U.S. patent application number 10/490616 was filed with the patent office on 2004-10-07 for external preparation for the skin.
Invention is credited to Kakoki, Hiroyuki, Miyahara, Reiji, Oguchi, Nozomi, Ohmori, Takashi.
Application Number | 20040197361 10/490616 |
Document ID | / |
Family ID | 19115613 |
Filed Date | 2004-10-07 |
United States Patent
Application |
20040197361 |
Kind Code |
A1 |
Oguchi, Nozomi ; et
al. |
October 7, 2004 |
External preparation for the skin
Abstract
A skin treatment composition that characteristically contains
alkylene polyglycol dineopentanoate having a specific structure.
The object is to provide a skin treatment composition that gives a
refreshing sensation at the time of application and contains an oil
component that is highly safe with low skin irritation. The skin
treatment composition specifically contains diethyleneglycol
dineopentanoate, triethyleneglycol dineopentanoate,
tetraethyleneglycol dineopentanoate, dipropyleneglycol
dineopentanoate, tripropyleneglycol dineopentanoate, etc.
Dipropyleneglycol dineopentanoate and tripropyleneglycol
dineopentanoate are particularly preferable in terms of the
sensation at the time of application; they provide a skin treatment
composition that is particularly superior in absorption into the
skin and a sensation of permeation and highly safe.
Inventors: |
Oguchi, Nozomi; (Kanagawa,
JP) ; Miyahara, Reiji; (Kanagawa, JP) ;
Kakoki, Hiroyuki; (Kanagawa, JP) ; Ohmori,
Takashi; (Kanagawa, JP) |
Correspondence
Address: |
Law Offices of Townsend & Banta
South Building Suite 900
601 Pennsylvania Avenue NW
Washington
DC
20004
US
|
Family ID: |
19115613 |
Appl. No.: |
10/490616 |
Filed: |
March 25, 2004 |
PCT Filed: |
September 24, 2002 |
PCT NO: |
PCT/JP02/09755 |
Current U.S.
Class: |
424/401 |
Current CPC
Class: |
A61Q 5/00 20130101; A61Q
17/04 20130101; A61Q 5/02 20130101; A61K 8/39 20130101; A61P 17/00
20180101; A61Q 1/06 20130101; A61Q 1/14 20130101; A61Q 19/10
20130101; A61Q 1/12 20130101; A61Q 19/00 20130101; A61Q 1/02
20130101 |
Class at
Publication: |
424/401 |
International
Class: |
A61K 007/00 |
Foreign Application Data
Date |
Code |
Application Number |
Sep 26, 2001 |
JP |
2001-293922 |
Claims
1. A skin treatment composition that characteristically contains an
alkylene polyglycol dineopentanoate represented by the following
general formula (1): 5(In this formula, m denotes an integer 2-4,
and n denotes an integer 2-3.)
2. The skin treatment composition of claim 1 wherein the compound
represented by formula (1) is tripropyleneglycol
dineopentanoate.
3. Tripropyleneglycol dineopentanoate represented by general
formula (2) as follows: 6
4. The skin treatment composition of claim 2, wherein the treatment
composition is an emulsion, and a blend ratio of the alkylene
polyglycol dineopentanoate therein is 0.001-50.0% (mass percentage)
of the total composition.
5. The skin treatment composition of claim 2, wherein the treatment
composition is an emulsion, and a blend ratio of the alkylene
polyglycol dineopentanoate therein is 0.1-30.0% (mass percentage)
of the total composition.
6. The skin treatment composition of claim 1, further comprising
one or more selected from the group consisting of a powder, liquid
fats and oils, solid fats and oils, waxes, hydrocarbons, higher
fatty acids, higher alcohols, esters, silicones, anionic
surfactants, cationic surfactants, ampholytic surfactants, nonionic
surfactants, humectants, water-soluble polymers, thickeners,
coating agents, ultraviolet absorbents, sequestering agents, lower
alcohols, polyhydric alcohols, sugars, amino acids, organic amines,
polymer emulsions, pH adjusting agents, skin nutrients, vitamins,
antioxidants, antioxidation assistants, perfumes, and water.
7. The skin treatment composition of claim 2, further comprising
one or more selected from the group consisting of a powder, liquid
fats and oils, solid fats and oils, waxes, hydrocarbons, higher
fatty acids, higher alcohols, esters, silicones, anionic
surfactants, cationic surfactants, ampholytic surfactants, nonionic
surfactants, humectants, water-soluble polymers, thickeners,
coating agents, ultraviolet absorbents, sequestering agents, lower
alcohols, polyhydric alcohols, sugars, amino acids, organic amines,
polymer emulsions, pH adjusting agents, skin nutrients, vitamins,
antioxidants, antioxidation assistants, perfumes, and water.
8. A method of treating skin comprising applying to the skin the
composition of claim 1.
9. A method of treating skin comprising applying to the skin the
composition of claim 2.
10. A method of producing alkylene polyglycol dineopentanoate of
Formula (1): 7wherein m denotes an integer 2-4, and n denotes an
integer 2-3, comprising reacting pivaloyl chloride with
polyethylene glycol according to the reaction scheme as follows:
8
11. The method of claim 10, wherein resultant reaction solution is
rinsed with ammonium chloride and then extracted with ethyl acetate
to form a resultant extract solution.
12. The method of claim 11, wherein the resultant extract solution
is concentrated and purified by column chromatography.
Description
TECHNICAL FIELD
[0001] The present invention relates to a skin treatment
composition that gives a refreshing sensation at the time of
application and contains an oil component that is highly safe with
low skin irritation.
BACKGROUND ART
[0002] Silicone oil has been added frequently to skin treatment
compositions as an oil component that gives a refreshing sensation
at the time of application.
[0003] However, since silicone oil has poor solubility with drugs
and/or ultraviolet absorbents, hydrocarbon type oil components that
give a refreshing sensation at the time of application have been
desired.
[0004] However, an oil component that gives a refreshing sensation
at the time of application has a small molecular weight and
therefore a higher percutaneous absorption into the skin. As
result, skin irritation such as tingling tends to become more
pronounced.
[0005] In view of the aforementioned problem, the inventors
conducted earnest research and discovered that a skin treatment
composition that gives a refreshing sensation at the time of
application and is highly safe with low skin irritation can be
obtained by blending in a specific alkylene polyglycol
dineopentanoate as an oil component, and thus completed the present
invention.
[0006] The object of the present invention is to provide a skin
treatment composition that has a particularly refreshing sensation
at the time of application and is highly safe.
DISCLOSURE OF INVENTION
[0007] That is, the present invention provides a skin treatment
composition that characteristically contains an alkylene polyglycol
dineopentanoate represented by the following general formula (1):
1
[0008] (In this formula, m denotes an integer 2-4, and n denotes an
integer 2-3.)
[0009] Also, the present invention provides the aforementioned skin
treatment composition wherein the compound represented by general
formula (1) is tripropyleneglycol dineopentanoate represented by
general formula (2): 2
[0010] (In this formula, m denotes an integer 2-4.)
BEST MODE FOR CARRYING OUT THE INVENTION
[0011] The present invention is described in detail below.
[0012] The oil component of general formula (1) used in the present
invention is a prior art hydrocarbon type oil component.
[0013] In the present invention, it is preferable to use a diester
obtained by the condensation reaction between neopentyl chloride
and polyethylene glycol.
[0014] The synthesis scheme is shown below: 3
[0015] The reaction solution obtained by the aforementioned
synthesis scheme is rinsed several times with an ammonium chloride
aqueous solution and subjected to extraction with ethyl acetate;
the extract solution is concentrated and roughly purified by column
chromatography, and further purified by vacuum distillation.
[0016] (In general formula (1), m denotes an integer 2-4.) If m is
1, then the compound is volatile and malodorous. If m is five or
more, the refreshing sensation at the time of application tends to
be diminished.
[0017] Specific examples of alkylene polyglycol dineopentanoate
that satisfies general formula (1) include diethyleneglycol
dineopentanoate, triethyleneglycol dineopentanoate,
tetraethyleneglycol dineopentanoate, dipropyleneglycol
dineopentanoate, and tripropyleneglycol dineopentanoate.
[0018] Dipropyleneglycol dineopentanoate and tripropyleneglycol
dineopentanoate are particularly preferable in terms of the
sensation at the time of application; they provide a skin treatment
composition that is particularly superior in terms of absorption
into the skin and a sensation of permeation as well as being highly
safe.
[0019] The blend ratio of the alkylene polyglycol dineopentanoate
is not limited in particular. It is determined based on the
formulation and the type of the product.
[0020] Usually, in the case of emulsified skin treatment
compositions, the blend ratio is 0.001-50.0% (mass percentage),
preferably 0.1-30.0% (mass percentage), of the total
composition.
[0021] If it is less than 0.001%, then the effect of adding the oil
component is not manifested; if it is more than 50.0%, then
stickiness is felt after application.
[0022] The oil component of general formula (1) gives a refreshing
sensation at the time of application, and is superior as an oil
component to be blended into the base agent of skin treatment
compositions such as cosmetics and quasi-drugs.
[0023] It is highly safe and superior in absorption into the skin
as a hydrocarbon type oil component replacing silicone oil.
[0024] Also, drugs and ultraviolet absorbents can be easily blended
in when the base agent contains the oil component of general
formula (1).
[0025] The skin treatment composition of the present invention is
prepared by blending the aforementioned oil component into an
existing skin treatment composition base agent.
[0026] In addition to the aforementioned oil components, other
ingredients used in skin treatment compositions can be blended as
necessary in the skin treatment composition of the present
invention; examples of such ingredients include powder ingredients,
liquid fats and oils, solid fats and oils, waxes, hydrocarbons,
higher fatty acids, higher alcohols, esters, silicones, anionic
surfactants, cationic surfactants, ampholytic surfactants, nonionic
surfactants, humectants, water-soluble polymers, thickeners,
coating agents, ultraviolet absorbents, sequestering agents, lower
alcohols, polyhydric alcohols, sugars, amino acids, organic amines,
polymer emulsions, pH adjusting agents, skin nutrients, vitamins,
antioxidants, antioxidation assistants, perfumes, and water; and
the skin treatment composition can be prepared for the target
formulation with a conventional method.
[0027] Specific ingredients which can be blended in are listed
below. The skin treatment composition of the present invention can
be prepared by blending the aforementioned essential ingredients
and any one, two or more of the following ingredients.
[0028] Examples of the powder ingredients include inorganic powders
(for example, talc, kaolin, mica, sericite, muscovite, phlogopite,
synthetic mica, lepidolite, biotite, vermiculite, magnesium
carbonate, calcium carbonate, aluminum silicate, barium silicate,
calcium silicate, magnesium silicate, strontium silicate, tungstic
acid metal salt, magnesium, silica, zeolite, barium sulfate, firing
calcium sulfate (calcined gypsum), calcium phosphate,
fluorine-apatite, hydroxy apatite, ceramic powder, metallic soaps
(for example, myristic acid zinc, calcium palmitate, and aluminum
stearate), and boron nitride); organic powders (for example,
polyamide resin powder (nylon powder), polyethylene powder, poly
methyl methacrylate powder, polystyrene powder, powders of the
copolymer resin of styrene and acrylic acid, benzoguanamine resin
powder, polytetrafluoroethylene powder, and cellulose powder);
inorganic white pigments (for example, titanium dioxide and zinc
oxide); inorganic red pigments (for example, iron oxide (red iron
oxide) and iron titanate); inorganic brown pigments (for example,
.gamma.-iron oxide); inorganic yellow pigments (for example, yellow
iron oxide and loess); inorganic black pigments (for example, black
iron oxide and low oxides of titanium); inorganic purple pigments
(for example, manganese violet, cobalt violet); inorganic green
pigments (for example, chromium oxide, chromium hydroxide, and
cobalt titanate); inorganic blue pigments (for example, ultramarine
blue and Berlin blue); pearl pigment (for example, titania coated
mica, titania coated bismuth oxychloride, titania coated talc,
coloration titania coated mica, bismuth oxychloride, fish scale
flakes); metal powder pigments (for example, aluminium powder,
copper powder); organic pigments such as Zr, barium or aluminium
rake (for example, organic pigments such as red 201, red 202, red
204, red 205, red 220, red 226, red 228, red 405, orange 203,
orange 204, yellow 205, yellow 401 and blue 404, as well as red 3,
red 104, red 106, red 227, red 230, red 401, red 505, orange 205,
yellow 4, yellow 5, yellow 202, yellow 203, green 3 and blue 1; and
natural colors (for example, chlorophyll and .beta.-carotene).
[0029] Examples of the liquid fats and oils include avocado oil,
tsubaki oil, turtle fatty acid, macademia nut oil, corn oil, mink
oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, persic oil,
wheat germ oil, sasanqua oil, castor oil, linseed oil, safflower
oil, cotton seed oil, perilla oil, soybean oil, peanut oil, tea
seed oil, Japanese nutmeg oil, rice bran oil, Chinese gimlet oil,
Japan gimlet oil, jojoba oil, germ oil, and triglycerin.
[0030] Examples of the solid fats and oils include cacao butter,
coconut oil, hydrogenated coconut oil, palm oil, palm kernel oil,
Japanese core wax nucleus oil, hydrogenated oil, Japanese core wax,
and hydrogenated castor oil.
[0031] Examples of the waxes include beeswax, candelilla wax,
cotton wax, carnauba wax, bayberry wax, tree wax, whale wax, montan
wax, bran wax, lanolin, kapok wax, lanolin acetate, liquid lanolin,
sugar cane wax, lanolin fatty acid isopropyl ester, hexyl laurate,
reduced lanolin, jojoba wax, hard lanolin, shellac wax, POE lanolin
alcohol ether, POE lanolin alcohol acetate, POE cholesterol ether,
lanolin fatty acid polyethylene glycol, and POE hydrogenated
lanolin ethyl alcohol ether.
[0032] Examples of the hydrocarbon oils include liquid petrolatum,
ozocerite, squalane, pristane, paraffin, ceresin, squalene,
petrolatum, and microcrystallin wax.
[0033] Examples of the higher fatty acids include lauric acid,
myristic acid, palmitic acid, stearic acid, behenic acid, oleic
acid, undecylenic acid, tall oil fatty acid, isostearic acid,
linolic acid, linoleic acid, eicosapentaenoic acid (EPA), and
docosahexaenoic acid (DHA).
[0034] Examples of the higher alcohols include straight chain
alcohols (for example, lauryl alcohol, cetyl alcohol, stearyl
alcohol, behenyl alcohol, myristyl alcohol, oleyl alcohol, and
cetostearyl alcohol) and branched chain ethyl alcohols (for
example, mono stearyl glycerin ether (batyl alcohol),
2-decyltetradecynol, lanolin alcohol, cholesterol, phytosterol,
hexyl dodecanol, iso stearyl alcohol, and octyl dodecanol).
[0035] Examples of the ester oils include isopropyl myristate,
cetyl octanoate, octyl dodecyl myristate, isopropyl palmitate,
butyl stearate, hexyl laurate, myristil myristate, decyl oleate,
dimethyl hexyl decyl octanoate, cetyl lactate, myristil lactate,
lanolin acetate, iso cetyl stearate, iso cetyl isostearate,
cholesteryl hydroxy 12-stearate, di-2-ethylene glycol
ethylhexanoate, dipentaerythritol fatty acid ester, n-alkylene
glycol monoisostearate, neopentyl glycol dicaprate, diisostearyl
malate, glyceryl di-2-heptylundecanoate, trimethylolpropane
tri-2-ethylhexanoate, trimethylolpropane triisostearate,
tetra-2-pentaerythritol ethylhexanoate, glycerin
tri-2-ethylhexanoate, glyceryl trioctanoate, glycerin
triisopalmitate, trimethylolpropane triisostearate, cetyl 2-ethyl
hexanoate, 2-ethylhexyl palmitate, glycerin trimyristate,
tri-2-heptyl undecanoic acid glyceride, methyl castor oil fatty
acid, oleyl oleate, aceto glyceride, 2-heptyl undecyl palmitate,
diisobutyl adipate, 2-octyldodecyl N-lauroyl-L-glutamate,
di-2-heptyl undecyl adipate, ethyl laurate, di-2-ethylhexyl
sebacate, 2-hexyl decyl myristate, 2-hexyl decyl palmitate, 2-hexyl
decyl adipate, diisopropyl sebacate, 2-ethylhexyl succinate, and
triethyl citrate.
[0036] Examples of the silicone oils include chain polysiloxanes
(for example, dimethylpolysiloxane, methylphenyl polysiloxane, and
diphenyl polysiloxane); ring polysiloxanes (for example,
octamethylcyclotetrasilox- ane, decamethyl cyclopenta siloxane, and
dodecamethyl cyclohexa siloxane), silicone resins forming a
three-dimensional network structure, silicone rubbers, and various
modified polysiloxanes (amino-modified polysiloxane,
polyether-modified polysiloxane, alkyl-modified polysiloxane, and
and fluorine-modified polysiloxane).
[0037] Examples of the anionic surfactants include fatty acid soaps
(for example, sodium laurate and sodium palmitate); higher alkyl
sulfuric ester salts (for example, sodium lauryl sulfate and
potassium laurylsulfate); alkylether sulfuric ester salts (for
example, POE-triethanolamine laurylsulfate and sodium POE-lauryl
sulfate); N-acyl sarcosinic acids (for example, sodium N-lauroyl
sarcosinate); higher fatty acid ester sulfates (for example,
hydrogenated coconut oil aliphatic acid glycerin sodium sulfate);
N-acyl glutamates (for example, mono sodium N-lauroylglutamate,
disodium N-stearoylglutamate, and sodium N-myristoyl-L-glutamate);
sulfated oils (for example, turkey red oil); POE-alkylether
carboxylic acid; POE-alkylarylether carboxylate; .alpha.-olefin
sulfonate; higher fatty acid ester sulfonates; sec-alcohol
sulfates; higher fatty acid alkyl amide sulfates; sodium lauroyl
monoethanolamine succinates; ditriethanolamine
N-palmitoylaspartate; and sodium caseinate.
[0038] Examples of the cationic surfactants include
alkyltrimethylammonium salts (for example, stearyltrimethyl
ammonium chloride and lauryltrimethyl ammonium chloride)
alkylpyridinium salts (for example, cetylpyridinium chloride),
distearyldimethylammonium chloride dialkyldimethylammonium salt;
poly (N,N'-dimethyl-3,5-methylene piperidinium) chloride; alkyl
quaternary ammonium salts; alkyl dimethylbenzyl ammonium salts;
alkyl isoquinolinium salts; dialkylmorpholine salts; POE alkyl
amines; alkyl amine salts; polyamine fatty acid derivatives;
amylalcohol fatty acid derivatives; benzalkonium chloride; and
benzethonium chloride.
[0039] Examples of the ampholytic surfactants include: imidazoline
type ampholytic surfactants (for example,
2-undecyl-N,N,N-(hydroxyethyl carboxymethyl)-2-imidazoline sodium
salt and 2-coco yl-2-imidazolinium hydroxide-1-carboxyethyloxy 2
sodium salt); and betaine type surfactants (for example,
2-heptadecyl-n-carboxymethyl-n-hydroxyethyl imidazolinium betaine,
lauryldimethylaminoacetic acid betaine, alkyl betaine, amide
betaine, and sulfobetaine).
[0040] Examples of the lipophilic nonionic surface active agent
include sorbitan fatty acid esters (for example, sorbitan mono
oleate, sorbitan mono isostearate, sorbitan mono laurate, sorbitan
mono palmitate, sorbitan mono stearate, sorbitan sesqui oleate,
sorbitan trioleate, diglycerol sorbitan penta-2-ethylhexylate,
diglycerol sorbitan tetra-2-ethylhexylate); glycerin polyglycerin
aliphatic acids (for example, mono-cottonseed oil fatty acid
glycerin, glyceryl monoerucate, glycerin sesquioleate, glyceryl
monostearate, .alpha.,.alpha.'-glyceryl oleate pyroglutamate,
glyceryl mono stearate mono malate); propylene glycol fatty acid
esters (for example, propylene glycol monostearate) hydrogenated
castor oil derivatives; and glycerin alkylethers.
[0041] Examples of the hydrophilic nonionic surface active agents
include: POE-sorbitan fatty acid esters (for example, POE-sorbitan
monooleate, POE-sorbitan monostearate, POE-sorbitan monoolate, and
POE-sorbitan tetraoleate); POE sorbitol fatty acid esters (for
example, POE sorbitol monolaurate, POE-sorbitol monooleate,
POE-sorbitolpentaoleate, and POE-sorbitol monostearate);
POE-glycerin fatty acid esters (for example, POE-monooleates such
as POE-glycerin monostearate, POE-glycerin monoisostearate, and
POE-glycerin triisostearate); POE-fatty acid esters (for example,
POE-distearate, POE-monodioleate, and ethylene glycol distearate);
POE-alkylethers (for example, POE-lauryl ether, POE-oleyl ether,
POE-stearyl ether, POE-behenyl ether, POE-2-octyl dodecyl ether,
and POE-cholestanol ether); POE/POP-alkylethers (for example,
POE/POP-cetyl ether, POE/POP-2-decyl tetradecyl ether,
POE/POP-monobutyl ether, POE/POP-lanolin hydrate, and
POE/POP-glycerin ether); POE-castor oil hydrogenated castor oil
derivatives (for example, POE-castor oil, POE-hydrogenated castor
oil, POE-hydrogenated castor oil monoisostearate, POE-hydrogenated
castor oil triisostearate, POE-hydrogenated castor oil
monopyroglutamic monoisostearic diester, and POE-hydrogenated
castor oil maleic acid); POE-beeswax/lanolin derivatives (for
example, POE-sorbitol beeswax); alkanol amides (for example,
coconut fatty acid diethanol amide,. lauric acid monoethanol amide,
and aliphatic acid isopropanol amide); POE-propylene glycol fatty
acid esters; POE-alkyl amine; POE-fatty acid amide; sucrose fatty
acid ester; alkyl ethoxy dimethylamine oxides; and trioleyl
phosphoric acid.
[0042] Examples of the humectant include polyethylene glycol,
propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol,
maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfuric
acid, charonic acid, atelocollagen, cholesteryl-12-hydroxy
stearate, sodium lactate, bile salt, dl-pyrrolidone carboxylic acid
salt, short chain soluble collagen, diglycerin (EO)PO adduct,
chestnut rose fruit extract, yarrow extract, and sweet clover
extract.
[0043] Examples of the natural water-soluble polymer include:
plant-type polymers (for example, gum arabic, gum tragacanth,
galactan, guar gum, carob gum, karaya gum, carrageenan, pectin,
agar, quince seed (Cydonia oblonga), algae colloids (brown algae
extract), starches (rice, corn, potato, and wheat), and
glycyrrhizic acid); microorganism-type polymers (for example,
xanthan gum, dextran, succinoglucan, and pullulan); and animal-type
polymers (for example, collagen, casein, albumin, and gelatin).
[0044] Examples of the semisynthetic water-soluble polymers
include: starch-type polymers (for example, carboxymethyl starch
and methylhydroxypropyl starch); cellulosic polymers (for example,
methyl cellulose, ethyl cellulose, methylhydroxypropyl cellulose,
hydroxyethyl cellulose, cellulose sodium sulfate, hydroxypropyl
cellulose, carboxymetyl-cellulose, sodium carboxymethyl cellulose,
crystal cellulose, and cellulose powder); and alginic acid-type
polymers (for example, sodium alginate and propyleneglycol
alginate).
[0045] Examples of the synthetic water-soluble polymers include:
vinyl polymers (for example, polyvinyl alcohol, polyvinyl methyl
ether, polyvinylpyrrolidone, carboxy vinyl polymer);
polyoxyethylene-type polymers (for example, a copolymer of
polyethylene glycol 20,000, 40,000, or 60,000 and polyoxyethylene
polyoxypropylene); acrylic polymers (for example, sodium
polyacrylate, polyethylacrylate, and polyacrylamide);
polyethyleneimine; and cationic polymers.
[0046] Examples of the thickeners include: gum arabic, carrageenan,
karaya gum, gum tragacanth, carob gum, quince seed (Cydonia
oblonga), casein, dextrin, gelatin, sodium pectate, sodium
arginate, methyl cellulose, ethyl cellulose, CMC, hydroxy ethyl
cellulose, hydroxypropyl cellulose, PVA, PVM, PVP, sodium
polyacrylate, carboxy vinyl polymer, locust bean gum, guar gum,
tamarind gum, cellulose dialkyl dimethylammonium sulfate, xanthan
gum, aluminum magnesium silicate, bentonite, hectorite, AlMg
silicate (beagum), laponite, and silicic acid anhydride.
[0047] Examples of the ultraviolet absorbents include the
following.
[0048] (1) Benzoic Acid-Type Ultraviolet Absorbents
[0049] For example, paraminobenzoic acid (hereafter abbreviated as
PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester,
N,N-diethoxy PABA ethyl ester, N,N-dimethyl PABA ethyl ester, N,
N-dimethyl PABA butyl ester, and N,N-dimethyl PABA ethyl ester.
[0050] (2) Anthranilic Acid-Type Ultraviolet Absorbents
[0051] For example, homo mentyl-N-acetyl anthranilate.
[0052] (3) Salicylic Acid-Type Ultraviolet Absorbents
[0053] For example, amyl salicylate, mentyl salicylate, homo mentyl
salicylate, octyl salicylate, phenyl salicylate, benzil salicylate,
and p-isopropanol phenyl salicylate.
[0054] (4) Cinnamic Acid-Type Ultraviolet Absorbents
[0055] For example, octyl cinnamate, ethyl-4-isopropyl cinnamate,
methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropyl cinnamate,
methyl-2,4-diisopropyl cinnamate, propyl-p-methoxy cinnamate,
isopropyl-p-methoxy cinnamate, isoamyl-p-methoxy cinnamate,
octyl-p-methoxy cinnamate (2-ethylhexyl-p-methoxy cinnamate),
2-ethoxyethyl-p-methoxy cinnamate, cyclohexyl-p-methoxy cinnamate,
ethyl-.alpha.-cyano-.beta.-phenyl cinnamate,
2-ethylhexyl-.alpha.-cyano-.- beta.-phenyl cinnamate, and glyceryl
mono-2-ethyl hexanoyl-diparamethoxy cinnamate.
[0056] (5) Triazine-Type Ultraviolet Absorbents
[0057] For example, bisresorsinyl triazine.
[0058] More specifically,
bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4--
methoxyphenyl)1,3,5-triazine,
2,4,6-tris{4-(20ethylhexyloxycarbonyl)anilin- o}1,3,5-triazine,
etc.
[0059] (6) Other Ultraviolet Absorbents
[0060] For example, 3-(4'-methylbenzylidene)-d, 1-camphor,
3-benzylidene-d, 1-camphor, 2-phenyl-5-methyl benzoxazol,
2-(2'-hydroxy-5'-methylphenyl) benzotriazol,
2-(2'-hydroxy-5'-t-octylphen- yl) benzotriazol,
2-(2'-hydroxy-5'-methylphenyl benzotriazol, dibenzaladine,
dianisoylmethane, and 4-methoxy-4'-t-butyl dibenzoyl-methane,
5-(3,3-dimethyl-2-norbornylidene)-3-pentane-2-one. Pyridazinone
derivatives such as dimorpholino pyridazine.
[0061] Examples of the sequestering agents include: 1-hydroxy
ethane-1,1-diphosphonic acid, 1-hydroxy ethane-1,1-diphosphonic
acid tetrasodium salt, disodium edetate, trisodium edetate,
tetrasodium edetate, sodium citrate, sodium polyphosphate, sodium
metaphosphate, gluconic acid, phosphoric acid, citric acid,
ascorbic acid, succinic acid, and trisodium
ethylenediaminehydroxyethyl triacetate.
[0062] Examples of the lower alcohols include ethanol, propanol,
isopropanol, isobutanol, and t-butyl alcohol.
[0063] Examples of the polyhydric alcohols include: dihydric
alcohols (for example, ethylene glycol, propylene glycol,
trimethylene glycol, 1,2-butylene glycol, 1,3-butylene glycol,
tetramethylene glycol, 2,3-butylene glycol, pentamethylene glycol,
2-butene-1,4-diol, hexylene glycol, and octylene glycol); trihydric
alcohols (for example, glycerin and trimethylolpropane);
tetrahydric alcohols (for example, pentaerythritol such as
1,2,6-hexanetriol) pentahydric alcohols (for example, xylitol);
hexahydric alcohols (for example, sorbitol, mannitol); polyhydric
alcohol polymers (for example, diethylene glycol, dipropylene
glycol, triethylene glycol, polypropylene glycol, tetraethylene
glycol, diglycerin, polyethylene glycol, triglycerin,
tetraglycerin, and polyglycerin); dihydric alcohol alkylethers (for
example, ethylene glycol monomethyl ether, ethylene glycol
monoethyl ether, ethylene glycol monobutyl ether, ethylene glycol
monophenyl ether, ethylene glycol monohexyl ether, ethylene glycol
mono 2-methyl hexyl ether, ethylene glycol isoamyl ether, ethylene
glycol benzyl ether, ethylene glycol isopropyl ether, ethylene
glycol dimethylether, ethylene glycol diethyl ether, and ethylene
glycol dibutyl ether); dihydric alcohol ether esters (for example,
ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl
ether acetate, ethylene glycol monobutyl ether acetate, ethylene
glycol monophenyl ether acetate, ethylene glycol diadipate,
ethylene glycol disuccinate, diethylene glycol monoethyl ether
acetate, diethylene glycol monobutyl ether acetate, propylene
glycolmonomethyl ether acetate, propylene glycol monoethyl ether
acetate, propylene glycol monopropyl ether acetate, and propylene
glycol monophenyl ether acetate); glycerin mono alkyl ethers (for
example, xylyl alcohol, selachyl alcohol, and batyl alcohol); sugar
alcohols (for example, sorbitol, maltitol, maltotriose, mannitol,
sucrose, erythritol, glucose, fructose, starch amylolysis sugar,
maltose, xylitose, and alcohol prepared by the reduction of starch
amylolysis sugar); glysolid; tetrahydro furfuryl alcohol;
POE-tetrahydro furfuryl alcohol; POP-butyl ether; POP-POE-butyl
ether; tripolyoxypropylene glycerin ether; POP-glycerin ether,
POP-glycerin ether phosphoric acid; POP/POE-pentane erythritol
ether, and polyglycerin.
[0064] Examples of the monosaccharides include: trioses (for
example, D-glyceryl aldehyde and dihydroxyacetone); tetroses (for
example, D-etythrose, D-erythrulose, D-threose, and erythritol);
pentoses (for example, L-arabinose, D-xylose, L-lyxose,
D-arabinose, D-ribose, D-ribulose, D-xylulose, and L-xylulose);
hexoses (for example, D-glucose, D-talose, D-psicose, D-galactose,
D-fructose, L-galactose, L-mannose, and D-tagatose); heptoses (for
example, aldoheptose and heprose); octoses (for example, octurose);
deoxysugars (for example, 2-deoxy-D-ribose, 6-deoxy-L-galactose,
and 6-deoxy-L-mannose); amino sugars (for example, D-glucosamine,
D-galactosamine, sialic acid, amino uronic acid, and muramic acid);
and uronic acid (for example, D-glucuronic acid, D-mannuronic acid,
L-guluronic acid, D-galacturonic acid, and L-iduronic acid).
[0065] Examples of the oligosaccharides include sucrose,
umbelliferose, lactose, planteose, isolignoses,
.alpha.,.alpha.-trehalose, raffinose, lignoses, umbilicine,
stachyose and verbascose.
[0066] Examples of the polysaccharides include cellulose, quince
seed, chondroitin sulfate, starch, galactan, dermatan sulfate,
glycogen, gum arabic, heparan sulfate, hyaluronic acid, traganth
gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfuric
acid, guar gum, dextran, kerato sulfate, locustbean gum,
succinoglucane, and charonic acid.
[0067] Examples of the amino acids include neutral amino acids (for
example, threonine and cysteine) and basic amino acids (for
example, hydroxylysine). Examples of the amino acid derivatives
include sodium acyl sarcosinate (sodium N-lauroyl sarcosinate),
acyl glutamate, acyl .beta.-alanine sodium, glutathione, and
pyrrolidone carboxylic acid.
[0068] Examples of the organic amines include monoethanolamine,
diethanolamine, triethanolamine, morpholine, triisopropanolamine,
2-amino-2-carbinyl-1,3-propanediol, and
2-amino-2-carbinyl-1-propanol.
[0069] Examples of the high polymer emulsions include acrylic resin
emulsions, ethyl polyacrylate emulsions, acryl resin liquids,
polyacrylic alkyl ester emulsions, polyvinyl acetate resin
emulsions, and natural rubber latex.
[0070] Examples of the pH adjustment agents include buffers such as
lactic acid-sodium lactate, citric acid-sodium citrate, and
succinic acid-sodium succinate.
[0071] Examples of the vitamins include vitamins A, B1, B2, B6, C
and E as well as their derivatives, pantothenic acid and its
derivatives, and biotin.
[0072] Examples of the antioxidants include tocopherols, dibutyl
hydroxytoluene, butyl hydroxyanisole, and gallic ester.
[0073] Examples of the antioxidation auxiliary agents include
phosphoric acid, citric acid, ascorbic acid, maleic acid, malonic
acid, succinic acid, fumaric acid, cephalin, hexameta phosphate,
phytic acid, and ethylene diamine tetraacetic acid.
[0074] Examples of other possible ingredients include antiseptics
(methylparaben, ethylparaben, butylparaben, and phenoxyethanol);
anti-inflammatory agents (for example, glycyrrhizic acid
derivatives, glycyrrhetinic acid derivatives, salicylic acid
derivatives, hinokitiol, zinc oxide, and allantoin); whitening
agents (for example, creeping saxifrage extract and arbutin);
various extracts (for example, Phellodendri Cortex, goldthread,
lithospermum root, Paeonia lactiflora, Swertia japonica, Birch,
sage, loquat, carrot, aloe,. Malva sylvestris, Iris, grape, Coix
ma-yuen, sponge gourd, lily, saffron, Cnidium officinale, sheng
jiang, Hypericum erectum, Ononis, garlic, Guinea pepper, chen pi,
Ligusticum acutilobum, and seaweed), activators (royal jelly,
photosensitizer, and cholesterol derivatives); blood circulation
promoting agents (for example, nonyl acid valenyl amide, nicotinic
acid benzyl esters, nicotinic acid .beta.-butoxy ethyl esters,
capsaicin, gingeron, cantharis tincture, Ichthammol, tannic acid,
.alpha.-borneol, tocopherol nicotinate, inositol hexanicotinate,
cyclandelate, cinnarizine, tolazoline, acetylcholine, verapamil,
cepharanthine, and .beta.-orizanol); anti-seborrhea agents (for
example, sulfur and thiantol); and antiinflammatory agents (for
example, tranexamic acid, thiotaurine, and hypotaurine).
[0075] Any formulation can be used for the skin treatment
composition of the present invention.
[0076] The product form of the skin treatment composition of the
present invention is also arbitrary.
[0077] It can be used in lotions, emulsions, creams, facial
cosmetics such as packs; makeup cosmetics such as foundations,
lipsticks, eye shadow; body cosmetics; aroma cosmetics; skin
cleaners such as makeup removers and body shampoos; and
ointments.
[0078] A skin treatment composition having an ultraviolet absorbent
or various drugs is also preferable.
EXAMPLES
[0079] The present invention is described in detail below by
referring to Examples. The present invention is not limited to
them.
[0080] The blend ratios are in mass-percentage (%) units unless
specified otherwise.
[0081] First, the test method and evaluation method used in
Examples and Comparative examples are described below.
[0082] "Test Method Using Patch Test"
[0083] The test was conducted using a Finn Chamber (8 mm in
diameter) with 24 hour-occlusion. Test subjects were 46 male and
female healthy volunteers (33 males and 13 females) whose ages
range from 22 to 59 (average 42); 0.03 ml of the original specimen
of alkylene polyglycol dineopentanoate was applied on the bent side
of the forearm of the test subjects for 24 hours. The application
site was secured with an elastic bandage; three hours after the
removal of the bandage and the adhesive plaster the first
evaluation (after-24-hours evaluation) was conducted according to
the evaluation criteria of Table 1, and 24 hours later another
evaluation (after-48-hours evaluation) was conducted with the same
criteria.
1TABLE 1 Evaluation criteria of the patch test Degree of skin
reaction Evaluation No reaction - Negative Mild erythema .+-.
Equivocal Erythema + Weakly positive Erythema + edema ++ Moderately
positive Erythema + edema + +++ Strongly positive papule + serous
papule + small blister Large blister ++++ Strongest positive
[0084] "Evaluation (1): Refreshing Sensation on the Skin"
[0085] The refreshing sensation on the skin during use was
evaluated with actual use test by ten specialized panelists. The
evaluation criteria are as follows:
[0086] .circleincircle. . . . Eight or more specialized panelists
reported a refreshing sensation on the skin during use.
[0087] .largecircle. . . . Six or more and less than eight
specialized panelists reported a refreshing sensation on the skin
during use.
[0088] .DELTA. . . . Three or more and less than six specialized
panelists reported a refreshing sensation on the skin during
use.
[0089] X . . . Less than three specialized panelists reported a
refreshing sensation on the skin during use.
[0090] "Evaluation (2): Permeating Sensation on the Skin"
[0091] The permeating sensation on the skin during use was
evaluated with actual use test by ten specialized panelists. The
evaluation criteria are as follows:
[0092] .circleincircle. . . . Eight or more specialized panelists
reported a permeating sensation on the skin during use.
[0093] .largecircle. . . . Six or more and less than eight
specialized panelists reported a permeating sensation on the skin
during use.
[0094] .DELTA. . . . Three or more and less than six specialized
panelists reported a permeating sensation on the skin during
use.
[0095] X . . . Less than three specialized panelists reported a
permeating sensation on the skin during use.
[0096] "Evaluation (3): Non-Stickiness on the Skin"
[0097] The non-stickiness on the skin during use was evaluated with
actual use test by ten specialized panelists. The evaluation
criteria are as follows:
[0098] .circleincircle. . . . Eight or more specialized panelists
reported non-stickiness on the skin during use.
[0099] .largecircle. . . . Six or more and less than eight
specialized panelists reported non-stickiness on the skin during
use.
[0100] .DELTA. . . . Three or more and less than six specialized
panelists reported non-stickiness on the skin during use.
[0101] X . . . Less than three specialized panelists reported
non-stickiness on the skin during use.
Examples 1-12
Comparative Examples 1-6
[0102] The positive patch test ratio was measured for Examples 1-3
and Comparative examples 1-3. Skin treatment compositions
(emulsions) of Examples 4-12 and Comparative examples 4-6 having
the blend compositions listed in Table 3, Table 4, and Table 5 were
prepared with a conventional method and the evaluation test was
conducted for the aforementioned evaluations (1), (2), and (3). The
results are shown in the tables.
[0103] The alkylene polyglycol dineopentanoate used here was
prepared as follows: using the synthesis scheme described below,
neopentyl chloride and polyethylene glycol were reacted for six
hours at 0.degree. C. to room temperature, HCl was removed, and a
diester form was prepared by means of a condensation reaction.
[0104] The polyethylene glycols used here are diethylene glycol,
triethylene glycol, tetraethylene glycol, dipropylene glycol, and
tripropylene glycol.
[0105] The reaction solution was rinsed several times with an
ammonium chloride aqueous solution and subjected to extraction with
ethyl acetate; the extract solution was concentrated and roughly
purified by column chromatography, and further purified by vacuum
distillation. The purity of the preparation for use was 99% or
higher. 4
[0106] Results of the 24 hour-occlusion patch test for the original
specimen of alkylene polyglycol dineopentanoate
2 TABLE 2 Number Evaluation Positive Equivocal Negative Positive
Samples (persons) time (hrs) ++++ +++ ++ + .+-. - ratio (%)
Examples 1 Tripropyleneglycol 46 24 0 0 0 0 0 46 0 dineopentanoate
48 0 0 0 0 0 46 0 2 Dipropyleneglycol 46 24 0 0 0 0 0 46 0
dineopentanoate 48 0 0 0 0 0 46 0 3 Tetrapropyleneglycol 46 24 0 0
0 0 0 46 0 dineopentanoate 48 0 0 0 0 0 46 0 Comparative 1 Isocetyl
oleate 46 24 0 0 2 2 3 39 8.7 example 48 0 0 0 4 2 40 8.7 2 Liquid
petrolatum 46 24 0 0 0 1 3 42 2.2 48 0 0 0 0 2 44 0 3 Isononyl
nonanoate 46 24 0 1 4 5 5 31 22 48 0 0 5 4 5 32 20
[0107] Table 2 shows that alkylene polyglycol dineopentanoate
exhibits low irritation.
3 TABLE 3 Examples Ingredients 4 5 6 7 Dineopentanoic 0.001 0.1 1.0
5.0 acidtripropylene glycol Sodium hexamethaphosphate 0.01 0.01
0.01 0.01 Trisodium edetate 0.03 0.03 0.03 0.03 1,3-butylene glycol
5 5 5 5 Potassium hydroxide 0.1 0.1 0.1 0.1 Carboxyvinyl polymer
0.1 0.1 0.1 0.1 Phenoxy ethanol 0.15 0.15 0.15 0.15 Purified water
Balance Balance Balance Balance Evaluation (1): Refreshing
.largecircle. .circleincircle. .circleincircle. .circleincircle.
sensation on the skin Evaluation (2): Permeating .largecircle.
.circleincircle. .circleincircle. .circleincircle. sensation on the
skin Evaluation (3): .largecircle. .circleincircle.
.circleincircle. .circleincircle. Non-stickiness on the skin
[0108]
4 TABLE 4 Examples Ingredients 8 9 10 11 12 Tripropyleneglycol 5 --
-- -- -- dineopentanoate Dipropyleneglycol -- 5 -- -- --
dineopentanoate Tetraethyleneglycol -- -- 5 -- -- dineopentanoate
Triethyleneglycol -- -- -- 5 -- dineopentanoate Diethyleneglycol --
-- -- -- 5 dineopentanoate Sodium 0.01 0.01 0.01 0.01 0.01
hexamethaphosphate Trisodium edetate 0.03 0.03 0.03 0.03 0.03
1,3-butylene glycol 5 5 5 5 5 Potassium hydroxide 0.1 0.1 0.1 0.1
0.1 Carboxyvinyl polymer 0.1 0.1 0.1 0.1 0.1 Phenoxy ethanol 0.15
0.15 0.15 0.15 0.15 Purified water Balance Balance Balance Balance
Balance Evaluation (1): .circleincircle. .circleincircle.
.circleincircle. .circleincircle. .circleincircle. Refreshing
sensation on the skin Evaluation (2): .circleincircle.
.circleincircle. .circleincircle. .circleincircle. .circleincircle.
Permeating sensation on the skin Evaluation (3): .circleincircle.
.circleincircle. .circleincircle. .circleincircle. .circleincircle.
Non-stickiness on the skin
[0109]
5 TABLE 5 Comparative example Ingredients 4 5 6 Tripropyleneglycol
-- -- -- dineopentanoate Decamethyl cyclopentane 5 -- -- siloxane
Isocetyl oleate -- 5 -- Liquid petrolatum -- -- 5 Sodium
hexamethaphosphate 0.01 0.01 0.01 Trisodium edetate 0.03 0.03 0.03
1,3-butylene glycol 5 5 5 Potassium hydroxide 0.1 0.1 0.1
Carboxyvinyl polymer 0.1 0.1 0.1 Phenoxy ethanol 0.15 0.15 0.15
Purified water Balance Balance Balance Evaluation (1): Refreshing
.circleincircle. .circleincircle. .largecircle. sensation on the
skin Evaluation (2): Permeating .circleincircle. .circleincircle.
.DELTA. sensation on the skin Evaluation (3): .circleincircle.
.circleincircle. .circleincircle. Non-stickiness on the skin
[0110] Stability Test for Sunscreen Formulations Containing a
Slightly Soluble Ultraviolet Absorbent
[0111] The sunscreens listed in Table 6 were stored at 0.degree. C.
for two months and then observed with a microscope to ascertain the
presence of precipitation of a slightly-soluble ultraviolet
absorbent
(2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)1,3,5--
triazine)).
6 TABLE 6 Comparative Ingredients Example 13 example 7
Tripropyleneglycol 25 -- dineopentanoate Decamethyl cyclopentane --
25 siloxane 2-ethylhexyl-p- 7 7 methoxycinnamate
2,4-bis{[4-(2-ethylhexyloxy)- 3 3 2-hydroxy]phenyl}-6-(4-
methoxyphenyl) 1,3,5-triazine 1,3-butylene glycol 5 5 Alcohol 5 5
Polyethylene glycol 2 -- dipolyhydroxy stearate Dimeticone copolyol
-- 2 Preservative Appropriate Appropriate amount amount Purified
water Balance Balance Precipitation of crystals .largecircle. X
.largecircle.: No precipitation observed, X: Precipitation
observed
[0112] The results above show that the sunscreens (emulsions)
containing the oil component of the present invention do not cause
precipitation of a slightly soluble ultraviolet absorbent even when
they are stored at low temperatures for a long period of time,
indicating superior stability of the formulations.
[0113] The results above show that the skin treatment compositions
(emulsions) of the present invention exhibit superior effects for
all the evaluation items. Other Examples of the present invention
are shown below.
Example 14
Cream
[0114]
7 A. Oil phase Stearic acid 10.0 mass % Stearyl alcohol 4.0 Butyl
stearate 8.0 Glyceryl monostearate 2.0 Vitamin E acetate 0.5
Vitamin A palmitate 0.1 Tripropyleneglycol dineopentanoate 5.0
Macadamia nut oil 1.0 Tea seed oil 3.0 Perfume 0.4 Phenoxy ethanol
Appropriate amount B. Water phase Glycerin 4.0 1,2 pentane diol 3.0
Sodium hyaluronate 1.0 Potassium hydroxide 2.0 Magnesium ascorbate
phosphate 0.1 L-arginine hydrochloride 0.01 Trisodium edetate 0.05
Purified water Balance
[0115] (Preparation Method and Evaluation)
[0116] Oil phase A and water phase B were each heated up to
70.degree. C. to be dissolved completely. The A phase was added to
the B phase, followed by emulsification by means of an emulsifier.
The emulsion was cooled by a heat exchanger to obtain cream. The
obtained cream exhibited superior smoothness, no stickiness, and
sustained moisture retention.
Example 15
Cream
[0117]
8 A. Oil phase Cetanol 4.0 mass % Petrolatum 7.0 Isopropyl
myristate 8.0 Squalane 10.0 Glyceryl monostearate 2.2 POE(20)
sorbitan monostearate 2.8 Tripropyleneglycol dineopentanoate 10.0
Vitamin E nicotinate 2.0 Perfume 0.3 .delta. -tocopherol 0.05
Phenoxyethanol 0.05 B. Water phase Glycerin 10.0 Sodium hyaluronate
0.02 Dipropylene glycol 4.0 Sodium pyrrolidone carboxylate 1.0
Disodium edetate 0.01 Purified water Balance
[0118] (Preparation Method and Evaluation)
[0119] Cream was obtained in the same manner as in Example 11. The
obtained cream exhibited superior smoothness, no stickiness, and
sustained moisture retention.
Example 16
Foundation
[0120]
9 A. Oil phase Cetanol 3.5 mass % Deodorized lanolin 4.0 Jojoba oil
5.0 Petrolatum 2.0 Squalane 6.0 Glyceryl monostearate 2.5 POE(60)
hydrogenated castor oil 1.5 POE(20) cetyl ether 1.0
Tripropyleneglycol dineopentanoate 2.0 Pyridoxine tripalmitate 0.1
Paraben 0.1 Perfume 0.3 B. Water phase Propylene glycol 10.0 Powder
preparation 12.0 Trisodium ethylenediamine 1.0 hydroxyethyl
triacetate Purified water Balance
[0121] (Preparation Method and Evaluation)
[0122] Foundation was obtained in the same manner as in Example 13.
The obtained foundation had a superior refreshing sensation and
permeating sensation.
Example 17
Sunscreen Emulsion
[0123]
10 A. Oil phase Volatile cyclic silicone 26.5 mass % Titanium
dioxide fine particles 10.0 (Dextrin fatty acid ester-treated: 40
nm) Zinc oxide fine particles (Dextrin fatty acid ester-treated: 60
nm) 10.0 Talc (Dextrin fatty acid ester-treated) 4.0
Tripropyleneglycol dineopentanoate 4.0 Organically modified
montmorillonite 0.5 Octylmethoxy cinnamate 7.5 Phenoxy ethanol 0.1
Perfume Appropriate amount B. Water phase Purified water 26.5
Dipropylene glycol 7.0
[0124] (Preparation method and evaluation)
[0125] The oil phase and the water phase were each mixed and
dissolved separately. Dispersion of titanium dioxide in the oil
phase was thoroughly conducted, to which the water phase was added,
and emulsification was performed using an homogenizer. The obtained
sunscreen emulsion exhibited a superior refreshing sensation.
Example 18
Emulsion
[0126]
11 A. Oil phase Squalane 5.0 mass % Oleyl oleate 3.0 Petrolatum 2.0
Sorbitan sesquioleate 0.8 Polyoxyethylene oleyl ether (2OEO) 1.2
Triethyleneglycol dineopentanoate 2.0 Tripropyleneglycol
dineopentanoate 2.0 Evening primrose oil 0.5 Perfume 0.3 Phenoxy
ethanol 0.2 B. Water phase 1,3-butylene glycol 4.5 Ethanol 3.0
Carboxyvinyl polymer 0.2 Potassium hydroxide 0.1 L-arginine
L-aspartate 0.01 Trisodium edetate 0.05 Purified water Balance
[0127] (Preparation Method and Evaluation)
[0128] The oil phase and the water phase were each mixed and
dissolved. The water phase was added to the oil phase, followed by
emulsification by means of a homogenizer. The obtained emulsion
exhibited superior smoothness, no stickiness, and sustained
moisture retention.
Example 19
Lotion
[0129]
12 A. Alcohol phase Ethanol 5.0 mass % POE oleyl ether 2.0
Tripropyleneglycol dineopentanoate 1.0 2-ethylhexyl-P-dimethylamino
benzoate 0.18 Perfume 0.05 B. Water phase 1,3-butylene glycol 9.5
Sodium pyrrolidone carboxylate 0.5 Nicotinamide 0.3 Glycerin 5.0
Purified water Balance
[0130] (Preparation Method and Evaluation)
[0131] The alcohol phase A was added to the water phase B, followed
by solubilization to obtain a lotion. The obtained lotion exhibited
superior smoothness, no stickiness, and sustained moisture
retention.
Example 20
[0132] Solid Powdery Foundation
13 Silicone-treated sericite 15 mass % Silicone-treated mica 20
Silicone-treated synthetic mica 10 Silicone-treated talc Balance
Zinc oxide 2 Methylsiloxane network polymer 4 spherical powder
Boron nitride 3 Zinc myristate 2 Crushed liquid titanated mica 3
Silicone-treated titanium oxide 10 Silicone-treated iron oxide 4
Silicone-treated zinc oxide 5 Tripropyleneglycol dineopentanoate 1
Dimethyl polysiloxane 4 2-ethylhexyl-p-methoxycinnamate 3
Polyoxyethylene/alkyl co-modified silicone 1 Sorbitan
sesquiisostearate 1 Paraben Appropriate amount .delta. -tocopherol
Appropriate amount Perfume Appropriate amount
[0133] (Preparation Method and Evaluation)
[0134] The powder components, the oil components, and the crushed
liquid titanated mica in the recipe were dispersed/mixed in ethyl
alcohol by using a sand grinder mill having 3 mm-diameter zirconia
beads. After distilling ethyl alcohol, the mixture was. crushed
once with a pulverizer; it was then packed in a container (inner
tray made of resin) and molded by means of a dry press with a prior
art method to obtain solid powdery foundation. The obtained solid
powdery foundation exhibited a superior refreshing sensation.
Example 21
Cleansing Oil
[0135]
14 Liquid petrolatum 68 mass % Dimethyl polysiloxane 2 Ethanol 0.3
Isostearic acid 0.5 Lauric acid 0.1 Cetyl 2-ethylhexanoate 10
Tripropyleneglycol dineopentanoate 5.0 PEG-12 diisostearate 4 PEG-8
diisostearate 1 Coconut fatty acid diethanol amide 0.1 PEG-10
diisostearate 3 Tetrakis (2-hydroxyisopropyl) ethylenediamine 0.1
Vitamin E 0.1 Purified water Balance
[0136] (Preparation Method and Evaluation)
[0137] The cleansing oil was obtained by mixing and dissolving. The
obtained cleansing oil exhibited superior smoothness, no
stickiness, and sustained moisture retention.
Example 22
Hair Shampoo
[0138]
15 Polyoxyethylene laurylsulfate triethanolamine salt 10.0 Lauric
acid diethanol amide 5.0 Lauryldimethylaminoacetic acid betaine 5.0
Ethylene glycol distearate 3.0 Propylene glycol 2.0 Sodium benzoate
0.5 Tripropyleneglycol dineopentanoate 2.0 Coloring agent
Appropriate amount Perfume Appropriate amount Purified water
Balance
[0139] (Preparation Method and Evaluation)
[0140] The aforementioned components were mixed with a conventional
method to prepare a hair shampoo having a pearly look. Head hair
washed with the obtained hair shampoo exhibited no stickiness and
was nicely smooth even without the use of a conventional hair rinse
after washing the hair.
Example 23
Hair Shampoo
[0141]
16 Sodium polyoxyethylene (EO average 3 moles) 10.0 lauryl ether
sulfate Sodium cocoyl propyldimethyl glycine 7.0 Tripropyleneglycol
dineopentanoate 5.0 Cationated cellulose ether 3.0 Coloring agent
Appropriate amount Perfume Appropriate amount Purified water
Balance
[0142] (Preparation Method and Evaluation)
[0143] The aforementioned components were mixed with a conventional
method to prepare a clear hair shampoo. Head hair washed with the
obtained hair shampoo exhibited no stickiness and was nicely smooth
even without the use of a conventional hair rinse after washing the
hair.
Example 24
Hair Shampoo
[0144]
17 Sodium dodecane-1,2-diol acetate ether 10.0 mass % Lauric acid
diethanol amide 5.0 Sodium N-lauroyl-N'-carboxymethyl-N7- 8.0
(2-hydroxyethyl) ethylenediamine Ethylene glycol distearate 3.0
Propylene glycol 2.0 Sodium benzoate 0.5 Tripropyleneglycol
dineopentanoate 2.0 Coloring agent Appropriate amount Perfume
Appropriate amount Purified water Balance
[0145] (Preparation Method and Evaluation)
[0146] The aforementioned components were mixed with a conventional
method to prepare a hair shampoo having a pearly look. Head hair
washed with the obtained hair shampoo was superior in terms of
tactile sensation of the hair during and after use, especially in
terms of smoothness, and it was a hair cleaning agent that
exhibited good foaming and cleansing effects even if a styling
agent had been applied on the hair.
Example 25
Hair Shampoo
[0147]
18 Sodium dodecane-1,2-diol acetate ether 10.0 mass % Sodium
N-lauroyl-N'-carboxymethyl-N'- 8.0 (2-hydroxyethyl)
ethylenediaraine Tripropyleneglycol dineopentanoate 5.0 Cationated
cellulose ether 3.0 Coloring agent Appropriate amount Perfume
Appropriate amount Purified water Balance
[0148] (Preparation Method and Evaluation)
[0149] The aforementioned components were mixed with a conventional
method to prepare a clear hair shampoo. Head hair washed with the
obtained hair shampoo was superior in tactile sensation of the hair
during and after use, especially in terms of smoothness, and it was
a hair cleaning agent that exhibited good foaming and cleansing
effects even if a styling agent had been applied on the hair.
Example 26
Hair Rinse
[0150]
19 Cetyltrimethyl ammonium chloride 0.6 mass % Cetostearyl alcohol
(C16/C18 = 6/4) 4.0 Dimethyl polysiloxane (5 cs) 3.0 Glyceryl
monostearate 1.0 Liquid petrolatum 3.0 Tripropyleneglycol
dineopentanoate 8.0 Glycerol monostearate 1.0 Glycerin 5.0
Propylene glycol 5.0 Preservative Appropriate amount Coloring agent
Appropriate amount Perfume Appropriate amount Purified water
Balance
[0151] (Evaluation)
[0152] This hair rinse gave a moist texture to the hair without
stickiness, and improvesed the smooth and supple texture, thus
giving superior sensation during use.
Example 27
Hair Treatment Cream
[0153]
20 Behenyltrimethyl ammonium chloride 3.0 mass % Cetostearyl
alcohol (C16/C18 = 6/4) 6.5 Behenyl alcohol 2.0 Dimethyl
polysiloxane (20 cs) 3.0 2-octyldodecanol 2.0 Polyoxyethylene
hydrogenated castor oil derivative 0.3 (Ethylene oxide 60 mole
adduct) Polyoxyethylene stearyl ether 1.0 (Ethylene oxide 4 mole
adduct) Soy lecithin 0.5 Liquid petrolatum 3.0 Tripropyleneglycol
dineopentanoate 5.0 Glycerin 10.0 Dipropylene glycol 5.0
Preservative Appropriate amount Coloring agent Appropriate amount
Perfume Appropriate amount Purified water Balance
[0154] (Evaluation)
[0155] This hair treatment cream gave moist texture to the hair
without stickiness, and improved the smooth and supple texture,
thus giving superior sensation during use.
Example 28
Hair Rinse
[0156]
21 Stearic acid diethylaminoethyl amide 0.6 mass % Cetyl alcohol
2.0 Stearyl alcohol 1.0 Dimethyl polysiloxane (5 cs) 3.0 Glycerol
monostearate 1.0 Liquid petrolatum 3.0 Tripropyleneglycol
dineopentanoate 8.0 Glycerol monostearate 1.0 Glycerin 5.0
Propylene glycol 5.0 L-glutamic acid 0.6 Preservative Appropriate
amount Coloring agent Appropriate amount Perfume Appropriate amount
Purified water Balance
[0157] (Evaluation)
[0158] This hair rinse gave a moist texture to the hair without
stickiness, and improved the smooth and supple texture, thus giving
superior sensation during use.
Example 29
Hair Treatment Cream
[0159]
22 Stearic acid dimethylaminopropyl amide 3.0 wt % Cetyl alcohol
6.5 Behenyl alcohol 2.0 Stearic acid 2.0 Dimethyl polysiloxane (20
cs) 3.0 2-octyldodecanol 2.0 Polyoxyethylene hydrogenated castor
oil derivative 0.3 (Ethylene oxide 60 mole adduct) Polyoxyethylene
stearyl ether 1.0 (Ethylene oxide 4 mole adduct) Liquid petrolatum
3.0 Tripropyleneglycol dineopentanoate 5.0 Glycerin 10.0
Dipropylene glycol 5.0 L-glutamic acid 1.0 Preservative Appropriate
amount Coloring agent Appropriate amount Perfume Appropriate amount
Purified water Balance
[0160] (Evaluation)
[0161] This hair treatment cream gives moist texture to the hair
without stickiness, and improves the smooth and supple texture,
thus giving superior sensation during use.
Example 30
Make Cleansing Gel
[0162]
23 Hydroxyethyl cellulose 0.1 mass % Carboxyvinyl polymer 0.4 Alkyl
acrylate/methacrylate copolymer 0.2 Trisodium edetate Appropriate
amount Coconut fatty acid diethanol amide 0.1 Polyethylene glycol
monoisostearate 0.5 Tripropyleneglycol dineopentanoate 5.0
Potassium hydroxide Appropriate amount Alcohol 5.0 Polyoxyethylene
hydrogenated castor 0.3 Preservative Appropriate amount
Decamethylcyclopentasiloxane 18.0 Methylpolysiloxane 3.0 Perfume
Appropriate amount Purified water Balance
[0163] (Preparation Method and Evaluation)
[0164] The aforementioned components were emulsified by an
emulsifier with a conventional method to obtain a make cleansing
gel. The obtained make cleansing gel was easy to rinse off, and
exhibited superior effects in terms of usability, safety, and the
cosmetic-removal effect.
Example 31
Make cleansing Gel
[0165]
24 Hydroxyethyl cellulose 0.05 mass % Carboxyvinyl polymer 0.45
Alkyl acrylate/methacrylate copolymer 0.1 Trisodium edetate
Appropriate amount Sodium methyl cocoyl taurate 0.01 Polyethylene
glycol monoisostearate 3.0 Tripropyleneglycol dineopentanoate 7.0
Poly(sodium aspartate) liquid Appropriate amount Chamomille extract
Appropriate amount Potassium hydroxide Appropriate amount Alcohol
5.0 Polyoxyethylene hydrogenated castor 0.1 Preservative
Appropriate amount Decamethylcyclopentasiloxane 18.0
Methylpolysiloxane 3.0 Perfume Appropriate amount Purified water
Balance
[0166] (Preparation Method and Evaluation)
[0167] The aforementioned components were emulsified by an
emulsifier with a conventional method to obtain a make cleansing
gel. The obtained make cleansing gel was easy to rinse off, and
exhibited superior effects in terms of usability, safety, and the
cosmetic-removal effect.
Example 32
Body Shampoo
[0168]
25 Hydroxypropylmethyl cellulose 0.1 mass % Glycerin 10.0
Dipropylene glycol 5.0 Triethanolamine laurate 12.0
Lauryldimethylaminoacetic acid betaine 5.0 Coconut fatty acid
diethanol amide 3.0 Tripropyleneglycol dineopentanoate 5.0
Chamomille extract Appropriate amount Trisodium edetate Appropriate
amount Preservative Appropriate amount Coloring agent Appropriate
amount Perfume Appropriate amount Purified water Balance
[0169] (Preparation Method and Evaluation)
[0170] The aforementioned components were stirred and dissolved
with a conventional method, followed by cooling by a heat exchanger
to obtain a body shampoo. The obtained body shampoo was easy to
rinse off, and exhibited superior effects in terms of usability,
safety, and the cosmetic-removal effect.
Example 33
Lipstick
[0171]
26 (1) Carnauba wax 1.0 mass % (2) Candelilla wax 2.0 (3) Ceresin
10.0 (4) Squalane Balance (5) Glyceryl triisooctanoate 9.0 (6)
Glyceryl diisostearate 13.0 (7) Tripropyleneglycol dineopentanoate
5.0 (8) Silicone resin 8.0 (9) Hydroxypropyl-.beta.-cyclodextrin
1.0 (10) Cholesteryl macadamiate 3.5 (11) Synthetic sodium
magnesium silicate 0.5 (12) Hydrophobic silica 0.5 (13) Purified
water 2.0 (14) Boron nitride 10.0 (15) Coloring agent Appropriate
amount (16) Preservative Appropriate amount (17) Perfume
Appropriate amount
[0172] (Preparation Method and Evaluation)
[0173] (11) and (12) were dispersed in (10), previously heated up
to 60.degree. C., and (9) and (13) were added to this mixture,
followed by thorough stirring. This was added to separately heated
and dissolved (1)-(8), followed by thorough stirring, and (14)-(17)
were added, followed by dispersing and stirring; the product was
then packed in a container to obtaine a lipstick. The obtained
lipstick was superior in terms of the sensation during use, and
safety thereof.
Industrial Applicability
[0174] The present invention can provide a skin treatment
composition that gives a refreshing sensation at the time of
application and contains an oil component that is highly safe with
low skin irritation.
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