JP6474560B2 - Defoamer for food - Google Patents
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- JP6474560B2 JP6474560B2 JP2014160960A JP2014160960A JP6474560B2 JP 6474560 B2 JP6474560 B2 JP 6474560B2 JP 2014160960 A JP2014160960 A JP 2014160960A JP 2014160960 A JP2014160960 A JP 2014160960A JP 6474560 B2 JP6474560 B2 JP 6474560B2
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- 235000013305 food Nutrition 0.000 title claims description 56
- 239000013530 defoamer Substances 0.000 title description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 50
- 239000000194 fatty acid Substances 0.000 claims description 50
- 229930195729 fatty acid Natural products 0.000 claims description 50
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 50
- 239000002518 antifoaming agent Substances 0.000 claims description 43
- -1 fatty acid ester Chemical class 0.000 claims description 38
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 238000007127 saponification reaction Methods 0.000 claims description 32
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 25
- 229960002446 octanoic acid Drugs 0.000 claims description 25
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 239000000470 constituent Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- 238000004519 manufacturing process Methods 0.000 description 53
- 238000005886 esterification reaction Methods 0.000 description 44
- 239000003054 catalyst Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- 239000007789 gas Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000007664 blowing Methods 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 229920000223 polyglycerol Polymers 0.000 description 18
- 239000006260 foam Substances 0.000 description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 229910001873 dinitrogen Inorganic materials 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
- 235000011187 glycerol Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 235000018102 proteins Nutrition 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 8
- 108090000623 proteins and genes Proteins 0.000 description 8
- 229940105990 diglycerin Drugs 0.000 description 7
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000007879 food anti-foaming agent Nutrition 0.000 description 6
- 235000003084 food emulsifier Nutrition 0.000 description 6
- 235000013361 beverage Nutrition 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 3
- WOKDXPHSIQRTJF-UHFFFAOYSA-N 3-[3-[3-[3-[3-[3-[3-[3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)CO WOKDXPHSIQRTJF-UHFFFAOYSA-N 0.000 description 3
- 102000011632 Caseins Human genes 0.000 description 3
- 108010076119 Caseins Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000013527 bean curd Nutrition 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 235000013322 soy milk Nutrition 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000013580 sausages Nutrition 0.000 description 2
- 229940080237 sodium caseinate Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000021107 fermented food Nutrition 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Description
本発明は、食品用消泡剤に関する。 The present invention relates to a food antifoaming agent.
食品の製造工程では、泡の発生により生産効率の低下や最終製品の品質不良をもたらす場合がある。例えば、ハム・ソーセージ類の製造では、ピックル液（塩漬剤の溶液）を用いる処理工程においてタンパク素材に起因する泡が発生すると、最終製品であるハム・ソーセージ類の品質不良につながる。また、ビート糖の製造では、酵素処理した糖蜜に生石灰を加え、ショ糖石灰として糖分を回収するステフェン工程において泡立ちによるライントラブルが発生すると、生産効率が低下する。 In the food manufacturing process, the generation of bubbles may lead to a decrease in production efficiency and poor quality of the final product. For example, in the production of ham and sausages, if foam caused by a protein material is generated in a treatment process using a pickle solution (salted solution), the quality of the final product, ham and sausages, is reduced. In addition, in the production of beet sugar, if a line trouble due to foaming occurs in the stefene process in which quick lime is added to molasses treated with enzyme and sugar is recovered as sucrose lime, production efficiency decreases.
このような問題に対し、従来シリコーン樹脂系消泡剤や食品用乳化剤を利用した消泡剤が用いられている。しかし、シリコーン樹脂系消泡剤は、食品に使用するには安全性のイメージが悪いという問題がある。また、シリコーン樹脂系消泡剤は、食品添加物としての使用量に制限があり、その制限内の使用では十分な効果を得難いという問題もある。このため、近時このような問題の少ない食品用乳化剤を利用した消泡剤が好まれる傾向にある。 Conventionally, antifoaming agents using silicone resin antifoaming agents and food emulsifiers have been used for such problems. However, silicone resin-based antifoaming agents have a problem that their safety image is poor for use in foods. In addition, the amount of the silicone resin antifoaming agent used is limited as a food additive, and there is also a problem that it is difficult to obtain a sufficient effect when used within the limitation. For this reason, recently, there is a tendency to favor an antifoaming agent using a food emulsifier with few such problems.
食品用乳化剤を利用した消泡剤としては、例えば、グリセリンの重合度が６以上、かつＨＬＢ値が７以下であるポリグリセリン脂肪酸エステルを有効成分とする飲料用消泡剤（特許文献１）、ポリグリセリンの平均重合度が４〜１２で、その構成脂肪酸とケン化価を特定したポリグリセリン脂肪酸エステルを有効成分とする飲料用消泡剤（特許文献２及び３）、クエン酸モノグリセリドとＨＬＢ値が１０〜１６のポリグリセリン脂肪酸エステルを含有することを特徴とする抑泡剤（特許文献４）、ポリグリセリンの平均重合度が２〜２０で、主構成脂肪酸にベヘン酸を有してなり、ケン化価が１１０〜１６０であるポリグリセリン脂肪酸エステルを有効成分とする低酸性飲料用消泡剤（特許文献５）、ポリグリセリン不飽和脂肪酸エステル１２〜１５重量％、グリセリン不飽和脂肪酸エステル８〜１２重量％、グリセリン飽和脂肪酸エステル４〜８重量％、及び糖類６５〜７６重量％を含有することを特徴とする食品用消泡剤（特許文献６）、ジグリセリンとカプリル酸及び／又はカプリン酸とのエステル化化合物であって、モノ、ジ、トリ、テトラエステル体が特定の比率であるポリグリセリン脂肪酸エステルからなる食品用消泡剤（特許文献７）等が提案されている。 As an antifoaming agent using a food emulsifier, for example, a beverage antifoaming agent comprising a polyglycerol fatty acid ester having a polymerization degree of glycerin of 6 or more and an HLB value of 7 or less (Patent Document 1), Defoaming agent for beverages (Patent Documents 2 and 3) containing polyglycerin fatty acid esters whose polyglycerin average polymerization degree is 4 to 12 and whose constituent fatty acids and saponification values are specified as active ingredients, citric acid monoglyceride and HLB value Containing 10 to 16 polyglycerin fatty acid ester (Patent Document 4), polyglycerin having an average degree of polymerization of 2 to 20, and having behenic acid as the main constituent fatty acid, Anti-foaming agent for low-acid beverages containing polyglycerin fatty acid ester having a saponification value of 110 to 160 as an active ingredient (Patent Document 5), polyglycerin unsaturated fatty acid ester 1 A defoamer for foods containing -15% by weight, glycerin unsaturated fatty acid ester 8-12% by weight, glycerin saturated fatty acid ester 4-8% by weight, and sugars 65-76% by weight (Patent Document 6) ), An esterified compound of diglycerin and caprylic acid and / or capric acid, and a defoamer for foods comprising a polyglycerin fatty acid ester having a specific ratio of mono-, di-, tri-, and tetra-esters (Patent Document) 7) etc. are proposed.
ここで、食品の製造において泡が発生する原因としては、例えば、液体原料に対し撹拌や振動等の物理的な衝撃が加えられること、加熱による沸騰や微生物による発酵等により液体原料中で気体が生成すること、ポンプ等により液体原料に気体が供給されること等がある。そして、食品の製造において、このような原因が長時間連続して起こると、従来の食品用消泡剤を使用しても必ずしも満足できる効果が得られないのが現状である。従って、食品の製造において泡を抑制する効果が長時間持続する食品用消泡剤が求められていた。 Here, as the cause of the generation of bubbles in the production of food, for example, a physical impact such as stirring or vibration is applied to the liquid raw material, the gas is generated in the liquid raw material due to boiling by heating, fermentation by microorganisms, or the like. In some cases, gas is supplied to the liquid raw material by a pump or the like. In the production of food, when such a cause occurs continuously for a long time, even if a conventional antifoaming agent for food is used, a satisfactory effect is not always obtained. Accordingly, there has been a demand for a defoamer for foods that has a long-lasting effect of suppressing foam in the production of food.
本発明は、食品の製造において泡を抑制する効果が長時間持続する食品用消泡剤を提供することを課題とする。 This invention makes it a subject to provide the antifoamer for foodstuffs which the effect which suppresses foam in manufacture of foodstuff lasts for a long time.
本発明者は、上記課題を解決するため、鋭意検討した結果、特定の条件を満たすポリグリセリン脂肪酸エステルを食品用消泡剤として用いることにより、通気により発生する泡を十分に抑制できることを見出し、この知見に基づいて本発明をなすに至った。 As a result of intensive studies to solve the above problems, the present inventor found that by using a polyglycerin fatty acid ester satisfying specific conditions as a defoaming agent for food, foam generated by aeration can be sufficiently suppressed, The present invention has been made based on this finding.
即ち、本発明は、条件（Ａ）：ポリグリセリンの平均重合度が３〜１２、条件（Ｂ）：構成脂肪酸がカプリル酸及び条件（Ｃ）：ケン化価が２００〜２５０を満たすポリグリセリン脂肪酸エステルを有効成分とする食品用消泡剤、
からなっている。
That is, the present invention is such that the condition (A): the average polymerization degree of polyglycerol is 3 to 12, the condition (B): the constituent fatty acid is caprylic acid, and the condition (C): the polyglycerol fatty acid satisfying the saponification value is 200 to 250. An antifoaming agent for foods containing ester as an active ingredient,
It is made up of.
本発明の食品用消泡剤を食品の製造に使用すると、泡を抑制する効果が長時間持続する。 When the antifoaming agent for food of the present invention is used for the production of food, the effect of suppressing foam lasts for a long time.
本発明の食品用消泡剤において有効成分として用いられるポリグリセリン脂肪酸エステルは、下記条件（Ａ）、（Ｂ）及び（Ｃ）を満たすものである。
（Ａ）ポリグリセリンの平均重合度が３〜１２
（Ｂ）構成脂肪酸がカプリル酸
（Ｃ）ケン化価が２００〜２５０
The polyglycerin fatty acid ester used as an active ingredient in the food antifoaming agent of the present invention satisfies the following conditions (A), (B) and (C).
(A) The average degree of polymerization of polyglycerin is 3-12
(B) Constituent fatty acid is caprylic acid (C) Saponification value is 200-250
［条件（Ａ）について］
本発明に用いられるポリグリセリン脂肪酸エステルを構成するポリグリセリンは、平均重合度が３〜１２である。ポリグリセリンの平均重合度がこのような範囲であると、食品の製造において泡を抑制する効果が長時間持続する。具体的なポリグリセリンとしては、例えば、トリグリセリン（平均重合度３）、テトラグリセリン（平均重合度４）、ペンタグリセリン（平均重合度５）、ヘキサグリセリン（平均重合度６）、ヘプタグリセリン（平均重合度７）、オクタグリセリン（平均重合度８）、デカグリセリン（平均重合度１０）等が挙げられる。
[Condition (A)]
The polyglycerin constituting the polyglycerin fatty acid ester used in the present invention has an average degree of polymerization of 3-12. When the average degree of polymerization of polyglycerin is within such a range, the effect of suppressing foam in food production lasts for a long time. Specific examples of polyglycerin include, for example, triglycerin (average degree of polymerization 3), tetraglycerin (average degree of polymerization 4), pentaglycerin (average degree of polymerization 5), hexaglycerin (average degree of polymerization 6), heptaglycerin (average). Polymerization degree 7), octaglycerin (average polymerization degree 8), decaglycerol (average polymerization degree 10), etc. are mentioned.
ここで、ポリグリセリンの平均重合度（ｎ）は、次式（式１）及び（式２）に基づき算出される。 Here, the average degree of polymerization (n) of polyglycerin is calculated based on the following formulas (formula 1) and (formula 2).
分子量＝７４ｎ＋１８・・・（１）
水酸基価＝５６１１０（ｎ＋２）／分子量・・・（２）
Molecular weight = 74n + 18 (1)
Hydroxyl value = 56110 (n + 2) / Molecular weight (2)
尚、上記（式２）中の水酸基価は、「基準油脂分析試験法（Ｉ）」（社団法人 日本油化学会編）の［２．３．６−１９９６ ヒドロキシル価］に従って測定される。 In addition, the hydroxyl value in the above (Formula 2) is measured in accordance with [2.3.6-1996 Hydroxyl Number] of “Standard Oil Analysis Test Method (I)” (edited by Japan Oil Chemists' Society).
［条件（Ｂ）について］
本発明に用いられるポリグリセリン脂肪酸エステルは、炭素数が８のカプリル酸を構成脂肪酸とする。構成脂肪酸がカプリル酸であることにより、食品の製造において泡を抑制する効果が長時間持続する。
[Condition (B)]
The polyglycerin fatty acid ester used in the present invention uses caprylic acid having 8 carbon atoms as a constituent fatty acid. When the constituent fatty acid is caprylic acid, the effect of suppressing foam in the production of food lasts for a long time.
［条件（Ｃ）について］
本発明に用いられるポリグリセリン脂肪酸エステルは、ケン化価が２００〜２５０である。ケン化価が２００未満であるか、又は２５０を超えると、食品の製造において泡を抑制する効果が長時間持続できないため好ましくない。上記ケン化価は、「基準油脂分析試験法（Ｉ）」（社団法人日本油化学会編）の[２．３．２−１９９６ケン化価]に従って測定される。尚、上記ケン化価の単位は「ｍｇ」である。
[Condition (C)]
The polyglycerol fatty acid ester used in the present invention has a saponification value of 200 to 250. If the saponification value is less than 200 or exceeds 250, the effect of suppressing foam in the production of food cannot be sustained for a long time, which is not preferable. The saponification value is measured according to [2.3.2-1996 saponification value] of “Standard Oil Analysis Test Method (I)” (edited by Japan Oil Chemists' Society). The unit of the saponification value is “mg”.
上記条件（Ａ）、（Ｂ）及び（Ｃ）を満たすポリグリセリン脂肪酸エステル（以下、「本発明のポリグリセリン脂肪酸エステル」ともいう）は、ポリグリセリンと脂肪酸とのエステル化生成物であり、自体公知のエステル化反応等により製造される。 The polyglycerol fatty acid ester satisfying the above conditions (A), (B) and (C) (hereinafter also referred to as “polyglycerol fatty acid ester of the present invention”) is an esterification product of polyglycerol and a fatty acid, It is produced by a known esterification reaction or the like.
本発明のポリグリセリン脂肪酸エステルの原料となるポリグリセリンとしては、平均重合度が３〜１２のポリグリセリンが好ましく用いられる。また、本発明のポリグリセリン脂肪酸エステルの原料となる脂肪酸としては、カプリル酸が好ましく用いられる。 As a polyglycerol used as the raw material of the polyglycerol fatty acid ester of the present invention, a polyglycerol having an average degree of polymerization of 3 to 12 is preferably used. In addition, caprylic acid is preferably used as the fatty acid as a raw material for the polyglycerol fatty acid ester of the present invention.
ポリグリセリンと脂肪酸とのエステル化反応により本発明のポリグリセリン脂肪酸エステルを製造するにあたり、ポリグリセリンに対する脂肪酸の仕込み量は、次の通りであることが好ましい。例えば、デカグリセリン及びカプリル酸を用いる場合、デカグリセリン１モルに対してカプリル酸が５．０〜７．８モルであることが好ましい。また、トリグリセリン及びカプリル酸を用いる場合、トリグリセリン１モルに対してカプリル酸が１．６〜２．５モルであることが好ましい。 In producing the polyglycerin fatty acid ester of the present invention by esterification reaction of polyglycerin and fatty acid, the amount of fatty acid charged to polyglycerin is preferably as follows. For example, when using decaglycerol and caprylic acid, it is preferable that caprylic acid is 5.0-7.8 mol with respect to 1 mol of decaglycerol. Moreover, when using triglycerol and caprylic acid, it is preferable that caprylic acid is 1.6-2.5 mol with respect to 1 mol of triglycerol.
また、上記エステル化反応は、通常アルカリを触媒として用いて行われる。アルカリ触媒としては、例えば水酸化カリウム、水酸化ナトリウム、炭酸カリウム、炭酸ナトリウム等が挙げられる。アルカリ触媒の使用量は、全仕込み量（乾燥物換算）１００質量％中、０．０１〜１．０質量％、好ましくは０．０５〜０．５質量％である。 Moreover, the said esterification reaction is normally performed using an alkali as a catalyst. Examples of the alkali catalyst include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and the like. The usage-amount of an alkali catalyst is 0.01-1.0 mass% in the total preparation amount (dry matter conversion) 100 mass%, Preferably it is 0.05-0.5 mass%.
また、上記エステル化反応は、例えば攪拌機、加熱用のジャケット、邪魔板、不活性ガス吹き込み管、温度計及び冷却器付き水分分離器等を備えた通常の反応容器に、ポリグリセリン、脂肪酸及び触媒を供給して攪拌混合し、窒素又は二酸化炭素等の任意の不活性ガス雰囲気下で、エステル化反応により生成する水を系外に除去しながら、所定温度で一定時間加熱して行われるのが好ましい。反応温度は、通常１８０〜２６０℃であり、好ましくは２００〜２５０℃である。また、反応における圧力条件は、減圧下又は常圧下であり、反応時間は、通常０．５〜１５時間であり、好ましくは１〜４時間である。また、反応の終点は、反応混合物の酸価を測定し、その酸価が３以下であることを目安として決定するのが好ましい。 The esterification reaction is carried out in a normal reaction vessel equipped with, for example, a stirrer, a heating jacket, a baffle plate, an inert gas blowing tube, a thermometer and a water separator with a cooler, and the like. The mixture is stirred and mixed, and heated at a predetermined temperature for a certain period of time while removing water generated by the esterification reaction outside of the system under any inert gas atmosphere such as nitrogen or carbon dioxide. preferable. The reaction temperature is usually 180 to 260 ° C, preferably 200 to 250 ° C. Moreover, the pressure conditions in reaction are under pressure reduction or a normal pressure, Reaction time is 0.5 to 15 hours normally, Preferably it is 1 to 4 hours. The end point of the reaction is preferably determined by measuring the acid value of the reaction mixture and using the acid value of 3 or less as a guide.
エステル化反応終了後、必要により反応混合物中に残存する触媒を中和する。エステル化の反応温度が２００℃を超える場合、中和処理は、反応混合物を１２０〜２００℃に冷却してから行うのが好ましい。また、触媒として水酸化ナトリウムを使用した場合、中和処理では、反応混合物にリン酸（８５質量％）を添加し、良く混合することが好ましい。この場合、中和処理で添加するリン酸（８５質量％）の量は、以下に示す中和反応式（式１）で計算されるリン酸量を０．８５で除した量（以下、「基準リン酸量」という）以上であることが好ましく、基準リン酸量の２〜３倍量であることがより好ましい。尚、基準リン酸量は、具体的には、水酸化ナトリウム１．０ｇに対し、０．９６ｇである。 After completion of the esterification reaction, the catalyst remaining in the reaction mixture is neutralized as necessary. When the reaction temperature of esterification exceeds 200 degreeC, it is preferable to perform a neutralization process after cooling a reaction mixture to 120-200 degreeC. Moreover, when sodium hydroxide is used as a catalyst, it is preferable to add phosphoric acid (85 mass%) to the reaction mixture and mix well in the neutralization treatment. In this case, the amount of phosphoric acid (85% by mass) added in the neutralization treatment is the amount obtained by dividing the phosphoric acid amount calculated by the neutralization reaction formula (formula 1) shown below by 0.85 (hereinafter, “ The reference phosphoric acid amount is preferred), and more preferably 2 to 3 times the reference phosphoric acid amount. The reference phosphoric acid amount is specifically 0.96 g with respect to 1.0 g of sodium hydroxide.
中和処理後、その温度で、好ましくは０．５時間以上、更に好ましくは１〜１０時間放置するのが好ましい。また、未反応のポリグリセリンが下層に分離した場合はそれを除去するのが好ましい。また、必要に応じて、常法に従い、脱色、脱臭等の処理を行うことができる。 After the neutralization treatment, it is preferably left at that temperature for preferably 0.5 hours or more, more preferably 1 to 10 hours. Moreover, when unreacted polyglycerin isolate | separates into a lower layer, it is preferable to remove it. If necessary, treatments such as decolorization and deodorization can be performed according to a conventional method.
本発明のポリグリセリン脂肪酸エステルは、そのまま食品用消泡剤として使用することができる。また、本発明のポリグリセリン脂肪酸エステルを有効成分として配合した製剤を食品用消泡剤として使用しても良い。このような製剤の形態に特に制限はないが、例えば、本発明のポリグリセリン脂肪酸エステルを油脂、乳化剤、アルコール等と溶融混合して得られる油性製剤、本発明のポリグリセリン脂肪酸エステルを澱粉、デキストリン等の粉末基材に吸着させて得られる粉末製剤、本発明のポリグリセリン脂肪酸エステルを水、エタノール、液糖等の極性分散媒に分散して得られる水中油型乳化製剤等が挙げられる。 The polyglycerol fatty acid ester of the present invention can be used as it is as an antifoaming agent for food. Moreover, you may use the formulation which mix | blended the polyglycerol fatty acid ester of this invention as an active ingredient as an antifoamer for foodstuffs. There is no particular limitation on the form of such a preparation. For example, an oily preparation obtained by melt-mixing the polyglycerin fatty acid ester of the present invention with oils, emulsifiers, alcohols, etc., and the polyglycerin fatty acid ester of the present invention in starch, dextrin Examples thereof include powder preparations obtained by adsorbing to a powder base material such as oil-in-water emulsion preparations obtained by dispersing the polyglycerin fatty acid ester of the present invention in a polar dispersion medium such as water, ethanol and liquid sugar.
尚、本発明における食品とは、ヒトが摂取する食品及びその製造のための食品素材のみならず、家畜用飼料及びペットフード並びにその製造のための飼料用素材や、ヒト、家畜又はペット用の医薬及びサプリメント並びにその製造のための原料をも包含する。 The food in the present invention is not only food for human consumption and food material for its production, but also for livestock feed and pet food and feed material for its production, for human, livestock or pet use. Also included are pharmaceuticals and supplements and ingredients for their production.
本発明の食品用消泡剤は、食品の製造工程で発生する泡の消泡又は泡立ちの抑制、製造された食品の運搬時や販売時等における泡立ちの抑制に使用することができる。具体的には、例えば、大豆磨砕物である「呉」を蒸煮して豆乳を得る工程を含む豆腐、油揚げ、凍豆腐、豆乳飲料等の製造における使用、発酵工程又は培養工程を含む乳製品等の発酵食品、抗生物質、乳酸菌等の微生物の生産における使用、飲料の製造や製糖等における使用が挙げられる。とりわけ、本発明の食品用消泡剤は、食品の製造において泡を抑制する効果が長時間持続するため、そのような効果の持続が求められる食品の製造工程で好ましく使用できる。 The antifoaming agent for food of the present invention can be used for defoaming foam or suppressing foaming generated in the production process of food, and suppressing foaming during transportation or sale of the manufactured food. Specifically, for example, the use in the production of tofu, fried tofu, frozen tofu, soymilk beverages, etc., including the step of steaming the soy ground product “Kure” to obtain soy milk, dairy products including the fermentation step or culture step, etc. Examples thereof include use in the production of microorganisms such as fermented foods, antibiotics, and lactic acid bacteria, and use in beverage production and sugar production. In particular, the antifoaming agent for foods of the present invention can be preferably used in the production process of foods that are required to maintain such effects because the effect of suppressing foams lasts for a long time in the production of foods.
また、本発明の食品用消泡剤は、タンパク質に起因する泡の消泡又は泡立ちを抑制する効果に優れているため、食品若しくはその原料又はそれらの製造過程における中間原料がタンパク質を含有するものである場合に、そのタンパク質に起因する泡の消泡又は泡立ちを抑制する目的で好ましく使用できる。そのようなタンパク質としては、例えば、牛乳、脱脂粉乳、全粉乳、濃縮乳、クリーム等の乳由来のタンパク質（例えば、カゼインナトリウム）や、豆乳、大豆等の豆由来のタンパク質、卵、動物由来のタンパク質が挙げられる。 In addition, since the antifoaming agent for food of the present invention is excellent in the effect of suppressing foam defoaming or foaming caused by protein, food or its raw material or intermediate raw material in the production process thereof contains protein When it is, it can use preferably for the purpose of suppressing the defoaming or foaming of the foam resulting from the protein. Examples of such proteins include proteins derived from milk such as milk, skim milk powder, whole milk powder, concentrated milk, cream, etc. (eg, sodium caseinate), proteins derived from beans such as soy milk and soybeans, eggs, and animals. Examples include proteins.
本発明の食品用消泡剤を食品に添加して使用する際の添加量に特に制限はないが、例えば、食品若しくはその原料又はそれらの製造過程における中間原料に対し、１０〜２０００ｐｐｍ、好ましくは１０〜５００ｐｐｍ添加することができる。 The amount of addition when the antifoaming agent for food of the present invention is added to food is not particularly limited, but for example, 10 to 2000 ppm, preferably with respect to food or its raw materials or intermediate raw materials in the production process thereof. 10-500 ppm can be added.
以下に本発明を実施例に基づいてより具体的に説明するが、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited thereto.
［製造例１］
先ず、攪拌機、温度計、ガス吹込管及び水分離器を取り付けた反応釜にグリセリン２０ｋｇを仕込み、触媒として水酸化ナトリウム２０ｗ／ｖ％水溶液１００ｍｌを加え、窒素ガス気流中２５０℃で４時間グリセリン縮合反応を行った。得られた反応生成物を約９０℃まで冷却し、リン酸（８５重量％）約２０ｇを添加して中和した後ろ過し、ろ液を１６０℃、２５０Ｐａの条件下で減圧蒸留してグリセリンを除き、更に蒸留残液を、２００℃、２０Ｐａの高真空条件下で真空蒸留してジグリセリンを回収し、更に蒸留残液を、２４０℃、２０Ｐの高真空条件下で真空蒸留し、ジグリセリン８％、トリグリセリン８４％及びテトラグリセリン７．５％を含む留分約１．５ｋｇを得た。該留分に対して１％の活性炭を加え、減圧下にて脱色処理した後ろ過した。得られたトリグリセリン混合物は、水酸基価が１１６５、その平均重合度が約３．０であった。
次に、撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記方法で得たトリグリセリン混合物１７０．８ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１７９．２ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１）約３００ｇを得た。該試作品１のケン化価は２０８．３であった。
[Production Example 1]
First, 20 kg of glycerin was charged into a reaction kettle equipped with a stirrer, thermometer, gas blowing pipe and water separator, 100 ml of a 20 w / v% sodium hydroxide aqueous solution was added as a catalyst, and glycerin condensation was performed at 250 ° C. for 4 hours in a nitrogen gas stream. Reaction was performed. The obtained reaction product was cooled to about 90 ° C., neutralized by adding about 20 g of phosphoric acid (85% by weight), filtered, and the filtrate was distilled under reduced pressure at 160 ° C. and 250 Pa for glycerin. The distiller was further distilled under vacuum at 200 ° C. and 20 Pa under high vacuum conditions to recover diglycerin, and the distiller was further vacuum distilled under high vacuum conditions at 240 ° C. and 20 P. About 1.5 kg of a fraction containing 8% glycerol, 84% triglycerol and 7.5% tetraglycerol was obtained. 1% activated carbon was added to the fraction, decolorized under reduced pressure, and filtered. The obtained triglycerin mixture had a hydroxyl value of 1165 and an average degree of polymerization of about 3.0.
Next, in a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 170.8 g of the triglycerin mixture obtained by the above method, caprylic acid (trade name: NAA-82; day) 179.2 g (manufactured by Oil Co., Ltd.) was added, 1.75 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst, and the esterification reaction was performed at 200 ° C. for 1 hour under a normal pressure in a nitrogen gas stream. The esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 300 g of a food antifoam (prototype 1) which is a polyglycerin fatty acid ester. The saponification value of the prototype 1 was 208.3.
［製造例２］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例１で得たトリグリセリン混合物１４９．１ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）２００．９ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品２）約３００ｇを得た。該試作品２のケン化価は２３７．４であった。
[Production Example 2]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 149.1 g of the triglycerin mixture obtained in Production Example 1 above, caprylic acid (trade name: NAA-82; NOF Corporation) 200.9 g) was added, and 1.75 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. After esterification at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure, the temperature was further increased to 230 ° C. The esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 300 g of an antifoaming agent for food (prototype 2) which is a polyglycerol fatty acid ester. The saponification value of the prototype 2 was 237.4.
［製造例３］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例１で得たトリグリセリン混合物１４０．０ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）２１０．０ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品３）約３００ｇを得た。該試作品３のケン化価は２４７．９であった。
[Production Example 3]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 140.0 g of the triglycerin mixture obtained in Production Example 1 above, caprylic acid (trade name: NAA-82; NOF) 210.0 g) was added, and 1.75 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. After esterification at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure, the temperature was further increased to 230 ° C. The esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 300 g of a food antifoam (prototype 3) which is a polyglycerin fatty acid ester. The saponification value of the prototype 3 was 247.9.
［製造例４］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、テトラグリセリン（商品名：ポリグリセリン＃３１０；平均重合度４；阪本薬品工業社製）１２９．９ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１７０．１ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品４）約２５０ｇを得た。該試作品４のケン化価は２４１．０であった。
[Production Example 4]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 129.9 g of tetraglycerin (trade name: polyglycerin # 310; average polymerization degree 4; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 170.1 g of caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) was added, and 1.5 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. Under normal pressure and in a nitrogen gas stream at 200 ° C. for 1 hour. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 250 g of a food antifoam (prototype 4), which is a polyglycerin fatty acid ester. The saponification value of the prototype 4 was 241.0.
［製造例５］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、ヘキサグリセリン（商品名：ポリグリセリン＃５００；平均重合度６；阪本薬品工業社製）１４１．３ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１５８．７ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品５）約２４０ｇを得た。該試作品５のケン化価は２２６．６であった。
[Production Example 5]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 141.3 g of hexaglycerin (trade name: polyglycerin # 500; average polymerization degree 6; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 158.7 g of caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) was added, and 1.5 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. Under normal pressure and in a nitrogen gas stream at 200 ° C. for 1 hour. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 240 g of a food antifoam (prototype 5) which is a polyglycerin fatty acid ester. The saponification value of the prototype 5 was 226.6.
［製造例６］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた１Ｌの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）５２０．０ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）４８０．０ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液５．０ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約３時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品６）約８５０ｇを得た。該試作品６のケン化価は２０６．６であった。
[Production Example 6]
To a 1 L four-necked flask equipped with a stirrer, a thermometer, a gas blowing tube and a water separator, 520.0 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 480.0 g of caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) was added, and 5.0 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst. Under normal pressure and in a nitrogen gas stream at 200 ° C. for 1 hour. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 3 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 850 g of a food antifoam (prototype 6) which is a polyglycerin fatty acid ester. The saponification value of the prototype 6 was 206.6.
［製造例７］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）１７２．９ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１７７．１ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液1.７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約３時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品７）約２８０ｇを得た。該試作品７のケン化価は２１５．６であった。
[Production Example 7]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 172.9 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 177.1 g of caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) was added, and 1.75 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 3 hours until the acid value became 2.0 or less. The resulting reaction mixture was cooled to obtain about 280 g of a food antifoam (prototype 7) which is a polyglycerin fatty acid ester. The saponification value of the prototype 7 was 215.6.
［製造例８］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）１３４．４ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１６５．６ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液1.５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２．５時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品８）約２３０ｇを得た。該試作品８のケン化価は２３６．６であった。
[Production Example 8]
In a 500 mL four-necked flask equipped with a stirrer, a thermometer, a gas blowing tube and a water separator, 134.4 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 165.6 g of caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) was added, and 1.5 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. Under normal pressure and in a nitrogen gas stream at 200 ° C. for 1 hour. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 2.5 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 230 g of a food antifoaming agent (prototype 8) which is a polyglycerol fatty acid ester. The saponification value of the prototype 8 was 236.6.
［製造例９］
攪拌機、温度計、ガス吹込管及び水分離器を取り付けた反応釜にグリセリン２０ｋｇを仕込み、触媒として水酸化ナトリウム２０ｗ／ｖ％水溶液１００ｍＬを加え、窒素ガス気流中２５０°で４時間グリセリン縮合反応を行った。得られた反応生成物を約９０℃まで冷却し、リン酸（８５重量％）約２０ｇを添加して中和した後ろ過し、ろ液を１６０℃、２５０Ｐａの条件下で減圧蒸留してグリセリンを除き、続いて２００℃、２０Ｐａの高真空条件下で真空蒸留してグリセリン３％、ジグリセリン９２％、トリグリセリン５％を含む留分約３．０ｋｇを得た。該留分に対して１質量％の活性炭を加え、減圧下にて脱色処理した後ろ過した。得られたジグリセリン混合物は、水酸基価が１３５９、その平均重合度が約２．０であった。
次に、撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記方法で得たジグリセリン混合物１７６．６ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１２３．４ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価１．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品９）約２７０ｇを得た。該試作品９のケン化価は１６４．５であった。
[Production Example 9]
Into a reaction kettle equipped with a stirrer, thermometer, gas blowing tube and water separator, 20 kg of glycerin was added, 100 mL of a 20 w / v% sodium hydroxide aqueous solution was added as a catalyst, and a glycerin condensation reaction was performed at 250 ° in a nitrogen gas stream for 4 hours. went. The obtained reaction product was cooled to about 90 ° C., neutralized by adding about 20 g of phosphoric acid (85% by weight), filtered, and the filtrate was distilled under reduced pressure at 160 ° C. and 250 Pa for glycerin. Subsequently, vacuum distillation was performed under high vacuum conditions of 200 ° C. and 20 Pa to obtain about 3.0 kg of a fraction containing 3% glycerin, 92% diglycerin and 5% triglycerin. 1% by mass of activated carbon was added to the fraction, decolorized under reduced pressure, and filtered. The obtained diglycerin mixture had a hydroxyl value of 1359 and an average degree of polymerization of about 2.0.
Next, in a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 176.6 g of the diglycerin mixture obtained by the above method, caprylic acid (trade name: NAA-82; day) (Manufactured by Oil Co., Ltd.) was charged with 123.4 g of sodium hydroxide, and 1.5 mL of a 10 w / v% sodium hydroxide solution was added as a catalyst. The esterification reaction was carried out for about 2 hours until the acid value became 1.0 or less. The obtained reaction mixture was cooled to obtain about 270 g of a food antifoam (prototype 9) which is a polyglycerin fatty acid ester. The saponification value of the prototype 9 was 164.5.
［製造例１０］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例９で得たジグリセリン混合物１２５．１ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１７４．９ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価１．０以下となるまで約２．５時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１０）約２７０ｇを得た。該試作品１０のケン化価は２３９．９であった。
[Production Example 10]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 125.1 g of the diglycerin mixture obtained in Production Example 9 above, caprylic acid (trade name: NAA-82; NOF Corporation) 174.9g), sodium hydroxide 10w / v% aqueous solution 1.5mL was added as a catalyst, and esterification was performed at 200 ° C for 1 hour in a nitrogen gas stream under normal pressure, and the temperature was further increased to 230 ° C. The esterification reaction was carried out for about 2.5 hours until the acid value became 1.0 or less. The obtained reaction mixture was cooled to obtain about 270 g of a food antifoam (prototype 10) which is a polyglycerin fatty acid ester. The saponification value of the prototype 10 was 239.9.
［製造例１１］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例９で得たジグリセリン混合物１０９．２ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１９０．８ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価１．０以下となるまで約３時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１１）約２７０ｇを得た。該試作品１１のケン化価は２６６．６であった。
[Production Example 11]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 109.2 g of the diglycerin mixture obtained in Production Example 9 above, caprylic acid (trade name: NAA-82; NOF Corporation) 190.8 g) was added, and 1.5 mL of a 10 w / v% sodium hydroxide aqueous solution was added as a catalyst. After esterification at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure, the temperature was further increased to 230 ° C. The esterification reaction was carried out for about 3 hours until the acid value became 1.0 or less. The obtained reaction mixture was cooled to obtain about 270 g of a food antifoam (prototype 11) which is a polyglycerin fatty acid ester. The saponification value of the prototype 11 was 266.6.
［製造例１２］
撹拌機、温度計、ガス吹込管および水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例１で得たトリグリセリン混合物７６．５ｇ、ラウリン酸（商品名：ラウリン酸９８；ミヨシ油脂社製）２２３．５ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約３時間エステル化反応を行った。得られた反応混合物を冷却して食品用消泡剤（試作品１２）約２６０ｇを得た。該試作品１２のケン化価は２２０．５であった。
[Production Example 12]
In a 500 mL four-necked flask equipped with a stirrer, a thermometer, a gas blowing tube and a water separator, 76.5 g of the triglycerin mixture obtained in Production Example 1 above, lauric acid (trade name: lauric acid 98; Miyoshi oil and fat 223.5 g), sodium hydroxide 10 w / v% aqueous solution 1.5 mL was added, and the esterification reaction was performed at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure. The esterification reaction was carried out for about 3 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 260 g of a food antifoam (prototype 12). The saponification value of the prototype 12 was 220.5.
［製造例１３］
撹拌機、温度計、ガス吹込管および水分離器を取り付けた１Ｌの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）１２７．８ｇ、カプリン酸（商品名：ＮＡＡ−１０２；日油社製）１７２．２ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却して食品用消泡剤（試作品１３）約２５０ｇを得た。該試作品１３のケン化価は２０４．０であった。
[Production Example 13]
To a 1 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), 127.8 g, Capric acid (trade name: NAA-102; manufactured by NOF Corporation) was charged with 172.2 g, and 1.5 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 250 g of a food antifoam (prototype 13). The saponification value of the prototype 13 was 204.0.
［製造例１４］
撹拌機、温度計、ガス吹込管および水分離器を取り付けた１Ｌの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）９５．７ｇ、ラウリン酸（商品名：ラウリン酸９８；ミヨシ油脂社製）２０４．３ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価３．０以下となるまで約３時間エステル化反応を行った。得られた反応混合物を冷却して食品用消泡剤（試作品１４）約２６０ｇを得た。該試作品１４のケン化価は２０６．７であった。
[Production Example 14]
In a 1 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 95.7 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), 204.3 g of lauric acid (trade name: lauric acid 98; manufactured by Miyoshi Oil & Fats Co., Ltd.) was added, and 1.5 mL of a 10 w / v% sodium hydroxide aqueous solution was added as a catalyst. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 3 hours until the acid value became 3.0 or less. The obtained reaction mixture was cooled to obtain about 260 g of a food antifoam (prototype 14). The saponification value of the prototype 14 was 206.7.
［製造例１５］
撹拌機、温度計、ガス吹込管および水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例１で得たトリグリセリン混合物１７１．３ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１２８．７ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価１．０以下となるまで約１時間エステル化反応を行った。得られた反応混合物を冷却して食品用消泡剤（試作品１５）約２６０ｇを得た。該試作品１５のケン化価は１６８．７であった。
[Production Example 15]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 171.3 g of the triglycerin mixture obtained in Production Example 1 above, caprylic acid (trade name: NAA-82; NOF) 128.7 g), and 1.5 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst. After esterification at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure, the temperature was further raised to 230 ° C. The esterification reaction was carried out for about 1 hour until the acid value became 1.0 or less. The obtained reaction mixture was cooled to obtain about 260 g of a food antifoam (prototype 15). The saponification value of the prototype 15 was 168.7.
［製造例１６］
撹拌機、温度計、ガス吹込管および水分離器を取り付けた５００ｍＬの四つ口フラスコに、上記製造例１で得たトリグリセリン混合物１０７．１ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１９２．９ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液１．５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価１．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却して食品用消泡剤（試作品１６）約２５０ｇを得た。該試作品１６のケン化価は２６６．６であった。
[Production Example 16]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 107.1 g of the triglycerin mixture obtained in Production Example 1 above, caprylic acid (trade name: NAA-82; NOF Corporation) 192.9 g) was added, 1.5 mL of a 10 w / v aqueous solution of sodium hydroxide was added as a catalyst, esterified at 200 ° C. for 1 hour in a nitrogen gas stream under normal pressure, and the temperature was further increased to 230 ° C. The esterification reaction was carried out for about 2 hours until the acid value became 1.0 or less. The obtained reaction mixture was cooled to obtain about 250 g of a food antifoam (prototype 16). The saponification value of the prototype 16 was 266.6.
［製造例１７］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）２１６．６ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）１３３．４ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液1.７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約２時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１７）約２９０ｇを得た。該試作品１７のケン化価は１６０．９であった。
[Production Example 17]
In a 500 mL four-necked flask equipped with a stirrer, a thermometer, a gas blowing tube, and a water separator, 216.6 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), Capillic acid (trade name: NAA-82; manufactured by NOF Corporation) was charged with 133.4 g, and 1.75 mL of a 10 w / v% aqueous solution of sodium hydroxide was added as a catalyst. Under normal pressure and in a nitrogen gas stream at 200 ° C. for 1 hour. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 2 hours until the acid value became 2.0 or less. The resulting reaction mixture was cooled to obtain about 290 g of a food antifoam (prototype 17), which is a polyglycerin fatty acid ester. The saponification value of the prototype 17 was 160.9.
［製造例１８］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた５００ｍＬの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）１４３．５ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）２０６．５ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液1.７５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価２．０以下となるまで約５時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１８）約２９０ｇを得た。該試作品１８のケン化価は２５３．１であった。
[Production Example 18]
In a 500 mL four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 143.5 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), Capillic acid (trade name: NAA-82; manufactured by NOF Corporation) is charged with 206.5 g, and 1.75 mL of a 10 w / v% aqueous solution of sodium hydroxide is added as a catalyst. After the esterification reaction, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 5 hours until the acid value became 2.0 or less. The obtained reaction mixture was cooled to obtain about 290 g of an antifoaming agent for food (prototype 18) which is a polyglycerin fatty acid ester. The saponification value of the prototype 18 was 253.1.
［製造例１９］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた１Ｌの四つ口フラスコに、デカグリセリン（商品名：ポリグリセリン＃７５０；平均重合度１０；阪本薬品工業社製）３４１．１ｇ、カプリル酸（商品名：ＮＡＡ−８２；日油社製）５５８．９ｇを仕込み、触媒として水酸化ナトリウム１０ｗ／ｖ％水溶液４.５ｍＬを加え、常圧下、窒素ガス気流中、２００℃で１．５時間エステル化反応した後、さらに温度を２３０℃に上げ、酸価３．０以下となるまで約７時間エステル化反応を行った。得られた反応混合物を冷却してポリグリセリン脂肪酸エステルである食品用消泡剤（試作品１９）約２９０ｇを得た。該試作品１９のケン化価は２６６．７であった。
[Production Example 19]
To a 1 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, 341.1 g of decaglycerin (trade name: polyglycerin # 750; average polymerization degree 10; manufactured by Sakamoto Pharmaceutical Co., Ltd.), Caprylic acid (trade name: NAA-82; manufactured by NOF Corporation) (558.9 g) was added, and a sodium hydroxide 10 w / v% aqueous solution (4.5 mL) was added as a catalyst, followed by 1. at 200 ° C. in a nitrogen gas stream under normal pressure. After the esterification reaction for 5 hours, the temperature was further raised to 230 ° C., and the esterification reaction was carried out for about 7 hours until the acid value became 3.0 or less. The obtained reaction mixture was cooled to obtain about 290 g of an antifoaming agent for food (prototype 19) which is a polyglycerol fatty acid ester. The saponification value of the prototype 19 was 266.7.
製造例１〜１９で得た食品用消泡剤（試作品１〜１９）のうち、試作品１〜８について、ポリグリセリンの平均重合度、構成脂肪酸の種類及びケン化価（ｍｇ）を表１に示す。また、これら食品用消泡剤のうち、試作品９〜１９について、ポリグリセリンの平均重合度、構成脂肪酸の種類及びケン化価（ｍｇ）を表２に示す。ここで、表１に示す試作品１〜８は本発明の実施例であり、表２に示す試作品９〜１９は、これらに対する比較例である。また、表２には、比較例として、市販の食品用乳化剤（市販品１〜６）並びにこれらについてポリグリセリンの平均重合度、構成脂肪酸の種類及びケン化価（ｍｇ）を併せて示す。 Among the antifoaming agents for foods obtained in Production Examples 1 to 19 (prototypes 1 to 19), the average degree of polymerization of polyglycerol, the type of constituent fatty acid, and the saponification value (mg) are shown for prototypes 1 to 8. It is shown in 1. Table 2 shows the average degree of polymerization of polyglycerin, the type of constituent fatty acids, and the saponification value (mg) for prototypes 9 to 19 among these antifoaming agents for food. Here, prototypes 1 to 8 shown in Table 1 are examples of the present invention, and prototypes 9 to 19 shown in Table 2 are comparative examples for these. Moreover, in Table 2, as a comparative example, the commercially available emulsifier for foodstuffs (commercial goods 1-6) and the average polymerization degree of polyglycerol, the kind of constituent fatty acid, and a saponification value (mg) are shown collectively about these.
［消泡性能の評価試験］
上記製造例１〜１９で製造した食品用消泡剤（試作品１〜１９）及び市販の食品用乳化剤（表２に示す市販品１〜６）について下記試験方法により消泡性能の評価試験を実施した。また、対照として、消泡剤・乳化剤を使用せずに同様に試験を実施した。結果を表３に示す。
＜試験方法＞
カゼインナトリウム５．０ｇ及びグラニュー糖５００．０ｇの混合物に水道水を加えて全体で５ｋｇとした。これを約７０℃に加温し、カゼインナトリウムが溶解するまで撹拌した。次に、これを２５℃まで冷却した後、蒸発した水分を補正するために減少した重量分の水道水を加えた。これを再び２５℃に調整し、試験液とした。
上記試験液２００ｇを５００ｍＬ容トールビーカーに入れ、食品用消泡剤又は食品用乳化剤０．０１ｇを添加し、マグネチックスターラー（３５×８ｍｍの撹拌子使用）を用いて５００ｒｐｍにて３０秒間撹拌し、食品用消泡剤又は食品用乳化剤を試験液に分散させた。その後、ガラスボールフィルター（製品名：キノシタボールフィルター５０１Ｇ−４；木下理化工業製）を通じて乾燥窒素を０．３（Ｌ／分）の速度で試験液に送り込み、微細な泡を発生させた。そして、通気の開始から１０分以内に泡の上面の位置がビーカーの５００ｍＬ目盛りに到達した場合は、消泡効果が十分に得られていない（即ち、「×」）と判定した上で、その到達時間を記録し、試験を終了した。また、通気の開始から１０分が経過しても泡の上面の位置がビーカーの５００ｍＬ目盛りに到達しなかった場合は、消泡効果が十分に得られている（即ち、「○」）と判定した上で、ビーカーの目盛りを利用して泡の上面の位置（ｍＬ）を読み取り、試験を終了した。
[Evaluation test of defoaming performance]
About the antifoaming agent for foodstuffs manufactured in the said manufacture examples 1-19 (prototypes 1-19) and the commercially available emulsifier for foodstuffs (commercial goods 1-6 shown in Table 2), the evaluation test of antifoaming performance is carried out by the following test method. Carried out. Further, as a control, the same test was conducted without using an antifoaming agent / emulsifier. The results are shown in Table 3.
<Test method>
Tap water was added to a mixture of sodium casein 5.0 g and granulated sugar 500.0 g to make a total of 5 kg. This was heated to about 70 ° C. and stirred until sodium caseinate was dissolved. Next, after cooling this to 25 ° C., a reduced weight of tap water was added to correct the evaporated water. This was again adjusted to 25 ° C. to obtain a test solution.
Add 200 g of the above test solution to a 500 mL tall beaker, add 0.01 g of a food antifoam or food emulsifier, and stir at 500 rpm for 30 seconds using a magnetic stirrer (using a 35 × 8 mm stirrer). The food antifoaming agent or food emulsifier was dispersed in the test solution. Thereafter, dry nitrogen was fed into the test solution at a rate of 0.3 (L / min) through a glass ball filter (product name: Kinoshita Ball Filter 501G-4; manufactured by Kinoshita Rika Kogyo) to generate fine bubbles. And when the position of the upper surface of the foam reaches the 500 mL scale of the beaker within 10 minutes from the start of ventilation, it is determined that the defoaming effect is not sufficiently obtained (that is, “×”), The arrival time was recorded and the test was terminated. Further, if the position of the upper surface of the foam does not reach the 500 mL scale of the beaker even after 10 minutes have passed since the start of ventilation, it is determined that the defoaming effect is sufficiently obtained (that is, “◯”). Then, the position (mL) of the upper surface of the foam was read using the scale of the beaker, and the test was completed.
表３から明らかなように、本発明の食品用消泡剤（試作品１〜８）の使用により、試験液への通気開始から１０分が経過しても、その泡の上面の位置は５００ｍＬ以下であり、十分に泡が抑制されていた。これに対し、比較例の食品用消泡剤及び食品用乳化剤（試作品９〜１９及び市販品１〜６）を添加した場合、並びに食品用消泡剤等を添加しなかった場合では、試験液への通気開始から１０分以内に泡の上面の位置が５００ｍＬに到達し、十分な効果が得られなかった。 As is clear from Table 3, the use of the antifoaming agent for food of the present invention (prototypes 1 to 8) allows the position of the top surface of the foam to be 500 mL even after 10 minutes have passed since the start of aeration to the test solution. The bubbles were sufficiently suppressed. On the other hand, when the food antifoaming agent and the food emulsifier of the comparative example (prototypes 9 to 19 and commercial products 1 to 6) were added, and when the food antifoaming agent was not added, the test The position of the upper surface of the foam reached 500 mL within 10 minutes from the start of aeration to the liquid, and a sufficient effect was not obtained.
Claims (1)
（Ａ）ポリグリセリンの平均重合度が３〜１２
（Ｂ）構成脂肪酸がカプリル酸
（Ｃ）ケン化価が２００〜２５０ An antifoaming agent for foods comprising a polyglycerin fatty acid ester satisfying the following conditions (A), (B) and (C) as an active ingredient.
(A) The average degree of polymerization of polyglycerin is 3-12
(B) Constituent fatty acid is caprylic acid (C) Saponification value is 200-250
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