JP2000001468A - Glyceryl etherified polyhydric alcohol sulfuric acid compound, anionic surface-active agent and detergent composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful as an anionic surface-active agent applicable to detergents for dishes and vegetables, shampoos, body shampoos, hand soaps, house detergents and oral cavity products of e.g. dentifrice or a mouth-rinsing agent. SOLUTION: This compound is shown by the formula R1O(G)n-(A)mOSO3M [R1 is a 6-30C higher alkyl or alkenyl; G is shown by formula I or II (B is H or SO3M); A is a 4-8C polyhydric alcohol residue; (n) is an average condensation molar number of 1 to 10; (m) an average condensation molar number of 1 to 5; and M is H or a salt-formable cationic ion], e.g. lauryl glyceryl ether erythritol sodium sulfate. A compound of the formula may be produced by subjecting a glycidyl ether and polyhydric alcohol to condensation reaction in the presence of e.g. basic catalyst for obtaining a glyceryl etherified polyhydric alcohol as a raw material, by reacting the resultant product with a sulfating reagent and by neutralizing it with an alkaline aqueous solution.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention provides good foaming even in the presence of acidic to weakly alkaline (pH 4 to 8), high hardness hard water, and oily soil, and has low irritation to skin and hair. And a glyceryl etherified polyhydric alcohol sulfate compound useful as a detergent component excellent in use feel, such as a slimy feeling upon rinsing and a small feeling on the skin, and an anionic surfactant comprising the same. And a cleaning composition using the same.

[0002]

2. Description of the Related Art Conventionally, petroleum-based anionic surfactants and nonionic surfactants have been widely used as components of detergents generally used for household purposes such as clothing, tableware, hair, and body. I have. Recently, surfactants used in the above applications have excellent detergency, foaming power, good foaming feeling during rinsing, a good feeling of use such as refreshing feeling after rinsing, and skin irritation. And a high performance level with multiple functions such as environmental safety.
Therefore, in order to satisfy such demands, development has been advanced from both sides of a detergent composition and a surfactant. In the case of a detergent composition, the pH is changed from weakly acidic to neutral to suppress irritation to the skin, while a surfactant can be used under the same conditions, and the cleaning performance, stability, Surfactants that are selected from the viewpoint of feel and environmental safety, and whose constituent elements are composed of carbon, hydrogen, and oxygen and have no problem even when discharged into the environment, have been proposed as next-generation surfactants. For example, Japanese Patent Publication No. 52-18170 discloses an alkyl glyceryl etherified polyhydric alcohol as a new surfactant.
In Japanese Patent Application Laid-Open No. 9-2988, glyceryl etherified polyhydric alcohol using an alkenyl group is used as a detergent, emulsifier, dispersant and the like for toiletries and cosmetics. Are introduced as bases and emulsifiers for cosmetics. However, in the case of an alkyl glyceryl etherified polyhydric alcohol, although it has the characteristics of being less irritating to the skin and having excellent hard water resistance and excellent detergency against oily stains, dishwashing / vegetable detergents, shampoos, etc. When applied as a surfactant, compared to existing petroleum surfactants, especially in the presence of oily dirt, not only the foaming power is significantly reduced, but also a slimy feeling when rinsing,
There is a serious problem in practical use that the feeling of persistence is extremely poor. Therefore, it is not satisfactory from the practicality point of view, and after further improving the foaming power in the coexistence of oily dirt, a surfactant excellent in slimy feeling and residual feeling when rinsing is required. I was

[0003]

The inventors of the present invention have studied in detail the relationship between the chemical structure of a glyceryl etherified polyhydric alcohol-based surfactant, the surfactant activity, the skin irritation, and the like. It has been found that foaming power is improved by using a sulfate ester salt at the terminal of the hydrophilic group, thereby completing the present invention. That is, the present invention is hypoallergenic to the skin, even in the presence of oily stains, has good foaming, and has a good feeling of use such as a slimy feeling upon rinsing and a feeling of residue on the skin, It is an object of the present invention to provide a glyceryl etherified polyhydric alcohol sulfate compound useful as a detergent component and an anionic surfactant comprising the same, and to provide a detergent composition containing the anionic surfactant.

[0004]

According to the present invention, there is provided a glyceryl etherified polyhydric alcohol sulfate compound represented by the following general formula (1).

Embedded image Further, according to the present invention, there is provided an anionic surfactant comprising the compound and a detergent composition containing at least one of the anionic surfactant.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the above general formula (1), R ¹
Is a linear or branched higher alkyl or alkenyl group having 6 to 30 carbon atoms. The optimal carbon chain length is
It is greatly affected by the type of polyhydric alcohol residue and the number of condensation thereof, and preferably has 10 to 24 carbon atoms in terms of foaming power and detergency, and has a decyl group, a dodecyl group, a tetradecyl group, and a hexadecyl group. Octadecyl group, octadecenyl group, undecyl group, 2-hexyldecyl group, 2
-Octylundecyl group, 2-decyltetradecyl group and the like, and they can be used alone or in combination. G is a glycerin residue represented by the following general formula (2) or (3).

Embedded image

Embedded image In the above formula, B represents hydrogen or SO ₃ M. n is an average number of condensed moles of G and is a number of 1 to 10, preferably 1 to 5.

A represents a polyhydric alcohol residue having 4 to 8 carbon atoms. Such residues include, in addition to ordinary aliphatic polyhydric alcohols, polyhydric alcohol residues in which two hydroxyl groups have been removed from polyhydric alcohols such as sugar alcohols, monosaccharides, and disaccharides. Those polyhydric alcohols include neomethylolpropane, trimethylolethane,
Trimethylolpropane, pentaerythritol, glucose, galactose, xylose, lactose, mannose, talose, rhamnose, arabinose, glucosylmannose, lyxose, allose, altrose, growth, idose, ribose, erythrose, threose, psicose, fructose, sorbose, tagatose , Pentulose, tetrose, sucrose, maltose, isomaltose, cellobiose, lactose, trehalose, koujibiose, sophorose, nigerose,
Laminaribiose, isomaltose, gentiobiose, melibiose, branteobiose, turanose,
Vicianose, agarobiose, silaviose, rutinose, primeprose, xylobiose, rhodimenaviose, erythritol, mesoerythritol, maltitol, lactitol, D-threitol, D-arabinitol, ribitol, xylitol, sorbitol, galactitol, D-mannitol, alititol, higher alditol And the like. m is an average number of condensed moles of the polyhydric alcohol residue, and is a number of 1 to 5. Preferably, it is a number of 1 to 2 in terms of foaming power and detergency.

The counter ion M of the sulfate group is hydrogen or a salt-forming cation. Salt-forming cations include sodium,
Examples include alkali metal ions such as potassium and lithium; alkaline earth metal ions such as calcium and magnesium; ammonium ions; and organic ammonium ions derived from organic amines. As the organic ammonium ion, it is preferable to use one derived from an alkanolamine (such as mono-, di- or tri-ethanolamine, n- or iso-propanolamine). Two or more of these cations can be used in combination.

The compound represented by the above general formula (1) according to the present invention can be produced by combining known methods. For example, a glyceryl etherified polyhydric alcohol, which is a known substance produced by condensing a glycidyl ether and a polyhydric alcohol in the presence of a basic catalyst or the like, is used as a raw material. It can be produced by neutralization. Sulfating reagents include sulfuric anhydride, chlorosulfonic acid, sulfamic acid,
A commonly used sulfating reagent such as an alkyl sulfate, an acyl sulfate, or an adduct thereof with a Lewis base can be used. Examples of the Lewis base include trimethylamine, triethylamine, pyridine, dimethylformamide, dimethylacetamide, dioxane and the like. In the sulfation reaction, the primary sulfate of the glyceryl etherified polyhydric alcohol is selectively used at a high temperature of the produced sulfate by using a mild sulfating reagent which is reactive from the viewpoint of hydrolysis resistance during long-term storage. It is preferable to prepare a primary sulfate having good hydrolysis resistance by sulfation. In this case, as the sulfating reagent, for example, an alkyl sulfate having a lower alkyl group is used. Examples of the alkyl sulfate include methyl sulfate, ethyl sulfate, propyl sulfate, butyl sulfate, and the like. As a counter ion of these alkyl sulfate salts, an alkali metal ion, an alkaline earth metal ion or the like is used, and examples thereof include sodium, potassium, magnesium, and calcium.

A glyceryl etherified polyhydric alcohol,
Although the reaction with these alkyl sulfates proceeds without a catalyst, the use of an acidic catalyst is preferred in view of the reaction rate and the quality of the product such as color tone and odor. Examples of such an acidic catalyst include sulfuric acid, hydrochloric acid, phosphoric acid, p-toluenesulfonic acid, an acidic ion exchange resin, and a solid acid. The amount of the acid catalyst used is 0.0001 to 1 with respect to its precursor.
0% by weight, preferably 0.001 to 2% by weight.
The reaction molar ratio of the sulfating reagent to the glyceryl etherified polyhydric alcohol is selected from the amount of the glyceryl etherified polyhydric alcohol remaining as unreacted, the number of moles of the sulfate group added, and their reactivity. It is preferable to leave the glyceryl etherified polyhydric alcohol from the viewpoints of further improving the detergency against the skin and further reducing the irritation to the skin. For this purpose, the smaller the molar ratio of the sulfating reagent to the glyceryl etherified polyhydric alcohol, the better. On the other hand, if you get a sufficient reaction rate,
In order to improve the solubility of the product, the larger the reaction molar ratio, the better. The reaction temperature is 0 to 50 ° C, preferably room temperature. The reaction time is 1 to 10 hours. This reaction can be carried out without a solvent, but it is preferable to use a solvent in order to lower the viscosity of the reaction solution and allow the reaction to proceed smoothly. Such solvents include 1,4-
Examples include dioxane, tetrahydrofuran, hexane, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, dimethylformamide, dimethylacetamide, pyridine, dimethylsulfoxide and the like. The amount used is suitably 1.0 to 5.0 in weight ratio to the precursor. In the reaction of the glyceryl etherified polyhydric alcohol and alkyl sulfate, with the progress of the reaction,
Lower alcohol is a by-product. The completion of the reaction can be expedited by removing the lower alcohol out of the system. Examples of such a method include a method in which the reaction is performed under a reduced pressure of 0.1 to 100 Torr, a method in which the reaction is performed under a nitrogen stream, and the like. After the completion of the sulfation reaction, the solvent is distilled off under reduced pressure to obtain the anionic surfactant of the present invention.

The glyceryl etherified polyhydric alcohol sulfate obtained as described above is a product in which the primary hydroxyl group of the glyceryl etherified polyhydric alcohol is selectively sulfated. This is excellent in stability at high temperatures and under long-term storage.

The glyceryl etherified polyhydric alcohol, which is a precursor of the compound of the present invention, is produced by reacting glycidyl ether with a polyhydric alcohol. In this case, the reaction is as shown in the following reaction formula. A polyhydric alcohol is added to the oxirane ring of glycidyl ether to obtain a compound represented by the formula and the formula, and any of them can be used as a raw material of the anionic surfactant of the present invention.

Embedded image

In the reaction between glycidyl ether and sugar alcohol, a compound in which a primary alcohol of sugar alcohol is added to an oxirane ring of glycidyl ether and a compound in which a secondary alcohol of sugar alcohol is added are obtained. Although it can be used as the anionic surfactant raw material of the present invention, from the viewpoint of the foaming power of the resulting anionic surfactant, a sugar alcohol to which a primary alcohol is added is preferable. Such a compound can be obtained by ketalizing a sugar alcohol in advance, glyceryl etherification, and then deketalization. The reaction example is shown below.

[0013]

Embedded image (In the above formula, R ¹ has the same meaning as described above, and R ² , R ³ and R ⁴ represent a lower alkyl group.)

The ketalization and deketalization reactions proceed almost quantitatively in the presence of an acidic catalyst. As the acidic catalyst, inorganic acids such as sulfuric acid, hydrochloric acid and phosphoric acid, and organic acids such as paratoluenesulfonic acid and benzenesulfonic acid are used.
As the lower ketone used in the ketalization reaction, those having a lower alkyl group are preferable from the viewpoint of separation and purification after the reaction, and examples thereof include acetone and methyl ethyl ketone. The lower alcohol used in the deketalization reaction includes methanol, ethanol, normal or isopropanol, normal or isobutanol, and the like.

Since the glyceryl etherified polyhydric alcohol acts as a nonionic surfactant, it is desirable that part of the glyceryl etherified polyhydric alcohol remains in the reaction product in the above reaction. Therefore, the reaction molar ratio of the sulfating reagent to the glyceryl etherified polyhydric alcohol is selected in view of the amount of the glyceryl etherified polyhydric alcohol remaining as unreacted and their reactivity. It is preferable to leave the glyceryl etherified polyhydric alcohol from the viewpoint of further improving the foaming power and further reducing the irritation to the skin. For this purpose, the reaction of the sulfating reagent with the glyceryl etherified polyhydric alcohol is preferable. The smaller the mole, the better. On the other hand, the larger the better, in order to obtain a sufficient reaction rate. The reaction molar ratio is generally 0.1 to 2.0,
Preferably it is 0.2 to 1.5. When the reaction molar ratio is large, a product having improved solubility obtained by reacting a mole of the sulfating reagent with 2 moles per mole of the glyceryl etherified polyhydric alcohol can be obtained.

The reaction product (anionic surfactant) obtained as described above contains a small amount of sulfate and the like in addition to unreacted glyceryl etherified polyhydric alcohol. This reaction product can be used as an anionic surfactant having excellent detergency and bubble power only by adjusting the pH, but when used as a high-purity product such as a surfactant for a liquid detergent. Is recrystallization, solvent extraction, silica gel column chromatography, ion exchange resin,
Purification can also be performed using a known purification method such as electrodialysis.

The anionic surfactant of the present invention can be used in combination with an existing surfactant. When the anionic surfactant of the present invention is used in combination with a specific nonionic surfactant, it is possible to achieve not only a further improvement in detergency but also a further reduction in irritation to skin and hair. Examples of the nonionic surfactants include glyceryl etherified polyhydric alcohols which are precursors of the anionic surfactant of the present invention, particularly, alkyl glyceryl etherified erythritol, mesoerythritol, maltitol, xylitol, sorbitol, glucose and the like. Other examples include higher alcohol ethoxylates, higher alcohol ethoxypropoxylates, fatty acid alkanolamides, alkylamine oxides, alkylamidoamine oxides, and acylglucamides.

The anionic surfactant of the present invention can be used in combination with existing anionic surfactants and amphoteric surfactants. In this case, the anionic surfactant is used in combination for the purpose of further improving the detergency and foaming power. Specific examples thereof include alkyl sulfates, polyoxyethylene alkyl sulfates, α-sulfo fatty acid ester salts, α-olefin sulfonate salts, alkyl or hydroxyalkyl ether carboxylate salts, N-
Acylated taurine, N-acylated methyltaurine, N-
Acylated glycine, N-acylated aspartic acid, N-
Acylated sarcosine, N-acylated glutamic acid, higher fatty acid salt, alkylbenzene sulfonate, alkyl sulfonate, monoalkyl phosphate, alkyl amide ether sulfate, fatty acid monoglyceride sulfate, alkyl iminodicarboxylate, Lower amide type N-acyl amino acid salts, alkyltartaric acid alkylamides, malic acid alkylamides, citric acid alkylamides and the like.

The amphoteric surfactant is used in combination for the purpose of further improving foaming power and mildness to the skin.
Specific examples thereof include amide amino acid type amphoteric surfactants, long-chain alkyl dimethyl carboxymethyl betaines,
Examples include sulfobetaine, imidazolium betaine, glycine-type and alanine-type amphoteric surfactants, carboxybetaine, sulfobetaine, phosphobetaine, amide amino acids, and imidazolinium betaine-based surfactants.

When the anionic surfactant (A) represented by the general formula (1) is used by mixing with the existing surfactant (B), the mixing ratio (A) / (B) is 98/2 to 5/95 by weight, preferably 80/20 to 20/8.
0. If the mixing ratio is smaller than this, the characteristics of the anionic surfactant of the present invention cannot be sufficiently exhibited. The amount of the anionic surfactant of the present invention incorporated into the detergent composition varies depending on the dosage form of the detergent.
It is preferably 0.5 to 50% by weight, 1 to 70% by weight in the case of a paste, and 1 to 80% by weight in the case of a solid. The pH when the detergent is dissolved in water varies depending on the type and use of the surfactant to be blended, but the preferred range is pH 5 to 8 for shampoo, body shampoo and kitchen detergent, and 7 to 11 for clothing detergent. If the pH is less than 4.9 and the pH is 11.1 or more, it is not preferable from the viewpoint of irritation to the skin and damage to the washing target.

The cleaning composition of the present invention may contain, if necessary, known auxiliary components to be added to the cleaning composition. Such auxiliary components include builders, humectants, viscosity modifiers, preservatives, anti-inflammatory agents, antioxidants, ultraviolet absorbers, sequestering agents, migration inhibitors, bactericides, water-soluble polymers Examples include compounds, water-soluble inorganic salts, organic and inorganic compounds used for pH adjustment, pearlescent agents, pigments, enzymes, bleaching agents and the like.

[0022]

According to the present invention, foaming is good even in the presence of acidic to weakly alkaline (pH 4 to 8) or high hardness hard water and oily soil, and there is little irritation to skin and hair. In addition, the present invention provides a novel anionic surfactant useful as a detergent component having an excellent use feeling such as a slimy feeling upon rinsing and a feeling of remaining on the skin. Therefore, the detergent composition containing the surfactant of the present invention is a dishwashing vegetable detergent, shampoo, body shampoo, hand soap,
It can be widely used as oral care products such as household cleaners, toothpastes and mouthwashes.

[0023]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail based on embodiments.

Example 1 In a 500 ml four-necked flask equipped with a vacuum stirrer, a Liebig condenser, and a thermometer, 36.5 g of lauryl glyceryl ether erythritol, 14.8 g of sodium ethyl sulfate, 200 ml of dioxane, and 0.1 ml of concentrated sulfuric acid. 1m
l was charged. After stirring at room temperature for 1 hour, the pressure was gradually reduced from normal pressure while stirring the inside of the flask to remove by-produced ethyl alcohol and dioxane, and kept under reduced pressure of 50 mmHg over 3 hours. Subsequently, after dioxane was distilled off, the resulting solid was washed with methylene chloride to remove sulfuric acid, and 45.2 g of sodium lauryl glyceryl ether erythritol sulfate (yellow solid) (yield 95).
%, Purity by high performance liquid chromatography is 98%)
I got

Example 2 The procedure of Example 1 was repeated, except that the reaction molar ratio of sodium ethyl sulfate was changed to 1/2, and 55.2% by weight of sodium lauryl glyceryl ether erythritol sulfate and lauryl glyceryl ether erythritol were used.
8% by weight of a mixture (light yellow solid) (96% yield, quantitative method according to Example 1) was obtained.

Example 3 Example 1 was repeated, except that myristyl glyceryl ether xylitol was used instead of lauryl glyceryl ether erythritol, and sodium myristyl glyceryl ether xylitol sulfate (light yellow solid) (94% yield) was used. , Purity 97%, and the quantification method according to Example 1).

Examples 4 to 6 and Comparative Examples 1 to 2 The compounds obtained in Examples 1 to 3 were evaluated for their detergency, foaming power and feel upon use as follows.
Table 1 shows the results. Table 1 also shows the results for sodium laurate or polyoxyethylene (P = 3) lauryl ether sulfate for comparison.

1) Detergency Dirt (tallow / soybean oil weight ratio = 5/5, about 0.15 g) adheres to the inner wall of a polypropylene cup having a capacity of 200 ml, and each polypropylene cup has a pH of 6.5 to 7.5.
180 ml of an aqueous solution (liquid detergent) having a surfactant concentration of 2.0 wt% adjusted to 7 ° DH was added, and the rotating blade was rotated in the polypropylene cup for 5 minutes at a temperature of 25 ° C. to wash the inside of the polypropylene cup. The detergency of each liquid detergent is (◎) when the value of the detergency (%) calculated by the following equation exceeds 41%, and (４０) is 31 to 40%.
11 to 30 were evaluated as (△), and the case of 10% or less was evaluated as (x). 2) Foaming power Mixed soil (tallow / soybean oil weight ratio = 5/5) as a soil component was added to 20 ml of a 2.0% by weight aqueous solution of surfactant adjusted to pH 6.5 to 7.5. 2% by weight was added, and this was put into a 100 ml stoppered Epton tube, shaken at room temperature for 20 times for 10 seconds, and the foam volume was measured when the aqueous solution and the bubble interface became clear. still,
The following criteria were used for evaluation. ◎: When the foam volume (ml) exceeds 81 ○: When the volume is 66 to 80 Δ: When the foam volume is 51 to 65 ×: When the volume is 50 or less 3) Feeling in use pH 6.5 to 7.5 Surfactant concentration adjusted to 2% by weight
After squeezing the sponge 20 times in the aqueous solution, the sensory evaluation was performed on the slimy feeling when the hand was rinsed with running water and the residual feeling on the skin. The average value of 5 panelists was calculated, and when the average value was 2.5 or more: ◎, when 2.0 to 2.5:
、, 1.5 to 2.0: Δ, less than 1.5: × In addition, the following criteria were used for evaluation. 3: Excellent 2: Normal 1: Inferior

[0029]

[Table 1]

Next, examples of specific formulations using the anionic surfactant of the present invention as a detergent component will be shown.

Example 7 (Cleaning composition for tableware and vegetables) (% by weight) Polyoxyethylene lauryl alcohol (P = 10) 13 Compound of Example 2 12 n-Dodecyldimethylamine oxide 3 Ethanol 5 Dye, flavor Suitable amount Purification Water Balance This dishwashing vegetable detergent was less irritating to the skin, and had good detergency and foaming power.

Example 8 (Shampoo composition) (% by weight) Compound of Example 8 8 Lauroyl N-methyltaurine Na 8 Coconut fatty acid diethanolamide 2 Alkylimidozolinium betaine 2 Propylene glycol 5 Dye, perfume Appropriate amount Purified water Balance This shampoo Had low irritation to the skin, good foaming, little slimy feeling upon rinsing, and good use feeling.

Example 9 (Shampoo composition) (% by weight) Compound of Example 3 10 Lauroyl N-methyltaurine Na 6 Coconut fatty acid diethanolamide 22-decyltetradecyltrimethylammonium chloride 0.2 Citric acid Appropriate amount Perfume, dye Appropriate amount Purified water balance This shampoo was hypoallergenic to the skin, had good foaming, had little slimy feeling upon rinsing, and had a good feel after shampooing.

Example 10 (Body soap) (% by weight) Compound of Example 1 10 Lauroyl glutamate Na 7 Coconut fatty acid diethanolamide 3 Ethylene glycol fatty acid ester 3 Ethanol 3 Propylene glycol 5 Dye, perfume Appropriate amount Purified water balance It was less irritating to the skin, excellent in foaming, less slimy upon rinsing, less likely to remain on the skin, and had a good feel upon use.

Example 11 (hand soap) (% by weight) Compound of Example 15 15 Coconut fatty acid diethanolamide 4 Amidopropyltrimethylamine laurate 3 2-decyltetradecyltrimethylammonium chloride 0.3 Ethylene glycol fatty acid ester 0.7 Propylene glycol 5 Dye, perfume Appropriate amount Purified water balance This hand soap was less irritating to the skin, had fine foaming, had less residual feeling on the skin during rinsing, and had a good feel upon use.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Kenji Yokoi 1-7-7 Honjo, Sumida-ku, Tokyo F-Term in Lion Corporation (reference) 4C083 AC122 AC302 AC392 AC562 AC642 AC662 AC692 AC712 AC781 AC782 AC792 BB05 CC23 CC38 EE06 EE07 EE10 4D077 AB10 BA03 BA07 BA13 CA02 CA03 CA04 CA12 DC02Y DC12Y DC20Y DC24Y DC56Y DC57Y DD29Y DD35Y DD36Y DE02Y DE08Y DE17Y DE29Y 4H003 AB30 AC08 AC15 BA12 DA01 DA02 DA05 DA17 FA20 AB02 FA02 AB18 FA21 AB20 FA02 A

Claims (3)

[Claims] 1. A glyceryl etherified polyhydric alcohol sulfate compound represented by the following general formula (1). Embedded image 2. An anionic surfactant comprising the glyceryl etherified polyhydric alcohol sulfate compound according to claim 1. 3. A detergent composition comprising at least one anionic surfactant according to claim 2.