JPH0832778B2 - Alkyl polyoxyalkylene carboxylate ester - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to surfactants useful as emollients in skin care compositions.

 The present invention provides compounds of formula I:

In the above formula, R represents a C ₈ -C ₂₂ alkyl, R ₁ represents a C ₁ -C ₂₂ alkyl, m represents an integer of 0 or 1 to 4, n represents an integer of 3 to 20, o Represents an integer of 1 to 4 and p is 0
Alternatively, it represents an integer of 1 to 20. However, when 1) R ₁ is C ₁ -C ₃ alkyl, p is 0, and 2) m is 0.
And n is an integer of 6 to 20.

R is preferably C ₁₀ -C ₁₈ alkyl, more preferably
It is a C ₁₀ -C ₁₆ alkyl.

R ₁ is preferably C ₆ when p is other than 0.
To C ₁₈ alkyl, more preferably C _{10 to} C ₁₆ alkyl.

When p is 0, R ₁ is preferably C ₃ -C ₁₈ alkyl, especially isopropyl or cetyl.

 The variable m is preferably 0 or 2.

The variable n is preferably 6-18 when m is 0,
More preferably, it is 6-14.

The variable n is preferably 6 to when m is other than 0.
12, more preferably 3-10.

The variable o is preferably 1-3, more preferably 1 or 2, especially 1.

The variable p is preferably 0 or an integer from 1 to 16, more preferably 0 or an integer from 1 to 12, most preferably 0.

All alkyl groups are straight or branched unless otherwise specified.

 Preferred compounds are of formula Ia below.

In the above formula, R 'represents a C ₁₀ -C ₁₈ alkyl, R _1' is p '
Is 0, it represents C ₃ -C ₁₈ alkyl, or P ′.
Is other than 0, it represents C ₆ -C ₁₈ alkyl, m is the same as defined above, n ′ represents an integer of 6 to 18 when m is 0, or m is 0. In the case of other than, it represents an integer of 3 to 12, o'represents an integer of 1 to 3, and p'represents 0 or an integer of 1 to 16.

More preferred compounds are those of formula Ib below.

In the above formula, R ″ represents C ₁₀ -C ₁₆ alkyl, and R ₁ ″ is p ″.
Is 0 to C ₃ -C ₁₈ alkyl, P ″ is other than 0 to C ₁₀ -C ₁₆ alkyl, m is the same as the above definition, and n ″ is m When 0, it represents an integer of 6 to 14, or when m is other than 0, 3
Represents an integer of ~ 10, o ″ represents an integer of 1 or 2,
p ″ represents 0 or an integer of 1 to 12.

Most preferred compounds are those of formula Ic below, especially where R ₁ ″ is isopropyl or cetyl.

In the above formula, R ″, n ″ and R ₁ ″ are the same as those defined above, and m ′ represents 0 or 2.

Suitable alcohol precursors of the alkyl polyoxyalkylene carboxylate esters of this invention are straight or branched chain secondary alcohols having 8 to 22 carbon atoms. It is also possible to use a mixture of alcohols, which is the case with commercial alcohols, which are often obtained as a mixture of several alcohols in general. A specific example is C ₁₂ commercially available from Union Carbide.
~ C ₁₅ A mixture of straight chain alcohols, C ₁₂ ~ C containing about 20% branching commercially available from Shell Chemical Company.
A mixture of ₁₅ predominantly linear alcohols and an alcohol mixture commercially available from Exxon Chemical Company with at least 70 mole% branched 1-decanol. When alcohol mixtures are used, the number of carbon atoms in the alcohol is stated as the average number that can be determined by gas phase chromatography and hydroxyl number.

The compounds of formula I are prepared by conventional methods. For example, the alkyl polyoxyalkylene carboxylate esters of this invention are carboxyalkyl adducts obtained by propoxylation and / or ethoxylation of straight or branched chain primary alcohols having 8 to 22 carbon atoms. Can be prepared by esterification of the resulting carboxyalkylated acid with a linear or branched primary alcohol which may contain one or more ethylene oxide groups.

The alkoxylation step can be performed, for example, by adding 0.2 to
It can be carried out in the presence of an alkaline catalyst, for example sodium or potassium hydroxide, in an amount of 1% by weight.

If desired, small amounts of reducing agents can be added to the alcohol or mixture thereof to be alkoxylated to minimize discoloration of the resulting polyalkoxylated alcohol. Suitable reducing agents that can be used include sodium borohydride, lithium aluminum hydride and diborane, preferably sodium borohydride.

In the preparation of a polyoxyalkylated alcohol in which the polyoxyalkylene chain contains a first propylene oxide block and a second ethylene oxide block, propylene oxide is introduced in an amount calculated to give the desired degree of propoxylation, The resulting mixture is reacted until the propylene oxide is consumed (indicated by the drop in reaction pressure). A calculated amount of ethylene oxide can likewise be introduced and reacted to give a second block which completes this alkoxylation. Normally, the alkoxylation product is finally treated with a weak acid, such as glacial acetic acid, to neutralize the basic catalyst residue.

It is understood that the individual alkoxylation operations are to introduce the desired average number of alkylene oxide units per alcohol molecule. Thus, for example, the initial treatment of the alcohol mixture with mmol propylene oxide per mole of alcohol results in the propoxylation of each alcohol moiety with propylene oxide such that on average there are m propylene oxide moieties per alcohol moiety. . However, in this case, some alcohol moieties will bond with more than m propylene oxide units and some will bond with less than m propylene oxide units. Generally, the maximum number of propyleneoxy units in a single molecule will not exceed 8 and the number of ethyleneoxy units in a single molecule will not exceed 30. The variation in the number of alkylene oxide moieties is not critical as long as the average number of units in each block is within the stated limits of m and n in formula I above. Thus, m and n in formula I are average values, and in some cases other than integers.

Alkylation is carried out under normal temperature conditions, for example at 140 to 160 ° C., below atmospheric pressure and without the interposition of water.

The resulting alkyl polyalkoxide intermediate is then carboxyalkylated by Williamson synthesis involving reaction with the appropriate chloro- or bromo-carboxylic acid or salt thereof in the presence of sodium hydroxide or sodium metal. Such reactions are usually not complete, so reaction products often contain small amounts of uncarboxylated alkyl polyalkoxides. Although there are methods of separating uncarboxylated materials as well as performing essentially complete carboxyl alkylation, they are usually time consuming and uneconomical. Fortunately, it has been found that small amounts of such uncarboxylated materials are not particularly harmful, or even advantageous. Preferably, the carboxyalkyl group is a carboxymethyl group, ie the variable o is preferably 1.

The alkyl polyalkoxide carboxylic acid is then combined with a linear or branched C _{1 to} C ₂₂ primary alcohol, optionally containing one or more ethylene oxide groups, and from 5: 1 or more to 1: Esterification is achieved by reacting in the presence of a catalyst at a molar ratio of alcohol to carboxylic acid of up to 1. Typical catalyst is sulfuric acid,
Includes hydrogen chloride, p-toluene sulfonic acid and boron trifluoride. The water produced may be removed, for example by azeotropic distillation, in order to concentrate the reaction. Alternatively, one of the reactants (usually an alcohol) may be used in large excess.
For example, the vacuum dried alkyl polyalkoxide carboxylic acid can be dissolved in an excess molar amount of anhydrous alcohol that forms a low boiling azeotrope with water. An acidic catalyst is then added to the mixture until the reaction is substantially complete (usually 2
Allow to proceed at reflux for ~ 48 hours. Then excess alcohol and water are removed by distillation at atmospheric pressure,
The ester is obtained by decantation. Alternatively, the anhydrous alkyl polyalkoxide carboxylic acid is mixed with an equimolar amount of high boiling alcohol. Then add the acidic catalyst,
The resulting mixture is heated under vacuum and the reaction water is heated to 120 ° -200
Remove at a temperature of °. After collecting the theoretical amount of water, the mixture is cooled, the vacuum is released with nitrogen and the ester is obtained by decantation.

The compounds of formula I are useful as surfactants and as emulsifiers, dispersants, lubricants, wetting agents, leveling agents, softeners, etc.
Textile, leather, paper, lacquer, personal care, for example,
Suitable for use in toiletries, cosmetics and rubber industry. For example, they can be used as humectants, softeners or lubricants in the treatment and finishing of textile materials, and also water-insoluble liquids or solid substances (eg hydrocarbons, higher alcohols, oils, fats, waxes and resins).
Is suitable for converting into a creamy emulsion, a clear solution or a fine stable dispersion.

The compounds of formula I are also useful as emulsifiers for insecticide compositions and agricultural sprays such as DDT, 2,4-D, etc., added to petroleum products, hydraulic fluids, lubricating oils, cutting oils and greases. Useful as a coating agent and can be used as a coating aid for use in coatings containing hydrophilic film-forming colloids, for example, as a tackifier in the adhesive layer of adhesive tapes in the photographic industry. It can also be used as a foaming agent, an emulsifier and a softening agent in various foods.

The alkyl polyoxyalkylene carboxylate esters of the present invention are especially useful in skin care compositions such as
It is useful as an essential emollient component in skin creams, lotions and the like. These formulations improve not only the moisturizing and conditioning properties of the skin care composition, but also the tactile properties. Such skin care compositions will normally contain 0.5 to 15% by weight, preferably 1 to 13% by weight, more preferably 1.5 to 12% by weight of alkyl polyoxyalkylene carboxylate ester. Alkyl polyalkoxyl carboxylate esters are preferably used as the sole emollient component and are a total replacement for conventional fatty ester emollients such as isopropyl myristate, isopropyl palmitate and similar compounds. . Alternatively, the carboxylate ester can be used with a conventional fatty ester emollient, which can reduce the amount of conventional fatty ester emollient used.

Skin care compositions may include other ingredients normally found in such compositions. For example, fatty alcohols can be used as auxiliaries to stabilize the composition and provide a cosmetically acceptable viscosity. In general, C ₁₄ -C ₂₂ alkanol which is substantially saturated, is used. Typical examples of suitable fatty alcohols are cetyl alcohol and stearyl alcohol.

Emulsifiers may also be used, such as cationic types, such as quaternary ammonium compounds, such as
Dimethyl distearyl ammonium chloride, amphoteric,
It may be, for example, betaine or sulfobetaine, and nonionic, for example polyethylene glycol monostearate.

Lubricants are commonly used to improve the activity of skin care compositions. This may be a silicone oil, for example dimethylpolysiloxane or other conventional polysiloxane or olive oil.

Moisturizers may be present in the skin care composition if desired. Typical humectants that can be used include propylene glycol and polyethylene glycol.

The amount of water or aqueous vehicle compounded will depend on the desired consistency of the final product. The amount of water can be varied to prepare, for example, a thick fluid liquid or lotion, a semi-liquid thick cream or paste.

The skin care composition is generally 1.5-10%, preferably 2-8.5% fatty alcohol, 1.5-12%, preferably 2-10% emulsifier and 0.75-50%, preferably 1-.
Contains 35% lubricant (all% are by weight).

Other conventional additives commonly used in skin care compositions can be used. Perfume oils that mask the odor and give a cosmetic appeal can be used. Non-toxic, compatible dyes may optionally be used to color the composition. Preservatives such as methylparaben, propylparaben and formaldehyde may be used.

Also, other ingredients useful for providing a skin care composition for a particular application can be used. For example, a sunscreen additive such as octyldimethylparaaminobenzoic acid may be used. Skin protectants such as zinc oxide may be used to protect the skin. Essential oils such as menthol can also be used as a drug.

The skin care composition of the present invention exhibits good consistency, can be evenly applied to the skin, is quickly absorbed, dries quickly and gives the skin a soft and smooth appearance. Upon application, it has good tactile properties and does not give an oily or greasy feel.

The examples below serve to further illustrate the invention. Parts in the examples are by weight and temperatures are in ° C.

Example 1 iso-dodecyl dipropoxy hexaethoxymethyl methyl carboxylic acid, isopropyl ester iso _{-C 10 H 21 O (C 3} H 6 O) 2 (C 2 H 4 O) 6 CH 2 COOCH (CH 3) 2 A) dipropoxy hexa Preparation of ethoxyisodecyl alcohol In a reaction vessel, with stirring, 705 parts of decyl alcohol (a mixture of primary aliphatic alcohols in which at least 70 mol% is branched 1-decanol, boiling range 216-223 °,
20/20 ° specific gravity 0.838, refractive index n _D ²⁰ 1.400, pour point −53
Viscosity at 20 °, 22.5 cm stroke and 20 °
Water solubility <0.05 g / 100 g, commercially available from Exxon Chemical Company), 10.6 parts potassium hydroxide (in pellet form) and 0.12 parts sodium borohydride. The system is evacuated, purged with nitrogen three times at 60 ° and then heated to 100 °. 260 parts of propylene oxide are then added in 60 minutes and the reaction temperature is raised to 155 °. After further reacting the reaction mixture until the pressure of the reaction system has dropped to about 10 mbar, the above procedure is repeated while adding another 257 parts of propylene oxide over 60 minutes.
After further reaction of the propoxylated alcohol reaction mixture until the pressure of the reaction system has dropped again to about 10 mbar, the above procedure is repeated while adding 1178 parts of ethylene oxide over 60 minutes. When the reaction is complete, the reaction system is purged with nitrogen, cooled to 85 ° and a further 0.12 part of sodium borohydride is added. The reaction system is then held under nitrogen pressure at 80-90 ° for 2 hours, the catalyst present is neutralized with glacial acetic acid and the product is filtered to give a translucent pale yellow liquid having the formula: obtain.

Iso _{-C 10 H 21 (OC 3 H} 6) 2 (OC 2 H 4) 6 OH B) compound 957.6 parts prepared prepared above in A) of isodecyl dipropoxy hexaethoxymethyl carboxylate, alternately 25
Equimolar amounts of sodium hydroxide (71.2 parts) and sodium monochloroacetate (207.7 parts) are added portionwise over a period of 3 and a half hours in a temperature range of -50 °. Once the addition is complete,
The temperature of the resulting reaction mixture is held at 50 ° for 30 minutes and then raised to 75 ° in 30 minutes. The reaction mixture was held at a temperature of 75 ° for 90 minutes, then cooled to 50 ° and 175 parts in 600 parts water.
Acidify with 1 part of sulfuric acid (50% strength) and then separate the water-soluble salts to obtain an oil of the formula:

C ₁₀ H ₂₁ O (C ₃ H ₆ O) ₂ (C ₂ H ₄ O) ₆ CH ₂ COOH C) Preparation of the title compound 158.7 parts of the compound prepared in B) above were placed under vacuum in a reaction vessel. Heat to 60 °. After collecting 12.7 parts of water, the reaction vessel is cooled and the vacuum is released. 100 parts of anhydrous isopropanol (molar ratio alcohol: acid about 8: 1) are then placed in the reaction vessel, after which a catalytic amount (25 drops) of 98% sulfuric acid is added to the reaction mixture. The resulting mixture is then heated to reflux temperature and kept at this temperature for 24 hours. After removing isopropanol and water by distillation, decantation gives the title compound.

Example 2 isododecyl dipropoxy hexaethoxymethyl carboxylate, prepared in cetyl esters iso _{-C 10 H 21 O (C 3} H 6 O) 2 (C 2 H 4 O) 6 CH 2 COOC 16 H 33 above Example 1B) 158.7 parts of the compound are heated to 50 ° under vacuum in a reaction vessel. After collecting 14 parts of water, the reaction vessel is cooled and the vacuum is released. Next, equimolar amount (48.2 parts)
The cetyl alcohol of 1. is placed in a reaction vessel and the mixture is heated until the alcohol is completely dissolved. Amount of catalyst (about 5 drops)
98% sulfuric acid is then added and the resulting mixture is placed under vacuum.
Heat to 130 °. After 3 hours, collect 3.9 parts of water. Cool the mixture to 5 ° and recover the title compound by decantation.

Example 3 Lauryl hexaethoxymethyl carboxylic acid, cetyl ester C ₁₂ H ₂₅ O (C ₂ H ₄ O) ₆ CH ₂ COOC ₁₆ H ₃₃ A) Preparation of hexaethoxylauryl alcohol 664.7 parts of lauryl in a reaction vessel with stirring Add alcohol and 8.5 parts potassium hydroxide (in pellet form). The system was purged with nitrogen at 100 °, then 160
Heat to 0 ° C, at which point the addition of 1059 parts ethylene oxide to the reaction mixture is begun. The temperature of the resulting reaction mixture is maintained at 160 ° -170 ° during the addition of ethylene oxide. When the addition of ethylene oxide is complete, the reaction mixture is cooled to give the compound of formula

Preparation of C ₁₂ H ₂₅ O (OC ₂ H ₄ ) ₆ OH B) laurylhexaethoxymethylcarboxylic acid The procedure of Example 1B) was essentially repeated, substituting approximately the same amount of the compound prepared in Example 1A). Using the compound prepared in A) above, the compound of the following formula is obtained.

C ₁₂ H ₂₅ O (C ₂ H ₄ O) ₆ CH ₂ COOH C) Preparation of the title compound The procedure of Example 2 was essentially repeated to give the compound of Example 1B) 158.
The title compound is obtained using 101.6 parts of the compound prepared in B) above instead of 7 parts.

Example 4 Lauryl hexaethoxymethyl carboxylic acid, isopropyl ester C ₁₂ H ₂₅ O (C ₂ H ₄ O) ₆ CH ₂ COOH (CH ₃ ) ₂ Essentially repeating the procedure of Example 1C), replacing the compound of Example 1B) Use approximately the same amount of the compound of Example 3B) as above to give the title compound.

Example 5 A) Essentially the procedure of Example 3A) is repeated, using the appropriate starting alcohol and the appropriate amount of ethylene oxide.
The following compound is obtained.

a) R ^a (OC ₂ H ₄ ) ₈ OH, where R ^a is a predominantly linear C ₁₂ -C containing about 20% branching.
It is the residue of a mixture of ₁₅ alcohols. Available from Shell Chemical Company.

b) R ^b (OC ₂ H ₄ ) ₁₂ OH In the above formula, R ^b is the residue of a mixture of C _{12 to} C ₁₅ straight chain alcohols. Available from Union Carbide.

c) R ^c (OC ₂ H ₄ ) ₁₁ OH In the above formula, R ^c is the residue of a primary aliphatic alcohol in which at least 70 mol% is branched 1-decanol. Available from Exxon Chemical Company.

d) R ^d (OC ₂ H ₄ ) ₁₀ OH where R ^d is the commercially available residue of isoskiallyl alcohol containing a mixture of branched methyl isomers.

e) C ₁₆ H ₃₃ (OC ₂ H ₄ ) ₁₀ OH B) essentially repeating the procedure of Example 3B), eg instead of the compound prepared in 3A), approximately equal amounts of compound 5A)
The following compounds are obtained using a) to e).

a) R ^a O (C ₂ H ₄ O) ₈ CH ₂ COOH b) R ^b O (C ₂ H ₄ O) ₁₂ CH ₂ COOH c) R ^c O (C ₂ H ₄ O) ₁₁ CH ₂ COOH d) R ^d O (C ₂ H ₄ O) ₁₀ CH ₂ COOH e) C ₁₆ H ₃₃ O (C ₂ H ₄ O) ₁₀ CH ₂ COOH C) a) essentially the same procedure as in Example 2 Instead of the compound produced, approximately equal amounts of compound 5B) a)
~ E) are used to obtain the following compounds:

a) R ^a O (C ₂ H ₄ O) ₈ CH ₂ COOH ₁₆ H ₃₃ b) R ^b O (C ₂ H ₄ O) ₁₂ CH ₂ COOC ₁₆ H ₃₃ c) R ^c O (C ₂ H ₄ O) ₁₁ CH ₂ COOC ₁₆ H ₃₃ d) R ^d O (C ₂ H ₄ O) ₁₀ CH ₂ COOC ₁₆ H ₃₃ e) C ₁₆ H ₃₃ O (C ₂ H ₄ O) ₁₀ CH ₂ COO ₁₆ H ₃₃ Example 6 ~ 10 By essentially repeating the procedure of Example 1C), substituting the compounds prepared in Example 1B) with approximately equal amounts of the compounds of Examples 5B) a) to e), the compounds 5C) a) to e). Isopropyl ester corresponding to is obtained.

It should be understood that in all the above examples the numbers of propyleneoxy units and ethyleneoxy units are average values.

Example 11 A body cream composition comprises the following ingredients:

Ingredients wt% Cetyl alcohol 2.5 Stearyl alcohol 5.0 Light silicone oil 1.0 Pationic SSL ^R (amphoteric emulsifier) 1.5 Water 82.6 Propylene glycol 5.0 Compound of Example 1 2.0 The above composition is heated to 70 ° with water and the remaining ingredients are added to 70%.
It is prepared by heating to 0 ° C., slowly adding water to the heated component mixture with stirring, and then cooling the resulting mixture to room temperature.

Examples 12-14 In the composition of Example 11, the compound of Example 1 can be replaced by the compounds of Examples 7, 8 and 9.

Example 15 An oil-in-water body lotion composition comprises the following ingredients:

Ingredients% by weight A. Polyethylene glycol (400) Monostearate 2.5 Olive oil 47.5 Propylparaben 0.15 Compound of Example 2 2.5 B. Methylparaben 0.15 Water 46.8 The above composition is combined with ingredients of A and heated to 70 °, B Are prepared by heating the components of the above together to 70 °, adding A to B with stirring and then cooling the resulting mixture to room temperature.

Examples 16-18 In the composition of Example 15, the compound of Example 2 is added to Example 5C) b),
It can be replaced by the compounds of c) and d).

Example 19 An oil-in-water body lotion composition comprises the following ingredients.

Ingredients wt.% A. Arlacel 60 (nonionic emulsifier) 2 Tween 60 (polysorbate) 3 Compound of Example 1 B. Water 85 The above composition is heated to 70 ° with ingredients of A together and water is changed to 72 It is prepared by heating to 0 ° C., slowly adding water to the heated ingredient mixture with stirring, and then cooling the resulting mixture to room temperature.

Examples 20-21 In the composition of Example 19, the compound of Example 2 was added to Examples 7 and 8
Can be replaced by

Claims (10)

[Claims] 1. A compound represented by the following formula I: In the above formula, R represents a C ₈ -C ₂₂ alkyl, R ₁ represents a C ₁ -C ₂₂ alkyl, m represents an integer of 0 or 1 to 4, n is 3
Represents an integer of -20, o represents an integer of 1 to 4, and p represents 0 or an integer of 1 to 20. However, when 1) R ₁ is C ₁ -C ₃ alkyl, p is 0, and when 2) m is 0, n is an integer of 6-20. 2. The compound according to claim 1, which is represented by the following formula Ia. In the above formula, R'represents C ₁₀ -C ₁₈ alkyl, R ₁ 'represents C ₃ -C ₁₈ alkyl when p'is 0, or P'is other than 0. Represents C ₆ -C ₁₈ alkyl,
m is the same as defined in claim 1, n'represents an integer of 6 to 18 when m is 0, or 3 to 12 when m is other than 0. , O'represents an integer of 1 to 3, and p'represents 0 or an integer of 1 to 16. 3. The compound according to claim 2, which is represented by the following formula Ib. In the above formula, R ″ represents C ₁₀ -C ₁₆ alkyl, R ₁ ″ represents C ₃ -C ₁₈ alkyl when p ″ is 0, and C when P ″ is other than 0. Represents _{10 to} C ₁₆ alkyl, m is the same as defined above, n ″ represents an integer of 6 to 14 when m is 0, or 3 when m is not 0.
Represents an integer of 10, o ″ represents an integer of 1 or 2, p ″
Represents 0 or an integer of 1 to 12. 4. The compound according to claim 3, which is represented by the following formula Ic. In the above formula, R ″, n ″ and R ₁ ″ are the same as defined in claim 3, and m ′ represents 0 or 2. 5. R ₁ ″ is isopropyl or cetyl,
The compound according to claim 4. 6. The compound according to claim 1, which is represented by the following formula. Iso-C ₁₀ H ₂₁ O (C ₃ H ₆ O) ₂ (C ₂ H ₄ O) ₆ CH ₂ COOCH (CH ₃ ) ₂ 7. The compound according to claim 1, which is represented by the following formula. R ^a O (C ₂ H ₄ O) ₈ CH ₂ COOC ₁₆ H _{33 In the} above formula, R ^a is a predominantly linear C _12-15 containing 20% branching.
Represents the residue of a mixture of alcohols. 8. The compound according to claim 1, which is represented by the following formula. R ^a O (C ₂ H ₄ O) ₈ CH ₂ COOCH (CH ₃ ) _{2 In the} above formula, R ^a is the same as defined in claim 7. 9. The following formula I, [In the above formula, R represents a C ₈ -C ₂₂ alkyl, R ₁ represents a C ₁ -C ₂₂ alkyl, m represents an integer of 0 or 1 to 4, n represents an integer of 3 to 20, o represents an integer of 1 to 4, p is 0
Alternatively, it represents an integer of 1 to 20. However, when 1) R ₁ is C ₁ -C ₃ alkyl, p is 0, and 2) m is 0.
And n is an integer of 6 to 20], the skin care composition comprising at least one compound represented by the formula [5] in an amount of 0.5 to 15% by weight. 10. A skin care composition according to claim 9 wherein the compound of formula I is the only emollient component.