JPH09176181A - New glycoside compound and nonionic surfactant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound which is a specific glycoside compound containing a (poly)glycerol residue, excellent in safety, surface-activating and emulsifying actions and foaming properties and suitable as an nonionic surfactant for a foaming agent for brushing teeth and a detergent, etc., for kitchens! SOLUTION: This new glycoside compound is represented by formula I [Z(OH)q-1 is a sugar residue after removing OH group bonded to the carbon at the anomeric position in (q)×OH groups bonded to a sugar compound represented by the formula [Z(OH)q ]; the formula, O[C3 H5 (OH)O]x is a glycerol residue after removing 2 H atoms from glycerol or a polyglycerol H-O[C3 H5 (OH) O]x -H; R<1> is a 1-30C aliphatic group; R<2> is a 2-4C lower alkylene; (t) is 1-20; (x) is 1-10} and is useful as a nonionic surfactant, etc., excellent in safety and surface activating and emulsifying actions and foaming properties. The compound is obtained by reacting the sugar compound represented by the formula, Z(OH)q with a glycerol derivative represented by formula II.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel glycoside compound and a nonionic surfactant.

[0002]

2. Description of the Related Art Nonionic surfactants are generally known to have excellent skin mildness and safety, and are widely used in cosmetics such as foaming agents for toothpaste, kitchen detergents, skin care and hair care. ing. As the nonionic surfactant, ethylene oxide or propylene oxide adduct of higher alcohol, glycerin esters such as glycerin fatty acid ester and polyglycerin fatty acid ester,
Many are known, such as sugar alcohol esters such as sorbitan fatty acid ester, and oligosaccharide esters such as sucrose fatty acid ester and maltose fatty acid ester. However, these nonionic surfactants have various properties such as excellent solubilization of oils such as ethylene oxide or propylene oxide adducts of higher alcohols, and excellent emulsifying power such as sucrose fatty acid esters and glycerin esters. Although it has the features of
Generally, foaming is poor, and for use in products requiring foaming such as foaming agents for toothpaste, kitchen detergents, skin care cosmetics, hair care cosmetics, compared to anionic surfactants such as sodium lauryl sulfate, Since the foaming is significantly inferior, it is not used alone but is currently used in combination with various additives or other surfactants to improve the foaming. On the other hand, various glycosides are known as nonionic surfactants having high safety to the human body (JP-A-60-204794, JP-A-4-244094,
JP-A-6-145188). However, these glycosides, like the above-mentioned nonionic surfactants, also have the drawback of being inferior in foaming property, and are also inferior in foam stability. In addition, the above-mentioned glycosides are not yet satisfactory in terms of emulsification of oil components and dispersibility of fine solid particles.

[0003]

DISCLOSURE OF THE INVENTION The present invention provides a glycoside compound which is highly safe to the human body and which has an excellent surface-active action, and an excellent foaming property, and an emulsifying action for emulsifying an oily liquid into water and a liquid. It is an object of the present invention to provide a surfactant excellent in the dispersing action of the above fine solid particles.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention. That is, according to the present invention, a glycoside compound represented by the following general formula (1). [Z (OH) q- _1] -O [C ₃ H ₅ (OH) O] x - in ^{[(R 2 O) t-R} 1 ] (1) (wherein, [Z (OH) q- ₁ ] represents a sugar residue obtained by removing the hydroxyl group bonded to the anomeric position carbon of the q hydroxyl groups bonded to the saccharide compound of the formula [Z (OH) q], -O [C ₃ H ₅ (OH ) O] x- is glycerin or polyglycerin H—O [C ₃ H ₅ (OH) O] x—H to 2
Represents a glycerin residue excluding hydrogen atoms, R ¹ represents an aliphatic group having 1 to 30 carbon atoms, R ² represents a lower alkylene group having 2 to 4 carbon atoms, and t represents a number of 1 to 20. , X
Indicates a number from 1 to 10). Further, according to the present invention, there is provided a nonionic surfactant comprising the glycoside compound.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The sugars represented by Z (OH) q include monosaccharides, oligosaccharides and sugar polymers. Less than,
These sugars will be described in detail. (1) Monosaccharides Monosaccharides include those represented by the following general formula (2). CnH ₂ nOn (2) In the above formula, n represents a number of 5 or 6. Specific examples of such monosaccharides include arabinose, ribose, xylose, xylulose, ribulose, glucose, galactose, fructose, mannose, sorbose, talose, fucose, glucoheptose, sedoheptulose,
Examples thereof include mannoheptulose and glucoheptulose. (2) Oligosaccharides Examples of oligosaccharides include those represented by the following formula. _{P (CnH 2 nOn) - (} P-1) H 2 O (3) In the formula, n is a number of 5 or 6. P shows the number of 1-10. Such oligosaccharides include maltose, lactose, cellobiose, isomaltose, gentiobiose, laminaribiose, xylobiose, mannobiose, maltotriose, cellotriose, manninotriose, maltotetraose, polysaccharides (cellulose, hemicellulose, (Starch, inulin, dextrin, dextran, xylan, etc.) are hydrolyzed into low molecular weight compounds. (3) Sugar Polymer As the sugar polymer, for example, a mannose polymer, a glucose polymer and the like can be mentioned.

The glycoside compound represented by the general formula (1) of the present invention is represented by the following general formula (4) Z (OH) q (4) (wherein Z is a sugar compound in which a hydroxyl group contained therein is removed). A skeleton, and (OH) q represents q hydroxyl groups bonded to the sugar skeleton) and a sugar compound represented by the following general formula (5) HO [C ₃ H ₅ (OH) O] x-[( R ² O) t-R ¹ ] (5) (In the formula, R ¹ represents an aliphatic group having 1 to 30 carbon atoms, R ² represents a lower alkylene group having 2 to 4 carbon atoms, and x represents 1 to 10
The glycerin derivative is represented by the formula (1). The reaction in this case can be represented by the following equation. Z (OH) q + HO [C ₃ H ₅ (OH) O] x - [(R ² O) -R ^1] (6) → [Z (OH) q- _1] -O [C ₃ H ₅ (OH) O]-[(R ² O) -R ¹ ] In the glycoside compound represented by the general formula (1), the glycerin or polyglycerin residue is derived from unpolymerized or polymerized glycerin. The carbon number of the aliphatic group R ¹ is 1 to 30, preferably 8 to 24, corresponding to the unpolymerized or polymerized glycerin residue.
It is. The aliphatic group R ¹ includes a linear or branched saturated or unsaturated alkyl group. Examples of such an aliphatic group include methyl, ethyl, propyl, butyl, hexyl, octyl, decyl, undecyl, dodecyl, decenyl, undecenyl, dodecenyl, tridecyl, tetradecyl, pentadecyl, pentadecenyl, hexadecyl, octadecyl, nonadecyl, eicosyl. ,
Heneicosyl, hexadecenyl, octadecenyl, nonadecenyl and the like can be mentioned. X, which represents the polymerization number of glycerin, is a number of 1 to 10, and preferably a number of 1 to 8. Examples of the lower alkyleneoxy group (R ² O) include ethyleneoxy group, (iso) propyleneoxy group and butyleneoxy group. The polyalkyleneoxy group (R ² O) t may consist of a single alkyleneoxy group or a mixed alkyleneoxy group. t is a number from 1 to 20, but preferably 1
It is a number of -10. The glycerin derivative represented by the general formula (5) is a glycerin or polyglycerin (poly) such as an alkyl (poly) alkyleneoxy halide or an alkyl (poly) alkyleneoxy sulfate metal salt.
It can be obtained by reacting an alkylating agent containing an alkyleneoxy group. The glycoside compound represented by the general formula (1) is a compound in which hydrophilicity due to a glycerin or polyglycerin residue and a (poly) alkyleneoxy group and hydrophobicity due to an aliphatic group are appropriately balanced, Shows excellent surfactant activity.

The glycoside compound represented by the general formula (1) is preferably a mixture of stereoisomers at the anomeric position, and the weight ratio of the stereoisomers at the anomeric position, α-form and β-form, is 80 / 20-5 / 95,
Preferably 70/30 to 10/90, more preferably 6
It is 0/40 to 50/50. Weight ratio of α form and β form α
When / β deviates from the above range, the foamability of the surfactant tends to be poor, the water solubility of the surfactant tends to be low, and the feeling of foam tends to be poor. In general, in order to produce a foam having excellent foam stability by using a surfactant with good foamability, generally, an oil / water interface and an air / water interface are used.
It is important to mix the surfactant regularly at the liquid interface, and from this viewpoint, the glycoside represented by the general formula (1) has an α-form or β-form rather than a mixture of the α-form and β-form. Although it was considered that the body used alone had a foaming force and a surface-active effect excellent in foam stability,
Surprisingly, it was found that when used in the form of a mixture of α- and β-forms, a synergistic effect was obtained, and that the α- and β-forms exhibited a superior surface-active effect than when they were used alone. It was

The glycoside compound represented by the general formula (1) is
It can be synthesized according to a chemical method or an enzymatic method. As a chemical method, the Fischer method [BIO
INDUSTRY, 10 , 408 (1993)] is known.

As a method for adjusting the ratio of the α-form and the β-form of the glycoside compound, a method of mixing a high-purity α-form and a high-purity β-form at a predetermined ratio, an α-form with a high α-form content ratio A method of adding the β-form at a predetermined ratio to the mixture of β-form and
An enzyme that selectively hydrolyzes the α-form with a mixture of the α-form and the β-form having a high α-form content, for example, α-amylase, α
-Glucosidase, α-galactosidase, α-glycosidase such as α-mannosidase, α-transglycosidase, and a method of hydrolyzing a certain amount of α-form in the presence of α-transglycosidase such as α-galactosyltransferase. .

The nonionic surfactant comprising the glycoside of the general formula (1) according to the present invention exhibits excellent foaming property and foam stability, and produces a foam having a refreshing and good foam feeling. It is a thing. The nonionic activator of the present invention is used in various applications where nonionic activators have been conventionally used, such as toothpaste (particularly with enzyme), as a foaming agent for other oral compositions, or as a kitchen detergent, It can be effectively used as a main agent for detergents for washing vegetables and fruits, and also for skin care such as shampoos, body shampoos, face wash and hair care products. Further, since it has a high mild property and is less likely to cause protein denaturation, it can be suitably used for liquid detergents, particularly for enzyme-containing liquid detergents, wool detergents and the like.

By using the surfactant comprising the glycoside compound represented by the general formula (1) according to the present invention as an emulsifier, an oil-in-water emulsion composition having good emulsion stability can be obtained. In this oil-in-water emulsified composition, the oil component to be emulsified in water is selected according to the purpose of use of the emulsified composition, and examples thereof include olive oil, soybean oil, rapeseed oil, peanut oil, and camellia oil. Fats and oils;
In addition to animal fats and oils such as beef tallow and fish oil, liquid paraffin, wax, petrolatum, higher fatty acids or esters thereof, higher alcohols or esters thereof and the like can be mentioned. Examples of the aqueous liquid for emulsifying the oil include water, an aqueous solution, a mixed liquid of water and a water-soluble organic solvent (for example, alcohol such as ethanol or glycerin) and water, and the like. The proportion of oil in the emulsified composition is not particularly limited, but is 1 to 90.
%, Preferably 20 to 60% by weight. The ratio of the emulsifier in the emulsified composition is 0.1 to 20% by weight, preferably 0.1 to 10% by weight. The emulsified composition may be, for example, food such as dressing, whipped cream, mayonnaise, ice cream; emulsified cosmetics such as cream and emulsion. A known method can be adopted as a method for preparing the emulsified composition. Moreover, when producing an emulsion composition, an appropriate oil phase component and aqueous phase component can be blended depending on the intended use and the like. The emulsion composition obtained by using the glycoside of the present invention is excellent in emulsification property of oil content contained therein and emulsion stability, and
Since the emulsifier is composed of a nonionic glycoside compound, it has high safety for the human body.

By using the surfactant comprising the glycoside compound represented by the general formula (1) according to the present invention as a dispersant, a dispersion liquid of fine solid particles having good dispersion stability can be obtained. In this dispersion, the fine solid particles dispersed in the dispersion medium are selected according to the purpose of use of the dispersion, and examples thereof include carbon black, titanium oxide, silicon dioxide, silicon, zeolite, diamond, calcium phosphate, and carbonic acid. One or more of inorganic fine solid particles such as calcium and zinc oxide and organic fine solid particles such as azo pigments and phthalocyanine pigments can be used in combination. The average particle size of these fine solid particles can be usually 0.1 to 10 μm. Also,
The dispersion medium is also appropriately selected, and examples thereof include monohydric alcohols such as water, methanol, ethanol and butanol, polyhydric alcohols such as propylene glycol, hexylene glycol, glycerin and polyethylene glycol, halogenated hydrocarbons such as trichloroethylene and dichloroethane, and others. An organic solvent, a mixture of water and an organic solvent, or the like can be used. The dispersion amount of the fine solid is not particularly limited, and is usually used in the range of 0.1 to 20% by weight, preferably 0.5 to 10% by weight of the whole dispersion liquid, and the fine solid particles are used as a dispersion medium. The amount of the dispersant used in the case of the dispersion can be 0.01 to 20% by weight, particularly 0.1 to 10% by weight. Specific examples of the dispersion include liquid detergent, liquid toothpaste, abrasives, colloidal emulsion, paint, wet ink, wet pigment dispersion, and the like. A known method can be adopted. Further, in the case of producing a dispersion liquid, appropriate components can be added depending on the purpose of use and the like. In this case, as the dispersant, if necessary, a conventionally-used dispersant such as other nonionic surfactants or anionic surfactants may be added. The dispersant used as these auxiliary components is preferably used in an amount of 90% by weight or less based on the total amount of the dispersant. The dispersion obtained by using the glycoside compound of the present invention has excellent dispersibility and dispersion stability of the fine solid particles contained therein, and the dispersant is composed of a nonionic glycoside. Therefore, it has high safety for the human body.

[0013]

Next, the present invention will be described in more detail by way of examples.

Example 1 Using a sugar compound and a glycerin derivative as reaction raw materials, Fi
The glucoside compound having the structure shown in Table 1 was synthesized by the scher method. In Table 1, glucoside compounds are shown corresponding to the following structural formulas. [MA- (OH) q- _1] -O [C ₃ H ₅ (OH) O] x - in ^{[(R 2 O) t-R} 1 ] (A) In this equation, [mA- (OH) q- ₁ ] is the formula [mA
-(OH) q] (sugar compound (average degree of polymerization is m
Among the hydroxyl groups bonded to the glucose (A) polymer, the sugar residue excluding the hydroxyl group bonded to the anomeric carbon is shown. Further, the formula -O [C ₃ H ₅ (OH) O] x - ^{[(R 2 O) t-R} 1 ] has the formula HO [C ₃ H ₅ (OH) O] x - [(R ² O) t-R ¹ ]] is a glycerin derivative residue obtained by removing a hydrogen atom from the glycerin derivative represented by Table 1 also shows the weight ratio α / β of the α-form and β-form of the glucoside compound.

[0015]

[Table 1]

Example 2 Glucose (C ₆ H ₁₂ O ₆ ) and diethylene oxide decyl glycerin [C ₁₂ H ₂₅ O (CH ₂ CH ₂ O) ₂ CH (CH ₂
OH) CH ₂ OH] as a raw material, and by the Fischer method, diethylene oxide decyl glyceryl glucoside represented by the general formula (A) (in the general formula (A), R = dodecyl group, m = 1.5, x = 1) , T = 2) 1
50 parts by weight was dissolved in methanol as a solvent at a concentration of 80% by weight, and this solution was dissolved in an anion exchange resin (trade name: D
owex 1, OH type, grain size 200-400 mesh,
After being adsorbed on a column packed with (Dow Chemical Co.),
Pass methanol through the adsorption column as an eluent,
The body was separated by adsorption. By this adsorption separation, 85 parts by weight of α form and 43 parts by weight of β form were obtained with a purity of 100%.

Example 3 The α-form and β-form isolated in the above Example 2 were mixed at the ratio shown in Table 2, and the product No. E and F were obtained. Separately synthesized diethyleneoxytetradecyl diglyceryl glucoside was also isolated by the same operation as in Reference Example 2 to obtain β
The body is obtained and this is the product number. G.

[0018]

[Table 2]

Example 4 Product Nos. Obtained in Examples 1 to 3 For the glucosides A to G and the commercially available nonionic surfactants H, I, and J, the foaming performance, foam feeling, emulsification performance, and dispersion performance were measured as follows, and the measurement results are shown in Table 3. Show. The specific contents of the commercially available nonionic surfactants H, I, and J are as follows. H: sucrose ester (ryoto sugar ester, P
-1670, manufactured by Mitsubishi Chemical Foods, Inc. I: 9 mol ethylene oxide 9 adduct of alcohol having 12 to 13 carbon atoms J: Alkyl polyglucoside (Glucopon 600 csu)
p, made by Henkel)

(Measurement of Foaming Performance) 10 ml of a 0.5% by weight aqueous solution of a sample was put in an Epton tube (100 ml), and 25
After keeping the temperature constant in a water bath at 0 ° C., the mixture was shaken 20 times for 10 seconds, and the foam volume V (1) 30 seconds after the end of the shaking and the foam volume V (2) after 5 minutes were measured. (Evaluation of Bubble Feeling) A sample was dissolved in water at a concentration of 0.5% by weight, 50 ml of this aqueous solution was placed in a 100 ml sample bottle with a lid, and this was shaken 10 times at 40 ° C. The face was washed and evaluated. ◯: Refreshing feeling Δ: Slight refreshing feeling ×: Weak refreshing feeling (measurement of emulsification performance) 10 ml of 0.5% by weight aqueous solution of the sample
In a test tube with a 30 ml stopper, and further add 10 m of salad oil.
1 was added, and the mixture was vigorously shaken 30 times at 30 ° C., and then left still at 30 ° C. for 30 minutes, and the volume (ml) of the aqueous phase (separated water) separated at the bottom of the test tube was measured. (Measurement of dispersion performance) 30 ml of 0.5% by weight aqueous solution of sample
Was placed in a 50 ml stoppered test tube, 0.3 g of carbon black was further added, and the mixture was vigorously shaken 30 times at 30 ° C.,
The mixture was allowed to stand at 30 ° C. for 30 minutes for separation. Next, insert a 1 ml pipette into the test tube so that the tip of the pipette is at a position corresponding to 1.5 ml from the bottom of the test tube, and
ml was sampled. 1 ml of this test solution was diluted 50 times with distilled water, and carbon black was dispersed for 10 minutes using an ultrasonic oscillator. After dispersion, the turbidity of the dispersion was measured by an absorptiometer (slit width 0.05 m, manufactured by Hitachi, Ltd.).
m, wavelength 480 nm), and the amount of carbon black dispersed was determined from a calibration curve prepared in advance.

[0021]

[Table 3] * Show a comparative example

Next, examples of compositions containing the glycoside compound of the present invention will be shown. [Composition No. 1] Shampoo Glucoside (Product No. A) 10.5 (% by weight) Lauryl ethoxy sulfate sodium salt 3.5 Cocoyl diethanolamide 2.0 Sodium sulfate 1.5 Fragrance / pigment appropriate amount water balance ━━━━━━━ ━━━━━━━━━━━━━━━━━━━━━ Total 100.0

[Composition No. 2) Toothpaste composition Dibasic calcium phosphate dihydrate 45.5 (% by weight) Glycerin 5.0 Sorbitol 15.0 Sodium carboxymethylcellulose 1.0 Glucoside (Product No. B) 1.5 Flavors and sweeteners Suitable amount Water balance ━━━━━━━━━━━━━━━━━━━━━━━━━━━ Total 100.0

[Composition No. 3] Liquid stone glucoside (Product No. C) 20.0 (wt%) Lauryl sulfate sodium salt 10.0 Fragrance / emulsifier Appropriate amount of water Residue ━━━━━━━━━━━━━━ ━━━━━━━━━━━━ Total 100.0

[Composition No. 4) Vegetable dishwashing agent Alcohol ethoxylate sulfate sodium salt 20.0 (% by weight) Glucoside (Product No. D) 10.0 Lauryl alkanolamide 5.0 Fragrance / emulsifier Appropriate amount of water Residue ━━━━━━ ━━━━━━━━━━━━━━━━━━━━━ Total 100.0

[Composition No. 5] Cold Cream Glucoside (Product No. E) 10 parts by weight Liquid paraffin 25 parts by weight Lanolin 10 parts by weight Isopropyl myristate 12 parts by weight Fragrances, dyes, appropriate amount water balance ━━━━━━━━━━━━━━━━━ ━━━━━━━━━━━ Total 100.0

[Composition No. 6] Vanishing cream Glucoside (Product No. B) 5.5% by weight Stearic acid 13.2% by weight Propylene glycol 24.0% by weight Glycerin 6.0% by weight Sodium hydroxide 0.6% by weight Fragrance Suitable amount Purified water Residue ━━━━━━━━━━━━━━━━━━━━━━━━━ Total 100.0% by weight

[Composition No. 7] Emulsifying medium for metal drawing processing Potassium oleate 20 parts by weight Hexadecyl alcohol 25 parts by weight Beef tallow 25 parts by weight Borax 50 parts by weight Glucoside (Product No. A) 25 parts by weight Water 400 parts by weight

[Composition No. 8] Pigment Dispersion Titanium oxide (1 μm diameter) 10% by weight Sodium alginate 5% by weight Glucoside (Product No. B) 2% by weight Water residue ━━━━━━━━━━━━━━━━━━━━ ━━━━━━━ Total 100.0% by weight

[Composition No. 9] Liquid detergent Glucoside (Product No. D) 13.0% by weight Sodium metasilicate 6.0% by weight Perfume 0.5% by weight Water balance ━━━━━━━━━━━━━━━━━━ ━━━━━━━━ Total 100.0% by weight

[Composition Example No. 10] Cleaning agent containing abrasive glucoside (product No. A) 3.5% by weight P.I. O. E. FIG. Nonyl phenyl ether 3.0% by weight Sodium benzoate 3.5% by weight Urea 5.0% by weight Sodium hydroxide 1.0% by weight Silica powder (100 mesh pass) 54.0% by weight Perfume, pigment Appropriate amount of water residue ━━ ━━━━━━━━━━━━━━━━━━━━━━━━ Total 100.0% by weight

[0032]

INDUSTRIAL APPLICABILITY The nonionic surfactant comprising the glycoside compound of the present invention exhibits excellent foaming property and foam stability and produces a foam having a refreshing and good foam feeling. The nonionic activator comprising the glycoside compound of the present invention is used in various applications where the nonionic activator has been conventionally used, such as toothpaste (particularly with enzyme),
It can be effectively used as a foaming agent for other oral compositions, as a main agent for detergents such as kitchen detergents, and for skin care such as shampoos, body soaps, soaps, facial cleansers, and hair care products. Further, since it has a high mild property and is less likely to cause protein denaturation, it can be suitably used for liquid detergents, particularly for enzyme-containing liquid detergents, wool detergents and the like. The emulsified composition formed using the glycoside compound of the present invention is excellent in emulsification property and oil stability of the oil contained therein, and the emulsifier thereof is composed of a nonionic glycoside. Therefore, it has high stability to the human body. The dispersion formed by using the glycoside compound of the present invention has excellent dispersibility of fine solid particles contained therein and dispersion stability, and the dispersant is composed of a nonionic glycoside. Therefore, it is highly safe for the human body.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication C08G 65/28 NQP C08G 65/28 NQP 65/34 NQS 65/34 NQS C11D 1/68 C11D 1 / 68 (72) Inventor Masahiro Sato 1-3-7 Honjo, Sumida-ku, Tokyo Within Lion Co., Ltd.

Claims (3)

[Claims] 1. A glycoside compound represented by the following general formula (1). [Z (OH) q- _1] -O [C ₃ H ₅ (OH) O] x - in ^{[(R 2 O) t-R} 1 ] (1) (wherein, [Z (OH) q- ₁ ] represents a sugar residue obtained by removing the hydroxyl group bonded to the anomeric position carbon of the q hydroxyl groups bonded to the saccharide compound of the formula [Z (OH) q], -O [C ₃ H ₅ (OH ) O] x- is glycerin or polyglycerin H—O [C ₃ H ₅ (OH) O] x—H to 2
Represents a glycerin residue excluding hydrogen atoms, R ¹ represents an aliphatic group having 1 to 30 carbon atoms, R ² represents a lower alkylene group having 2 to 4 carbon atoms, and t represents a number of 1 to 20. , X
Indicates a number from 1 to 10) 2. The glycoside compound represented by the general formula (1) is composed of a mixture of α-form and β-form anomeric isomers, and the weight ratio of the α-form and the β-form is 80/20 to 5/95. Item 1. A glycoside compound. 3. A nonionic surfactant comprising the glycoside compound according to claim 1 or 2.