough method produces bread which
has better volume and flavor than bread produced with the continuous-mix
:,~ method while the latter method is notable in that it produces bread with
very fine grain at a lower manufacturing cost.
: TYPICAL BREAD FORMULA - (SPONGE-DOUGH PROCESS)
Percent of Flour
` Sponge:
Flour 65.0
Water 42.0
Yeast 2.0
Yeast food 0.5
Mix time: 4.5 minutes.
Ferment time: ~.5 hours at 87F. and 80~ humidity.
*Trademark ~ ;
7 ~
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. .~ ..

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,
Dough (includes the fermented sponge):
Flour 35.0
Water 27.0
Sugar 6.0
Salt 2.3
Milk powder 4.0
Shortening 3.0
- Dough conditioner, test level.
Mix time: 9.5 minutes.
Floor time: 30 minutes.
Proof time: 1 hour at 98F. and 95% humidity.
Bake time: 20 minutes at 450F.
TYPICAL BREAD FORMULA - (CONTINUOUS MIX PROCESS)
~ Brew _ Percent of FlourWeight (Grams)
; 10 Water 67.0 3484.0
Sugar 8.0 416.0
Salt 2.25 117.0 -
Nonfat dry milk 3.00 156.0
Yeast food 0.50 26.0
Calcium phosphate (dibasic) 0.lO 5.2
Calcium propionate 0.10 5.2
~east 2.50 130.0
Brew fermented for 2-1/2 hours at 86F
;~, ~.
Dough or Premix
; ~
Flour 100.0 5200.0
Brew - 4235.0
' Shortening blend 3.0 156.0
Lard (148.0)
Flakes ( 8.0)
` Standard oxidation solution 52.0 ml.
Emulsifier As needed
Flour, brew, shortening blend, and oxidation solution are mixed
~ together in a Hobart* Mixer for 45 seconds on low speed and 15
`~ seconds on #2 speed. Premix is transferred to loading cylinder.
Standard Ox dant Solution
Water (distilled) 1000 ml.
` Iodate 1.250 gm.
Bromate 5.000 gm.
BREAD SOFT~ESS TEST
`~ Bread softness data are obtained with a Baker Compressimeter*,
available from Wallace & Tiernan of Belleville, New Jersey. Ten slices
of bread are selected from one loaf and the amount of stress in grams
required to exert a stain (or compression) of 3 mm. in a 1 cm. slice is
determined. The "compressimeter value" is the arithmetical average of
the ten slices of one loaf taken at the end of four days' storage. A
*Trademarks
- 8 -
. ~
,

~'73~
lower mean compressimeter value indicates softer bread and a higher
value indicates firmer bread.
Bread volume for each test batch is determined by conventional
methods using a rapeseed displacement technique. Volume determinations
are made 2~ hours after baking. Bread volumes are statistical means of
four loaves. Proofed doughs are dropped 9-3/4 inches against a solid
surface. Bread is packaged in l-mil. polyethylene bags and stored at
room temperature.
l`he following examples are included for a better understanding
of the invention. In the examples, Tandem* 22H dough strengthener/crumb
'.~
~ softener is 1 part polyoxyethylene sorbitan monostearate blended with 3
,~ parts of a 50:50 mixture of hydrated mono- and di-glyceride, and "SMG"
is succinylated monoglyceride which contains about 10~ unreacted mono-
; glycerides. Flour X and Flour Y are brands of flour. The typical
sponge-dough formula described above is used, unless otherwise indicated.
EXAMPLE 1 (Control)
~,` Bread is prepared using no conditioners or softeners. The
following results are obtained:
Bread Volume
Undropped Volume, ml. Dropped Volume, ml. Fourth Day Softness
~ 2,381 1,844 18.2
`; EXAMPLE 2 ~Control)
. .
~ Eight ounces of powdered distilled monoglyceride is added to ~ '
- a formula as the softener. No dough strengthening effects are observed
and the rate oE crumb staling is not retarded. In other words, the
powdered monoglyceride does not hydrate and become an active ingredient
of the bread dough. A strengthener/softener effect is observed when
- the monoglyceride powder is melted in fat and used in the same formula.
Use of a mixture of monoglyceride powder with succinylated powder is
similar in that the monoglyceride powder is inactive. However, when
melt blended to a homogeneous mass, powdered and chilled, the powder so
formed is found to result in giving bakery products both strength and
softness.
*Trademark
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E ~AMPLE 21
To a 250 ml. beaker, 75 grams of Myverol 18-04 monogly-
ceride and 25 grams of Myvatem dispersing agent are added. The
mixture is heated to 80C. and stirred for one minute. The
molten mixture is then poured out and cooled for 24 hours. The
resulting solid is powdered in a Waring Blender using dry ice.
The dry ice evaporates and the powder is then sieved to an
approximate size of 150-300 microns and is ready for use as a
strengthener/softener. Bread is baked using the typical sponge-
dough formula. The following results are obtained with thebread using the prepared powder added to the sponge.
Bread Volume
; Undropped Voiurne, ml. Dropped Volume, ml. Fourth Day Softness
2,425 2,012 8.7
E XAMPLE 22
To a 250 ml. beaker, 90 grams of succinylated monogly-
ceride/distilled monoglyceride at a ratio of 2 :1 and 10 grams
of diacetyl tartaric acid ester of monoglyceride are added. A
powdered emulsifier is prepared frorn this mixture by the
procedure described in Example 21. Bread is prepared with the
powder, and the following results are obtained.
Bread Volume
Undropped Volume, ml. Dropped Volume, ml. Fourth Day Softness
- 2,431 2,162 11.0
` _XAMPLE 23
To a 250 ml. beaker, 75 grams of Myverol 18-04 mono~
glyceride and 25 grams of ethoxylated monoglyceride are added.
A powdered emulsifier is prepared from this mixture by the
procedure described in Example 21. Bread is prepared with the
powder, and the following results are obtained.
: 30 Bread Volume
Undropped ~olume, ml. Drop~ed Volume,~ Fourth Day Softness
2,387 2,075 9.2
2 -

L'73~i~
.
EXAMPLE 24
.,
To a 250 ml. beaker, 75 grams of Myverol 18-04 monogly-
s ceride and 25 grams of polyoxyethylene sorbitan monostearate
(Polysorbate ~0) are added. A powdered emulsifier is prepared
from this mixture by the procedure described in Example 21.
Bread is prepared with the powder, and the following results are
obtained.
Bread Volume
Undropped Volume, ml. Dropped Volume, ml. Fourth Day Softness
: 2,456 2,000 ~.7
EXAMPLE 25
Example 24 is repeated using sodium stearoyl-2-lactylate/ -
18-04 in a ratio of 3:1. Bread properties using 8 oz. of this
composition per 100 lb. flour are as follows.
Bread Volume
Undropped Volume, ml. Dropped Volume, ml. Fourth Day Softness
2425 1988 7.4
It will be apparent from the above examples that the
desirable characteristics of strength and softness are obtained
using the claimed powder. The examples illustrate that a
relatively low concentration of the powder is required. Control
Example 2 illustrates the necessity of melt blending and powdering
the mass.
Unless otherwise specified, all percentages, ratios,
parts, etc. are by weight.
The invention has been described in detail with parti-
cular reference to certain preferred embodiments thereof, but
it will be understood that variations and modifications can be
effected within the spirit and scope of the invention.
'.`.:
~ -13-

Representative Drawing

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Administrative Status

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Event History

Description Date
Inactive: Expired (old Act Patent) latest possible expiry date 1999-02-02
Grant by Issuance 1982-02-02

Abandonment History

There is no abandonment history.

Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
EASTMAN KODAK COMPANY
Past Owners on Record
DAN F. BUCK
JAMES L. SUGGS
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Claims 1994-02-03 3 89
Abstract 1994-02-03 1 18
Cover Page 1994-02-03 1 16
Drawings 1994-02-03 1 12
Descriptions 1994-02-03 14 465