JP6334237B2 - Lip cosmetics - Google Patents

Description

  The present invention relates to a lip cosmetic.

Oil-type lip cosmetics containing silicone with nonionic hydrophilic groups in the molecule will form water and gel on the lips when used by applying to the lips. Are better.
For example, Patent Document 1 describes a makeup cosmetic that contains a silicone having a nonionic hydrophilic group in its molecule, has excellent makeup finish, has good pigment dispersion, and exhibits a bright appearance color. Yes. Patent Document 2 describes an oily solid cosmetic containing a silicone having a nonionic hydrophilic group in the molecule and having excellent usability, finish, and long lasting makeup.

JP 2005-194525 A Japanese Patent Laid-Open No. 5-178722

  In such cosmetics, when an organic pigment is contained, if the heated and melted state is maintained for a long time during heating, silicone having nonionic hydrophilic groups in the molecule exists in the oil phase. Therefore, there is a problem that the organic pigment is likely to aggregate due to the interaction between the hydrophilic silicone and the organic pigment, and the color tends to be dull. In particular, if heat is applied for a long time during filling, the aggregation of organic pigments becomes noticeable, the appearance color of the cosmetic changes, and it is very stable to perform toning and production that brings the color closer to the target color. It was difficult.

  The present inventor uses a specific hydrophobic surface-treated organic pigment and uses a silicone containing a nonionic hydrophilic group in the molecule and a specific liquid oil component in combination, so that the organic pigment aggregates during heating. Even if heat is applied for a long time during filling, changes in the appearance color of the cosmetics are suppressed, making it possible to stably perform toning and production that brings colors closer to the target color, and smoothing during application It was found that lip cosmetics excellent in pod color persistence can be obtained.

The present invention includes the following components (A), (B) and (C):
(A) General formula (1)
(C _n H _{2n + 1} COO) _a Ti (OC _m H _{2m + 1} ) _b (1)
(In the formula, n represents an integer of 1 to 26, m represents an integer of 1 to 12, a and b each represents an integer of 1 to 3, and have a relationship of a + b = 4. The alkyl group is linear or branched and may be a single chain length or a complex chain length)
0.01 to 10% by weight of an organic pigment surface-treated with an alkoxytitanium alkylate represented by
(B) 0.1 to 30% by mass of a silicone containing 0.1 to 50% by mass of a nonionic hydrophilic group in the molecule,
(C) Oil agent selected from ester oil and higher alcohol liquid at 25 ° C. 1 to 95% by mass
Relates to a lip cosmetic containing

  The lip cosmetic of the present invention improves the dispersibility in the oil component by treating the organic pigment with a specific hydrophobic surface treatment, suppresses the aggregation of the organic pigment at the time of heating and melting, and heats the filling for a long time. Even if it is applied, the change in the color of the cosmetic is suppressed, and the toning and production of bringing the color closer to the target color can be performed stably. In particular, the color change of the red organic pigment to yellow is prevented, and color dullness is prevented. In addition, it is excellent in smoothness and color persistence during application.

The organic pigment of component (A) is surface-treated with an alkoxytitanium alkylate represented by the general formula (1).
In the general formula (1), from the viewpoint of imparting water repellency, n is preferably an integer of 13 to 19, m is preferably an integer of 1 to 4, and is preferably an integer of a = 3 and b = 1.
Examples of the alkoxytitanium alkylate represented by the general formula (1) include isopropyl triisostearoyl titanate, isopropyl triisomyristyroyl titanate, methyl triisostearoyl titanate, methyl triisomyristyroyl titanate, and ethyl triisostearoyl titanate. Titanate, ethyl triisomyristylyl titanate and the like can be mentioned, and one kind or a combination of two or more kinds can be used.
Among these, n is an integer of 17, m is an integer of 2 to 3, a = 3 and b = 1 from the viewpoint of improving the dispersibility of the organic pigment in the oil component and improving the smoothness during coating. Is preferable, and isopropyl triisostearoyl titanate is more preferable.
In addition, in this surface treatment, in addition to the surface treatment with the alkoxytitanium alkylate represented by the general formula (1), silicone treatment, alkyl treatment, fatty acid treatment, Lauroyl lysine treatment, lecithin treatment, N-acyl amino acid treatment, metal soap treatment, fluorine compound treatment and the like can be used in combination with one or more kinds within a range not impairing the effects of the present invention.

  Examples of the organic pigment include synthetic organic pigments and natural organic pigments, and any organic pigment may be used as long as it is used in ordinary cosmetics. For example, Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red 202, Red 204, Red 205, Red 220, Red 226, Red 227, Red 228, Red 230, Red 401, Red 405, Red 505, Orange 203, Orange 204 No., orange 205 and other synthetic organic pigments. Moreover, natural organic pigments such as β-carotene, caramel, and paprika pigments can be mentioned. Among them, red 3, red 104, red 106, red 201, red 202, red 204, red 205, red 220, red 226, red 227, red 228, red 230 A red synthetic organic pigment selected from Red 401, Red 405, and Red 505 is preferable, Red 201 and Red 202 are more preferable, and Red 202 is more preferable.

  As a surface treatment method, for example, an organic pigment and a solvent are agitated and mixed with a mixer, and an alkoxytitanium alkylate represented by the general formula (1) is added thereto under a droplet or by spraying, and then constant. Stir at high speed for a long time. Next, the solvent is removed by heating and evaporating at 80 to 250 ° C. while continuing to stir, and then pulverizing and aging at 80 to 250 ° C., whereby a surface-treated organic pigment can be obtained. As the solvent, an organic solvent, water, or the like can be used. As the organic solvent, a volatile organic solvent is preferable, and a volatile hydrocarbon oil and a lower alcohol having 1 to 4 carbon atoms are more preferable, and isopropyl alcohol is more preferable. The surface treatment can also be performed by directly spraying the treatment agent onto the organic pigment.

  The amount of the alkoxy titanium alkylate represented by the general formula (1) in the component (A) organic pigment improves the dispersibility of the organic pigment in the oil component and improves the smoothness during coating. Therefore, 0.1 to 25% by mass is preferable, 3 to 20% by mass is more preferable, 6 to 13% by mass is further preferable, and 8 to 12% by mass is further more preferable.

  Further, in addition to component (A), untreated red No. 3, red 104, red 106, red 201, red 202, red 204, red 205, red 220, red 226, red 227 No., Red 228, Red 230, Red 401, Red 405, and Red synthetic organic pigment selected from Red 505, and a hydrophobic treatment agent applied to normal cosmetic powders, A red synthetic organic pigment subjected to silicone treatment, alkyl treatment, fatty acid treatment, lauroyllysine treatment, lecithin treatment, N-acylamino acid treatment, metal soap treatment, fluorine compound treatment and the like can be used in combination. The red synthetic organic pigment other than the component (A) is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 1% by mass or less, based on the total amount of the red synthetic organic pigment. Even more preferably not.

  The organic pigment of component (A) can be used singly or in combination of two or more. The content of the organic pigment in addition to the purpose of toning a color that is attractive as a lip cosmetic is the dispersibility of the organic pigment in the oil component. From the point of improving, it is 0.01 mass% or more in the whole composition, 0.02 mass% or more is preferable, 0.03 mass% or more is more preferable, 10 mass% or less is preferable, and 4 mass% or less is preferable. 1 mass% or less is more preferable. Moreover, content of a component (A) is 0.01-10 mass% in the whole composition, 0.02-4 mass% is preferable, and 0.03-1 mass% is more preferable.

  The silicone skeleton containing 0.1 to 50% by mass of the nonionic hydrophilic group of the component (B) used in the present invention is not limited as long as it has a silicone skeleton in the main chain. What is represented by Formula (2) is preferable.

(In the formula, R1 to R9 may be the same or different and each represents a linear or branched hydrocarbon group having 1 to 32 carbon atoms, and Q represents a substituent having a nonionic hydrophilic group. 1 ≦ (m ≦ 500, 1 ≦ n ≦ 50)

In the formula (2), the linear or branched hydrocarbon group having 1 to 32 carbon atoms represented by R1 to R9 is preferably a linear or branched hydrocarbon group having 1 to 22 carbon atoms. A linear or branched hydrocarbon group of 1 to 18 is more preferable. Q is not limited as long as it has a nonionic hydrophilic group, and examples thereof include a polyoxyalkylene group, a (poly) glyceryl group, a sugar residue, a polyamide group, and a polyurethane group. Polyoxyalkylene group, an alkyl glyceryl ether group _{preferably, - (CH 2) a -O-} (C 2 H 4 O) b - (C 3 H 6 O) a polyoxyalkylene group represented by _d R10, or An alkylglyceryl ether group represented by — (CH ₂ ) _e —O—CH ₂ —CH (OR 11) —CH ₂ OR 12 is preferable (a represents a number of 1 to 18, b and d are average numbers, , 1 to 50, and e represents a number of 3 to 20. R10, R11, and R12 represent a hydrogen atom or a linear or branched hydrocarbon group having 1 to 18 carbon atoms. The substituent having a nonionic hydrophilic group represented by Q is contained in the molecule in an amount of 0.1 to 50% by mass, preferably 5 to 25% by mass.
M is 1 ≦ m ≦ 500, preferably 5 ≦ m ≦ 200, and more preferably 20 ≦ m ≦ 100. n is 1 ≦ n ≦ 50, preferably 2 ≦ n ≦ 30, more preferably 3 ≦ n ≦ 20.

As silicone of the component (B) represented by Formula (2), polyoxyalkylene modified silicone and alkyl glyceryl ether modified silicone are preferable.
Examples of the polyoxyalkylene-modified silicone include SH3771M, SH3772M, SH3773M, SH3775M, SH3749, DC5200 manufactured by Toray Dow Corning, and KF-6011, KF-6012, KF-6013, and KF- manufactured by Shin-Etsu Chemical Co., Ltd. 6015, KF-6016, KF6017, KF-6004 and the like.

Alkyl glyceryl ether-modified silicone, in formula (2), Q is _{- (CH 2) e -O-} CH 2 -CH (OR11) are preferred those represented by -CH ₂ OR12, R11 is a R12 be the same or different A hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms is preferable, and a hydrogen atom is more preferable.

  Such an alkyl glyceryl ether-modified silicone is prepared by, for example, reacting an organohydrogenpolysiloxane having at least one silicon-hydrogen bond with a corresponding alkenyl glyceryl ether according to the method described in JP-A-4-134014. Can be manufactured.

  The component (B) silicone can be used alone or in combination of two or more, and the content can be improved by improving the adhesion to the lips with a gel obtained by mixing with water, improving the hardness of the coating film, and the like. From the point of being excellent in the sustained effect of the coating film due to the effect of the above, it is 0.1% by mass or more in the total composition, preferably 0.5% by mass or more, more preferably 1% by mass or more, and 30% by mass or less, 20 mass% or less is preferable and 10 mass% or less is more preferable. Moreover, content of a component (B) is 0.1-30 mass% in all the compositions, 0.5-20 mass% is preferable, and 1-10 mass% is more preferable.

  In the present invention, the mass ratio (B) / (A) of the components (A) and (B) is improved when the dispersibility of the organic pigment in the oil component is improved by a specific hydrophobic surface treatment. The aggregation of organic pigments is suppressed, and even when heat is applied for a long time, the change in color is suppressed, in particular, the color change to reddish organic pigments is prevented, and the color blur is reduced. In terms of preventing and excellent in smoothness and color persistence at the time of application, 0.5 or more is preferable, 2 or more is more preferable, 5 or more is more preferable, 500 or less is preferable, 300 or less is more preferable, and 50 or less is further preferable. Moreover, 0.5-500 are preferable, as for the mass ratio (B) / (A) of a component (A) and (B), 2-300 are more preferable, and 5-50 are more preferable.

The oil agent of component (C) is selected from ester oils and higher alcohols and is liquid at 25 ° C. Here, the liquid state at 25 ° C. has fluidity, and includes pastes.
The oil agent selected from such ester oils and higher alcohols may be those used in ordinary cosmetics, for example, vegetable oils such as jojoba oil and olive oil; animal oils such as liquid lanolin; fatty acid esters and polycarboxylic acid esters. , Fatty acid polyhydric alcohol ester, hydroxy fatty acid ester, and other ester oils such as octyl methoxycinnamate, octyl paradimethylaminobenzoate, dl-α-tocopherol, dl-α-tocopherol nicotinate; Examples include higher alcohols.
Of these, fatty acid esters and polyvalent carboxylic acid esters which are liquid at 25 ° C. from the viewpoint of excellent compatibility with silicone containing 0.1 to 50% by mass of the nonionic hydrophilic group of component (B) in the molecule , Fatty acid polyhydric alcohol ester, hydroxy fatty acid ester, and higher alcohol are preferable. Among them, diisostearyl malate, neopentyl glycol dicaprate, isotridecyl isononanoate, 2-ethylhexyl paramethoxycinnamate, octyldodecanol, N- Lauroyl-L-glutamate di (phytosteryl, behenyl, 2-octyldodecyl), tri (capryl capric acid) glycerin, octyldodecyl myristate are more preferable, diisostearyl malate, neopentyl glycol dicaprate, isotride isononanoate Le, 2-ethylhexyl p-methoxycinnamate, octyl dodecanol, N- lauroyl -L- glutamic acid di (phytosteryl, behenyl 2-octyldodecyl) is more preferred.

  The oil agent selected from the ester oil and higher alcohol of component (C) can be used alone or in combination of two or more, and the content is 1 in the whole composition from the viewpoint of vividly showing the gloss and the coating color of the lips. 30% by mass or more, preferably 40% by mass or more, more preferably 95% by mass or less, 85% by mass or less, and more preferably 75% by mass or less. Moreover, content of a component (C) is 1-95 mass% in the whole composition, 30-85 mass% is preferable and 40-75 mass% is more preferable.

  In the present invention, the mass ratio (C) / (B) of the components (B) and (C) is preferably 0.5 or more, more preferably 2 or more, from the viewpoint of excellent smoothness and color persistence during coating. The above is more preferable, 300 or less is preferable, 50 or less is more preferable, and 30 or less is more preferable. Moreover, 0.5-300 are preferable, as for the mass ratio (C) / (B) of a component (B) and (C), 2-50 are more preferable, and 5-30 are more preferable.

The lip cosmetic of the present invention can further contain (D) a solid wax at 25 ° C., imparts appropriate hardness to the lip cosmetic, suppresses oil seepage, and imparts moisture. The durability of the coating film can be improved. Here, the solid indicates a solid property at 25 ° C. and has a melting point of 40 ° C. or higher.
The wax of component (D) is not limited as long as it is used in ordinary cosmetics, for example, mineral waxes such as ozokerite and ceresin; petroleum waxes such as paraffin, microcrystalline wax and petrolatum; Synthetic hydrocarbons such as Tropsch wax and polyethylene wax; plant waxes such as carnauba wax, candelilla wax, rice wax, tree wax, sunflower wax, hydrogenated jojoba oil; animal waxes such as beeswax and whale wax; silicone wax; Synthetic waxes such as fluorine wax and synthetic beeswax; fatty acids, higher alcohols and derivatives thereof.

The wax preferably has a melting point of 50 ° C. or higher and 140 ° C. or lower from the viewpoint of imparting appropriate hardness to the lip cosmetic, suppressing oil seepage, imparting moisture, and improving the durability of the coating film. 60 degreeC or more and 120 degrees C or less are more preferable, and melting | fusing point 60 degrees C or more and 110 degrees C or less are still more preferable.
Component (D) is a microfiber having a melting point of 60 ° C. or higher and 110 ° C. or lower because it imparts an appropriate hardness to the lip cosmetic, is smooth during application, has excellent adhesion to the lips, and is excellent in the durability of the coating film. Crystalline wax, paraffin, ceresin and polyethylene wax are preferred.

  The component (D) wax can be used singly or in combination of two or more, and the content imparts a suitable hardness to the lip cosmetic, suppresses oil seepage, provides moisture, and provides a coating film. From the point which improves the sustainability of this, 1 mass% or more is preferable in the whole composition, 5 mass% or more is more preferable, 7 mass% or more is further more preferable, 12 mass% or more is further more preferable, 30 mass% or less is 30 mass% or less. Preferably, 25 mass% or less is more preferable, 23 mass% or less is more preferable, and 21 mass% or less is further more preferable. Moreover, 1-30 mass% is preferable in the whole composition, as for content of a component (D), 5-25 mass% is more preferable, 7-23 mass% is further more preferable, 12-21 mass% is still more preferable. .

  The lip cosmetic of the present invention, in addition to the above-mentioned components, components used in ordinary cosmetics within a range not impairing the effects of the present invention, for example, powders such as inorganic pigments and clay minerals; Surfactants, lower alcohols, polyhydric alcohols, polymer compounds, UV absorbers other than those described above, antioxidants, fragrances, preservatives, humectants, thickeners, water, and the like can be contained.

The lip cosmetic of the present invention can be produced by a usual method, for example, by heating and dissolving the base material other than the color material, mixing uniformly, and then adding the color material material and further mixing, Can be manufactured.
Further, the lip cosmetic of the present invention can be obtained as a solid or non-solid product, and can be used as a lipstick, lip balm, lip gloss, lip liner or the like.
This invention discloses the following compositions further regarding embodiment mentioned above.

<1> The following components (A), (B) and (C):
(A) General formula (1)
(C _n H _{2n + 1} COO) _a Ti (OC _m H _{2m + 1} ) _b (1)
(In the formula, n represents an integer of 1 to 26, m represents an integer of 1 to 12, a and b each represents an integer of 1 to 3, and have a relationship of a + b = 4. The alkyl group is linear or branched and may be a single chain length or a complex chain length)
0.01 to 10% by weight of an organic pigment surface-treated with an alkoxytitanium alkylate represented by
(B) 0.1 to 30% by mass of a silicone containing 0.1 to 50% by mass of a nonionic hydrophilic group in the molecule,
(C) Oil agent selected from ester oil and higher alcohol liquid at 25 ° C. 1 to 95% by mass
Lip cosmetics containing.

<2> In the component (A), the alkoxytitanium alkylate for surface-treating the organic pigment is preferably an integer of 13 to 19 in the general formula (1), m is an integer of 1 to 4, and a = 3 And b = 1, wherein n is an integer of 17, m is an integer of 2 to 3, and a = 3 and b = 1 are more preferable.
<3> In the component (A), the alkoxytitanium alkylate for surface-treating the organic pigment is preferably isopropyltriisostearoyl titanate, isopropyltriisomyristyroyl titanate, methyltriisostearoyl titanate, methyltriisomyristyroyl Lip cosmetics according to the above <1> or <2>, wherein titanate, ethyl triisostearoyl titanate, ethyl triisomyristyroyl titanate, isopropyl triisostearoyl titanate is more preferable.

<4> In component (A), the organic pigment is preferably Red No. 3, Red No. 104, Red No. 106, Red No. 201, Red No. 202, Red No. 204, Red No. 205, Red No. 220, Red 226 No., Red No. 227, Red No. 228, Red No. 230, Red No. 401, Red No. 405, Red No. 505, Orange No. 203, Orange No. 204, Orange No. 205, β-carotene, caramel, paprika dye, The lip cosmetic according to any one of <1> to <3>, wherein a red synthetic organic pigment is more preferable, Red 201 and Red 202 are more preferable, and Red 202 is even more preferable.
The processing amount of the alkoxytitanium alkylate represented by the general formula (1) in the organic pigment of <5> component (A) is preferably 0.1 to 25% by mass, and more preferably 3 to 20% by mass. The lip cosmetic according to any one of <1> to <4>, preferably 6 to 13% by mass, more preferably 8 to 12% by mass.

The content of the <6> component (A) is preferably 0.02% by mass or more, more preferably 0.03% by mass or more, preferably 4% by mass or less, and preferably 1% by mass or less in the total composition. The lip cosmetic according to any one of <1> to <5>, wherein is more preferable.
<7> Silicone containing 0.1 to 50% by mass of the nonionic hydrophilic group of component (B) in the molecule is preferably the following structural formula (2)

(In the formula, R1 to R9 may be the same or different and each represents a linear or branched hydrocarbon group having 1 to 32 carbon atoms, and Q represents a substituent having a nonionic hydrophilic group. 1 ≦ (m ≦ 500, 1 ≦ n ≦ 50)
The lip cosmetic according to any one of <1> to <6>, which is represented by:
<8> The lip cosmetic according to <7>, wherein the silicone of the component (B) represented by the structural formula (2) is preferably a polyoxyalkylene-modified silicone or an alkylglyceryl ether-modified silicone.

<9> The silicone of the component (B) represented by the structural formula (2) is preferably an alkyl glyceryl ether-modified silicone, and in the formula (2), Q is — (CH ₂ ) _e —O—CH. _{2 -CH (OR11) -CH 2 OR12} (R11 and R12 may be the same or different, preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, more preferably a hydrogen atom .e is 3 to 20 The lip cosmetic described in the above <7> or <8> is more preferable.
The content of <10> component (B) is preferably 0.5% by mass or more, more preferably 1% by mass or more, preferably 20% by mass or less, and more preferably 10% by mass or less in the total composition. The lip cosmetic according to any one of the above items <1> to <9>.
<11> The mass ratio (B) / (A) of the components (A) and (B) is preferably 0.5 or more, more preferably 2 or more, further preferably 5 or more, and preferably 500 or less. The lip cosmetic according to any one of <1> to <10>, more preferably 300 or less, and still more preferably 50 or less.

The oil agent of <12> component (C) is preferably a fatty acid ester, a polycarboxylic acid ester, a fatty acid polyhydric alcohol ester, a hydroxy fatty acid ester, a higher alcohol that is liquid at 25 ° C., and diisostearyl malate, Neopentyl glycol dicaprate, isotridecyl isononanoate, 2-ethylhexyl paramethoxycinnamate, octyldodecanol, N-lauroyl-L-glutamate di (phytosteryl, behenyl, 2-octyldodecyl), tri (capryl, capric acid) glycerin Octyldodecyl myristate is more preferred, diisostearyl malate, neopentyl glycol dicaprate, isotridecyl isononanoate, 2-ethylhexyl paramethoxycinnamate, octyldodecanol, N-lauroyl-L Glutamate di (phytosteryl, behenyl 2-octyldodecyl) is more preferable that the <1> to lip cosmetic as claimed in any one of <11>.
The content of <13> component (C) is preferably 30% by mass or more, more preferably 40% by mass or more, preferably 85% by mass or less, more preferably 75% by mass or less in the total composition. The lip cosmetic according to any one of <1> to <12>.
<14> The mass ratio (C) / (B) of the components (B) and (C) is preferably 0.5 or more, more preferably 2 or more, further preferably 5 or more, and preferably 300 or less. The lip cosmetic according to any one of <1> to <13>, wherein 50 or less is more preferable, and 30 or less is more preferable.

<15> The lip cosmetic according to any one of <1> to <14>, further comprising (D) a solid wax at 25 ° C.
<16> The wax of component (D) is preferably a melting point of 50 ° C. or more and 140 ° C. or less, more preferably a melting point of 60 ° C. or more and 120 ° C. or less, and further preferably a melting point of 60 ° C. or more and 110 ° C. or less. <15> The lip cosmetic.
<17> The lip cosmetic according to <15> or <16>, wherein the component (D) is preferably a microcrystalline wax, paraffin, ceresin, or polyethylene wax having a melting point of 60 ° C. or higher and 110 ° C. or lower.
The content of <18> component (D) is preferably 1% by mass or more in the total composition, more preferably 5% by mass or more, further preferably 7% by mass or more, and further more preferably 12% by mass or more. The lip cosmetic according to any one of <15> to <17>, preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 23% by mass or less, and still more preferably 21% by mass or less. .

Production Example 1
In a Henschel mixer, 900 g of red No. 202 is added, followed by 200 g of isopropyl alcohol and stirred. Next, add 100 g of isopropyl triisostearoyl titanate and stir well. Thereafter, heat is applied to the Henschel mixer, and if necessary, the pressure in the Henschel mixer is reduced to remove isopropyl alcohol. Subsequently, the pigment powder is taken out from the Henschel mixer, heated at 105 ° C. for 6 hours, and then pulverized. In this way, Red No. 202 having surface-coated isopropyl triisostearoyl titanate was obtained.

Production Example 2
In Production Example 1, 100 g of n-octyltriethoxysilane was used in place of isopropyltriisostearoyl titanate, and by the same method as in Production Example 1, red 202 having a surface-coated n-octyltriethoxysilane was obtained. It was.

Production Example 3 (Production of both terminal alkyl-modified / dimethylsiloxane / methyl (undecylglyceryl ether) siloxane copolymer):
(1) STEP-1 (synthesis of tetramethyldisiloxane having an alkyl group different from other alkyl groups in the silicone chain at both ends of the silicone chain):
1,4,8 g of 1,1,3,3-tetramethyldisiloxane and 1.0 g of Spiers catalyst (2-propanol solution of 2 mass% chloroplatinic acid) were added to a three-necked flask and heated to 70 ° C. At 70 ° C. under a nitrogen atmosphere, 174.2 g of α-olefin (“Linearene 168” manufactured by Idemitsu Kosan Co., Ltd., 57/43 (mass ratio) mixture of carbon numbers 16 and 18)) was added dropwise, followed by stirring for 2 hours. It was. After cooling, the reaction system was neutralized with an aqueous sodium hydroxide solution, and purified by distillation under reduced pressure. From the 1H-NMR spectrum (400 MHz) of the obtained product, the obtained product was a 1,1,3,3-tetramethyldisiloxane derivative having an alkyl group having 16 and 18 carbon atoms at both ends. It was confirmed that there was (22.1 g, yield; 85%).

(2) STEP-2 (Synthesis of organohydrogenpolysiloxane having an alkyl group different from other alkyl groups in the silicone chain at both ends of the silicone chain and having a silicon-hydrogen bond in the silicone chain):
4,4.8 g of a 1,1,3,3-tetramethyldisiloxane derivative having an alkyl group having 16 and 18 carbon atoms at both ends synthesized in (1), 78.6 g of decamethylcyclopentasiloxane, 1,3 , 5,7-tetramethylcyclotetrasiloxane 19.8 g, n-heptane 50 g, and activated clay 5 g were added to a three-necked flask and refluxed for 12 hours. After cooling, distillation purification was performed under reduced pressure. From the 1H-NMR spectrum of the obtained product, the obtained product was a dimethylsiloxane / methylsiloxane copolymer having 16 and 18 alkyl groups at both ends (m = 23, n = 4). (132.8 g, yield; 95%).

(3) STEP-3 (Synthesis of polysiloxane in which both ends are substituted with alkyl groups and the side chains are graft-modified with alkyl glyceryl ether groups):
50.0 g of a dimethylsiloxane / methylsiloxane copolymer having an alkyl group having 16 and 18 carbon atoms at both ends synthesized in (2), 61.0 g of 10-undecenyl glyceryl ether, 5% by mass platinum-supporting carbon 0.25 g of the catalyst was added to a three-necked flask and stirred at 70 ° C. for 3 hours. After cooling, distillation purification was performed under reduced pressure. From the 1H-NMR spectrum of the obtained product, the obtained product was a dimethylsiloxane methyl (undecyl glyceryl ether) siloxane copolymer (m = 23, n = 4) (63.0 g, yield; 95%).
The obtained copolymer is a random copolymer as follows in General formula (2).
R ¹ and R ⁹ = an alkyl group whose mode of carbon number is 18;
R ^{2 to} R ⁸ = methyl group,
An alkyl glyceryl ether group represented by Q = — (CH ₂ ) ₁₁ —O—CH ₂ —CH (OH) —CH ₂ OH (e = 11, R 11 and R 12 = hydrogen atom),
m (average value) = 23,
n (average value) = 4.0

Examples 1-4, Comparative Examples 1-2 (stick lipstick)
Stick lipsticks having the compositions shown in Table 1 were produced, and changes in appearance color due to the influence of heat history at 100 ° C., smoothness during application, and color persistence after 5 hours of application were evaluated. The results are also shown in Table 1.

(Production method)
The base material (other than the colorant) was heated and dissolved at 105 ° C. for 30 minutes and mixed uniformly with a disper. Next, the colorant raw material was added and further mixed uniformly for 15 minutes. After defoaming, the mixture was cooled and solidified to room temperature. A necessary amount was cut out from this lipstick bulk A, heated and dissolved at 100 ° C. using a microwave oven, poured into a mold, solidified by cooling, and stick lipstick A was obtained.

(Evaluation method)
(1) Change in appearance color due to influence of 100 ° C. thermal history:
A required amount is cut out from the lipstick bulk A obtained by the above production method, and a stirrer is placed in the lipstick bulk B heated and dissolved at 100 ° C. using a microwave oven. After stirring, the mixture was poured into a mold and solidified by cooling to obtain stick lipstick B. The appearance color of the stick lipstick B was evaluated by the following 10 criteria by 10 specialist panelists using the appearance color of the lipstick A (no stirring) molded by the above production method as a reference color.
Further, the lipstick bulk B was stirred with a magnetic stirrer with a hot plate at 100 ° C. for 0.5 hours, and the lipstick bulk C heated for a total of about 1 hour was poured into a mold and cooled and solidified to obtain a stick lipstick C. The color appearance of the stick lipstick C was also evaluated in the same manner.
The heating time here is the time for the lipstick bulk to reach 100 ° C.
The result was shown as an integrated value of 10 people.
4: The color of the appearance color is not different from the reference color.
3: The color of the appearance color is slightly different from the reference color.
2: The appearance color is different from the reference color.
1: The color of the appearance color is significantly different from the reference color.

(2) Change in appearance color due to influence of heat history at 100 ° C. (measured value):
The appearance color of the lipstick was defined by the CIE 1976 L * a * b * color system, and the appearance color was measured using a color difference meter CR-300 (manufactured by MINOLTA).
The lipstick bulk A obtained by the above manufacturing method is poured into a transparent resin container having a diameter of 43 mm and a height of 6 mm, and cooled and solidified to obtain lipstick A ′, and its appearance color (L0 *, a0 *, b0 *) Measured and used as a reference color. Next, a stir bar is placed in the lipstick bulk A and stirred for 1 hour at 100 ° C. using a magnetic stirrer with a hot plate, and the resulting lipstick bulk D is poured into a transparent resin container having a diameter of 43 mm and a height of 6 mm. The lipstick D was obtained by cooling and solidification, and the appearance color was measured (L1 *, a1 *, b1 *).
The heating time is the time from when the temperature reaches 100 ° C.
The change in appearance color of lipstick D obtained by stirring and dissolving with a stirrer at 100 ° C. for 1 hour was determined as a color difference calculated by the following formula.
ΔE * = ((L1 * −L0 *) ² + (a1 * −a0 *) ² + (b1 * −b0 *) ² ) ^0.5
The change in redness of lipstick D obtained by stirring and dissolving with a stirrer at 100 ° C. for 1 hour was determined as the color difference of a * calculated by the following formula.
Δa * = a1 * −a0 *
The closer Δa * is to 0, the more stable the hue is, and the more negative the value is, the lower the saturation reddish, which means that it looks red due to its appearance and yellowness.

(3) Smoothness during application:
Ten professional panelists evaluated the smoothness when each lipstick was applied to the lips according to the following criteria. The result was shown as an integrated value of 10 people.
4; Smooth.
3; Slightly smooth.
2; Not very smooth.
1: Not smooth

(4) Color duration 5 hours after application:
Ten specialist panelists applied each lipstick to their lips and evaluated the color persistence after 5 hours according to the following criteria. The result was shown as an integrated value of 10 people.
4; The color is persistent.
3; Slight color persists.
2; The color does not last much.
1: The color is not sustained.

Example 5 (Liquid lipstick)
A liquid lipstick having the composition shown in Table 2 was produced, and in the same manner as in Examples 1 to 4, the change in appearance color due to the influence of the heat history at 100 ° C., the smoothness during application, and the color persistence after 5 hours of application were evaluated. . The results are also shown in Table 2.

(Production method)
The base material (other than the colorant) was heated and dissolved at 105 ° C. for 30 minutes and mixed uniformly with a disper. Next, the colorant raw material was added, and the mixture was further uniformly mixed for 15 minutes, defoamed, and then cooled and solidified to room temperature. Thereafter, the necessary amount was cut out, dissolved by heating at 100 ° C. using a microwave oven, poured into a transparent container, cooled and solidified, and a liquid lipstick was obtained.

Claims (6)

The following components (A), (B) and (C):
(A) General formula (1)
(C _n H _{2n + 1} COO) _a Ti (OC _m H _{2m + 1} ) _b (1)
(In the formula, n represents an integer of 1 to 26, m represents an integer of 1 to 12, a and b each represents an integer of 1 to 3, and have a relationship of a + b = 4. The alkyl group is linear or branched and may be a single chain length or a complex chain length)
0.01 to 10% by weight of an organic pigment surface-treated with an alkoxytitanium alkylate represented by
(B) 0.1 to 30% by mass of a silicone containing 0.1 to 50% by mass of a nonionic hydrophilic group in the molecule,
(C) 40 to 95% by mass of an oil agent selected from ester oil and higher alcohol liquid at 25 ° C
Lip cosmetics containing.   The lip cosmetic according to claim 1, wherein the mass ratio (B) / (A) of the components (A) and (B) is 0.5 to 500.   In the component (A), the alkoxytitanium alkylate represented by the general formula (1) is isopropyltriisostearoyl titanate, isopropyltriisomyristyroyl titanate, methyltriisostearoyl titanate, methyltriisomyristyroyl titanate, ethyl The lip cosmetic according to claim 1 or 2, which is one or more selected from triisostearoyl titanate and ethyl triisomyristyroyl titanate. The lip cosmetic according to any one of claims 1 to 3, wherein the component (A) has a treatment amount of 6 to 25% by mass of the alkoxytitanium alkylate represented by the general formula (1).   Furthermore, (D) The oily cosmetics of any one of Claims 1-4 containing a solid wax at 25 degreeC. The lip cosmetic according to any one of claims 1 to 5, wherein the mass ratio (C) / (B) of the components (B) and (C) is 5 to 300.