JP5089899B2 - Polyoxyethylene sorbitan fatty acid ester composition - Google Patents
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Description
本発明は、高品質なポリオキシエチレンソルビタン脂肪酸エステル組成物及びその製造法に関する。 The present invention relates to a high-quality polyoxyethylene sorbitan fatty acid ester composition and a method for producing the same.
ポリオキシエチレンソルビタン脂肪酸エステルは、ソルビトール及び／又はその無水物と脂肪酸との部分エステルの混合物であるソルビタン脂肪酸エステル（モノエステル、トリエステル）にエチレンオキサイドを付加させたもので、非イオン界面活性剤として有用であり、化粧品、洗浄剤等に広く使用されている。 Polyoxyethylene sorbitan fatty acid ester is a nonionic surfactant obtained by adding ethylene oxide to sorbitan fatty acid ester (monoester, triester), which is a mixture of partial esters of sorbitol and / or its anhydride and fatty acid. And is widely used in cosmetics, cleaning agents and the like.
また、２００３年には新規指定の食品添加物として、ポリソルベート２０（ポリオキシエチレン（２０）ソルビタンモノラウリン酸エステル）、ポリソルベート６０（ポリオキシエチレン（２０）ソルビタンモノステアリン酸エステル）、ポリソルベート６５（ポリオキシエチレン（２０）ソルビタントリステアリン酸エステル）、ポリソルベート８０（ポリオキシエチレン（２０）ソルビタンモノオレイン酸エステル）が指定されている。 Further, in 2003, as newly specified food additives, polysorbate 20 (polyoxyethylene (20) sorbitan monolaurate), polysorbate 60 (polyoxyethylene (20) sorbitan monostearate), polysorbate 65 (polyoxyester) Ethylene (20) sorbitan tristearate) and polysorbate 80 (polyoxyethylene (20) sorbitan monooleate) are specified.
品質の良好なポリオキシエチレンソルビタン脂肪酸エステルの製造法としては、例えば特許文献１に、ポリオキシエチレンソルビタン脂肪酸エステルに対して、特定のリン酸化合物を添加することにより、加熱着色が改良されることが記載されている。しかし、これら従来の製造法で得られるポリオキシエチレンソルビタン脂肪酸エステルは、風味が悪く、食品添加物としては不十分である。 As a method for producing a polyoxyethylene sorbitan fatty acid ester having good quality, for example, in Patent Document 1, by adding a specific phosphoric acid compound to polyoxyethylene sorbitan fatty acid ester, heat coloring can be improved. Is described. However, the polyoxyethylene sorbitan fatty acid esters obtained by these conventional production methods have poor flavor and are insufficient as food additives.
また、特許文献２にはポリオキシエチレンソルビタン脂肪酸エステルの風味を改善する方法が開示されている。 Patent Document 2 discloses a method for improving the flavor of polyoxyethylene sorbitan fatty acid ester.
ポリオキシエチレンソルビタン脂肪酸エステルを食品添加物として用いる場合には様々な規格を満たす必要があり、また、外観が透明で低温安定性に優れるものが要望されている。しかし、かかるポリオキシエチレンソルビタン脂肪酸エステルについてはこれまで報告されていない。
本発明の課題は、外観が透明で低温安定性に優れ、更に食品添加物として用いることができる程に高品質なポリオキシエチレンソルビタン脂肪酸エステル組成物及びその製造法を提供することにある。 An object of the present invention is to provide a polyoxyethylene sorbitan fatty acid ester composition that is transparent in appearance and excellent in low-temperature stability and that can be used as a food additive, and a method for producing the same.
本発明は、ソルビタン脂肪酸エステルにエチレンオキサイドを付加させて得られるポリオキシエチレンソルビタン脂肪酸エステル組成物であって、該ポリオキシエチレンソルビタン脂肪酸エステル組成物中の脂肪酸組成が、パルミチン酸量４５〜７５重量％、ステアリン酸量１５〜４５重量％であり、且つ、該組成物中の水分量が１重量％以下、２０℃のｐＨが４．５〜６．０であるポリオキシエチレンソルビタン脂肪酸エステル組成物、並びにその製造法を提供する。
The present invention is a polyoxyethylene sorbitan fatty acid ester composition obtained by adding ethylene oxide to sorbitan fatty acid esters, fatty acid group formed of the polyoxyethylene sorbitan fatty acid ester composition is the amount of palmitic acid 45 A polyoxyethylene sorbitan fatty acid ester having 75% by weight, an amount of stearic acid of 15 to 45% by weight, a water content of the composition of 1% by weight or less, and a pH of 4.5 to 6.0 at 20 ° C. Compositions and methods for their production are provided.
本発明により、外観が透明で低温安定性に優れた高品質なポリオキシエチレンソルビタン脂肪酸エステル組成物を提供することができ、特に食品添加物として有用なポリオキシエチレンソルビタン脂肪酸エステル組成物を提供することができる。 According to the present invention, it is possible to provide a high-quality polyoxyethylene sorbitan fatty acid ester composition that is transparent in appearance and excellent in low-temperature stability, and particularly provides a polyoxyethylene sorbitan fatty acid ester composition that is useful as a food additive. be able to.
本発明におけるポリオキシエチレンソルビタン脂肪酸エステル組成物中の脂肪酸組成は、全脂肪酸中のパルミチン酸量が４５〜７５重量％、ステアリン酸量が１５〜４５重量％である。食品添加物として用いる場合には、全脂肪酸中のパルミチン酸量は６０〜６９重量％が好ましく、６０〜６８重量％がより好ましい。また、ステアリン酸量は３１〜４０重量％が好ましく、３２〜４０重量％がより好ましい。脂肪酸組成は上記パルミチン酸やステアリン酸以外にもミリスチン酸等のその他の高級脂肪酸が多少含まれていても構わない。具体的には１０重量％以内、より好ましくは５重量％以内である。
Fatty acid group forming a polyoxyethylene sorbitan fatty acid ester composition of the present invention, the amount of palmitic acid 45-75% by weight of the total fatty acids, the amount of stearic acid is 15 to 45 wt%. When used as a food additive, palmitic acid content in the total fatty acids is preferably from 60 to 69 wt%, more preferably 60 to 68 wt%. The amount of stearic acid is preferably 31 to 40% by weight, and more preferably 32 to 40% by weight. Sets formed fatty acid may be contained some other higher fatty acids such as myristic acid also outside these palmitic acid and stearic San以. Specifically, it is within 10% by weight, more preferably within 5% by weight.
尚、本発明において、ポリオキシエチレンソルビタン脂肪酸エステル組成物の脂肪酸組成は、以下の方法で分析することができる。
In the present invention, the fatty acid group forming a polyoxyethylene sorbitan fatty acid ester composition can be analyzed by the following method.
５０mlサンプル管にポリオキシエチレンソルビタン脂肪酸エステル組成物を０．２ｇ計り取る。１／２Ｎ水酸化カリウム水溶液を５ml加え、１００℃、１時間の条件で鹸化分解を行う。その後、水５mlを加え、pH１になるまで２Ｎ塩酸水溶液を加える。ジエチルエーテル１０mlで抽出を３回行い、抽出されたジエチルエーテル層を水洗する。その後ジエチルエーテルを留去した後、ガスクロマトグラフィーにて脂肪酸組成を分析する。
Weigh 0.2 g of polyoxyethylene sorbitan fatty acid ester composition into a 50 ml sample tube. 5 ml of 1 / 2N potassium hydroxide aqueous solution is added, and saponification decomposition is performed at 100 ° C. for 1 hour. Then 5 ml of water is added and 2N aqueous hydrochloric acid is added until pH 1 is reached. Extraction is performed 3 times with 10 ml of diethyl ether, and the extracted diethyl ether layer is washed with water. After then distilling off the diethyl ether, to analyze sets fatty acid formation by gas chromatography.
本発明のポリオキシエチレンソルビタン脂肪酸エステル組成物の製造原料であるソルビタン脂肪酸エステルは、ソルビトール及び／又はソルビタンと、脂肪酸とを、窒素ガス気流下、通常１６０〜２８０℃の温度で、生成水を留去させながら反応させることにより合成することができる。より具体的には、特開２００２−２８４７７３号に記載の方法等が利用できる。 The sorbitan fatty acid ester, which is a raw material for producing the polyoxyethylene sorbitan fatty acid ester composition of the present invention, contains sorbitol and / or sorbitan and a fatty acid in a stream of nitrogen gas at a temperature of usually 160 to 280 ° C. It can be synthesized by reacting while leaving. More specifically, the method described in JP-A-2002-284773 can be used.
原料脂肪酸としては、ポリオキシエチレンソルビタン脂肪酸エステル組成物の脂肪酸組成と同様の組成を有するものを用いることが好ましい。また、原料脂肪酸の鹸化価は、２０９〜２１４が好ましく、食品添加物として用いる場合は２１０〜２１２が更に好ましい。
As the raw material fatty acid, it is preferable to use those having the same composition as the fatty acid group forming a polyoxyethylene sorbitan fatty acid ester composition. The saponification value of the raw fatty acid is preferably 209 to 214, and more preferably 210 to 212 when used as a food additive.
ソルビトールはエステル化反応時にソルビトール自身の分子内脱水反応が起こり、水１分子の脱水でソルビタンに、水２分子の脱水でソルバイドになる。従って、本発明で対象となるポリオキシエチレンソルビタン脂肪酸エステル組成物は、ソルビトールエステル、ソルビタンエステル、ソルバイドエステルの混合物にエチレンオキサイドを付加反応させたものである。 Sorbitol undergoes an intramolecular dehydration reaction during the esterification reaction, and becomes sorbitan by dehydration of one molecule of water and becomes sorbide by dehydration of two molecules of water. Therefore, the polyoxyethylene sorbitan fatty acid ester composition which is the subject of the present invention is obtained by adding ethylene oxide to a mixture of sorbitol ester, sorbitan ester and sorbide ester.
ソルビタン脂肪酸エステルを得る際の脂肪酸の使用量は、ソルビトール及び／又はソルビタンに対してモル比で、脂肪酸：ソルビトール及び／又はソルビタン＝（０．５〜５）：１が好ましく、（０．８〜３．５）：１が特に好ましい。 The amount of fatty acid used in obtaining the sorbitan fatty acid ester is preferably a fatty acid: sorbitol and / or sorbitan = (0.5 to 5): 1 in a molar ratio with respect to sorbitol and / or sorbitan, (0.8 to 3.5): 1 is particularly preferred.
ソルビトール及び／又はソルビタンと脂肪酸との反応で得られるソルビタン脂肪酸エステルは、ソルビトール及び／又はソルビタンと脂肪酸との部分エステルの混合物であるが、これらの中で本発明に用いるソルビタン脂肪酸エステルは、平均エステル化度においてモノエステル又はトリエステルが好ましく、モノエステルがより好ましい。また、ソルビタン脂肪酸エステルの鹸化価は、１４５〜１５６が好ましく、１４６〜１５３が更に好ましい。 The sorbitan fatty acid ester obtained by the reaction of sorbitol and / or sorbitan and a fatty acid is a mixture of sorbitol and / or a partial ester of sorbitan and a fatty acid. Among them, the sorbitan fatty acid ester used in the present invention is an average ester. In terms of the degree of conversion, monoesters or triesters are preferred, and monoesters are more preferred. The saponification value of sorbitan fatty acid ester is preferably 145 to 156, more preferably 146 to 153.
本発明のポリオキシエチレンソルビタン脂肪酸エステル組成物は、ソルビタン脂肪酸エステルにエチレンオキサイドを付加させることにより得られる。エチレンオキサイドの平均付加モル数は、１５〜３０が好ましく、特に食品添加物として用いる場合は２０〜２５が更に好ましく、２０〜２２が特に好ましい。 The polyoxyethylene sorbitan fatty acid ester composition of the present invention is obtained by adding ethylene oxide to a sorbitan fatty acid ester. The average added mole number of ethylene oxide is preferably 15 to 30, more preferably 20 to 25, and particularly preferably 20 to 22 when used as a food additive.
ソルビタン脂肪酸エステルへのエチレンオキサイドの付加反応は、従来から知られる触媒を使用することができ、特に限定されないが、例えば水酸化カリウム、水酸化ナトリウム、ナトリウムメチラート等のアルカリ金属触媒、脂肪酸石鹸類等が使用される。エチレンオキサイド付加反応の反応温度は８０〜２００℃が好ましく、１４０〜１８０℃が更に好ましい。また、反応圧力は０．１〜０．８ＭＰａが好ましく、０．１〜０．６ＭＰａが更に好ましい。 The addition reaction of ethylene oxide to sorbitan fatty acid ester can use a conventionally known catalyst, and is not particularly limited. For example, alkali metal catalysts such as potassium hydroxide, sodium hydroxide and sodium methylate, fatty acid soaps Etc. are used. The reaction temperature of the ethylene oxide addition reaction is preferably 80 to 200 ° C, more preferably 140 to 180 ° C. The reaction pressure is preferably from 0.1 to 0.8 MPa, more preferably from 0.1 to 0.6 MPa.
本発明のポリオキシエチレンソルビタン脂肪酸エステル組成物は、外観が透明で優れた低温安定性を得る観点から、水分量が１重量％以下で、２０℃のｐＨが４．５〜６．０である。食品添加物として用いる場合は、水分量は０．５重量％以下が好ましく、２０℃のｐＨは５．０〜６．０が好ましい。 The polyoxyethylene sorbitan fatty acid ester composition of the present invention has a water content of 1% by weight or less and a pH at 20 ° C. of 4.5 to 6.0 from the viewpoint of transparent appearance and excellent low temperature stability. . When used as a food additive, the water content is preferably 0.5% by weight or less, and the pH at 20 ° C. is preferably 5.0 to 6.0.
尚、ポリオキシエチレンソルビタン脂肪酸エステル組成物の水分量は、ＪＩＳ Ｋ ００６８の方法に準じて測定し、ｐＨは、ポリオキシエチレンソルビタン脂肪酸エステル組成物を５重量％水溶液に希釈して２０℃の条件下、ガラス電極（東亜電波製）で測定する。 The water content of the polyoxyethylene sorbitan fatty acid ester composition is measured according to the method of JIS K 0068, and the pH is a condition of 20 ° C. by diluting the polyoxyethylene sorbitan fatty acid ester composition into a 5% by weight aqueous solution. Lower, measure with a glass electrode (manufactured by Toa Denpa).
本発明のポリオキシエチレンソルビタン脂肪酸エステル組成物は、上記のようなソルビタン脂肪酸エステルにエチレンオキサイドを付加して得られる反応粗製物を、脱色処理、中和処理、水蒸気処理、蒸留処理及び水分調整から選ばれる少なくとも１種の処理を行なうことにより得ることができる。特に脱色処理及び／又は中和処理後に、必要により水蒸気処理を行うか又は蒸留処理を行い、更に水分を調整して、水分量が１重量％以下、２０℃のｐＨが４．５〜６．０のポリオキシエチレンソルビタン脂肪酸エステル組成物を得ることが好ましい。 The polyoxyethylene sorbitan fatty acid ester composition of the present invention comprises a reaction crude product obtained by adding ethylene oxide to the sorbitan fatty acid ester as described above, from decolorization treatment, neutralization treatment, steam treatment, distillation treatment and moisture adjustment. It can be obtained by performing at least one selected treatment. In particular, after the decolorization treatment and / or neutralization treatment, if necessary, a steam treatment or a distillation treatment is carried out to further adjust the water content, so that the water content is 1% by weight or less and the pH at 20 ° C. is 4.5-6. It is preferred to obtain a zero polyoxyethylene sorbitan fatty acid ester composition.
脱色処理は、一般に過酸化水素等の脱色剤を用いて行う。脱色剤の添加量は、３５％過酸化水素水の場合、反応粗製物１００重量部に対し、０．０１〜１．０重量部が好ましく、０．０５〜０．５重量部が更に好ましい。脱色処理の温度は、７０〜１００℃が好ましく、処理時間は０．５〜２時間が好ましい。この脱色処理では同時に反応粗製物が中和される。 The decoloring treatment is generally performed using a decoloring agent such as hydrogen peroxide. In the case of 35% hydrogen peroxide solution, the addition amount of the decolorizing agent is preferably 0.01 to 1.0 part by weight, more preferably 0.05 to 0.5 part by weight with respect to 100 parts by weight of the reaction crude product. The temperature for the decolorization treatment is preferably 70 to 100 ° C., and the treatment time is preferably 0.5 to 2 hours. In this decolorization treatment, the reaction crude product is simultaneously neutralized.
この脱色処理の代わりに、あるいは脱色処理と併用して、中和処理を行うこともできる。中和処理に用いられる中和剤は特に限定されないが、例えばリン酸、硫酸等の鉱酸、あるいは酢酸、乳酸、クエン酸等の有機酸を使用することができ、これら２種以上を混合あるいは併用してもよい。中和剤は、反応粗製物のｐＨが４．５〜６．０となるように添加することが好ましい。 A neutralization treatment can also be performed in place of or in combination with the decolorization treatment. Although the neutralizing agent used for the neutralization treatment is not particularly limited, for example, a mineral acid such as phosphoric acid and sulfuric acid, or an organic acid such as acetic acid, lactic acid, and citric acid can be used. You may use together. The neutralizing agent is preferably added so that the reaction crude product has a pH of 4.5 to 6.0.
水蒸気処理は、ソルビタン脂肪酸エステルにエチレンオキサイドを付加して得られる反応粗製物に、水蒸気を流通等で接触させることにより該反応粗製物中の不純物等を水蒸気と共に系外へ除去する処理である。 The steam treatment is a treatment for removing impurities and the like in the reaction crude product out of the system together with water vapor by bringing steam into contact with the reaction crude product obtained by adding ethylene oxide to sorbitan fatty acid ester.
また蒸留処理は、ソルビタン脂肪酸エステルにエチレンオキサイドを付加して得られる反応粗製物に、水を添加して該反応粗製物中の不純物等を水と共に蒸留により系外へ除去する処理である。 The distillation treatment is a treatment in which water is added to a reaction crude product obtained by adding ethylene oxide to sorbitan fatty acid ester, and impurities and the like in the reaction crude product are removed out of the system together with water.
水蒸気処理又は蒸留処理で使用する水蒸気又は水の量は、反応粗製物１００重量部に対して６〜２０重量部が好ましく、８〜１２重量部がより好ましい。水蒸気処理又は蒸留処理の温度は、処理を効率良く行い、工業的に設備にかかる負荷を小さくする観点から、６０〜２００℃が好ましく、８０〜１６０℃が更に好ましい。水蒸気処理は常圧又は減圧下で行うことができるが、一般的には減圧下で行う方が効率的であり、その場合の圧力は２７ｋＰａ以下が好ましく、７ｋＰａ以下が更に好ましい。また、蒸留処理は、減圧下で行い、圧力は２７ｋＰａ以下が好ましく、７ｋＰａ以下が更に好ましい。 The amount of water vapor or water used in the water vapor treatment or distillation treatment is preferably 6 to 20 parts by weight, more preferably 8 to 12 parts by weight with respect to 100 parts by weight of the reaction crude product. The temperature of the steam treatment or the distillation treatment is preferably 60 to 200 ° C., more preferably 80 to 160 ° C. from the viewpoint of efficiently performing the treatment and reducing the industrial load on the equipment. Although the steam treatment can be performed under normal pressure or reduced pressure, it is generally more efficient to perform the treatment under reduced pressure. In this case, the pressure is preferably 27 kPa or less, and more preferably 7 kPa or less. Further, the distillation treatment is performed under reduced pressure, and the pressure is preferably 27 kPa or less, and more preferably 7 kPa or less.
水分調整は、水分量が１重量％以下となるように、減圧下で脱水することが好ましい。この場合の温度は110〜130℃が好ましく、115〜120℃が更に好ましい。また、圧力は2.7ｋＰａ以下が好ましく、1.3ｋＰａ以下が更に好ましい。 In the moisture adjustment, it is preferable to dehydrate under reduced pressure so that the moisture content is 1% by weight or less. In this case, the temperature is preferably 110 to 130 ° C, more preferably 115 to 120 ° C. The pressure is preferably 2.7 kPa or less, and more preferably 1.3 kPa or less.
例中の「％」は、特記しない限り「重量％」である。 “%” In the examples is “% by weight” unless otherwise specified.
実施例１
パルミチン酸／ステアリン酸＝６３％／３７％（鹸化価＝２１０．６）に調整した脂肪酸５４１．３ｇ、７０％ソルビト−ル水溶液（JIS品）４４２．０ｇ、４８％水酸化ナトリウム４．２ｇ、７５％リン酸１．６ｇを温度計、攪拌器、窒素管、留出/減圧管を装着した２Ｌ四つ口フラスコにとり、窒素ガスにより反応系内を十分に窒素置換し、空気を追い出した後、加熱し２４５℃の温度で精製水を留去させながら５時間エステル化反応を行い、濾過により触媒を除去した。生成物の鹸化価は１４９．８ｍｇＫＯＨ/ｇであった。この方法で得られたソルビタン脂肪酸エステル４８０．８ｇと４８％水酸化カリウム０．４７ｇをオートクレ−ブ（容量５リットル）にとり、１１０℃、２．７ｋＰａ（２０torr）で１時間脱水した後、１５５℃でエチレンオキサイド９９１ｇを０．４ＭＰａで圧入しながら２．５時間で付加反応を行った。
Example 1
541.3 g of fatty acid adjusted to palmitic acid / stearic acid = 63% / 37% (saponification number = 20.6), 442.0 g of 70% aqueous sorbitol solution (JIS product), 4.2 g of 48% sodium hydroxide, After 1.6 g of 75% phosphoric acid was placed in a 2 L four-necked flask equipped with a thermometer, stirrer, nitrogen tube, and distillation / decompression tube, the reaction system was sufficiently purged with nitrogen and purged of air. The esterification reaction was carried out for 5 hours while heating and distilling off purified water at a temperature of 245 ° C., and the catalyst was removed by filtration. The saponification value of the product was 149.8 mg KOH / g. 480.8 g of sorbitan fatty acid ester and 0.47 g of 48% potassium hydroxide obtained by this method were placed in an autoclave (capacity 5 liters), dehydrated at 110 ° C. and 2.7 kPa (20 torr) for 1 hour, and then 155 ° C. Then, an addition reaction was carried out in 2.5 hours while injecting 991 g of ethylene oxide at 0.4 MPa.
反応終了後、同一温度で１時間熟成を行った後、９０℃まで冷却した。後処理として、得られた反応粗製物に３５％過酸化水素水溶液２．８６ｇを加えて１時間処理した。その後９０℃、２．７ｋＰａ（２０torr）で０．５時間脱水し、８８％乳酸０．４８ｇで０．５時間かけて中和し、水分０．１％、ｐＨ（２０℃）５．２のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。 After completion of the reaction, the mixture was aged at the same temperature for 1 hour and then cooled to 90 ° C. As a post-treatment, 2.86 g of 35% aqueous hydrogen peroxide solution was added to the obtained reaction crude product and treated for 1 hour. Thereafter, the mixture was dehydrated at 90 ° C. and 2.7 kPa (20 torr) for 0.5 hour, neutralized with 0.48 g of 88% lactic acid over 0.5 hour, water content 0.1%, pH (20 ° C.) 5.2. A polyoxyethylene (EO average added mole number = 22) sorbitan fatty acid ester composition was obtained.
実施例２
実施例１において、乳酸中和後に水を７．０ｇ添加する以外の条件は同じにして、エチレンオキサイドの付加反応を行った。
その結果、水分０．５％、ｐＨ（２０℃）５．２のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。
Example 2
In Example 1, the addition reaction of ethylene oxide was carried out under the same conditions except that 7.0 g of water was added after lactic acid neutralization.
As a result, a polyoxyethylene (EO average added mole number = 22) sorbitan fatty acid ester composition having a water content of 0.5% and a pH (20 ° C.) of 5.2 was obtained.
実施例３
実施例１において、８８％乳酸０.４４ｇを用いて中和した以外は、実施例１と同様にして、水分０．１％、ｐＨ（２０℃）５．９のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。
Example 3
In Example 1, polyoxyethylene (EO average addition of 0.1% water, pH (20 ° C.) 5.9) was the same as Example 1 except that neutralization was performed using 0.44 g of 88% lactic acid. Number of moles = 22) A sorbitan fatty acid ester composition was obtained.
比較例１
実施例１において、原料脂肪酸組成がパルミチン酸／ステアリン酸＝５０％／５０％（鹸化価＝２０７．８）であるソルビタン脂肪酸エステル（エマゾ−ルＳ-10Ｖ 花王製 鹸化価＝150.9）を４８４．４ｇ用いる以外は、実施例１と同様にして、水分０．１％、ｐＨ（２０℃）５．５のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。
Comparative Example 1
In Example 1, a sorbitan fatty acid ester (Emerzol S-10V Kao saponification number = 150.9) having a raw fatty acid composition of palmitic acid / stearic acid = 50% / 50% (saponification number = 207.8) 484. Except that 4 g was used, a polyoxyethylene (EO average added mole number = 22) sorbitan fatty acid ester composition having a water content of 0.1% and a pH (20 ° C.) of 5.5 was obtained in the same manner as in Example 1.
比較例２
実施例１において、乳酸中和後に水を３８．５ｇ添加する以外は、実施例１と同様にして、水分２．７％、ｐＨ（２０℃）５．５のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。
Comparative Example 2
In Example 1, except that 38.5 g of water was added after neutralization of lactic acid, polyoxyethylene (EO average addition mole of 2.7% water, pH (20 ° C.) 5.5) was obtained in the same manner as in Example 1. Number = 22) A sorbitan fatty acid ester composition was obtained.
比較例３
実施例１において、８８％乳酸０.３８ｇを用いて中和した以外は、実施例１と同様にして、水分０．１％、ｐＨ（２０℃）６．３のポリオキシエチレン（ＥＯ平均付加モル数＝２２）ソルビタン脂肪酸エステル組成物を得た。
Comparative Example 3
In Example 1, polyoxyethylene (EO average addition of 0.1% water, pH (20 ° C.) 6.3) was obtained in the same manner as in Example 1 except that neutralization was performed using 0.38 g of 88% lactic acid. Number of moles = 22) A sorbitan fatty acid ester composition was obtained.
実施例１〜３及び比較例１〜３で得られたポリオキシエチレンソルビタン脂肪酸エステル組成物について、前記の方法で脂肪酸組成を分析し、また、下記方法で外観及び流動性を評価した。結果を表１に示す。
For the polyoxyethylene sorbitan fatty acid ester compositions obtained in Examples 1-3 and Comparative Examples 1-3 were analyzed fatty acid group formed by the above method, was also evaluated the appearance and fluidity in the following manner. The results are shown in Table 1.
＜外観の評価法＞
外観はＵＶ-1600（島津製）10ｍｍセルにて常温で透過率を測定し、下記基準で評価した。
<Appearance evaluation method>
Appearance was measured at room temperature using a UV-1600 (manufactured by Shimadzu) 10 mm cell and evaluated according to the following criteria.
透過率９５％以上：○
透過率９５％未満８０％以上（薄い白濁）：△
透過率８０％未満（白濁）：×
＜流動性の評価法＞
ガラス容器に対象物をとり、２２℃の恒温水槽に入れ２時間後に容器を傾けることにより、下記基準で評価した。
Transmittance 95% or more: ○
Transmittance less than 95% 80% or more (light turbidity): Δ
Transmittance less than 80% (white turbidity): ×
<Evaluation method of fluidity>
The object was placed in a glass container, placed in a constant temperature water bath at 22 ° C., and the container was tilted after 2 hours, and evaluated according to the following criteria.
すばやく流動する：○
飴状で流動しにくい：△
かろうじて流動するか若しくは流動しない：×
Flow quickly: ○
Difficult to flow in bowl shape: △
Barely or not flowing: ×
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