Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Basic ingredient is starch based batter – dough product – etc.
Reexamination Certificate
2003-01-13
2004-11-16
Tran, Lien (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Basic ingredient is starch based batter, dough product, etc.
C426S553000, C426S601000, C516S029000, C516S073000, C560S180000
Reexamination Certificate
active
06818244
ABSTRACT:
FIELD OF THE INVENTION
The invention relates to a mixture comprising diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids. Diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids are generally known as baking ingredients for baked products. More particularly, they are generally known for yeast-leavened products such as bread (especially white bread), tin bread, rolls, hard rolls, German crispy rolls, buns, rusks etc. These esters are able to improve the products in various respects as good leavening expressed as specific volume; even pores and acceptable crustiness. They are also known to improve the properties of dough such as its stability and rheology and are therefore often referred to as dough conditioners. The esters are further used in baking aids and in improved flour. The ED number of mixtures of diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids is E472e (DATEM).
BACKGROUND OF THE INVENTION
The art has long described mixtures comprising diacetyl tartaric acid esters of mono-and diglycerides based on C12 to C22 fatty acids and their preparation. U.S. Pat. No. 2,236,516 (Frank J. Cahn et al) is an early patent specification disclosing products obtained by reacting diacetyl tartaric acid with glyceryl monostearate. U.S. Pat. No. 2,689,797 (Morris H. Joffe) discloses improvements in bread obtained by the incorporation of diacetyl tartaric esters of unsaturated and partially saturated mono and/or partial glycerides. U.S. Pat. No. 2,938,027 (Martell M. Gladstone) discloses the reaction between mixtures of acetylated anhydrides of food acids such as e.g. tartaric acid containing 4 to 95% of diacetylated tartaric acid and e.g. free acetic anhydride with partial glycerides of fatty acids to obtain improved products. U.S. Pat. No. 3,443,969 (Nobuo Nakejima et al) discloses diacetyltartaric esters of purified (molecular distilled) monoglycerides of vegetable oils. GB-A-1,220,488 (Aktieselskabet Grindstedvaerket) discloses the preparation of an emulsifier obtained by reacting, e.g., distilled glycerol monostearate with diacetyl tartaric anhydride in certain molar ratios followed by prolonged heating to 135-190° C. as to obtain by polymerization a satisfactory oil-in-water emulsifier of higher molecular weight, which apparently contains polymeric esters due to splitting off acetic acid and water. GB-A-1,344,518 (Dynamit Nobel A.G.) discloses solid acetyltartaric esters obtained by reacting at least partially acetylated tartaric acid with partial glycerides containing 55-65% monoglyceride and an iodine value below 5 which contain per mole of partial glyceride 0.91-1.8 mole tartaric acid residues and 1.8-3.4 mole acetic acid residues. These esters are free flowing powders whereas the traditional esters have a waxy or honey-like consistency. This difference in physical properties is due to the fact that these powders contain appreciable quantities of say about 0.3 mol % of glyceride esters of monoacetyl tartaric residues and/or even non-acetylated tartaric acid residues. Conventional acetylated tartaric acid esters of mono- and/or diglycerides are mono- and/or diglyceride esters of (almost) pure diacetylated tartaric acid (anhydride). The products according to the present invention are also very low in esters of monoacetylated tartaric acid (anhydride).
Although the current diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids are valuable products they are often somewhat defective as to:
1 specific volume of the baked product obtained;
2. stability as to leavening under the influence of yeast; and/or
3. stability properties of the dough prepared.
SUMMARY AND OBJECTS OF THE INVENTION
It is an object of the present invention to provide a mixture comprising diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids yielding a performance which is improved in at least one of the properties mentioned above. Moreover, the present invention also provides a process for the preparation of the aforementioned mixture(s) of the diacetyl tartaric acid esters of mono- and diglycerides based on C12 to C22 fatty acids by reaction of diacetylated tartaric acid anhydride and mono- and diglycerides C12 to C22 fatty acids at a relatively low temperature combined with a short reaction time, which is more economical than most of the current processes.
BRIEF DESCRIPTION OF THE DRAWING
The FIGURE is a plot from a NMR.
DETAILED DESCRIPTION OF THE INVENTION
The invention therefore provides in a first embodiment a mixture comprising diacetyl tartaric acid esters on mono- and diglycerides based on C12 to C22 fatty acids. The mixture comprises diacetyl tartaric acid glycerol monoesters containing: (A) one fatty acid group, one diacetylated tartaric acid monoester group and a free hydroxyl group and (B) one fatty acid group and two diacetylated tartaric acid monoester groups, wherein
1. the concentration of (A) above in the total mixture, obtained by dividing the molar amount of (A) by the sum of the molar amounts of all components in the mixture and multiplying by 100, is at least 45%, preferably at least 50%, and
2. the fraction obtained by dividing the molar amount of (A) above by the combined molar amounts of (A) and (B) taken together is at least 0.70, preferably at least 0.72 and in which the molar amounts are determined by the NMR method herein described.
These NMR measurements were performed at 50° C. in CDCl
3
on a Jeol JNMR EX400 FT-NMR spectrometer operating at 400 MHz for
1
H. Typically, 20 mg of sample was dissolved in 0.5 ml of solvent. To prevent overlap of the H
2
O resonance with resonances of the product, the pH of the sample was lowered to approximately 4 by adding acetic acid. The pulse delay (PD) time had to be chosen such that full relaxation of the signals takes place (PD>5T
1
).
The contents of (A) and (B) (mol %) can be calculated from the integral values:
P:&dgr;=4.0 ppm to 4.5 ppm
Q:&dgr;=4.7 ppm to 4.9 ppm
R:&dgr;=5.0 ppm to 5.2 ppm
S:&dgr;=5.2 ppm to 5.4 ppm,
e.g from the graph as illustrated in
FIG. 1
by the formulae:
(
A
)
=
[
P
-
(
4
Q
+
2
R
+
4
S
)
5
P
′
+
Q
+
R
+
S
]
·
100
[
mol
%
]
(
B
)
=
[
S
P
′
+
Q
+
R
+
S
]
·
100
[
mol
%
]
P
′
=
P
-
(
4
Q
+
2
R
+
4
S
)
5
N.B. All these integral values have to be corrected for glycerol mono-, di- and triesters of C14 to C18 fatty acids, if any, first.
Or, in words, in the formulae:
(A) equals a fraction of which the numerator is 100 times (P minus the sum of 4 times Q plus twice R plus 4 times S) divided by 5 and the denominator is (the sum of P′ plus Q plus R plus S in which P′ is P minus the sum of 4 times Q plus twice R plus four times S) divided by 5; and
(B) equals a fraction of which the numerator is S multiplied by 100 and the denominator is (the sum of P′ plus Q plus R plus S in which P′ is P minus the sum of 4 times Q plus twice R plus four times S) divided by 5.
In case a product is at stake which contains fatty acid triglyceride as an extender as may be the case the NMR data measured need to be corrected for this percentage of triglyceride. Therefore the amount of triglyceride, if present, has to be determined and the method disclosed by P. Quinlan and H. J. Weiser Jr in JAOCS 35, 325-6 (1958) was found suitable. We used a modified method employing toluene (technical grade) instead of benzene and silicagel 60, no 1.07734.110 cx Merck, 20-230 mesh which activated with 9 wt % of water instead of 5% of water. The NMR signals of the specific fatty acid triglycerides which are needed are known from Sadtler Index of 1 H-NMR spectra (Sadtler Research Laboratories (Biorad) Philadelphia, Pa., USA).
In case a product is at stake in which mono- and/or diglycerides are used as an extender, the analysis of the percentage diglycerides was carried out by proton NMR applying the same method as used for the deter
Coenders Peter Johannes
Gombert Johannes Durk
Roest Martin Robert
Stegeman Pieter Hendrik Paul
Van Schie Bartholomeous Jozef
Fitch Even Tabin & Flannery
Quest International B.V.
Tran Lien
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