CA2039818A1 - Liquid defoaming agent for food and method of use thereof - Google Patents

Liquid defoaming agent for food and method of use thereof

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Publication number
CA2039818A1
CA2039818A1 CA002039818A CA2039818A CA2039818A1 CA 2039818 A1 CA2039818 A1 CA 2039818A1 CA 002039818 A CA002039818 A CA 002039818A CA 2039818 A CA2039818 A CA 2039818A CA 2039818 A1 CA2039818 A1 CA 2039818A1
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Prior art keywords
defoaming agent
liquid defoaming
acid diglyceride
test
liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002039818A
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French (fr)
Inventor
Seishi Takenawa
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Fujisawa Pharmaceutical Co Ltd
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Fujisawa Pharmaceutical Co Ltd
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Publication of CA2039818A1 publication Critical patent/CA2039818A1/en
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Abstract

ABSTRACT OF THE DISCLOSURE
The liquid defoaming agent for food of the present invention contains low fatty acid diglyceride as the essential component thereof and is made to contain lecithin and/or inorganic carrier, and the defoaming agent can exhibit excellent defoaming effect even at ambient temperature as well as during heating, in the process of producing various foodstuffs.

Description

2~818 LIQUID DEFOAMING AGENT FOR FOOD AND METHOD OF USE THEREOF

BACKGROUND OF THE INVENTION
1. Field of the Invention The present invention relates to a liquid defoaming agent for food which is to be added in order to suppress foam generated during the process of producing bean curd and soybean milk, the process of producing proce5sed milk products, the process of producing a processed tea product, and other processes of producing various foods. The present~invention relates to a useful method for uslng a liquid defoaming agent for food.
2. Description of the Prior Art In the process of producing or processing various foods, there are contained those generating foam, and the foam generation causes distinct deterioration of productivity and quality of products.
In the general process of producing bean curd having traditionally been carried out, for example, soy bean is immersed in water and finely milled into "go", which is then heated in an iron pot to remove bean-curd refuse. The foaming during the heating or the foaming of the soybean milk in the bean-curd refuse removed from the heated "go", induces various disadvantages eg. boiling-liquid overflow from the iron pot.

.
' ~~In order to suppress such foaming, therefore, various types of defoaming agents have been developed.
. " ' 1 ~ '.
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I

2039~1 8 Japanese Patent Publication No. 53137-87 discloses a defoaming agent for food comprising one type of low fatty acid diglyceride or a mixture of two types thereof. Japanese Patent Laid-open No. 83559/1985 discloses a defoaming agent for bean curd, with essential components thereof comprising polyrecinoleic acid esters, soybean phospholipid, salts such as calcium carbonate, calcium phosphate, etc., and fats and oils from animals and vegetables. Furthermore, Japanese Patent Laid-open No. 22914/1976 discloses a defoaming agent in which three components, ie. oils from animals and vegetables, phospholipid, calcium carbonate compounds, are mixed.
In recent years, there has been developed and widely propagated a method comprising adding water into water-absorbing soybean for milling, filtering the milled soy bean at ambient temperature, separating soybean milk from bean-curd refuse to heat the soybean milk. Even in the method, foam is generated during the separation process or during the handling process after the separation, for example, during the transportation process through pipelines, causing a variety of disadvantages eg~
problems such as promotion of pump's wear and tear due to the intruslon of air bubble into pipes transporting soybean milk to an iron pot, and the overflow of bubble from a storage tank of soybean milk. Most of conventional defoaming agents have been developed for the prLncipal subje~t to suppress foaming at the !

, 203~818 heating stage, and any foaming agent can exhibit such effect at a certain degree, as long as it may be soluble at high-temperature condition. However, in the modified process in which bean-curd refuse is separated at ambient temperature described hereinabove, conventional defoaming agents cannot sufficiently be dissolved, so that little defoaming effect may be e~pected therefrom. Thus, there has been desired a defoaming agent to exert excellent defoaming effect even under the condition at room temperature.
Such defoaming agent is required not only in the process of producing bean curd and soybean milk but also in terms of suppressing foaming during the various processes illustrated hereinbelow, and there has been desired a defoaming agent exhibiting excellent defoaming effect in various fields of food production;
(a) process of producing ice-mix powder employing cow's milk and sheep's milk, whole milk powder, skimmilk powder, modified milk powder, casein, etc; and process of producing the processed foods employing them, eg. ice cream, ice milk, lactoice, ice candy, pudding, coffee whitener, yogurt drinks:
(b) process of processing coffee drinks, instant coffee and coffee powder; and process of producing the processed foods employing them:
(c) pFocess of producing cacao beans, e,c~. process of producing cocoa powder and cocoa drinks:
(d) process of producing green teas (middle-grade green tea, 2~3~8~8 powdered tea), fermented teas (tea, uron tea, etc.): and process of producing processed foods employing their powder and extracted liquid.
(e) process of compounding binding agents (filling agents) during the production of ham and sausage:
(f) process of preparing bean paste using adzuki beans:
(g) process of producing boiled beans using soybean, kidney bean, horse bean, etc.:
(h) other processes of producing various foods (process of producing foodstuffs employing potatoes, process of producing Worcester sauce, process of producing jellies, etc.).

OBJECT OF THE INVENTION
The present invention has been achieved under such circumstances, and the object of the invention is to provide a li~uid defoaming agent for food, capable of exhibiting excellent defoaming effect at room temperature as well as during heating in the process of producing various foods and the process of processing them. The other object of the present invention is to provide a useful method of using such liquid defoaming agent as described above.
, :

SUMMARY OF THE INVENTION
The present invention with the objects having been achieved ~ 4 ,~' .. .
:.'' , ~._ 2~3~
`s a liquid defoaming agent summarized in the respect such that inorganic carrier is contained in addition to low fatty acid diglyceride and leci-thin. The liquid defoaming agent described above is undoubtedly useful in suppressing the foam generated during the process of producing bean curd and soybean milk, and is also useful as the defoaming agen-t for other foodstuffs.
Depending on the subjective foods (for example, individual foods from (a) to (h) hereinabove described), a two-component system comprising low fatty acid diglyceride and lecithin, or one comprising low fatty acid diglyceride and inorganic carrier, may also exhibit defoaming effect. When these defoaming agents are used, an appropriate amount of the agents may be added during an appropriate periodical point in the process of producing the individual foods described above (or prior to the blending process).

DETAILED DESCRIPTION OF THE INVENTION
The present inventors have investigated a defoaming agent capable of exhibiting excellen-t defoaming effect even at ambient temperature in the process of producing various foodstuffs. As a result, the inventors have found that a combination of three components, ie. (A) low fatty acid diglyceride, (B) lecithin and (C) inorganic carrier, can exhibit excellent defoaming effect at ambient temperature, and they have achieved the invention.
The present invention is based on the combination of the 2~39~ ~
three components from (A) to (C), but it has been found that the use of the two components, such as a combination of 1. low fatty acid diglyceride and lecithin and a combination of 2. low fatty acid diglyceride and inorganic carrier, is also effective on some kinds of foodstuffs. No component of the three can e~hibit defoaming effect when used singly, but it is surprising that the combination of low fatty acid diglyceride, lecithin and/or inorganic carrier exhibits the defoaming effect through the synergistic effect of the two or three components.
The defoaming agent of the present invention is provided in the liquid form by the combined use of the three components (or two components), and such liquid defoaming agent easily can be mixed with soybean milk and "go" at room temperature, and is therefore easy to be handled, thereby exerting e~cellent defoaming effect at ambient temperature. The defoaming agent of the present invention not only exhibits such effect at room temperature as described above, but also can be used at high temperature, so the agent exhibits superb defoaming ePfect, for example, in a traditional process where bean-curd refuse is separated after heating.
Low fatty acid diglyceride to be used in the present invention is in the liquid form, which is obtained by subjecting a low fatty acid having carbon atoms from 6 to 12, such as caproic acid, caprylic acid, capric acld, lauric acid, etc. along : :

- .

2~81~
~ith glycerin, to esterification, and the single type or two or more types of the low fatty acid diglyceride can be used in combination. Appropriately, the content of low fatty acid diglyceride in the defoaming agent of the present invention is approximately 5 to 96 % by weight (in the case of using edible oils and additives described hereinbelow, the ratio is e~pressed as a ratio to the entire amount of the defoaming agents including them; it is the same hereinafter.) In accordance with the present invention, the use of such liquid components enables to form thorough suspension even in the case of using the inorganic carrier described hereinafter, which has contributed the achievement of the object of the present invention.
As the lecithin to be used in the present invention, there may be used synthesized lecithin besides natural lecithin such as soybean lecithin and egg-yolk lecithin. It is appropriate that the content of lecithin is about 2 - 70 % by weight. The aforementioned lecithin of the present invention can be generally available in liquid, but the lecithin in solid may be also usable.
As the lnorganic carrier to be used in the present invention, there may be lllustrated calcium carbonate, calcium hydroxide, magnesium carbonate, tertiary calcium phosphate; they may be used singly or in combination. Of the inorganic carriers, the salt of alkaline earth metal carbonate is preferable; calcium .~
~ .
- . . . .

2~3~
carbonate and magnesium carbonate are more preferable.
Appropriately, the content of such inorganic carrier is about 2 to 25 % by weight.
The defoaming agent of the present inven-tion can be used in combination with edible oils as a diluent, whereby the agent can be made into a defoaming agent excellent in handling. The edible oils to be used in the present invention may be adequately in liquid and edible, including for example veaetable oils such as soybean oi.l, soybean shirasimeyu, rape seed oil, coconut oil, palm oil, rice powder oil, etc., animal oils such as whale oil, sardine oil, etc.
For the purpose of viscosity adjustment, various additives may be contained in the defoaming agent of the present invention, other than the individual components. As such additives, fatty acid monoglyceride, sucrose fatty acid ester, polyglycerine fatty acid ester, hardened oil, etc. may be included. Of the additives illustrated, sucrose fatty acid ester is for lowering the viscosity and the others are for increasing the viscosity.
As is demonstrated in the gist described above, the defoaming agent of the present invention oan be used suitably when the various individual foodstuffs from (a) to (h) are ~produced, with no limitation of the use thereof to the case of producing bean curd and soybean milk, and two components consisting of low fatty acid diglyceride and lecithin or .

' ~ 2~3~ 8 .norganic carrier may generally be enough; but as the defoaming agent to be used in the process of producing bean curd and soybean milk, there may be used the one containing the three components described above.
There is no limitation concerning the time when the defoaming agent of the present invention is added, and the defoaming agent can be used at a time appropriately selected, such as those when food materials are dissolved or agitated or at the final stage as,merchandise (for example at packaging). In the process of producing bean curd, for example, the time may be any stage of 1. adding water into water-absorbing soybean and milling the soybean at room temperature, 2. handling the milled "go" at ambient temperature to separate bean-curd refuse, 3. the stage of soybean milk after the separation of soybean milk from bean-curd refuse, or 4. the stage of heating "go". There is no limitation on the added ratio of the deEoaming agent oE the present invention, which is about 0.001 to 0.1 % by weight.
When the defoaming agent of the present inventlon is used, the agent is appropriately dispersed even by employing an appropriate mixture of each of the components and the additives described above, but it is a preferable embodiment to use the defoaming agent formulated through addition of surfactants such as emulsifier or addition of emulslfying process, so as to be readily dispersible in water.
There is no limitation~on the procedure for preparing the ..
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2 ~
defoaming agent of the present invention, and the following procedure is just illustrated. Given amounts of a diluent such as soybean oil, etc. and caprylic acid diglyceride are dissolved and agitated at an appropriate temperature (for example at about 60 C), to which is then added a viscosity adjuster such as glycerine fatty acid ester, sucrose fatty acid ester, etc.
followed by subsequent mixing of lecithin, and then an inorganic carrier is added and mixed at an appropriate temperature (for example at about 55 ), followed by cooling down to about 30 C
to prepare a product.
There are exemplified testing examples hereinbelow.
Test example 1 Water (350 ml) was added to 200g of water-absorbing soybeans, which were then milled with a mixer to separate soybean milk from bean-curd refuse. The soybean milk (300 ml) separated was placed in a 500-ml beaker, to which was simultaneously added each of the components shown in Table 1 as a defoaming agent (but No.1 is the case without addition), which was then stirred with a handheld mixer for two minutes to foam the soybean milk. After left to stand for one minute, the height of the foam was measured to obtain the results as shown in Table 2.
: Table 1 Test No. Defoaming agent Added amount (~) _ ._ i 1 No addltion . _ - - .
l .
. 10:
.

.

~, ~ ~ 3 ~
2 Caprylic acid diglyceride 0.3 . 3 Soybean lecithin (60% product) 0.3 .
. Calcium carbonate 0.3 Caprylic acid dlglyceride 0.15 Soybean lecithin (60% product) 0.15 .
6 Caprylic acid diglyceride 0.15 Calcium carbonate 0.15 7 Caprylic acid diglyceride 0.15 Soybean lecithin (60% product) 0.075 Calcium carbonate 0.075 8 Soybean lecithin (60% product) 0.15 Calcium carbonate 0.15 Table 2 _ _ - .
Test No. Foam height (mm) Test No. Foam height (mm) _ 4 ~2 ~ 8 ~2 As shown clearly in Table 2, the defoaming agent satisfying the requirements of.the present invention (Test No.7) exhibits excellent defoaming effect even at low temperature. The lac~ of any essential component of the present invention cannot achieve the desired defoaming effect. In the defoamlng agent of the present invention, similar defoaming effect was observed in the case of uslng magnesium carbonate or tertiary calcium phosphate .

2~3~8~ ~
instead of calcium carbonate.
Test example 2 Water (25 1) was added to 12.5 kg of water-absorbing soybean, and each of the components shown in Table 3 was added to -the milled product obtained by milling the soybean (but No.9 is the case without addition), which was then steam-boiled in an iron pot to measure the height of foam in the iron pot. The height of the foam was measured to obtain the results as shown in Table 4.
Table 3 ¦Test No. Defoaming agent Added amount (%) 9 No addition . ~
Caprylic acid diglyceride 30 11 ¦ Soybean lecithin (60% product) 30 12 Calcium carbonate 30 13 Caprylic acid diglyceride 15 Soybean lecithin (60% product) 15 Caprylic acid diglyceride 15 Calcium carbonate 15 Caprylic acid diglyceride -~ 15 : : Soybean lecithin (50% product) 7.5 Calcium carbonate 7.5 16 Powdery defoaming: agent commercially 30 available tglycerin fatty acid ester containing C18 as the principal component (monogIyceride), lecithin and calcium carbonatel ---; 2~3~18 Table 4 _ _ _ Test No. Foam height (cm) Test No. Foam height (cm) 9 overflow from pot 13 23 same as above 14 overflow from pot 11 same as above 15 9 12 same as above 16 11 As shown clearly in Table 4, the defoaming agent satisfying the requirements of the present-invention (Test No.15) exhibits more e~cellent defoaming effect even at high temperature, compared with the conventional products. In the defoaming agent of the present invention, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead oE calcium carbonate.
Test e~ample 3 A 3 % aqueous solution of sodium caseinate (300 ml) was placed in a 500-ml beaker, to which was simultaneously added each of the components shown in Table 5 as a defoaming agent (but No.17 is the case without addition), wh1ch was then stirred with a handheld mixer for two minutes to foam:the solution of sodium caseinate.~The height of the foam was:measured immed1ately after : ~ the stirring, to obtain the results as shown in Table 6.

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Table 5 ~ -est No. Defoaming agent Added amount (%) 17 No addition 18 Silicone emulsion* (30 % product) O.Ol 19 Caprylic acid diglyceride 0.01 .
Calcium carbonate 0.01 :
21 Soybean lecithin (60 % product) 0.01 _ _ 22 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 _ ._ 23 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 24 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 _ Calcium carbonate I 0.001 * Silicone èmulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 6 _ _ Test No. Foam height (mm) Test No. Foam height (mm) _ .
17 80 21 77 .

73 1 24 : 7 As shown clearly in Table 6, the defoamlng agent satisfying the requirements of the present invention (Test No.24) exhibits more excellent defoaming effect on the solution of sodium caseinate. It is also indicated that two components comprising .
: 14 2~g~ 8 lecithin or calcium carbonate added to caprylic acid diglyceride (Test Nos.22 and 23) also have the defoaming effect. In the defoaming agents of Test Nos. 22 and 24, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 4 Three-hundred milliliters of a 3 % solution of the concentrated whey protein of cheese (WPC) was placed in a 500-ml beaker, to which was simultaneously added each of the components as a defoaming agent, shown in Table 7 hereinbelow (but No.25 is the case without addition). The mixture was agitated with a handheld mi~er for two minutes to foam the WPC solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 8.
Table 7 Test No. Defoaming agent Added amount (%) .
25 No addition _ 26 Silicone emulsion* (30 % product) 0.01 27 Caprylic acid diglyceride 0.01 28 Calcium carbonate 0.01 . . .
29 Soybean lecithin (60 % product) ~ 0.01 ~ _ _. .
; 30 Caprylic acid diglyceride ~ ~ 0.009 Calcium carbonate 0.001 : : _ :
31 Caprylic acid diglyceride ~ 0.009 !

2 0 ~
Soybean lecithin (60% product) 0.001 32 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 Calcium carbonate 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 8 _ ... __ Test No. Foam height (mm) Test No. Foam height (mm) . _ ~

As shown clearly in Table 8, the defoaming agent satisfying the re~uirements of the presen-t invention (Test No.32) exhibits more e~cellent defoaming effect on the WPC solution. It is also indicated that two components comprising lecithin or calcium carbonate added to caprylic acid diglyceride (Tes-t Nos.30 and 31) also have the defoaming effect. In the defoaming agents of Test Nos. 30 and 32, similar defoaming effect was observed in the case of using magnesium carbona-te or tertiary calcium phosphate instead of calcium carbonate.
Test Example 5 Two hundred grams of coffee beans commercially available were milled and e~tracted into 3 1 of hot water, and the resulting coffee e~tract in solution was cooled to room ~.6 .

2 ~ 3 9 8 1 ~
temperature. The solution of 300 ml was placed in a 500-ml beaker, to which was simultaneously added each of the components shown in Table 9 (but No.33 is the case without addition) and agitated with a handheld mi~er for two minutes to foam the coffee solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 10.
Table 9 _ . . . _ . _ Tes-t No. Defoaming agent Added amount (%) _ 33 No addition 34 Silicone emulsion* (30 % product) 0.01 Caprylic acid diglyceride . 0.01 36 Calcium carbonate 0.01 .
37 Soybean lecithin (60 % product) 0.01 _ _ 38 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 _ 39 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 _ __ . 40 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) ~ 0.001 : Calcium carbonate ~ 0.001 * S1licone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 10 _ Test No. Foam height (mm) Test No. Foam height (mm) ~ ~ .

. 17 ,~....

2~9~ ~
~3 45 37 43 36 45 _ 40 _ As shown clearly in Table 10, the defoaming agent satisfying the requirements of the present invention (Test No.40) exhibits more excellent defoaming effect on the coffee e~tract in - solution. It is also indicated that two components comprising lecithin or calcium carbona-te added to caprylic acid diglyceride (Test Nos.38 and 39) also have the defoaming effect. In the defoaming agents of Test Nos. 38 and 40, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Tesk Example 6 Three hundred milliliters of a 10 % solution of powdery egg white werè placed in a 500-ml beaker, to which was simultaneously added each of the components shown in Table 11 (but No.41 is the case without addition) and agitated with a handheld mixer for two minutes to oam the solution of powdery egg white. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 12.
Table 11 Test No. Defoaming agent Added amount (%) .' 41 No addition _ S1licone emulslon* (30 ~product) 0.05 , 2~3~
43 Caprylic acid diglyceride 0.05 . _ 44 Calcium carbonate 0.05 Soybean lecithin (60 % product) 0.05 _ .
46 Caprylic acid diglyceride 0.045 Soybean lecithin (60 % product) 0.005 __ _ . _ 47 Caprylic acid diglyceride 0.040 . . Soybean lecithin (60% product) 0.005 Calcium carbonate 0.005 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 12 _ Test No. Foam height (mm) Test No. Foam height (mm) 42. 42 46 32 4351 . 47 15 As shown clearly in Table 12, the defoaming agent sa-tisfying the requirements af -the present invention (Test No.47) exhibits more excellent defoaming effect on the solution of powdery egg white. It is also indicated that two components comprising caprylic acid diglyceride and soybean lecithin also have a slight degree of the defoaming effect. In the defoaming agent of Test No. 47, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead .

. 19 2~
~f calcium carbonate.
Test Example 7 Five hundred grams of adzuki beans after washing in water were placed in a pot along with 2.5 l of water and heated. On boiling, fire was weakened and heating was continued for two hours. After cooling to room temperature, the total weight of the adzu~i beans and the boiled soup was adjusted to 4 kg by adding water. The solution (including adzuki beans) was milled with a house-hold mixer and the resulting solution (300 ml~ was placed in a 500-ml beaker, to which was added each of the components shown in Table 13 (No.48 is the case without addition) and stirred with a handheld mixer for two minutes to foam the solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 14.
Table 13 _ _ Test No. De~oaming agent Added amount (%) :
48 No addition 49 Silicone emulsion* (30 % product) 0.01 _ Caprylic acid diglyceride 0.01 51 Magnesium carbonate 0.01 52 Soybean lecithin (60 % product) 0.01 _ _ _ ~
53 Caprylic acid diglyceride ~ ; ~0.009 Magnesium carbonate ; ~ 0.001 54 Caprylic acid dlglyceride 0.009 Soybean lecithin (60% product) 0.001 . _ :

2 ~
- - - ~
Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 Magnesium carbonate 0.001 .
* Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.
Table 14 . _ .
Test No. Foam height (mm) Test No. Foam height (mm) _ ~0 10 54 8 . 51 30 55 3 . .
As shown clearly in Table 14, the defoaming agent satisfying the requirements of the present invention (Test No.55) exhibits more excellent defoaming effect on the boiled soup of adzuki beans. It is also indicated that two components (Test Nos.53.and 54) also have a slight degree of the defoaming effect. In the defoaming agents of Test Nos.53 and 55, similar defoaming effect was observed in the case of using calclum carbonate or tertiary calcium phosphate instead of magnesium carbonate.
Te~t Example 8 Three hundred milliliters of:a 10% solution of skimmilk powder were placed in a 500-ml beaker, to whlch was simultaneously added each of the components~shown in Table 15 . (No.56 is the case without addition), and stirred with a handheld 2~3~818 ~ixer for two minutes to foam the solution of skimmilk powder.
The height of the foam immediately after the agitation was measured to obtain the results shown in Table 16.
Table 15 . ... __ Test No. Defoaming agent Added amount (%) . ._._____ _ . .
56 No addition _ .... ___ 57 Silicone emulsion* (30 % product) 0.01 _ , 58 Caprylic acid diglyceride 0.01 59 Calcium carbonate 0.01 _ Soybean lecithin (60 % product) 0.01 _ . , ~ 61 Caprylic acid diglyceride 0.009 : Calcium carbonate 0.001 .
62 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 . _ 63 Caprylic acid.diglyceride 0.008 Soybean lecithin (60 % product) 0.001 .
Calcium carbonate 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.
Table 16 : :
Test No. Foam heigh-t (mm) Test No. Foam height (mm) : .
56 : 48 60 ;: ~

:
58 45 62 : 3 : : : :
59 50 j 63 : : 4 .

,: -2~3~
As shown clearly in Table 16, the defoaming agent satisfyingthe requirements of the present invention (Test No.63) exhibits more excellent defoaming effect on the solution of skimmilk powder. It is also indicated that two components (Test Nos. 61 and 62) also have a slight degree o~ the defoaming effect. In the defoaming agents of Test Nos. 61 and 63, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 9 Three hundred ml of a 3 % solution of powdered tea were placed in a 500-ml beaker, to which was simultaneously added each ! f the components shown in Table 17 (No.64 is the case without addition), and stirred with a handheld mixer for two minutes to foam the solution of the powder:d tea. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 18.
Table 17 _ Test No. Defoaming agent Added amount (%) .
; 64 No addition ~ 6~ Silicone emulsion* (30 % product) 0.01 66 Caprylic acid diglyceride ~ ~ ~ 0.01 ., _ . .
67 Calcium carbonate ~ ~ 0.01 ! 68 Soybean lecithin (60 % product) 0.01 . _ __ 69 Caprylic acid diglyceride 0.009 ~3~8~ ~
Calcïum carbonate 0.001 _ --- .
Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 71 Caprylic acid diglyceride 0.008 Soybean lecithin (60 % product) 0.001 Calcium carbonate 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.
Table 18 Test No. Foam height (mm) Test No. Foam height (mm) As shown clearly in Table 18, the defoaming agent satisfying the requirements oE the present invention (Test No.71) exhibits more e.Ycellent de~oaming effect on the solution of powdered tea.
It is also indicated that two components (Test Nos.69 and 70) also have a slight degree of the defoarning effect. In the defoaming agents of Test Nos. 69 and 71, similar defoamlng effect uas observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 10 Three hundred mill~iliters of a solution of Worcester sauce were placed in a 500-ml beaker, to which was simultaneously added . 24 .

:

each of the components shown in Table 19 (No.72 is the case without addition), and stirred with a handheld mixer for two minutes to foam the solution of Worcester sauce. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 20.
Table 19 ..
Test No. Defoaming agent Added amount (%) _ _ . _ .... _ 72 No addi-tion ¦ -73 Silicone emulsion* (30 % product~ _ __ 74 Caprylic acid diglyceride 0.01 . .
Calcium carbonate 0.01 76 Soybean lecithin (60 % product) 0.01 _ 77 Caprylic acid diglyceride 0.009 . Calcium carbonate 0.001 . _ .
78 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 . . _ 79 Caprylic acid diglyceride 0.008 Soybean lecithin (60 % product) 0.001 Calcium carbonate 0.001 * ~ Silicone emulsion : "Silica pet"; (produc-t name) manufactured by Shin-etsu Chemical Industry, K.K~.

Table 20 ~ ~: : ~ . .~ ....... __ Test No. Foam height (mm) Tes-t No. Foam height (mm) 73 1 0 1 77 ~ 9~
74 20 78 0 .

_ As shown clearly in Table 20, the defoaming agent satisfying the requirements of the present invention (Test No.79) exhibits more excellent defoaming effect on the solution of Worcester sauce. It is also indicated that two components where either one of lecithin and calcium carbonate is added to caprylic acid diglyceride (Test Nos.77 and 78) also have the defoaming effect on the foaming of the solution of Worcester sauce. In the defoaming agents (Test Nos. 77 and 79), similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example ll Six-hundred and sixty grams of potato (species, Danshaku) were minced, to which was added 5.5 l of water and ground with a mixer. The resulting solution of 300 ml was placed in a 500-ml beaker, to which was added each of the components shown in Table 21 (but No.80 is the case without addition) and stirred with a handheld mixer for two minutes to foam the solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 22.
Table 21 Test No. ¦Defoaming agent ~ Added amount (%) ~1 - I
80 lNo addition ~_ ___ ___ ~9~
_ 81 Silicone emulsion* (30 % product) 0.01 82 Caprylic acid diglyceride 0.01 83 Calcium carbonate 0.01 84 Soybean lecithin t60 % product) 0.01 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 .. _ _ 86 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 _ ._... __ 87 Caprylic acid diglyceride 0.008 Soybean lecithin (60 % product) 0.001 Calcium carbonate 0.001 . .
* Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 22 Test No. Foam height (mm) Test No. Foam height (mm) ..... __ 81 2~ 85 11 82 40 86 7 .

_ As shown clearly in Table 22, the defoaming agent satisfying-the requirements of -the present invention (Test No.87) exhibits more excellent defoaming effect on the solution of minced potato. It is also indicated that two components where either one of lecithin or calcium carbonate is added to caprylic acid . : 27 . . _~

liglyceride (Test Nos. 85 and 86) also have the defoaming effect.
In the defoaming agents Test Nos. 85 and 87, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 12 The tea extract solution, extracted by adding 3 1 of hot water to 75 g of tea commercially available, was cooled to room temperature. The solution (300 ml) was placed in a 500-ml beaker, to which was added each of the components shown in Table 23 as a defoaming a~ent (but No.88 is the case without addition), stirred with a handheld mixer for two minutes to foam the tea solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 24.
Table 23 Test No. Defoaming agent Added amount (%) 88 No addition _ 89 Silicone emulsion* (30 % product) 0.01 _ _ Caprylic acid diglyceride 0.01 91 Calcium carbonate 0.01 92 Soybean lecithin (60 % product) 0.01 _ 93 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 _ _ .
94 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) _ _ Caprylic acid diglyceFide -0.008 ~ 28 ~ , .

3~8~8 ~ ¦ Soybean lecithin (60% product) ¦ 0.001 ¦ Calcium carbonate - ¦ 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.
Table 24 Test No. Foam height (mm) Test No. Foam height (mm) 11 94 o 91 42 _ 95 0 As shown clearly in Table 24, the defoaming agent satisfying the requirements of the present invention (Test No.95) exhibits more excellent defoaming effect on the tea extract solution. Two components (Test Nos. 93 and 94) were observed to also have the defoaming effect. In the defoaming agents of Test Nos. 93 and 95, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 13 ', The uron tea extract solution, extracted by adding 3.25 1 of ¦ hot water to 75 g of uron tea commerclally available, was cooled ' to room temperature. The solution (300 ml) was placed ln a 500-j ml beaker, to which was added each~of the components shown in Table 25 as a defoaming agent (but No.96 is the case without . ~ '.

' 2~3~
addition), stirred with a handheld mixer for two minutes to foam the uron-tea extract solution. The height of the foam immediately after -the agitation was measured to obtain the results shown in Table 26.
Table 25 Test No. Defoaming agent Added amount (%) No addition _ _ 97 Silicone emulsion* (30 % product) 0.01 ... . .. ._ . 98 Caprylic acid diglyceride 0.01 99 Calcium carbonate 0.01 . .
100 Soybean lecithin (60 % product) . 0.01 101 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 102 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) . 0.009 _ _ 103 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 Calcium carbonate ~ 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.
: Table 26 Test No. Foam height (mm) Test No Foam helght (mm) : 96 : ~3 100 10 : 97 2 101 5 98 28 102 ~ 3 .

As shown clearly ln Table 26, the defoaming agent satisfying the requirements of the present invention (Test No.103) exhibits more excellent defoaming effect on the uron-tea extract solution. Two components (Test Nos. 101 and 102) were observed to also have the defoaming effect. In the defoaming agents of Test Nos. 101 and 103, similar defoaming effec-t was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 14 Three-hundred milliliters of a 10 % solution of a pudding powder commercially available [manufactured by House Food Industry, k.K., "Pudding Mix" ] were placed in,a 500-ml beaker, to which was simultaneously added each of the components shown in Table 27 as a de~oaming agent (but No.104 is the case without addition), stirred with a handheld mixer for two minutes to foam the tea solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 28.

Table 27 . .
Test No. Defoaming agent Added amount (%) . ~ .
104 No addition ~ _ . ..... _.. _ 105 Silicone emulsion* (30 % product) ~ 0.01 :
106 Caprylic acid dlglycerlde 0.01 107 Calcium carbonate , _ _ .
, ' 31 1 :

1..1 2~39~ 8 _ - `108 Soybean lecithin (60 % product) 0.01 .__ .__ 109 Caprylic acid diglyceride 0.009 Calcium carbonate 0.001 .
110 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 ____ ..
111 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 Calcium carbonate 0.001 .
* Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 28 ._ _ _ _ .
~ Test No. Foam height (mm) Test No. Foam height (mm) . _ O . . .
104 47 10~ 57 107 _ 111 _ -As shown clearly in Table 28, the defoaming agent satisfying the requirements of the present invention (Test No.111) exhibits more excellent defoaming effect on the pudding solution. Two components (Test Nos. 109 and llO) were observed to also have the defoaming effect. In the defoaming agents of Test Nos. 109 and 111, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test ExampIe 15 2~3~

Three-hundred milliliters of a 10 % solution of a jelly powder commercially available [manufactured by House Food Industry, k.K., "Jellyace (melon)" ] were placed in a 500-ml beaker, to which was simultaneously added each of the components shown in Table 29 as a defoaming agent (but No.112 is the case without addition), stirred with a handheld mixer for two minutes to foam the tea solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 30.

Table 29 .
Test No. Defoaming agent Added amount (%) - : _ 112 No addition _ _ .
113 Silicone emulsion* (30 % product) 0.01 ..
114 Caprylic acid diglyceride 0.01 . __ _ . ._ 115 Calcium carbonate 0.01 116 Soybean leci-thin (60 % product) 0.01 117 Caprylic acid diglyceride 0.009 .

Calcium carbonate 0.001 ~ . _ . _ .
118 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 .
119 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 Calcium carbonate 0.001 * Silicone emulsion : "Silica pet" (produc-t name:) manufactured : 33 I

2~3~18 y Shin-etsu Chemical Industry, K.K.

Table 30 Test No. Foam height (mm) Test No. Foam height (mm) . . __ As shown clearly in Table 30, the defoaming agent satisfying the requirements of the present invention (Test No.119) exhibits more excellent defoaming effect on the jelly solution. Two components of caprylic acid diglyceride and soybean lecithin (Test No. 118) were observed to also have the defoaming effect.
In the defoaming agent of Test No. 119, similar defoaming effect was observed in the case of using magnesium car-bonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 16 The solution (300 ml), obtained by adding skimmilk powder to a 0.3 % solution of locust bean gum to a final concentration of 3 %, was placed in a 500-ml beaker, to which was simultaneously added each of the components in Table 31 (but No.120 is the case wlthout addition) and stirred with a handheld mixer to foam the solution. The height of the foam immediately after the agitation was measured to obtain the results shown in Table 32.
Table 31 ¦Test No. ¦Defoaming aeent - ¦ Added amount (%~¦

34 l l :

- 2~3~18 , .
120 No addition 121 Silicone emulsion* (30 % product) 0.05 122 Caprylic acid diglyceride 0.05 123 Calcium carbonate 0.05 124 Soybean lecithin (60 % product) 0.05 _ _ 125 Caprylic acid diglyceride 0.045 Calcium carbonate 0.005 126 Caprylic acid diglyceride 0.045 Soybean lec1thin (60% product) 0.005 127 Caprylic acid diglyceride 0.040 Soybean lecithin (60% product) 0.005 _ Calcium carbonate 0 005 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

Table 32 . .
Test No. Foam height (mm) Test No. Foam height (mm) _ 120 69 12~ 72 121 0 125 ' 6 As shown clearly in Table 32, the defoaming agent satisfying the requirements of the present invention (Test No.127) exhibits more excellent de~oaming effect on the mixed soluti,on of locust bean gum and skimmilk powder. Two components (Test Nos.125 and 126) ~.

2 ~
~ere observed to also have the defoaming effect. In the defoaming agents of Test Nos.125 and 127, similar defoaming effect was observed in the case of using magnesium carbonate or tertiary calcium phosphate instead of calcium carbonate.
Test Example 17 A lO % solution (300 ml) of skimmilk powder was placed in a 500-ml beaker, to which was simultaneously added each of the components in Table 33 (but No.128 is the case without addition) and stirred with a handheld mixer to foam the solution of skimmilk powder.
The height of the foam immediately after the agitation was meas-ured to obtain the results shown in Table 34.
Table 33 Test No. Defoaming agent Added amount ~%) 128 No addition .. ~
129 ~ 0.01 130 Caprylic acid diglyceride 0.01 _ .
131 Magnesium carbonate 0.01 132 Soybea~ lecithin (60 % product) 0.01 133 Caprylic acid diglyceride 0.009 Magnesium carbonate 0.001 _ 134 Caprylic acld diglyceride 0.009 _ Soybean lecithin (60Yo product) ~ 0.001 135 Caprylic acid diglyceride ~ 0.008 Soybean lecithin (60% product) 0.001 __ _ Magneslum carbonate 0.001 ., ~ " 36 L

2~3~

* Silicone emulsion : "Silica pet" (product name) manufacturedby Shin-etsu Chemical Industry, K.K.
Table 34 ..~
Test No. Foam height (mm) Test No. Foam height (mm) 131 52 135 _ As shown clearly in Table 34, the defoaming agent satisfying the requirements of -the present invention-(Test No.135) exhibits more excellent defoaming effect on the solution of skimmilk powder.
Two components (Test Nos.133 and 134) were observed to also have the defoaming effect.
Test Example 18 A 10 % solution (300 ml) of skimmilk powder was placed in a 500-ml beaker, to which was simultaneously added each of the components in Table 35 (but No.136 is -the case without addition) an~d stirred with a handheld mixer to foam the solution of skimmilk powder. The height of the foam immediately after the agitation was measured -to obtain the results shown in Table 36.
Table 35 ~Test No. Defoaming agent Added omount (Y~) 2~3~8~8 ,~ ..
36 No addition . ~ ._ 137 Silicone emulsion* (30 % product) 0.01 . .
138 Caprylic acid diglyceride 0.01 139 Tertiary calcium phosphate 0.01 .
140 Soybean lecithin (60 % product) 0.01 . .~ ._ ...
141 Caprylic acid diglyceride 0.009 Tertiary calcium.phosphate 0.001 .... ___ _ .. .... _ 142 Caprylic acid diglyceride 0.009 Soybean lecithin (60% product) 0.001 143 Caprylic acid diglyceride 0.008 Soybean lecithin (60% product) 0.001 L... .. ~ . Tertiary calcium.l.phosphate 0.001 * Silicone emulsion : "Silica pet" (product name) manufactured by Shin-etsu Chemical Industry, K.K.

I'able 36 _ Test No. Foam height (mm) Test No. Foam height (mm) _ _ As shown clearly in Table 36, the defoaming agent satisfying the requirements of the present invention (Test No.143) exhibits more excellent defoaming effect on the solution of skimmilk powder. Two components (Test No. 141 and 143) were observed to also have the defoaming effect.

- 2~39~ ~

There will now be shown embodiments.
EXAMPLES
E~ample 1 To a mi~ed solution comprising 1 kg of caprylic acid diglyceride (Sunfat GDC-S, manufactured by Taiyo Chemical K.K.), 2 kg of soybean lecithin (manufactured by Ajinomoto K.K.) and 6 kg of soybean shirashimeyu was added 1 kg of calcium carbonate to obtain 10 kg of a liquid defoaming agent.
Example 2 To a mixed solution comprising 1.5 kg of caprylic acid diglyceride (Sunfat GDC-S, manufactured by Taiyo Chemical K.K.), 2 kg of soybean lecithin (manufactured by Ajinomoto K.K.) and 6 kg of soybean shirashimeyu was added 0.5 kg of calcium carbonate to obtain 10 kg of a liquid defoaming agent.
E~ample 3 To a mixed solution comprising 1 kg of caprylic acid diglycerlde (Sunfat GDC-S, manufactured by Taiyo Chemical K.K.), 2 kg of soybean lecithin (manufactured by Aiinomoto K.K.) and 6 kg of soybean shirashimeYu was added 0.5 kg of glycerin fatty acid e~ster (Sunsoft No. 8000, manufactured by Taiyo Chemical K.K.~, which was melted and dissolved, followed by addition of 1 kg of~calcium carbonate to obtain 10 kg of a liquld defoaming 2~3~
.gent.
Example 4 To a mixed solution comprising 7.6 kg of caprylic acid diglyceride (Sunfat GDC-S) and 1 kg of soybean lecithin (manufactured by Ajinomoto K.K.) was added 0.4 kg of glycerin fatty acid ester (Sunsoft No.2500), which was melted and dissolved, followed by addition of 1 kg of calcium carbonate, to obtain 10 kg of a liquid defoaming agent.
Example 5 To a mixed solution comprising 1 kg of caprylic acid diglyceride (Sunfat GDC-S), 1.5 kg of soybean lecithln (manufactured by Ajinomoto K.K.) and 6.5 kg of soybean shirashimeyu was added 0.5 kg of glycerin fatty acid ester (Sunsoft No.2500), which was melted and dissolved, followed by addition of 0.5 kg of magnesium carbonate, to obtain 10 kg of a liquid defoaming agent.
Example 6 To a mixed solution comprising 6.5 kg of caprylic acid diglyceride (Sunfat GDC-S), 1.5 kg of soybean lecithin (manufactured by Ajinomoto K.K.) and 1 kg of soybean shirashimeYu was added 0.5 kg of glycerin fatty acld ester~(Sunsoft No.2500), which was melted and dissolved, followed by~additlon of 0.5 kg of magnesium carbonate, to obtain 10 kg of a liquid defoaming agent.
Example 7 ¦ To 9 kg of capryIic acid diglyceride (Sunfat GDC-S) was . :

2~3~818 added 1 kg of soybean lecithin (manufactured by Ajinomoto K.K.) to obtain 10 kg of a liquid defoaming agent.
Example 8 To 8.5 kg of caprylic acid diglyceride (Sunfat GDC-S) was added 0.5 kg of soybean lecithin (manufactured by Ajinomoto K.K.), which was then melted and dissolved, followed by addition of 1 kg of magnesium carbonate, to obtain 10 kg of a liquid defoaming agent.
Example 9 To 1 kg of caprylic acid diglyceride (Sunfat GDC-S) and 7.5 kg of soybean shirashimeyu was added 0.5 kg of glycerin fatty acid ester (Sunsoft No. 2500), which was then melted and dissolved, followed by addition of 0.5 kg of magnesium carbonate, to obtain 10 kg of a liquid defoaming agent.

, ; 41 ~ -' ':

-_ _ ~ _~ _ ._ _ ___ ~ . . . . .. . -

Claims (16)

  1. The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

    l. A liquid defoaming agent for food containing lecithin and/or inorganic carrier in addition to low fatty acid diglyceride.
  2. 2. The liquid defoaming agent for food according to claim 1, wherein the low fatty acid diglyceride is in the liquid form, obtained by esterifying a low fatty acid having 6 to 12 carbon atoms with glycerin.
  3. 3. The liquid defoaming agent for food according to claim 2, wherein the low fatty acid diglyceride is caprylic acid diglyceride.
  4. 4. The liquid defoaming agent for food according to any one of claims 1 to 3, wherein the inorganic carrier is calcium carbonate, magnesium carbonate or tertiary calcium phosphate.
  5. 5. The liquid defoaming agent for food according to claim 1, containing caprylic acid diglyceride, lecithin and magnesium carbonate.
  6. 6. The liquid defoaming agent for food according to any one of claims 1 to 4, containing at least one selected from the group consisting of diluent, viscosity adjuster and emulsifier.
  7. 7. The liquid defoaming agent for food according to claim 6, wherein the diluent is edibie oil.
  8. 8. The liquid defoaming agent according to claim 7, containing caprylic acid diglyceride, lecithin, magnesium carbonate and edible oil.
  9. 42 A method for using a liquid defoaming agent for food, characterized by adding the liquid defoaming agent of claim 1, at an appropriate stage of the process of producing ice-miskimmilkx powder, whole milk powder, skimmilk powder, modified milk powder, casein or the like, or of the process of producing the processed foods using them.
  10. 10. A method for using a liquid defoaming agent for food, characterized by adding the liquid defoaming agent of claim 1, at an appropriate stage of the process of producing coffee drinks, instant coffee, and coffee powder or of the process of producing the processed foods using them.
  11. 11. A method for using a liquid defoaming agent for food, characterized by adding the liquid defoaming agent of claim 1, at an appropriate stage of the process of processing cacao beans.
  12. 12. A method for using a liquid defoaming agent for food, characterized by adding the liquid defoaming agent of claim 1, at an appropriate stage of the process of producing green tea and fermented tea, or of the process of producing the processed foods using the powder and extract solution thereof.
  13. 13. A method for using a liquid defoaming agent, characterized by adding the liquid defoaming agent of claim 1, prior to the process of blending a binding agent at the process of producing ham and sausage.
  14. 14. A method for using a liquid defoaming agent, characterized by adding the liquid defoaming agent of claim 1, prior to the process of preparing bean paste.
  15. 15. A method for using a liquid defoaming agent, characterized by adding the liquid defoaming agent of claim 1, at an appropriate stage of preparing boiled beans.
  16. 16. A method for using a liquid defoaming agent, characterized by adding a liquid defoaming agent containing low fatty acid diglyceride, lecithin and inorganic carrier at an appropriate stage of the process of producing bean curd or soybean milk.
CA002039818A 1990-04-05 1991-04-04 Liquid defoaming agent for food and method of use thereof Abandoned CA2039818A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP9099390 1990-04-05
JP2-90993 1990-04-05
JP2-155915 1990-06-13
JP15591590 1990-06-13
JP2-173799 1990-06-29
JP17379990 1990-06-29

Publications (1)

Publication Number Publication Date
CA2039818A1 true CA2039818A1 (en) 1991-10-06

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ID=27306589

Family Applications (1)

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Country Link
CA (1) CA2039818A1 (en)

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