(en)A basic agent for use in cosmetics comprising an alkylene oxide derivative represented by the following formula (I) is provided:

Z-{O(AO) l (EO) m -(BO) n H} a (I)
(where Z represents a residue of a compound having 3 to 9 hydroxyl groups with the hydroxyl groups removed, a is from 3 to 9, AO represents an oxyalkylene group of 3 to 4 carbon atoms, EO represents oxyethylene group, l and m represent average additional mol numbers of the oxyalkylene groups of 3 to 4 carbon atoms and the oxyethylene groups, respectively, and 1≦l=50, 1≦m≦50, the weight ratio (AO/EO) of AO to EO is from 1/5 to 5/1, AO and EO may be added in a random form or may be added in a lock form. BO represents oxyalkylene group with a number of carbon atoms of 4, and n is an average additional mol number and 0.5≦n≦5).

1.ApplicationNumber: US-66451205-A
1.PublishNumber: US-2007280897-A1
2.Date Publish: 20071206
3.Inventor: MARUYAMA KEI-ICHI
TEZUKA YOJI

4.Inventor Harmonized: MARUYAMA KEI-ICHI(JP)
TEZUKA YOJI(JP)

5.Country: US
6.Claims:
(en)A basic agent for use in cosmetics comprising an alkylene oxide derivative represented by the following formula (I) is provided:

Z-{O(AO) l (EO) m -(BO) n H} a (I)
(where Z represents a residue of a compound having 3 to 9 hydroxyl groups with the hydroxyl groups removed, a is from 3 to 9, AO represents an oxyalkylene group of 3 to 4 carbon atoms, EO represents oxyethylene group, l and m represent average additional mol numbers of the oxyalkylene groups of 3 to 4 carbon atoms and the oxyethylene groups, respectively, and 1≦l=50, 1≦m≦50, the weight ratio (AO/EO) of AO to EO is from 1/5 to 5/1, AO and EO may be added in a random form or may be added in a lock form. BO represents oxyalkylene group with a number of carbon atoms of 4, and n is an average additional mol number and 0.5≦n≦5).

7.Description:
(en)TECHNICAL FIELD OF THE INVENTION
The present invention concerns a basic agent for use in cosmetics having both excellent feel and moisturizing effect, and cosmetics blended therewith.
BACKGROUND ART
Humectants have become essential for cosmetics and there is a tendency to favor those having high moist and refreshing feel in view of the recent trend of consumers. However, humectants and cosmetics capable of coping with such demands have not sufficiently been obtained yet.
For example, while watersoluble polyhydric alcohols typically represented by glycerin, polypropylene glycol and 1,3-butylene glycol have excellent moist feel, sticky feel in noted when blending them at a high concentration. When blending triglyceride or silicone oil, etc. intending to provide smooth feel, since there is no compatibility between both of then, a great amount of an emulsifier is necessary, which lowers the smooth feel or moist feel.
In view of the above, for providing properties of both of moist and smooth feel with a water soluble basic agent, while cosmetics blended with N-acetyl basic amino acid (for example, in Japanese Patent publication No. 2002-87928A), poly-γ-glutamic acid crosslinked polymer (or example, in Japanese Patent publication No. 2003-12442A, or PEG dialkyl ether (for example, in Japanese Patent publication No. 10-167948A) have been reported, none of them have yet provided a sufficient effect at present.
Further, in a case of egg cosmetics for moisture retention, they became dry when an applied portion is washed away with a soap or the like, and it is necessary to compensate for the loss of moist skin feel, for example, by re-applying another moisturizing cosmetic such as cream.
While Japanese Patent publication No. 2003-113023A discloses skin cosmetics comprising an alkylene aside derivative, the state after wading away the applied portion with a soap or the like has not yet been studied.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a basic agent for use in cosmetics having both excellent feel and moisturizing effect, while keeping moisture even after cleaning, as well as cosmetics blended therewith.
That is, the present invention is shown below:
(1) A basic agent for use in cosmetics, comprising an alkylene oxide derivative represented by the following formula (I):

Z-{O(AO) l (EO) m -(BO) n H} a (I)

(where Z represents a residue of a compound having 3 to 9 hydroxyl groups with the hydroxyl groups removed, a is from 3 to 9, AO represents an oxyalkylene group of 3 to 4 carbon atoms, EO represents oxyethylene group, l and m each represents an average additional mol number of the oxyalkylene groups of 3 to 4 carbon atoms and the oxyethylene groups, respectively, and 1≦l≦50, 1≦m≦50, the weight ratio (AO/EO) of AO to EO is from 1/5 to 5/1, AO and EO may be added in a random form or may be added in a block form. BO represents an oxyalkylene group with a number of carbon atoms of 4, and n is an average additional mol number thereof, which is: 0.5≦n≦5).
(2) The basic agent for use in cosmetics in which AO and EO are added in a random form.
(3) The cosmetics blended with the basic agent for use in cosmetics.
(4) The cosmetics containing the basic agent for use in cosmetics by from 0.05 to 50% by weight and a water-soluble polyhydric alcohol by from 0.05 to 50% by weight
The basic agent for use in cosmetics of the invention has both properties of excellent smooth and moist feel, good to the touch and providing most Effective performance when blended in the cosmetics.
BEST MODES FOR CARRYING OUT THE INVENTION
In the alkylene oxide derivative shown by the formula (I), Z represents a residue of a compound having 3 to 9 hydroxyl groups with the hydroxyl groups removed, and a is a number of the hydroxyl groups of the compound Z, which is from 3 to 9. The compound having from 3 to 9 hydroxyl groups includes, for example, glycerin and trimethylol propane for a=3, erythritol, pentaerythritol, sorbitan, alkyl glycoside, and diglycerin for a=4, xylytol for a=5, dipentaerythritol, sorbitol and inositol for a=6, sucrose and trehalose for a=8, maltitol for a=9, and mixtures thereof. Preferably, Z is a residue of a compound having 3 to 9 hydroxyl groups with the hydroxyl groups removed, which satisfies 3≦a≦6. In a case where it is 2 or less, a sufficient moist feel cannot be obtained and, on the other hand, in a case where the number of functional groups is 10 or more, it results in sticky feel.
AO represents an oxyalkylene group of 3 to 4 carbon atoms and includes, for example, oxypropylene group, oxybutylene group, oxyisobutylene group, oxy-t-butylene group, oxytrimethylene group, and oxytetramethylene group. Preferred are oxypropylene group and oxybutylene group and more preferred is oxypropylene group.
l is an average additional mol number of AO, which is: 1≦l≦50 and, preferably, 2≦l≦20. m is an average additional mol number of EO, which is: 1≦m≦50 and, preferably, 2≦m≦20. In a case where AO is 0, it results in sticky feel and in a case where it exceeds 50, the moist feel is deteriorated. Further, in a case where EO is 0, the moist feel is deteriorated and in a case where it exceeds 50, it results in sticky feel.
The weight ratio (AO/EO) of AO to EO is from 1/5 to 5/1 and, preferably, from 1/4 to 4/1. In a case where it is less than 1/5, it results in sticky feel and, in a case, where it is more than 5/1, the moist feel is deteriorated.
The sequence of the addition of AO and EO is not particularly specified and they may be added in a block form or may be added in a random form. Preferably, they are added at random
BO represents an oxyalkylene group with the number of carbon atoms of 4 and includes, for example, oxybutylene group, oxyisobutylene group, oxytetramethylene group, and oxy-t-butylene group. Oxybutylene group is preferred.
n is an average additional mol number of BO, which is 0.5≦n≦5, preferably, 0.8≦n≦3 and, more preferably, 1≦n≦3. In a case where it is less than 0.5, it results in sticky feel and, in a case where it exceeds 5, the moist feel is deteriorates.
In the formula (1), it is necessary that (BO)n is bonded to a terminal hydrogen atom.
The alkylene oxide derivative shown by the formula (I) of the invention can be produced by a known method. For example, it can be obtained by addition polymerization of ethylene oxide and an alkylene oxide of 3 to 4 carbon atoms to a compound having three or more hydroxyl groups and then reacting an alkylene oxide with a number of carbon atoms of 4.
In the step of addition polymerization of ethylene oxide (EO) and an alkylene oxide (AO) 3 to 4 carbon atoms to the compound having three or more hydroxyl groups, EO and AO may be put to random polymerization or block polymerization. However, it is necessary that BO is reacted after the addition polymerization of EO and AO.
Further, the form of the cosmetics blended with the basic agent for use in the cosmetics of the invention is not particularly restricted, and it may include aqueous cosmetics, water-in-oil type or oil-in-water type emulsion cosmetics, or oily cosmetics. And it may be of forms such as shampoo, rinse, body soap, face washing agent, skin lotion, milky lotion, cam, hair conditioner, lipstick, and hair growing agent.
The blending amount of the basic agent for use in cosmetics in the cosmetics after the invention is not particularly restricted and usually it is Mended ranging from 0.01 to 70% by weight
Further, by blending a water-soluble polyhydric alcohol as cosmetics, both the feel and the moisturizing effect are further improved. A combination comprising preferably from 0.05 to 50% by weight of the basic agent of the invention and from 0.05 to 50% of the water-soluble polyhydric alcohol, more preferably, from 0.1 to 25% by weight of the basic agent of the invention and from 0.1 to 25% by weight uf the water-soluble polyhydric alcohdl, and, further preferably, from 1 to 10% by weight of the basic agent of the invention and from 1 to 10% by weight of the watersoluble polyhydic alcohol is more effective.
The water-soluble polyhydric alcohol is a water-soluble compound having two or more hydroxyl groups in the molecule and includes, for example, propylene glycol, dipropylene glycol, isoprene glycol, 1,3-butylene glycol glycerin, diglycerin, polyethylene glycol, sorbitol, maltitol, methyl glucoside, alkyl glucoside, and alkylene oxide adducts thereof. Among them, dipropylene glycol, iropropylene glycol, 1,3-butylene glycol, glycol, diglycerin, polyethylene glycol, methyl glycoside, and ethylene oxide adducts thereof are preferred.
In cosmetics of the invention, other ingredients may also be contained within a range that does not deteriorate the performance of the invention. For example, they include lower alcohols, hydrocarbon oils, natural oils and fats, synthetic triglycerides, aster ails, waxes, silicone derivatives, oily basic agents, anionic surfactants, amphoteric surfactants, nonionic surfactants, cationic surfactants, semi-polar surfactants, water-soluble high molecular materials, organic or inorganic salts, pH adjusting agents, sterilizers, chelating agents, antioxidants, UV-ray absorbents, vitamins, natural extracts derived from animal and plants, dyes, pigments, and perfumes.


EXAMPLES
Synthesis Example 1
Synthesis of polyoxybutylene (10 mol) polyoxyethylene (20 mol) polyoxypropylene (20 mol) sorbitol ether (polyoxyethylene and polyoxypropylene form block polymer)
12 g of potassium hydroxide as a cat along with 182 g of sorbitol was charged into an autoclave and, after replacing air in the autoclave with dry nitrogen, the catalyst was completely dissolved at 140° C. under stirring. Then, 1160 g of propylene oxide was dropped by a dropping device and stirred for 2 hours. Successively, 880 g of ethylene aide was dropped by the dropping device and stirred for 2 hours. Further, 720 g of butylene oxide was dropped by the dropping device and reacted under stirring for 2 hours. Then, the on composition was taken out of the autoclave, neutralized with hydrogen chloride to pH 6-7, and treated for removing the contained water at a reduced pressure of 0.095 MPa (gage pressure, at 100° C. for one hour. Further, filtration was conducted to remove the salt formed after the treatment to obtain a basin agent as Compound 1.
Synthesis Example 2
Synthesis of polyoxybutylene (5 mol), polyoxyethylene (10 mol), polyoxopropylene (10 mol), glycerin ether (polyoxyethylene and polyoxypropylene form random polymer)
6 g of potassium hydroxide as a catalyst along with 92 g of glycerin was charged into an autoclave and, after replacing air in the autoclave with dry nitrogen, the catalyst was completely dissolved at 140° C. under stirring. Then, a mixture of 440 g of ethylene wide and 680 g of propylene oxide was dropped by a dropping device and stirred for 2 hour. Further, 360 g of butylene oxide was dropped by the dropping device and reacted under stirring for 2 hours. Then, a reaction composition was taken out of the autoclave, neutralized with hydrogen chloride to pH 6-7, and treated for removing the contained water at a reduced pressure of 0.095 MPa (gage pressure), at 100° C. for one hour. Further, filtration was conducted to remove the salt formed after the treatment to obtain a basic agent as Compound 2.
Synthesis Examples 3 to 11
In the same manner as in the Synthesis Example 1 or Synthesis Example 2, synthesis of compounds shown in Table 1 was conducted.
TABLE 1 Absence of Moist Compound Z a l m n EO/PO stiky feel feel EXAMPLE 1 1 Sorbitol 6 3.3 3.3 1.7 1.3/1 36 38 2 2 Glycerin 3 3.3 3.3 1.7 1.3/1 47 46 3 3 Sucrose 8 6.3 6.3 1.9 1.3/1 37 43 4 4 Glycerin 3 1.7 6 1.7 1/4.7 36 43 5 5 Glycerin 3 6 1.7 1.7 4.6/1 44 35 6 6 Sorbitol 6 5 5 4 1.3/1 45 38 7 Compound 2:glycerin = 50:50 — — — — — — 47 48 COMPARATIVE 1 7 Sorbitol 6 5 5 0 1.3/1 33 42 EXAMPLE 2 8 Glycerin 3 6.7 0 0 1/0 23 41 3 9 Glycerin 3 0 6.7 0 0/1 43 24 4 10 C6H13O(EO)6C6H13 1/0 40 32 5 Glycerin — 3 — — — — 15 45 6 Propylene glycol — 2 — — — — 18 42 7 Polyethylene glycol — 2 7 0 0 1/0 21 39 (molecular weight 300) 8 Lysine hydrogen chloride — — — — — — 17 41

Examples 1 to 7 and Comparative Examples 1 to 8
Tests shown below were conducted using each of basic agents for use in the cosmetics. Results are shown in Table 1. Each of the blending amounts is based on the weight percentage.
(Functional Evaluation)
An aqueous 10 wt % solution of each conpound was prepared and evaluation was made for the moist feel and absence of stickiness (smooth feel) by 10 expert panellers. As the evaluation method, a sample was applied after cleaning the upper arm and a total value of the evaluation in five ranks for the moist feel and absence of sticky feel from just al to 30 min after application was adopted. It was judged favorable for those with scores of 35 or higher.
<Absence of Sticky Feel (Smooth Feel)>
5: Spreading is excellent, with an extremely light feel with no resistance felt when rubbed on the skin
4: Spreading is good, with a light feel without any resistance felt when rubbed on the skin
3: Spreading is somewhat poor, with a slight resistance felt when rubbed on the skin
2: Spreading is poor, with heavy resistance felt when rubbed on the skin
1: Spreading is extremely poor, with an extremely heavy resistance felt when rubbed on the skin
<Moist Feel>
5: No dryness at all, with sufficient mist feel
4: No dryness with moist feel
3: Some dryness with somewhat insufficient moist feel
2: Dryness with insufficient moist fed
1: Considerable dryness with extremely insufficient moist feel
The basic agent of the invention satisfies the sores both for the moist feel and absence of stickiness. However, Comparative Examples 1 to 8 can not satisfy the two properties simultaneous.
Examples 8 to 17 and Comparative Examples 9 to 15
The compounds 1 to 10, glycerin, sorbitol, polyethylene glycol (molecular weight: 300) and lysine hydrogen chloride were blended to aqueous phase portion. Oil phase portion having the following composition in the basic agent was heated to 80° C. to dissolve uniformly, and the aqueous phase portion was gradually added thereto and stirred at the same temperature. They were then cooled to 40° C. to form lotion and the same evaluation items as in Example 1 was conducted The results are shown in Table 2.
Oil phase portion Behenyl alcohol 2.0 wt % Squalane 6.0 wt % Isopropyl millistate 0.5 wt % Sorbitan monostearate 1.0 wt % Glycerin monostearate 1.0 wt % Polyoxyethylene (20 mol) dodecyl ether 1.5 wt % Perfume approximate amount Preservatives approximate amount Aqueous phase portion Humectant Refer to Table 3 Purified water balance (to make-up the entire portion to 100)

For the prepared lotion, evaluation was conducted by the method described above for the moist feel and absence of sticky feel (smooth fed), and evaluation after cleaning was conducted by the following method.
(Evaluation After Cleaning)
After conducting a functional evaluation for the formulated product described above by 10 expert panellers, total value for evaluation in five ranks for the feeling 15 min after cleaning the upper arm portion with the soap was adopted. Those with scores of 35 or higher were judged favorable.
<Feel After Cleaning>
5: Almost fee from sin dryness, with moist feel
4: No skin dryness, with somewhat moist feel
3: A little skin dryness, but not reaching a feel of skin roughness
2: A little more skin dryness, with a feel approaching that of in roughness
1: Extreme skin dryness with feel of skin roughness
TABLE 2 Humectant blend Examples Comparative Examples (Wt. %) 8 9 10 11 12 13 14 15 16 17 9 10 11 12 13 14 15 Compound 1 20 — — — — — — — — — — — — — — — Compound 2 — 20 — — — — 10 10 5 15 — — — — — — — Compound 3 — — 20 — — — — — — — — — — — — — — Compound 4 — — — 20 — — — — — — — — — — — — — Compound 5 — — — — 20 — — — — — — — — — — — — Compound 6 — — — — — 20 — — — — — — — — — — — Compound 7 — — — — — — — — — — 20 — — — — — — Compound 8 — — — — — — — — — — — 20 — — — — — Compound 9 — — — — — — — — — — — — 20 — — — — Compound 10 — — — — — — — — — — — — — 20 — — — Glycerin — — — — — — 10 — 15 5 — — — — 20 — 10 Sorbitol — — — — — — — 10 — — — — — — — 10 — Polyethylene glycol — — — — — — — — — — — — — — — 10 — (MW: 300) Lysine hydrogen — — — — — — — — — — — — — — — — 10 Absence of sticky 36 44 36 35 45 44 47 46 44 47 30 20 45 40 13 15 12 feel Moist feel 37 43 44 43 38 37 48 47 48 44 40 39 22 30 46 45 42 Feel after cleaning 37 41 40 38 35 35 43 42 40 39 29 24 16 23 30 35 28

In the same manner, as in the results of evaluation items for the basic agents per se, cosmetics of the invention sat all of the absence of sticky feel, moist feel, and feel after cleaning in view of Examples 8 to 17. However, none of Comparative Examples 9 to 15 simultaneously satisfies the three properties.